Riboflavin

Details

• Internal ID: 17944223-7c64-402e-a911-383f96c3a8d7
• Taxonomy: Organoheterocyclic compounds > Pteridines and derivatives > Alloxazines and isoalloxazines > Flavins
• IUPAC Name: 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
• SMILES (Canonical): CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(CO)O)O)O
• SMILES (Isomeric): CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@@H]([C@@H](CO)O)O)O
• InChI: 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
• InChI Key: AUNGANRZJHBGPY-SCRDCRAPSA-N
• Popularity: 29,870 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀N₄O₆
• Molecular Weight: 376.40 g/mol
• Exact Mass: 376.13828437 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -1.50
• Atomic LogP (AlogP): -1.72
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• vitamin B2
• 83-88-5
• Lactoflavin
• Riboflavine
• Vitamin G
• Lactoflavine
• Flavaxin
• Riboflavinum
• Beflavin
• Beflavine
• (-)-riboflavin
• Lactobene
• Ribocrisina
• Riboderm
• Riboflavina
• Ribotone
• Vitaflavine
• Flaxain
• Ribipca
• Ribosyn
• Ribovel
• Vitamin Bi
• Flavin BB
• Russupteridine Yellow III
• Vitasan B2
• Fiboflavin
• Dermadram
• Aqua-Flave
• HYRE
• Bisulase
• Riboflavinequinone
• 7,8-Dimethyl-10-ribitylisoalloxazine
• 6,7-Dimethyl-9-D-ribitylisoalloxazine
• E101
• Lacto-flavin
• Hyflavin
• vitamin-b2
• HSDB 817
• C.I. Food Yellow 15
• Riboflavine [INN-French]
• Riboflavinum [INN-Latin]
• Riboflavina [INN-Spanish]
• Riboflavin (Vit B2)
• CCRIS 1904
• Ins no.101(iii)
• CHEBI:17015
• Ins-101(iii)
• Riboflavin (Vitamin B2)
• C17H20N4O6
• UNII-TLM2976OFR
• 7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine
• EINECS 201-507-1
• E-101(iii)
• TLM2976OFR
• Vitamin b2 (as riboflavin)
• NSC 33298
• Vitamin B-2
• 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione
• DTXSID8021777
• AI3-14697
• INS NO. 101(I)
• Isoalloxazine, 7,8-dimethyl-10-D-ribityl-
• C.I. 50900
• NSC-33298
• NCI-0033298
• Riboflavin [USP:INN:BAN]
• Riboflavin [USAN:INN:JAN]
• D-Ribitol, 1-deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo(g)pteridin-10(2H)-yl)-
• DTXCID401777
• Isoalloxazine, 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-
• 1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol
• 7,8-dimethyl-10-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione
• Benzo(g)pteridine-2,4(3H,10H)-dione, 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-
• RIBOFLAVIN (II)
• RIBOFLAVIN [II]
• MFCD00005022
• RIBOFLAVIN (MART.)
• RIBOFLAVIN [MART.]
• RIBOFLAVIN (USP-RS)
• RIBOFLAVIN [USP-RS]
• Vitamin B2 (Riboflavin)
• 7,8-DIMETHYL-10-(1'-D-RIBITYL)ISOALLOXAZINE
• RIBOFLAVIN (EP MONOGRAPH)
• RIBOFLAVIN [EP MONOGRAPH]
• RIBOFLAVIN (USP MONOGRAPH)
• RIBOFLAVIN [USP MONOGRAPH]
• 1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol
• 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione
• 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione
• Vitamin B 2
• 1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol
• 1217461-14-7
• 7,8-dimethyl-10-ribityl-nu-isoalloxazine
• vitaminum b2
• C17-H20-N4-O6
• 1kyv
• 2ccb
• 2vxa
• ()-Riboflavin
• 1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo(g)pteridin-10(2H)-yl)-D-ribitol
• 1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo(g)pteridin-10(2H)-yl)pentitol
• 5-deoxy-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo(g)pteridin-10(2H)-yl)-D-ribitol
• 5-deoxy-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol
• 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo(g)pteridine-2,4(3H,10H)-dione
• San Yellow B
• CAS-83-88-5
• NCGC00017291-05
• Bisulase (TN)
• 7,8-dimethyl-10-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)benzo(g)pteridine-2,4(3H,10H)-dione
• Food Yellow 15
• Prestwick_442
• 2fl5
• 2vx9
• 4d1y
• RIBOFLAVIN [MI]
• RIBOFLAVIN [FCC]
• RIBOFLAVIN [INN]
• RIBOFLAVIN [JAN]
• Vitamin B2; E101
• Prestwick3_000634
• RIBOFLAVIN [HSDB]
• RIBOFLAVIN [INCI]
• LACTOFLAVIN [INCI]
• RIBOFLAVIN [VANDF]
• D04QST
• Epitope ID:161730
• RIBOFLAVINUM [HPUS]
• SCHEMBL7706
• CHEMBL1534
• RIBOFLAVIN [WHO-DD]
• RIBOFLAVIN [WHO-IP]
• VITAMIN B2 [VANDF]
• BSPBio_000628
• MLS001066391
• BPBio1_000692
• GTPL6578
• Riboflavin (JP17/USP/INN)
• RIBOFLAVINE; VITAMIN B2
• RIBOFLAVIN [ORANGE BOOK]
• A11HA04
• S01XA26
• VITAMIN B2 [GREEN BOOK]
• (-)-Riboflavin, 97-103%
• HMS2096P10
• Benzo[g]pteridine riboflavin deriv.
• HY-B0456
• Riboflavin(B2);7,8-Dimethyl-10-((2S,3S,4R)-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione
• RIBOFLAVINUM [WHO-IP LATIN]
• Tox21_110813
• Tox21_111714
• Tox21_201633
• Tox21_302980
• 6,7-Dimethyl-9-ribitylisoalloxazine
• BDBM50362895
• s2540
• Riboflavin (B2), analytical standard
• Tox21_111714_1
• CS-O-31031
• DB00140
• LS-2192
• NCGC00091288-01
• NCGC00091288-02
• NCGC00091288-03
• NCGC00091288-04
• NCGC00091288-05
• NCGC00179498-01
• NCGC00256408-01
• NCGC00259182-01
• AS-15936
• SMR000112236
• R0020
• (-)-Riboflavin, tested according to Ph.Eur.
• C00255
• D00050
• EN300-6477227
• (-)-Riboflavin, meets USP testing specifications
• A840676
• A934900
• Q130365
• (-)-Riboflavin, from Eremothecium ashbyii, >=98%
• W-104132
• Z2216887959
• RIBOFLAVIN SODIUM PHOSPHATE IMPURITY D [EP IMPURITY]
• Riboflavin, European Pharmacopoeia (EP) Reference Standard
• Riboflavin, United States Pharmacopeia (USP) Reference Standard
• 7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-isoalloxazine
• Riboflavin, Pharmaceutical Secondary Standard; Certified Reference Material
• 3,10-Dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzopteridine-2,4-dione
• 7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-Benzo[g]pteridine-2,4(3H,10H)-dione
• d-ribitol, 1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo(g)pteridin-10(-2H)-yl)-
• Riboflavin for peak identification, European Pharmacopoeia (EP) Reference Standard
• (-)-Riboflavin, 100 mug/mL (1% ammonium acetate in 50:50 methanol:water), certified reference material, ampule of 1 mL
• (-)-Riboflavin, BioReagent, suitable for cell culture, suitable for insect cell culture, >=98%
• 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrakis(oxidanyl)pentyl]benzo[g]pteridine-2,4-dione
• 7,8-dimethyl-2,4-dioxo-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl](2,4a,10a-C,1,3-)-2H,3H,4H,10H-benzo[g]pteridin-3-yl
• InChI=1/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/s

