NP-MRD: Showing NP-Card for (1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol (NP0211755)

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Record Information

Version

2.0

Created at

2022-09-05 10:10:22 UTC

Updated at

2022-09-05 10:10:22 UTC

NP-MRD ID

NP0211755

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol

Description

Enmenol 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. (1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol is found in Isodon rubescens. (1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol was first documented in 2012 (PMID: 23302530). Based on a literature review a small amount of articles have been published on Enmenol (PMID: 30989952) (PMID: 29320879) (PMID: 31607167) (PMID: 28861970).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052212102D          

 26 30  0  0  1  0            999 V2000
   -0.9961   -0.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2167    0.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437    0.8570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5375    1.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3754    1.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7588    0.6239    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6825    0.4487    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0318    0.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2309   -0.6714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5720   -1.0232    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0353   -1.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4824   -1.2333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8068   -1.9918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9502   -0.4456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7290   -0.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4073   -1.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3252   -1.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2705   -0.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1071    0.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352    1.0012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2108    1.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2313   -0.1724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4341   -0.5342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3214   -1.3515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6708    0.4530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1878    1.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 12  1  1  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  1  0  0  0
 10 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  6  0  0  0
  2 23  1  0  0  0  0
 23 24  1  6  0  0  0
 22 25  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END

     RDKit          2D

 56 60  0  0  0  0  0  0  0  0999 V2000
    2.0421    5.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8853    3.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000    2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3828   -0.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2954    0.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    2.5981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6491   -0.9642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6491   -1.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6491   -3.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -3.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -3.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000   -2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491   -3.5623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500    1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5862    2.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0239    4.2221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5000    2.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    4.0753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4124    5.7037    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8286    5.9752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9028    3.7960    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8991    0.3349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8991    2.2632    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2863   -1.4724    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4095   -0.5130    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0861   -1.3808    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491    0.9642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7580   -0.8169    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0000    2.5981    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6491    0.9642    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9856   -0.2832    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2500   -1.2990    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9071   -0.8170    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7461   -2.6569    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9916   -0.2857    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7981   -4.5264    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8321   -4.8203    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7461   -2.5393    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0865   -4.5781    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4895   -5.3743    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4895   -5.3743    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0865   -4.5781    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9183   -2.1098    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5706   -5.0602    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9101    2.7472    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5156    4.3789    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2565    3.4369    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0970    4.7563    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  7  1  0
  7  8  1  1
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 12 14  1  0
 22 10  1  1
 22 25  1  0
 25 26  1  0
 25  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  3  2  1  0
  2  1  2  3
  2 23  1  0
 23 24  1  0
 14 15  1  0
  6 22  1  0
 14  7  1  0
 23 22  1  0
  6  7  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 20 51  1  6
 21 52  1  0
  8 35  1  0
  8 36  1  0
 11 37  1  0
 12 38  1  1
 13 39  1  0
 14 40  1  6
 25 55  1  1
 26 56  1  0
  3 29  1  1
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  6
  1 27  1  0
  1 28  1  0
 23 53  1  1
 24 54  1  0
M  END


  Mrv1652309052212102D          

 26 30  0  0  1  0            999 V2000
   -0.9961   -0.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2167    0.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0437    0.8570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5375    1.4840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3754    1.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7588    0.6239    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6825    0.4487    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0318    0.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2309   -0.6714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5720   -1.0232    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0353   -1.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4824   -1.2333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8068   -1.9918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9502   -0.4456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7290   -0.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4073   -1.2606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3252   -1.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2705   -0.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1071    0.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3352    1.0012    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2108    1.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2313   -0.1724    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4341   -0.5342    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3214   -1.3515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6708    0.4530    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1878    1.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 14 12  1  1  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  1  0  0  0
 10 22  1  0  0  0  0
  6 22  1  0  0  0  0
 22 23  1  6  0  0  0
  2 23  1  0  0  0  0
 23 24  1  6  0  0  0
 22 25  1  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0211755

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC[C@H](O)[C@]23CO[C@@](O)([C@@H](O)[C@H]12)[C@@]12[C@H](O)[C@@H](CC[C@@H]31)C(=C)[C@H]2O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O6/c1-9-10-4-5-11-18-8-26-20(25,19(11,14(9)22)15(10)23)16(24)13(18)17(2,3)7-6-12(18)21/h10-16,21-25H,1,4-8H2,2-3H3/t10-,11-,12-,13+,14+,15+,16-,18+,19-,20-/m0/s1

