MiMeDB: Showing metabocard for beta-cyclopiazonate (MMDBc0055743)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:03:57 UTC

Update Date

2022-08-12 20:09:27 UTC

Metabolite ID

MMDBc0055743

Metabolite Identification

Common Name

beta-cyclopiazonate

Description

CHEBI:58067, also known as b-cyclopiazonate, belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Based on a literature review very few articles have been published on CHEBI:58067.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222032D          

 26 28  0  0  1  0            999 V2000
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3763    5.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313    4.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0792    3.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587    3.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2508    3.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363    2.5945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4382    4.2555    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.1538    4.6147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044    2.6714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5960    3.7877    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 12  3  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15  6  2  0  0  0  0
 16  9  1  6  0  0  0
 17 12  2  0  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 17  1  0  0  0  0
 21 10  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  1  0  0  0  0
 22 20  2  0  0  0  0
 23 12  1  0  0  0  0
 24 19  2  0  0  0  0
 25 20  1  0  0  0  0
 16 26  1  1  0  0  0
M  CHG  1  23  -1
M  END


  Mrv1652306172222032D          

 26 28  0  0  1  0            999 V2000
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3763    5.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313    4.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0792    3.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587    3.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2508    3.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5363    2.5945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4382    4.2555    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.1538    4.6147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0044    2.6714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5960    3.7877    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 12  3  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 15  6  2  0  0  0  0
 16  9  1  6  0  0  0
 17 12  2  0  0  0  0
 18 13  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 17  1  0  0  0  0
 21 10  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  1  0  0  0  0
 22 20  2  0  0  0  0
 23 12  1  0  0  0  0
 24 19  2  0  0  0  0
 25 20  1  0  0  0  0
 16 26  1  1  0  0  0
M  CHG  1  23  -1
M  END
> <DATABASE_ID>
MMDBc0055743

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(CC2=CNC3=CC=CC(CC=C(C)C)=C23)N=C(O)\C(=C(\C)[O-])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O3/c1-11(2)7-8-13-5-4-6-15-18(13)14(10-21-15)9-16-19(24)17(12(3)23)20(25)22-16/h4-7,10,16,21,23H,8-9H2,1-3H3,(H,22,25)/p-1/b17-12-/t16-/m0/s1

> <INCHI_KEY>
HLDTVPRYVAHRIQ-BQGMYUGNSA-M

> <FORMULA>
C20H21N2O3

> <MOLECULAR_WEIGHT>
337.4

> <EXACT_MASS>
337.155766124

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
36.85507971816822

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(2S,4E)-5-hydroxy-2-{[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-3-oxo-3,4-dihydro-2H-pyrrol-4-ylidene]ethan-1-olate

> <JCHEM_LOGP>
3.9218290133333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.710450343446539

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.226514152175549

> <JCHEM_PKA_STRONGEST_BASIC>
1.1945659828313862

> <JCHEM_POLAR_SURFACE_AREA>
88.51

> <JCHEM_REFRACTIVITY>
110.3876

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-[(3E,5S)-2-hydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-4-oxo-5H-pyrrol-3-ylidene]ethanolate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.569   9.728   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.045   8.264   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.143   5.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.015   7.119   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.483   7.280   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.335   5.613   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0      -1.001   4.843   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0      -4.551   7.944   0.000  0.00  0.00           O-1
HETATM   24  O   UNK     0       0.287   8.614   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.742   4.987   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       1.113   7.070   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4    5    6                                                       
CONECT    5    4   13                                                       
CONECT    6    4   15                                                       
CONECT    7    8   11                                                       
CONECT    8    7   13                                                       
CONECT    9   14   16                                                       
CONECT   10   14   21                                                       
CONECT   11    1    2    7                                                  
CONECT   12    3   17   23                                                  
CONECT   13    5    8   18                                                  
CONECT   14    9   10   18                                                  
CONECT   15    6   18   21                                                  
CONECT   16    9   19   22   26                                             
CONECT   17   12   19   20                                                  
CONECT   18   13   14   15                                                  
CONECT   19   16   17   24                                                  
CONECT   20   17   22   25                                                  
CONECT   21   10   15                                                       
CONECT   22   16   20                                                       
CONECT   23   12                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
CONECT   26   16                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

Synonyms

Value	Source
beta-Cyclopiazonate	ChEBI
b-Cyclopiazonate	Generator
b-Cyclopiazonic acid	Generator
beta-Cyclopiazonic acid	Generator
Β-cyclopiazonate	Generator
Β-cyclopiazonic acid	Generator

Molecular Formula

C₂₀H₂₁N₂O₃

Average Mass

337.4

Monoisotopic Mass

337.155766124

IUPAC Name

1-[(2S,4E)-5-hydroxy-2-{[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-3-oxo-3,4-dihydro-2H-pyrrol-4-ylidene]ethan-1-olate

Traditional Name

1-[(3E,5S)-2-hydroxy-5-{[4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}-4-oxo-5H-pyrrol-3-ylidene]ethanolate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC2=CNC3=CC=CC(CC=C(C)C)=C23)N=C(O)\C(=C(\C)[O-])C1=O

InChI Identifier

InChI=1S/C20H22N2O3/c1-11(2)7-8-13-5-4-6-15-18(13)14(10-21-15)9-16-19(24)17(12(3)23)20(25)22-16/h4-7,10,16,21,23H,8-9H2,1-3H3,(H,22,25)/p-1/b17-12-/t16-/m0/s1

InChI Key

HLDTVPRYVAHRIQ-BQGMYUGNSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Substituted pyrrole
Benzenoid
Pyrrole
Pyrroline
Heteroaromatic compound
Vinylogous acid
Cyclic carboximidic acid
Ketone
Lactim
Cyclic ketone
Enolate
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic anion (CHEBI:58067 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	3.92	ChemAxon
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	1.19	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.51 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.39 m³·mol⁻¹	ChemAxon
Polarizability	36.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26331022

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

136181834

PDB ID

Not Available

ChEBI ID

58067

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for beta-cyclopiazonate (MMDBc0055743)

MOL for #<Metabolite:0x00007fed1550eb28>

3D MOL for #<Metabolite:0x00007fed1550eb28>

3D SDF for #<Metabolite:0x00007fed1550eb28>

3D-SDF for #<Metabolite:0x00007fed1550eb28>

PDB for #<Metabolite:0x00007fed1550eb28>

3D PDB for #<Metabolite:0x00007fed1550eb28>

SMILES for #<Metabolite:0x00007fed1550eb28>

INCHI for #<Metabolite:0x00007fed1550eb28>

Structure for #<Metabolite:0x00007fed1550eb28>

3D Structure for #<Metabolite:0x00007fed1550eb28>