MiMeDB: Showing metabocard for Penostatin A (MMDBc0015788)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 06:33:22 UTC

Update Date

2022-08-31 06:39:52 UTC

Metabolite ID

MMDBc0015788

Metabolite Identification

Common Name

Penostatin A

Description

Penostatin A 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 A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152108332D          

 32 34  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
    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
    7.2149    4.2826    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
    7.2149    5.6174    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
    7.6998    4.9500    0.0000 C   0  0  1  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
    8.5248    4.9500    0.0000 O   0  0  0  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
    8.0743    5.6851    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
 10  9  2  0  0  0  0
 15  2  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 12  1  0  0  0  0
 17 14  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 11  1  0  0  0  0
 19 18  1  0  0  0  0
 20 13  1  0  0  0  0
 21 10  1  1  0  0  0
 21 15  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 17 23  1  1  0  0  0
 24 20  2  0  0  0  0
 25 21  1  0  0  0  0
 25 22  1  0  0  0  0
 26  9  1  0  0  0  0
 27 10  1  0  0  0  0
 17 28  1  6  0  0  0
 18 29  1  1  0  0  0
 19 30  1  6  0  0  0
 21 31  1  6  0  0  0
 22 32  1  1  0  0  0
M  END


  Mrv1652305152108332D          

 32 34  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
    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
    7.2149    4.2826    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
    7.2149    5.6174    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
    7.6998    4.9500    0.0000 C   0  0  1  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
    8.5248    4.9500    0.0000 O   0  0  0  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
    8.0743    5.6851    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
 10  9  2  0  0  0  0
 15  2  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 12  1  0  0  0  0
 17 14  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 11  1  0  0  0  0
 19 18  1  0  0  0  0
 20 13  1  0  0  0  0
 21 10  1  1  0  0  0
 21 15  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 17 23  1  1  0  0  0
 24 20  2  0  0  0  0
 25 21  1  0  0  0  0
 25 22  1  0  0  0  0
 26  9  1  0  0  0  0
 27 10  1  0  0  0  0
 17 28  1  6  0  0  0
 18 29  1  1  0  0  0
 19 30  1  6  0  0  0
 21 31  1  6  0  0  0
 22 32  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0015788

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O3/c1-3-4-5-6-7-8-9-10-21-15(2)11-19-18-14-17(23)12-16(18)13-20(24)22(19)25-21/h9-11,13,17-19,21-23H,3-8,12,14H2,1-2H3/b10-9+/t17-,18+,19-,21-,22+/m0/s1

> <INCHI_KEY>
ONCGMAFAIBLDNP-GYGBFYAFSA-N

> <FORMULA>
C22H32O3

> <MOLECULAR_WEIGHT>
344.495

> <EXACT_MASS>
344.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.16276311259277

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4aR,8R,9aS,9bS)-8-hydroxy-2-methyl-3-[(1E)-non-1-en-1-yl]-3H,4aH,5H,7H,8H,9H,9aH,9bH-cyclopenta[f]chromen-5-one

> <ALOGPS_LOGP>
4.67

> <JCHEM_LOGP>
4.601002502

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.2653132715533

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.180122082807035

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3700017792388275

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
103.58099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4aR,8R,9aS,9bS)-8-hydroxy-2-methyl-3-[(1E)-non-1-en-1-yl]-3H,4aH,7H,8H,9H,9aH,9bH-cyclopenta[f]chromen-5-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      -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       6.668  13.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669  12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.468   7.994   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.468  10.486   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.373   9.240   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      15.913   9.240   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.002   7.700   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       8.002  10.780   0.000  0.00  0.00           O+0
HETATM   26  H   UNK     0       5.335  10.780   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       6.668  14.630   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      15.072  10.612   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      10.669   9.240   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       9.336  11.550   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       8.002  13.860   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       8.002   9.240   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2   15                                                            
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   10   26                                                  
CONECT   10    9   21   27                                                  
CONECT   11   15   19                                                       
CONECT   12   16   17                                                       
CONECT   13   16   20                                                       
CONECT   14   17   18                                                       
CONECT   15    2   11   21                                                  
CONECT   16   12   13   18                                                  
CONECT   17   12   14   23   28                                             
CONECT   18   14   16   19   29                                             
CONECT   19   11   18   22   30                                             
CONECT   20   13   22   24                                                  
CONECT   21   10   15   25   31                                             
CONECT   22   19   20   25   32                                             
CONECT   23   17                                                            
CONECT   24   20                                                            
CONECT   25   21   22                                                       
CONECT   26    9                                                            
CONECT   27   10                                                            
CONECT   28   17                                                            
CONECT   29   18                                                            
CONECT   30   19                                                            
CONECT   31   21                                                            
CONECT   32   22                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

Synonyms

Not Available

Molecular Formula

C₂₂H₃₂O₃

Average Mass

344.495

Monoisotopic Mass

344.23514489

IUPAC Name

(3S,4aR,8R,9aS,9bS)-8-hydroxy-2-methyl-3-[(1E)-non-1-en-1-yl]-3H,4aH,5H,7H,8H,9H,9aH,9bH-cyclopenta[f]chromen-5-one

Traditional Name

(3S,4aR,8R,9aS,9bS)-8-hydroxy-2-methyl-3-[(1E)-non-1-en-1-yl]-3H,4aH,7H,8H,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[C@]([H])(O)C[C@@]3([H])[C@]2([H])C=C1C

InChI Identifier

InChI=1S/C22H32O3/c1-3-4-5-6-7-8-9-10-21-15(2)11-19-18-14-17(23)12-16(18)13-20(24)22(19)25-21/h9-11,13,17-19,21-23H,3-8,12,14H2,1-2H3/b10-9+/t17-,18+,19-,21-,22+/m0/s1

InChI Key

ONCGMAFAIBLDNP-GYGBFYAFSA-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
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Alcohol
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	0.014 g/L	ALOGPS
logP	4.67	ALOGPS
logP	4.6	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	16.18	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.58 m³·mol⁻¹	ChemAxon
Polarizability	41.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

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

8490966

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Penostatin A

METLIN ID

Not Available

PubChem Compound

10315501

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 A (MMDBc0015788)

MOL for #<Metabolite:0x00005634c0f5fcf8>

3D MOL for #<Metabolite:0x00005634c0f5fcf8>

3D SDF for #<Metabolite:0x00005634c0f5fcf8>

3D-SDF for #<Metabolite:0x00005634c0f5fcf8>

PDB for #<Metabolite:0x00005634c0f5fcf8>

3D PDB for #<Metabolite:0x00005634c0f5fcf8>

SMILES for #<Metabolite:0x00005634c0f5fcf8>

INCHI for #<Metabolite:0x00005634c0f5fcf8>

Structure for #<Metabolite:0x00005634c0f5fcf8>

3D Structure for #<Metabolite:0x00005634c0f5fcf8>