NP-MRD: Showing NP-Card for 3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid (NP0240705)

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Record Information

Version

2.0

Created at

2022-09-07 00:35:39 UTC

Updated at

2022-09-07 00:35:40 UTC

NP-MRD ID

NP0240705

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid

Description

3-[(3S,3aS,5aS,6R,7S)-3,3a,6-trimethyl-3-[(2R)-1-[(2Z)-4-methyl-5-oxo-2,5-dihydrofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,7H-cyclopenta[a]naphthalen-6-yl]propanoic acid belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid is found in Abies sibirica. Based on a literature review very few articles have been published on 3-[(3S,3aS,5aS,6R,7S)-3,3a,6-trimethyl-3-[(2R)-1-[(2Z)-4-methyl-5-oxo-2,5-dihydrofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,7H-cyclopenta[a]naphthalen-6-yl]propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072202352D          

 34 37  0  0  1  0            999 V2000
   -0.6549   -0.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6102   -1.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -0.8508    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9943   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -0.0980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3745   -0.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0180   -2.9285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
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  7  8  2  0  0  0  0
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 18 20  1  0  0  0  0
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 20 22  1  0  0  0  0
 16 22  1  0  0  0  0
 11 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  1  1  0  0  0
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  7 27  1  0  0  0  0
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  4 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309072202352D          

 34 37  0  0  1  0            999 V2000
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   -1.0180   -2.9285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  1  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 16 22  1  0  0  0  0
 11 23  1  0  0  0  0
  8 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
  7 27  1  0  0  0  0
 27 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240705

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](\C=C1/OC(=O)C(C)=C1)[C@]1(C)CCC2=C3C=C[C@@H](C(C)=C)[C@](C)(CCC(O)=O)[C@@H]3CC[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O4/c1-18(2)23-9-8-22-24(28(23,5)13-12-26(31)32)10-15-30(7)25(22)11-14-29(30,6)20(4)17-21-16-19(3)27(33)34-21/h8-9,16-17,20,23-24H,1,10-15H2,2-7H3,(H,31,32)/b21-17-/t20-,23+,24-,28+,29+,30-/m1/s1

> <INCHI_KEY>
SEDSTERUSLKVFG-VMUGRQMYSA-N

> <FORMULA>
C30H40O4

> <MOLECULAR_WEIGHT>
464.646

> <EXACT_MASS>
464.292659768

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.79616671968535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(3S,3aS,5aS,6R,7S)-3,3a,6-trimethyl-3-[(2R)-1-[(2Z)-4-methyl-5-oxo-2,5-dihydrofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1H,2H,3H,3aH,4H,5H,5aH,6H,7H-cyclopenta[a]naphthalen-6-yl]propanoic acid

> <JCHEM_LOGP>
6.042351190000001

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.7654911020122706

> <JCHEM_PKA_STRONGEST_BASIC>
-6.9979510129865075

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
138.7507

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3S,3aS,5aS,6R,7S)-3,3a,6-trimethyl-3-[(2R)-1-[(2Z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1H,2H,4H,5H,5aH,7H-cyclopenta[a]naphthalen-6-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      -1.222  -0.327   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.411  -1.636   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.139  -2.993   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.128  -1.588   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.856  -0.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.395  -0.183   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.207  -1.492   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.746  -1.444   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.740  -0.268   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.166  -0.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.053  -2.386   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.261  -3.912   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.592  -2.338   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.403  -3.647   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.320  -0.981   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.859  -0.932   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.725   0.341   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.204  -0.089   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.421   0.855   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.252  -1.628   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      15.525  -2.494   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      12.803  -2.149   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.557  -2.753   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.501  -3.970   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.829  -4.110   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.290  -4.158   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.479  -2.849   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.939  -2.897   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.934  -4.437   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.660  -3.754   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.761  -5.290   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.519  -6.147   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.417  -7.683   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.900  -5.466   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   28                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   27                                                  
CONECT    8    7    9   23                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   23                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   16                                                       
CONECT   23   11    8   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26    7   28                                                  
CONECT   28   27    4   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
3-[(3S,3AS,5as,6R,7S)-3,3a,6-trimethyl-3-[(2R)-1-[(2Z)-4-methyl-5-oxo-2,5-dihydrofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1H,2H,3H,3ah,4H,5H,5ah,6H,7H-cyclopenta[a]naphthalen-6-yl]propanoate	Generator

Chemical Formula

C₃₀H₄₀O₄

Average Mass

464.6460 Da

Monoisotopic Mass

464.29266 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H](\C=C1/OC(=O)C(C)=C1)[C@]1(C)CCC2=C3C=C[C@@H](C(C)=C)[C@](C)(CCC(O)=O)[C@@H]3CC[C@@]12C

InChI Identifier

InChI=1S/C30H40O4/c1-18(2)23-9-8-22-24(28(23,5)13-12-26(31)32)10-15-30(7)25(22)11-14-29(30,6)20(4)17-21-16-19(3)27(33)34-21/h8-9,16-17,20,23-24H,1,10-15H2,2-7H3,(H,31,32)/b21-17-/t20-,23+,24-,28+,29+,30-/m1/s1

InChI Key

SEDSTERUSLKVFG-VMUGRQMYSA-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
Abies sibirica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Enol ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
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

162896168

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid (NP0240705)

MOL for NP0240705 (3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid)

3D MOL for NP0240705 (3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid)

3D SDF for NP0240705 (3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid)

3D-SDF for NP0240705 (3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid)

PDB for NP0240705 (3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid)

3D PDB for NP0240705 (3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid)

SMILES for NP0240705 (3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid)

INCHI for NP0240705 (3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid)

Structure for NP0240705 (3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid)

3D Structure for NP0240705 (3-[(3s,3as,5as,6r,7s)-3,3a,6-trimethyl-3-[(2r)-1-[(2z)-4-methyl-5-oxofuran-2-ylidene]propan-2-yl]-7-(prop-1-en-2-yl)-1h,2h,4h,5h,5ah,7h-cyclopenta[a]naphthalen-6-yl]propanoic acid)