NP-MRD: Showing NP-Card for 1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole (NP0257049)

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Record Information

Version

2.0

Created at

2022-09-07 22:03:44 UTC

Updated at

2022-09-07 22:03:45 UTC

NP-MRD ID

NP0257049

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole

Description

AC1LCR41 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. 1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole is found in Psychotria colorata, Psychotria forsteriana, Psychotria milnei and Psychotria oleoides. AC1LCR41 is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171502082D          

 52 63  0  0  0  0            999 V2000
    7.7911    5.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3194    4.6594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4946    4.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2551    3.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9320    3.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5898    3.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2666    3.4082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0272    2.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4537    1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0554    1.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2305    1.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8040    1.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2024    2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2743    2.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3767    2.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7189    1.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9588    1.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8564    2.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5141    3.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2438    3.9840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4189    3.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7421    4.4394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7258    5.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843    3.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3547    3.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1795    3.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9401    2.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5041    1.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2647    0.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3446    0.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    1.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366    2.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598    2.6730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8020    2.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9772    2.1588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694    2.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212    1.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4146    0.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    1.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    0.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    1.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774    0.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379   -0.1470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9146   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131   -0.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9554   -0.6613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -0.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505    1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539    1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.5999    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
  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
  5 13  1  0  0  0  0
  8 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 18 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 31 39  1  0  0  0  0
 34 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 40 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 40 52  1  0  0  0  0
 47 52  1  0  0  0  0
M  END


  Mrv1533004171502082D          

 52 63  0  0  0  0            999 V2000
    7.7911    5.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3194    4.6594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4946    4.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2551    3.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9320    3.3819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5898    3.8799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2666    3.4082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0272    2.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4537    1.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0554    1.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2305    1.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8040    1.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2024    2.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2743    2.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3767    2.0653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7189    1.5673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9588    1.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8564    2.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5141    3.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2438    3.9840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4189    3.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7421    4.4394    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7258    5.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0843    3.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3547    3.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1795    3.1783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9401    2.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5041    1.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2647    0.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3446    0.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    1.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1366    2.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4598    2.6730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8020    2.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9772    2.1588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694    2.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6212    1.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4146    0.8976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0724    1.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3427    0.6162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    1.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6774    0.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4379   -0.1470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9146   -0.8637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6131   -0.1633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9554   -0.6613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2785   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4750   -0.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890    0.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1505    1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9539    1.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5179    0.5999    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
  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
  5 13  1  0  0  0  0
  8 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 18 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 27 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 31 39  1  0  0  0  0
 34 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 40 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  0  0  0  0
 40 52  1  0  0  0  0
 47 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257049

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1CCC2(C1NC1=CC=CC=C21)C1=CC=CC2=C1NC1N(C)CCC21C1=CC=CC2=C1NC1N(C)CCC21C12CCN(C)C1NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C44H50N8/c1-49-23-19-41(27-11-5-7-17-33(27)45-37(41)49)29-13-9-14-30-35(29)47-38-42(30,20-24-50(38)2)31-15-10-16-32-36(31)48-40-44(32,22-26-52(40)4)43-21-25-51(3)39(43)46-34-18-8-6-12-28(34)43/h5-18,37-40,45-48H,19-26H2,1-4H3

> <INCHI_KEY>
AVQUGAAZHJLAOQ-UHFFFAOYSA-N

> <FORMULA>
C44H50N8

> <MOLECULAR_WEIGHT>
690.94

> <EXACT_MASS>
690.415843642

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
78.09051143377275

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methyl-7-{1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl}-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-7-yl)-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indole

> <ALOGPS_LOGP>
5.14

> <JCHEM_LOGP>
5.367756423333334

> <ALOGPS_LOGS>
-4.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
12

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.689033733120198

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.271448797000243

> <JCHEM_PKA_STRONGEST_BASIC>
7.6516125523919865

> <JCHEM_POLAR_SURFACE_AREA>
61.080000000000005

> <JCHEM_REFRACTIVITY>
235.8833999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl-7-{1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-3a-yl}-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-7-yl)-2H,3H,8H,8aH-pyrrolo[2,3-b]indole

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      14.543   9.961   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      13.663   8.697   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      12.123   8.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.676   7.193   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.940   6.313   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.168   7.243   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      15.431   6.362   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      14.984   4.888   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.780   3.570   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.037   2.221   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.497   2.191   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.701   3.509   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.444   4.858   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.712   5.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.903   3.855   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.675   2.926   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.256   3.524   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.065   5.052   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.293   5.982   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       9.788   7.437   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       8.249   7.406   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.985   8.287   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       6.955   9.827   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.757   7.357   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.262   5.902   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.802   5.933   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.355   4.459   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.408   3.335   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.961   1.861   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.243   1.519   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.408   2.635   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.855   4.109   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       4.592   4.990   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       3.364   4.060   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       1.824   4.030   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       1.063   5.368   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.159   2.563   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.641   1.676   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.868   2.605   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.373   1.150   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.601   2.080   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.864   1.199   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0       6.417  -0.274   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0       7.307  -1.612   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.878  -0.305   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0       3.650  -1.234   0.000  0.00  0.00           N+0
HETATM   47  C   UNK     0       2.387  -0.354   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       0.887  -0.704   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -0.166   0.420   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       0.281   1.894   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       1.781   2.244   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       2.833   1.120   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13   14                                             
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5    8                                                  
CONECT   14    5   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   18   21   27                                             
CONECT   27   26   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   39                                                  
CONECT   32   31   27   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   31   34   40                                             
CONECT   40   39   41   45   52                                             
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   40   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   52                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   40   47                                                  
MASTER        0    0    0    0    0    0    0    0   52    0  126    0
END

View in JSmol

Synonyms

Value	Source
Quadrigemine a	MeSH
Quadrigemine a, stereoisomer	MeSH
Quadrigemine-C	MeSH
Quadrigemine C	MeSH
Quadrigemine-a	MeSH
Quadrigemine-b	MeSH

Chemical Formula

C₄₄H₅₀N₈

Average Mass

690.9400 Da

Monoisotopic Mass

690.41584 Da

IUPAC Name

1-methyl-7-{1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl}-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-7-yl)-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indole

Traditional Name

1-methyl-7-{1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-3a-yl}-2H,3H,8H,8aH-pyrrolo[2,3-b]indol-7-yl)-2H,3H,8H,8aH-pyrrolo[2,3-b]indole

CAS Registry Number

Not Available

SMILES

CN1CCC2(C1NC1=CC=CC=C21)C1=CC=CC2=C1NC1N(C)CCC21C1=CC=CC2=C1NC1N(C)CCC21C12CCN(C)C1NC1=CC=CC=C21

InChI Identifier

InChI=1S/C44H50N8/c1-49-23-19-41(27-11-5-7-17-33(27)45-37(41)49)29-13-9-14-30-35(29)47-38-42(30,20-24-50(38)2)31-15-10-16-32-36(31)48-40-44(32,22-26-52(40)4)43-21-25-51(3)39(43)46-34-18-8-6-12-28(34)43/h5-18,37-40,45-48H,19-26H2,1-4H3

InChI Key

AVQUGAAZHJLAOQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Psychotria colorata	LOTUS Database	35616633
Psychotria forsteriana	LOTUS Database	35616633
Psychotria milnei	LOTUS Database	35616633
Psychotria oleoides	LOTUS Database	35616633

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
Indole
Dihydroindole
Secondary aliphatic/aromatic amine
Benzenoid
N-alkylpyrrolidine
Pyrrole
Pyrrolidine
Azacycle
Secondary amine
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	5.14	ALOGPS
logP	5.37	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	14.27	ChemAxon
pKa (Strongest Basic)	7.65	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	61.08 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	235.88 m³·mol⁻¹	ChemAxon
Polarizability	78.09 Å³	ChemAxon
Number of Rings	12	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

635745

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole (NP0257049)

MOL for NP0257049 (1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole)

3D MOL for NP0257049 (1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole)

3D SDF for NP0257049 (1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole)

3D-SDF for NP0257049 (1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole)

PDB for NP0257049 (1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole)

3D PDB for NP0257049 (1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole)

SMILES for NP0257049 (1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole)

INCHI for NP0257049 (1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole)

Structure for NP0257049 (1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole)

3D Structure for NP0257049 (1-methyl-7-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-3a-(1-methyl-3a-{1-methyl-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-3a-yl}-2h,3h,8h,8ah-pyrrolo[2,3-b]indol-7-yl)-2h,3h,8h,8ah-pyrrolo[2,3-b]indole)