NP-MRD: Showing NP-Card for Lysergic acid (NP0057926)

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Record Information

Version

2.0

Created at

2022-04-28 03:17:13 UTC

Updated at

2022-04-28 03:17:13 UTC

NP-MRD ID

NP0057926

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lysergic acid

Description

Lysergic acid, also known as lysergate or acid, lysergic, belongs to the class of organic compounds known as lysergic acids. These are derivatives of lysergic acid are amides in which the amidic moiety is formed by a small peptide or an alkylamide. Lysergic acid is found in Claviceps purpurea . Lysergic acid was first documented in 2022 (PMID: 35458717). Based on a literature review a small amount of articles have been published on lysergic acid (PMID: 35401281) (PMID: 35343858) (PMID: 35341564).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -2.1148   -2.2917   -1.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7554   -1.3186   -0.1644 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7149   -0.2246   -0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5235    0.8051    0.7643 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4021    1.9639    0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9023    3.0863    0.2998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7730    1.8138    0.3937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0956    1.2026    0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1742    0.4729    0.2675 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2523    0.8631    0.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6102    2.1645    0.6745 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9673    2.4702    0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9304    1.5079    0.4785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5921    0.2082    0.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2051   -0.9507   -0.1497 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2610   -1.9174   -0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0026   -1.3283   -0.2159 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -0.0413    0.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6135   -1.8071   -0.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4284   -0.7769   -0.4973 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3963   -3.1162   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0751   -2.7577   -0.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3593   -1.8211   -2.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7222   -0.6812   -0.2335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5332    0.2234   -1.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7952    0.3506    1.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2835    1.1847    1.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8878    2.1077    1.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8422    2.8662    0.8569 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2351    3.4937    0.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9865    1.7390    0.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2387   -1.0650   -0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4048   -2.9518   -0.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6000   -2.5014   -1.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4491   -2.4858    0.5470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4918   -0.4871   -1.5663 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  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
  4  5  1  0
  5  7  1  0
  5  6  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
  4 26  1  1
  8 28  1  0
 20 36  1  6
 19 34  1  0
 19 35  1  0
 16 33  1  0
 15 32  1  0
 13 31  1  0
 12 30  1  0
 11 29  1  0
  7 27  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
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    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  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057926

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)/t10-,14-/m1/s1

> <INCHI_KEY>
ZAGRKAFMISFKIO-QMTHXVAHSA-N

> <FORMULA>
C16H16N2O2

> <MOLECULAR_WEIGHT>
268.316

> <EXACT_MASS>
268.121177763

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.99178738129313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
-0.7841138707024823

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.028098747735392

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6504738493156754

> <JCHEM_PKA_STRONGEST_BASIC>
8.264743896734274

> <JCHEM_POLAR_SURFACE_AREA>
56.33

> <JCHEM_REFRACTIVITY>
77.6219

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.11e-01 g/l

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

> <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       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.788   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.122   1.540   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                                                  
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   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Value	Source
(8beta)-9,10-Didehydro-6-methylergoline-8-carboxylic acid	ChEBI
(8b)-9,10-Didehydro-6-methylergoline-8-carboxylate	Generator
(8b)-9,10-Didehydro-6-methylergoline-8-carboxylic acid	Generator
(8beta)-9,10-Didehydro-6-methylergoline-8-carboxylate	Generator
(8Β)-9,10-didehydro-6-methylergoline-8-carboxylate	Generator
(8Β)-9,10-didehydro-6-methylergoline-8-carboxylic acid	Generator
Lysergate	Generator
Acid, lysergic	MeSH

Chemical Formula

C₁₆H₁₆N₂O₂

Average Mass

268.3160 Da

Monoisotopic Mass

268.12118 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)/t10-,14-/m1/s1

InChI Key

ZAGRKAFMISFKIO-QMTHXVAHSA-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 lysergic acids. These are derivatives of lysergic acid are amides in which the amidic moiety is formed by a small peptide or an alkylamide.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ergoline and derivatives

Sub Class

Lysergic acids and derivatives

Direct Parent

Lysergic acids

Alternative Parents

Substituents

Lysergic acid
Indoloquinoline
Benzoquinoline
Pyrroloquinoline
Quinoline-3-carboxylic acid
Quinoline
3-alkylindole
Indole
Indole or derivatives
Isoindole or derivatives
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Amino acid
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Hydrocarbon derivative
Organic oxygen compound
Amine
Organopnictogen compound
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

ergoline alkaloid (CHEBI:6604 )

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	1.68	ALOGPS
logP	-0.78	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.65	ChemAxon
pKa (Strongest Basic)	8.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	56.33 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.62 m³·mol⁻¹	ChemAxon
Polarizability	28.99 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00011201

Chemspider ID

6461

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lysergic acid

METLIN ID

Not Available

PubChem Compound

6717

PDB ID

Not Available

ChEBI ID

6604

Good Scents ID

Not Available

References

General References

Lowe H, Toyang N, Steele B, Grant J, Ali A, Gordon L, Ngwa W: Psychedelics: Alternative and Potential Therapeutic Options for Treating Mood and Anxiety Disorders. Molecules. 2022 Apr 14;27(8):2520. doi: 10.3390/molecules27082520. [PubMed:35458717 ]
Haslacher D, Novkovic N, Buthut M, Heinz A, Soekadar SR: Pathological Delta Oscillations in Hallucinogen Persisting Perception Disorder: A Case Report. Front Psychiatry. 2022 Mar 24;13:867314. doi: 10.3389/fpsyt.2022.867314. eCollection 2022. [PubMed:35401281 ]
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Showing NP-Card for Lysergic acid (NP0057926)

MOL for NP0057926 (Lysergic acid)

3D MOL for NP0057926 (Lysergic acid)

3D SDF for NP0057926 (Lysergic acid)

3D-SDF for NP0057926 (Lysergic acid)

PDB for NP0057926 (Lysergic acid)

3D PDB for NP0057926 (Lysergic acid)

SMILES for NP0057926 (Lysergic acid)

INCHI for NP0057926 (Lysergic acid)

Structure for NP0057926 (Lysergic acid)

3D Structure for NP0057926 (Lysergic acid)