NP-MRD: Showing NP-Card for tetrahydro-8-hydroxymanzamine A (NP0033193)

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Record Information

Version

2.0

Created at

2021-06-19 23:48:19 UTC

Updated at

2021-06-30 00:02:49 UTC

NP-MRD ID

NP0033193

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tetrahydro-8-hydroxymanzamine A

Provided By

JEOL Database JEOL Logo

Description

CHEMBL443503 belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. tetrahydro-8-hydroxymanzamine A is found in Acanthostrongylophora. tetrahydro-8-hydroxymanzamine A was first documented in 2007 (Hamann, M., et al.). Based on a literature review very few articles have been published on CHEMBL443503.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101483D          

 90 97  0  0  0  0            999 V2000
   -2.5107   -0.8789    5.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4096   -1.6951    5.7611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1810   -2.3715    6.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719   -3.1999    7.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8312   -3.3703    6.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6094   -2.7033    4.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130   -1.8774    4.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4974   -1.3717    3.4230 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5892   -1.8372    2.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -1.5985    1.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1837   -0.7490    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903    0.5795    0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958    1.5872    0.0253 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9378    2.5143    1.0737 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1163    2.4085   -1.0683 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4046    3.1233   -0.6297 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1693    3.7310   -1.8144 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2889    2.8360   -2.3674 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8599    1.4788   -2.9332 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.1228   -0.1345   -4.3923 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1123   -0.3942   -2.9650 N   0  0  2  0  0  0  0  0  0  0  0  0
    0.6098   -1.5887   -2.4946 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1347   -2.3652   -1.4070 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8105   -1.4391   -0.3775 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8103   -0.4776   -1.1228 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2553   -0.9619   -0.8979 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5824   -0.4760    0.5133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0535   -0.7358    0.8620 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3489   -0.7299    2.3611 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9440    0.5284    3.1187 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.9947    0.8835    0.5919 N   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.4331   -0.3224    4.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1838   -1.0053   -4.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5891   -1.2801   -2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000   -2.2907   -3.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8550    0.5833    3.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3982    1.6089    1.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6430    2.8752    2.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9629    3.5637    1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.4402    2.8340   -0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
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 35 34  1  0  0  0  0
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M  END

     RDKit          3D

 90 97  0  0  0  0  0  0  0  0999 V2000
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   -1.4096   -1.6951    5.7611 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202101483D          

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M  END
> <DATABASE_ID>
NP0033193

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2N([H])C3=C(N=C([H])C([H])=C3C2=C([H])C([H])=C1[H])C1=C([H])[C@@]2(O[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[N@@]3C([H])([H])C([H])([H])[C@]1([H])[C@]1(C([H])([H])[C@@]4([H])N(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C4([H])[H])[C@@]21[H])C3([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C36H48N4O2/c41-30-14-11-13-26-27-15-18-37-32(33(27)38-31(26)30)28-23-36(42)17-8-4-1-2-5-9-19-39-21-16-29(28)35(24-39)22-25-12-7-3-6-10-20-40(25)34(35)36/h11,13-15,18,23,25,29,34,38,41-42H,1-10,12,16-17,19-22,24H2/t25-,29-,34+,35-,36-/m0/s1

> <INCHI_KEY>
BHRFYFSYVSXAIC-LMPWOBKPSA-N

> <FORMULA>
C36H48N4O2

> <MOLECULAR_WEIGHT>
568.806

> <EXACT_MASS>
568.377726802

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
66.24948932198001

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,12R,13S,22R)-25-{8-hydroxy-9H-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1^{2,22}.0^{2,12}.0^{4,11}]heptacos-25-en-13-ol

