NP-MRD: Showing NP-Card for (+)-Neoacrimarine-H (NP0066624)

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Record Information

Version

2.0

Created at

2022-04-28 10:51:23 UTC

Updated at

2022-04-28 10:51:23 UTC

NP-MRD ID

NP0066624

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Neoacrimarine-H

Description

11-Hydroxy-6-{[(9S,10S)-9-hydroxy-8,8-dimethyl-2-oxo-2H,8H,9H,10H-pyrano[2,3-h]chromen-10-yl]oxy}-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one 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. (+)-Neoacrimarine-H is found in Citrus paradisi . Based on a literature review very few articles have been published on 11-hydroxy-6-{[(9S,10S)-9-hydroxy-8,8-dimethyl-2-oxo-2H,8H,9H,10H-pyrano[2,3-h]chromen-10-yl]oxy}-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212512D          

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M  END

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  Mrv1652304282212512D          

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    1.1705    1.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0329    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4454    0.9355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6829    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2704    2.3645    0.0000 C   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
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
  3 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  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
  1 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 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
 16 23  2  0  0  0  0
 20 24  1  0  0  0  0
 25 24  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 30 31  1  1  0  0  0
 29 32  1  0  0  0  0
 29 33  1  0  0  0  0
 27 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 26 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 36 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066624

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C2=C(O[C@@H]3[C@H](O)C(C)(C)OC4=CC=C5C=CC(=O)OC5=C34)C=CC=C2C(=O)C2=C(O)C=C3OC(C)(C)C=CC3=C12

> <INCHI_IDENTIFIER>
InChI=1S/C33H29NO8/c1-32(2)14-13-17-22(41-32)15-19(35)24-27(17)34(5)26-18(28(24)37)7-6-8-21(26)39-30-25-20(42-33(3,4)31(30)38)11-9-16-10-12-23(36)40-29(16)25/h6-15,30-31,35,38H,1-5H3/t30-,31-/m0/s1

> <INCHI_KEY>
KYDGDSAPWLVOME-CONSDPRKSA-N

> <FORMULA>
C33H29NO8

> <MOLECULAR_WEIGHT>
567.594

> <EXACT_MASS>
567.189316898

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
58.892866023167144

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.60

> <JCHEM_LOGP>
5.544316221666666

> <ALOGPS_LOGS>
-4.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.828264032230905

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.941970436426637

> <JCHEM_PKA_STRONGEST_BASIC>
-3.748741998497093

> <JCHEM_POLAR_SURFACE_AREA>
114.76000000000002

> <JCHEM_REFRACTIVITY>
156.08300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-hydroxy-6-{[(13S,14S)-13-hydroxy-12,12-dimethyl-4-oxo-3,11-dioxatricyclo[8.4.0.0^{2,7}]tetradeca-1,5,7,9-tetraen-14-yl]oxy}-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-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      -4.565  -3.588   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.795  -4.922   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.565  -6.256   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.105  -6.256   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.875  -4.922   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.105  -3.588   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.875  -2.255   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.415  -2.255   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.185  -3.588   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -8.415  -4.922   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0     -10.544  -2.865   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.544  -4.311   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.795  -7.589   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.255  -4.922   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.485  -6.256   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.485  -3.588   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.255  -2.255   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -3.795  -2.255   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -4.565  -0.921   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.485  -0.921   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.055  -0.921   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.825  -2.255   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.055  -3.588   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.255   0.413   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.485   1.746   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.255   3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.485   4.414   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.055   4.414   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.825   3.080   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.055   1.746   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.825   0.413   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.185   3.803   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.185   2.357   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.255   5.747   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.795   5.747   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.565   4.414   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.795   3.080   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -4.565   1.746   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -6.105   1.746   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -6.875   0.413   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -6.875   3.080   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -6.105   4.414   0.000  0.00  0.00           C+0
CONECT    1    2    6   18                                                  
CONECT    2    1    3   14                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9    5                                                       
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13    3                                                            
CONECT   14    2   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17    1   19                                                  
CONECT   19   18                                                            
CONECT   20   17   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16                                                       
CONECT   24   20   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27   37                                                  
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   32   33                                             
CONECT   30   29   25   31                                                  
CONECT   31   30                                                            
CONECT   32   29                                                            
CONECT   33   29                                                            
CONECT   34   27   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   42                                                  
CONECT   37   36   26   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   36                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₂₉NO₈

Average Mass

567.5940 Da

Monoisotopic Mass

567.18932 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CN1C2=C(O[C@@H]3[C@H](O)C(C)(C)OC4=CC=C5C=CC(=O)OC5=C34)C=CC=C2C(=O)C2=C(O)C=C3OC(C)(C)C=CC3=C12

InChI Identifier

InChI=1S/C33H29NO8/c1-32(2)14-13-17-22(41-32)15-19(35)24-27(17)34(5)26-18(28(24)37)7-6-8-21(26)39-30-25-20(42-33(3,4)31(30)38)11-9-16-10-12-23(36)40-29(16)25/h6-15,30-31,35,38H,1-5H3/t30-,31-/m0/s1

InChI Key

KYDGDSAPWLVOME-CONSDPRKSA-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
Citrus paradisi	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

Angular pyranocoumarin
Pyranocoumarin
Acridone
Pyranochromene
Chromenopyridine
2,2-dimethyl-1-benzopyran
Dihydroquinolone
Coumarin
1-benzopyran
Dihydroquinoline
Benzopyran
Chromane
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Benzenoid
Pyridine
Pyran
Heteroaromatic compound
Vinylogous amide
Vinylogous acid
Secondary alcohol
Lactone
Oxacycle
Azacycle
Ether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	4.6	ALOGPS
logP	5.54	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	8.94	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	114.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	156.08 m³·mol⁻¹	ChemAxon
Polarizability	58.89 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

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

162907000

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Neoacrimarine-H (NP0066624)

MOL for NP0066624 ((+)-Neoacrimarine-H)

3D MOL for NP0066624 ((+)-Neoacrimarine-H)

3D SDF for NP0066624 ((+)-Neoacrimarine-H)

3D-SDF for NP0066624 ((+)-Neoacrimarine-H)

PDB for NP0066624 ((+)-Neoacrimarine-H)

3D PDB for NP0066624 ((+)-Neoacrimarine-H)

SMILES for NP0066624 ((+)-Neoacrimarine-H)

INCHI for NP0066624 ((+)-Neoacrimarine-H)

Structure for NP0066624 ((+)-Neoacrimarine-H)

3D Structure for NP0066624 ((+)-Neoacrimarine-H)