NP-MRD: Showing NP-Card for dihydroprogesterone (NP0320410)

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Record Information

Version

2.0

Created at

2022-09-11 22:02:41 UTC

Updated at

2022-09-11 22:02:41 UTC

NP-MRD ID

NP0320410

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dihydroprogesterone

Description

(20S)-20-hydroxypregn-4-en-3-one, also known as 20alpha-dihydroprogesterone or 20alpha-hydroxy-4-pregnen-3-one, 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. dihydroprogesterone is found in Homo sapiens and Mus musculus. Thus, (20S)-20-hydroxypregn-4-en-3-one is considered to be a steroid lipid molecule (20S)-20-hydroxypregn-4-en-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF 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

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
    5.5607    0.4892    0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1714    0.2236    0.9673 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1198   -0.9778    1.6379 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1231    0.3556   -0.0975 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3304   -0.6071   -1.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -0.9119   -1.7908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0316   -0.0328   -0.9871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3883   -0.4299   -0.9120 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0205   -0.1362   -2.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4247   -0.6878   -2.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1541   -0.1398   -1.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4645    0.0906   -1.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3094    0.6268   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5043    0.9147   -0.3764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7184    0.8350    1.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2667    1.2734    0.9086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5069    0.1481    0.2550 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6610   -1.0682    1.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    0.5211    0.0654 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3748    0.5830    1.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0843    0.9938    1.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7497   -0.0171    0.3615 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6748   -1.3981    0.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1638    1.0029    1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4553    1.1734   -0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1104   -0.4372    0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9632    1.0244    1.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3708   -0.9199    2.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0727    1.3750   -0.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9648   -0.1650   -2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7634   -1.5440   -0.8731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8813   -0.6123   -2.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6997   -1.9849   -1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0868    0.9986   -1.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5918   -1.4818   -0.6900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1036    0.9663   -2.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4566   -0.5628   -3.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4242   -1.8064   -2.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9149   -0.3976   -3.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9439   -0.1164   -2.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2280    1.6620    1.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6944   -0.1007    1.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3271    2.1591    0.2324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8798    1.5696    1.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6018   -1.5839    0.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7402   -0.7119    2.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8182   -1.7572    1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0429    1.5291   -0.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4453   -0.3443    1.9649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8514    1.3854    1.9786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5160    0.9922    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841    1.9966    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6745   -1.8672    0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3986   -2.1072    0.5347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8609   -1.3776    2.0685 H   0  0  0  0  0  0  0  0  0  0  0  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
  4  2  1  0
  2  1  1  0
  2  3  1  0
 22  4  1  0
 22  7  1  0
 19  8  1  0
 17 11  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
  2 27  1  1
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 28  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>
NP0320410

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

Synonyms

Value	Source
(20S)-Hydroxypregn-4-en-3-one	ChEBI
(S)-20-Hydroxypregn-4-en-3-one	ChEBI
20alpha-Dihydroprogesterone	ChEBI
20alpha-Hydroxy-4-pregnen-3-one	ChEBI
20alpha-Hydroxypregn-4-en-3-one	ChEBI
20alpha-Hydroxyprogesterone	ChEBI
Dihydroprogesterone	ChEBI
20a-Dihydroprogesterone	Generator
20α-Dihydroprogesterone	Generator
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
20 alpha Dihydroprogesterone	MeSH
20-alpha-Hydroxyprogesterone	MeSH
20alpha Hydroxypregn 4 ene 3 one	MeSH
20 alpha-Hydroxyprogesterone	MeSH
20-alpha-Dihydroprogesterone	MeSH
20 alpha Hydroxy 4 pregnen 3 one	MeSH
20 alpha Hydroxyprogesterone	MeSH
20 alpha-Dihydroprogesterone	MeSH
20 alpha-Hydroxy-4-pregnen-3-one	MeSH
20-alpha-Hydroxy- pregn-4-en-3-one	MeSH
20alpha-Hydroxypregn-4-ene-3-one	MeSH
Pregn 4 en 3 one, 20 alpha hydroxy	MeSH
(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

Chemical Formula

C₂₁H₃₂O₂

Average Mass

316.4776 Da

Monoisotopic Mass

316.24023 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Homo sapiens	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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