> <ALOGPS_LOGP>
5.91

> <JCHEM_LOGP>
4.6173990712701185

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
11.644318018663432

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.491769294504795

> <JCHEM_PKA_STRONGEST_BASIC>
14.814815700086887

> <JCHEM_POLAR_SURFACE_AREA>
75.62

> <JCHEM_REFRACTIVITY>
169.4759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,12R,13S,22R)-25-{8-hydroxy-9H-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1^{2,22}.0^{2,12}.0^{4,11}]heptacos-25-en-13-ol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 90 97  0  0  0  0  0  0  0  0999 V2000
   -2.5107   -0.8789    5.6943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4096   -1.6951    5.7611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1810   -2.3715    6.9573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0719   -3.1999    7.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8312   -3.3703    6.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6094   -2.7033    4.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5130   -1.8774    4.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4974   -1.3717    3.4230 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5892   -1.8372    2.7187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -1.5985    1.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1837   -0.7490    0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903    0.5795    0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5958    1.5872    0.0253 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9378    2.5143    1.0737 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1163    2.4085   -1.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4046    3.1233   -0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1693    3.7310   -1.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2889    2.8360   -2.3674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8599    1.4788   -2.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0335    1.5956   -4.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5698    0.2374   -4.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1228   -0.1345   -4.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1123   -0.3942   -2.9650 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6098   -1.5887   -2.4946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347   -2.3652   -1.4070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8105   -1.4391   -0.3775 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8103   -0.4776   -1.1228 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2553   -0.9619   -0.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5824   -0.4760    0.5133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0535   -0.7358    0.8620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3489   -0.7299    2.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9440    0.5284    3.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5043    1.8065    2.5063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4865    2.6092    1.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9578    1.9943    0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9947    0.8835    0.5919 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9269    0.9470   -0.5091 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5403   -0.4609   -2.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1246   -2.1704    0.9429 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338   -2.9652    1.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4858   -3.2571    3.0857 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111   -2.6645    3.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4331   -0.3224    4.9051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8725   -2.2427    7.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0967   -3.7168    8.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6947   -4.0175    6.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1834   -0.7419    3.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0336    0.9809    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052    2.0920    1.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3268    1.7739   -1.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5733    3.1844   -1.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0704    2.4550   -0.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1278    3.9326    0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4814    4.0317   -2.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6475    4.6549   -1.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8271    3.3930   -3.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0156    2.6565   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7678    0.9048   -3.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3303    0.9082   -2.1673 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6680    2.0695   -4.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1745    2.2600   -4.0796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2688   -0.5593   -4.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6046    0.2960   -5.8597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5164    0.6960   -4.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1838   -1.0053   -4.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5891   -1.2801   -2.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8000   -2.2907   -3.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9086   -2.9888   -1.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5486   -3.0768   -0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3856   -2.1125    0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3471   -2.0501   -0.9908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9415   -0.5073   -1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0029   -1.0821    1.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7255   -0.0524    0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3265   -1.7341    0.4926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4251   -0.8967    2.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8500   -1.5888    2.8280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3356    0.4311    4.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8550    0.5833    3.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8376    2.4517    3.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3982    1.6089    1.9037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6430    2.8752    2.3531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9629    3.5637    1.4410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7691    1.7369   -0.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4402    2.8340   -0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3186    1.6029   -1.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9857   -1.3442   -3.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0577    0.4016   -3.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7353   -3.3883    1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0975   -3.9085    3.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
 35 34  1  0
  9  8  1  0
  8  7  1  0
  6 42  1  0
  9 10  2  0
 10 11  1  0
 11 26  1  0
 34 33  1  0
 10 39  1  0
 11 12  2  0
 27 37  1  0
 37 13  1  0
 13 12  1  0
 27 26  1  0
