MiMeDB: Showing metabocard for Alternapyrone C (MMDBc0023894)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 13:47:40 UTC

Update Date

2022-08-31 06:48:49 UTC

Metabolite ID

MMDBc0023894

Metabolite Identification

Common Name

Alternapyrone C

Description

Alternapyrone C belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review very few articles have been published on Alternapyrone C.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152115472D          

 33 33  0  0  0  0            999 V2000
   -3.9849    4.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    8.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151    9.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526    9.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526   12.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8099    4.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474    7.0125    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
   -2.3349    7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    9.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    9.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8099    6.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    8.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0474    5.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    6.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651    9.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724    8.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026    9.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   10.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   12.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224    5.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526   11.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151   10.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151   12.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4599    6.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    6.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6776   11.2993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   12.7283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   11.2993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 18  2  1  0  0  0  0
 18 10  1  0  0  0  0
 18 14  2  0  0  0  0
 19  3  1  0  0  0  0
 19 12  2  0  0  0  0
 19 13  1  0  0  0  0
 20  4  1  0  0  0  0
 12 20  1  4  0  0  0
 20 15  2  0  0  0  0
 21  5  1  0  0  0  0
 21 13  1  0  0  0  0
 22  6  1  0  0  0  0
 23  7  1  0  0  0  0
 24  8  1  0  0  0  0
 14 24  1  4  0  0  0
 24 16  1  0  0  0  0
 25 11  1  0  0  0  0
 15 25  1  4  0  0  0
 25 17  1  0  0  0  0
 26 22  1  0  0  0  0
 26 23  2  0  0  0  0
 27 21  1  0  0  0  0
 27 22  2  0  0  0  0
 28 23  1  0  0  0  0
 29 16  1  0  0  0  0
 30 17  1  0  0  0  0
 31 26  1  0  0  0  0
 32 28  2  0  0  0  0
 33 27  1  0  0  0  0
 33 28  1  0  0  0  0
M  END


  Mrv1652305152115472D          

 33 33  0  0  0  0            999 V2000
   -3.9849    4.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    5.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    8.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151    9.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526    9.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526   12.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8099    4.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7474    7.0125    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
   -2.3349    7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    9.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    9.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8099    6.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    8.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0474    5.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9849    6.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9651    9.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724    8.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026    9.8704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   10.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4401   12.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2224    5.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    7.7270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8526   11.2993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151   10.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6151   12.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4599    6.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5099    6.2980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6776   11.2993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   12.7283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2026   11.2993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 18  2  1  0  0  0  0
 18 10  1  0  0  0  0
 18 14  2  0  0  0  0
 19  3  1  0  0  0  0
 19 12  2  0  0  0  0
 19 13  1  0  0  0  0
 20  4  1  0  0  0  0
 12 20  1  4  0  0  0
 20 15  2  0  0  0  0
 21  5  1  0  0  0  0
 21 13  1  0  0  0  0
 22  6  1  0  0  0  0
 23  7  1  0  0  0  0
 24  8  1  0  0  0  0
 14 24  1  4  0  0  0
 24 16  1  0  0  0  0
 25 11  1  0  0  0  0
 15 25  1  4  0  0  0
 25 17  1  0  0  0  0
 26 22  1  0  0  0  0
 26 23  2  0  0  0  0
 27 21  1  0  0  0  0
 27 22  2  0  0  0  0
 28 23  1  0  0  0  0
 29 16  1  0  0  0  0
 30 17  1  0  0  0  0
 31 26  1  0  0  0  0
 32 28  2  0  0  0  0
 33 27  1  0  0  0  0
 33 28  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0023894

> <DATABASE_NAME>
MIME

> <SMILES>
CCC(CO)C=C(C)CCCC(CO)C=C(C)C=C(C)CC(C)C1=C(C)C(O)=C(C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C28H44O5/c1-8-24(16-29)14-18(2)10-9-11-25(17-30)15-20(4)12-19(3)13-21(5)27-22(6)26(31)23(7)28(32)33-27/h12,14-15,21,24-25,29-31H,8-11,13,16-17H2,1-7H3

> <INCHI_KEY>
BEOXKIXIEOFDGJ-UHFFFAOYSA-N

> <FORMULA>
C28H44O5

> <MOLECULAR_WEIGHT>
460.655

> <EXACT_MASS>
460.318874517

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.365166731849065

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[14-ethyl-15-hydroxy-8-(hydroxymethyl)-4,6,12-trimethylpentadeca-4,6,12-trien-2-yl]-4-hydroxy-3,5-dimethyl-2H-pyran-2-one

> <ALOGPS_LOGP>
4.76

> <JCHEM_LOGP>
5.355788541333332

> <ALOGPS_LOGS>
-5.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.590673319161162

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.729695234125447

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3514815688996435

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
140.251

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[14-ethyl-15-hydroxy-8-(hydroxymethyl)-4,6,12-trimethylpentadeca-4,6,12-trien-2-yl]-4-hydroxy-3,5-dimethylpyran-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      -7.438   9.089   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  10.423   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.572  15.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.262  14.424   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.882  17.091   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.192  18.425   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.192  23.759   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.978   9.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.128  13.090   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      -4.358  14.424   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.262  17.091   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.572  18.425   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.978  11.756   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.048  15.757   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -11.288  10.423   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.048  13.090   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.438  11.756   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.802  17.091   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.508  15.757   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.112  18.425   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.422  19.758   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.422  22.426   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.748  10.423   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.818  14.424   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.192  21.092   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.882  19.758   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.882  22.426   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -12.058  11.756   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -2.818  11.756   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.732  21.092   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.112  23.759   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       4.112  21.092   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5   21                                                            
CONECT    6   22                                                            
CONECT    7   23                                                            
CONECT    8    1   24                                                       
CONECT    9   10   11                                                       
CONECT   10    9   18                                                       
CONECT   11    9   25                                                       
CONECT   12   19   20                                                       
CONECT   13   19   21                                                       
CONECT   14   18   24                                                       
CONECT   15   20   25                                                       
CONECT   16   24   29                                                       
CONECT   17   25   30                                                       
CONECT   18    2   10   14                                                  
CONECT   19    3   12   13                                                  
CONECT   20    4   12   15                                                  
CONECT   21    5   13   27                                                  
CONECT   22    6   26   27                                                  
CONECT   23    7   26   28                                                  
CONECT   24    8   14   16                                                  
CONECT   25   11   15   17                                                  
CONECT   26   22   23   31                                                  
CONECT   27   21   22   33                                                  
CONECT   28   23   32   33                                                  
CONECT   29   16                                                            
CONECT   30   17                                                            
CONECT   31   26                                                            
CONECT   32   28                                                            
CONECT   33   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

Synonyms

Not Available

Molecular Formula

C₂₈H₄₄O₅

Average Mass

460.655

Monoisotopic Mass

460.318874517

IUPAC Name

6-[14-ethyl-15-hydroxy-8-(hydroxymethyl)-4,6,12-trimethylpentadeca-4,6,12-trien-2-yl]-4-hydroxy-3,5-dimethyl-2H-pyran-2-one

Traditional Name

6-[14-ethyl-15-hydroxy-8-(hydroxymethyl)-4,6,12-trimethylpentadeca-4,6,12-trien-2-yl]-4-hydroxy-3,5-dimethylpyran-2-one

CAS Registry Number

Not Available

SMILES

CCC(CO)C=C(C)CCCC(CO)C=C(C)C=C(C)CC(C)C1=C(C)C(O)=C(C)C(=O)O1

InChI Identifier

InChI=1S/C28H44O5/c1-8-24(16-29)14-18(2)10-9-11-25(17-30)15-20(4)12-19(3)13-21(5)27-22(6)26(31)23(7)28(32)33-27/h12,14-15,21,24-25,29-31H,8-11,13,16-17H2,1-7H3

InChI Key

BEOXKIXIEOFDGJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpenoid
Diterpene lactone
Long chain fatty alcohol
Fatty alcohol
Pyranone
Fatty acyl
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0037 g/L	ALOGPS
logP	4.76	ALOGPS
logP	5.36	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	7.73	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	140.25 m³·mol⁻¹	ChemAxon
Polarizability	53.37 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	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

78444713

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139591185

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 Alternapyrone C (MMDBc0023894)

MOL for #<Metabolite:0x00007f922eeb0290>

3D MOL for #<Metabolite:0x00007f922eeb0290>

3D SDF for #<Metabolite:0x00007f922eeb0290>

3D-SDF for #<Metabolite:0x00007f922eeb0290>

PDB for #<Metabolite:0x00007f922eeb0290>

3D PDB for #<Metabolite:0x00007f922eeb0290>

SMILES for #<Metabolite:0x00007f922eeb0290>

INCHI for #<Metabolite:0x00007f922eeb0290>

Structure for #<Metabolite:0x00007f922eeb0290>

3D Structure for #<Metabolite:0x00007f922eeb0290>