Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1416)
Drug Name
Riboflavin
Synonyms
Ribipca; Ribocrisina; Riboderm; Riboflavina; Riboflavina [INN-Spanish]; Riboflavine; Riboflavine [INN-French]; Riboflavinequinone; Riboflavinum; Riboflavinum [INN-Latin]; Ribosyn; Ribotone; Ribovel; Russupteridine Yellow III; Vitaflavine; Vitamin Bi; Aqua-Flave; Beflavin; Beflavine; Dermadram; Fiboflavin; Flavaxin; Flavin BB; Flaxain; Hyflavin; Lactobene; Lactoflavin; Lactoflavine; Vitamin G; Vitasan B2; riboflavin; vitamin B2; (-)-riboflavin; 6,7-Dimethyl-9-D-ribitylisoalloxazine; 7,8-Dimethyl-10-ribitylisoalloxazine; 83-88-5; E101; HYRE
Indication Acne vulgaris [ICD11: ED80] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 376.4 Topological Polar Surface Area 155
Heavy Atom Count 27 Rotatable Bond Count 5
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
493570
PubChem SID
3554 ; 219403 ; 587736 ; 2105997 ; 3134373 ; 7847118 ; 7890227 ; 8144638 ; 10312678 ; 10321452 ; 11528372 ; 14829102 ; 17389635 ; 22390365 ; 24714797 ; 24871529 ; 24888074 ; 24899340 ; 24899370 ; 24899397 ; 24899415 ; 38681417 ; 46392395 ; 46393994 ; 46394126 ; 46507342 ; 47193671 ; 47291288 ; 47662476 ; 47810933 ; 48414969 ; 48416517 ; 48424048 ; 48425597 ; 49698597 ; 50124213 ; 53788970 ; 57405728 ; 57654584 ; 57654591 ; 78187904 ; 81044568 ; 84943984 ; 87575598 ; 91697343 ; 103566330 ; 109761311 ; 121363265 ; 124890711 ; 124890712
ChEBI ID
CHEBI:17015
CAS Number
83-88-5
TTD Drug ID
D04QST
Formula
C17H20N4O6
Canonical SMILES
CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(CO)O)O)O
InChI
1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1
InChIKey
AUNGANRZJHBGPY-SCRDCRAPSA-N
The Predicted Metabolic Roadmap of This Drug
The Full List of Predicted Drug Metabolites (PDM) of This Drug
PDM Name PDM ID PubChem ID Reaction PDM Level Biosystem
Riboflavin M1 PDM007295 N. A. Oxidation - Aliphatic hydroxylation of methyl carbon adjacent to aromatic ring AndFromCyProduct 1 Human
Riboflavin M2 PDM007296 N. A. Oxidation - Aliphatic hydroxylation of methyl carbon adjacent to aromatic ring AndFromCyProduct 1 Human
Riboflavin M3 PDM007297 N. A. Oxidation - Oxidation of primary alcohol to aldehyde 1 Human
Riboflavin M30 PDM007324 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Riboflavin M31 PDM007325 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Riboflavin M32 PDM007326 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Riboflavin M33 PDM007327 N. A. Conjugation - Alkyl-OH-glucuronidation 1 Human
Riboflavin M34 PDM007328 N. A. Conjugation - Sulfation of primary alcohol 1 Human
Riboflavin M35 PDM007329 N. A. Conjugation - Sulfation of secondary alcohol 1 Human
Riboflavin M36 PDM007330 N. A. Conjugation - Sulfation of secondary alcohol 1 Human
Riboflavin M37 PDM007331 N. A. Conjugation - Sulfation of secondary alcohol 1 Human
Riboflavin M10 PDM007304 N. A. Conjugation - Sulfation of primary alcohol 2 Human
Riboflavin M11 PDM007305 N. A. Conjugation - Sulfation of secondary alcohol 2 Human
Riboflavin M12 PDM007306 N. A. Conjugation - Sulfation of secondary alcohol 2 Human
Riboflavin M13 PDM007307 N. A. Conjugation - Sulfation of secondary alcohol 2 Human
Riboflavin M14 PDM007308 N. A. Conjugation - Alkyl-OH-glucuronidation 2 Human
Riboflavin M15 PDM007309 N. A. Conjugation - Alkyl-OH-glucuronidation 2 Human
Riboflavin M16 PDM007310 N. A. Conjugation - Alkyl-OH-glucuronidation 2 Human
Riboflavin M17 PDM007311 N. A. Conjugation - Alkyl-OH-glucuronidation 2 Human