 33 32  1  0
 39 40  2  0
 32 31  1  0
 40 41  1  0
 41 42  2  0
 31 30  1  0
 27 38  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 38  1  0
  7  2  2  0
 23 22  1  0
 13 15  1  0
 29 30  1  0
 22 21  1  0
  2  3  1  0
 21 20  1  0
 20 19  1  0
  3  4  2  0
 18 17  1  0
 29 36  1  0
 17 16  1  0
 15 16  1  0
 37 36  1  0
  4  5  1  0
 27 28  1  6
 28 29  1  0
 19 18  1  0
  5  6  2  0
 13 14  1  1
  7  6  1  0
 36 35  1  0
 42  9  1  0
  2  1  1  0
 29 73  1  1
 35 84  1  0
 35 85  1  0
 34 82  1  0
 34 83  1  0
 33 80  1  0
 33 81  1  0
 32 78  1  0
 32 79  1  0
 31 76  1  0
 31 77  1  0
 30 74  1  0
 30 75  1  0
 17 54  1  0
 17 55  1  0
 40 89  1  0
 41 90  1  0
  3 44  1  0
  4 45  1  0
  5 46  1  0
  8 47  1  0
 37 86  1  6
 26 70  1  1
 25 68  1  0
 25 69  1  0
 24 66  1  0
 24 67  1  0
 38 87  1  0
 38 88  1  0
 22 64  1  0
 22 65  1  0
 21 62  1  0
 21 63  1  0
 20 60  1  0
 20 61  1  0
 19 58  1  0
 19 59  1  0
 18 56  1  0
 18 57  1  0
 16 52  1  0
 16 53  1  0
 28 71  1  0
 28 72  1  0
 14 49  1  0
 12 48  1  0
 15 50  1  0
 15 51  1  0
  1 43  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.511  -0.879   5.694  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.410  -1.695   5.761  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.181  -2.372   6.957  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.072  -3.200   7.101  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.831  -3.370   6.045  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.609  -2.703   4.821  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.513  -1.877   4.701  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.497  -1.372   3.423  0.00  0.00           N+0
HETATM    9  C   UNK     0       0.589  -1.837   2.719  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.993  -1.599   1.407  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.184  -0.749   0.532  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.290   0.580   0.685  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.596   1.587   0.025  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.938   2.514   1.074  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.116   2.409  -1.068  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.405   3.123  -0.630  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.169   3.731  -1.814  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.289   2.836  -2.367  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.860   1.479  -2.933  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.034   1.596  -4.217  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.570   0.237  -4.764  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.123  -0.135  -4.392  0.00  0.00           C+0
HETATM   23  N   UNK     0      -0.112  -0.394  -2.965  0.00  0.00           N+0
HETATM   24  C   UNK     0       0.610  -1.589  -2.495  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.135  -2.365  -1.407  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.811  -1.439  -0.378  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.810  -0.478  -1.123  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.255  -0.962  -0.898  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.582  -0.476   0.513  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.053  -0.736   0.862  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.349  -0.730   2.361  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.944   0.528   3.119  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.504   1.807   2.506  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.487   2.609   1.703  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.958   1.994   0.401  0.00  0.00           C+0
HETATM   36  N   UNK     0      -2.995   0.884   0.592  0.00  0.00           N+0
HETATM   37  C   UNK     0      -1.927   0.947  -0.509  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.540  -0.461  -2.655  0.00  0.00           C+0
HETATM   39  N   UNK     0       2.125  -2.170   0.943  0.00  0.00           N+0
HETATM   40  C   UNK     0       2.834  -2.965   1.773  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.486  -3.257   3.086  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.311  -2.664   3.574  0.00  0.00           C+0
HETATM   43  H   UNK     0      -2.433  -0.322   4.905  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.873  -2.243   7.786  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.097  -3.717   8.043  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.695  -4.018   6.169  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.183  -0.742   3.032  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.034   0.981   1.373  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.705   2.092   1.508  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.327   1.774  -1.922  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.573   3.184  -1.429  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.070   2.455  -0.075  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.128   3.933   0.057  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.481   4.032  -2.612  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.648   4.655  -1.464  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.827   3.393  -3.144  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.016   2.656  -1.565  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.768   0.905  -3.159  0.00  0.00           H+0
HETATM   59  H   UNK     0       2.330   0.908  -2.167  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.668   2.070  -4.977  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.175   2.260  -4.080  0.00  0.00           H+0
HETATM   62  H   UNK     0       2.269  -0.559  -4.485  0.00  0.00           H+0
HETATM   63  H   UNK     0       1.605   0.296  -5.860  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.516   0.696  -4.720  0.00  0.00           H+0
HETATM   65  H   UNK     0      -0.184  -1.005  -4.987  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.589  -1.280  -2.114  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.800  -2.291  -3.317  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.909  -2.989  -1.876  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.549  -3.077  -0.932  0.00  0.00           H+0
HETATM   70  H   UNK     0      -1.386  -2.112   0.273  0.00  0.00           H+0
HETATM   71  H   UNK     0      -3.347  -2.050  -0.991  0.00  0.00           H+0
HETATM   72  H   UNK     0      -3.942  -0.507  -1.626  0.00  0.00           H+0
HETATM   73  H   UNK     0      -3.003  -1.082   1.221  0.00  0.00           H+0
HETATM   74  H   UNK     0      -5.726  -0.052   0.334  0.00  0.00           H+0
HETATM   75  H   UNK     0      -5.327  -1.734   0.493  0.00  0.00           H+0
HETATM   76  H   UNK     0      -6.425  -0.897   2.498  0.00  0.00           H+0
HETATM   77  H   UNK     0      -4.850  -1.589   2.828  0.00  0.00           H+0
HETATM   78  H   UNK     0      -5.336   0.431   4.140  0.00  0.00           H+0
HETATM   79  H   UNK     0      -3.855   0.583   3.225  0.00  0.00           H+0
HETATM   80  H   UNK     0      -5.838   2.452   3.330  0.00  0.00           H+0
HETATM   81  H   UNK     0      -6.398   1.609   1.904  0.00  0.00           H+0
HETATM   82  H   UNK     0      -3.643   2.875   2.353  0.00  0.00           H+0
HETATM   83  H   UNK     0      -4.963   3.564   1.441  0.00  0.00           H+0
