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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:47:41 UTC

Update Date

2021-09-26 22:50:39 UTC

HMDB ID

HMDB0243545

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Posiphen

Description

Posiphen belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Based on a literature review a significant number of articles have been published on Posiphen. This compound has been identified in human blood as reported by (PMID: 31557052 ). Posiphen is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Posiphen is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0256419
     RDKit          3D
Phenserine
 48 51  0  0  0  0  0  0  0  0999 V2000
   -3.7696    0.6306   -2.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5048    0.7490   -0.7706 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1286    2.0607   -0.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573    1.7750    0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8021    0.4863    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0431    0.7946    2.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6642   -0.4191    0.7413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3770   -0.3267    1.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5545   -1.3025    0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375   -1.1833    1.4881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595   -0.5511    0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5021   -0.1292   -0.3737 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1473   -0.4349    1.2431 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2554    0.1647    0.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2118    0.7363   -0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3414    1.3216   -1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5439    1.3347   -0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5889    0.7614    0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4972    0.1960    1.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1880   -2.3997    0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1155   -2.4879   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0465   -1.4997    0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296   -1.3603   -0.3786 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0767   -2.3252   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9858   -0.1687    0.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8612    0.0336   -1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4310    0.2056   -2.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4726    1.6406   -2.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2155    2.8578   -0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7106    2.2270    0.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1294    1.6575   -0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    2.5902    0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0324    1.2338    2.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2342    1.4832    2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9261   -0.1377    2.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1043    0.5564    1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3176   -0.8444    2.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2942    0.7611   -1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2488    1.7615   -2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4046    1.7908   -1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5353    0.7722    1.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5569   -0.2524    2.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8959   -3.1899    0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3501   -3.3734   -0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1748   -2.2810   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279   -3.3624   -0.9732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7717   -2.1761   -2.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8039   -0.3765    0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25  2  1  0
 25  5  1  0
 22  7  1  0
 19 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
M  END

  Mrv1652309102122472D          

 25 28  0  0  0  0            999 V2000
    2.0724   -0.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    0.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005   -0.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774    0.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379    0.9720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131    0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9554    1.4863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785    1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539   -0.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890    0.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750    1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4136   -0.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2170   -0.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4564    0.1852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7810   -1.2064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5844   -1.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1484   -1.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9519   -1.4337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1913   -0.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6273   -0.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8239   -0.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9716    2.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9359    1.6298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
  7 24  1  0  0  0  0
  5 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0243545

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC2(C)C1N(C)C1=C2C=C(OC(=O)NC2=CC=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H23N3O2/c1-20-11-12-22(2)18(20)23(3)17-10-9-15(13-16(17)20)25-19(24)21-14-7-5-4-6-8-14/h4-10,13,18H,11-12H2,1-3H3,(H,21,24)

> <INCHI_KEY>
PBHFNBQPZCRWQP-UHFFFAOYSA-N

> <FORMULA>
C20H23N3O2

> <MOLECULAR_WEIGHT>
337.423

> <EXACT_MASS>
337.179026993

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.22788481317009

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-phenylcarbamate

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
4.250101519

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.859102064672115

> <JCHEM_PKA_STRONGEST_BASIC>
6.582511444360409

> <JCHEM_POLAR_SURFACE_AREA>
44.81

> <JCHEM_REFRACTIVITY>
99.95519999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3a,8-trimethyl-2H,3H,8aH-pyrrolo[2,3-b]indol-5-yl N-phenylcarbamate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0256419
     RDKit          3D
Phenserine
 48 51  0  0  0  0  0  0  0  0999 V2000
   -3.7696    0.6306   -2.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5048    0.7490   -0.7706 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1286    2.0607   -0.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573    1.7750    0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8021    0.4863    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0431    0.7946    2.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6642   -0.4191    0.7413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3770   -0.3267    1.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5545   -1.3025    0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375   -1.1833    1.4881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595   -0.5511    0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5021   -0.1292   -0.3737 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1473   -0.4349    1.2431 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2554    0.1647    0.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2118    0.7363   -0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3414    1.3216   -1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5439    1.3347   -0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5889    0.7614    0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4972    0.1960    1.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1880   -2.3997    0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1155   -2.4879   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0465   -1.4997    0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296   -1.3603   -0.3786 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0767   -2.3252   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9858   -0.1687    0.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8612    0.0336   -1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4310    0.2056   -2.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4726    1.6406   -2.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2155    2.8578   -0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7106    2.2270    0.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1294    1.6575   -0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    2.5902    0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0324    1.2338    2.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2342    1.4832    2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9261   -0.1377    2.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1043    0.5564    1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3176   -0.8444    2.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2942    0.7611   -1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2488    1.7615   -2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4046    1.7908   -1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5353    0.7722    1.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5569   -0.2524    2.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8959   -3.1899    0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3501   -3.3734   -0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1748   -2.2810   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279   -3.3624   -0.9732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7717   -2.1761   -2.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8039   -0.3765    0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25  2  1  0
 25  5  1  0
 22  7  1  0
 19 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
M  END

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       3.868  -1.065   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.373   0.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.601  -0.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.864   0.341   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       6.417   1.814   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       4.878   1.845   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.650   2.774   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.387   1.894   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.833   0.420   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.781  -0.704   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.281  -0.354   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.166   1.120   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.887   2.244   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.772  -1.478   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.272  -1.128   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.719   0.346   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0      -3.325  -2.252   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -4.824  -1.902   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.877  -3.026   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.377  -2.676   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -7.824  -1.202   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.771  -0.079   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.271  -0.428   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.680   4.314   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.347   3.042   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6    9                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24    7                                                            
CONECT   25    5                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0243545
HETATM    1  C1  UNL     1      -6.093   0.609  -0.433  1.00  0.00           C  
HETATM    2  N1  UNL     1      -4.794   1.006  -0.059  1.00  0.00           N  
HETATM    3  C2  UNL     1      -4.550   1.362   1.289  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.053   1.087   1.489  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.526   1.092   0.080  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.335   2.457  -0.509  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.400   0.185  -0.158  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.038   0.321  -0.270  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.823  -0.765  -0.515  1.00  0.00           C  
HETATM   10  O1  UNL     1       2.194  -0.520  -0.608  1.00  0.00           O  
HETATM   11  C9  UNL     1       3.072  -0.830   0.482  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.459  -1.341   1.450  1.00  0.00           O  
HETATM   13  N2  UNL     1       4.405  -0.562   0.386  1.00  0.00           N  
HETATM   14  C10 UNL     1       5.722  -0.297   0.292  1.00  0.00           C  
HETATM   15  C11 UNL     1       6.707  -0.361   1.225  1.00  0.00           C  
HETATM   16  C12 UNL     1       8.007  -0.034   0.942  1.00  0.00           C  
HETATM   17  C13 UNL     1       8.393   0.378  -0.299  1.00  0.00           C  
HETATM   18  C14 UNL     1       7.415   0.452  -1.265  1.00  0.00           C  
HETATM   19  C15 UNL     1       6.131   0.142  -1.034  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.275  -2.015  -0.649  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.096  -2.142  -0.535  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.956  -1.089  -0.295  1.00  0.00           C  
HETATM   23  N3  UNL     1      -3.387  -0.977  -0.129  1.00  0.00           N  
HETATM   24  C19 UNL     1      -4.178  -2.033   0.414  1.00  0.00           C  
HETATM   25  C20 UNL     1      -3.682   0.350  -0.618  1.00  0.00           C  
HETATM   26  H1  UNL     1      -6.520   1.437  -1.078  1.00  0.00           H  
HETATM   27  H2  UNL     1      -6.152  -0.286  -1.107  1.00  0.00           H  
HETATM   28  H3  UNL     1      -6.788   0.536   0.431  1.00  0.00           H  
HETATM   29  H4  UNL     1      -5.173   0.835   2.041  1.00  0.00           H  
HETATM   30  H5  UNL     1      -4.690   2.459   1.412  1.00  0.00           H  
HETATM   31  H6  UNL     1      -2.596   1.807   2.160  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.981   0.032   1.850  1.00  0.00           H  
HETATM   33  H8  UNL     1      -2.442   2.413  -1.613  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.093   3.162  -0.137  1.00  0.00           H  
HETATM   35  H10 UNL     1      -1.319   2.864  -0.335  1.00  0.00           H  
HETATM   36  H11 UNL     1       0.404   1.319  -0.169  1.00  0.00           H  
HETATM   37  H12 UNL     1       4.579  -1.216   1.555  1.00  0.00           H  
HETATM   38  H13 UNL     1       6.469  -0.680   2.256  1.00  0.00           H  
HETATM   39  H14 UNL     1       8.739  -0.116   1.757  1.00  0.00           H  
HETATM   40  H15 UNL     1       9.402   0.629  -0.505  1.00  0.00           H  
HETATM   41  H16 UNL     1       7.726   0.788  -2.272  1.00  0.00           H  
HETATM   42  H17 UNL     1       5.361   0.203  -1.798  1.00  0.00           H  
HETATM   43  H18 UNL     1       0.918  -2.872  -0.837  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.511  -3.153  -0.646  1.00  0.00           H  
HETATM   45  H20 UNL     1      -3.865  -2.343   1.459  1.00  0.00           H  
HETATM   46  H21 UNL     1      -4.133  -2.995  -0.172  1.00  0.00           H  
HETATM   47  H22 UNL     1      -5.252  -1.744   0.557  1.00  0.00           H  
HETATM   48  H23 UNL     1      -3.598   0.447  -1.712  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   25
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6    7   25
CONECT    6   33   34   35
CONECT    7    8    8   22
CONECT    8    9   36
CONECT    9   10   20   20
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   37
CONECT   14   15   15   19
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   18   40
CONECT   18   19   19   41
CONECT   19   42
CONECT   20   21   43
CONECT   21   22   22   44
CONECT   22   23
CONECT   23   24   25
CONECT   24   45   46   47
CONECT   25   48
END

