NP-MRD: Showing NP-Card for caesalpinin MB (NP0027560)

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Record Information

Version

2.0

Created at

2021-06-19 19:41:17 UTC

Updated at

2021-06-29 23:53:44 UTC

NP-MRD ID

NP0027560

Secondary Accession Numbers

None

Natural Product Identification

Common Name

caesalpinin MB

Provided By

JEOL Database JEOL Logo

Description

caesalpinin MB is found in Caesalpiniacrista and Caesalpinia crista . caesalpinin MB was first documented in 2004 (Kalauni, S. K., et al.). Based on a literature review very few articles have been published on methyl (1S,2S,3S,7R,10R,11S)-3-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁶]Heptadeca-12(16),13-diene-11-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121413D          

 61 64  0  0  0  0            999 V2000
   -0.0472    4.3436    6.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4855    3.9059    5.2113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253    2.5474    5.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2189    1.7495    5.9480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154    2.1775    3.6744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4919    1.9446    3.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710    2.6912    4.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7173    2.0011    3.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4158    0.8848    3.1650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690    0.8708    3.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031   -0.2258    2.3152 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9621    0.2252    1.9218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2325    0.9225    3.1327 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2038    1.3511    2.7749 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0285    0.2799    2.0572 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3012   -0.2976    0.8234 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9992    0.8668    0.0112 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -1.2137   -0.0807 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3470   -0.3706   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7700    2.1649    4.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3881   -1.0997    2.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9840   -0.4807    1.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0998    1.0133    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9669    0.7599    1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -0.5061    2.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3445    0.6046   -0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
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 10  6  2  0  0  0  0
 12 13  1  0  0  0  0
 18 16  1  0  0  0  0
 28 23  1  0  0  0  0
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  6  5  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 21 18  1  0  0  0  0
 18 19  1  6  0  0  0
 12 11  1  0  0  0  0
 13  5  1  0  0  0  0
 10 11  1  0  0  0  0
 22 21  1  0  0  0  0
 18 20  1  0  0  0  0
 22 23  1  0  0  0  0
 13 39  1  1  0  0  0
 28 29  1  1  0  0  0
  5  3  1  0  0  0  0
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 23 24  1  0  0  0  0
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  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
   -0.0472    4.3436    6.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4855    3.9059    5.2113 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0154    2.1775    3.6744 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192121413D          

 61 64  0  0  0  0            999 V2000
   -0.0472    4.3436    6.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4855    3.9059    5.2113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253    2.5474    5.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2189    1.7495    5.9480 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0690    0.8708    3.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6292    0.5159   -2.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9634   -1.7347   -1.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9840   -0.4807    1.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1706    2.2482    2.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9669    0.7599    1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -0.5061    2.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3445    0.6046   -0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0327    0.0644   -0.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9409    0.4439   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500   -0.9928   -1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7199   -2.8090    0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3291   -3.1413    1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9971   -2.5856   -1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -1.0715   -1.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4346   -2.8461   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3158   -3.3983   -0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6916   -2.0956    0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914    0.7373   -3.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5178    0.3245   -3.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8331    1.3645   -1.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -2.9326    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8908   -2.4895    2.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5797   -1.7557    3.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  6  2  0  0  0  0
 12 13  1  0  0  0  0
 18 16  1  0  0  0  0
 28 23  1  0  0  0  0
 28 16  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 21 18  1  0  0  0  0
 18 19  1  6  0  0  0
 12 11  1  0  0  0  0
 13  5  1  0  0  0  0
 10 11  1  0  0  0  0
 22 21  1  0  0  0  0
 18 20  1  0  0  0  0
 22 23  1  0  0  0  0
 13 39  1  1  0  0  0
 28 29  1  1  0  0  0
  5  3  1  0  0  0  0
 28 12  1  0  0  0  0
 23 24  1  0  0  0  0
 16 15  1  0  0  0  0
 24 25  1  0  0  0  0
 15 14  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 16 17  1  6  0  0  0
  3  2  1  0  0  0  0
 14 13  1  0  0  0  0
  3  4  2  0  0  0  0
 12 38  1  6  0  0  0
  2  1  1  0  0  0  0
 22 53  1  0  0  0  0
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 14 41  1  0  0  0  0
 11 36  1  0  0  0  0
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 29 59  1  0  0  0  0
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 29 61  1  0  0  0  0
  5 33  1  6  0  0  0
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  7 34  1  0  0  0  0
  8 35  1  0  0  0  0
 21 51  1  0  0  0  0
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 19 45  1  0  0  0  0
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 26 56  1  0  0  0  0
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 26 58  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027560

