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Showing NP-Card for (2r,5e,10r)-5-methyl-2-[(2r)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate (NP0196678)

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Record Information
Version2.0
Created at2022-09-04 14:48:24 UTC
Updated at2022-09-04 14:48:24 UTC
NP-MRD IDNP0196678
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r,5e,10r)-5-methyl-2-[(2r)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate
DescriptionIsoacetylcoriacenone belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom). (2r,5e,10r)-5-methyl-2-[(2r)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate is found in Dictyota spiralis. (2r,5e,10r)-5-methyl-2-[(2r)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate was first documented in 1993 (PMID: 8277314). Based on a literature review very few articles have been published on isoacetylcoriacenone.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0196678 ((2r,5e,10r)-5-methyl-2-[(2r)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate)


  Mrv1652309042216482D          

 25 26  0  0  1  0            999 V2000
   -1.4800    1.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8811    1.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0903    1.4248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731    0.3876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743   -0.1799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4521   -1.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196   -1.6034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3726   -0.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504   -0.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635    0.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    0.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9748   -0.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7001   -0.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4674   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389   -1.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357   -1.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197   -1.5999    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5266   -2.3252    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2981   -2.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581   -3.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650   -3.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966   -4.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6035   -5.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0350   -5.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2212   -5.2042    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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
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3D MOL for NP0196678 ((2r,5e,10r)-5-methyl-2-[(2r)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate)

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3D SDF for NP0196678 ((2r,5e,10r)-5-methyl-2-[(2r)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate)

  Mrv1652309042216482D          

 25 26  0  0  1  0            999 V2000
   -1.4800    1.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8811    1.1899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0903    1.4248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731    0.3876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743   -0.1799    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4521   -1.0046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196   -1.6034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3726   -0.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504   -0.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8635    0.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    0.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9748   -0.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7001   -0.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4674   -0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389   -1.2897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7357   -1.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9197   -1.5999    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5266   -2.3252    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2981   -2.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581   -3.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650   -3.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9966   -4.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6035   -5.1820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0350   -5.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2212   -5.2042    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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196678

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCC=C(C)C)[C@H]1CC\C(C)=C\CCC2[C@@H](OC(C)=O)C(=O)C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O3/c1-14(2)8-6-10-16(4)18-13-12-15(3)9-7-11-19-20(18)21(24)22(19)25-17(5)23/h8-9,16,18-20,22H,6-7,10-13H2,1-5H3/b15-9+/t16-,18-,19?,20?,22-/m1/s1

> <INCHI_KEY>
SOAIWELMVRCOAD-GIAKDNIESA-N

> <FORMULA>
C22H34O3

> <MOLECULAR_WEIGHT>
346.511

> <EXACT_MASS>
346.250794955

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
40.65633531181828

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,5E,10R)-5-methyl-2-[(2R)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate

> <JCHEM_LOGP>
5.395953699

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.938113330709566

> <JCHEM_PKA_STRONGEST_BASIC>
-6.982430081331709

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
102.83739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5E,10R)-5-methyl-2-[(2R)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0196678 ((2r,5e,10r)-5-methyl-2-[(2r)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate)
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PDB for NP0196678 ((2r,5e,10r)-5-methyl-2-[(2r)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate)
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      -2.763   3.280   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.645   2.221   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.168   2.660   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.003   0.723   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.885  -0.336   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.844  -1.875   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.903  -2.993   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.696  -1.834   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.654  -0.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.612   0.912   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.121   1.220   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.686  -0.213   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.040  -0.947   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.473  -0.381   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.553  -2.407   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.240  -3.213   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.717  -2.986   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.983  -4.340   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.556  -4.382   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.789  -5.653   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.055  -7.007   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.860  -8.319   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.126  -9.673   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.932 -10.986   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.413  -9.715   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   17                                                  
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

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3D PDB for NP0196678 ((2r,5e,10r)-5-methyl-2-[(2r)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate)
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SMILES for NP0196678 ((2r,5e,10r)-5-methyl-2-[(2r)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate)
C[C@H](CCC=C(C)C)[C@H]1CC\C(C)=C\CCC2[C@@H](OC(C)=O)C(=O)C12
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INCHI for NP0196678 ((2r,5e,10r)-5-methyl-2-[(2r)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate)
InChI=1S/C22H34O3/c1-14(2)8-6-10-16(4)18-13-12-15(3)9-7-11-19-20(18)21(24)22(19)25-17(5)23/h8-9,16,18-20,22H,6-7,10-13H2,1-5H3/b15-9+/t16-,18-,19?,20?,22-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC22H34O3
Average Mass346.5110 Da
Monoisotopic Mass346.25079 Da
IUPAC Name(2R,5E,10R)-5-methyl-2-[(2R)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate
Traditional Name(2R,5E,10R)-5-methyl-2-[(2R)-6-methylhept-5-en-2-yl]-11-oxobicyclo[7.2.0]undec-5-en-10-yl acetate
CAS Registry NumberNot Available
SMILES
C[C@H](CCC=C(C)C)[C@H]1CC\C(C)=C\CCC2[C@@H](OC(C)=O)C(=O)C12
InChI Identifier
InChI=1S/C22H34O3/c1-14(2)8-6-10-16(4)18-13-12-15(3)9-7-11-19-20(18)21(24)22(19)25-17(5)23/h8-9,16,18-20,22H,6-7,10-13H2,1-5H3/b15-9+/t16-,18-,19?,20?,22-/m1/s1
InChI KeySOAIWELMVRCOAD-GIAKDNIESA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Dictyota spiralisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAlpha-acyloxy ketones  
Alternative Parents
Substituents
  • Alpha-acyloxy ketone
    • 

  • Ketone
    • 

  • Carboxylic acid ester
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.4ChemAxon
pKa (Strongest Acidic)16.94ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity102.84 m³·mol⁻¹ChemAxon
Polarizability40.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24694847  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44584503  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Bouaicha N, Pesando D, Puel D, Tringali C: Cytotoxic diterpenoids from the brown alga Dilophus ligulatus. J Nat Prod. 1993 Oct;56(10):1747-52. doi: 10.1021/np50100a013. [PubMed:8277314  ] 
  2. LOTUS database [Link]