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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-08-13 09:23:58 UTC

Update Date

2022-03-07 02:49:20 UTC

HMDB ID

HMDB0004031

Secondary Accession Numbers

HMDB0013594
HMDB04031
HMDB13594

Metabolite Identification

Common Name

11beta-Hydroxyprogesterone

Description

11beta-Hydroxyprogesterone is a normal human metabolite. Plasma 11beta-Hydroxyprogesterone concentrations does not vary significantly as a function of age, sex, or phase of the menstrual cycle, in contrast to 17-hydroxyprogesterone. Increased plasma 11beta-Hydroxyprogesterone levels in late-onset adrenal 21-hydroxylase deficiency suggest a mild defect of the mineralocorticoid pathway. 21-hydroxylase deficiency (OMIM 201910 ) is probably the most frequent (if not the most frequent) autosomal recessive genetic disease, occurring in almost 1% of Caucasians and about 3% of Ashkenazi Jews. 21-hydroxylase deficiency is unusual among genetic diseases in that approximately 95% of the mutant alleles have apparently been generated by recombination between a normally active gene (CYP21) and a closely linked pseudogene (CYP21P). There are 4 recognized clinical forms of congenital adrenal hyperplasia, the majority of cases being associated with 21-hydroxylase deficiency: salt-wasting (SW), simple virilizing (SV), nonclassic (NC) late-onset (also called attenuated and acquired), and cryptic. (PMID: 3546944 , 2537337 ). 11beta-hydroxyprogesterone acts as a mineralocorticoid agonist in stimulating Na+ absorption in mammalian principal cortical collecting duct cells.It activates the transiently expressed hMR in COS-7 cells in a dose-dependent manner (ED(50): 10(-8) M) and, like aldosterone, stimulated Ams I(sc) in mpkCCD(cl4) cells. Docking 11OHP within the hMR-ligand-binding domain homology model revealed that the agonist activity of 11OHP is caused by contacts between its 11 beta-hydroxyl group and Asn770. Furthermore, 11OHP was unable to activate the mutant hMR/N770A, in which Ala is substituted for Asn at position 770. These findings demonstrate that in the absence of the 21-hydroxyl group, the 11 beta-hydroxyl group can produce the contact with the hMR-Asn770 required for the hMR activation leading to stimulated Na(+) absorption.

Structure

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

  Mrv1652308132018492D          

 27 30  0  0  0  0            999 V2000
 9999.287510000.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.285510000.8428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1482 9997.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.424810001.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.713410000.0077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9999 9998.7732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.4248 9998.7732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0003 9997.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7148 9998.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.713010000.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.998510000.4261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.9985 9999.6010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7130 9999.1886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5745 9999.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8600 9999.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8600 9998.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5745 9997.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2890 9998.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2890 9999.1796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.427510000.4261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.4275 9999.6011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2121 9999.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.697010000.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.212110000.6811    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.467110001.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.915010002.0788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.274010001.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 11  2  1  1  0  0  0
 12  6  1  6  0  0  0
  9 13  1  0  0  0  0
 13  5  1  1  0  0  0
 16  3  2  0  0  0  0
 19  1  1  1  0  0  0
 12 19  1  0  0  0  0
 18  8  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  1  0  0  0
 25 27  1  0  0  0  0
 25 26  2  0  0  0  0
 13 21  1  0  0  0  0
 21  7  1  6  0  0  0
 10 20  1  0  0  0  0
 20  4  1  1  0  0  0
M  END

HMDB0004031
     RDKit          3D
11beta-Hydroxyprogesterone
 54 57  0  0  0  0  0  0  0  0999 V2000
    5.5741    1.0275   -0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2261    0.9851   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0629    1.6154    0.9074 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041    0.2381   -0.6730 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3763   -1.2549   -0.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0350   -1.9556   -0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0820   -0.8260   -0.5429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2481   -1.0429    0.1147 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0778   -1.9993   -0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1129   -1.3907   -1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9450   -0.3822   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1142   -0.0648   -1.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9127    0.9380   -0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9409    1.4268   -1.1960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4888    1.3826    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9693    1.5981    0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3940    0.2328    0.3386 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7624   -0.6450    1.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9161    0.3174    0.1028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1881    1.3131    0.9537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0085    0.9249    2.2545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1769    1.5364    0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8837    0.2345    0.2275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3292   -0.2394    1.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3156    1.0406    0.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6956    1.9921   -1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7294    0.2168   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817    0.5768   -1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0717   -1.6178   -0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7215   -1.5505   -1.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0447   -2.4832    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8405   -2.7169   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9709   -0.4414   -1.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463   -1.3903    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5993   -2.7473   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925   -2.5827   -1.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8042   -2.2254   -1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6674   -1.0018   -2.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5060   -0.5391   -2.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7010    0.5550    1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9989    2.3135    0.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438    1.9515    1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7867    2.3158   -0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598   -1.3031    1.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493   -0.0210    2.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6537   -1.2761    1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7938    0.6855   -0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147    2.2741    0.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458    0.8688    2.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7727    2.2457    0.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9531    1.8950   -0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -1.0704    1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3068    0.6228    2.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141   -0.5571    1.5882 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  0
  5  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  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  7  1  0
 19  8  1  0
 17 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  6
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  6
  8 34  1  1
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  6
 20 48  1  1
 21 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

  Mrv1652308132018492D          

 27 30  0  0  0  0            999 V2000
 9999.287510000.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.285510000.8428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1482 9997.9399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.424810001.2572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.713410000.0077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9999 9998.7732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10001.4248 9998.7732    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
10000.0003 9997.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7148 9998.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.713010000.8386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.998510000.4261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.9985 9999.6010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.7130 9999.1886    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.5745 9999.5921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8600 9999.1796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8600 9998.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5745 9997.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2890 9998.3545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2890 9999.1796    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.427510000.4261    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.4275 9999.6011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2121 9999.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.697010000.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.212110000.6811    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.467110001.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.915010002.0788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.274010001.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 11  2  1  1  0  0  0
 12  6  1  6  0  0  0
  9 13  1  0  0  0  0
 13  5  1  1  0  0  0
 16  3  2  0  0  0  0
 19  1  1  1  0  0  0
 12 19  1  0  0  0  0
 18  8  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 20  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  1  0  0  0
 25 27  1  0  0  0  0
 25 26  2  0  0  0  0
 13 21  1  0  0  0  0
 21  7  1  6  0  0  0
 10 20  1  0  0  0  0
 20  4  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0004031

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@H](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/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18-,19+,20-,21+/m0/s1

> <INCHI_KEY>
BFZHCUBIASXHPK-ATWVFEABSA-N

> <FORMULA>
C21H30O3

> <MOLECULAR_WEIGHT>
330.4611

> <EXACT_MASS>
330.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.11860709950443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
2.8398396036666673

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.545038962490786

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.87532633266298

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2594841269974141

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
94.2978

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004031
     RDKit          3D
11beta-Hydroxyprogesterone
 54 57  0  0  0  0  0  0  0  0999 V2000
    5.5741    1.0275   -0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2261    0.9851   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0629    1.6154    0.9074 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041    0.2381   -0.6730 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3763   -1.2549   -0.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0350   -1.9556   -0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0820   -0.8260   -0.5429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2481   -1.0429    0.1147 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0778   -1.9993   -0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1129   -1.3907   -1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9450   -0.3822   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1142   -0.0648   -1.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9127    0.9380   -0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9409    1.4268   -1.1960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4888    1.3826    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9693    1.5981    0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3940    0.2328    0.3386 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7624   -0.6450    1.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9161    0.3174    0.1028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1881    1.3131    0.9537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0085    0.9249    2.2545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1769    1.5364    0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8837    0.2345    0.2275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3292   -0.2394    1.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3156    1.0406    0.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6956    1.9921   -1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7294    0.2168   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817    0.5768   -1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0717   -1.6178   -0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7215   -1.5505   -1.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0447   -2.4832    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8405   -2.7169   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9709   -0.4414   -1.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463   -1.3903    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5993   -2.7473   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925   -2.5827   -1.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8042   -2.2254   -1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6674   -1.0018   -2.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5060   -0.5391   -2.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7010    0.5550    1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9989    2.3135    0.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438    1.9515    1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7867    2.3158   -0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598   -1.3031    1.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493   -0.0210    2.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6537   -1.2761    1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7938    0.6855   -0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147    2.2741    0.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458    0.8688    2.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7727    2.2457    0.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9531    1.8950   -0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -1.0704    1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3068    0.6228    2.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141   -0.5571    1.5882 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  0
  5  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  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  7  1  0
 19  8  1  0
 17 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  6
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  6
  8 34  1  1
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  6
 20 48  1  1
 21 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 13-AUG-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-AUG-20         0                                  
HETATM    1  C   UNK     0    8665.3378666.681   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8665.3338668.240   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8661.3438662.821   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8669.3268669.013   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0    8667.9988666.681   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8666.6668664.377   0.000  0.00  0.00           H+0
HETATM    7  H   UNK     0    8669.3268664.377   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0    8666.6678662.825   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8668.0018663.595   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.9988668.232   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8666.6648667.462   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8666.6648665.922   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.9988665.152   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.0068665.905   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8662.6728665.135   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8662.6728663.595   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.0068662.825   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.3398663.595   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8665.3398665.135   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.3318667.462   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.3318665.922   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.7968665.446   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8671.7018666.692   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8670.7968667.938   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8671.2728669.403   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0    8670.2418670.547   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0    8672.7788669.723   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   11                                                            
CONECT    3   16                                                            
CONECT    4   20                                                            
CONECT    5   13                                                            
CONECT    6   12                                                            
CONECT    7   21                                                            
CONECT    8    9   18                                                       
CONECT    9    8   13                                                       
CONECT   10   11   20                                                       
CONECT   11   10   12    2                                                  
CONECT   12   11   13    6   19                                             
CONECT   13   12    9    5   21                                             
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17    3                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19    8                                                  
CONECT   19   14   18    1   12                                             
CONECT   20   21   24   10    4                                             
CONECT   21   20   22   13    7                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   20   23   25                                                  
CONECT   25   24   27   26                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0004031
HETATM    1  C1  UNL     1       5.574   1.027  -0.737  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.226   0.985  -0.120  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.063   1.615   0.907  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.104   0.238  -0.673  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.376  -1.255  -0.782  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.035  -1.956  -0.530  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.082  -0.826  -0.543  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.248  -1.043   0.115  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.078  -1.999  -0.666  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.113  -1.391  -1.565  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.945  -0.382  -0.888  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.114  -0.065  -1.378  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.913   0.938  -0.683  1.00  0.00           C  
HETATM   14  O2  UNL     1      -5.941   1.427  -1.196  1.00  0.00           O  
HETATM   15  C13 UNL     1      -4.489   1.383   0.660  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.969   1.598   0.599  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.394   0.233   0.339  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.762  -0.645   1.508  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.916   0.317   0.103  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.188   1.313   0.954  1.00  0.00           C  
HETATM   21  O3  UNL     1      -0.009   0.925   2.255  1.00  0.00           O  
HETATM   22  C19 UNL     1       1.177   1.536   0.285  1.00  0.00           C  
HETATM   23  C20 UNL     1       1.884   0.235   0.228  1.00  0.00           C  
HETATM   24  C21 UNL     1       2.329  -0.239   1.572  1.00  0.00           C  
HETATM   25  H1  UNL     1       6.316   1.041   0.075  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.696   1.992  -1.307  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.729   0.217  -1.475  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.782   0.577  -1.676  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.072  -1.618  -0.027  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.722  -1.550  -1.783  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.045  -2.483   0.455  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.841  -2.717  -1.299  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.971  -0.441  -1.569  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.046  -1.390   1.151  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.599  -2.747  -0.032  1.00  0.00           H  
HETATM   36  H12 UNL     1      -0.393  -2.583  -1.316  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.804  -2.225  -1.863  1.00  0.00           H  
HETATM   38  H14 UNL     1      -1.667  -1.002  -2.516  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.506  -0.539  -2.301  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.701   0.555   1.360  1.00  0.00           H  
HETATM   41  H17 UNL     1      -4.999   2.313   0.981  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.644   1.951   1.576  1.00  0.00           H  
HETATM   43  H19 UNL     1      -2.787   2.316  -0.223  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.960  -1.303   1.848  1.00  0.00           H  
HETATM   45  H21 UNL     1      -3.049  -0.021   2.405  1.00  0.00           H  
HETATM   46  H22 UNL     1      -3.654  -1.276   1.301  1.00  0.00           H  
HETATM   47  H23 UNL     1      -0.794   0.686  -0.962  1.00  0.00           H  
HETATM   48  H24 UNL     1      -0.715   2.274   0.880  1.00  0.00           H  
HETATM   49  H25 UNL     1      -0.846   0.869   2.739  1.00  0.00           H  
HETATM   50  H26 UNL     1       1.773   2.246   0.858  1.00  0.00           H  
HETATM   51  H27 UNL     1       0.953   1.895  -0.736  1.00  0.00           H  
HETATM   52  H28 UNL     1       1.773  -1.070   1.999  1.00  0.00           H  
HETATM   53  H29 UNL     1       2.307   0.623   2.302  1.00  0.00           H  
HETATM   54  H30 UNL     1       3.414  -0.557   1.588  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5   23   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   23   33
CONECT    8    9   19   34
CONECT    9   10   35   36
CONECT   10   11   37   38
CONECT   11   12   12   17
CONECT   12   13   39
CONECT   13   14   14   15
CONECT   15   16   40   41
CONECT   16   17   42   43
CONECT   17   18   19
CONECT   18   44   45   46
CONECT   19   20   47
CONECT   20   21   22   48
CONECT   21   49
CONECT   22   23   50   51
CONECT   23   24
CONECT   24   52   53   54
END

HMDB0004031
     RDKit          3D
11beta-Hydroxyprogesterone
 54 57  0  0  0  0  0  0  0  0999 V2000
    5.5741    1.0275   -0.7370 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2261    0.9851   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0629    1.6154    0.9074 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041    0.2381   -0.6730 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3763   -1.2549   -0.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0350   -1.9556   -0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0820   -0.8260   -0.5429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2481   -1.0429    0.1147 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0778   -1.9993   -0.6658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1129   -1.3907   -1.5649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9450   -0.3822   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1142   -0.0648   -1.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9127    0.9380   -0.6835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9409    1.4268   -1.1960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4888    1.3826    0.6600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9693    1.5981    0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3940    0.2328    0.3386 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7624   -0.6450    1.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9161    0.3174    0.1028 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1881    1.3131    0.9537 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0085    0.9249    2.2545 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1769    1.5364    0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8837    0.2345    0.2275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3292   -0.2394    1.5717 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3156    1.0406    0.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6956    1.9921   -1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7294    0.2168   -1.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7817    0.5768   -1.6759 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0717   -1.6178   -0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7215   -1.5505   -1.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0447   -2.4832    0.4554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8405   -2.7169   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9709   -0.4414   -1.5689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0463   -1.3903    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5993   -2.7473   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925   -2.5827   -1.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8042   -2.2254   -1.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6674   -1.0018   -2.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5060   -0.5391   -2.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7010    0.5550    1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9989    2.3135    0.9808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438    1.9515    1.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7867    2.3158   -0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598   -1.3031    1.8480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493   -0.0210    2.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6537   -1.2761    1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7938    0.6855   -0.9618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147    2.2741    0.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458    0.8688    2.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7727    2.2457    0.8578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9531    1.8950   -0.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -1.0704    1.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3068    0.6228    2.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4141   -0.5571    1.5882 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  0
  5  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  2  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  7  1  0
 19  8  1  0
 17 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  6
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  6
  8 34  1  1
  9 35  1  0
  9 36  1  0
 10 37  1  0
 10 38  1  0
 12 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  6
 20 48  1  1
 21 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(11beta)-11-Hydroxypregn-4-ene-3,20-dione	ChEBI
21-Deoxycorticosterone	ChEBI
(11b)-11-Hydroxypregn-4-ene-3,20-dione	Generator
(11Β)-11-hydroxypregn-4-ene-3,20-dione	Generator
11b-Hydroxyprogesterone	Generator
11Β-hydroxyprogesterone	Generator
Pregn-4-ene-11 beta-ol-3,20-dione	MeSH
Hylutin	MeSH
Hyprogest	MeSH
11-Hydroxyprogesterone, (11alpha,17alpha)-(+-)-isomer	MeSH
11-Hydroxyprogesterone	MeSH
Duralutin	MeSH
Prodrox	MeSH
11 beta-Hydroxy-4-pregnen-3,20-dione	MeSH
11-Hydroxyprogesterone, (11beta)-isomer	MeSH
11-Hydroxyprogesterone, (11alpha)-(+-)-isomer	MeSH
11-Hydroxyprogesterone, (9beta,10alpha,11alpha)-isomer	MeSH
11 alpha-Hydroxyprogesterone	MeSH
11ohp Compound	MeSH
Hy-gestrone	MeSH
Pergestron	MeSH
Pro-depo	MeSH
Gesterol	MeSH
11-Hydroxyprogesterone, (11alpha)-isomer	MeSH
11beta-Hydroxy-4-pregnene-3,20-dione	HMDB
11beta-Hydroxy-P4	HMDB
11beta-Hydroxyprogesterone	HMDB
11β-Hydroxy-4-pregnene-3,20-dione	HMDB
11β-Hydroxy-P4	HMDB
Pregn-4-en-11beta-ol-3,20-dione	HMDB
Pregn-4-en-11β-ol-3,20-dione	HMDB
Pregn-4-ene-11beta-ol-3,20-dione	HMDB
Pregn-4-ene-11β-ol-3,20-dione	HMDB
delta4-Pregnene-11beta-ol-3,20-dione	HMDB
Δ4-Pregnene-11β-ol-3,20-dione	HMDB

