MiMeDB: Showing metabocard for Tilivalline (MMDBc0020325)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 10:18:52 UTC

Update Date

2022-08-31 06:46:37 UTC

Metabolite ID

MMDBc0020325

Metabolite Identification

Common Name

Tilivalline

Description

Tilivalline belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine. Tilivalline is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Tilivalline.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152112182D          

 27 31  0  0  1  0            999 V2000
    3.1747    5.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5980    6.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050    1.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    1.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9522    4.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194    0.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7987    5.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8068    2.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795    2.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184    1.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569    3.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1530    4.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084    1.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7702    3.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5762    5.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6293    2.3347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2685    2.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1364    2.9855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4829    2.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5691    1.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8370    4.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9614    2.9947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219    1.5325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4431    3.4137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5783    0.3580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2966    3.0897    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5675    3.6889    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  5  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15  7  2  0  0  0  0
 15 12  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  2  0  0  0  0
 18 14  1  6  0  0  0
 18 16  1  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 13  1  0  0  0  0
 21 11  1  0  0  0  0
 21 15  1  0  0  0  0
 22 18  1  0  0  0  0
 22 19  1  0  0  0  0
 23 10  1  0  0  0  0
 23 16  1  0  0  0  0
 23 20  1  0  0  0  0
 24 17  1  0  0  0  0
 25 20  2  0  0  0  0
 16 26  1  6  0  0  0
 18 27  1  1  0  0  0
M  END


  Mrv1652305152112182D          

 27 31  0  0  1  0            999 V2000
    3.1747    5.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5980    6.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050    1.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4911    1.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9522    4.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9194    0.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7987    5.8399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8068    2.3995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8795    2.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184    1.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9569    3.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1530    4.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3084    1.5491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7702    3.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5762    5.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6293    2.3347    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2685    2.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1364    2.9855    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4829    2.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5691    1.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8370    4.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9614    2.9947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219    1.5325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4431    3.4137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5783    0.3580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2966    3.0897    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5675    3.6889    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  5  1  1  0  0  0  0
  6  3  2  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15  7  2  0  0  0  0
 15 12  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  2  0  0  0  0
 18 14  1  6  0  0  0
 18 16  1  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 13  1  0  0  0  0
 21 11  1  0  0  0  0
 21 15  1  0  0  0  0
 22 18  1  0  0  0  0
 22 19  1  0  0  0  0
 23 10  1  0  0  0  0
 23 16  1  0  0  0  0
 23 20  1  0  0  0  0
 24 17  1  0  0  0  0
 25 20  2  0  0  0  0
 16 26  1  6  0  0  0
 18 27  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0020325

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12CCCN1C(=O)C1=C(N[C@@]2([H])C2=CNC3=CC=CC=C23)C(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H19N3O2/c24-17-9-3-6-13-19(17)22-18(16-8-4-10-23(16)20(13)25)14-11-21-15-7-2-1-5-12(14)15/h1-3,5-7,9,11,16,18,21-22,24H,4,8,10H2/t16-,18-/m0/s1

> <INCHI_KEY>
AJZNARCWDDMOPL-WMZOPIPTSA-N

> <FORMULA>
C20H19N3O2

> <MOLECULAR_WEIGHT>
333.391

> <EXACT_MASS>
333.147726864

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
35.4056385014813

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7S,8S)-11-hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),11,13-trien-2-one

