Natural Product: NPC180575

Natural Product ID:  NPC180575
Common Name:   Bupleurynol
IUPAC Name:   (2Z,9E,11E)-octadeca-2,9,11-trien-5,7-diyn-1-ol
Synonyms:   Bupleurynol
Molecular Formula:   C18H24O
Standard InCHIKey:  NSVMMMROPMMCOH-LLBVTOMBSA-N
Standard InCHI:  InChI=1S/C18H24O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h7-10,16-17,19H,2-6,15,18H2,1H3/b8-7+,10-9+,17-16-
Canonical SMILES:  CCCCCC/C=C/C=C/C#CC#CC/C=CCO
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
NPO16425 Bupleurum longiradiatum Species Apiaceae Eukaryota PMID[19994846]
NPO16425 Bupleurum longiradiatum Species Apiaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT116 Cell Line HL-60 Homo sapiens IC50 = 11000 nM 19994846

  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 NPC180575 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
0.9318 High Similarity NPC269074
0.907 High Similarity NPC206906
0.907 High Similarity NPC304151
0.8889 High Similarity NPC276825
0.875 High Similarity NPC71053
0.875 High Similarity NPC59408
0.8723 High Similarity NPC31194
0.8723 High Similarity NPC153538
0.8723 High Similarity NPC248884
0.8723 High Similarity NPC85079
0.8696 High Similarity NPC19834
0.8696 High Similarity NPC35141
0.8696 High Similarity NPC55063
0.8696 High Similarity NPC124183
0.8667 High Similarity NPC101616
0.86 High Similarity NPC110732
0.8542 High Similarity NPC72699
0.8542 High Similarity NPC249670
0.8542 High Similarity NPC474642
0.8542 High Similarity NPC473913
0.8542 High Similarity NPC328784
0.8542 High Similarity NPC291437
0.84 Intermediate Similarity NPC34577
0.84 Intermediate Similarity NPC61177
0.8372 Intermediate Similarity NPC15934
0.8367 Intermediate Similarity NPC93639
0.8367 Intermediate Similarity NPC151782
0.8333 Intermediate Similarity NPC471275
0.8333 Intermediate Similarity NPC302310
0.8333 Intermediate Similarity NPC471276
0.8333 Intermediate Similarity NPC471280
0.8333 Intermediate Similarity NPC125122
0.8261 Intermediate Similarity NPC138935
0.8261 Intermediate Similarity NPC108195
0.8222 Intermediate Similarity NPC149668
0.82 Intermediate Similarity NPC142092
0.8182 Intermediate Similarity NPC103236
0.8182 Intermediate Similarity NPC329762
0.8182 Intermediate Similarity NPC27444
0.8163 Intermediate Similarity NPC471281
0.8163 Intermediate Similarity NPC477727
0.8163 Intermediate Similarity NPC199286
0.8 Intermediate Similarity NPC76198
0.8 Intermediate Similarity NPC224148
0.8 Intermediate Similarity NPC197272
0.8 Intermediate Similarity NPC294278
0.8 Intermediate Similarity NPC256656
0.8 Intermediate Similarity NPC129263
0.8 Intermediate Similarity NPC329608
0.8 Intermediate Similarity NPC165447
0.8 Intermediate Similarity NPC9273
0.8 Intermediate Similarity NPC89824
0.8 Intermediate Similarity NPC170776
0.8 Intermediate Similarity NPC475477
0.8 Intermediate Similarity NPC55383
0.8 Intermediate Similarity NPC477723
0.8 Intermediate Similarity NPC471959
0.7885 Intermediate Similarity NPC256209
0.7885 Intermediate Similarity NPC49059
0.7778 Intermediate Similarity NPC44542
0.7736 Intermediate Similarity NPC474644
0.7692 Intermediate Similarity NPC284224
0.7674 Intermediate Similarity NPC213767
0.7609 Intermediate Similarity NPC269823
0.7593 Intermediate Similarity NPC473865
0.7593 Intermediate Similarity NPC474643
0.7556 Intermediate Similarity NPC29091
0.7556 Intermediate Similarity NPC182840
0.7556 Intermediate Similarity NPC255042
0.7556 Intermediate Similarity NPC103213
0.7547 Intermediate Similarity NPC473532
0.7547 Intermediate Similarity NPC48058
0.75 Intermediate Similarity NPC216416
0.7455 Intermediate Similarity NPC212730
0.7455 Intermediate Similarity NPC265551
0.7455 Intermediate Similarity NPC193975
0.7455 Intermediate Similarity NPC472445
0.7447 Intermediate Similarity NPC256766
0.7447 Intermediate Similarity NPC213538
0.7442 Intermediate Similarity NPC58957
0.7407 Intermediate Similarity NPC146551
0.7407 Intermediate Similarity NPC473725
0.7407 Intermediate Similarity NPC473896
0.7407 Intermediate Similarity NPC477725
0.7407 Intermediate Similarity NPC470963
0.7407 Intermediate Similarity NPC152668
0.7407 Intermediate Similarity NPC473721
0.7407 Intermediate Similarity NPC477726
0.7407 Intermediate Similarity NPC473910
0.7407 Intermediate Similarity NPC471239
0.7407 Intermediate Similarity NPC474513
0.7407 Intermediate Similarity NPC475353
0.7407 Intermediate Similarity NPC473735
0.7292 Intermediate Similarity NPC116934
0.7273 Intermediate Similarity NPC470967
0.7273 Intermediate Similarity NPC471960
0.7273 Intermediate Similarity NPC473847
0.7273 Intermediate Similarity NPC477661
0.7273 Intermediate Similarity NPC470966
0.7273 Intermediate Similarity NPC470968
0.7273 Intermediate Similarity NPC470969
0.7273 Intermediate Similarity NPC475384
0.7273 Intermediate Similarity NPC311648
0.7273 Intermediate Similarity NPC249645
0.7273 Intermediate Similarity NPC161838
0.7273 Intermediate Similarity NPC470964
0.7273 Intermediate Similarity NPC55412
0.7222 Intermediate Similarity NPC269615
0.7209 Intermediate Similarity NPC250734
0.72 Intermediate Similarity NPC157096
0.7193 Intermediate Similarity NPC222852
0.717 Intermediate Similarity NPC106531
0.7143 Intermediate Similarity NPC48968
0.7143 Intermediate Similarity NPC594
0.7143 Intermediate Similarity NPC470970
0.7115 Intermediate Similarity NPC26960
0.7115 Intermediate Similarity NPC182102
0.7091 Intermediate Similarity NPC329686
0.7069 Intermediate Similarity NPC471278
0.7018 Intermediate Similarity NPC469373
0.7 Intermediate Similarity NPC76976
0.7 Intermediate Similarity NPC160628
0.7 Intermediate Similarity NPC140501
0.6981 Remote Similarity NPC473672
0.6981 Remote Similarity NPC474495
0.6957 Remote Similarity NPC34873
0.6957 Remote Similarity NPC40434
0.6949 Remote Similarity NPC271282
0.6949 Remote Similarity NPC325929
0.6949 Remote Similarity NPC66460
0.6939 Remote Similarity NPC252978
0.6909 Remote Similarity NPC300121
0.6897 Remote Similarity NPC473652
0.6852 Remote Similarity NPC208638
0.6833 Remote Similarity NPC29697
0.6792 Remote Similarity NPC475071
0.6792 Remote Similarity NPC474460
0.6792 Remote Similarity NPC473768
0.6786 Remote Similarity NPC471991
0.678 Remote Similarity NPC327112
0.6735 Remote Similarity NPC249801
0.6735 Remote Similarity NPC46248
0.6735 Remote Similarity NPC31121
0.6727 Remote Similarity NPC477724
0.6727 Remote Similarity NPC187361
0.6727 Remote Similarity NPC474496
0.6727 Remote Similarity NPC26102
0.6667 Remote Similarity NPC474362
0.6667 Remote Similarity NPC29234
0.6667 Remote Similarity NPC472808
0.6667 Remote Similarity NPC474202
0.6667 Remote Similarity NPC475984
0.6667 Remote Similarity NPC244038
0.6667 Remote Similarity NPC324224
0.6667 Remote Similarity NPC168407
0.6607 Remote Similarity NPC56028
0.6607 Remote Similarity NPC163912
0.6607 Remote Similarity NPC305288
0.6607 Remote Similarity NPC167759
0.6604 Remote Similarity NPC267110
0.6557 Remote Similarity NPC470965
0.6545 Remote Similarity NPC35756
0.65 Remote Similarity NPC299730
0.6491 Remote Similarity NPC273023
0.6491 Remote Similarity NPC474913
0.6491 Remote Similarity NPC317899
0.6491 Remote Similarity NPC297020
0.6471 Remote Similarity NPC267514
0.6471 Remote Similarity NPC145755
0.6452 Remote Similarity NPC470320
0.6452 Remote Similarity NPC226592
0.6444 Remote Similarity NPC62779
0.6441 Remote Similarity NPC181872
0.6429 Remote Similarity NPC303672
0.6429 Remote Similarity NPC119655
0.6429 Remote Similarity NPC217188
0.64 Remote Similarity NPC208936
0.6379 Remote Similarity NPC477049
0.6379 Remote Similarity NPC24216
0.6379 Remote Similarity NPC306420
0.6379 Remote Similarity NPC104138
0.6379 Remote Similarity NPC261158
0.6364 Remote Similarity NPC196831
0.6349 Remote Similarity NPC477525
0.6349 Remote Similarity NPC245947
0.6349 Remote Similarity NPC255863
0.6349 Remote Similarity NPC136164
0.6349 Remote Similarity NPC308844
0.6333 Remote Similarity NPC318306
0.6333 Remote Similarity NPC322002
0.6333 Remote Similarity NPC322186
0.6316 Remote Similarity NPC189677
0.6316 Remote Similarity NPC124382
0.6316 Remote Similarity NPC123669
0.6316 Remote Similarity NPC13011
0.6304 Remote Similarity NPC182392
0.6296 Remote Similarity NPC475153
0.6271 Remote Similarity NPC474869
0.6271 Remote Similarity NPC471279
0.6271 Remote Similarity NPC121034

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC180575 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
0.7273 Intermediate Similarity NPD4219 Approved
0.7 Intermediate Similarity NPD4265 Approved
0.678 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6604 Remote Similarity NPD4220 Pre-registration
0.6207 Remote Similarity NPD342 Phase 1
0.6032 Remote Similarity NPD3210 Clinical (unspecified phase)
0.5909 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5873 Remote Similarity NPD4194 Approved
0.5873 Remote Similarity NPD4192 Approved
0.5873 Remote Similarity NPD4191 Approved
0.5873 Remote Similarity NPD4193 Approved
0.5741 Remote Similarity NPD39 Approved
0.5714 Remote Similarity NPD4732 Discontinued
0.5667 Remote Similarity NPD4627 Clinical (unspecified phase)
0.5645 Remote Similarity NPD585 Clinical (unspecified phase)
0.5625 Remote Similarity NPD368 Approved
0.5614 Remote Similarity NPD2268 Discontinued

Structure

External Identifiers

PubChem CID   5315554
ChEMBL   CHEMBL1086773
ZINC  

Physicochemical Properties

Molecular Weight:  256.18
ALogP:  1.6116
MLogP:  3.33
XLogP:  6.444
# Rotatable Bonds:  10
Polar Surface Area:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  19

Download Data

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Structure MOL file  
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Similar NPs/Drugs