NP-MRD: Showing NP-Card for 4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid (NP0290518)

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Record Information

Version

2.0

Created at

2022-09-09 21:14:38 UTC

Updated at

2022-09-09 21:14:39 UTC

NP-MRD ID

NP0290518

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid

Description

4-(3,6-Dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Based on a literature review very few articles have been published on 4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -4.7863   -0.2477    0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4807    0.4202    0.2938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5203    0.1473    1.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2650    0.9173    1.0766 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2208    0.3731    1.8101 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3127   -0.6619    1.0534 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7531   -0.9213    1.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6382    0.2065    1.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6406    0.0796    0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8715   -1.2204   -0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5251    1.1876   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3327    2.2849    0.5378 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5555    1.0427   -0.9101 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0675   -0.3420   -0.3850 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6530   -1.5126   -1.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7733    0.8961   -0.3316 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8243    0.9822   -1.3725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1135    1.4847   -0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1858   -0.1404   -0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7740   -1.3162    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4849    0.3369    0.8986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232   -0.6036    1.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3843    1.9762    1.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539   -1.5881    1.3668 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0844   -1.8150    0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830   -1.2090    2.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4868    1.1760    1.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0709   -1.9670    0.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204   -1.5205   -1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7601   -1.1785   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4761    0.9308   -1.9138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0129   -0.2129   -0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6532   -1.6765   -0.5271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7126   -1.4591   -2.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0600   -2.4228   -0.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0957    1.7883   -0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0882    0.0307   -1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5609    1.7172   -2.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8858    2.3958   -0.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8920    1.6413   -1.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 13  1  0
 11 12  2  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 18  1  0
 18 17  1  0
 17 16  1  0
 16 14  1  0
 16  4  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 14 32  1  6
  6 24  1  1
  7 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
  4 23  1  1
  3 22  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 18 39  1  0
 18 40  1  0
 17 37  1  0
 17 38  1  0
 16 36  1  1
M  END


  Mrv1652309092223142D          

 18 19  0  0  0  0            999 V2000
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    0.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909   -0.6205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284    0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    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
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0290518

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C(CC=C(C)C(O)=O)OC2C=C(C)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-9-4-6-12-11(3)13(18-14(12)8-9)7-5-10(2)15(16)17/h5,8,11-14H,4,6-7H2,1-3H3,(H,16,17)

> <INCHI_KEY>
ACWHPYSUDDTJQF-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.338

> <EXACT_MASS>
250.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.98968853887544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid

> <JCHEM_LOGP>
3.118946775

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.682234835331536

> <JCHEM_PKA_STRONGEST_BASIC>
-4.199917975587815

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
71.7435

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid

> <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       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.023   1.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.793   2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.793   0.175   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.023  -1.158   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -7.333   0.175   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.744   5.553   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    4   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
4-(3,6-Dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoate	Generator

Chemical Formula

C₁₅H₂₂O₃

Average Mass

250.3380 Da

Monoisotopic Mass

250.15689 Da

IUPAC Name

4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid

Traditional Name

4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC1C(CC=C(C)C(O)=O)OC2C=C(C)CCC12

InChI Identifier

InChI=1S/C15H22O3/c1-9-4-6-12-11(3)13(18-14(12)8-9)7-5-10(2)15(16)17/h5,8,11-14H,4,6-7H2,1-3H3,(H,16,17)

InChI Key

ACWHPYSUDDTJQF-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 benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Branched fatty acid
Heterocyclic fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Tetrahydrofuran
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxygen 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	3.12	ChemAxon
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.74 m³·mol⁻¹	ChemAxon
Polarizability	27.99 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

163089877

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid (NP0290518)

MOL for NP0290518 (4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid)

3D MOL for NP0290518 (4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid)

3D SDF for NP0290518 (4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid)

3D-SDF for NP0290518 (4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid)

PDB for NP0290518 (4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid)

3D PDB for NP0290518 (4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid)

SMILES for NP0290518 (4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid)

INCHI for NP0290518 (4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid)

Structure for NP0290518 (4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid)

3D Structure for NP0290518 (4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid)