riboflavin (CHEBI:17015)

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CHEBI:17015 - riboflavin

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ChEBI Name	riboflavin

ChEBI ID	CHEBI:17015

Definition	D-Ribitol in which the hydroxy group at position 5 is substituted by a 7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl moiety. It is a nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables, but the richest natural source is yeast. The free form occurs only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin-adenine dinucleotide.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:45214, CHEBI:15044, CHEBI:27299, CHEBI:8843, CHEBI:529204

Supplier Information	ZINC000008218444

Download	Molfile XML SDF

more structures >>

Molfile

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The Resolver thinks Mol

RBF - Ideal conformer

Mrv1927 07202109543D

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Time for openFile(RBF - Ideal conformer

Mrv1927 07202109543D

47 49 0 0 0 0 999 V2000

0.6650 -2.4850 0.5130 N 0 0 0 0 0 0 0 0 0 0 0 0

1.3120 -3.6110 0.2220 C 0 0 0 0 0 0 0 0 0 0 0 0

0.7410 -4.6680 0.4280 O 0 0 0 0 0 0 0 0 0 0 0 0

2.5520 -3.6550 -0.2850 N 0 0 0 0 0 0 0 0 0 0 0 0

3.2480 -2.5230 -0.5400 C 0 0 0 0 0 0 0 0 0 0 0 0

4.3730 -2.5610 -1.0000 O 0 0 0 0 0 0 0 0 0 0 0 0

2.5810 -1.2380 -0.2360 C 0 0 0 0 0 0 0 0 0 0 0 0

3.1620 -0.0840 -0.4440 N 0 0 0 0 0 0 0 0 0 0 0 0

2.5300 1.0610 -0.1570 C 0 0 0 0 0 0 0 0 0 0 0 0

3.1740 2.2930 -0.3880 C 0 0 0 0 0 0 0 0 0 0 0 0

2.5330 3.4600 -0.0980 C 0 0 0 0 0 0 0 0 0 0 0 0

3.2280 4.7730 -0.3480 C 0 0 0 0 0 0 0 0 0 0 0 0

1.2450 3.4520 0.4260 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5580 4.7570 0.7380 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5910 2.2630 0.6630 C 0 0 0 0 0 0 0 0 0 0 0 0

1.2210 1.0560 0.3760 C 0 0 0 0 0 0 0 0 0 0 0 0

0.5710 -0.1370 0.6110 N 0 0 0 0 0 0 0 0 0 0 0 0

1.2180 -1.2990 0.3180 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.7860 -0.1540 1.1640 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.8030 -0.1270 0.0210 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.6180 1.0610 -0.7520 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.2200 -0.1450 0.5980 C 0 0 2 0 0 0 0 0 0 0 0 0

-3.4040 -1.3320 1.3710 O 0 0 0 0 0 0 0 0 0 0 0 0

-4.2360 -0.1170 -0.5450 C 0 0 2 0 0 0 0 0 0 0 0 0

-4.0520 1.0700 -1.3190 O 0 0 0 0 0 0 0 0 0 0 0 0

-5.6530 -0.1350 0.0320 C 0 0 1 0 0 0 0 0 0 0 0 0

-6.6010 -0.2270 -1.0340 O 0 0 0 0 0 0 0 0 0 0 0 0

2.9590 -4.5160 -0.4720 H 0 0 0 0 0 0 0 0 0 0 0 0

4.1740 2.3120 -0.7950 H 0 0 0 0 0 0 0 0 0 0 0 0

3.0070 5.1140 -1.3600 H 0 0 0 0 0 0 0 0 0 0 0 0

2.8740 5.5140 0.3690 H 0 0 0 0 0 0 0 0 0 0 0 0

4.3040 4.6430 -0.2350 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0050 5.0950 -0.1380 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.1310 4.6150 1.5710 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3040 5.5040 1.0080 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4090 2.2680 1.0710 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9270 -1.0600 1.7540 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9310 0.7190 1.7990 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.6580 -1.0000 -0.6150 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7320 1.8790 -0.2500 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.3640 0.7290 1.2340 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.2900 -2.1510 0.8680 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.0920 -0.9910 -1.1810 H 0 0 0 0 0 0 0 0 0 0 0 0

