NP-MRD: Showing NP-Card for Dehydroandrosterone (NP0334746)

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Record Information

Version

2.0

Created at

2024-09-10 19:47:17 UTC

Updated at

2024-09-10 19:47:17 UTC

NP-MRD ID

NP0334746

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dehydroandrosterone

Description

Dehydroandrosterone, also known as isoandrostenolone or DHEA, 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. Thus, dehydroandrosterone is considered to be a steroid lipid molecule. It was first documented in 1985 (PMID: 3157236). Dehydroandrosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 9001956) (PMID: 10774538).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231220312D          

 24 27  0  0  1  0            999 V2000
   15.7667   -5.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7667   -6.0307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4812   -6.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1956   -6.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1956   -5.2056    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.4812   -4.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9101   -6.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6246   -6.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6246   -5.2056    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.9101   -4.7931    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.3390   -4.7931    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.3390   -3.9681    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   18.6246   -3.5556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9101   -3.9681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1238   -5.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6087   -4.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1238   -3.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0522   -6.4432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4253   -3.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3787   -2.9286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9101   -5.6182    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.1956   -4.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6246   -4.3806    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.4253   -5.6136    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  1  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  2  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
  2 18  1  6  0  0  0
 12 19  1  1  0  0  0
 17 20  2  0  0  0  0
 10 21  1  6  0  0  0
  5 22  1  1  0  0  0
  9 23  1  1  0  0  0
 11 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0334746

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14+,15+,16+,18+,19+/m1/s1

> <INCHI_KEY>
FMGSKLZLMKYGDP-HKQXQEGQSA-N

> <FORMULA>
C19H28O2

> <MOLECULAR_WEIGHT>
288.4244

> <EXACT_MASS>
288.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
33.95878993379053

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,5R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
3.361705055333334

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.957705855663583

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.204289505502594

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972434077338853

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
84.65889999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dehydroandrosterone

> <JCHEM_VEBER_RULE>
1

$$$$

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  C   UNK     0      29.431  -9.717   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.431 -11.257   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.765 -12.027   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      32.098 -11.257   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.098  -9.717   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.765  -8.947   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.432 -12.027   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.766 -11.257   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.766  -9.717   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.432  -8.947   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.099  -8.947   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.099  -7.407   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.766  -6.637   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      33.432  -7.407   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.564  -9.423   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.470  -8.177   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.564  -6.931   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      28.097 -12.027   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      36.261  -5.876   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      38.040  -5.467   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0      33.432 -10.487   0.000  0.00  0.00           H+0
HETATM   22  C   UNK     0      32.098  -8.177   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      34.766  -8.177   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      36.261 -10.479   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   22                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   23                                             
CONECT   10    9    5   14   21                                             
CONECT   11    9   12   15   24                                             
CONECT   12   11   13   17   19                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   20                                                  
CONECT   18    2                                                            
CONECT   19   12                                                            
CONECT   20   17                                                            
CONECT   21   10                                                            
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24   11                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
3a-Hydroxy-5-androsten-17-one	HMDB
3a-Hydroxy-androst-5-en-17-one	HMDB
Androst-5-en-3a-ol-17-one	HMDB
D5-Androstene-3a-ol-17-one	HMDB
Isoandrostenolone	HMDB
Androstenolone	HMDB
Dehydroisoandrosterone	HMDB
5 Androsten 3 beta hydroxy 17 one	HMDB
5 Androsten 3 ol 17 one	HMDB
5-Androsten-3-ol-17-one	HMDB
DHEA	HMDB
Dehydroepiandrosterone	HMDB
5-Androsten-3-beta-hydroxy-17-one	HMDB
Prasterone	HMDB
Prasterone, 3 alpha isomer	HMDB
Prasterone, 3 alpha-isomer	HMDB

Chemical Formula

C₁₉H₂₈O₂

Average Mass

288.4244 Da

Monoisotopic Mass

288.20893 Da

IUPAC Name

(1S,2R,5R,10R,11S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one

Traditional Name

dehydroandrosterone

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14+,15+,16+,18+,19+/m1/s1

InChI Key

FMGSKLZLMKYGDP-HKQXQEGQSA-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 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

Androgen-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
3-alpha-hydroxysteroid
Oxosteroid
17-oxosteroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Secondary alcohol
Ketone
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

C19 steroids (androgens) and derivatives (LMST02020103 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.53	ALOGPS
logP	3.36	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.2	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	0	ChemAxon
Refractivity	84.66 m³·mol⁻¹	ChemAxon
Polarizability	33.96 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

HMDB0005962

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023792

KNApSAcK ID

Not Available

Chemspider ID

118560

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dehydroepiandrosterone

METLIN ID

Not Available

PubChem Compound

134506

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Eil'bart VL: [Seasonal and circadian rhythms of the excretion of androgens and their fractions in peptic ulcer patients in the remission phase in the markedly continental climate of Transbaikalia]. Ter Arkh. 1985;57(1):80-4. [PubMed:3157236 ]
Dehennin L, Lafarge P, Dailly P, Bailloux D, Lafarge JP: Combined profile of androgen glucuro- and sulfoconjugates in post-competition urine of sportsmen: a simple screening procedure using gas chromatography-mass spectrometry. J Chromatogr B Biomed Appl. 1996 Dec 6;687(1):85-91. doi: 10.1016/s0378-4347(96)00131-4. [PubMed:9001956 ]
Uralets VP, Gillette PA: Over-the-counter delta5 anabolic steroids 5-androsen-3,17-dione; 5-androsten-3beta, 17beta-diol; dehydroepiandrosterone; and 19-nor-5-androsten-3,17-dione: excretion studies in men. J Anal Toxicol. 2000 Apr;24(3):188-93. doi: 10.1093/jat/24.3.188. [PubMed:10774538 ]

Showing NP-Card for Dehydroandrosterone (NP0334746)

MOL for NP0334746 (Dehydroandrosterone)

3D MOL for NP0334746 (Dehydroandrosterone)

3D SDF for NP0334746 (Dehydroandrosterone)

3D-SDF for NP0334746 (Dehydroandrosterone)

PDB for NP0334746 (Dehydroandrosterone)

3D PDB for NP0334746 (Dehydroandrosterone)

SMILES for NP0334746 (Dehydroandrosterone)

INCHI for NP0334746 (Dehydroandrosterone)

Structure for NP0334746 (Dehydroandrosterone)

3D Structure for NP0334746 (Dehydroandrosterone)