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9609	96.09%
Caco-2	-	0.8020	80.20%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.3960	39.60%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9413	94.13%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.5593	55.93%
P-glycoprotein inhibitior	-	0.7935	79.35%
P-glycoprotein substrate	-	0.7126	71.26%
CYP3A4 substrate	+	0.5190	51.90%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	-	0.8793	87.93%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	+	0.7302	73.02%
CYP2D6 inhibition	-	0.9516	95.16%
CYP1A2 inhibition	+	0.8531	85.31%
CYP2C8 inhibition	-	0.8495	84.95%
CYP inhibitory promiscuity	-	0.9203	92.03%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7700	77.00%
Carcinogenicity (trinary)	Non-required	0.6445	64.45%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9840	98.40%
Skin irritation	-	0.7892	78.92%
Skin corrosion	-	0.9477	94.77%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5444	54.44%
Micronuclear	+	0.9300	93.00%
Hepatotoxicity	-	0.9676	96.76%
skin sensitisation	-	0.8829	88.29%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	IV	0.6176	61.76%
Estrogen receptor binding	+	0.6157	61.57%
Androgen receptor binding	+	0.6159	61.59%
Thyroid receptor binding	-	0.6155	61.55%
Glucocorticoid receptor binding	+	0.6460	64.60%
Aromatase binding	+	0.6293	62.93%
PPAR gamma	+	0.6031	60.31%
Honey bee toxicity	-	0.9577	95.77%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	-	0.8580	85.80%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	11220.2 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	8912.5 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	39810.7 nM	Potency	via CMAUP
CHEMBL1293236	P46063	ATP-dependent DNA helicase Q1	39810.7 nM	Potency	via CMAUP
CHEMBL5990	P38398	Breast cancer type 1 susceptibility protein	7943.3 nM	Potency	via CMAUP
CHEMBL4801	P29466	Caspase-1	31622.8 nM	Potency	via CMAUP
CHEMBL3468	P55210	Caspase-7	31622.8 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	19952.6 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	15848.9 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	19952.6 nM	Potency	via CMAUP
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	8912.5 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.55%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.02%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	95.61%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.52%	96.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	92.53%	93.10%
CHEMBL1937	Q92769	Histone deacetylase 2	92.28%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.44%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.66%	93.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.15%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.56%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.93%	86.92%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.59%	90.08%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	82.68%	92.68%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.19%	93.40%
CHEMBL1781	P11387	DNA topoisomerase I	81.99%	97.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.96%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.46%	90.71%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.38%	93.65%
CHEMBL3401	O75469	Pregnane X receptor	80.37%	94.73%

Plants that contains it

• Arabidopsis thaliana
• Changium smyrnioides
• Crocus sativus
• Ginkgo biloba
• Hippophae rhamnoides
• Humulus scandens
• Lycium chinense
• Malus pumila
• Morus alba
• Onobrychis viciifolia
• Oryza sativa
• Panax ginseng
• Phragmites australis
• Solanum tuberosum
• Taraxacum mongolicum
• Vigna radiata
• Ziziphus jujuba

Cross-Links

• PubChem: 493570
• NPASS: NPC94167
• ChEMBL: CHEMBL1534
• LOTUS: LTS0223882
• wikiData: Q130365