MiMeDB: Showing metabocard for Oocydin A (MMDBc0024669)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 14:28:39 UTC

Update Date

2025-10-07 16:07:28 UTC

Metabolite ID

MMDBc0024669

Metabolite Identification

Common Name

Oocydin A

Description

Oocydin A is a chlorinated macrolide belonging to the chemical class of polyketides. Its chemical structure features a complex arrangement of carbon rings and halogen substituents, which contribute to its bioactivity. Oocydin A is produced by the rhizobacterium Serratia plymuthica, specifically strains such as 4Rx5 and A153, which are known to synthesize various bioactive secondary metabolites, including the antifungal and anti-oomycete haterumalide (PMID:30533641 ). The biosynthesis of oocydin A is mediated by a large trans-acyltransferase polyketide synthase gene cluster, with involvement from several key enzymes, including hydroxymethylglutaryl-coenzyme A synthase and flavin-dependent tailoring enzymes (PMID:25753587 ). Additionally, the regulation of its biosynthesis is influenced by quorum sensing mechanisms and the RNA chaperone Hfq (PMID:25753587 ). Oocydin A's biological pathways include its role as an antifungal and anti-oomycete agent, making it significant in the context of plant-associated bacteria (PMID:26914969 ). The compound's unique structure and biosynthetic pathways highlight its potential applications in agriculture and medicine.

Structure

MOL SDF PDB SMILES InChI

Oocydin A
  Mrv1652309242002252D          

 32 33  0  0  0  0            999 V2000
    4.3005   -1.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5572   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7408    0.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5572    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0428    1.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2995    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4745    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312    1.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169    0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7018    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5678   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5678    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352   -0.8974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9888   -0.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563   -1.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5701   -1.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4100   -0.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4962    0.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8288    0.5942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2499    0.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1489   -1.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312   -1.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4745   -1.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910   -2.4747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2995   -1.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0428   -1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5572   -1.9574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2558   -2.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4400   -2.8484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7702   -3.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4831    2.7485    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 14 22  1  1  0  0  0
 11 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  6 32  1  0  0  0  0
 27  2  1  0  0  0  0
 13  9  1  0  0  0  0
M  END

Oocydin A
  Mrv1652309242002252D          

 32 33  0  0  0  0            999 V2000
    4.3005   -1.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5572   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7408    0.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5572    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0428    1.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2995    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4745    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312    1.5862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169    0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7018    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5678   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5678    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352   -0.8974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9888   -0.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6563   -1.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5701   -1.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4100   -0.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4962    0.1092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8288    0.5942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2499    0.4448    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1489   -1.7179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7312   -1.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4745   -1.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2910   -2.4747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2995   -1.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0428   -1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5572   -1.9574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2558   -2.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4400   -2.8484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7702   -3.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4831    2.7485    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 14 22  1  1  0  0  0
 11 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  6 32  1  0  0  0  0
 27  2  1  0  0  0  0
 13  9  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0024669

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)OC1CC(=O)O[C@H]2C[C@H](CC\C(Cl)=C/C\C=C1\C)O[C@H]2[C@@H](O)\C=C(/C)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H31ClO8/c1-13(10-21(27)28)9-18(26)23-20-11-17(31-23)8-7-16(24)6-4-5-14(2)19(30-15(3)25)12-22(29)32-20/h5-6,9,17-20,23,26H,4,7-8,10-12H2,1-3H3,(H,27,28)/b13-9+,14-5-,16-6+/t17-,18-,19?,20-,23-/m0/s1

> <INCHI_KEY>
OAWOFENLLWPBEQ-AQHKLOSRSA-N

> <FORMULA>
C23H31ClO8

> <MOLECULAR_WEIGHT>
470.94

> <EXACT_MASS>
470.1707457

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.94635871469891

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,5S)-5-[(1S,6Z,9E,13S,15S)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoic acid

> <ALOGPS_LOGP>
2.61

> <JCHEM_LOGP>
2.1041259063333326

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.73851888108507

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9818337219166695

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3527452171049594

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
118.71109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E,5S)-5-[(1S,6Z,9E,13S,15S)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-SEP-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Oocydin A                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-SEP-20         0                                  
HETATM    1  C   UNK     0       8.028  -1.914   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.640  -1.246   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.983   0.256   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.640   1.757   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.680   2.961   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.292   3.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.752   3.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.365   2.961   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.405   1.246   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.310   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.405  -1.246   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.060  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.060   0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.306  -1.675   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.713  -1.049   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.958  -1.954   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.797  -3.486   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.365  -1.328   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.526   0.204   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.280   1.109   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -7.933   0.830   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.145  -3.207   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.365  -2.450   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.752  -3.118   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.410  -4.619   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.292  -3.118   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.680  -2.450   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.640  -3.654   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.078  -5.087   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.555  -5.317   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.038  -6.292   0.000  0.00  0.00           C+0
HETATM   32 Cl   UNK     0       4.635   5.130   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   23                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    9                                                       
CONECT   14   12   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   14                                                            
CONECT   23   11   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28    2                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    6                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

