Natural Product: NPC267217

Natural Product ID:  NPC267217
Common Name:   Karakoline
IUPAC Name:  
Synonyms:   Karacoline; Karakoline
Molecular Formula:   C22H35NO4
Standard InCHIKey:  HKQZUYOVMYOFIT-NHNXFQBOSA-N
Standard InCHI:  InChI=1S/C22H35NO4/c1-4-23-10-20(2)6-5-16(24)22-12-7-11-14(27-3)9-21(26,17(12)18(11)25)13(19(22)23)8-15(20)22/h11-19,24-26H,4-10H2,1-3H3/t11-,12-,13-,14+,15-,16+,17-,18+,19?,20+,21+,22-/m1/s1
Canonical SMILES:  CCN1C[C@]2(C)CC[C@@H]([C@]34C1[C@@H](C[C@H]23)[C@@]1(O)C[C@@H]([C@H]2C[C@@H]4[C@@H]1[C@H]2O)OC)O
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO4902 Aconitum carmichaelii Species Ranunculaceae Eukaryota TM-MC*
NPO7490 Aconitum japonicum Species Ranunculaceae Eukaryota TM-MC*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT414 Individual Protein Neuronal acetylcholine receptor protein alpha-7 subunit Rattus norvegicus IC50 = 1800 nM 8941400
NPT2 Others Unspecified EC50 = 85113.8 nM 20594622
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 19.97 % 23062825
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -5.97 % 23062825

