NP-MRD: Showing NP-Card for (1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate (NP0259226)

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Record Information

Version

2.0

Created at

2022-09-08 01:01:17 UTC

Updated at

2022-09-08 01:01:17 UTC

NP-MRD ID

NP0259226

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate

Description

CARIBAEOSIDE belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate is found in Erythropodium caribaeorum. Based on a literature review very few articles have been published on CARIBAEOSIDE.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309082203012D          

 48 52  0  0  1  0            999 V2000
    5.9567    0.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1362    0.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6513    1.2195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1362    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1362    2.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6513    3.3793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1362    4.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3813    2.2994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667    3.6343    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8667    4.4593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1522    4.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377    4.4593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1522    5.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377    6.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377    6.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7703    7.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0252    8.2038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5403    8.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8502    8.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1052    7.4192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820    3.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5971    2.7119    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5971    1.8869    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0820    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667    0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5811   -0.2730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5811   -1.0980    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2956   -1.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2956   -2.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5811   -2.7480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5811   -3.5730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -2.3355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1522   -2.7480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -1.5105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1522   -1.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377   -1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377   -2.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232   -1.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826    1.4744    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8826    0.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682    0.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5971    0.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682    2.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826    3.1244    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4953    3.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2700    3.8528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  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
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  9 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 23 40  1  0  0  0  0
 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 40 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 22 46  1  0  0  0  0
 46 47  1  6  0  0  0
 46 48  1  1  0  0  0
M  END


  Mrv1652309082203012D          

 48 52  0  0  1  0            999 V2000
    5.9567    0.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1362    0.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6513    1.2195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1362    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1362    2.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6513    3.3793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1362    4.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3813    2.2994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667    3.6343    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8667    4.4593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1522    4.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377    4.4593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1522    5.6968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377    6.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377    6.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7703    7.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0252    8.2038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5403    8.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8502    8.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1052    7.4192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820    3.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5971    2.7119    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5971    1.8869    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0820    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667    0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5811   -0.2730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5811   -1.0980    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2956   -1.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2956   -2.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5811   -2.7480    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5811   -3.5730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -2.3355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1522   -2.7480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8667   -1.5105    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1522   -1.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377   -1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4377   -2.3355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7232   -1.0980    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826    1.4744    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8826    0.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682    0.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5971    0.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682    2.7119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8826    3.1244    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4953    3.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2700    3.8528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  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
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  9 21  1  0  0  0  0
 22 21  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 28 27  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 23 40  1  0  0  0  0
 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 40 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 22 46  1  0  0  0  0
 46 47  1  6  0  0  0
 46 48  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0259226

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@]12O[C@@](C)(C=C1)[C@H](C[C@@H]1[C@H](\C=C2\CO[C@@H]2OC[C@@H](O)[C@@H](O)[C@@H]2OC(C)=O)[C@H](C=C[C@@]1(C)O)C(C)C)OC(=O)\C=C\C1=CN(C)C=N1

> <INCHI_IDENTIFIER>
InChI=1S/C35H48N2O11/c1-20(2)24-10-11-33(4,42)26-15-28(47-29(40)9-8-23-16-37(6)19-36-23)34(5)12-13-35(43-7,48-34)22(14-25(24)26)17-44-32-31(46-21(3)38)30(41)27(39)18-45-32/h8-14,16,19-20,24-28,30-32,39,41-42H,15,17-18H2,1-7H3/b9-8+,22-14-/t24-,25-,26-,27-,28+,30-,31+,32-,33-,34+,35-/m1/s1

> <INCHI_KEY>
KGOMYXIKIJGWKS-DKNGGRFKSA-N

> <FORMULA>
C35H48N2O11

> <MOLECULAR_WEIGHT>
672.772

> <EXACT_MASS>
672.325810374

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
70.45329436190389

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4R,5R,8S,9S,10Z,12R)-11-({[(2R,3S,4R,5R)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-12-methoxy-1,5-dimethyl-8-(propan-2-yl)-15-oxatricyclo[10.2.1.0^{4,9}]pentadeca-6,10,13-trien-2-yl (2E)-3-(1-methyl-1H-imidazol-4-yl)prop-2-enoate

