NP-MRD: Showing NP-Card for Isofebrifugine (NP0051233)

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Record Information

Version

2.0

Created at

2022-04-27 22:37:30 UTC

Updated at

2022-04-27 22:37:30 UTC

NP-MRD ID

NP0051233

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isofebrifugine

Description

3-{[(2S,3aS,7aR)-2-hydroxy-octahydrofuro[3,2-b]pyridin-2-yl]methyl}-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. Isofebrifugine is found in Dichroa febrifuga , Hydrangea macrophylla and Hydrangea umbellata. Based on a literature review very few articles have been published on 3-{[(2S,3aS,7aR)-2-hydroxy-octahydrofuro[3,2-b]pyridin-2-yl]methyl}-3,4-dihydroquinazolin-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
    1.8757    0.2382   -2.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1306    0.4891   -0.9738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1114   -0.2482   -0.3264 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8223   -1.2537   -0.9481 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962   -1.9835   -0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0938   -1.7132    1.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3843   -0.7054    1.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4056    0.0174    0.9951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7106    0.9985    1.5984 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487    1.7143    0.9467 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482    1.4697   -0.3414 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4303    2.2320   -1.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9319    1.6165   -0.9074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8862    2.3808   -1.5783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4077    1.4936    0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5165    0.5007    0.2782 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9324   -0.2494    1.4003 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9795   -1.1507    0.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5188   -2.0509   -0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7609   -1.3248   -1.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7381   -0.4640   -0.6344 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0003    0.3364   -1.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6268   -1.4977   -1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3677   -2.7756   -0.7617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8595   -2.2917    1.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5853   -0.4667    2.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2143    2.5041    1.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6572    2.3099   -2.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3557    3.2725   -0.6512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6016    3.3034   -1.6931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6134    0.9990    1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7548    2.4435    0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3096    0.9339   -0.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3910    0.3800    2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4154   -1.7479    1.7103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7644   -0.4641    0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4100   -2.4933   -0.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8359   -2.8341    0.2274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4447   -0.6832   -1.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3179   -2.1094   -1.9322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0930   -1.1261    0.0117 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  6
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 13  1  0
  2 11  1  0
 21 16  1  0
  3  8  1  0
 14 30  1  0
 12 28  1  0
 12 29  1  0
 10 27  1  0
  7 26  1  0
  6 25  1  0
  5 24  1  0
  4 23  1  0
 15 31  1  0
 15 32  1  0
 16 33  1  6
 17 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  1
M  END


  Mrv1652304282200372D          

 22 25  0  0  1  0            999 V2000
    0.0825    5.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5306    6.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3152    6.1090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4868    5.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737    4.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890    5.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0452    3.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4321    3.3910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8298    3.6881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4429    4.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2714    5.0471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0013    2.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3882    2.3291    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9033    1.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1187    1.9166    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1187    2.7416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9033    2.9965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958    3.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102    2.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3102    1.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958    1.5041    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0013    1.7771    0.0000 O   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  4 11  1  0  0  0  0
  9 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 13 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 13 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051233

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@]1(CN2C=NC3=CC=CC=C3C2=O)C[C@@H]2NCCC[C@H]2O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H19N3O3/c20-15-11-4-1-2-5-12(11)18-10-19(15)9-16(21)8-13-14(22-16)6-3-7-17-13/h1-2,4-5,10,13-14,17,21H,3,6-9H2/t13-,14+,16-/m0/s1

> <INCHI_KEY>
YLYLCQRQSRDSQR-LZWOXQAQSA-N

> <FORMULA>
C16H19N3O3

> <MOLECULAR_WEIGHT>
301.346

> <EXACT_MASS>
301.142641484

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.439031540772675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(2S,3aS,7aR)-2-hydroxy-octahydrofuro[3,2-b]pyridin-2-yl]methyl}-3,4-dihydroquinazolin-4-one

> <ALOGPS_LOGP>
0.13

> <JCHEM_LOGP>
1.0312317483333333

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.60697263857697

> <JCHEM_PKA_STRONGEST_BASIC>
9.167425894151183

> <JCHEM_POLAR_SURFACE_AREA>
74.16000000000001

> <JCHEM_REFRACTIVITY>
82.06569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2S,3aS,7aR)-2-hydroxy-hexahydro-3H-furo[3,2-b]pyridin-2-yl]methyl}quinazolin-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       0.154  10.849   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.990  11.879   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.455  11.403   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.775   9.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.631   8.867   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.166   9.343   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.951   7.360   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.807   6.330   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      -3.416   6.884   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -4.560   7.915   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -4.240   9.421   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -3.736   5.378   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.591   4.348   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.686   3.102   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.222   3.578   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.222   5.118   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.686   5.594   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.112   5.888   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.446   5.118   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.446   3.578   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.112   2.808   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      -3.736   3.317   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    4                                                       
CONECT   12    9   13                                                       
CONECT   13   12   14   17   22                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   13                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15                                                       
CONECT   22   13                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₉N₃O₃

Average Mass

301.3460 Da

Monoisotopic Mass

301.14264 Da

IUPAC Name

3-{[(2S,3aS,7aR)-2-hydroxy-octahydrofuro[3,2-b]pyridin-2-yl]methyl}-3,4-dihydroquinazolin-4-one

Traditional Name

3-{[(2S,3aS,7aR)-2-hydroxy-hexahydro-3H-furo[3,2-b]pyridin-2-yl]methyl}quinazolin-4-one

CAS Registry Number

Not Available

SMILES

O[C@@]1(CN2C=NC3=CC=CC=C3C2=O)C[C@@H]2NCCC[C@H]2O1

InChI Identifier

InChI=1S/C16H19N3O3/c20-15-11-4-1-2-5-12(11)18-10-19(15)9-16(21)8-13-14(22-16)6-3-7-17-13/h1-2,4-5,10,13-14,17,21H,3,6-9H2/t13-,14+,16-/m0/s1

InChI Key

YLYLCQRQSRDSQR-LZWOXQAQSA-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
Dichroa febrifuga	Plant	KNApSAcK
Hydrangea macrophylla	Plant	KNApSAcK
Hydrangea umbellata	Plant	KNApSAcK

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
Piperidine
Pyrimidine
Benzenoid
Heteroaromatic compound
Tetrahydrofuran
Hemiacetal
Lactam
Secondary aliphatic amine
Oxacycle
Secondary amine
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Amine
Organic nitrogen 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	0.13	ALOGPS
logP	1.03	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	11.61	ChemAxon
pKa (Strongest Basic)	9.17	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.07 m³·mol⁻¹	ChemAxon
Polarizability	31.44 Å³	ChemAxon
Number of Rings	4	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

137795500

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isofebrifugine (NP0051233)

MOL for NP0051233 (Isofebrifugine)

3D MOL for NP0051233 (Isofebrifugine)

3D SDF for NP0051233 (Isofebrifugine)

3D-SDF for NP0051233 (Isofebrifugine)

PDB for NP0051233 (Isofebrifugine)

3D PDB for NP0051233 (Isofebrifugine)

SMILES for NP0051233 (Isofebrifugine)

INCHI for NP0051233 (Isofebrifugine)

Structure for NP0051233 (Isofebrifugine)

3D Structure for NP0051233 (Isofebrifugine)