MiMeDB: Showing metabocard for 3-O-acetyl-5-methylbotcinolide (MMDBc0005536)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 23:06:13 UTC

Update Date

2022-08-31 06:23:56 UTC

Metabolite ID

MMDBc0005536

Metabolite Identification

Common Name

3-O-acetyl-5-methylbotcinolide

Description

3-O-acetyl-5-methylbotcinolide belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Based on a literature review very few articles have been published on 3-O-acetyl-5-methylbotcinolide.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152101062D          

 33 33  0  0  0  0            999 V2000
   -3.7861   -4.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9739   -1.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9743   -1.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2794   -3.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6224    0.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4668   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0717   -3.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3572   -4.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427   -3.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2138   -3.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5007   -4.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864   -1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1619   -1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -3.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0921   -0.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283   -4.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2152   -3.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296   -2.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989   -1.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7494   -1.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0186   -2.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9741   -0.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3743   -1.3139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283   -5.0293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296   -4.2043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6686   -0.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7331   -2.9668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4815   -0.0835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3866   -3.0846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2797   -0.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2152   -2.9668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2138   -2.9668    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5007   -5.0293    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  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  2  1  0  0  0  0
 13  3  1  0  0  0  0
 14  4  1  0  0  0  0
 15  5  1  0  0  0  0
 16  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 14  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 13  1  0  0  0  0
 22  6  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 15  2  0  0  0  0
 24 16  1  0  0  0  0
 25 17  2  0  0  0  0
 26 19  1  0  0  0  0
 27 21  2  0  0  0  0
 28 22  1  0  0  0  0
 29 14  1  0  0  0  0
 29 21  1  0  0  0  0
 30 15  1  0  0  0  0
 30 20  1  0  0  0  0
 31 17  1  0  0  0  0
 31 18  1  0  0  0  0
 32 10  1  0  0  0  0
 33 11  1  0  0  0  0
M  END


  Mrv1652305152101062D          

 33 33  0  0  0  0            999 V2000
   -3.7861   -4.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9739   -1.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9743   -1.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2794   -3.8599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6224    0.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4668   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0717   -3.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3572   -4.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6427   -3.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2138   -3.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5007   -4.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7864   -1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1619   -1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5616   -3.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0921   -0.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283   -4.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2152   -3.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296   -2.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989   -1.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7494   -1.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0186   -2.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9741   -0.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3743   -1.3139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283   -5.0293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9296   -4.2043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6686   -0.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7331   -2.9668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4815   -0.0835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3866   -3.0846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2797   -0.3954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2152   -2.9668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2138   -2.9668    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5007   -5.0293    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  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  2  1  0  0  0  0
 13  3  1  0  0  0  0
 14  4  1  0  0  0  0
 15  5  1  0  0  0  0
 16  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 14  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 13  1  0  0  0  0
 22  6  1  0  0  0  0
 22 19  1  0  0  0  0
 22 20  1  0  0  0  0
 23 15  2  0  0  0  0
 24 16  1  0  0  0  0
 25 17  2  0  0  0  0
 26 19  1  0  0  0  0
 27 21  2  0  0  0  0
 28 22  1  0  0  0  0
 29 14  1  0  0  0  0
 29 21  1  0  0  0  0
 30 15  1  0  0  0  0
 30 20  1  0  0  0  0
 31 17  1  0  0  0  0
 31 18  1  0  0  0  0
 32 10  1  0  0  0  0
 33 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0005536

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(C(O)CCCC)=C(\[H])C(=O)OC1C(C)OC(=O)C(C)C(OC(C)=O)C(C)(O)C(O)C1C

> <INCHI_IDENTIFIER>
InChI=1S/C22H36O9/c1-7-8-9-16(24)10-11-17(25)31-18-12(2)19(26)22(6,28)20(30-15(5)23)13(3)21(27)29-14(18)4/h10-14,16,18-20,24,26,28H,7-9H2,1-6H3/b11-10+

> <INCHI_KEY>
GCTUDEYVOWVAEW-ZHACJKMWSA-N

> <FORMULA>
C22H36O9

> <MOLECULAR_WEIGHT>
444.521

> <EXACT_MASS>
444.235932739

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.87994664942158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2E)-4-hydroxyoct-2-enoate

