NP-MRD: Showing NP-Card for {8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid (NP0197047)

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Record Information

Version

2.0

Created at

2022-09-04 15:14:36 UTC

Updated at

2022-09-04 15:14:36 UTC

NP-MRD ID

NP0197047

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid

Description

2-{8-Formyl-3,6,8-trimethyl-2-oxo-octahydro-2H-cyclohepta[b]furan-7-yl}acetic acid belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. {8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid is found in Ambrosia artemisiifolia. 2-{8-Formyl-3,6,8-trimethyl-2-oxo-octahydro-2H-cyclohepta[b]furan-7-yl}acetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -3.5693   -0.4452    1.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9039   -0.4448    0.3445 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7875   -1.7826   -0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6044   -2.7312   -0.1861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6062   -1.8295   -0.9915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9002   -0.5850   -0.8332 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4130   -0.0677    0.4418 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3007    1.4404    0.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0765    1.7960    0.8711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1719    1.4899   -0.0966 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9073    2.2262   -1.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5054    0.0694   -0.2891 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0070   -0.6158    0.9295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2495   -0.0841    1.5194 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8781    0.8375    1.0078 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6623   -0.7100    2.7113 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5290   -0.7646   -1.0450 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7843   -0.6892   -2.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708   -2.2010   -0.7000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7219   -2.8050   -1.3188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563   -1.3498    1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8552   -0.1925    2.5002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3043    0.4126    1.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3757    0.2673   -0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3326    0.0546   -1.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0691   -0.5359    1.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6443    1.8428   -0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9820    1.7804    1.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0959    2.9187    1.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2427    1.3830    1.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0737    1.9954    0.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0206    3.3289   -1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7172    2.0068   -2.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0990    2.0984   -1.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4169    0.1013   -0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727   -0.6217    1.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2616   -1.6910    0.6727 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6092   -1.0685    2.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0925    0.0505   -3.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8360   -0.4890   -2.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5244   -1.6667   -3.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3762   -2.7294    0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 12 17  1  0
 17 18  1  0
 17 19  1  1
 19 20  2  0
 17  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  6  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  6
  7 26  1  1
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  1
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  6
 13 36  1  0
 13 37  1  0
 16 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
  6 25  1  6
M  END


  Mrv1533004191518262D          

 20 21  0  0  0  0            999 V2000
    4.3735    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    1.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    0.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    1.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7017    0.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3533    1.8011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    2.4686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    2.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    2.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    3.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7442    3.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2795    4.1529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    2.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7050    3.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208    3.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0351    3.7115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8222    2.2985    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197047

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CCC(C)C(CC(O)=O)C(C)(C=O)C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-8-4-5-10-9(2)14(19)20-13(10)15(3,7-16)11(8)6-12(17)18/h7-11,13H,4-6H2,1-3H3,(H,17,18)

> <INCHI_KEY>
ZECPBXBUYRVNDP-UHFFFAOYSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.336

> <EXACT_MASS>
282.146723808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
29.21136898259063

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{8-formyl-3,6,8-trimethyl-2-oxo-octahydro-2H-cyclohepta[b]furan-7-yl}acetic acid

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
1.8964343730000006

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.387839625148998

> <JCHEM_PKA_STRONGEST_BASIC>
-6.817976532312929

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
70.72189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3H-cyclohepta[b]furan-7-yl}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       8.164   3.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.624   3.362   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.956   1.975   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.454   1.632   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.250   2.592   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.786   2.116   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.310   0.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.881   3.362   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.659   3.362   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.786   4.608   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.250   4.132   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.454   5.092   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.250   6.052   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.123   6.480   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.255   7.752   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.956   4.750   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.916   5.954   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.439   5.724   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.399   6.928   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.001   4.291   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13   14   16                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16   12    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
2-{8-formyl-3,6,8-trimethyl-2-oxo-octahydro-2H-cyclohepta[b]furan-7-yl}acetate	Generator

Chemical Formula

C₁₅H₂₂O₅

Average Mass

282.3360 Da

Monoisotopic Mass

282.14672 Da

IUPAC Name

2-{8-formyl-3,6,8-trimethyl-2-oxo-octahydro-2H-cyclohepta[b]furan-7-yl}acetic acid

Traditional Name

{8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3H-cyclohepta[b]furan-7-yl}acetic acid

CAS Registry Number

Not Available

SMILES

CC1C2CCC(C)C(CC(O)=O)C(C)(C=O)C2OC1=O

InChI Identifier

InChI=1S/C15H22O5/c1-8-4-5-10-9(2)14(19)20-13(10)15(3,7-16)11(8)6-12(17)18/h7-11,13H,4-6H2,1-3H3,(H,17,18)

InChI Key

ZECPBXBUYRVNDP-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
Ambrosia artemisiifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	1.81	ALOGPS
logP	1.9	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.39	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.72 m³·mol⁻¹	ChemAxon
Polarizability	29.21 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

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 {8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid (NP0197047)

MOL for NP0197047 ({8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid)

3D MOL for NP0197047 ({8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid)

3D SDF for NP0197047 ({8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid)

3D-SDF for NP0197047 ({8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid)

PDB for NP0197047 ({8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid)

3D PDB for NP0197047 ({8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid)

SMILES for NP0197047 ({8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid)

INCHI for NP0197047 ({8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid)

Structure for NP0197047 ({8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid)

3D Structure for NP0197047 ({8-formyl-3,6,8-trimethyl-2-oxo-hexahydro-3h-cyclohepta[b]furan-7-yl}acetic acid)