NP-MRD: Showing NP-Card for (-)-Maoecrystal P (NP0080716)

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Record Information

Version

2.0

Created at

2022-04-29 01:42:57 UTC

Updated at

2022-04-29 01:42:57 UTC

NP-MRD ID

NP0080716

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Maoecrystal P

Description

Maoecrystal P belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. (-)-Maoecrystal P is found in Isodon eriocalyx and Rabdosia eriocalyx. (-)-Maoecrystal P was first documented in 2002 (PMID: 12502334). Based on a literature review a small amount of articles have been published on maoecrystal P (PMID: 22624550) (PMID: 29205726).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292203422D          

 25 29  0  0  1  0            999 V2000
   -0.1866    1.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1877    0.6624    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7925    0.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0869   -0.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8662    0.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4871   -0.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0502    1.0059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3537    1.5762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4694    1.4122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5720    1.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5479    2.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1325    2.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7863    1.2632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545    2.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4377    2.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123    2.2361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4704    1.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4841    1.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3002    1.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9097    0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1640    0.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8877   -0.9088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3060   -0.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1227   -0.6832    0.0000 C   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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  4  1  6  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  6  0  0  0
  9 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
  8 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  2  0  0  0  0
  5 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
M  END

     RDKit          3D

 47 51  0  0  0  0  0  0  0  0999 V2000
    5.0475   -0.1808   -0.4922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7924    0.2090   -0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7786   -0.1058   -1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8962   -0.6435   -2.5261 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4895    0.3691   -0.8216 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9224    1.5692   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1425    1.0080    0.6735 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5797    0.0828    1.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8927   -1.0893    1.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9523   -0.7690   -0.0030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4826   -0.6833    0.3585 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7470   -0.2053    1.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0933   -0.1616    2.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185   -0.5924    1.0234 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5936   -2.0450    0.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1540   -2.0268    0.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4973   -2.9764   -0.0505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7193    0.3055   -0.1815 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6689   -0.0331   -1.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9460    1.7309    0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2890    0.1799   -0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8438    0.8077   -1.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6556    1.5958   -2.3850 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5655    0.6860   -1.9410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9275    0.8468   -3.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3618   -0.7544   -1.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7698    0.0762    0.2843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3430    2.2873   -0.7999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1931    2.0234    0.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7771    1.7830    1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9992    0.6262    2.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4801   -0.3253    2.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4599   -1.7163    1.9126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7290   -1.7262    0.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -1.6530   -0.7220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3402    0.8050    1.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3220   -0.9367    2.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9521   -0.5734    1.3829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1537   -2.2772   -0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8337   -2.6907    1.4896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5324   -0.5684   -0.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1208    0.8922   -1.7258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2672   -0.7154   -2.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0928    2.3896   -0.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0594    1.7977    1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8507    2.1843   -0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9646    1.1934   -3.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  6
 18 20  1  0
 18 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 11 16  1  1
 11 12  1  0
 12 13  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  6
  3  4  2  0
  3  2  1  0
  2  1  2  3
  5 24  1  0
 24 25  2  0
 24 22  1  0
 22 23  1  0
 22 21  2  0
 21 18  1  0
 13 14  1  0
  5 10  1  0
 21 11  1  0
  2  7  1  0
 19 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 14 38  1  1
 15 39  1  0
 15 40  1  0
 12 36  1  0
 12 37  1  0
 10 35  1  6
  9 33  1  0
  9 34  1  0
  8 31  1  0
  8 32  1  0
  7 30  1  1
  6 28  1  0
  6 29  1  0
  1 26  1  0
  1 27  1  0
 23 47  1  0
M  END


  Mrv1652304292203422D          

 25 29  0  0  1  0            999 V2000
   -0.1866    1.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1877    0.6624    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7925    0.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5208    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0869   -0.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8662    0.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4871   -0.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0502    1.0059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3537    1.5762    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4694    1.4122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5720    1.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5479    2.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1325    2.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7863    1.2632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6545    2.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4377    2.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123    2.2361    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4704    1.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4841    1.4575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3002    1.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9097    0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1640    0.0413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8877   -0.9088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3060   -0.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1227   -0.6832    0.0000 C   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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10  4  1  6  0  0  0
 10 11  1  0  0  0  0
  1 11  1  0  0  0  0
 11 12  2  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  6  0  0  0
  9 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
  8 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  8 21  1  0  0  0  0
 21 22  2  0  0  0  0
  5 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0080716

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)[C@H]2CC(=O)[C@@]3(CO2)[C@@H]2CC[C@@H]4C[C@]2(C(=O)C4=C)C(=O)C(O)=C13

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O5/c1-9-10-4-5-11-19(7-10,16(9)23)17(24)14(22)15-18(2,3)13-6-12(21)20(11,15)8-25-13/h10-11,13,22H,1,4-8H2,2-3H3/t10-,11-,13-,19+,20-/m1/s1

> <INCHI_KEY>
PTXBJCCXMBZGPW-ZUIFNPILSA-N

> <FORMULA>
C20H22O5

> <MOLECULAR_WEIGHT>
342.391

> <EXACT_MASS>
342.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
34.86250797485926

