NP-MRD: Showing NP-Card for Melosatin B (NP0050885)

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Record Information

Version

2.0

Created at

2022-04-27 22:20:52 UTC

Updated at

2022-04-27 22:20:53 UTC

NP-MRD ID

NP0050885

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Melosatin B

Description

4-(5-Phenylpentyl)-2,3-dihydro-1H-indole-2,3-dione belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole. Melosatin B is found in Melochia tomentosa . 4-(5-Phenylpentyl)-2,3-dihydro-1H-indole-2,3-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -3.9232    3.4974   -1.5219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0054    2.2930   -1.1739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9539    1.2898   -1.5075 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6173    0.0736   -0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2488   -1.1402   -0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7509   -2.2066   -0.1679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5963   -2.0432    0.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9473   -0.8305    0.6357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292   -0.6659    1.4150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4459   -0.7155    0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6736   -0.5234    1.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0427   -0.5457    1.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2097    0.5480    0.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5458    0.5923   -0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734    1.3259   -0.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8268    1.3295   -0.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0485    0.6078   -1.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0247   -0.1191   -2.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7924   -0.1187   -1.7244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4634    0.2173   -0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0656    1.6148   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0554    2.1269    0.2655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7645    1.4588   -2.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1565   -1.2488   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2860   -3.1395   -0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2541   -2.9156    1.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7056    0.2877    1.9828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -1.4901    2.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3593   -1.7485    0.1536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417    0.0130   -0.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4557    0.4339    2.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5128   -1.3154    2.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2724   -1.5447    0.6248 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7451   -0.3050    1.8868 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.3931   -0.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9944    1.5336    0.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4140    1.8861    0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6509    1.9022   -0.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0144    0.6085   -2.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1640   -0.7029   -3.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0111   -0.7142   -2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  8 20  2  0
 20 21  1  0
 21 22  2  0
 21  2  1  0
 20  4  1  0
 19 14  1  0
  3 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END


  Mrv1533004171503542D          

 22 24  0  0  0  0            999 V2000
    2.1190   -2.0202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7065   -1.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860   -1.2195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0420   -0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490   -0.3805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  8 20  2  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0050885

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1NC2=CC=CC(CCCCCC3=CC=CC=C3)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H19NO2/c21-18-17-15(12-7-13-16(17)20-19(18)22)11-6-2-5-10-14-8-3-1-4-9-14/h1,3-4,7-9,12-13H,2,5-6,10-11H2,(H,20,21,22)

> <INCHI_KEY>
FHHUFXFTSWTUMR-UHFFFAOYSA-N

> <FORMULA>
C19H19NO2

> <MOLECULAR_WEIGHT>
293.366

> <EXACT_MASS>
293.141578856

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.95952984935347

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(5-phenylpentyl)-2,3-dihydro-1H-indole-2,3-dione

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
5.471612248333334

> <ALOGPS_LOGS>
-5.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.923477775996682

> <JCHEM_PKA_STRONGEST_BASIC>
-5.327215820215976

> <JCHEM_POLAR_SURFACE_AREA>
46.17

> <JCHEM_REFRACTIVITY>
88.61619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.43e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
melosatin B

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       3.955  -3.771   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.185  -2.437   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.654  -2.276   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.812  -1.030   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.318  -0.710   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    8    4   21                                                  
CONECT   21   20    2   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₉NO₂

Average Mass

293.3660 Da

Monoisotopic Mass

293.14158 Da

IUPAC Name

4-(5-phenylpentyl)-2,3-dihydro-1H-indole-2,3-dione

Traditional Name

melosatin B

CAS Registry Number

Not Available

SMILES

O=C1NC2=CC=CC(CCCCCC3=CC=CC=C3)=C2C1=O

InChI Identifier

InChI=1S/C19H19NO2/c21-18-17-15(12-7-13-16(17)20-19(18)22)11-6-2-5-10-14-8-3-1-4-9-14/h1,3-4,7-9,12-13H,2,5-6,10-11H2,(H,20,21,22)

InChI Key

FHHUFXFTSWTUMR-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Melochia tomentosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolines

Direct Parent

Indolines

Alternative Parents

Substituents

Dihydroindole
Aryl ketone
Monocyclic benzene moiety
Benzenoid
Vinylogous amide
Carboxamide group
Ketone
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indoles (CHEBI:6740 )

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	4.5	ALOGPS
logP	5.47	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	8.92	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.17 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	88.62 m³·mol⁻¹	ChemAxon
Polarizability	32.96 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

C00001747

Chemspider ID

Not Available

KEGG Compound ID

C09222

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

Not Available

Showing NP-Card for Melosatin B (NP0050885)

MOL for NP0050885 (Melosatin B)

3D MOL for NP0050885 (Melosatin B)

3D SDF for NP0050885 (Melosatin B)

3D-SDF for NP0050885 (Melosatin B)

PDB for NP0050885 (Melosatin B)

3D PDB for NP0050885 (Melosatin B)

SMILES for NP0050885 (Melosatin B)

INCHI for NP0050885 (Melosatin B)

Structure for NP0050885 (Melosatin B)

3D Structure for NP0050885 (Melosatin B)