NP-MRD: Showing NP-Card for Indobinine (NP0067431)

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Record Information

Version

2.0

Created at

2022-04-28 12:17:27 UTC

Updated at

2022-04-28 12:17:27 UTC

NP-MRD ID

NP0067431

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Indobinine

Description

ZINC14517206 belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Indobinine is found in Rauwolfia serpentina. ZINC14517206 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
    0.9258   -2.0076   -0.4715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167   -0.9959    0.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7617   -0.8204    0.6710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3416    0.3820   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7125    0.5752    0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1425    1.4912    1.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4626    1.3176    1.5316 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9138    0.3358    0.7365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1723   -0.1892    0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2833   -1.2085   -0.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2223   -1.7100   -1.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9725   -1.1732   -0.8795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8155   -0.1414    0.0399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5515   -0.0296    0.4504 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8714   -0.1462    0.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8383   -0.0598    1.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1500    0.5538    0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039    0.2641   -0.5721 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524    0.5493   -1.5985 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2590    1.0195   -0.9166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7990   -0.6760    1.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4159   -1.6888    0.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6909    1.2671    0.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3968    0.1293   -1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947    2.2040    1.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0667    1.8717    2.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0405    0.1820    1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2870   -1.6089   -0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3164   -2.5057   -1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0850   -1.5204   -1.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0910   -1.0977   -0.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3206    0.6321    1.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8880   -1.0230    1.7049 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1282    1.6489    1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9184    0.1526    1.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4844    0.9145   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9953   -0.7831   -0.6213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8831    1.2368   -2.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2807   -0.4487   -2.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5298    1.9163   -0.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5048    1.1903   -1.6966 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 13  5  1  0
 20 15  1  0
 13  8  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 17 34  1  0
 17 35  1  0
 18 36  1  0
 18 37  1  0
 19 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
M  END


  Mrv1533004261511332D          

 20 22  0  0  0  0            999 V2000
    3.8184   -0.8334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8184   -0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1039    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3895   -0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6750    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9213    0.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3693    0.6817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7818    1.3961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5269    2.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0789    2.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8859    2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1408    1.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5888    1.2246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5329    0.4041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2474   -0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9618    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6763   -0.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6763   -0.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9618   -1.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2474   -0.8334    0.0000 C   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  1  0  0  0  0
  5  6  2  0  0  0  0
  6  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  5 13  1  0  0  0  0
  8 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067431

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C(CCC1=CNC2=CC=CC=C12)OC1CCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO2/c19-17(20-14-6-2-1-3-7-14)11-10-13-12-18-16-9-5-4-8-15(13)16/h4-5,8-9,12,14,18H,1-3,6-7,10-11H2

> <INCHI_KEY>
WRQDMKSMJOELTQ-UHFFFAOYSA-N

> <FORMULA>
C17H21NO2

> <MOLECULAR_WEIGHT>
271.36

> <EXACT_MASS>
271.15722892

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.676512393120362

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
cyclohexyl 3-(1H-indol-3-yl)propanoate

> <ALOGPS_LOGP>
4.36

> <JCHEM_LOGP>
4.099489350999999

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.16477771704231

> <JCHEM_PKA_STRONGEST_BASIC>
-7.045154798809591

> <JCHEM_POLAR_SURFACE_AREA>
42.09

> <JCHEM_REFRACTIVITY>
78.83640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.24e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclohexyl 3-(1H-indol-3-yl)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  O   UNK     0       7.128  -1.556   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.128  -0.016   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.794   0.754   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.460  -0.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.127   0.754   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.720   0.128   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.689   1.272   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.459   2.606   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.983   4.071   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.014   5.215   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.520   4.895   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.996   3.430   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.966   2.286   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.461   0.754   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.795  -0.016   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.129   0.754   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.462  -0.016   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.462  -1.556   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.129  -2.326   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.795  -1.556   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5    8                                                  
CONECT   14    2   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₁NO₂

Average Mass

271.3600 Da

Monoisotopic Mass

271.15723 Da

IUPAC Name

cyclohexyl 3-(1H-indol-3-yl)propanoate

Traditional Name

cyclohexyl 3-(1H-indol-3-yl)propanoate

CAS Registry Number

Not Available

SMILES

O=C(CCC1=CNC2=CC=CC=C12)OC1CCCCC1

InChI Identifier

InChI=1S/C17H21NO2/c19-17(20-14-6-2-1-3-7-14)11-10-13-12-18-16-9-5-4-8-15(13)16/h4-5,8-9,12,14,18H,1-3,6-7,10-11H2

InChI Key

WRQDMKSMJOELTQ-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
Rauvolfia serpentina	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
3-alkylindole
Indole
Fatty acid ester
Substituted pyrrole
Benzenoid
Fatty acyl
Pyrrole
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Carbonyl group
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
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	4.36	ALOGPS
logP	4.1	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	16.16	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	42.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	78.84 m³·mol⁻¹	ChemAxon
Polarizability	30.68 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

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

13946437

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Indobinine (NP0067431)

MOL for NP0067431 (Indobinine)

3D MOL for NP0067431 (Indobinine)

3D SDF for NP0067431 (Indobinine)

3D-SDF for NP0067431 (Indobinine)

PDB for NP0067431 (Indobinine)

3D PDB for NP0067431 (Indobinine)

SMILES for NP0067431 (Indobinine)

INCHI for NP0067431 (Indobinine)

Structure for NP0067431 (Indobinine)

3D Structure for NP0067431 (Indobinine)