MiMeDB: Showing metabocard for chanoclavine-I aldehyde (MMDBc0055794)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:06:43 UTC

Update Date

2022-08-12 20:09:28 UTC

Metabolite ID

MMDBc0055794

Metabolite Identification

Common Name

chanoclavine-I aldehyde

Description

chanoclavine-I aldehyde(1+) belongs to the class of organic compounds known as clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines. Based on a literature review a significant number of articles have been published on chanoclavine-I aldehyde(1+).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222062D          

 22 24  0  0  1  0            999 V2000
    1.8992    3.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7060    2.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514    1.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189    1.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3141    2.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713   -0.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7798    4.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6644    3.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725    1.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987    1.9867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6913    0.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661    1.5017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3588    0.8306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6198    1.8373    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.9463   -0.4389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1300    4.6372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0793    3.1120    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5581    2.5065    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9524    2.3222    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
 10  1  1  0  0  0  0
 10  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  4  1  0  0  0  0
 13  6  1  1  0  0  0
 13 12  1  0  0  0  0
 14  5  2  0  0  0  0
 15  7  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 16 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17  2  1  0  0  0  0
 15 17  1  6  0  0  0
 18  8  1  0  0  0  0
 18 14  1  0  0  0  0
 19  9  2  0  0  0  0
 20  6  1  0  0  0  0
 13 21  1  6  0  0  0
 15 22  1  1  0  0  0
M  CHG  1  17   1
M  END
> <DATABASE_ID>
MMDBc0055794

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\C)C=O)[C@]1([H])C2=C3C(C[C@@]1([H])[NH2+]C)=CNC3=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2O/c1-10(9-19)6-13-12-4-3-5-14-16(12)11(8-18-14)7-15(13)17-2/h3-6,8-9,13,15,17-18H,7H2,1-2H3/p+1/b10-6+/t13-,15-/m1/s1

> <INCHI_KEY>
XFKPUSAZRRAPSC-HEESEWQSSA-O

> <FORMULA>
C16H19N2O

> <MOLECULAR_WEIGHT>
255.34

> <EXACT_MASS>
255.14918966

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.316016308737815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6R,7R)-N-methyl-7-[(1E)-2-methyl-3-oxoprop-1-en-1-yl]-2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(11),3,8(12),9-tetraen-6-aminium

> <JCHEM_LOGP>
2.1872995379999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.04948866899722

> <JCHEM_PKA_STRONGEST_BASIC>
10.239607662341466

> <JCHEM_POLAR_SURFACE_AREA>
49.47

> <JCHEM_REFRACTIVITY>
89.4062

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6R,7R)-N-methyl-7-[(1E)-2-methyl-3-oxoprop-1-en-1-yl]-2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(11),3,8(12),9-tetraen-6-aminium

> <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       3.545   5.606   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.785   4.961   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.589   2.803   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.835   3.708   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.750   1.272   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.186   5.233   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.056   1.272   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.173  -0.819   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.189   7.707   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.973   6.182   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.649   0.645   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.242   3.082   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.971   3.708   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.157   0.645   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.217   2.803   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.403   1.550   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       8.624   3.430   0.000  0.00  0.00           N+1
HETATM   18  N   UNK     0       3.633  -0.819   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       3.976   8.656   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       7.615   5.809   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       4.775   4.679   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       7.378   4.335   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   17                                                            
CONECT    3    4    5                                                       
CONECT    4    3   12                                                       
CONECT    5    3   14                                                       
CONECT    6   10   13   20                                                  
CONECT    7   11   15                                                       
CONECT    8   11   18                                                       
CONECT    9   10   19                                                       
CONECT   10    1    6    9                                                  
CONECT   11    7    8   16                                                  
CONECT   12    4   13   16                                                  
CONECT   13    6   12   15   21                                             
CONECT   14    5   16   18                                                  
CONECT   15    7   13   17   22                                             
CONECT   16   11   12   14                                                  
CONECT   17    2   15                                                       
CONECT   18    8   14                                                       
CONECT   19    9                                                            
CONECT   20    6                                                            
CONECT   21   13                                                            
CONECT   22   15                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

Synonyms

Value	Source
Chanoclavine-I aldehyde	ChEBI

Molecular Formula

C₁₆H₁₉N₂O

Average Mass

255.34

Monoisotopic Mass

255.14918966

IUPAC Name

(6R,7R)-N-methyl-7-[(1E)-2-methyl-3-oxoprop-1-en-1-yl]-2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(11),3,8(12),9-tetraen-6-aminium

Traditional Name

(6R,7R)-N-methyl-7-[(1E)-2-methyl-3-oxoprop-1-en-1-yl]-2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(11),3,8(12),9-tetraen-6-aminium

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\C)C=O)[C@]1([H])C2=C3C(C[C@@]1([H])[NH2+]C)=CNC3=CC=C2

InChI Identifier

InChI=1S/C16H18N2O/c1-10(9-19)6-13-12-4-3-5-14-16(12)11(8-18-14)7-15(13)17-2/h3-6,8-9,13,15,17-18H,7H2,1-2H3/p+1/b10-6+/t13-,15-/m1/s1

InChI Key

XFKPUSAZRRAPSC-HEESEWQSSA-O

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Clavines and derivatives

Direct Parent

Clavines and derivatives

Alternative Parents

Substituents

Chanoclavine skeleton
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
Alpha,beta-unsaturated aldehyde
Enal
Pyrrole
Heteroaromatic compound
Secondary amine
Secondary aliphatic amine
Organoheterocyclic compound
Azacycle
Hydrocarbon derivative
Amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aldehyde
Organic nitrogen compound
Carbonyl group
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indole alkaloid cation (CHEBI:71487 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	2.19	ChemAxon
pKa (Strongest Acidic)	17.05	ChemAxon
pKa (Strongest Basic)	10.24	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.47 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.41 m³·mol⁻¹	ChemAxon
Polarizability	28.32 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	9	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

28533614

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70698348

PDB ID

Not Available

ChEBI ID

71487

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 chanoclavine-I aldehyde (MMDBc0055794)

MOL for #<Metabolite:0x00007fecf801e310>

3D MOL for #<Metabolite:0x00007fecf801e310>

3D SDF for #<Metabolite:0x00007fecf801e310>

3D-SDF for #<Metabolite:0x00007fecf801e310>

PDB for #<Metabolite:0x00007fecf801e310>

3D PDB for #<Metabolite:0x00007fecf801e310>

SMILES for #<Metabolite:0x00007fecf801e310>

INCHI for #<Metabolite:0x00007fecf801e310>

Structure for #<Metabolite:0x00007fecf801e310>

3D Structure for #<Metabolite:0x00007fecf801e310>