ContaminantDB: Phomopsin A

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 04:49:32 UTC

Update Date

2026-04-06 11:15:53 UTC

Accession Number

CHEM002991

Identification

Common Name

Phomopsin A

Class

Small Molecule

Description

Phomopsin A, a peptide mycotoxin originally derived from Phomopsis leptostromiformis, has been shown to be a potent microtubule inhibitor.

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Amide
Amine
Ether
Food Toxin
Fungal Toxin
Natural Compound
Organic Compound
Organochloride

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Phomopsin	HMDB
Phomopside b	HMDB
Phomopside a	HMDB
(2E)-2-{[(2E)-2-({[(2S)-1-[(3R,4S,7S,10S,11S)-14-chloro-3-ethyl-6,9,11,15-tetrahydroxy-3-methyl-10-(methylamino)-7-(prop-1-en-2-yl)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaene-4-carbonyl]-2,5-dihydro-1H-pyrrol-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-methylpent-2-en-1-ylidene]amino}but-2-enedioate	HMDB

Chemical Formula

C₃₆H₄₅ClN₆O₁₂

Average Molecular Mass

789.229 g/mol

Monoisotopic Mass

788.278 g/mol

CAS Registry Number

64925-80-0

IUPAC Name

Not Available

Traditional Name

(2E)-2-[(2E)-2-{[(2S)-1-[(3R,4S,7S,10S,11S)-14-chloro-3-ethyl-11,15-dihydroxy-3-methyl-10-(methylamino)-6,9-dioxo-7-(prop-1-en-2-yl)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-triene-4-carbonyl]-2,5-dihydropyrrol-2-yl]formamido}-3-methylpent-2-enamido]but-2-enedioic acid

SMILES

[H]\C(C(O)=O)=C(/N=C(O)C(\N=C(O)[C@]1([H])C=CCN1C(=O)[C@@]1([H])N=C(O)[C@@]([H])(N=C(O)[C@@]([H])(NC)[C@@]([H])(O)C2=CC(Cl)=C(O)C(O[C@]1(C)CC)=C2)C(C)=C)=C(\C)CC)C(O)=O

InChI Identifier

InChI=1S/C36H45ClN6O12/c1-8-17(5)25(32(50)39-20(35(53)54)15-23(44)45)41-30(48)21-11-10-12-43(21)34(52)29-36(6,9-2)55-22-14-18(13-19(37)28(22)47)27(46)26(38-7)33(51)40-24(16(3)4)31(49)42-29/h10-11,13-15,21,24,26-27,29,38,46-47H,3,8-9,12H2,1-2,4-7H3,(H,39,50)(H,40,51)(H,41,48)(H,42,49)(H,44,45)(H,53,54)/b20-15+,25-17+/t21-,24-,26-,27-,29+,36+/m0/s1

InChI Key

FAFRRYBYQKPKSY-AJSRVUJESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Cyclic alpha peptide
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Macrolactam
Alpha-amino acid amide
Alpha-amino acid or derivatives
Pyrroline carboxylic acid or derivatives
Alkyl aryl ether
Aralkylamine
Aryl chloride
Aryl halide
N-acyl-amine
Benzenoid
Dicarboxylic acid or derivatives
Vinylogous amide
Tertiary carboxylic acid amide
Pyrroline
Amino acid
Lactam
Amino acid or derivatives
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Oxacycle
Azacycle
Carboxylic acid
Organoheterocyclic compound
Secondary aliphatic amine
Secondary amine
Ether
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Kinetochore
Microtubule
Tubulin

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Cell cycle	Not Available	map04110
Apoptosis	Not Available	map04210

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	1.64	ALOGPS
logP	-2.5	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	1.98	ChemAxon
pKa (Strongest Basic)	7.57	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	273.03 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	197.6 m³·mol⁻¹	ChemAxon
Polarizability	75.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0076-0132001900-f51ce03e49cde5d092e3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00rx-7694521200-83f7ddb6d9d8de9e3b95	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03kd-9673000000-c629c0b7a3d70ea93080	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-0011430900-8d7c589702cfb1213103	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00mo-3211112900-a8fefafa5544f3a6e775	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-029x-9878440000-a29d9278fbc970f30ab1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00p3-0003000900-58a8365b810ce0be0d88	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03ei-8249010800-b13a1bc7a997869aa059	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-8930001000-5afa9ae83e003a999f2b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zgl-0110629400-3c204e2539b5fa8c9e59	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uec-1410977200-70217645495a16b80677	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fr-6734901300-6c39182ee0b774a6f145	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Phomopsin A, a peptide mycotoxin originally derived from Phomopsis leptostromiformis, has been shown to be a potent microtubule inhibitor.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0030447

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00024794

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

HOS

Wikipedia Link

Not Available

Chemspider ID

4943049

ChEBI ID

Not Available

PubChem Compound ID

6438581

Kegg Compound ID

C19955

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Phomopsin A (CHEM002991)

Structure for CHEM002991: Phomopsin A