NP-MRD: Showing NP-Card for gamma-dichroine (NP0262518)

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Record Information

Version

2.0

Created at

2022-09-08 05:21:36 UTC

Updated at

2022-09-08 05:21:37 UTC

NP-MRD ID

NP0262518

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gamma-dichroine

Description

3-[3-(3-Hydroxypiperidin-2-yl)-2-oxopropyl]-3,4-dihydroquinazolin-4-one 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. gamma-dichroine is found in Hydrangea febrifuga. 3-[3-(3-Hydroxypiperidin-2-yl)-2-oxopropyl]-3,4-dihydroquinazolin-4-one is a very strong basic 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
   -0.4431   -1.6937   -1.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4352   -0.7663   -0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1721   -0.8598    0.8809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6214   -0.4753    0.7415 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7379    0.9260    0.4809 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8803    1.3783   -0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0521    0.4838   -0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8768   -0.9311    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4162   -1.3021   -0.2049 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2819   -1.0446   -1.5348 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2867    0.5097   -0.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243    0.3534   -0.7027 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3204    0.0760   -1.8901 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6586   -0.0847   -2.0119 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4823    0.0225   -0.9536 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8477   -0.1380   -1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6607   -0.0212    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1169    0.2581    1.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7341    0.4168    1.3758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9078    0.3044    0.2725 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5211    0.4658    0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0121    0.7209    1.4814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0752   -1.9140    1.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287   -0.2291    1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0740   -0.6412    1.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5078    1.5218    1.2769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2352    2.3262    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5564    1.7933   -1.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9413    0.8848    0.2257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3694    0.4557   -1.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4971   -1.6275   -0.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0392   -1.0685    1.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391   -2.3756    0.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7100   -0.3356   -1.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0230    1.3116    0.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0527    0.8414   -1.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6549   -0.0108   -2.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966   -0.3599   -2.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7141   -0.1574   -0.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7489    0.3521    2.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2787    0.6337    2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  4  9  1  0
 21 12  1  0
 20 15  1  0
 10 34  1  0
  9 33  1  6
  8 31  1  0
  8 32  1  0
  7 29  1  0
  7 30  1  0
  6 27  1  0
  6 28  1  0
  5 26  1  0
  4 25  1  1
  3 23  1  0
  3 24  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END


  Mrv1533004171519352D          

 22 24  0  0  0  0            999 V2000
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    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
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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  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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0262518

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CCCNC1CC(=O)CN1C=NC2=CC=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19N3O3/c20-11(8-14-15(21)6-3-7-17-14)9-19-10-18-13-5-2-1-4-12(13)16(19)22/h1-2,4-5,10,14-15,17,21H,3,6-9H2

> <INCHI_KEY>
FWVHWDSCPKXMDB-UHFFFAOYSA-N

> <FORMULA>
C16H19N3O3

> <MOLECULAR_WEIGHT>
301.346

> <EXACT_MASS>
301.142641484

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.43170792767578

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]-3,4-dihydroquinazolin-4-one

> <ALOGPS_LOGP>
0.01

> <JCHEM_LOGP>
0.33671957200000013

> <ALOGPS_LOGS>
-2.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.912393507081465

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.475525513862745

> <JCHEM_PKA_STRONGEST_BASIC>
9.284795636826106

> <JCHEM_POLAR_SURFACE_AREA>
82.0

> <JCHEM_REFRACTIVITY>
83.43919999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-dichroine

> <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       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -2.667  -7.700   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   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   21                                                  
CONECT   21   20   12   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Isofebrifugine	MeSH

Chemical Formula

C₁₆H₁₉N₃O₃

Average Mass

301.3460 Da

Monoisotopic Mass

301.14264 Da

IUPAC Name

3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]-3,4-dihydroquinazolin-4-one

Traditional Name

gamma-dichroine

CAS Registry Number

Not Available

SMILES

OC1CCCNC1CC(=O)CN1C=NC2=CC=CC=C2C1=O

InChI Identifier

InChI=1S/C16H19N3O3/c20-11(8-14-15(21)6-3-7-17-14)9-19-10-18-13-5-2-1-4-12(13)16(19)22/h1-2,4-5,10,14-15,17,21H,3,6-9H2

InChI Key

FWVHWDSCPKXMDB-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
Dichroa febrifuga	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
Pyrimidone
Beta-aminoketone
Piperidine
Pyrimidine
Benzenoid
Heteroaromatic compound
1,2-aminoalcohol
Ketone
Lactam
Secondary alcohol
Secondary aliphatic amine
Azacycle
Secondary amine
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Alcohol
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	0.01	ALOGPS
logP	0.34	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.48	ChemAxon
pKa (Strongest Basic)	9.28	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.44 m³·mol⁻¹	ChemAxon
Polarizability	30.43 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

115723

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for gamma-dichroine (NP0262518)

MOL for NP0262518 (gamma-dichroine)

3D MOL for NP0262518 (gamma-dichroine)

3D SDF for NP0262518 (gamma-dichroine)

3D-SDF for NP0262518 (gamma-dichroine)

PDB for NP0262518 (gamma-dichroine)

3D PDB for NP0262518 (gamma-dichroine)

SMILES for NP0262518 (gamma-dichroine)

INCHI for NP0262518 (gamma-dichroine)

Structure for NP0262518 (gamma-dichroine)

3D Structure for NP0262518 (gamma-dichroine)