> <INCHI_KEY>
XWWQJYXCACMZIO-YSMIGFKBSA-N

> <FORMULA>
C20H30O6

> <MOLECULAR_WEIGHT>
366.454

> <EXACT_MASS>
366.204238686

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
88.65787455652924

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5S,7R,8R,9R,10S,11R,15S,18R)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecane-7,9,10,15,18-pentol

> <JCHEM_LOGP>
-0.37894641566666626

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.468413203576752

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.613790809511295

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9702649229524782

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
92.49380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5S,7R,8R,9R,10S,11R,15S,18R)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1^{5,8}.0^{1,11}.0^{2,8}]octadecane-7,9,10,15,18-pentol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.859  -0.479   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.405   0.026   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.082   1.600   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.003   2.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.567   2.607   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.283   1.165   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.007   0.837   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.793   0.081   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.164  -1.253   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.934  -1.910   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.933  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.634  -2.302   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.239  -3.718   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.507  -0.832   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.961  -1.477   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.227  -2.353   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.207  -2.819   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.972  -0.275   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.667   1.260   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.226   1.869   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.993   3.391   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.298  -0.322   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.810  -0.997   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.600  -2.523   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.252   0.846   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.217   2.046   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8   14   20                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   22                                             
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15                                                  
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    7   21                                                  
CONECT   21   20                                                            
CONECT   22   10    6   23   25                                             
CONECT   23   22    2   24                                                  
CONECT   24   23                                                            
CONECT   25   22    3   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₆

Average Mass

366.4540 Da

Monoisotopic Mass

366.20424 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)CC[C@H](O)[C@]23CO[C@@](O)([C@@H](O)[C@H]12)[C@@]12[C@H](O)[C@@H](CC[C@@H]31)C(=C)[C@H]2O

InChI Identifier

InChI=1S/C20H30O6/c1-9-10-4-5-11-18-8-26-20(25,19(11,14(9)22)15(10)23)16(24)13(18)17(2,3)7-6-12(18)21/h10-16,21-25H,1,4-8H2,2-3H3/t10-,11-,12-,13+,14+,15+,16-,18+,19-,20-/m0/s1

InChI Key

XWWQJYXCACMZIO-YSMIGFKBSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 rubescens	LOTUS Database	35616633

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
Oxane
Cyclic alcohol
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00031761

Chemspider ID

24660167

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46883404

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang LX, Liu YL, Wu H, Chen SQ, Dai LP: [Studies on chemical constituents of Isodon henryi]. Zhongguo Zhong Yao Za Zhi. 2019 Jan;44(2):319-323. doi: 10.19540/j.cnki.cjcmm.20181101.009. [PubMed:30989952 ]
Dai LP, Zhang LX, Liu YL, Wu H, Liu RX, Zhao M, Tian SS, Jiang X, Chen SQ: Isolation and purification of diterpenoids from the aerial parts of Isodon excisoides target-guided by UPLC-LTQ-Orbitrap-MS. Nat Prod Res. 2018 Oct;32(20):2424-2430. doi: 10.1080/14786419.2017.1419225. Epub 2018 Jan 10. [PubMed:29320879 ]
Wu YX, Zhang W, Li JC, Liu N: Chemical constituents of flowers and fruits of Rabdosia excisa. Chin J Nat Med. 2012 Jan;10(1):43-7. doi: 10.1016/S1875-5364(12)60010-7. [PubMed:23302530 ]
Jiang X, Zhang LX, Feng QM, Wu H, Liu YL, Wang DQ, Dai LP, Wang ZM: A new ent-kaurane diterpene from Isodon henryi. Nat Prod Res. 2021 Jul;35(14):2346-2352. doi: 10.1080/14786419.2019.1675067. Epub 2019 Oct 12. [PubMed:31607167 ]
Tian TT, Ma YH, Xie WW, Jin YR, Xu HJ, Zhang LT, Du YF: [Simultaneous determination of 4 diterpenoids in Rabdosia japonica var.glaucocalyx by HPLC-ESI-MS/MS and cluster analysis]. Zhongguo Zhong Yao Za Zhi. 2016 Jan;41(2):250-256. doi: 10.4268/cjcmm20160215. [PubMed:28861970 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol (NP0211755)

MOL for NP0211755 ((1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol)

3D MOL for NP0211755 ((1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol)

3D SDF for NP0211755 ((1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol)

3D-SDF for NP0211755 ((1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol)

PDB for NP0211755 ((1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol)

3D PDB for NP0211755 ((1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol)

SMILES for NP0211755 ((1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol)

INCHI for NP0211755 ((1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol)

Structure for NP0211755 ((1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol)

3D Structure for NP0211755 ((1s,2s,5s,7r,8r,9r,10s,11r,15s,18r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-7,9,10,15,18-pentol)