NP-MRD: Showing NP-Card for 5alpha-Androst-16-en-3-one (NP0047962)

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Record Information

Version

2.0

Created at

2022-03-17 20:48:47 UTC

Updated at

2022-03-17 20:48:47 UTC

NP-MRD ID

NP0047962

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5alpha-Androst-16-en-3-one

Description

5Alpha-Androst-16-en-3-one, also known as 3-keto-5alpha,16-androstene or androstenone, 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. 5Alpha-Androst-16-en-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5alpha-androst-16-en-3-one has been detected, but not quantified in, parsnips and wild celeries. This could make 5alpha-androst-16-en-3-one a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307472D          

 20 23  0  0  0  0            999 V2000
    2.1794    0.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3365    0.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8734    1.8884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1906    2.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3653    2.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4468    2.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9608    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4756    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6441    1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2877    0.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1486    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411    1.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7271    1.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5392    1.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1953    1.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8195    1.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6168    1.5048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0532    1.9404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  9  3  2  0  0  0  0
 10  8  1  0  0  0  0
 11  7  1  0  0  0  0
 13  5  1  0  0  0  0
 13 12  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 16  4  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 17 15  1  0  0  0  0
 18  1  1  0  0  0  0
 18  9  1  0  0  0  0
 18 10  1  0  0  0  0
 18 16  1  0  0  0  0
 19  2  1  0  0  0  0
 19 11  1  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
 20 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047962

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3C(CCC4CC(=O)CCC34C)C1CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13,15-17H,4-8,10-12H2,1-2H3

> <INCHI_KEY>
HFVMLYAGWXSTQI-UHFFFAOYSA-N

> <FORMULA>
C19H28O

> <MOLECULAR_WEIGHT>
272.425

> <EXACT_MASS>
272.214015518

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
32.86380914314622

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-one

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
4.280147043

> <ALOGPS_LOGS>
-6.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.352808751886174

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
83.20419999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.068   0.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.628   1.361   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.364   3.525   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.089   4.389   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.682   5.435   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.834   5.164   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.660   1.903   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.888   1.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.936   2.046   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.404   0.818   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.144   1.632   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.191   4.528   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.675   4.257   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.183   3.351   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.357   3.715   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.873   3.444   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.365   2.538   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.396   1.996   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.151   2.809   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.699   3.622   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2   19                                                            
CONECT    3    4    9                                                       
CONECT    4    3   16                                                       
CONECT    5    6   13                                                       
CONECT    6    5   15                                                       
CONECT    7   11   14                                                       
CONECT    8   10   17                                                       
CONECT    9    3   18                                                       
CONECT   10    8   18                                                       
CONECT   11    7   19                                                       
CONECT   12   13   14                                                       
CONECT   13    5   12   19                                                  
CONECT   14    7   12   20                                                  
CONECT   15    6   16   17                                                  
CONECT   16    4   15   18                                                  
CONECT   17    8   15   19                                                  
CONECT   18    1    9   10   16                                             
CONECT   19    2   11   13   17                                             
CONECT   20   14                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
5a-Androst-16-en-3-one	Generator
5Α-androst-16-en-3-one	Generator
(5alpha)-Androst-16-en-3-one	HMDB
16-(5alpha)Androsten-3-one	HMDB
3-Keto-5alpha,16-androstene	HMDB
Androst-16-en-3-one	HMDB
Androstenone	HMDB
5 alpha-Androst-16-en-3-one	MeSH
Androst-16-en-3-one, (5beta)-isomer	MeSH
AEON steroid	MeSH
5alpha-Androst-16-en-3-one	MeSH

Chemical Formula

C₁₉H₂₈O

Average Mass

272.4250 Da

Monoisotopic Mass

272.21402 Da

IUPAC Name

2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-one

Traditional Name

2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-13-en-5-one

CAS Registry Number

18339-16-7

SMILES

CC12CCC3C(CCC4CC(=O)CCC34C)C1CC=C2

InChI Identifier

InChI=1S/C19H28O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13,15-17H,4-8,10-12H2,1-2H3

InChI Key

HFVMLYAGWXSTQI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pastinaca sativa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Oxosteroid
3-oxosteroid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.62	ALOGPS
logP	4.28	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.2 m³·mol⁻¹	ChemAxon
Polarizability	32.86 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

HMDB0034406

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012796

KNApSAcK ID

Not Available

Chemspider ID

78208

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

86705

PDB ID

Not Available

ChEBI ID

37894

Good Scents ID

Not Available

References

General References

Showing NP-Card for 5alpha-Androst-16-en-3-one (NP0047962)

MOL for NP0047962 (5alpha-Androst-16-en-3-one)

3D MOL for NP0047962 (5alpha-Androst-16-en-3-one)

3D SDF for NP0047962 (5alpha-Androst-16-en-3-one)

3D-SDF for NP0047962 (5alpha-Androst-16-en-3-one)

PDB for NP0047962 (5alpha-Androst-16-en-3-one)

3D PDB for NP0047962 (5alpha-Androst-16-en-3-one)

SMILES for NP0047962 (5alpha-Androst-16-en-3-one)

INCHI for NP0047962 (5alpha-Androst-16-en-3-one)

Structure for NP0047962 (5alpha-Androst-16-en-3-one)

3D Structure for NP0047962 (5alpha-Androst-16-en-3-one)