MiMeDB: Showing metabocard for Chloropupukeanolide A (MMDBc0003236)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 21:22:08 UTC

Update Date

2025-10-07 16:04:41 UTC

Metabolite ID

MMDBc0003236

Metabolite Identification

Common Name

Chloropupukeanolide A

Description

Chloropupukeanolide A is a polyketide compound. There is little literature on this metabolite, indicating that further research is needed to fully understand its properties and potential biological activities.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142123222D          

 49 56  0  0  1  0            999 V2000
    8.6049    2.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8702    1.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5418    3.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0769    1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5653    0.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405    3.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1761    2.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4550    2.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890    4.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3202    2.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5932   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0489   -0.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6868    1.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9597    1.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8837    2.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7170    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924    0.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3364    0.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4642    4.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4181   -0.0142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4954    2.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8864    0.7747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0674    3.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6166    1.4280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8422    0.6934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2426    3.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893    2.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4325    0.5169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4335    2.0029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4415    1.4145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7410    0.7920    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6220    1.2792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2738    2.0897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5939   -0.0198    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0362    4.9649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8188   -0.7354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8146    4.2236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7496    3.3964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3830    0.1210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3847    2.9734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0986    2.1077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2664    1.4010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    2.7950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1021    2.1045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2923    1.8495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2430   -0.0277    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2581    0.0382    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9891    2.1641    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0173    0.7069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  7  2  0  0  0  0
 16  3  1  0  0  0  0
 16  9  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 18 12  2  0  0  0  0
 18 17  1  0  0  0  0
 19  9  1  0  0  0  0
 20 11  1  0  0  0  0
 21 10  2  0  0  0  0
 22 13  1  0  0  0  0
 23 19  2  0  0  0  0
 23 21  1  0  0  0  0
 24 17  1  0  0  0  0
 25 20  1  0  0  0  0
 26 23  1  0  0  0  0
 28  4  1  1  0  0  0
 28 12  1  0  0  0  0
 28 14  1  0  0  0  0
 29 13  1  0  0  0  0
 29 14  1  0  0  0  0
 29 27  1  1  0  0  0
 30  8  1  6  0  0  0
 30 24  1  0  0  0  0
 30 25  1  0  0  0  0
 31 22  1  0  0  0  0
 31 28  1  0  0  0  0
 32 18  1  1  0  0  0
 32 31  1  0  0  0  0
 33 29  1  0  0  0  0
 33 32  1  0  0  0  0
 31 34  1  6  0  0  0
 35 19  1  0  0  0  0
 20 36  1  1  0  0  0
 37 26  2  0  0  0  0
 38 27  2  0  0  0  0
 39  5  1  0  0  0  0
 39 22  1  0  0  0  0
 40  6  1  0  0  0  0
 40 27  1  0  0  0  0
 41 21  1  0  0  0  0
 33 41  1  6  0  0  0
 42 25  1  0  0  0  0
 42 30  1  0  0  0  0
 43 26  1  0  0  0  0
 43 33  1  0  0  0  0
 44 24  1  0  0  0  0
 45 32  1  0  0  0  0
 45 44  1  0  0  0  0
 20 46  1  6  0  0  0
 22 47  1  1  0  0  0
 24 48  1  6  0  0  0
 25 49  1  6  0  0  0
M  END


