AFCDB: vellosimine (FDB031253)

Record Information

Version

1.0

Creation date

2015-05-07 21:26:22 UTC

Update date

2019-11-26 03:22:13 UTC

Primary ID

FDB031253

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

vellosimine

Description

Vellosimine is a member of the class of compounds known as macroline alkaloids. Macroline alkaloids are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. Vellosimine is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Vellosimine can be found in a number of food items such as caraway, italian oregano, star anise, and fox grape, which makes vellosimine a potential biomarker for the consumption of these food products.

CAS Number

Not Available

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	2.51	ALOGPS
logP	2.46	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	15.29	ChemAxon
pKa (Strongest Basic)	5.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	36.1 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.18 m³·mol⁻¹	ChemAxon
Polarizability	33.33 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

Chemical Formula

C19H20N2O

IUPAC name

15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde

InChI Identifier

InChI=1S/C19H20N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,10,13,15,17-18,20H,7-9H2,1H3

InChI Key

MHASSCPGKAMILD-UHFFFAOYSA-N

Isomeric SMILES

CC=C1CN2C3CC4=C(NC5=CC=CC=C45)C2CC1C3C=O

Average Molecular Weight

292.382

Monoisotopic Molecular Weight

292.157563272

Classification

Description

Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Sarpagine-skeleton
Vobasan skeleton
Beta-carboline
Pyridoindole
3-alkylindole
Indole
Indole or derivatives
Quinuclidine
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (VELLOSIMINE )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-502966b71b3fa4b51088	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0090000000-8c8a72ed22a2c42f48f3	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-005a-0980000000-393d345529d5f12f002e	2019-02-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-eb9636b759144711f704	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-0090000000-1377844617e62b912753	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0090000000-c96869b275c60a9d52bc	2019-02-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-30850ca9637e3e228dfd	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002f-0090000000-ac575a3d12360d46fa43	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000000-a66b6223d1fbd7db0b92	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-74a3146908205cd6ebec	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0090000000-60735b38d43fc092aca2	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01p9-0190000000-a1d7ba384146d50c2c3f	2021-10-21	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

vellosimine (FDB031253)

Structure for FDB031253 (vellosimine)