Synonyms

Not Available

Molecular Formula

C₂₃H₃₁ClO₈

Average Mass

470.94

Monoisotopic Mass

470.1707457

IUPAC Name

(3E,5S)-5-[(1S,6Z,9E,13S,15S)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoic acid

Traditional Name

(3E,5S)-5-[(1S,6Z,9E,13S,15S)-5-(acetyloxy)-10-chloro-6-methyl-3-oxo-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-15-yl]-5-hydroxy-3-methylpent-3-enoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC(=O)O[C@H]2C[C@H](CC\C(Cl)=C/C\C=C1\C)O[C@H]2[C@@H](O)\C=C(/C)CC(O)=O

InChI Identifier

InChI=1S/C23H31ClO8/c1-13(10-21(27)28)9-18(26)23-20-11-17(31-23)8-7-16(24)6-4-5-14(2)19(30-15(3)25)12-22(29)32-20/h5-6,9,17-20,23,26H,4,7-8,10-12H2,1-3H3,(H,27,28)/b13-9+,14-5-,16-6+/t17-,18-,19?,20-,23-/m0/s1

InChI Key

OAWOFENLLWPBEQ-AQHKLOSRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Tricarboxylic acid or derivatives
Monosaccharide
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Chloroalkene
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
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	0.027 g/L	ALOGPS
logP	2.61	ALOGPS
logP	2.1	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	3.98	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	118.71 m³·mol⁻¹	ChemAxon
Polarizability	46.95 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	195.7
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	45.2
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	567.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	443.1
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	474.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	187.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2632.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	145.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	419.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	398.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	152.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	162.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	165.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	19.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	323.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	101.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	377.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1329.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1151.4

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Oocydin A_TMS_1	CC(=O)OC1CC(=O)O[C@H]2C[C@H](CC/C(Cl)=C\C/C=C\1C)O[C@H]2[C@H](/C=C(\C)CC(=O)O)O[Si](C)(C)C	standard non polar	2025-10-23	2684.49
Gas Chromatography	Oocydin A_TMS_2	CC(=O)OC1CC(=O)O[C@H]2C[C@H](CC/C(Cl)=C\C/C=C\1C)O[C@H]2[C@@H](O)/C=C(\C)CC(=O)O[Si](C)(C)C	standard non polar	2025-10-23	2044.24
Gas Chromatography	Oocydin A_TMS_3	CC(=O)OC1CC(=O)O[C@H]2C[C@H](CC/C(Cl)=C\C/C=C\1C)O[C@H]2[C@H](/C=C(\C)CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	standard non polar	2025-10-23	1710.71
Gas Chromatography	Oocydin A_TMS_1	CC(=O)OC1CC(=O)O[C@H]2C[C@H](CC/C(Cl)=C\C/C=C\1C)O[C@H]2[C@H](/C=C(\C)CC(=O)O)O[Si](C)(C)C	standard polar	2025-10-23	1406.78
Gas Chromatography	Oocydin A_TMS_2	CC(=O)OC1CC(=O)O[C@H]2C[C@H](CC/C(Cl)=C\C/C=C\1C)O[C@H]2[C@@H](O)/C=C(\C)CC(=O)O[Si](C)(C)C	standard polar	2025-10-23	2647.45
Gas Chromatography	Oocydin A_TMS_3	CC(=O)OC1CC(=O)O[C@H]2C[C@H](CC/C(Cl)=C\C/C=C\1C)O[C@H]2[C@H](/C=C(\C)CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	standard polar	2025-10-23	3366.56

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated 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
Bacteria/Eubacteria	Proteobacteria	1	Human	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

145720628

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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 Oocydin A (MMDBc0024669)

MOL for #<Metabolite:0x00007f9ab40bbf70>

3D MOL for #<Metabolite:0x00007f9ab40bbf70>

3D SDF for #<Metabolite:0x00007f9ab40bbf70>

3D-SDF for #<Metabolite:0x00007f9ab40bbf70>

PDB for #<Metabolite:0x00007f9ab40bbf70>

3D PDB for #<Metabolite:0x00007f9ab40bbf70>

SMILES for #<Metabolite:0x00007f9ab40bbf70>

INCHI for #<Metabolite:0x00007f9ab40bbf70>

Structure for #<Metabolite:0x00007f9ab40bbf70>

3D Structure for #<Metabolite:0x00007f9ab40bbf70>