-4.1660 1.8880 -0.8160 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.7650 -0.9950 0.6930 H 0 0 0 0 0 0 0 0 0 0 0 0

-5.8280 0.7810 0.5950 H 0 0 0 0 0 0 0 0 0 0 0 0

-7.5220 -0.2440 -0.7410 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 18 2 0 0 0 0

2 3 2 0 0 0 0

2 4 1 0 0 0 0

4 5 1 0 0 0 0

4 28 1 0 0 0 0

5 6 2 0 0 0 0

5 7 1 0 0 0 0

7 8 2 0 0 0 0

7 18 1 0 0 0 0

8 9 1 0 0 0 0

9 10 1 0 0 0 0

9 16 2 0 0 0 0

10 11 2 0 0 0 0

10 29 1 0 0 0 0

11 12 1 0 0 0 0

11 13 1 0 0 0 0

12 30 1 0 0 0 0

12 31 1 0 0 0 0

12 32 1 0 0 0 0

13 14 1 0 0 0 0

13 15 2 0 0 0 0

14 33 1 0 0 0 0

14 34 1 0 0 0 0

14 35 1 0 0 0 0

15 16 1 0 0 0 0

15 36 1 0 0 0 0

16 17 1 0 0 0 0

17 18 1 0 0 0 0

17 19 1 0 0 0 0

19 20 1 0 0 0 0

19 37 1 0 0 0 0

19 38 1 0 0 0 0

20 21 1 0 0 0 0

20 22 1 0 0 0 0

20 39 1 6 0 0 0

21 40 1 0 0 0 0

22 23 1 0 0 0 0

22 24 1 0 0 0 0

22 41 1 1 0 0 0

23 42 1 0 0 0 0

24 25 1 0 0 0 0

24 26 1 0 0 0 0

24 43 1 6 0 0 0

25 44 1 0 0 0 0

26 27 1 0 0 0 0

26 45 1 0 0 0 0

26 46 1 0 0 0 0

27 47 1 0 0 0 0

M END): 19 ms

reading 47 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

47 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Molfile

Wikipedia	License
Protoporphyrin IX is an organic compound, classified as a porphyrin, that plays an important role in living organisms as a precursor to other critical compounds like heme (hemoglobin) and chlorophyll. It is a deeply colored solid that is not soluble in water. The name is often abbreviated as PPIX. Protoporphyrin IX contains a porphine core, a tetrapyrrole macrocycle with a marked aromatic character. Protoporphyrin IX is essentially planar, except for the N-H bonds that are bent out of the plane of the rings, in opposite (trans) directions.
Read full article at Wikipedia

Formula

C17H20N4O6

Net Charge

Average Mass

376.369

Monoisotopic Mass

376.13828

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

SMILES

CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1

Metabolite of Species	Details
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Mangifera indica (NCBI:txid29780)	See: PubMed
Escherichia coli (NCBI:txid562)	See: PubMed
Homo sapiens (NCBI:txid9606)	Found in blood (UBERON:0000178). See: Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Homo sapiens (NCBI:txid9606)	Found in saliva (UBERON:0001836). See: Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Homo sapiens (NCBI:txid9606)	Found in urine (BTO:0001419). See: Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Homo sapiens (NCBI:txid9606)	Found in cerebrospinal fluid (UBERON:0001359). See: PubMed
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study
Homo sapiens (NCBI:txid9606)	From MetaboLights See: MetaboLights Study

Roles Classification
Chemical Role(s):	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.

