NP-MRD: Showing NP-Card for lysergol (NP0184113)

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Record Information

Version

2.0

Created at

2022-09-03 23:09:55 UTC

Updated at

2022-09-03 23:09:55 UTC

NP-MRD ID

NP0184113

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lysergol

Description

Lysergol 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. Lysergol is a very strong basic compound (based on its pKa). Lysergol is a potentially toxic compound. Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Usually the gastrointestinal effects precede the central nervous system effects. Lysergol is an alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi (most within Claviceps), and in the morning glory family of plants (Convolvulaceae), including the hallucinogenic seeds of Rivea corymbosa (ololiuhqui), Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea. Treatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
    1.9599   -2.7110   -0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114   -1.6379    0.3421 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3275   -0.9577    1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5366    0.4910    0.8136 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3786    0.7171   -0.3875 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4795    2.1113   -0.5770 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1858    1.1450    0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1774    0.4561    0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1353    1.1343    0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2805    2.5031    0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5634    2.9877    0.0823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6629    2.1442   -0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4958    0.7654   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2594   -0.3111   -0.5198 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4653   -1.4244   -0.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1627   -1.0279   -0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2070    0.3292   -0.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9139   -1.7818   -0.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3392   -0.9445   -0.2501 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2029   -3.5172   -0.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8246   -3.1318    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863   -2.3727   -1.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -1.0807    2.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239   -1.4352    1.0609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0232    0.9643    1.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0007    0.2451   -1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4120    0.3806   -0.1642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4519    2.5767    0.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0308    2.1524    1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4814    3.1689    0.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8209    4.0365    0.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6490    2.5387   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2766   -0.3010   -0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7987   -2.4373   -0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9029   -2.5313   -1.0317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8969   -2.3875    0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5837   -0.8566   -1.3544 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  1  0
  4  7  1  0
  7  8  2  0
  8 19  1  0
 19 18  1  0
 18 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9 17  2  0
 19  2  1  0
 17 16  1  0
  9  8  1  0
 17 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  1
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
 19 37  1  6
 18 35  1  0
 18 36  1  0
 15 34  1  0
 14 33  1  0
 12 32  1  0
 11 31  1  0
 10 30  1  0
M  END


  Mrv0541 02241212302D          

 19 22  0  0  0  0            999 V2000
   -2.2715   -0.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5575   -1.3911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5585   -2.2161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8445   -2.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1296   -2.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8425   -0.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1714    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9964    1.1143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8455   -3.4545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1315   -3.8679    0.0000 O   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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 12 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184113

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CC(CO)C=C2C1CC1=CNC3=CC=CC2=C13

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,10,15,17,19H,6,8-9H2,1H3

> <INCHI_KEY>
BIXJFIJYBLJTMK-UHFFFAOYSA-N

> <FORMULA>
C16H18N2O

> <MOLECULAR_WEIGHT>
254.3269

> <EXACT_MASS>
254.141913208

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.832785088229976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaen-4-yl}methanol

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
1.518688484333333

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.037243950734204

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.382463847168651

> <JCHEM_PKA_STRONGEST_BASIC>
7.930318605766813

> <JCHEM_POLAR_SURFACE_AREA>
39.260000000000005

> <JCHEM_REFRACTIVITY>
77.83749999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lysergol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.240  -1.825   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.907  -2.597   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.909  -4.137   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.576  -4.908   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.242  -4.140   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.240  -2.600   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.573  -1.828   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.860   2.080   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.578  -6.448   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.245  -7.220   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    6   17                                                  
CONECT   17   16    9   12                                                  
CONECT   18    4   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Value	Source
Lysergol, (8alpha)-isomer	MeSH
Isolysergol	MeSH

Chemical Formula

C₁₆H₁₈N₂O

Average Mass

254.3269 Da

Monoisotopic Mass

254.14191 Da

IUPAC Name

{6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaen-4-yl}methanol

Traditional Name

lysergol

CAS Registry Number

Not Available

SMILES

CN1CC(CO)C=C2C1CC1=CNC3=CC=CC2=C13

InChI Identifier

InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,10,15,17,19H,6,8-9H2,1H3

InChI Key

BIXJFIJYBLJTMK-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, 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 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
Heteroaromatic compound
Pyrrole
1,3-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Amine
Organopnictogen compound
Alcohol
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
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	2.17	ALOGPS
logP	1.52	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	15.38	ChemAxon
pKa (Strongest Basic)	7.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	39.26 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.84 m³·mol⁻¹	ChemAxon
Polarizability	28.83 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lysergol

METLIN ID

Not Available

PubChem Compound

3982

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for lysergol (NP0184113)

MOL for NP0184113 (lysergol)

3D MOL for NP0184113 (lysergol)

3D SDF for NP0184113 (lysergol)

3D-SDF for NP0184113 (lysergol)

PDB for NP0184113 (lysergol)

3D PDB for NP0184113 (lysergol)

SMILES for NP0184113 (lysergol)

INCHI for NP0184113 (lysergol)

Structure for NP0184113 (lysergol)

3D Structure for NP0184113 (lysergol)