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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:53 UTC

HMDB ID

HMDB0015196

Secondary Accession Numbers

HMDB15196

Metabolite Identification

Common Name

Acetophenazine

Description

Acetophenazine is only found in individuals that have used or taken this drug.It is an antipsychotic drug of moderate-potency. It is used in the treatment of disorganized and psychotic thinking. It is also used to help treat false perceptions (e.g. hallucinations or delusions).Acetophenazine blocks postsynaptic mesolimbic dopaminergic D1 and D2 receptors in the brain; depresses the release of hypothalamic and hypophyseal hormones and is believed to depress the reticular activating system thus affecting basal metabolism, body temperature, wakefulness, vasomotor tone, and emesis.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02231215132D          

 29 32  0  0  0  0            999 V2000
   -0.8484   -0.6703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8484   -2.3203    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340   -1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629   -1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629   -1.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340   -1.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805   -0.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774   -0.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774   -2.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805   -2.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -1.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -1.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8484    0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805    1.8047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    2.6297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    1.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805    2.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950    3.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950    1.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239    3.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4384    2.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1529    3.0422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239   -1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094   -0.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    0.1547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
 13  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  3  2  0  0  0  0
  5  4  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 26  7  1  0  0  0  0
 25  8  2  0  0  0  0
 11  9  2  0  0  0  0
 12 10  1  0  0  0  0
 12 26  2  0  0  0  0
 25 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 19 16  1  0  0  0  0
 21 16  1  0  0  0  0
 18 17  1  0  0  0  0
 20 17  1  0  0  0  0
 22 17  1  0  0  0  0
 21 18  1  0  0  0  0
 20 19  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 26 28  1  0  0  0  0
 28 27  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

HMDB0015196
     RDKit          3D
Acetophenazine
 58 61  0  0  0  0  0  0  0  0999 V2000
   -3.9348    4.8990   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2760    3.6307   -1.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302    3.6298   -2.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5115    2.4074   -0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3308    2.4019    0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5057    1.2339    1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9029    0.0770    1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0739    0.0366    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8826    1.2394   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4087   -1.1309   -0.3861 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5406   -1.0671   -1.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0967   -0.8510   -1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2392    0.4007   -0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    0.5100   -0.2265 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1201   -0.4761    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -0.1190    1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3047    0.5101    0.1857 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3374    1.3849    0.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4156    0.5350    1.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8631   -0.3735    0.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8772    0.5645   -1.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4505    0.2806   -1.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5291   -2.4177    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8164   -3.5014   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655   -4.7678    0.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438   -4.9759    1.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3551   -3.9300    1.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2805   -2.6820    1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2303   -1.3549    2.1178 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0077    4.6860   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4732    5.2872    0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682    5.6741   -1.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8363    3.3281    1.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1729    1.2855    2.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    1.3170   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6926   -2.0407   -2.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8288   -0.2536   -2.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585   -1.7178   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4377   -0.7671   -2.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3055    0.5913    0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0315    1.2624   -1.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1685   -1.4544    0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3959   -0.5405    1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4096    0.5635    2.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0160   -1.0240    1.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0100    2.1415    1.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7767    1.9357   -0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2237    1.1799    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9765   -0.0551    2.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5249    0.0867   -0.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    1.5685   -1.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217   -0.1422   -1.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058    0.8598   -2.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743   -0.8169   -1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760   -3.4430   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089   -5.6002   -0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7163   -5.9497    1.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9908   -4.0564    2.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 10 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
  9  4  1  0
 22 14  1  0
 28 23  1  0
 29  7  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  6 34  1  0
  9 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  0
M  END


  Mrv0541 02231215132D          

 29 32  0  0  0  0            999 V2000
   -0.8484   -0.6703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8484   -2.3203    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340   -1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629   -1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629   -1.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340   -1.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805   -0.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774   -0.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2774   -2.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805   -2.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -1.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -1.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8484    0.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805    1.8047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    2.6297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    1.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5805    2.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950    3.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950    1.3922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239    3.0422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4384    2.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1529    3.0422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9918   -1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239   -1.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094   -0.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0094    0.1547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  1  1  0  0  0  0
 13  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  2  1  0  0  0  0
  6  3  1  0  0  0  0
  7  3  2  0  0  0  0
  5  4  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 26  7  1  0  0  0  0
 25  8  2  0  0  0  0
 11  9  2  0  0  0  0
 12 10  1  0  0  0  0
 12 26  2  0  0  0  0
 25 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 19 16  1  0  0  0  0
 21 16  1  0  0  0  0
 18 17  1  0  0  0  0
 20 17  1  0  0  0  0
 22 17  1  0  0  0  0
 21 18  1  0  0  0  0
 20 19  1  0  0  0  0
 23 22  1  0  0  0  0
 24 23  1  0  0  0  0
 26 28  1  0  0  0  0
 28 27  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015196

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H29N3O2S/c1-18(28)19-7-8-23-21(17-19)26(20-5-2-3-6-22(20)29-23)10-4-9-24-11-13-25(14-12-24)15-16-27/h2-3,5-8,17,27H,4,9-16H2,1H3

> <INCHI_KEY>
WNTYBHLDCKXEOT-UHFFFAOYSA-N

> <FORMULA>
C23H29N3O2S

> <MOLECULAR_WEIGHT>
411.56

> <EXACT_MASS>
411.198047877

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
46.67707657970997

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)ethan-1-one

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
2.6456206516666665

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.184498311746577

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.464547169765439

> <JCHEM_PKA_STRONGEST_BASIC>
8.06622490611481

> <JCHEM_POLAR_SURFACE_AREA>
47.02

> <JCHEM_REFRACTIVITY>
121.69669999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetophenazine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015196
     RDKit          3D
Acetophenazine
 58 61  0  0  0  0  0  0  0  0999 V2000
   -3.9348    4.8990   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2760    3.6307   -1.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302    3.6298   -2.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5115    2.4074   -0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3308    2.4019    0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5057    1.2339    1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9029    0.0770    1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0739    0.0366    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8826    1.2394   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4087   -1.1309   -0.3861 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5406   -1.0671   -1.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0967   -0.8510   -1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2392    0.4007   -0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    0.5100   -0.2265 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1201   -0.4761    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -0.1190    1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3047    0.5101    0.1857 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3374    1.3849    0.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4156    0.5350    1.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8631   -0.3735    0.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8772    0.5645   -1.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4505    0.2806   -1.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5291   -2.4177    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8164   -3.5014   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655   -4.7678    0.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438   -4.9759    1.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3551   -3.9300    1.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2805   -2.6820    1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2303   -1.3549    2.1178 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0077    4.6860   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4732    5.2872    0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682    5.6741   -1.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8363    3.3281    1.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1729    1.2855    2.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    1.3170   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6926   -2.0407   -2.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8288   -0.2536   -2.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585   -1.7178   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4377   -0.7671   -2.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3055    0.5913    0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0315    1.2624   -1.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1685   -1.4544    0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3959   -0.5405    1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4096    0.5635    2.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0160   -1.0240    1.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0100    2.1415    1.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7767    1.9357   -0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2237    1.1799    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9765   -0.0551    2.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5249    0.0867   -0.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    1.5685   -1.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217   -0.1422   -1.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058    0.8598   -2.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743   -0.8169   -1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760   -3.4430   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089   -5.6002   -0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7163   -5.9497    1.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9908   -4.0564    2.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 10 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
  9  4  1  0
 22 14  1  0
 28 23  1  0
 29  7  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  6 34  1  0
  9 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      -1.584  -1.251   0.000  0.00  0.00           N+0
HETATM    2  S   UNK     0      -1.584  -4.331   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      -0.250  -2.021   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.917  -2.021   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.917  -3.561   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.250  -3.561   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.084  -1.251   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.251  -1.251   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.251  -4.331   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.084  -4.331   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.585  -3.561   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.417  -3.561   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.584   0.289   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.250   1.059   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.250   2.599   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       1.084   3.369   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       3.751   4.909   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.751   3.369   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.084   4.909   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.417   5.679   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.417   2.599   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.085   5.679   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.418   4.909   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.752   5.679   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.585  -2.021   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.417  -2.021   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.085  -2.021   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.751  -1.251   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.751   0.289   0.000  0.00  0.00           O+0
