NP-MRD: Showing NP-Card for Acrimarine I (NP0083395)

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Record Information

Version

2.0

Created at

2022-04-29 04:27:31 UTC

Updated at

2022-04-29 04:27:31 UTC

NP-MRD ID

NP0083395

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acrimarine I

Description

Acrimarine I 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. Acrimarine I is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Acrimarine I has been detected, but not quantified in, citrus. Acrimarine I is found in Citrus aurantium, Citrus hybrids and Citrus paradisi. This could make acrimarine I a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061311482D          

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M  END

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  Mrv0541 05061311482D          

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    1.4459    6.6489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2560    2.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9058    2.9071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946    3.8425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657    5.7135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2546    1.0361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0  0  0  0
  9  7  1  0  0  0  0
 11 10  2  0  0  0  0
 13 12  2  0  0  0  0
 17  1  1  0  0  0  0
 17  2  1  0  0  0  0
 17 14  2  0  0  0  0
 18 10  1  0  0  0  0
 18 15  2  0  0  0  0
 19  8  1  0  0  0  0
 20 12  1  0  0  0  0
 21 15  1  0  0  0  0
 22 14  1  0  0  0  0
 22 21  1  0  0  0  0
 23  9  2  0  0  0  0
 24 16  2  0  0  0  0
 24 18  1  0  0  0  0
 25 16  1  0  0  0  0
 25 21  2  0  0  0  0
 26 11  1  0  0  0  0
 27 22  1  0  0  0  0
 29 19  2  0  0  0  0
 29 23  1  0  0  0  0
 30 20  1  0  0  0  0
 30 28  2  0  0  0  0
 31 19  1  0  0  0  0
 31 28  1  0  0  0  0
 32 27  2  0  0  0  0
 32 28  1  0  0  0  0
 33 20  2  0  0  0  0
 33 27  1  0  0  0  0
 34  3  1  0  0  0  0
 34  4  1  0  0  0  0
 34 13  1  0  0  0  0
 35  5  1  0  0  0  0
 35 29  1  0  0  0  0
 35 30  1  0  0  0  0
 36 23  1  0  0  0  0
 37 26  2  0  0  0  0
 38 31  2  0  0  0  0
 39 32  1  0  0  0  0
 40  6  1  0  0  0  0
 40 25  1  0  0  0  0
 41 24  1  0  0  0  0
 41 26  1  0  0  0  0
 42 33  1  0  0  0  0
 42 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083395

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=C2C=CC(=O)OC2=C1)C(C=C(C)C)C1=C(O)C2=C(N(C)C3=C(C=CC=C3O)C2=O)C2=C1OC(C)(C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C34H31NO7/c1-17(2)14-22(21-15-18-10-11-26(37)41-24(18)16-25(21)40-6)27-32(39)28-30(20-12-13-34(3,4)42-33(20)27)35(5)29-19(31(28)38)8-7-9-23(29)36/h7-16,22,36,39H,1-6H3

> <INCHI_KEY>
GSUYTELQWICLMF-UHFFFAOYSA-N

> <FORMULA>
C34H31NO7

> <MOLECULAR_WEIGHT>
565.6124

> <EXACT_MASS>
565.210052351

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
60.65924545693139

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,11-dihydroxy-12-[1-(7-methoxy-2-oxo-2H-chromen-6-yl)-3-methylbut-2-en-1-yl]-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one

> <ALOGPS_LOGP>
5.52

> <JCHEM_LOGP>
6.868280238999999

> <ALOGPS_LOGS>
-5.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.989017104124276

