ChemFOnt: Showing chemical card for 6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000124770)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:51:11 UTC

Chemfont ID

CFc000124770

Molecule Identification

Common Name

6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Definition

6-{[(2s)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of (8r)-8-acetyl-10-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-6,7,8,11-tetrahydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione. 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
6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₃₃H₃₇NO₁₇

Average Molecular Weight

719.649

Monoisotopic Molecular Weight

719.206148735

IUPAC Name

6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]C1(N)CC([H])(OC2([H])C[C@@](O)(C(C)=O)C([H])(O)C3=C2C(OC2([H])OC([H])(C(O)=O)C([H])(O)C([H])(O)C2([H])O)=C2C(=O)C4=C(C=CC=C4OC)C(=O)C2=C3O)OC([H])(C)C1([H])O

InChI Identifier

InChI=1S/C33H37NO17/c1-9-21(36)12(34)7-15(48-9)49-14-8-33(46,10(2)35)30(43)20-17(14)28(50-32-27(42)25(40)26(41)29(51-32)31(44)45)19-18(24(20)39)22(37)11-5-4-6-13(47-3)16(11)23(19)38/h4-6,9,12,14-15,21,25-27,29-30,32,36,39-43,46H,7-8,34H2,1-3H3,(H,44,45)/t9?,12?,14?,15?,21?,25?,26?,27?,29?,30?,32?,33-/m1/s1

InChI Key

TVDOFLPFBKHNIP-MVGXRIISSA-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
Aminoglycoside core
Tetracenequinone
9,10-anthraquinone
1,4-anthraquinone
Phenolic glycoside
Anthracene
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Tetralin
Anisole
Aryl ketone
Amino saccharide
Beta-hydroxy acid
Alkyl aryl ether
Pyran
Hydroxy acid
Oxane
Benzenoid
Monosaccharide
Tertiary alcohol
Alpha-hydroxy ketone
Vinylogous acid
Amino acid or derivatives
Amino acid
Ketone
1,2-aminoalcohol
Secondary alcohol
Acetal
Polyol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Primary amine
Carbonyl group
Organooxygen compound
Amine
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0144361)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.13 g/L	ALOGPS
logP	0.15	ALOGPS
logP	-3.5	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	2.18	ChemAxon
pKa (Strongest Basic)	9.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	302.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	166.11 m³·mol⁻¹	ChemAxon
Polarizability	69.24 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

HMDB0144361

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-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000124770)

MOL for CFc000124770 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000124770 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000124770 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000124770 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000124770 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000124770 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000124770 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000124770 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000124770 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000124770 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-1,2,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)