Showing Compound Riboflavine (FDB012160)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:01 UTC

Update date

2020-09-17 15:38:30 UTC

Primary ID

FDB012160

Secondary Accession Numbers

FDB031145

Chemical Information

FooDB Name

Riboflavine

Description

Riboflavin, also known as lactoflavin or vitamin B2, belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring. It occurs in the free form 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. Riboflavin is a drug which is used for the treatment of ariboflavinosis (vitamin b2 deficiency). The antioxidant activity of riboflavin is principally derived from its role as a precursor of FAD and the role of this cofactor in the production of the antioxidant reduced glutathione. Riboflavin is an extremely weak basic (essentially neutral) compound (based on its pKa). Riboflavin exists in all living species, ranging from bacteria to humans. Binds to riboflavin hydrogenase, riboflavin kinase, and riboflavin synthase. In humans, riboflavin is involved in the metabolic disorder called the medium chain acyl-coa dehydrogenase deficiency (mcad) pathway. Outside of the human body, Riboflavin is found, on average, in the highest concentration within a few different foods, such as saffrons, saskatoon berries, and leavening agents and in a lower concentration in grape wines, hippoglossus (common halibut), and spiny lobsters. Riboflavin has also been detected, but not quantified in, several different foods, such as bog bilberries, lowbush blueberries, greenthread tea, nanking cherries, and black radish. This could make riboflavin a potential biomarker for the consumption of these foods. Riboflavin is a potentially toxic compound. Nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. The richest natural source is yeast.

CAS Number

83-88-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(-)-Riboflavin	HMDB
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol	HMDB
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol, 9CI	db_source
1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol	ChEBI
6,7-Dimethyl-9-D-ribitylisoalloxazine	ChEBI
6,7-Dimethyl-9-ribitylisoalloxazine	HMDB
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)-benzo[g]pteridine-2,4(3H,10H)-dione	HMDB
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	ChEBI
7,8-Dimethyl-10-ribitylisoalloxazine	ChEBI

Showing 1 to 10 of 47 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.66 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.92	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	5.97	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.27 m³·mol⁻¹	ChemAxon
Polarizability	37.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C17H20N4O6

IUPAC name

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

InChI Identifier

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

Isomeric 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

Average Molecular Weight

376.3639

Monoisotopic Molecular Weight

376.138284392

Classification

Description

Belongs to the class of organic compounds known as flavins. Flavins are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pteridines and derivatives

Sub Class

Alloxazines and isoalloxazines

Direct Parent

Flavins

Alternative Parents

Substituents

Flavin
Diazanaphthalene
Quinoxaline
Pyrimidone
Pyrazine
Pyrimidine
Benzenoid
Heteroaromatic compound
Vinylogous amide
Secondary alcohol
Lactam
Polyol
Azacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

flavin (CHEBI:17015 )
Water-soluble vitamins (C00255 )

Ontology

Physiological effect

Health effect:

Health condition:

Anorexia nervosa

Food

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Subcellular:

Organ and components:

Cell and elements:

Extracellular

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Alcoholism

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Essential vitamin

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	-1.46	HANSCH,C ET AL. (1995)
Experimental pKa	pKa2 10.2 (25°)	DFC
Experimental Water Solubility	0.0847 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Isoelectric point	Not Available
Mass Composition	C 54.25%; H 5.36%; N 14.89%; O 25.51%	DFC
Melting Point	Mp 280° dec.	DFC
Optical Rotation	[a]D -125 (20N NaOH)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Riboflavine, non-derivatized, GC-MS Spectrum	splash10-006x-4980000000-dd278a577316361d270a	Spectrum
GC-MS	Riboflavine, non-derivatized, GC-MS Spectrum	splash10-006x-4980000000-dd278a577316361d270a	Spectrum
Predicted GC-MS	Riboflavine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0btc-9014000000-75f046dc3c6cb008690e	Spectrum
Predicted GC-MS	Riboflavine, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0zfs-5146149000-f9db57dd1ccd4a014604	Spectrum
Predicted GC-MS	Riboflavine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Riboflavine, TMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0a4i-0091000000-a82c54d3153103fcdb1f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0091000000-a82c54d3153103fcdb1f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0090000000-2aff124ee1fc62c13844	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0090000000-f8b29c3e2c601a944a6c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0090000000-4e8c9bd38ea0f5ae9a94	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090000000-5288e9226616bb75603c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0093000000-5999e10d04a53f4dae9b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0091000000-8f391045e25f26d53384	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-08fv-0290000000-b4d5f66b726c01d08c55	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-4690000000-d195fd5aee22ece7f2ec	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0039000000-549fbc0a59262f64680e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0195000000-58354696aaddaffc0fd8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0f76-9231000000-67715e21d6e9ce2655fe	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-0090000000-838afb0228d293bee0a3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2190000000-b659be001c9aa265c257	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-0090000000-21473bfb7f4a3eafd059	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0019000000-86365dedafa031aa7787	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-4390000000-ac1b59ab7cc2209f4241	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00dj-4900000000-72d33eb27b9bd6a13d9e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-004l-0569000000-874b71fdc78d04853bf0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-0239000000-659ca9fae9643f3ce73d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004l-0569000000-874b71fdc78d04853bf0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0006-0092000000-1f1be5508c1d50d8dff7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0006-0092000000-74bf0b86efe72fe37198	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-057i-0069000000-bb0522be4472e049dbc5	2017-09-14	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17015

Phenol-Explorer ID

Not Available

DrugBank ID

DB00140

HMDB ID

HMDB00244

CRC / DFC (Dictionary of Food Compounds) ID

HDV43-H:HDV43-H

EAFUS ID

3302

Dr. Duke ID

VITAMIN-B-2|VIT-B2|RIBOFLAVIN

BIGG ID

34409

KNApSAcK ID

Not Available

HET ID

RBF

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Riboflavin

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anti arabiflavinotic			DUKE
anti carpal-tunnel			DUKE
anti cataract	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cephalagic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cervicaldysplasic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti cheilitic			DUKE
anti cheilotic			DUKE
anti decubitic			DUKE
anti glossitic			DUKE
anti keratitic			DUKE

Showing 1 to 10 of 16 entries

Enzymes

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Name	Gene Name	UniProt ID
Glycogen phosphorylase, liver form	PYGL	P06737
Lysophosphatidic acid phosphatase type 6	ACP6	Q9NPH0
Lysosomal acid phosphatase	ACP2	P11117
Prostatic acid phosphatase	ACPP	P15309
Putative uncharacterized protein ACP1	ACP1	B5MCC7
Solute carrier family 52, riboflavin transporter, member 1	SLC52A1	Q9NWF4
Testicular acid phosphatase	ACPT	Q9BZG2