NP-MRD: Showing NP-Card for (4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one (NP0194040)

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Record Information

Version

2.0

Created at

2022-09-04 11:37:20 UTC

Updated at

2022-09-04 11:37:20 UTC

NP-MRD ID

NP0194040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one

Description

(4S)-4-[(1Z)-2-[(2S,5S,9R)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]Nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one is found in Aspergillus rugulosus. Based on a literature review very few articles have been published on (4S)-4-[(1Z)-2-[(2S,5S,9R)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]Nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042213372D          

 28 30  0  0  1  0            999 V2000
    0.0045    0.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930   -0.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325   -1.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335   -1.8506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254   -0.8220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6193   -1.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3882   -0.0297    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6577    1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    1.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8955    0.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5797   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3727   -0.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8955   -0.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6577   -1.1076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7907   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4199   -0.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7356   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5765   -0.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4199    0.7325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0486    1.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0656    2.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9070    1.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3490    0.6991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1724    0.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3774   -0.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6808   -0.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6289   -1.4173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0452   -0.0680    0.0000 C   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  2  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 23 28  1  0  0  0  0
M  END


  Mrv1652309042213372D          

 28 30  0  0  1  0            999 V2000
    0.0045    0.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930   -0.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325   -1.0499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0335   -1.8506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0254   -0.8220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6193   -1.3947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3882   -0.0297    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6577    1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5798    1.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8955    0.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5797   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3727   -0.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8955   -0.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6577   -1.1076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7907   -1.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4199   -0.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7356   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5765   -0.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4199    0.7325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0486    1.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0656    2.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9070    1.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3490    0.6991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1724    0.6472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3774   -0.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6808   -0.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6289   -1.4173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0452   -0.0680    0.0000 C   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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  2  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 22  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 23 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0194040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)C(=C)[C@@H]1[C@@]2(C)CC(C)=CC1(C)[C@@H](\C(C)=C/[C@H]1CC(=O)C=C1)C(C)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O2/c1-8-22(28)19(5)24-25(6)13-16(2)14-26(24,7)23(18(4)15-25)17(3)11-20-9-10-21(27)12-20/h9-11,14-15,20,23-24H,5,8,12-13H2,1-4,6-7H3/b17-11-/t20-,23-,24+,25-,26?/m0/s1

> <INCHI_KEY>
FMKMRACZTYQJQI-AZGAKODRSA-N

> <FORMULA>
C26H34O2

> <MOLECULAR_WEIGHT>
378.556

> <EXACT_MASS>
378.255880335

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.13954148762558

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-4-[(1Z)-2-[(2S,5S,9R)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one

> <JCHEM_LOGP>
5.5112824246666685

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.239368292247963

> <JCHEM_PKA_STRONGEST_BASIC>
-4.738676255922098

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
120.05359999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-4-[(1Z)-2-[(2S,5S,9R)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.008   0.791   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.734  -0.834   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.434  -1.960   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.062  -3.454   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.914  -1.534   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.023  -2.603   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.591  -0.055   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.094   1.957   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.949   3.565   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.672   1.367   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.082  -0.055   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.696  -0.267   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.672  -1.478   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.094  -2.068   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.343  -3.659   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.517  -1.478   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.106  -0.055   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.676  -0.377   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.517   1.367   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.691   2.538   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.722   4.143   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.293   2.605   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.118   1.305   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.655   1.208   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.038  -0.284   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.738  -1.109   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.641  -2.646   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.551  -0.127   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    2    8   14                                                  
CONECT    8    7    9   10   19                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    7   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    8   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   23                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₂

Average Mass

378.5560 Da

Monoisotopic Mass

378.25588 Da

IUPAC Name

(4S)-4-[(1Z)-2-[(2S,5S,9R)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one

Traditional Name

(4S)-4-[(1Z)-2-[(2S,5S,9R)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one

CAS Registry Number

Not Available

SMILES

CCC(=O)C(=C)[C@@H]1[C@@]2(C)CC(C)=CC1(C)[C@@H](\C(C)=C/[C@H]1CC(=O)C=C1)C(C)=C2

InChI Identifier

InChI=1S/C26H34O2/c1-8-22(28)19(5)24-25(6)13-16(2)14-26(24,7)23(18(4)15-25)17(3)11-20-9-10-21(27)12-20/h9-11,14-15,20,23-24H,5,8,12-13H2,1-4,6-7H3/b17-11-/t20-,23-,24+,25-,26?/m0/s1

InChI Key

FMKMRACZTYQJQI-AZGAKODRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus rugulosus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Alpha-branched alpha,beta-unsaturated-ketone
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Cyclic ketone
Ketone
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	5.51	ChemAxon
pKa (Strongest Acidic)	18.24	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.05 m³·mol⁻¹	ChemAxon
Polarizability	44.14 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

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

163185840

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one (NP0194040)

MOL for NP0194040 ((4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one)

3D MOL for NP0194040 ((4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one)

3D SDF for NP0194040 ((4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one)

3D-SDF for NP0194040 ((4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one)

PDB for NP0194040 ((4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one)

3D PDB for NP0194040 ((4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one)

SMILES for NP0194040 ((4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one)

INCHI for NP0194040 ((4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one)

Structure for NP0194040 ((4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one)

3D Structure for NP0194040 ((4s)-4-[(1z)-2-[(2s,5s,9r)-1,3,5,7-tetramethyl-9-(3-oxopent-1-en-2-yl)bicyclo[3.3.1]nona-3,7-dien-2-yl]prop-1-en-1-yl]cyclopent-2-en-1-one)