CONECT    1    3    4   13                                                  
CONECT    2    5    6                                                       
CONECT    3    1    6    7                                                  
CONECT    4    1    5    8                                                  
CONECT    5    2    4    9                                                  
CONECT    6    2    3   10                                                  
CONECT    7    3   26                                                       
CONECT    8    4   25                                                       
CONECT    9    5   11                                                       
CONECT   10    6   12                                                       
CONECT   11    9   25                                                       
CONECT   12   10   26                                                       
CONECT   13    1   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   19   21                                                  
CONECT   17   18   20   22                                                  
CONECT   18   17   21                                                       
CONECT   19   16   20                                                       
CONECT   20   17   19                                                       
CONECT   21   16   18                                                       
CONECT   22   17   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25    8   11                                                       
CONECT   26    7   12   28                                                  
CONECT   27   28                                                            
CONECT   28   26   27   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0015196
HETATM    1  C1  UNL     1      -3.935   4.899  -0.580  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.276   3.631  -1.011  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.530   3.630  -2.014  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.511   2.407  -0.255  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.331   2.402   0.845  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.506   1.234   1.524  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.903   0.077   1.158  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.074   0.037   0.063  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.883   1.239  -0.652  1.00  0.00           C  
HETATM   10  N1  UNL     1      -2.409  -1.131  -0.386  1.00  0.00           N  
HETATM   11  C9  UNL     1      -1.541  -1.067  -1.550  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.097  -0.851  -1.231  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.239   0.401  -0.497  1.00  0.00           C  
HETATM   14  N2  UNL     1       1.667   0.510  -0.227  1.00  0.00           N  
HETATM   15  C12 UNL     1       2.120  -0.476   0.729  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.517  -0.119   1.153  1.00  0.00           C  
HETATM   17  N3  UNL     1       4.305   0.510   0.186  1.00  0.00           N  
HETATM   18  C14 UNL     1       5.337   1.385   0.610  1.00  0.00           C  
HETATM   19  C15 UNL     1       6.416   0.535   1.295  1.00  0.00           C  
HETATM   20  O2  UNL     1       6.863  -0.373   0.324  1.00  0.00           O  
HETATM   21  C16 UNL     1       3.877   0.564  -1.141  1.00  0.00           C  
HETATM   22  C17 UNL     1       2.451   0.281  -1.423  1.00  0.00           C  
HETATM   23  C18 UNL     1      -2.529  -2.418   0.263  1.00  0.00           C  
HETATM   24  C19 UNL     1      -1.816  -3.501  -0.248  1.00  0.00           C  
HETATM   25  C20 UNL     1      -1.865  -4.768   0.326  1.00  0.00           C  
HETATM   26  C21 UNL     1      -2.644  -4.976   1.443  1.00  0.00           C  
HETATM   27  C22 UNL     1      -3.355  -3.930   1.967  1.00  0.00           C  
HETATM   28  C23 UNL     1      -3.280  -2.682   1.367  1.00  0.00           C  
HETATM   29  S1  UNL     1      -4.230  -1.355   2.118  1.00  0.00           S  
HETATM   30  H1  UNL     1      -5.008   4.686  -0.443  1.00  0.00           H  
HETATM   31  H2  UNL     1      -3.473   5.287   0.367  1.00  0.00           H  
HETATM   32  H3  UNL     1      -3.768   5.674  -1.371  1.00  0.00           H  
HETATM   33  H4  UNL     1      -4.836   3.328   1.166  1.00  0.00           H  
HETATM   34  H5  UNL     1      -5.173   1.286   2.397  1.00  0.00           H  
HETATM   35  H6  UNL     1      -2.262   1.317  -1.528  1.00  0.00           H  
HETATM   36  H7  UNL     1      -1.693  -2.041  -2.122  1.00  0.00           H  
HETATM   37  H8  UNL     1      -1.829  -0.254  -2.248  1.00  0.00           H  
HETATM   38  H9  UNL     1       0.358  -1.718  -0.668  1.00  0.00           H  
HETATM   39  H10 UNL     1       0.438  -0.767  -2.231  1.00  0.00           H  
HETATM   40  H11 UNL     1      -0.306   0.591   0.424  1.00  0.00           H  
HETATM   41  H12 UNL     1       0.032   1.262  -1.202  1.00  0.00           H  
HETATM   42  H13 UNL     1       2.169  -1.454   0.211  1.00  0.00           H  
HETATM   43  H14 UNL     1       1.396  -0.541   1.552  1.00  0.00           H  
HETATM   44  H15 UNL     1       3.410   0.563   2.046  1.00  0.00           H  
HETATM   45  H16 UNL     1       4.016  -1.024   1.536  1.00  0.00           H  
HETATM   46  H17 UNL     1       5.010   2.142   1.337  1.00  0.00           H  
HETATM   47  H18 UNL     1       5.777   1.936  -0.242  1.00  0.00           H  
HETATM   48  H19 UNL     1       7.224   1.180   1.666  1.00  0.00           H  
HETATM   49  H20 UNL     1       5.976  -0.055   2.119  1.00  0.00           H  
HETATM   50  H21 UNL     1       7.525   0.087  -0.257  1.00  0.00           H  
HETATM   51  H22 UNL     1       4.131   1.569  -1.585  1.00  0.00           H  
HETATM   52  H23 UNL     1       4.522  -0.142  -1.747  1.00  0.00           H  
HETATM   53  H24 UNL     1       2.106   0.860  -2.284  1.00  0.00           H  
HETATM   54  H25 UNL     1       2.374  -0.817  -1.644  1.00  0.00           H  
HETATM   55  H26 UNL     1      -1.176  -3.443  -1.106  1.00  0.00           H  
HETATM   56  H27 UNL     1      -1.309  -5.600  -0.081  1.00  0.00           H  
HETATM   57  H28 UNL     1      -2.716  -5.950   1.931  1.00  0.00           H  
HETATM   58  H29 UNL     1      -3.991  -4.056   2.863  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3    3    4
CONECT    4    5    5    9
CONECT    5    6   33
CONECT    6    7    7   34
CONECT    7    8   29
CONECT    8    9    9   10
CONECT    9   35
CONECT   10   11   23
CONECT   11   12   36   37
CONECT   12   13   38   39
CONECT   13   14   40   41
CONECT   14   15   22
CONECT   15   16   42   43
CONECT   16   17   44   45
CONECT   17   18   21
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   50
CONECT   21   22   51   52
CONECT   22   53   54
CONECT   23   24   24   28
CONECT   24   25   55
CONECT   25   26   26   56
CONECT   26   27   57
CONECT   27   28   28   58
CONECT   28   29
END

