NP-MRD: Showing NP-Card for 3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid (NP0160597)

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Record Information

Version

2.0

Created at

2022-09-02 18:34:50 UTC

Updated at

2022-09-02 18:34:50 UTC

NP-MRD ID

NP0160597

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid

Description

CHEMBL516883 belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. 3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid is found in Calophyllum brasiliense. Based on a literature review very few articles have been published on CHEMBL516883.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220342D          

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  Mrv1652309022220342D          

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 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160597

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1OC2=C(C(=O)[C@@H]1C)C(=O)C(CCC(C)=C)(C=C(C)C)C(O)=C2C(CC(O)=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H34O6/c1-16(2)12-13-29(15-17(3)4)27(33)23(21(14-22(30)31)20-10-8-7-9-11-20)26-24(28(29)34)25(32)18(5)19(6)35-26/h7-11,15,18-19,21,33H,1,12-14H2,2-6H3,(H,30,31)/t18-,19+,21?,29?/m1/s1

> <INCHI_KEY>
GZNWWAGBASVLIH-KDEHGAQWSA-N

> <FORMULA>
C29H34O6

> <MOLECULAR_WEIGHT>
478.585

> <EXACT_MASS>
478.235538815

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.39213593754546

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2S,3R)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-3,4,5,6-tetrahydro-2H-1-benzopyran-8-yl]-3-phenylpropanoic acid

> <ALOGPS_LOGP>
3.35

> <JCHEM_LOGP>
5.085738073333335

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.796315369636222

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.376160927644948

> <JCHEM_PKA_STRONGEST_BASIC>
-4.898791598138642

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
137.35029999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.92e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2S,3R)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.914  -6.651   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.397  -6.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.407  -7.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.870  -4.937   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.860  -3.757   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.850  -2.043   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.840  -3.222   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.357  -2.955   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.313  -4.669   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+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   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001   3.850   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -2.667   0.000   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   11   34                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   13   21                                                  
CONECT   21   20                                                            
CONECT   22   14   23   34                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   22    6   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₄O₆

Average Mass

478.5850 Da

Monoisotopic Mass

478.23554 Da

IUPAC Name

3-[(2S,3R)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-3,4,5,6-tetrahydro-2H-1-benzopyran-8-yl]-3-phenylpropanoic acid

Traditional Name

3-[(2S,3R)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1OC2=C(C(=O)[C@@H]1C)C(=O)C(CCC(C)=C)(C=C(C)C)C(O)=C2C(CC(O)=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C29H34O6/c1-16(2)12-13-29(15-17(3)4)27(33)23(21(14-22(30)31)20-10-8-7-9-11-20)26-24(28(29)34)25(32)18(5)19(6)35-26/h7-11,15,18-19,21,33H,1,12-14H2,2-6H3,(H,30,31)/t18-,19+,21?,29?/m1/s1

InChI Key

GZNWWAGBASVLIH-KDEHGAQWSA-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
Calophyllum brasiliense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
Aromatic monoterpenoid
Benzopyran
Bicyclic monoterpenoid
Monoterpenoid
Dihydropyranone
Monocyclic benzene moiety
Benzenoid
Vinylogous ester
Ketone
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Enol
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	3.35	ALOGPS
logP	5.09	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.38	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	8	ChemAxon
Refractivity	137.35 m³·mol⁻¹	ChemAxon
Polarizability	51.39 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

44566695

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid (NP0160597)

MOL for NP0160597 (3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid)

3D MOL for NP0160597 (3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid)

3D SDF for NP0160597 (3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid)

3D-SDF for NP0160597 (3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid)

PDB for NP0160597 (3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid)

3D PDB for NP0160597 (3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid)

SMILES for NP0160597 (3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid)

INCHI for NP0160597 (3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid)

Structure for NP0160597 (3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid)

3D Structure for NP0160597 (3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid)