ChemFOnt: Showing chemical card for 3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid (CFc000123641)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:49:27 UTC

Chemfont ID

CFc000123641

Molecule Identification

Common Name

3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid

Definition

3,4,5-trihydroxy-6-{[(3s)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 2,2,2-trifluoro-n-(3-hydroxy-2-methyl-6-{[(3s)-3,5,9,12-tetrahydroxy-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-4-yl)ethanimidic acid. 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-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylate	Generator

Chemical Formula

C₄₀H₄₄F₃NO₂₀

Average Molecular Weight

915.774

Monoisotopic Molecular Weight

915.24087731

IUPAC Name

Traditional Name

3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-2,4-dihydro-1H-tetracen-5-yl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]C1(C)OC([H])(CC([H])(N=C(O)C(F)(F)F)C1([H])O)OC1([H])C[C@@](O)(CC2=C(OC3([H])OC([H])(C(O)=O)C([H])(O)C([H])(O)C3([H])O)C3=C(C(O)=C12)C(=O)C1=C(C=CC(O)=C1OC)C3=O)C(=O)COC(=O)CCCC

InChI Identifier

InChI=1S/C40H44F3NO20/c1-4-5-6-20(47)60-12-19(46)39(58)10-15-22(18(11-39)62-21-9-16(26(48)13(2)61-21)44-38(57)40(41,42)43)28(50)24-25(27(49)14-7-8-17(45)34(59-3)23(14)29(24)51)33(15)63-37-32(54)30(52)31(53)35(64-37)36(55)56/h7-8,13,16,18,21,26,30-32,35,37,45,48,50,52-54,58H,4-6,9-12H2,1-3H3,(H,44,57)(H,55,56)/t13?,16?,18?,21?,26?,30?,31?,32?,35?,37?,39-/m0/s1

InChI Key

MZNHAXBPSAKCRA-XKSJXXCFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Anthracyclines

Sub Class

Not Available

Direct Parent

Anthracyclines

Alternative Parents

Substituents

Anthracycline
Anthracyclinone-skeleton
Tetracenequinone
Hydroxyanthraquinone
1,4-anthraquinone
9,10-anthraquinone
Phenolic glycoside
Anthracene
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Tetralin
Anisole
Aryl ketone
Beta-hydroxy acid
Fatty acid ester
Alpha-acyloxy ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acyl
Dicarboxylic acid or derivatives
Hydroxy acid
Benzenoid
Monosaccharide
Pyran
Oxane
Tertiary alcohol
Alpha-hydroxy ketone
Vinylogous acid
Secondary alcohol
Ketone
Carboxylic acid ester
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Ether
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organofluoride
Organohalogen compound
Alkyl halide
Alkyl fluoride
Organopnictogen compound
Alcohol
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0143232)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	1.5	ALOGPS
logP	-0.58	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	-3.1	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	335.16 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	202.54 m³·mol⁻¹	ChemAxon
Polarizability	86.86 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0143232

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 3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid (CFc000123641)

MOL for CFc000123641 (3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid)

3D MOL for CFc000123641 (3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid)

3D SDF for CFc000123641 (3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid)

3D-SDF for CFc000123641 (3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid)

PDB for CFc000123641 (3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid)

3D PDB for CFc000123641 (3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid)

SMILES for CFc000123641 (3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid)

INCHI for CFc000123641 (3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid)

Structure for CFc000123641 (3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid)

3D Structure for CFc000123641 (3,4,5-trihydroxy-6-{[(3S)-3,9,12-trihydroxy-1-({5-hydroxy-6-methyl-4-[(2,2,2-trifluoro-1-hydroxyethylidene)amino]oxan-2-yl}oxy)-10-methoxy-6,11-dioxo-3-[2-(pentanoyloxy)acetyl]-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}oxane-2-carboxylic acid)