Milk Composition Database: Showing metabocard for Riboflavin (BMDB0000244)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:18 UTC

Update Date

2020-06-04 20:46:39 UTC

MCDB ID

BMDB0000244

Secondary Accession Numbers

BMDB00244

Metabolite Identification

Common Name

Riboflavin

Description

Riboflavin, also known as vitamin B2 or lactoflavin, 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. Riboflavin is a drug which is used for the treatment of ariboflavinosis (vitamin b2 deficiency). Riboflavin exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Riboflavin exists in all living species, ranging from bacteria to humans. Riboflavin is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	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
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
e101	ChEBI
Lactoflavin	ChEBI
Riboflavina	ChEBI
RIBOFLAVINE	ChEBI
Riboflavinum	ChEBI
Vitamin b2	ChEBI
Vitamin g	ChEBI
Bisulase	Kegg
(-)-Riboflavin	HMDB
1-Deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10(2H)-yl)-D-ribitol	HMDB
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
Beflavin	HMDB
Beflavine	HMDB
Benzo[g]pteridine riboflavin deriv.	HMDB
e 101	HMDB
Flavaxin	HMDB
Flavin BB	HMDB
Flaxain	HMDB
FOOD Yellow 15	HMDB
Hyre	HMDB
Lactobene	HMDB
Lactoflavine	HMDB
Ribipca	HMDB
Ribocrisina	HMDB
Riboderm	HMDB
Ribosyn	HMDB
Ribotone	HMDB
Ribovel	HMDB
Russupteridine yellow III	HMDB
San yellow b	HMDB
Vitaflavine	HMDB
Vitasan b2	HMDB
Vitamin b 2	HMDB

Chemical Formula

C₁₇H₂₀N₄O₆

Average Molecular Weight

376.3639

Monoisotopic Molecular Weight

376.138284392

IUPAC Name

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

Traditional Name

riboflavin

CAS Registry Number

83-88-5

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

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

Chemical Taxonomy

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	290 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.085 mg/mL	Not Available
LogP	-1.46	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-006x-4980000000-dd278a577316361d270a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-006x-4980000000-dd278a577316361d270a	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0btc-9014000000-75f046dc3c6cb008690e	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0zfs-5146149000-f9db57dd1ccd4a014604	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0a4i-0091000000-a82c54d3153103fcdb1f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0a4i-0091000000-a82c54d3153103fcdb1f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0090000000-2aff124ee1fc62c13844	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0090000000-f8b29c3e2c601a944a6c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0a4i-0090000000-4e8c9bd38ea0f5ae9a94	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090000000-5288e9226616bb75603c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0093000000-5999e10d04a53f4dae9b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0091000000-8f391045e25f26d53384	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-08fv-0290000000-b4d5f66b726c01d08c55	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-4690000000-d195fd5aee22ece7f2ec	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0039000000-549fbc0a59262f64680e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0195000000-58354696aaddaffc0fd8	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0f76-9231000000-67715e21d6e9ce2655fe	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-0090000000-838afb0228d293bee0a3	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2190000000-b659be001c9aa265c257	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0a4i-0090000000-21473bfb7f4a3eafd059	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-004i-0019000000-86365dedafa031aa7787	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-4390000000-ac1b59ab7cc2209f4241	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00dj-4900000000-72d33eb27b9bd6a13d9e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-004l-0569000000-874b71fdc78d04853bf0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-0239000000-659ca9fae9643f3ce73d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004l-0569000000-874b71fdc78d04853bf0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0006-0092000000-1f1be5508c1d50d8dff7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0006-0092000000-74bf0b86efe72fe37198	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-057i-0069000000-bb0522be4472e049dbc5	2017-09-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	5.048 uM	PMID: 17558655	details
Detected and Quantified	3.268 uM	USDA Food Co...	details
Detected and Quantified	3.268 uM	USDA Food Co...	details
Detected and Quantified	4.915 uM	USDA Food Co...	details
Detected and Quantified	3.72 uM	USDA Food Co...	details
Detected and Quantified	2.79 uM	USDA Food Co...	details
Detected and Quantified	5.101 uM	USDA Food Co...	details
Detected and Quantified	4.597 uM	USDA Food Co...	details
Detected and Quantified	4.915 uM	USDA Food Co...	details
Detected and Quantified	5.155 uM	USDA Food Co...	details
Detected and Quantified	4.65 uM	USDA Food Co...	details
Detected and Quantified	4.836 uM	USDA Food Co...	details
Detected and Quantified	4.836 uM	USDA Food Co...	details
Detected and Quantified	4.676 uM	Fooddata+, T...	details
Detected and Quantified	4.676 uM	Fooddata+, T...	details
Detected and Quantified	4.278 uM	USDA Food Co...	details
Detected and Quantified	5.155 uM	USDA Food Co...	details
Detected and Quantified	4.597 uM	USDA Food Co...	details
Detected and Quantified	5.155 uM	USDA Food Co...	details
Detected and Quantified	4.915 uM	USDA Food Co...	details
Detected and Quantified	4.915 uM	USDA Food Co...	details
Detected and Quantified	4.517 uM	Fooddata+, T...	details
Detected and Quantified	4.543 uM	Fooddata+, T...	details
Detected and Quantified	4.517 uM	Fooddata+, T...	details
Detected and Quantified	4.49 uM	USDA Food Co...	details
Detected and Quantified	4.49 uM	USDA Food Co...	details
Detected and Quantified	4.597 uM	Fooddata+, T...	details
Detected and Quantified	4.57 uM	Fooddata+, T...	details
Detected and Quantified	4.57 uM	Fooddata+, T...	details
Detected and Quantified	4.251 uM	Park, Y. W; Juáre...	details
Detected and Quantified	19 - 63 uM	PMID: 17558655	details
Detected and Quantified	3.72 - 4.38 uM	PMID: 22081685	details
Detected and Quantified	6.0 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	5.8 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	6.3 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	5.8 +/- 0.1 uM	PMID: 30994344	details

External Links

HMDB ID

HMDB0000244

DrugBank ID

DB00140

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Riboflavin

METLIN ID

Not Available

PubChem Compound

493570

PDB ID

Not Available

ChEBI ID

17015

References

Synthesis Reference

Tishler, Max; Pfister, Karl, III; Babson, R. D.; Ladenburg, Kurt; Fleming, Ann J. Reaction between o-aminoazo compounds and barbituric acid. A new synthesis of riboflavin. Journal of the American Chemical Society (1947), 69 1487-92.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Agostini TS, Scherer R, Godoy HT: Simultaneous determination of B-group vitamins in enriched Brazilian dairy products. Crit Rev Food Sci Nutr. 2007;47(5):435-9. doi: 10.1080/10408390600846309. [PubMed:17558655 ]
Gaucheron F: Milk and dairy products: a unique micronutrient combination. J Am Coll Nutr. 2011 Oct;30(5 Suppl 1):400S-9S. [PubMed:22081685 ]
Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. (2007). Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013. Small Ruminant Research.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
USDA Food Composition Databases [Link]
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Riboflavin (BMDB0000244)

Structure for BMDB0000244 (Riboflavin)