Molecule

4-Hydroxytryptamine; 2'-N-Di-Me, O-phosphate

AlkaPlorer ID: AK006190

Synonym: Psilocybine, Indocybin, CY 39

IUPAC Name: [3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate

SMILES: CN(C)CCC1=CNC2=CC=CC(OP(=O)(O)O)=C12

InChI: InChI=1S/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)

InChIKey: QVDSEJDULKLHCG-UHFFFAOYSA-N

PubChem CID: 10624

CAS: 520-52-5

LOTUS: LTS0193685

NPASS: NPC106937

COCONUT: CNP0163590

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain
Psilocybe mexicana	Psilocybe	Strophariaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Linaria vulgaris	Linaria	Plantaginaceae	Lamiales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	Conocybe	Bolbitiaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Coleophoma crateriformis	Coleophoma	Dermateaceae	Helotiales	Leotiomycetes	Ascomycota	Fungi	Eukaryota
Ulmus rubra	Ulmus	Ulmaceae	Rosales	Magnoliopsida	Streptophyta	Viridiplantae	Eukaryota
None	Psilocybe	Strophariaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota
Inocybe aeruginascens	Inocybe	Inocybaceae	Agaricales	Agaricomycetes	Basidiomycota	Fungi	Eukaryota

Molecule Weight: 284.252

TPSA？: 85.79

MolLogP？: 1.7435

Number of H-Donors: 3

Number of H-Acceptors: 3

RingCount: 2

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Homo sapiens	Serotonin 2a (5-HT2a) receptor	EC50	3475.0	nM	10.1016/j.bmcl.2005.06.104
Homo sapiens	Serotonin 2b (5-HT2b) receptor	EC50	74.0	nM	10.1016/j.bmcl.2005.06.104
Homo sapiens	Serotonin 2c (5-HT2c) receptor	EC50	506.0	nM	10.1016/j.bmcl.2005.06.104
Mus musculus	Mus musculus	Activity	nan	None	10.1021/acs.jnatprod.9b01061
Mus musculus	Mus musculus	ED50	0.4	mg.kg-1	10.1021/acs.jnatprod.9b01061
None	Unchecked	Ac50	1.122	uM	None
None	Unchecked	AC50	1122.0	nM	None

AKRT ID	Reaction	Reaction Link ID
AKRT010393	CN(C)CCc1c[nH]c2cccc(O)c12>>CN(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12	R08480
AKRT010394	CN(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12.C[SAH]>>C[N+](C)(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12	RXN-19123
AKRT010395	CN(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12>>CN(C)CCc1c[nH]c2cccc(O)c12	R12142
AKRT010753	CNCCc1c[nH]c2cccc(OP(=O)(O)O)c12.C[33S]>>CN(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12	None
AKRT010754	CNCCc1c[nH]c2cccc(OP(=O)(O)O)c12.C[SAH]>>CN(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12	RXN-19092
AKRT014562	C[SAH].CNCCc1c[nH]c2cccc(OP(=O)(O)O)c12>>CN(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12	enzymemap_27178
AKRT014596	C[SAH].C[SAH].NCCc1c[nH]c2cccc(OP(=O)(O)O)c12>>CN(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12	RXN-19093