NP-MRD: Showing NP-Card for (-)-Aristoloterpenate II (NP0072730)

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Record Information

Version

2.0

Created at

2022-04-28 18:01:51 UTC

Updated at

2022-04-28 18:01:51 UTC

NP-MRD ID

NP0072730

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Aristoloterpenate II

Description

(1R,2Z,6Z,10E)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 9-nitro-14,16-dioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]Heptadeca-1(10),2,4,6,8,11,13(17)-heptaene-11-carboxylate belongs to the class of organic compounds known as aristolochic acids and derivatives. These are organic heterocyclic compounds with a structure characterized by a nitrophenanthro[3,4-d][1,3]dioxole ring system substituted at position 5, 6, and 8 by a carboxyl group (or a derivative thereof), a nitro group, and a methoxy group, respectively. (-)-Aristoloterpenate II is found in Aristolochia heterophylla and Aristolochia heterophylla Hemsl . Based on a literature review very few articles have been published on (1R,2Z,6Z,10E)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 9-nitro-14,16-dioxatetracyclo[8.7.0.0²,⁷.0¹³,¹⁷]Heptadeca-1(10),2,4,6,8,11,13(17)-heptaene-11-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282220012D          

 39 43  0  0  1  0            999 V2000
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M  END

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M  CHG  2  21   1  23  -1
M  END


  Mrv1652304282220012D          

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  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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  1  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
 14 25  1  0  0  0  0
 24 26  1  0  0  0  0
 20 27  1  0  0  0  0
 16 28  1  0  0  0  0
 28 29  2  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
  7 32  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  2  0  0  0  0
  2 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
  1 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0072730

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C\CC\C(C=O)=C\[C@@H](C\C(C)=C\CC1)OC(=O)C1=C2C(=CC3=CC=CC=C3C2=C2OCOC2=C1)N(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H29NO7/c1-19-7-5-9-20(2)13-23(14-21(17-33)10-6-8-19)39-31(34)25-16-27-30(38-18-37-27)29-24-12-4-3-11-22(24)15-26(28(25)29)32(35)36/h3-4,8-9,11-12,14-17,23H,5-7,10,13,18H2,1-2H3/b19-8-,20-9+,21-14-/t23-/m1/s1

> <INCHI_KEY>
XJBILGKCOVAJTM-BLPKUJFBSA-N

> <FORMULA>
C31H29NO7

> <MOLECULAR_WEIGHT>
527.573

> <EXACT_MASS>
527.194402278

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
56.05570115128924

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2Z,6Z,10E)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 9-nitro-14,16-dioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylate

> <ALOGPS_LOGP>
5.32

> <JCHEM_LOGP>
6.818879123666667

> <ALOGPS_LOGS>
-6.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.688151481807556

> <JCHEM_POLAR_SURFACE_AREA>
107.65

> <JCHEM_REFRACTIVITY>
149.52909999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.64e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2Z,6Z,10E)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 9-nitro-14,16-dioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylate

> <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       3.973   3.551   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.270   4.381   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.200   5.920   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.832   6.628   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.535   5.798   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.605   4.260   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.308   3.430   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.059   4.138   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.129   5.676   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.168   6.506   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.098   8.045   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.395   8.875   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.270   8.753   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.340  10.292   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.707  11.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.246  10.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.076  12.227   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.146  13.765   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.438  15.133   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.140  15.963   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.602  16.033   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.765  15.325   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.836  13.786   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.666  12.489   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.957  11.122   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.204  12.559   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.606  17.431   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.954   9.562   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.493   9.492   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.156   3.056   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.466   1.680   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.057   1.910   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0       3.762   8.166   0.000  0.00  0.00           N+0
HETATM   34  O   UNK     0       3.072   9.543   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       5.059   8.996   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.637   3.673   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.708   2.134   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.410   1.304   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.043   2.013   0.000  0.00  0.00           C+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3   36                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   33                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   32                                                  
CONECT    8    7    9   30                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   28                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24   14                                                       
CONECT   26   24                                                            
CONECT   27   20                                                            
CONECT   28   16   29                                                       
CONECT   29   28                                                            
CONECT   30    8   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31    7                                                       
CONECT   33    4   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36    2   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38    1                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
(1R,2Z,6Z,10E)-3-Formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 9-nitro-14,16-dioxatetracyclo[8.7.0.0,.0,]heptadeca-1(10),2,4,6,8,11,13(17)-heptaene-11-carboxylic acid	Generator

Chemical Formula

C₃₁H₂₉NO₇

Average Mass

527.5730 Da

Monoisotopic Mass

527.19440 Da

IUPAC Name

(1R,2Z,6Z,10E)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 9-nitro-14,16-dioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylate

Traditional Name

(1R,2Z,6Z,10E)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 9-nitro-14,16-dioxatetracyclo[8.7.0.0^{2,7}.0^{13,17}]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylate

CAS Registry Number

Not Available

SMILES

C\C1=C\CC\C(C=O)=C\[C@@H](C\C(C)=C\CC1)OC(=O)C1=C2C(=CC3=CC=CC=C3C2=C2OCOC2=C1)N(=O)=O

InChI Identifier

InChI=1S/C31H29NO7/c1-19-7-5-9-20(2)13-23(14-21(17-33)10-6-8-19)39-31(34)25-16-27-30(38-18-37-27)29-24-12-4-3-11-22(24)15-26(28(25)29)32(35)36/h3-4,8-9,11-12,14-17,23H,5-7,10,13,18H2,1-2H3/b19-8-,20-9+,21-14-/t23-/m1/s1

InChI Key

XJBILGKCOVAJTM-BLPKUJFBSA-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 heterophylla	LOTUS Database	35616633
Aristolochia heterophylla Hemsl	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aristolochic acids and derivatives. These are organic heterocyclic compounds with a structure characterized by a nitrophenanthro[3,4-d][1,3]dioxole ring system substituted at position 5, 6, and 8 by a carboxyl group (or a derivative thereof), a nitro group, and a methoxy group, respectively.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Aristolochic acids and derivatives

Direct Parent

Aristolochic acids and derivatives

Alternative Parents

Substituents

Aristolochic acid or derivatives
2-nitronaphthalene
1-nitronaphthalene
1-naphthalenecarboxylic acid or derivatives
Naphthalene
Benzodioxole
Nitroaromatic compound
Organic nitro compound
C-nitro compound
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aldehyde
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	5.32	ALOGPS
logP	6.82	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	107.65 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	149.53 m³·mol⁻¹	ChemAxon
Polarizability	56.06 Å³	ChemAxon
Number of Rings	5	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

163184351

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Aristoloterpenate II (NP0072730)

MOL for NP0072730 ((-)-Aristoloterpenate II)

3D MOL for NP0072730 ((-)-Aristoloterpenate II)

3D SDF for NP0072730 ((-)-Aristoloterpenate II)

3D-SDF for NP0072730 ((-)-Aristoloterpenate II)

PDB for NP0072730 ((-)-Aristoloterpenate II)

3D PDB for NP0072730 ((-)-Aristoloterpenate II)

SMILES for NP0072730 ((-)-Aristoloterpenate II)

INCHI for NP0072730 ((-)-Aristoloterpenate II)

Structure for NP0072730 ((-)-Aristoloterpenate II)

3D Structure for NP0072730 ((-)-Aristoloterpenate II)