ChemFOnt: Showing chemical card for (6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid (CFc000124764)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:51:10 UTC

Chemfont ID

CFc000124764

Molecule Identification

Common Name

(6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid

Definition

(6-{[(3s)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of (8s)-8-acetyl-10-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-3,6,8,11-tetrahydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione. It is generated by Sulfotransferase family cytosolic 2B member 1 (O00204) and Sulfotransferase enzymes via a sulfation-of-secondary-alcohol reaction. This sulfation-of-secondary-alcohol occurs in humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonate	Generator
(6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulphonate	Generator
(6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulphonic acid	Generator

Chemical Formula

C₂₇H₂₉NO₁₄S

Average Molecular Weight

623.58

Monoisotopic Molecular Weight

623.130875792

IUPAC Name

(6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid

Traditional Name

(6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy}-4-amino-2-methyloxan-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=C(C=C(O)C=C2OC)C4=O)C(C)=O)OC([H])(C)C1([H])OS(O)(=O)=O

InChI Identifier

InChI=1S/C27H29NO14S/c1-9-26(42-43(36,37)38)14(28)6-17(40-9)41-16-8-27(35,10(2)29)7-13-19(16)25(34)21-20(23(13)32)22(31)12-4-11(30)5-15(39-3)18(12)24(21)33/h4-5,9,14,16-17,26,30,32,34-35H,6-8,28H2,1-3H3,(H,36,37,38)/t9?,14?,16?,17?,26?,27-/m0/s1

InChI Key

XITKPOXGKKXQAU-DLGGVOOKSA-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
Anthracycline
Aminoglycoside core
Tetracenequinone
1,4-anthraquinone
Hydroxyanthraquinone
9,10-anthraquinone
Anthracene
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Tetralin
Monosaccharide sulfate
Anisole
Aryl ketone
Amino saccharide
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Sulfuric acid ester
Benzenoid
Sulfate-ester
Sulfuric acid monoester
Alkyl sulfate
Oxane
Monosaccharide
Tertiary alcohol
Vinylogous acid
Organic sulfuric acid or derivatives
Alpha-hydroxy ketone
Ketone
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic nitrogen compound
Carbonyl group
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Amine
Organopnictogen compound
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0144355)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.1 g/L	ALOGPS
logP	0.71	ALOGPS
logP	1.06	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
pKa (Strongest Basic)	8.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	249.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	144.86 m³·mol⁻¹	ChemAxon
Polarizability	60.42 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

HMDB0144355

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-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid (CFc000124764)

MOL for CFc000124764 ((6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid)

3D MOL for CFc000124764 ((6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid)

3D SDF for CFc000124764 ((6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid)

3D-SDF for CFc000124764 ((6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid)

PDB for CFc000124764 ((6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid)

3D PDB for CFc000124764 ((6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid)

SMILES for CFc000124764 ((6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid)

INCHI for CFc000124764 ((6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid)

Structure for CFc000124764 ((6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid)

3D Structure for CFc000124764 ((6-{[(3S)-3-acetyl-3,5,8,12-tetrahydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}-4-amino-2-methyloxan-3-yl)oxidanesulfonic acid)