ChemFOnt: Showing chemical card for Cinnamoyl-CoA (CFc000281429)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:48 UTC

Chemfont ID

CFc000281429

Molecule Identification

Common Name

Cinnamoyl-CoA

Definition

Cinnamoyl-coa is a member of the class of compounds known as 2-enoyl coas. 2-enoyl coas are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain. Cinnamoyl-coa is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Cinnamoyl-coa can be found in sorghum, which makes cinnamoyl-coa a potential biomarker for the consumption of this food product. Cinnamoyl-Coenzyme A is an intermediate in the phenylpropanoids metabolic pathway .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-{2-[(2-{[(2E)-3-phenylprop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}butanimidate	Generator
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-{2-[(2-{[(2E)-3-phenylprop-2-enoyl]sulphanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}butanimidate	Generator
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-N-{2-[(2-{[(2E)-3-phenylprop-2-enoyl]sulphanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}butanimidic acid	Generator

Chemical Formula

C₃₀H₄₂N₇O₁₇P₃S

Average Molecular Weight

897.677

Monoisotopic Molecular Weight

897.157073179

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-2,2-dimethyl-3-({2-[(2-{[(2E)-3-phenylprop-2-enoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-({2-[(2-{[(2E)-3-phenylprop-2-enoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

76109-04-1

SMILES

OC(C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C(=O)NCCC(=O)NCCSC(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C30H42N7O17P3S/c1-30(2,25(41)28(42)33-11-10-20(38)32-12-13-58-21(39)9-8-18-6-4-3-5-7-18)15-51-57(48,49)54-56(46,47)50-14-19-24(53-55(43,44)45)23(40)29(52-19)37-17-36-22-26(31)34-16-35-27(22)37/h3-9,16-17,19,23-25,29,40-41H,10-15H2,1-2H3,(H,32,38)(H,33,42)(H,46,47)(H,48,49)(H2,31,34,35)(H2,43,44,45)/b9-8+/t19-,23-,24-,25?,29-/m1/s1

InChI Key

JVNVHNHITFVWIX-WAFZYBDGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

2-enoyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Cinnamic acid or derivatives
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Styrene
Aminopyrimidine
Monoalkyl phosphate
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Fatty amide
Monocyclic benzene moiety
Phosphoric acid ester
Alkyl phosphate
Benzenoid
Imidolactam
Pyrimidine
Imidazole
Heteroaromatic compound
Tetrahydrofuran
Azole
Amino acid or derivatives
Carbothioic s-ester
Thiocarboxylic acid ester
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Organic nitrogen compound
Organosulfur compound
Primary amine
Organopnictogen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Monolignols (C00540 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301913)

Food

Cereal and cereal product

Cereal

Sorghum (FooDB: FOOD00177)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Flavonoid Biosynthesis (PathBank: SMP0012021)
Stilbenoid, Diarylheptanoid, and Gingerol Biosynthesis (PathBank: SMP0063461)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.81 g/L	ALOGPS
logP	0.16	ALOGPS
logP	-4.4	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	202.62 m³·mol⁻¹	ChemAxon
Polarizability	82 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0301913

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001607

KNApSAcK ID

Not Available

Chemspider ID

4444058

KEGG Compound ID

C00540

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280356

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Cinnamoyl-CoA (CFc000281429)

MOL for CFc000281429 (Cinnamoyl-CoA)

3D MOL for CFc000281429 (Cinnamoyl-CoA)

3D SDF for CFc000281429 (Cinnamoyl-CoA)

3D-SDF for CFc000281429 (Cinnamoyl-CoA)

PDB for CFc000281429 (Cinnamoyl-CoA)

3D PDB for CFc000281429 (Cinnamoyl-CoA)

SMILES for CFc000281429 (Cinnamoyl-CoA)

INCHI for CFc000281429 (Cinnamoyl-CoA)

Structure for CFc000281429 (Cinnamoyl-CoA)

3D Structure for CFc000281429 (Cinnamoyl-CoA)