HETATM   84  H   UNK     0      -4.769   1.737  -0.289  0.00  0.00           H+0
HETATM   85  H   UNK     0      -3.440   2.834  -0.085  0.00  0.00           H+0
HETATM   86  H   UNK     0      -2.319   1.603  -1.299  0.00  0.00           H+0
HETATM   87  H   UNK     0      -1.986  -1.344  -3.135  0.00  0.00           H+0
HETATM   88  H   UNK     0      -2.058   0.402  -3.095  0.00  0.00           H+0
HETATM   89  H   UNK     0       3.735  -3.388   1.338  0.00  0.00           H+0
HETATM   90  H   UNK     0       3.098  -3.909   3.697  0.00  0.00           H+0
CONECT    1    2   43                                                       
CONECT    2    7    3    1                                                  
CONECT    3    2    4   44                                                  
CONECT    4    3    5   45                                                  
CONECT    5    4    6   46                                                  
CONECT    6   42    5    7                                                  
CONECT    7    8    2    6                                                  
CONECT    8    9    7   47                                                  
CONECT    9    8   10   42                                                  
CONECT   10    9   11   39                                                  
CONECT   11   10   26   12                                                  
CONECT   12   11   13   48                                                  
CONECT   13   37   12   15   14                                             
CONECT   14   13   49                                                       
CONECT   15   13   16   50   51                                             
CONECT   16   17   15   52   53                                             
CONECT   17   18   16   54   55                                             
CONECT   18   17   19   56   57                                             
CONECT   19   20   18   58   59                                             
CONECT   20   21   19   60   61                                             
CONECT   21   22   20   62   63                                             
CONECT   22   23   21   64   65                                             
CONECT   23   24   38   22                                                  
CONECT   24   25   23   66   67                                             
CONECT   25   26   24   68   69                                             
CONECT   26   11   27   25   70                                             
CONECT   27   37   26   38   28                                             
CONECT   28   27   29   71   72                                             
CONECT   29   30   36   28   73                                             
CONECT   30   31   29   74   75                                             
CONECT   31   32   30   76   77                                             
CONECT   32   33   31   78   79                                             
CONECT   33   34   32   80   81                                             
CONECT   34   35   33   82   83                                             
CONECT   35   34   36   84   85                                             
CONECT   36   29   37   35                                                  
CONECT   37   27   13   36   86                                             
CONECT   38   27   23   87   88                                             
CONECT   39   10   40                                                       
CONECT   40   39   41   89                                                  
CONECT   41   40   42   90                                                  
CONECT   42    6   41    9                                                  
CONECT   43    1                                                            
CONECT   44    3                                                            
CONECT   45    4                                                            
CONECT   46    5                                                            
CONECT   47    8                                                            
CONECT   48   12                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   15                                                            
CONECT   52   16                                                            
CONECT   53   16                                                            
CONECT   54   17                                                            
CONECT   55   17                                                            
CONECT   56   18                                                            
CONECT   57   18                                                            
CONECT   58   19                                                            
CONECT   59   19                                                            
CONECT   60   20                                                            
CONECT   61   20                                                            
CONECT   62   21                                                            
CONECT   63   21                                                            
CONECT   64   22                                                            
CONECT   65   22                                                            
CONECT   66   24                                                            
CONECT   67   24                                                            
CONECT   68   25                                                            
CONECT   69   25                                                            
CONECT   70   26                                                            
CONECT   71   28                                                            
CONECT   72   28                                                            
CONECT   73   29                                                            
CONECT   74   30                                                            
CONECT   75   30                                                            
CONECT   76   31                                                            
CONECT   77   31                                                            
CONECT   78   32                                                            
CONECT   79   32                                                            
CONECT   80   33                                                            
CONECT   81   33                                                            
CONECT   82   34                                                            
CONECT   83   34                                                            
CONECT   84   35                                                            
CONECT   85   35                                                            
CONECT   86   37                                                            
CONECT   87   38                                                            
CONECT   88   38                                                            
CONECT   89   40                                                            
CONECT   90   41                                                            
MASTER        0    0    0    0    0    0    0    0   90    0  194    0
END