  Mrv1652305142123222D          

 49 56  0  0  1  0            999 V2000
    8.6049    2.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8702    1.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5418    3.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0769    1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5653    0.2301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1405    3.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1761    2.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4550    2.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2890    4.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3202    2.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5932   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0489   -0.0530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6868    1.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9597    1.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8837    2.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7170    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924    0.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3364    0.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4642    4.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4181   -0.0142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4954    2.8310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8864    0.7747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0674    3.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6166    1.4280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8422    0.6934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2426    3.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893    2.7909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4325    0.5169    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4335    2.0029    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4415    1.4145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7410    0.7920    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6220    1.2792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2738    2.0897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5939   -0.0198    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.0362    4.9649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8188   -0.7354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8146    4.2236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7496    3.3964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3830    0.1210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3847    2.9734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0986    2.1077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2664    1.4010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    2.7950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1021    2.1045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2923    1.8495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2430   -0.0277    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2581    0.0382    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9891    2.1641    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0173    0.7069    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  7  2  0  0  0  0
 16  3  1  0  0  0  0
 16  9  2  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 18 12  2  0  0  0  0
 18 17  1  0  0  0  0
 19  9  1  0  0  0  0
 20 11  1  0  0  0  0
 21 10  2  0  0  0  0
 22 13  1  0  0  0  0
 23 19  2  0  0  0  0
 23 21  1  0  0  0  0
 24 17  1  0  0  0  0
 25 20  1  0  0  0  0
 26 23  1  0  0  0  0
 28  4  1  1  0  0  0
 28 12  1  0  0  0  0
 28 14  1  0  0  0  0
 29 13  1  0  0  0  0
 29 14  1  0  0  0  0
 29 27  1  1  0  0  0
 30  8  1  6  0  0  0
 30 24  1  0  0  0  0
 30 25  1  0  0  0  0
 31 22  1  0  0  0  0
 31 28  1  0  0  0  0
 32 18  1  1  0  0  0
 32 31  1  0  0  0  0
 33 29  1  0  0  0  0
 33 32  1  0  0  0  0
 31 34  1  6  0  0  0
 35 19  1  0  0  0  0
 20 36  1  1  0  0  0
 37 26  2  0  0  0  0
 38 27  2  0  0  0  0
 39  5  1  0  0  0  0
 39 22  1  0  0  0  0
 40  6  1  0  0  0  0
 40 27  1  0  0  0  0
 41 21  1  0  0  0  0
 33 41  1  6  0  0  0
 42 25  1  0  0  0  0
 42 30  1  0  0  0  0
 43 26  1  0  0  0  0
 43 33  1  0  0  0  0
 44 24  1  0  0  0  0
 45 32  1  0  0  0  0
 45 44  1  0  0  0  0
 20 46  1  6  0  0  0
 22 47  1  1  0  0  0
 24 48  1  6  0  0  0
 25 49  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0003236

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]12O[C@]1(CC=C(C)C)[C@]1([H])OO[C@]34C(=C[C@@]5(C)C[C@@](C[C@@]([H])(OC)[C@@]35Cl)(C(=O)OC)[C@@]43OC(=O)C4=C(O)C=C(C)C=C4O3)C1=C[C@]2([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C33H35ClO11/c1-15(2)7-8-30-24-17(11-20(36)25(30)42-30)18-12-28(4)14-29(27(38)40-6)13-22(39-5)31(28,34)32(18,45-44-24)33(29)41-21-10-16(3)9-19(35)23(21)26(37)43-33/h7,9-12,20,22,24-25,35-36H,8,13-14H2,1-6H3/t20-,22+,24+,25-,28-,29-,30+,31-,32+,33+/m0/s1

> <INCHI_KEY>
HKLJTOFDHIFETB-VZDNXQFBSA-N

> <FORMULA>
C33H35ClO11

> <MOLECULAR_WEIGHT>
643.08

> <EXACT_MASS>
642.1867896

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
63.92119071447462

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1'S,2R,4'R,5'S,7'S,8'S,13'R,15'S,17'R,18'R)-18'-chloro-5,8'-dihydroxy-17'-methoxy-7,13'-dimethyl-5'-(3-methylbut-2-en-1-yl)-4-oxo-4H-2',3',6'-trioxaspiro[1,3-benzodioxine-2,19'-hexacyclo[13.3.1.0^{1,11}.0^{4,10}.0^{5,7}.0^{13,18}]nonadecane]-9',11'-diene-15'-carboxylate