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12C([H])([H])C([H])([H])[C@@]3([H])[C@]([H])(C(=O)OC([H])([H])[H])C4=C(OC([H])=C4[H])C([H])([H])[C@]3([H])[C@@]1(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])C2(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O6/c1-13(24)29-18-7-9-21(2,3)23(26)10-6-14-16(22(18,23)4)12-17-15(8-11-28-17)19(14)20(25)27-5/h8,11,14,16,18-19,26H,6-7,9-10,12H2,1-5H3/t14-,16+,18+,19+,22+,23-/m1/s1

> <INCHI_KEY>
YKYVQVVITOKCCL-AOKVBNASSA-N

> <FORMULA>
C23H32O6

> <MOLECULAR_WEIGHT>
404.503

> <EXACT_MASS>
404.21988875

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
44.143315863523526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,2S,3S,7R,10R,11S)-3-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylate

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
2.7914123899999983

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.969530784565762

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8237331331623396

> <JCHEM_POLAR_SURFACE_AREA>
85.97

> <JCHEM_REFRACTIVITY>
105.628

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2S,3S,7R,10R,11S)-3-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
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   -2.4031   -0.2258    2.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9621    0.2252    1.9218 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.0963   -2.5004   -0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050   -1.5429    0.0211 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.9840   -0.4807    1.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2983   -0.5061    2.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3445    0.6046   -0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0327    0.0644   -0.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9409    0.4439   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500   -0.9928   -1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5215   -1.9456    1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7199   -2.8090    0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3291   -3.1413    1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9971   -2.5856   -1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -1.0715   -1.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4346   -2.8461   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3158   -3.3983   -0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6916   -2.0956    0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914    0.7373   -3.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8331    1.3645   -1.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -2.9326    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8908   -2.4895    2.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5797   -1.7557    3.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  6  2  0
 12 13  1  0
 18 16  1  0
 28 23  1  0
 28 16  1  0
  6  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 21 18  1  0
 18 19  1  6
 12 11  1  0
 13  5  1  0
 10 11  1  0
 22 21  1  0
 18 20  1  0
 22 23  1  0
 13 39  1  1
 28 29  1  1
  5  3  1  0
 28 12  1  0
 23 24  1  0
 16 15  1  0
 24 25  1  0
 15 14  1  0
 25 26  1  0
 25 27  2  0
 16 17  1  6
  3  2  1  0
 14 13  1  0
  3  4  2  0
 12 38  1  6
  2  1  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  1
 15 42  1  0
 15 43  1  0
 14 40  1  0
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 11 36  1  0
 11 37  1  0
 29 59  1  0
 29 60  1  0
 29 61  1  0
  5 33  1  6
 17 44  1  0
  7 34  1  0
  8 35  1  0
 21 51  1  0
 21 52  1  0
 19 45  1  0
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 20 50  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.047   4.344   6.498  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.486   3.906   5.211  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.525   2.547   5.071  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.219   1.750   5.948  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.015   2.178   3.674  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.492   1.945   3.680  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.571   2.691   4.216  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.717   2.001   3.883  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.416   0.885   3.165  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.069   0.871   3.047  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.403  -0.226   2.315  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.962   0.225   1.922  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.233   0.923   3.133  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.204   1.351   2.775  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.029   0.280   2.057  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.301  -0.298   0.823  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.999   0.867   0.011  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.229  -1.214  -0.081  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.347  -0.371  -0.764  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.975  -2.332   0.679  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.395  -1.841  -1.230  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.096  -2.500  -0.772  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.805  -1.543   0.021  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.213  -0.468  -0.859  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.318  -0.698  -1.625  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.629   0.516  -2.445  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.963  -1.735  -1.647  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.084  -0.935   1.272  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.079  -2.077   2.314  0.00  0.00           C+0
