Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Beta-Cortol (HMDB05821)

Record Information
Version 3.5
Creation Date 2007-04-12 07:11:37 -0600
Update Date 2013-05-29 13:42:10 -0600
HMDB ID HMDB05821
Secondary Accession Numbers None
Metabolite Identification
Common Name Beta-Cortol
Description Beta-Cortol is a normal androgen metabolite present in adults. It has been found in the urine of infants as well. Beta-Cortol is the 5b enantiomer of beta-allocortol. Beta-cortol levels are significantly higher in premenopausal women with leiomyomas than in age-matched healthy premenopausal control women. Uterine leiomyomas are tumors closely associated with estrogen levels and it has been noted that the development of leiomyomas depends on the condition of menstruation, perimenopause and pregnancy. (PMID: 14698830 Link_out, 14616886 Link_out, 14643447 Link_out, 15635046 Link_out, 14709852 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (3alpha,5beta,11beta,20R) Pregnane-3,11,17,20,21-pentol
  2. 3alpha,11beta,17,20beta,21-Pentahydroxypregnane
  3. 5beta-Pregnan-3alpha,11beta,20,20beta,21-pentol
  4. 5beta-Pregnane-3alpha,11beta,17,20beta,21-pentol 20beta-Cortol
  5. 5beta-Pregnane-3alpha,11beta,17alpha,20beta,21-pentol
  6. b-Cortol
  7. beta-Cortol
  8. Cortol-20beta
  9. Pregnane-3alpha,11beta,17,20beta,21-pentol
Chemical Formula C21H36O5
Average Molecular Weight 368.5075
Monoisotopic Molecular Weight 368.256274262
IUPAC Name (1S,2S,5R,7R,10S,11S,14R,15S,17S)-14-[(1R)-1,2-dihydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14,17-triol
Traditional IUPAC Name (1S,2S,5R,7R,10S,11S,14R,15S,17S)-14-[(1R)-1,2-dihydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,14,17-triol
CAS Registry Number 667-65-2
SMILES [H][C@@]12CC[C@](O)([C@H](O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier InChI=1S/C21H36O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-18,22-26H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,17-,18-,19+,20+,21+/m1/s1
InChI Key FFPUNPBUZDTHJI-ZFOKFBPFSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Gluco/mineralocorticoids, Progestogins and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
Substituents
  • 1,2 Diol
  • 11 Hydroxy Steroid
  • 17 Hydroxy Steroid
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Cyclic Alcohol
  • Cyclohexane
  • Decaline
  • Primary Alcohol
  • Secondary Alcohol
  • Tertiary Alcohol
Direct Parent Gluco/mineralocorticoids, Progestogins and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.05 g/L ALOGPS
LogP 1.43 ALOGPS
LogP 0.5 ChemAxon
LogS -2.55 ALOGPS
pKa (strongest acidic) 12.99 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 101.15 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 98.37 ChemAxon
Polarizability 41.82 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Comment Normal
Urine Detected and Quantified
0.18 +/- 0.15 umol/mmol creatinine Adult (>18 years old) Female Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected and Quantified 0.059 +/- 0.045 umol/mmol creatinine Adult (>18 years old) Female Thyroid cancer
Associated Disorders and Diseases
Disease References
Thyroid cancer
  • Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. Pubmed: 14643447 Link_out
    Associated OMIM IDs None
    DrugBank ID Not Available
    DrugBank Metabolite ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB023774
    KNApSAcK ID Not Available
    Chemspider ID 215388 Link_out
    KEGG Compound ID Not Available
    BioCyc ID Not Available
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB05821 Link_out
    Metagene Link HMDB05821 Link_out
    METLIN ID Not Available
    PubChem Compound 246164 Link_out
    PDB ID Not Available
    ChEBI ID Not Available
    References
    Synthesis Reference Not Available
    Material Safety Data Sheet (MSDS) Not Available
    General References
    1. Vrbanac JJ, Sweeley CC, Pinkston JD: Automated metabolic profiling analysis of urinary steroids by a gas chromatography mass spectrometry data system. Biomed Mass Spectrom. 1983 Mar;10(3):155-61. Pubmed: 6850067 Link_out
    2. Shamim W, Yousufuddin M, Bakhai A, Coats AJ, Honour JW: Gender differences in the urinary excretion rates of cortisol and androgen metabolites. Ann Clin Biochem. 2000 Nov;37 ( Pt 6):770-4. Pubmed: 11085621 Link_out
    3. Jung BH, Bai SW, Chung BC: Endogenous urinary steroids in premenopausal women with uterine leiomyomas. Int J Gynaecol Obstet. 2004 Jan;84(1):55-60. Pubmed: 14698830 Link_out
    4. Swords FM, Carroll PV, Kisalu J, Wood PJ, Taylor NF, Monson JP: The effects of growth hormone deficiency and replacement on glucocorticoid exposure in hypopituitary patients on cortisone acetate and hydrocortisone replacement. Clin Endocrinol (Oxf). 2003 Nov;59(5):613-20. Pubmed: 14616886 Link_out
    5. Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. Pubmed: 14643447 Link_out
    6. Heckmann M, Hartmann MF, Kampschulte B, Gack H, Bodeker RH, Gortner L, Wudy SA: Assessing cortisol production in preterm infants: do not dispose of the nappies. Pediatr Res. 2005 Mar;57(3):412-8. Epub 2005 Jan 5. Pubmed: 15635046 Link_out
    7. Homma K, Hasegawa T, Masumoto M, Takeshita E, Watanabe K, Chiba H, Kurosawa T, Takahashi T, Matsuo N: Reference values for urinary steroids in Japanese newborn infants: gas chromatography/mass spectrometry in selected ion monitoring. Endocr J. 2003 Dec;50(6):783-92. Pubmed: 14709852 Link_out