NP-MRD: Showing NP-Card for (1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol (NP0213417)

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Record Information

Version

2.0

Created at

2022-09-05 12:24:04 UTC

Updated at

2022-09-05 12:24:04 UTC

NP-MRD ID

NP0213417

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol

Description

Kalihinol F belongs to the class of organic compounds known as biflorane and serrulatane diterpenoids. These are diterpenoids with a structure based either on the biflorane or the serrulatane skeleton. (1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol is found in Acanthella cavernosa. (1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol was first documented in 2003 (PMID: 14646195). Based on a literature review very few articles have been published on Kalihinol F (PMID: 23790486).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052214242D          

 28 30  0  0  1  0            999 V2000
    1.4289    1.6500    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0374    0.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784    0.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0139    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008    2.0445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4871    2.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3075    2.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666    2.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5733    3.6854    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.6595    4.5059    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    2.6864    1.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3882   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -2.2820    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.7973   -2.9140    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1100   -0.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    0.2871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  3  2  1  6  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  3  0  0  0  0
 10 16  1  0  0  0  0
  6 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 21 22  3  0  0  0  0
 19 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
M  CHG  6   1  -1   2   1  14   1  15  -1  21   1  22  -1
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
    0.3786   -2.6202    1.3659 C   0  0  0  0  0  3  0  0  0  0  0  0
   -0.2076   -2.0429    0.5218 N   0  0  0  0  0  4  0  0  0  0  0  0
   -0.9138   -1.3745   -0.5046 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1535    0.0628   -0.1520 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6135    0.2946    0.0464 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2844   -0.0002   -1.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2424   -1.4775   -1.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1255   -2.1877   -0.7969 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6148   -2.9092    0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7315   -3.2301   -1.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9979    1.6268    0.5856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8685    2.7624   -0.3955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3724    1.5237    0.9684 N   0  0  0  0  0  4  0  0  0  0  0  0
   -5.4868    1.4411    1.2689 C   0  0  0  0  0  3  0  0  0  0  0  0
   -2.2223    1.8517    1.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7391    1.7746    1.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2499    0.5876    0.9048 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1030    0.9490    0.3265 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0267    2.1267   -0.6151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0633    1.3075    1.4546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2668    0.4479    1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0602    0.2475   -0.3776 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9625   -0.8439   -0.8294 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3789   -0.2556   -0.8505 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0122   -2.0454    0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6781   -1.2668   -2.1403 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.4325   -1.6342   -3.2215 C   0  0  0  0  0  3  0  0  0  0  0  0
    1.7014   -0.0878   -0.3708 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2252   -1.4588   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8952    0.6551   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0073   -0.4704    0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6955    0.5119   -2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3164    0.3505   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2043   -1.8861   -1.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3256   -1.7348   -2.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7287   -2.7490    0.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0781   -2.5839    1.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4948   -4.0048    0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1821   -4.0726   -1.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3575    2.5023   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479    3.2148   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2794    3.5615    0.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4688    2.8671    2.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5657    1.1458    2.6247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4011    2.7363    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2909    1.7491    2.6880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0548   -0.2339    1.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5904    3.0133   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5197    1.9186   -1.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0193    2.4647   -0.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3730    2.3695    1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6949    1.0173    2.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069   -0.5374    1.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144    0.9261    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2836    1.1646   -0.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1214   -0.9749   -0.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4508    0.6570   -0.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6354    0.0428   -1.8852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6250   -2.8183   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524   -1.8380    1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304   -2.5334    0.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 25  1  0
 23 26  1  0
 26 27  3  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  6
 18 28  1  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 11  1  0
 11 12  1  0
 11 13  1  1
 13 14  3  0
 11  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  6
  8  3  1  0
  3  2  1  0
  2  1  3  0
  3  4  1  0
 28 22  1  0
  4 17  1  0
  4  5  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
 25 60  1  0
 25 61  1  0
 22 55  1  6
 21 53  1  0
 21 54  1  0
 20 51  1  0
 20 52  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 17 47  1  1
 16 45  1  0
 16 46  1  0
 15 43  1  0
 15 44  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
  5 31  1  1
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
  3 29  1  6
  4 30  1  6
M  CHG  6   1  -1   2   1  13   1  14  -1  26   1  27  -1
M  END


  Mrv1652309052214242D          

 28 30  0  0  1  0            999 V2000
    1.4289    1.6500    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0374    0.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6784    0.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0139    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008    2.0445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4871    2.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3075    2.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666    2.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5733    3.6854    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    3.6595    4.5059    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    2.6864    1.6320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3882   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -2.2820    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.7973   -2.9140    0.0000 C   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1100   -0.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2773    0.2871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  3  2  1  6  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  3  0  0  0  0
 10 16  1  0  0  0  0
  6 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 21 22  3  0  0  0  0
 19 23  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
M  CHG  6   1  -1   2   1  14   1  15  -1  21   1  22  -1
M  END
> <DATABASE_ID>
NP0213417