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
5.008195447000001

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.683792819561916

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.803263019853231

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3745340367977397

> <JCHEM_POLAR_SURFACE_AREA>
142.51

> <JCHEM_REFRACTIVITY>
157.93410000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1'S,2R,4'R,5'S,7'S,8'S,13'R,15'S,17'R,18'R)-18'-chloro-5,8'-dihydroxy-17'-methoxy-7,13'-dimethyl-5'-(3-methylbut-2-en-1-yl)-4-oxo-2',3',6'-trioxaspiro[1,3-benzodioxine-2,19'-hexacyclo[13.3.1.0^{1,11}.0^{4,10}.0^{5,7}.0^{13,18}]nonadecane]-9',11'-diene-15'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         0                                  
HETATM    1  C   UNK     0      16.062   4.885   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.691   2.597   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.211   6.702   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.610   1.926   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.055   0.429   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.129   7.021   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.395   4.928   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.049   4.180   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.873   7.985   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.931   5.318   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.441  -0.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.558  -0.099   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.149   2.981   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.525   2.491   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.716   4.137   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.672   6.668   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.693   1.345   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.095   1.380   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.333   7.951   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.980  -0.027   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.391   5.285   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.521   1.446   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.592   6.601   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.484   2.666   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.772   1.294   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.053   6.567   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.087   5.210   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.407   0.965   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.543   3.739   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.024   2.640   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.117   1.478   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.761   2.388   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.111   3.901   0.000  0.00  0.00           C+0
HETATM   34 Cl   UNK     0       4.842  -0.037   0.000  0.00  0.00          Cl+0
HETATM   35  O   UNK     0       7.534   9.268   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      12.728  -1.373   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       5.254   7.884   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       5.133   6.340   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       2.582   0.226   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       2.585   5.550   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       7.651   3.934   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      13.564   2.615   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       5.312   5.217   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       9.524   3.928   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       8.012   3.452   0.000  0.00  0.00           O+0
HETATM   46  H   UNK     0      13.520  -0.052   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0       4.215   0.071   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      11.180   4.040   0.000  0.00  0.00           H+0
HETATM   49  H   UNK     0      11.232   1.320   0.000  0.00  0.00           H+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   28                                                            
CONECT    5   39                                                            
CONECT    6   40                                                            
CONECT    7    8   15                                                       
CONECT    8    7   30                                                       
CONECT    9   16   19                                                       
CONECT   10   16   21                                                       
CONECT   11   17   20                                                       
CONECT   12   18   28                                                       
CONECT   13   22   29                                                       
CONECT   14   28   29                                                       
CONECT   15    1    2    7                                                  
CONECT   16    3    9   10                                                  
CONECT   17   11   18   24                                                  
CONECT   18   12   17   32                                                  
CONECT   19    9   23   35                                                  
CONECT   20   11   25   36   46                                             
CONECT   21   10   23   41                                                  
CONECT   22   13   31   39   47                                             
CONECT   23   19   21   26                                                  
CONECT   24   17   30   44   48                                             
CONECT   25   20   30   42   49                                             
CONECT   26   23   37   43                                                  
CONECT   27   29   38   40                                                  
CONECT   28    4   12   14   31                                             
CONECT   29   13   14   27   33                                             
CONECT   30    8   24   25   42                                             
CONECT   31   22   28   32   34                                             
CONECT   32   18   31   33   45                                             
CONECT   33   29   32   41   43                                             
CONECT   34   31                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   26                                                            
CONECT   38   27                                                            
CONECT   39    5   22                                                       
CONECT   40    6   27                                                       
CONECT   41   21   33                                                       
CONECT   42   25   30                                                       
CONECT   43   26   33                                                       
CONECT   44   24   45                                                       
CONECT   45   32   44                                                       
CONECT   46   20                                                            
CONECT   47   22                                                            
CONECT   48   24                                                            
CONECT   49   25                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  112    0
END

Synonyms

Not Available

Molecular Formula

C₃₃H₃₅ClO₁₁

Average Mass

643.08

Monoisotopic Mass

642.1867896

IUPAC Name

methyl (1'S,2R,4'R,5'S,7'S,8'S,13'R,15'S,17'R,18'R)-18'-chloro-5,8'-dihydroxy-17'-methoxy-7,13'-dimethyl-5'-(3-methylbut-2-en-1-yl)-4-oxo-4H-2',3',6'-trioxaspiro[1,3-benzodioxine-2,19'-hexacyclo[13.3.1.0^{1,11}.0^{4,10}.0^{5,7}.0^{13,18}]nonadecane]-9',11'-diene-15'-carboxylate

Traditional Name

methyl (1'S,2R,4'R,5'S,7'S,8'S,13'R,15'S,17'R,18'R)-18'-chloro-5,8'-dihydroxy-17'-methoxy-7,13'-dimethyl-5'-(3-methylbut-2-en-1-yl)-4-oxo-2',3',6'-trioxaspiro[1,3-benzodioxine-2,19'-hexacyclo[13.3.1.0^{1,11}.0^{4,10}.0^{5,7}.0^{13,18}]nonadecane]-9',11'-diene-15'-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@]12O[C@]1(CC=C(C)C)[C@]1([H])OO[C@]34C(=C[C@@]5(C)C[C@@](C[C@@]([H])(OC)[C@@]35Cl)(C(=O)OC)[C@@]43OC(=O)C4=C(O)C=C(C)C=C4O3)C1=C[C@]2([H])O

InChI Identifier

InChI=1S/C33H35ClO11/c1-15(2)7-8-30-24-17(11-20(36)25(30)42-30)18-12-28(4)14-29(27(38)40-6)13-22(39-5)31(28,34)32(18,45-44-24)33(29)41-21-10-16(3)9-19(35)23(21)26(37)43-33/h7,9-12,20,22,24-25,35-36H,8,13-14H2,1-6H3/t20-,22+,24+,25-,28-,29-,30+,31-,32+,33+/m0/s1