HMDB0015196
     RDKit          3D
Acetophenazine
 58 61  0  0  0  0  0  0  0  0999 V2000
   -3.9348    4.8990   -0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2760    3.6307   -1.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5302    3.6298   -2.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5115    2.4074   -0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3308    2.4019    0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5057    1.2339    1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9029    0.0770    1.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0739    0.0366    0.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8826    1.2394   -0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4087   -1.1309   -0.3861 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5406   -1.0671   -1.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0967   -0.8510   -1.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2392    0.4007   -0.4968 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6673    0.5100   -0.2265 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1201   -0.4761    0.7295 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5169   -0.1190    1.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3047    0.5101    0.1857 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3374    1.3849    0.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4156    0.5350    1.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8631   -0.3735    0.3236 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8772    0.5645   -1.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4505    0.2806   -1.4232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5291   -2.4177    0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8164   -3.5014   -0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655   -4.7678    0.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438   -4.9759    1.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3551   -3.9300    1.9673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2805   -2.6820    1.3669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2303   -1.3549    2.1178 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0077    4.6860   -0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4732    5.2872    0.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7682    5.6741   -1.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8363    3.3281    1.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1729    1.2855    2.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    1.3170   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6926   -2.0407   -2.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8288   -0.2536   -2.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3585   -1.7178   -0.6680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4377   -0.7671   -2.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3055    0.5913    0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0315    1.2624   -1.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1685   -1.4544    0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3959   -0.5405    1.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4096    0.5635    2.0458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0160   -1.0240    1.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0100    2.1415    1.3372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7767    1.9357   -0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2237    1.1799    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9765   -0.0551    2.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5249    0.0867   -0.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308    1.5685   -1.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5217   -0.1422   -1.7465 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1058    0.8598   -2.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3743   -0.8169   -1.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760   -3.4430   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089   -5.6002   -0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7163   -5.9497    1.9312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9908   -4.0564    2.8626 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 10 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
  9  4  1  0
 22 14  1  0
 28 23  1  0
 29  7  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  5 33  1  0
  6 34  1  0
  9 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 13 40  1  0
 13 41  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 24 55  1  0
 25 56  1  0
 26 57  1  0
 27 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Tindal	HMDB
Acetophenazine, (Z)-2-maleate (1:2) salt	HMDB
Acetophenazine, ion (1+)	HMDB
Acetophenazine maleate	HMDB

Chemical Formula

C₂₃H₂₉N₃O₂S

Average Molecular Weight

411.56

Monoisotopic Molecular Weight

411.198047877

IUPAC Name

1-(10-{3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl}-10H-phenothiazin-2-yl)ethan-1-one

Traditional Name

acetophenazine

CAS Registry Number

2751-68-0

SMILES

CC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C1

InChI Identifier

InChI=1S/C23H29N3O2S/c1-18(28)19-7-8-23-21(17-19)26(20-5-2-3-6-22(20)29-23)10-4-9-24-11-13-25(14-12-24)15-16-27/h2-3,5-8,17,27H,4,9-16H2,1H3

InChI Key

WNTYBHLDCKXEOT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazines

Sub Class

Phenothiazines

Direct Parent

Phenothiazines

Alternative Parents

Substituents

Phenothiazine
Alkyldiarylamine
Diarylthioether
Acetophenone
Aryl thioether
Tertiary aliphatic/aromatic amine
Aryl ketone
Aryl alkyl ketone
N-alkylpiperazine
Para-thiazine
1,4-diazinane
Piperazine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
1,2-aminoalcohol
Ketone
Thioether
Azacycle
Alkanolamine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Primary alcohol
Organic oxide
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenothiazines (CHEBI:2401 )
N-(2-hydroxyethyl)piperazine (CHEBI:2401 )
N-alkylpiperazine (CHEBI:2401 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.06 g/L	Not Available
LogP	3.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.06 g/L	ALOGPS
logP	3.48	ALOGPS
logP	2.65	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	15.46	ChemAxon
pKa (Strongest Basic)	8.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.02 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	121.7 m³·mol⁻¹	ChemAxon
Polarizability	46.68 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	193.227	31661259
DarkChem	[M-H]-	193.94	31661259
DeepCCS	[M+H]+	196.741	30932474
DeepCCS	[M-H]-	194.383	30932474
DeepCCS	[M-2H]-	228.299	30932474
DeepCCS	[M+Na]+	203.527	30932474
AllCCS	[M+H]+	198.4	32859911
AllCCS	[M+H-H2O]+	196.2	32859911
AllCCS	[M+NH4]+	200.5	32859911
AllCCS	[M+Na]+	201.1	32859911
AllCCS	[M-H]-	195.0	32859911
AllCCS	[M+Na-2H]-	195.3	32859911
AllCCS	[M+HCOO]-	195.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.4 minutes	32390414
Predicted by Siyang on May 30, 2022	10.388 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.96 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	130.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	812.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	190.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	304.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	420.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	665.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	807.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	193.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	874.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	230.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	320.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	355.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	556.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	223.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Acetophenazine	CC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C1	4578.2	Standard polar	33892256
Acetophenazine	CC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C1	3509.0	Standard non polar	33892256
Acetophenazine	CC(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN3CCN(CCO)CC3)C2=C1	3529.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Acetophenazine,1TMS,isomer #1	CC(=O)C1=CC=C2SC3=CC=CC=C3N(CCCN3CCN(CCO[Si](C)(C)C)CC3)C2=C1	3557.5	Semi standard non polar	33892256
Acetophenazine,1TBDMS,isomer #1	CC(=O)C1=CC=C2SC3=CC=CC=C3N(CCCN3CCN(CCO[Si](C)(C)C(C)(C)C)CC3)C2=C1	3765.9	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01063	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01063	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01063

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16708

KEGG Compound ID

C06807

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Acetophenazine

METLIN ID

Not Available

PubChem Compound

17676

PDB ID

Not Available

ChEBI ID

2401

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Tam SW, Cook L: Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. Proc Natl Acad Sci U S A. 1984 Sep;81(17):5618-21. [PubMed:6147851 ]
Jones GL, Woodbury DM: Spin-label study of phenothiazine interactions with erythrocyte ghost membranes: a possible membrane-mediated antisickling action. J Pharmacol Exp Ther. 1978 Oct;207(1):203-11. [PubMed:702341 ]

Enzymes

Enzyme Details

1. D(2) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:: DRD2
Uniprot ID:: P14416
Molecular weight:: 50618.9

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Seeman P: Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38. [PubMed:11873706 ]
Tam SW, Cook L: Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. Proc Natl Acad Sci U S A. 1984 Sep;81(17):5618-21. [PubMed:6147851 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. D(1A) dopamine receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:: DRD1
Uniprot ID:: P21728
Molecular weight:: 49292.8

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Showing metabocard for Acetophenazine (HMDB0015196)

MOL for HMDB0015196 (Acetophenazine)

3D MOL for HMDB0015196 (Acetophenazine)

3D SDF for HMDB0015196 (Acetophenazine)

3D-SDF for HMDB0015196 (Acetophenazine)

PDB for HMDB0015196 (Acetophenazine)

3D PDB for HMDB0015196 (Acetophenazine)

SMILES for HMDB0015196 (Acetophenazine)

INCHI for HMDB0015196 (Acetophenazine)

Structure for HMDB0015196 (Acetophenazine)

3D Structure for HMDB0015196 (Acetophenazine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References