NP-MRD: Showing NP-Card for (1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one (NP0275268)

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Record Information

Version

2.0

Created at

2022-09-08 22:57:32 UTC

Updated at

2022-09-08 22:57:32 UTC

NP-MRD ID

NP0275268

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one

Description

Brassicicene C belongs to the class of organic compounds known as fusicoccane diterpenoids. These are diterpenoids with a structure based on a 20-carbon dicyclopenta[a,d]cyclooctane skeleton (5->8->5 ring system) known as fusicoccane. (1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one was first documented in 2009 (PMID: 19700326). Based on a literature review a small amount of articles have been published on brassicicene C (PMID: 21299202) (PMID: 19097780).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092200572D          

 25 27  0  0  1  0            999 V2000
    5.6524    0.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1502    0.7297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3322    0.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300    1.2765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2316    0.7086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334    1.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3408    2.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184    2.5745    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2027    1.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405    1.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783    1.8123    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3625    2.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401    2.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043    3.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8069    2.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797    3.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475    1.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4147    1.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509    1.2765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1157    0.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783    3.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405    3.6524    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4405    4.4774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    3.3367    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7860    3.9201    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
  4  3  1  6  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  6  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
    3.9909    1.8797   -1.8338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3459    1.0774   -0.8756 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6307   -0.2460   -1.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9814   -1.2034   -0.2295 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2399   -2.5186   -0.5236 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5517   -0.8396    1.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518   -1.0916    2.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2196   -1.4475    1.3204 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5412   -0.9065   -0.0117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8012   -0.2775   -0.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5178    0.1946   -1.1226 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4771    0.5180   -0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6992    0.4071   -0.5739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0765    0.6395   -0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3574    1.1932    1.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7009    1.6889   -1.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5688   -0.1264   -1.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3368   -0.0053   -2.9449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2682   -0.8352   -1.9568 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6416   -0.9900   -3.2994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4387    0.9999    1.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963    0.6032    1.9484 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9657    1.1741    1.2907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181   -0.8770    1.9250 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1015   -1.3961    3.3621 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0795    1.6338   -1.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6614    1.6502   -2.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7879    2.9327   -1.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3657   -0.4048   -2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7411   -0.3998   -1.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6911   -2.6168   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8452    0.2197    1.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4520   -1.4536    1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7749   -1.9547    2.7788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2469   -0.1889    2.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1318   -2.5533    1.3488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4169   -0.0211   -1.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5516    1.1149   -1.8237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6991   -0.2802   -0.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8312    2.1057    1.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4648    1.5894    1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4440    0.4083    2.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9038    2.4196   -1.3279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0857    1.1857   -1.9787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5053    2.2468   -0.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3786   -1.7911   -1.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3658   -1.0599   -4.1363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0192   -1.8862   -3.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0288   -0.1251   -3.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5955    2.0725    1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2121    0.4798    1.9362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1076    1.0062    3.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7439    2.0428    0.8508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8926   -1.3575    1.3994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651   -1.0619    3.9642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0509   -1.0599    3.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0838   -2.5084    3.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8 24  1  0
 24 25  1  0
 24 22  1  0
 22 23  1  0
 22 21  1  0
 21 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 11  1  0
 11 10  1  0
 10  9  2  0
  9  4  1  0
  9  8  1  0
 11 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  6
 24 54  1  6
 25 55  1  0
 25 56  1  0
 25 57  1  0
 22 52  1  1
 23 53  1  0
 21 50  1  0
 21 51  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 16 45  1  0
 19 46  1  1
 20 47  1  0
 20 48  1  0
 20 49  1  0
 11 38  1  6
 10 37  1  0
M  END


  Mrv1652309092200572D          

 25 27  0  0  1  0            999 V2000
    5.6524    0.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1502    0.7297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3322    0.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8300    1.2765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2316    0.7086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5334    1.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3408    2.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5184    2.5745    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2027    1.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405    1.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783    1.8123    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3625    2.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401    2.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0043    3.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8069    2.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797    3.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475    1.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4147    1.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0509    1.2765    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1157    0.4540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6783    3.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4405    3.6524    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4405    4.4774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2027    3.3367    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7860    3.9201    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
  4  3  1  6  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  6  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0275268

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC[C@@]1(O)CC[C@H]2[C@@H](C)[C@@H](O)CC3=C(C(C)C)C(=O)[C@@H](C)[C@@H]3\C=C1/2

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O4/c1-11(2)19-16-9-18(22)12(3)14-6-7-21(24,10-25-5)17(14)8-15(16)13(4)20(19)23/h8,11-15,18,22,24H,6-7,9-10H2,1-5H3/b17-8+/t12-,13+,14+,15+,18+,21+/m1/s1

