NP-MRD: Showing NP-Card for 3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid (NP0237576)

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Record Information

Version

2.0

Created at

2022-09-06 20:45:21 UTC

Updated at

2022-09-06 20:45:21 UTC

NP-MRD ID

NP0237576

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid

Description

3-[2-(Furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-3,6-dihydro-2H-pyran-3-yl]propanoic acid belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid is found in Xylocarpus granatum. 3-[2-(Furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-3,6-dihydro-2H-pyran-3-yl]propanoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231519222D          

 36 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004231519222D          

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 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 25 29  1  0  0  0  0
 24 30  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0237576

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1C(C)C(=O)C(CC(=O)C2=CC(=O)OC(C3=COC=C3)C2(C)CCC(O)=O)=CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O9/c1-15-18(11-22(31)34-5)26(2,3)13-17(24(15)33)10-20(28)19-12-23(32)36-25(16-7-9-35-14-16)27(19,4)8-6-21(29)30/h7,9,12-15,18,25H,6,8,10-11H2,1-5H3,(H,29,30)

> <INCHI_KEY>
IYEWDOOFXNMWEJ-UHFFFAOYSA-N

> <FORMULA>
C27H32O9

> <MOLECULAR_WEIGHT>
500.544

> <EXACT_MASS>
500.20463261

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
50.701235298584265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-3,6-dihydro-2H-pyran-3-yl]propanoic acid

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
3.7428445409999993

> <ALOGPS_LOGS>
-4.34

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.960253462084616

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.291868225315647

> <JCHEM_PKA_STRONGEST_BASIC>
-2.887919844265881

> <JCHEM_POLAR_SURFACE_AREA>
137.18

> <JCHEM_REFRACTIVITY>
128.5888

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2H-pyran-3-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -6.868  12.745   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.534  13.515   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.200  12.745   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.200  11.205   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.867  13.515   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.533  12.745   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.199  13.515   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.199  15.055   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.134  12.745   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.468  13.515   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.134  11.205   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.199  10.435   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.533  11.205   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.349   9.899   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.072  11.151   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.468  10.435   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.468   8.895   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.134   8.125   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.802   8.125   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.136   8.895   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.469   8.125   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.803   8.895   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.469   6.585   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.136   5.815   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.136   4.275   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.890   3.370   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.366   1.905   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.906   1.905   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.381   3.370   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.802   6.585   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.986   5.279   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.263   6.531   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.540   5.172   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.001   5.118   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.815   6.424   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -0.722   3.758   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                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   30                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   25                                                       
CONECT   30   24   19   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
3-[2-(Furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-3,6-dihydro-2H-pyran-3-yl]propanoate	Generator

Chemical Formula

C₂₇H₃₂O₉

Average Mass

500.5440 Da

Monoisotopic Mass

500.20463 Da

IUPAC Name

3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-3,6-dihydro-2H-pyran-3-yl]propanoic acid

Traditional Name

3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2H-pyran-3-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)CC1C(C)C(=O)C(CC(=O)C2=CC(=O)OC(C3=COC=C3)C2(C)CCC(O)=O)=CC1(C)C

InChI Identifier

InChI=1S/C27H32O9/c1-15-18(11-22(31)34-5)26(2,3)13-17(24(15)33)10-20(28)19-12-23(32)36-25(16-7-9-35-14-16)27(19,4)8-6-21(29)30/h7,9,12-15,18,25H,6,8,10-11H2,1-5H3,(H,29,30)

InChI Key

IYEWDOOFXNMWEJ-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
Xylocarpus granatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Dihydropyranone
Cyclohexenone
Pyran
Furan
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Carboxylic acid
Organoheterocyclic compound
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	3.15	ALOGPS
logP	3.74	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	137.18 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	128.59 m³·mol⁻¹	ChemAxon
Polarizability	50.7 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid (NP0237576)

MOL for NP0237576 (3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid)

3D MOL for NP0237576 (3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid)

3D SDF for NP0237576 (3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid)

3D-SDF for NP0237576 (3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid)

PDB for NP0237576 (3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid)

3D PDB for NP0237576 (3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid)

SMILES for NP0237576 (3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid)

INCHI for NP0237576 (3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid)

Structure for NP0237576 (3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid)

3D Structure for NP0237576 (3-[2-(furan-3-yl)-4-{2-[4-(2-methoxy-2-oxoethyl)-3,3,5-trimethyl-6-oxocyclohex-1-en-1-yl]acetyl}-3-methyl-6-oxo-2h-pyran-3-yl]propanoic acid)