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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 09:23:04 UTC

Update Date

2022-09-22 17:43:51 UTC

HMDB ID

HMDB0004030

Secondary Accession Numbers

HMDB04030

Metabolite Identification

Common Name

21-Deoxycortisol

Description

Plasma 21-deoxycortisol (21DF) is an excellent marker of 21-hydroxylase deficiency. Currently, it is the only marker able to detect heterozygous carriers with 21-hydroxylase deficiency after Adrenocorticotropic Hormone (ACTH) stimulation. The syndrome of congenital adrenal hyperplasia (CAH) comprises the spectrum of autosomal recessive enzymatic disorders that impair cortisol biosynthesis. The hormonal pattern and clinical manifestations result from hyperstimulation of the adrenal cortex by excessive production of ACTH, untied from the negative feedback exerted by reduced cortisol levels, and the ultimate accumulation of F precursors and androgens. These abnormalities predispose the female newborn to ambiguous genitalia (female pseudohermaphroditism) and precocious puberty that may occur in both sexes. CAH due to 21-hydroxylase deficiency (21OHD) comprises nearly 90% of all cases, with an estimated worldwide incidence of 1 in 14,000 live births. Because 21-deoxycortisol (21DF) is an 11b-hydroxylase (11bOH) derivative of 17-hydroxyprogesterone (17OHP), its serum levels are parallel and proportionally elevated in patients with 21OHD but decreased or undetectable in those with 11b-hydroxylase deficiency (11bOHD), another genetic disorder. Due to the marked buildup of 17OHP in 21OHD, this precursor steroid can proceed directly to 11-hydroxylation, producing distinct elevations of 21DF (PMID: 16551734 , 10731638 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB04030.mol
  Mrv0541 02231219512D          

 28 31  0  0  0  0            999 V2000
   -2.5330   -0.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8185   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041   -0.7127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8185   -0.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -0.7127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3896   -0.3002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0394   -0.3002    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0394    0.5248    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3249    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    0.5248    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8240   -0.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3089    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240    0.7797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5717    1.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244    1.5802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    0.1123    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0394    1.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9199    1.1568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0394   -1.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -1.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2475   -1.9502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6436    1.9502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    0.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
  9 20  1  1  0  0  0
 12 21  1  1  0  0  0
  5 22  1  1  0  0  0
 14 23  1  6  0  0  0
 11 24  1  6  0  0  0
 10 25  1  6  0  0  0
  2 26  2  0  0  0  0
 18 27  2  0  0  0  0
 18 28  1  0  0  0  0
M  END

HMDB0004030
     RDKit          3D
21-Deoxycortisol
 55 58  0  0  0  0  0  0  0  0999 V2000
    4.8170    1.0437   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3487   -0.3612   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0449   -1.1004   -1.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1773   -0.9191    0.1535 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2645   -2.3212    0.0244 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190   -0.4984    1.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1343    0.4576    1.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145   -0.2106    1.0141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1160    0.5262    0.6606 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7687    1.2372    1.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231    2.0403    1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8645    1.0158    0.6829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0765    0.9981    1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0241    0.0038    0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9922   -0.3382    1.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7728   -0.5534   -0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3255   -1.0537   -0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747    0.0802   -0.3338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2474    0.8704   -1.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0498   -0.5293    0.0637 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4130   -1.2451   -1.0638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0809   -2.4880   -1.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0302   -1.5455   -0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8534   -0.4457   -0.3153 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8887    0.7581   -1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8623    1.0704   -0.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1546    1.7452    0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9909    1.4187   -1.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0112   -2.6088    0.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2735   -0.0300    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277   -1.3947    2.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509    1.4820    1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387    0.3858    2.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8851   -1.2239    1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    1.2791   -0.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901    0.5292    2.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419    1.9329    2.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505    2.5692    0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3742    2.7308    1.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4100    1.7257    1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8827    0.2543   -1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4003   -1.4436   -0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1314   -1.4981   -1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643   -1.8104    0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336    1.4745   -1.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220    1.5565   -1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3615    0.1829   -2.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2573   -1.2436    0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5952   -0.7350   -2.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121   -2.7710   -2.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684   -2.5095   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -1.6727   -1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9189    1.7276   -0.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0256    0.7709   -1.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796    0.6840   -1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  6
 24  4  1  0
 24  8  1  0
 20  9  1  0
 18 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  1
  9 35  1  6
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 13 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  1
 21 49  1  6
 22 50  1  0
 23 51  1  0
 23 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
M  END

