NP-MRD: Showing NP-Card for Penniclavine (NP0057942)

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Record Information

Version

2.0

Created at

2022-04-28 03:17:54 UTC

Updated at

2022-04-28 03:17:54 UTC

NP-MRD ID

NP0057942

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Penniclavine

Description

Penniclavine 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. Penniclavine is found in Aconitum pendulum, Argyreia nervosa , Balansia epichloe, Claviceps purpurea , Ipomoea capillacea, Ipomoea hederacea , Pharbitis nil and Pennisetum typhoideum . Penniclavine was first documented in 2015 (PMID: 25747328). Based on a literature review very few articles have been published on Penniclavine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 41  0  0  0  0  0  0  0  0999 V2000
   -1.3036    3.0554    0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3020    1.7943    0.1438 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3941    0.9328    0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414   -0.1084   -0.5638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6873    0.5797   -1.7642 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7578   -0.9774   -0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7034   -1.6991    0.8175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2852   -0.9141   -0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2031   -0.3292   -0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523   -1.1284   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0549   -2.4975    0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2981   -3.1272    0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -2.3857    0.0486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4511   -1.0227   -0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3534   -0.0018   -0.1314 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6915    1.1753   -0.2215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3153    0.9181   -0.2063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2251   -0.4237   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1073    1.7410   -0.2917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0604    1.0752    0.3575 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5882    3.7263    0.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3141    3.5223    0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1211    3.0030    1.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0800    0.3930    1.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3378    1.4740    0.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0025    0.3210   -2.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6949   -0.4190   -0.3900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7783   -1.7060   -1.1911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -2.6081    0.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2804   -1.9484   -0.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1244   -3.0162    0.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3400   -4.2111    0.1900 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4540   -2.8788    0.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3750   -0.1414   -0.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0941    2.1756   -0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655    1.8450   -1.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3257    2.7330    0.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1494    1.0792    1.4646 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  6
  4  6  1  0
  6  7  1  0
  4  8  1  0
  8  9  2  0
  9 20  1  0
 20 19  1  0
 19 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10 18  2  0
 20  2  1  0
 18 17  1  0
 10  9  1  0
 18 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
 20 38  1  1
 19 36  1  0
 19 37  1  0
 16 35  1  0
 15 34  1  0
 13 33  1  0
 12 32  1  0
 11 31  1  0
M  END


  Mrv1652304282205172D          

 20 23  0  0  1  0            999 V2000
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   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
    1.7486    1.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    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  2  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 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    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
    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 N   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
    4.4306    1.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0433    2.2531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8179    0.8538    0.0000 O   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  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 11 17  1  0  0  0  0
  9 18  1  1  0  0  0
 18 19  1  0  0  0  0
  9 20  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0057942

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C[C@](O)(CO)C=C2[C@H]1CC1=CNC3=CC=CC2=C13

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2O2/c1-18-8-16(20,9-19)6-12-11-3-2-4-13-15(11)10(7-17-13)5-14(12)18/h2-4,6-7,14,17,19-20H,5,8-9H2,1H3/t14-,16+/m1/s1

> <INCHI_KEY>
KCHBNRCSCHMJFD-ZBFHGGJFSA-N

> <FORMULA>
C16H18N2O2

> <MOLECULAR_WEIGHT>
270.332

> <EXACT_MASS>
270.136827828

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.646446583226087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,7R)-4-(hydroxymethyl)-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaen-4-ol

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
0.8635081023333335

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.165368197960802

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.207267930460567

> <JCHEM_PKA_STRONGEST_BASIC>
7.494416145615921

> <JCHEM_POLAR_SURFACE_AREA>
59.49000000000001

> <JCHEM_REFRACTIVITY>
78.9254

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,7R)-4-(hydroxymethyl)-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaen-4-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       0.335   3.522   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.264   2.570   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.479   4.553   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454  -0.000   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       6.121  -0.770   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.270   2.846   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.547   4.206   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.993   1.594   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   16                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18   20                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13    3   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    2                                                       
CONECT   17   11                                                            
CONECT   18    9   19                                                       
CONECT   19   18                                                            
CONECT   20    9                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈N₂O₂

Average Mass

270.3320 Da

Monoisotopic Mass

270.13683 Da

IUPAC Name

(4S,7R)-4-(hydroxymethyl)-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaen-4-ol

Traditional Name

(4S,7R)-4-(hydroxymethyl)-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaen-4-ol

CAS Registry Number

Not Available

SMILES

CN1C[C@](O)(CO)C=C2[C@H]1CC1=CNC3=CC=CC2=C13

InChI Identifier

InChI=1S/C16H18N2O2/c1-18-8-16(20,9-19)6-12-11-3-2-4-13-15(11)10(7-17-13)5-14(12)18/h2-4,6-7,14,17,19-20H,5,8-9H2,1H3/t14-,16+/m1/s1

InChI Key

KCHBNRCSCHMJFD-ZBFHGGJFSA-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 pendulum	Plant	KNApSAcK
Argyreia nervosa	Plant	KNApSAcK
Balansia epichloe	LOTUS Database	35616633
Claviceps purpurea	Fungi	KNApSAcK
Ipomoea capillacea	LOTUS Database	35616633
Ipomoea hederacea	Plant	KNApSAcK
Ipomoea nil	Plant	KNApSAcK
Pennisetum americanum	Plant	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

Clavine skeleton
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
Tertiary alcohol
Heteroaromatic compound
Pyrrole
1,3-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
1,2-diol
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organopnictogen compound
Alcohol
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organooxygen compound
Primary 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	1.25	ALOGPS
logP	0.86	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	13.21	ChemAxon
pKa (Strongest Basic)	7.49	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	59.49 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.93 m³·mol⁻¹	ChemAxon
Polarizability	29.65 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

C00011220

Chemspider ID

103117

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Penniclavine

METLIN ID

Not Available

PubChem Compound

115247

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Paulke A, Kremer C, Wunder C, Wurglics M, Schubert-Zsilavecz M, Toennes SW: Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high. Forensic Sci Int. 2015 Apr;249:281-93. doi: 10.1016/j.forsciint.2015.02.011. Epub 2015 Feb 19. [PubMed:25747328 ]

Showing NP-Card for Penniclavine (NP0057942)

MOL for NP0057942 (Penniclavine)

3D MOL for NP0057942 (Penniclavine)

3D SDF for NP0057942 (Penniclavine)

3D-SDF for NP0057942 (Penniclavine)

PDB for NP0057942 (Penniclavine)

3D PDB for NP0057942 (Penniclavine)

SMILES for NP0057942 (Penniclavine)

INCHI for NP0057942 (Penniclavine)

Structure for NP0057942 (Penniclavine)

3D Structure for NP0057942 (Penniclavine)