NP-MRD: Showing NP-Card for Ignavine (NP0067202)

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Record Information

Version

2.0

Created at

2022-04-28 11:34:14 UTC

Updated at

2022-04-28 11:34:15 UTC

NP-MRD ID

NP0067202

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ignavine

Description

Ignavine is found in Aconitum calliantum, Aconitum carmichaeli , Aconitum grossedentatum, Aconitum hakusanense Nakai, Aconitum japonicum, Aconitum kamtschaticum, Aconitum lucidusculum Nakai., Aconitum sanyoense, Aconitum senanense Nakai, Aconitum subcuneatum Nakai, Aconitum tasiromontanum, Aconitum tortuosum and Aconitum zuccarini.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282213342D          

 33 40  0  0  1  0            999 V2000
    5.5936    0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1956    1.0998    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1303    1.9677    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3824    2.3429    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7177    1.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.9482    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4814    0.7044    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3495   -0.2707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6805   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1580   -0.5190    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0232   -1.3329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9663    0.0845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8503    0.1712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8228    0.0511    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9061   -0.1728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1905    1.5947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3045    3.1642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2 33  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282213342D          

 33 40  0  0  1  0            999 V2000
    5.5936    0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3045    3.1642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8820    3.0294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0067202

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CN3[C@H]4C[C@@]56[C@@H]7C[C@@H](C[C@@]5(O)[C@@](C[C@@H](OC(=O)C5=CC=CC=C5)[C@@H]1O)([C@H]37)[C@@H]24)C(=C)[C@H]6O

> <INCHI_IDENTIFIER>
InChI=1S/C27H31NO5/c1-13-15-8-16-20-26-11-18(33-23(31)14-6-4-3-5-7-14)22(30)24(2)12-28(20)17(19(24)26)10-25(16,21(13)29)27(26,32)9-15/h3-7,15-22,29-30,32H,1,8-12H2,2H3/t15-,16+,17-,18+,19+,20+,21+,22-,24+,25+,26+,27-/m0/s1

> <INCHI_KEY>
FOIZZXKAYVIZQC-WGBWXJBQSA-N

> <FORMULA>
C27H31NO5

> <MOLECULAR_WEIGHT>
449.547

> <EXACT_MASS>
449.220223102

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
70.98084448008183

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R,4R,5S,8R,9S,11S,13R,14S,16S,17R,18R)-4,13,18-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl benzoate

> <ALOGPS_LOGP>
0.72

> <JCHEM_LOGP>
1.1096593376666672

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.879137690446509

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.359732542583075

> <JCHEM_PKA_STRONGEST_BASIC>
8.78017484797113

> <JCHEM_POLAR_SURFACE_AREA>
90.23

> <JCHEM_REFRACTIVITY>
119.2363

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,4R,5S,8R,9S,11S,13R,14S,16S,17R,18R)-4,13,18-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl benzoate

> <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      10.441   0.678   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.699   2.053   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.576   3.673   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.180   4.373   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.940   3.422   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081   1.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.365   1.315   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.119  -0.505   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.870  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.568  -0.517   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.665   1.464   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.360   2.342   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.055   1.544   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.657  -0.003   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.212  -0.535   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.028  -0.969   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.777  -2.488   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.670   0.158   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.321   0.319   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.136   0.095   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       9.158  -0.323   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       5.956   2.977   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.035   5.907   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.635   6.547   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.380   5.655   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.489   8.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.089   8.721   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.944  10.254   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.199  11.147   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.599  10.506   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.744   8.973   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.856   4.530   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.176   2.486   0.000  0.00  0.00           C+0
CONECT    1    2   21                                                       
CONECT    2    1    3    7   33                                             
CONECT    3    2    4   32                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11   20                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   16   19                                             
CONECT   11   10    6   12   22                                             
CONECT   12   11   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17                                                  
CONECT   17   16                                                            
CONECT   18   13   19                                                       
CONECT   19   18   10   20                                                  
CONECT   20   19    6   21                                                  
CONECT   21   20    1    8                                                  
CONECT   22   11                                                            
CONECT   23    4   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32    3                                                            
CONECT   33    2                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₁NO₅

Average Mass

449.5470 Da

Monoisotopic Mass

449.22022 Da

IUPAC Name

(1R,3R,4R,5S,8R,9S,11S,13R,14S,16S,17R,18R)-4,13,18-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl benzoate

Traditional Name

(1R,3R,4R,5S,8R,9S,11S,13R,14S,16S,17R,18R)-4,13,18-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl benzoate

CAS Registry Number

Not Available

SMILES

C[C@]12CN3[C@H]4C[C@@]56[C@@H]7C[C@@H](C[C@@]5(O)[C@@](C[C@@H](OC(=O)C5=CC=CC=C5)[C@@H]1O)([C@H]37)[C@@H]24)C(=C)[C@H]6O

InChI Identifier

InChI=1S/C27H31NO5/c1-13-15-8-16-20-26-11-18(33-23(31)14-6-4-3-5-7-14)22(30)24(2)12-28(20)17(19(24)26)10-25(16,21(13)29)27(26,32)9-15/h3-7,15-22,29-30,32H,1,8-12H2,2H3/t15-,16+,17-,18+,19+,20+,21+,22-,24+,25+,26+,27-/m0/s1

InChI Key

FOIZZXKAYVIZQC-WGBWXJBQSA-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
Aconitum calliantum	Plant	KNApSAcK
Aconitum carmichaelii	Plant	KNApSAcK
Aconitum grossedentatum	Plant	KNApSAcK
Aconitum hakusanense Nakai	Plant	KNApSAcK
Aconitum japonicum	Plant	KNApSAcK
Aconitum kamtschaticum	Plant	KNApSAcK
Aconitum lucidusculum Nakai.	Plant	KNApSAcK
Aconitum sanyoense	Plant	KNApSAcK
Aconitum senanense Nakai	Plant	KNApSAcK
Aconitum subcuneatum Nakai	Plant	KNApSAcK
Aconitum tasiromontanum	Plant	KNApSAcK
Aconitum tortuosum	Plant	KNApSAcK
Aconitum zuccarini	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	0.72	ALOGPS
logP	1.11	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	13.36	ChemAxon
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	119.24 m³·mol⁻¹	ChemAxon
Polarizability	70.98 Å³	ChemAxon
Number of Rings	8	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

Not Available

References

General References

Not Available

Showing NP-Card for Ignavine (NP0067202)

MOL for NP0067202 (Ignavine)

3D MOL for NP0067202 (Ignavine)

3D SDF for NP0067202 (Ignavine)

3D-SDF for NP0067202 (Ignavine)

PDB for NP0067202 (Ignavine)

3D PDB for NP0067202 (Ignavine)

SMILES for NP0067202 (Ignavine)

INCHI for NP0067202 (Ignavine)

Structure for NP0067202 (Ignavine)

3D Structure for NP0067202 (Ignavine)