RDKit          3D

90 97  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₄₈N₄O₂

Average Mass

568.8060 Da

Monoisotopic Mass

568.37773 Da

IUPAC Name

(1R,2R,4S,12R,13S,22R)-25-{8-hydroxy-9H-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1^{2,22}.0^{2,12}.0^{4,11}]heptacos-25-en-13-ol

Traditional Name

(1R,2R,4S,12R,13S,22R)-25-{8-hydroxy-9H-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1^{2,22}.0^{2,12}.0^{4,11}]heptacos-25-en-13-ol

CAS Registry Number

Not Available

SMILES

[H]OC1=C2N([H])C3=C(N=C([H])C([H])=C3C2=C([H])C([H])=C1[H])C1=C([H])[C@@]2(O[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[N@@]3C([H])([H])C([H])([H])[C@]1([H])[C@]1(C([H])([H])[C@@]4([H])N(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C4([H])[H])[C@@]21[H])C3([H])[H]

InChI Identifier

InChI=1S/C36H48N4O2/c41-30-14-11-13-26-27-15-18-37-32(33(27)38-31(26)30)28-23-36(42)17-8-4-1-2-5-9-19-39-21-16-29(28)35(24-39)22-25-12-7-3-6-10-20-40(25)34(35)36/h11,13-15,18,23,25,29,34,38,41-42H,1-10,12,16-17,19-22,24H2/t25-,29-,34+,35-,36-/m0/s1

InChI Key

BHRFYFSYVSXAIC-LMPWOBKPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acanthostrongylophora	JEOL database	Hamann, M., et al, J. Nat. Prod. 70, 1397 (2007)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Azaspirodecane
Hydroxyindole
Indole
Indole or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
N-alkylpyrrolidine
Piperidine
Pyridine
Heteroaromatic compound
Tertiary alcohol
Pyrrole
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Amine
Organic nitrogen compound
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	5.91	ALOGPS
logP	4.62	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	14.81	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	75.62 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	169.48 m³·mol⁻¹	ChemAxon
Polarizability	66.25 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	Yes	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

23314524

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44448188

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hamann, M., et al. (2007). Hamann, M., et al, J. Nat. Prod. 70, 1397 (2007). J. Nat. Prod..

Showing NP-Card for tetrahydro-8-hydroxymanzamine A (NP0033193)

MOL for NP0033193 (tetrahydro-8-hydroxymanzamine A)

3D MOL for NP0033193 (tetrahydro-8-hydroxymanzamine A)

3D SDF for NP0033193 (tetrahydro-8-hydroxymanzamine A)

3D-SDF for NP0033193 (tetrahydro-8-hydroxymanzamine A)

PDB for NP0033193 (tetrahydro-8-hydroxymanzamine A)

3D PDB for NP0033193 (tetrahydro-8-hydroxymanzamine A)

SMILES for NP0033193 (tetrahydro-8-hydroxymanzamine A)

INCHI for NP0033193 (tetrahydro-8-hydroxymanzamine A)

Structure for NP0033193 (tetrahydro-8-hydroxymanzamine A)

3D Structure for NP0033193 (tetrahydro-8-hydroxymanzamine A)