NP-MRD: Showing NP-Card for (1r,2s,3s)-3-[(1r,2s,5r)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid (NP0290912)

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Record Information

Version

2.0

Created at

2022-09-09 21:48:12 UTC

Updated at

2022-09-09 21:48:12 UTC

NP-MRD ID

NP0290912

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s)-3-[(1r,2s,5r)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid

Description

(1R,2S,3S)-3-[(1R,2S,5R)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]Octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid 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. Based on a literature review very few articles have been published on (1R,2S,3S)-3-[(1R,2S,5R)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]Octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092223482D          

 26 28  0  0  1  0            999 V2000
   -0.5840    0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    0.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044   -0.8453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6208   -1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676   -1.8928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044    1.0085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6087    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1231    1.4699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087   -0.6617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1231   -1.3067    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3985   -1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6689   -0.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776   -0.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7403   -1.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1944   -2.2522    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8930   -3.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8984   -2.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8778   -3.5071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6229   -2.2878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858   -2.0887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399   -2.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313   -2.5438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1027   -3.4893    0.0000 O   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  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  4  7  1  0  0  0  0
  8  7  1  1  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  1  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    5.2090    1.0946    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9927    0.6400    0.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0849    0.1826   -0.8310 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6418    0.5343   -0.3531 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2308    1.5341   -1.3303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3056    2.7352   -1.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9358    1.2319    0.9916 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1725    0.4499    1.4443 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7632   -0.9568    1.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5560   -1.8296    1.6925 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3401   -1.2749    1.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9017   -0.6938   -0.1483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5112   -0.9520   -0.4133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5417   -2.5313   -0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9302   -0.7609   -1.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8973    0.3132   -2.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4712    1.1303   -1.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    0.7296    0.3342 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5876    1.8056    1.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6252    0.6850    0.9918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360   -0.2784    1.6971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4942    1.7279    0.8051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6014   -0.5929    0.5171 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7345   -1.5859    0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6540   -1.3243   -0.5695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8525   -2.7850    0.9224 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6976    1.1809   -0.8681 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343    1.4197    0.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3095    0.5474   -1.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1883   -0.9431   -0.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8570    1.3732   -2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1281    1.1330    1.7090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391    2.2782    0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6070    0.8356    2.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750   -0.8492    2.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2442   -2.3905    1.1805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4373   -1.4480   -0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6033   -2.8375    0.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4060   -2.9002   -0.8960 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3560   -2.9405   -0.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0016   -0.7618   -2.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4317   -1.7022   -2.2731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3886    1.0055   -2.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7596   -0.0486   -2.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0538    2.1857   -1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5663    1.3270   -1.2975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7313    2.2456    0.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2224    1.2626    2.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3007    2.5603    1.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0572    1.8833   -0.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3618   -0.6948    1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7922   -2.9497    1.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 23  1  0
 23 24  1  0
 24 26  1  0
 24 25  2  0
 18 20  1  1
 20 22  1  0
 20 21  2  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  1  0
  7  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  4  5  1  6
  5  6  2  0
 23 13  1  0
  4 12  1  0
  2  8  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 23 51  1  1
 26 52  1  0
 22 50  1  0
 12 37  1  6
 11 35  1  0
 11 36  1  0
  8 34  1  1
  7 32  1  0
  7 33  1  0
  3 29  1  0
  3 30  1  0
  1 27  1  0
  1 28  1  0
  5 31  1  0
M  END


  Mrv1652309092223482D          

 26 28  0  0  1  0            999 V2000
   -0.5840    0.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    0.4941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593   -0.3309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044   -0.8453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6208   -1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676   -1.8928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044    1.0085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6087    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1231    1.4699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666    0.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6087   -0.6617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1231   -1.3067    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3985   -1.7013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6689   -0.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4776   -0.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7403   -1.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1944   -2.2522    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8930   -3.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8984   -2.6824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8778   -3.5071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6229   -2.2878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858   -2.0887    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399   -2.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313   -2.5438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1027   -3.4893    0.0000 O   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  1  0  0  0  0
  4  5  1  1  0  0  0
  5  6  2  0  0  0  0
  4  7  1  0  0  0  0
  8  7  1  1  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  1  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 18 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0290912

