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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:00 UTC

HMDB ID

HMDB0000353

Secondary Accession Numbers

HMDB00353

Metabolite Identification

Common Name

3b,15b,17a-Trihydroxy-pregnenone

Description

3b,15b,17a-Trihydroxy-pregnenone is a major 15 beta-hydroxylated metabolite unique to the human perinatal period. (PMID 8750436 ). The chemical synthesis of 15β-hydroxylated steroids is for use in the (a) development of new immunoassay techniques for application to newborn screening programs and fetal well-being; (b) development of new anti-androgenic drugs; and (c) study of androgen/estrogen interaction in late pregnancy.

Structure

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

3b,15b,17a-Trihydroxy-Pregnenone.mol
  Mrv0541 02231218282D          

 28 31  0  0  0  0            999 V2000
   -2.1951   -1.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1951   -0.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806   -0.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806   -2.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -1.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -2.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6628   -1.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6628   -0.8143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3773   -0.4018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1619   -0.6567    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6468    0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619    0.6782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9623    1.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5557    2.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773    0.4232    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3773    1.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6628    0.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517    0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -0.4018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7662   -0.8143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7662    0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096    1.0268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4168   -1.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9096   -2.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806    0.4232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -1.2268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6628    0.0107    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773   -1.2268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  1  0  0  0
 12 22  1  6  0  0  0
 10 23  1  1  0  0  0
  1 24  1  0  0  0  0
  3 25  2  0  0  0  0
 19 26  1  6  0  0  0
  8 27  1  1  0  0  0
  9 28  1  6  0  0  0
M  END

HMDB0000353
     RDKit          3D
3b,15b,17a-Trihydroxy-pregnenone
 57 60  0  0  0  0  0  0  0  0999 V2000
    4.5434    1.8421    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3773    0.3691   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1936   -0.1311   -0.7512 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1517    0.2111   -2.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2620   -1.6699   -0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236   -2.1551   -0.6623 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5140   -2.8388    0.4856 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0532   -0.8944   -0.8546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3312   -0.8578   -0.4140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2110   -1.9669   -0.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6151   -1.7711   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1334   -0.3940   -0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4399   -0.2723    0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0705    1.0121   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4435    1.0445   -0.3354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2661    2.0625   -0.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8207    1.9737   -0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895    3.0540   -0.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1323    0.7009   -0.1030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8885    0.4609    1.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9388    0.4559   -0.9394 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0876    1.4782   -1.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2712    1.4141   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8802    0.0827   -0.0474 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0583   -0.3053    1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9484    2.3453    0.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4010    2.3530   -0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6166    2.0527    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3381   -0.0089    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2942   -0.0753   -0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5734    1.0521   -2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8785   -2.0349    0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7211   -2.0490   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6125   -2.8534   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546   -3.7782    0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1610   -0.5997   -1.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3889   -0.8776    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1643   -2.0685   -2.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8298   -2.9171   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7691   -2.1971    0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2601   -2.4179   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3491   -0.1929   -1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0836   -1.0881   -0.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3377   -0.3687    1.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0006    1.5844    0.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7591    2.9785   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9121    0.7978    1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6346    1.0721    1.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371   -0.5856    1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3224    0.1832   -1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5855    1.3229   -2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2013    2.5258   -1.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375    2.1151   -0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254    1.8853    0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5761    0.5709    1.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524   -0.4719    1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7381   -1.1598    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  1
 24  3  1  0
 24  8  1  0
 21  9  1  0
 19 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
  7 35  1  0
  8 36  1  6
  9 37  1  1
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 15 45  1  0
 16 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  6
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 25 55  1  0
 25 56  1  0
 25 57  1  0
M  END

3b,15b,17a-Trihydroxy-Pregnenone.mol
  Mrv0541 02231218282D          

 28 31  0  0  0  0            999 V2000
   -2.1951   -1.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1951   -0.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806   -0.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806   -2.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -1.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -2.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6628   -1.6393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6628   -0.8143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3773   -0.4018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1619   -0.6567    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6468    0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619    0.6782    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9623    1.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5557    2.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773    0.4232    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3773    1.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6628    0.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517    0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -0.4018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7662   -0.8143    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7662    0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096    1.0268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4168   -1.4413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9096   -2.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4806    0.4232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -1.2268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6628    0.0107    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3773   -1.2268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  1  0  0  0
 12 22  1  6  0  0  0
 10 23  1  1  0  0  0
  1 24  1  0  0  0  0
  3 25  2  0  0  0  0
 19 26  1  6  0  0  0
  8 27  1  1  0  0  0
  9 28  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0000353

