NP-MRD: Showing NP-Card for 2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate (NP0220147)

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Record Information

Version

2.0

Created at

2022-09-05 21:22:29 UTC

Updated at

2022-09-05 21:22:29 UTC

NP-MRD ID

NP0220147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate

Description

2-[8-Methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]Dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 2-[8-Methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]Dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171514062D          

 29 31  0  0  0  0            999 V2000
    2.1460   -5.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7724   -4.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2226   -3.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491   -3.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0252   -3.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2993   -2.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9257   -1.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3759   -1.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0024   -0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390    0.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4753    1.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2380    1.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729    0.8259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3409    0.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -0.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4735   -0.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9765   -0.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882   -1.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487    1.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7705    0.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1798   -0.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9239   -1.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532    0.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4896    0.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262    1.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526    2.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1028    3.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9486   -4.5464    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  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  4  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  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
  2 29  1  0  0  0  0
M  END


  Mrv1533004171514062D          

 29 31  0  0  0  0            999 V2000
    2.1460   -5.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7724   -4.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2226   -3.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8491   -3.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0252   -3.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2993   -2.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9257   -1.7369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3759   -1.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0024   -0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5390    0.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4753    1.1392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2380    1.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729    0.8259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3409    0.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6557   -0.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4735   -0.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9765   -0.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882   -1.5110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8487    1.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7705    0.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1798   -0.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9239   -1.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532    0.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4896    0.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262    1.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6526    2.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1028    3.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9486   -4.5464    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  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  4  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  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
  2 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220147

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)CC1OCC2=C1C(C=COC(=O)C=C(C)C)C1(C)CCC(C2C1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O4/c1-15(2)11-23(27)28-10-8-21-24-20(14-29-22(24)12-17(5)26)19-13-25(21,6)9-7-18(19)16(3)4/h8,10-11,18-19,21-22H,3,7,9,12-14H2,1-2,4-6H3

> <INCHI_KEY>
FJVYVOXCOKDRON-UHFFFAOYSA-N

> <FORMULA>
C25H34O4

> <MOLECULAR_WEIGHT>
398.543

> <EXACT_MASS>
398.245709575

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.501024686616276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
4.83

> <JCHEM_LOGP>
4.390288101333332

> <ALOGPS_LOGS>
-5.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.70588188586894

> <JCHEM_PKA_STRONGEST_BASIC>
-4.205330583168848

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
116.10409999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.006  -9.942   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.308  -8.569   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.149  -7.279   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.452  -5.906   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.914  -5.823   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.292  -4.615   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.595  -3.242   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.435  -1.952   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.738  -0.579   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.739   0.591   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.621   2.126   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.044   2.714   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.043   1.542   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.236   0.230   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.824  -1.194   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.350  -1.397   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.290  -0.176   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.938  -2.821   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.451   3.128   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.305   1.059   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.202  -0.697   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.725  -2.161   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.033   0.304   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.914   1.840   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.916   3.009   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.218   4.382   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.320   4.465   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.059   5.673   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.771  -8.487   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   11   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20    9   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   19   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    2                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
2-[8-Methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0,]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoic acid	Generator
2-[8-Methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₅H₃₄O₄

Average Mass

398.5430 Da

Monoisotopic Mass

398.24571 Da

IUPAC Name

2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate

Traditional Name

2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)CC1OCC2=C1C(C=COC(=O)C=C(C)C)C1(C)CCC(C2C1)C(C)=C

InChI Identifier

InChI=1S/C25H34O4/c1-15(2)11-23(27)28-10-8-21-24-20(14-29-22(24)12-17(5)26)19-13-25(21,6)9-7-18(19)16(3)4/h8,10-11,18-19,21-22H,3,7,9,12-14H2,1-2,4-6H3

InChI Key

FJVYVOXCOKDRON-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Fatty acid ester
Fatty acyl
Dihydrofuran
Enol ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
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
logP	4.83	ALOGPS
logP	4.39	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	18.71	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	116.1 m³·mol⁻¹	ChemAxon
Polarizability	45.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

85429108

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate (NP0220147)

MOL for NP0220147 (2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate)

3D MOL for NP0220147 (2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate)

3D SDF for NP0220147 (2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate)

3D-SDF for NP0220147 (2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate)

PDB for NP0220147 (2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate)

3D PDB for NP0220147 (2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate)

SMILES for NP0220147 (2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate)

INCHI for NP0220147 (2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate)

Structure for NP0220147 (2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate)

3D Structure for NP0220147 (2-[8-methyl-5-(2-oxopropyl)-11-(prop-1-en-2-yl)-4-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-en-7-yl]ethenyl 3-methylbut-2-enoate)