NP-MRD: Showing NP-Card for (1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium) (NP0256018)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 20:43:23 UTC

Updated at

2022-09-07 20:43:23 UTC

NP-MRD ID

NP0256018

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium)

Description

Kalihinol B 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. (1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium) is found in Acanthella pulcherrima. (1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium) was first documented in 2015 (PMID: 25815413). Based on a literature review very few articles have been published on Kalihinol B (PMID: 28337330).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072222432D          

 27 29  0  0  1  0            999 V2000
   -0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  2  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  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5390   -1.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517   -1.9371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8986    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    0.6320    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.4895    1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  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
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6085   -2.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2494   -2.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850   -3.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9719   -3.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581   -4.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1444   -5.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376   -4.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786   -4.4287    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2574   -3.2820    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  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  6  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  1  0  0  0
 13 14  3  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 22 27  1  0  0  0  0
 18 27  1  0  0  0  0
M  CHG  2   2   1  13   1
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
   -0.5071    3.6695   -0.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0158    2.7251   -0.3454 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.6450    1.5764    0.2223 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0291    0.2953   -0.2554 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9451   -0.7459   -0.7842 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3127   -0.2699   -1.1930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3988    1.2002   -1.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0885    1.8033   -0.0538 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3883    3.3053   -0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9652    1.3929    0.9336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1509   -1.9943   -0.0027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0276   -1.9246    1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8033   -2.9057   -0.9015 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.3221   -3.6456   -1.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8712   -2.7035    0.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2230   -1.7466    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0692   -0.3486    0.6908 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2372    0.2332    0.9684 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3860    1.6351    1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9122   -0.6452    2.0383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2819   -0.9414    1.4826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3763    0.0215    0.3521 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2888   -0.4576   -0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6939   -0.6817   -0.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3284    0.6496   -1.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6619   -1.9145   -1.5454 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1145    0.1083   -0.1479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0658    4.5198   -1.2811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5483    1.6215    1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3483    0.6219   -1.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5197   -1.1271   -1.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0450   -0.5200   -0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7197   -0.7837   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6175    1.5441   -2.1036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4088    1.4509   -1.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0484    3.6889   -1.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4652    3.5035   -0.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8198    3.7971    0.6111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5761    1.6493    1.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069   -2.7685    1.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1194   -2.0640    0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9690   -0.9933    1.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7811   -4.3121   -2.2933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8673   -2.9624    1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6895   -3.6299   -0.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -1.5956   -0.9895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797   -2.1528    0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6346   -0.5638    1.6324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6638    2.0272    2.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6026    2.2990    0.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3705    1.6912    1.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0766   -0.0522    2.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -1.5226    2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4275   -1.9997    1.1829 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0735   -0.7607    2.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8094    0.9717    0.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0938    0.2725    0.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3110   -0.9153   -1.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7870   -1.5131    0.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8722    1.5017   -1.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3105    1.0206   -2.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8975    0.3653   -2.6960 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
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  1
 18 27  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  6
 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  1
  8  3  1  0
  3  2  1  0
  2  1  3  0
  3  4  1  0
 27 22  1  0
  4 17  1  0
  4  5  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  0
 25 61  1  0
 25 62  1  0
 22 56  1  1
 21 54  1  0
 21 55  1  0
 20 52  1  0
 20 53  1  0
 19 49  1  0
 19 50  1  0
 19 51  1  0
 17 48  1  1
 16 46  1  0
 16 47  1  0
 15 44  1  0
 15 45  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 14 43  1  0
  5 31  1  6
  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  1
  1 28  1  0
  4 30  1  6
M  CHG  2   2   1  13   1
M  END


  Mrv1652309072222432D          

 27 29  0  0  1  0            999 V2000
   -0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -2.4750    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  2  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  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5390   -1.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517   -1.9371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8986    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592    0.6320    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.4895    1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  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
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6085   -2.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2494   -2.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5850   -3.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9719   -3.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0581   -4.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1444   -5.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376   -4.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8786   -4.4287    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2574   -3.2820    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  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  6  0  0  0
  5 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  1  0  0  0
 13 14  3  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 22 27  1  0  0  0  0
 18 27  1  0  0  0  0
M  CHG  2   2   1  13   1
M  END
> <DATABASE_ID>
NP0256018

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(Cl)C1CC[C@@](C)(O1)C1CC[C@](C)([N+]#C)C2CC[C@@](C)(O)[C@H]([N+]#C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H35ClN2O2/c1-19(2,23)16-10-13-22(5,27-16)15-8-11-20(3,25-7)14-9-12-21(4,26)18(24-6)17(14)15/h6-7,14-18,26H,8-13H2,1-5H3/q+2/t14?,15?,16?,17?,18-,20+,21-,22-/m1/s1

