ChemFOnt: Showing chemical card for 6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000125568)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:52:24 UTC

Chemfont ID

CFc000125568

Molecule Identification

Common Name

6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-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-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid 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. Based on a literature review very few articles have been published on 6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

Chemical Formula

C₃₂H₃₃NO₁₅

Average Molecular Weight

671.608

Monoisotopic Molecular Weight

671.185019367

IUPAC Name

6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-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-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-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)(CC3=C(O)C4=C(C(=O)C5=CC=CC=C5C4=O)C(OC4([H])OC([H])(C(O)=O)C([H])(O)C([H])(O)C4([H])O)=C23)C(C)=O)OC(=C)C1([H])O

InChI Identifier

InChI=1S/C32H33NO15/c1-10-21(35)15(33)7-17(45-10)46-16-9-32(44,11(2)34)8-14-18(16)28(47-31-27(41)25(39)26(40)29(48-31)30(42)43)20-19(24(14)38)22(36)12-5-3-4-6-13(12)23(20)37/h3-6,15-17,21,25-27,29,31,35,38-41,44H,1,7-9,33H2,2H3,(H,42,43)/t15?,16?,17?,21?,25?,26?,27?,29?,31?,32-/m0/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0145159)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.65 g/L	ALOGPS
logP	0.15	ALOGPS
logP	-2.6	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.3	ChemAxon
pKa (Strongest Basic)	9.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	272.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	158.78 m³·mol⁻¹	ChemAxon
Polarizability	65.43 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

HMDB0145159

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-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000125568)

MOL for CFc000125568 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000125568 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000125568 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000125568 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000125568 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000125568 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000125568 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000125568 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000125568 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000125568 (6-{[(2S)-2-acetyl-4-[(4-amino-5-hydroxy-6-methylideneoxan-2-yl)oxy]-2,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)