NP-MRD: Showing NP-Card for excoecarin T1 dimethyl ester (NP0030914)

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Record Information

Version

2.0

Created at

2021-06-19 22:08:34 UTC

Updated at

2021-06-29 23:59:11 UTC

NP-MRD ID

NP0030914

Secondary Accession Numbers

None

Natural Product Identification

Common Name

excoecarin T1 dimethyl ester

Provided By

JEOL Database JEOL Logo

Description

Methyl 2-[(2R,4aS,5R,6S,8aS)-5-(2-methoxy-2-oxoethyl)-2,5,8a-trimethyl-2-[(2S)-oxiran-2-yl]-octahydro-2H-1-benzopyran-6-yl]-2-methylpropanoate belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. excoecarin T1 dimethyl ester is found in Excoecaria agallocha. excoecarin T1 dimethyl ester was first documented in 2003 (Konishi, T., et al.). Based on a literature review very few articles have been published on methyl 2-[(2R,4aS,5R,6S,8aS)-5-(2-methoxy-2-oxoethyl)-2,5,8a-trimethyl-2-[(2S)-oxiran-2-yl]-octahydro-2H-1-benzopyran-6-yl]-2-methylpropanoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100083D          

 64 66  0  0  0  0            999 V2000
   -1.4750    1.2385    4.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8549    0.2715    3.8088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7197   -0.4115    3.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9348   -0.2664    3.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9780   -1.3874    2.1228 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4414   -0.8220    0.7576 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0937   -2.0446   -0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7046    0.2816    0.9651 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1355   -0.0996    1.5851 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.7895    1.2087    2.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0566    0.6019    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 28  1  0  0  0  0
  8 37  1  1  0  0  0
  8 16  1  0  0  0  0
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 17 18  1  0  0  0  0
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M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202100083D          

 64 66  0  0  0  0            999 V2000
   -1.4750    1.2385    4.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8549    0.2715    3.8088 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9348   -0.2664    3.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9780   -1.3874    2.1228 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.1336   -1.0486    2.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7895    1.2087    2.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041    1.7124    1.6294 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791    1.7410    3.1313 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6158    2.9606    3.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9409    1.1133   -0.3315 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3228    1.7070   -0.9338 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3705    0.6449   -1.2939 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.8750    0.1149   -3.2251 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1016   -0.6260   -3.7142 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9144   -1.3159   -3.3104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879   -0.2293   -0.6778 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8860   -1.0779   -0.2682 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6770   -0.1591   -0.0053 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.3517   -0.0398   -0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7361   -1.6521    0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0759   -0.9577    1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4561   -0.7154    3.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289   -1.0910    3.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8849   -2.0747    2.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9715    3.2959    4.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6231    2.7996    4.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6212    3.7329    2.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6166    1.9497   -0.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4445    0.5070   -1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536    2.4326   -0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    2.2963   -1.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4709   -1.0560   -2.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9593    0.4540   -3.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578   -0.4722   -2.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7502    2.4463   -0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6724    2.5829   -2.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8622    1.4949   -1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3150    0.6695   -3.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3262   -0.5979   -4.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9706   -0.7077   -3.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3711    0.3585    0.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9457   -0.8771   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1757   -1.6367    0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666   -1.8241   -1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0566    0.6019    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 28  1  0  0  0  0
  8 37  1  1  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
 16 17  1  0  0  0  0
 28 64  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 28 18  1  0  0  0  0
 23 21  1  0  0  0  0
  6  5  1  1  0  0  0
 21 22  1  6  0  0  0
  6  8  1  0  0  0  0
  6  7  1  0  0  0  0
  9 11  1  0  0  0  0
  3  5  1  0  0  0  0
  3  4  2  0  0  0  0
  9 12  1  1  0  0  0
  3  2  1  0  0  0  0
  9  8  1  0  0  0  0
 12 14  1  0  0  0  0
 28 27  1  0  0  0  0
 12 13  2  0  0  0  0
 18 20  1  0  0  0  0
 14 15  1  0  0  0  0
 20 21  1  0  0  0  0
  2  1  1  0  0  0  0
 25 23  1  0  0  0  0
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 23 24  1  0  0  0  0
 21 26  1  0  0  0  0
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  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
 16 47  1  0  0  0  0
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  7 34  1  0  0  0  0
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  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 24 58  1  0  0  0  0
 24 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030914