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12[C@H](O)C[C@](O)(CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O4/c1-4-21(25)11-16(23)18-14-6-5-12-9-13(22)10-17(24)20(12,3)15(14)7-8-19(18,21)2/h10,12,14-16,18,22-23,25H,4-9,11H2,1-3H3/t12?,14-,15+,16-,18-,19+,20+,21-/m1/s1

> <INCHI_KEY>
YXMCPINQJVUPGV-HETPMVKVSA-N

> <FORMULA>
C21H32O4

> <MOLECULAR_WEIGHT>
348.4764

> <EXACT_MASS>
348.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.74363072054646

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,10R,11S,12R,14R,15S)-14-ethyl-5,12,14-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
2.5158013876666674

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.172119882097082

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.746149664673526

> <JCHEM_PKA_STRONGEST_BASIC>
-2.875143237851356

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
97.50559999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,10R,11S,12R,14R,15S)-14-ethyl-5,12,14-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000353
     RDKit          3D
3b,15b,17a-Trihydroxy-pregnenone
 57 60  0  0  0  0  0  0  0  0999 V2000
    4.5434    1.8421    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3773    0.3691   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1936   -0.1311   -0.7512 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1517    0.2111   -2.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2620   -1.6699   -0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236   -2.1551   -0.6623 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5140   -2.8388    0.4856 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0532   -0.8944   -0.8546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3312   -0.8578   -0.4140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2110   -1.9669   -0.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6151   -1.7711   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1334   -0.3940   -0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4399   -0.2723    0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0705    1.0121   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4435    1.0445   -0.3354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2661    2.0625   -0.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8207    1.9737   -0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895    3.0540   -0.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1323    0.7009   -0.1030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8885    0.4609    1.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9388    0.4559   -0.9394 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0876    1.4782   -1.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2712    1.4141   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8802    0.0827   -0.0474 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0583   -0.3053    1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9484    2.3453    0.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4010    2.3530   -0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6166    2.0527    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3381   -0.0089    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2942   -0.0753   -0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5734    1.0521   -2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8785   -2.0349    0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7211   -2.0490   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6125   -2.8534   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546   -3.7782    0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1610   -0.5997   -1.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3889   -0.8776    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1643   -2.0685   -2.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8298   -2.9171   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7691   -2.1971    0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2601   -2.4179   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3491   -0.1929   -1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0836   -1.0881   -0.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3377   -0.3687    1.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0006    1.5844    0.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7591    2.9785   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9121    0.7978    1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6346    1.0721    1.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371   -0.5856    1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3224    0.1832   -1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5855    1.3229   -2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2013    2.5258   -1.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375    2.1151   -0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254    1.8853    0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5761    0.5709    1.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524   -0.4719    1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7381   -1.1598    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  1
 24  3  1  0
 24  8  1  0
 21  9  1  0
 19 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
  7 35  1  0
  8 36  1  6
  9 37  1  1
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 15 45  1  0
 16 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  6
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 25 55  1  0
 25 56  1  0
 25 57  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3b,15b,17a-Trihydroxy-Pregnenone.mol              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.098  -3.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.098  -1.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.764  -0.750   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.764  -3.830   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.430  -3.060   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.097  -3.830   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.237  -3.060   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.237  -1.520   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.571  -0.750   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.036  -1.226   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.941   0.020   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.036   1.266   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.663   2.760   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.771   3.830   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.571   0.790   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.571   2.330   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.237   1.560   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.097   0.790   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.097  -0.750   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.430  -1.520   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.430   0.020   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.431   1.917   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.511  -2.690   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.431  -3.830   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.764   0.790   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0      -0.097  -2.290   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.237   0.020   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.571  -2.290   0.000  0.00  0.00           H+0
