ChemFOnt: Showing chemical card for Leucopelargonidin 3-O-alpha-L-rhamno-beta-D-glucopyranoside (CFc000282135)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:12 UTC

Chemfont ID

CFc000282135

Molecule Identification

Common Name

Leucopelargonidin 3-O-alpha-L-rhamno-beta-D-glucopyranoside

Definition

Leucopelargonidin 3-o-alpha-l-rhamno-beta-d-glucopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Leucopelargonidin 3-o-alpha-l-rhamno-beta-d-glucopyranoside can be found in loquat, which makes leucopelargonidin 3-o-alpha-l-rhamno-beta-d-glucopyranoside a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Leucopelargonidin 3-O-a-L-rhamno-b-D-glucopyranoside	Generator
Leucopelargonidin 3-O-α-L-rhamno-β-D-glucopyranoside	Generator

Chemical Formula

C₂₇H₃₄O₁₅

Average Molecular Weight

598.5499

Monoisotopic Molecular Weight

598.189770418

IUPAC Name

2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4,5,7-triol

Traditional Name

2-(4-hydroxyphenyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4,5,7-triol

CAS Registry Number

None

SMILES

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3C(O)C4=C(O)C=C(O)C=C4OC3C3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C27H34O15/c1-9-17(31)20(34)22(36)26(39-9)38-8-15-18(32)21(35)23(37)27(41-15)42-25-19(33)16-13(30)6-12(29)7-14(16)40-24(25)10-2-4-11(28)5-3-10/h2-7,9,15,17-37H,8H2,1H3/t9-,15+,17-,18+,19?,20+,21-,22+,23+,24?,25?,26+,27-/m0/s1

InChI Key

NODFKYJZPMLAJM-PATRHMBYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
Leucoanthocyanidin-skeleton
4-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
4'-hydroxyflavonoid
Flavan
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Chromane
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Oxane
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302619)

Food

Fruit

Tropical fruit

Loquat (FooDB: FOOD00076)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	8.62 g/L	ALOGPS
logP	-0.72	ALOGPS
logP	-1.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.08	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	248.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.51 m³·mol⁻¹	ChemAxon
Polarizability	57.6 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0302619

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005419

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Leucopelargonidin 3-O-alpha-L-rhamno-beta-D-glucopyranoside (CFc000282135)

MOL for CFc000282135 (Leucopelargonidin 3-O-alpha-L-rhamno-beta-D-glucopyranoside)

3D MOL for CFc000282135 (Leucopelargonidin 3-O-alpha-L-rhamno-beta-D-glucopyranoside)

3D SDF for CFc000282135 (Leucopelargonidin 3-O-alpha-L-rhamno-beta-D-glucopyranoside)

3D-SDF for CFc000282135 (Leucopelargonidin 3-O-alpha-L-rhamno-beta-D-glucopyranoside)

PDB for CFc000282135 (Leucopelargonidin 3-O-alpha-L-rhamno-beta-D-glucopyranoside)

3D PDB for CFc000282135 (Leucopelargonidin 3-O-alpha-L-rhamno-beta-D-glucopyranoside)

SMILES for CFc000282135 (Leucopelargonidin 3-O-alpha-L-rhamno-beta-D-glucopyranoside)

INCHI for CFc000282135 (Leucopelargonidin 3-O-alpha-L-rhamno-beta-D-glucopyranoside)

Structure for CFc000282135 (Leucopelargonidin 3-O-alpha-L-rhamno-beta-D-glucopyranoside)

3D Structure for CFc000282135 (Leucopelargonidin 3-O-alpha-L-rhamno-beta-D-glucopyranoside)