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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:11 UTC
Update Date2019-07-23 06:06:57 UTC
HMDB IDHMDB0030651
Secondary Accession Numbers
  • HMDB30651
Metabolite Identification
Common NameMukurozidiol
DescriptionMukurozidiol, also known as byak-angelicin, belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group. Mukurozidiol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Mukurozidiol has been detected, but not quantified in, a few different foods, such as citrus, herbs and spices, and lemons. This could make mukurozidiol a potential biomarker for the consumption of these foods.
Structure
Data?1563862017
Synonyms
ValueSource
BiacangelicinHMDB
BjacangelicinHMDB
BjakangelicinHMDB
Byak-angelicinHMDB
ByakangelicinHMDB
ByankagelicineHMDB
Chemical FormulaC17H18O7
Average Molecular Weight334.3206
Monoisotopic Molecular Weight334.10525293
IUPAC Name9-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-7H-furo[3,2-g]chromen-7-one
Traditional Name9-(2,3-dihydroxy-3-methylbutoxy)-4-methoxyfuro[3,2-g]chromen-7-one
CAS Registry Number482-25-7
SMILES
COC1=C2C=CC(=O)OC2=C(OCC(O)C(C)(C)O)C2=C1C=CO2
InChI Identifier
InChI=1S/C17H18O7/c1-17(2,20)11(18)8-23-16-14-10(6-7-22-14)13(21-3)9-4-5-12(19)24-15(9)16/h4-7,11,18,20H,8H2,1-3H3
InChI KeyPKRPFNXROFUNDE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct Parent5-methoxypsoralens
Alternative Parents
Substituents
  • 5-methoxypsoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Tertiary alcohol
  • Furan
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactone
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point117 - 118 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP1.79ALOGPS
logP1ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)13.2ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.36 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity84.63 m³·mol⁻¹ChemAxon
Polarizability33.46 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9021000000-12ad37832d5b3de8a251Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01qi-9733800000-d31e4a379f71b1469a37Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0390000000-c586449ed45eaee81d8aSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0290000000-796c6a46fff10057402aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-1019000000-3e264c7c7edefbc26387Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fri-6379000000-510238678d6075731097Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-5190000000-373623545e67ed55afe5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1179000000-ed28fa0609b236d64228Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-0190000000-f8292e207a57ca902087Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p9-1690000000-b0fdb0d762b64ab18847Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002557
KNApSAcK IDNot Available
Chemspider ID535438
KEGG Compound IDC09141
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound616063
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ngwendson JN, Bedir E, Efange SM, Okunji CO, Iwu MM, Schuster BG, Khan IA: Constituents of Peucedanum zenkeri seeds and their antimicrobial effects. Pharmazie. 2003 Aug;58(8):587-9. [PubMed:12967040 ]
  2. Marumoto S, Miyazawa M: beta-secretase inhibitory effects of furanocoumarins from the root of Angelica dahurica. Phytother Res. 2010 Apr;24(4):510-3. doi: 10.1002/ptr.2967. [PubMed:20041416 ]
  3. Kwon OS, Song YS, Shin KH, Ryu JC: Identification of new urinary metabolites of byakangelicin, a component of Angelicae dahuricae Radix, in rats. Arch Pharm Res. 2003 Aug;26(8):606-11. [PubMed:12967195 ]
  4. Chen Q, Li P, He J, Zhang Z, Liu J: Supercritical fluid extraction for identification and determination of volatile metabolites from Angelica dahurica by GC-MS. J Sep Sci. 2008 Oct;31(18):3218-24. doi: 10.1002/jssc.200800325. [PubMed:18705001 ]
  5. Zhao AH, Yang XB, Yang XW, Zhang YB, Xu W, Liu JX: Biotransformation products of phellopterin by rat liver microsomes and the inhibition on NO production in LPS-activated RAW264.7 cells. J Asian Nat Prod Res. 2012;14(10):956-65. doi: 10.1080/10286020.2012.729506. [PubMed:23046467 ]
  6. Zhang Y, Xu H, Chen X, Chen C, Wang H, Meng F, Yang H, Huang L: Simultaneous quantification of 17 constituents from Yuanhu Zhitong tablet using rapid resolution liquid chromatography coupled with a triple quadrupole electrospray tandem mass spectrometry. J Pharm Biomed Anal. 2011 Nov 1;56(3):497-504. doi: 10.1016/j.jpba.2011.06.008. Epub 2011 Jun 16. [PubMed:21733652 ]
  7. Chen Z, Wang J, Chen D, Fan G, Wu Y: Sodium desoxycholate-assisted capillary electrochromatography with methacrylate ester-based monolithic column on fast separation and determination of coumarin analogs in Angelica dahurica extract. Electrophoresis. 2012 Sep;33(18):2884-91. doi: 10.1002/elps.201200120. Epub 2012 Aug 28. [PubMed:22930555 ]
  8. Song DK, Kim JY, Li G, Lee KS, Seo CS, Yan JJ, Jung JS, Kim HJ, Chang HW, Son JK: Agents protecting against sepsis from the roots of Angelica dahurica. Biol Pharm Bull. 2005 Feb;28(2):380-2. [PubMed:15684506 ]
  9. Chen Y, Fan G, Chen B, Xie Y, Wu H, Wu Y, Yan C, Wang J: Separation and quantitative analysis of coumarin compounds from Angelica dahurica (Fisch. ex Hoffm) Benth. et Hook. f by pressurized capillary electrochromatography. J Pharm Biomed Anal. 2006 Apr 11;41(1):105-16. Epub 2005 Nov 28. [PubMed:16318908 ]
  10. Piao XL, Park IH, Baek SH, Kim HY, Park MK, Park JH: Antioxidative activity of furanocoumarins isolated from Angelicae dahuricae. J Ethnopharmacol. 2004 Aug;93(2-3):243-6. [PubMed:15234759 ]
  11. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
Mukurozidiol → {[3-hydroxy-1-({4-methoxy-7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)-3-methylbutan-2-yl]oxy}sulfonic aciddetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Mukurozidiol → 3,4,5-trihydroxy-6-{[3-hydroxy-4-({4-methoxy-7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)-2-methylbutan-2-yl]oxy}oxane-2-carboxylic aciddetails
Mukurozidiol → 3,4,5-trihydroxy-6-{[3-hydroxy-1-({4-methoxy-7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)-3-methylbutan-2-yl]oxy}oxane-2-carboxylic aciddetails