Molecule

Riboflavin

AlkaPlorer ID: AK001880

Synonym: None

IUPAC Name: 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]benzo[g]pteridine-2,4-dione

Structure

SMILES: CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO)C1=NC(=O)NC(=O)C1=N2

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

InChIKey: AUNGANRZJHBGPY-SCRDCRAPSA-N

Reference

Biosynthesis of riboflavin. An unusual rearrangement in the formation of 6,7-dimethyl-8-ribityllumazine

PubChem CID: 493570

CAS: 13123-37-0

LOTUS: LTS0223882

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Eremothecium gossypii	Eremothecium	Saccharomycetaceae	Saccharomycetales	Saccharomycetes	Ascomycota	Fungi	Eukaryota

Properties Information

Molecule Weight: 376.36900000000014

TPSA？: 161.56

MolLogP？: -1.7235599999999995

Number of H-Donors: 5

Number of H-Acceptors: 9

RingCount: 3

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bacillus anthracis	Anthrax lethal factor	Potency	31622.8	nM	None
Cenchrus americanus	Cenchrus americanus	Activity	3.9	cm	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	9.5	g	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	11.4	cm	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	43.0	%	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	50.0	%	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	55.0	%	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	61.0	%	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	62.0	%	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	62.0	cm	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	63.0	%	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	64.0	%	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	67.0	%	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	69.0	%	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	92.0	%	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	1281.0	kg/ha	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	Activity	nan	None	10.1016/j.cropro.2007.02.012
Cenchrus americanus	Cenchrus americanus	TIME	1032.0	hr	10.1016/j.cropro.2007.02.012
Chlorocebus sabaeus	Vero C1008	CC50	50100.0	nM	10.6019/CHEMBL4651402
Chlorocebus sabaeus	Vero C1008	pCC50	4.3	None	10.6019/CHEMBL4651402
Escherichia coli	GroEL/GroES	IC50	18000.0	nM	10.1016/j.bmcl.2019.02.028
Escherichia coli	GroEL/GroES	IC50	100000.0	nM	10.1016/j.bmcl.2019.02.028
Escherichia coli	GroEL/GroES	Inhibition	57.0	%	10.1016/j.bmcl.2019.02.028
Escherichia coli	GroEL/GroES	Inhibition	78.0	%	10.1016/j.bmcl.2019.02.028
Escherichia coli K-12	Beta-lactamase AmpC	Inhibition	5.0	%	10.1021/jm030191r
Escherichia coli (strain K12)	60 kDa chaperonin	IC50	250000.0	nM	10.1016/j.bmcl.2019.02.028
Gallus gallus	Riboflavin-binding protein	Kd	5.0	nM	10.1021/ml100296z
Gallus gallus	Riboflavin-binding protein	Kd	6.6	nM	10.1021/ml100296z
Gallus gallus	Riboflavin-binding protein	Kd	34.0	nM	10.1021/ml100296z
Gallus gallus	Riboflavin-binding protein	Kd	46.0	nM	10.1021/ml100296z
Gallus gallus	Riboflavin-binding protein	Ki	350.0	nM	10.1021/ml100296z
Homo sapiens	15-hydroxyprostaglandin dehydrogenase [NAD+]	Potency	11220.2	nM	None
Homo sapiens	A-375	Activity	61.7	%	10.1021/acs.jmedchem.2c01262
Homo sapiens	A-375	Activity	nan	None	10.1021/acs.jmedchem.2c01262
Homo sapiens	A-375	Drug metabolism	nan	None	10.1021/acs.jmedchem.2c01262
Homo sapiens	Aldehyde dehydrogenase 1A1	Potency	8912.5	nM	None
Homo sapiens	Androgen Receptor	Inhibition	223.0	%	10.1073/pnas.0708036104
Homo sapiens	Androgen Receptor	Potency	1412.5	nM	None
Homo sapiens	Arachidonate 15-lipoxygenase	Potency	39810.7	nM	None
Homo sapiens	ATP-dependent DNA helicase Q1	Potency	39810.7	nM	None
Homo sapiens	Bile acid receptor FXR	Potency	35481.3	nM	None
Homo sapiens	Bile acid receptor FXR	Potency	44668.4	nM	None
Homo sapiens	Breast cancer type 1 susceptibility protein	Potency	7943.3	nM	None
Homo sapiens	Caspase-1	Potency	31622.8	nM	None
Homo sapiens	Caspase-7	Potency	31622.8	nM	None
Homo sapiens	Chymotrypsin C	Inhibition	5.0	%	10.1021/jm030191r
