NP-MRD: Showing NP-Card for methyl 4-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate (NP0224026)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 02:16:49 UTC

Updated at

2022-09-06 02:16:49 UTC

NP-MRD ID

NP0224026

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate

Description

Costinone B belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated. methyl 4-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate is found in Isatis costata. Based on a literature review very few articles have been published on Costinone B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062204162D          

 24 26  0  0  0  0            999 V2000
    1.1809   -3.5477    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
    0.8838   -2.1500    0.0000 C   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
   -0.1712   -0.6979    0.0000 O   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
    0.8838    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371    1.2687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470    2.8379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739    2.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2428    1.1957    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  8 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 24  1  0  0  0  0
  4 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224026

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO\C=C1\C(=O)N(C2=CC=CC=C12)C1=CC(=CC=C1O)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C18H15NO5/c1-23-10-13-12-5-3-4-6-14(12)19(17(13)21)15-9-11(18(22)24-2)7-8-16(15)20/h3-10,20H,1-2H3/b13-10+

> <INCHI_KEY>
BOKWTIBYYIPGGY-JLHYYAGUSA-N

> <FORMULA>
C18H15NO5

> <MOLECULAR_WEIGHT>
325.32

> <EXACT_MASS>
325.095022587

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.60487852816023

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4-hydroxy-3-[(3E)-3-(methoxymethylidene)-2-oxo-2,3-dihydro-1H-indol-1-yl]benzoate

> <JCHEM_LOGP>
2.4064422476666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.551595452086249

> <JCHEM_PKA_STRONGEST_BASIC>
-2.132808010851143

> <JCHEM_POLAR_SURFACE_AREA>
76.07000000000001

> <JCHEM_REFRACTIVITY>
87.59140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-hydroxy-3-[(3E)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.680  -5.158   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.143   1.728   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.333   3.192   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.839   3.513   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.869   2.368   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.315   4.977   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.821   5.297   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.698   4.337   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.204   4.017   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.680   2.552   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.187   2.232   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   19                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   10   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    8   18                                                  
CONECT   18   17                                                            
CONECT   19    7   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19    4                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₅NO₅

Average Mass

325.3200 Da

Monoisotopic Mass

325.09502 Da

IUPAC Name

methyl 4-hydroxy-3-[(3E)-3-(methoxymethylidene)-2-oxo-2,3-dihydro-1H-indol-1-yl]benzoate

Traditional Name

methyl 4-hydroxy-3-[(3E)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate

CAS Registry Number

Not Available

SMILES

CO\C=C1\C(=O)N(C2=CC=CC=C12)C1=CC(=CC=C1O)C(=O)OC

InChI Identifier

InChI=1S/C18H15NO5/c1-23-10-13-12-5-3-4-6-14(12)19(17(13)21)15-9-11(18(22)24-2)7-8-16(15)20/h3-10,20H,1-2H3/b13-10+

InChI Key

BOKWTIBYYIPGGY-JLHYYAGUSA-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
Isatis costata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Acylaminobenzoic acid and derivatives

Alternative Parents

Substituents

Acylaminobenzoic acid or derivatives
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
Benzoate ester
Indole or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Tertiary carboxylic acid amide
Methyl ester
Vinylogous ester
Carboxamide group
Carboxylic acid ester
Lactam
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
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	2.41	ChemAxon
pKa (Strongest Acidic)	7.55	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	87.59 m³·mol⁻¹	ChemAxon
Polarizability	33.6 Å³	ChemAxon
Number of Rings	3	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

10019698

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11845224

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-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate (NP0224026)

MOL for NP0224026 (methyl 4-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate)

3D MOL for NP0224026 (methyl 4-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate)

3D SDF for NP0224026 (methyl 4-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate)

3D-SDF for NP0224026 (methyl 4-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate)

PDB for NP0224026 (methyl 4-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate)

3D PDB for NP0224026 (methyl 4-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate)

SMILES for NP0224026 (methyl 4-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate)

INCHI for NP0224026 (methyl 4-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate)

Structure for NP0224026 (methyl 4-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate)

3D Structure for NP0224026 (methyl 4-hydroxy-3-[(3e)-3-(methoxymethylidene)-2-oxoindol-1-yl]benzoate)