Chemical Formula

C₂₁H₃₀O₃

Average Molecular Weight

330.4611

Monoisotopic Molecular Weight

330.219494826

IUPAC Name

(1S,2R,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

Traditional Name

(1S,2R,10S,11S,14S,15S,17S)-14-acetyl-17-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

CAS Registry Number

600-57-7

SMILES

[H][C@@]12CC[C@H](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/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15-,16+,17-,18-,19+,20-,21+/m0/s1

InChI Key

BFZHCUBIASXHPK-ATWVFEABSA-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
11-hydroxysteroid
11-beta-hydroxysteroid
Hydroxysteroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

11beta-hydroxy steroid (CHEBI:28247 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030168 )

Ontology

Not Available

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	MetCCS_train_pos	182.315	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.064 g/L	ALOGPS
logP	2.65	ALOGPS
logP	2.84	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	18.88	ChemAxon
pKa (Strongest Basic)	-0.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.3 m³·mol⁻¹	ChemAxon
Polarizability	38.12 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
DeepCCS	[M-2H]-	216.538	30932474
DeepCCS	[M+Na]+	191.617	30932474
AllCCS	[M+H]+	183.6	32859911
AllCCS	[M+H-H2O]+	180.7	32859911
AllCCS	[M+NH4]+	186.2	32859911
AllCCS	[M+Na]+	187.0	32859911
AllCCS	[M-H]-	188.7	32859911
AllCCS	[M+Na-2H]-	189.0	32859911
AllCCS	[M+HCOO]-	189.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
11beta-Hydroxyprogesterone	[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	3967.8	Standard polar	33892256
11beta-Hydroxyprogesterone	[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	2883.0	Standard non polar	33892256
11beta-Hydroxyprogesterone	[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C	3209.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
11beta-Hydroxyprogesterone,1TMS,isomer #1	CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	3023.9	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,1TMS,isomer #2	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3074.9	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,1TMS,isomer #3	CC(=O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	2937.1	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,1TMS,isomer #4	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3049.1	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	3005.4	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2898.4	Standard non polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	3264.2	Standard polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #2	CC(=O)[C@H]1CC[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@]12C	2855.4	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #2	CC(=O)[C@H]1CC[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@]12C	2881.1	Standard non polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #2	CC(=O)[C@H]1CC[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@]12C	3276.4	Standard polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2954.4	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	2866.3	Standard non polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #3	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O[Si](C)(C)C)C[C@]12C	3357.6	Standard polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #4	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	2977.6	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #4	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	2984.7	Standard non polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #4	CC(O[Si](C)(C)C)=C1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3273.5	Standard polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #5	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	2936.4	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #5	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	2962.2	Standard non polar	33892256
11beta-Hydroxyprogesterone,2TMS,isomer #5	C=C(O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3358.5	Standard polar	33892256
11beta-Hydroxyprogesterone,3TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[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@]12C	2871.6	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,3TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[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@]12C	2942.9	Standard non polar	33892256
11beta-Hydroxyprogesterone,3TMS,isomer #1	CC(O[Si](C)(C)C)=C1CC[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@]12C	3244.1	Standard polar	33892256
11beta-Hydroxyprogesterone,3TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CC[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@]12C	2857.0	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,3TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CC[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@]12C	2915.3	Standard non polar	33892256
11beta-Hydroxyprogesterone,3TMS,isomer #2	C=C(O[Si](C)(C)C)[C@H]1CC[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@]12C	3319.5	Standard polar	33892256
11beta-Hydroxyprogesterone,1TBDMS,isomer #1	CC(=O)[C@H]1CC[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@]12C	3259.3	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,1TBDMS,isomer #2	CC(O[Si](C)(C)C(C)(C)C)=C1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3311.4	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,1TBDMS,isomer #3	CC(=O)[C@H]1CC[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@]12C	3185.6	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,1TBDMS,isomer #4	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C	3276.1	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[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@]12C	3480.5	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[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@]12C	3409.2	Standard non polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[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@]12C	3501.9	Standard polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #2	CC(=O)[C@H]1CC[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@]12C	3309.6	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #2	CC(=O)[C@H]1CC[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@]12C	3340.5	Standard non polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #2	CC(=O)[C@H]1CC[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@]12C	3502.0	Standard polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[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@]12C	3416.0	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[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@]12C	3373.1	Standard non polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #3	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[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@]12C	3566.8	Standard polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #4	CC(O[Si](C)(C)C(C)(C)C)=C1CC[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@]12C	3455.1	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #4	CC(O[Si](C)(C)C(C)(C)C)=C1CC[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@]12C	3407.2	Standard non polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #4	CC(O[Si](C)(C)C(C)(C)C)=C1CC[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@]12C	3512.3	Standard polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #5	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[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@]12C	3386.4	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #5	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[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@]12C	3383.7	Standard non polar	33892256
11beta-Hydroxyprogesterone,2TBDMS,isomer #5	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[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@]12C	3572.7	Standard polar	33892256
11beta-Hydroxyprogesterone,3TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[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@]12C	3506.3	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,3TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[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@]12C	3556.0	Standard non polar	33892256
11beta-Hydroxyprogesterone,3TBDMS,isomer #1	CC(O[Si](C)(C)C(C)(C)C)=C1CC[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@]12C	3525.8	Standard polar	33892256
11beta-Hydroxyprogesterone,3TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[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@]12C	3488.4	Semi standard non polar	33892256
11beta-Hydroxyprogesterone,3TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[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@]12C	3528.7	Standard non polar	33892256
11beta-Hydroxyprogesterone,3TBDMS,isomer #2	C=C(O[Si](C)(C)C(C)(C)C)[C@H]1CC[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@]12C	3567.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 11beta-Hydroxyprogesterone GC-MS (2 MEOX; 1 TMS)	splash10-0ffx-4910000000-0cca73076134866f5851	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 11beta-Hydroxyprogesterone GC-MS (2 MEOX; 1 TMS)	splash10-0ffx-4900000000-22180c23fc90db83965b	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 11beta-Hydroxyprogesterone 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 - 11beta-Hydroxyprogesterone 10V, Negative-QTOF	splash10-004i-0009000000-3acdbd949ad93c49c37e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxyprogesterone 20V, Negative-QTOF	splash10-004i-0029000000-7853a5e8535805da7f8a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxyprogesterone 40V, Negative-QTOF	splash10-000t-0192000000-a1d7b9a7a78d30b7da27	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxyprogesterone 10V, Positive-QTOF	splash10-001i-0009000000-bbcb8feda689de8948d5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxyprogesterone 20V, Positive-QTOF	splash10-03ei-1293000000-97a70cab30be8e37a1a0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11beta-Hydroxyprogesterone 40V, Positive-QTOF	splash10-08fu-3690000000-bfbef046ba46172a3844	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Bladder
Epidermis
Fibroblasts
Intestine
Kidney
Neuron
Ovary
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen
Testis
Thyroid Gland

