NP-MRD: Showing NP-Card for (3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol (NP0149252)

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Record Information

Version

2.0

Created at

2022-09-02 05:07:13 UTC

Updated at

2022-09-02 05:07:14 UTC

NP-MRD ID

NP0149252

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol

Description

Vasicinol 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. (3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol is found in Linaria vulgaris and Sida cordifolia. (3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol was first documented in 2015 (PMID: 25849329). Based on a literature review a small amount of articles have been published on Vasicinol (PMID: 35422700) (PMID: 34834066) (PMID: 33488726) (PMID: 35809281).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207072D          

 15 17  0  0  1  0            999 V2000
    5.4957    0.6979    0.0000 O   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
    4.7812    1.9354    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    1.9354    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
    4.0668    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  2  7  1  0  0  0  0
  6  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  1  0  0  0
 12 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
  5 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149252

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2O2/c14-8-1-2-9-7(5-8)6-13-4-3-10(15)11(13)12-9/h1-2,5,10,14-15H,3-4,6H2/t10-/m1/s1

> <INCHI_KEY>
WEFMOGRHGUPGMA-SNVBAGLBSA-N

> <FORMULA>
C11H12N2O2

> <MOLECULAR_WEIGHT>
204.229

> <EXACT_MASS>
204.089877634

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.48339612537733

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-1H,2H,3H,9H-pyrrolo[2,1-b]quinazoline-3,7-diol

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
0.5483974663854023

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.753383745749261

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.672293183949076

> <JCHEM_PKA_STRONGEST_BASIC>
9.671176665248787

> <JCHEM_POLAR_SURFACE_AREA>
56.06

> <JCHEM_REFRACTIVITY>
58.282300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-1H,2H,3H,9H-pyrrolo[2,1-b]quinazoline-3,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0      10.259   1.303   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+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   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.590   2.073   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.924   4.383   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    9   15                                                  
CONECT   15   14    5                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂N₂O₂

Average Mass

204.2290 Da

Monoisotopic Mass

204.08988 Da

IUPAC Name

(3R)-1H,2H,3H,9H-pyrrolo[2,1-b]quinazoline-3,7-diol

Traditional Name

(3R)-1H,2H,3H,9H-pyrrolo[2,1-b]quinazoline-3,7-diol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C11H12N2O2/c14-8-1-2-9-7(5-8)6-13-4-3-10(15)11(13)12-9/h1-2,5,10,14-15H,3-4,6H2/t10-/m1/s1

InChI Key

WEFMOGRHGUPGMA-SNVBAGLBSA-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
Linaria vulgaris	LOTUS Database	35616633
Sida cordifolia	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
Phenol
1-hydroxy-2-unsubstituted benzenoid
N-alkylpyrrolidine
Imidolactam
Benzenoid
Pyrrolidine
Secondary alcohol
Organic 1,3-dipolar compound
Azacycle
Carboxylic acid amidine
Amidine
Propargyl-type 1,3-dipolar organic compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Amine
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	0.19	ALOGPS
logP	0.55	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	56.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	58.28 m³·mol⁻¹	ChemAxon
Polarizability	21.48 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

C00002201

Chemspider ID

4954700

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6452262

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 ]
Tehreem S, Rahman S, Bhatti MS, Uddin R, Khan MN, Tauseef S, El-Seedi HR, Bin Muhsinah A, Uddin J, Musharraf SG: A UPLC-DAD-Based Bio-Screening Assay for the Evaluation of the Angiotensin Converting Enzyme Inhibitory Potential of Plant Extracts and Compounds: Pyrroquinazoline Alkaloids from Adhatoda vasica as a Case Study. Molecules. 2021 Nov 18;26(22). pii: molecules26226971. doi: 10.3390/molecules26226971. [PubMed:34834066 ]
Sebola TE, Uche-Okereafor NC, Mekuto L, Makatini MM, Green E, Mavumengwana V: Antibacterial and Anticancer Activity and Untargeted Secondary Metabolite Profiling of Crude Bacterial Endophyte Extracts from Crinum macowanii Baker Leaves. Int J Microbiol. 2020 Dec 10;2020:8839490. doi: 10.1155/2020/8839490. eCollection 2020. [PubMed:33488726 ]
Liu W, Shi X, Yang Y, Cheng X, Liu Q, Han H, Yang B, He C, Wang Y, Jiang B, Wang Z, Wang C: In vitro and in vivo metabolism and inhibitory activities of vasicine, a potent acetylcholinesterase and butyrylcholinesterase inhibitor. PLoS One. 2015 Apr 7;10(4):e0122366. doi: 10.1371/journal.pone.0122366. eCollection 2015. [PubMed:25849329 ]
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 ]
LOTUS database [Link]

Showing NP-Card for (3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol (NP0149252)

MOL for NP0149252 ((3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol)

3D MOL for NP0149252 ((3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol)

3D SDF for NP0149252 ((3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol)

3D-SDF for NP0149252 ((3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol)

PDB for NP0149252 ((3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol)

3D PDB for NP0149252 ((3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol)

SMILES for NP0149252 ((3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol)

INCHI for NP0149252 ((3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol)

Structure for NP0149252 ((3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol)

3D Structure for NP0149252 ((3r)-1h,2h,3h,9h-pyrrolo[2,1-b]quinazoline-3,7-diol)