Mrv0541 07251413582D          

 19 20  0  0  0  0            999 V2000
    0.0000   -2.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991   -1.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9840   -2.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991   -2.8359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5610   -0.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8159    0.2397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6229    0.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7540   -0.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2639    0.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.5185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.5185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.7190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.1060    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9280   -0.9029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  6  1  0  0  0  0
  4  1  1  0  0  0  0
  3  4  2  0  0  0  0
  4  8  1  0  0  0  0
  3 14  1  0  0  0  0
 14  5  2  0  0  0  0
  5  2  1  0  0  0  0
  6  7  2  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
 12  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
 10 11  1  0  0  0  0
 14 15  1  0  0  0  0
 15 18  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <ID>
CHEBI:8614

> <NAME>
psilocybin

> <DEFINITION>
A tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional phosphoryloxy substituent at position 4. The major hallucinogenic alkaloid isolated from Psilocybe mushrooms (also known as Teonanácatl or "magic mushrooms").

> <STAR>
3

> <SYNONYM>
Psilocybine; Psilocybin; psilocin phosphate ester; O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine; Indocybin; 4-phosphoryloxy-N,N-dimethyltryptamine; 3-(2-Dimethylaminoethyl)indol-4-yl dihydrogen phosphate; 3-(2-(Dimethylamino)ethyl)-1H-indol-4-ol dihydrogen phosphate ester

> <IUPAC_NAME>
3-[2-(dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate

> <INN>
psilocybinum; psilocybine; psilocibina

> <FORMULA>
C12H17N2O4P

> <MASS>
284.24810

> <MONOISOTOPIC_MASS>
284.09259

> <CHARGE>
0

> <SMILES>
CN(C)CCc1c[nH]c2cccc(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

> <BEILSTEIN_REGISTRY_NUMBER>
273158

> <CAS_REGISTRY_NUMBER>
520-52-5

> <REAXYS_REGISTRY_NUMBER>
273158

> <CHEMIDPLUS>
520-52-5

> <KEGG_COMPOUND_ACCESSION>
C07576

> <NIST_CHEMISTRY_WEBBOOK>
520-52-5

> <WIKIPEDIA_ACCESSION>
Psilocybin

> <PUBMED_CITATION>
14437505; 14578010; 17874073; 22836372; 22887928; 23044373; 23171696; 23627783; 23717644; 23785166; 23861318; 23909006; 24413570; 24444771; 24882567; 24904332; 24904346; 24989126; 25007546; 27210031; 27568263; 27568266; 27856683; 27909163; 27909164; 27909167; 27909168; 27909170; 27909171; 27909173; 27909174; 27909175; 28074670; 28101325; 28353056; 28422113; 28443617; 28481178; 28548221; 28585222; 28637246; 28678583; 28711736; 28763571; 28768346; 28781400; 28790944; 28918722; 29020861; 29030624; 29039233

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