ChemFOnt: Showing chemical card for 3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid (CFc000109315)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:28:03 UTC

Chemfont ID

CFc000109315

Molecule Identification

Common Name

3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid

Definition

3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 15,17-dihydroxy-11,18-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14(19),15,17-heptaen-13-one. It is generated by UDP-glucuronosyltransferase 1-1 (P22309) enzyme via an aromatic-OH-glucuronidation reaction. This aromatic-OH-glucuronidation occurs in humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4,5-Trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0,.0,.0,]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylate	Generator
3,4,5-Trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylate	Generator

Chemical Formula

C₂₅H₂₂O₁₄

Average Molecular Weight

546.437

Monoisotopic Molecular Weight

546.100955388

IUPAC Name

3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid

Traditional Name

3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid

CAS Registry Number

None

SMILES

COC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(OC3OC(C(O)C(O)C3O)C(O)=O)C=C(O)C(OC)=C1O2

InChI Identifier

InChI=1S/C25H22O14/c1-33-9-6-11-12(7-3-4-35-24(7)36-11)20-13(9)15(27)14-10(5-8(26)19(34-2)21(14)38-20)37-25-18(30)16(28)17(29)22(39-25)23(31)32/h3-7,16-18,22,24-26,28-30H,1-2H3,(H,31,32)

InChI Key

AXFHXDUVFWWFJM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sterigmatocystins. These are a group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. And Bipolaris spp.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Sterigmatocystins

Sub Class

Not Available

Direct Parent

Sterigmatocystins

Alternative Parents

Substituents

Sterigmatocystin backbone
Phenolic glycoside
Xanthone
Dibenzopyran
1-o-glucuronide
O-glucuronide
Xanthene
Glucuronic acid or derivatives
Chromone
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Coumaran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Alkyl aryl ether
Pyranone
Hydroxy acid
Monosaccharide
Benzenoid
Pyran
Oxane
Vinylogous ester
Dihydrofuran
Heteroaromatic compound
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Monocarboxylic acid or derivatives
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0128906)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.22 g/L	ALOGPS
logP	0.99	ALOGPS
logP	0.04	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.33	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	199.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	124.16 m³·mol⁻¹	ChemAxon
Polarizability	50.6 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0128906

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB087757

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

131835201

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid (CFc000109315)

MOL for CFc000109315 (3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid)

3D MOL for CFc000109315 (3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid)

3D SDF for CFc000109315 (3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid)

3D-SDF for CFc000109315 (3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid)

PDB for CFc000109315 (3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid)

3D PDB for CFc000109315 (3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid)

SMILES for CFc000109315 (3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid)

INCHI for CFc000109315 (3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid)

Structure for CFc000109315 (3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid)

3D Structure for CFc000109315 (3,4,5-trihydroxy-6-({17-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-15-yl}oxy)oxane-2-carboxylic acid)