ChemFOnt: Showing chemical card for Rotundifoline (CFc000282277)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:29 UTC

Chemfont ID

CFc000282277

Molecule Identification

Common Name

Rotundifoline

Definition

Rotundifoline is a member of the class of compounds known as indolizidines. Indolizidines are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. Rotundifoline is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Rotundifoline can be found in mentha (mint) and spearmint, which makes rotundifoline a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Methyl (2E)-2-[(6'r,7's)-6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoic acid	Generator

Chemical Formula

C₂₂H₂₈N₂O₅

Average Molecular Weight

400.4681

Monoisotopic Molecular Weight

400.199822016

IUPAC Name

methyl (2E)-2-[(6'R,7'S)-6'-ethyl-4-hydroxy-2-oxo-1,2,3',5',6',7',8',8'a-octahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate

Traditional Name

methyl (2E)-2-[(6'R,7'S)-6'-ethyl-4-hydroxy-2-oxo-3',5',6',7',8',8'a-hexahydro-1H,2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate

CAS Registry Number

None

SMILES

CC[C@H]1CN2CCC3(C2C[C@@H]1\C(=C/OC)C(=O)OC)C(=O)NC1=C3C(O)=CC=C1

InChI Identifier

InChI=1S/C22H28N2O5/c1-4-13-11-24-9-8-22(19-16(23-21(22)27)6-5-7-17(19)25)18(24)10-14(13)15(12-28-2)20(26)29-3/h5-7,12-14,18,25H,4,8-11H2,1-3H3,(H,23,27)/b15-12+/t13-,14-,18?,22?/m0/s1

InChI Key

IXWWTVSMMIIIFZ-LWWKTLCYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indolizidines

Sub Class

Not Available

Direct Parent

Indolizidines

Alternative Parents

Substituents

Indole or derivatives
Dihydroindole
Indolizidine
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxylic acid ester
Amino acid or derivatives
Lactam
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organooxygen compound
Carbonyl group
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302761)

Food

Herb and spice

Herb

Spearmint (FooDB: FOOD00112)
Mentha (FooDB: FOOD00109)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.42 g/L	ALOGPS
logP	2.64	ALOGPS
logP	1.04	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.84	ChemAxon
pKa (Strongest Basic)	10.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.1 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.99 m³·mol⁻¹	ChemAxon
Polarizability	42.39 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0302761

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006127

KNApSAcK ID

Not Available

Chemspider ID

4478900

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321000

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Rotundifoline (CFc000282277)

MOL for CFc000282277 (Rotundifoline)

3D MOL for CFc000282277 (Rotundifoline)

3D SDF for CFc000282277 (Rotundifoline)

3D-SDF for CFc000282277 (Rotundifoline)

PDB for CFc000282277 (Rotundifoline)

3D PDB for CFc000282277 (Rotundifoline)

SMILES for CFc000282277 (Rotundifoline)

INCHI for CFc000282277 (Rotundifoline)

Structure for CFc000282277 (Rotundifoline)

3D Structure for CFc000282277 (Rotundifoline)