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Record Information
Version2.0
Created at2022-09-07 23:09:27 UTC
Updated at2022-09-07 23:09:27 UTC
NP-MRD IDNP0257891
Secondary Accession NumbersNone
Natural Product Identification
Common Name5β-dihydrotestosterone
Description5B-Dihydrotestosterone, also known as 5-beta-DHT or 5-Β-DHT, 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, 5b-dihydrotestosterone is considered to be a steroid lipid molecule. 5B-Dihydrotestosterone is a drug. 5B-Dihydrotestosterone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5B-dihydrotestosterone can be converted into testosterone; which is catalyzed by the enzyme 3-oxo-5-beta-steroid 4-dehydrogenase. 5β-dihydrotestosterone is found in Mus musculus. 5β-dihydrotestosterone was first documented in 1977 (PMID: 591837). In humans, 5b-dihydrotestosterone is involved in androgen and estrogen metabolism (PMID: 10357254) (PMID: 11430920) (PMID: 15758151) (PMID: 17804019) (PMID: 18276759) (PMID: 19215525).
Structure
Thumb
Synonyms
Chemical FormulaC19H30O2
Average Mass290.4403 Da
Monoisotopic Mass290.22458 Da
IUPAC Name(1S,2S,7R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
Traditional Name5β-dihydrotestosterone
CAS Registry NumberNot Available
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=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/h12,14-17,21H,3-11H2,1-2H3/t12-,14+,15+,16+,17+,18+,19+/m1/s1
InChI KeyNVKAWKQGWWIWPM-MISPCMORSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Mus musculusLOTUS Database
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
  • 3-oxosteroid
  • 3-oxo-5-beta-steroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • 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
logP3.37ALOGPS
logP3.41ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.6 m³·mol⁻¹ChemAxon
Polarizability34.46 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006770
DrugBank IDDB07447
Phenol Explorer Compound IDNot Available
FoodDB IDFDB024072
KNApSAcK IDNot Available
Chemspider ID10827
KEGG Compound IDC05293
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11302
PDB IDNot Available
ChEBI ID428206
Good Scents IDNot Available
References
General References
  1. Perusquia M, Villalon CM: Possible role of Ca2+ channels in the vasodilating effect of 5beta-dihydrotestosterone in rat aorta. Eur J Pharmacol. 1999 Apr 29;371(2-3):169-78. doi: 10.1016/s0014-2999(99)00161-2. [PubMed:10357254 ]
  2. Bordallo C, Rubin JM, Varona AB, Cantabrana B, Hidalgo A, Sanchez M: Increases in ornithine decarboxylase activity in the positive inotropism induced by androgens in isolated left atrium of the rat. Eur J Pharmacol. 2001 Jun 22;422(1-3):101-7. doi: 10.1016/s0014-2999(01)01039-1. [PubMed:11430920 ]
  3. Perusquia M, Navarrete E, Jasso-Kamel J, Montano LM: Androgens induce relaxation of contractile activity in pregnant human myometrium at term: a nongenomic action on L-type calcium channels. Biol Reprod. 2005 Aug;73(2):214-21. doi: 10.1095/biolreprod.104.036954. Epub 2005 Mar 9. [PubMed:15758151 ]
  4. Perusquia M, Navarrete E, Gonzalez L, Villalon CM: The modulatory role of androgens and progestins in the induction of vasorelaxation in human umbilical artery. Life Sci. 2007 Sep 1;81(12):993-1002. doi: 10.1016/j.lfs.2007.07.024. Epub 2007 Aug 7. [PubMed:17804019 ]
  5. Montano LM, Calixto E, Figueroa A, Flores-Soto E, Carbajal V, Perusquia M: Relaxation of androgens on rat thoracic aorta: testosterone concentration dependent agonist/antagonist L-type Ca2+ channel activity, and 5beta-dihydrotestosterone restricted to L-type Ca2+ channel blockade. Endocrinology. 2008 May;149(5):2517-26. doi: 10.1210/en.2007-1288. Epub 2008 Feb 14. [PubMed:18276759 ]
  6. Schumacher M, Hutchison RE, Hutchison JB: Inhibition of hypothalamic aromatase activity by 5 Beta-dihydrotestosterone. J Neuroendocrinol. 1991 Apr 1;3(2):221-6. doi: 10.1111/j.1365-2826.1991.tb00266.x. [PubMed:19215525 ]
  7. Massa R, Cresti L, Martini L: Metabolism of testosterone in the anterior pituitary gland and the central nervous system of the European starling (Sturnus vulgaris). J Endocrinol. 1977 Dec;75(3):347-54. doi: 10.1677/joe.0.0750347. [PubMed:591837 ]
  8. LOTUS database [Link]