ChemFOnt: Showing chemical card for (6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid (CFc000125548)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:52:22 UTC

Chemfont ID

CFc000125548

Molecule Identification

Common Name

(6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid

Definition

(6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic 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 (6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonate	Generator
(6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulphonate	Generator
(6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulphonic acid	Generator

Chemical Formula

C₂₆H₂₇NO₁₃S

Average Molecular Weight

593.56

Monoisotopic Molecular Weight

593.120311107

IUPAC Name

(6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid

Traditional Name

(6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

[H]C1(N)CC([H])(OC2([H])C[C@@](O)(CC3=C(O)C4=C(C(O)=C23)C(=O)C2=CC=CC=C2C4=O)C(C)=O)OC([H])(CO)C1([H])OS(O)(=O)=O

InChI Identifier

InChI=1S/C26H27NO13S/c1-10(29)26(34)7-13-18(15(8-26)38-17-6-14(27)25(16(9-28)39-17)40-41(35,36)37)24(33)20-19(23(13)32)21(30)11-4-2-3-5-12(11)22(20)31/h2-5,14-17,25,28,32-34H,6-9,27H2,1H3,(H,35,36,37)/t14?,15?,16?,17?,25?,26-/m0/s1

InChI Key

XOWVUDXDNMWEQG-DMLGKAOXSA-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
Anthracene
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Monosaccharide sulfate
Tetralin
Aryl ketone
Amino saccharide
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Oxane
Monosaccharide
Benzenoid
Vinylogous acid
Tertiary alcohol
Organic sulfuric acid or derivatives
Alpha-hydroxy ketone
Ketone
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Primary alcohol
Primary amine
Carbonyl group
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Primary aliphatic amine
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0145139)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.32 g/L	ALOGPS
logP	0.01	ALOGPS
logP	0.48	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
pKa (Strongest Basic)	7.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	240.21 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	137.96 m³·mol⁻¹	ChemAxon
Polarizability	57.26 Å³	ChemAxon
Number of Rings	5	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

HMDB0145139

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-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid (CFc000125548)

MOL for CFc000125548 ((6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

3D MOL for CFc000125548 ((6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

3D SDF for CFc000125548 ((6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

3D-SDF for CFc000125548 ((6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

PDB for CFc000125548 ((6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

3D PDB for CFc000125548 ((6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

SMILES for CFc000125548 ((6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

INCHI for CFc000125548 ((6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

Structure for CFc000125548 ((6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)

3D Structure for CFc000125548 ((6-{[(3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-(hydroxymethyl)oxan-3-yl)oxidanesulfonic acid)