NP-MRD: Showing NP-Card for methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate (NP0291022)

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Record Information

Version

2.0

Created at

2022-09-09 21:57:27 UTC

Updated at

2022-09-09 21:57:27 UTC

NP-MRD ID

NP0291022

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate

Description

Subergorgic acid methyl ester belongs to the class of organic compounds known as angular triquinanes. These are triquinane with a structure based on a [6.3.0.0^1,5] Undecane carbon skeleton. methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate is found in Subergorgia suberosa. methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate was first documented in 2002 (PMID: 12141868). Based on a literature review very few articles have been published on subergorgic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    5.3633    0.6709   -0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9573    0.5972   -0.0606 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2676   -0.5909   -0.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9813   -1.5823   -0.6117 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8171   -0.6658   -0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1281   -1.7643   -0.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3025   -1.4901   -0.3927 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0750   -2.2193   -1.4582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8040   -1.9262    0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0203   -1.0478    1.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5652    0.2669    0.5595 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7453    0.7687   -0.2837 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5220    1.8019    0.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0146    1.4940   -1.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8927    0.5596   -1.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4783    0.3826   -2.8209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4685   -0.0199   -0.4061 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8976    0.4565    0.0368 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3771    1.6553   -0.7436 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6740    1.6205    0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7670    0.6798   -1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8392   -0.1559    0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5399   -2.7471   -0.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8832   -3.3180   -1.2851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1508   -2.0770   -1.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6773   -2.0136   -2.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0929   -1.6535    1.7816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525   -3.0077    0.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8988   -1.4713    0.6196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2869   -0.9320    2.2287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3523    1.0361    1.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3558   -0.0456   -0.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5791    1.8585    0.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5232    1.4403    1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0035    2.7785    0.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7025    2.4625   -0.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6625    1.6546   -2.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8828    0.6101    1.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7443    2.4212   -0.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2447    1.4039   -1.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284    2.1088   -1.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  6
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 17 15  1  6
 17 18  1  0
 18 19  1  0
 18  5  1  0
 17  7  1  0
 17 11  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  6 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  6
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 18 38  1  1
 19 39  1  0
 19 40  1  0
 19 41  1  0
M  END

  Mrv1652309092223572D          

 19 21  0  0  1  0            999 V2000
   -0.7164   -2.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -1.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5890   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9245   -2.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190   -0.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864    0.4468    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8190    0.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5663    1.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213    0.4468    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4887   -0.0381    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2733    0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4088   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9239   -1.4901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538   -0.0381    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8989   -0.8227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6440   -1.6073    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  6  0  0  0
 11 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0291022

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C[C@@]2(C)CC[C@@H]3[C@@H](C)CC(=O)[C@]23[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O3/c1-9-7-13(17)16-10(2)11(14(18)19-4)8-15(16,3)6-5-12(9)16/h8-10,12H,5-7H2,1-4H3/t9-,10+,12+,15+,16+/m0/s1

> <INCHI_KEY>
SJNFRYWQDFKLRC-DUEXZNCYSA-N

> <FORMULA>
C16H22O3

> <MOLECULAR_WEIGHT>
262.349

> <EXACT_MASS>
262.156894568

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
29.18099911285336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,2S,5R,8R,9S)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0^{1,5}]undec-3-ene-3-carboxylate

> <JCHEM_LOGP>
3.0047948133333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.771005212845049

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
72.87389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,5R,8R,9S)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0^{1,5}]undec-3-ene-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.337  -3.866   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.432  -2.621   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.099  -2.782   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.726  -4.188   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.005  -1.536   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.529  -0.071   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.775   0.834   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.529   1.739   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.251   2.299   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.791   2.299   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.266   0.834   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.512  -0.071   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.977   0.405   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.036  -1.536   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.496  -1.536   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.591  -2.782   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.021  -0.071   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.545  -1.536   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.069  -3.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   17                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11    7   18                                             
CONECT   18   17    5   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
Subergorgate methyl ester	Generator

Chemical Formula

C₁₆H₂₂O₃

Average Mass

262.3490 Da

Monoisotopic Mass

262.15689 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C[C@@]2(C)CC[C@@H]3[C@@H](C)CC(=O)[C@]23[C@@H]1C

InChI Identifier

InChI=1S/C16H22O3/c1-9-7-13(17)16-10(2)11(14(18)19-4)8-15(16,3)6-5-12(9)16/h8-10,12H,5-7H2,1-4H3/t9-,10+,12+,15+,16+/m0/s1

InChI Key

SJNFRYWQDFKLRC-DUEXZNCYSA-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
Subergorgia suberosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular triquinanes. These are triquinane with a structure based on a [6.3.0.0^1,5] Undecane carbon skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Angular triquinanes

Alternative Parents

Substituents

Angular triquinane sesquiterpenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Ketone
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00050238

Chemspider ID

8168463

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9992881

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang GH, Ahmed AF, Kuo YH, Sheu JH: Two new subergane-based sesquiterpenes from a Taiwanese Gorgonian coral Subergorgia suberosa. J Nat Prod. 2002 Jul;65(7):1033-6. doi: 10.1021/np0106586. [PubMed:12141868 ]
LOTUS database [Link]

Showing NP-Card for methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate (NP0291022)

MOL for NP0291022 (methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate)

3D MOL for NP0291022 (methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate)

3D SDF for NP0291022 (methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate)

3D-SDF for NP0291022 (methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate)

PDB for NP0291022 (methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate)

3D PDB for NP0291022 (methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate)

SMILES for NP0291022 (methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate)

INCHI for NP0291022 (methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate)

Structure for NP0291022 (methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate)

3D Structure for NP0291022 (methyl (1r,2s,5r,8r,9s)-2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylate)