MiMeDB: Showing metabocard for 1,4-diacetoxypalitantin (MMDBc0019473)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 09:31:54 UTC

Update Date

2022-08-31 06:45:29 UTC

Metabolite ID

MMDBc0019473

Metabolite Identification

Common Name

1,4-diacetoxypalitantin

Description

1,4-diacetoxypalitantin belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom). 1,4-diacetoxypalitantin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152111312D          

 32 32  0  0  1  0            999 V2000
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 12  2  1  0  0  0  0
 13  3  1  0  0  0  0
 14  9  1  6  0  0  0
 14 10  1  0  0  0  0
 15 11  1  6  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 12  2  0  0  0  0
 20 13  2  0  0  0  0
 16 21  1  1  0  0  0
 22 17  2  0  0  0  0
 23 11  1  0  0  0  0
 23 12  1  0  0  0  0
 24 13  1  0  0  0  0
 18 24  1  1  0  0  0
 25  6  1  0  0  0  0
 26  7  1  0  0  0  0
 27  8  1  0  0  0  0
 28  9  1  0  0  0  0
 14 29  1  1  0  0  0
 15 30  1  6  0  0  0
 16 31  1  6  0  0  0
 18 32  1  6  0  0  0
M  END


  Mrv1652305152111312D          

 32 32  0  0  1  0            999 V2000
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  2  0  0  0  0
 12  2  1  0  0  0  0
 13  3  1  0  0  0  0
 14  9  1  6  0  0  0
 14 10  1  0  0  0  0
 15 11  1  6  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 12  2  0  0  0  0
 20 13  2  0  0  0  0
 16 21  1  1  0  0  0
 22 17  2  0  0  0  0
 23 11  1  0  0  0  0
 23 12  1  0  0  0  0
 24 13  1  0  0  0  0
 18 24  1  1  0  0  0
 25  6  1  0  0  0  0
 26  7  1  0  0  0  0
 27  8  1  0  0  0  0
 28  9  1  0  0  0  0
 14 29  1  1  0  0  0
 15 30  1  6  0  0  0
 16 31  1  6  0  0  0
 18 32  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0019473

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(CCC)=C([H])C([H])=C([H])[C@]1([H])C[C@@]([H])(O)[C@@]([H])(OC(C)=O)C(=O)[C@@]1([H])COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H26O6/c1-4-5-6-7-8-9-14-10-16(21)18(24-13(3)20)17(22)15(14)11-23-12(2)19/h6-9,14-16,18,21H,4-5,10-11H2,1-3H3/b7-6+,9-8+/t14-,15+,16-,18-/m1/s1

> <INCHI_KEY>
RFSDHLTWOBLSFU-OQBXEDPBSA-N

> <FORMULA>
C18H26O6

> <MOLECULAR_WEIGHT>
338.4

> <EXACT_MASS>
338.172938557

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.85809673471203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1R,3R,4R,6S)-3-(acetyloxy)-6-[(1E,3E)-hepta-1,3-dien-1-yl]-4-hydroxy-2-oxocyclohexyl]methyl acetate

> <ALOGPS_LOGP>
2.27

> <JCHEM_LOGP>
1.9172784523333328

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.379914117179531

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.61958565464376

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2459912319781923

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
90.1411

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,3R,4R,6S)-3-(acetyloxy)-6-[(1E,3E)-hepta-1,3-dien-1-yl]-4-hydroxy-2-oxocyclohexyl]methyl acetate

> <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      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0      -2.667   7.700   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.334   6.930   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.334   5.390   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.667   4.620   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.000  -1.540   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8   26                                                  
CONECT    8    7    9   27                                                  
CONECT    9    8   14   28                                                  
CONECT   10   14   16                                                       
CONECT   11   15   23                                                       
CONECT   12    2   19   23                                                  
CONECT   13    3   20   24                                                  
CONECT   14    9   10   15   29                                             
CONECT   15   11   14   17   30                                             
CONECT   16   10   18   21   31                                             
CONECT   17   15   18   22                                                  
CONECT   18   16   17   24   32                                             
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   11   12                                                       
CONECT   24   13   18                                                       
CONECT   25    6                                                            
CONECT   26    7                                                            
CONECT   27    8                                                            
CONECT   28    9                                                            
CONECT   29   14                                                            
CONECT   30   15                                                            
CONECT   31   16                                                            
CONECT   32   18                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

Synonyms

Not Available

Molecular Formula

C₁₈H₂₆O₆

Average Mass

338.4

Monoisotopic Mass

338.172938557

IUPAC Name

[(1R,3R,4R,6S)-3-(acetyloxy)-6-[(1E,3E)-hepta-1,3-dien-1-yl]-4-hydroxy-2-oxocyclohexyl]methyl acetate

Traditional Name

[(1R,3R,4R,6S)-3-(acetyloxy)-6-[(1E,3E)-hepta-1,3-dien-1-yl]-4-hydroxy-2-oxocyclohexyl]methyl acetate

CAS Registry Number

Not Available

SMILES

[H]C(CCC)=C([H])C([H])=C([H])[C@]1([H])C[C@@]([H])(O)[C@@]([H])(OC(C)=O)C(=O)[C@@]1([H])COC(C)=O

InChI Identifier

InChI=1S/C18H26O6/c1-4-5-6-7-8-9-14-10-16(21)18(24-13(3)20)17(22)15(14)11-23-12(2)19/h6-9,14-16,18,21H,4-5,10-11H2,1-3H3/b7-6+,9-8+/t14-,15+,16-,18-/m1/s1

InChI Key

RFSDHLTWOBLSFU-OQBXEDPBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-acyloxy ketones

Alternative Parents

Substituents

Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	2.27	ALOGPS
logP	1.92	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	90.14 m³·mol⁻¹	ChemAxon
Polarizability	36.86 Å³	ChemAxon
Number of Rings	1	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
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

78441524

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588503

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 1,4-diacetoxypalitantin (MMDBc0019473)

MOL for #<Metabolite:0x00007fecc6316838>

3D MOL for #<Metabolite:0x00007fecc6316838>

3D SDF for #<Metabolite:0x00007fecc6316838>

3D-SDF for #<Metabolite:0x00007fecc6316838>

PDB for #<Metabolite:0x00007fecc6316838>

3D PDB for #<Metabolite:0x00007fecc6316838>

SMILES for #<Metabolite:0x00007fecc6316838>

INCHI for #<Metabolite:0x00007fecc6316838>

Structure for #<Metabolite:0x00007fecc6316838>

3D Structure for #<Metabolite:0x00007fecc6316838>