NP-MRD: Showing NP-Card for Aristolodione (NP0084500)

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Record Information

Version

2.0

Created at

2022-04-29 05:13:30 UTC

Updated at

2022-04-29 05:13:31 UTC

NP-MRD ID

NP0084500

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aristolodione

Description

Grevilline D belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4. Grevilline D is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Grevilline D has been detected, but not quantified in, mushrooms. Aristolodione is found in Aristolochia chilensis, Aristolochia heterophylla, Aristolochia kaempferi and Piper longum . This could make grevilline D a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -3.3964   -1.8410    0.6156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7101   -1.5066   -0.6444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3467   -1.4748   -0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7536   -2.7209   -0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5292   -3.8809   -0.7767 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5853   -2.8584   -0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3934   -1.7616   -0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8285   -0.5030   -0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6117    0.6077    0.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0859    1.8751    0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2767    1.9818   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8470    3.2515   -0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1848    3.4582   -0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9778    2.3651   -0.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4650    1.0782   -0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1211    0.8870   -0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5716   -0.3820   -0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0135    0.5014    0.1712 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8340    1.7056    0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6546   -0.7578    0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9017   -0.9035    0.2381 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8405   -1.9366   -0.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3234   -3.1037   -0.1661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8969   -1.3089    1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3202   -2.9169    0.8043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4229   -1.4498    0.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1156   -4.7876   -0.8261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0756   -3.8216   -0.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6996    2.7489    0.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1777    4.0901    0.1162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6038    4.4722   -0.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0356    2.5175   -0.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1617    0.3266   -0.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5668    2.1351    1.3745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6084    2.4618   -0.4152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8915    1.4517    0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7 22  1  0
 22 23  2  0
 22 20  1  0
 20 21  2  0
 20 18  1  0
 18 19  1  0
 18  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  8  1  0
 17  3  1  0
  8  7  1  0
  8  9  2  0
 16 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  0
  6 28  1  0
 19 34  1  0
 19 35  1  0
 19 36  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
M  END


  Mrv0541 05061307002D          

 23 26  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  7  1  0  0  0  0
 10  6  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 12  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  2  0  0  0  0
 16 11  1  0  0  0  0
 17 13  2  0  0  0  0
 17 15  1  0  0  0  0
 18 16  1  0  0  0  0
 19  1  1  0  0  0  0
 19 12  1  0  0  0  0
 19 18  1  0  0  0  0
 20 13  1  0  0  0  0
 21 16  2  0  0  0  0
 22 18  2  0  0  0  0
 23  2  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084500

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2C(=O)C(=O)N(C)C3=CC4=CC=CC=C4C1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C18H13NO4/c1-19-12-7-9-5-3-4-6-10(9)15-14(12)11(16(21)18(19)22)8-13(20)17(15)23-2/h3-8,20H,1-2H3

> <INCHI_KEY>
JGDZUWXHWYXMSD-UHFFFAOYSA-N

> <FORMULA>
C18H13NO4

> <MOLECULAR_WEIGHT>
307.3001

> <EXACT_MASS>
307.084457909

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.340239426751765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-hydroxy-16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
2.3333265559999994

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.925657359902802

> <JCHEM_PKA_STRONGEST_BASIC>
-4.560395109624618

> <JCHEM_POLAR_SURFACE_AREA>
66.84

> <JCHEM_REFRACTIVITY>
84.93539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-hydroxy-16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

> <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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.334   2.310   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   23                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4   10                                                       
CONECT    7    9   12                                                       
CONECT    8   11   13                                                       
CONECT    9    5    7   10                                                  
CONECT   10    6    9   15                                                  
CONECT   11    8   14   16                                                  
CONECT   12    7   14   19                                                  
CONECT   13    8   17   20                                                  
CONECT   14   11   12   15                                                  
CONECT   15   10   14   17                                                  
CONECT   16   11   18   21                                                  
CONECT   17   13   15   23                                                  
CONECT   18   16   19   22                                                  
CONECT   19    1   12   18                                                  
CONECT   20   13                                                            
CONECT   21   16                                                            
CONECT   22   18                                                            
CONECT   23    2   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
Piperadione	HMDB

Chemical Formula

C₁₈H₁₃NO₄

Average Mass

307.3001 Da

Monoisotopic Mass

307.08446 Da

IUPAC Name

15-hydroxy-16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

Traditional Name

15-hydroxy-16-methoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(17),2,4,6,8,13,15-heptaene-11,12-dione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2C(=O)C(=O)N(C)C3=CC4=CC=CC=C4C1=C23

InChI Identifier

InChI=1S/C18H13NO4/c1-19-12-7-9-5-3-4-6-10(9)15-14(12)11(16(21)18(19)22)8-13(20)17(15)23-2/h3-8,20H,1-2H3

InChI Key

JGDZUWXHWYXMSD-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
Aristolochia chilensis	LOTUS Database	35616633
Aristolochia heterophylla	LOTUS Database	35616633
Aristolochia kaempferi	LOTUS Database	35616633
Piper longum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
Hydroquinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Dihydropyranone
Monocyclic benzene moiety
Pyran
Enol ester
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Cyclic ketone
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Enol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.89	ALOGPS
logP	2.33	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.93	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.84 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	84.94 m³·mol⁻¹	ChemAxon
Polarizability	31.34 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

HMDB0033246

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011265

KNApSAcK ID

Not Available

Chemspider ID

20124986

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Aristolodione (NP0084500)

MOL for NP0084500 (Aristolodione)

3D MOL for NP0084500 (Aristolodione)

3D SDF for NP0084500 (Aristolodione)

3D-SDF for NP0084500 (Aristolodione)

PDB for NP0084500 (Aristolodione)

3D PDB for NP0084500 (Aristolodione)

SMILES for NP0084500 (Aristolodione)

INCHI for NP0084500 (Aristolodione)

Structure for NP0084500 (Aristolodione)

3D Structure for NP0084500 (Aristolodione)