NP-MRD: Showing NP-Card for 4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate (NP0198022)

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Record Information

Version

2.0

Created at

2022-09-04 16:24:05 UTC

Updated at

2022-09-04 16:24:06 UTC

NP-MRD ID

NP0198022

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate

Description

4,9,12-Trimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]Pentadec-9-en-2-yl pyridine-3-carboxylate belongs to the class of organic compounds known as dolabellane and neodolabellane diterpenoids. These are diterpenoids with a structure based on the dolabellane skeleton (3a,6,10-trimethyl-1-(propan-2-yl)-cyclopenta[11]annulene) or the neodolabellane skeleton. 4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate is found in Nigella sativa. 4,9,12-Trimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]Pentadec-9-en-2-yl pyridine-3-carboxylate is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251505152D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004251505152D          

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    2.2359   -2.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4426   -3.2115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2376   -3.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8259   -2.8535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4443   -4.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2394   -4.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4461   -5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8578   -5.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0627   -5.6076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8560   -4.8089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4408   -2.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3830   -3.9146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 18  8  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 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
 24 25  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
 28 38  1  0  0  0  0
  3 38  1  0  0  0  0
  6 38  1  0  0  0  0
  2 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0198022

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C1CCC2(C)C1C(CC1(C)OC1CCC(C)=CC2OC(=O)C1=CC=CN=C1)OC(=O)C1=CC=CN=C1

> <INCHI_IDENTIFIER>
InChI=1S/C32H38N2O5/c1-20(2)24-12-13-31(4)27(38-30(36)23-9-7-15-34-19-23)16-21(3)10-11-26-32(5,39-26)17-25(28(24)31)37-29(35)22-8-6-14-33-18-22/h6-9,14-16,18-19,25-28H,10-13,17H2,1-5H3

> <INCHI_KEY>
VUAQSLCKQTUSSY-UHFFFAOYSA-N

> <FORMULA>
C32H38N2O5

> <MOLECULAR_WEIGHT>
530.665

> <EXACT_MASS>
530.278072332

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
57.21308877047528

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate

> <ALOGPS_LOGP>
4.63

> <JCHEM_LOGP>
5.275443096666667

> <ALOGPS_LOGS>
-5.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.5408340015027693

> <JCHEM_POLAR_SURFACE_AREA>
90.91000000000001

> <JCHEM_REFRACTIVITY>
149.062

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -0.081  -7.145   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.297  -6.458   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.391  -4.920   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.202  -3.941   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.767  -2.508   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.304  -2.602   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.319  -1.418   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.453  -1.369   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.038  -0.762   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.857   0.768   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.091   1.689   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.442   1.375   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.792   0.454   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.207   1.062   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.388   2.591   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.154   3.513   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       0.261   2.905   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.547   0.168   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.038   0.554   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.602   1.987   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.865  -0.745   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.468  -1.265   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.854  -2.756   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.240  -4.247   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.756  -3.836   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.345  -5.320   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.272  -3.424   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.174  -4.504   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.559  -5.995   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.044  -6.406   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.142  -5.326   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.429  -7.897   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.914  -8.308   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.299  -9.799   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.201 -10.879   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       5.717 -10.467   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       5.331  -8.977   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.690  -4.093   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.582  -7.307   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   38                                             
CONECT    7    6                                                            
CONECT    8    6    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    8   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   25                                                       
CONECT   25   24   23   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   38                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
CONECT   38   28    3    6                                                  
CONECT   39    2                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
4,9,12-Trimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0,]pentadec-9-en-2-yl pyridine-3-carboxylic acid	Generator
4,9,12-Trimethyl-15-(propan-2-ylidene)-11-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-2-yl pyridine-3-carboxylic acid	Generator

Chemical Formula

C₃₂H₃₈N₂O₅

Average Mass

530.6650 Da

Monoisotopic Mass

530.27807 Da

IUPAC Name

4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate

Traditional Name

4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate

CAS Registry Number

Not Available

SMILES

CC(C)=C1CCC2(C)C1C(CC1(C)OC1CCC(C)=CC2OC(=O)C1=CC=CN=C1)OC(=O)C1=CC=CN=C1

InChI Identifier

InChI=1S/C32H38N2O5/c1-20(2)24-12-13-31(4)27(38-30(36)23-9-7-15-34-19-23)16-21(3)10-11-26-32(5,39-26)17-25(28(24)31)37-29(35)22-8-6-14-33-18-22/h6-9,14-16,18-19,25-28H,10-13,17H2,1-5H3

InChI Key

VUAQSLCKQTUSSY-UHFFFAOYSA-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
Nigella sativa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dolabellane and neodolabellane diterpenoids. These are diterpenoids with a structure based on the dolabellane skeleton (3a,6,10-trimethyl-1-(propan-2-yl)-cyclopenta[11]annulene) or the neodolabellane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Dolabellane and neodolabellane diterpenoids

Alternative Parents

Substituents

Dolabellane diterpenoid
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Dicarboxylic acid or derivatives
Pyridine
Heteroaromatic compound
Carboxylic acid ester
Dialkyl ether
Oxirane
Ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Azacycle
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.63	ALOGPS
logP	5.28	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Basic)	3.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	90.91 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	149.06 m³·mol⁻¹	ChemAxon
Polarizability	57.21 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

85434653

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate (NP0198022)

MOL for NP0198022 (4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate)

3D MOL for NP0198022 (4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate)

3D SDF for NP0198022 (4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate)

3D-SDF for NP0198022 (4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate)

PDB for NP0198022 (4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate)

3D PDB for NP0198022 (4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate)

SMILES for NP0198022 (4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate)

INCHI for NP0198022 (4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate)

Structure for NP0198022 (4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate)

3D Structure for NP0198022 (4,9,12-trimethyl-15-(propan-2-ylidene)-2-(pyridine-3-carbonyloxy)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-11-yl pyridine-3-carboxylate)