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	0.00002 +/- 0.00001 uM	Adult (>18 years old)	Both	Normal	2537337	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023284

KNApSAcK ID

Not Available

Chemspider ID

91968

KEGG Compound ID

C05498

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

11β-Hydroxyprogesterone

METLIN ID

Not Available

PubChem Compound

101788

PDB ID

Not Available

ChEBI ID

28247

Food Biomarker Ontology

Not Available

VMH ID

M00285

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Rosenkranz, G.; Pataki, J.; Djerassi, Carl. Steroids. XXIX. Synthesis of 11b-hydroxyprogesterone. Journal of Organic Chemistry (1952), 17 290-3.

Material Safety Data Sheet (MSDS)

Not Available

General References

Holtta-Vuori M, Maatta J, Ullrich O, Kuismanen E, Ikonen E: Mobilization of late-endosomal cholesterol is inhibited by Rab guanine nucleotide dissociation inhibitor. Curr Biol. 2000 Jan 27;10(2):95-8. [PubMed:10662671 ]
Herrero P, Soto PF, Dence CS, Kisrieva-Ware Z, Delano DA, Peterson LR, Gropler RJ: Impact of hormone replacement on myocardial fatty acid metabolism: potential role of estrogen. J Nucl Cardiol. 2005 Sep-Oct;12(5):574-81. [PubMed:16171718 ]
Laatikainen T, Apter D, Wahlstrom T: Steroids in spermatic and peripheral vein blood in testicular feminization. Fertil Steril. 1980 Nov;34(5):461-4. [PubMed:7439411 ]
Tuckey RC: Progesterone synthesis by the human placenta. Placenta. 2005 Apr;26(4):273-81. [PubMed:15823613 ]
Lambert JJ, Belelli D, Peden DR, Vardy AW, Peters JA: Neurosteroid modulation of GABAA receptors. Prog Neurobiol. 2003 Sep;71(1):67-80. [PubMed:14611869 ]
Antic T, Perry KT, Harrison K, Zaytsev P, Pins M, Campbell SC, Picken MM: Mixed epithelial and stromal tumor of the kidney and cystic nephroma share overlapping features: reappraisal of 15 lesions. Arch Pathol Lab Med. 2006 Jan;130(1):80-5. [PubMed:16390243 ]
Shikone T, Matzuk MM, Perlas E, Finegold MJ, Lewis KA, Vale W, Bradley A, Hsueh AJ: Characterization of gonadal sex cord-stromal tumor cell lines from inhibin-alpha and p53-deficient mice: the role of activin as an autocrine growth factor. Mol Endocrinol. 1994 Aug;8(8):983-95. [PubMed:7997239 ]
Barnhill SD, Zhang Z, Madyastha KR: Evaluation of a new biochemical index for the estimation of bone demineralization using artificial intelligence. Contemp Orthop. 1995 Apr;30(4):315-8. [PubMed:10150355 ]
Saxena BB, Clavio A, Singh M, Rathnam P, Bukharovich EY, Reimers TJ Jr, Saxena A, Perkins S: Effect of immunization with bovine luteinizing hormone receptor on ovarian function in cats. Am J Vet Res. 2003 Mar;64(3):292-8. [PubMed:12661868 ]
Wiebe JP: Nongenomic actions of steroids on gonadotropin release. Recent Prog Horm Res. 1997;52:71-99; discussion 99-101. [PubMed:9238848 ]
Celayir S, Ilce Z, Dervisoglu S: The sex hormone receptors in the bladder in childhood - I: preliminary report in male subjects. Eur J Pediatr Surg. 2002 Oct;12(5):312-7. [PubMed:12469257 ]
Agoulnik IU, Krause WC, Bingman WE 3rd, Rahman HT, Amrikachi M, Ayala GE, Weigel NL: Repressors of androgen and progesterone receptor action. J Biol Chem. 2003 Aug 15;278(33):31136-48. Epub 2003 May 27. [PubMed:12771131 ]
Beer R, Barnhill SD, Madyastha KR: Comparative study of a biochemical index for the estimation of bone demineralization and dual photon absorptiometry. Contemp Orthop. 1995 Mar;30(3):230-4. [PubMed:10150317 ]
Pepe GJ, Albrecht ED: Actions of placental and fetal adrenal steroid hormones in primate pregnancy. Endocr Rev. 1995 Oct;16(5):608-48. [PubMed:8529574 ]
Feuring M, Christ M, Roell A, Schueller P, Losel R, Dempfle CE, Schultz A, Wehling M: Alterations in platelet function during the ovarian cycle. Blood Coagul Fibrinolysis. 2002 Jul;13(5):443-7. [PubMed:12138372 ]
Rasmussen KM, Kjolhede CL: Prepregnant overweight and obesity diminish the prolactin response to suckling in the first week postpartum. Pediatrics. 2004 May;113(5):e465-71. [PubMed:15121990 ]
Parikh P, Chan TY, Epstein JI, Argani P: Incidental stromal-predominant mixed epithelial-stromal tumors of the kidney: a mimic of intraparenchymal renal leiomyoma. Arch Pathol Lab Med. 2005 Jul;129(7):910-4. [PubMed:15974815 ]
Money SR, Muss W, Thelmo WL, Boeckl O, Pimpl W, Kaindl H, Sungler P, Kirwin J, Waclawicek H, Jaffe BM, et al.: Immunocytochemical localization of estrogen and progesterone receptors in human thyroid. Surgery. 1989 Dec;106(6):975-8; discussion 979. [PubMed:2686061 ]
Karalis K, Goodwin G, Majzoub JA: Cortisol blockade of progesterone: a possible molecular mechanism involved in the initiation of human labor. Nat Med. 1996 May;2(5):556-60. [PubMed:8616715 ]
Sereda MW, Meyer zu Horste G, Suter U, Uzma N, Nave KA: Therapeutic administration of progesterone antagonist in a model of Charcot-Marie-Tooth disease (CMT-1A). Nat Med. 2003 Dec;9(12):1533-7. Epub 2003 Nov 9. [PubMed:14608378 ]
Fiet J, Gueux B, Raux-DeMay MC, Kuttenn F, Vexiau P, Brerault JL, Couillin P, Galons H, Villette JM, Julien R, et al.: Increased plasma 21-deoxycorticosterone (21-DB) levels in late-onset adrenal 21-hydroxylase deficiency suggest a mild defect of the mineralocorticoid pathway. J Clin Endocrinol Metab. 1989 Mar;68(3):542-7. [PubMed:2537337 ]
Gueux B, Fiet J, Galons H, Bonete R, Villette JM, Vexiau P, Pham-Huu-Trung MT, Raux-Eurin MC, Gourmelen M, Brerault JL, et al.: The measurement of 11 beta-hydroxy-4-pregnene-3,20-dione (21-deoxycorticosterone) by radioimmunoassay in human plasma. J Steroid Biochem. 1987 Jan;26(1):145-50. [PubMed:3546944 ]

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

Progesterone + Reduced ferredoxin + Oxygen → 11beta-Hydroxyprogesterone + 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

Progesterone + Reduced ferredoxin + Oxygen → 11beta-Hydroxyprogesterone + Oxidized ferredoxin + Water	details

Enzyme Details

4. 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

5. 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

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

Showing metabocard for 11beta-Hydroxyprogesterone (HMDB0004031)

MOL for HMDB0004031 (11beta-Hydroxyprogesterone)

3D MOL for HMDB0004031 (11beta-Hydroxyprogesterone)

3D SDF for HMDB0004031 (11beta-Hydroxyprogesterone)

3D-SDF for HMDB0004031 (11beta-Hydroxyprogesterone)

PDB for HMDB0004031 (11beta-Hydroxyprogesterone)

3D PDB for HMDB0004031 (11beta-Hydroxyprogesterone)

SMILES for HMDB0004031 (11beta-Hydroxyprogesterone)

INCHI for HMDB0004031 (11beta-Hydroxyprogesterone)

Structure for HMDB0004031 (11beta-Hydroxyprogesterone)

3D Structure for HMDB0004031 (11beta-Hydroxyprogesterone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions