ContaminantDB: 24-Acetyl- 25-cinnamoylvulgaroside

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 04:56:55 UTC

Update Date

2016-11-09 01:21:08 UTC

Accession Number

CHEM034481

Identification

Common Name

24-Acetyl- 25-cinnamoylvulgaroside

Class

Small Molecule

Description

24-Acetyl- 25-cinnamoylvulgaroside is found in fruits. 24-Acetyl- 25-cinnamoylvulgaroside is a constituent of Cydonia vulgaris (quince).

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(2-{2-[(acetyloxy)methyl]-2-hydroxy-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-1-yl}-1-hydroxyethyl)-5-oxo-2,5-dihydrofuran-2-yl (2E)-3-phenylprop-2-enoic acid	HMDB

Chemical Formula

C₃₆H₄₈O₈

Average Molecular Mass

608.762 g/mol

Monoisotopic Mass

608.335 g/mol

CAS Registry Number

172616-89-6

IUPAC Name

3-(2-{2-[(acetyloxy)methyl]-2-hydroxy-4b,8,8,10a-tetramethyl-tetradecahydrophenanthren-1-yl}-1-hydroxyethyl)-5-oxo-2,5-dihydrofuran-2-yl (2E)-3-phenylprop-2-enoate

Traditional Name

3-(2-{2-[(acetyloxy)methyl]-2-hydroxy-4b,8,8,10a-tetramethyl-decahydrophenanthren-1-yl}-1-hydroxyethyl)-5-oxo-2H-furan-2-yl (2E)-3-phenylprop-2-enoate

SMILES

CC(=O)OCC1(O)CCC2C(C)(CCC3C(C)(C)CCCC23C)C1CC(O)C1=CC(=O)OC1OC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C36H48O8/c1-23(37)42-22-36(41)19-15-28-34(4)17-9-16-33(2,3)27(34)14-18-35(28,5)29(36)21-26(38)25-20-31(40)44-32(25)43-30(39)13-12-24-10-7-6-8-11-24/h6-8,10-13,20,26-29,32,38,41H,9,14-19,21-22H2,1-5H3/b13-12+

InChI Key

IMXZIJOCFAKDPZ-OUKQBFOZSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as cheilanthane sesterterpenoids. These are sesterterpnoids with a structure based on the cheilanthane backbone. Cheilanthane is a tricyclic compound consisting of a tetradecahydrophenanthrene ring system that carries two methyl groups at the 1-position, one methyl group at the 4a-,7-, and 8a-positions, as well as a 3-methylpentyl group at the 8-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Cheilanthane sesterterpenoids

Alternative Parents

Substituents

Cheilanthane sesterterpenoid
13-hydroxysteroid
Hydroxysteroid
16-hydroxysteroid
Steroid
Hydrophenanthrene
Phenanthrene
Cinnamic acid or derivatives
Cinnamic acid ester
Tricarboxylic acid or derivatives
Styrene
Acylal
Fatty acid ester
Benzenoid
Fatty acyl
Monocyclic benzene moiety
2-furanone
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Cyclic alcohol
Dihydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00048 g/L	ALOGPS
logP	4.93	ALOGPS
logP	6.26	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	165.89 m³·mol⁻¹	ChemAxon
Polarizability	67.16 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001u-2633190000-9d6d5ca2aa4672f3bd2d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00lr-4820239000-43c870bf8ffab89fca64	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("24-Acetyl- 25-cinnamoylvulgaroside,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001l-1601392000-ed849e7889dae11750d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1911330000-7361063af552ec79a14b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uec-4922520000-43c164d0158c6aa95412	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-3900122000-a899209a228552cc85c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-9521600000-7b7188d8bc02ccaca69a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-9800400000-450cbfef1a933e686a5a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0610589000-81937a8764769d8bebc8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-1900010000-d2d8b15a6449ae7d322c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-1901010000-0e2251febc21792b3918	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kb-0100490000-75bda764b069c4caf505	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9200002000-3c5745a1619227a865dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056u-9300000000-220ed1ea5f735f87b788	Spectrum