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.097517928949038

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2353882009105535

> <JCHEM_POLAR_SURFACE_AREA>
105.53000000000002

> <JCHEM_REFRACTIVITY>
163.1538

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,11-dihydroxy-12-[1-(7-methoxy-2-oxochromen-6-yl)-3-methylbut-2-en-1-yl]-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.302   7.191   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.366   5.427   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.817  -0.716   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.191   1.228   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.195  -1.267   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.358   8.337   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.236   1.061   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.228   2.225   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.732  -0.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.699   8.337   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.203   9.792   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.326  -0.394   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.838  -0.685   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.846   4.553   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.683   6.591   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   8.919   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.854   5.718   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.187   8.046   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.715   1.934   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.179   1.061   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.830   6.300   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334   4.844   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.219  -0.685   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.179   9.210   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.838   7.464   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.195  10.956   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.326   3.680   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.195   2.807   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.211   0.479   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.691   1.352   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.707   3.098   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.187   3.971   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.830   2.225   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.846   0.479   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       2.699   0.188   0.000  0.00  0.00           N+0
HETATM   36  O   UNK     0       4.715  -2.140   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       2.699  12.411   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       4.211   4.553   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       1.691   5.427   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -3.350   7.173   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       0.683  10.665   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -2.342   1.934   0.000  0.00  0.00           O+0
CONECT    1   17                                                            
CONECT    2   17                                                            
CONECT    3   34                                                            
CONECT    4   34                                                            
CONECT    5   35                                                            
CONECT    6   40                                                            
CONECT    7    8    9                                                       
CONECT    8    7   19                                                       
CONECT    9    7   23                                                       
CONECT   10   11   18                                                       
CONECT   11   10   26                                                       
CONECT   12   13   20                                                       
CONECT   13   12   34                                                       
CONECT   14   17   22                                                       
CONECT   15   18   21                                                       
CONECT   16   24   25                                                       
CONECT   17    1    2   14                                                  
CONECT   18   10   15   24                                                  
CONECT   19    8   29   31                                                  
CONECT   20   12   30   33                                                  
CONECT   21   15   22   25                                                  
CONECT   22   14   21   27                                                  
CONECT   23    9   29   36                                                  
CONECT   24   16   18   41                                                  
CONECT   25   16   21   40                                                  
CONECT   26   11   37   41                                                  
CONECT   27   22   32   33                                                  
CONECT   28   30   31   32                                                  
CONECT   29   19   23   35                                                  
CONECT   30   20   28   35                                                  
CONECT   31   19   28   38                                                  
CONECT   32   27   28   39                                                  
CONECT   33   20   27   42                                                  
CONECT   34    3    4   13   42                                             
CONECT   35    5   29   30                                                  
CONECT   36   23                                                            
CONECT   37   26                                                            
CONECT   38   31                                                            
CONECT   39   32                                                            
CONECT   40    6   25                                                       
CONECT   41   24   26                                                       
CONECT   42   33   34                                                       
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
2-(4-oxo-4-Phenylbutyl)-1-indanone	HMDB

Chemical Formula

C₃₄H₃₁NO₇

Average Mass

565.6124 Da

Monoisotopic Mass

565.21005 Da

IUPAC Name

6,11-dihydroxy-12-[1-(7-methoxy-2-oxo-2H-chromen-6-yl)-3-methylbut-2-en-1-yl]-2,2,5-trimethyl-5,10-dihydro-2H-1-oxa-5-azatetraphen-10-one

Traditional Name

6,11-dihydroxy-12-[1-(7-methoxy-2-oxochromen-6-yl)-3-methylbut-2-en-1-yl]-2,2,5-trimethyl-1-oxa-5-azatetraphen-10-one

CAS Registry Number

Not Available

SMILES

COC1=C(C=C2C=CC(=O)OC2=C1)C(C=C(C)C)C1=C(O)C2=C(N(C)C3=C(C=CC=C3O)C2=O)C2=C1OC(C)(C)C=C2

InChI Identifier

InChI=1S/C34H31NO7/c1-17(2)14-22(21-15-18-10-11-26(37)41-24(18)16-25(21)40-6)27-32(39)28-30(20-12-13-34(3,4)42-33(20)27)35(5)29-19(31(28)38)8-7-9-23(29)36/h7-16,22,36,39H,1-6H3

InChI Key

GSUYTELQWICLMF-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
Citrus aurantium	LOTUS Database	35616633
Citrus hybrids	Plant	KNApSAcK
Citrus paradisi	LOTUS Database	35616633

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
Coumarin
Dihydroquinolone
8-hydroxyquinoline
Benzopyran
Dihydroquinoline
1-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyridine
Pyran
Benzenoid
Vinylogous amide
Vinylogous acid
Heteroaromatic compound
Lactone
Azacycle
Ether
Oxacycle
Organic oxide
Organic oxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organooxygen compound
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	5.52	ALOGPS
logP	6.87	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	9.1	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	163.15 m³·mol⁻¹	ChemAxon
Polarizability	60.66 Å³	ChemAxon
Number of Rings	6	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

HMDB0040387

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020119

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

102145465

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Acrimarine I (NP0083395)

MOL for NP0083395 (Acrimarine I)

3D MOL for NP0083395 (Acrimarine I)

3D SDF for NP0083395 (Acrimarine I)

3D-SDF for NP0083395 (Acrimarine I)

PDB for NP0083395 (Acrimarine I)

3D PDB for NP0083395 (Acrimarine I)

SMILES for NP0083395 (Acrimarine I)

INCHI for NP0083395 (Acrimarine I)

Structure for NP0083395 (Acrimarine I)

3D Structure for NP0083395 (Acrimarine I)