HMDB04030.mol
  Mrv0541 02231219512D          

 28 31  0  0  0  0            999 V2000
   -2.5330   -0.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8185   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041   -0.7127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8185   -0.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -0.7127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3896   -0.3002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0394   -0.3002    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0394    0.5248    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3249    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    0.5248    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8240   -0.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3089    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240    0.7797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5717    1.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244    1.5802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    0.1123    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0394    1.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9199    1.1568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0394   -1.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -1.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2475   -1.9502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6436    1.9502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    0.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
  9 20  1  1  0  0  0
 12 21  1  1  0  0  0
  5 22  1  1  0  0  0
 14 23  1  6  0  0  0
 11 24  1  6  0  0  0
 10 25  1  6  0  0  0
  2 26  2  0  0  0  0
 18 27  2  0  0  0  0
 18 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004030

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O4/c1-12(22)21(25)9-7-16-15-5-4-13-10-14(23)6-8-19(13,2)18(15)17(24)11-20(16,21)3/h10,15-18,24-25H,4-9,11H2,1-3H3/t15-,16-,17+,18+,19-,20-,21-/m0/s1

> <INCHI_KEY>
LCZBQMKVFQNSJR-CZUPSRJTSA-N

> <FORMULA>
C21H30O4

> <MOLECULAR_WEIGHT>
346.4605

> <EXACT_MASS>
346.214409448

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.58506522323546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14R,15S,17R)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
2.29

