NP-MRD: Showing NP-Card for (1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate (NP0249902)

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Record Information

Version

2.0

Created at

2022-09-07 12:35:33 UTC

Updated at

2022-09-07 12:35:33 UTC

NP-MRD ID

NP0249902

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate

Description

3,5-Bis(3-methyl-2-butenyl)-4-hydroxybenzoic acid 1-isopropyl-4-methyl-3-cyclohexen-1beta-yl ester belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group. (1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate is found in Piper aduncum. Based on a literature review very few articles have been published on 3,5-Bis(3-methyl-2-butenyl)-4-hydroxybenzoic acid 1-isopropyl-4-methyl-3-cyclohexen-1beta-yl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072214352D          

 30 31  0  0  1  0            999 V2000
   -3.1178    1.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034    0.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889    1.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034   -0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889   -0.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889   -1.3402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -1.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9744   -2.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600   -2.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545   -2.5777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2600   -3.8152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4545   -4.2277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0758   -4.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2064   -5.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882   -4.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7367   -3.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5492   -3.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0795   -3.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919   -3.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7973   -4.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9848   -4.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889   -2.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034   -2.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1178   -2.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8323   -2.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5468   -2.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2612   -2.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5468   -3.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034   -1.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1178   -1.3402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 68 69  0  0  0  0  0  0  0  0999 V2000
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    4.3922   -2.9830    0.5114 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0476   -2.4078    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3774    1.5280    1.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7488    1.5797    0.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5320    2.8080    1.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9599    3.5400    0.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5788    4.7839   -0.0640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7173    5.4607    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0069    5.5252   -1.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772    0.4343    0.5400 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309072214352D          

 30 31  0  0  1  0            999 V2000
   -3.1178    1.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4034    0.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0249902

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@]1(CCC(C)=CC1)OC(=O)C1=CC(CC=C(C)C)=C(O)C(CC=C(C)C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O3/c1-18(2)8-10-22-16-24(17-23(25(22)28)11-9-19(3)4)26(29)30-27(20(5)6)14-12-21(7)13-15-27/h8-9,12,16-17,20,28H,10-11,13-15H2,1-7H3/t27-/m0/s1

> <INCHI_KEY>
PYSQNLGCMZDKLK-MHZLTWQESA-N

> <FORMULA>
C27H38O3

> <MOLECULAR_WEIGHT>
410.598

> <EXACT_MASS>
410.282095084

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.24978517667655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate

> <JCHEM_LOGP>
7.979073493333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.105185796654753

> <JCHEM_PKA_STRONGEST_BASIC>
-6.168646995644992

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
128.5964

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.820   2.118   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.486   1.348   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.153   2.118   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.486  -0.192   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.153  -0.962   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.153  -2.502   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.819  -3.272   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.819  -4.812   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.485  -5.582   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.848  -4.812   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -0.485  -7.122   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.848  -7.892   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.141  -9.071   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.385 -10.519   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.658  -8.804   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.375  -6.445   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.892  -6.177   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.882  -7.357   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.398  -7.089   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.355  -8.804   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.838  -9.071   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.153  -5.582   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.486  -4.812   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.820  -5.582   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.154  -4.812   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.487  -5.582   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.821  -4.812   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.487  -7.122   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.486  -3.272   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.820  -2.502   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   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   22                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   16   21                                             
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   12   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   12                                                       
CONECT   22    8   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   23    6   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
3,5-Bis(3-methyl-2-butenyl)-4-hydroxybenzoate 1-isopropyl-4-methyl-3-cyclohexen-1b-yl ester	Generator
3,5-Bis(3-methyl-2-butenyl)-4-hydroxybenzoate 1-isopropyl-4-methyl-3-cyclohexen-1beta-yl ester	Generator
3,5-Bis(3-methyl-2-butenyl)-4-hydroxybenzoate 1-isopropyl-4-methyl-3-cyclohexen-1β-yl ester	Generator
3,5-Bis(3-methyl-2-butenyl)-4-hydroxybenzoic acid 1-isopropyl-4-methyl-3-cyclohexen-1b-yl ester	Generator
3,5-Bis(3-methyl-2-butenyl)-4-hydroxybenzoic acid 1-isopropyl-4-methyl-3-cyclohexen-1β-yl ester	Generator

Chemical Formula

C₂₇H₃₈O₃

Average Mass

410.5980 Da

Monoisotopic Mass

410.28210 Da

IUPAC Name

(1R)-4-methyl-1-(propan-2-yl)cyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate

Traditional Name

(1R)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate

CAS Registry Number

Not Available

SMILES

CC(C)[C@]1(CCC(C)=CC1)OC(=O)C1=CC(CC=C(C)C)=C(O)C(CC=C(C)C)=C1

InChI Identifier

InChI=1S/C27H38O3/c1-18(2)8-10-22-16-24(17-23(25(22)28)11-9-19(3)4)26(29)30-27(20(5)6)14-12-21(7)13-15-27/h8-9,12,16-17,20,28H,10-11,13-15H2,1-7H3/t27-/m0/s1

InChI Key

PYSQNLGCMZDKLK-MHZLTWQESA-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
Piper aduncum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

p-Hydroxybenzoic acid alkyl esters

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
P-menthane monoterpenoid
Monoterpenoid
Monocyclic monoterpenoid
Aromatic monoterpenoid
Benzoyl
Phenol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	7.98	ChemAxon
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-6.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	128.6 m³·mol⁻¹	ChemAxon
Polarizability	49.25 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	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

101661252

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate (NP0249902)

MOL for NP0249902 ((1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate)

3D MOL for NP0249902 ((1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate)

3D SDF for NP0249902 ((1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate)

3D-SDF for NP0249902 ((1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate)

PDB for NP0249902 ((1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate)

3D PDB for NP0249902 ((1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate)

SMILES for NP0249902 ((1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate)

INCHI for NP0249902 ((1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate)

Structure for NP0249902 ((1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate)

3D Structure for NP0249902 ((1r)-1-isopropyl-4-methylcyclohex-3-en-1-yl 4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)benzoate)