CONECT    1    2    4   24                                                  
CONECT    2    1    3                                                       
CONECT    3    2   20   25                                                  
CONECT    4    1    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19   27                                             
CONECT    9    8   10   15   28                                             
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15   22                                             
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12    9   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    8   20   26                                             
CONECT   20   19    3    5   21                                             
CONECT   21   20                                                            
CONECT   22   12                                                            
CONECT   23   10                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26   19                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0000353
HETATM    1  C1  UNL     1       4.543   1.842   0.026  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.377   0.369  -0.008  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.194  -0.131  -0.751  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.152   0.211  -2.078  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.262  -1.670  -0.716  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.824  -2.155  -0.662  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.514  -2.839   0.486  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.053  -0.894  -0.855  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.331  -0.858  -0.414  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.211  -1.967  -0.900  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.615  -1.771  -0.392  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.133  -0.394  -0.512  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.440  -0.272   0.216  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.071   1.012  -0.189  1.00  0.00           C  
HETATM   15  O3  UNL     1      -6.444   1.044  -0.335  1.00  0.00           O  
HETATM   16  C13 UNL     1      -4.266   2.063  -0.389  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.821   1.974  -0.220  1.00  0.00           C  
HETATM   18  O4  UNL     1      -2.190   3.054  -0.178  1.00  0.00           O  
HETATM   19  C15 UNL     1      -2.132   0.701  -0.103  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.889   0.461   1.385  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.939   0.456  -0.939  1.00  0.00           C  
HETATM   22  C18 UNL     1       0.088   1.478  -1.117  1.00  0.00           C  
HETATM   23  C19 UNL     1       1.271   1.414  -0.155  1.00  0.00           C  
HETATM   24  C20 UNL     1       1.880   0.083  -0.047  1.00  0.00           C  
HETATM   25  C21 UNL     1       2.058  -0.305   1.382  1.00  0.00           C  
HETATM   26  H1  UNL     1       3.948   2.345   0.831  1.00  0.00           H  
HETATM   27  H2  UNL     1       4.401   2.353  -0.942  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.617   2.053   0.311  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.338  -0.009   1.027  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.294  -0.075  -0.463  1.00  0.00           H  
HETATM   31  H6  UNL     1       3.573   1.052  -2.313  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.879  -2.035   0.102  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.721  -2.049  -1.663  1.00  0.00           H  
HETATM   34  H9  UNL     1       1.612  -2.853  -1.524  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.755  -3.778   0.462  1.00  0.00           H  
HETATM   36  H11 UNL     1       1.161  -0.600  -1.926  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.389  -0.878   0.698  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.164  -2.068  -2.002  1.00  0.00           H  
HETATM   39  H14 UNL     1      -0.830  -2.917  -0.472  1.00  0.00           H  
HETATM   40  H15 UNL     1      -2.769  -2.197   0.619  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.260  -2.418  -1.061  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.349  -0.193  -1.594  1.00  0.00           H  
HETATM   43  H18 UNL     1      -5.084  -1.088  -0.167  1.00  0.00           H  
HETATM   44  H19 UNL     1      -4.338  -0.369   1.306  1.00  0.00           H  
HETATM   45  H20 UNL     1      -7.001   1.584   0.344  1.00  0.00           H  
HETATM   46  H21 UNL     1      -4.759   2.979  -0.683  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.912   0.798   1.724  1.00  0.00           H  
HETATM   48  H23 UNL     1      -2.635   1.072   1.977  1.00  0.00           H  
HETATM   49  H24 UNL     1      -2.137  -0.586   1.681  1.00  0.00           H  
HETATM   50  H25 UNL     1      -1.322   0.183  -1.973  1.00  0.00           H  
HETATM   51  H26 UNL     1       0.585   1.323  -2.130  1.00  0.00           H  
HETATM   52  H27 UNL     1      -0.201   2.526  -1.148  1.00  0.00           H  
HETATM   53  H28 UNL     1       2.038   2.115  -0.602  1.00  0.00           H  
HETATM   54  H29 UNL     1       1.025   1.885   0.828  1.00  0.00           H  
HETATM   55  H30 UNL     1       2.576   0.571   1.875  1.00  0.00           H  
HETATM   56  H31 UNL     1       1.152  -0.472   1.958  1.00  0.00           H  
HETATM   57  H32 UNL     1       2.738  -1.160   1.549  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    5   24
CONECT    4   31
CONECT    5    6   32   33
CONECT    6    7    8   34
CONECT    7   35
CONECT    8    9   24   36
CONECT    9   10   21   37
CONECT   10   11   38   39
CONECT   11   12   40   41
CONECT   12   13   19   42
CONECT   13   14   43   44
CONECT   14   15   16   16
CONECT   15   45
CONECT   16   17   46
CONECT   17   18   18   19
CONECT   19   20   21
CONECT   20   47   48   49
CONECT   21   22   50
CONECT   22   23   51   52
CONECT   23   24   53   54
CONECT   24   25
CONECT   25   55   56   57
END

HMDB0000353
     RDKit          3D
3b,15b,17a-Trihydroxy-pregnenone
 57 60  0  0  0  0  0  0  0  0999 V2000
    4.5434    1.8421    0.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3773    0.3691   -0.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1936   -0.1311   -0.7512 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1517    0.2111   -2.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2620   -1.6699   -0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236   -2.1551   -0.6623 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5140   -2.8388    0.4856 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0532   -0.8944   -0.8546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3312   -0.8578   -0.4140 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2110   -1.9669   -0.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6151   -1.7711   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1334   -0.3940   -0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4399   -0.2723    0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0705    1.0121   -0.1894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4435    1.0445   -0.3354 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2661    2.0625   -0.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8207    1.9737   -0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1895    3.0540   -0.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1323    0.7009   -0.1030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8885    0.4609    1.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9388    0.4559   -0.9394 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0876    1.4782   -1.1171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2712    1.4141   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8802    0.0827   -0.0474 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0583   -0.3053    1.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9484    2.3453    0.8306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4010    2.3530   -0.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6166    2.0527    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3381   -0.0089    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2942   -0.0753   -0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5734    1.0521   -2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8785   -2.0349    0.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7211   -2.0490   -1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6125   -2.8534   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546   -3.7782    0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1610   -0.5997   -1.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3889   -0.8776    0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1643   -2.0685   -2.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8298   -2.9171   -0.4720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7691   -2.1971    0.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2601   -2.4179   -1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3491   -0.1929   -1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0836   -1.0881   -0.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3377   -0.3687    1.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0006    1.5844    0.3442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7591    2.9785   -0.6832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9121    0.7978    1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6346    1.0721    1.9766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1371   -0.5856    1.6814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3224    0.1832   -1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5855    1.3229   -2.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2013    2.5258   -1.1481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375    2.1151   -0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254    1.8853    0.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5761    0.5709    1.8748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1524   -0.4719    1.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7381   -1.1598    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  6
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  1
 24  3  1  0
 24  8  1  0
 21  9  1  0
 19 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
  7 35  1  0
  8 36  1  6
  9 37  1  1
 10 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 15 45  1  0
 16 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  6
 22 51  1  0
 22 52  1  0
 23 53  1  0
 23 54  1  0
 25 55  1  0
 25 56  1  0
 25 57  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3beta,15beta)3,15,17-Trihydroxy-pregn-5-en-20-one	HMDB
3b,15b,17a-Trihydroxy-5-pregnen-20-one	HMDB
3beta,15beta,17alpha-Trihydroxy-5-pregnen-20-one	HMDB
3 beta,15 beta,17 alpha-Trihydroxy-5-pregnen-20-one	MeSH

Chemical Formula

C₂₁H₃₂O₄

Average Molecular Weight

348.4764

Monoisotopic Molecular Weight

348.230059512

IUPAC Name

(1S,2S,10R,11S,12R,14R,15S)-14-ethyl-5,12,14-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one

Traditional Name

(1S,2S,10R,11S,12R,14R,15S)-14-ethyl-5,12,14-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-3-one

CAS Registry Number

80380-40-1

SMILES

[H][C@@]12[C@H](O)C[C@](O)(CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C

InChI Identifier

InChI=1S/C21H32O4/c1-4-21(25)11-16(23)18-14-6-5-12-9-13(22)10-17(24)20(12,3)15(14)7-8-19(18,21)2/h10,12,14-16,18,22-23,25H,4-9,11H2,1-3H3/t12?,14-,15+,16-,18-,19+,20+,21-/m1/s1

InChI Key

YXMCPINQJVUPGV-HETPMVKVSA-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
3-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
1-oxosteroid
Oxosteroid
17-hydroxysteroid
Cyclohexenone
Cyclic alcohol
Tertiary alcohol
Vinylogous acid
Secondary alcohol
Ketone
Polyol
Enol
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000353)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0000353)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000353)

Source

Endogenous

Endogenous (HMDB: HMDB0000353)