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC267217 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC8009
1.0 High Similarity NPC83047
1.0 High Similarity NPC48127
0.9703 High Similarity NPC139778
0.8909 High Similarity NPC208118
0.8909 High Similarity NPC96080
0.8909 High Similarity NPC99905
0.8899 High Similarity NPC475887
0.8376 Intermediate Similarity NPC476497
0.8305 Intermediate Similarity NPC476967
0.8291 Intermediate Similarity NPC476501
0.8214 Intermediate Similarity NPC476502
0.7769 Intermediate Similarity NPC212106
0.776 Intermediate Similarity NPC474210
0.7611 Intermediate Similarity NPC287764
0.7417 Intermediate Similarity NPC476504
0.7377 Intermediate Similarity NPC476503
0.735 Intermediate Similarity NPC476499
0.7273 Intermediate Similarity NPC201712
0.7222 Intermediate Similarity NPC155985
0.719 Intermediate Similarity NPC470594
0.719 Intermediate Similarity NPC470593
0.7182 Intermediate Similarity NPC475249
0.7179 Intermediate Similarity NPC476498
0.7143 Intermediate Similarity NPC309249
0.7129 Intermediate Similarity NPC109533
0.7091 Intermediate Similarity NPC473537
0.7054 Intermediate Similarity NPC475518
0.7043 Intermediate Similarity NPC46981
0.7027 Intermediate Similarity NPC252564
0.7009 Intermediate Similarity NPC312637
0.7 Intermediate Similarity NPC476955
0.6887 Remote Similarity NPC21035
0.6855 Remote Similarity NPC238323
0.6768 Remote Similarity NPC304499
0.6726 Remote Similarity NPC220111
0.6724 Remote Similarity NPC212874
0.6696 Remote Similarity NPC289140
0.6694 Remote Similarity NPC28224
0.6607 Remote Similarity NPC174117
0.66 Remote Similarity NPC475458
0.6585 Remote Similarity NPC165396
0.6579 Remote Similarity NPC91604
0.6571 Remote Similarity NPC296734
0.6569 Remote Similarity NPC302578
0.6569 Remote Similarity NPC128951
0.6569 Remote Similarity NPC476233
0.6569 Remote Similarity NPC192046
0.6569 Remote Similarity NPC477227
0.6569 Remote Similarity NPC185915
0.6569 Remote Similarity NPC105208
0.6566 Remote Similarity NPC252182
0.6566 Remote Similarity NPC470071
0.6566 Remote Similarity NPC187471
0.6566 Remote Similarity NPC1340
0.6535 Remote Similarity NPC317242
0.6505 Remote Similarity NPC18857
0.6505 Remote Similarity NPC67657
0.65 Remote Similarity NPC473994
0.65 Remote Similarity NPC153719
0.6496 Remote Similarity NPC241879
0.6491 Remote Similarity NPC292819
0.6471 Remote Similarity NPC163597
0.6466 Remote Similarity NPC262050
0.6465 Remote Similarity NPC192192
0.6465 Remote Similarity NPC232925
0.6465 Remote Similarity NPC63588
0.6465 Remote Similarity NPC251201
0.6455 Remote Similarity NPC228059
0.6442 Remote Similarity NPC477282
0.6442 Remote Similarity NPC269333
0.6442 Remote Similarity NPC81074
0.6442 Remote Similarity NPC287452
0.6436 Remote Similarity NPC477508
0.6429 Remote Similarity NPC167644
0.6429 Remote Similarity NPC474756
0.6429 Remote Similarity NPC311246
0.6423 Remote Similarity NPC478137
0.6417 Remote Similarity NPC470595
0.6415 Remote Similarity NPC475388
0.641 Remote Similarity NPC470592
0.6408 Remote Similarity NPC133596
0.6408 Remote Similarity NPC11907
0.64 Remote Similarity NPC100586
0.64 Remote Similarity NPC157422
0.64 Remote Similarity NPC221196
0.64 Remote Similarity NPC39485
0.64 Remote Similarity NPC109457
0.64 Remote Similarity NPC127094
0.6396 Remote Similarity NPC279329
0.6389 Remote Similarity NPC232044
0.6389 Remote Similarity NPC273290
0.6389 Remote Similarity NPC266651
0.6381 Remote Similarity NPC7479
0.6381 Remote Similarity NPC257296
0.6381 Remote Similarity NPC248944
0.6373 Remote Similarity NPC243027
0.6373 Remote Similarity NPC196136
0.6373 Remote Similarity NPC158208
0.6372 Remote Similarity NPC113500
0.6372 Remote Similarity NPC477224
0.6372 Remote Similarity NPC3538
0.6364 Remote Similarity NPC254037
0.6364 Remote Similarity NPC477820
0.6364 Remote Similarity NPC66407
0.6364 Remote Similarity NPC129829
0.6346 Remote Similarity NPC471769
0.6339 Remote Similarity NPC59006
0.6339 Remote Similarity NPC293609
0.6339 Remote Similarity NPC36372
0.6337 Remote Similarity NPC470610
0.6333 Remote Similarity NPC317534
0.633 Remote Similarity NPC471240
0.6321 Remote Similarity NPC192456
0.6311 Remote Similarity NPC472359
0.6306 Remote Similarity NPC323156
0.63 Remote Similarity NPC282454
0.6296 Remote Similarity NPC320824
0.6296 Remote Similarity NPC227260
0.6286 Remote Similarity NPC476176
0.6283 Remote Similarity NPC277774
0.6275 Remote Similarity NPC10476
0.6275 Remote Similarity NPC48795
0.6275 Remote Similarity NPC192501
0.6275 Remote Similarity NPC228994
0.6273 Remote Similarity NPC210658
0.6273 Remote Similarity NPC5943
0.6273 Remote Similarity NPC472396
0.6273 Remote Similarity NPC161928
0.6271 Remote Similarity NPC176012
0.6262 Remote Similarity NPC470611
0.626 Remote Similarity NPC265275
0.626 Remote Similarity NPC246399
0.626 Remote Similarity NPC48886
0.626 Remote Similarity NPC94881
0.626 Remote Similarity NPC34977
0.625 Remote Similarity NPC473542
0.625 Remote Similarity NPC474574
0.625 Remote Similarity NPC64081
0.6239 Remote Similarity NPC290612
0.6238 Remote Similarity NPC473279
0.623 Remote Similarity NPC147835
0.623 Remote Similarity NPC253645
0.623 Remote Similarity NPC85001
0.623 Remote Similarity NPC95920
0.6228 Remote Similarity NPC473774
0.6228 Remote Similarity NPC45959
0.6228 Remote Similarity NPC473503
0.6228 Remote Similarity NPC175
0.6228 Remote Similarity NPC30687
0.6228 Remote Similarity NPC252253
0.6228 Remote Similarity NPC309866
0.6228 Remote Similarity NPC24960
0.6226 Remote Similarity NPC16449
0.6226 Remote Similarity NPC474714
0.6216 Remote Similarity NPC281004
0.6216 Remote Similarity NPC128475
0.6214 Remote Similarity NPC231680
0.6214 Remote Similarity NPC91387
0.6214 Remote Similarity NPC270306
0.6212 Remote Similarity NPC470537
0.621 Remote Similarity NPC124358
0.6207 Remote Similarity NPC477223
0.6207 Remote Similarity NPC477222
0.6204 Remote Similarity NPC232023
0.6204 Remote Similarity NPC478054
0.6202 Remote Similarity NPC242692
0.62 Remote Similarity NPC107919
0.6198 Remote Similarity NPC478053
0.6195 Remote Similarity NPC473830
0.6195 Remote Similarity NPC149966
0.6195 Remote Similarity NPC5632
0.6195 Remote Similarity NPC204881
0.6194 Remote Similarity NPC478139
0.619 Remote Similarity NPC147993
0.619 Remote Similarity NPC471045
0.6182 Remote Similarity NPC131365
0.6182 Remote Similarity NPC321340
0.6182 Remote Similarity NPC215968
0.6182 Remote Similarity NPC119633
0.6182 Remote Similarity NPC270957
0.6182 Remote Similarity NPC155531
0.6182 Remote Similarity NPC171698
0.6174 Remote Similarity NPC469710
0.6174 Remote Similarity NPC473065
0.6174 Remote Similarity NPC473067
0.6174 Remote Similarity NPC473064
0.6174 Remote Similarity NPC92196
0.6168 Remote Similarity NPC73515
0.6167 Remote Similarity NPC470596
0.6167 Remote Similarity NPC475239
0.6162 Remote Similarity NPC48079
0.6161 Remote Similarity NPC473472
0.6161 Remote Similarity NPC82955
0.6161 Remote Similarity NPC102725
0.6161 Remote Similarity NPC74258
0.6154 Remote Similarity NPC473638
0.6154 Remote Similarity NPC470145
0.614 Remote Similarity NPC144790
0.614 Remote Similarity NPC149400

