Jump To Section:

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:30 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0003069

Secondary Accession Numbers

HMDB03069

Metabolite Identification

Common Name

20alpha-Dihydroprogesterone

Description

20alpha-Dihydroprogesterone is a biologically active 20-alpha-reduced metabolite of progesterone. It is converted from progesterone to 20-alpha-hydroxypregn-4-en-3-one by the 20-alpha-hydroxysteroid dehydrogenase in the corpus luteum and the placenta. Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation), and embryogenesis of humans and other species. Progesterone belongs to a class of hormones called progestagens, and is the major naturally occurring human progestagen (Wikipedia ). During implantation and gestation, progesterone appears to decrease the maternal immune response to allow for the acceptance of the pregnancy. Progesterone decreases contractility of the uterine smooth muscle. The fetus metabolizes placental progesterone in the production of adrenal mineralo- and glucosteroids. A drop in progesterone levels is possibly one step that facilitates the onset of labour. In addition, progesterone inhibits lactation during pregnancy. The fall in progesterone levels following delivery is one of the triggers for milk production (Wikipedia ).

Structure

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

  Mrv1652305082018502D          

 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
 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
 9998.5744 9999.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8599 9999.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8599 9998.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5744 9997.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2889 9998.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2889 9999.1802    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9999 9999.5941    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9999 9997.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7144 9998.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7144 9999.1816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.712710000.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.998210000.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.427210000.4276    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.4272 9999.6026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2118 9999.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.696710000.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.211810000.6826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.211810001.5076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.925510001.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.496210001.9201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.925510001.0951    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 13  1  0  0  0  0
 13  5  1  6  0  0  0
 16  4  1  1  0  0  0
  9  2  2  0  0  0  0
 13 12  1  0  0  0  0
 12  1  1  1  0  0  0
 11 14  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 27  1  6  0  0  0
 24 25  1  0  0  0  0
 24 26  1  1  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 20  6  1  6  0  0  0
 16 20  1  0  0  0  0
 17 19  1  0  0  0  0
 19  3  1  1  0  0  0
M  END

HMDB0003069
     RDKit          3D
20alpha-Dihydroprogesterone
 55 58  0  0  0  0  0  0  0  0999 V2000
    4.2774    0.9389   -1.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3190    0.1077   -0.7061 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3508   -0.8436   -0.9065 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0751   -0.6626   -0.4519 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2476   -1.4491    0.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8648   -1.4953    1.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9829   -0.9729    0.4235 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3302   -0.4362    0.8240 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1000   -1.4141    1.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3078   -0.6623    2.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0830   -0.2043    1.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4047   -0.2008    1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2396    0.2305    0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3605    0.7253    0.2580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7557    0.0815   -1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3097   -0.3535   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5037    0.2340   -0.2540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6139    1.7644   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0778   -0.1349   -0.4660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3067    0.9499   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161    0.5828   -1.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8528    0.1407   -0.1842 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0556    1.2650    0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6602    0.4762   -2.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726    1.9937   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082    1.0114   -2.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6649    0.7329    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2376   -0.3881   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -1.3159   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5994   -2.4633    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9885   -0.9919    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6233   -2.5863    1.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8311   -0.9604    2.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8344   -1.7360   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2931    0.5205    1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4276   -1.7348    2.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4776   -2.2601    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9015   -1.3459    2.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9193    0.1999    2.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8743   -0.5213    2.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9396    0.9910   -1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3528   -0.7328   -1.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2227   -1.4635   -1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8899   -0.0884   -2.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6448    2.1038   -0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3072    2.1700   -1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0043    2.1511    0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9873   -1.0508   -1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3775    1.9314   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7964    1.0995   -2.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6262    1.4946   -1.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1690   -0.2597   -2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2583    2.0498    0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099    1.8013    0.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9989    0.9809    1.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
 21 22  1  0
 22 23  1  1
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  1
  3 28  1  0
  4 29  1  6
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  6
  8 35  1  1
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  6
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

  Mrv1652305082018502D          

 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
 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
 9998.5744 9999.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8599 9999.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8599 9998.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5744 9997.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2889 9998.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.2889 9999.1802    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9999 9999.5941    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.9999 9997.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7144 9998.3565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7144 9999.1816    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.712710000.8402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.998210000.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.427210000.4276    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.4272 9999.6026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10002.2118 9999.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.696710000.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.211810000.6826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.211810001.5076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10002.925510001.9201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.496210001.9201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.925510001.0951    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 16  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 13  1  0  0  0  0
 13  5  1  6  0  0  0
 16  4  1  1  0  0  0
  9  2  2  0  0  0  0
 13 12  1  0  0  0  0
 12  1  1  1  0  0  0
 11 14  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 27  1  6  0  0  0
 24 25  1  0  0  0  0
 24 26  1  1  0  0  0
 23 19  1  0  0  0  0
 23 22  1  0  0  0  0
 20  6  1  6  0  0  0
 16 20  1  0  0  0  0
 17 19  1  0  0  0  0
 19  3  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0003069

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12-13,16-19,22H,4-11H2,1-3H3/t13-,16-,17+,18-,19-,20-,21+/m0/s1

> <INCHI_KEY>
RWBRUCCWZPSBFC-RXRZZTMXSA-N

> <FORMULA>
C21H32O2

> <MOLECULAR_WEIGHT>
316.4776

> <EXACT_MASS>
316.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.98478138831439

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
3.9411035990000007

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.08781018820673

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.003403431948026

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0476375452966558

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
93.73339999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0003069
     RDKit          3D
20alpha-Dihydroprogesterone
 55 58  0  0  0  0  0  0  0  0999 V2000
    4.2774    0.9389   -1.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3190    0.1077   -0.7061 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3508   -0.8436   -0.9065 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0751   -0.6626   -0.4519 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2476   -1.4491    0.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8648   -1.4953    1.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9829   -0.9729    0.4235 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3302   -0.4362    0.8240 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1000   -1.4141    1.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3078   -0.6623    2.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0830   -0.2043    1.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4047   -0.2008    1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2396    0.2305    0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3605    0.7253    0.2580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7557    0.0815   -1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3097   -0.3535   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5037    0.2340   -0.2540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6139    1.7644   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0778   -0.1349   -0.4660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3067    0.9499   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161    0.5828   -1.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8528    0.1407   -0.1842 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0556    1.2650    0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6602    0.4762   -2.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726    1.9937   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082    1.0114   -2.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6649    0.7329    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2376   -0.3881   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -1.3159   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5994   -2.4633    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9885   -0.9919    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6233   -2.5863    1.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8311   -0.9604    2.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8344   -1.7360   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2931    0.5205    1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4276   -1.7348    2.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4776   -2.2601    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9015   -1.3459    2.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9193    0.1999    2.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8743   -0.5213    2.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9396    0.9910   -1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3528   -0.7328   -1.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2227   -1.4635   -1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8899   -0.0884   -2.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6448    2.1038   -0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3072    2.1700   -1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0043    2.1511    0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9873   -1.0508   -1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3775    1.9314   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7964    1.0995   -2.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6262    1.4946   -1.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1690   -0.2597   -2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2583    2.0498    0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099    1.8013    0.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9989    0.9809    1.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
 21 22  1  0
 22 23  1  1
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  1
  3 28  1  0
  4 29  1  6
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  6
  8 35  1  1
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  6
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

HEADER    PROTEIN                                 08-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAY-20         0                                  
HETATM    1  C   UNK     0    8665.3378666.681   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8661.3438662.821   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8669.3268669.013   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0    8667.9988666.681   0.000  0.00  0.00           H+0
HETATM    5  H   UNK     0    8666.6668664.377   0.000  0.00  0.00           H+0
HETATM    6  H   UNK     0    8669.3268664.377   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0    8664.0068665.906   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8662.6728665.136   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.6728663.596   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8664.0068662.826   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8665.3398663.596   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.3398665.136   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8666.6668665.909   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8666.6668662.829   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8668.0008663.599   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8668.0008665.139   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.9978668.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8666.6638667.465   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8669.3318667.465   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8669.3318665.925   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8670.7958665.449   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8671.7018666.695   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.7958667.941   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8670.7958669.481   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8672.1288670.251   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0    8669.4608670.251   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0    8672.1288668.711   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2    9                                                            
CONECT    3   19                                                            
CONECT    4   16                                                            
CONECT    5   13                                                            
CONECT    6   20                                                            
CONECT    7    8   12                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    2                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12    7   11   13    1                                             
CONECT   13   16   18    5   12                                             
CONECT   14   15   11                                                       
CONECT   15   14   16                                                       
CONECT   16   13   15    4   20                                             
CONECT   17   18   19                                                       
CONECT   18   17   13                                                       
CONECT   19   20   23   17    3                                             
CONECT   20   19   21    6   16                                             
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   24   27   19   22                                             
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   23                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0003069
HETATM    1  C1  UNL     1       4.277   0.939  -1.961  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.319   0.108  -0.706  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.351  -0.844  -0.907  1.00  0.00           O  
HETATM    4  C3  UNL     1       3.075  -0.663  -0.452  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.248  -1.449   0.830  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.865  -1.495   1.482  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.983  -0.973   0.424  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.330  -0.436   0.824  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.100  -1.414   1.665  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.308  -0.662   2.190  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.083  -0.204   1.010  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.405  -0.201   1.143  1.00  0.00           C  
HETATM   13  C12 UNL     1      -5.240   0.231   0.042  1.00  0.00           C  
HETATM   14  O2  UNL     1      -6.361   0.725   0.258  1.00  0.00           O  
HETATM   15  C13 UNL     1      -4.756   0.082  -1.354  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.310  -0.353  -1.395  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.504   0.234  -0.254  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.614   1.764  -0.293  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.078  -0.135  -0.466  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.307   0.950  -1.175  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.116   0.583  -1.426  1.00  0.00           C  
HETATM   22  C20 UNL     1       1.853   0.141  -0.184  1.00  0.00           C  
HETATM   23  C21 UNL     1       2.056   1.265   0.786  1.00  0.00           C  
HETATM   24  H1  UNL     1       3.660   0.476  -2.758  1.00  0.00           H  
HETATM   25  H2  UNL     1       3.973   1.994  -1.747  1.00  0.00           H  
HETATM   26  H3  UNL     1       5.308   1.011  -2.371  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.665   0.733   0.127  1.00  0.00           H  
HETATM   28  H5  UNL     1       6.238  -0.388  -0.922  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.885  -1.316  -1.323  1.00  0.00           H  
HETATM   30  H7  UNL     1       3.599  -2.463   0.551  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.988  -0.992   1.517  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.623  -2.586   1.627  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.831  -0.960   2.435  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.834  -1.736  -0.370  1.00  0.00           H  
HETATM   35  H12 UNL     1      -0.293   0.520   1.384  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.428  -1.735   2.490  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.478  -2.260   1.066  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.902  -1.346   2.825  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.919   0.200   2.771  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.874  -0.521   2.081  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.940   0.991  -1.962  1.00  0.00           H  
HETATM   42  H19 UNL     1      -5.353  -0.733  -1.815  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.223  -1.464  -1.303  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.890  -0.088  -2.383  1.00  0.00           H  
HETATM   45  H22 UNL     1      -3.645   2.104  -0.103  1.00  0.00           H  
HETATM   46  H23 UNL     1      -2.307   2.170  -1.263  1.00  0.00           H  
HETATM   47  H24 UNL     1      -2.004   2.151   0.564  1.00  0.00           H  
HETATM   48  H25 UNL     1      -0.987  -1.051  -1.094  1.00  0.00           H  
HETATM   49  H26 UNL     1      -0.378   1.931  -0.647  1.00  0.00           H  
HETATM   50  H27 UNL     1      -0.796   1.099  -2.160  1.00  0.00           H  
HETATM   51  H28 UNL     1       1.626   1.495  -1.806  1.00  0.00           H  
HETATM   52  H29 UNL     1       1.169  -0.260  -2.150  1.00  0.00           H  
HETATM   53  H30 UNL     1       1.258   2.050   0.640  1.00  0.00           H  
HETATM   54  H31 UNL     1       3.010   1.801   0.642  1.00  0.00           H  
HETATM   55  H32 UNL     1       1.999   0.981   1.841  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   27
CONECT    3   28
CONECT    4    5   22   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   22   34
CONECT    8    9   19   35
CONECT    9   10   36   37
CONECT   10   11   38   39
CONECT   11   12   12   17
CONECT   12   13   40
CONECT   13   14   14   15
CONECT   15   16   41   42
CONECT   16   17   43   44
CONECT   17   18   19
CONECT   18   45   46   47
CONECT   19   20   48
CONECT   20   21   49   50
CONECT   21   22   51   52
CONECT   22   23
CONECT   23   53   54   55
END