HETATM   30  H   UNK     0      -0.051   5.437   6.503  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.731   3.991   7.276  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.974   4.000   6.692  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.815   3.022   3.001  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.529   3.616   4.775  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.770   2.165   4.067  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.388  -1.100   2.971  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.984  -0.481   1.424  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.100   1.013   1.167  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.169   0.184   3.943  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.739   1.647   3.686  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.171   2.248   2.143  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.967   0.760   1.758  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.298  -0.506   2.769  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.345   0.605  -0.662  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.033   0.064  -0.030  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.941   0.444  -1.373  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.950  -0.993  -1.437  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.522  -1.946   1.545  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.720  -2.809   0.029  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.329  -3.141   1.012  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.997  -2.586  -1.767  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.149  -1.071  -1.974  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.435  -2.846  -1.667  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.316  -3.398  -0.186  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.692  -2.096   0.357  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.791   0.737  -3.111  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.518   0.325  -3.053  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.833   1.365  -1.787  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.629  -2.933   1.933  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.891  -2.490   2.610  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.580  -1.756   3.230  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1                                                       
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6   13    3   33                                             
CONECT    6   10    5    7                                                  
CONECT    7    6    8   34                                                  
CONECT    8    7    9   35                                                  
CONECT    9    8   10                                                       
CONECT   10    6    9   11                                                  
CONECT   11   12   10   36   37                                             
CONECT   12   13   11   28   38                                             
CONECT   13   12    5   39   14                                             
CONECT   14   15   13   40   41                                             
CONECT   15   16   14   42   43                                             
CONECT   16   18   28   15   17                                             
CONECT   17   16   44                                                       
CONECT   18   16   21   19   20                                             
CONECT   19   18   45   46   47                                             
CONECT   20   18   48   49   50                                             
CONECT   21   18   22   51   52                                             
CONECT   22   21   23   53   54                                             
CONECT   23   28   22   24   55                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   56   57   58                                             
CONECT   27   25                                                            
CONECT   28   23   16   29   12                                             
CONECT   29   28   59   60   61                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    5                                                            
CONECT   34    7                                                            
CONECT   35    8                                                            
CONECT   36   11                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   17                                                            
CONECT   45   19                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   22                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   26                                                            
CONECT   57   26                                                            
CONECT   58   26                                                            
CONECT   59   29                                                            
CONECT   60   29                                                            
CONECT   61   29                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

RDKit          3D

61 64  0  0  0  0  0  0  0  0999 V2000
   -0.0472    4.3436    6.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4855    3.9059    5.2113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253    2.5474    5.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2189    1.7495    5.9480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0154    2.1775    3.6744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4919    1.9446    3.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5710    2.6912    4.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7173    2.0011    3.8827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4158    0.8848    3.1650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690    0.8708    3.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4031   -0.2258    2.3152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9621    0.2252    1.9218 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2325    0.9225    3.1327 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2038    1.3511    2.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285    0.2799    2.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3012   -0.2976    0.8234 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9992    0.8668    0.0112 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -1.2137   -0.0807 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3470   -0.3706   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9753   -2.3322    0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3952   -1.8409   -1.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0963   -2.5004   -0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050   -1.5429    0.0211 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2131   -0.4675   -0.8591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3181   -0.6977   -1.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6292    0.5159   -2.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9634   -1.7347   -1.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835   -0.9350    1.2723 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0786   -2.0773    2.3143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0514    5.4370    6.5032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7313    3.9910    7.2762 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    4.0003    6.6925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8146    3.0222    3.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5287    3.6159    4.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7700    2.1649    4.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3881   -1.0997    2.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9840   -0.4807    1.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0998    1.0133    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1687    0.1844    3.9434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7387    1.6470    3.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1706    2.2482    2.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9669    0.7599    1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -0.5061    2.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3445    0.6046   -0.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0327    0.0644   -0.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9409    0.4439   -1.3725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500   -0.9928   -1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5215   -1.9456    1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7199   -2.8090    0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3291   -3.1413    1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9971   -2.5856   -1.7673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -1.0715   -1.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4346   -2.8461   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3158   -3.3983   -0.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6916   -2.0956    0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7914    0.7373   -3.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5178    0.3245   -3.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8331    1.3645   -1.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292   -2.9326    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8908   -2.4895    2.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5797   -1.7557    3.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  6  2  0
 12 13  1  0
 18 16  1  0
 28 23  1  0
 28 16  1  0
  6  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 21 18  1  0
 18 19  1  6
 12 11  1  0
 13  5  1  0
 10 11  1  0
 22 21  1  0
 18 20  1  0
 22 23  1  0
 13 39  1  1
 28 29  1  1
  5  3  1  0
 28 12  1  0
 23 24  1  0
 16 15  1  0
 24 25  1  0
 15 14  1  0
 25 26  1  0
 25 27  2  0
 16 17  1  6
  3  2  1  0
 14 13  1  0
  3  4  2  0
 12 38  1  6
  2  1  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  1
 15 42  1  0
 15 43  1  0
 14 40  1  0
 14 41  1  0
 11 36  1  0
 11 37  1  0
 29 59  1  0
 29 60  1  0
 29 61  1  0
  5 33  1  6
 17 44  1  0
  7 34  1  0
  8 35  1  0
 21 51  1  0
 21 52  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 26 56  1  0
 26 57  1  0
 26 58  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
M  END

View in JSmol

Synonyms

Value	Source
Methyl (1S,2S,3S,7R,10R,11S)-3-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0,.0,]heptadeca-12(16),13-diene-11-carboxylic acid	Generator

Chemical Formula

C₂₃H₃₂O₆

Average Mass

404.5030 Da

Monoisotopic Mass

404.21989 Da

IUPAC Name

methyl (1S,2S,3S,7R,10R,11S)-3-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylate

Traditional Name

methyl (1S,2S,3S,7R,10R,11S)-3-(acetyloxy)-7-hydroxy-2,6,6-trimethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-diene-11-carboxylate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]12C([H])([H])C([H])([H])[C@@]3([H])[C@]([H])(C(=O)OC([H])([H])[H])C4=C(OC([H])=C4[H])C([H])([H])[C@]3([H])[C@@]1(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])C2(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C23H32O6/c1-13(24)29-18-7-9-21(2,3)23(26)10-6-14-16(22(18,23)4)12-17-15(8-11-28-17)19(14)20(25)27-5/h8,11,14,16,18-19,26H,6-7,9-10,12H2,1-5H3/t14-,16+,18+,19+,22+,23-/m1/s1

InChI Key

YKYVQVVITOKCCL-AOKVBNASSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Caesalpiniacrista	JEOL database	Kalauni, S. K., et al, J. Nat. Prod. 67, 1859 (2004)
Guilandina crista	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Naphthofuran
Benzofuran
Dicarboxylic acid or derivatives
Cyclic alcohol
Heteroaromatic compound
Furan
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.49	ALOGPS
logP	2.79	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.97	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.97 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.63 m³·mol⁻¹	ChemAxon
Polarizability	44.14 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

9548009

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11373092

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kalauni, S. K., et al. (2004). Kalauni, S. K., et al, J. Nat. Prod. 67, 1859 (2004). J. Nat. Prod..

Showing NP-Card for caesalpinin MB (NP0027560)

MOL for NP0027560 (caesalpinin MB)

3D MOL for NP0027560 (caesalpinin MB)

3D SDF for NP0027560 (caesalpinin MB)

3D-SDF for NP0027560 (caesalpinin MB)

PDB for NP0027560 (caesalpinin MB)

3D PDB for NP0027560 (caesalpinin MB)

SMILES for NP0027560 (caesalpinin MB)

INCHI for NP0027560 (caesalpinin MB)

Structure for NP0027560 (caesalpinin MB)

3D Structure for NP0027560 (caesalpinin MB)