Biological Role(s):	Escherichia coli metabolite Any bacterial metabolite produced during a metabolic reaction in Escherichia coli. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). cofactor An organic molecule or ion (usually a metal ion) that is required by an enzyme for its activity. It may be attached either loosely (coenzyme) or tightly (prosthetic group). food colouring A food additive that imparts colour to food. In European countries, E-numbers for permitted food colours are from E 100 to E 199, divided into yellows (E 100-109), oranges (E 110-119), reds (E 120-129), blues and violets (E 130-139), greens (E 140-149), browns and blacks (E 150-159), and others (E 160-199). plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. human urinary metabolite Any metabolite (endogenous or exogenous) found in human urine samples. fundamental metabolite Any metabolite produced by all living cells. water-soluble vitamin (role) Any vitamin that dissolves in water and readily absorbed into tissues for immediate use. Unlike the fat-soluble vitamins, they are not stored in the body and need to be replenished regularly in the diet and will rarely accumulate to toxic levels since they are quickly excreted from the body via urine. (via B vitamin )

Application(s):	photosensitizing agent A chemical compound that can be excited by light of a specific wavelength and subsequently transfer energy to a chosen reactant. This is commonly molecular oxygen within a cancer tissue, which is converted to (highly rective) singlet state oxygen. This rapidly reacts with any nearby biomolecules, ultimately killing the cancer cells. food colouring A food additive that imparts colour to food. In European countries, E-numbers for permitted food colours are from E 100 to E 199, divided into yellows (E 100-109), oranges (E 110-119), reds (E 120-129), blues and violets (E 130-139), greens (E 140-149), browns and blacks (E 150-159), and others (E 160-199). anti-inflammatory agent Any compound that has anti-inflammatory effects. nutraceutical A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance. (via B vitamin )

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	riboflavin (CHEBI:17015) has role Escherichia coli metabolite (CHEBI:76971) riboflavin (CHEBI:17015) has role anti-inflammatory agent (CHEBI:67079) riboflavin (CHEBI:17015) has role antioxidant (CHEBI:22586) riboflavin (CHEBI:17015) has role cofactor (CHEBI:23357) riboflavin (CHEBI:17015) has role food colouring (CHEBI:77182) riboflavin (CHEBI:17015) has role fundamental metabolite (CHEBI:78675) riboflavin (CHEBI:17015) has role human urinary metabolite (CHEBI:84087) riboflavin (CHEBI:17015) has role mouse metabolite (CHEBI:75771) riboflavin (CHEBI:17015) has role photosensitizing agent (CHEBI:47868) riboflavin (CHEBI:17015) has role plant metabolite (CHEBI:76924) riboflavin (CHEBI:17015) is a flavin (CHEBI:30527) riboflavin (CHEBI:17015) is a vitamin B₂ (CHEBI:176838) riboflavin (CHEBI:17015) is conjugate acid of riboflavin(1−) (CHEBI:57986)

Incoming	7,8-didemethyl-8-hydroxy-5-deazariboflavin (CHEBI:43034) has functional parent riboflavin (CHEBI:17015) 8-amino-8-demethylriboflavin (CHEBI:137336) has functional parent riboflavin (CHEBI:17015) 8-demethyl-8-(methylamino)riboflavin (CHEBI:137340) has functional parent riboflavin (CHEBI:17015) dihydroriboflavins (CHEBI:15031) has functional parent riboflavin (CHEBI:17015) riboflavin cyclic 4',5'-phosphate (CHEBI:15045) has functional parent riboflavin (CHEBI:17015) riboflavin sodium phosphate (CHEBI:32098) has functional parent riboflavin (CHEBI:17015) roseoflavin (CHEBI:72346) has functional parent riboflavin (CHEBI:17015) vitamin B complex (CHEBI:75782) has part riboflavin (CHEBI:17015) riboflavin(1−) (CHEBI:57986) is conjugate base of riboflavin (CHEBI:17015)

IUPAC Name

1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol

INNs	Sources
riboflavin	WHO MedNet
riboflavina	WHO MedNet
riboflavine	WHO MedNet
riboflavinum	WHO MedNet

Synonyms

Sources

1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol

NIST Chemistry WebBook Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

5-deoxy-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol

ChEBI

6,7-dimethyl-9-D-ribitylisoalloxazine

Note: (2004-06-30) Uses obsolete isoalloxazine skeletal numbering system.