> <JCHEM_LOGP>
2.0924144806666662

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.898303639452848

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.69243261354676

> <JCHEM_PKA_STRONGEST_BASIC>
-2.846863247473988

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
95.69779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
21-deoxycortisol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004030
     RDKit          3D
21-Deoxycortisol
 55 58  0  0  0  0  0  0  0  0999 V2000
    4.8170    1.0437   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3487   -0.3612   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0449   -1.1004   -1.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1773   -0.9191    0.1535 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2645   -2.3212    0.0244 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190   -0.4984    1.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1343    0.4576    1.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145   -0.2106    1.0141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1160    0.5262    0.6606 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7687    1.2372    1.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231    2.0403    1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8645    1.0158    0.6829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0765    0.9981    1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0241    0.0038    0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9922   -0.3382    1.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7728   -0.5534   -0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3255   -1.0537   -0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747    0.0802   -0.3338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2474    0.8704   -1.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0498   -0.5293    0.0637 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4130   -1.2451   -1.0638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0809   -2.4880   -1.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0302   -1.5455   -0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8534   -0.4457   -0.3153 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8887    0.7581   -1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8623    1.0704   -0.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1546    1.7452    0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9909    1.4187   -1.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0112   -2.6088    0.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2735   -0.0300    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277   -1.3947    2.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509    1.4820    1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387    0.3858    2.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8851   -1.2239    1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    1.2791   -0.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901    0.5292    2.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419    1.9329    2.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505    2.5692    0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3742    2.7308    1.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4100    1.7257    1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8827    0.2543   -1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4003   -1.4436   -0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1314   -1.4981   -1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643   -1.8104    0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336    1.4745   -1.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220    1.5565   -1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3615    0.1829   -2.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2573   -1.2436    0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5952   -0.7350   -2.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121   -2.7710   -2.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684   -2.5095   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -1.6727   -1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9189    1.7276   -0.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0256    0.7709   -1.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796    0.6840   -1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  6
 24  4  1  0
 24  8  1  0
 20  9  1  0
 18 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  1
  9 35  1  6
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 13 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  1
 21 49  1  6
 22 50  1  0
 23 51  1  0
 23 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB04030.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.728  -1.330   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.728  -2.870   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.395  -3.640   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.061  -2.870   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.061  -1.330   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.395  -0.560   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.727  -3.640   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.606  -2.870   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.606  -1.330   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.727  -0.560   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.940  -0.560   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.940   0.980   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.606   1.750   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.727   0.980   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.405  -1.036   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.310   0.210   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.405   1.455   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.801   2.106   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.032   2.950   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       0.606   0.210   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       1.940   2.520   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.061   0.210   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.717   2.159   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0       1.940  -2.100   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.727  -2.100   0.000  0.00  0.00           H+0
HETATM   26  O   UNK     0      -6.062  -3.640   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.935   3.640   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.062   1.223   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   22                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   20                                             
CONECT   10    9    5   14   25                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   21                                             
CONECT   13   12   14                                                       
CONECT   14   13   10   23                                                  
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18   19                                             
CONECT   18   17   27   28                                                  
CONECT   19   17                                                            
CONECT   20    9                                                            
CONECT   21   12                                                            
CONECT   22    5                                                            
CONECT   23   14                                                            
CONECT   24   11                                                            
CONECT   25   10                                                            
CONECT   26    2                                                            
CONECT   27   18                                                            
CONECT   28   18                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0004030
HETATM    1  C1  UNL     1       4.817   1.044  -0.503  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.349  -0.361  -0.554  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.045  -1.100  -1.272  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.177  -0.919   0.153  1.00  0.00           C  
HETATM    5  O2  UNL     1       3.265  -2.321   0.024  1.00  0.00           O  
HETATM    6  C4  UNL     1       3.319  -0.498   1.620  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.134   0.458   1.842  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.115  -0.211   1.014  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.116   0.526   0.661  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.769   1.237   1.816  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.923   2.040   1.196  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.864   1.016   0.683  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.077   0.998   1.160  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.024   0.004   0.676  1.00  0.00           C  
HETATM   15  O3  UNL     1      -5.992  -0.338   1.397  1.00  0.00           O  
HETATM   16  C13 UNL     1      -4.773  -0.553  -0.678  1.00  0.00           C  
HETATM   17  C14 UNL     1      -3.325  -1.054  -0.636  1.00  0.00           C  
HETATM   18  C15 UNL     1      -2.375   0.080  -0.334  1.00  0.00           C  
HETATM   19  C16 UNL     1      -2.247   0.870  -1.628  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.050  -0.529   0.064  1.00  0.00           C  
HETATM   21  C18 UNL     1      -0.413  -1.245  -1.064  1.00  0.00           C  
HETATM   22  O4  UNL     1      -1.081  -2.488  -1.197  1.00  0.00           O  
HETATM   23  C19 UNL     1       1.030  -1.546  -0.970  1.00  0.00           C  
HETATM   24  C20 UNL     1       1.853  -0.446  -0.315  1.00  0.00           C  
HETATM   25  C21 UNL     1       1.889   0.758  -1.186  1.00  0.00           C  
HETATM   26  H1  UNL     1       5.862   1.070  -0.047  1.00  0.00           H  
HETATM   27  H2  UNL     1       4.155   1.745   0.009  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.991   1.419  -1.530  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.011  -2.609   0.606  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.273  -0.030   1.834  1.00  0.00           H  
HETATM   31  H6  UNL     1       3.128  -1.395   2.235  1.00  0.00           H  
HETATM   32  H7  UNL     1       2.351   1.482   1.561  1.00  0.00           H  
HETATM   33  H8  UNL     1       1.839   0.386   2.916  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.885  -1.224   1.412  1.00  0.00           H  
HETATM   35  H10 UNL     1       0.022   1.279  -0.140  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.190   0.529   2.555  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.042   1.933   2.242  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.450   2.569   0.320  1.00  0.00           H  
HETATM   39  H14 UNL     1      -2.374   2.731   1.908  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.410   1.726   1.932  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.883   0.254  -1.401  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.400  -1.444  -0.876  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.131  -1.498  -1.637  1.00  0.00           H  
HETATM   44  H19 UNL     1      -3.264  -1.810   0.163  1.00  0.00           H  
HETATM   45  H20 UNL     1      -1.334   1.475  -1.672  1.00  0.00           H  
HETATM   46  H21 UNL     1      -3.122   1.557  -1.665  1.00  0.00           H  
HETATM   47  H22 UNL     1      -2.362   0.183  -2.511  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.257  -1.244   0.890  1.00  0.00           H  
HETATM   49  H24 UNL     1      -0.595  -0.735  -2.053  1.00  0.00           H  
HETATM   50  H25 UNL     1      -1.112  -2.771  -2.152  1.00  0.00           H  
HETATM   51  H26 UNL     1       1.268  -2.510  -0.439  1.00  0.00           H  
HETATM   52  H27 UNL     1       1.454  -1.673  -1.991  1.00  0.00           H  
HETATM   53  H28 UNL     1       1.919   1.728  -0.675  1.00  0.00           H  
HETATM   54  H29 UNL     1       1.026   0.771  -1.924  1.00  0.00           H  
HETATM   55  H30 UNL     1       2.780   0.684  -1.839  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    3    4
CONECT    4    5    6   24
CONECT    5   29
CONECT    6    7   30   31
CONECT    7    8   32   33
CONECT    8    9   24   34
CONECT    9   10   20   35
CONECT   10   11   36   37
CONECT   11   12   38   39
CONECT   12   13   13   18
CONECT   13   14   40
CONECT   14   15   15   16
CONECT   16   17   41   42
CONECT   17   18   43   44
CONECT   18   19   20
CONECT   19   45   46   47
CONECT   20   21   48
CONECT   21   22   23   49
CONECT   22   50
CONECT   23   24   51   52
CONECT   24   25
CONECT   25   53   54   55
END

HMDB0004030
     RDKit          3D
21-Deoxycortisol
 55 58  0  0  0  0  0  0  0  0999 V2000
    4.8170    1.0437   -0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3487   -0.3612   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0449   -1.1004   -1.2722 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1773   -0.9191    0.1535 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2645   -2.3212    0.0244 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3190   -0.4984    1.6196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1343    0.4576    1.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1145   -0.2106    1.0141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1160    0.5262    0.6606 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7687    1.2372    1.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9231    2.0403    1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8645    1.0158    0.6829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0765    0.9981    1.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0241    0.0038    0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9922   -0.3382    1.3974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7728   -0.5534   -0.6782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3255   -1.0537   -0.6362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3747    0.0802   -0.3338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2474    0.8704   -1.6279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0498   -0.5293    0.0637 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4130   -1.2451   -1.0638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0809   -2.4880   -1.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0302   -1.5455   -0.9702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8534   -0.4457   -0.3153 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8887    0.7581   -1.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8623    1.0704   -0.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1546    1.7452    0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9909    1.4187   -1.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0112   -2.6088    0.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2735   -0.0300    1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277   -1.3947    2.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509    1.4820    1.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8387    0.3858    2.9163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8851   -1.2239    1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0220    1.2791   -0.1396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1901    0.5292    2.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0419    1.9329    2.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4505    2.5692    0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3742    2.7308    1.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4100    1.7257    1.9318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8827    0.2543   -1.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4003   -1.4436   -0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1314   -1.4981   -1.6370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643   -1.8104    0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3336    1.4745   -1.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1220    1.5565   -1.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3615    0.1829   -2.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2573   -1.2436    0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5952   -0.7350   -2.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1121   -2.7710   -2.1519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684   -2.5095   -0.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -1.6727   -1.9912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9189    1.7276   -0.6745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0256    0.7709   -1.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796    0.6840   -1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  6
 24  4  1  0
 24  8  1  0
 20  9  1  0
 18 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  1
  9 35  1  6
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 13 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  1
 21 49  1  6
 22 50  1  0
 23 51  1  0
 23 52  1  0
 25 53  1  0
 25 54  1  0
 25 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11b,17-Dihydroxy-pregn-4-ene-3,20-dione	HMDB
11b,17-Dihydroxy-progesterone	HMDB
11b,17a-Dihydroxypregn-4-ene-3,20-dione	HMDB
11b,17a-Dihydroxyprogesterone	HMDB
21-Dehydrohydrocortisone	HMDB
21-Deoxyhydrocortisone	HMDB
21-Desoxycortisol	HMDB
4-Pregnene-11beta,17alpha-diol-3,20-dione	HMDB
Pregn-4-ene-11b,17a-diol-3,20-dione	HMDB

Chemical Formula

C₂₁H₃₀O₄

Average Molecular Weight

346.4605

Monoisotopic Molecular Weight

346.214409448

IUPAC Name

(1S,2R,10S,11S,14R,15S,17R)-14-acetyl-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

21-deoxycortisol

CAS Registry Number

641-77-0

SMILES

[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C21H30O4/c1-12(22)21(25)9-7-16-15-5-4-13-10-14(23)6-8-19(13,2)18(15)17(24)11-20(16,21)3/h10,15-18,24-25H,4-9,11H2,1-3H3/t15-,16-,17+,18+,19-,20-,21-/m0/s1

InChI Key

LCZBQMKVFQNSJR-CZUPSRJTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
Hydroxysteroid
Oxosteroid
11-alpha-hydroxysteroid
11-hydroxysteroid
17-hydroxysteroid
Delta-4-steroid
Cyclohexenone
Tertiary alcohol
Alpha-hydroxy ketone
Cyclic alcohol
Secondary alcohol
Ketone
Cyclic ketone
Organic oxide
Organooxygen compound
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect

Endocrine system disorder

Congenital Adrenal Hyperplasia (HMDB: HMDB0004030)

Renal system and urinary system

Renal disorder

Testicular adrenal rest tumors (HMDB: HMDB0004030)

Observation

Preterm birth (HMDB: HMDB0004030)

Genetic disorder

Inborn errors of metabolism

Genetic hormonal aberration

Congenital adrenal hyperplasia

21-hydroxylase deficiency (HMDB: HMDB0004030)
11-beta-hydroxylase deficiency (HMDB: HMDB0004030)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 16551734)

Cellular substructure

Organ

Gland

Adrenal Gland (HMDB: HMDB0004030)
Adrenal Gland (HMDB: HMDB0004030)

Testicle (HMDB: HMDB0004030)
Testicle (HMDB: HMDB0004030)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0004030)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0004030)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004030)

Source

Endogenous

Endogenous (HMDB: HMDB0004030)

Animal

Animal (HMDB: HMDB0004030)

Exogenous

Food

Food (HMDB: HMDB0004030)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0004030)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0004030)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0004030)
Steroidogenesis (PathBank: SMP0063672)

Disease pathway

Apparent Mineralocorticoid Excess Syndrome (PathBank: SMP0120649)
3-beta-Hydroxysteroid Dehydrogenase Deficiency (PathBank: SMP0120650)
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase Deficiency (PathBank: SMP0120672)
11-beta-Hydroxylase Deficiency (CYP11B1) (PathBank: SMP0120858)
Corticosterone Methyl Oxidase I Deficiency (CMO I) (PathBank: SMP0120860)
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH (HMDB: HMDB0004030)
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH (PathBank: SMP0120470)
21-Hydroxylase Deficiency (CYP21) (PathBank: SMP0120640)
17-alpha-Hydroxylase Deficiency (CYP17) (PathBank: SMP0120849)
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase Deficiency (PathBank: SMP0120450)
Corticosterone Methyl Oxidase II Deficiency (CMO II) (PathBank: SMP0120642)

Lipid metabolism pathway (HMDB: HMDB0004030)

Cellular process

Cell signaling (HMDB: HMDB0004030)

Biochemical process

Lipid transport (HMDB: HMDB0004030)

System process

Reproduction (HMDB: HMDB0004030)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0004030)

Molecular messenger

Hormone (HMDB: HMDB0004030)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0004030)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.06 g/L	ALOGPS
logP	2.29	ALOGPS
logP	2.09	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.7 m³·mol⁻¹	ChemAxon
Polarizability	38.59 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	183.991	31661259
DarkChem	[M-H]-	179.192	31661259
DeepCCS	[M-2H]-	218.742	30932474
DeepCCS	[M+Na]+	193.746	30932474
AllCCS	[M+H]+	185.9	32859911
AllCCS	[M+H-H2O]+	183.2	32859911
AllCCS	[M+NH4]+	188.4	32859911
AllCCS	[M+Na]+	189.1	32859911
AllCCS	[M-H]-	190.8	32859911
AllCCS	[M+Na-2H]-	191.2	32859911
AllCCS	[M+HCOO]-	191.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.47 minutes	32390414
Predicted by Siyang on May 30, 2022	12.7283 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.29 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2530.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	217.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	183.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	176.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	550.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	561.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	82.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1031.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	440.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1381.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	333.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	401.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	290.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	299.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	17.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
21-Deoxycortisol	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	4025.3	Standard polar	33892256
21-Deoxycortisol	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2891.0	Standard non polar	33892256
21-Deoxycortisol	[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)C[C@@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	3214.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
21-Deoxycortisol,1TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3169.1	Semi standard non polar	33892256
21-Deoxycortisol,1TMS,isomer #2	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	3086.7	Semi standard non polar	33892256
21-Deoxycortisol,1TMS,isomer #3	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3026.5	Semi standard non polar	33892256
21-Deoxycortisol,1TMS,isomer #4	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3061.3	Semi standard non polar	33892256
21-Deoxycortisol,2TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	3099.3	Semi standard non polar	33892256
21-Deoxycortisol,2TMS,isomer #2	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3078.9	Semi standard non polar	33892256
21-Deoxycortisol,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3137.6	Semi standard non polar	33892256
21-Deoxycortisol,2TMS,isomer #4	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	2946.4	Semi standard non polar	33892256
21-Deoxycortisol,2TMS,isomer #5	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	2992.5	Semi standard non polar	33892256
21-Deoxycortisol,2TMS,isomer #6	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	2975.2	Semi standard non polar	33892256
21-Deoxycortisol,3TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	2965.9	Semi standard non polar	33892256
21-Deoxycortisol,3TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	2992.6	Standard non polar	33892256
21-Deoxycortisol,3TMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	3274.5	Standard polar	33892256
21-Deoxycortisol,3TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	3048.7	Semi standard non polar	33892256
21-Deoxycortisol,3TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	2974.9	Standard non polar	33892256
21-Deoxycortisol,3TMS,isomer #2	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	3339.4	Standard polar	33892256
21-Deoxycortisol,3TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3015.7	Semi standard non polar	33892256
21-Deoxycortisol,3TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3072.0	Standard non polar	33892256
21-Deoxycortisol,3TMS,isomer #3	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3385.0	Standard polar	33892256
21-Deoxycortisol,3TMS,isomer #4	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	2880.7	Semi standard non polar	33892256
21-Deoxycortisol,3TMS,isomer #4	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	2957.8	Standard non polar	33892256
21-Deoxycortisol,3TMS,isomer #4	C=C(O[Si](C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	3427.4	Standard polar	33892256
21-Deoxycortisol,4TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	2943.5	Semi standard non polar	33892256
21-Deoxycortisol,4TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	3014.3	Standard non polar	33892256
21-Deoxycortisol,4TMS,isomer #1	C=C(O[Si](C)(C)C)[C@@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C)C[C@@]21C	3280.8	Standard polar	33892256
21-Deoxycortisol,1TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3406.1	Semi standard non polar	33892256
21-Deoxycortisol,1TBDMS,isomer #2	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3329.1	Semi standard non polar	33892256
21-Deoxycortisol,1TBDMS,isomer #3	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3280.4	Semi standard non polar	33892256
21-Deoxycortisol,1TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3315.2	Semi standard non polar	33892256
21-Deoxycortisol,2TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3584.6	Semi standard non polar	33892256
21-Deoxycortisol,2TBDMS,isomer #2	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3561.1	Semi standard non polar	33892256
21-Deoxycortisol,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3613.7	Semi standard non polar	33892256
21-Deoxycortisol,2TBDMS,isomer #4	CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3394.9	Semi standard non polar	33892256
21-Deoxycortisol,2TBDMS,isomer #5	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3471.4	Semi standard non polar	33892256
21-Deoxycortisol,2TBDMS,isomer #6	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3457.6	Semi standard non polar	33892256
21-Deoxycortisol,3TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3634.8	Semi standard non polar	33892256
21-Deoxycortisol,3TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3628.6	Standard non polar	33892256
21-Deoxycortisol,3TBDMS,isomer #1	CC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3520.0	Standard polar	33892256
21-Deoxycortisol,3TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3735.7	Semi standard non polar	33892256
21-Deoxycortisol,3TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3653.8	Standard non polar	33892256
21-Deoxycortisol,3TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3581.9	Standard polar	33892256
21-Deoxycortisol,3TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3714.7	Semi standard non polar	33892256
21-Deoxycortisol,3TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3663.9	Standard non polar	33892256
21-Deoxycortisol,3TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O)C[C@@]21C	3615.9	Standard polar	33892256
21-Deoxycortisol,3TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3534.0	Semi standard non polar	33892256
21-Deoxycortisol,3TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3572.8	Standard non polar	33892256
21-Deoxycortisol,3TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3671.5	Standard polar	33892256
21-Deoxycortisol,4TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3753.5	Semi standard non polar	33892256
21-Deoxycortisol,4TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3749.7	Standard non polar	33892256
21-Deoxycortisol,4TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)[C@@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC[C@]4(C)[C@H]3[C@H](O[Si](C)(C)C(C)(C)C)C[C@@]21C	3539.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 21-Deoxycortisol GC-MS (Non-derivatized) - 70eV, Positive	splash10-05mo-2957000000-d023e738b8e5b9a63cd2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 21-Deoxycortisol GC-MS (2 TMS) - 70eV, Positive	splash10-004i-2116900000-05061eac5c0a64618c6f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 21-Deoxycortisol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Deoxycortisol 10V, Positive-QTOF	splash10-004j-0009000000-71aa430e3e20af8b2c95	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Deoxycortisol 20V, Positive-QTOF	splash10-01t9-0259000000-2fb2818f214612a10bbf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Deoxycortisol 40V, Positive-QTOF	splash10-0a4u-2690000000-3dd37cf0a48974795770	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Deoxycortisol 10V, Negative-QTOF	splash10-0002-0009000000-2d39ebc543dfc8393535	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Deoxycortisol 20V, Negative-QTOF	splash10-0f9b-0029000000-17d7de8bb31c25cb6a4a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Deoxycortisol 40V, Negative-QTOF	splash10-0kp0-1096000000-a21e11412ea47ba1ded2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Deoxycortisol 10V, Negative-QTOF	splash10-0002-0009000000-19287cb485f1fddca890	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Deoxycortisol 20V, Negative-QTOF	splash10-0002-0009000000-d1621dd0a863681c08e9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Deoxycortisol 40V, Negative-QTOF	splash10-0udr-0079000000-0ce5cfb77bffcbe17979	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Deoxycortisol 10V, Positive-QTOF	splash10-002b-0009000000-f6d8370e2ec523e5bab7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Deoxycortisol 20V, Positive-QTOF	splash10-03di-1924000000-3c950cee78e9c59f06f0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 21-Deoxycortisol 40V, Positive-QTOF	splash10-06tf-7960000000-15e137fe577c2459aaf6	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Adrenal Gland
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Steroidogenesis
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia due to 21-hydroxylase Deficiency		Not Available
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH		Not Available
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia due to 17 Alpha-hydroxylase Deficiency		Not Available
17-alpha-hydroxylase deficiency (CYP17)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00107 (0.00081 - 0.00124) uM	Adult (>18 years old)	Not Specified	Normal	16551734	details
Blood	Detected and Quantified	0.0029 ( 0.0010 - 0.0079) uM	Newborn (0-30 days old)	Both	Normal	17456574	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00234 (0.00008-0.04071) uM	Adult (>18 years old)	Not Specified	21-Hydroxylase deficiency	16551734	details
Blood	Detected and Quantified	0.048 (0.014 - 0.320) uM	Newborn (0-30 days old)	Not Specified	Congenital adrenal hyperplasia	17456574	details
Blood	Detected and Quantified	0.0056 (0.0022-0.0149) uM	Newborn (0-30 days old)	Both	Preterm birth	17456574	details
Blood	Detected and Quantified	0.0054 +/- 0.008 uM	Adult (>18 years old)	Male	Bilateral testicular adrenal rest tumors	17595257	details
Blood	Detected and Quantified	0.00110 (0.00081 - 0.00196) uM	Adult (>18 years old)	Both	11-beta-Hydroxylase deficiency	16551734	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