Homo sapiens	Cytochrome P450 3A4	Potency	19952.6	nM	None
Homo sapiens	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Potency	15848.9	nM	None
Homo sapiens	Homo sapiens	DILI_Concern	nan	None	10.1016/j.drudis.2016.02.015
Homo sapiens	Homo sapiens	DILI_severity_class	0.0	None	10.1016/j.drudis.2016.02.015
Homo sapiens	HSP60/HSP10	IC50	100000.0	nM	10.1016/j.bmcl.2019.02.028
Homo sapiens	Lymphoblastoid cell	Potency	15848.9	nM	None
Homo sapiens	Lymphoblastoid cell	Potency	39810.7	nM	None
Homo sapiens	MAP kinase ERK2	Potency	19952.6	nM	None
Homo sapiens	Nuclear factor erythroid 2-related factor 2	Potency	33491.5	nM	None
Homo sapiens	Nuclear factor NF-kappa-B p105 subunit	Potency	44668.4	nM	None
Homo sapiens	Peroxisome proliferator-activated receptor delta	Potency	28183.8	nM	None
Homo sapiens	Peroxisome proliferator-activated receptor delta	Potency	39810.7	nM	None
Homo sapiens	Peroxisome proliferator-activated receptor gamma	Potency	63095.7	nM	None
Homo sapiens	Retinoid X receptor alpha	Potency	28183.8	nM	None
Homo sapiens	Retinoid X receptor alpha	Potency	39810.7	nM	None
Homo sapiens	Solute carrier organic anion transporter family member 1B1	Inhibition	75.9	%	10.1124/mol.112.084152
Homo sapiens	Solute carrier organic anion transporter family member 1B3	Inhibition	72.6	%	10.1124/mol.112.084152
Homo sapiens	Thiosulfate sulfurtransferase	IC50	8800.0	nM	10.1016/j.bmcl.2019.02.028
Homo sapiens	Thyroid hormone receptor beta-1	Potency	0.7	nM	None
Homo sapiens	TNF-alpha	Potency	53080.4	nM	None
Homo sapiens	Tyrosyl-DNA phosphodiesterase 1	Potency	8912.5	nM	None
Homo sapiens	Tyrosyl-DNA phosphodiesterase 1	Potency	21136.0	nM	None
Homo sapiens	Tyrosyl-DNA phosphodiesterase 1	Potency	29855.4	nM	None
Homo sapiens	Vitamin D receptor	Potency	31622.8	nM	None
Homo sapiens	Vitamin D receptor	Potency	44668.4	nM	None
Mus musculus	Solute carrier family 22 member 6	Activity	nan	None	10.1074/jbc.274.3.1519
Rattus norvegicus	Inositol monophosphatase 1	Potency	10000.0	nM	None
Severe acute respiratory syndrome coronavirus 2	Replicase polyprotein 1ab	Inhibition	8.693	%	10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2	Replicase polyprotein 1ab	Inhibition	38.64	%	10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Hit score	0.1705	None	10.1101/2020.04.21.054387
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	IC50	11200.0	nM	10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	IC50	11220.18	nM	10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	IC50	50100.0	nM	10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	IC50	50118.72	nM	10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	-0.23	%	10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	-0.09	%	10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition	2.82	%	10.21203/rs.3.rs-23951/v1
Severe acute respiratory syndrome coronavirus 2	SARS-CoV-2	Inhibition index	0.1711	None	10.1101/2020.04.03.023846
Sus scrofa	Malate dehydrogenase mitochondrial	Inhibition	5.0	%	10.1021/jm030191r
None	ADMET	Activity	nan	None	10.1021/acs.jmedchem.2c01262
None	Hepatotoxicity	Hepatotoxicity	nan	None	10.1021/tx900326k
None	Molecular identity unknown	Potency	28183.8	nM	None
None	NON-PROTEIN TARGET	Activity	nan	None	10.1039/C3MD00149K
None	NON-PROTEIN TARGET	EC50	300000.0	nM	10.1039/C3MD00149K
None	No relevant target	EC50	129000.0	nM	10.1039/C3MD00149K
None	Phospholipidosis	Phospholipidosis	nan	None	10.1080/15376510701857262
None	Unchecked	Ac50	0.3162	uM	None
None	Unchecked	Ac50	12.59	uM	None
None	Unchecked	AC50	316.2	nM	None
None	Unchecked	AC50	12589.3	nM	None
None	Unchecked	Activity	11.2	%	10.1021/acs.jmedchem.2c01262
None	Unchecked	Drug metabolism	nan	None	10.1021/acs.jmedchem.2c01262
None	Unchecked	IC50	63000.0	nM	10.1016/j.bmcl.2019.02.028
None	Unchecked	Potency	5955.7	nM	None
None	Unchecked	Potency	7497.8	nM	None
None	Unchecked	Potency	31622.8	nM	None
None	Unchecked	Potency	35481.3	nM	None
None	Unchecked	Potency	39810.7	nM	None

