NP-MRD: Showing NP-Card for 3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione (NP0308093)

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Record Information

Version

2.0

Created at

2022-09-11 01:39:25 UTC

Updated at

2022-09-11 01:39:25 UTC

NP-MRD ID

NP0308093

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione

Description

3-(3,4-Dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]Non-3-ene-2,9-dione belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 3-(3,4-Dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]Non-3-ene-2,9-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004181500372D          

 39 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004181500372D          

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    0.0049    1.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5111    1.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352    0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477    0.9438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727   -0.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5852   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1727   -1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5852   -2.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3477   -1.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352   -2.6285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352   -1.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5206    0.2293    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  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  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 18 24  1  0  0  0  0
  7 24  1  0  0  0  0
 24 25  2  0  0  0  0
 18 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 31 38  1  0  0  0  0
  2 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308093

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1CC2(CC=C(C)C)C(=O)C(C(=O)C3=CC=C(O)C(O)=C3)=C(O)C(CC=C(C)C)(C2=O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O6/c1-19(2)9-11-23-18-32(15-13-20(3)4)28(37)26(27(36)22-10-12-24(34)25(35)17-22)29(38)33(30(32)39,31(23,7)8)16-14-21(5)6/h9-10,12-14,17,23,34-35,38H,11,15-16,18H2,1-8H3

> <INCHI_KEY>
OVMABFYNCKRCRE-UHFFFAOYSA-N

> <FORMULA>
C33H42O6

> <MOLECULAR_WEIGHT>
534.693

> <EXACT_MASS>
534.298139072

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
59.08789115713516

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione

> <ALOGPS_LOGP>
5.30

> <JCHEM_LOGP>
7.580605053666668

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.01984023428228

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2859780059722974

> <JCHEM_PKA_STRONGEST_BASIC>
-6.329947982345208

> <JCHEM_POLAR_SURFACE_AREA>
111.9

> <JCHEM_REFRACTIVITY>
157.90629999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  C   UNK     0      -4.705  -2.239   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.935  -0.906   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.395  -0.906   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.625   0.428   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.085   0.428   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.504  -0.995   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.927  -1.584   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.927  -3.124   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.593  -3.894   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.593  -5.434   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.740  -6.204   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.927  -6.204   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.350  -0.995   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.439  -2.084   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.939   0.428   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.350   1.851   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.439   2.940   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.927   2.440   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.927   3.980   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.261   4.750   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.261   6.290   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.594   7.060   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.927   7.060   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.424   0.428   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.178   1.333   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.504   1.851   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.009   3.309   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.954   2.346   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.479   0.428   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.249   1.762   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.249  -0.906   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.789  -0.906   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.559  -2.239   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.789  -3.573   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.559  -4.907   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.249  -3.573   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.479  -4.907   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.479  -2.239   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -4.705   0.428   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13   24                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   29                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   24   26                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   18    7   25                                                  
CONECT   25   24                                                            
CONECT   26   18    5   27   28                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   15   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   38                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   31                                                       
CONECT   39    2                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₂O₆

Average Mass

534.6930 Da

Monoisotopic Mass

534.29814 Da

IUPAC Name

3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione

Traditional Name

3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CCC1CC2(CC=C(C)C)C(=O)C(C(=O)C3=CC=C(O)C(O)=C3)=C(O)C(CC=C(C)C)(C2=O)C1(C)C

InChI Identifier

InChI=1S/C33H42O6/c1-19(2)9-11-23-18-32(15-13-20(3)4)28(37)26(27(36)22-10-12-24(34)25(35)17-22)29(38)33(30(32)39,31(23,7)8)16-14-21(5)6/h9-10,12-14,17,23,34-35,38H,11,15-16,18H2,1-8H3

InChI Key

OVMABFYNCKRCRE-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

Not Available

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

Aromatic monoterpenoid
Bicyclic monoterpenoid
Benzoyl
Catechol
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Cyclohexenone
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Enol
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	5.3	ALOGPS
logP	7.58	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	157.91 m³·mol⁻¹	ChemAxon
Polarizability	59.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione (NP0308093)

MOL for NP0308093 (3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

3D MOL for NP0308093 (3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

3D SDF for NP0308093 (3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

3D-SDF for NP0308093 (3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

PDB for NP0308093 (3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

3D PDB for NP0308093 (3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

SMILES for NP0308093 (3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

INCHI for NP0308093 (3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

Structure for NP0308093 (3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)

3D Structure for NP0308093 (3-(3,4-dihydroxybenzoyl)-4-hydroxy-6,6-dimethyl-1,5,7-tris(3-methylbut-2-en-1-yl)bicyclo[3.3.1]non-3-ene-2,9-dione)