ChemFOnt: Showing chemical card for (4-amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonic acid (CFc000123730)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:49:35 UTC

Chemfont ID

CFc000123730

Molecule Identification

Common Name

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

Definition

(4-amino-2-methyl-6-{[(3s)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of (8s)-10-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-3,6,8,11-tetrahydroxy-8-(2-hydroxyacetyl)-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
(4-Amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonate	Generator
(4-Amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulphonate	Generator
(4-Amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulphonic acid	Generator

Chemical Formula

C₂₇H₂₉NO₁₅S

Average Molecular Weight

639.58

Monoisotopic Molecular Weight

639.125790412

IUPAC Name

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

Traditional Name

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

InChI Identifier

InChI=1S/C27H29NO15S/c1-9-26(43-44(37,38)39)13(28)5-17(41-9)42-15-7-27(36,16(31)8-29)6-12-19(15)25(35)21-20(23(12)33)22(32)11-3-10(30)4-14(40-2)18(11)24(21)34/h3-4,9,13,15,17,26,29-30,33,35-36H,5-8,28H2,1-2H3,(H,37,38,39)/t9?,13?,15?,17?,26?,27-/m0/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0143321)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.42 g/L	ALOGPS
logP	0.39	ALOGPS
logP	0.25	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	-2	ChemAxon
pKa (Strongest Basic)	8.93	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	269.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	146.57 m³·mol⁻¹	ChemAxon
Polarizability	61.32 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

HMDB0143321

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 (4-amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonic acid (CFc000123730)

MOL for CFc000123730 ((4-amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonic acid)

3D MOL for CFc000123730 ((4-amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonic acid)

3D SDF for CFc000123730 ((4-amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonic acid)

3D-SDF for CFc000123730 ((4-amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonic acid)

PDB for CFc000123730 ((4-amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonic acid)

3D PDB for CFc000123730 ((4-amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonic acid)

SMILES for CFc000123730 ((4-amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonic acid)

INCHI for CFc000123730 ((4-amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonic acid)

Structure for CFc000123730 ((4-amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonic acid)

3D Structure for CFc000123730 ((4-amino-2-methyl-6-{[(3S)-3,5,8,12-tetrahydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl]oxy}oxan-3-yl)oxidanesulfonic acid)