ChemFOnt: Showing chemical card for 6-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000108008)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 21:26:08 UTC

Chemfont ID

CFc000108008

Molecule Identification

Common Name

6-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Definition

6-{[(16s)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of (1s,16r)-5,7,11-trihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-9-one. It is generated by UDP-glucuronosyltransferase 1-1 (P22309) enzyme via an alkyl-OH-glucuronidation reaction. This alkyl-OH-glucuronidation occurs in humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₃₃H₄₈N₂O₁₁S

Average Molecular Weight

680.81

Monoisotopic Molecular Weight

680.297881548

IUPAC Name

Traditional Name

CAS Registry Number

None

SMILES

[H]C12CC([H])(N=C(O)CC([H])(O)C(C)(C)C(=O)C(=C)C([H])(OC3([H])OC([H])(C(O)=O)C([H])(O)C([H])(O)C3([H])O)C([H])(C)CCC[C@]1(C)O2)C(C)=CC1=CSC(C)=N1

InChI Identifier

InChI=1S/C33H48N2O11S/c1-15-9-8-10-33(7)22(46-33)12-20(16(2)11-19-14-47-18(4)34-19)35-23(37)13-21(36)32(5,6)29(41)17(3)27(15)44-31-26(40)24(38)25(39)28(45-31)30(42)43/h11,14-15,20-22,24-28,31,36,38-40H,3,8-10,12-13H2,1-2,4-7H3,(H,35,37)(H,42,43)/t15?,20?,21?,22?,24?,25?,26?,27?,28?,31?,33-/m0/s1

InChI Key

HULKYQFUEHINSW-AEIVZSKRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

O-glucuronide
1-o-glucuronide
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
2,4-disubstituted 1,3-thiazole
Beta-hydroxy acid
Oxane
Hydroxy acid
Pyran
Monosaccharide
Azole
Heteroaromatic compound
Cyclic carboximidic acid
Thiazole
Secondary alcohol
Ketone
Cyclic ketone
Acetal
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Oxacycle
Azacycle
Polyol
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carbonyl group
Organic nitrogen compound
Alcohol
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0127599)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	2.24	ALOGPS
logP	1.83	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	3.69	ChemAxon
pKa (Strongest Basic)	3.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	211.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	169.32 m³·mol⁻¹	ChemAxon
Polarizability	71.56 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0127599

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB086460

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-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000108008)

MOL for CFc000108008 (6-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D MOL for CFc000108008 (6-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D SDF for CFc000108008 (6-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D-SDF for CFc000108008 (6-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

PDB for CFc000108008 (6-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D PDB for CFc000108008 (6-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

SMILES for CFc000108008 (6-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

INCHI for CFc000108008 (6-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Structure for CFc000108008 (6-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

3D Structure for CFc000108008 (6-{[(16S)-5,7-dihydroxy-8,8,12,16-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-10-methylidene-9-oxo-17-oxa-4-azabicyclo[14.1.0]heptadec-4-en-11-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)