Structure

Physi-Chem Properties

Molecular Weight:  184.15
Volume:  211.12
LogP:  3.834
LogD:  2.222
LogS:  -3.135
# Rotatable Bonds:  9
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.44
Synthetic Accessibility Score:  1.907
Fsp3:  0.727
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.058
MDCK Permeability:  2.883379602280911e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.694
30% Bioavailability (F30%):  0.47

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.397
Plasma Protein Binding (PPB):  94.39244842529297%
Volume Distribution (VD):  0.263
Pgp-substrate:  3.295198917388916%

ADMET: Metabolism

CYP1A2-inhibitor:  0.068
CYP1A2-substrate:  0.331
CYP2C19-inhibitor:  0.024
CYP2C19-substrate:  0.375
CYP2C9-inhibitor:  0.069
CYP2C9-substrate:  0.975
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.32
CYP3A4-inhibitor:  0.025
CYP3A4-substrate:  0.041

ADMET: Excretion

Clearance (CL):  2.475
Half-life (T1/2):  0.8

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.068
Drug-inuced Liver Injury (DILI):  0.016
AMES Toxicity:  0.01
Rat Oral Acute Toxicity:  0.155
Maximum Recommended Daily Dose:  0.025
Skin Sensitization:  0.894
Carcinogencity:  0.147
Eye Corrosion:  0.982
Eye Irritation:  0.989
Respiratory Toxicity:  0.729

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC180534

Natural Product ID:  NPC180534
Common Name*:   Undecylenic Acid
IUPAC Name:   undec-10-enoic acid
Synonyms:   Undecylenic Acid
Standard InCHIKey:  FRPZMMHWLSIFAZ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H20O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2H,1,3-10H2,(H,12,13)
SMILES:  C=CCCCCCCCCC(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1276010
PubChem CID:   5634
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000262] Fatty acids and conjugates
          • [CHEMONTID:0003086] Medium-chain fatty acids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO7019 Hypericum sampsonii Species Hypericaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.phytochem.2004.08.014]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. DOI[10.5012/bkcs.2003.24.11.1699]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[12510838]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[15646793]
NPO7019 Hypericum sampsonii Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[18038963]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[21625478]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. root n.a. PMID[21657081]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[26048790]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[27444348]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota Roots n.a. n.a. PMID[31464439]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7019 Hypericum sampsonii Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7019 Hypericum sampsonii Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3807 Morinda lucida Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8920 Balanocarpus heimii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO8451 Chilo sacchariphagus Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7019 Hypericum sampsonii Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12283 Macrothelypteris torresiana Species Thelypteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3523 Botryllus tyreus Species Styelidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO565 Poria obliqua Species Coccinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16249 Dendrobium bicameratum Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24758 Angelica dahurica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 0.8 nM PMID[511317]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 39810.7 nM PMID[511317]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 149279.44 nM PMID[511318]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 122179.97 nM PMID[511318]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 80723.5 nM PMID[511318]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100693.17 nM PMID[511318]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 83176.38 nM PMID[511318]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 109647.82 nM PMID[511318]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 93756.2 nM PMID[511318]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 141905.75 nM PMID[511318]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 152054.75 nM PMID[511318]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 797.99 nM PMID[511318]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 66988.46 nM PMID[511318]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 109647.82 nM PMID[511318]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 171790.84 nM PMID[511318]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 105196.19 nM PMID[511318]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 120503.59 nM PMID[511318]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 112201.85 nM PMID[511318]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 145211.16 nM PMID[511318]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 127057.41 nM PMID[511318]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 149968.48 nM PMID[511318]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 148593.56 nM PMID[511318]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 124738.35 nM PMID[511318]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 105196.19 nM PMID[511318]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 27733.2 nM PMID[511318]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 17139.57 nM PMID[511318]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 21379.62 nM PMID[511318]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 128528.67 nM PMID[511318]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 131522.48 nM PMID[511318]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 101624.87 nM PMID[511318]
NPT168 Cell Line P388 Mus musculus GI50 n.a. 80352.61 nM PMID[511318]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 85310.01 nM PMID[511318]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 114287.83 nM PMID[511318]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 108143.4 nM PMID[511318]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 103038.61 nM PMID[511318]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 167880.4 nM PMID[511318]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 109900.58 nM PMID[511318]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 76559.66 nM PMID[511318]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 115611.22 nM PMID[511318]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 90991.33 nM PMID[511318]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 152054.75 nM PMID[511318]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 135207.26 nM PMID[511318]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 137720.95 nM PMID[511318]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 94188.96 nM PMID[511318]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 79799.47 nM PMID[511318]
NPT552 Cell Line P388/ADR Mus musculus GI50 n.a. 72276.98 nM PMID[511318]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 106169.56 nM PMID[511318]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 113240.04 nM PMID[511318]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 109144.03 nM PMID[511318]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 105681.75 nM PMID[511318]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 179060.59 nM PMID[511318]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 127643.88 nM PMID[511318]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 76207.9 nM PMID[511318]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 118032.06 nM PMID[511318]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 154881.66 nM PMID[511318]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 134896.29 nM PMID[511318]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 41304.75 nM PMID[511318]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 93110.79 nM PMID[511318]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 125025.9 nM PMID[511318]
NPT738 Cell Line SN12K1 Homo sapiens GI50 n.a. 92044.96 nM PMID[511318]
NPT612 Individual Protein Canalicular multispecific organic anion transporter 1 Homo sapiens IC50 > 133000.0 nM PMID[511320]
NPT1249 Individual Protein Canalicular multispecific organic anion transporter 2 Homo sapiens IC50 > 133000.0 nM PMID[511320]
NPT1028 Individual Protein Multidrug resistance-associated protein 4 Homo sapiens IC50 = 63900.0 nM PMID[511320]
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT20 Organism Candida albicans Candida albicans IC50 > 542700.0 nM PMID[511316]
NPT187 Organism Issatchenkia orientalis Pichia kudriavzevii IC50 > 542700.0 nM PMID[511316]
NPT188 Organism Candida parapsilosis Candida parapsilosis IC50 > 542700.0 nM PMID[511316]
NPT186 Organism Candida tropicalis Candida tropicalis IC50 > 542700.0 nM PMID[511316]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 = 25300.0 nM PMID[511316]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 271300.0 nM PMID[511316]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MFC = 542.7 uM PMID[511316]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 = 2700.0 nM PMID[511316]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MIC = 135700.0 nM PMID[511316]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans MFC = 271.3 uM PMID[511316]
NPT21 Organism Aspergillus niger Aspergillus niger IC50 = 414900.0 nM PMID[511316]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes IC50 = 378900.0 nM PMID[511316]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MIC = 542700.0 nM PMID[511316]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes IC50 = 279000.0 nM PMID[511316]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum IC50 = 111300.0 nM PMID[511316]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum MIC = 542700.0 nM PMID[511316]
NPT329 Organism Trichophyton rubrum Trichophyton rubrum IC50 = 270000.0 nM PMID[511316]
NPT2 Others Unspecified AC50 n.a. 17782.8 nM PMID[511319]
NPT2 Others Unspecified Ac50 n.a. 0.631 uM PMID[511319]
NPT2 Others Unspecified Ac50 n.a. 17.78 uM PMID[511319]
NPT2 Others Unspecified AC50 n.a. 631.0 nM PMID[511319]
NPT713 Individual Protein Bile salt export pump Homo sapiens IC50 > 133000.0 nM PMID[511320]
NPT2 Others Unspecified Potency n.a. 4252.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 33488.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76958.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 29847 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54482.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 24336.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 6007 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 43641.2 nM PubChem BioAssay data set

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC180534 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
0.9167 High Similarity NPC18357
0.9167 High Similarity NPC281245
0.898 High Similarity NPC139029
0.898 High Similarity NPC294548
0.898 High Similarity NPC36061
0.898 High Similarity NPC1813
0.88 High Similarity NPC87564
0.88 High Similarity NPC85813
0.88 High Similarity NPC25417
0.88 High Similarity NPC6095
0.88 High Similarity NPC281972
0.88 High Similarity NPC424
0.88 High Similarity NPC261831
0.88 High Similarity NPC88966
0.88 High Similarity NPC32467
0.88 High Similarity NPC154245
0.88 High Similarity NPC290563
0.8723 High Similarity NPC216130
0.8627 High Similarity NPC54766
0.86 High Similarity NPC70387
0.86 High Similarity NPC321062
0.8571 High Similarity NPC470410
0.8571 High Similarity NPC470412
0.8462 Intermediate Similarity NPC187777
0.8462 Intermediate Similarity NPC18951
0.8462 Intermediate Similarity NPC477201
0.8462 Intermediate Similarity NPC179764
0.84 Intermediate Similarity NPC92114
0.8367 Intermediate Similarity NPC224227
0.8333 Intermediate Similarity NPC207292
0.8302 Intermediate Similarity NPC225929
0.8269 Intermediate Similarity NPC274290
0.8269 Intermediate Similarity NPC473863
0.82 Intermediate Similarity NPC262968
0.8163 Intermediate Similarity NPC5413
0.8163 Intermediate Similarity NPC149821
0.8148 Intermediate Similarity NPC34416
0.8039 Intermediate Similarity NPC161366
0.8 Intermediate Similarity NPC59051
0.8 Intermediate Similarity NPC274927
0.8 Intermediate Similarity NPC106851
0.7885 Intermediate Similarity NPC139545
0.7885 Intermediate Similarity NPC39633
0.7885 Intermediate Similarity NPC309606
0.7885 Intermediate Similarity NPC71761
0.7857 Intermediate Similarity NPC243532
0.7857 Intermediate Similarity NPC174447
0.7857 Intermediate Similarity NPC122521
0.7857 Intermediate Similarity NPC251042
0.7857 Intermediate Similarity NPC235242
0.7843 Intermediate Similarity NPC28205
0.7818 Intermediate Similarity NPC267817
0.7778 Intermediate Similarity NPC301585
0.7778 Intermediate Similarity NPC183424
0.7778 Intermediate Similarity NPC261080
0.7778 Intermediate Similarity NPC201844
0.7778 Intermediate Similarity NPC294085
0.7778 Intermediate Similarity NPC113928
0.7778 Intermediate Similarity NPC279026
0.7778 Intermediate Similarity NPC214610
0.7778 Intermediate Similarity NPC14227
0.7778 Intermediate Similarity NPC118968
0.7778 Intermediate Similarity NPC301696
0.7778 Intermediate Similarity NPC154186
0.7719 Intermediate Similarity NPC174560
0.7719 Intermediate Similarity NPC125312
0.7719 Intermediate Similarity NPC40082
0.7719 Intermediate Similarity NPC201939
0.76 Intermediate Similarity NPC91495
0.7593 Intermediate Similarity NPC28779
0.7593 Intermediate Similarity NPC228473
0.7593 Intermediate Similarity NPC223677
0.7593 Intermediate Similarity NPC200845
0.7593 Intermediate Similarity NPC128061
0.7593 Intermediate Similarity NPC10316
0.7593 Intermediate Similarity NPC52264
0.7556 Intermediate Similarity NPC268826
0.7551 Intermediate Similarity NPC117572
0.75 Intermediate Similarity NPC284212
0.7458 Intermediate Similarity NPC470320
0.7458 Intermediate Similarity NPC328089
0.7458 Intermediate Similarity NPC68343
0.7447 Intermediate Similarity NPC307783
0.7447 Intermediate Similarity NPC216630
0.7447 Intermediate Similarity NPC196924
0.7447 Intermediate Similarity NPC209970
0.7447 Intermediate Similarity NPC171736
0.7447 Intermediate Similarity NPC149184
0.7407 Intermediate Similarity NPC137538
0.7407 Intermediate Similarity NPC87394
0.7333 Intermediate Similarity NPC318420
0.7333 Intermediate Similarity NPC245947
0.7333 Intermediate Similarity NPC326268
0.7333 Intermediate Similarity NPC136164
0.7333 Intermediate Similarity NPC255863
0.7292 Intermediate Similarity NPC67462
0.7273 Intermediate Similarity NPC45626
0.717 Intermediate Similarity NPC48162
0.717 Intermediate Similarity NPC470411
0.7167 Intermediate Similarity NPC234767
0.7167 Intermediate Similarity NPC226592
0.7143 Intermediate Similarity NPC325977
0.7143 Intermediate Similarity NPC19305
0.7143 Intermediate Similarity NPC74845
0.7143 Intermediate Similarity NPC255837
0.7119 Intermediate Similarity NPC328776
0.7119 Intermediate Similarity NPC477829
0.7119 Intermediate Similarity NPC321838
0.7119 Intermediate Similarity NPC320305
0.7115 Intermediate Similarity NPC250919
0.7111 Intermediate Similarity NPC155263
0.7111 Intermediate Similarity NPC134782
0.7097 Intermediate Similarity NPC26500
0.7097 Intermediate Similarity NPC330426
0.7097 Intermediate Similarity NPC271921
0.7097 Intermediate Similarity NPC148192
0.7097 Intermediate Similarity NPC60120
0.7097 Intermediate Similarity NPC22101
0.7097 Intermediate Similarity NPC104537
0.7097 Intermediate Similarity NPC127091
0.7097 Intermediate Similarity NPC99619
0.7059 Intermediate Similarity NPC42304
0.7037 Intermediate Similarity NPC310746
0.7037 Intermediate Similarity NPC129458
0.7 Intermediate Similarity NPC55023
0.7 Intermediate Similarity NPC8219
0.6984 Remote Similarity NPC141481
0.6984 Remote Similarity NPC53302
0.6984 Remote Similarity NPC48218
0.6984 Remote Similarity NPC473559
0.6984 Remote Similarity NPC476614
0.6984 Remote Similarity NPC324981
0.6949 Remote Similarity NPC229252
0.6949 Remote Similarity NPC143857
0.6949 Remote Similarity NPC45097
0.6909 Remote Similarity NPC10081
0.6909 Remote Similarity NPC225066
0.6897 Remote Similarity NPC329819
0.6889 Remote Similarity NPC156630
0.6885 Remote Similarity NPC53642
0.6885 Remote Similarity NPC470325
0.6875 Remote Similarity NPC143396
0.6875 Remote Similarity NPC317583
0.6875 Remote Similarity NPC48930
0.6863 Remote Similarity NPC30195
0.6863 Remote Similarity NPC314679
0.6863 Remote Similarity NPC12438
0.6825 Remote Similarity NPC475443
0.6825 Remote Similarity NPC473829
0.6809 Remote Similarity NPC305660
0.6809 Remote Similarity NPC54980
0.6809 Remote Similarity NPC201622
0.6809 Remote Similarity NPC22903
0.68 Remote Similarity NPC270796
0.6792 Remote Similarity NPC207815
0.6792 Remote Similarity NPC163345
0.6786 Remote Similarity NPC322461
0.678 Remote Similarity NPC329550
0.6769 Remote Similarity NPC476660
0.6769 Remote Similarity NPC42526
0.6735 Remote Similarity NPC163746
0.6735 Remote Similarity NPC103286
0.6731 Remote Similarity NPC21844
0.6731 Remote Similarity NPC324004
0.6731 Remote Similarity NPC328497
0.6727 Remote Similarity NPC303765
0.6721 Remote Similarity NPC54925
0.6721 Remote Similarity NPC477707
0.6667 Remote Similarity NPC320119
0.6667 Remote Similarity NPC327112
0.6667 Remote Similarity NPC223249
0.6667 Remote Similarity NPC142423
0.6667 Remote Similarity NPC472328
0.6667 Remote Similarity NPC219536
0.6667 Remote Similarity NPC328311
0.6667 Remote Similarity NPC288667
0.6667 Remote Similarity NPC31551
0.6667 Remote Similarity NPC308294
0.6615 Remote Similarity NPC473772
0.6604 Remote Similarity NPC131770
0.6604 Remote Similarity NPC106872
0.6604 Remote Similarity NPC324793
0.6604 Remote Similarity NPC477878
0.6604 Remote Similarity NPC200618
0.66 Remote Similarity NPC71317
0.66 Remote Similarity NPC129972
0.66 Remote Similarity NPC301528
0.6567 Remote Similarity NPC326024
0.6562 Remote Similarity NPC472875
0.6557 Remote Similarity NPC113293
0.6552 Remote Similarity NPC327388
0.6545 Remote Similarity NPC178586
0.6545 Remote Similarity NPC477458
0.6538 Remote Similarity NPC166287
0.6538 Remote Similarity NPC172042
0.6531 Remote Similarity NPC40597
0.6531 Remote Similarity NPC28598
0.6531 Remote Similarity NPC149299
0.6531 Remote Similarity NPC256163
0.6531 Remote Similarity NPC165533

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC180534 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
1.0 High Similarity NPD622 Approved
0.898 High Similarity NPD3172 Approved
0.88 High Similarity NPD4266 Approved
0.88 High Similarity NPD3195 Phase 2
0.88 High Similarity NPD3196 Approved
0.88 High Similarity NPD3194 Approved
0.82 Intermediate Similarity NPD29 Approved
0.82 Intermediate Similarity NPD28 Approved
0.8163 Intermediate Similarity NPD3173 Approved
0.7778 Intermediate Similarity NPD9448 Phase 2
0.7778 Intermediate Similarity NPD9655 Approved
0.7778 Intermediate Similarity NPD633 Phase 3
0.7551 Intermediate Similarity NPD3174 Discontinued
0.7551 Intermediate Similarity NPD4222 Approved
0.7458 Intermediate Similarity NPD3197 Phase 1
0.7447 Intermediate Similarity NPD2270 Approved
0.72 Intermediate Similarity NPD39 Approved
0.7 Intermediate Similarity NPD3199 Clinical (unspecified phase)
0.6863 Remote Similarity NPD634 Phase 3
0.6809 Remote Similarity NPD3206 Approved
0.68 Remote Similarity NPD5326 Phase 3
0.6667 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6538 Remote Similarity NPD9430 Approved
0.6538 Remote Similarity NPD9431 Approved
0.6296 Remote Similarity NPD5343 Approved
0.6275 Remote Similarity NPD387 Clinical (unspecified phase)
0.619 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6154 Remote Similarity NPD7331 Phase 2
0.614 Remote Similarity NPD3186 Phase 1
0.6122 Remote Similarity NPD9513 Phase 1
0.6111 Remote Similarity NPD3732 Approved
0.6061 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6038 Remote Similarity NPD2699 Approved
0.6 Remote Similarity NPD77 Approved
0.6 Remote Similarity NPD9450 Approved
0.5972 Remote Similarity NPD4756 Discovery
0.5946 Remote Similarity NPD5368 Approved
0.5932 Remote Similarity NPD615 Clinical (unspecified phase)
0.5932 Remote Similarity NPD3730 Approved
0.5932 Remote Similarity NPD3729 Clinical (unspecified phase)
0.5932 Remote Similarity NPD3728 Approved
0.5932 Remote Similarity NPD8971 Approved
0.589 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5867 Remote Similarity NPD5369 Approved
0.5806 Remote Similarity NPD6109 Phase 1
0.5789 Remote Similarity NPD4270 Approved
0.5789 Remote Similarity NPD6435 Approved
0.5789 Remote Similarity NPD4269 Approved
0.5741 Remote Similarity NPD6097 Approved
0.5741 Remote Similarity NPD6096 Approved
0.5733 Remote Similarity NPD4252 Approved
0.5714 Remote Similarity NPD7154 Phase 3
0.5714 Remote Similarity NPD5362 Discontinued
0.5694 Remote Similarity NPD8039 Approved
0.569 Remote Similarity NPD9638 Phase 2
0.5676 Remote Similarity NPD4271 Approved
0.5676 Remote Similarity NPD4268 Approved
0.5672 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5658 Remote Similarity NPD857 Phase 3
0.5658 Remote Similarity NPD226 Approved
0.56 Remote Similarity NPD9449 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data