> <INCHI_KEY>
YLLBODFFVLSPFD-WUTMYOKYSA-N

> <FORMULA>
C22H35ClN2O2

> <MOLECULAR_WEIGHT>
394.98

> <EXACT_MASS>
394.2376089

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.111511751608056

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,5R,6R)-4-[(2R)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-N1,N5-dimethylidyne-decahydronaphthalene-1,5-bis(aminium)

> <JCHEM_LOGP>
-0.6051115980852249

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
15.825305215792849

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.338979263894224

> <JCHEM_PKA_STRONGEST_BASIC>
-3.524687287774637

> <JCHEM_POLAR_SURFACE_AREA>
38.18

> <JCHEM_REFRACTIVITY>
107.8971

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,6R)-4-[(2R)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-N1,N5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium)

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.000  -4.620   0.000  0.00  0.00           N+1
HETATM    3  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.873  -2.364   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.150  -3.616   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.677   1.180   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.657   1.180   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0       4.647   2.359   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.136  -4.459   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.199  -4.459   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.825  -5.866   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.681  -6.896   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.842  -8.428   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.003  -9.959   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.310  -8.589   0.000  0.00  0.00           C+0
HETATM   26 Cl   UNK     0       5.373  -8.267   0.000  0.00  0.00          Cl+0
HETATM   27  O   UNK     0       2.347  -6.126   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9   10                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12   13   15                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    4   18                                                  
CONECT   18   17   19   20   27                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27   22   18                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₅ClN₂O₂

Average Mass

394.9800 Da

Monoisotopic Mass

394.23761 Da

IUPAC Name

(1S,5R,6R)-4-[(2R)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-N1,N5-dimethylidyne-decahydronaphthalene-1,5-bis(aminium)

Traditional Name

(1S,5R,6R)-4-[(2R)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-N1,N5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium)

CAS Registry Number

Not Available

SMILES

CC(C)(Cl)C1CC[C@@](C)(O1)C1CC[C@](C)([N+]#C)C2CC[C@@](C)(O)[C@H]([N+]#C)C12

InChI Identifier

InChI=1S/C22H35ClN2O2/c1-19(2,23)16-10-13-22(5,27-16)15-8-11-20(3,25-7)14-9-12-21(4,26)18(24-6)17(14)15/h6-7,14-18,26H,8-13H2,1-5H3/q+2/t14?,15?,16?,17?,18-,20+,21-,22-/m1/s1

InChI Key

YLLBODFFVLSPFD-WUTMYOKYSA-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 pulcherrima	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
Carbonitrile
Ether
Dialkyl ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Alkyl halide
Alkyl chloride
Alcohol
Organic cation
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	-0.61	ChemAxon
pKa (Strongest Acidic)	13.34	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.18 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	107.9 m³·mol⁻¹	ChemAxon
Polarizability	44.11 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

129906619

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Daub ME, Prudhomme J, Ben Mamoun C, Le Roch KG, Vanderwal CD: Antimalarial Properties of Simplified Kalihinol Analogues. ACS Med Chem Lett. 2017 Feb 16;8(3):355-360. doi: 10.1021/acsmedchemlett.7b00013. eCollection 2017 Mar 9. [PubMed:28337330 ]
Daub ME, Prudhomme J, Le Roch K, Vanderwal CD: Synthesis and potent antimalarial activity of kalihinol B. J Am Chem Soc. 2015 Apr 22;137(15):4912-5. doi: 10.1021/jacs.5b01152. Epub 2015 Apr 9. [PubMed:25815413 ]
LOTUS database [Link]

Showing NP-Card for (1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium) (NP0256018)

MOL for NP0256018 ((1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium))

3D MOL for NP0256018 ((1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium))

3D SDF for NP0256018 ((1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium))

3D-SDF for NP0256018 ((1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium))

PDB for NP0256018 ((1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium))

3D PDB for NP0256018 ((1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium))

SMILES for NP0256018 ((1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium))

INCHI for NP0256018 ((1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium))

Structure for NP0256018 ((1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium))

3D Structure for NP0256018 ((1s,5r,6r)-4-[(2r)-5-(2-chloropropan-2-yl)-2-methyloxolan-2-yl]-6-hydroxy-1,6-dimethyl-n1,n5-dimethylidyne-octahydronaphthalene-1,5-bis(aminium))