ContaminantDB: Nepitrin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 21:46:31 UTC

Update Date

2016-11-09 01:17:54 UTC

Accession Number

CHEM024544

Identification

Common Name

Nepitrin

Class

Small Molecule

Description

Nepitrin is found in herbs and spices. Nepitrin is a constituent of rosemary (Rosmarinus officinalis)

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
5,3',4'-Trihydroxy-6-methoxyflavone	MeSH
6-Methoxy-luteolin 7-glucoside	MeSH
6-Methoxyluteolin 7-glucoside	MeSH
3',4',5-Trihydroxy-6-methoxy-7-(glucosyloxy)flavone	HMDB
6-Methoxyluteolin-7-glucoside	HMDB
Eupafolin-7-glucoside	HMDB
Eupatolin 7-glucoside	HMDB
Nepetin 7-glucoside	HMDB
Nepitrin	MeSH

Chemical Formula

C₂₂H₂₂O₁₂

Average Molecular Mass

478.403 g/mol

Monoisotopic Mass

478.111 g/mol

CAS Registry Number

569-90-4

IUPAC Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

Traditional Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-6-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

SMILES

COC1=C(O)C2=C(OC(=CC2=O)C2=CC(O)=C(O)C=C2)C=C1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C22H22O12/c1-31-21-14(33-22-20(30)19(29)17(27)15(7-23)34-22)6-13-16(18(21)28)11(26)5-12(32-13)8-2-3-9(24)10(25)4-8/h2-6,15,17,19-20,22-25,27-30H,7H2,1H3/t15-,17-,19+,20-,22-/m1/s1

InChI Key

DMXHXBGUNHLMQO-IWLDQSELSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
6-methoxyflavonoid-skeleton
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Chromone
Benzopyran
1-benzopyran
Anisole
Catechol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Primary alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1 g/L	ALOGPS
logP	0.64	ALOGPS
logP	-0.023	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.55	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.5 m³·mol⁻¹	ChemAxon
Polarizability	46.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-08mi-9303700000-f9574a35f849db5c12c7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-057i-3331019000-38b2cafd26dd84df6bc2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-016r-0139800000-7381f32c2b8ee1a69f17	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0159100000-979d75d706753b47e369	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ktb-2497000000-991fd2ec43cf5a239cc8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00or-2305900000-999ea13afeedb13c8e40	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-2279300000-3724520d9cb4bc0f4b8b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01bd-4192000000-8c921c243c884d46107c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-016r-0009400000-f9e020672b78a8b5d2f7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0009100000-6d263fc476cff759693e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0009000000-d4d9bcf99cd318117dc6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000900000-9b72f8c346f02232b738	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0005900000-560bf2b0d639545ffeb4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0009100000-a0e7174b3d26a8851a40	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0030548

FooDB ID

FDB002423

Phenol Explorer ID

Not Available

KNApSAcK ID

C00004400

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

107783

ChEBI ID

581221

PubChem Compound ID

120742

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Agarwal OP: The anti-inflammatory action of nepitrin, a flavonoid. Agents Actions. 1982 Jul;12(3):298-302.

2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Nepitrin (CHEM024544)

Structure for CHEM024544: Nepitrin