HMDB0256419
     RDKit          3D
Phenserine
 48 51  0  0  0  0  0  0  0  0999 V2000
   -3.7696    0.6306   -2.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5048    0.7490   -0.7706 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1286    2.0607   -0.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6573    1.7750    0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8021    0.4863    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0431    0.7946    2.3311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6642   -0.4191    0.7413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3770   -0.3267    1.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5545   -1.3025    0.9908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375   -1.1833    1.4881 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595   -0.5511    0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5021   -0.1292   -0.3737 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1473   -0.4349    1.2431 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2554    0.1647    0.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2118    0.7363   -0.6313 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3414    1.3216   -1.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5439    1.3347   -0.5469 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5889    0.7614    0.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4972    0.1960    1.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1880   -2.3997    0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1155   -2.4879   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0465   -1.4997    0.0074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296   -1.3603   -0.3786 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0767   -2.3252   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9858   -0.1687    0.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8612    0.0336   -1.9380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4310    0.2056   -2.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4726    1.6406   -2.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2155    2.8578   -0.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7106    2.2270    0.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1294    1.6575   -0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2344    2.5902    0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0324    1.2338    2.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2342    1.4832    2.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9261   -0.1377    2.9367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1043    0.5564    1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3176   -0.8444    2.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2942    0.7611   -1.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2488    1.7615   -2.2109 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4046    1.7908   -1.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5353    0.7722    1.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5569   -0.2524    2.2590 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8959   -3.1899    0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3501   -3.3734   -0.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1748   -2.2810   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7279   -3.3624   -0.9732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7717   -2.1761   -2.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8039   -0.3765    0.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  9 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25  2  1  0
 25  5  1  0
 22  7  1  0
 19 14  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  6 33  1  0
  6 34  1  0
  6 35  1  0
  8 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-({1,3a,8-trimethyl-1H,2H,3H,3ah,8H,8ah-pyrrolo[2,3-b]indol-5-yl}oxy)-N-phenylmethanimidate	HMDB

Chemical Formula

C₂₀H₂₃N₃O₂

Average Molecular Weight

337.423

Monoisotopic Molecular Weight

337.179026993

IUPAC Name

1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-phenylcarbamate

Traditional Name

1,3a,8-trimethyl-2H,3H,8aH-pyrrolo[2,3-b]indol-5-yl N-phenylcarbamate

CAS Registry Number

Not Available

SMILES

CN1CCC2(C)C1N(C)C1=C2C=C(OC(=O)NC2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C20H23N3O2/c1-20-11-12-22(2)18(20)23(3)17-10-9-15(13-16(17)20)25-19(24)21-14-7-5-4-6-8-14/h4-10,13,18H,11-12H2,1-3H3,(H,21,24)

InChI Key

PBHFNBQPZCRWQP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

Pyrroloindole
Phenylcarbamic acid ester
Indole
Dialkylarylamine
Monocyclic benzene moiety
Benzenoid
N-alkylpyrrolidine
Pyrrole
Pyrrolidine
Carbamic acid ester
Carbonic acid derivative
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0256419)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.38	ALOGPS
logP	4.25	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	6.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	44.81 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.96 m³·mol⁻¹	ChemAxon
Polarizability	37.23 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	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	177.718	30932474
DeepCCS	[M-H]-	175.36	30932474
DeepCCS	[M-2H]-	209.416	30932474
DeepCCS	[M+Na]+	185.089	30932474
AllCCS	[M+H]+	183.0	32859911
AllCCS	[M+H-H2O]+	179.8	32859911
AllCCS	[M+NH4]+	185.9	32859911
AllCCS	[M+Na]+	186.7	32859911
AllCCS	[M-H]-	187.8	32859911
AllCCS	[M+Na-2H]-	187.0	32859911
AllCCS	[M+HCOO]-	186.3	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Posiphen,1TMS,isomer #1	CN1CCC2(C)C3=CC(OC(=O)N(C4=CC=CC=C4)[Si](C)(C)C)=CC=C3N(C)C12	2681.1	Semi standard non polar	33892256
Posiphen,1TMS,isomer #1	CN1CCC2(C)C3=CC(OC(=O)N(C4=CC=CC=C4)[Si](C)(C)C)=CC=C3N(C)C12	2679.3	Standard non polar	33892256
Posiphen,1TMS,isomer #1	CN1CCC2(C)C3=CC(OC(=O)N(C4=CC=CC=C4)[Si](C)(C)C)=CC=C3N(C)C12	3328.9	Standard polar	33892256
Posiphen,1TBDMS,isomer #1	CN1CCC2(C)C3=CC(OC(=O)N(C4=CC=CC=C4)[Si](C)(C)C(C)(C)C)=CC=C3N(C)C12	2892.0	Semi standard non polar	33892256
Posiphen,1TBDMS,isomer #1	CN1CCC2(C)C3=CC(OC(=O)N(C4=CC=CC=C4)[Si](C)(C)C(C)(C)C)=CC=C3N(C)C12	2912.1	Standard non polar	33892256
Posiphen,1TBDMS,isomer #1	CN1CCC2(C)C3=CC(OC(=O)N(C4=CC=CC=C4)[Si](C)(C)C(C)(C)C)=CC=C3N(C)C12	3437.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Posiphen GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-6698000000-e41a753cda66f9a58ff4	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Posiphen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Posiphen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Posiphen 10V, Positive-QTOF	splash10-000i-0039000000-97a7c1a98138ca950847	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Posiphen 20V, Positive-QTOF	splash10-0a4i-0039000000-572a7cd2da2d15f3f579	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Posiphen 40V, Positive-QTOF	splash10-07bf-8955000000-17481df8176b0745e850	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Posiphen 10V, Negative-QTOF	splash10-014r-0095000000-5eea2f1ba882134909d3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Posiphen 20V, Negative-QTOF	splash10-00li-1095000000-0f8260f94f56f3771707	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Posiphen 40V, Negative-QTOF	splash10-11bl-3896000000-a49bb34c2eba2f55b436	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

532649

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

612745

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Posiphen (HMDB0243545)

MOL for HMDB0243545 (Posiphen)

3D MOL for HMDB0243545 (Posiphen)

3D SDF for HMDB0243545 (Posiphen)

3D-SDF for HMDB0243545 (Posiphen)

PDB for HMDB0243545 (Posiphen)

3D PDB for HMDB0243545 (Posiphen)

SMILES for HMDB0243545 (Posiphen)

INCHI for HMDB0243545 (Posiphen)

Structure for HMDB0243545 (Posiphen)

3D Structure for HMDB0243545 (Posiphen)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra