General Information of the Compound
Compound ID
CP0045725
Compound Name
(4R,7R)-N,N-diethyl-6-methyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
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Synonyms
50-37-3
Barrels
Clearlight
Cubes
Cupcakes
D-Lsd
D-Lysergic acid diethylamide
Delysid
Greenies
Heavenly Blue
LSD (alkaloid)
LSD 25
LSD-25
LYSERGIC ACID DIETHYLAMIDE
Lisergide [DCIT]
Lysergamid
Lysergamide, N,N-diethyl-
Lysergaure diethylamid
Lysergic acid diethylamide-25
Lysergide
Lysergidum
Lysergidum [INN-Latin]
Lysergsaeurediaethylamid
Lysergsauerediaethylamid
Microdots
N,N-Diethyl-D-lysergamide
N,N-Diethyllysergamide
Pearly gates
Royal blue
Spoonies
Sunshine
Trippers
Ubergluben
Wedding bells
Yellows
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Structure
Formula
C20H25N3O
Molecular Weight
323.44
Canonical SMILES
CCN(CC)C(=O)[C@H]1CN(C)[C@@H]2Cc3c[nH]c4cccc(C2=C1)c34
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InChI
InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1
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InChIKey
VAYOSLLFUXYJDT-RDTXWAMCSA-N
CAS
50-37-3
Physicochemical Property
logP
2.906
Rotatable Bonds
3
Heavy Atom Count
24
Polar Areas
39.34
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Complexity
24

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 5761
SID: 15976361
ChEMBL ID
CHEMBL263881
DrugBank ID
DB04829
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT00819, 5-hydroxytryptamine receptor 1A
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
Ki = 1.259 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 1.1 nM
Protein ID: PT00825, 5-hydroxytryptamine receptor 2A
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000025 HEK-293T Homo sapiens (Human)  4
1
EC50 = 5.19 nM
   TI
   LI
   LO
   TS
2
EC50 = 5.38 nM
   TI
   LI
   LO
   TS
3
EC50 = 12.9 nM
   TI
   LI
   LO
   TS
4
EC50 = 13.2 nM
   TI
   LI
   LO
   TS
CL000068 A-549 Homo sapiens (Human)  2
1
Ki = 2.6 nM
   TI
   LI
   LO
   TS
2
Ki = 4 nM
   TI
   LI
   LO
   TS
CL000006 HEK293 Homo sapiens (Human)  3
1
Ki = 3.1 nM
   TI
   LI
   LO
   TS
2
Ki = 3.162 nM
   TI
   LI
   LO
   TS
3
Ki = 3.5 nM
   TI
   LI
   LO
   TS
Protein ID: PT00939, 5-hydroxytryptamine receptor 2C
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293 Homo sapiens (Human)  1
1
Ki = 5.012 nM
   TI
   LI
   LO
   TS
Protein ID: PT01354, 5-hydroxytryptamine receptor 6
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000017 HeLa Homo sapiens (Human)  1
1
Ki = 6.31 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 6.9 nM
Protein ID: PT01005, D(2) dopamine receptor
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000011 CHO Cricetulus griseus (Chinese hamster)  1
1
Ki = 125.89 nM
   TI
   LI
   LO
   TS
Biochemical Assays
1 Ki = 120 nM
Clinical Information about the Compound
Drug 1 ( LYSERGIC ACID DIETHYLAMIDE )
Drug Name LYSERGIC ACID DIETHYLAMIDE
Indication
Addictive disorder
Withdrawn from market
Target(s)
5-HT 2A receptor (HTR2A)
Inhibitor
5-HT 1A receptor (HTR1A)
Inhibitor