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])([H])OC(=O)C([H])([H])[C@]1(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])[C@@]2(O[C@](C([H])([H])[H])(C([H])([H])C([H])([H])[C@@]12[H])[C@@]1([H])OC1([H])[H])C([H])([H])[H])C(C(=O)OC([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H36O6/c1-19(2,18(24)26-7)14-8-10-21(4)15(20(14,3)12-17(23)25-6)9-11-22(5,28-21)16-13-27-16/h14-16H,8-13H2,1-7H3/t14-,15+,16+,20-,21+,22-/m1/s1

> <INCHI_KEY>
LOMIMFGOZFHXSO-XMOSRXQISA-N

> <FORMULA>
C22H36O6

> <MOLECULAR_WEIGHT>
396.524

> <EXACT_MASS>
396.251188879

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
43.23123582526614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(2R,4aS,5R,6S,8aS)-5-(2-methoxy-2-oxoethyl)-2,5,8a-trimethyl-2-[(2S)-oxiran-2-yl]-octahydro-2H-1-benzopyran-6-yl]-2-methylpropanoate

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.235543404999997

> <ALOGPS_LOGS>
-5.35

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9114067683261093

> <JCHEM_POLAR_SURFACE_AREA>
74.36000000000001

> <JCHEM_REFRACTIVITY>
103.77780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[(2R,4aS,5R,6S,8aS)-5-(2-methoxy-2-oxoethyl)-2,5,8a-trimethyl-2-[(2S)-oxiran-2-yl]-hexahydro-1-benzopyran-6-yl]-2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
   -1.4750    1.2385    4.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9348   -0.2664    3.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0937   -2.0446   -0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7046    0.2816    0.9651 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1355   -0.0996    1.5851 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1141   -0.7210    0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336   -1.0486    2.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7895    1.2087    2.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041    1.7124    1.6294 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7969    0.7317   -1.8432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8372    1.8719   -1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8750    0.1149   -3.2251 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1016   -0.6260   -3.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9144   -1.3159   -3.3104 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8860   -1.0779   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7126   -2.7165   -0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2571    1.0031    1.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3517   -0.0398   -0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7361   -1.6521    0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0759   -0.9577    1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4561   -0.7154    3.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289   -1.0910    3.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9715    3.2959    4.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6231    2.7996    4.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6212    3.7329    2.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6166    1.9497   -0.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4445    0.5070   -1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536    2.4326   -0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    2.2963   -1.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4709   -1.0560   -2.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1578   -0.4722   -2.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.9706   -0.7077   -3.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3711    0.3585    0.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9457   -0.8771   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1757   -1.6367    0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666   -1.8241   -1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0566    0.6019    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 28  1  0
  8 37  1  1
  8 16  1  0
  9 10  1  0
 16 17  1  0
 28 64  1  1
 17 18  1  0
 18 19  1  6
 28 18  1  0
 23 21  1  0
  6  5  1  1
 21 22  1  6
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  6  7  1  0
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  3  4  2  0
  9 12  1  1
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 12 14  1  0
 28 27  1  0
 12 13  2  0
 18 20  1  0
 14 15  1  0
 20 21  1  0
  2  1  1  0
 25 23  1  0
 24 25  1  0
 23 24  1  0
 21 26  1  0
 26 27  1  0
  5 32  1  0
  5 33  1  0
 16 47  1  0
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 17 49  1  0
 17 50  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
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 19 52  1  0
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 23 57  1  6
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  7 34  1  0
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 11 41  1  0
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 15 44  1  0
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 15 46  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 24 58  1  0
 24 59  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.475   1.238   4.656  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.855   0.272   3.809  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.720  -0.412   3.015  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.935  -0.266   3.012  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.978  -1.387   2.123  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.441  -0.822   0.758  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.094  -2.045  -0.015  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.705   0.282   0.965  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.135  -0.100   1.585  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.114  -0.721   0.557  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.134  -1.049   2.795  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.789   1.209   2.095  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.804   1.712   1.629  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.079   1.741   3.131  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.616   2.961   3.644  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.941   1.113  -0.332  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.323   1.707  -0.934  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.371   0.645  -1.294  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.882  -0.154  -2.514  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.535   1.409  -1.678  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.797   0.732  -1.843  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.837   1.872  -1.798  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.875   0.115  -3.225  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.102  -0.626  -3.714  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.914  -1.316  -3.310  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.088  -0.229  -0.678  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.886  -1.078  -0.268  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.677  -0.159  -0.005  0.00  0.00           C+0
HETATM   29  H   UNK     0      -1.999   1.992   4.059  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.160   0.751   5.356  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.690   1.738   5.230  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.669  -2.221   1.942  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.202  -1.865   2.720  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.655  -1.769  -0.907  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.762  -2.647   0.608  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.713  -2.716  -0.325  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.257   1.003   1.662  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.352  -0.040  -0.266  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.736  -1.652   0.132  0.00  0.00           H+0
HETATM   40  H   UNK     0       4.076  -0.958   1.031  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.456  -0.715   3.584  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.129  -1.091   3.257  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.885  -2.075   2.512  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.972   3.296   4.462  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.623   2.800   4.040  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.621   3.733   2.869  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.617   1.950  -0.117  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.444   0.507  -1.088  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.754   2.433  -0.230  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.066   2.296  -1.824  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.471  -1.056  -2.688  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.959   0.454  -3.423  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.158  -0.472  -2.445  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.750   2.446  -0.868  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.672   2.583  -2.617  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.862   1.495  -1.878  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.315   0.670  -3.968  0.00  0.00           H+0
HETATM   58  H   UNK     0      -5.326  -0.598  -4.773  0.00  0.00           H+0
HETATM   59  H   UNK     0      -5.971  -0.708  -3.075  0.00  0.00           H+0
HETATM   60  H   UNK     0      -4.371   0.359   0.207  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.946  -0.877  -0.891  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.176  -1.637   0.625  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.667  -1.824  -1.036  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.057   0.602   0.695  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    3    1                                                       
CONECT    3    5    4    2                                                  
CONECT    4    3                                                            
CONECT    5    6    3   32   33                                             
CONECT    6   28    5    8    7                                             
CONECT    7    6   34   35   36                                             
CONECT    8   37   16    6    9                                             
CONECT    9   10   11   12    8                                             
CONECT   10    9   38   39   40                                             
CONECT   11    9   41   42   43                                             
CONECT   12    9   14   13                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   44   45   46                                             
CONECT   16    8   17   47   48                                             
CONECT   17   16   18   49   50                                             
CONECT   18   17   19   28   20                                             
CONECT   19   18   51   52   53                                             
CONECT   20   18   21                                                       
CONECT   21   23   22   20   26                                             
CONECT   22   21   54   55   56                                             
CONECT   23   21   25   24   57                                             
CONECT   24   25   23   58   59                                             
CONECT   25   23   24                                                       
CONECT   26   21   27   60   61                                             
CONECT   27   28   26   62   63                                             
CONECT   28    6   64   18   27                                             
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38   10                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   11                                                            
CONECT   44   15                                                            
CONECT   45   15                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   19                                                            
CONECT   54   22                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   24                                                            
CONECT   60   26                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
CONECT   63   27                                                            
CONECT   64   28                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  132    0
END

RDKit          3D

64 66  0  0  0  0  0  0  0  0999 V2000
   -1.4750    1.2385    4.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8549    0.2715    3.8088 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7197   -0.4115    3.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9348   -0.2664    3.0118 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9780   -1.3874    2.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4414   -0.8220    0.7576 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0937   -2.0446   -0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7046    0.2816    0.9651 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1355   -0.0996    1.5851 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1141   -0.7210    0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1336   -1.0486    2.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7895    1.2087    2.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041    1.7124    1.6294 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791    1.7410    3.1313 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6158    2.9606    3.6440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9409    1.1133   -0.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3228    1.7070   -0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3705    0.6449   -1.2939 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8823   -0.1544   -2.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5353    1.4094   -1.6778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7969    0.7317   -1.8432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8372    1.8719   -1.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8750    0.1149   -3.2251 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.1016   -0.6260   -3.7142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9144   -1.3159   -3.3104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879   -0.2293   -0.6778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8860   -1.0779   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6770   -0.1591   -0.0053 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9992    1.9915    4.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1603    0.7507    5.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6897    1.7380    5.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6688   -2.2212    1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2020   -1.8649    2.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6552   -1.7687   -0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7619   -2.6470    0.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -2.7165   -0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2571    1.0031    1.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3517   -0.0398   -0.2659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7361   -1.6521    0.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0759   -0.9577    1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4561   -0.7154    3.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289   -1.0910    3.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8849   -2.0747    2.5119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9715    3.2959    4.4615 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6231    2.7996    4.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6212    3.7329    2.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6166    1.9497   -0.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4445    0.5070   -1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536    2.4326   -0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    2.2963   -1.8240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4709   -1.0560   -2.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9593    0.4540   -3.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1578   -0.4722   -2.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7502    2.4463   -0.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6724    2.5829   -2.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8622    1.4949   -1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3150    0.6695   -3.9683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3262   -0.5979   -4.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9706   -0.7077   -3.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3711    0.3585    0.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9457   -0.8771   -0.8906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1757   -1.6367    0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6666   -1.8241   -1.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0566    0.6019    0.6948 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 28  1  0
  8 37  1  1
  8 16  1  0
  9 10  1  0
 16 17  1  0
 28 64  1  1
 17 18  1  0
 18 19  1  6
 28 18  1  0
 23 21  1  0
  6  5  1  1
 21 22  1  6
  6  8  1  0
  6  7  1  0
  9 11  1  0
  3  5  1  0
  3  4  2  0
  9 12  1  1
  3  2  1  0
  9  8  1  0
 12 14  1  0
 28 27  1  0
 12 13  2  0
 18 20  1  0
 14 15  1  0
 20 21  1  0
  2  1  1  0
 25 23  1  0
 24 25  1  0
 23 24  1  0
 21 26  1  0
 26 27  1  0
  5 32  1  0
  5 33  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
 19 51  1  0
 19 52  1  0
 19 53  1  0
 23 57  1  6
 22 54  1  0
 22 55  1  0
 22 56  1  0
  7 34  1  0
  7 35  1  0
  7 36  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 24 58  1  0
 24 59  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Methyl 2-[(2R,4as,5R,6S,8as)-5-(2-methoxy-2-oxoethyl)-2,5,8a-trimethyl-2-[(2S)-oxiran-2-yl]-octahydro-2H-1-benzopyran-6-yl]-2-methylpropanoic acid	Generator