ChemIDplus Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dione

ChEBI

7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine

ChemIDplus Indicates when synonyms have been adapted from the specified source i.e. not exact copies.

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

IUPAC

7,8-dimethyl-10-ribitylisoalloxazine

KEGG COMPOUND

E101

ChEBI

lactoflavin

KEGG COMPOUND

riboflavin (vit B2)

DrugCentral

Vitamin B2

KEGG COMPOUND

vitamin B₂

ChEBI

vitamin G

DrugBank

vitasan B2

ChemIDplus

Brand Names	Sources
Aqua-Flave	ChemIDplus
Beflavin	ChemIDplus
Beflavine	ChemIDplus
Bisulase	KEGG DRUG
Dermadram	ChemIDplus
Fiboflavin	ChemIDplus
Flavaxin	ChemIDplus
Flavin Bb	ChemIDplus
Flaxain	ChemIDplus
Hyflavin	ChemIDplus

Manual Xrefs	Databases
2834	DrugCentral
431981	ChemSpider
C00001552	KNApSAcK
C00255	KEGG COMPOUND
D00050	KEGG DRUG
DB00140	DrugBank
FDB012160	FooDB
HMDB0000244	HMDB
LSM-4084	LINCS
RBF	PDBeChem
Riboflavin	Wikipedia
RIBOFLAVIN	MetaCyc
US2807611	Patent
US2876169	Patent
View more database links

Registry Numbers	Types	Sources
83-88-5	CAS Registry Number	KEGG COMPOUND
83-88-5	CAS Registry Number	NIST Chemistry WebBook
83-88-5	CAS Registry Number	ChemIDplus
97831	Reaxys Registry Number	Reaxys

Citations	Types	Sources
10566553	PubMed citation	Europe PMC
11399071	PubMed citation	Europe PMC
11606856	PubMed citation	Europe PMC
12083520	PubMed citation	Europe PMC
12354259	PubMed citation	Europe PMC
12927541	PubMed citation	Europe PMC
14963913	PubMed citation	Europe PMC
16273338	PubMed citation	Europe PMC
16460756	PubMed citation	Europe PMC
16658098	PubMed citation	Europe PMC
182198	PubMed citation	Europe PMC
18832377	PubMed citation	Europe PMC
19169240	PubMed citation	Europe PMC
19212411	PubMed citation	Europe PMC
19854891	PubMed citation	Europe PMC
22770225	PubMed citation	Europe PMC
2369885	PubMed citation	Europe PMC
23818044	PubMed citation	Europe PMC
24643482	PubMed citation	Europe PMC
24816110	PubMed citation	Europe PMC
25108762	PubMed citation	Europe PMC
25468971	PubMed citation	Europe PMC
25887755	PubMed citation	Europe PMC
2631092	PubMed citation	Europe PMC
29937405	PubMed citation	Europe PMC
3142982	PubMed citation	Europe PMC
33154451	PubMed citation	Europe PMC
33304888	PubMed citation	Europe PMC
33886098	PubMed citation	Europe PMC
33892358	PubMed citation	Europe PMC
34156642	PubMed citation	Europe PMC
3592624	PubMed citation	Europe PMC
3878498	PubMed citation	Europe PMC
4019261	PubMed citation	Europe PMC
6475825	PubMed citation	Europe PMC
6546833	PubMed citation	Europe PMC
6650303	PubMed citation	Europe PMC
7101408	PubMed citation	Europe PMC
7883462	PubMed citation	Europe PMC
8487103	PubMed citation	Europe PMC
8604671	PubMed citation	Europe PMC
8678471	PubMed citation	Europe PMC
8976642	PubMed citation	Europe PMC
9184778	PubMed citation	Europe PMC
9808225	PubMed citation	Europe PMC
9874201	PubMed citation	Europe PMC

Last Modified

20 July 2021

CHEBI:17015 - riboflavin

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