ChemFOnt: Showing chemical card for (S)-Higenamine (CFc000335551)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:28:10 UTC

Chemfont ID

CFc000335551

Molecule Identification

Common Name

(S)-Higenamine

Definition

Higenamine, also known as norcoclaurine or (+-)-demethylcoclaurine, is a member of the class of compounds known as benzylisoquinolines. Benzylisoquinolines are organic compounds containing an isoquinoline to which a benzyl group is attached. Higenamine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Higenamine is a sweet, fruity, and milky tasting compound found in custard apple and opium poppy, which makes higenamine a potential biomarker for the consumption of these food products. Higenamine (norcoclaurine) is a chemical compound found in a variety of plants including Nandina domestica (fruit), Aconitum carmichaelii (root), Asarum heterotropioides, Galium divaricatum (stem and vine), Annona squamosa, and Nelumbo nucifera (lotus seeds) .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-1,2,3,4-Tetrahydro-1-((4-hydroxyphenyl)methyl)-6,7-isoquinolinediol	ChEBI
(+-)-Demethylcoclaurine	ChEBI
(+-)-Norcoclaurine	ChEBI
(+-)-O-Demethylcoclaurine	ChEBI
(R,S)-Norcoclaurine	ChEBI
6,7-Dihydroxy-1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline	ChEBI
Higenamine	ChEBI
Norcoclaurine	ChEBI
(+)-Demethylcoclaurine	HMDB
(R)-Norcoclaurine	HMDB
Higenamine hydrobromide, (+-)-isomer	MeSH, HMDB
Higenamine oxalate (1:1), (+-)-isomer	MeSH, HMDB
Higenamine, tartrate (1:1), R-(r,r)-(+-)-isomer	MeSH, HMDB
1-(P-Hydroxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline	MeSH, HMDB
O-Demethylcoclaurine	MeSH, HMDB
Higenamine hydrochloride, (S)-isomer	MeSH, HMDB
1(S)-Norcoclaurine	MeSH, HMDB

Chemical Formula

C₁₆H₁₇NO₃

Average Molecular Weight

271.3111

Monoisotopic Molecular Weight

271.120843415

IUPAC Name

1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Traditional Name

higenamine

CAS Registry Number

22672-77-1

SMILES

OC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C1

InChI Identifier

InChI=1S/C16H17NO3/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14/h1-4,8-9,14,17-20H,5-7H2

InChI Key

WZRCQWQRFZITDX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Tetrahydroisoquinoline
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Secondary aliphatic amine
Secondary amine
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

norcoclaurine (CHEBI:18418 )

Functional Ontology

Sweet

Disposition

Source

Exogenous

Exogenous (HMDB: HMDB0033103)

Food

Herb and spice

Spice

Opium poppy (FooDB: FOOD00438)

Fruit

Tropical fruit

Custard apple (FooDB: FOOD00014)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	1.73	ALOGPS
logP	2.23	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	8.75	ChemAxon
pKa (Strongest Basic)	9.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	72.72 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.6 m³·mol⁻¹	ChemAxon
Polarizability	29.25 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon