MiMeDB: Showing metabocard for Festuclavine (MMDBc0011539)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 03:22:41 UTC

Update Date

2022-08-31 06:33:12 UTC

Metabolite ID

MMDBc0011539

Metabolite Identification

Common Name

Festuclavine

Description

Costaclavine, also known as festuclavin or pyroclavin, 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. Costaclavine is a very strong basic compound (based on its pKa). Costaclavine is a naturally occuring alkaloid of the ergoline family. Costaclavine is a potentially toxic compound. Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Usually the gastrointestinal effects precede the central nervous system effects. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. Convulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212302D          

 18 21  0  0  0  0            999 V2000
   -0.8455   -3.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8445   -2.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296   -2.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425   -0.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5575   -1.3911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5585   -2.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2715   -0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  4 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 15  1  0  0  0  0
 10 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0011539

> <DATABASE_NAME>
MIME

> <SMILES>
CC1CC2C(CC3=CNC4=CC=CC2=C34)N(C)C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-5,8,10,13,15,17H,6-7,9H2,1-2H3

> <INCHI_KEY>
VLMZMRDOMOGGFA-UHFFFAOYSA-N

> <FORMULA>
C16H20N2

> <MOLECULAR_WEIGHT>
240.3434

> <EXACT_MASS>
240.16264865

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.488498022559344

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene

> <ALOGPS_LOGP>
3.30

> <JCHEM_LOGP>
3.102702792

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.350714133254595

> <JCHEM_PKA_STRONGEST_BASIC>
9.012155443883788

> <JCHEM_POLAR_SURFACE_AREA>
19.03

> <JCHEM_REFRACTIVITY>
75.2346

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.578  -6.448   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.576  -4.908   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.242  -4.140   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.240  -2.600   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.573  -1.828   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.860   2.080   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -2.907  -2.597   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -2.909  -4.137   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.240  -1.825   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    4   15                                                  
CONECT   15   14    7   10                                                  
CONECT   16    5   17   18                                                  
CONECT   17   16    2                                                       
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

Synonyms

Value	Source
Costaclavin	MeSH
Festuclavin	MeSH
Costaclavin, (8alpha)-isomer	MeSH
Epicostaclavin	MeSH
Festuclavine	MeSH
Pyroclavin	MeSH
Costaclavin, (8beta)-isomer	MeSH

Molecular Formula

C₁₆H₂₀N₂

Average Mass

240.3434

Monoisotopic Mass

240.16264865

IUPAC Name

4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene

Traditional Name

4,6-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),9,12,14-tetraene

CAS Registry Number

Not Available

SMILES

CC1CC2C(CC3=CNC4=CC=CC2=C34)N(C)C1

InChI Identifier

InChI=1S/C16H20N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-5,8,10,13,15,17H,6-7,9H2,1-2H3

InChI Key

VLMZMRDOMOGGFA-UHFFFAOYSA-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
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	3.3	ALOGPS
logP	3.1	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	17.35	ChemAxon
pKa (Strongest Basic)	9.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	19.03 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.23 m³·mol⁻¹	ChemAxon
Polarizability	28.49 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-6be4a2b67c74f1f5d111	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-1390000000-4a259d4c8d5b68cd3b2c	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zi0-2900000000-3fbba04bb9c466370d7b	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-ce3715cce5fb96e3ba97	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0190000000-9700c8865ff16031ac91	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-1930000000-04069754b980121bcd52	2016-08-03	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

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	6	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100077

PDB ID

Not Available

ChEBI ID

Not Available

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 Festuclavine (MMDBc0011539)

MOL for #<Metabolite:0x00007feced190370>

3D MOL for #<Metabolite:0x00007feced190370>

3D SDF for #<Metabolite:0x00007feced190370>

3D-SDF for #<Metabolite:0x00007feced190370>

PDB for #<Metabolite:0x00007feced190370>

3D PDB for #<Metabolite:0x00007feced190370>

SMILES for #<Metabolite:0x00007feced190370>

INCHI for #<Metabolite:0x00007feced190370>

Structure for #<Metabolite:0x00007feced190370>

3D Structure for #<Metabolite:0x00007feced190370>