NP-MRD: Showing NP-Card for 10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one (NP0202390)

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Record Information

Version

2.0

Created at

2022-09-04 21:35:47 UTC

Updated at

2022-09-04 21:35:48 UTC

NP-MRD ID

NP0202390

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one

Description

Neoacrimarine C belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. 10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one is found in Citrus hassaku. Based on a literature review very few articles have been published on Neoacrimarine C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042223352D          

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M  END

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M  END


  Mrv1652309042223352D          

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    1.5246    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0352   -0.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    0.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0260    0.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8256    1.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7651    1.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9550    1.0361    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
  3  4  2  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
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 18 28  2  0  0  0  0
 22 28  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 17 33  1  0  0  0  0
 33 34  1  0  0  0  0
 16 35  2  0  0  0  0
 11 35  1  0  0  0  0
  2 35  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
 40 41  2  0  0  0  0
  4 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202390

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=C(C3C(O)C(C)(C)OC4=CC=C5C=CC(=O)OC5=C34)C(O)=CC=C2CC2=C(O)C=C3OC(C)(C)C=CC3=C12

> <INCHI_IDENTIFIER>
InChI=1S/C33H31NO7/c1-32(2)13-12-18-23(40-32)15-21(36)19-14-17-6-9-20(35)25(28(17)34(5)29(18)19)27-26-22(41-33(3,4)31(27)38)10-7-16-8-11-24(37)39-30(16)26/h6-13,15,27,31,35-36,38H,14H2,1-5H3

> <INCHI_KEY>
PRNXRICNFQLLPG-UHFFFAOYSA-N

> <FORMULA>
C33H31NO7

> <MOLECULAR_WEIGHT>
553.611

> <EXACT_MASS>
553.210052342

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
58.527425747963925

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(7,11-dihydroxy-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-6-yl)-13-hydroxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-4-one

> <JCHEM_LOGP>
5.306813216666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.143564566804509

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.495633869389684

> <JCHEM_PKA_STRONGEST_BASIC>
-3.490234555890087

> <JCHEM_POLAR_SURFACE_AREA>
108.69000000000001

> <JCHEM_REFRACTIVITY>
156.3248

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
14-(7,11-dihydroxy-2,2,5-trimethyl-10H-1-oxa-5-azatetraphen-6-yl)-13-hydroxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.358   1.352   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.383  -2.140   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.870  -2.431   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.366  -3.887   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.350  -1.558   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.179   0.479   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.174   2.283   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.342   3.680   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   4.844   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.838   6.300   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.830   7.464   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.683   7.173   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.187   5.718   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.699   5.427   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.203   3.971   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.195   2.807   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.699   1.352   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.683   3.098   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.179   4.553   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.350   6.591   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.358   5.427   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.330   6.622   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.704   4.677   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.854   3.971   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.354   3.622   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.399  -0.394   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.249   0.312   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.874   2.256   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   41                                                  
CONECT    5    4    6   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   35                                                  
CONECT   17   16   18   33                                                  
CONECT   18   17   19   28                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   18   22                                                  
CONECT   29   19   30                                                       
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   17   34                                                  
CONECT   34   33                                                            
CONECT   35   16   11    2                                                  
CONECT   36    5   37                                                       
CONECT   37   36   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37   41                                                       
CONECT   41   40    4                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₃₁NO₇

Average Mass

553.6110 Da

Monoisotopic Mass

553.21005 Da

IUPAC Name

14-(7,11-dihydroxy-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-6-yl)-13-hydroxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-4-one

Traditional Name

14-(7,11-dihydroxy-2,2,5-trimethyl-10H-1-oxa-5-azatetraphen-6-yl)-13-hydroxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-4-one

CAS Registry Number

Not Available

SMILES

CN1C2=C(C3C(O)C(C)(C)OC4=CC=C5C=CC(=O)OC5=C34)C(O)=CC=C2CC2=C(O)C=C3OC(C)(C)C=CC3=C12

InChI Identifier

InChI=1S/C33H31NO7/c1-32(2)13-12-18-23(40-32)15-21(36)19-14-17-6-9-20(35)25(28(17)34(5)29(18)19)27-26-22(41-33(3,4)31(27)38)10-7-16-8-11-24(37)39-30(16)26/h6-13,15,27,31,35-36,38H,14H2,1-5H3

InChI Key

PRNXRICNFQLLPG-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
Citrus hassaku	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Pyranocoumarins

Direct Parent

Angular pyranocoumarins

Alternative Parents

Substituents

Angular pyranocoumarin
Acridine
Benzoquinoline
Pyranochromene
2,2-dimethyl-1-benzopyran
Alkyldiarylamine
Chromane
Benzopyran
1-benzopyran
Tertiary aliphatic/aromatic amine
Alkyl aryl ether
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Heteroaromatic compound
Tertiary amine
Secondary alcohol
Lactone
Azacycle
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organonitrogen compound
Organic oxide
Organic oxygen compound
Organooxygen compound
Amine
Organic nitrogen compound
Alcohol
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	5.31	ChemAxon
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	156.32 m³·mol⁻¹	ChemAxon
Polarizability	58.53 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00019982

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

101696940

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one (NP0202390)

MOL for NP0202390 (10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

3D MOL for NP0202390 (10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

3D SDF for NP0202390 (10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

3D-SDF for NP0202390 (10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

PDB for NP0202390 (10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

3D PDB for NP0202390 (10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

SMILES for NP0202390 (10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

INCHI for NP0202390 (10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

Structure for NP0202390 (10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)

3D Structure for NP0202390 (10-(7,11-dihydroxy-2,2,5-trimethyl-10h-1-oxa-5-azatetraphen-6-yl)-9-hydroxy-8,8-dimethyl-9h,10h-pyrano[2,3-h]chromen-2-one)