NP-MRD: Showing NP-Card for 11b-Hydroxyprogesterone (NP0136759)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-12 15:22:51 UTC

Updated at

2022-05-12 15:22:52 UTC

NP-MRD ID

NP0136759

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11b-Hydroxyprogesterone

Description

11B-Hydroxyprogesterone, also known as 21-deoxycorticosterone, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. Plasma 11b-Hydroxyprogesterone concentrations does not vary significantly as a function of age, sex, or phase of the menstrual cycle, in contrast to 17-hydroxyprogesterone. There are 4 recognized clinical forms of congenital adrenal hyperplasia, the majority of cases being associated with 21-hydroxylase deficiency: Salt-wasting (SW), simple virilizing (SV), nonclassic (NC) late-onset (also called attenuated and acquired), and cryptic. 11B-Hydroxyprogesterone is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, 11b-hydroxyprogesterone participates in a number of enzymatic reactions. In particular, 11b-hydroxyprogesterone can be converted into corticosterone through its interaction with the enzyme steroid 21-hydroxylase. In addition, 11b-hydroxyprogesterone can be biosynthesized from 21-deoxycortisol; which is catalyzed by the enzyme steroid 17-alpha-hydroxylase/17,20 lyase. 11B-Hydroxyprogesterone is a normal human metabolite. In humans, 11b-hydroxyprogesterone is involved in the metabolic disorder called the 11-beta-hydroxylase deficiency (cyp11b1) pathway. Docking 11OHP within the hMR-ligand-binding domain homology model revealed that the agonist activity of 11OHP is caused by contacts between its 11 beta-hydroxyl group and Asn770. 21-Hydroxylase deficiency is unusual among genetic diseases in that approximately 95% of the mutant alleles have apparently been generated by recombination between a normally active gene (CYP21) and a closely linked pseudogene (CYP21P). These findings demonstrate that in the absence of the 21-hydroxyl group, the 11 beta-hydroxyl group can produce the contact with the hMR-Asn770 required for the hMR activation leading to stimulated Na(+) absorption. It activates the transiently expressed hMR in COS-7 cells in a dose-dependent manner (ED(50): 10(-8) M) and, like aldosterone, stimulated Ams I(sc) in mpkCCD(cl4) cells. 21-Hydroxylase deficiency (OMIM 201910 ) is probably the most frequent (if not the most frequent) autosomal recessive genetic disease, occurring in almost 1% of Caucasians and about 3% of Ashkenazi Jews.

Structure

MOL 3D MOL SDF PDB SMILES InChI

HMDB04031.mol
  Mrv1652304202019512D          

 27 30  0  0  0  0            999 V2000
   -2.3522   -0.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522   -1.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -2.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -1.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -0.8115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6377   -0.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -2.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -1.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -0.8115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2088   -0.3990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2201   -0.3990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2201    0.4260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5057    0.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088    0.4260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0048   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4897    0.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048    0.6810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2597    1.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3064    1.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057    0.0135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233    0.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -1.2240    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7391    1.0580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201   -1.2240    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0667   -2.0490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667    1.6371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6763    2.0490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 17 18  1  1  0  0  0
 12 19  1  1  0  0  0
  9 20  1  1  0  0  0
  5 21  1  1  0  0  0
 10 22  1  6  0  0  0
 14 23  1  6  0  0  0
 11 24  1  6  0  0  0
  2 25  2  0  0  0  0
 18 26  1  0  0  0  0
 18 27  2  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    2.5417    1.2368   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0752   -0.1762   -0.2836 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2954   -0.4581   -1.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0951   -0.9845   -1.3156 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0430   -2.3899   -1.1674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843   -0.4211   -0.2230 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0263    0.3027    0.8345 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8002    0.3762    2.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0927    1.1684    1.8609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033    0.6183    0.6824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0658    0.2593    0.8271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8029   -0.2956   -0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0256   -0.2600   -0.3868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9609   -0.9051   -1.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8912    0.1061   -1.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0170    0.5077   -0.5695 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4715    1.9004   -0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2008   -0.5141    0.9060 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1352   -0.3531    2.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3453   -1.1533    1.5018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2186   -1.0906   -0.0283 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4958   -0.5793   -0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1480   -1.2218   -1.4558 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1049    0.6000   -0.1553 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1309    1.5652    0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2048    1.3331   -1.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7196    1.9790   -0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8791   -1.2345   -2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2775    0.4215   -2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6046   -0.8759   -2.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7781   -2.6902   -0.6982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3538   -1.2681    0.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1024    1.3198    0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203    0.9619    2.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0316   -0.6112    2.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8963    2.2301    1.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7064    1.0167    2.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5988    0.3534    1.7631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5761   -1.8645   -1.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5416   -1.0442   -2.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3712   -0.1087   -2.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4805    1.0527   -1.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1395    2.3786   -1.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4891    1.8366   -1.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3915    2.5684   -0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9545   -1.5979    0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4353    0.6657    2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7354   -0.8475    2.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1478   -2.1952    1.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2887   -0.7435    1.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0641   -2.1123   -0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5722    1.2381   -0.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 24  1  0
 22 23  2  0
 21  2  1  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
  2 18  1  0
 16  6  1  0
  7 18  1  0
 16 10  1  0
 18 46  1  6
 19 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  6
 24 52  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  6
  5 31  1  0
  6 32  1  1
  7 33  1  6
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 11 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
M  END

HMDB04031.mol
  Mrv1652304202019512D          

 27 30  0  0  0  0            999 V2000
   -2.3522   -0.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522   -1.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -2.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -1.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233   -0.8115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6377   -0.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -2.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -1.6365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057   -0.8115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2088   -0.3990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2201   -0.3990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2201    0.4260    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5057    0.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088    0.4260    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0048   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4897    0.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0048    0.6810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2597    1.4656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3064    1.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5057    0.0135    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9233    0.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -1.2240    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7391    1.0580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2201   -1.2240    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0667   -2.0490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667    1.6371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6763    2.0490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 17 18  1  1  0  0  0
 12 19  1  1  0  0  0
  9 20  1  1  0  0  0
  5 21  1  1  0  0  0
 10 22  1  6  0  0  0
 14 23  1  6  0  0  0
 11 24  1  6  0  0  0
  2 25  2  0  0  0  0
 18 26  1  0  0  0  0
 18 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0136759

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-19-8-7-12(21)9-11(19)3-4-13-14-5-6-15(18(23)24)20(14,2)10-16(22)17(13)19/h9,13-17,22H,3-8,10H2,1-2H3,(H,23,24)/t13-,14-,15+,16+,17+,19-,20-/m0/s1

> <INCHI_KEY>
XEFVQCSDIKHROY-CAPFDLLWSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.4339

> <EXACT_MASS>
332.198759384

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.96161026588132

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14S,15S,17R)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-14-carboxylic acid

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
2.5102140810000004

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.028999386154727

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.677539271019291

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2595135928704847

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
90.74669999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,10S,11S,14S,15S,17R)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-14-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB04031.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  C   UNK     0      -4.391  -1.515   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.391  -3.055   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.057  -3.825   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.723  -3.055   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.723  -1.515   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.057  -0.745   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.390  -3.825   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.944  -3.055   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.944  -1.515   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.390  -0.745   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.278  -0.745   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.278   0.795   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.944   1.565   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.390   0.795   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.742  -1.221   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.647   0.025   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.742   1.271   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.218   2.736   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.439   2.327   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       0.944   0.025   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0      -1.723   0.025   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      -0.390  -2.285   0.000  0.00  0.00           H+0
HETATM   23  O   UNK     0      -1.380   1.975   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0       2.278  -2.285   0.000  0.00  0.00           H+0
HETATM   25  O   UNK     0      -5.725  -3.825   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.725   3.056   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       3.129   3.825   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   21                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   20                                             
CONECT   10    9    5   14   22                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10   23                                                  
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17   26   27                                                  
CONECT   19   12                                                            
CONECT   20    9                                                            
CONECT   21    5                                                            
CONECT   22   10                                                            
CONECT   23   14                                                            
CONECT   24   11                                                            
CONECT   25    2                                                            
CONECT   26   18                                                            
CONECT   27   18                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
(11beta)-11-Hydroxypregn-4-ene-3,20-dione	HMDB
11-beta-Hydroxypregn-4-ene-3,20-dione	HMDB
11-beta-Hydroxyprogesterone	HMDB
11beta-Hydroxypregn-4-ene-3,20-dione	HMDB
11beta-Hydroxyprogesterone	HMDB
21-Deoxycorticosterone	HMDB

Chemical Formula

C₂₀H₂₈O₄

Average Mass

332.4339 Da

Monoisotopic Mass

332.19876 Da

IUPAC Name

(1S,2R,10S,11S,14S,15S,17R)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-14-carboxylic acid

Traditional Name

(1S,2R,10S,11S,14S,15S,17R)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-14-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H28O4/c1-19-8-7-12(21)9-11(19)3-4-13-14-5-6-15(18(23)24)20(14,2)10-16(22)17(13)19/h9,13-17,22H,3-8,10H2,1-2H3,(H,23,24)/t13-,14-,15+,16+,17+,19-,20-/m0/s1

InChI Key

XEFVQCSDIKHROY-CAPFDLLWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

20-hydroxysteroid
Androgen-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
11-hydroxysteroid
11-alpha-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	1.97	ALOGPS
logP	2.51	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-0.26	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.75 m³·mol⁻¹	ChemAxon
Polarizability	36.96 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

External Links

HMDB ID

HMDB0004031

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023284

KNApSAcK ID

Not Available

Chemspider ID

24840621

KEGG Compound ID

C05498

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

7005

PubChem Compound

44263342

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 11b-Hydroxyprogesterone (NP0136759)

MOL for NP0136759 (11b-Hydroxyprogesterone)

3D MOL for NP0136759 (11b-Hydroxyprogesterone)

3D SDF for NP0136759 (11b-Hydroxyprogesterone)

3D-SDF for NP0136759 (11b-Hydroxyprogesterone)

PDB for NP0136759 (11b-Hydroxyprogesterone)

3D PDB for NP0136759 (11b-Hydroxyprogesterone)

SMILES for NP0136759 (11b-Hydroxyprogesterone)

INCHI for NP0136759 (11b-Hydroxyprogesterone)

Structure for NP0136759 (11b-Hydroxyprogesterone)

3D Structure for NP0136759 (11b-Hydroxyprogesterone)