NP-MRD: Showing NP-Card for lysergene (NP0171355)

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Record Information

Version

2.0

Created at

2022-09-03 07:50:29 UTC

Updated at

2022-09-03 07:50:29 UTC

NP-MRD ID

NP0171355

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lysergene

Description

Lysergene belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline. lysergene was first documented in 1996 (PMID: 8923801). Based on a literature review very few articles have been published on Lysergene.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 37  0  0  0  0  0  0  0  0999 V2000
   -2.5789    2.9869    0.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8038    1.9532    1.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5908    1.8288    0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1371    0.6063   -0.0043 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0742    0.4419   -0.8023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5202    1.4586   -1.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6850    1.1895   -2.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3566   -0.0347   -2.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8815   -1.0454   -1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036   -2.3034   -1.0641 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2707   -2.7799   -0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3365   -1.7940    0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7302   -0.7454   -0.7237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1329   -1.7319    0.8916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8265   -0.6314    0.4823 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8890   -0.4099    1.3736 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1747   -0.7823    0.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0090    0.8358    2.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3412    3.7434    0.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4769    3.1038    1.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0584    2.6626   -0.1007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0791    2.4037   -1.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1227    1.9274   -2.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2514   -0.2222   -2.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386   -2.7955   -1.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078   -3.7708    0.2655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -1.6183    1.9519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639   -2.7221    0.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2903   -1.0407   -0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1628   -0.4190   -0.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0235   -0.2954    1.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2570   -1.8747    0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0804    0.9365    2.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3684    0.9387    2.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 18  1  0
 18  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  4 15  1  0
 15 14  1  0
 14 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5 13  2  0
 15 16  1  0
 13 12  1  0
  5  4  1  0
 13  9  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
 15 29  1  6
 14 27  1  0
 14 28  1  0
 11 26  1  0
 10 25  1  0
  8 24  1  0
  7 23  1  0
  6 22  1  0
M  END


  Mrv1652309032209502D          

 18 21  0  0  1  0            999 V2000
    4.7079   -0.4125    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
    1.8500   -0.4125    0.0000 C   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
    0.1794   -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 N   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
    1.1355   -0.0000    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  1  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    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
  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  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 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
  5 13  2  0  0  0  0
  9 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0171355

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC(=C)C=C2[C@H]1CC1=CNC3=CC=CC2=C13

> <INCHI_IDENTIFIER>
InChI=1S/C16H16N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8,15,17H,1,7,9H2,2H3/t15-/m1/s1

> <INCHI_KEY>
MVCNPXUMKZNDRO-OAHLLOKOSA-N

> <FORMULA>
C16H16N2

> <MOLECULAR_WEIGHT>
236.318

> <EXACT_MASS>
236.131348523

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.47193838011629

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
2.6441182929999996

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.995381463974997

> <JCHEM_PKA_STRONGEST_BASIC>
7.420193470797362

> <JCHEM_POLAR_SURFACE_AREA>
19.03

> <JCHEM_REFRACTIVITY>
75.7081

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7R)-6-methyl-4-methylidene-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.787  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.944  -2.537   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.479  -3.013   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.335  -1.982   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.655  -0.476   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.250   0.770   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.120  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.121   2.310   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    5    9                                                  
CONECT   14   12   15                                                       
CONECT   15   14    4   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆N₂

Average Mass

236.3180 Da

Monoisotopic Mass

236.13135 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CN1CC(=C)C=C2[C@H]1CC1=CNC3=CC=CC2=C13

InChI Identifier

InChI=1S/C16H16N2/c1-10-6-13-12-4-3-5-14-16(12)11(8-17-14)7-15(13)18(2)9-10/h3-6,8,15,17H,1,7,9H2,2H3/t15-/m1/s1

InChI Key

MVCNPXUMKZNDRO-OAHLLOKOSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoloquinolines. These are polycyclic aromatic compounds containing an indole fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Indoloquinolines

Direct Parent

Indoloquinolines

Alternative Parents

Substituents

Ergoline skeleton
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Alkaloid or derivatives
Aralkylamine
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organonitrogen compound
Organic nitrogen compound
Amine
Hydrocarbon derivative
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	2.88	ALOGPS
logP	2.64	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	17	ChemAxon
pKa (Strongest Basic)	7.42	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	19.03 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.71 m³·mol⁻¹	ChemAxon
Polarizability	27.47 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

10390293

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lysergene

METLIN ID

Not Available

PubChem Compound

12312578

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Pertz H: Naturally occurring clavines: antagonism/partial agonism at 5-HT2A receptors and antagonism at alpha 1-adrenoceptors in blood vessels. Planta Med. 1996 Oct;62(5):387-92. doi: 10.1055/s-2006-957922. [PubMed:8923801 ]
LOTUS database [Link]

Showing NP-Card for lysergene (NP0171355)

MOL for NP0171355 (lysergene)

3D MOL for NP0171355 (lysergene)

3D SDF for NP0171355 (lysergene)

3D-SDF for NP0171355 (lysergene)

PDB for NP0171355 (lysergene)

3D PDB for NP0171355 (lysergene)

SMILES for NP0171355 (lysergene)

INCHI for NP0171355 (lysergene)

Structure for NP0171355 (lysergene)

3D Structure for NP0171355 (lysergene)