ChemFOnt: Showing chemical card for (+)-Erythraline (CFc000011472)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:59:14 UTC

Chemfont ID

CFc000011472

Molecule Identification

Common Name

(+)-Erythraline

Definition

(+)-Erythraline is found in green vegetables. (+)-Erythraline is an alkaloid from Erythrina glauca (gallito) Alitretinoin (9-cis-retinoic acid) is a naturally-occurring endogenous retinoid indicated for topical treatment of cutaneous lesions in patients with AIDS-related Kaposi's sarcoma. Alitretinoin inhibits the growth of Kaposi's sarcoma (KS) cells in vitro. Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately control anterior/posterior patterning in early developmental stages. Retinoic acid acts by binding to heterodimers of the retinoic acid receptor (RAR) and the retinoid X receptor (RXR), which then bind to retinoic acid response elements (RAREs) in the regulatory regions of direct targets (including Hox genes), thereby activating gene transcription. Retinoic acid receptors mediate transcription of different sets of genes of cell differentiation, thus it also depends on the target cells. (+)-Erythraline is one of the target genes is the gene of the retinoic acid receptor itself which occurs during positive regulation. Control of retinoic acid levels is maintained by a suite of proteins. Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912 ). It is an important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth and embryonic development. (+)-Erythraline is an excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute)

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Erythraline	HMDB

Chemical Formula

C₁₈H₁₉NO₃

Average Molecular Weight

297.3484

Monoisotopic Molecular Weight

297.136493479

IUPAC Name

19-methoxy-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2(10),3,8,15,17-pentaene

Traditional Name

19-methoxy-5,7-dioxa-13-azapentacyclo[11.7.0.0¹,¹⁶.0²,¹⁰.0⁴,⁸]icosa-2(10),3,8,15,17-pentaene

CAS Registry Number

466-77-3

SMILES

COC1CC23N(CC=C2C=C1)CCC1=C3C=C2OCOC2=C1

InChI Identifier

InChI=1S/C18H19NO3/c1-20-14-3-2-13-5-7-19-6-4-12-8-16-17(22-11-21-16)9-15(12)18(13,19)10-14/h2-3,5,8-9,14H,4,6-7,10-11H2,1H3

InChI Key

TVOFUERNMZTYRM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as erythrinanes. These are erythrina alkaloids possessing either a 6-5-6-6-membered indoloisoquinoline core or a derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Erythrina alkaloids

Sub Class

Erythrinanes

Direct Parent

Erythrinanes

Alternative Parents

Substituents

Erythrinane skeleton
Tetrahydroisoquinoline
Benzodioxole
Indole or derivatives
Aralkylamine
Benzenoid
Pyrroline
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Dialkyl ether
Ether
Azacycle
Acetal
Organoheterocyclic compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030258)
Cell membrane (HMDB: HMDB0030258)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030258)

Source

Endogenous

Endogenous (HMDB: HMDB0030258)

Plant

Plant (HMDB: HMDB0030258)

Exogenous

Food

Food (HMDB: HMDB0030258)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0030258)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.05 g/L	ALOGPS
logP	2.01	ALOGPS
logP	2	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Basic)	9.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.93 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.28 m³·mol⁻¹	ChemAxon
Polarizability	32.08 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030258

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002082

KNApSAcK ID

C00027355

Chemspider ID

26504826

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12308897

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (+)-Erythraline (CFc000011472)

MOL for CFc000011472 ((+)-Erythraline)

3D MOL for CFc000011472 ((+)-Erythraline)

3D SDF for CFc000011472 ((+)-Erythraline)

3D-SDF for CFc000011472 ((+)-Erythraline)

PDB for CFc000011472 ((+)-Erythraline)

3D PDB for CFc000011472 ((+)-Erythraline)

SMILES for CFc000011472 ((+)-Erythraline)

INCHI for CFc000011472 ((+)-Erythraline)

Structure for CFc000011472 ((+)-Erythraline)

3D Structure for CFc000011472 ((+)-Erythraline)