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC267217 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.7345 Intermediate Similarity NPD7646 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD7991 Discontinued
0.7091 Intermediate Similarity NPD7919 Phase 3
0.7091 Intermediate Similarity NPD7920 Phase 3
0.7027 Intermediate Similarity NPD8088 Phase 1
0.7 Intermediate Similarity NPD7755 Approved
0.7 Intermediate Similarity NPD7754 Approved
0.6957 Remote Similarity NPD6920 Discontinued
0.693 Remote Similarity NPD7911 Approved
0.693 Remote Similarity NPD7987 Approved
0.693 Remote Similarity NPD7912 Approved
0.693 Remote Similarity NPD7986 Approved
0.681 Remote Similarity NPD8040 Discontinued
0.6752 Remote Similarity NPD7989 Approved
0.6752 Remote Similarity NPD7990 Approved
0.6667 Remote Similarity NPD8418 Phase 2
0.6636 Remote Similarity NPD8308 Discontinued
0.6555 Remote Similarity NPD8174 Phase 2
0.6555 Remote Similarity NPD6415 Discontinued
0.6475 Remote Similarity NPD8077 Approved
0.6475 Remote Similarity NPD8078 Approved
0.6381 Remote Similarity NPD6928 Phase 2
0.62 Remote Similarity NPD4267 Clinical (unspecified phase)
0.619 Remote Similarity NPD6940 Discontinued
0.616 Remote Similarity NPD8298 Phase 2
0.6 Remote Similarity NPD8171 Discontinued
0.598 Remote Similarity NPD4787 Phase 1
0.5965 Remote Similarity NPD6700 Approved
0.5965 Remote Similarity NPD6701 Clinical (unspecified phase)
0.5913 Remote Similarity NPD6703 Approved
0.5913 Remote Similarity NPD6702 Approved
0.587 Remote Similarity NPD8449 Approved
0.5827 Remote Similarity NPD8450 Suspended
0.5741 Remote Similarity NPD6115 Approved
0.5741 Remote Similarity NPD6118 Approved
0.5741 Remote Similarity NPD6114 Approved
0.5741 Remote Similarity NPD6697 Approved
0.5664 Remote Similarity NPD394 Phase 3

Structure

External Identifiers

PubChem CID   5281278
ChEMBL   CHEMBL1242438
ZINC  

Physicochemical Properties

Molecular Weight:  377.26
ALogP:  -2.568
MLogP:  3.33
XLogP:  0.869
# Rotatable Bonds:  8
Polar Surface Area:  73.16
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  6
# Heavy Atoms:  27

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs