Np mrd loader

Showing NP-Card for Androstenol (NP0334598)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-09-10 19:04:54 UTC
Updated at2024-09-10 19:04:54 UTC
NP-MRD IDNP0334598
Secondary Accession NumbersNone
Natural Product Identification
Common NameAndrostenol
DescriptionAndrostenol 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. Androstenol was first documented in 2021 (PMID: 34675855). Based on a literature review a small amount of articles have been published on Androstenol (PMID: 38313522) (PMID: 37942135) (PMID: 35458576) (PMID: 34864067).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0334598 (Androstenol)

ATE
  Mrv2104 05252321372D          

 25 28  0  0  0  0            999 V2000
    3.2286    0.4743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4165    0.3291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1362   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241   -0.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8847    0.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725    0.8146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5407    1.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7922    0.0387    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5119   -0.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0199   -0.1065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3002   -0.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5517    0.5242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2714    1.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638    0.3790    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0151    0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6441   -0.3969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1123   -1.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040   -1.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4687   -0.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6980    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7929   -0.1173    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2709    1.3638    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -0.5529    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281    0.9706    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2239    0.9459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2 21  1  1  0  0  0
  3  4  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
  6  8  1  0  0  0  0
  6 22  1  6  0  0  0
  7 13  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 23  1  6  0  0  0
 11 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 24  1  1  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 25  1  6  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  1  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
Download

3D MOL for NP0334598 (Androstenol)

Download
3D SDF for NP0334598 (Androstenol)
ATE
  Mrv2104 05252321372D          

 25 28  0  0  0  0            999 V2000
    3.2286    0.4743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4165    0.3291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1362   -0.4468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241   -0.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8847    0.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725    0.8146    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5407    1.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7922    0.0387    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5119   -0.7372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0199   -0.1065    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3002   -0.8824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5517    0.5242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2714    1.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3638    0.3790    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0151    0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6441   -0.3969    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1123   -1.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040   -1.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4687   -0.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6980    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7929   -0.1173    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2709    1.3638    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3565   -0.5529    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281    0.9706    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2239    0.9459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2 21  1  1  0  0  0
  3  4  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
  6  8  1  0  0  0  0
  6 22  1  6  0  0  0
  7 13  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 23  1  6  0  0  0
 11 17  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 24  1  1  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 25  1  6  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  1  0  0  0
 16 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0334598

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14+,15-,16-,17-,18-,19-/s2

> <INCHI_KEY>
KRVXMNNRSSQZJP-YVDVFZGQNA-N

> <FORMULA>
C19H30O

> <MOLECULAR_WEIGHT>
274.448

> <EXACT_MASS>
274.229665586

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
33.66968019841896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,3bR,5aS,7R,9aS,9bS,11aR)-9a,11a-dimethyl-3H,3aH,3bH,4H,5H,5aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol

> <JCHEM_LOGP>
4.072646241333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.29639632111979

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3569562491422038

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
84.23230000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
androstenol

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0334598 (Androstenol)
Download
PDB for NP0334598 (Androstenol)
HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ATE                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  O   UNK     0       6.027   0.885   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.511   0.614   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.988  -0.834   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.472  -1.105   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.518   1.792   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.002   1.521   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.009   2.698   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.479   0.072   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.956  -1.376   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.037  -0.199   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.560  -1.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.030   0.979   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.507   2.427   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.546   0.707   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.762   1.653   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.069  -0.741   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.076  -1.918   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.741  -2.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.608  -0.691   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.036   0.788   0.000  0.00  0.00           C+0
HETATM   21  H   UNK     0       5.213  -0.219   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.372   2.546   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.665  -1.032   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.732   1.812   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.285   1.766   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    5   21                                             
CONECT    3    2    4                                                       
CONECT    4    3    8                                                       
CONECT    5    2    6                                                       
CONECT    6    5    7    8   22                                             
CONECT    7    6   13                                                       
CONECT    8    4    6    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11   12   23                                             
CONECT   11   10   17                                                       
CONECT   12   10   13   14   24                                             
CONECT   13    7   12                                                       
CONECT   14   12   15   16   25                                             
CONECT   15   14   20                                                       
CONECT   16   14   17   18   19                                             
CONECT   17   11   16                                                       
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   15   19                                                       
CONECT   21    2                                                            
CONECT   22    6                                                            
CONECT   23   10                                                            
CONECT   24   12                                                            
CONECT   25   14                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

Download
3D PDB for NP0334598 (Androstenol)
Download
SMILES for NP0334598 (Androstenol)
[H][C@@]12CC=C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@]([H])(O)CC[C@]12C
Download
INCHI for NP0334598 (Androstenol)
InChI=1/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14+,15-,16-,17-,18-,19-/s2
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC19H30O
Average Mass274.4480 Da
Monoisotopic Mass274.22967 Da
IUPAC Name(3aS,3bR,5aS,7R,9aS,9bS,11aR)-9a,11a-dimethyl-3H,3aH,3bH,4H,5H,5aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol
Traditional Nameandrostenol
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC=C[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@]([H])(O)CC[C@]12C
InChI Identifier
InChI=1/C19H30O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,13-17,20H,4-8,10-12H2,1-2H3/t13-,14+,15-,16-,17-,18-,19-/s2
InChI KeyKRVXMNNRSSQZJP-YVDVFZGQNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassAndrostane steroids  
Direct ParentAndrogens and derivatives  
Alternative Parents
Substituents
  • Androgen-skeleton
    • 

  • 3-alpha-hydroxysteroid
    • 

  • Hydroxysteroid
    • 

  • 3-hydroxysteroid
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.07ChemAxon
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.23 m³·mol⁻¹ChemAxon
Polarizability33.67 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAndrostenol  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Sankarganesh D, Balasundaram A, Doss C GP, Azhwar R, Achiraman S, Archunan G: Mechanistic Insights into the Binding of Boar Salivary Pheromones and Putative Molecule with Receptor Proteins: A Comparative Computational Approach. ACS Omega. 2024 Jan 17;9(4):4986-5001. doi: 10.1021/acsomega.3c09211. eCollection  2024 Jan 30. [PubMed:38313522  ] 
  2. Shi Y, Zhu R: Analysis of damage-associated molecular patterns in amyotrophic lateral sclerosis based on ScRNA-seq and bulk RNA-seq data. Front Neurosci. 2023 Oct 24;17:1259742. doi: 10.3389/fnins.2023.1259742.  eCollection 2023. [PubMed:37942135  ] 
  3. Tabassum S, Ahmad S, Rehman Khan KU, Tabassum F, Khursheed A, Zaman QU, Bukhari NA, Alfagham A, Hatamleh AA, Chen Y: Phytochemical Profiling, Antioxidant, Anti-Inflammatory, Thrombolytic, Hemolytic Activity In Vitro and In Silico Potential of Portulacaria afra. Molecules. 2022 Apr 7;27(8):2377. doi: 10.3390/molecules27082377. [PubMed:35458576  ] 
  4. Beaton AA, Jones L, Benton D, Richards G: Judgements of attractiveness of the opposite sex and nostril differences in self-rated mood: The effects of androstenol. Biol Psychol. 2022 Jan;167:108237. doi: 10.1016/j.biopsycho.2021.108237. Epub  2021 Dec 2. [PubMed:34864067  ] 
  5. Damon F, Mezrai N, Magnier L, Leleu A, Durand K, Schaal B: Olfaction in the Multisensory Processing of Faces: A Narrative Review of the Influence of Human Body Odors. Front Psychol. 2021 Oct 5;12:750944. doi: 10.3389/fpsyg.2021.750944. eCollection  2021. [PubMed:34675855  ]