NP-MRD: Showing NP-Card for 17-Hydroxyprogesterone (NP0000699)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2021-10-07 20:39:33 UTC

NP-MRD ID

NP0000699

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-Hydroxyprogesterone

Description

17-Hydroxyprogesterone also known as 17-OH progesterone (17-OHP), or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone. Formally it is a 17alpha-hydroxy steroid that is the 17alpha-hydroxy derivative of progesterone. 17-Hydroxyprogesterone is found in all vertebrates. It is a chemical intermediate in the biosynthesis of many endogenous steroids, including androgens, estrogens, glucocorticoids, mineralocorticoids and neurosteroids. In particular, 17-Hydroxyprogesterone serves as an intermediate in the biosynthesis of hydrocortisone and gonadal steroid hormones. It is derived from progesterone via the enzyme known as 17-hydroxylase, a cytochrome P450 enzyme also known as CYP17A1. It can also be biosynthesized from 17-hydroxypregnenolone via the enzyme 3beta-hydroxysteroid dehydrogenase/delta5-4 isomerase (PMID: 1955079 ). 17-OHP is an agonist of the progesterone receptor (PR). It is also an antagonist of the mineralocorticoid receptor (MR) as well as a partial agonist of the glucocorticoid receptor (GR). 17-Hydroxyprogesterone is a natural progestin and in pregnancy it increases in the third trimester primarily due to fetal adrenal production. 17-Hydroxyprogesterone is primarily produced in the adrenal glands and to some degree in the gonads, specifically the corpus luteum of the ovary. Normal levels are 3-90 ng/dl in children, and in women, 15-70 ng/dl prior to ovulation, and 35-290 ng/dl during the luteal phase. Measurements of levels of 17-hydroxyprogesterone are useful in the evaluation of patients with suspected congenital adrenal hyperplasia as the typical enzymes that are defective, namely 21-hydroxylase, lead to a build-up of 17-OHP. 17-OHP levels can also be used to measure contribution of progestational activity of the corpus luteum during pregnancy as progesterone but not 17-OHP is also contributed by the placenta.

Structure

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

17-Hydroxyprogesterone.mol
  Mrv1652305261923522D          

 27 30  0  0  0  0            999 V2000
   -1.8185   -0.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330   -0.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2475   -1.9502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8185   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -0.7127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0393   -0.3002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8240   -0.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3089    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240    0.7797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5717    1.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    0.6552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6436    1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0393    0.5248    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0393    1.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    0.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -0.3002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1041   -0.7127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1041    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884    1.5334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -1.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    0.1123    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0393   -1.1252    0.0000 H   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
  1 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  1  0  0  0
 13 24  1  6  0  0  0
 21 25  1  6  0  0  0
  9 26  1  1  0  0  0
 10 27  1  6  0  0  0
M  END

HMDB0000374
     RDKit          3D
17-Hydroxyprogesterone
 54 57  0  0  0  0  0  0  0  0999 V2000
   -4.9720   -0.9828    0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2846   -1.0946   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716   -1.9423   -1.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758   -0.2365   -0.7900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7515   -0.4888   -2.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4507    1.2496   -0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0736    1.9005   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1244    0.7532   -0.6698 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2188    0.9180   -0.0683 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9390    2.0000   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2384    2.2767   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    1.0106   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3306    1.1015   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933   -0.0866   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3785   -0.0314    0.3250 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6212   -1.3908   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1805   -1.2421   -0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4069   -0.3198    0.0384 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6521   -0.8555    1.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9663   -0.3761   -0.3318 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2163   -1.4788    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -1.6138   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9298   -0.3419    0.0667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1562    0.0498    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0950   -1.0724    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8650    0.0122    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574   -1.8333    1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2692    0.0719   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9467    1.6225   -1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630    1.4812    0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246    2.5670   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959    2.4630    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389    0.4456   -1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    1.1641    1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579    1.5393   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    2.8947   -0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535    3.0794   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    2.5885    0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8009    2.0675   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1921   -1.7421   -1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378   -2.0862    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128   -2.2217   -1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -0.7457   -1.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496   -0.5539    1.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9188   -0.4327    2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.9538    1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.5886   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769   -2.4524    0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645   -1.1923    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -1.8965   -1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6798   -2.4036    0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7340    0.9886    1.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    0.1626    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7073   -0.7509    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  6
  4  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  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  6
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

17-Hydroxyprogesterone.mol
  Mrv1652305261923522D          

 27 30  0  0  0  0            999 V2000
   -1.8185   -0.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330   -0.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5330   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2475   -1.9502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8185   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1041   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -1.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249   -0.7127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0393   -0.3002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8240   -0.5552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3089    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240    0.7797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5717    1.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2475    0.6552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6436    1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0393    0.5248    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0393    1.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    0.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    0.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -0.3002    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1041   -0.7127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1041    0.1123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884    1.5334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -1.1252    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3249    0.1123    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0393   -1.1252    0.0000 H   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 10 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
  1 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  1  0  0  0
 13 24  1  6  0  0  0
 21 25  1  6  0  0  0
  9 26  1  1  0  0  0
 10 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0000699

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

> <INCHI_KEY>
DBPWSSGDRRHUNT-CEGNMAFCSA-N

> <FORMULA>
C21H30O3

> <MOLECULAR_WEIGHT>
330.4611

> <EXACT_MASS>
330.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.895190581319426

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
3.4011792776666674

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.598886675440433

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.699646444874293

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8049652826185154

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
94.10529999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000374
     RDKit          3D
17-Hydroxyprogesterone
 54 57  0  0  0  0  0  0  0  0999 V2000
   -4.9720   -0.9828    0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2846   -1.0946   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716   -1.9423   -1.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758   -0.2365   -0.7900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7515   -0.4888   -2.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4507    1.2496   -0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0736    1.9005   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1244    0.7532   -0.6698 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2188    0.9180   -0.0683 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9390    2.0000   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2384    2.2767   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    1.0106   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3306    1.1015   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933   -0.0866   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3785   -0.0314    0.3250 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6212   -1.3908   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1805   -1.2421   -0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4069   -0.3198    0.0384 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6521   -0.8555    1.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9663   -0.3761   -0.3318 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2163   -1.4788    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -1.6138   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9298   -0.3419    0.0667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1562    0.0498    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0950   -1.0724    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8650    0.0122    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574   -1.8333    1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2692    0.0719   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9467    1.6225   -1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630    1.4812    0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246    2.5670   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959    2.4630    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389    0.4456   -1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    1.1641    1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579    1.5393   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    2.8947   -0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535    3.0794   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    2.5885    0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8009    2.0675   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1921   -1.7421   -1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378   -2.0862    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128   -2.2217   -1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -0.7457   -1.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496   -0.5539    1.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9188   -0.4327    2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.9538    1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.5886   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769   -2.4524    0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645   -1.1923    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -1.8965   -1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6798   -2.4036    0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7340    0.9886    1.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    0.1626    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7073   -0.7509    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  6
  4  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  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  6
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 17-Hydroxyprogesterone.mol                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -3.395  -0.560   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.728  -1.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.728  -2.870   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -6.062  -3.640   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.395  -3.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.061  -2.870   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.727  -3.640   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.606  -2.870   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.606  -1.330   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.940  -0.560   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.405  -1.036   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.310   0.210   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.405   1.455   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.801   2.106   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.062   1.223   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.935   3.640   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.940   0.980   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.940   2.520   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.606   1.750   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.727   0.980   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.727  -0.560   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.061  -1.330   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.061   0.210   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.778   2.862   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0      -0.727  -2.100   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.606   0.210   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.940  -2.100   0.000  0.00  0.00           H+0
CONECT    1    2   22                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   21   26                                             
CONECT   10    9   11   17   27                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17   24                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   10   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    9   22   25                                             
CONECT   22   21    1    6   23                                             
CONECT   23   22                                                            
CONECT   24   13                                                            
CONECT   25   21                                                            
CONECT   26    9                                                            
CONECT   27   10                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0000374
HETATM    1  C1  UNL     1      -4.972  -0.983   0.875  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.285  -1.095  -0.423  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.672  -1.942  -1.210  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.176  -0.236  -0.790  1.00  0.00           C  
HETATM    5  O2  UNL     1      -2.751  -0.489  -2.123  1.00  0.00           O  
HETATM    6  C4  UNL     1      -3.451   1.250  -0.717  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.074   1.901  -0.521  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.124   0.753  -0.670  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.219   0.918  -0.068  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.939   2.000  -0.875  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.238   2.277  -0.120  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.011   1.011  -0.059  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.331   1.101  -0.096  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.193  -0.087  -0.043  1.00  0.00           C  
HETATM   15  O3  UNL     1       6.379  -0.031   0.325  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.621  -1.391  -0.443  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.180  -1.242  -0.887  1.00  0.00           C  
HETATM   18  C15 UNL     1       2.407  -0.320   0.038  1.00  0.00           C  
HETATM   19  C16 UNL     1       2.652  -0.855   1.456  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.966  -0.376  -0.332  1.00  0.00           C  
HETATM   21  C18 UNL     1       0.216  -1.479   0.395  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.191  -1.614  -0.116  1.00  0.00           C  
HETATM   23  C20 UNL     1      -1.930  -0.342   0.067  1.00  0.00           C  
HETATM   24  C21 UNL     1      -2.156   0.050   1.486  1.00  0.00           C  
HETATM   25  H1  UNL     1      -6.095  -1.072   0.693  1.00  0.00           H  
HETATM   26  H2  UNL     1      -4.865   0.012   1.327  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.757  -1.833   1.557  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.269   0.072  -2.740  1.00  0.00           H  
HETATM   29  H5  UNL     1      -3.947   1.622  -1.638  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.063   1.481   0.172  1.00  0.00           H  
HETATM   31  H7  UNL     1      -1.925   2.567  -1.398  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.996   2.463   0.406  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.039   0.446  -1.710  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.221   1.164   1.004  1.00  0.00           H  
HETATM   35  H11 UNL     1       1.158   1.539  -1.861  1.00  0.00           H  
HETATM   36  H12 UNL     1       0.318   2.895  -0.927  1.00  0.00           H  
HETATM   37  H13 UNL     1       2.753   3.079  -0.643  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.961   2.588   0.894  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.801   2.068  -0.168  1.00  0.00           H  
HETATM   40  H16 UNL     1       5.192  -1.742  -1.339  1.00  0.00           H  
HETATM   41  H17 UNL     1       4.738  -2.086   0.394  1.00  0.00           H  
HETATM   42  H18 UNL     1       2.713  -2.222  -1.009  1.00  0.00           H  
HETATM   43  H19 UNL     1       3.209  -0.746  -1.884  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.650  -0.554   1.820  1.00  0.00           H  
HETATM   45  H21 UNL     1       1.919  -0.433   2.170  1.00  0.00           H  
HETATM   46  H22 UNL     1       2.530  -1.954   1.474  1.00  0.00           H  
HETATM   47  H23 UNL     1       0.839  -0.589  -1.422  1.00  0.00           H  
HETATM   48  H24 UNL     1       0.777  -2.452   0.286  1.00  0.00           H  
HETATM   49  H25 UNL     1       0.165  -1.192   1.461  1.00  0.00           H  
HETATM   50  H26 UNL     1      -1.233  -1.897  -1.187  1.00  0.00           H  
HETATM   51  H27 UNL     1      -1.680  -2.404   0.521  1.00  0.00           H  
HETATM   52  H28 UNL     1      -2.734   0.989   1.597  1.00  0.00           H  
HETATM   53  H29 UNL     1      -1.204   0.163   2.060  1.00  0.00           H  
HETATM   54  H30 UNL     1      -2.707  -0.751   2.014  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    4
CONECT    4    5    6   23
CONECT    5   28
CONECT    6    7   29   30
CONECT    7    8   31   32
CONECT    8    9   23   33
CONECT    9   10   20   34
CONECT   10   11   35   36
CONECT   11   12   37   38
CONECT   12   13   13   18
CONECT   13   14   39
CONECT   14   15   15   16
CONECT   16   17   40   41
CONECT   17   18   42   43
CONECT   18   19   20
CONECT   19   44   45   46
CONECT   20   21   47
CONECT   21   22   48   49
CONECT   22   23   50   51
CONECT   23   24
CONECT   24   52   53   54
END

HMDB0000374
     RDKit          3D
17-Hydroxyprogesterone
 54 57  0  0  0  0  0  0  0  0999 V2000
   -4.9720   -0.9828    0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2846   -1.0946   -0.4229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6716   -1.9423   -1.2099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1758   -0.2365   -0.7900 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7515   -0.4888   -2.1229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4507    1.2496   -0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0736    1.9005   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1244    0.7532   -0.6698 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2188    0.9180   -0.0683 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9390    2.0000   -0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2384    2.2767   -0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    1.0106   -0.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3306    1.1015   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933   -0.0866   -0.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3785   -0.0314    0.3250 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6212   -1.3908   -0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1805   -1.2421   -0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4069   -0.3198    0.0384 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6521   -0.8555    1.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9663   -0.3761   -0.3318 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2163   -1.4788    0.3953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1913   -1.6138   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9298   -0.3419    0.0667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1562    0.0498    1.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0950   -1.0724    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8650    0.0122    1.3271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7574   -1.8333    1.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2692    0.0719   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9467    1.6225   -1.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630    1.4812    0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9246    2.5670   -1.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9959    2.4630    0.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389    0.4456   -1.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    1.1641    1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579    1.5393   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178    2.8947   -0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7535    3.0794   -0.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    2.5885    0.8941 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8009    2.0675   -0.1681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1921   -1.7421   -1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7378   -2.0862    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128   -2.2217   -1.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2090   -0.7457   -1.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6496   -0.5539    1.8198 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9188   -0.4327    2.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301   -1.9538    1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.5886   -1.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7769   -2.4524    0.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1645   -1.1923    1.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2334   -1.8965   -1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6798   -2.4036    0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7340    0.9886    1.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2043    0.1626    2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7073   -0.7509    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  6
  4  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  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 23  4  1  0
 23  8  1  0
 20  9  1  0
 18 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  6
  9 34  1  1
 10 35  1  0
 10 36  1  0
 11 37  1  0
 11 38  1  0
 13 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  6
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 24 52  1  0
 24 53  1  0
 24 54  1  0
M  END

View in JSmol

Synonyms

Value	Source
17-Hydroxypregn-4-en-3,20-dione	ChEBI
17alpha-Hydroxy-4-pregnene-3,20-dione	ChEBI
17alpha-Hydroxy-progesterone	ChEBI
delta(4)-Pregnene-17alpha-ol-3,20-dione	ChEBI
Hidroxiprogesterona	ChEBI
Hydroxyprogesterone	ChEBI
Hydroxyprogesteronum	ChEBI
Pregn-4-ene-3,20-dione-17-ol	ChEBI
17a-Hydroxy-4-pregnene-3,20-dione	Generator
17Α-hydroxy-4-pregnene-3,20-dione	Generator
17a-Hydroxy-progesterone	Generator
17Α-hydroxy-progesterone	Generator
delta(4)-Pregnene-17a-ol-3,20-dione	Generator
Δ(4)-pregnene-17α-ol-3,20-dione	Generator
Δ(4)-pregnene-17a-ol-3,20-dione	HMDB
17-alpha-Hydroxyprogesterone	HMDB
17-Hydroxypregn-4-ene-3,20-dione	HMDB
17-OH Progesterone	HMDB
17-OHP	HMDB
17a-Hydroxypregn-4-ene-3,20-dione	HMDB
17a-Hydroxyprogesterone	HMDB
17alpha-Hydroxyprogesterone	HMDB
D4-Pregnen-17a-ol-3,20-dione	HMDB
Gestageno	HMDB
Gestageno gador	HMDB
Pregn-4-en-17a-ol-3,20-dione	HMDB
Prodix	HMDB
Prodox	HMDB
17 Hydroxyprogesterone	HMDB
17-Hydroxyprogesterone, (17 alpha)-isomer	HMDB
17 alpha Hydroxyprogesterone	HMDB
17 alpha-Hydroxyprogesterone	HMDB
17-Hydroxyprogesterone, (9 beta, 10 alpha)-isomer	HMDB

Chemical Formula

C₂₁H₃₀O₃

Average Mass

330.4611 Da

Monoisotopic Mass

330.21949 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

68-96-2

SMILES

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

InChI Identifier

InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

InChI Key

DBPWSSGDRRHUNT-CEGNMAFCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Vitex agnus-castus	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-oxosteroid
3-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Alpha-hydroxy ketone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

17alpha-hydroxy steroid (CHEBI:17252 )
Progestagens (C01176 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030161 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	219 - 220 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0065 mg/mL	Not Available
LogP	3.17	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	2.99	ALOGPS
logP	3.4	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.7	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.11 m³·mol⁻¹	ChemAxon
Polarizability	37.9 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

