NP-MRD: Showing NP-Card for 5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid (NP0220831)

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Record Information

Version

2.0

Created at

2022-09-05 22:15:03 UTC

Updated at

2022-09-05 22:15:03 UTC

NP-MRD ID

NP0220831

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid

Description

5-{[7-Hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxo-5,8-dihydro-2H-chromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid is found in Clusia nemorosa. 5-{[7-Hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxo-5,8-dihydro-2H-chromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171507382D          

 37 38  0  0  0  0            999 V2000
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    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 29 36  1  0  0  0  0
  7 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004171507382D          

 37 38  0  0  0  0            999 V2000
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    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4256   -2.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 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
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  4  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 32 35  1  0  0  0  0
 28 35  1  0  0  0  0
 29 36  1  0  0  0  0
  7 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0220831

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)C1=C(O)C(CC=C(C)C)(CC(CC=C(C)C(O)=O)C(C)=C)C2=C(C=CC(C)(C)O2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H42O6/c1-10-20(6)25(32)24-26(33)23-14-15-30(8,9)37-28(23)31(27(24)34,16-13-18(2)3)17-22(19(4)5)12-11-21(7)29(35)36/h11,13-15,20,22,34H,4,10,12,16-17H2,1-3,5-9H3,(H,35,36)

> <INCHI_KEY>
NOXCMVJSVNXOIM-UHFFFAOYSA-N

> <FORMULA>
C31H42O6

> <MOLECULAR_WEIGHT>
510.671

> <EXACT_MASS>
510.298139072

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.990400996367384

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxo-5,8-dihydro-2H-chromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid

> <ALOGPS_LOGP>
4.81

> <JCHEM_LOGP>
6.486806416333334

> <ALOGPS_LOGS>
-5.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.642812530913105

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7389625637305515

> <JCHEM_PKA_STRONGEST_BASIC>
-4.88504023084677

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
151.4655

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.14e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid

> <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      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.990  -4.260   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.506  -3.992   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.496  -5.172   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.013  -4.905   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.970  -6.619   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.990  -4.260   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.463  -5.707   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.053  -5.974   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.580  -7.421   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.097  -7.689   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.087  -6.509   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.623  -9.136   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.140  -9.403   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.634 -10.316   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.453  -6.887   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.926  -8.334   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.970  -6.619   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.518  -2.043   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.528  -3.757   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   36                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   16   28                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   17   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   10   29   35                                                  
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34   35                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   32   28                                                       
CONECT   36   29    7   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Value	Source
5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxo-5,8-dihydro-2H-chromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoate	Generator

Chemical Formula

C₃₁H₄₂O₆

Average Mass

510.6710 Da

Monoisotopic Mass

510.29814 Da

IUPAC Name

5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxo-5,8-dihydro-2H-chromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid

Traditional Name

5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)C1=C(O)C(CC=C(C)C)(CC(CC=C(C)C(O)=O)C(C)=C)C2=C(C=CC(C)(C)O2)C1=O

InChI Identifier

InChI=1S/C31H42O6/c1-10-20(6)25(32)24-26(33)23-14-15-30(8,9)37-28(23)31(27(24)34,16-13-18(2)3)17-22(19(4)5)12-11-21(7)29(35)36/h11,13-15,20,22,34H,4,10,12,16-17H2,1-3,5-9H3,(H,35,36)

InChI Key

NOXCMVJSVNXOIM-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
Clusia nemorosa	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
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Pyran
Vinylogous ester
Vinylogous acid
Ketone
Carboxylic acid derivative
Carboxylic acid
Enol
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
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	4.81	ALOGPS
logP	6.49	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	3.74	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	151.47 m³·mol⁻¹	ChemAxon
Polarizability	55.99 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

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 5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid (NP0220831)

MOL for NP0220831 (5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid)

3D MOL for NP0220831 (5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid)

3D SDF for NP0220831 (5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid)

3D-SDF for NP0220831 (5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid)

PDB for NP0220831 (5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid)

3D PDB for NP0220831 (5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid)

SMILES for NP0220831 (5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid)

INCHI for NP0220831 (5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid)

Structure for NP0220831 (5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid)

3D Structure for NP0220831 (5-{[7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-en-1-yl)-6-(2-methylbutanoyl)-5-oxochromen-8-yl]methyl}-2,6-dimethylhepta-2,6-dienoic acid)