> <INCHI_KEY>
JYZGDIADQSQUAG-DKLZGWCZSA-N

> <FORMULA>
C21H32O4

> <MOLECULAR_WEIGHT>
348.483

> <EXACT_MASS>
348.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
40.04774687038528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4S,9S,10R,11S,14R)-9,14-dihydroxy-14-(methoxymethyl)-4,10-dimethyl-6-(propan-2-yl)tricyclo[9.3.0.0^{3,7}]tetradeca-1,6-dien-5-one

> <JCHEM_LOGP>
2.3300406550000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.783869562938474

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.443908621862139

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7061603394838557

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
99.58899999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,9S,10R,11S,14R)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0^{3,7}]tetradeca-1,6-dien-5-one

> <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      10.551   0.140   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.614   1.362   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.087   1.161   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.149   2.383   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.032   1.323   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.462   3.187   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.103   4.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.568   4.806   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.978   3.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.556   2.794   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.133   3.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.543   4.806   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.008   4.685   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.008   5.856   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.506   5.575   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.522   7.308   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.649   3.187   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.774   2.598   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.962   2.383   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.083   0.848   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.133   6.228   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.556   6.818   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.556   8.358   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.978   6.228   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.067   7.317   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6    9                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11   20                                                  
CONECT   20   19                                                            
CONECT   21   12   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    8   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₄

Average Mass

348.4830 Da

Monoisotopic Mass

348.23006 Da

IUPAC Name

(3S,4S,9S,10R,11S,14R)-9,14-dihydroxy-14-(methoxymethyl)-4,10-dimethyl-6-(propan-2-yl)tricyclo[9.3.0.0^{3,7}]tetradeca-1,6-dien-5-one

Traditional Name

(3S,4S,9S,10R,11S,14R)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0^{3,7}]tetradeca-1,6-dien-5-one

CAS Registry Number

Not Available

SMILES

COC[C@@]1(O)CC[C@H]2[C@@H](C)[C@@H](O)CC3=C(C(C)C)C(=O)[C@@H](C)[C@@H]3\C=C1/2

InChI Identifier

InChI=1S/C21H32O4/c1-11(2)19-16-9-18(22)12(3)14-6-7-21(24,10-25-5)17(14)8-15(16)13(4)20(19)23/h8,11-15,18,22,24H,6-7,9-10H2,1-5H3/b17-8+/t12-,13+,14+,15+,18+,21+/m1/s1

InChI Key

JYZGDIADQSQUAG-DKLZGWCZSA-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 fusicoccane diterpenoids. These are diterpenoids with a structure based on a 20-carbon dicyclopenta[a,d]cyclooctane skeleton (5->8->5 ring system) known as fusicoccane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Fusicoccane diterpenoids

Alternative Parents

Substituents

Fusicoccane diterpenoid
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.33	ChemAxon
pKa (Strongest Acidic)	13.44	ChemAxon
pKa (Strongest Basic)	-0.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.59 m³·mol⁻¹	ChemAxon
Polarizability	40.05 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

C00038637

Chemspider ID

78440351

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586980

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ono Y, Minami A, Noike M, Higuchi Y, Toyomasu T, Sassa T, Kato N, Dairi T: Dioxygenases, key enzymes to determine the aglycon structures of fusicoccin and brassicicene, diterpene compounds produced by fungi. J Am Chem Soc. 2011 Mar 2;133(8):2548-55. doi: 10.1021/ja107785u. Epub 2011 Feb 7. [PubMed:21299202 ]
Hashimoto M, Higuchi Y, Takahashi S, Osada H, Sakaki T, Toyomasu T, Sassa T, Kato N, Dairi T: Functional analyses of cytochrome P450 genes responsible for the early steps of brassicicene C biosynthesis. Bioorg Med Chem Lett. 2009 Oct 1;19(19):5640-3. doi: 10.1016/j.bmcl.2009.08.026. Epub 2009 Aug 8. [PubMed:19700326 ]
Minami A, Tajima N, Higuchi Y, Toyomasu T, Sassa T, Kato N, Dairi T: Identification and functional analysis of brassicicene C biosynthetic gene cluster in Alternaria brassicicola. Bioorg Med Chem Lett. 2009 Feb 1;19(3):870-4. doi: 10.1016/j.bmcl.2008.11.108. Epub 2008 Dec 6. [PubMed:19097780 ]
LOTUS database [Link]

Showing NP-Card for (1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one (NP0275268)

MOL for NP0275268 ((1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one)

3D MOL for NP0275268 ((1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one)

3D SDF for NP0275268 ((1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one)

3D-SDF for NP0275268 ((1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one)

PDB for NP0275268 ((1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one)

3D PDB for NP0275268 ((1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one)

SMILES for NP0275268 ((1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one)

INCHI for NP0275268 ((1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one)

Structure for NP0275268 ((1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one)

3D Structure for NP0275268 ((1e,3s,4s,9s,10r,11s,14r)-9,14-dihydroxy-6-isopropyl-14-(methoxymethyl)-4,10-dimethyltricyclo[9.3.0.0³,⁷]tetradeca-1,6-dien-5-one)