NP-MRD: Showing NP-Card for 3a,7a-Dihydroxy-5b-cholestanate (NP0334727)

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Record Information

Version

2.0

Created at

2024-09-10 19:42:08 UTC

Updated at

2024-09-10 19:42:08 UTC

NP-MRD ID

NP0334727

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a,7a-Dihydroxy-5b-cholestanate

Description

3A,7a-Dihydroxy-5b-cholestanate belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. 3A,7a-Dihydroxy-5b-cholestanate is an extremely weak basic (essentially neutral) compound (based on its pKa). 20 Alpha-dihydroxyprogesterone is a biologically weaker progestin. Progestin facilitates estrogen induction of the preovulatory luteinizing hormone (LH) surge. Howevever periovulatory levels of 20 alpha-dihydroxyprogesterone do not play a role in modulating the estrogen-induced bioactive LH surge. It is known that 20 alpha-dihydroxyprogesterone is increased at midcycle but its importance in regulating LH has not been studied.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231219482D          

 27 30  0  0  1  0            999 V2000
   21.6149   -8.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6605   -8.9807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4156  -12.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8647   -9.6396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.8647  -10.4645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.1502  -10.8770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.4357  -10.4645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.6452   -9.3882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.1502   -9.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6850  -10.8826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.6452  -10.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4357   -9.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1267  -10.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1634  -11.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8647   -8.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6784  -11.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4226  -12.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2391   -9.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9205  -10.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6914  -10.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1385  -10.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9068  -12.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9922   -9.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1315  -11.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2878  -11.0836    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5383  -11.4815    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.0446  -10.1159    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
  2 23  1  0  0  0  0
  3 24  2  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 15  1  1  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  5 25  1  6  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  6 26  1  1  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  7 27  1  6  0  0  0
  8 13  1  0  0  0  0
  8 18  1  0  0  0  0
  9 12  1  0  0  0  0
 10 16  1  0  0  0  0
 10 19  1  0  0  0  0
 10 20  1  1  0  0  0
 11 13  1  0  0  0  0
 14 17  1  0  0  0  0
 16 17  1  0  0  0  0
 16 22  2  0  0  0  0
 18 23  1  0  0  0  0
 19 21  1  0  0  0  0
 21 24  1  0  0  0  0
 22 24  1  0  0  0  0
M  END


  Mrv0541 02231219482D          

 27 30  0  0  1  0            999 V2000
   21.6149   -8.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6605   -8.9807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4156  -12.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8647   -9.6396    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.8647  -10.4645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.1502  -10.8770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.4357  -10.4645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.6452   -9.3882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.1502   -9.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6850  -10.8826    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.6452  -10.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4357   -9.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1267  -10.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1634  -11.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8647   -8.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6784  -11.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4226  -12.1716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2391   -9.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9205  -10.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6914  -10.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1385  -10.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9068  -12.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9922   -9.4644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1315  -11.7479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2878  -11.0836    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5383  -11.4815    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.0446  -10.1159    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
  2 23  1  0  0  0  0
  3 24  2  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 15  1  1  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  5 25  1  6  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  6 26  1  1  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  7 27  1  6  0  0  0
  8 13  1  0  0  0  0
  8 18  1  0  0  0  0
  9 12  1  0  0  0  0
 10 16  1  0  0  0  0
 10 19  1  0  0  0  0
 10 20  1  1  0  0  0
 11 13  1  0  0  0  0
 14 17  1  0  0  0  0
 16 17  1  0  0  0  0
 16 22  2  0  0  0  0
 18 23  1  0  0  0  0
 19 21  1  0  0  0  0
 21 24  1  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334727

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O3/c1-19-8-5-15(23)13-14(19)3-4-16-17(19)6-9-20(2)18(16)7-10-21(20,24)11-12-22/h13,16-18,22,24H,3-12H2,1-2H3/t16-,17+,18+,19+,20+,21+/m1/s1

> <INCHI_KEY>
ABBVGECYEGYVPY-CEGNMAFCSA-N

> <FORMULA>
C21H32O3

> <MOLECULAR_WEIGHT>
332.477

> <EXACT_MASS>
332.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
39.12857279601086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14S,15S)-14-hydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.6590497383333336