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
1.924947351

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.352395443974423

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.94991256316128

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8715557607132842

> <JCHEM_POLAR_SURFACE_AREA>
139.58999999999997

> <JCHEM_REFRACTIVITY>
110.86009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2E)-4-hydroxyoct-2-enoate

> <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      -7.067  -7.848   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.818  -2.984   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.285  -2.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.255  -7.205   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.495   0.174   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.471  -0.156   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.734  -7.078   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.400  -7.848   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.066  -7.078   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.399  -7.078   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.935  -7.848   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.335  -3.252   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.769  -3.252   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.782  -5.758   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.505  -1.006   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.733  -7.848   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.268  -7.078   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.602  -4.768   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.105  -1.918   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.999  -1.918   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.501  -4.768   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.552  -1.391   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.032  -2.453   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.733  -9.388   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.602  -7.848   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.115  -0.738   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.835  -5.538   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.632  -0.156   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.322  -5.758   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       7.989  -0.738   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.268  -5.538   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0      -0.399  -5.538   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.935  -9.388   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5   15                                                            
CONECT    6   22                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   16                                                       
CONECT   10   11   16   32                                                  
CONECT   11   10   17   33                                                  
CONECT   12    2   18   19                                                  
CONECT   13    3   20   21                                                  
CONECT   14    4   18   29                                                  
CONECT   15    5   23   30                                                  
CONECT   16    9   10   24                                                  
CONECT   17   11   25   31                                                  
CONECT   18   12   14   31                                                  
CONECT   19   12   22   26                                                  
CONECT   20   13   22   30                                                  
CONECT   21   13   27   29                                                  
CONECT   22    6   19   20   28                                             
CONECT   23   15                                                            
CONECT   24   16                                                            
CONECT   25   17                                                            
CONECT   26   19                                                            
CONECT   27   21                                                            
CONECT   28   22                                                            
CONECT   29   14   21                                                       
CONECT   30   15   20                                                       
CONECT   31   17   18                                                       
CONECT   32   10                                                            
CONECT   33   11                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

Synonyms

Not Available

Molecular Formula

C₂₂H₃₆O₉

Average Mass

444.521

Monoisotopic Mass

444.235932739

IUPAC Name

7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2E)-4-hydroxyoct-2-enoate

Traditional Name

7-(acetyloxy)-5,6-dihydroxy-2,4,6,8-tetramethyl-9-oxooxonan-3-yl (2E)-4-hydroxyoct-2-enoate

CAS Registry Number

Not Available

SMILES

[H]\C(C(O)CCCC)=C(\[H])C(=O)OC1C(C)OC(=O)C(C)C(OC(C)=O)C(C)(O)C(O)C1C

InChI Identifier

InChI=1S/C22H36O9/c1-7-8-9-16(24)10-11-17(25)31-18-12(2)19(26)22(6,28)20(30-15(5)23)13(3)21(27)29-14(18)4/h10-14,16,18-20,24,26,28H,7-9H2,1-6H3/b11-10+

InChI Key

GCTUDEYVOWVAEW-ZHACJKMWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.44 g/L	ALOGPS
logP	1.83	ALOGPS
logP	1.92	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.95	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.59 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	110.86 m³·mol⁻¹	ChemAxon
Polarizability	47.88 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

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

78444551

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584453

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 3-O-acetyl-5-methylbotcinolide (MMDBc0005536)

MOL for #<Metabolite:0x00007f9250657158>

3D MOL for #<Metabolite:0x00007f9250657158>

3D SDF for #<Metabolite:0x00007f9250657158>

3D-SDF for #<Metabolite:0x00007f9250657158>

PDB for #<Metabolite:0x00007f9250657158>

3D PDB for #<Metabolite:0x00007f9250657158>

SMILES for #<Metabolite:0x00007f9250657158>

INCHI for #<Metabolite:0x00007f9250657158>

Structure for #<Metabolite:0x00007f9250657158>

3D Structure for #<Metabolite:0x00007f9250657158>