NP-MRD: Showing NP-Card for (-)-peganine (NP0247197)

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Record Information

Version

2.0

Created at

2022-09-07 08:56:54 UTC

Updated at

2022-09-07 08:56:55 UTC

NP-MRD ID

NP0247197

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-peganine

Description

Vasicine, also known as peganine, belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring. (-)-peganine is found in Justicia adhatoda, Anisotes trisulcus, Galega lindblomii, Galega officinalis, Justicia pectoralis, Nitraria komarovii, Peganum harmala and Peganum nigellastrum. (-)-peganine was first documented in 2022 (PMID: 35422700). Based on a literature review a small amount of articles have been published on Vasicine (PMID: 35809281) (PMID: 36049600) (PMID: 35850647) (PMID: 35691257).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072210562D          

 14 16  0  0  1  0            999 V2000
    1.5983   -3.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 N   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
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 14  1  0  0  0  0
  5 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247197

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CCN2CC3=CC=CC=C3N=C12

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O/c14-10-5-6-13-7-8-3-1-2-4-9(8)12-11(10)13/h1-4,10,14H,5-7H2/t10-/m0/s1

> <INCHI_KEY>
YIICVSCAKJMMDJ-JTQLQIEISA-N

> <FORMULA>
C11H12N2O

> <MOLECULAR_WEIGHT>
188.23

> <EXACT_MASS>
188.094963014

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.452892101894985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-3-ol

> <JCHEM_LOGP>
0.6625927100000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.752518371435471

> <JCHEM_PKA_STRONGEST_BASIC>
8.22105827193539

> <JCHEM_POLAR_SURFACE_AREA>
35.83

> <JCHEM_REFRACTIVITY>
56.30140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       2.983  -6.323   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       4.924  -2.843   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.258  -5.153   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       4.924  -4.383   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   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    2    5                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

View in JSmol

Synonyms

Value	Source
Peganine hydrochloride dihydrate	MeSH
Vasicine monohydrochloride, (R)-isomer	MeSH
Vasicine, (+-)-isomer	MeSH
Peganine	MeSH
Vasicine hydrochloride, (R)-isomer	MeSH

Chemical Formula

C₁₁H₁₂N₂O

Average Mass

188.2300 Da

Monoisotopic Mass

188.09496 Da

IUPAC Name

(3S)-1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-3-ol

Traditional Name

(3S)-1H,2H,3H,9H-pyrrolo[2,1-b]quinazolin-3-ol

CAS Registry Number

Not Available

SMILES

O[C@H]1CCN2CC3=CC=CC=C3N=C12

InChI Identifier

InChI=1S/C11H12N2O/c14-10-5-6-13-7-8-3-1-2-4-9(8)12-11(10)13/h1-4,10,14H,5-7H2/t10-/m0/s1

InChI Key

YIICVSCAKJMMDJ-JTQLQIEISA-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
Adhatoda vasica	LOTUS Database	35616633
Anisotes trisulcus	LOTUS Database	35616633
Galega lindblomii	LOTUS Database	35616633
Galega officinalis	LOTUS Database	35616633
Justicia pectoralis	LOTUS Database	35616633
Nitraria komarovii	LOTUS Database	35616633
Peganum harmala	LOTUS Database	35616633
Peganum nigellastrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Benzodiazines

Direct Parent

Quinazolines

Alternative Parents

Substituents

Quinazoline
N-alkylpyrrolidine
Benzenoid
Imidolactam
Pyrrolidine
Secondary alcohol
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Amidine
Carboxylic acid amidine
Alcohol
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
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	0.66	ChemAxon
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	8.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	35.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	56.3 m³·mol⁻¹	ChemAxon
Polarizability	20.45 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00002149

Chemspider ID

580873

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vasicine

METLIN ID

Not Available

PubChem Compound

667496

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Iftikhar F, Rahman S, Khan MBN, Khan K, Khan MN, Uddin R, Musharraf SG: In Vitro and In Vivo Studies for the Investigation of gamma-Globin Gene Induction by Adhatoda vasica: A Pre-Clinical Study of HbF Inducers for beta-Thalassemia. Front Pharmacol. 2022 Mar 29;13:797853. doi: 10.3389/fphar.2022.797853. eCollection 2022. [PubMed:35422700 ]
Shoaib A: A systematic ethnobotanical review of Adhatoda vasica (L.), Nees. Cell Mol Biol (Noisy-le-grand). 2022 Jan 2;67(4):248-263. doi: 10.14715/cmb/2021.67.4.28. [PubMed:35809281 ]
Zhang Y, Du W, Zhu D, Li M, Qu L, Rao G, Lin Y, Tong X, Sun Y, Huang F: Vasicine alleviates 2,4-dinitrochlorobenzene-induced atopic dermatitis and passive cutaneous anaphylaxis in BALB/c mice. Clin Immunol. 2022 Nov;244:109102. doi: 10.1016/j.clim.2022.109102. Epub 2022 Aug 30. [PubMed:36049600 ]
Thangaraju P, Narasimhan G, Ramamurthy VA, Gurunthalingam MP, Yella SST, Venkatesan S, Thangaraju E: Molecular Docking Analysis of Adhatoda vasica with Thromboxane A(2) Receptor (TXA(2)R) (6IIU) and Antiviral Molecules for Possible Dengue Complications. Infect Disord Drug Targets. 2023;23(1):e180722206836. doi: 10.2174/1871526522666220718101544. [PubMed:35850647 ]
Singh B, Sahu PM, Aloria M, Reddy SS, Prasad J, Sharma RA: Azotobacter chroococcum and Pseudomonas putida enhance pyrroloquinazoline alkaloids accumulation in Adhatoda vasica hairy roots by biotization. J Biotechnol. 2022 Jul 20;353:51-60. doi: 10.1016/j.jbiotec.2022.05.011. Epub 2022 Jun 10. [PubMed:35691257 ]
LOTUS database [Link]

Showing NP-Card for (-)-peganine (NP0247197)

MOL for NP0247197 ((-)-peganine)

3D MOL for NP0247197 ((-)-peganine)

3D SDF for NP0247197 ((-)-peganine)

3D-SDF for NP0247197 ((-)-peganine)

PDB for NP0247197 ((-)-peganine)

3D PDB for NP0247197 ((-)-peganine)

SMILES for NP0247197 ((-)-peganine)

INCHI for NP0247197 ((-)-peganine)

Structure for NP0247197 ((-)-peganine)

3D Structure for NP0247197 ((-)-peganine)