NP-MRD: Showing NP-Card for Tinyatoxin (NP0052057)

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Record Information

Version

2.0

Created at

2022-04-27 23:14:10 UTC

Updated at

2022-04-27 23:14:10 UTC

NP-MRD ID

NP0052057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tinyatoxin

Description

[(1R,2S,6R,10S,11R,13R,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]Octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxyphenyl)acetate belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds. Tinyatoxin is found in Apis cerana, Euphorbia hirta, Euphorbia lactea, Euphorbia poisonii and Euphorbia tirucalli . Based on a literature review very few articles have been published on [(1R,2S,6R,10S,11R,13R,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0¹,¹⁰.0²,⁶.0¹¹,¹⁵]Octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxyphenyl)acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282201142D          

 44 50  0  0  1  0            999 V2000
    2.9559    0.5811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3514   -0.1429    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0319   -0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2380   -1.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676   -0.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5254    0.1767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1433    0.7233    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9303    1.4355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1408    1.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183    1.2936    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7186    0.6342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0447    0.0870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4735   -0.2162    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2051    0.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447   -0.3782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0508   -0.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7741   -0.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968   -1.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0217   -1.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4240   -0.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0013   -0.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1764   -0.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1135    1.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256    1.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668    2.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5518    1.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0958   -1.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7285   -2.4701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5862   -3.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8113   -3.5659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2189   -3.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9938   -3.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1360   -2.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9109   -2.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5435   -2.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4013   -3.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6264   -4.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3184   -2.6797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1622    0.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7621   -0.5569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2678    0.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5223    1.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9919    1.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8698   -0.7847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 13 15  1  0  0  0  0
  7 15  1  1  0  0  0
 13 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 10 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  8 26  1  1  0  0  0
  4 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 35 38  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
  1 42  1  1  0  0  0
 41 43  1  0  0  0  0
  2 44  1  6  0  0  0
M  END


  Mrv1652304282201142D          

 44 50  0  0  1  0            999 V2000
    2.9559    0.5811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3514   -0.1429    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0319   -0.9035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2380   -1.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676   -0.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5254    0.1767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1433    0.7233    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9303    1.4355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1408    1.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4183    1.2936    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7186    0.6342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0447    0.0870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4735   -0.2162    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2051    0.6577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447   -0.3782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0508   -0.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7741   -0.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968   -1.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0217   -1.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4240   -0.8893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0013   -0.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1764   -0.1926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1135    1.9243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9256    1.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668    2.7002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5518    1.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0958   -1.9406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7285   -2.4701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5862   -3.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8113   -3.5659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2189   -3.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9938   -3.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1360   -2.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9109   -2.4333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5435   -2.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4013   -3.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6264   -4.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3184   -2.6797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1622    0.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7621   -0.5569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2678    0.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5223    1.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9919    1.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8698   -0.7847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 13 15  1  0  0  0  0
  7 15  1  1  0  0  0
 13 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 10 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  8 26  1  1  0  0  0
  4 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 35 38  1  0  0  0  0
  2 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
  1 42  1  1  0  0  0
 41 43  1  0  0  0  0
  2 44  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0052057

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@@]2(O[C@]3(CC4=CC=CC=C4)O[C@@H]2[C@@H]2C=C(COC(=O)CC4=CC=C(O)C=C4)C[C@@]4(O)[C@H](C=C(C)C4=O)[C@@]12O3)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C36H38O8/c1-21(2)34-17-23(4)36-28(32(34)42-35(43-34,44-36)19-25-8-6-5-7-9-25)15-26(18-33(40)29(36)14-22(3)31(33)39)20-41-30(38)16-24-10-12-27(37)13-11-24/h5-15,23,28-29,32,37,40H,1,16-20H2,2-4H3/t23-,28+,29+,32-,33-,34-,35+,36-/m1/s1

> <INCHI_KEY>
WWZMXEIBZCEIFB-KDNHGMAXSA-N

> <FORMULA>
C36H38O8

> <MOLECULAR_WEIGHT>
598.692

> <EXACT_MASS>
598.256668184

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
73.2468733592598

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,6R,10S,11R,13R,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^{1,10}.0^{2,6}.0^{11,15}]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxyphenyl)acetate

> <ALOGPS_LOGP>
4.53

> <JCHEM_LOGP>
5.746544119999999

> <ALOGPS_LOGS>
-5.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.595341410606679