Animal

Animal (HMDB: HMDB0000353)

Exogenous

Food

Food (HMDB: HMDB0000353)

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: HMDB0000353)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0000353)

Molecular messenger

Hormone (HMDB: HMDB0000353)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0000353)

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	0.15 g/L	ALOGPS
logP	2.27	ALOGPS
logP	2.52	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.75	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	97.51 m³·mol⁻¹	ChemAxon
Polarizability	39.74 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
AllCCS	[M+H]+	186.965	32859911
AllCCS	[M-H]-	191.131	32859911
DeepCCS	[M-2H]-	216.916	30932474
DeepCCS	[M+Na]+	191.708	30932474
AllCCS	[M+H]+	187.0	32859911
AllCCS	[M+H-H2O]+	184.3	32859911
AllCCS	[M+NH4]+	189.4	32859911
AllCCS	[M+Na]+	190.2	32859911
AllCCS	[M-H]-	191.1	32859911
AllCCS	[M+Na-2H]-	191.6	32859911
AllCCS	[M+HCOO]-	192.3	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.	5.84 minutes	32390414
Predicted by Siyang on May 30, 2022	13.3046 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.35 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2637.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	220.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	185.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	234.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	691.5 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	596.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	77.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1039.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	456.0 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	1551.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	365.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	437.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	224.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	257.5 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	36.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3b,15b,17a-Trihydroxy-pregnenone	[H][C@@]12[C@H](O)C[C@](O)(CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C	3506.1	Standard polar	33892256
3b,15b,17a-Trihydroxy-pregnenone	[H][C@@]12[C@H](O)C[C@](O)(CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C	2887.7	Standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone	[H][C@@]12[C@H](O)C[C@](O)(CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2CC(O)=CC(=O)[C@]12C	3231.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3b,15b,17a-Trihydroxy-pregnenone,1TMS,isomer #1	CC[C@@]1(O)C[C@@H](O[Si](C)(C)C)[C@H]2[C@@H]3CCC4CC(O)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3032.8	Semi standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone,1TMS,isomer #2	CC[C@@]1(O[Si](C)(C)C)C[C@@H](O)[C@H]2[C@@H]3CCC4CC(O)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3053.7	Semi standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone,1TMS,isomer #3	CC[C@@]1(O)C[C@@H](O)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3081.7	Semi standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone,2TMS,isomer #1	CC[C@@]1(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@H]2[C@@H]3CCC4CC(O)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3014.1	Semi standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone,2TMS,isomer #2	CC[C@@]1(O)C[C@@H](O[Si](C)(C)C)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3008.4	Semi standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone,2TMS,isomer #3	CC[C@@]1(O[Si](C)(C)C)C[C@@H](O)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3052.5	Semi standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone,3TMS,isomer #1	CC[C@@]1(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3009.7	Semi standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone,1TBDMS,isomer #1	CC[C@@]1(O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3CCC4CC(O)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3273.0	Semi standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone,1TBDMS,isomer #2	CC[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@H]2[C@@H]3CCC4CC(O)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3293.0	Semi standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone,1TBDMS,isomer #3	CC[C@@]1(O)C[C@@H](O)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C(C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3297.8	Semi standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone,2TBDMS,isomer #1	CC[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3CCC4CC(O)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3470.3	Semi standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone,2TBDMS,isomer #2	CC[C@@]1(O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C(C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3438.0	Semi standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone,2TBDMS,isomer #3	CC[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C(C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3485.0	Semi standard non polar	33892256
3b,15b,17a-Trihydroxy-pregnenone,3TBDMS,isomer #1	CC[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C(C)(C)C)=CC(=O)[C@]4(C)[C@H]3CC[C@@]21C	3636.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pc0-1379000000-4fda3117bd2a30543902	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (3 TMS) - 70eV, Positive	splash10-0f72-1003390000-9df556b4de735cd61cab	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-05	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 - 3b,15b,17a-Trihydroxy-pregnenone 10V, Positive-QTOF	splash10-01q9-0009000000-10a1dfe2e84fcfd5c473	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 20V, Positive-QTOF	splash10-01pk-0169000000-661db42ac36a91f59d81	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 40V, Positive-QTOF	splash10-08mr-1791000000-e3973b00ae9e66e66089	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 10V, Negative-QTOF	splash10-0002-0009000000-100b460713f046c8f5b3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 20V, Negative-QTOF	splash10-004j-0019000000-498b06b4d446462cb069	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 40V, Negative-QTOF	splash10-0kc2-2198000000-113e6dfe5d58729f4546	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 10V, Positive-QTOF	splash10-0002-0009000000-3c6e240d9bc66c6c9374	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 20V, Positive-QTOF	splash10-03ea-1229000000-315820479cd99f2a5174	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 40V, Positive-QTOF	splash10-00fr-0690000000-ba831c278d3e46642e9f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 10V, Negative-QTOF	splash10-0002-0009000000-7a1691459f834500eb02	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 20V, Negative-QTOF	splash10-002b-0009000000-f12a6db5f5c4c63fc709	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3b,15b,17a-Trihydroxy-pregnenone 40V, Negative-QTOF	splash10-0w2a-0029000000-fe86834a83d0507e779b	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB021976

