NP-MRD: Showing NP-Card for Gambogefic acid D (NP0332282)

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Record Information

Version

2.0

Created at

2023-12-22 20:04:21 UTC

Updated at

2024-09-03 04:18:42 UTC

NP-MRD ID

NP0332282

Natural Product DOI

https://doi.org/10.57994/1483

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gambogefic acid D

Description

Gambogefic acid D is also known as gambogefate D. Based on a literature review very few articles have been published on Gambogefic acid D.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 12222320042D          

 53 59  0  0  1  0            999 V2000
   -0.1362   -0.5735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091   -0.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9467    0.6343    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5045    1.3308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7535    0.9530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7517    1.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1527    2.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4058    0.4184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9213   -0.2257    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0490   -0.3939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5251   -0.6354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0990   -1.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799   -2.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511   -1.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5217   -0.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1481   -2.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769   -1.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -2.9444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836   -1.3425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5989   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8305   -2.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1880   -0.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9793   -0.7568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1972   -0.4943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066    0.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7173   -0.9302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5429   -0.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205   -0.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6321    0.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8072    0.9556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1661   -0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9777   -0.3621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4437    0.2667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2553    0.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0669    0.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4080    1.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6009   -0.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3234   -0.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5118   -0.9909    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0458   -1.6198    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2342   -1.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0629   -2.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3473   -2.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4226   -1.9159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8886   -1.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0770   -1.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0146   -2.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8863   -3.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5362   -3.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6530   -3.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2630   -2.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615    0.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5039    1.4096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  5  3  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  8  5  1  0  0  0  0
  8  9  1  6  0  0  0
 10  8  1  0  0  0  0
 10 11  1  0  0  0  0
 11  2  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 23 20  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
  3 25  1  0  0  0  0
 10 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 32 31  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 39 38  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
 31 45  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 27 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 47 50  1  0  0  0  0
 47 51  1  0  0  0  0
 28 52  1  0  0  0  0
  8 52  1  0  0  0  0
 52 53  2  0  0  0  0
M  END


  Mrv2104 12222320042D          

 53 59  0  0  1  0            999 V2000
   -0.1362   -0.5735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7091   -0.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9467    0.6343    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5045    1.3308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7535    0.9530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7517    1.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1527    2.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4058    0.4184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9213   -0.2257    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0490   -0.3939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5251   -0.6354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0990   -1.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2799   -2.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511   -1.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5217   -0.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1481   -2.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769   -1.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -2.9444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836   -1.3425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5989   -1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8305   -2.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1880   -0.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9793   -0.7568    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1972   -0.4943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066    0.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7173   -0.9302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5429   -0.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205   -0.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6321    0.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8072    0.9556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1661   -0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9777   -0.3621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4437    0.2667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2553    0.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0669    0.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4080    1.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6009   -0.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3234   -0.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5118   -0.9909    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0458   -1.6198    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2342   -1.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0629   -2.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3473   -2.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4226   -1.9159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8886   -1.2871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0770   -1.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0146   -2.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8863   -3.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5362   -3.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6530   -3.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2630   -2.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2615    0.5855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5039    1.4096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  1  0  0  0
  5  3  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  8  5  1  0  0  0  0
  8  9  1  6  0  0  0
 10  8  1  0  0  0  0
 10 11  1  0  0  0  0
 11  2  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 23 20  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
  3 25  1  0  0  0  0
 10 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 32 31  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 39 38  1  0  0  0  0
 32 39  1  0  0  0  0
 39 40  1  1  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 41 44  1  0  0  0  0
 31 45  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 27 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 47 50  1  0  0  0  0
 47 51  1  0  0  0  0
 28 52  1  0  0  0  0
  8 52  1  0  0  0  0
 52 53  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332282

