MiMeDB: Showing metabocard for fumigaclavine B (MMDBc0055991)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:12:43 UTC

Update Date

2022-08-12 20:09:31 UTC

Metabolite ID

MMDBc0055991

Metabolite Identification

Common Name

fumigaclavine B

Description

fumigaclavine B(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 small amount of articles have been published on fumigaclavine B(1+).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222122D          

 23 26  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
    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  1  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
    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
    2.5645    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939    1.6495    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6914    1.9520    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
  9  1  1  1  0  0  0
  9  8  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17  7  1  0  0  0  0
 17 12  1  0  0  0  0
 18  2  1  0  0  0  0
 18  8  1  0  0  0  0
 18 13  1  0  0  0  0
 16 19  1  1  0  0  0
  9 20  1  6  0  0  0
 13 21  1  1  0  0  0
 15 22  1  6  0  0  0
 16 23  1  6  0  0  0
M  CHG  1  17   1
M  END
> <DATABASE_ID>
MMDBc0055991

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(C)CN(C)[C@]2([H])CC3=C[NH2+]C4=CC=CC(=C34)[C@@]2([H])[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O/c1-9-8-18(2)13-6-10-7-17-12-5-3-4-11(14(10)12)15(13)16(9)19/h3-5,7,9,13,15-17,19H,6,8H2,1-2H3/p+1/t9-,13+,15+,16-/m0/s1

> <INCHI_KEY>
JUXRVSRUBIFVKE-CIGJXOAISA-O

> <FORMULA>
C16H21N2O

> <MOLECULAR_WEIGHT>
257.356

> <EXACT_MASS>
257.164839724

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.670458776938545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.7990977190000013

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.559147971459453

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.487535709674546

> <JCHEM_PKA_STRONGEST_BASIC>
8.141947608795798

> <JCHEM_POLAR_SURFACE_AREA>
40.08

> <JCHEM_REFRACTIVITY>
88.09140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

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

> <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       8.788   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       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.454  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.120  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.264   2.570   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.787  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+1
HETATM   18  N   UNK     0       6.121  -0.770   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       7.454   3.080   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0       6.121   0.770   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       4.842   3.079   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       6.891   3.644   0.000  0.00  0.00           H+0
CONECT    1    9                                                            
CONECT    2   18                                                            
CONECT    3    4    5                                                       
CONECT    4    3   11                                                       
CONECT    5    3   12                                                       
CONECT    6   10   13                                                       
CONECT    7   10   17                                                       
CONECT    8    9   18                                                       
CONECT    9    1    8   16   20                                             
CONECT   10    6    7   14                                                  
CONECT   11    4   14   15                                                  
CONECT   12    5   14   17                                                  
CONECT   13    6   15   18   21                                             
CONECT   14   10   11   12                                                  
CONECT   15   11   13   16   22                                             
CONECT   16    9   15   19   23                                             
CONECT   17    7   12                                                       
CONECT   18    2    8   13                                                  
CONECT   19   16                                                            
CONECT   20    9                                                            
CONECT   21   13                                                            
CONECT   22   15                                                            
CONECT   23   16                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

Synonyms

Value	Source
Fumigaclavine b	ChEBI

Molecular Formula

C₁₆H₂₁N₂O

Average Mass

257.356

Monoisotopic Mass

257.164839724

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@]1(C)CN(C)[C@]2([H])CC3=C[NH2+]C4=CC=CC(=C34)[C@@]2([H])[C@@]1([H])O

InChI Identifier

InChI=1S/C16H20N2O/c1-9-8-18(2)13-6-10-7-17-12-5-3-4-11(14(10)12)15(13)16(9)19/h3-5,7,9,13,15-17,19H,6,8H2,1-2H3/p+1/t9-,13+,15+,16-/m0/s1

InChI Key

JUXRVSRUBIFVKE-CIGJXOAISA-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

Clavine skeleton
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
3-alkylindole
Quinoline
Isoindole or derivatives
Indole or derivatives
Indole
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Alcohol
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ammonium ion (CHEBI:67146 )
organic cation (CHEBI:67146 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	1.8	ChemAxon
pKa (Strongest Acidic)	14.49	ChemAxon
pKa (Strongest Basic)	8.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.08 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	88.09 m³·mol⁻¹	ChemAxon
Polarizability	29.67 Å³	ChemAxon
Number of Rings	4	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	2

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

28533135

KEGG Compound ID

Not Available

BioCyc ID

CPD-12330

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70678820

PDB ID

Not Available

ChEBI ID

67146

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 fumigaclavine B (MMDBc0055991)

MOL for #<Metabolite:0x00007fecf7f04dd0>

3D MOL for #<Metabolite:0x00007fecf7f04dd0>

3D SDF for #<Metabolite:0x00007fecf7f04dd0>

3D-SDF for #<Metabolite:0x00007fecf7f04dd0>

PDB for #<Metabolite:0x00007fecf7f04dd0>

3D PDB for #<Metabolite:0x00007fecf7f04dd0>

SMILES for #<Metabolite:0x00007fecf7f04dd0>

INCHI for #<Metabolite:0x00007fecf7f04dd0>

Structure for #<Metabolite:0x00007fecf7f04dd0>

3D Structure for #<Metabolite:0x00007fecf7f04dd0>