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,8S,13R)-10-hydroxy-12,12-dimethyl-6-methylidene-14-oxapentacyclo[11.2.2.1^{5,8}.0^{1,11}.0^{2,8}]octadec-10-ene-7,9,16-trione

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
2.3677592376666663

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.30394510085261

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.433106091327913

> <JCHEM_PKA_STRONGEST_BASIC>
-4.039619395105306

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
90.198

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,8S,13R)-10-hydroxy-12,12-dimethyl-6-methylidene-14-oxapentacyclo[11.2.2.1^{5,8}.0^{1,11}.0^{2,8}]octadec-10-ene-7,9,16-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -0.348   2.650   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.350   1.237   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.479   0.136   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.839   0.976   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.896  -0.202   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.350   0.332   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.509  -0.682   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.694   1.878   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.394   2.942   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.743   2.636   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.068   3.384   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.023   4.923   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.114   3.965   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.468   2.358   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.955   4.478   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.417   5.172   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.676   4.174   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.478   3.210   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.370   2.721   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.894   2.496   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.298   1.542   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.773   0.077   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.524  -1.696   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.571  -1.108   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.096  -1.275   0.000  0.00  0.00           C+0
CONECT    1    2   11                                                       
CONECT    2    1    3   14                                                  
CONECT    3    2    4   24   25                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6   23                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   18   21                                             
CONECT    9    8   10   15                                                  
CONECT   10    9    4   11   13                                             
CONECT   11   10    1   12                                                  
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13    2                                                       
CONECT   15    9   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17    8                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    8   22                                                  
CONECT   22   21                                                            
CONECT   23    5                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₅

Average Mass

342.3910 Da

Monoisotopic Mass

342.14672 Da

IUPAC Name

(1S,2S,5R,8S,13R)-10-hydroxy-12,12-dimethyl-6-methylidene-14-oxapentacyclo[11.2.2.1^{5,8}.0^{1,11}.0^{2,8}]octadec-10-ene-7,9,16-trione

Traditional Name

(1S,2S,5R,8S,13R)-10-hydroxy-12,12-dimethyl-6-methylidene-14-oxapentacyclo[11.2.2.1^{5,8}.0^{1,11}.0^{2,8}]octadec-10-ene-7,9,16-trione

CAS Registry Number

Not Available

SMILES

CC1(C)[C@H]2CC(=O)[C@@]3(CO2)[C@@H]2CC[C@@H]4C[C@]2(C(=O)C4=C)C(=O)C(O)=C13

InChI Identifier

InChI=1S/C20H22O5/c1-9-10-4-5-11-19(7-10,16(9)23)17(24)14(22)15-18(2,3)13-6-12(21)20(11,15)8-25-13/h10-11,13,22H,1,4-8H2,2-3H3/t10-,11-,13-,19+,20-/m1/s1

InChI Key

PTXBJCCXMBZGPW-ZUIFNPILSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Isodon eriocalyx	Plant	KNApSAcK
Rabdosia eriocalyx	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Substituents

Kaurane diterpenoid
Naphthopyran
Naphthalene
Cyclohexenone
Oxane
Pyran
Ketone
Dialkyl ether
Enol
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	1.97	ALOGPS
logP	2.37	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	90.2 m³·mol⁻¹	ChemAxon
Polarizability	34.86 Å³	ChemAxon
Number of Rings	5	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

C00046125

Chemspider ID

16738128

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20056132

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang WG, Li XN, Du X, Wu HY, Liu X, Su J, Li Y, Pu JX, Sun HD: Laxiflorolides A and B, epimeric bishomoditerpene lactones from Isodon eriocalyx. J Nat Prod. 2012 Jun 22;75(6):1102-7. doi: 10.1021/np300106j. Epub 2012 May 24. [PubMed:22624550 ]
Niu XM, Li SH, Mei SX, Na Z, Zhao QS, Lin ZW, Sun HD: Cytotoxic 3,20-epoxy-ent-kaurane diterpenoids from Isodon eriocalyx var. laxiflora. J Nat Prod. 2002 Dec;65(12):1892-6. doi: 10.1021/np020059e. [PubMed:12502334 ]
Su F, Lu Y, Kong L, Liu J, Luo T: Total Synthesis of Maoecrystal P: Application of a Strained Bicyclic Synthon. Angew Chem Int Ed Engl. 2018 Jan 15;57(3):760-764. doi: 10.1002/anie.201711084. Epub 2017 Dec 19. [PubMed:29205726 ]

Showing NP-Card for (-)-Maoecrystal P (NP0080716)

MOL for NP0080716 ((-)-Maoecrystal P)

3D MOL for NP0080716 ((-)-Maoecrystal P)

3D SDF for NP0080716 ((-)-Maoecrystal P)

3D-SDF for NP0080716 ((-)-Maoecrystal P)

PDB for NP0080716 ((-)-Maoecrystal P)

3D PDB for NP0080716 ((-)-Maoecrystal P)

SMILES for NP0080716 ((-)-Maoecrystal P)

INCHI for NP0080716 ((-)-Maoecrystal P)

Structure for NP0080716 ((-)-Maoecrystal P)

3D Structure for NP0080716 ((-)-Maoecrystal P)