NP-MRD: Showing NP-Card for (1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one (NP0237204)

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Record Information

Version

2.0

Created at

2022-09-06 20:16:46 UTC

Updated at

2022-09-06 20:16:46 UTC

NP-MRD ID

NP0237204

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Longikaurin A 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. (1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one is found in Isodon adenolomus, Isodon longitubus, Isodon phyllostachys and Isodon trichocarpus. (1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one was first documented in 2012 (PMID: 22739166). Based on a literature review a small amount of articles have been published on Longikaurin A (PMID: 28454308) (PMID: 24651440) (PMID: 28801140) (PMID: 23985029).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062222162D          

 25 29  0  0  1  0            999 V2000
    7.8690    0.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0976    0.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4364    0.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5383   -0.6783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6431    0.5023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1349    1.3161    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5023    2.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3525    2.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9517    1.5171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2374    1.1121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7335    1.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2098    1.1472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5253    1.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611    1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183    0.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1762   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5153   -0.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6135   -0.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9373    0.2496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4058   -0.5525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0749   -1.3082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082   -0.3537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8443   -0.9808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633   -0.0011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8469    0.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9  2  1  1  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
  6 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 19 16  1  6  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -4.3587    0.6683   -1.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717    0.0946   -0.9625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2135   -0.5536   -1.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9729   -0.8703   -2.5569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445   -0.6803   -0.1226 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8633    0.6492    0.2326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6416    1.4563    1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1022    1.2255    1.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5749   -0.0078    0.5233 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5484   -1.1091    0.8232 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0266   -2.3386    0.3457 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5814    0.3920    0.6912 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0870    1.6725    1.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5696    1.8387    1.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1791    1.4546   -0.0798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7898    0.0488   -0.4726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3353   -0.1526   -1.8950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4878   -0.9052    0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180   -0.0618   -0.5531 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8139   -1.4142   -0.9610 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5780   -1.4714   -2.3383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3975   -1.7319   -0.1395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8871   -2.9634   -0.5347 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0531   -1.8773    1.1904 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5218   -0.7034    1.7218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2478    1.1146   -1.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2206    0.7066   -2.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7414    1.2315   -0.7282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2486    1.3641    2.2421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4770    2.5487    0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6776    2.0891    0.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4938    1.1688    2.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5683   -0.2949    0.8665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2591   -1.1393    1.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8953   -2.5837    0.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7536    1.7594    2.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6311    2.5587    0.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7749    2.9407    1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0690    1.3597    2.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9744    2.2042   -0.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2941    1.4360    0.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0885   -1.2103   -2.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8783    0.5438   -2.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4363   -0.0588   -1.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4958   -1.1632   -0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9994   -1.8502    0.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7564   -0.4228    1.3977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803    0.6502   -1.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5561   -2.2343   -0.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7678   -0.6043   -2.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8511   -3.6530    0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1216   -0.3051    2.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5342   -0.8158    2.2113 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 18  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 12 13  1  1
 12 25  1  0
 25 24  1  0
 24 22  1  0
 22 23  1  6
 22 20  1  0
 20 21  1  0
 20 19  1  0
 22  5  1  0
  5 10  1  0
 10 11  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  9  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
 19 16  1  0
  6  5  1  0
 19 12  1  0
  5  3  1  6
  6 12  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 15 40  1  0
 15 41  1  0
 14 38  1  0
 14 39  1  0
 13 36  1  0
 13 37  1  0
 25 52  1  0
 25 53  1  0
 23 51  1  0
 20 49  1  6
 21 50  1  0
 19 48  1  6
 10 34  1  1
 11 35  1  0
  9 33  1  6
  8 31  1  0
  8 32  1  0
  7 29  1  0
  7 30  1  0
  6 28  1  6
  1 26  1  0
  1 27  1  0
M  END


  Mrv1652309062222162D          

 25 29  0  0  1  0            999 V2000
    7.8690    0.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0976    0.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4364    0.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5383   -0.6783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6431    0.5023    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1349    1.3161    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5023    2.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3525    2.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9517    1.5171    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2374    1.1121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7335    1.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2098    1.1472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5253    1.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611    1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183    0.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1762   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5153   -0.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6135   -0.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9373    0.2496    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4058   -0.5525    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0749   -1.3082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3082   -0.3537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8443   -0.9808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633   -0.0011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8469    0.7367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9  2  1  1  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  6  0  0  0
  6 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 19 16  1  6  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 12 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237204

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC[C@]23CO[C@](O)([C@@H](O)[C@H]12)[C@@]12[C@H](O)[C@@H](CC[C@@H]31)C(=C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O5/c1-10-11-5-6-12-18-8-4-7-17(2,3)13(18)16(23)20(24,25-9-18)19(12,14(10)21)15(11)22/h11-13,15-16,22-24H,1,4-9H2,2-3H3/t11-,12-,13+,15+,16-,18+,19-,20+/m0/s1

