NP-MRD: Showing NP-Card for Atalaphyllidine (NP0066632)

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Record Information

Version

2.0

Created at

2022-04-28 10:51:40 UTC

Updated at

2022-04-28 10:51:40 UTC

NP-MRD ID

NP0066632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Atalaphyllidine

Description

Atolaphyllidine belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. Atalaphyllidine is found in Atalantia buxifolia, Atalantia macrophylla, Citrus sinensis grafted on Citrus limonia , Glycosmis citrifolia, Glycosmis macranta, Glycosmis macrantha, Glycosmis parviflora, Oriciopsis glaberrima ENGL. and Severinia buxifolia . Atolaphyllidine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
   -4.5911    0.5147   -1.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6787    0.3885    0.2071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5454    0.5689    1.4518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7188    1.5135    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4139    1.3247    0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8391    0.0070    0.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7217   -1.0761    0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1876   -2.3329    0.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1862   -2.5973   -0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5671   -3.8968   -0.1319 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236   -1.5146   -0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3963   -1.7248   -0.1626 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9186   -2.8589   -0.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2314   -0.6299   -0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6062   -0.8412   -0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4446    0.2351   -0.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9317    1.4900   -0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599    1.7051   -0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1551    3.0078   -0.0654 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6931    0.6384   -0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3432    0.8320   -0.0356 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5145   -0.2183   -0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1035   -0.8725    0.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4286   -0.2128   -0.8595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9692    0.2195   -1.8936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9839    1.5492   -1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8679    1.6328    1.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4679   -0.0485    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9824    0.2683    2.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1210    2.5483    0.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8194    2.1975    0.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8946   -3.1740    0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3799   -4.4021   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9756   -1.8408   -0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042    0.0835   -0.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6145    2.3261   -0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2376    3.3901   -0.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0516    1.8006    0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2 23  1  0
 23  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 22  6  2  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  6  7  1  0
 22 11  1  0
 20 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  8 32  1  0
 10 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 19 37  1  0
 21 38  1  0
  5 31  1  0
  4 30  1  0
M  END


  Mrv1533004171516192D          

 23 26  0  0  0  0            999 V2000
    2.0414   -1.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2418   -2.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0323   -1.4389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8424   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -0.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9226   -0.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926    0.4321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4627   -0.9711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -0.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -0.0357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -1.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6230   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1631   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8931   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8129   -3.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5428   -2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7327   -2.3743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1926   -1.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825   -1.9066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1124   -2.6861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3023   -2.8421    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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  2  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=CC(O)=C3C(=O)C4=CC=CC(O)=C4NC3=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H15NO4/c1-18(2)7-6-9-13(23-18)8-12(21)14-16(9)19-15-10(17(14)22)4-3-5-11(15)20/h3-8,20-21H,1-2H3,(H,19,22)

> <INCHI_KEY>
QMIBOFBCPAGGAC-UHFFFAOYSA-N

> <FORMULA>
C18H15NO4

> <MOLECULAR_WEIGHT>
309.321

> <EXACT_MASS>
309.100107967

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.36913644214972

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,11-dihydroxy-2,2-dimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one

> <ALOGPS_LOGP>
4.30

> <JCHEM_LOGP>
5.142771571333332

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.429301092380669

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.769854881509112

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0756240556873076

> <JCHEM_POLAR_SURFACE_AREA>
78.79

> <JCHEM_REFRACTIVITY>
87.41690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,11-dihydroxy-2,2-dimethyl-5H-1-oxa-5-azatetraphen-10-one

> <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  C   UNK     0       3.811  -3.392   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.156  -4.141   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.185  -5.336   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.660  -2.686   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.172  -2.395   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.677  -0.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.189  -0.649   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       9.693   0.807   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.197  -1.813   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.709  -1.522   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.213  -0.067   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.717  -2.686   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.230  -2.395   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.238  -3.559   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.734  -5.014   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.221  -5.305   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.717  -6.760   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.213  -4.141   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      10.701  -4.432   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       9.693  -3.268   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.181  -3.559   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.677  -5.014   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.164  -5.305   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   23                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   20                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    9   21                                                  
CONECT   21   20    5   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    2                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₅NO₄

Average Mass

309.3210 Da

Monoisotopic Mass

309.10011 Da

IUPAC Name

6,11-dihydroxy-2,2-dimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one

Traditional Name

6,11-dihydroxy-2,2-dimethyl-5H-1-oxa-5-azatetraphen-10-one

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=CC(O)=C3C(=O)C4=CC=CC(O)=C4NC3=C2C=C1

InChI Identifier

InChI=1S/C18H15NO4/c1-18(2)7-6-9-13(23-18)8-12(21)14-16(9)19-15-10(17(14)22)4-3-5-11(15)20/h3-8,20-21H,1-2H3,(H,19,22)

InChI Key

QMIBOFBCPAGGAC-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, 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
Atalantia buxifolia	LOTUS Database	35616633
Atalantia macrophylla	Plant	KNApSAcK
Citrus sinensis grafted on Citrus limonia	Plant	KNApSAcK
Glycosmis citrifolia	Plant	KNApSAcK
Glycosmis macranta	Plant	KNApSAcK
Glycosmis macrantha	LOTUS Database	35616633
Glycosmis parviflora	LOTUS Database	35616633
Oriciopsis glaberrima ENGL.	Plant	KNApSAcK
Severinia buxifolia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Benzoquinolines

Direct Parent

Acridones

Alternative Parents

Substituents

Acridone
Chromenopyridine
2,2-dimethyl-1-benzopyran
Dihydroquinolone
8-hydroxyquinoline
Benzopyran
Dihydroquinoline
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous acid
Vinylogous amide
Azacycle
Oxacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen 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	4.3	ALOGPS
logP	5.14	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.77	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.79 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.42 m³·mol⁻¹	ChemAxon
Polarizability	32.37 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

5479542

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Atalaphyllidine (NP0066632)

MOL for NP0066632 (Atalaphyllidine)

3D MOL for NP0066632 (Atalaphyllidine)

3D SDF for NP0066632 (Atalaphyllidine)

3D-SDF for NP0066632 (Atalaphyllidine)

PDB for NP0066632 (Atalaphyllidine)

3D PDB for NP0066632 (Atalaphyllidine)

SMILES for NP0066632 (Atalaphyllidine)

INCHI for NP0066632 (Atalaphyllidine)

Structure for NP0066632 (Atalaphyllidine)

3D Structure for NP0066632 (Atalaphyllidine)