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.992330355654328

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.275116104037867

> <JCHEM_PKA_STRONGEST_BASIC>
-2.413699285730961

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
95.47709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
20a-dihydroxyprogesterone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      40.348 -16.233   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      44.166 -16.764   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      30.642 -22.694   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      38.947 -17.994   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      38.947 -19.534   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      37.614 -20.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      36.280 -19.534   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      40.404 -17.525   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      37.614 -17.224   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.879 -20.314   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      40.404 -20.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.280 -17.994   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.303 -18.764   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.638 -21.908   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      38.947 -16.732   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.866 -21.918   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      36.256 -22.720   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      41.513 -17.038   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.452 -19.446   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.891 -18.983   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.992 -20.259   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      33.426 -22.765   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      42.919 -17.667   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      31.979 -21.929   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0      39.737 -20.689   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      38.338 -21.432   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      37.417 -18.883   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4    5    8    9   15                                             
CONECT    5    4    6   11   25                                             
CONECT    6    5    7   14   26                                             
CONECT    7    6   10   12   27                                             
CONECT    8    1    4   13   18                                             
CONECT    9    4   12                                                       
CONECT   10    7   16   19   20                                             
CONECT   11    5   13                                                       
CONECT   12    7    9                                                       
CONECT   13    8   11                                                       
CONECT   14    6   17                                                       
CONECT   15    4                                                            
CONECT   16   10   17   22                                                  
CONECT   17   14   16                                                       
CONECT   18    8   23                                                       
CONECT   19   10   21                                                       
CONECT   20   10                                                            
CONECT   21   19   24                                                       
CONECT   22   16   24                                                       
CONECT   23    2   18                                                       
CONECT   24    3   21   22                                                  
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
3a,7a-Dihydroxy-5b-cholestanic acid	Generator
17,20a-Dihydroxy-4-pregnen-3-one	HMDB
17,20a-Dihydroxy-pregn-4-en-3-one	HMDB
17a,20a-Dihydroxy-4-pregnen-3-one	HMDB
17a,20a-Dihydroxypregn-4-ene-3-one	HMDB
17a,20a-Dihydroxyprogesterone	HMDB
17a-Hydroxy-20a-dihydroprogesterone	HMDB
20a-Dihydroxyprogesterone	HMDB
3alpha,7alpha-Dihydroxy-5beta-cholestanate	HMDB
Pregn-4-ene-17a,20a-diol-3-one	HMDB
(20S)-Isomer OF 17,20-dihydroxy-4-pregnen-3-one	MeSH
17 alpha,20 alpha-Dihydroxyprogesterone	MeSH
17,20 beta-Dihydroxy-4-pregnen-3-one	MeSH
17,20-Dihydroxy-4-pregnen-3-one	MeSH
17,20beta-P	MeSH
17,20beta-Dihydroxy-4-pregnen-3-one	MeSH
17a,20a-DHP	MeSH
17alpha,20beta-DP	MeSH
4-Pregnene-17 alpha,20 alpha-diol-3-one	MeSH
Maturation-inducing steroid	MeSH

Chemical Formula

C₂₁H₃₂O₃

Average Mass

332.4770 Da

Monoisotopic Mass

332.23514 Da

IUPAC Name

(1S,2R,10R,11S,14S,15S)-14-hydroxy-14-(2-hydroxyethyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

20a-dihydroxyprogesterone

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C21H32O3/c1-19-8-5-15(23)13-14(19)3-4-16-17(19)6-9-20(2)18(16)7-10-21(20,24)11-12-22/h13,16-18,22,24H,3-12H2,1-2H3/t16-,17+,18+,19+,20+,21+/m1/s1

InChI Key

ABBVGECYEGYVPY-CEGNMAFCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

Progestogin-skeleton
21-hydroxysteroid
Pregnane-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Delta-4-steroid
Cyclohexenone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Primary alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Alcohol
Organooxygen compound
Organic oxide
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	2.79	ALOGPS
logP	2.66	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.48 m³·mol⁻¹	ChemAxon
Polarizability	39.13 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

HMDB0003851

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023238

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

107835

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3a,7a-Dihydroxy-5b-cholestanate (NP0334727)

MOL for NP0334727 (3a,7a-Dihydroxy-5b-cholestanate)

3D MOL for NP0334727 (3a,7a-Dihydroxy-5b-cholestanate)

3D SDF for NP0334727 (3a,7a-Dihydroxy-5b-cholestanate)

3D-SDF for NP0334727 (3a,7a-Dihydroxy-5b-cholestanate)

PDB for NP0334727 (3a,7a-Dihydroxy-5b-cholestanate)

3D PDB for NP0334727 (3a,7a-Dihydroxy-5b-cholestanate)

SMILES for NP0334727 (3a,7a-Dihydroxy-5b-cholestanate)

INCHI for NP0334727 (3a,7a-Dihydroxy-5b-cholestanate)

Structure for NP0334727 (3a,7a-Dihydroxy-5b-cholestanate)

3D Structure for NP0334727 (3a,7a-Dihydroxy-5b-cholestanate)