> <INCHI_KEY>
PSVHVXLCVSKJGM-MHRDNBEJSA-N

> <FORMULA>
C20H28O5

> <MOLECULAR_WEIGHT>
348.439

> <EXACT_MASS>
348.193674002

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
36.93623302125356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.7714192610000006

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.633682329849716

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.513660395182495

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2195628270560386

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
90.36179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      14.689   0.706   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.249   1.252   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.015   0.262   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.205  -1.266   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.534   0.938   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.585   2.457   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.271   3.906   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.858   3.982   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.977   2.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.643   2.076   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.703   3.295   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.858   2.141   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.581   3.117   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.154   2.462   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.888   0.911   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.929  -0.266   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.695  -1.187   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.745  -1.572   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.350   0.466   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.224  -1.031   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.607  -2.442   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.909  -0.660   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.909  -1.831   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.705  -0.002   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.047   1.375   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10   22                                             
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    2   10                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10                                                            
CONECT   12    6   13   19   25                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   12   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    5   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   12                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₅

Average Mass

348.4390 Da

Monoisotopic Mass

348.19367 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]23CO[C@](O)([C@@H](O)[C@H]12)[C@@]12[C@H](O)[C@@H](CC[C@@H]31)C(=C)C2=O

InChI Identifier

InChI=1S/C20H28O5/c1-10-11-5-6-12-18-8-4-7-17(2,3)13(18)16(23)20(24,25-9-18)19(12,14(10)21)15(11)22/h11-13,15-16,22-24H,1,4-9H2,2-3H3/t11-,12-,13+,15+,16-,18+,19-,20+/m0/s1

InChI Key

PSVHVXLCVSKJGM-MHRDNBEJSA-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 adenolomus	LOTUS Database	35616633
Isodon longitubus	LOTUS Database	35616633
Isodon phyllostachys	LOTUS Database	35616633
Isodon trichocarpus	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
Hemiacetal
Ketone
Secondary alcohol
Oxacycle
Polyol
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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

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

58924179

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102117144

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yuan Y, Du Y, Hu XY, Liu MY, Du JK, Liu XM, Yu HE, Wang TZ, Pu JX, Zhong Q, Zou QF: Longikaurin A, a natural ent-kaurane, suppresses stemness in nasopharyngeal carcinoma cells. Oncol Lett. 2017 Mar;13(3):1672-1680. doi: 10.3892/ol.2017.5625. Epub 2017 Jan 19. [PubMed:28454308 ]
Liao YJ, Bai HY, Li ZH, Zou J, Chen JW, Zheng F, Zhang JX, Mai SJ, Zeng MS, Sun HD, Pu JX, Xie D: Longikaurin A, a natural ent-kaurane, induces G2/M phase arrest via downregulation of Skp2 and apoptosis induction through ROS/JNK/c-Jun pathway in hepatocellular carcinoma cells. Cell Death Dis. 2014 Mar 20;5(3):e1137. doi: 10.1038/cddis.2014.66. [PubMed:24651440 ]
Che Y, Wang J, Yuan Z, Li Y, Lu Z, Zhang Z, Zhang J, Wan J, Sun H, Chen Z, Pu J, He J: The therapeutic effects of Longikaurin A, a natural ent-kauranoid, in esophageal squamous cell carcinoma depend on ROS accumulation and JNK/p38 MAPK activation. Toxicol Lett. 2017 Oct 5;280:106-115. doi: 10.1016/j.toxlet.2017.08.005. Epub 2017 Aug 8. [PubMed:28801140 ]
Zou QF, Du JK, Zhang H, Wang HB, Hu ZD, Chen SP, Du Y, Li MZ, Xie D, Zou J, Sun HD, Pu JX, Zeng MS: Anti-tumour activity of longikaurin A (LK-A), a novel natural diterpenoid, in nasopharyngeal carcinoma. J Transl Med. 2013 Aug 28;11:200. doi: 10.1186/1479-5876-11-200. [PubMed:23985029 ]
Zhao S, Pu JX, Sun HD, Wu YL: [Longikaurin A induces apoptosis of multiple myeloma H929 cells]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2012 Jun;20(3):611-5. [PubMed:22739166 ]
LOTUS database [Link]

Showing NP-Card for (1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one (NP0237204)

MOL for NP0237204 ((1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D MOL for NP0237204 ((1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D SDF for NP0237204 ((1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D-SDF for NP0237204 ((1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

PDB for NP0237204 ((1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D PDB for NP0237204 ((1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

SMILES for NP0237204 ((1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

INCHI for NP0237204 ((1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

Structure for NP0237204 ((1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)

3D Structure for NP0237204 ((1r,2s,5s,8r,9s,10s,11r,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one)