Natural Product: NPC248884

Natural Product ID:  NPC248884
Common Name:   Falcarindiol
IUPAC Name:   (3R,8S,9Z)-heptadeca-1,9-dien-4,6-diyne-3,8-diol
Synonyms:   (3R,8S)-Falcarindiol; (3S,8S)-Falcarindiol; Falcarindiol
Molecular Formula:   C17H24O2
Standard InCHIKey:  QWCNQXNAFCBLLV-YWALDVPYSA-N
Standard InCHI:  InChI=1S/C17H24O2/c1-3-5-6-7-8-9-10-14-17(19)15-12-11-13-16(18)4-2/h4,10,14,16-19H,2-3,5-9H2,1H3/b14-10-/t16-,17+/m1/s1
Canonical SMILES:  CCCCCCC/C=C[C@@H](C#CC#C[C@@H](C=C)O)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
NPO15462 Angelica sinensis Species Apiaceae Eukaryota roots Purchased from Kiu Shun Trading Ltd., Vancouver, Canada 2000 PMID[16643021]
NPO24374 Brunsvigia orientalis Species Amaryllidaceae Eukaryota UNPD*
NPO25131 Parmelia weberi Species Parmeliaceae Eukaryota UNPD*
NPO24758 Angelica dahurica Species Apiaceae Eukaryota TCMSP*
NPO18129 Notopterygii rhizoma et radix NA NA NA TCMSP*
NPO29710 Saposhnikoviae radix NA NA NA TCMSP*
NPO29700 Peucedani radix NA NA NA TCMSP*
NPO29661 Glehniae radix NA NA NA TCMSP*
NPO2921 Angelica acutiloba Species Apiaceae Eukaryota TM-MC*
NPO24758 Angelica dahurica Species Apiaceae Eukaryota TM-MC*
NPO15394 Angelica decursiva Species Apiaceae Eukaryota TM-MC*
NPO11438 Angelica gigas Species Apiaceae Eukaryota TM-MC*
NPO15462 Angelica sinensis Species Apiaceae Eukaryota TM-MC*
NPO22033 Cnidium officinale Species Apiaceae Eukaryota TM-MC*
NPO8874 Glehnia littoralis Species Apiaceae Eukaryota TM-MC*
NPO18951 Ligusticum sinense Species Apiaceae Eukaryota TM-MC*
NPO24644 Hansenia forbesii Species Apiaceae Eukaryota TM-MC*
NPO2392 Hansenia weberbaueriana Species Apiaceae Eukaryota TM-MC*
NPO2953 Ostericum grosseserratum Species Apiaceae Eukaryota TM-MC*
NPO4340 Peucedanum praeruptorum Species Apiaceae Eukaryota TM-MC*
NPO3509 Angelica furcijuga Species Apiaceae Eukaryota roots Miyazaki prefecture, Japan PMID[9873511]
NPO18101 Cicuta virosa Species Apiaceae Eukaryota subterranean part PMID[11087575]
NPO25695 Oplopanax horridus Species Araliaceae Eukaryota PMID[20218656]
NPO21056 Angelica keiskei Species Apiaceae Eukaryota Stems PMID[25891102]
NPO25695 Oplopanax horridus Species Araliaceae Eukaryota PMID[9392889]
NPO25663 Piscidia piscipula Species Fabaceae Eukaryota UNPD*
NPO23922 Helichrysum oxyphyllum Species Asteraceae Eukaryota UNPD*
NPO23679 Streptomyces roseiscleroticus Species Streptomycetaceae Bacteria UNPD*
NPO163 Daucus carota Species Apiaceae Eukaryota TCM_Taiwan*
NPO28058 Seseli grandivittatum Species Apiaceae Eukaryota TCM_Taiwan*
NPO638 Aralia fargesii Species Araliaceae Eukaryota TCM_Taiwan*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified ED50 = 3.2 ug/ml 9871635
NPT29 Organism Rattus norvegicus Rattus norvegicus IC50 > 100000 nM 9873511
NPT29 Organism Rattus norvegicus Rattus norvegicus Inhibition = -33 % 9873511
NPT32 Organism Mus musculus Mus musculus IC50 = 4400 nM 9873511
NPT32 Organism Mus musculus Mus musculus LD50 > 200 mg/kg 11087575
NPT805 Protein Complex GABA-A receptor; anion channel Rattus norvegicus IC50 > 10000 nM 11087575
NPT1069 Individual Protein Mu opioid receptor Rattus norvegicus Activity > 50 % 18166466
NPT1167 Individual Protein Delta opioid receptor Mus musculus Activity > 50 % 18166466
NPT272 Individual Protein Kappa opioid receptor Homo sapiens Activity > 50 % 18166466
NPT1069 Individual Protein Mu opioid receptor Rattus norvegicus Ki = 1125 nM 18166466
NPT1167 Individual Protein Delta opioid receptor Mus musculus Ki = 1096 nM 18166466
NPT272 Individual Protein Kappa opioid receptor Homo sapiens Ki = 2515 nM 18166466
NPT1857 Individual Protein Dopamine D1 receptor Rattus norvegicus Ki = 192 nM 18166466
NPT1857 Individual Protein Dopamine D1 receptor Rattus norvegicus Activity > 50 % 18166466
NPT2 Others Unspecified GI50 = 660 nM 8792622
NPT2 Others Unspecified TGI = 2200 nM 8792622
NPT2 Others Unspecified LC50 = 7600 nM 8792622
NPT30 Individual Protein Cyclooxygenase-1 Homo sapiens IC50 = 66000 nM 16038536
NPT176 Organism Artemia salina Artemia salina LC50 = 3.32 ug/ml 8254353
NPT116 Cell Line HL-60 Homo sapiens IC50 = 8900 nM 15387667
NPT453 Cell Line HT-1080 Homo sapiens IC50 = 13000 nM 15387667
NPT114 Cell Line LoVo Homo sapiens IC50 = 4300 nM 15387667
NPT114 Cell Line LoVo Homo sapiens IC50 > 40000 nM 15387667
NPT19 Organism Escherichia coli Escherichia coli MIC = 25 ug/ml 9392889
NPT19 Organism Escherichia coli Escherichia coli MIC > 50 ug/ml 9392889
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC > 50 ug/ml 9392889
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 50 ug/ml 9392889
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 25 ug/ml 9392889
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 6.25 ug/ml 9392889
NPT20 Organism Candida albicans Candida albicans MIC = 25 ug/ml 9392889
NPT1785 Individual Protein Serotonin 7 (5-HT7) receptor Homo sapiens IC50 = 117500 nM 16643021
NPT1785 Individual Protein Serotonin 7 (5-HT7) receptor Homo sapiens Inhibition = 61 % 16643021
NPT19 Organism Escherichia coli Escherichia coli MIC = 2.5 ug/ml 10217726
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 12.5 ug/ml 10217726
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 25 ug/ml 10217726
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 12.5 ug/ml 10217726
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 6.2 ug/ml 20218656
NPT319 Cell Line B16 Mus musculus IC50 = 2.9 ug/ml 22450129
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens IC50 = 8.22 ug/ml 25891102
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 97.85 % 25891102

  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 NPC248884 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 NPC31194
1.0 High Similarity NPC85079
0.9783 High Similarity NPC72699
0.9574 High Similarity NPC151782
0.9565 High Similarity NPC125122
0.9565 High Similarity NPC471276
0.9565 High Similarity NPC471275
0.9565 High Similarity NPC471280
0.9565 High Similarity NPC153538
0.9556 High Similarity NPC124183
0.9556 High Similarity NPC55063
0.9556 High Similarity NPC35141
0.9556 High Similarity NPC19834
0.9362 High Similarity NPC473913
0.9362 High Similarity NPC474642
0.9362 High Similarity NPC471281
0.9362 High Similarity NPC199286
0.9362 High Similarity NPC477727
0.9362 High Similarity NPC249670
0.9333 High Similarity NPC269074
0.9167 High Similarity NPC329608
0.9167 High Similarity NPC165447
0.9167 High Similarity NPC294278
0.9167 High Similarity NPC76198
0.9167 High Similarity NPC9273
0.9167 High Similarity NPC89824
0.9167 High Similarity NPC224148
0.9167 High Similarity NPC197272
0.9167 High Similarity NPC471959
0.9167 High Similarity NPC256656
0.9167 High Similarity NPC477723
0.9167 High Similarity NPC475477
0.9167 High Similarity NPC93639
0.9167 High Similarity NPC55383
0.9167 High Similarity NPC170776
0.9111 High Similarity NPC101616
0.9 High Similarity NPC256209
0.9 High Similarity NPC49059
0.898 High Similarity NPC142092
0.8776 High Similarity NPC71053
0.8776 High Similarity NPC59408
0.8723 High Similarity NPC180575
0.8667 High Similarity NPC304151
0.8627 High Similarity NPC110732
0.8627 High Similarity NPC48058
0.8627 High Similarity NPC473532
0.8571 High Similarity NPC328784
0.8571 High Similarity NPC291437
0.8491 Intermediate Similarity NPC193975
0.8462 Intermediate Similarity NPC473910
0.8462 Intermediate Similarity NPC477726
0.8462 Intermediate Similarity NPC473721
0.8462 Intermediate Similarity NPC474644
0.8462 Intermediate Similarity NPC475353
0.8462 Intermediate Similarity NPC474513
0.8462 Intermediate Similarity NPC473725
0.8462 Intermediate Similarity NPC477725
0.8462 Intermediate Similarity NPC473896
0.8462 Intermediate Similarity NPC473735
0.8462 Intermediate Similarity NPC471239
0.8462 Intermediate Similarity NPC146551
0.8462 Intermediate Similarity NPC470963
0.84 Intermediate Similarity NPC129263
0.8367 Intermediate Similarity NPC302310
0.8302 Intermediate Similarity NPC470964
0.8302 Intermediate Similarity NPC477661
0.8302 Intermediate Similarity NPC161838
0.8302 Intermediate Similarity NPC471960
0.8302 Intermediate Similarity NPC473865
0.8302 Intermediate Similarity NPC474643
0.8302 Intermediate Similarity NPC470967
0.8302 Intermediate Similarity NPC475384
0.8302 Intermediate Similarity NPC470966
0.8302 Intermediate Similarity NPC470969
0.8302 Intermediate Similarity NPC473847
0.8302 Intermediate Similarity NPC311648
0.8302 Intermediate Similarity NPC470968
0.8298 Intermediate Similarity NPC108195
0.8261 Intermediate Similarity NPC149668
0.8148 Intermediate Similarity NPC48968
0.8148 Intermediate Similarity NPC212730
0.8148 Intermediate Similarity NPC594
0.8148 Intermediate Similarity NPC265551
0.8148 Intermediate Similarity NPC470970
0.8113 Intermediate Similarity NPC152668
0.8077 Intermediate Similarity NPC34577
0.8077 Intermediate Similarity NPC61177
0.8039 Intermediate Similarity NPC474495
0.8039 Intermediate Similarity NPC473672
0.8036 Intermediate Similarity NPC471278
0.8 Intermediate Similarity NPC15934
0.7959 Intermediate Similarity NPC157096
0.7895 Intermediate Similarity NPC66460
0.7895 Intermediate Similarity NPC271282
0.7895 Intermediate Similarity NPC325929
0.7872 Intermediate Similarity NPC206906
0.7857 Intermediate Similarity NPC473652
0.7826 Intermediate Similarity NPC27444
0.7826 Intermediate Similarity NPC329762
0.7826 Intermediate Similarity NPC103236
0.7818 Intermediate Similarity NPC44542
0.7759 Intermediate Similarity NPC29697
0.7755 Intermediate Similarity NPC276825
0.7736 Intermediate Similarity NPC477724
0.7736 Intermediate Similarity NPC26102
0.7736 Intermediate Similarity NPC187361
0.7586 Intermediate Similarity NPC168407
0.7586 Intermediate Similarity NPC475984
0.7556 Intermediate Similarity NPC216416
0.75 Intermediate Similarity NPC472445
0.75 Intermediate Similarity NPC473768
0.75 Intermediate Similarity NPC475071
0.7458 Intermediate Similarity NPC470965
0.7407 Intermediate Similarity NPC474496
0.7407 Intermediate Similarity NPC284224
0.7358 Intermediate Similarity NPC29234
0.7347 Intermediate Similarity NPC116934
0.7333 Intermediate Similarity NPC226592
0.7333 Intermediate Similarity NPC470320
0.7333 Intermediate Similarity NPC213767
0.7308 Intermediate Similarity NPC475153
0.7292 Intermediate Similarity NPC269823
0.7241 Intermediate Similarity NPC222852
0.7234 Intermediate Similarity NPC255042
0.7234 Intermediate Similarity NPC182840
0.7234 Intermediate Similarity NPC29091
0.7234 Intermediate Similarity NPC103213
0.7222 Intermediate Similarity NPC35756
0.7222 Intermediate Similarity NPC473705
0.72 Intermediate Similarity NPC138935
0.7193 Intermediate Similarity NPC471277
0.7193 Intermediate Similarity NPC471279
0.717 Intermediate Similarity NPC474460
0.717 Intermediate Similarity NPC182102
0.717 Intermediate Similarity NPC26960
0.7143 Intermediate Similarity NPC317899
0.7143 Intermediate Similarity NPC256766
0.7143 Intermediate Similarity NPC213538
0.7143 Intermediate Similarity NPC46248
0.7143 Intermediate Similarity NPC249801
0.7111 Intermediate Similarity NPC58957
0.7091 Intermediate Similarity NPC217188
0.7069 Intermediate Similarity NPC181872
0.7059 Intermediate Similarity NPC474362
0.7059 Intermediate Similarity NPC474202
0.7059 Intermediate Similarity NPC160628
0.7059 Intermediate Similarity NPC76976
0.7059 Intermediate Similarity NPC140501
0.7 Intermediate Similarity NPC252978
0.6984 Remote Similarity NPC473752
0.6981 Remote Similarity NPC267110
0.6964 Remote Similarity NPC269615
0.6949 Remote Similarity NPC473866
0.6949 Remote Similarity NPC474267
0.6949 Remote Similarity NPC122239
0.6897 Remote Similarity NPC474577
0.6897 Remote Similarity NPC121034
0.6889 Remote Similarity NPC250734
0.6885 Remote Similarity NPC55068
0.6875 Remote Similarity NPC306850
0.6863 Remote Similarity NPC145755
0.6863 Remote Similarity NPC267514
0.6852 Remote Similarity NPC473487
0.6852 Remote Similarity NPC20934
0.6852 Remote Similarity NPC288381
0.6842 Remote Similarity NPC329686
0.6842 Remote Similarity NPC227135
0.6833 Remote Similarity NPC327112
0.68 Remote Similarity NPC31121
0.6786 Remote Similarity NPC475723
0.678 Remote Similarity NPC469373
0.678 Remote Similarity NPC226848
0.6727 Remote Similarity NPC244038
0.6724 Remote Similarity NPC324224
0.6724 Remote Similarity NPC55412
0.6724 Remote Similarity NPC249645
0.6724 Remote Similarity NPC472808
0.6721 Remote Similarity NPC477829
0.6667 Remote Similarity NPC136164
0.6667 Remote Similarity NPC300121
0.6667 Remote Similarity NPC308844
0.6667 Remote Similarity NPC255863
0.6667 Remote Similarity NPC329424
0.6667 Remote Similarity NPC189677
0.6667 Remote Similarity NPC245947
0.6667 Remote Similarity NPC40434
0.6667 Remote Similarity NPC475931
0.6667 Remote Similarity NPC34873
0.6607 Remote Similarity NPC106531
0.6596 Remote Similarity NPC79544
0.6557 Remote Similarity NPC130807
0.6557 Remote Similarity NPC471081
0.6552 Remote Similarity NPC232247
0.6552 Remote Similarity NPC251666
0.6552 Remote Similarity NPC474913
0.6538 Remote Similarity NPC474413
0.6538 Remote Similarity NPC473539
0.6522 Remote Similarity NPC81989
0.6522 Remote Similarity NPC62779
0.6508 Remote Similarity NPC300593

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC248884 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
0.7059 Intermediate Similarity NPD4265 Approved
0.6885 Remote Similarity NPD3210 Clinical (unspecified phase)
0.6833 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6724 Remote Similarity NPD4219 Approved
0.6271 Remote Similarity NPD4627 Clinical (unspecified phase)
0.623 Remote Similarity NPD585 Clinical (unspecified phase)
0.619 Remote Similarity NPD368 Approved
0.6176 Remote Similarity NPD3212 Clinical (unspecified phase)
0.6071 Remote Similarity NPD4220 Pre-registration
0.6 Remote Similarity NPD342 Phase 1
0.6 Remote Similarity NPD3197 Phase 1
0.597 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5844 Remote Similarity NPD5332 Approved
0.5844 Remote Similarity NPD5331 Approved
0.5833 Remote Similarity NPD8264 Approved
0.5818 Remote Similarity NPD39 Approved
0.5775 Remote Similarity NPD4732 Discontinued
0.5692 Remote Similarity NPD4194 Approved
0.5692 Remote Similarity NPD4193 Approved
0.5692 Remote Similarity NPD4191 Approved
0.5692 Remote Similarity NPD4192 Approved
0.569 Remote Similarity NPD2268 Discontinued
0.5667 Remote Similarity NPD3172 Approved
0.56 Remote Similarity NPD5784 Clinical (unspecified phase)
0.56 Remote Similarity NPD4271 Approved
0.56 Remote Similarity NPD7322 Clinical (unspecified phase)
0.56 Remote Similarity NPD4268 Approved

Structure

External Identifiers

PubChem CID   5281148
ChEMBL   CHEMBL69018
ZINC  

Physicochemical Properties

Molecular Weight:  260.18
ALogP:  0.2016
MLogP:  3.11
XLogP:  4.573
# Rotatable Bonds:  11
Polar Surface Area:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  0
# Heavy Atoms:  19

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
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