21-Hydroxylase deficiency
Tonetto-Fernandes V, Lemos-Marini SH, Kuperman H, Ribeiro-Neto LM, Verreschi IT, Kater CE: Serum 21-Deoxycortisol, 17-Hydroxyprogesterone, and 11-deoxycortisol in classic congenital adrenal hyperplasia: clinical and hormonal correlations and identification of patients with 11beta-hydroxylase deficiency among a large group with alleged 21-hydroxylase deficiency. J Clin Endocrinol Metab. 2006 Jun;91(6):2179-84. Epub 2006 Mar 21. [PubMed:16551734 ]
Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency
Janzen N, Peter M, Sander S, Steuerwald U, Terhardt M, Holtkamp U, Sander J: Newborn screening for congenital adrenal hyperplasia: additional steroid profile using liquid chromatography-tandem mass spectrometry. J Clin Endocrinol Metab. 2007 Jul;92(7):2581-9. Epub 2007 Apr 24. [PubMed:17456574 ]
Preterm birth
Janzen N, Peter M, Sander S, Steuerwald U, Terhardt M, Holtkamp U, Sander J: Newborn screening for congenital adrenal hyperplasia: additional steroid profile using liquid chromatography-tandem mass spectrometry. J Clin Endocrinol Metab. 2007 Jul;92(7):2581-9. Epub 2007 Apr 24. [PubMed:17456574 ]
Testicular adrenal rest tumors
Claahsen-van der Grinten HL, Otten BJ, Sweep FC, Span PN, Ross HA, Meuleman EJ, Hermus AR: Testicular tumors in patients with congenital adrenal hyperplasia due to 21-hydroxylase deficiency show functional features of adrenocortical tissue. J Clin Endocrinol Metab. 2007 Sep;92(9):3674-80. Epub 2007 Jun 26. [PubMed:17595257 ]
11-beta-Hydroxylase deficiency
Tonetto-Fernandes V, Lemos-Marini SH, Kuperman H, Ribeiro-Neto LM, Verreschi IT, Kater CE: Serum 21-Deoxycortisol, 17-Hydroxyprogesterone, and 11-deoxycortisol in classic congenital adrenal hyperplasia: clinical and hormonal correlations and identification of patients with 11beta-hydroxylase deficiency among a large group with alleged 21-hydroxylase deficiency. J Clin Endocrinol Metab. 2006 Jun;91(6):2179-84. Epub 2006 Mar 21. [PubMed:16551734 ]

Associated OMIM IDs

201910 (21-Hydroxylase deficiency)
201910 (Congenital Adrenal Hyperplasia, due to 21-Hydroxylase-Deficiency)
202010 (11-beta-Hydroxylase deficiency)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023283

KNApSAcK ID

Not Available

Chemspider ID

193458

KEGG Compound ID

C05497

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

21-Deoxycortisol

METLIN ID

7004

PubChem Compound

222803

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

M00603

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Hill, Martin; Lapcik, Oldrich; Hampl, Richard; Starka, Luboslav; Putz, Zdenek. Radioimmunoassay of three deoxycorticoids in human plasma following HPLC separation. Steroids (1995), 60(9), 615-20.

Material Safety Data Sheet (MSDS)

Not Available

General References

Solish SB, Goldsmith MA, Voutilainen R, Miller WL: Molecular characterization of a Leydig cell tumor presenting as congenital adrenal hyperplasia. J Clin Endocrinol Metab. 1989 Dec;69(6):1148-52. [PubMed:2555382 ]
Gueux B, Fiet J, Couillin P, Raux-Demay MC, Mornet E, Galons H, Villette JM, Boue J, Dreux C: Prenatal diagnosis of 21-hydroxylase deficiency congenital adrenal hyperplasia by simultaneous radioimmunoassay of 21-deoxycortisol and 17-hydroxyprogesterone in amniotic fluid. J Clin Endocrinol Metab. 1988 Mar;66(3):534-7. [PubMed:3258316 ]
Finkelstein M, Litvin Y, Mizrachi Y, Neiman G, Rosler A: Apparent double defect in C11 beta and C21-steroid hydroxylation in congenital adrenal hyperplasia. J Steroid Biochem. 1983 Jul;19(1B):675-81. [PubMed:6310249 ]
Penny R, Vecsei P: Congenital adrenal hyperplasia due to combined 21- and 11 beta-hydroxylase deficiency. J Endocrinol Invest. 1989 Nov;12(10):723-8. [PubMed:2614011 ]
Fiet J, Gueux B, Raux-Demay MC, Kuttenn F, Vexiau P, Gourmelen M, Couillin P, Mornet E, Villette JM, Brerault JL, et al.: [21-deoxycortisol. A new marker of virilizing adrenal hyperplasia caused by 21-hydroxylase deficiency]. Presse Med. 1989 Dec 2;18(40):1965-9. [PubMed:2531882 ]
Tonetto-Fernandes V, Lemos-Marini SH, Kuperman H, Ribeiro-Neto LM, Verreschi IT, Kater CE: Serum 21-Deoxycortisol, 17-Hydroxyprogesterone, and 11-deoxycortisol in classic congenital adrenal hyperplasia: clinical and hormonal correlations and identification of patients with 11beta-hydroxylase deficiency among a large group with alleged 21-hydroxylase deficiency. J Clin Endocrinol Metab. 2006 Jun;91(6):2179-84. Epub 2006 Mar 21. [PubMed:16551734 ]
Fiet J, Boudi A, Giton F, Villette JM, Boudou P, Soliman H, Morineau G, Galons H: Plasma 21-deoxycortisol: comparison of a time-resolved fluoroimmunoassay using a biotinylated tracer with a radioimmunossay using (125)iodine. J Steroid Biochem Mol Biol. 2000 Jan-Feb;72(1-2):55-60. [PubMed:10731638 ]

Enzymes

Enzyme Details

1. Cytochrome P450 11B1, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:: CYP11B1
Uniprot ID:: P15538
Molecular weight:: 57572.44

Reactions

17-Hydroxyprogesterone + Reduced ferredoxin + Oxygen → 21-Deoxycortisol + Oxidized ferredoxin + Water	details

Enzyme Details

2. Steroid 17-alpha-hydroxylase/17,20 lyase

General function:: Involved in monooxygenase activity
Specific function:: Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation and the 17,20-lyase reaction. Involved in sexual development during fetal life and at puberty.
Gene Name:: CYP17A1
Uniprot ID:: P05093
Molecular weight:: 57369.995

Reactions

21-Deoxycortisol + Acceptor + Water → 11beta-Hydroxyprogesterone + Reduced acceptor + Oxygen	details

Enzyme Details

3. Cytochrome P450 11B2, mitochondrial

General function:: Involved in monooxygenase activity
Specific function:: Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name:: CYP11B2
Uniprot ID:: P19099
Molecular weight:: 57559.62

Reactions

17-Hydroxyprogesterone + Reduced ferredoxin + Oxygen → 21-Deoxycortisol + Oxidized ferredoxin + Water	details

Enzyme Details

4. Cytochrome P450 21-hydroxylase

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: P450-CYP21B
Uniprot ID:: Q16874
Molecular weight:: 56000.9

Enzyme Details

5. Cytochrome P450, family 21, subfamily A, polypeptide 2

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP21A2
Uniprot ID:: Q08AG9
Molecular weight:: 55972.9

Enzyme Details

6. Steroid 21-hydroxylase

General function:: Not Available
Specific function:: Specifically catalyzes the 21-hydroxylation of steroids. Required for the adrenal synthesis of mineralocorticoids and glucocorticoids.
Gene Name:: CYP21A2
Uniprot ID:: P08686
Molecular weight:: 56000.94

Reactions

21-Deoxycortisol + Reduced acceptor + Oxygen → Cortisol + Acceptor + Water	details

Showing metabocard for 21-Deoxycortisol (HMDB0004030)

MOL for HMDB0004030 (21-Deoxycortisol)

3D MOL for HMDB0004030 (21-Deoxycortisol)

3D SDF for HMDB0004030 (21-Deoxycortisol)

3D-SDF for HMDB0004030 (21-Deoxycortisol)

PDB for HMDB0004030 (21-Deoxycortisol)

3D PDB for HMDB0004030 (21-Deoxycortisol)

SMILES for HMDB0004030 (21-Deoxycortisol)

INCHI for HMDB0004030 (21-Deoxycortisol)

Structure for HMDB0004030 (21-Deoxycortisol)

3D Structure for HMDB0004030 (21-Deoxycortisol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions