Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2008-08-06 13:21:05 UTC
Update Date2021-09-14 15:40:02 UTC
HMDB IDHMDB0006756
Secondary Accession Numbers
  • HMDB06756
Metabolite Identification
Common Name21-Hydroxy-5b-pregnane-3,11,20-trione
Description21-Hydroxy-5beta-pregnane-3,11,20-trione is an intermediate in C21-Steroid hormone metabolism. 21-Hydroxy-5beta-pregnane-3,11,20-trione is the. second to last step in the synthesis of 3alpha,20alpha,21-Trihydroxy-5beta-pregnane-11-one and is converted from 11-Dehydrocorticosterone via the enzyme 3-oxo-5beta-steroid 4-dehydrogenase (EC 1.3.99.6). It is then converted to 3alpha,21-Dihydroxy-5beta-pregnane-11,20-dione via the enzyme 3-alpha-hydroxysteroid dehydrogenase (EC 1.1.1.50).
Structure
Data?1582752404
Synonyms
ValueSource
3alpha-Hydroxy-5beta-pregnane-20-oneHMDB
21-Hydroxy-5beta-pregnane-3,11,20-trioneHMDB
Chemical FormulaC21H30O4
Average Molecular Weight346.4605
Monoisotopic Molecular Weight346.214409448
IUPAC Name(1S,2S,7R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,17-dione
Traditional Name(1S,2S,7R,10S,11S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-5,17-dione
CAS Registry Number10417-86-4
SMILES
[H][C@@]12CCC(C(=O)CO)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C
InChI Identifier
InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12,14-16,19,22H,3-11H2,1-2H3/t12-,14+,15+,16?,19-,20+,21+/m1/s1
InChI KeyZDUVZJUTJOBJHS-HNEBDTNWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
logP10(2.63) g/LALOGPS
logP10(2.45) g/LChemAxon
logS10(-3.8) g/LALOGPS
pKa (Strongest Acidic)13.86ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.25 m³·mol⁻¹ChemAxon
Polarizability38.67 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.28931661259
DarkChem[M-H]-181.35231661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#1C[C@]12CC(=O)[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@]34C)[C@@H]1CCC2C(=O)CO[Si](C)(C)C3233.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#2C[C@]12CC(=O)[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@]34C)[C@@H]1CCC2=C(CO)O[Si](C)(C)C3177.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#3C[C@]12CC(O[Si](C)(C)C)=C3[C@@H](CC[C@@H]4CC(=O)CC[C@]34C)[C@@H]1CCC2C(=O)CO3106.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#4C[C@]12CC(=O)[C@H]3[C@@H](CC[C@@H]4CC(=O)CC[C@]34C)[C@@H]1CCC2C(=CO)O[Si](C)(C)C3206.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#5C[C@]12CCC(=O)C[C@H]1CC[C@@H]1[C@@H]2C(O[Si](C)(C)C)=C[C@]2(C)C(C(=O)CO)CC[C@@H]123067.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#6C[C@]12CC(=O)[C@H]3[C@@H](CC[C@@H]4CC(O[Si](C)(C)C)=CC[C@]34C)[C@@H]1CCC2C(=O)CO3217.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TMS,#7C[C@]12CC(=O)[C@H]3[C@@H](CC[C@@H]4C=C(O[Si](C)(C)C)CC[C@]34C)[C@@H]1CCC2C(=O)CO3219.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#1CC(C)(C)[Si](C)(C)OCC(=O)C1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C3490.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#2CC(C)(C)[Si](C)(C)OC(CO)=C1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C3435.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#3CC(C)(C)[Si](C)(C)OC1=C2[C@@H](CC[C@@H]3CC(=O)CC[C@]23C)[C@@H]2CCC(C(=O)CO)[C@@]2(C)C13344.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#4CC(C)(C)[Si](C)(C)OC(=CO)C1CC[C@H]2[C@@H]3CC[C@@H]4CC(=O)CC[C@]4(C)[C@H]3C(=O)C[C@]12C3430.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#5CC(C)(C)[Si](C)(C)OC1=C[C@]2(C)C(C(=O)CO)CC[C@H]2[C@@H]2CC[C@@H]3CC(=O)CC[C@]3(C)[C@@H]123280.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#6CC(C)(C)[Si](C)(C)OC1=CC[C@]2(C)[C@H]3C(=O)C[C@]4(C)C(C(=O)CO)CC[C@H]4[C@@H]3CC[C@@H]2C13464.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
21-Hydroxy-5b-pregnane-3,11,20-trione,1TBDMS,#7CC(C)(C)[Si](C)(C)OC1=C[C@H]2CC[C@H]3[C@@H]4CCC(C(=O)CO)[C@@]4(C)CC(=O)[C@@H]3[C@@]2(C)CC13454.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fki-1988000000-fba247baf630a72103512017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione GC-MS (1 TMS) - 70eV, Positivesplash10-0udr-2639300000-c9ca38b4ccbbd8f2986e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 10V, Positive-QTOFsplash10-002b-0019000000-24f7d25b96d058ce27ec2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 20V, Positive-QTOFsplash10-016r-0139000000-14964e5f3294355276492017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 40V, Positive-QTOFsplash10-0a4s-3293000000-fdc80d45785ab54b814f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 10V, Negative-QTOFsplash10-0002-0009000000-804a5ed2772af86708b72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 20V, Negative-QTOFsplash10-05p2-1029000000-b83f2a0acc0792e5262b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 40V, Negative-QTOFsplash10-0a4r-5092000000-c68952d24a29d9931c162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 10V, Negative-QTOFsplash10-002b-0009000000-33bcf2e22dc5313c0e4a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 20V, Negative-QTOFsplash10-03ys-0049000000-9e885d9932104c5647742021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 40V, Negative-QTOFsplash10-006t-0193000000-d4a852e1dae01823cdfc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 10V, Positive-QTOFsplash10-002b-0009000000-962664f8be4e6a4a1d652021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 20V, Positive-QTOFsplash10-03fr-0269000000-d077f7e8c79f38b5e3ed2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 21-Hydroxy-5b-pregnane-3,11,20-trione 40V, Positive-QTOFsplash10-03di-4690000000-b76906ca897f4798e3712021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Sepsis
details
Associated Disorders and Diseases
Disease References
Sepsis
  1. Stewart CJ, Embleton ND, Marrs ECL, Smith DP, Fofanova T, Nelson A, Skeath T, Perry JD, Petrosino JF, Berrington JE, Cummings SP: Longitudinal development of the gut microbiome and metabolome in preterm neonates with late onset sepsis and healthy controls. Microbiome. 2017 Jul 12;5(1):75. doi: 10.1186/s40168-017-0295-1. [PubMed:28701177 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024063
KNApSAcK IDNot Available
Chemspider ID23141070
KEGG Compound IDC05480
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779614
PDB IDNot Available
ChEBI ID88767
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid dehydrogenase activity. The biotransformation of the pesticide chlordecone (kepone) to its corresponding alcohol leads to increased biliary excretion of the pesticide and concomitant reduction of its neurotoxicity since bile is the major excretory route.
Gene Name:
AKR1C4
Uniprot ID:
P17516
Molecular weight:
37094.57
Reactions
3a,21-Dihydroxy-5b-pregnane-11,20-dione + NAD → 21-Hydroxy-5b-pregnane-3,11,20-trione + NADH + Hydrogen Iondetails
3a,21-Dihydroxy-5b-pregnane-11,20-dione + NADP → 21-Hydroxy-5b-pregnane-3,11,20-trione + NADPH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
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.
Gene Name:
AKR1D1
Uniprot ID:
P51857
Molecular weight:
32889.38