NP-MRD: Showing NP-Card for (1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid (NP0246601)

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Record Information

Version

2.0

Created at

2022-09-07 08:07:39 UTC

Updated at

2022-09-07 08:07:39 UTC

NP-MRD ID

NP0246601

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid

Description

(1S,2S,4R,5R,8R,9S,11S)-2-({[(2R,3S,4S,5R,6R)-3-hydroxy-5-methoxy-6-methyl-4-{[(2Z)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0²,¹¹.0⁴,⁸]Tridec-12-ene-1-carboxylic acid belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. (1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid is found in Parascedosporium putredinis. Based on a literature review very few articles have been published on (1S,2S,4R,5R,8R,9S,11S)-2-({[(2R,3S,4S,5R,6R)-3-hydroxy-5-methoxy-6-methyl-4-{[(2Z)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0²,¹¹.0⁴,⁸]Tridec-12-ene-1-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072210072D          

 43 47  0  0  1  0            999 V2000
   -2.5810   -0.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8055   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303   -1.7206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4548   -2.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8795   -3.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1040   -3.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0797   -2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552   -2.1094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045   -3.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2953   -3.2922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5198   -2.4983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0555   -1.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3195   -2.2958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5440   -1.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688   -0.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1933   -0.1167    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9162   -0.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   -0.1008    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4049   -0.1359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8610   -0.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6930    0.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0467    1.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593    0.6940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4907    0.4714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7204    1.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214    1.4611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9563   -0.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2812   -0.1561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1828    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3311    1.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1374    1.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7351    2.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6539    2.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537    0.8377    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4899    1.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2826    1.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1016    2.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8948   -2.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6703   -3.6810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2455   -4.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8705   -3.8835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6460   -4.6774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1537   -4.8799    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 28 27  1  1  0  0  0
 16 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 30 34  1  0  0  0  0
 16 34  1  0  0  0  0
 24 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 13 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 10 41  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
M  END


  Mrv1652309072210072D          

 43 47  0  0  1  0            999 V2000
   -2.5810   -0.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8055   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2303   -1.7206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4548   -2.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8795   -3.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1040   -3.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0797   -2.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8552   -2.1094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5045   -3.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2953   -3.2922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5198   -2.4983    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0555   -1.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3195   -2.2958    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5440   -1.5019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9688   -0.9106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1933   -0.1167    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9162   -0.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   -0.1008    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4049   -0.1359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8610   -0.8233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6930    0.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0467    1.1501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593    0.6940    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4907    0.4714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7204    1.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5214    1.4611    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9563   -0.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2812   -0.1561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1828    0.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3311    1.1575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1374    1.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7351    2.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6539    2.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0537    0.8377    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4899    1.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2826    1.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1016    2.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8948   -2.8871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6703   -3.6810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2455   -4.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8705   -3.8835    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6460   -4.6774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1537   -4.8799    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  6  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 24 27  1  0  0  0  0
 28 27  1  1  0  0  0
 16 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 30 34  1  0  0  0  0
 16 34  1  0  0  0  0
 24 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 13 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  6  0  0  0
 39 41  1  0  0  0  0
 10 41  1  0  0  0  0
 41 42  1  1  0  0  0
 42 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246601

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@@H](C)O[C@@H](OC[C@@]23C[C@@H]4[C@H](C)CC[C@H]4[C@@]4(CO)C[C@H]2C=C(C(C)C)[C@@]34C(O)=O)[C@@H](O)[C@@H]1OC(=O)C(\C)=C/C=C/C

> <INCHI_IDENTIFIER>
InChI=1S/C34H50O9/c1-8-9-10-20(5)29(37)43-28-26(36)30(42-21(6)27(28)40-7)41-17-33-15-23-19(4)11-12-24(23)32(16-35)14-22(33)13-25(18(2)3)34(32,33)31(38)39/h8-10,13,18-19,21-24,26-28,30,35-36H,11-12,14-17H2,1-7H3,(H,38,39)/b9-8+,20-10-/t19-,21-,22-,23-,24-,26+,27-,28+,30-,32+,33+,34+/m1/s1

> <INCHI_KEY>
QPMNLDCROSGTCI-OOKLOIGGSA-N

> <FORMULA>
C34H50O9

> <MOLECULAR_WEIGHT>
602.765

> <EXACT_MASS>
602.34548319

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
79.23858905110995

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4R,5R,8R,9S,11S)-2-({[(2R,3S,4S,5R,6R)-3-hydroxy-5-methoxy-6-methyl-4-{[(2Z,4E)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

