ChemFOnt: Showing chemical card for Celosianin (CFc000282505)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:55 UTC

Chemfont ID

CFc000282505

Molecule Identification

Common Name

Celosianin

Definition

Celosianin is also known as 4-coumaroylamaranthin. Celosianin is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Celosianin can be found in spinach, which makes celosianin a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-Coumaroylamaranthin	MetaCyc

Chemical Formula

C₃₉H₃₈N₂O₂₁

Average Molecular Weight

870.7198

Monoisotopic Molecular Weight

870.196706288

IUPAC Name

(2S,4E)-4-{2-[(2S)-2-carboxylato-5-{[(3R,4S,5S,6R)-3-{[(3R,4S,5S,6S)-6-carboxylato-4,5-dihydroxy-3-{[(2Z)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-hydroxy-2,3-dihydro-1H-1λ⁵-indol-1-ylium-1-ylidene]ethylidene}-1,2,3,4-tetrahydropyridin-1-ium-2,6-dicarboxylate

Traditional Name

CAS Registry Number

None

SMILES

OC[C@H]1OC(OC2=C(O)C=C3C(C[C@@H](C([O-])=O)[N+]3=C\C=C3/C[C@H]([NH2+]C(=C3)C([O-])=O)C([O-])=O)=C2)[C@H](OC2O[C@@H]([C@@H](O)[C@H](O)[C@H]2OC(=O)\C=C/C2=CC=C(O)C=C2)C([O-])=O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C39H40N2O21/c42-14-25-27(46)28(47)33(62-39-32(30(49)29(48)31(61-39)37(56)57)60-26(45)6-3-15-1-4-18(43)5-2-15)38(59-25)58-24-12-17-11-22(36(54)55)41(21(17)13-23(24)44)8-7-16-9-19(34(50)51)40-20(10-16)35(52)53/h1-9,12-13,20,22,25,27-33,38-39,42,46-49H,10-11,14H2,(H6,43,44,45,50,51,52,53,54,55,56,57)/p-2/t20-,22-,25+,27+,28-,29-,30-,31-,32+,33+,38?,39?/m0/s1

InChI Key

VYAFZESLHLWKCS-AHJBFHQGSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as betacyanins and derivatives. These are organic compounds containing a glycoside of indolium-2-carboxylic acid attached, with the nitrogen ring of the indolium ring attached to an ethylpyridine-2,6-dicarboxylic acid derivative. Betacyanins are red nitrogenous pigments found in certain plants, such as beetroots.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Betalains

Sub Class

Betacyanins and derivatives

Direct Parent

Betacyanins and derivatives

Alternative Parents

Substituents

Betacyanin
Betaxanthin skeleton
Pentacarboxylic acid or derivatives
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Coumaric acid ester
Glucuronic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Indolecarboxylic acid
Indolecarboxylic acid derivative
Cinnamic acid ester
Disaccharide
Glycosyl compound
O-glycosyl compound
L-alpha-amino acid
Alpha-amino acid
Alpha-amino acid or derivatives
Indole or derivatives
Styrene
Tetrahydropyridine
1-hydroxy-2-unsubstituted benzenoid
Phenol
Beta-hydroxy acid
Fatty acid ester
Hydropyridine
Oxane
Hydroxy acid
Monocyclic benzene moiety
Pyran
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid salt
Carboxylic acid ester
Shiff base
Amino acid
Secondary alcohol
Amino acid or derivatives
Secondary amine
Acetal
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Secondary aliphatic amine
Azacycle
Oxacycle
Organic salt
Primary alcohol
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic oxide
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organonitrogen compound
Amine
Organooxygen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302989)

Food

Vegetable

Leaf vegetable

Spinach (FooDB: FOOD00178)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.062 g/L	ALOGPS
logP	1.48	ALOGPS
logP	-4.1	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	1.44	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	384.97 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	267.46 m³·mol⁻¹	ChemAxon
Polarizability	82.65 Å³	ChemAxon
Number of Rings	6	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

HMDB0302989

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007160

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

54740360

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Celosianin (CFc000282505)

MOL for CFc000282505 (Celosianin)

3D MOL for CFc000282505 (Celosianin)

3D SDF for CFc000282505 (Celosianin)

3D-SDF for CFc000282505 (Celosianin)

PDB for CFc000282505 (Celosianin)

3D PDB for CFc000282505 (Celosianin)

SMILES for CFc000282505 (Celosianin)

INCHI for CFc000282505 (Celosianin)

Structure for CFc000282505 (Celosianin)

3D Structure for CFc000282505 (Celosianin)