MiMeDB: Showing metabocard for Alternapyrone B (MMDBc0023893)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 13:47:37 UTC

Update Date

2022-08-31 06:48:48 UTC

Metabolite ID

MMDBc0023893

Metabolite Identification

Common Name

Alternapyrone B

Description

Alternapyrone B 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 B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152115472D          

 33 33  0  0  0  0            999 V2000
   -6.4599    4.8691    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
   -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
   -6.0474    5.5836    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
   -4.8099    6.2980    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
   -1.0974    8.4414    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
   -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
   -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
   -1.0974    7.0125    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
    4.6776   11.2993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724    7.0125    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
    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
  9  1  1  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 17  2  1  0  0  0  0
 17  9  1  0  0  0  0
 13 17  1  4  0  0  0
 18  3  1  0  0  0  0
 18 11  1  0  0  0  0
 18 13  2  0  0  0  0
 19  4  1  0  0  0  0
 19 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20  5  1  0  0  0  0
 14 20  1  4  0  0  0
 20 16  2  0  0  0  0
 21  6  1  0  0  0  0
 21 15  1  0  0  0  0
 22  7  1  0  0  0  0
 23  8  1  0  0  0  0
 24 12  1  0  0  0  0
 16 24  1  4  0  0  0
 25 22  1  0  0  0  0
 25 23  2  0  0  0  0
 26 21  1  0  0  0  0
 26 22  2  0  0  0  0
 27 24  1  0  0  0  0
 28 23  1  0  0  0  0
 29 25  1  0  0  0  0
 30 27  2  0  0  0  0
 31 27  1  0  0  0  0
 32 28  2  0  0  0  0
 33 26  1  0  0  0  0
 33 28  1  0  0  0  0
M  END


  Mrv1652305152115472D          

 33 33  0  0  0  0            999 V2000
   -6.4599    4.8691    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
   -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
   -6.0474    5.5836    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
   -4.8099    6.2980    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
   -1.0974    8.4414    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
   -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
   -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
   -1.0974    7.0125    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
    4.6776   11.2993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2724    7.0125    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
    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
  9  1  1  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 17  2  1  0  0  0  0
 17  9  1  0  0  0  0
 13 17  1  4  0  0  0
 18  3  1  0  0  0  0
 18 11  1  0  0  0  0
 18 13  2  0  0  0  0
 19  4  1  0  0  0  0
 19 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20  5  1  0  0  0  0
 14 20  1  4  0  0  0
 20 16  2  0  0  0  0
 21  6  1  0  0  0  0
 21 15  1  0  0  0  0
 22  7  1  0  0  0  0
 23  8  1  0  0  0  0
 24 12  1  0  0  0  0
 16 24  1  4  0  0  0
 25 22  1  0  0  0  0
 25 23  2  0  0  0  0
 26 21  1  0  0  0  0
 26 22  2  0  0  0  0
 27 24  1  0  0  0  0
 28 23  1  0  0  0  0
 29 25  1  0  0  0  0
 30 27  2  0  0  0  0
 31 27  1  0  0  0  0
 32 28  2  0  0  0  0
 33 26  1  0  0  0  0
 33 28  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0023893

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O5/c1-9-17(2)13-18(3)11-10-12-24(27(30)31)16-20(5)14-19(4)15-21(6)26-22(7)25(29)23(8)28(32)33-26/h13-14,16-17,21,24,29H,9-12,15H2,1-8H3,(H,30,31)

> <INCHI_KEY>
NBTZRFXBXREKRF-UHFFFAOYSA-N

> <FORMULA>
C28H42O5

> <MOLECULAR_WEIGHT>
458.639

> <EXACT_MASS>
458.303224452

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.279867945948084

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[6-(4-hydroxy-3,5-dimethyl-2-oxo-2H-pyran-6-yl)-2,4-dimethylhepta-1,3-dien-1-yl]-6,8-dimethyldec-6-enoic acid

> <ALOGPS_LOGP>
6.10

> <JCHEM_LOGP>
7.008963731666665

> <ALOGPS_LOGS>
-5.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.730190699611123

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.7866769355622605

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9788313047529735

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
138.23890000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[6-(4-hydroxy-3,5-dimethyl-6-oxopyran-2-yl)-2,4-dimethylhepta-1,3-dien-1-yl]-6,8-dimethyldec-6-enoic acid

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

Synonyms

Not Available

Molecular Formula

C₂₈H₄₂O₅

Average Mass

458.639

Monoisotopic Mass

458.303224452

IUPAC Name

2-[6-(4-hydroxy-3,5-dimethyl-2-oxo-2H-pyran-6-yl)-2,4-dimethylhepta-1,3-dien-1-yl]-6,8-dimethyldec-6-enoic acid

Traditional Name

2-[6-(4-hydroxy-3,5-dimethyl-6-oxopyran-2-yl)-2,4-dimethylhepta-1,3-dien-1-yl]-6,8-dimethyldec-6-enoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H42O5/c1-9-17(2)13-18(3)11-10-12-24(27(30)31)16-20(5)14-19(4)15-21(6)26-22(7)25(29)23(8)28(32)33-26/h13-14,16-17,21,24,29H,9-12,15H2,1-8H3,(H,30,31)

InChI Key

NBTZRFXBXREKRF-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
Medium-chain fatty acid
Methyl-branched fatty acid
Pyranone
Hydroxy fatty acid
Heterocyclic fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	0.0018 g/L	ALOGPS
logP	6.1	ALOGPS
logP	7.01	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.79	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	138.24 m³·mol⁻¹	ChemAxon
Polarizability	52.28 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

78444712

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139591184

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 B (MMDBc0023893)

MOL for #<Metabolite:0x00007f9205dcaa48>

3D MOL for #<Metabolite:0x00007f9205dcaa48>

3D SDF for #<Metabolite:0x00007f9205dcaa48>

3D-SDF for #<Metabolite:0x00007f9205dcaa48>

PDB for #<Metabolite:0x00007f9205dcaa48>

3D PDB for #<Metabolite:0x00007f9205dcaa48>

SMILES for #<Metabolite:0x00007f9205dcaa48>

INCHI for #<Metabolite:0x00007f9205dcaa48>

Structure for #<Metabolite:0x00007f9205dcaa48>

3D Structure for #<Metabolite:0x00007f9205dcaa48>