NP-MRD: Showing NP-Card for 4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one (NP0281628)

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Record Information

Version

2.0

Created at

2022-09-09 08:05:42 UTC

Updated at

2022-09-09 08:05:42 UTC

NP-MRD ID

NP0281628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one

Description

4-Hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]Non-3-en-2-one belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one is found in Hypericum perforatum. Based on a literature review very few articles have been published on 4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]Non-3-en-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092210052D          

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M  END

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M  END


  Mrv1652309092210052D          

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    2.7203   -3.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913   -3.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0219   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913    1.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2913    1.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0058    2.2857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769    2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376    1.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769    3.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535    0.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369    1.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3692   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1942   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6067   -0.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4317   -0.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8442   -1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8442   -0.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535   -0.7919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6369   -1.3753    0.0000 O   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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  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
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  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
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 30 36  2  0  0  0  0
 15 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281628

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)C12CC(CC=C(C)C)(CC(CC=C(C)C)C1CCC=C(C)C)C(O)=C(CC=C(C)C)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C34H52O3/c1-22(2)12-11-13-29-27(16-14-23(3)4)20-33(19-18-25(7)8)21-34(29,30(35)26(9)10)32(37)28(31(33)36)17-15-24(5)6/h12,14-15,18,26-27,29,36H,11,13,16-17,19-21H2,1-10H3

> <INCHI_KEY>
QOVWXXKVLJOKNW-UHFFFAOYSA-N

> <FORMULA>
C34H52O3

> <MOLECULAR_WEIGHT>
508.787

> <EXACT_MASS>
508.391645534

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
62.60454018531289

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one

> <JCHEM_LOGP>
9.521660448333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.935973915054202

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.846125522309439

> <JCHEM_PKA_STRONGEST_BASIC>
-6.516201669868587

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
161.4624

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one

> <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      -3.873  -1.316   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.475   0.172   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.564   1.261   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.987   0.570   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.589   2.058   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.101   2.456   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.988   1.367   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.398  -0.055   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.142  -0.055   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.912  -1.389   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.142  -2.723   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.912  -4.056   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.398  -2.723   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.988  -1.478   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.410  -2.068   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.410  -3.608   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.744  -4.378   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.744  -5.918   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.078  -6.688   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.410  -6.688   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.907  -0.055   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.410   1.957   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.410   3.497   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.744   4.267   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.077   4.267   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.257   3.497   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.077   5.807   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.833   1.367   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.922   2.456   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.423  -0.055   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.963  -0.055   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.733  -1.389   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.273  -1.389   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.043  -2.723   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.043  -0.055   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.833  -1.478   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.922  -2.567   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15                                                       
CONECT   15   14   16   21   36                                             
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   15   22                                                       
CONECT   22   21    7   23   28                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   36                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   30   15   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₅₂O₃

Average Mass

508.7870 Da

Monoisotopic Mass

508.39165 Da

IUPAC Name

4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one

Traditional Name

4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)C12CC(CC=C(C)C)(CC(CC=C(C)C)C1CCC=C(C)C)C(O)=C(CC=C(C)C)C2=O

InChI Identifier

InChI=1S/C34H52O3/c1-22(2)12-11-13-29-27(16-14-23(3)4)20-33(19-18-25(7)8)21-34(29,30(35)26(9)10)32(37)28(31(33)36)17-15-24(5)6/h12,14-15,18,26-27,29,36H,11,13,16-17,19-21H2,1-10H3

InChI Key

QOVWXXKVLJOKNW-UHFFFAOYSA-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
Hypericum perforatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Cyclohexenone
Vinylogous acid
Ketone
Enol
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	9.52	ChemAxon
pKa (Strongest Acidic)	5.85	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	161.46 m³·mol⁻¹	ChemAxon
Polarizability	62.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

163090547

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one (NP0281628)

MOL for NP0281628 (4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one)

3D MOL for NP0281628 (4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one)

3D SDF for NP0281628 (4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one)

3D-SDF for NP0281628 (4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one)

PDB for NP0281628 (4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one)

3D PDB for NP0281628 (4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one)

SMILES for NP0281628 (4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one)

INCHI for NP0281628 (4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one)

Structure for NP0281628 (4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one)

3D Structure for NP0281628 (4-hydroxy-3,5,7-tris(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-1-(2-methylpropanoyl)bicyclo[3.3.1]non-3-en-2-one)