NP-MRD: Showing NP-Card for (2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid (NP0257579)

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Record Information

Version

1.0

Created at

2022-09-07 22:44:36 UTC

Updated at

2022-09-07 22:44:37 UTC

NP-MRD ID

NP0257579

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid

Description

(2Z)-4-[(1R,3aS,5R,6R,6aR,12aS,14R)-9-(3-Methyl-2-butenyl)-3,3,13,13,14-pentamethyl-5,6-dimethoxy-8-hydroxy-3,3a,4,5,6,6a-hexahydro-1,5-methano-10,11-(epoxyethano)-7,16-dioxo-7H-furo[3,4-d]xanthene-1-yl]-2-methyl-2-butenoic acid belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. (2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid is found in Garcinia acuminata. Based on a literature review very few articles have been published on (2Z)-4-[(1R,3aS,5R,6R,6aR,12aS,14R)-9-(3-Methyl-2-butenyl)-3,3,13,13,14-pentamethyl-5,6-dimethoxy-8-hydroxy-3,3a,4,5,6,6a-hexahydro-1,5-methano-10,11-(epoxyethano)-7,16-dioxo-7H-furo[3,4-d]xanthene-1-yl]-2-methyl-2-butenoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309082200442D          

 45 50  0  0  1  0            999 V2000
    0.8280    2.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5574    1.9884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8675    1.1575    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5710    0.6784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1466    1.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681    2.1487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9193    0.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5433    1.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5566    2.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3227    1.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0022    1.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8535    1.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2842    2.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8902    3.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1090    2.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4781    0.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8541   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0747    0.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3963   -0.3604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5296   -0.2158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2646   -0.9557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8927   -0.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3264    0.5232    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5108    0.8801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3441    0.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014   -0.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -0.5251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6342   -0.6555    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3812   -1.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1514   -1.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1858   -2.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9169   -3.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4892   -3.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236   -3.9321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7581   -2.7255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2226   -1.4181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9820   -1.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4036   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5739   -2.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1745   -0.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0881   -1.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4082   -1.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9965   -0.7980    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7429   -1.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1841    0.0054    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  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 10 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 21 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 17 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 40 43  1  0  0  0  0
 43 44  1  6  0  0  0
 43 45  1  0  0  0  0
 16 45  1  0  0  0  0
M  END


  Mrv1652309082200442D          

 45 50  0  0  1  0            999 V2000
    0.8280    2.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5574    1.9884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8675    1.1575    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5710    0.6784    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1466    1.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681    2.1487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9193    0.9733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5433    1.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5566    2.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3227    1.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0022    1.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8535    1.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2842    2.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8902    3.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1090    2.4531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4781    0.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8541   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0747    0.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3963   -0.3604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5296   -0.2158    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2646   -0.9557    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8927   -0.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3264    0.5232    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5108    0.8801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3441    0.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014   -0.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1056   -0.5251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6342   -0.6555    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3812   -1.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1514   -1.8416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1858   -2.6659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9169   -3.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4892   -3.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236   -3.9321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7581   -2.7255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2226   -1.4181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9820   -1.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4036   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5739   -2.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1745   -0.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0881   -1.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4082   -1.7506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9965   -0.7980    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7429   -1.2692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1841    0.0054    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  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 10 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  0  0  0  0
 21 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 17 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
 40 43  1  0  0  0  0
 43 44  1  6  0  0  0
 43 45  1  0  0  0  0
 16 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257579

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1[C@H]2C(=O)C3=C(O)C(CC=C(C)C)=C4O[C@H](C)C(C)(C)C4=C3O[C@@]22[C@H]3C[C@]1(OC)C(=O)[C@]2(C\C=C(\C)C(O)=O)OC3(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C35H44O10/c1-16(2)11-12-19-24(36)21-25(37)22-28(41-9)33(42-10)15-20-32(7,8)45-34(30(33)40,14-13-17(3)29(38)39)35(20,22)44-27(21)23-26(19)43-18(4)31(23,5)6/h11,13,18,20,22,28,36H,12,14-15H2,1-10H3,(H,38,39)/b17-13-/t18-,20+,22-,28-,33-,34+,35+/m1/s1

> <INCHI_KEY>
WLNGEHPSYXBRGK-GACALEMSSA-N

> <FORMULA>
C35H44O10

> <MOLECULAR_WEIGHT>
624.727

> <EXACT_MASS>
624.293447617

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
66.77477459962549

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-4-[(1S,2S,7R,14R,15R,16R,18R)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0^{2,14}.0^{2,18}.0^{4,12}.0^{5,9}]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid

> <JCHEM_LOGP>
5.800768260000002

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.0956036714589485

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.711650843698409

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6858743851659015

> <JCHEM_POLAR_SURFACE_AREA>
137.82

> <JCHEM_REFRACTIVITY>
165.49190000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-4-[(1S,2S,7R,14R,15R,16R,18R)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0^{2,14}.0^{2,18}.0^{4,12}.0^{5,9}]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid

> <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       1.546   4.567   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.907   3.712   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.486   2.161   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.799   1.266   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.874   2.433   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.914   4.011   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       7.316   1.817   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.481   2.824   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.506   4.415   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.936   2.319   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.204   3.346   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.793   3.305   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.597   4.619   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.862   5.972   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.137   4.579   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.226   0.807   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.061  -0.201   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.606   0.304   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.340  -0.673   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.722  -0.403   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.227  -1.784   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.533  -0.197   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.476   0.977   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.954   1.643   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.642   1.469   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.683  -0.362   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.197  -0.980   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.050  -1.224   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.445  -2.686   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.883  -3.438   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.947  -4.976   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.312  -5.690   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.647  -5.801   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.711  -7.340   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       3.282  -5.088   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       2.282  -2.647   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       3.700  -3.283   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.620  -4.643   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.805  -4.773   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.659  -1.620   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       9.498  -2.960   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      10.095  -3.268   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      11.193  -1.490   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      12.587  -2.369   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      11.544   0.010   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   18                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17   45                                                  
CONECT   17   16   18   40                                                  
CONECT   18   17    7   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    4   21   28                                             
CONECT   21   20   22   37                                                  
CONECT   22   21   23                                                       
CONECT   23   22    3   24   26                                             
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   20   29   36                                             
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                                                            
CONECT   36   28   37                                                       
CONECT   37   36   21   38   39                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   17   41   42   43                                             
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   40   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   16                                                       
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Value	Source
(2Z)-4-[(1R,3AS,5R,6R,6ar,12as,14R)-9-(3-methyl-2-butenyl)-3,3,13,13,14-pentamethyl-5,6-dimethoxy-8-hydroxy-3,3a,4,5,6,6a-hexahydro-1,5-methano-10,11-(epoxyethano)-7,16-dioxo-7H-furo[3,4-D]xanthene-1-yl]-2-methyl-2-butenoate	Generator

Chemical Formula

C₃₅H₄₄O₁₀

Average Mass

624.7270 Da

Monoisotopic Mass

624.29345 Da

IUPAC Name

(2Z)-4-[(1S,2S,7R,14R,15R,16R,18R)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0^{2,14}.0^{2,18}.0^{4,12}.0^{5,9}]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@H]2C(=O)C3=C(O)C(CC=C(C)C)=C4O[C@H](C)C(C)(C)C4=C3O[C@@]22[C@H]3C[C@]1(OC)C(=O)[C@]2(C\C=C(\C)C(O)=O)OC3(C)C

InChI Identifier

InChI=1S/C35H44O10/c1-16(2)11-12-19-24(36)21-25(37)22-28(41-9)33(42-10)15-20-32(7,8)45-34(30(33)40,14-13-17(3)29(38)39)35(20,22)44-27(21)23-26(19)43-18(4)31(23,5)6/h11,13,18,20,22,28,36H,12,14-15H2,1-10H3,(H,38,39)/b17-13-/t18-,20+,22-,28-,33-,34+,35+/m1/s1

InChI Key

WLNGEHPSYXBRGK-GACALEMSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Garcinia acuminata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
Aromatic monoterpenoid
Monoterpenoid
Coumaran
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
Phenol
Oxepane
Benzenoid
Vinylogous acid
Oxolane
Ketone
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	5.8	ChemAxon
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	137.82 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	165.49 m³·mol⁻¹	ChemAxon
Polarizability	66.77 Å³	ChemAxon
Number of Rings	6	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

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

101258583

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid (NP0257579)

MOL for NP0257579 ((2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid)

3D MOL for NP0257579 ((2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid)

3D SDF for NP0257579 ((2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid)

3D-SDF for NP0257579 ((2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid)

PDB for NP0257579 ((2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid)

3D PDB for NP0257579 ((2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid)

SMILES for NP0257579 ((2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid)

INCHI for NP0257579 ((2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid)

Structure for NP0257579 ((2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid)

3D Structure for NP0257579 ((2z)-4-[(1s,2s,7r,14r,15r,16r,18r)-11-hydroxy-15,16-dimethoxy-6,6,7,20,20-pentamethyl-10-(3-methylbut-2-en-1-yl)-13,17-dioxo-3,8,19-trioxahexacyclo[14.4.1.0²,¹⁴.0²,¹⁸.0⁴,¹².0⁵,⁹]henicosa-4,9,11-trien-18-yl]-2-methylbut-2-enoic acid)