> <JCHEM_LOGP>
2.656774600999997

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.069005441150402

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.801532126900618

> <JCHEM_PKA_STRONGEST_BASIC>
5.946668449293446

> <JCHEM_POLAR_SURFACE_AREA>
168.03

> <JCHEM_REFRACTIVITY>
175.84790000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R,5R,8S,9S,10Z,12R)-11-({[(2R,3S,4R,5R)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0^{4,9}]pentadeca-6,10,13-trien-2-yl (2E)-3-(1-methylimidazol-4-yl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      11.119   1.191   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.588   1.030   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.682   2.276   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.588   3.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.588   5.062   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.682   6.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.588   7.554   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.178   4.292   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.218   6.784   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.218   8.324   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.884   9.094   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.550   8.324   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.884  10.634   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.550  11.404   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.550  12.944   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.305  13.849   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.780  15.314   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       2.875  16.560   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.320  15.314   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       5.796  13.849   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       5.753   6.308   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.848   5.062   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.848   3.522   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.753   2.276   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.218   1.800   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.218   0.260   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.551  -0.510   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.551  -2.050   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       9.885  -2.820   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.885  -4.360   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.551  -5.130   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.551  -6.670   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.218  -4.360   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.884  -5.130   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       7.218  -2.820   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.884  -2.050   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       4.550  -2.820   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.550  -4.360   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       3.217  -2.050   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       3.514   2.752   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.514   1.212   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.181   0.442   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.848   0.442   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.181   3.522   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       2.181   5.062   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       3.514   5.832   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.791   7.192   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       4.237   7.192   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8   25                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6    3                                                       
CONECT    9    6   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   15                                                       
CONECT   21    9   22                                                       
CONECT   22   21   23   46                                                  
CONECT   23   22   24   40                                                  
CONECT   24   23   25                                                       
CONECT   25   24    3   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   28   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   23   41   44                                                  
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   40   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   22   47   48                                             
CONECT   47   46                                                            
CONECT   48   46                                                            
MASTER        0    0    0    0    0    0    0    0   48    0  104    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₄₈N₂O₁₁

Average Mass

672.7720 Da

Monoisotopic Mass

672.32581 Da

IUPAC Name

(1S,2S,4R,5R,8S,9S,10Z,12R)-11-({[(2R,3S,4R,5R)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-12-methoxy-1,5-dimethyl-8-(propan-2-yl)-15-oxatricyclo[10.2.1.0^{4,9}]pentadeca-6,10,13-trien-2-yl (2E)-3-(1-methyl-1H-imidazol-4-yl)prop-2-enoate

Traditional Name

(1S,2S,4R,5R,8S,9S,10Z,12R)-11-({[(2R,3S,4R,5R)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0^{4,9}]pentadeca-6,10,13-trien-2-yl (2E)-3-(1-methylimidazol-4-yl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CO[C@@]12O[C@@](C)(C=C1)[C@H](C[C@@H]1[C@H](\C=C2\CO[C@@H]2OC[C@@H](O)[C@@H](O)[C@@H]2OC(C)=O)[C@H](C=C[C@@]1(C)O)C(C)C)OC(=O)\C=C\C1=CN(C)C=N1

InChI Identifier

InChI=1S/C35H48N2O11/c1-20(2)24-10-11-33(4,42)26-15-28(47-29(40)9-8-23-16-37(6)19-36-23)34(5)12-13-35(43-7,48-34)22(14-25(24)26)17-44-32-31(46-21(3)38)30(41)27(39)18-45-32/h8-14,16,19-20,24-28,30-32,39,41-42H,15,17-18H2,1-7H3/b9-8+,22-14-/t24-,25-,26-,27-,28+,30-,31+,32-,33-,34+,35-/m1/s1

InChI Key

KGOMYXIKIJGWKS-DKNGGRFKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Erythropodium caribaeorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Glycosyl compound
O-glycosyl compound
Imidazolyl carboxylic acid derivative
Fatty acid ester
Ketal
Dicarboxylic acid or derivatives
Monosaccharide
N-substituted imidazole
Oxane
Fatty acyl
Azole
Dihydrofuran
Imidazole
Heteroaromatic compound
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Oxacycle
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Organonitrogen compound
Organic oxygen compound
Alcohol
Organic nitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.66	ChemAxon
pKa (Strongest Acidic)	12.8	ChemAxon
pKa (Strongest Basic)	5.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	168.03 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	175.85 m³·mol⁻¹	ChemAxon
Polarizability	70.45 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00028011

Chemspider ID

28478247

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57396455

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate (NP0259226)

MOL for NP0259226 ((1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

3D MOL for NP0259226 ((1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

3D SDF for NP0259226 ((1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

3D-SDF for NP0259226 ((1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

PDB for NP0259226 ((1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

3D PDB for NP0259226 ((1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

SMILES for NP0259226 ((1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

INCHI for NP0259226 ((1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

Structure for NP0259226 ((1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)

3D Structure for NP0259226 ((1s,2s,4r,5r,8s,9s,10z,12r)-11-({[(2r,3s,4r,5r)-3-(acetyloxy)-4,5-dihydroxyoxan-2-yl]oxy}methyl)-5-hydroxy-8-isopropyl-12-methoxy-1,5-dimethyl-15-oxatricyclo[10.2.1.0⁴,⁹]pentadeca-6,10,13-trien-2-yl (2e)-3-(1-methylimidazol-4-yl)prop-2-enoate)