NP-MRD: Showing NP-Card for Chanoclavine-II (NP0057936)

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Record Information

Version

2.0

Created at

2022-04-28 03:17:38 UTC

Updated at

2022-04-28 03:17:38 UTC

NP-MRD ID

NP0057936

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chanoclavine-II

Description

Chanoclavine II belongs to the class of organic compounds known as clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines. Chanoclavine-II is found in Claviceps purpurea . Based on a literature review very few articles have been published on Chanoclavine II.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.0084    2.7225    1.3145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5488    1.3715    1.0707 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611    1.3110   -0.2492 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0222    1.6440   -1.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1933    0.8071   -0.9560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5819    0.9195   -1.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1337   -0.2494   -0.6124 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1451   -1.1040   -0.2488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0780   -2.3904    0.2500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8403   -2.9598    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6520   -2.2732    0.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7350   -1.0019   -0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592   -0.4483   -0.4625 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4820   -0.1467   -0.4931 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5785   -0.5724    0.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8420   -0.3900    0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2457    0.2687   -1.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9285   -0.8315    0.9847 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7775   -1.7548    0.3964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8368    3.0108    0.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4444    2.7456    2.3352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1854    3.4576    1.3077 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1287    1.1467    1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9411    1.9521   -0.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2382    2.7196   -1.3065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6282    1.3161   -2.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0795    1.8033   -1.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1412   -0.4724   -0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0104   -2.9142    0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7896   -3.9761    0.9043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3255   -2.7092    0.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6744   -0.2647   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3459   -1.0637    1.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4369    0.7483   -1.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8303   -0.4665   -1.7745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9779    1.0751   -0.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4567   -1.3075    1.8839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5320    0.0113    1.3791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6866   -1.7344    0.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 12 13  1  0
 14  3  1  0
 13  5  1  0
 13  8  2  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  1
  4 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 14 32  1  6
 15 33  1  0
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv1652304282205172D          

 19 21  0  0  1  0            999 V2000
   -0.4959   -1.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578   -1.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9252   -1.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -0.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    0.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5821   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    0.0135    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4326   -0.4714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3463   -1.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377   -2.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5127   -2.4121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862   -0.1359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8537   -0.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8805    0.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457    1.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7611    1.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1114    2.4642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2954    0.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
  8 13  1  6  0  0  0
 13 14  1  0  0  0  0
  7 15  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057936

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H]1CC2=CNC3=CC=CC([C@@H]1\C=C(/C)CO)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O/c1-10(9-19)6-13-12-4-3-5-14-16(12)11(8-18-14)7-15(13)17-2/h3-6,8,13,15,17-19H,7,9H2,1-2H3/b10-6+/t13-,15+/m0/s1

> <INCHI_KEY>
SAHHMCVYMGARBT-GJTNBUKJSA-N

> <FORMULA>
C16H20N2O

> <MOLECULAR_WEIGHT>
256.349

> <EXACT_MASS>
256.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
29.530475447217967

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-2-methyl-3-[(6R,7S)-6-(methylamino)-2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(11),3,8(12),9-tetraen-7-yl]prop-2-en-1-ol

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.8734520346666668

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.05514168238115

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.159183302278649

> <JCHEM_PKA_STRONGEST_BASIC>
10.340094389376212

> <JCHEM_POLAR_SURFACE_AREA>
48.05

> <JCHEM_REFRACTIVITY>
78.9742

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.64e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-2-methyl-3-[(6R,7S)-6-(methylamino)-2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(11),3,8(12),9-tetraen-7-yl]prop-2-en-1-ol

> <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      -0.926  -2.412   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.481  -3.038   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.727  -2.133   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.566  -0.601   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.159   0.025   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.087  -0.880   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.295   0.025   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.541  -0.880   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.380  -2.412   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.973  -3.038   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.497  -4.503   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.957  -4.503   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       5.948  -0.254   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       7.194  -1.159   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.510   1.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.939   2.126   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.154   3.651   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.941   4.600   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.151   1.177   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8   15                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11    2                                                       
CONECT   13    8   14                                                       
CONECT   14   13                                                            
CONECT   15    7   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀N₂O

Average Mass

256.3490 Da

Monoisotopic Mass

256.15756 Da

IUPAC Name

(2E)-2-methyl-3-[(6R,7S)-6-(methylamino)-2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(11),3,8(12),9-tetraen-7-yl]prop-2-en-1-ol

Traditional Name

(2E)-2-methyl-3-[(6R,7S)-6-(methylamino)-2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(11),3,8(12),9-tetraen-7-yl]prop-2-en-1-ol

CAS Registry Number

Not Available

SMILES

CN[C@@H]1CC2=CNC3=CC=CC([C@@H]1\C=C(/C)CO)=C23

InChI Identifier

InChI=1S/C16H20N2O/c1-10(9-19)6-13-12-4-3-5-14-16(12)11(8-18-14)7-15(13)17-2/h3-6,8,13,15,17-19H,7,9H2,1-2H3/b10-6+/t13-,15+/m0/s1

InChI Key

SAHHMCVYMGARBT-GJTNBUKJSA-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
Claviceps purpurea	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as clavines and derivatives. These are hydroxy and dehydro derivatives of 6,8-dimethylergolenes and the corresponding ergolines.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Clavines and derivatives

Direct Parent

Clavines and derivatives

Alternative Parents

Substituents

Chanoclavine skeleton
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
Pyrrole
Heteroaromatic compound
Organoheterocyclic compound
Azacycle
Secondary amine
Secondary aliphatic amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Amine
Alcohol
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	1.91	ALOGPS
logP	1.87	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	15.16	ChemAxon
pKa (Strongest Basic)	10.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	48.05 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.97 m³·mol⁻¹	ChemAxon
Polarizability	29.53 Å³	ChemAxon
Number of Rings	3	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

C00011214

Chemspider ID

32702224

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chanoclavine II

METLIN ID

Not Available

PubChem Compound

15559894

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Chanoclavine-II (NP0057936)

MOL for NP0057936 (Chanoclavine-II)

3D MOL for NP0057936 (Chanoclavine-II)

3D SDF for NP0057936 (Chanoclavine-II)

3D-SDF for NP0057936 (Chanoclavine-II)

PDB for NP0057936 (Chanoclavine-II)

3D PDB for NP0057936 (Chanoclavine-II)

SMILES for NP0057936 (Chanoclavine-II)

INCHI for NP0057936 (Chanoclavine-II)

Structure for NP0057936 (Chanoclavine-II)

3D Structure for NP0057936 (Chanoclavine-II)