> <JCHEM_LOGP>
4.532609376

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.338936299624265

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.197441193881562

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7764435263053455

> <JCHEM_POLAR_SURFACE_AREA>
131.75

> <JCHEM_REFRACTIVITY>
161.64990000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R,5R,8R,9S,11S)-2-({[(2R,3S,4S,5R,6R)-3-hydroxy-5-methoxy-6-methyl-4-{[(2Z,4E)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.818  -0.626   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.237  -2.108   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.163  -3.212   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.582  -4.694   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.508  -5.798   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.927  -7.279   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.016  -5.419   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.596  -3.938   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.942  -6.523   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.551  -6.145   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.970  -4.663   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.104  -3.560   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.463  -4.285   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.882  -2.804   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.808  -1.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.227  -0.218   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.577  -1.130   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.817  -0.188   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.356  -0.254   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.207  -1.537   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.894   1.189   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.687   2.147   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.404   1.295   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.783   0.880   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.211   2.359   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.707   2.727   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.785  -0.943   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.525  -0.291   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.341   0.975   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.618   2.161   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.257   3.658   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.372   4.719   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.221   4.093   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.967   1.564   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.781   2.871   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.261   3.297   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       2.056   4.230   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       3.537  -5.389   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.118  -6.871   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.192  -7.975   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.625  -7.249   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.206  -8.731   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -0.287  -9.109   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   41                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   38                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   28   34                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23   25   27   34                                             
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27   16   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   30   16   24   35                                             
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   13   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   10   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,4R,5R,8R,9S,11S)-2-({[(2R,3S,4S,5R,6R)-3-hydroxy-5-methoxy-6-methyl-4-{[(2Z)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0,.0,]tridec-12-ene-1-carboxylate	Generator

Chemical Formula

C₃₄H₅₀O₉

Average Mass

602.7650 Da

Monoisotopic Mass

602.34548 Da

IUPAC Name

(1S,2S,4R,5R,8R,9S,11S)-2-({[(2R,3S,4S,5R,6R)-3-hydroxy-5-methoxy-6-methyl-4-{[(2Z,4E)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

Traditional Name

(1S,2S,4R,5R,8R,9S,11S)-2-({[(2R,3S,4S,5R,6R)-3-hydroxy-5-methoxy-6-methyl-4-{[(2Z,4E)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0^{2,11}.0^{4,8}]tridec-12-ene-1-carboxylic acid

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@@H](C)O[C@@H](OC[C@@]23C[C@@H]4[C@H](C)CC[C@H]4[C@@]4(CO)C[C@H]2C=C(C(C)C)[C@@]34C(O)=O)[C@@H](O)[C@@H]1OC(=O)C(\C)=C/C=C/C

InChI Identifier

InChI=1S/C34H50O9/c1-8-9-10-20(5)29(37)43-28-26(36)30(42-21(6)27(28)40-7)41-17-33-15-23-19(4)11-12-24(23)32(16-35)14-22(33)13-25(18(2)3)34(32,33)31(38)39/h8-10,13,18-19,21-24,26-28,30,35-36H,11-12,14-17H2,1-7H3,(H,38,39)/b9-8+,20-10-/t19-,21-,22-,23-,24-,26+,27-,28+,30-,32+,33+,34+/m1/s1

InChI Key

QPMNLDCROSGTCI-OOKLOIGGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Parascedosporium putredinis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Sesquiterpenoid
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxide
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4.53	ChemAxon
pKa (Strongest Acidic)	4.2	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	131.75 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	161.65 m³·mol⁻¹	ChemAxon
Polarizability	79.24 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

Not Available

Chemspider ID

78440066

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24939410

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,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid (NP0246601)

MOL for NP0246601 ((1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D MOL for NP0246601 ((1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D SDF for NP0246601 ((1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D-SDF for NP0246601 ((1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

PDB for NP0246601 ((1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D PDB for NP0246601 ((1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

SMILES for NP0246601 ((1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

INCHI for NP0246601 ((1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

Structure for NP0246601 ((1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)

3D Structure for NP0246601 ((1s,2s,4r,5r,8r,9s,11s)-2-({[(2r,3s,4s,5r,6r)-3-hydroxy-5-methoxy-6-methyl-4-{[(2z,4e)-2-methylhexa-2,4-dienoyl]oxy}oxan-2-yl]oxy}methyl)-9-(hydroxymethyl)-13-isopropyl-5-methyltetracyclo[7.4.0.0²,¹¹.0⁴,⁸]tridec-12-ene-1-carboxylic acid)