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.496077775705707

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8507489946897175

> <JCHEM_POLAR_SURFACE_AREA>
111.52

> <JCHEM_REFRACTIVITY>
163.64180000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.63e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2S,6R,10S,11R,13R,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^{1,10}.0^{2,6}.0^{11,15}]octadeca-3,8-dien-8-yl]methyl (4-hydroxyphenyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.518   1.085   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.256  -0.267   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.660  -1.687   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.178  -2.106   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.926  -1.208   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.847   0.330   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   1.350   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.603   2.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.130   3.349   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.781   2.415   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.341   1.184   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.083   0.162   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.884  -0.404   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.383   1.228   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.697  -0.706   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.095  -1.726   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.445  -1.704   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.234  -3.027   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.774  -3.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.525  -1.660   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.736  -0.337   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.196  -0.360   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.212   3.592   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.728   3.321   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.311   5.040   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.763   3.692   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.912  -3.623   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.093  -4.611   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.828  -6.128   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.381  -6.656   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.009  -7.116   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.455  -6.588   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.721  -5.071   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.167  -4.542   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.348  -5.531   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.082  -7.048   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.636  -7.576   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      11.794  -5.002   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       7.769   0.018   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       8.889  -1.040   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       7.967   1.545   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.575   2.204   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.318   2.283   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       7.224  -1.465   0.000  0.00  0.00           O+0
CONECT    1    2    7   42                                                  
CONECT    2    1    3   39   44                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    1    8   15                                             
CONECT    8    7    9   26                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   14   23                                             
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   16                                             
CONECT   14   13   10                                                       
CONECT   15   13    7                                                       
CONECT   16   13   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   10   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    8                                                            
CONECT   27    4   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   35                                                            
CONECT   39    2   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41    1                                                       
CONECT   43   41                                                            
CONECT   44    2                                                            
MASTER        0    0    0    0    0    0    0    0   44    0  100    0
END

View in JSmol

Synonyms

Value	Source
[(1R,2S,6R,10S,11R,13R,15R,17R)-13-Benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0,.0,.0,]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxyphenyl)acetic acid	Generator

Chemical Formula

C₃₆H₃₈O₈

Average Mass

598.6920 Da

Monoisotopic Mass

598.25667 Da

IUPAC Name

[(1R,2S,6R,10S,11R,13R,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^{1,10}.0^{2,6}.0^{11,15}]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxyphenyl)acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@@]2(O[C@]3(CC4=CC=CC=C4)O[C@@H]2[C@@H]2C=C(COC(=O)CC4=CC=C(O)C=C4)C[C@@]4(O)[C@H](C=C(C)C4=O)[C@@]12O3)C(C)=C

InChI Identifier

InChI=1S/C36H38O8/c1-21(2)34-17-23(4)36-28(32(34)42-35(43-34,44-36)19-25-8-6-5-7-9-25)15-26(18-33(40)29(36)14-22(3)31(33)39)20-41-30(38)16-24-10-12-27(37)13-11-24/h5-15,23,28-29,32,37,40H,1,16-20H2,2-4H3/t23-,28+,29+,32-,33-,34-,35+,36-/m1/s1

InChI Key

WWZMXEIBZCEIFB-KDNHGMAXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Euphorbia hirta	LOTUS Database	35616633
Euphorbia lactea	Plant	KNApSAcK
Euphorbia poisonii	Plant	KNApSAcK
Euphorbia tirucalli	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Rhamnofolane and daphnane diterpenoids

Alternative Parents

Substituents

Daphnane diterpenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Ortho ester
Dioxepane
Carboxylic acid orthoester
1,3-dioxepane
Benzenoid
Monocyclic benzene moiety
Meta-dioxane
Tertiary alcohol
Meta-dioxolane
Orthocarboxylic acid derivative
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	4.53	ALOGPS
logP	5.75	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	163.64 m³·mol⁻¹	ChemAxon
Polarizability	73.25 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

162971223

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tinyatoxin (NP0052057)

MOL for NP0052057 (Tinyatoxin)

3D MOL for NP0052057 (Tinyatoxin)

3D SDF for NP0052057 (Tinyatoxin)

3D-SDF for NP0052057 (Tinyatoxin)

PDB for NP0052057 (Tinyatoxin)

3D PDB for NP0052057 (Tinyatoxin)

SMILES for NP0052057 (Tinyatoxin)

INCHI for NP0052057 (Tinyatoxin)

Structure for NP0052057 (Tinyatoxin)

3D Structure for NP0052057 (Tinyatoxin)