ChemFOnt: Showing chemical card for 6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000159961)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:48:14 UTC

Chemfont ID

CFc000159961

Molecule Identification

Common Name

Definition

6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton. Based on a literature review very few articles have been published on 6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,7H,7ah-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₃₁H₃₆O₁₉

Average Molecular Weight

712.61

Monoisotopic Molecular Weight

712.185078939

IUPAC Name

Traditional Name

6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC=C(OC2OC(C(O)C(O)C2O)C(O)=O)C=C1)C(=O)OCC1(O)C=CC2C1C(OC1OC(CO)C(O)C(O)C1O)OC=C2C(O)=O

InChI Identifier

InChI=1S/C31H36O19/c32-9-16-19(34)20(35)23(38)30(48-16)50-28-18-14(15(10-45-28)26(40)41)7-8-31(18,44)11-46-17(33)6-3-12-1-4-13(5-2-12)47-29-24(39)21(36)22(37)25(49-29)27(42)43/h1-8,10,14,16,18-25,28-30,32,34-39,44H,9,11H2,(H,40,41)(H,42,43)/b6-3+

InChI Key

MUABVDWKEKGSII-ZZXKWVIFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Phenolic glycoside
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Cinnamic acid ester
Cinnamic acid or derivatives
O-glycosyl compound
Iridoid-skeleton
Glycosyl compound
Monoterpenoid
Bicyclic monoterpenoid
Aromatic monoterpenoid
Tricarboxylic acid or derivatives
Phenoxy compound
Styrene
Phenol ether
Fatty acid ester
Beta-hydroxy acid
Fatty acyl
Benzenoid
Pyran
Oxane
Monosaccharide
Hydroxy acid
Monocyclic benzene moiety
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.89 g/L	ALOGPS
logP	-0.98	ALOGPS
logP	-2.5	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.19	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	308.89 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	158.58 m³·mol⁻¹	ChemAxon
Polarizability	68.44 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

HMDB0179553

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

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 6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000159961)

MOL for CFc000159961 (6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000159961 (6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000159961 (6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000159961 (6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000159961 (6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000159961 (6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000159961 (6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000159961 (6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000159961 (6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000159961 (6-{4-[(1E)-3-[(4-carboxy-7-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,7H,7aH-cyclopenta[c]pyran-7-yl)methoxy]-3-oxoprop-1-en-1-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)