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@]3([H])[C@H](OC)[C@@]4([H])C(=O)C5=C(O[C@@]14[C@@](C\C=C(/C)C(O)=O)(OC2(C)C)C3=O)C(=C1OC(C)(C)[C@@]2([H])CCC(C)=C[C@@]2([H])C1=C5O)C(C)(C)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C39H48O9/c1-11-35(4,5)27-31-24(20-16-18(2)12-13-22(20)36(6,7)46-31)28(40)25-29(41)26-30(45-10)21-17-23-37(8,9)48-38(33(21)42,15-14-19(3)34(43)44)39(23,26)47-32(25)27/h11,14,16,20-23,26,30,40H,1,12-13,15,17H2,2-10H3,(H,43,44)/b19-14+/t20-,21-,22+,23+,26-,30+,38+,39?/m1/s1

> <INCHI_KEY>
JOMHTDXJZCTLEI-ZAUWTNOKSA-N

> <FORMULA>
C39H48O9

> <MOLECULAR_WEIGHT>
660.804

> <EXACT_MASS>
660.329833126

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
0.0

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-4-[(1S,2S,9S,14R,19R,20S,21R,23R)-16-hydroxy-20-methoxy-8,8,12,25,25-pentamethyl-5-(2-methylbut-3-en-2-yl)-18,22-dioxo-3,7,24-trioxaheptacyclo[19.4.1.0^{2,19}.0^{2,23}.0^{4,17}.0^{6,15}.0^{9,14}]hexacosa-4(17),5,12,15-tetraen-23-yl]-2-methylbut-2-enoic acid

> <JCHEM_LOGP>
6.803151451333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.398677108149935

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.482159209491163

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8304244701843975

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
180.59700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-4-[(1S,2S,9S,14R,19R,20S,21R,23R)-16-hydroxy-20-methoxy-8,8,12,25,25-pentamethyl-5-(2-methylbut-3-en-2-yl)-18,22-dioxo-3,7,24-trioxaheptacyclo[19.4.1.0^{2,19}.0^{2,23}.0^{4,17}.0^{6,15}.0^{9,14}]hexacosa-4(17),5,12,15-tetraen-23-yl]-2-methylbut-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-DEC-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-DEC-23         0                                  
HETATM    1  O   UNK     0      -0.254  -1.070   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.324  -0.307   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.767   1.184   0.000  0.00  0.00           C+0
HETATM    4  H   UNK     0       0.942   2.484   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0       3.273   1.779   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.270   3.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.152   4.508   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.491   0.781   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       5.453  -0.421   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       3.825  -0.735   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.847  -1.186   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.918  -2.905   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.389  -3.862   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.029  -3.140   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.974  -1.601   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.276  -3.957   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.637  -3.235   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.221  -5.496   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.649  -2.506   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.985  -2.877   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.417  -4.655   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.084  -1.717   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.828  -1.413   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       0.368  -0.923   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       0.572   0.060   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.072  -1.736   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.613  -1.505   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.132  -0.055   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.647   0.221   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.974   1.784   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.643  -0.952   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.158  -0.676   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0      10.162   0.498   0.000  0.00  0.00           H+0
HETATM   34  C   UNK     0      11.677   0.774   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.192   1.051   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.828   2.521   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.188  -0.123   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.670  -1.573   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.155  -1.850   0.000  0.00  0.00           C+0
HETATM   40  H   UNK     0      13.152  -3.024   0.000  0.00  0.00           H+0
HETATM   41  C   UNK     0      11.637  -3.300   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.184  -3.879   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      11.848  -4.916   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      10.122  -3.576   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       9.125  -2.403   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       7.610  -2.679   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.494  -4.498   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       7.254  -6.197   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       8.468  -7.145   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.686  -5.669   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.091  -5.404   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.088   1.093   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       6.541   2.631   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    5   25                                             
CONECT    4    3                                                            
CONECT    5    3    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10   52                                             
CONECT    9    8                                                            
CONECT   10    8   11   23   26                                             
CONECT   11   10    2   12   19                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   11   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   10   24   25                                             
CONECT   24   23                                                            
CONECT   25   23    3                                                       
CONECT   26   10   27                                                       
CONECT   27   26   28   46                                                  
CONECT   28   27   29   52                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   45                                                  
CONECT   32   31   33   34   39                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   32   40   41                                             
CONECT   40   39                                                            
CONECT   41   39   42   43   44                                             
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   41   45                                                       
CONECT   45   31   44   46                                                  
CONECT   46   45   27   47                                                  
CONECT   47   46   48   50   51                                             
CONECT   48   47   49                                                       
CONECT   49   48                                                            
CONECT   50   47                                                            
CONECT   51   47                                                            
CONECT   52   28    8   53                                                  
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  118    0
END

View in JSmol

Synonyms

Value	Source
Gambogefate D	Generator

Chemical Formula

C₃₉H₄₈O₉

Average Mass

660.8040 Da

Monoisotopic Mass

660.32983 Da

IUPAC Name

(2E)-4-[(1S,2S,9S,14R,19R,20S,21R,23R)-16-hydroxy-20-methoxy-8,8,12,25,25-pentamethyl-5-(2-methylbut-3-en-2-yl)-18,22-dioxo-3,7,24-trioxaheptacyclo[19.4.1.0^{2,19}.0^{2,23}.0^{4,17}.0^{6,15}.0^{9,14}]hexacosa-4(17),5,12,15-tetraen-23-yl]-2-methylbut-2-enoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@]3([H])[C@H](OC)[C@@]4([H])C(=O)C5=C(O[C@@]14[C@@](C\C=C(/C)C(O)=O)(OC2(C)C)C3=O)C(=C1OC(C)(C)[C@@]2([H])CCC(C)=C[C@@]2([H])C1=C5O)C(C)(C)C=C

InChI Identifier

InChI=1S/C39H48O9/c1-11-35(4,5)27-31-24(20-16-18(2)12-13-22(20)36(6,7)46-31)28(40)25-29(41)26-30(45-10)21-17-23-37(8,9)48-38(33(21)42,15-14-19(3)34(43)44)39(23,26)47-32(25)27/h11,14,16,20-23,26,30,40H,1,12-13,15,17H2,2-10H3,(H,43,44)/b19-14+/t20-,21-,22+,23+,26-,30+,38+,39?/m1/s1

InChI Key

JOMHTDXJZCTLEI-ZAUWTNOKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	Carbon¹³ NMR Spectrum (1D, 151 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2023-12-22	View Spectrum
1D NMR	Proton NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2023-12-22	View Spectrum
NOESY NMR	[Proton, Proton] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2023-12-22	View Spectrum
1D NMR	Proton NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2023-12-22	View Spectrum
HMBC NMR	[Proton, Carbon¹³] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2023-12-22	View Spectrum
COSY NMR	[Proton, Proton] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2023-12-22	View Spectrum
HMQC NMR	[Proton, Carbon¹³] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2023-12-22	View Spectrum
1D NMR	Proton NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2023-12-22	View Spectrum
1D NMR	Proton NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2023-12-22	View Spectrum
1D NMR	Carbon¹³ NMR Spectrum (1D, 151 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Not Available	Not Available	2023-12-22	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	6.8	ChemAxon
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	180.6 m³·mol⁻¹	ChemAxon
Polarizability	0 Å³	ChemAxon
Number of Rings	7	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gambogefic acid D (NP0332282)

MOL for NP0332282 (Gambogefic acid D)

3D MOL for NP0332282 (Gambogefic acid D)

3D SDF for NP0332282 (Gambogefic acid D)

3D-SDF for NP0332282 (Gambogefic acid D)

PDB for NP0332282 (Gambogefic acid D)

3D PDB for NP0332282 (Gambogefic acid D)

SMILES for NP0332282 (Gambogefic acid D)

INCHI for NP0332282 (Gambogefic acid D)

Structure for NP0332282 (Gambogefic acid D)

3D Structure for NP0332282 (Gambogefic acid D)