InChI Key

HKLJTOFDHIFETB-VZDNXQFBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-4-unsubstituted benzenoids

Direct Parent

1-hydroxy-4-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Ortho-dioxane
Dicarboxylic acid or derivatives
Vinylogous acid
Methyl ester
Carboxylic acid ester
Lactone
Dialkyl peroxide
Secondary alcohol
Acetal
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Alkyl chloride
Alkyl halide
Organohalogen compound
Organochloride
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	3.6	ALOGPS
logP	5.01	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.8	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	142.51 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	157.93 m³·mol⁻¹	ChemAxon
Polarizability	63.92 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	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	16.1
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (void)	2025-10-23	37.8
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	656.5
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	684.3
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	864.3
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	205.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3934.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	91.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	474.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	621.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	239.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	176.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	244.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	9.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	224.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	113.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	543.2
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1897.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1565.1

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Chloropupukeanolide A_TMS_1	COC(=O)[C@]12C[C@@H](OC)[C@@]3(Cl)[C@@]4(OO[C@@H]5C(=C[C@H](O)[C@@H]6O[C@@]65CC=C(C)C)C4=C[C@@]3(C)C1)[C@]21OC(=O)C2=C(C=C(C)C=C2O[Si](C)(C)C)O1	standard non polar	2025-10-23	1400.04
Gas Chromatography	Chloropupukeanolide A_TMS_2	COC(=O)[C@]12C[C@@H](OC)[C@@]3(Cl)[C@@]4(OO[C@@H]5C(=C[C@H](O[Si](C)(C)C)[C@@H]6O[C@@]65CC=C(C)C)C4=C[C@@]3(C)C1)[C@]21OC(=O)C2=C(O)C=C(C)C=C2O1	standard non polar	2025-10-23	1807.92
Gas Chromatography	Chloropupukeanolide A_TMS_3	COC(=O)[C@]12C[C@@H](OC)[C@@]3(Cl)[C@@]4(OO[C@@H]5C(=C[C@H](O[Si](C)(C)C)[C@@H]6O[C@@]65CC=C(C)C)C4=C[C@@]3(C)C1)[C@]21OC(=O)C2=C(C=C(C)C=C2O[Si](C)(C)C)O1	standard non polar	2025-10-23	69.357
Gas Chromatography	Chloropupukeanolide A_TMS_1	COC(=O)[C@]12C[C@@H](OC)[C@@]3(Cl)[C@@]4(OO[C@@H]5C(=C[C@H](O)[C@@H]6O[C@@]65CC=C(C)C)C4=C[C@@]3(C)C1)[C@]21OC(=O)C2=C(C=C(C)C=C2O[Si](C)(C)C)O1	standard polar	2025-10-23	1935.93
Gas Chromatography	Chloropupukeanolide A_TMS_2	COC(=O)[C@]12C[C@@H](OC)[C@@]3(Cl)[C@@]4(OO[C@@H]5C(=C[C@H](O[Si](C)(C)C)[C@@H]6O[C@@]65CC=C(C)C)C4=C[C@@]3(C)C1)[C@]21OC(=O)C2=C(O)C=C(C)C=C2O1	standard polar	2025-10-23	2792.63
Gas Chromatography	Chloropupukeanolide A_TMS_3	COC(=O)[C@]12C[C@@H](OC)[C@@]3(Cl)[C@@]4(OO[C@@H]5C(=C[C@H](O[Si](C)(C)C)[C@@H]6O[C@@]65CC=C(C)C)C4=C[C@@]3(C)C1)[C@]21OC(=O)C2=C(C=C(C)C=C2O[Si](C)(C)C)O1	standard polar	2025-10-23	3816.43

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
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

78436528

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45102451

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 Chloropupukeanolide A (MMDBc0003236)

MOL for #<Metabolite:0x00007f2e38363680>

3D MOL for #<Metabolite:0x00007f2e38363680>

3D SDF for #<Metabolite:0x00007f2e38363680>

3D-SDF for #<Metabolite:0x00007f2e38363680>

PDB for #<Metabolite:0x00007f2e38363680>

3D PDB for #<Metabolite:0x00007f2e38363680>

SMILES for #<Metabolite:0x00007f2e38363680>

INCHI for #<Metabolite:0x00007f2e38363680>

Structure for #<Metabolite:0x00007f2e38363680>

3D Structure for #<Metabolite:0x00007f2e38363680>