MiMeDB: Showing metabocard for Penostatin C (MMDBc0012608)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 04:06:44 UTC

Update Date

2022-08-31 06:34:46 UTC

Metabolite ID

MMDBc0012608

Metabolite Identification

Common Name

Penostatin C

Description

Penostatin C belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Penostatin C is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152106062D          

 30 32  0  0  1  0            999 V2000
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6998    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2149    4.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2149    5.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.8375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  9  2  0  0  0  0
 16  2  1  0  0  0  0
 16 14  2  0  0  0  0
 17 11  1  0  0  0  0
 17 15  2  0  0  0  0
 18 12  1  0  0  0  0
 18 17  1  0  0  0  0
 19 14  1  0  0  0  0
 19 18  1  0  0  0  0
 20 15  1  0  0  0  0
 21 13  1  1  0  0  0
 21 16  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 20  2  0  0  0  0
 24 21  1  0  0  0  0
 24 22  1  0  0  0  0
 25  9  1  0  0  0  0
 26 13  1  0  0  0  0
 18 27  1  1  0  0  0
 19 28  1  6  0  0  0
 21 29  1  6  0  0  0
 22 30  1  1  0  0  0
M  END


  Mrv1652305152106062D          

 30 32  0  0  1  0            999 V2000
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6998    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2149    4.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2149    5.6174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    6.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013    5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    7.8375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    7.4250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  9  2  0  0  0  0
 16  2  1  0  0  0  0
 16 14  2  0  0  0  0
 17 11  1  0  0  0  0
 17 15  2  0  0  0  0
 18 12  1  0  0  0  0
 18 17  1  0  0  0  0
 19 14  1  0  0  0  0
 19 18  1  0  0  0  0
 20 15  1  0  0  0  0
 21 13  1  1  0  0  0
 21 16  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 20  2  0  0  0  0
 24 21  1  0  0  0  0
 24 22  1  0  0  0  0
 25  9  1  0  0  0  0
 26 13  1  0  0  0  0
 18 27  1  1  0  0  0
 19 28  1  6  0  0  0
 21 29  1  6  0  0  0
 22 30  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0012608

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CCCCCCC)=C(\[H])[C@]1([H])O[C@@]2([H])C(=O)C=C3C=CC[C@@]3([H])[C@]2([H])C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O2/c1-3-4-5-6-7-8-9-13-21-16(2)14-19-18-12-10-11-17(18)15-20(23)22(19)24-21/h9-11,13-15,18-19,21-22H,3-8,12H2,1-2H3/b13-9+/t18-,19+,21+,22-/m1/s1

> <INCHI_KEY>
HWLGMVWNJRZMKV-MHNZBMDGSA-N

> <FORMULA>
C22H30O2

> <MOLECULAR_WEIGHT>
326.48

> <EXACT_MASS>
326.224580206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.4962443666418

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4aR,9aS,9bS)-2-methyl-3-[(1E)-non-1-en-1-yl]-3H,4aH,5H,9H,9aH,9bH-cyclopenta[f]chromen-5-one

> <ALOGPS_LOGP>
5.47

> <JCHEM_LOGP>
5.625799372333335

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.43805074249253

> <JCHEM_PKA_STRONGEST_BASIC>
-4.256123882228669

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
103.02809999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.95e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4aR,9aS,9bS)-2-methyl-3-[(1E)-non-1-en-1-yl]-3H,4aH,9H,9aH,9bH-cyclopenta[f]chromen-5-one

> <JCHEM_VEBER_RULE>
1

$$$$

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      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  14.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000  12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  12.320   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.373   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.468   7.994   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.468  10.486   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003  10.010   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  10.010   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.002   7.700   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002  10.780   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       5.335  10.780   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       6.668  14.630   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      10.669   9.240   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       9.336  11.550   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       8.002  13.860   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       8.002   9.240   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2   16                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   13   25                                                  
CONECT   10   11   12                                                       
CONECT   11   10   17                                                       
CONECT   12   10   18                                                       
CONECT   13    9   21   26                                                  
CONECT   14   16   19                                                       
CONECT   15   17   20                                                       
CONECT   16    2   14   21                                                  
CONECT   17   11   15   18                                                  
CONECT   18   12   17   19   27                                             
CONECT   19   14   18   22   28                                             
CONECT   20   15   22   23                                                  
CONECT   21   13   16   24   29                                             
CONECT   22   19   20   24   30                                             
CONECT   23   20                                                            
CONECT   24   21   22                                                       
CONECT   25    9                                                            
CONECT   26   13                                                            
CONECT   27   18                                                            
CONECT   28   19                                                            
CONECT   29   21                                                            
CONECT   30   22                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

Synonyms

Not Available

Molecular Formula

C₂₂H₃₀O₂

Average Mass

326.48

Monoisotopic Mass

326.224580206

IUPAC Name

(3S,4aR,9aS,9bS)-2-methyl-3-[(1E)-non-1-en-1-yl]-3H,4aH,5H,9H,9aH,9bH-cyclopenta[f]chromen-5-one

Traditional Name

(3S,4aR,9aS,9bS)-2-methyl-3-[(1E)-non-1-en-1-yl]-3H,4aH,9H,9aH,9bH-cyclopenta[f]chromen-5-one

CAS Registry Number

Not Available

SMILES

[H]\C(CCCCCCC)=C(\[H])[C@]1([H])O[C@@]2([H])C(=O)C=C3C=CC[C@@]3([H])[C@]2([H])C=C1C

InChI Identifier

InChI=1S/C22H30O2/c1-3-4-5-6-7-8-9-13-21-16(2)14-19-18-12-10-11-17(18)15-20(23)22(19)24-21/h9-11,13-15,18-19,21-22H,3-8,12H2,1-2H3/b13-9+/t18-,19+,21+,22-/m1/s1

InChI Key

HWLGMVWNJRZMKV-MHNZBMDGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Pyran
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	5.47	ALOGPS
logP	5.63	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	18.44	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.03 m³·mol⁻¹	ChemAxon
Polarizability	39.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	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
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

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

8240508

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10064968

PDB ID

Not Available

ChEBI ID

Not Available

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 Penostatin C (MMDBc0012608)

MOL for #<Metabolite:0x00007fdb70d1d2d0>

3D MOL for #<Metabolite:0x00007fdb70d1d2d0>

3D SDF for #<Metabolite:0x00007fdb70d1d2d0>

3D-SDF for #<Metabolite:0x00007fdb70d1d2d0>

PDB for #<Metabolite:0x00007fdb70d1d2d0>

3D PDB for #<Metabolite:0x00007fdb70d1d2d0>

SMILES for #<Metabolite:0x00007fdb70d1d2d0>

INCHI for #<Metabolite:0x00007fdb70d1d2d0>

Structure for #<Metabolite:0x00007fdb70d1d2d0>

3D Structure for #<Metabolite:0x00007fdb70d1d2d0>