NP-MRD: Showing NP-Card for methyl 1h,4h-cyclopenta[b]indole-1-carboxylate (NP0220810)

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Record Information

Version

1.0

Created at

2022-09-05 22:13:32 UTC

Updated at

2022-09-05 22:13:32 UTC

NP-MRD ID

NP0220810

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 1h,4h-cyclopenta[b]indole-1-carboxylate

Description

Methyl 1H,4H-cyclopenta[b]indole-1-carboxylate belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. methyl 1h,4h-cyclopenta[b]indole-1-carboxylate is found in Rhazya stricta. It was first documented in 2022 (PMID: 36075691). Based on a literature review a significant number of articles have been published on methyl 1H,4H-cyclopenta[b]indole-1-carboxylate (PMID: 36075690) (PMID: 36075689) (PMID: 36075688) (PMID: 36075687).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062200132D          

 16 18  0  0  0  0            999 V2000
    1.7331   -3.9376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7168   -3.1128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4230   -2.6863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1455   -3.0846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068   -1.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7299   -1.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693   -0.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7942   -0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4519   -0.0860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288   -0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9322   -0.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4962   -0.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568   -1.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534   -1.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894   -1.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645   -1.3635    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  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  2  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
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
  8 16  2  0  0  0  0
  5 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220810

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1C=CC2=C1C1=CC=CC=C1N2

> <INCHI_IDENTIFIER>
InChI=1S/C13H11NO2/c1-16-13(15)9-6-7-11-12(9)8-4-2-3-5-10(8)14-11/h2-7,9,14H,1H3

> <INCHI_KEY>
ZQBJNKLSHWFEPJ-UHFFFAOYSA-N

> <FORMULA>
C13H11NO2

> <MOLECULAR_WEIGHT>
213.236

> <EXACT_MASS>
213.078978598

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
22.78713578716127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 1H,4H-cyclopenta[b]indole-1-carboxylate

> <JCHEM_LOGP>
2.089111386333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.885820414893345

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.02639117647151

> <JCHEM_PKA_STRONGEST_BASIC>
-7.164892869268954

> <JCHEM_POLAR_SURFACE_AREA>
42.09

> <JCHEM_REFRACTIVITY>
62.02880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 1H,4H-cyclopenta[b]indole-1-carboxylate

> <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       3.235  -7.350   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.205  -5.811   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.523  -5.014   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.872  -5.758   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.493  -3.475   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.229  -2.594   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.676  -1.121   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.216  -1.090   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       6.444  -0.161   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       7.707  -1.041   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.207  -0.691   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.260  -1.815   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.813  -3.289   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.313  -3.639   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.260  -2.515   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.720  -2.545   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   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15    8    5                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
Methyl 1H,4H-cyclopenta[b]indole-1-carboxylic acid	Generator

Chemical Formula

C₁₃H₁₁NO₂

Average Mass

213.2360 Da

Monoisotopic Mass

213.07898 Da

IUPAC Name

methyl 1H,4H-cyclopenta[b]indole-1-carboxylate

Traditional Name

methyl 1H,4H-cyclopenta[b]indole-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1C=CC2=C1C1=CC=CC=C1N2

InChI Identifier

InChI=1S/C13H11NO2/c1-16-13(15)9-6-7-11-12(9)8-4-2-3-5-10(8)14-11/h2-7,9,14H,1H3

InChI Key

ZQBJNKLSHWFEPJ-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
Rhazya stricta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Benzenoid
Pyrrole
Methyl ester
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
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	2.09	ChemAxon
pKa (Strongest Acidic)	13.03	ChemAxon
pKa (Strongest Basic)	-7.2	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	2	ChemAxon
Refractivity	62.03 m³·mol⁻¹	ChemAxon
Polarizability	22.79 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

85702936

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abioye AI, Sudfeld CR, Hughes MD, Aboud S, Muhihi A, Ulenga N, Nagu TJ, Wang M, Mugusi F, Fawzi WW: Iron status among HIV-infected adults during the first year of antiretroviral therapy in Tanzania. HIV Med. 2022 Sep 8. doi: 10.1111/hiv.13396. [PubMed:36075691 ]
Authors unspecified: Resources Round-up. Altern Lab Anim. 2022 Sep 8:2611929221121256. doi: 10.1177/02611929221121256. [PubMed:36075690 ]
Kim JU, Khan W, Arowoshola L, Ahmad M: Correspondence. Eur Heart J Qual Care Clin Outcomes. 2022 Aug 26. pii: 6677390. doi: 10.1093/ehjqcco/qcac051. [PubMed:36075689 ]
DaVault L: Field Amputations Facilitated by a Surgical Extraction Team. Am Surg. 2022 Sep 8:31348221114521. doi: 10.1177/00031348221114521. [PubMed:36075688 ]
Szanyi J, Walles JK, Tesfaye F, Gudeta AN, Bjorkman P: Intrauterine HIV exposure is associated with linear growth restriction among Ethiopian children in the first 18 months of life. Trop Med Int Health. 2022 Sep;27(9):823-830. doi: 10.1111/tmi.13805. Epub 2022 Aug 17. [PubMed:36075687 ]
LOTUS database [Link]

Showing NP-Card for methyl 1h,4h-cyclopenta[b]indole-1-carboxylate (NP0220810)

MOL for NP0220810 (methyl 1h,4h-cyclopenta[b]indole-1-carboxylate)

3D MOL for NP0220810 (methyl 1h,4h-cyclopenta[b]indole-1-carboxylate)

3D SDF for NP0220810 (methyl 1h,4h-cyclopenta[b]indole-1-carboxylate)

3D-SDF for NP0220810 (methyl 1h,4h-cyclopenta[b]indole-1-carboxylate)

PDB for NP0220810 (methyl 1h,4h-cyclopenta[b]indole-1-carboxylate)

3D PDB for NP0220810 (methyl 1h,4h-cyclopenta[b]indole-1-carboxylate)

SMILES for NP0220810 (methyl 1h,4h-cyclopenta[b]indole-1-carboxylate)

INCHI for NP0220810 (methyl 1h,4h-cyclopenta[b]indole-1-carboxylate)

Structure for NP0220810 (methyl 1h,4h-cyclopenta[b]indole-1-carboxylate)

3D Structure for NP0220810 (methyl 1h,4h-cyclopenta[b]indole-1-carboxylate)