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
3.2674928209999994

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.874978265681815

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.605276572851084

> <JCHEM_PKA_STRONGEST_BASIC>
1.9695434722913845

> <JCHEM_POLAR_SURFACE_AREA>
68.36000000000001

> <JCHEM_REFRACTIVITY>
97.71599999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7S,8S)-11-hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),11,13-trien-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0       5.926  10.182   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.850  11.283   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.783   2.327   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.917   3.056   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.511   8.699   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.316   1.857   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.358  10.901   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.506   4.479   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.108   3.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.088   2.056   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.786   7.211   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.019   8.317   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.176   2.892   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.304   6.953   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.942   9.418   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.041   4.358   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.968   4.867   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.988   5.573   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.501   4.397   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.796   2.208   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.562   8.734   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       5.528   5.590   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       3.401   2.861   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       8.294   6.372   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.813   0.668   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       2.420   5.767   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.793   6.886   0.000  0.00  0.00           H+0
CONECT    1    2    5                                                       
CONECT    2    1    7                                                       
CONECT    3    6    9                                                       
CONECT    4    8   10                                                       
CONECT    5    1   12                                                       
CONECT    6    3   13                                                       
CONECT    7    2   15                                                       
CONECT    8    4   16                                                       
CONECT    9    3   17                                                       
CONECT   10    4   23                                                       
CONECT   11   14   21                                                       
CONECT   12    5   14   15                                                  
CONECT   13    6   19   20                                                  
CONECT   14   11   12   18                                                  
CONECT   15    7   12   21                                                  
CONECT   16    8   18   23   26                                             
CONECT   17    9   19   24                                                  
CONECT   18   14   16   22   27                                             
CONECT   19   13   17   22                                                  
CONECT   20   13   23   25                                                  
CONECT   21   11   15                                                       
CONECT   22   18   19                                                       
CONECT   23   10   16   20                                                  
CONECT   24   17                                                            
CONECT   25   20                                                            
CONECT   26   16                                                            
CONECT   27   18                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

Synonyms

Value	Source
(7S,8S)-11-Hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.0(3,7)]tetradeca-1(10),11,13-trien-2-one	ChEBI
Epitilivalline	ChEBI

Molecular Formula

C₂₀H₁₉N₃O₂

Average Mass

333.391

Monoisotopic Mass

333.147726864

IUPAC Name

(7S,8S)-11-hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),11,13-trien-2-one

Traditional Name

(7S,8S)-11-hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.0^{3,7}]tetradeca-1(10),11,13-trien-2-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCCN1C(=O)C1=C(N[C@@]2([H])C2=CNC3=CC=CC=C23)C(O)=CC=C1

InChI Identifier

InChI=1S/C20H19N3O2/c24-17-9-3-6-13-19(17)22-18(16-8-4-10-23(16)20(13)25)14-11-21-15-7-2-1-5-12(14)15/h1-3,5-7,9,11,16,18,21-22,24H,4,8,10H2/t16-,18-/m0/s1

InChI Key

AJZNARCWDDMOPL-WMZOPIPTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

1,4-benzodiazepine
3-alkylindole
Indole
Indole or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Secondary aliphatic/aromatic amine
Aralkylamine
Substituted pyrrole
Benzenoid
Pyrrole
Pyrrolidine
Tertiary carboxylic acid amide
Heteroaromatic compound
Vinylogous amide
Amino acid or derivatives
Lactam
Carboxamide group
Secondary amine
Carboxylic acid derivative
Azacycle
Organic oxide
Organopnictogen compound
Amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
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	0.21 g/L	ALOGPS
logP	3.12	ALOGPS
logP	3.27	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.61	ChemAxon
pKa (Strongest Basic)	1.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	68.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	97.72 m³·mol⁻¹	ChemAxon
Polarizability	35.41 Å³	ChemAxon
Number of Rings	5	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

Not Available

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
Bacteria	Proteobacteria	1	Human ; Human sputum; Human subgingival plaque; Human feces	Metabolic reconstruction

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

113792

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tilivalline

METLIN ID

Not Available

PubChem Compound

128363

PDB ID

Not Available

ChEBI ID

156292

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Tilivalline (MMDBc0020325)

MOL for #<Metabolite:0x00007fecf48d8608>

3D MOL for #<Metabolite:0x00007fecf48d8608>

3D SDF for #<Metabolite:0x00007fecf48d8608>

3D-SDF for #<Metabolite:0x00007fecf48d8608>

PDB for #<Metabolite:0x00007fecf48d8608>

3D PDB for #<Metabolite:0x00007fecf48d8608>

SMILES for #<Metabolite:0x00007fecf48d8608>

INCHI for #<Metabolite:0x00007fecf48d8608>

Structure for #<Metabolite:0x00007fecf48d8608>

3D Structure for #<Metabolite:0x00007fecf48d8608>