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Human Metabolome Database Version 2.5

 

Showing metabocard for 5b-Dihydrotestosterone (HMDB06770)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2008-08-06 17:25:44
Update Date 2009-05-05 21:01:10
Accession Number HMDB06770
Secondary Accession Numbers Not Available
Common Name 5b-Dihydrotestosterone
Description 5beta-Dihydrotestosterone is an intermediate in Androgen and estrogen metabolism. 5beta-Dihydrotestosterone is generated from Testosterone via the enzyme 3-oxo-5beta-steroid 4-dehydrogenase (EC 1.3.99.6).
Synonyms
  1. 17beta-hydroxy-5beta-androstan-3-one
  2. 5beta-Dihydrotestosterone
Chemical IUPAC Name (5R,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
Chemical Formula C19H30O2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Ketosteroids
Family
  • Mammalian Metabolite
Species
  • ketone
  • secondary alcohol
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 290.440
Monoisotopic Molecular Weight 290.224579
Isomeric SMILES C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2O
Canonical SMILES CC12CCC3C(CCC4CC(=O)CCC34C)C1CCC2O
KEGG Compound ID C05293 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06770 Link Image
Metagene Link HMDB06770 Link Image
METLIN ID Not Available
PubChem Compound 11302 Link Image
PubChem Substance Not Available
ChEBI ID Not Available
CAS Registry Number 571-22-2
InChI Identifier InChI=1/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
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 9.98e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 3.37 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Androgen and Estrogen Metabolism SMP00068 Link Image map00150 Link Image
General References Not Available
Metabolic Enzymes
  1. 3-oxo-5-beta-steroid 4-dehydrogenase
Enzyme 1 [top]
Enzyme 1 ID 5822
Enzyme 1 Name 3-oxo-5-beta-steroid 4-dehydrogenase
Enzyme 1 Synonyms
  1. Delta(4-3- ketosteroid 5-beta-reductase
  2. Aldo-keto reductase family 1 member D1
Enzyme 1 Gene Name AKR1D1
Enzyme 1 Protein Sequence >3-oxo-5-beta-steroid 4-dehydrogenase 
MDLSAASHRIPLSDGNSIPIIGLGTYSEPKSTPKGACATSVKVAIDTGYRHIDGAYIYQN
EHEVGEAIREKIAEGKVRREDIFYCGKLWATNHVPEMVRPTLERTLRVLQLDYVDLYIIE
VPMAFKPGDEIYPRDENGKWLYHKSNLCATWEAMEACKDAGLVKSLGVSNFNRRQLELIL
NKPGLKHKPVSNQVECHPYFTQPKLLKFCQQHDIVITAYSPLGTSRNPIWVNVSSPPLLK
DALLNSLGKRYNKTAAQIVLRFNIQRGVVVIPKSFNLERIKENFQIFDFSLTEEEMKDIE
ALNKNVRFVELLMWRDHPEYPFHDEY
Enzyme 1 Number of Residues 326
Enzyme 1 Molecular Weight 37377
Enzyme 1 Theoretical pI 7.58
Enzyme 1 GO Classification
Function
  • catalytic activity
  • oxidoreductase activity
Process
—
Component
—
Enzyme 1 General Function Not Available
Enzyme 1 Specific Function Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7- alpha,12-alpha-dihydroxy-4-cholesten-3-one and 7-alpha-hydroxy-4- cholesten-3-one can also act as substrates
Enzyme 1 Pathways
Enzyme 1 Reactions
  • 4,5beta-dihydrocortisone + NADP+ = cortisone + NADPH + H+
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 431857 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID P51857 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name AK1D1_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >981 bp 
ATGGATCTCAGTGCTGCAAGTCACCGCATACCTCTAAGTGATGGAAACAGCATTCCCATC
ATCGGACTTGGTACCTACTCAGAACCTAAATCGACCCCTAAGGGAGCCTGTGCAACATCG
GTGAAGGTTGCTATTGACACAGGGTACCGACATATTGATGGGGCCTACATCTACCAAAAT
GAACACGAAGTTGGGGAGGCCATCAGGGAGAAGATAGCAGAAGGAAAGGTGCGGAGGGAA
GATATCTTCTACTGTGGAAAGCTATGGGCTACAAATCATGTCCCAGAGATGGTCCGCCCA
ACCCTGGAGAGGACACTCAGGGTCCTCCAGCTAGATTATGTGGATCTTTACATCATTGAA
GTACCCATGGCCTTTAAGCCAGGAGATGAAATATACCCTAGAGATGAGAATGGCAAATGG
TTATATCACAAGTCAAATCTGTGTGCCACTTGGGAGGCGATGGAAGCTTGCAAAGACGCT
GGCTTGGTGAAATCCCTGGGAGTGTCCAATTTTAACCGCAGGCAGCTGGAGCTCATCCTG
AACAAGCCAGGACTCAAACACAAGCCAGTCAGCAACCAGGTTGAGTGCCATCCGTATTTC
ACCCAGCCAAAACTCTTGAAATTTTGCCAACAACATGACATTGTCATTACTGCATATAGC
CCTTTGGGGACCAGTAGGAATCCAATCTGGGTGAATGTTTCTTCTCCACCTTTGTTAAAG
GATGCACTTCTAAACTCATTGGGGAAAAGGTACAATAAGACAGCAGCTCAAATTGTTTTG
CGTTTCAACATCCAGCGAGGGGTGGTTGTCATTCCTAAAAGCTTTAATCTTGAAAGGATC
AAAGAAAATTTTCAGATCTTTGACTTTTCTCTCACTGAAGAAGAAATGAAGGACATTGAA
GCCTTGAATAAAAATGTCCGCTTTGTAGAATTGCTCATGTGGCGCGATCATCCTGAATAC
CCATTTCATGATGAATACTGA
Enzyme 1 GenBank Gene ID Z28339 Link Image
Enzyme 1 GeneCard ID AKR1D1 Link Image
Enzyme 1 GenAtlas ID AKR1D1 Link Image
Enzyme 1 HGNC ID HGNC:388 Link Image
Enzyme 1 Chromosome Location 7
Enzyme 1 Locus 7q32-q33
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Kondo KH, Kai MH, Setoguchi Y, Eggertsen G, Sjoblom P, Setoguchi T, Okuda KI, Bjorkhem I: Cloning and expression of cDNA of human delta 4-3-oxosteroid 5 beta-reductase and substrate specificity of the expressed enzyme. Eur J Biochem. 1994 Jan 15;219(1-2):357-63. [PubMed Link Image]
  2. Charbonneau A, The VL: Genomic organization of a human 5beta-reductase and its pseudogene and substrate selectivity of the expressed enzyme. Biochim Biophys Acta. 2001 Jan 26;1517(2):228-35. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available