NP-MRD: Showing NP-Card for (1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate (NP0158581)

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Record Information

Version

2.0

Created at

2022-09-02 16:11:52 UTC

Updated at

2022-09-02 16:11:52 UTC

NP-MRD ID

NP0158581

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate

Description

[(1S,4S,5S,6R,9S,10R,11R,12S,14R)-12-(benzoyloxy)-4-{[(2R)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-11-yl]methyl benzoate belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane. (1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate is found in Euphorbia esula. Based on a literature review very few articles have been published on [(1S,4S,5S,6R,9S,10R,11R,12S,14R)-12-(benzoyloxy)-4-{[(2R)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]Pentadeca-2,7-dien-11-yl]methyl benzoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022218112D          

 49 54  0  0  1  0            999 V2000
    0.3613   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9956   -0.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190   -1.1719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9381   -1.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.9524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5764   -2.0847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2647   -2.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4725   -3.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3711   -3.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7697   -2.6832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0519   -3.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7271   -1.8217    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0550   -2.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9496   -1.5083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2533   -1.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4780   -1.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130   -0.7447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1743   -2.0115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1393   -2.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9057   -1.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6020   -2.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9407   -0.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279   -1.5430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2412   -0.7181    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7203   -0.0465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3782    0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5569    0.7833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8572    1.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5151    2.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942    2.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8154    2.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1575    1.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6784    1.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885   -0.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723   -0.4094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2661    0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9489   -1.1421    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6323   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6171   -1.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5320   -2.4467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2001   -2.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1150   -3.7513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533   -2.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0384   -1.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7916   -1.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4597   -1.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3746   -2.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6214   -3.0781    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  1  6  0  0  0
  5  6  2  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  0  0  0  0
  4 36  1  0  0  0  0
 36 37  1  6  0  0  0
 25 38  1  0  0  0  0
 24 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 44 49  1  0  0  0  0
M  END


  Mrv1652309022218112D          

 49 54  0  0  1  0            999 V2000
    0.3613   -0.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9956   -0.6828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7995   -0.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3190   -1.1719    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9381   -1.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -0.9524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5764   -2.0847    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2647   -2.8701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4725   -3.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3711   -3.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7697   -2.6832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0519   -3.0897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7271   -1.8217    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0550   -2.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9496   -1.5083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2533   -1.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4780   -1.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130   -0.7447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1743   -2.0115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1393   -2.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9057   -1.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6020   -2.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9407   -0.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2279   -1.5430    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2412   -0.7181    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7203   -0.0465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3782    0.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5569    0.7833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8572    1.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5151    2.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9942    2.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8154    2.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1575    1.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6784    1.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5885   -0.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7723   -0.4094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2661    0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9489   -1.1421    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6323   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6171   -1.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5320   -2.4467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2001   -2.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1150   -3.7513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9533   -2.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0384   -1.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7916   -1.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4597   -1.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3746   -2.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6214   -3.0781    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  1  6  0  0  0
  5  6  2  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 25 35  1  0  0  0  0
 35 36  1  0  0  0  0
  4 36  1  0  0  0  0
 36 37  1  6  0  0  0
 25 38  1  0  0  0  0
 24 38  1  0  0  0  0
 38 39  1  6  0  0  0
 38 40  1  1  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 44 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0158581

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](C)C(=O)O[C@H]1C(C)=C[C@@]23[C@H](C)C[C@]4(OC(=O)C5=CC=CC=C5)[C@H]([C@H](C=C(C)[C@@H](O)[C@]12O)C3=O)[C@]4(C)COC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C40H46O9/c1-22(2)26(6)34(43)48-33-24(4)19-38-25(5)20-39(49-36(45)28-16-12-9-13-17-28)30(29(32(38)42)18-23(3)31(41)40(33,38)46)37(39,7)21-47-35(44)27-14-10-8-11-15-27/h8-19,22,25-26,29-31,33,41,46H,20-21H2,1-7H3/t25-,26-,29+,30-,31-,33+,37+,38+,39+,40+/m1/s1

> <INCHI_KEY>
NJTVEQAFXQUTID-WHSZRPALSA-N

> <FORMULA>
C40H46O9

> <MOLECULAR_WEIGHT>
670.799

> <EXACT_MASS>
670.314183061

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
95

> <JCHEM_AVERAGE_POLARIZABILITY>
73.12124645920711

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,5S,6R,9S,10R,11R,12S,14R)-11-[(benzoyloxy)methyl]-4-{[(2R)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-12-yl benzoate

> <ALOGPS_LOGP>
4.75

> <JCHEM_LOGP>
6.618156985666665

> <ALOGPS_LOGS>
-5.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.66079214279851