HMDB0003069
     RDKit          3D
20alpha-Dihydroprogesterone
 55 58  0  0  0  0  0  0  0  0999 V2000
    4.2774    0.9389   -1.9607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3190    0.1077   -0.7061 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3508   -0.8436   -0.9065 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0751   -0.6626   -0.4519 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2476   -1.4491    0.8303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8648   -1.4953    1.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9829   -0.9729    0.4235 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3302   -0.4362    0.8240 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1000   -1.4141    1.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3078   -0.6623    2.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0830   -0.2043    1.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4047   -0.2008    1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2396    0.2305    0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3605    0.7253    0.2580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7557    0.0815   -1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3097   -0.3535   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5037    0.2340   -0.2540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6139    1.7644   -0.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0778   -0.1349   -0.4660 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3067    0.9499   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1161    0.5828   -1.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8528    0.1407   -0.1842 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0556    1.2650    0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6602    0.4762   -2.7582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726    1.9937   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082    1.0114   -2.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6649    0.7329    0.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2376   -0.3881   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -1.3159   -1.3229 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5994   -2.4633    0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9885   -0.9919    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6233   -2.5863    1.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8311   -0.9604    2.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8344   -1.7360   -0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2931    0.5205    1.3844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4276   -1.7348    2.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4776   -2.2601    1.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9015   -1.3459    2.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9193    0.1999    2.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8743   -0.5213    2.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9396    0.9910   -1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3528   -0.7328   -1.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2227   -1.4635   -1.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8899   -0.0884   -2.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6448    2.1038   -0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3072    2.1700   -1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0043    2.1511    0.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9873   -1.0508   -1.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3775    1.9314   -0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7964    1.0995   -2.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6262    1.4946   -1.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1690   -0.2597   -2.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2583    2.0498    0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0099    1.8013    0.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9989    0.9809    1.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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
 21 22  1  0
 22 23  1  1
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  1
  3 28  1  0
  4 29  1  6
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  6
  8 35  1  1
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 12 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  6
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(20S)-Hydroxypregn-4-en-3-one	ChEBI
(S)-20-Hydroxypregn-4-en-3-one	ChEBI
20alpha-Hydroxy-4-pregnen-3-one	ChEBI
20alpha-Hydroxypregn-4-en-3-one	ChEBI
20alpha-Hydroxyprogesterone	ChEBI
Dihydroprogesterone	ChEBI
20a-Hydroxy-4-pregnen-3-one	Generator
20Α-hydroxy-4-pregnen-3-one	Generator
20a-Hydroxypregn-4-en-3-one	Generator
20Α-hydroxypregn-4-en-3-one	Generator
20a-Hydroxyprogesterone	Generator
20Α-hydroxyprogesterone	Generator
20a-Dihydroprogesterone	Generator
20Α-dihydroprogesterone	Generator
20 alpha Dihydroprogesterone	HMDB
20-alpha-Hydroxyprogesterone	HMDB
20alpha Hydroxypregn 4 ene 3 one	HMDB
20 alpha-Hydroxyprogesterone	HMDB
20-alpha-Dihydroprogesterone	HMDB
20 alpha Hydroxy 4 pregnen 3 one	HMDB
20 alpha Hydroxyprogesterone	HMDB
20 alpha-Dihydroprogesterone	HMDB
20 alpha-Hydroxy-4-pregnen-3-one	HMDB
20-alpha-Hydroxy- pregn-4-en-3-one	HMDB
20alpha-Hydroxypregn-4-ene-3-one	HMDB
Pregn 4 en 3 one, 20 alpha hydroxy	HMDB
(20S)-20-Hydroxypregn-4-en-3-one	HMDB
20(S)-Hydroxyprogesterone	HMDB
20-Hydroxypregn-4-en-3-one	HMDB
20alpha-Hydroxy-delta4-pregnen-3-one	HMDB
20alpha-Hydroxydihydroprogesterone	HMDB
20alpha-Progerol	HMDB
20Α-hydroxy-δ4-pregnen-3-one	HMDB
20Α-hydroxydihydroprogesterone	HMDB
20Α-progerol	HMDB
4-Pregnen-3-one-20alpha-ol	HMDB
4-Pregnen-3-one-20α-ol	HMDB
Pregn-4-en-20alpha-ol-3-one	HMDB
Pregn-4-en-20α-ol-3-one	HMDB
Pregn-4-ene-20alpha-ol-3-one	HMDB
Pregn-4-ene-20α-ol-3-one	HMDB
Progesterol-20alpha	HMDB
Progesterol-20α	HMDB
delta4-Pregnen-20alpha-ol-3-one	HMDB
delta4-Pregnene-20alpha-ol-3-one	HMDB
Δ4-pregnen-20α-ol-3-one	HMDB
Δ4-pregnene-20α-ol-3-one	HMDB
20alpha-Dihydroprogesterone	ChEBI

Chemical Formula

C₂₁H₃₂O₂

Average Molecular Weight

316.4776

Monoisotopic Molecular Weight

316.240230268

IUPAC Name

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

CAS Registry Number

145-14-2

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)O

InChI Identifier

InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12-13,16-19,22H,4-11H2,1-3H3/t13-,16-,17+,18-,19-,20-,21+/m0/s1

InChI Key

RWBRUCCWZPSBFC-RXRZZTMXSA-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-hydroxysteroid
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic ketone
Secondary alcohol
Ketone
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

20-hydroxypregn-4-en-3-one (CHEBI:28453 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030169 )

Ontology

Physiological effect

Health effect

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0003069)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 579026)

Cellular substructure

Organ

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0003069)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0003069)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0003069)

Source

Endogenous

Endogenous (HMDB: HMDB0003069)

Animal

Animal (HMDB: HMDB0003069)

Exogenous

Food

Food (HMDB: HMDB0003069)

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: HMDB0003069)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0003069)

Molecular messenger

Hormone (HMDB: HMDB0003069)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0003069)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	126 - 131 °C	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	0.01 g/L	ALOGPS
logP	3.52	ALOGPS
logP	3.94	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	19	ChemAxon
pKa (Strongest Basic)	-1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	93.73 m³·mol⁻¹	ChemAxon
Polarizability	37.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	211.632	30932474
DeepCCS	[M+Na]+	185.894	30932474
AllCCS	[M+H]+	182.5	32859911
AllCCS	[M+H-H2O]+	179.5	32859911
AllCCS	[M+NH4]+	185.2	32859911
AllCCS	[M+Na]+	185.9	32859911
AllCCS	[M-H]-	187.0	32859911
AllCCS	[M+Na-2H]-	187.4	32859911
AllCCS	[M+HCOO]-	188.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
20alpha-Dihydroprogesterone	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)O	3707.6	Standard polar	33892256
20alpha-Dihydroprogesterone	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)O	2756.3	Standard non polar	33892256
20alpha-Dihydroprogesterone	[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)O	2941.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
20alpha-Dihydroprogesterone,1TMS,isomer #1	C[C@H](O[Si](C)(C)C)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C	2977.4	Semi standard non polar	33892256
20alpha-Dihydroprogesterone,1TMS,isomer #2	C[C@H](O)[C@H]1CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@]4(C)[C@H]3CC[C@]12C	2853.0	Semi standard non polar	33892256
20alpha-Dihydroprogesterone,2TMS,isomer #1	C[C@H](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]3CC[C@]12C	2888.9	Semi standard non polar	33892256
20alpha-Dihydroprogesterone,2TMS,isomer #1	C[C@H](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]3CC[C@]12C	2913.3	Standard non polar	33892256
20alpha-Dihydroprogesterone,2TMS,isomer #1	C[C@H](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]3CC[C@]12C	3144.0	Standard polar	33892256
20alpha-Dihydroprogesterone,1TBDMS,isomer #1	C[C@H](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]3CC[C@]12C	3195.6	Semi standard non polar	33892256
20alpha-Dihydroprogesterone,1TBDMS,isomer #2	C[C@H](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]3CC[C@]12C	3114.5	Semi standard non polar	33892256
20alpha-Dihydroprogesterone,2TBDMS,isomer #1	C[C@H](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]3CC[C@]12C	3393.3	Semi standard non polar	33892256
20alpha-Dihydroprogesterone,2TBDMS,isomer #1	C[C@H](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]3CC[C@]12C	3390.2	Standard non polar	33892256
20alpha-Dihydroprogesterone,2TBDMS,isomer #1	C[C@H](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]3CC[C@]12C	3384.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 20alpha-Dihydroprogesterone GC-MS (1 MEOX; 1 TMS)	splash10-014i-2900000000-ae18472ab2a463c4119b	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 20alpha-Dihydroprogesterone GC-MS (1 MEOX; 1 TMS)	splash10-014i-2900000000-b2664861b879ecb9d0e7	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20alpha-Dihydroprogesterone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 20alpha-Dihydroprogesterone 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 - 20alpha-Dihydroprogesterone 10V, Negative-QTOF	splash10-014i-0009000000-be6e06313d0abca8e664	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Dihydroprogesterone 20V, Negative-QTOF	splash10-014i-0069000000-737690db427e28fac080	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Dihydroprogesterone 40V, Negative-QTOF	splash10-03di-0039000000-93ddfd7d092de4d1ee38	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Dihydroprogesterone 10V, Positive-QTOF	splash10-00kb-0096000000-0227d7c5a3786f9345e9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Dihydroprogesterone 20V, Positive-QTOF	splash10-00kb-0692000000-a3a76f499e60c3488846	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20alpha-Dihydroprogesterone 40V, Positive-QTOF	splash10-052f-9810000000-4023a910f32e5c7d7941	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Placenta
Testis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	22944140	details
Blood	Detected and Quantified	0.0199 (0.0190-0.0208) uM	Adult (>18 years old)	Female	Normal	579026	details
Blood	Detected and Quantified	0.0164 (0.0126 - 0.0199) uM	Adult (>18 years old)	Female	Normal	579026	details
Blood	Detected and Quantified	0.0731 (0.0199 -0.1263) uM	Adult (>18 years old)	Female	Normal	579026	details
Blood	Detected and Quantified	0.0070 (0.0008 - 0.0117) uM	Adult (>18 years old)	Female	Normal	947130	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Schizophrenia	22944140	details

Associated Disorders and Diseases

Disease References

Schizophrenia
Bicikova M, Hill M, Ripova D, Mohr P, Hampl R: Determination of steroid metabolome as a possible tool for laboratory diagnosis of schizophrenia. J Steroid Biochem Mol Biol. 2013 Jan;133:77-83. doi: 10.1016/j.jsbmb.2012.08.009. Epub 2012 Aug 24. [PubMed:22944140 ]

Associated OMIM IDs

181500 (Schizophrenia)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023103

KNApSAcK ID

Not Available

Chemspider ID

8612

KEGG Compound ID

C04042

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

20α-Dihydroprogesterone

METLIN ID

Not Available

PubChem Compound

8956

PDB ID

Not Available

ChEBI ID

28453

Food Biomarker Ontology

Not Available

VMH ID

APRGSTRN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Sanai Y; Suzuki T; Yanaihara T; Nakayama T 20 alpha-Dihydropregnenolone-sulfate and 20 alpha-dihydroprogesterone biosynthesis and metabolism in feto-placental unit. Nippon Sanka Fujinka Gakkai zasshi (1984), 36(2), 195-201.

Material Safety Data Sheet (MSDS)

Not Available

General References

Rovensky J, Radikova Z, Imrich R, Greguska O, Vigas M, Macho L: Gonadal and adrenal steroid hormones in plasma and synovial fluid of patients with rheumatoid arthritis. Endocr Regul. 2004 Dec;38(4):143-9. [PubMed:15841793 ]
Kaaks R, Berrino F, Key T, Rinaldi S, Dossus L, Biessy C, Secreto G, Amiano P, Bingham S, Boeing H, Bueno de Mesquita HB, Chang-Claude J, Clavel-Chapelon F, Fournier A, van Gils CH, Gonzalez CA, Gurrea AB, Critselis E, Khaw KT, Krogh V, Lahmann PH, Nagel G, Olsen A, Onland-Moret NC, Overvad K, Palli D, Panico S, Peeters P, Quiros JR, Roddam A, Thiebaut A, Tjonneland A, Chirlaque MD, Trichopoulou A, Trichopoulos D, Tumino R, Vineis P, Norat T, Ferrari P, Slimani N, Riboli E: Serum sex steroids in premenopausal women and breast cancer risk within the European Prospective Investigation into Cancer and Nutrition (EPIC). J Natl Cancer Inst. 2005 May 18;97(10):755-65. [PubMed:15900045 ]
Reinberg A, Smolensky MH, Hallek M, Smith KD, Steinberger E: Annual variation in semen characteristics and plasma hormone levels in men undergoing vasectomy. Fertil Steril. 1988 Feb;49(2):309-15. [PubMed:3123279 ]
Piasek M, Gomzi M: [Environmental tobacco smoke and children: assessment of exposure and health effects]. Lijec Vjesn. 2004 Nov-Dec;126(11-12):325-30. [PubMed:16082891 ]
Suzuki T, Hirato K, Ogawa K, Yanaihara T, Nakayama T: [Changes in steroids in amniotic fluid in relation to the initiation of labor]. Nihon Sanka Fujinka Gakkai Zasshi. 1984 Oct;36(10):1841-50. [PubMed:6238997 ]
Kalinka J, Szekeres-Bartho J: The impact of dydrogesterone supplementation on hormonal profile and progesterone-induced blocking factor concentrations in women with threatened abortion. Am J Reprod Immunol. 2005 Apr;53(4):166-71. [PubMed:15760377 ]
Raja A, Hashmi SN, Sultana N, Rashid H: Presentation of polycystic ovary syndrome and its management with clomiphene alone and in combination with metformin. J Ayub Med Coll Abbottabad. 2005 Apr-Jun;17(2):50-3. [PubMed:16092652 ]
Ma H, Penning TM: Conversion of mammalian 3alpha-hydroxysteroid dehydrogenase to 20alpha-hydroxysteroid dehydrogenase using loop chimeras: changing specificity from androgens to progestins. Proc Natl Acad Sci U S A. 1999 Sep 28;96(20):11161-6. [PubMed:10500147 ]
Stranahan D, Rausch D, Deng A, Gaspari A: The role of intradermal skin testing and patch testing in the diagnosis of autoimmune progesterone dermatitis. Dermatitis. 2006 Mar;17(1):39-42. [PubMed:16800278 ]
Stachenfeld NS, Taylor HS: Progesterone increases plasma volume independent of estradiol. J Appl Physiol (1985). 2005 Jun;98(6):1991-7. Epub 2005 Feb 17. [PubMed:15718411 ]
Kenis I, Tartakover-Matalon S, Cherepnin N, Drucker L, Fishman A, Pomeranz M, Lishner M: Simvastatin has deleterious effects on human first trimester placental explants. Hum Reprod. 2005 Oct;20(10):2866-72. Epub 2005 Jun 15. [PubMed:15958395 ]
Nichols AA: Cholestasis of pregnancy: a review of the evidence. J Perinat Neonatal Nurs. 2005 Jul-Sep;19(3):217-25. [PubMed:16106229 ]
Bruno-Ambrosius K, Yucel-Lindberg T, Twetman S: Salivary buffer capacity in relation to menarche and progesterone levels in saliva from adolescent girls: a longitudinal study. Acta Odontol Scand. 2004 Oct;62(5):269-72. [PubMed:15841814 ]
Nielsen FH: The alteration of magnesium, calcium and phosphorus metabolism by dietary magnesium deprivation in postmenopausal women is not affected by dietary boron deprivation. Magnes Res. 2004 Sep;17(3):197-210. [PubMed:15724868 ]
Stanczyk FZ, Paulson RJ, Roy S: Percutaneous administration of progesterone: blood levels and endometrial protection. Menopause. 2005 Mar;12(2):232-7. [PubMed:15772572 ]
Seppala M, Ranta T, Hirvonen E: Hyperprolactinaemia and luteal insufficiency. Lancet. 1976 Jan 31;1(7953):229-30. [PubMed:55535 ]
Rovensky J, Kvetnansky R, Radikova Z, Imrich R, Greguska O, Vigas M, Macho L: Hormone concentrations in synovial fluid of patients with rheumatoid arthritis. Clin Exp Rheumatol. 2005 May-Jun;23(3):292-6. [PubMed:15971415 ]
THOMAS GH: Ketonic metabolites of progesterone and 19-norprogesterone in rabbit urine. Biochem J. 1962 Jun;83:450-5. [PubMed:13920778 ]
Casey ML, MacDonald PC: Metabolism of deoxycorticosterone and deoxycorticosterone sulfate in men and women. J Clin Invest. 1982 Aug;70(2):312-9. [PubMed:7096569 ]
Grissom FE, Brooks CL, Littleton GK: The effect of placenta on lactogen receptor in pseudopregnant rabbits. Endocr Res. 1990;16(1):51-75. [PubMed:2158435 ]
Lappas M, Yee K, Permezel M, Rice GE: Release and regulation of leptin, resistin and adiponectin from human placenta, fetal membranes, and maternal adipose tissue and skeletal muscle from normal and gestational diabetes mellitus-complicated pregnancies. J Endocrinol. 2005 Sep;186(3):457-65. [PubMed:16135665 ]
Hosaka M, Oshima H, Nankin H, Troen P: Studies of the human testis. XI. Leydig cell clusters and levels of intratesticular testosterone and 20 alpha-dihydroprogesterone. J Clin Endocrinol Metab. 1978 Nov;47(5):1164-7. [PubMed:263345 ]
Longcope C, Franz C, Morello C, Baker R, Johnston CC Jr: Steroid and gonadotropin levels in women during the peri-menopausal years. Maturitas. 1986 Oct;8(3):189-96. [PubMed:3097458 ]
Halari R, Hines M, Kumari V, Mehrotra R, Wheeler M, Ng V, Sharma T: Sex differences and individual differences in cognitive performance and their relationship to endogenous gonadal hormones and gonadotropins. Behav Neurosci. 2005 Feb;119(1):104-17. [PubMed:15727517 ]
Tuckey RC: Progesterone synthesis by the human placenta. Placenta. 2005 Apr;26(4):273-81. [PubMed:15823613 ]
Auge AP, Longui CA, Almeida Prado RA, Rocha MN, Hirota A, Busso NE, Monte O, Aldrighi JM: Abnormal inhibin A and inhibin B secretion in obese women with and without insulin resistance. Gynecol Endocrinol. 2005 Jul;21(1):7-11. [PubMed:16048795 ]
Kivlighan KT, Granger DA, Schwartz EB: Blood contamination and the measurement of salivary progesterone and estradiol. Horm Behav. 2005 Mar;47(3):367-70. [PubMed:15708767 ]

Enzymes

Enzyme Details

1. Aldo-keto reductase family 1 member C1

General function:: Involved in oxidoreductase activity
Specific function:: Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:: AKR1C1
Uniprot ID:: Q04828
Molecular weight:: 36788.02

Showing metabocard for 20alpha-Dihydroprogesterone (HMDB0003069)

MOL for HMDB0003069 (20alpha-Dihydroprogesterone)

3D MOL for HMDB0003069 (20alpha-Dihydroprogesterone)

3D SDF for HMDB0003069 (20alpha-Dihydroprogesterone)

3D-SDF for HMDB0003069 (20alpha-Dihydroprogesterone)

PDB for HMDB0003069 (20alpha-Dihydroprogesterone)

3D PDB for HMDB0003069 (20alpha-Dihydroprogesterone)

SMILES for HMDB0003069 (20alpha-Dihydroprogesterone)

INCHI for HMDB0003069 (20alpha-Dihydroprogesterone)

Structure for HMDB0003069 (20alpha-Dihydroprogesterone)

3D Structure for HMDB0003069 (20alpha-Dihydroprogesterone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes