Showing Compound 22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester (FDB020135)

Record Information

Version

1.0

Creation date

2010-04-08 22:14:49 UTC

Update date

2019-11-26 03:18:31 UTC

Primary ID

FDB020135

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester

Description

22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. Based on a literature review a significant number of articles have been published on 22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester.

CAS Number

151194-18-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
22R-Acetoxy-1a,3b-dihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester	Generator
22R-Acetoxy-1a,3b-dihydroxyergosta-5,24E-dien-26-Oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester	Generator
22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester	Generator
22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucopyranoside 26-O-[b-D-glucopyranosyl-(1->4)-b-D-glucopyranosyl-(1->2)-6-acetyl-b-D-glucopyranosyl] ester	manual
22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester	manual
22R-Acetoxy-1α,3β-dihydroxyergosta-5,24E-dien-26-Oate 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester	Generator
22R-Acetoxy-1α,3β-dihydroxyergosta-5,24E-dien-26-Oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester	Generator
6-[(Acetyloxy)methyl]-3-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl (2Z)-5-(acetyloxy)-6-(3-hydroxy-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl)-2,3-dimethylhept-2-enoic acid	Generator

Showing 1 to 8 of 8 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.07 g/L	ALOGPS
logP	-0.88	ALOGPS
logP	-2.9	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.75	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	24	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	426.73 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	278.5 m³·mol⁻¹	ChemAxon
Polarizability	124.09 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C56H88O27

IUPAC name

6-[(acetyloxy)methyl]-3-{[3,4-dihydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4,5-dihydroxyoxan-2-yl (2Z)-5-(acetyloxy)-6-(3-hydroxy-2,15-dimethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl)-2,3-dimethylhept-2-enoate

InChI Identifier

InChI=1S/C56H88O27/c1-21(22(2)50(73)83-54-49(43(68)40(65)36(80-54)20-74-24(4)60)82-53-47(72)44(69)48(35(19-59)79-53)81-52-46(71)42(67)39(64)34(18-58)78-52)14-32(75-25(5)61)23(3)29-10-11-30-28-9-8-26-15-27(76-51-45(70)41(66)38(63)33(17-57)77-51)16-37(62)56(26,7)31(28)12-13-55(29,30)6/h8,23,27-49,51-54,57-59,62-72H,9-20H2,1-7H3/b22-21-

InChI Key

VGFQIQCRTFAIEC-DQRAZIAOSA-N

Isomeric SMILES

CC(C(C\C(C)=C(\C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC1OC(CO)C(OC2OC(CO)C(O)C(O)C2O)C(O)C1O)OC(C)=O)C1CCC2C3CC=C4CC(CC(O)C4(C)C3CCC12C)OC1OC(CO)C(O)C(O)C1O

Average Molecular Weight

1193.2817

Monoisotopic Molecular Weight

1192.55129761

Classification

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically 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

Steroidal glycosides

Alternative Parents

Substituents

Diterpene glycoside
Ergostane-skeleton
Steroidal glycoside
Oligosaccharide
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid ester
Diterpenoid
1-hydroxysteroid
Hydroxysteroid
Delta-5-steroid
Terpene glycoside
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Oxane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Organic oxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Subcellular:

Biofluid and excreta:

Urine

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Molecular messenger:

Signaling molecule

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 56.37%; H 7.43%; O 36.20%	DFC
Melting Point	Not Available
Optical Rotation	[a]25D -23 (c, 1 in MeOH)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0hl1-6900127051-d37b9a68c9b1d14210e2	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0i29-5500465392-5b804d21da80eac50f4a	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0n4i-4712343492-926844a72de13b4175f2	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0c04-8901003020-ad731974442cdc26f04b	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0c00-9702003020-b8853430b68b6fcff051	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ar3-9804000230-dd0d08caaa01ea8fcfbb	2017-10-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000f-3900112001-9ceae8e70c6e652a0bdf	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4j-6900003000-6dcd0ec1519735040da8	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9400001001-c40f6c665b40860ae629	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f8j-0900124003-89cfdfe9ac3e67c76e7c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fy6-1900113003-e95e285a0d83dfe160d1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-4900100000-838676562d5a7139afb4	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB40403

CRC / DFC (Dictionary of Food Compounds) ID

MKT20-O:MKT27-V

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

No data available in table

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester (FDB020135)

Structure for FDB020135 (22R-Acetoxy-1alpha,3beta-dihydroxyergosta-5,24E-dien-26-oic acid 3-O-b-D-glucoside 26-O-[b-D-glucosyl-(1->4)-b-D-glucosyl-(1->2)-6-acetyl-b-D-glucosyl] ester)