Chemical Formula

C₂₂H₃₆O₆

Average Mass

396.5240 Da

Monoisotopic Mass

396.25119 Da

IUPAC Name

methyl 2-[(2R,4aS,5R,6S,8aS)-5-(2-methoxy-2-oxoethyl)-2,5,8a-trimethyl-2-[(2S)-oxiran-2-yl]-octahydro-2H-1-benzopyran-6-yl]-2-methylpropanoate

Traditional Name

methyl 2-[(2R,4aS,5R,6S,8aS)-5-(2-methoxy-2-oxoethyl)-2,5,8a-trimethyl-2-[(2S)-oxiran-2-yl]-hexahydro-1-benzopyran-6-yl]-2-methylpropanoate

CAS Registry Number

Not Available

SMILES

[H]C([H])([H])OC(=O)C([H])([H])[C@]1(C([H])([H])[H])[C@]([H])(C([H])([H])C([H])([H])[C@@]2(O[C@](C([H])([H])[H])(C([H])([H])C([H])([H])[C@@]12[H])[C@@]1([H])OC1([H])[H])C([H])([H])[H])C(C(=O)OC([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H36O6/c1-19(2,18(24)26-7)14-8-10-21(4)15(20(14,3)12-17(23)25-6)9-11-22(5,28-21)16-13-27-16/h14-16H,8-13H2,1-7H3/t14-,15+,16+,20-,21+,22-/m1/s1

InChI Key

LOMIMFGOZFHXSO-XMOSRXQISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Excoecaria agallocha	JEOL database	Konishi, T., et al, Phytochemistry 64, 835 (2003)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Fatty acid ester
Dicarboxylic acid or derivatives
Oxane
Fatty acyl
Methyl ester
Carboxylic acid ester
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.57	ALOGPS
logP	3.24	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	103.78 m³·mol⁻¹	ChemAxon
Polarizability	43.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

10186453

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21576537

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Konishi, T., et al. (2003). Konishi, T., et al, Phytochemistry 64, 835 (2003). Phytochem..

Showing NP-Card for excoecarin T1 dimethyl ester (NP0030914)

MOL for NP0030914 (excoecarin T1 dimethyl ester)

3D MOL for NP0030914 (excoecarin T1 dimethyl ester)

3D SDF for NP0030914 (excoecarin T1 dimethyl ester)

3D-SDF for NP0030914 (excoecarin T1 dimethyl ester)

PDB for NP0030914 (excoecarin T1 dimethyl ester)

3D PDB for NP0030914 (excoecarin T1 dimethyl ester)

SMILES for NP0030914 (excoecarin T1 dimethyl ester)

INCHI for NP0030914 (excoecarin T1 dimethyl ester)

Structure for NP0030914 (excoecarin T1 dimethyl ester)

3D Structure for NP0030914 (excoecarin T1 dimethyl ester)