NP-MRD: Showing NP-Card for 7-Dehydropregnenolone (NP0334818)

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Record Information

Version

2.0

Created at

2024-09-10 20:05:38 UTC

Updated at

2024-09-10 20:05:38 UTC

NP-MRD ID

NP0334818

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-Dehydropregnenolone

Description

7-Dehydropregnenolone, also known as 7-DHP, belongs to the class of organic compounds known as 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton. 7-Dehydropregnenolone is the the single product of metabolism of 7-dehydrocholesterol by CYP11A1 (PMID 14657394 ). 7-Dehydropregnenolone was first documented in 2003 (PMID: 14657394). 7-Dehydropregnenolone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241204052D          

 23 26  0  0  1  0            999 V2000
   15.6604   -2.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8535   -2.7272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3015   -2.1144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5986   -3.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0830   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5986   -4.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8140   -4.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8140   -3.7667    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0994   -3.3543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3848   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3848   -4.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0994   -5.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0994   -5.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3848   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6703   -5.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6703   -5.0042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9564   -4.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2418   -5.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2418   -5.8292    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9564   -6.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5272   -6.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6703   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9584   -2.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
  8 23  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 16 22  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0334818

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O2/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/h4-5,15,17-19,23H,6-12H2,1-3H3/t15-,17?,18?,19?,20-,21+/m0/s1

> <INCHI_KEY>
QTVNPWWLYMFLEI-IOHSXPNESA-N

> <FORMULA>
C21H30O2

> <MOLECULAR_WEIGHT>
314.4617

> <EXACT_MASS>
314.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
36.81157695958644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2R,5S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-14-yl]ethan-1-one

> <ALOGPS_LOGP>
4.47

> <JCHEM_LOGP>
3.175778971333335

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.39919072944214

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.270805421445605

> <JCHEM_PKA_STRONGEST_BASIC>
-1.368149263445197

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
94.6067

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(2R,5S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-14-yl]ethanone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      29.233  -4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.727  -5.091   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      26.696  -3.947   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      27.251  -6.555   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.155  -7.801   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.251  -9.047   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.786  -8.571   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.786  -7.031   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.452  -6.261   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.118  -7.031   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.118  -8.571   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.452  -9.341   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.452 -10.881   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.118 -11.651   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.785 -10.881   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.785  -9.341   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.452  -8.571   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.118  -9.341   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      19.118 -10.881   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.452 -11.651   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      17.784 -11.651   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      21.785  -7.801   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.056  -5.516   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    4    7    9   23                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12    7   11   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   11   15   17   22                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   15   19                                                       
CONECT   21   19                                                            
CONECT   22   16                                                            
CONECT   23    8                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
7-DHP	HMDB
7-Dehydropregnenolone	MeSH

Chemical Formula

C₂₁H₃₀O₂

Average Mass

314.4617 Da

Monoisotopic Mass

314.22458 Da

IUPAC Name

1-[(2R,5S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-14-yl]ethan-1-one

Traditional Name

1-[(2R,5S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-7,9-dien-14-yl]ethanone

CAS Registry Number

Not Available

SMILES

CC(=O)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C

InChI Identifier

InChI=1S/C21H30O2/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/h4-5,15,17-19,23H,6-12H2,1-3H3/t15-,17?,18?,19?,20-,21+/m0/s1

InChI Key

QTVNPWWLYMFLEI-IOHSXPNESA-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 20-oxosteroids. These are steroid derivatives carrying a C=O group at the 20-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

20-oxosteroids

Alternative Parents

Substituents

20-oxosteroid
Androgen-skeleton
Androstane-skeleton
3-hydroxy-delta-5-steroid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Hydroxysteroid
Delta-5-steroid
Delta-7-steroid
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
Hydrocarbon derivative
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	4.47	ALOGPS
logP	3.18	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	18.27	ChemAxon
pKa (Strongest Basic)	-1.4	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	94.61 m³·mol⁻¹	ChemAxon
Polarizability	36.81 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

External Links

HMDB ID

HMDB0013121

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029294

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

53481610

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Guryev O, Carvalho RA, Usanov S, Gilep A, Estabrook RW: A pathway for the metabolism of vitamin D3: unique hydroxylated metabolites formed during catalysis with cytochrome P450scc (CYP11A1). Proc Natl Acad Sci U S A. 2003 Dec 9;100(25):14754-9. doi: 10.1073/pnas.2336107100. Epub 2003 Dec 1. [PubMed:14657394 ]

Showing NP-Card for 7-Dehydropregnenolone (NP0334818)

MOL for NP0334818 (7-Dehydropregnenolone)

3D MOL for NP0334818 (7-Dehydropregnenolone)

3D SDF for NP0334818 (7-Dehydropregnenolone)

3D-SDF for NP0334818 (7-Dehydropregnenolone)

PDB for NP0334818 (7-Dehydropregnenolone)

3D PDB for NP0334818 (7-Dehydropregnenolone)

SMILES for NP0334818 (7-Dehydropregnenolone)

INCHI for NP0334818 (7-Dehydropregnenolone)

Structure for NP0334818 (7-Dehydropregnenolone)

3D Structure for NP0334818 (7-Dehydropregnenolone)