Marvin  08151113352D          

 28 32  0  0  1  0            999 V2000
    2.3618   -1.8630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3618   -1.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6312   -0.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784   -2.2873    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0689   -2.2637    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1597   -1.4151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7996   -1.8630    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0689   -0.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0689   -3.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7996   -1.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6865   -2.1847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6784   -3.1123    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6312    0.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3854   -3.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8877   -1.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9241    0.6354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9712   -3.5366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6900   -1.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0689    0.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3854    0.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0579   -2.9420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6429   -2.9613    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2096    0.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5048    0.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2096   -0.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567   -3.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4577   -3.5366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2567   -2.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  1  0  0  0  0
  1 15  1  1  0  0  0
  3  2  1  0  0  0  0
  8  2  2  0  0  0  0
 13  3  2  0  0  0  0
  6  3  1  0  0  0  0
  4  6  1  6  0  0  0
 12  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  5  1  0  0  0  0
  5 22  1  1  0  0  0
 10  7  1  0  0  0  0
  7 11  1  1  0  0  0
 19  8  1  0  0  0  0
 10  8  1  0  0  0  0
 14  9  2  0  0  0  0
 18 11  1  0  0  0  0
 21 11  1  0  0  0  0
 12 17  1  6  0  0  0
 14 12  1  0  0  0  0
 16 13  1  0  0  0  0
 20 13  1  0  0  0  0
 18 15  1  0  0  0  0
 20 19  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  END
> <ID>
CHEBI:27808

> <NAME>
heroin

> <DEFINITION>
A morphinane alkaloid that is morphine bearing two acetyl substituents on the O-3 and O-6 positions. As with other opioids, heroin is used as both an analgesic and a recreational drug. Frequent and regular administration is associated with tolerance and physical dependence, which may develop into addiction. Its use includes treatment for acute pain, such as in severe physical trauma, myocardial infarction, post-surgical pain, and chronic pain, including end-stage cancer and other terminal illnesses.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:5680; CHEBI:24528

> <SYNONYM>
O,O'-Diacetylmorphine; Heroin; Diamorphine; Diacetylmorphine; Diacetylmorphine; 7,8-Dihydro-4,5-alpha-epoxy-17-methylmorphinan-3,6-alpha-diol diacetate; 3,6-Diacetylmorphine; (5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol diacetate (ester)

> <IUPAC_NAME>
17-methyl-7,8-didehydro-4,5alpha-epoxymorphinan-3,6alpha-diyl diacetate

> <FORMULA>
C21H23NO5

> <MASS>
369.41100

> <MONOISOTOPIC_MASS>
369.15762

> <CHARGE>
0

> <SMILES>
[H][C@]12C=C[C@H](OC(C)=O)[C@@H]3Oc4c(OC(C)=O)ccc5C[C@H]1N(C)CC[C@@]23c45

> <INCHI>
InChI=1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1

> <INCHIKEY>
GVGLGOZIDCSQPN-PVHGPHFFSA-N

> <CAS_REGISTRY_NUMBER>
561-27-3

> <REAXYS_REGISTRY_NUMBER>
99261

> <CHEMIDPLUS>
561-27-3

> <DRUGBANK_ACCESSION>
DB01452

> <KEGG_COMPOUND_ACCESSION>
C06534

> <KEGG_DRUG_ACCESSION>
D07286

> <NIST_CHEMISTRY_WEBBOOK>
561-27-3

> <WIKIPEDIA_ACCESSION>
Heroin

> <PUBMED_CITATION>
10454516; 11441925; 11448454; 11557911; 12965116; 14534521; 15212982; 15213301; 15550572; 15772255; 15843500; 16076083; 16333714; 20331562; 20649590; 20735218; 20810225; 20855171; 21235340; 21309955; 21362452; 21452028; 21527184; 21568984; 21608377; 21734607; 21740578; 2352148; 8858977; 8893832; 9918543

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