KNApSAcK ID

Not Available

Chemspider ID

117725

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133455

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Joannou, George E.; Reeder, Anthony Y. 15b-Hydroxysteroids. (Part V). Steroids of the human perinatal period: the synthesis of 3b,15b,17a-trihydroxy-5-pregnen-20-one from 15b,17a-dihydroxy-4-pregnen-3,20-dione. Steroids (1996), 61(1), 18-21.

Material Safety Data Sheet (MSDS)

Not Available

General References

Reeder AY, Joannou GE: 15 beta-hydroxysteroids (part I). Steroids of the human perinatal period: the synthesis of 3 beta,15 beta, 17 alpha-trihydroxy-5-pregnen-20-one. Steroids. 1996 Feb;61(2):74-81. [PubMed:8750436 ]
Joannou GE: Identification of 15 beta-hydroxylated C21 steroids in the neo-natal period: the role of 3 alpha,15 beta,17 alpha-trihydroxy-5 beta-pregnan-20-one in the perinatal diagnosis of congenital adrenal hyperplasia (CAH) due to a 21-hydroxylase deficiency. J Steroid Biochem. 1981 Sep;14(9):901-12. [PubMed:6975400 ]
Joannou GE, Reeder AY: 15 beta-hydroxysteroids (Part V). Steroids of the human perinatal period: the synthesis of 3 beta, 15 beta, 17 alpha-trihydroxy-5-pregnen-20-one from 15 beta, 17 alpha-dihydroxy-4-pregnen-3,20-dione. Steroids. 1996 Jan;61(1):18-21. [PubMed:8789731 ]
Joannou GE, Reeder AY: 15 beta-hydroxysteroids (part II). Steroids of the human perinatal period: the synthesis of 3 alpha,15 beta, 17 alpha-trihydroxy-5 beta-pregnan-20-one. Steroids. 1996 Feb;61(2):82-8. [PubMed:8750437 ]
Joannou GE, Reeder AY: 15 beta-hydroxysteroids (Part III). Steroids of the human perinatal period: the synthesis of 3 beta, 15 beta, 17 alpha-trihydroxy-5-pregnen-20-one. Application of n-butyl boronic acid protection of a 17,20-glycol. Steroids. 1996 Jan;61(1):11-7. [PubMed:8789730 ]

Showing metabocard for 3b,15b,17a-Trihydroxy-pregnenone (HMDB0000353)

MOL for HMDB0000353 (3b,15b,17a-Trihydroxy-pregnenone)

3D MOL for HMDB0000353 (3b,15b,17a-Trihydroxy-pregnenone)

3D SDF for HMDB0000353 (3b,15b,17a-Trihydroxy-pregnenone)

3D-SDF for HMDB0000353 (3b,15b,17a-Trihydroxy-pregnenone)

PDB for HMDB0000353 (3b,15b,17a-Trihydroxy-pregnenone)

3D PDB for HMDB0000353 (3b,15b,17a-Trihydroxy-pregnenone)

SMILES for HMDB0000353 (3b,15b,17a-Trihydroxy-pregnenone)

INCHI for HMDB0000353 (3b,15b,17a-Trihydroxy-pregnenone)

Structure for HMDB0000353 (3b,15b,17a-Trihydroxy-pregnenone)

3D Structure for HMDB0000353 (3b,15b,17a-Trihydroxy-pregnenone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra