Structure

Physi-Chem Properties

Molecular Weight:  232.15
Volume:  251.998
LogP:  3.306
LogD:  2.403
LogS:  -4.408
# Rotatable Bonds:  0
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  3
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.364
Synthetic Accessibility Score:  4.519
Fsp3:  0.667
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.652
MDCK Permeability:  2.533647057134658e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.395
30% Bioavailability (F30%):  0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.053
Plasma Protein Binding (PPB):  91.55156707763672%
Volume Distribution (VD):  2.131
Pgp-substrate:  10.719828605651855%

ADMET: Metabolism

CYP1A2-inhibitor:  0.53
CYP1A2-substrate:  0.523
CYP2C19-inhibitor:  0.678
CYP2C19-substrate:  0.802
CYP2C9-inhibitor:  0.513
CYP2C9-substrate:  0.159
CYP2D6-inhibitor:  0.244
CYP2D6-substrate:  0.136
CYP3A4-inhibitor:  0.847
CYP3A4-substrate:  0.258

ADMET: Excretion

Clearance (CL):  4.62
Half-life (T1/2):  0.246

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.242
Drug-inuced Liver Injury (DILI):  0.517
AMES Toxicity:  0.364
Rat Oral Acute Toxicity:  0.803
Maximum Recommended Daily Dose:  0.876
Skin Sensitization:  0.402
Carcinogencity:  0.206
Eye Corrosion:  0.373
Eye Irritation:  0.279
Respiratory Toxicity:  0.972

Download Data

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

  Natural Product: NPC178676

Natural Product ID:  NPC178676
Common Name*:   Helenine
IUPAC Name:   (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one
Synonyms:   Alantolactone; Eupatal; Helenine
Standard InCHIKey:  PXOYOCNNSUAQNS-AGNJHWRGSA-N
Standard InCHI:  InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h7,9,11,13H,2,4-6,8H2,1,3H3/t9-,11+,13+,15+/m0/s1
SMILES:  C[C@H]1CCC[C@]2(C)C[C@@H]3[C@H](C=C12)C(=C)C(=O)O3
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL136356
PubChem CID:   72724
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001283] Terpene lactones
          • [CHEMONTID:0001543] Sesquiterpene lactones
            • [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2009.03.042]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.3136/fstr.15.499]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB10.140]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB2010.000-3252]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[10364842]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[12392098]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota Roots n.a. n.a. PMID[14510592]
NPO30603 Saussurea lappa n.a. n.a. n.a. n.a. root n.a. PMID[18409040]
NPO30603 Saussurea lappa n.a. n.a. n.a. roots n.a. n.a. PMID[18579374]
NPO22238 Inula falconeri Species Asteraceae Eukaryota aerial parts Tibet, China n.a. PMID[21924800]
NPO23861 Inula racemosa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23451797]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24996657]
NPO30603 Saussurea lappa n.a. n.a. n.a. n.a. n.a. n.a. PMID[25068579]
NPO26488 Tagetes patula Species Asteraceae Eukaryota n.a. flower n.a. PMID[25539472]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. root n.a. PMID[25767328]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28248102]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[3572418]
NPO30603 Saussurea lappa n.a. n.a. n.a. n.a. root n.a. PMID[8541643]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. root n.a. Database[Article]
NPO30603 Saussurea lappa n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO23861 Inula racemosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26488 Tagetes patula Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7750 Inula magnifica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3825 Kerria japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23861 Inula racemosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26488 Tagetes patula Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7750 Inula magnifica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3825 Kerria japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30379 Inula heienium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26488 Tagetes patula Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30115 Aucklandia lappa n.a. n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3825 Kerria japonica Species Rosaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18609 Inula grandis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7750 Inula magnifica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23861 Inula racemosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17755 Inula helenium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25825 Saussurea lappa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22238 Inula falconeri Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26488 Tagetes patula Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18609 Inula grandis Species Asteraceae 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
NPT111 Cell Line K562 Homo sapiens IC50 = 700.0 nM PMID[565978]
NPT111 Cell Line K562 Homo sapiens GI = 30.0 % PMID[565978]
NPT111 Cell Line K562 Homo sapiens S = 53.0 % PMID[565978]
NPT111 Cell Line K562 Homo sapiens G2/M = 17.0 % PMID[565978]
NPT111 Cell Line K562 Homo sapiens Activity = 9.9 % PMID[565978]
NPT111 Cell Line K562 Homo sapiens c.v = 3.4 n.a. PMID[565978]
NPT2716 Individual Protein UDP-N-acetylglucosamine 1-carboxyvinyltransferase Escherichia coli K-12 IC50 > 50000.0 nM PMID[565979]
NPT2717 Individual Protein UDP-N-acetylglucosamine 1-carboxyvinyltransferase Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) IC50 > 50000.0 nM PMID[565979]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 1170.0 nM PMID[565982]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Activity = 47.03 % PMID[565983]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Activity = 40.3 % PMID[565983]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 4655.86 nM PMID[565984]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 3006.08 nM PMID[565984]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 10023.05 nM PMID[565984]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 4943.11 nM PMID[565984]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 4954.5 nM PMID[565984]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 2426.61 nM PMID[565984]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 1981.53 nM PMID[565984]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 11994.99 nM PMID[565984]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 4797.33 nM PMID[565984]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 10568.18 nM PMID[565984]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 3953.67 nM PMID[565984]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 3019.95 nM PMID[565984]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 12387.97 nM PMID[565984]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 6886.52 nM PMID[565984]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 1621.81 nM PMID[565984]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 12302.69 nM PMID[565984]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 7744.62 nM PMID[565984]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 6194.41 nM PMID[565984]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 9862.79 nM PMID[565984]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 17538.81 nM PMID[565984]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 16519.62 nM PMID[565984]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 14223.29 nM PMID[565984]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 1191.24 nM PMID[565984]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 2773.32 nM PMID[565984]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 3828.25 nM PMID[565984]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 12022.64 nM PMID[565984]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 3176.87 nM PMID[565984]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 3076.1 nM PMID[565984]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 15848.93 nM PMID[565984]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 1761.98 nM PMID[565984]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 4487.45 nM PMID[565984]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 10519.62 nM PMID[565984]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 3622.43 nM PMID[565984]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 3235.94 nM PMID[565984]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 15667.51 nM PMID[565984]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 16106.46 nM PMID[565984]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 3459.39 nM PMID[565984]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 4295.36 nM PMID[565984]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 4446.31 nM PMID[565984]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 12589.25 nM PMID[565984]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 14996.85 nM PMID[565984]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 4581.42 nM PMID[565984]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 11641.26 nM PMID[565984]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 22029.26 nM PMID[565984]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 2642.41 nM PMID[565984]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 16982.44 nM PMID[565984]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 6456.54 nM PMID[565984]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 5333.35 nM PMID[565984]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 17458.22 nM PMID[565984]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 5081.59 nM PMID[565984]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 16106.46 nM PMID[565984]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 4988.84 nM PMID[565984]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 3531.83 nM PMID[565984]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 7211.07 nM PMID[565984]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 1524.05 nM PMID[565984]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 4285.49 nM PMID[565984]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 15703.63 nM PMID[565984]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 7998.34 nM PMID[565984]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 6123.5 nM PMID[565984]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 1725.84 nM PMID[565984]
NPT737 Cell Line HUVEC Homo sapiens IC50 = 2.4 ug.mL-1 PMID[565985]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 1.3 ug.mL-1 PMID[565985]
NPT453 Cell Line HT-1080 Homo sapiens IC50 = 0.696 ug.mL-1 PMID[565985]
NPT81 Cell Line A549 Homo sapiens IC50 = 0.55 ug.mL-1 PMID[565985]
NPT111 Cell Line K562 Homo sapiens IC50 = 700.0 nM PMID[565988]
NPT35 Others n.a. LogP = 3.38 n.a. PMID[565980]
NPT25088 PROTEIN FAMILY Janus Kinase (JAK) Homo sapiens Inhibition = 25.0 % PMID[565981]
NPT207 Protein Family MAP kinase p38 Homo sapiens Inhibition = 25.0 % PMID[565981]
NPT840 Individual Protein Transcriptional activator Myb Gallus gallus IC50 = 23659.2 nM PMID[565986]
NPT27 Others Unspecified IC50 > 30000.0 nM PMID[565986]
NPT840 Individual Protein Transcriptional activator Myb Gallus gallus IC50 = 23640.0 nM PMID[565986]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 115.99 % PMID[565987]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 115.17 % PMID[565987]
NPT25209 PROTEIN-PROTEIN INTERACTION Transforming growth factor beta-1 proprotein/Mothers against decapentaplegic homolog 3 Mus musculus Inhibition = -27.73 % PMID[565989]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.46 % PMID[565990]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 19.88 % PMID[565991]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.29 % PMID[565992]

☑ 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 NPC178676 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
0.962 High Similarity NPC110405
0.9221 High Similarity NPC35574
0.9157 High Similarity NPC73995
0.9125 High Similarity NPC22611
0.9048 High Similarity NPC152467
0.9048 High Similarity NPC158488
0.9036 High Similarity NPC215831
0.8987 High Similarity NPC195424
0.8941 High Similarity NPC186363
0.8941 High Similarity NPC233345
0.8846 High Similarity NPC187568
0.8846 High Similarity NPC41780
0.881 High Similarity NPC277771
0.881 High Similarity NPC226863
0.8765 High Similarity NPC226988
0.8765 High Similarity NPC186276
0.8659 High Similarity NPC470948
0.8642 High Similarity NPC475665
0.8642 High Similarity NPC38642
0.8636 High Similarity NPC183012
0.8621 High Similarity NPC475657
0.8605 High Similarity NPC469595
0.8605 High Similarity NPC220454
0.8605 High Similarity NPC212679
0.8588 High Similarity NPC477128
0.8554 High Similarity NPC30486
0.8523 High Similarity NPC477129
0.8523 High Similarity NPC477130
0.8506 High Similarity NPC49420
0.8488 Intermediate Similarity NPC168131
0.8481 Intermediate Similarity NPC235906
0.8481 Intermediate Similarity NPC41017
0.8452 Intermediate Similarity NPC177932
0.8452 Intermediate Similarity NPC189311
0.8434 Intermediate Similarity NPC193198
0.8434 Intermediate Similarity NPC194637
0.8375 Intermediate Similarity NPC470240
0.8375 Intermediate Similarity NPC476794
0.8375 Intermediate Similarity NPC65603
0.8354 Intermediate Similarity NPC138408
0.8354 Intermediate Similarity NPC193351
0.8354 Intermediate Similarity NPC226669
0.8354 Intermediate Similarity NPC155587
0.8353 Intermediate Similarity NPC6979
0.8352 Intermediate Similarity NPC216478
0.8333 Intermediate Similarity NPC219011
0.8333 Intermediate Similarity NPC159635
0.8333 Intermediate Similarity NPC470011
0.8333 Intermediate Similarity NPC307164
0.8333 Intermediate Similarity NPC139566
0.8315 Intermediate Similarity NPC470697
0.8315 Intermediate Similarity NPC250075
0.8313 Intermediate Similarity NPC200513
0.8295 Intermediate Similarity NPC65513
0.8276 Intermediate Similarity NPC288699
0.8276 Intermediate Similarity NPC50488
0.8276 Intermediate Similarity NPC474396
0.8256 Intermediate Similarity NPC305029
0.8256 Intermediate Similarity NPC181103
0.8256 Intermediate Similarity NPC175293
0.8242 Intermediate Similarity NPC474343
0.8235 Intermediate Similarity NPC52628
0.8214 Intermediate Similarity NPC215294
0.8205 Intermediate Similarity NPC163003
0.8202 Intermediate Similarity NPC166346
0.8182 Intermediate Similarity NPC469372
0.8171 Intermediate Similarity NPC470244
0.8171 Intermediate Similarity NPC150646
0.8171 Intermediate Similarity NPC617
0.8171 Intermediate Similarity NPC470239
0.8171 Intermediate Similarity NPC182550
0.8152 Intermediate Similarity NPC252295
0.8152 Intermediate Similarity NPC23364
0.8148 Intermediate Similarity NPC316500
0.814 Intermediate Similarity NPC250981
0.814 Intermediate Similarity NPC329692
0.814 Intermediate Similarity NPC477920
0.814 Intermediate Similarity NPC85698
0.814 Intermediate Similarity NPC9231
0.814 Intermediate Similarity NPC220478
0.8132 Intermediate Similarity NPC112654
0.8118 Intermediate Similarity NPC100391
0.8111 Intermediate Similarity NPC476596
0.8101 Intermediate Similarity NPC295633
0.8101 Intermediate Similarity NPC269206
0.8101 Intermediate Similarity NPC58956
0.809 Intermediate Similarity NPC72845
0.8072 Intermediate Similarity NPC276356
0.8072 Intermediate Similarity NPC302426
0.8068 Intermediate Similarity NPC116620
0.8068 Intermediate Similarity NPC5509
0.8065 Intermediate Similarity NPC470906
0.8065 Intermediate Similarity NPC470761
0.8065 Intermediate Similarity NPC476303
0.8065 Intermediate Similarity NPC473219
0.8049 Intermediate Similarity NPC471220
0.8046 Intermediate Similarity NPC470012
0.8046 Intermediate Similarity NPC312561
0.8025 Intermediate Similarity NPC40353
0.8025 Intermediate Similarity NPC92489
0.8023 Intermediate Similarity NPC161957
0.8023 Intermediate Similarity NPC106416
0.8023 Intermediate Similarity NPC21471
0.8023 Intermediate Similarity NPC33570
0.8023 Intermediate Similarity NPC65661
0.8023 Intermediate Similarity NPC476678
0.8023 Intermediate Similarity NPC86316
0.8 Intermediate Similarity NPC140287
0.8 Intermediate Similarity NPC115021
0.8 Intermediate Similarity NPC222358
0.8 Intermediate Similarity NPC139692
0.8 Intermediate Similarity NPC476598
0.8 Intermediate Similarity NPC476355
0.8 Intermediate Similarity NPC254202
0.8 Intermediate Similarity NPC476597
0.7978 Intermediate Similarity NPC475776
0.7976 Intermediate Similarity NPC25684
0.7976 Intermediate Similarity NPC282293
0.7976 Intermediate Similarity NPC141810
0.7976 Intermediate Similarity NPC281949
0.7976 Intermediate Similarity NPC301477
0.7955 Intermediate Similarity NPC136879
0.7955 Intermediate Similarity NPC477302
0.7952 Intermediate Similarity NPC264227
0.7952 Intermediate Similarity NPC63649
0.7952 Intermediate Similarity NPC472965
0.7949 Intermediate Similarity NPC199557
0.7931 Intermediate Similarity NPC264127
0.7927 Intermediate Similarity NPC189206
0.7912 Intermediate Similarity NPC474841
0.7912 Intermediate Similarity NPC471446
0.7912 Intermediate Similarity NPC473434
0.7912 Intermediate Similarity NPC38830
0.7912 Intermediate Similarity NPC57117
0.7907 Intermediate Similarity NPC149869
0.7907 Intermediate Similarity NPC96055
0.7907 Intermediate Similarity NPC475100
0.7895 Intermediate Similarity NPC31058
0.7895 Intermediate Similarity NPC273005
0.7895 Intermediate Similarity NPC469606
0.7895 Intermediate Similarity NPC58329
0.7889 Intermediate Similarity NPC473944
0.7889 Intermediate Similarity NPC303697
0.7889 Intermediate Similarity NPC472814
0.7889 Intermediate Similarity NPC177037
0.7882 Intermediate Similarity NPC471218
0.7872 Intermediate Similarity NPC476299
0.7872 Intermediate Similarity NPC474012
0.7865 Intermediate Similarity NPC218927
0.7865 Intermediate Similarity NPC206001
0.7865 Intermediate Similarity NPC284561
0.7857 Intermediate Similarity NPC268827
0.7857 Intermediate Similarity NPC74673
0.7857 Intermediate Similarity NPC69271
0.7849 Intermediate Similarity NPC84335
0.7849 Intermediate Similarity NPC257726
0.7849 Intermediate Similarity NPC38530
0.7849 Intermediate Similarity NPC204054
0.7841 Intermediate Similarity NPC167877
0.7831 Intermediate Similarity NPC184737
0.7831 Intermediate Similarity NPC472960
0.7826 Intermediate Similarity NPC33473
0.7816 Intermediate Similarity NPC470223
0.7816 Intermediate Similarity NPC323765
0.7812 Intermediate Similarity NPC476237
0.7812 Intermediate Similarity NPC176883
0.7805 Intermediate Similarity NPC473223
0.7805 Intermediate Similarity NPC27205
0.7805 Intermediate Similarity NPC123360
0.7802 Intermediate Similarity NPC229976
0.7802 Intermediate Similarity NPC474185
0.7791 Intermediate Similarity NPC272814
0.7791 Intermediate Similarity NPC118423
0.7791 Intermediate Similarity NPC39588
0.7791 Intermediate Similarity NPC474193
0.7791 Intermediate Similarity NPC12283
0.7778 Intermediate Similarity NPC101651
0.7778 Intermediate Similarity NPC159748
0.7778 Intermediate Similarity NPC281942
0.7778 Intermediate Similarity NPC8062
0.7778 Intermediate Similarity NPC471818
0.7778 Intermediate Similarity NPC232426
0.7778 Intermediate Similarity NPC51486
0.7766 Intermediate Similarity NPC176845
0.7765 Intermediate Similarity NPC35089
0.7765 Intermediate Similarity NPC10276
0.7765 Intermediate Similarity NPC47635
0.7765 Intermediate Similarity NPC473420
0.7765 Intermediate Similarity NPC14203
0.7765 Intermediate Similarity NPC149237
0.7765 Intermediate Similarity NPC229584
0.7755 Intermediate Similarity NPC110496
0.7753 Intermediate Similarity NPC474845
0.7753 Intermediate Similarity NPC472302
0.7753 Intermediate Similarity NPC24816
0.7753 Intermediate Similarity NPC473229
0.7753 Intermediate Similarity NPC97884
0.7753 Intermediate Similarity NPC28227
0.7753 Intermediate Similarity NPC472220
0.775 Intermediate Similarity NPC129665

  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 NPC178676 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
0.8452 Intermediate Similarity NPD1694 Approved
0.8313 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD5330 Approved
0.7727 Intermediate Similarity NPD6684 Approved
0.7727 Intermediate Similarity NPD6409 Approved
0.7727 Intermediate Similarity NPD7146 Approved
0.7727 Intermediate Similarity NPD7521 Approved
0.7727 Intermediate Similarity NPD7334 Approved
0.7609 Intermediate Similarity NPD6399 Phase 3
0.7579 Intermediate Similarity NPD4225 Approved
0.7556 Intermediate Similarity NPD6903 Approved
0.7556 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD8039 Approved
0.7416 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD6672 Approved
0.7363 Intermediate Similarity NPD5737 Approved
0.734 Intermediate Similarity NPD7900 Approved
0.734 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7312 Intermediate Similarity NPD5693 Phase 1
0.7283 Intermediate Similarity NPD1695 Approved
0.7273 Intermediate Similarity NPD3667 Approved
0.7263 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD3573 Approved
0.7204 Intermediate Similarity NPD5207 Approved
0.7158 Intermediate Similarity NPD7748 Approved
0.7143 Intermediate Similarity NPD3618 Phase 1
0.7129 Intermediate Similarity NPD6008 Approved
0.7113 Intermediate Similarity NPD7902 Approved
0.7111 Intermediate Similarity NPD3668 Phase 3
0.7111 Intermediate Similarity NPD4786 Approved
0.7083 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD7638 Approved
0.6989 Remote Similarity NPD5208 Approved
0.6979 Remote Similarity NPD6001 Approved
0.697 Remote Similarity NPD7639 Approved
0.697 Remote Similarity NPD7640 Approved
0.6957 Remote Similarity NPD6098 Approved
0.6947 Remote Similarity NPD7515 Phase 2
0.6944 Remote Similarity NPD7115 Discovery
0.6923 Remote Similarity NPD3133 Approved
0.6923 Remote Similarity NPD3666 Approved
0.6923 Remote Similarity NPD3665 Phase 1
0.6915 Remote Similarity NPD6673 Approved
0.6915 Remote Similarity NPD6051 Approved
0.6915 Remote Similarity NPD6904 Approved
0.6915 Remote Similarity NPD6080 Approved
0.6907 Remote Similarity NPD5695 Phase 3
0.6869 Remote Similarity NPD5696 Approved
0.6854 Remote Similarity NPD4695 Discontinued
0.6842 Remote Similarity NPD5785 Approved
0.6842 Remote Similarity NPD5692 Phase 3
0.6827 Remote Similarity NPD6686 Approved
0.6774 Remote Similarity NPD5279 Phase 3
0.6771 Remote Similarity NPD6079 Approved
0.6771 Remote Similarity NPD6050 Approved
0.6771 Remote Similarity NPD6411 Approved
0.6771 Remote Similarity NPD5694 Approved
0.6768 Remote Similarity NPD6084 Phase 2
0.6768 Remote Similarity NPD6083 Phase 2
0.6737 Remote Similarity NPD5328 Approved
0.6731 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6731 Remote Similarity NPD5697 Approved
0.6703 Remote Similarity NPD5209 Approved
0.6667 Remote Similarity NPD6011 Approved
0.6667 Remote Similarity NPD6881 Approved
0.6667 Remote Similarity NPD6899 Approved
0.6636 Remote Similarity NPD6649 Approved
0.6636 Remote Similarity NPD6650 Approved
0.6635 Remote Similarity NPD6402 Approved
0.6635 Remote Similarity NPD7128 Approved
0.6635 Remote Similarity NPD5739 Approved
0.6635 Remote Similarity NPD6675 Approved
0.6604 Remote Similarity NPD6014 Approved
0.6604 Remote Similarity NPD6372 Approved
0.6604 Remote Similarity NPD6013 Approved
0.6604 Remote Similarity NPD6373 Approved
0.6604 Remote Similarity NPD6012 Approved
0.6598 Remote Similarity NPD5281 Approved
0.6598 Remote Similarity NPD5284 Approved
0.6598 Remote Similarity NPD8034 Phase 2
0.6598 Remote Similarity NPD8035 Phase 2
0.6588 Remote Similarity NPD4691 Approved
0.6585 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6571 Remote Similarity NPD5701 Approved
0.6562 Remote Similarity NPD6101 Approved
0.6562 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6559 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6542 Remote Similarity NPD6883 Approved
0.6542 Remote Similarity NPD7102 Approved
0.6542 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6542 Remote Similarity NPD7290 Approved
0.6531 Remote Similarity NPD4202 Approved
0.6531 Remote Similarity NPD5778 Approved
0.6531 Remote Similarity NPD5779 Approved
0.6522 Remote Similarity NPD4221 Approved
0.6522 Remote Similarity NPD4223 Phase 3
0.6509 Remote Similarity NPD7320 Approved
0.65 Remote Similarity NPD5349 Clinical (unspecified phase)
0.65 Remote Similarity NPD5220 Clinical (unspecified phase)
0.65 Remote Similarity NPD5222 Approved
0.65 Remote Similarity NPD5221 Approved
0.65 Remote Similarity NPD4697 Phase 3
0.6495 Remote Similarity NPD46 Approved
0.6495 Remote Similarity NPD6698 Approved
0.6489 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6481 Remote Similarity NPD6617 Approved
0.6481 Remote Similarity NPD8130 Phase 1
0.6481 Remote Similarity NPD6847 Approved
0.6481 Remote Similarity NPD6869 Approved
0.6471 Remote Similarity NPD4137 Phase 3
0.6463 Remote Similarity NPD5325 Clinical (unspecified phase)
0.6452 Remote Similarity NPD7154 Phase 3
0.6449 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6442 Remote Similarity NPD6052 Approved
0.6436 Remote Similarity NPD5173 Approved
0.6422 Remote Similarity NPD8297 Approved
0.6422 Remote Similarity NPD6882 Approved
0.6421 Remote Similarity NPD4519 Discontinued
0.6421 Remote Similarity NPD5690 Phase 2
0.6421 Remote Similarity NPD4623 Approved
0.6421 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6404 Remote Similarity NPD3701 Clinical (unspecified phase)
0.64 Remote Similarity NPD5210 Approved
0.64 Remote Similarity NPD4629 Approved
0.64 Remote Similarity NPD5654 Approved
0.6395 Remote Similarity NPD4747 Approved
0.6392 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6392 Remote Similarity NPD4753 Phase 2
0.6383 Remote Similarity NPD4197 Approved
0.6364 Remote Similarity NPD4058 Approved
0.6346 Remote Similarity NPD5211 Phase 2
0.6346 Remote Similarity NPD7632 Discontinued
0.6337 Remote Similarity NPD7732 Phase 3
0.633 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6322 Remote Similarity NPD5276 Approved
0.6316 Remote Similarity NPD5363 Approved
0.6316 Remote Similarity NPD5329 Approved
0.6311 Remote Similarity NPD5286 Approved
0.6311 Remote Similarity NPD4696 Approved
0.6311 Remote Similarity NPD5285 Approved
0.63 Remote Similarity NPD5282 Discontinued
0.6292 Remote Similarity NPD7339 Approved
0.6292 Remote Similarity NPD6942 Approved
0.6277 Remote Similarity NPD5362 Discontinued
0.6275 Remote Similarity NPD4755 Approved
0.6275 Remote Similarity NPD5959 Approved
0.6273 Remote Similarity NPD6053 Discontinued
0.6264 Remote Similarity NPD3617 Approved
0.6264 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6263 Remote Similarity NPD7637 Suspended
0.6262 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6262 Remote Similarity NPD6614 Approved
0.6261 Remote Similarity NPD6291 Clinical (unspecified phase)
0.625 Remote Similarity NPD4138 Approved
0.625 Remote Similarity NPD5205 Approved
0.625 Remote Similarity NPD4688 Approved
0.625 Remote Similarity NPD6422 Discontinued
0.625 Remote Similarity NPD4690 Approved
0.625 Remote Similarity NPD6274 Approved
0.625 Remote Similarity NPD5280 Approved
0.625 Remote Similarity NPD4693 Phase 3
0.625 Remote Similarity NPD6868 Approved
0.625 Remote Similarity NPD4694 Approved
0.625 Remote Similarity NPD4689 Approved
0.625 Remote Similarity NPD5223 Approved
0.6239 Remote Similarity NPD6371 Approved
0.6237 Remote Similarity NPD5369 Approved
0.6226 Remote Similarity NPD5141 Approved
0.6216 Remote Similarity NPD4632 Approved
0.6195 Remote Similarity NPD6317 Approved
0.619 Remote Similarity NPD5224 Approved
0.619 Remote Similarity NPD5225 Approved
0.619 Remote Similarity NPD4633 Approved
0.619 Remote Similarity NPD5226 Approved
0.6182 Remote Similarity NPD2181 Clinical (unspecified phase)
0.618 Remote Similarity NPD5733 Approved
0.618 Remote Similarity NPD4687 Approved
0.617 Remote Similarity NPD4269 Approved
0.617 Remote Similarity NPD4270 Approved
0.6163 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4700 Approved
0.6154 Remote Similarity NPD6404 Discontinued
0.6146 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6146 Remote Similarity NPD1696 Phase 3
0.614 Remote Similarity NPD6313 Approved
0.614 Remote Similarity NPD6335 Approved
0.614 Remote Similarity NPD6314 Approved
0.6136 Remote Similarity NPD5777 Approved
0.6132 Remote Similarity NPD5175 Approved
0.6132 Remote Similarity NPD5174 Approved
0.6129 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6111 Remote Similarity NPD6412 Phase 2
0.6105 Remote Similarity NPD4788 Approved
0.6087 Remote Similarity NPD7101 Approved
0.6087 Remote Similarity NPD7100 Approved
0.6082 Remote Similarity NPD5786 Approved
0.6071 Remote Similarity NPD6858 Approved
0.6071 Remote Similarity NPD7094 Approved
0.6058 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6053 Remote Similarity NPD6009 Approved

  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