Showing chemical card for 6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid (CFc000138162)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:13:15 UTC

Chemfont ID

CFc000138162

Molecule Identification

Common Name

6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Definition

6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton. 6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

MOL for CFc000138162 (6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

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3D MOL for CFc000138162 (6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

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3D SDF for CFc000138162 (6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

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3D-SDF for CFc000138162 (6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

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PDB for CFc000138162 (6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

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3D PDB for CFc000138162 (6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

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SMILES for CFc000138162 (6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

[H]C12CC[C@](O)(C(C)=O)[C@@]1(C)CCC1([H])C2([H])C([H])(OC2([H])OC([H])(C(O)=O)C([H])(O)C([H])(O)C2([H])O)C=C2CC(=O)CC[C@]12C

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INCHI for CFc000138162 (6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

InChI=1S/C27H38O10/c1-12(28)27(35)9-6-16-18-15(5-8-26(16,27)3)25(2)7-4-14(29)10-13(25)11-17(18)36-24-21(32)19(30)20(31)22(37-24)23(33)34/h11,15-22,24,30-32,35H,4-10H2,1-3H3,(H,33,34)/t15?,16?,17?,18?,19?,20?,21?,22?,24?,25-,26-,27-/m0/s1

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Structure for CFc000138162 (6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

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3D Structure for CFc000138162 (6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid)

Synonyms

Value	Source
6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₂₇H₃₈O₁₀

Average Molecular Weight

522.591

Monoisotopic Molecular Weight

522.246497424

IUPAC Name

6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-{[(2R,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-9-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]C12CC[C@](O)(C(C)=O)[C@@]1(C)CCC1([H])C2([H])C([H])(OC2([H])OC([H])(C(O)=O)C([H])(O)C([H])(O)C2([H])O)C=C2CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C27H38O10/c1-12(28)27(35)9-6-16-18-15(5-8-26(16,27)3)25(2)7-4-14(29)10-13(25)11-17(18)36-24-21(32)19(30)20(31)22(37-24)23(33)34/h11,15-22,24,30-32,35H,4-10H2,1-3H3,(H,33,34)/t15?,16?,17?,18?,19?,20?,21?,22?,24?,25-,26-,27-/m0/s1

InChI Key

VGWIPENKIHFJAH-WPZNQOSVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroid glucuronide conjugates

Alternative Parents

Gluco/mineralocorticoids, progestogins and derivatives
20-oxosteroids
17-hydroxysteroids
3-oxo delta-5-steroids
Delta-5-steroids
O-glucuronides
Hexoses
O-glycosyl compounds
Beta hydroxy acids and derivatives
Oxanes
Pyrans
Tertiary alcohols
Alpha-hydroxy ketones
Cyclic ketones
Cyclic alcohols and derivatives
Secondary alcohols
Monocarboxylic acids and derivatives
Oxacyclic compounds
Polyols
Carboxylic acids
Acetals
Hydrocarbon derivatives
Organic oxides

Substituents

Steroid-glucuronide-skeleton
Progestogin-skeleton
Pregnane-skeleton
20-oxosteroid
3-oxo-delta-5-steroid
3-oxosteroid
17-hydroxysteroid
Hydroxysteroid
Oxosteroid
Delta-5-steroid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Beta-hydroxy acid
Pyran
Oxane
Monosaccharide
Hydroxy acid
Alpha-hydroxy ketone
Cyclic alcohol
Tertiary alcohol
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Polyol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Acetal
Carbonyl group
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.81 g/L	ALOGPS
logP	1.14	ALOGPS
logP	0.44	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.85 m³·mol⁻¹	ChemAxon
Polarizability	54.38 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0157754

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