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT002312	CC(=O)NC(CCN(O)C(=O)/C=C(\C)CCO)CC(=O)OCC/C(C)=C/C(=O)N(O)CCCC1NC(=O)C(CCCN(O)C(=O)/C=C(/C)CCO)NC1=O.CC(=O)NC(CCN(O)C(=O)/C=C(\C)CCO)CC(=O)OCC/C(C)=C/C(=O)N(O)CCCC1NC(=O)C(CCCN(O)C(=O)/C=C(/C)CCO)NC1=O.Cc1cc2nc3c(=O)[n-]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C>>CC(=O)NC(CCCN(O)C(=O)/C=C(\C)CCO)C(=O)OCC/C(C)=C\C(=O)N(O)CCCC1NC(=O)C(CCCN(O)C(=O)/C=C(\C)CCO)NC1=O	MNXR153264
AKRT002313	CC(=O)NC(CCN(O)C(=O)/C=C(\C)CCO)CC(=O)OCC/C(C)=C/C(=O)N(O)CCCC1NC(=O)C(CCCN(O)C(=O)/C=C(/C)CCO)NC1=O.CC(=O)NC(CCN(O)C(=O)/C=C(\C)CCO)CC(=O)OCC/C(C)=C/C(=O)N(O)CCCC1NC(=O)C(CCCN(O)C(=O)/C=C(/C)CCO)NC1=O.Cc1cc2nc3c(=O)[n-]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C>>CC(=O)N[C@@H](CCCN(O)C(=O)/C=C(\C)CCO)C(=O)OCC/C(C)=C/C(=O)N(O)CCC[C@@H]1NC(=O)[C@H](CCCN(O)C(=O)/C=C(\C)CCO)NC1=O	MNXR153265
AKRT002314	CC(=O)NC(CCN(O)C(=O)/C=C(\C)CCO)CC(=O)OCC/C(C)=C/C(=O)N(O)CCCC1NC(=O)C(CCCN(O)C(=O)/C=C(/C)CCO)NC1=O.CC(=O)NC(CCN(O)C(=O)/C=C(\C)CCO)CC(=O)OCC/C(C)=C/C(=O)N(O)CCCC1NC(=O)C(CCCN(O)C(=O)/C=C(/C)CCO)NC1=O.Cc1cc2nc3c(=O)[n-]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C>>Cc1cc2c(cc1C)N(C[C@H](O)[C@H](O)[C@H](O)CO)C1=NC(=O)NC(=O)C1N2	MNXR153264
AKRT014971	Cc1cc2c(cc1C)N(C[C@H](O)[C@H](O)[C@H](O)CO)C1=NC(=O)NC(=O)C1N2>>Cc1cc2nc3c(=O)[n-]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C	MNXR135815
AKRT014976	Cc1cc2nc3[nH]c(=O)[nH]c(=O)c3nc2cc1C.OC[C@H](O)[C@H](O)[C@H](O)CO>>Cc1cc2nc3c(=O)[n-]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C	RIBOFLAVINASE-RXN
AKRT014977	Cc1cc2nc3c(=O)[n-]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C.N[C@@H](Cc1c[nH]cn1)C(=O)O>>Cc1cc2nc3c(=O)[n-]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1Cn1cnc(C[C@H](N)C(=O)O)c1	RXN-16419
AKRT014978	Cc1cc2nc3c(=O)[n-]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C>>Cc1cc2nc3[nH]c(=O)[nH]c(=O)c3nc2cc1C	RIBOFLAVINASE-RXN
AKRT014979	Cc1cc2nc3c(=O)[n-]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C>>OC[C@H](O)[C@H](O)[C@H](O)CO	RIBOFLAVINASE-RXN
AKRT014984	Cc1cc2nc3c(=O)[nH]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C>>Cc1cc2nc3[nH]c(=O)[nH]c(=O)c3nc2cc1C	R01732
AKRT014985	Cc1cc2nc3c(=O)[nH]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C>>OC[C@H](O)[C@H](O)[C@H](O)CO	R01732
AKRT014990	Cc1cc2nc[nH]c2cc1C.O=C(O)c1ccc[n+]([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c1>>Cc1cc2nc3c(=O)[n-]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C	MNXR97179
AKRT015271	Cc1nc2c(=O)[n-]c(=O)nc-2n(C[C@H](O)[C@H](O)[C@H](O)CO)c1C.Cc1nc2c(=O)[n-]c(=O)nc-2n(C[C@H](O)[C@H](O)[C@H](O)CO)c1C>>Cc1cc2nc3c(=O)[n-]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C	RIBOFLAVIN-SYN-RXN
AKRT015273	Cc1nc2c(=O)[nH]c(=O)nc-2n(CC(O)C(O)C(O)CO)c1C.Cc1nc2c(=O)[nH]c(=O)nc-2n(CC(O)C(O)C(O)CO)c1C>>Cc1cc2nc3c(=O)[n-]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C	MNXR192029
AKRT015275	Cc1nc2c(=O)[nH]c(=O)nc-2n(C[C@H](O)[C@H](O)[C@H](O)CO)c1C.Cc1nc2c(=O)[nH]c(=O)nc-2n(C[C@H](O)[C@H](O)[C@H](O)CO)c1C>>Cc1cc2nc3c(=O)[nH]c(=O)nc-3n(C[C@H](O)[C@H](O)[C@H](O)CO)c2cc1C	R00066