NP-MRD: Showing NP-Card for Kaurenoic acid thujanol ester (NP0046729)

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Record Information

Version

2.0

Created at

2022-03-17 20:11:56 UTC

Updated at

2022-03-17 20:11:56 UTC

NP-MRD ID

NP0046729

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kaurenoic acid thujanol ester

Description

Kaurenoic acid thujanol ester 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. Kaurenoic acid thujanol ester is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212502D          

 34 38  0  0  1  0            999 V2000
    0.9474   -0.8190    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6626   -1.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839   -0.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4378    0.0030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7306    0.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1397    1.2720    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4070    1.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6487    1.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    0.4460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9474    0.0060    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9376    0.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329    0.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4815    0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4815   -0.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329   -1.2315    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1544   -1.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203   -1.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4448   -1.9888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7365    0.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5539    0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3255   -0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694   -0.3790    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474   -1.6440    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419   -4.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669   -4.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8794   -3.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669   -2.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419   -2.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294   -3.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7044   -3.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5956   -3.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0081   -4.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0081   -2.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1831   -2.6596    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 34  1  0  0  0  0
 17 18  2  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  4 21  1  0  0  0  0
  9 22  1  1  0  0  0
  1 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
 26 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 29 34  1  0  0  0  0
M  END


  Mrv0541 02241212502D          

 34 38  0  0  1  0            999 V2000
    0.9474   -0.8190    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6626   -1.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3839   -0.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4378    0.0030    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7306    0.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1397    1.2720    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4070    1.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6487    1.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694    0.4460    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9474    0.0060    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9376    0.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329    0.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4815    0.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4815   -0.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2329   -1.2315    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1544   -1.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203   -1.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4448   -1.9888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7365    0.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5539    0.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3255   -0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6694   -0.3790    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474   -1.6440    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419   -4.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669   -4.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8794   -3.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4669   -2.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419   -2.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2294   -3.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7044   -3.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5956   -3.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0081   -4.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0081   -2.6596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1831   -2.6596    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  1 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  6  0  0  0
 17 34  1  0  0  0  0
 17 18  2  0  0  0  0
  6 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  4 21  1  0  0  0  0
  9 22  1  1  0  0  0
  1 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
 26 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 29 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@@](C)(CCC[C@@]21C)C(=O)OC1(CCC(C)=CC1)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O2/c1-20(2)30(16-10-21(3)11-17-30)32-26(31)28(6)14-7-13-27(5)24(28)12-15-29-18-22(4)23(19-29)8-9-25(27)29/h10,20,23-25H,4,7-9,11-19H2,1-3,5-6H3/t23-,24+,25+,27-,28-,29-,30?/m1/s1

> <INCHI_KEY>
CMRBNBQSOJNLFB-AHPUQKNMSA-N

> <FORMULA>
C30H46O2

> <MOLECULAR_WEIGHT>
438.685

> <EXACT_MASS>
438.349780716

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
53.225167952813194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methyl-1-(propan-2-yl)cyclohex-3-en-1-yl (1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

> <ALOGPS_LOGP>
6.58

> <JCHEM_LOGP>
7.802506856666667

> <ALOGPS_LOGS>
-6.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.129629331785493

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
132.17929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.40e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-isopropyl-4-methylcyclohex-3-en-1-yl (1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.768  -1.529   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.104  -2.319   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.450  -1.566   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.551   0.006   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.097   1.221   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.861   2.374   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.493   3.232   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.078   2.474   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.116   0.833   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.768   0.011   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.750   1.551   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.435   0.781   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.899   0.011   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.899  -1.529   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.435  -2.299   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.288  -3.659   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.158  -3.659   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.697  -3.712   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.975   1.210   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.501   1.418   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.208  -0.220   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       3.116  -0.707   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.768  -3.069   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      -1.198  -7.632   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.738  -7.632   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.508  -6.298   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.738  -4.965   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.198  -4.965   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.428  -6.298   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.048  -6.298   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.112  -6.298   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.882  -7.632   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.882  -4.965   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.342  -4.965   0.000  0.00  0.00           O+0
CONECT    1    2   10   15   23                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9   21                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10   22                                             
CONECT   10    9    1   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    1   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   34   18                                                  
CONECT   18   17                                                            
CONECT   19    6   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    4                                                       
CONECT   22    9                                                            
CONECT   23    1                                                            
CONECT   24   25   29                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24   31   34                                             
CONECT   30   26                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   17   29                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Kaurenoate thujanol ester	Generator

Chemical Formula

C₃₀H₄₆O₂

Average Mass

438.6850 Da

Monoisotopic Mass

438.34978 Da

IUPAC Name

4-methyl-1-(propan-2-yl)cyclohex-3-en-1-yl (1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

Traditional Name

1-isopropyl-4-methylcyclohex-3-en-1-yl (1S,4S,5R,9S,10R,13R)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate

CAS Registry Number

58-55-9

SMILES

[H][C@@]12CC[C@@H]3C[C@]1(CC3=C)CC[C@]1([H])[C@@](C)(CCC[C@@]21C)C(=O)OC1(CCC(C)=CC1)C(C)C

InChI Identifier

InChI=1S/C30H46O2/c1-20(2)30(16-10-21(3)11-17-30)32-26(31)28(6)14-7-13-27(5)24(28)12-15-29-18-22(4)23(19-29)8-9-25(27)29/h10,20,23-25H,4,7-9,11-19H2,1-3,5-6H3/t23-,24+,25+,27-,28-,29-,30?/m1/s1

InChI Key

CMRBNBQSOJNLFB-AHPUQKNMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Helianthus annuus L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.58	ALOGPS
logP	7.8	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	132.18 m³·mol⁻¹	ChemAxon
Polarizability	53.23 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

FDB005669

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Kaurenoic acid thujanol ester (NP0046729)

MOL for NP0046729 (Kaurenoic acid thujanol ester)

3D MOL for NP0046729 (Kaurenoic acid thujanol ester)

3D SDF for NP0046729 (Kaurenoic acid thujanol ester)

3D-SDF for NP0046729 (Kaurenoic acid thujanol ester)

PDB for NP0046729 (Kaurenoic acid thujanol ester)

3D PDB for NP0046729 (Kaurenoic acid thujanol ester)

SMILES for NP0046729 (Kaurenoic acid thujanol ester)

INCHI for NP0046729 (Kaurenoic acid thujanol ester)

Structure for NP0046729 (Kaurenoic acid thujanol ester)

3D Structure for NP0046729 (Kaurenoic acid thujanol ester)