NP-MRD: Showing NP-Card for (1r,4s,5r,9r,10s,13r,15s)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate (NP0294622)

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Record Information

Version

2.0

Created at

2022-09-10 03:15:34 UTC

Updated at

2022-09-10 03:15:34 UTC

NP-MRD ID

NP0294622

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4s,5r,9r,10s,13r,15s)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate

Description

(1R,4S,5R,9R,10S,13R,15S)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-15-yl (2S,3R)-2,3-dimethyloxirane-2-carboxylate 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. Based on a literature review very few articles have been published on (1R,4S,5R,9R,10S,13R,15S)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-15-yl (2S,3R)-2,3-dimethyloxirane-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102205152D          

 31 35  0  0  1  0            999 V2000
    0.0435   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566   -0.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4794    0.4660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3435    1.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5709    1.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0659    1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4350    2.3827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2128    2.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3899    2.3903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0291    3.1009    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0366    3.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2893    0.0832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5946    0.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4039    1.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9582    0.4175    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7638    0.5954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4487    1.3579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4599    1.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4246    1.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1914    0.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0719   -0.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2663   -0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7095   -0.3691    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.8140   -0.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  5  1  1  0  0  0
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  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 10  1  0  0  0  0
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  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
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 29 30  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  6  0  0  0
 12 31  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309102205152D          

 31 35  0  0  1  0            999 V2000
    0.0435   -0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4794    0.4660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.7638    0.5954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    5.4246    1.8624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 12 31  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0294622

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(C)CCC[C@]2(C)[C@@H]3CC[C@@H]4C[C@@]3(CC[C@H]12)[C@@H](OC(=O)[C@@]1(C)O[C@@H]1C)C4=C

> <INCHI_IDENTIFIER>
InChI=1S/C26H38O5/c1-15-17-8-9-19-23(3)11-7-12-24(4,21(27)29-6)18(23)10-13-26(19,14-17)20(15)30-22(28)25(5)16(2)31-25/h16-20H,1,7-14H2,2-6H3/t16-,17-,18+,19+,20+,23+,24-,25+,26-/m1/s1

> <INCHI_KEY>
ZLUFZWBQPPVUMF-RGWYKFSJSA-N

> <FORMULA>
C26H38O5

> <MOLECULAR_WEIGHT>
430.585

> <EXACT_MASS>
430.271924324

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
48.509733152884536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,5R,9R,10S,13R,15S)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-yl (2S,3R)-2,3-dimethyloxirane-2-carboxylate

> <JCHEM_LOGP>
5.0355973363333355

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.296252110725929

> <JCHEM_POLAR_SURFACE_AREA>
65.13

> <JCHEM_REFRACTIVITY>
116.00749999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,5R,9R,10S,13R,15S)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-15-yl (2S,3R)-2,3-dimethyloxirane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.081  -0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.599  -0.263   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.761   0.870   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.508   2.389   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.066   2.929   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.123   1.950   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.812   4.448   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.264   4.961   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.728   4.462   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.054   5.788   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.068   7.328   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.273   0.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.843   1.624   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.354   1.935   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.389   0.779   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.892   1.111   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.304   2.535   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.192   1.938   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.126   3.476   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.557   1.226   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.857   2.052   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.932  -0.025   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.468  -1.493   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.964  -1.825   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.924  -0.689   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.477  -2.163   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.392  -1.066   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.934  -2.642   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.356  -2.939   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.310  -1.708   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.386  -0.839   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    7   11                                                  
CONECT   11   10                                                            
CONECT   12    3   13   27   31                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17   18   22                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   16   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   15   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   12   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    2   31                                                  
CONECT   31   30   12                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1R,4S,5R,9R,10S,13R,15S)-5-(Methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0,.0,]hexadecan-15-yl (2S,3R)-2,3-dimethyloxirane-2-carboxylic acid	Generator

Chemical Formula

C₂₆H₃₈O₅

Average Mass

430.5850 Da

Monoisotopic Mass

430.27192 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(C)CCC[C@]2(C)[C@@H]3CC[C@@H]4C[C@@]3(CC[C@H]12)[C@@H](OC(=O)[C@@]1(C)O[C@@H]1C)C4=C

InChI Identifier

InChI=1S/C26H38O5/c1-15-17-8-9-19-23(3)11-7-12-24(4,21(27)29-6)18(23)10-13-26(19,14-17)20(15)30-22(28)25(5)16(2)31-25/h16-20H,1,7-14H2,2-6H3/t16-,17-,18+,19+,20+,23+,24-,25+,26-/m1/s1

InChI Key

ZLUFZWBQPPVUMF-RGWYKFSJSA-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 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
Oxirane carboxylic acid or derivatives
Oxirane carboxylic acid
Dicarboxylic acid or derivatives
Methyl ester
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

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

163188678

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4s,5r,9r,10s,13r,15s)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate (NP0294622)

MOL for NP0294622 ((1r,4s,5r,9r,10s,13r,15s)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate)

3D MOL for NP0294622 ((1r,4s,5r,9r,10s,13r,15s)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate)

3D SDF for NP0294622 ((1r,4s,5r,9r,10s,13r,15s)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate)

3D-SDF for NP0294622 ((1r,4s,5r,9r,10s,13r,15s)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate)

PDB for NP0294622 ((1r,4s,5r,9r,10s,13r,15s)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate)

3D PDB for NP0294622 ((1r,4s,5r,9r,10s,13r,15s)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate)

SMILES for NP0294622 ((1r,4s,5r,9r,10s,13r,15s)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate)

INCHI for NP0294622 ((1r,4s,5r,9r,10s,13r,15s)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate)

Structure for NP0294622 ((1r,4s,5r,9r,10s,13r,15s)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate)

3D Structure for NP0294622 ((1r,4s,5r,9r,10s,13r,15s)-5-(methoxycarbonyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-yl (2s,3r)-2,3-dimethyloxirane-2-carboxylate)