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.616195010962793

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5328269401346573

> <JCHEM_POLAR_SURFACE_AREA>
136.43000000000004

> <JCHEM_REFRACTIVITY>
182.62449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.72e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,5S,6R,9S,10R,11R,12S,14R)-11-[(benzoyloxy)methyl]-4-{[(2R)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0^{1,5}.0^{10,12}]pentadeca-2,7-dien-12-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.675  -0.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.858  -1.275   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.359  -0.910   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.329  -2.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.484  -3.024   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.389  -1.778   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.676  -3.891   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.094  -5.357   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.615  -5.886   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.426  -7.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.304  -5.009   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.964  -5.768   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.224  -3.400   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.969  -4.293   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.773  -2.816   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.473  -3.642   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.892  -2.929   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.958  -1.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.192  -3.755   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.127  -5.293   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.557  -3.042   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.857  -3.868   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.623  -1.503   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.892  -2.880   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.917  -1.341   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.811  -0.087   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.173   1.315   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.640   1.462   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.067   2.568   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.428   3.970   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.322   5.223   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.855   5.076   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.494   3.674   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.600   2.421   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.698  -0.315   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.175  -0.764   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.230   0.452   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.238  -2.132   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.514  -1.269   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.485  -3.035   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      10.326  -4.567   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      11.573  -5.471   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      11.415  -7.002   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      12.979  -4.842   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      13.138  -3.310   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      14.544  -2.682   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      15.791  -3.586   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      15.633  -5.117   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      14.227  -5.746   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   13   36                                             
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   24                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    4   14   15                                             
CONECT   14   13                                                            
CONECT   15   13    2   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    7   25   38                                                  
CONECT   25   24   26   35   38                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   25   36                                                       
CONECT   36   35    4   37                                                  
CONECT   37   36                                                            
CONECT   38   25   24   39   40                                             
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   49                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   44                                                       
MASTER        0    0    0    0    0    0    0    0   49    0  108    0
END

View in JSmol

Synonyms

Value	Source
[(1S,4S,5S,6R,9S,10R,11R,12S,14R)-12-(Benzoyloxy)-4-{[(2R)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0,.0,]pentadeca-2,7-dien-11-yl]methyl benzoic acid	Generator

Chemical Formula

C₄₀H₄₆O₉

Average Mass

670.7990 Da

Monoisotopic Mass

670.31418 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](C)C(=O)O[C@H]1C(C)=C[C@@]23[C@H](C)C[C@]4(OC(=O)C5=CC=CC=C5)[C@H]([C@H](C=C(C)[C@@H](O)[C@]12O)C3=O)[C@]4(C)COC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C40H46O9/c1-22(2)26(6)34(43)48-33-24(4)19-38-25(5)20-39(49-36(45)28-16-12-9-13-17-28)30(29(32(38)42)18-23(3)31(41)40(33,38)46)37(39,7)21-47-35(44)27-14-10-8-11-15-27/h8-19,22,25-26,29-31,33,41,46H,20-21H2,1-7H3/t25-,26-,29+,30-,31-,33+,37+,38+,39+,40+/m1/s1

InChI Key

NJTVEQAFXQUTID-WHSZRPALSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia esula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tigliane and ingenane diterpenoids. These are diterpenoids containing the tigliane or ingenane carbon skeleton. The tigliane skeleton is a tetracyclic ring that consists of the 4/7/6/3 ring junction. It is derived from casbane by 6,10- and 5,14-cyclizations and is a framework of phorbol. The ingenane skeleton is derived by rearrangement of tigliane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tigliane and ingenane diterpenoids

Alternative Parents

Substituents

Ingenane diterpenoid
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Fatty acid ester
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Tertiary alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
1,2-diol
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.75	ALOGPS
logS	-5.8	ALOGPS

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

162879706

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate (NP0158581)

MOL for NP0158581 ((1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate)

3D MOL for NP0158581 ((1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate)

3D SDF for NP0158581 ((1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate)

3D-SDF for NP0158581 ((1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate)

PDB for NP0158581 ((1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate)

3D PDB for NP0158581 ((1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate)

SMILES for NP0158581 ((1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate)

INCHI for NP0158581 ((1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate)

Structure for NP0158581 ((1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate)

3D Structure for NP0158581 ((1s,4s,5s,6r,9s,10r,11r,12s,14r)-11-[(benzoyloxy)methyl]-4-{[(2r)-2,3-dimethylbutanoyl]oxy}-5,6-dihydroxy-3,7,11,14-tetramethyl-15-oxotetracyclo[7.5.1.0¹,⁵.0¹⁰,¹²]pentadeca-2,7-dien-12-yl benzoate)