(−)-Riboflavin - Moligand™, BioReagent, for cell culture, for insect cell culture , CAS No.83-88-5

CAS: 83-88-5 Cat. No.: R434262 Formula: C₁₇H₂₀N₄O₆ Molecular Weight: 376.36 Beilstein Registry Number: 97825 EC Number: 201-507-1 PubChem CID: 493570

GRADE & PURITY BioReagent, Moligand™, for Cell culture, Suitable for insect cell culture

Synonyms

Q-200410 | Vitamin B2; E101 | 1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo(g)pteridin-10(2H)-yl)-D-ribitol | Ribovel | Vitamin G | 2vxa | D-Ribitol, 1-deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo(g)pteridin-10(2H)-yl)- | DTXCID401777 | E101 | In

Storage

Room temperature

Shipped In

Normal

Overview

Riboflavin is an essential vitamin soluble in water. Milk and eggs are found to be its major sources. Riboflavin is usually bound to enzymes in all tissues. During riboflavin localization in plasma, it is bound to albumin and specific immunoglobulins.

Application

(-)-Riboflavin has been used to administer intraperitoneally to experimental mice to study its protective role in stroke in middle cerebral artery occlusion. It has also been used with Krebs′ solution, to model ischemia-like conditions in vitro .

Specifications

Synonyms

Q-200410 | Vitamin B2; E101 | 1-deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo(g)pteridin-10(2H)-yl)-D-ribitol | Ribovel | Vitamin G | 2vxa | D-Ribitol, 1-deoxy-1-(3,4-dihydro-7,8-dimethyl-2,4-dioxobenzo(g)pteridin-10(2H)-yl)- | DTXCID401777 | E101 | In

Specifications & Purity

Moligand™, BioReagent, for cell culture, for insect cell culture

Biochemical and Physiological Mechanisms

Riboflavin serves as a precursor for the active enzyme cofactors riboflavin 5′-monophosphate (also called flavin mononucleotide or FMN) and flavin adenine dinucleotide (FAD). Riboflavin deficiency in the diet results in a well-defined syndrome known as ar

Storage

Room temperature

Shipped In

Normal

Grade

BioReagent, for Cell culture, Moligand™, Suitable for insect cell culture

Names and Identifiers

Pubchem Sid

504758946

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504758946

Canonical Smiles

CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)CC(C(C(CO)O)O)O

IUPAC Name

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

InChIKey

AUNGANRZJHBGPY-SCRDCRAPSA-N

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

Isomeric SMILES

CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@@H]([C@@H](CO)O)O)O

WGK Germany

1

RTECS

VJ1400000

PubChem CID

493570

Molecular Weight

376.36

Beilstein

97825

Reaxy-Rn

97825

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pteridines and derivatives
      • Subclass Alloxazines and isoalloxazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pteridines and derivatives
• Subclass: Alloxazines and isoalloxazines
• Intermediate Tree Nodes: Not available
• Direct Parent: Flavins
• Alternative Parents: Quinoxalines Pyrimidones Pyrazines Benzenoids Vinylogous amides Heteroaromatic compounds Secondary alcohols Lactams Polyols Azacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• 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
• Description: This compound belongs to the class of organic compounds known as flavins. These are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring.
• External Descriptors: Water-soluble vitamins

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

AR Tclin Androgen Receptor (11781 Activities)

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VDR Tclin Vitamin D receptor (26531 Activities)

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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TNF Tclin TNF-alpha (1897 Activities)

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THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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RXRA Tclin Retinoid X receptor alpha (3637 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

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NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)

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CASP1 Tchem Caspase-1 (6235 Activities)

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CTRC Tchem Chymotrypsin C (381 Activities)

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ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

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CASP7 Tchem Caspase-7 (3146 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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Homo sapiens (32628 Activities)

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A-375 (9258 Activities)

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Lymphoblastoid cell (5959 Activities)

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HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)

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BRCA1 Tchem Breast cancer type 1 susceptibility protein (15908 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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RECQL Tbio ATP-dependent DNA helicase Q1 (5575 Activities)

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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HSPD1 Tbio HSP60/HSP10 (366 Activities)

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TST Tchem Thiosulfate sulfurtransferase (144 Activities)

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Associated Targets(non-human)

ampC Beta-lactamase AmpC (62480 Activities)

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Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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MDH2 Malate dehydrogenase mitochondrial (131 Activities)

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lef Anthrax lethal factor (7585 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Slc22a6 Solute carrier family 22 member 6 (141 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

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Riboflavin-binding protein (12 Activities)

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Cenchrus americanus (77 Activities)

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groL GroEL/GroES (1042 Activities)

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groEL 60 kDa chaperonin (64 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: 0.1 M NaOH: 10mg/mL, clear, yellow to orange
• Specific Rotation[α]: -128.0 to -142.0 deg (C=0.5, JP Method)
• Melt Point(°C): 290°C
• Molecular Weight: 376.400 g/mol
• XLogP3: -1.500
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 376.138 Da
• Monoisotopic Mass: 376.138 Da
• Topological Polar Surface Area: 155.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 680.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Frequently Asked Questions

What is Moligand??

Moligand? is one of Aladdin Scientific's premium product lines, formulated for high-purity applications across multiple workflows. Compared to standard grades in the same workflow, Moligand? products typically offer tighter specifications, more rigorous QC, and stronger lot-to-lot consistency.

What does BioReagent mean?

BioReagent indicates that the product has been processed and tested for biological and biochemical applications. Specifications may include endotoxin limits, microbial controls, sterility, low DNase/RNase/protease activity, and verified biological activity where relevant.

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 83-88-5, the molecular formula is C17H20N4O6, and the molecular weight is 376.36 g/mol. InChIKey AUNGANRZJHBGPY-SCRDCRAPSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.