ChemFOnt: Showing chemical card for 6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000124777)

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

CFc000124777

Molecule Identification

Common Name

6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Definition

6-{[(3s)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-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 (8s)-8-acetyl-10-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-6,8,11-trihydroxy-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-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₃₃H₃₅NO₁₆

Average Molecular Weight

701.634

Monoisotopic Molecular Weight

701.195584051

IUPAC Name

6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-2,4-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)(CC3=C(OC4([H])OC([H])(C(O)=O)C([H])(O)C([H])(O)C4([H])O)C4=C(C(O)=C23)C(=O)C2=C(C=CC=C2OC)C4=O)C(C)=O)OC(=C)C1([H])O

InChI Identifier

InChI=1S/C33H35NO16/c1-10-22(36)14(34)7-17(47-10)48-16-9-33(45,11(2)35)8-13-19(16)25(39)20-21(23(37)12-5-4-6-15(46-3)18(12)24(20)38)29(13)49-32-28(42)26(40)27(41)30(50-32)31(43)44/h4-6,14,16-17,22,26-28,30,32,36,39-42,45H,1,7-9,34H2,2-3H3,(H,43,44)/t14?,16?,17?,22?,26?,27?,28?,30?,32?,33-/m0/s1

InChI Key

JLGUJRSZMNULRT-HYTGVJPXSA-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

Anthracyclinone-skeleton
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
Aryl ketone
Anisole
Beta-hydroxy acid
Alkyl aryl ether
Hydroxy acid
Monosaccharide
Oxane
Benzenoid
Pyran
Alpha-hydroxy ketone
Vinylogous acid
Tertiary alcohol
Amino acid or derivatives
Ketone
Secondary alcohol
Amino acid
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid
Polyol
Ether
Primary amine
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Amine
Organonitrogen compound
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0144368)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.69 g/L	ALOGPS
logP	0.19	ALOGPS
logP	-2.7	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.23	ChemAxon
pKa (Strongest Basic)	9.23	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	282.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	165.25 m³·mol⁻¹	ChemAxon
Polarizability	68.47 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

HMDB0144368

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-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000124777)

MOL for CFc000124777 (6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000124777 (6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000124777 (6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000124777 (6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000124777 (6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000124777 (6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000124777 (6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000124777 (6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000124777 (6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000124777 (6-{[(3S)-3-acetyl-1-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-3,12-dihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)