Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:14:04 UTC
NP-MRD IDNP0000256
Secondary Accession NumbersNone
Natural Product Identification
Common Name16-a-Hydroxypregnenolone
Description16-Alpha-hydroxypregnenolone, also known as (3beta,16alpha)-3,16-dihydroxypregn-5-en-20-one, is classified as a gluco/mineralocorticoid, a progestogin or aprogestogin derivative. Gluco/mineralocorticoids are steroids with a structure based on a hydroxylated prostane moiety. Thus, 16-alpha-hydroxypregnenolone is a steroid lipid molecule. 16-Alpha-hydroxypregnenolone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 16-Alpha-hydroxypregnenolone can be found primarily in blood, urine and in human umbilical cord tissue. Within the cell, 16-alpha-hydroxypregnenolone is primarily located in the membrane, and in the nucleus bound to cytoplasmic glucocorticoid receptors. 16-Alpha-hydroxypregnenolone exists in all vertebrates. 16-A-Hydroxypregnenolone is a normal urinary metabolite with increased total excretion in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency (PMID 6980322 ).
Structure
Thumb
Synonyms
ValueSource
(3beta,16alpha)-3,16-Dihydroxypregn-5-en-20-oneChEBI
16-alpha-HydroxypregnenoloneChEBI
(3b,16a)-3,16-Dihydroxypregn-5-en-20-oneGenerator
(3Β,16α)-3,16-dihydroxypregn-5-en-20-oneGenerator
16-Α-hydroxypregnenoloneGenerator
16 alpha-HydroxypregnenoloneHMDB
16-a-Hydroxy-pregnenoloneHMDB
16-alpha-Hydroxy-pregnenoloneHMDB
16alpha-HydroxypregnenoloneHMDB
3b,16a-Dihydroxypreg-5-en-20-oneHMDB
3b,16a-Dihydroxypregn-5-en-20-oneHMDB
3b,16a-Dihydroxypregnen-5-en-20-oneHMDB
5-Pregnene-3b,16a-diol-20-oneHMDB
Pregn-5-en-3b,16a-diol-20-oneHMDB
3 alpha,16 alpha-Dihydroxypregn-5-en-20-oneHMDB
3 beta,16 alpha-Dihydroxypregn-5-en-20-oneHMDB
3 beta,16 beta-Dihydroxypregn-5-en-20-oneHMDB
16a-HydroxypregnenoloneHMDB
16Α-hydroxypregnenoloneHMDB
16-a-HydroxypregnenoloneGenerator
Chemical FormulaC21H32O3
Average Mass332.4770 Da
Monoisotopic Mass332.23514 Da
IUPAC Name1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one
Traditional Name1-[(1S,2R,5S,10S,11S,13R,14R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone
CAS Registry Number520-88-7
SMILES
[H][C@@]12C[C@@H](O)[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C21H32O3/c1-12(22)19-18(24)11-17-15-5-4-13-10-14(23)6-8-20(13,2)16(15)7-9-21(17,19)3/h4,14-19,23-24H,5-11H2,1-3H3/t14-,15+,16-,17-,18+,19-,20-,21-/m0/s1
InChI KeyZAKJZPQDUPCXSD-YRWKUUEZSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
  • Animalia
  • 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-hydroxy-delta-5-steroid
    • 3-hydroxysteroid
    • 3-beta-hydroxysteroid
    • 16-hydroxysteroid
    • 16-alpha-hydroxysteroid
    • 3-beta-hydroxy-delta-5-steroid
    • Oxosteroid
    • Hydroxysteroid
    • Delta-5-steroid
    • Cyclic alcohol
    • Secondary alcohol
    • Ketone
    • Organooxygen compound
    • Hydrocarbon derivative
    • Organic oxygen compound
    • Carbonyl group
    • Alcohol
    • Organic oxide
    • Aliphatic homopolycyclic compound
    Molecular FrameworkAliphatic homopolycyclic compounds
    External Descriptors
    Physical Properties
    StateSolid
    Experimental Properties
    PropertyValueReference
    Melting PointNot AvailableNot Available
    Boiling PointNot AvailableNot Available
    Water SolubilityNot AvailableNot Available
    LogPNot AvailableNot Available
    Predicted Properties
    PropertyValueSource
    Water Solubility0.057 g/LALOGPS
    logP2.79ALOGPS
    logP2.35ChemAxon
    logS-3.8ALOGPS
    pKa (Strongest Acidic)14.75ChemAxon
    pKa (Strongest Basic)-1.4ChemAxon
    Physiological Charge0ChemAxon
    Hydrogen Acceptor Count3ChemAxon
    Hydrogen Donor Count2ChemAxon
    Polar Surface Area57.53 ŲChemAxon
    Rotatable Bond Count1ChemAxon
    Refractivity95.27 m³·mol⁻¹ChemAxon
    Polarizability38.92 ųChemAxon
    Number of Rings4ChemAxon
    BioavailabilityYesChemAxon
    Rule of FiveYesChemAxon
    Ghose FilterYesChemAxon
    Veber's RuleNoChemAxon
    MDDR-like RuleNoChemAxon
    External Links
    HMDB IDHMDB0000315
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FoodDB IDFDB021942
    KNApSAcK IDNot Available
    Chemspider ID4955002
    KEGG Compound IDC06390
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID5304
    PubChem Compound6452574
    PDB IDNot Available
    ChEBI ID771
    Good Scents IDNot Available
    References
    General References
    1. Lee SH, Nam SY, Chung BC: Altered profile of endogenous steroids in the urine of patients with prolactinoma. Clin Biochem. 1998 Oct;31(7):529-35. [PubMed:9812172 ]
    2. Shibusawa H, Sano Y, Yamamoto T, Kambegawa A, Ohkawa T, Satoh N, Okinaga S, Arai K: A radioimmunoassay of serum 16alpha-hydroxypregnenolone with specific antiserum. Endocrinol Jpn. 1978 Apr;25(2):185-9. [PubMed:668632 ]
    3. Homoki J, Teller WM: Increased urinary excretion of total 16 alpha-hydroxypregnenolone in newborn infants with congenital adrenal hyperplasia due to 21-hydroxylase deficiency. Klin Wochenschr. 1982 Apr 15;60(8):407-10. [PubMed:6980322 ]
    4. Den K, Haruyama T, Hagiwara H, Fujii KT, Kambegawa A, Takami T, Yoshida T, Takagi S: Plasma levels of 16 alpha-hydroxypregnenolone, 16 alpha-hydroxyprogesterone and 16 alpha-hydroxydehydroepiandrosterone in the fetus and neonates. Endocrinol Jpn. 1979 Aug;26(4):439-47. doi: 10.1507/endocrj1954.26.439. [PubMed:159171 ]
    5. Janoski AH, Kelly WG: On the metabolism of 16-alpha-hydroxy-C21-steroids. II. Evidence for the presence of a glucuronide of 16-alpha-hydroxypregnenolone in human urine and its utility in estimating the rates of production of 16-alpha-hydroxyprogesterone and 16-alpha-hydroxypregnenolone. J Clin Endocrinol Metab. 1969 Oct;29(10):1291-300. doi: 10.1210/jcem-29-10-1291. [PubMed:5353659 ]