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(CCC[C@](C)([C@H]1C(O)=O)C(O)=O)[C@@H]1CC(=O)[C@@H]2C[C@]1(CC2=C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O6/c1-11-8-20(10-21)9-12(11)13(22)7-14(20)18(2)5-4-6-19(3,17(25)26)15(18)16(23)24/h10,12,14-15H,1,4-9H2,2-3H3,(H,23,24)(H,25,26)/t12-,14+,15+,18+,19-,20-/m1/s1

> <INCHI_KEY>
LUMBHDRAYRAUHM-JBNFOXMESA-N

> <FORMULA>
C20H26O6

> <MOLECULAR_WEIGHT>
362.422

> <EXACT_MASS>
362.172938557

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.0946541780916

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3S)-3-[(1R,2S,5R)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid

> <JCHEM_LOGP>
2.317107887333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.69463278842536

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.625716989505117

> <JCHEM_PKA_STRONGEST_BASIC>
-6.962790449652971

> <JCHEM_POLAR_SURFACE_AREA>
108.74

> <JCHEM_REFRACTIVITY>
92.31619999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S)-3-[(1R,2S,5R)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.090   1.591   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.297   0.922   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.297  -0.618   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.501  -1.578   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.159  -3.079   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.313  -3.533   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.934   0.152   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.501   1.883   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.003   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.963   2.744   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.671   0.152   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.003  -1.235   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.963  -2.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.611  -3.176   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.982  -1.284   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.491  -1.590   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.982  -3.049   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.963  -4.204   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.400  -5.638   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.277  -5.007   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.239  -6.547   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.629  -4.271   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.453  -3.899   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.435  -5.054   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.925  -4.748   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.925  -6.513   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   12                                             
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    2    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    4   13                                                  
CONECT   13   12   14   15   23                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   23                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   13   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,3S)-3-[(1R,2S,5R)-1-Formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylate	Generator

Chemical Formula

C₂₀H₂₆O₆

Average Mass

362.4220 Da

Monoisotopic Mass

362.17294 Da

IUPAC Name

(1R,2S,3S)-3-[(1R,2S,5R)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid

Traditional Name

(1R,2S,3S)-3-[(1R,2S,5R)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@]1(CCC[C@](C)([C@H]1C(O)=O)C(O)=O)[C@@H]1CC(=O)[C@@H]2C[C@]1(CC2=C)C=O

InChI Identifier

InChI=1S/C20H26O6/c1-11-8-20(10-21)9-12(11)13(22)7-14(20)18(2)5-4-6-19(3,17(25)26)15(18)16(23)24/h10,12,14-15H,1,4-9H2,2-3H3,(H,23,24)(H,25,26)/t12-,14+,15+,18+,19-,20-/m1/s1

InChI Key

LUMBHDRAYRAUHM-JBNFOXMESA-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

Not Available

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
Dicarboxylic acid or derivatives
Ketone
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.32	ChemAxon
pKa (Strongest Acidic)	4.63	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.74 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.32 m³·mol⁻¹	ChemAxon
Polarizability	37.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163040058

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3s)-3-[(1r,2s,5r)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid (NP0290912)

MOL for NP0290912 ((1r,2s,3s)-3-[(1r,2s,5r)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid)

3D MOL for NP0290912 ((1r,2s,3s)-3-[(1r,2s,5r)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid)

3D SDF for NP0290912 ((1r,2s,3s)-3-[(1r,2s,5r)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid)

3D-SDF for NP0290912 ((1r,2s,3s)-3-[(1r,2s,5r)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid)

PDB for NP0290912 ((1r,2s,3s)-3-[(1r,2s,5r)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid)

3D PDB for NP0290912 ((1r,2s,3s)-3-[(1r,2s,5r)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid)

SMILES for NP0290912 ((1r,2s,3s)-3-[(1r,2s,5r)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid)

INCHI for NP0290912 ((1r,2s,3s)-3-[(1r,2s,5r)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid)

Structure for NP0290912 ((1r,2s,3s)-3-[(1r,2s,5r)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid)

3D Structure for NP0290912 ((1r,2s,3s)-3-[(1r,2s,5r)-1-formyl-6-methylidene-4-oxobicyclo[3.2.1]octan-2-yl]-1,3-dimethylcyclohexane-1,2-dicarboxylic acid)