MiMeDB: Showing metabocard for didehydroagroclavine (MMDBc0055917)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:10:42 UTC

Update Date

2022-08-12 20:09:29 UTC

Metabolite ID

MMDBc0055917

Metabolite Identification

Common Name

didehydroagroclavine

Description

didehydroagroclavine 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. didehydroagroclavine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on didehydroagroclavine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222102D          

 20 23  0  0  1  0            999 V2000
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486    1.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.8357    0.4382    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -0.8250    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  0  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  8  1  0  0  0  0
 17 14  1  0  0  0  0
 18  2  1  0  0  0  0
 18  9  2  0  0  0  0
 18 15  1  0  0  0  0
 13 19  1  6  0  0  0
 15 20  1  1  0  0  0
M  CHG  1  18   1
M  END
> <DATABASE_ID>
MMDBc0055917

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CC3=CNC4=CC=CC(=C34)[C@@]1([H])C=C(C)C=[N+]2C

> <INCHI_IDENTIFIER>
InChI=1S/C16H17N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8-9,13,15,17H,7H2,1-2H3/q+1/t13-,15-/m1/s1

> <INCHI_KEY>
CATKRDCRCIXECQ-UKRRQHHQSA-N

> <FORMULA>
C16H17N2

> <MOLECULAR_WEIGHT>
237.325

> <EXACT_MASS>
237.138624976

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.764530700434538

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,7R)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),3,5,9,12,14-hexaen-6-ium

> <JCHEM_LOGP>
-0.8999506531384125

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.032294590197097

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.561532159735773

> <JCHEM_POLAR_SURFACE_AREA>
18.799999999999997

> <JCHEM_REFRACTIVITY>
86.36330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,7R)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),3,5,9,12,14-hexaen-6-ium

> <JCHEM_VEBER_RULE>
1

$$$$

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       8.788   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.479   4.553   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.264   2.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.787  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       6.121  -0.770   0.000  0.00  0.00           N+1
HETATM   19  H   UNK     0       3.427   0.818   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.787  -1.540   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   18                                                            
CONECT    3    4    5                                                       
CONECT    4    3   12                                                       
CONECT    5    3   14                                                       
CONECT    6   10   13                                                       
CONECT    7   11   15                                                       
CONECT    8   11   17                                                       
CONECT    9   10   18                                                       
CONECT   10    1    6    9                                                  
CONECT   11    7    8   16                                                  
CONECT   12    4   13   16                                                  
CONECT   13    6   12   15   19                                             
CONECT   14    5   16   17                                                  
CONECT   15    7   13   18   20                                             
CONECT   16   11   12   14                                                  
CONECT   17    8   14                                                       
CONECT   18    2    9   15                                                  
CONECT   19   13                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

Synonyms

Value	Source
(2R,7R)-4,6-Dimethyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),3,5,9,12,14-hexaen-6-ium	ChEBI
6,7-Didehydroagroclavine	ChEBI

Molecular Formula

C₁₆H₁₇N₂

Average Mass

237.325

Monoisotopic Mass

237.138624976

IUPAC Name

(2R,7R)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),3,5,9,12,14-hexaen-6-ium

Traditional Name

(2R,7R)-4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),3,5,9,12,14-hexaen-6-ium

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC3=CNC4=CC=CC(=C34)[C@@]1([H])C=C(C)C=[N+]2C

InChI Identifier

InChI=1S/C16H17N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8-9,13,15,17H,7H2,1-2H3/q+1/t13-,15-/m1/s1

InChI Key

CATKRDCRCIXECQ-UKRRQHHQSA-N

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

Clavine skeleton
Benzoquinoline
Pyrroloquinoline
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Benzenoid
Heteroaromatic compound
Pyrrole
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic cation (CHEBI:65036 )
ergot alkaloid (CHEBI:65036 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-0.9	ChemAxon
pKa (Strongest Acidic)	16.56	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	18.8 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.36 m³·mol⁻¹	ChemAxon
Polarizability	27.76 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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	4	Human feces

Exposure Sources

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

28184754

KEGG Compound ID

C20457

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57339211

PDB ID

Not Available

ChEBI ID

65036

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 didehydroagroclavine (MMDBc0055917)

MOL for #<Metabolite:0x0000556b690e56f8>

3D MOL for #<Metabolite:0x0000556b690e56f8>

3D SDF for #<Metabolite:0x0000556b690e56f8>

3D-SDF for #<Metabolite:0x0000556b690e56f8>

PDB for #<Metabolite:0x0000556b690e56f8>

3D PDB for #<Metabolite:0x0000556b690e56f8>

SMILES for #<Metabolite:0x0000556b690e56f8>

INCHI for #<Metabolite:0x0000556b690e56f8>

Structure for #<Metabolite:0x0000556b690e56f8>

3D Structure for #<Metabolite:0x0000556b690e56f8>