HMDB0000374

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021992

KNApSAcK ID

Not Available

Chemspider ID

6002

KEGG Compound ID

C01176

BioCyc ID

17-ALPHA-HYDROXYPROGESTERONE

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

17252

Good Scents ID

rw1368781

References

General References

White PC, Tusie-Luna MT, New MI, Speiser PW: Mutations in steroid 21-hydroxylase (CYP21). Hum Mutat. 1994;3(4):373-8. [PubMed:8081391 ]
Mellon SH, Miller WL: Extraadrenal steroid 21-hydroxylation is not mediated by P450c21. J Clin Invest. 1989 Nov;84(5):1497-502. [PubMed:2808702 ]
Shackleton C, Malunowicz E: Apparent pregnene hydroxylation deficiency (APHD): seeking the parentage of an orphan metabolome. Steroids. 2003 Oct;68(9):707-17. [PubMed:14625002 ]
Gibney MJ, Walsh M, Brennan L, Roche HM, German B, van Ommen B: Metabolomics in human nutrition: opportunities and challenges. Am J Clin Nutr. 2005 Sep;82(3):497-503. [PubMed:16155259 ]
Sahin Y, Kelestimur F: 17-Hydroxyprogesterone responses to gonadotrophin-releasing hormone agonist buserelin and adrenocorticotrophin in polycystic ovary syndrome: investigation of adrenal and ovarian cytochrome P450c17alpha dysregulation. Hum Reprod. 1997 May;12(5):910-3. [PubMed:9194638 ]
Kirchengast S, Hartmann B, Huber J: Serum levels of sex hormones, thyroid hormones, growth hormone, IGF I, and cortisol and their relations to body fat distribution in healthy women dependent on their menopausal status. Z Morphol Anthropol. 1996 Sep;81(2):223-34. [PubMed:9270338 ]
Hampl R, Lachman M, Novak Z, Sulcova J, Starka L: Serum levels of steroid hormones in men with varicocele and oligospermia as compared to normozoospermic men. Exp Clin Endocrinol. 1992;100(3):117-9. [PubMed:1305061 ]
Ibanez L, de Zegher F, Potau N: Anovulation after precocious pubarche: early markers and time course in adolescence. J Clin Endocrinol Metab. 1999 Aug;84(8):2691-5. [PubMed:10443661 ]
Katagiri M, Kagawa N, Waterman MR: The role of cytochrome b5 in the biosynthesis of androgens by human P450c17. Arch Biochem Biophys. 1995 Mar 10;317(2):343-7. [PubMed:7893148 ]
al Saedi S, Dean H, Dent W, Cronin C: Reference ranges for serum cortisol and 17-hydroxyprogesterone levels in preterm infants. J Pediatr. 1995 Jun;126(6):985-7. [PubMed:7776113 ]
Gupta MK, Guryev OL, Auchus RJ: 5alpha-reduced C21 steroids are substrates for human cytochrome P450c17. Arch Biochem Biophys. 2003 Oct 15;418(2):151-60. [PubMed:14522586 ]
Escobar-Morreale HF, San Millan JL, Smith RR, Sancho J, Witchel SF: The presence of the 21-hydroxylase deficiency carrier status in hirsute women: phenotype-genotype correlations. Fertil Steril. 1999 Oct;72(4):629-38. [PubMed:10521100 ]
Wilson SC, Hodgins MB, Scott JS: Incomplete masculinization due to a deficiency of 17 beta-hydroxysteroid dehydrogenase: comparison of prepubertal and peripubertal siblings. Clin Endocrinol (Oxf). 1987 Apr;26(4):459-69. [PubMed:2820622 ]
Toscano V, Sancesario G, Bianchi P, Cicardi C, Casilli D, Giacomini P: Cerebrospinal fluid estrone in pseudotumor cerebri: a change in cerebral steroid hormone metabolism? J Endocrinol Invest. 1991 Feb;14(2):81-6. [PubMed:2061573 ]
Bolt RJ, Van Weissenbruch MM, Popp-Snijders C, Sweep FG, Lafeber HN, Delemarre-van de Waal HA: Maturity of the adrenal cortex in very preterm infants is related to gestational age. Pediatr Res. 2002 Sep;52(3):405-10. [PubMed:12193676 ]
Lorence MC, Naville D, Graham-Lorence SE, Mack SO, Murry BA, Trant JM, Mason JI: 3 beta-hydroxysteroid dehydrogenase/delta 5----4-isomerase expression in rat and characterization of the testis isoform. Mol Cell Endocrinol. 1991 Sep;80(1-3):21-31. doi: 10.1016/0303-7207(91)90139-j. [PubMed:1955079 ]

Showing NP-Card for 17-Hydroxyprogesterone (NP0000699)

MOL for NP0000699 (17-Hydroxyprogesterone)

3D MOL for NP0000699 (17-Hydroxyprogesterone)

3D SDF for NP0000699 (17-Hydroxyprogesterone)

3D-SDF for NP0000699 (17-Hydroxyprogesterone)

PDB for NP0000699 (17-Hydroxyprogesterone)

3D PDB for NP0000699 (17-Hydroxyprogesterone)

SMILES for NP0000699 (17-Hydroxyprogesterone)

INCHI for NP0000699 (17-Hydroxyprogesterone)

Structure for NP0000699 (17-Hydroxyprogesterone)

3D Structure for NP0000699 (17-Hydroxyprogesterone)