Natural Product: NPC226592

Natural Product ID:  NPC226592
Common Name:   (S)-17-Hydroxy-15E-Octadecen-9,11,13-Triynoic Acid
IUPAC Name:   (E,17S)-17-hydroxyoctadec-15-en-9,11,13-triynoic acid
Synonyms:  
Molecular Formula:   C18H22O3
Standard InCHIKey:  UQORHUYKZNBNLF-VOGRQWBCSA-N
Standard InCHI:  InChI=1S/C18H22O3/c1-17(19)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18(20)21/h13,15,17,19H,4,6,8,10,12,14,16H2,1H3,(H,20,21)/b15-13+/t17-/m0/s1
Canonical SMILES:  OC(=O)CCCCCCCC#CC#CC#C/C=C/[C@@H](O)C
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
NPO32829 ochanostachys amentacea Species Coulaceae Eukaryota Twigs PMID[11430012]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2345 Cell Line SW626 Homo sapiens ED50 = 0.36 ug/ml 26264503
NPT2 Others Unspecified ED50 > 20 ug/ml 20516271
NPT858 Cell Line LNCaP Homo sapiens ED50 = 0.3 ug/ml 20516271
NPT91 Cell Line KB Homo sapiens ED50 > 20 ug/ml 20516271
NPT136 Cell Line SK-N-SH Homo sapiens ED50 = 3.7 ug/ml 19596885
NPT726 Cell Line M109 Mus musculus ED50 = 5.4 ug/ml 25211145
NPT1034 Cell Line Lu1 Homo sapiens ED50 > 20 ug/ml 18537291
NPT91 Cell Line KB Homo sapiens ED50 = 1.1 ug/ml 22578169
NPT1851 Cell Line Col2 Homo sapiens ED50 = 9.9 ug/ml 17958396

  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 NPC226592 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
0.9667 High Similarity NPC470320
0.9016 High Similarity NPC477829
0.8889 High Similarity NPC136164
0.8889 High Similarity NPC255863
0.8889 High Similarity NPC245947
0.8615 High Similarity NPC99619
0.8615 High Similarity NPC26500
0.8571 High Similarity NPC29697
0.8548 High Similarity NPC243532
0.85 High Similarity NPC179764
0.85 High Similarity NPC187777
0.8413 Intermediate Similarity NPC271282
0.8413 Intermediate Similarity NPC66460
0.8413 Intermediate Similarity NPC201939
0.8413 Intermediate Similarity NPC325929
0.8413 Intermediate Similarity NPC475984
0.8358 Intermediate Similarity NPC143396
0.8333 Intermediate Similarity NPC473863
0.8333 Intermediate Similarity NPC54766
0.8333 Intermediate Similarity NPC274290
0.8308 Intermediate Similarity NPC318420
0.8308 Intermediate Similarity NPC326268
0.8281 Intermediate Similarity NPC470965
0.8254 Intermediate Similarity NPC327112
0.8167 Intermediate Similarity NPC49059
0.8167 Intermediate Similarity NPC256209
0.8065 Intermediate Similarity NPC225929
0.8 Intermediate Similarity NPC1813
0.8 Intermediate Similarity NPC294548
0.8 Intermediate Similarity NPC36061
0.8 Intermediate Similarity NPC139029
0.7969 Intermediate Similarity NPC235242
0.7966 Intermediate Similarity NPC284212
0.7903 Intermediate Similarity NPC477201
0.7887 Intermediate Similarity NPC227396
0.7879 Intermediate Similarity NPC328089
0.7879 Intermediate Similarity NPC68343
0.7869 Intermediate Similarity NPC85813
0.7869 Intermediate Similarity NPC290563
0.7869 Intermediate Similarity NPC88966
0.7869 Intermediate Similarity NPC6095
0.7869 Intermediate Similarity NPC424
0.7869 Intermediate Similarity NPC25417
0.7869 Intermediate Similarity NPC261831
0.7869 Intermediate Similarity NPC154245
0.7869 Intermediate Similarity NPC87564
0.7869 Intermediate Similarity NPC32467
0.7869 Intermediate Similarity NPC281972
0.7846 Intermediate Similarity NPC321838
0.7846 Intermediate Similarity NPC113293
0.7833 Intermediate Similarity NPC281245
0.7833 Intermediate Similarity NPC18357
0.7812 Intermediate Similarity NPC473652
0.7794 Intermediate Similarity NPC271921
0.7794 Intermediate Similarity NPC330426
0.7794 Intermediate Similarity NPC104537
0.7794 Intermediate Similarity NPC127091
0.7794 Intermediate Similarity NPC22101
0.7794 Intermediate Similarity NPC148192
0.7761 Intermediate Similarity NPC317881
0.7761 Intermediate Similarity NPC323045
0.7746 Intermediate Similarity NPC325627
0.7742 Intermediate Similarity NPC474513
0.7742 Intermediate Similarity NPC52264
0.7742 Intermediate Similarity NPC477726
0.7742 Intermediate Similarity NPC146551
0.7742 Intermediate Similarity NPC477725
0.7742 Intermediate Similarity NPC470963
0.7705 Intermediate Similarity NPC70387
0.7705 Intermediate Similarity NPC321062
0.7692 Intermediate Similarity NPC328311
0.7681 Intermediate Similarity NPC48218
0.7681 Intermediate Similarity NPC473559
0.7681 Intermediate Similarity NPC324981
0.7681 Intermediate Similarity NPC141481
0.7671 Intermediate Similarity NPC279537
0.7667 Intermediate Similarity NPC470410
0.7667 Intermediate Similarity NPC151782
0.7667 Intermediate Similarity NPC470411
0.7667 Intermediate Similarity NPC129263
0.7667 Intermediate Similarity NPC28205
0.7667 Intermediate Similarity NPC470412
0.7656 Intermediate Similarity NPC267817
0.7656 Intermediate Similarity NPC34416
0.7627 Intermediate Similarity NPC304162
0.7619 Intermediate Similarity NPC470968
0.7619 Intermediate Similarity NPC473847
0.7619 Intermediate Similarity NPC477661
0.7619 Intermediate Similarity NPC475384
0.7619 Intermediate Similarity NPC470967
0.7619 Intermediate Similarity NPC470966
0.7619 Intermediate Similarity NPC470964
0.7619 Intermediate Similarity NPC471960
0.7619 Intermediate Similarity NPC311648
0.7619 Intermediate Similarity NPC161838
0.7619 Intermediate Similarity NPC18951
0.7619 Intermediate Similarity NPC470969
0.7581 Intermediate Similarity NPC137538
0.7581 Intermediate Similarity NPC110732
0.7576 Intermediate Similarity NPC328776
0.7576 Intermediate Similarity NPC320305
0.7571 Intermediate Similarity NPC470436
0.7571 Intermediate Similarity NPC236208
0.7541 Intermediate Similarity NPC161366
0.7541 Intermediate Similarity NPC92114
0.7538 Intermediate Similarity NPC322002
0.7538 Intermediate Similarity NPC106851
0.7538 Intermediate Similarity NPC474267
0.7538 Intermediate Similarity NPC274927
0.7536 Intermediate Similarity NPC473829
0.7536 Intermediate Similarity NPC475443
0.7536 Intermediate Similarity NPC49863
0.75 Intermediate Similarity NPC193975
0.75 Intermediate Similarity NPC594
0.75 Intermediate Similarity NPC44542
0.75 Intermediate Similarity NPC48968
0.75 Intermediate Similarity NPC265551
0.75 Intermediate Similarity NPC224227
0.75 Intermediate Similarity NPC212730
0.75 Intermediate Similarity NPC472445
0.75 Intermediate Similarity NPC470970
0.75 Intermediate Similarity NPC323477
0.75 Intermediate Similarity NPC72699
0.7467 Intermediate Similarity NPC192006
0.7465 Intermediate Similarity NPC476660
0.7465 Intermediate Similarity NPC42526
0.746 Intermediate Similarity NPC128061
0.746 Intermediate Similarity NPC28779
0.746 Intermediate Similarity NPC10316
0.746 Intermediate Similarity NPC473910
0.746 Intermediate Similarity NPC473721
0.746 Intermediate Similarity NPC152668
0.746 Intermediate Similarity NPC473735
0.746 Intermediate Similarity NPC223677
0.746 Intermediate Similarity NPC473725
0.746 Intermediate Similarity NPC200845
0.746 Intermediate Similarity NPC475353
0.746 Intermediate Similarity NPC473896
0.7424 Intermediate Similarity NPC471278
0.7424 Intermediate Similarity NPC122521
0.7424 Intermediate Similarity NPC251042
0.7424 Intermediate Similarity NPC174447
0.7419 Intermediate Similarity NPC139545
0.7419 Intermediate Similarity NPC309606
0.7419 Intermediate Similarity NPC39633
0.7419 Intermediate Similarity NPC34577
0.7419 Intermediate Similarity NPC71761
0.7391 Intermediate Similarity NPC328653
0.7385 Intermediate Similarity NPC469373
0.7377 Intermediate Similarity NPC262968
0.7361 Intermediate Similarity NPC186531
0.7333 Intermediate Similarity NPC248884
0.7333 Intermediate Similarity NPC149821
0.7333 Intermediate Similarity NPC153538
0.7333 Intermediate Similarity NPC85079
0.7333 Intermediate Similarity NPC5413
0.7333 Intermediate Similarity NPC31194
0.7324 Intermediate Similarity NPC473772
0.7324 Intermediate Similarity NPC317583
0.7313 Intermediate Similarity NPC168407
0.7313 Intermediate Similarity NPC40082
0.7302 Intermediate Similarity NPC473532
0.7288 Intermediate Similarity NPC42304
0.7286 Intermediate Similarity NPC25298
0.7273 Intermediate Similarity NPC318306
0.7273 Intermediate Similarity NPC329249
0.7273 Intermediate Similarity NPC222852
0.7273 Intermediate Similarity NPC200446
0.726 Intermediate Similarity NPC470435
0.7246 Intermediate Similarity NPC320642
0.7237 Intermediate Similarity NPC469495
0.7231 Intermediate Similarity NPC323436
0.7213 Intermediate Similarity NPC59051
0.7206 Intermediate Similarity NPC54925
0.72 Intermediate Similarity NPC49392
0.72 Intermediate Similarity NPC190400
0.7188 Intermediate Similarity NPC228473
0.7188 Intermediate Similarity NPC45626
0.7183 Intermediate Similarity NPC218477
0.7179 Intermediate Similarity NPC88735
0.7179 Intermediate Similarity NPC47031
0.7167 Intermediate Similarity NPC180534
0.7167 Intermediate Similarity NPC207292
0.7164 Intermediate Similarity NPC229252
0.7164 Intermediate Similarity NPC143857
0.7162 Intermediate Similarity NPC474321
0.7162 Intermediate Similarity NPC92558
0.7143 Intermediate Similarity NPC61177
0.7143 Intermediate Similarity NPC187361
0.7143 Intermediate Similarity NPC284224
0.7143 Intermediate Similarity NPC217188
0.7143 Intermediate Similarity NPC26102
0.7143 Intermediate Similarity NPC477724
0.7143 Intermediate Similarity NPC201225
0.7143 Intermediate Similarity NPC209995
0.7123 Intermediate Similarity NPC319163
0.7123 Intermediate Similarity NPC320119
0.7123 Intermediate Similarity NPC67076
0.7121 Intermediate Similarity NPC329819
0.7105 Intermediate Similarity NPC116177

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC226592 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
0.8254 Intermediate Similarity NPD4246 Clinical (unspecified phase)
0.8154 Intermediate Similarity NPD3197 Phase 1
0.8 Intermediate Similarity NPD3172 Approved
0.7869 Intermediate Similarity NPD3194 Approved
0.7869 Intermediate Similarity NPD3196 Approved
0.7869 Intermediate Similarity NPD4266 Approved
0.7869 Intermediate Similarity NPD3195 Phase 2
0.7536 Intermediate Similarity NPD4247 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD28 Approved
0.7377 Intermediate Similarity NPD29 Approved
0.7333 Intermediate Similarity NPD3173 Approved
0.7237 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD5331 Approved
0.7215 Intermediate Similarity NPD5332 Approved
0.7167 Intermediate Similarity NPD622 Approved
0.7089 Intermediate Similarity NPD4269 Approved
0.7089 Intermediate Similarity NPD4270 Approved
0.7051 Intermediate Similarity NPD4252 Approved
0.7013 Intermediate Similarity NPD4268 Approved
0.7013 Intermediate Similarity NPD4271 Approved
0.7 Intermediate Similarity NPD5362 Discontinued
0.7 Intermediate Similarity NPD7154 Phase 3
0.6835 Remote Similarity NPD4822 Approved
0.6835 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6835 Remote Similarity NPD4821 Approved
0.6835 Remote Similarity NPD4819 Approved
0.6835 Remote Similarity NPD4820 Approved
0.6833 Remote Similarity NPD3174 Discontinued
0.6833 Remote Similarity NPD4222 Approved
0.6829 Remote Similarity NPD5363 Approved
0.6747 Remote Similarity NPD5786 Approved
0.6667 Remote Similarity NPD4756 Discovery
0.6625 Remote Similarity NPD5368 Approved
0.6557 Remote Similarity NPD39 Approved
0.6543 Remote Similarity NPD4790 Discontinued
0.6543 Remote Similarity NPD5369 Approved
0.6463 Remote Similarity NPD6435 Approved
0.6437 Remote Similarity NPD5785 Approved
0.6429 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6418 Remote Similarity NPD4627 Clinical (unspecified phase)
0.6377 Remote Similarity NPD6109 Phase 1
0.6375 Remote Similarity NPD3732 Approved
0.6364 Remote Similarity NPD7983 Approved
0.6353 Remote Similarity NPD4249 Approved
0.6349 Remote Similarity NPD5343 Approved
0.6322 Remote Similarity NPD5370 Suspended
0.6292 Remote Similarity NPD5779 Approved
0.6292 Remote Similarity NPD5778 Approved
0.6279 Remote Similarity NPD4250 Approved
0.6279 Remote Similarity NPD4251 Approved
0.6269 Remote Similarity NPD3730 Approved
0.6269 Remote Similarity NPD3729 Clinical (unspecified phase)
0.6269 Remote Similarity NPD3728 Approved
0.623 Remote Similarity NPD5326 Phase 3
0.6203 Remote Similarity NPD8039 Approved
0.618 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6167 Remote Similarity NPD2270 Approved
0.6129 Remote Similarity NPD2699 Approved
0.6102 Remote Similarity NPD633 Phase 3
0.6102 Remote Similarity NPD9448 Phase 2
0.6087 Remote Similarity NPD7839 Suspended
0.6067 Remote Similarity NPD6698 Approved
0.6067 Remote Similarity NPD46 Approved
0.6032 Remote Similarity NPD4265 Approved
0.6027 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6 Remote Similarity NPD7331 Phase 2
0.6 Remote Similarity NPD3704 Approved
0.5977 Remote Similarity NPD4623 Approved
0.5977 Remote Similarity NPD4519 Discontinued
0.5955 Remote Similarity NPD6101 Approved
0.5955 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5873 Remote Similarity NPD6096 Approved
0.5873 Remote Similarity NPD6097 Approved
0.5873 Remote Similarity NPD3199 Clinical (unspecified phase)
0.5867 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5833 Remote Similarity NPD3198 Approved
0.5833 Remote Similarity NPD9655 Approved
0.5824 Remote Similarity NPD6411 Approved
0.5821 Remote Similarity NPD6927 Phase 3
0.5811 Remote Similarity NPD3210 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5758 Remote Similarity NPD4220 Pre-registration
0.5714 Remote Similarity NPD342 Phase 1
0.5698 Remote Similarity NPD3667 Approved
0.5676 Remote Similarity NPD368 Approved
0.5667 Remote Similarity NPD3206 Approved
0.5652 Remote Similarity NPD7515 Phase 2
0.5652 Remote Similarity NPD7637 Suspended
0.5638 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5618 Remote Similarity NPD6422 Discontinued
0.5606 Remote Similarity NPD6125 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   10016854
ChEMBL   CHEMBL459819
ZINC  

Physicochemical Properties

Molecular Weight:  286.16
ALogP:  0.197
MLogP:  3.11
XLogP:  4.82
# Rotatable Bonds:  11
Polar Surface Area:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  0
# Heavy Atoms:  21

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Similar NPs/Drugs