NP-MRD: Showing NP-Card for Aristolactam AII (NP0068992)

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Record Information

Version

2.0

Created at

2022-04-28 14:16:18 UTC

Updated at

2022-04-28 14:16:18 UTC

NP-MRD ID

NP0068992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aristolactam AII

Description

15-Methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-1(16),2,4,6,8,10,12,14-octaene-11,14-diol belongs to the class of organic compounds known as aristolactams. These are phenanthrenic compounds containing a five-membered lactam ring and a 1,3-dioxolane ring fused to the phenanthrene ring system. Aristolactam AII is found in Aristolochia elegans , Aristolochia foveolata, Aristolochia heterophylla Hemsl , Aristolochia indica, Aristolochia kaempferi, Aristolochia liukiuensis, Aristolochia manshuriensis, Aristolochia mollissima, Aristolochia triangularis, Desmos rostrata, Fissistigma balansae, Fissistigma glaucescens , Fissistigma oldhamii, Goniothalamus cheliensis, Goniothalamus griffithii, Goniothalamus sesquipedalis, Goniothalamus tapis, Houttuynia cordata, Polyalthia crassa, Monocyclanthus vignei, Piper kadsura, Piper lolot, Saururus chinensis and Uvaria microcarpa. 15-Methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-1(16),2,4,6,8,10,12,14-octaene-11,14-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 34  0  0  0  0  0  0  0  0999 V2000
    1.9615   -2.6760   -0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3907   -1.9527    0.8515 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2911   -0.6067    0.6335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4669    0.1009    0.8398 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6577   -0.4672    1.2600 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5337    1.4831    0.6337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4219    2.1836    0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2806    1.4804    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7495    2.2784   -0.3886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9576    1.6525   -0.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0878    0.2903   -0.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3337   -0.3040   -0.5859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4945   -1.6456   -0.3569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4400   -2.4046    0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1740   -1.8360    0.2495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0228   -0.5010    0.0149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1944    0.1059    0.2260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2376    3.6019   -0.4705 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340    3.5735   -0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9513    4.5233   -0.0292 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0267   -3.7394   -0.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2427   -2.4984   -1.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9117   -2.2464   -0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7314   -1.4512    1.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4468    2.0380    0.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7988    2.2482   -0.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1438    0.3532   -0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4759   -2.0902   -0.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5156   -3.4622    0.2489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4159   -2.4645    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7952    4.4329   -0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 17  2  0
 17  8  1  0
  8  7  2  0
  7  6  1  0
  6  4  2  0
  4  5  1  0
  7 19  1  0
 19 20  2  0
 19 18  1  0
 18  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  4  3  1  0
 16 11  1  0
 16 17  1  0
  9  8  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  6 25  1  0
  5 24  1  0
 18 31  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
M  END


  Mrv1533004241514172D          

 20 23  0  0  0  0            999 V2000
    2.9748   -1.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1902   -1.9110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771   -1.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925   -1.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6209   -2.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794   -1.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486   -0.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  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
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 19  2  0  0  0  0
 19 20  1  0  0  0  0
  7 20  2  0  0  0  0
 11 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C3=C(C=C1O)C(=O)NC3=CC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C16H11NO3/c1-20-15-12(18)7-10-13-11(17-16(10)19)6-8-4-2-3-5-9(8)14(13)15/h2-7,18H,1H3,(H,17,19)

> <INCHI_KEY>
ZEKAIRFOYPDZNC-UHFFFAOYSA-N

> <FORMULA>
C16H11NO3

> <MOLECULAR_WEIGHT>
265.268

> <EXACT_MASS>
265.073893218

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.19381550684325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-hydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
2.6096017316666664

> <ALOGPS_LOGS>
-3.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.93576024916894

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.961487674340576

> <JCHEM_PKA_STRONGEST_BASIC>
-4.216851963006642

> <JCHEM_POLAR_SURFACE_AREA>
58.56

> <JCHEM_REFRACTIVITY>
76.878

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aristolactam aii

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       5.553  -3.091   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.088  -3.567   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.944  -2.537   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.479  -3.013   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.159  -4.519   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.335  -1.982   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.790   0.770   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       0.655   2.016   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.454  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.264  -1.030   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18    3   20                                                  
CONECT   20   19    7   11                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
Aristololactam a II	ChEMBL, MeSH
Aristolactam-aii	ChEMBL

Chemical Formula

C₁₆H₁₁NO₃

Average Mass

265.2680 Da

Monoisotopic Mass

265.07389 Da

IUPAC Name

14-hydroxy-15-methoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

Traditional Name

aristolactam aii

CAS Registry Number

Not Available

SMILES

COC1=C2C3=C(C=C1O)C(=O)NC3=CC1=CC=CC=C21

InChI Identifier

InChI=1S/C16H11NO3/c1-20-15-12(18)7-10-13-11(17-16(10)19)6-8-4-2-3-5-9(8)14(13)15/h2-7,18H,1H3,(H,17,19)

InChI Key

ZEKAIRFOYPDZNC-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 elegans	Plant	KNApSAcK
Aristolochia foveolata	Plant	KNApSAcK
Aristolochia heterophylla Hemsl	Plant	KNApSAcK
Aristolochia indica	LOTUS Database	35616633
Aristolochia kaempferi	LOTUS Database	35616633
Aristolochia liukiuensis	LOTUS Database	35616633
Aristolochia manshuriensis	Plant	KNApSAcK
Aristolochia mollissima	Plant	KNApSAcK
Aristolochia triangularis	Plant	KNApSAcK
Desmos rostrata	Plant	KNApSAcK
Fissistigma balansae	Plant	KNApSAcK
Fissistigma glaucescens	Plant	KNApSAcK
Fissistigma oldhamii	Plant	KNApSAcK
Goniothalamus cheliensis	LOTUS Database	35616633
Goniothalamus griffithii	LOTUS Database	35616633
Goniothalamus sesquipedalis	LOTUS Database	35616633
Goniothalamus tapis	LOTUS Database	35616633
Houttuynia cordata	LOTUS Database	35616633
Marsypopetalum crassum	Plant	KNApSAcK
Monocyclanthus vignei	Plant	KNApSAcK
Piper kadsura	LOTUS Database	35616633
Piper lolot	LOTUS Database	35616633
Saururus chinensis	LOTUS Database	35616633
Uvaria microcarpa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aristolactams. These are phenanthrenic compounds containing a five-membered lactam ring and a 1,3-dioxolane ring fused to the phenanthrene ring system.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aristolactams

Sub Class

Not Available

Direct Parent

Aristolactams

Alternative Parents

Substituents

Aristolactam
Phenanthrol
Phenanthrene
2-naphthol
Isoindolone
Naphthalene
Indole or derivatives
Isoindole or derivatives
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Lactam
Carboxylic acid derivative
Ether
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen 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	3.07	ALOGPS
logP	2.61	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.96	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.88 m³·mol⁻¹	ChemAxon
Polarizability	27.19 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

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

148657

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Aristolactam AII (NP0068992)

MOL for NP0068992 (Aristolactam AII)

3D MOL for NP0068992 (Aristolactam AII)

3D SDF for NP0068992 (Aristolactam AII)

3D-SDF for NP0068992 (Aristolactam AII)

PDB for NP0068992 (Aristolactam AII)

3D PDB for NP0068992 (Aristolactam AII)

SMILES for NP0068992 (Aristolactam AII)

INCHI for NP0068992 (Aristolactam AII)

Structure for NP0068992 (Aristolactam AII)

3D Structure for NP0068992 (Aristolactam AII)