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Record Information
Version2.0
Created at2022-05-11 16:49:17 UTC
Updated at2022-05-11 16:49:17 UTC
NP-MRD IDNP0087423
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Androstenediol
Description4-Androstenediol 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, 4-androstenediol is considered to be a steroid lipid molecule. There is also some conversion into estrogen, since testosterone is the metabolic precursor of the estrogens.4-Androstenediol is closer to testosterone structurally than 5-androstenediol, and has androgenic effects, acting as a weak partial agonist of the androgen receptor. Patrick Arnold holds a 1999 patent on "Use of 4-androstenediol to increase testosterone levels in humans". 4-Androstenediol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. However, due to its lower intrinsic activity in comparison, in the presence of full agonists like testosterone or dihydrotestosterone (DHT), 4-androstenediol has antagonistic actions, behaving more like an antiandrogen.4-Androstenediol is very weakly estrogenic. The conversion rate is about 15.76%, Almost triple that of 4-androstenedione, due to utilization of a different enzymatic pathway. 4-Androstenediol is found in Homo sapiens and Mus musculus. 4-Androstenediol was first documented in 2004 (PMID: 15370836). It has approximately 0.5% And 0.6% Of the affinity of estradiol at the ERα and ERβ, respectively.
Structure
Thumb
Synonyms
ValueSource
Androst-4-ene-3beta,17beta-diolKegg
Androst-4-ene-3b,17b-diolGenerator
Androst-4-ene-3β,17β-diolGenerator
(3b,17b)-Androst-4-ene-3,17-diolHMDB
3b,17b-Dihydroxy-4-androsteneHMDB
4-Androstene-3b,17b-diolHMDB
Androst-4-en-3b,17b-diolHMDB
D4-Androstene-3b,17b-diolHMDB
(3beta,17beta)-Androst-4-ene-3,17-diolHMDB
(3Β,17β)-androst-4-ene-3,17-diolHMDB
3beta,17beta-Dihydroxy-4-androsteneHMDB
3Β,17β-dihydroxy-4-androsteneHMDB
4-AndrostenediolHMDB
Chemical FormulaC19H30O2
Average Mass290.4403 Da
Monoisotopic Mass290.22458 Da
IUPAC Name(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol
Traditional Name(1S,2R,5S,10R,11S,14S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C19H30O2/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/h11,13-17,20-21H,3-10H2,1-2H3/t13-,14-,15-,16-,17-,18-,19-/m0/s1
InChI KeyBTTWKVFKBPAFDK-LOVVWNRFSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 17-hydroxysteroid
  • 3-beta-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-4-steroid
  • Delta-4-steroid
  • 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
logP3.1ALOGPS
logP2.95ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)17.5ChemAxon
pKa (Strongest Basic)-0.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity85.33 m³·mol⁻¹ChemAxon
Polarizability34.38 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0005849
DrugBank IDDB01526
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023781
KNApSAcK IDNot Available
Chemspider ID120071
KEGG Compound IDC14210
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Androstenediol
METLIN IDNot Available
PubChem Compound136297
PDB IDNot Available
ChEBI ID34386
Good Scents IDNot Available
References
General References
  1. Parr MK, Geyer H, Reinhart U, Schanzer W: Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements. Food Addit Contam. 2004 Jul;21(7):632-40. doi: 10.1080/02652030410001701602. [PubMed:15370836 ]