Riboflavin M18 PDM007312 N. A. Conjugation - Alkyl-OH-glucuronidation 2 Human
Riboflavin M19 PDM007313 N. A. Conjugation - Sulfation of primary alcohol 2 Human
Riboflavin M20 PDM007314 N. A. Conjugation - Sulfation of primary alcohol 2 Human
Riboflavin M21 PDM007315 N. A. Conjugation - Sulfation of secondary alcohol 2 Human
Riboflavin M22 PDM007316 N. A. Conjugation - Sulfation of secondary alcohol 2 Human
Riboflavin M23 PDM007317 N. A. Conjugation - Sulfation of secondary alcohol 2 Human
Riboflavin M24 PDM007318 N. A. Conjugation - Alkyl-OH-glucuronidation 2 Human
Riboflavin M25 PDM007319 N. A. Conjugation - Alkyl-OH-glucuronidation 2 Human
Riboflavin M26 PDM007320 N. A. Conjugation - Alkyl-OH-glucuronidation 2 Human
Riboflavin M27 PDM007321 N. A. Conjugation - Sulfation of secondary alcohol 2 Human
Riboflavin M28 PDM007322 N. A. Conjugation - Sulfation of secondary alcohol 2 Human
Riboflavin M29 PDM007323 N. A. Conjugation - Sulfation of secondary alcohol 2 Human
Riboflavin M4 PDM007298 N. A. Conjugation - Alkyl-OH-glucuronidation 2 Human
Riboflavin M5 PDM007299 N. A. Conjugation - Alkyl-OH-glucuronidation 2 Human
Riboflavin M6 PDM007300 N. A. Conjugation - Alkyl-OH-glucuronidation 2 Human
Riboflavin M7 PDM007301 N. A. Conjugation - Alkyl-OH-glucuronidation 2 Human
Riboflavin M8 PDM007302 N. A. Conjugation - Alkyl-OH-glucuronidation 2 Human
Riboflavin M9 PDM007303 N. A. Conjugation - Sulfation of primary alcohol 2 Human
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Acid phosphatase-like protein 1 (ACP6) DME0231 Homo sapiens
PPA6_HUMAN
3.1.3.2
[2]
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[3]
Eosinophil peroxidase (EPX) DME0244 Homo sapiens
PERE_HUMAN
1.11.1.7
[2]
NADPH-dependent nitroreductase (nfrA1) DME1243 Bacillus subtilis
NFRA1_BACSU
1.5.1.38
[4]
NADPH-dependent oxidoreductase (nfrA) DME1242 Staphylococcus aureus
NRFA_STAA8
1.6.5.2
[5]
Nitroreductase (NTR) DME1968 Salmonella typhimurium
A0A5K1UB29_SALTM
1.5.1.39
[6] , [7]
Prostatic acid phosphatase (ACP3) DME0232 Homo sapiens
PPAP_HUMAN
3.1.3.2
[2]
Tartrate-resistant acid ATPase (ACP5) DME0230 Homo sapiens
PPA5_HUMAN
3.1.3.2
[2]
Testicular acid phosphatase (ACP4) DME0229 Homo sapiens
PPAT_HUMAN
3.1.3.2
[2]
Xylosyl phosphatase (PXYLP1) DME0250 Homo sapiens
PXYP1_HUMAN
3.1.3.2
[2]
⏷ Show the Full List of 10  DME(s)
References
1 Riboflavin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 An atlas of human metabolism. Sci Signal. 2020 Mar 24;13(624). pii: eaaz1482. (Reaction HMR_6507)
3 Disruption of endogenous regulator homeostasis underlies the mechanism of rat CYP1A1 mRNA induction by metyrapone. Biochem J. 1998 Apr 1;331 ( Pt 1):273-81.
4 Conversion of NfsA, the major Escherichia coli nitroreductase, to a flavin reductase with an activity similar to that of Frp, a flavin reductase in Vibrio harveyi, by a single amino acid substitution. J Bacteriol. 1998 Jan;180(2):422-5.
5 Reduction of polynitroaromatic compounds: the bacterial nitroreductases. FEMS Microbiol Rev. 2008 May;32(3):474-500.
6 Purification and characterization of wild-type and mutant "classical" nitroreductases of Salmonella typhimurium. L33R mutation greatly diminishes binding of FMN to the nitroreductase of S. typhimurium. J Biol Chem. 1998 Sep 11;273(37):23922-8.
7 Prenatal diagnosis of junctional epidermolysis bullosa Herlitz type. Lancet. 1989 Oct 28;2(8670):1035-6. Letter

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.