ChemFOnt: Showing chemical card for Leptosine (CFc000282557)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:35:01 UTC

Chemfont ID

CFc000282557

Molecule Identification

Common Name

Leptosine

Definition

Leptosine, also known as leptosin j, is a member of the class of compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Leptosine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Leptosine can be found in american cranberry, which makes leptosine a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Leptosin J	MeSH
Leptosin I	MeSH

Chemical Formula

C₃₂H₃₂N₆O₇S₄

Average Molecular Weight

740.892

Monoisotopic Molecular Weight

740.121530168

IUPAC Name

37-hydroxy-7-(hydroxymethyl)-6,36-dimethyl-30-(propan-2-yl)-3-oxa-31,32,33,34-tetrathia-6,9,11,26,28,36-hexaazadecacyclo[28.4.2.1⁴,¹⁸.0¹,²⁸.0²,¹⁹.0⁴,⁹.0¹⁰,¹⁸.0¹²,¹⁷.0¹⁹,²⁷.0²⁰,²⁵]heptatriaconta-12,14,16,20,22,24-hexaene-5,8,29,35-tetrone

Traditional Name

37-hydroxy-7-(hydroxymethyl)-30-isopropyl-6,36-dimethyl-3-oxa-31,32,33,34-tetrathia-6,9,11,26,28,36-hexaazadecacyclo[28.4.2.1⁴,¹⁸.0¹,²⁸.0²,¹⁹.0⁴,⁹.0¹⁰,¹⁸.0¹²,¹⁷.0¹⁹,²⁷.0²⁰,²⁵]heptatriaconta-12,14,16,20,22,24-hexaene-5,8,29,35-tetrone

CAS Registry Number

None

SMILES

CC(C)C12SSSSC3(C4OC56C(O)C7(C(NC8=CC=CC=C78)N5C(=O)C(CO)N(C)C6=O)C44C(NC5=CC=CC=C45)N3C1=O)C(=O)N2C

InChI Identifier

InChI=1S/C32H32N6O7S4/c1-14(2)31-27(44)38-24-29(16-10-6-8-12-18(16)34-24)22(32(38,26(43)36(31)4)47-49-48-46-31)45-30-21(41)28(29)15-9-5-7-11-17(15)33-23(28)37(30)20(40)19(13-39)35(3)25(30)42/h5-12,14,19,21-24,33-34,39,41H,13H2,1-4H3

InChI Key

PZFMMBJJDMZAIP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Alpha-amino acid or derivatives
Indole
Dihydroindole
Thiodioxopiperazine
Dioxopiperazine
2,5-dioxopiperazine
Meta-oxazepine
Secondary aliphatic/aromatic amine
N-alkylpiperazine
N-methylpiperazine
1,4-diazinane
Oxane
Piperazine
Benzenoid
Pyrrolidine
Pyrrole
Tertiary carboxylic acid amide
Secondary alcohol
Amino acid or derivatives
Carboxamide group
Lactam
Oxacycle
Secondary amine
Azacycle
Carboxylic acid derivative
Amine
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303041)

Food

Fruit

Berry

American cranberry (FooDB: FOOD00192)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.85 g/L	ALOGPS
logP	3.26	ALOGPS
logP	2.86	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.78	ChemAxon
pKa (Strongest Basic)	2.18	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	154.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	183.31 m³·mol⁻¹	ChemAxon
Polarizability	73.07 Å³	ChemAxon
Number of Rings	10	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0303041

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007445

KNApSAcK ID

Not Available

Chemspider ID

138850

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

157801

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Leptosine (CFc000282557)

MOL for CFc000282557 (Leptosine)

3D MOL for CFc000282557 (Leptosine)

3D SDF for CFc000282557 (Leptosine)

3D-SDF for CFc000282557 (Leptosine)

PDB for CFc000282557 (Leptosine)

3D PDB for CFc000282557 (Leptosine)

SMILES for CFc000282557 (Leptosine)

INCHI for CFc000282557 (Leptosine)

Structure for CFc000282557 (Leptosine)

3D Structure for CFc000282557 (Leptosine)