NP-MRD: Showing NP-Card for methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate (NP0316870)

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Record Information

Version

1.0

Created at

2022-09-11 16:20:50 UTC

Updated at

2022-09-11 16:20:50 UTC

NP-MRD ID

NP0316870

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate

Description

Methyl 4-(1H-indol-3-yl)-2-methyl-4-oxobut-2-enoate belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate is found in Murraya paniculata. Methyl 4-(1H-indol-3-yl)-2-methyl-4-oxobut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
    6.0271    0.9263   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8441    0.1416   -0.1861 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6198    0.7559   -0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5768    1.9787    0.1895 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4043   -0.0197   -0.1158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4953   -1.4984   -0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2108    0.5167    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0111   -0.2399   -0.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0088   -1.5028   -0.2807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3140    0.3950    0.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4912    1.7360    0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8274    1.9840    0.4497 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5228    0.8497    0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8560    0.5122    0.2719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2818   -0.7870    0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3519   -1.7825   -0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0143   -1.4365   -0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5795   -0.1486    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9423    1.7119   -0.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1588    1.3570    0.9102 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9209    0.2795   -0.2736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1199   -2.0524    0.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0521   -1.7869   -1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5821   -1.7911   -0.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1573    1.5771    0.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7459    2.5183    0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2824    2.9072    0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6163    1.2637    0.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3526   -1.0387    0.0586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6438   -2.8106   -0.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2293   -2.1891   -0.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 10  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  6 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END


  Mrv1533004161504102D          

 18 19  0  0  0  0            999 V2000
   -2.6412   -1.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8342   -1.2669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371   -2.6646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.9238    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 12 17  1  0  0  0  0
  5 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316870

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(C)=CC(=O)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C14H13NO3/c1-9(14(17)18-2)7-13(16)11-8-15-12-6-4-3-5-10(11)12/h3-8,15H,1-2H3

> <INCHI_KEY>
DOTJZAALWJYBRD-UHFFFAOYSA-N

> <FORMULA>
C14H13NO3

> <MOLECULAR_WEIGHT>
243.262

> <EXACT_MASS>
243.089543283

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
25.639404157758513

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4-(1H-indol-3-yl)-2-methyl-4-oxobut-2-enoate

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
2.5868645893333335

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.77050147543498

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.014526712808237

> <JCHEM_PKA_STRONGEST_BASIC>
-6.776269016548157

> <JCHEM_POLAR_SURFACE_AREA>
59.160000000000004

> <JCHEM_REFRACTIVITY>
68.63680000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-(1H-indol-3-yl)-2-methyl-4-oxobut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -4.930  -2.685   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.424  -2.365   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.393  -3.509   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.869  -4.974   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.887  -3.189   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.680  -5.158   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.411  -1.724   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    9   12                                                  
CONECT   18    5                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4-(1H-indol-3-yl)-2-methyl-4-oxobut-2-enoic acid	Generator

Chemical Formula

C₁₄H₁₃NO₃

Average Mass

243.2620 Da

Monoisotopic Mass

243.08954 Da

IUPAC Name

methyl 4-(1H-indol-3-yl)-2-methyl-4-oxobut-2-enoate

Traditional Name

methyl 4-(1H-indol-3-yl)-2-methyl-4-oxobut-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(C)=CC(=O)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C14H13NO3/c1-9(14(17)18-2)7-13(16)11-8-15-12-6-4-3-5-10(11)12/h3-8,15H,1-2H3

InChI Key

DOTJZAALWJYBRD-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
Murraya paniculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

Substituents

Indole
Aryl ketone
Fatty acid ester
Substituted pyrrole
Benzenoid
Fatty acyl
Heteroaromatic compound
Enone
Pyrrole
Acryloyl-group
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Alpha,beta-unsaturated ketone
Vinylogous amide
Carboxylic acid ester
Ketone
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organic oxygen 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	2.53	ALOGPS
logP	2.59	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.01	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.16 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.64 m³·mol⁻¹	ChemAxon
Polarizability	25.64 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

73159299

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate (NP0316870)

MOL for NP0316870 (methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate)

3D MOL for NP0316870 (methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate)

3D SDF for NP0316870 (methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate)

3D-SDF for NP0316870 (methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate)

PDB for NP0316870 (methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate)

3D PDB for NP0316870 (methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate)

SMILES for NP0316870 (methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate)

INCHI for NP0316870 (methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate)

Structure for NP0316870 (methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate)

3D Structure for NP0316870 (methyl 4-(1h-indol-3-yl)-2-methyl-4-oxobut-2-enoate)