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)([N+]#[C-])[C@@H]1CC[C@@](C)(O1)C1CC[C@](C)([N+]#[C-])[C@H]2CC[C@@](C)(O)[C@H]([N+]#[C-])[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C23H33N3O2/c1-20(2,25-7)17-11-14-23(5,28-17)16-9-12-21(3,26-8)15-10-13-22(4,27)19(24-6)18(15)16/h15-19,27H,9-14H2,1-5H3/t15-,16?,17-,18-,19+,21-,22+,23+/m0/s1

> <INCHI_KEY>
WUFZGMUGDGETGF-WGFLCXBVSA-N

> <FORMULA>
C23H33N3O2

> <MOLECULAR_WEIGHT>
383.536

> <EXACT_MASS>
383.257277315

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
42.99523510043251

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4aS,5S,8aS)-1,5-diisocyano-8-[(2R,5S)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-decahydronaphthalen-2-ol

> <JCHEM_LOGP>
-3.3995353886278368

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
3

> <JCHEM_PKA>
15.646839932711508

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.338256006091267

> <JCHEM_PKA_STRONGEST_BASIC>
-3.524687287837401

> <JCHEM_POLAR_SURFACE_AREA>
42.540000000000006

> <JCHEM_REFRACTIVITY>
135.6972

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4aS,5S,8aS)-1,5-diisocyano-8-[(2R,5S)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol

> <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       2.667   3.080   0.000  0.00  0.00           C-1
HETATM    2  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.803   1.379   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.866   1.379   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.493   2.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.348   3.816   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.509   5.348   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.041   5.187   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.978   5.509   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       6.670   6.879   0.000  0.00  0.00           N+1
HETATM   15  C   UNK     0       6.831   8.411   0.000  0.00  0.00           C-1
HETATM   16  O   UNK     0       5.015   3.046   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.325  -4.260   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       4.345  -4.260   0.000  0.00  0.00           N+1
HETATM   22  C   UNK     0       3.355  -5.439   0.000  0.00  0.00           C-1
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.205  -0.716   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.518   0.536   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    7    8   16                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15                                                       
CONECT   15   14                                                            
CONECT   16   10    6                                                       
CONECT   17    5   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   23                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   19    4   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    3   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₃N₃O₂

Average Mass

383.5360 Da

Monoisotopic Mass

383.25728 Da

IUPAC Name

(1R,2R,4aS,5S,8aS)-1,5-diisocyano-8-[(2R,5S)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-decahydronaphthalen-2-ol

Traditional Name

(1R,2R,4aS,5S,8aS)-1,5-diisocyano-8-[(2R,5S)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol

CAS Registry Number

Not Available

SMILES

CC(C)([N+]#[C-])[C@@H]1CC[C@@](C)(O1)C1CC[C@](C)([N+]#[C-])[C@H]2CC[C@@](C)(O)[C@H]([N+]#[C-])[C@H]12

InChI Identifier

InChI=1S/C23H33N3O2/c1-20(2,25-7)17-11-14-23(5,28-17)16-9-12-21(3,26-8)15-10-13-22(4,27)19(24-6)18(15)16/h15-19,27H,9-14H2,1-5H3/t15-,16?,17-,18-,19+,21-,22+,23+/m0/s1

InChI Key

WUFZGMUGDGETGF-WGFLCXBVSA-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
Acanthella cavernosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflorane and serrulatane diterpenoids. These are diterpenoids with a structure based either on the biflorane or the serrulatane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Biflorane and serrulatane diterpenoids

Alternative Parents

Substituents

Biflorane diterpenoid
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Oxacycle
Organoheterocyclic compound
Organic isocyanide
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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
logP	-3.4	ChemAxon
pKa (Strongest Acidic)	13.34	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	3	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	42.54 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	135.7 m³·mol⁻¹	ChemAxon
Polarizability	43 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

34528837

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49767004

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sandoval IT, Manos EJ, Van Wagoner RM, Delacruz RG, Edes K, Winge DR, Ireland CM, Jones DA: Juxtaposition of chemical and mutation-induced developmental defects in zebrafish reveal a copper-chelating activity for kalihinol F. Chem Biol. 2013 Jun 20;20(6):753-63. doi: 10.1016/j.chembiol.2013.05.008. [PubMed:23790486 ]
Ohta E, Ohta S, Hongo T, Hamaguchi Y, Andoh T, Shioda M, Ikegami S: Inhibition of chromosome separation in fertilized starfish eggs by kalihinol F, a topoisomerase I inhibitor obtained from a marine sponge. Biosci Biotechnol Biochem. 2003 Nov;67(11):2365-72. doi: 10.1271/bbb.67.2365. [PubMed:14646195 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol (NP0213417)

MOL for NP0213417 ((1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol)

3D MOL for NP0213417 ((1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol)

3D SDF for NP0213417 ((1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol)

3D-SDF for NP0213417 ((1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol)

PDB for NP0213417 ((1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol)

3D PDB for NP0213417 ((1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol)

SMILES for NP0213417 ((1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol)

INCHI for NP0213417 ((1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol)

Structure for NP0213417 ((1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol)

3D Structure for NP0213417 ((1r,2r,4as,5s,8as)-1,5-diisocyano-8-[(2r,5s)-5-(2-isocyanopropan-2-yl)-2-methyloxolan-2-yl]-2,5-dimethyl-octahydronaphthalen-2-ol)