NP-MRD: Showing NP-Card for (1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate (NP0308962)

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Record Information

Version

2.0

Created at

2022-09-11 03:10:17 UTC

Updated at

2022-09-11 03:10:18 UTC

NP-MRD ID

NP0308962

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate

Description

Aristoloterpenate-II 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. (1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate is found in Aristolochia heterophylla. (1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate was first documented in 1999 (PMID: 10096848). Based on a literature review very few articles have been published on Aristoloterpenate-II.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205102D          

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M  CHG  2  21   1  23  -1
M  END

     RDKit          3D

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M  CHG  2  21   1  23  -1
M  END


  Mrv1652309112205102D          

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  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  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  2  0  0  0  0
 18 19  1  0  0  0  0
 14 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 20 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 18 30  1  0  0  0  0
 17 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 16 33  1  0  0  0  0
 10 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
  2 39  1  0  0  0  0
M  CHG  2  21   1  23  -1
M  END
> <DATABASE_ID>
NP0308962

> <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-AJNUOSSRSA-N

> <FORMULA>
C31H29NO7

> <MOLECULAR_WEIGHT>
527.573

> <EXACT_MASS>
527.194402278

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
54.825153290626595

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2Z,6E,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_LOGP>
6.818879123666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.688786113854817

> <JCHEM_POLAR_SURFACE_AREA>
104.97000000000001

> <JCHEM_REFRACTIVITY>
148.5249

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2Z,6E,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                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       6.690  -9.426   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.665 -10.811   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.927 -12.124   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.560 -11.416   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.490  -9.877   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.787  -9.047   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.757 -10.429   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.207 -12.159   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.717  -7.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.014  -6.679   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.067  -5.040   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.541  -4.431   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.935  -4.844   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.506  -2.894   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.803  -2.064   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.733  -0.525   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.366   0.183   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.068  -0.647   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.139  -2.185   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.841  -3.015   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.458  -4.614   0.000  0.00  0.00           N+1
HETATM   22  O   UNK     0       0.908  -5.134   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.396  -6.118   0.000  0.00  0.00           O-1
HETATM   24  C   UNK     0       1.474  -2.307   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.404  -0.768   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.036  -0.060   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.034   1.478   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.263   2.308   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.631   1.600   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.701   0.062   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.617   1.703   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.139   1.933   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.829   0.556   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.381  -7.387   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.451  -8.926   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.632  -9.978   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.819  -9.634   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.889 -11.172   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.592 -12.002   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   34                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   33                                                  
CONECT   17   16   18   31                                                  
CONECT   18   17   19   30                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25   18                                                  
CONECT   31   17   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   16                                                       
CONECT   34   10   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38    2                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Value	Source
Aristoloterpenic acid-II	Generator

Chemical Formula

C₃₁H₂₉NO₇

Average Mass

527.5730 Da

Monoisotopic Mass

527.19440 Da

IUPAC Name

(1R,2Z,6E,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,6E,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-AJNUOSSRSA-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
Aristolochia heterophylla	LOTUS Database	35616633

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
1-naphthalenecarboxylic acid or derivatives
1-nitronaphthalene
2-nitronaphthalene
Naphthalene
Benzodioxole
Nitroaromatic compound
Carboxylic acid ester
C-nitro compound
Organic nitro compound
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic salt
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aldehyde
Organopnictogen compound
Organic nitrogen compound
Organic cation
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	6.82	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	104.97 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	148.52 m³·mol⁻¹	ChemAxon
Polarizability	54.83 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

8522284

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10346826

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wu TS, Chan YY, Leu YL, Chen ZT: Sesquiterpene esters of aristolochic acid from the root and stem of Aristolochia heterophylla. J Nat Prod. 1999 Mar;62(3):415-8. doi: 10.1021/np980212y. [PubMed:10096848 ]
LOTUS database [Link]

Showing NP-Card for (1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate (NP0308962)

MOL for NP0308962 ((1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

3D MOL for NP0308962 ((1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

3D SDF for NP0308962 ((1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

3D-SDF for NP0308962 ((1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

PDB for NP0308962 ((1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

3D PDB for NP0308962 ((1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

SMILES for NP0308962 ((1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

INCHI for NP0308962 ((1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

Structure for NP0308962 ((1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)

3D Structure for NP0308962 ((1r,2z,6e,10e)-3-formyl-7,11-dimethylcyclododeca-2,6,10-trien-1-yl 6-nitro-2h-phenanthro[3,4-d][1,3]dioxole-5-carboxylate)