Structure

Physi-Chem Properties

Molecular Weight:  410.14
Volume:  404.022
LogP:  3.655
LogD:  3.315
LogS:  -4.888
# Rotatable Bonds:  3
TPSA:  83.45
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.779
Synthetic Accessibility Score:  4.023
Fsp3:  0.348
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.941
MDCK Permeability:  1.898057416838128e-05
Pgp-inhibitor:  0.565
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.33
Plasma Protein Binding (PPB):  90.4393310546875%
Volume Distribution (VD):  0.958
Pgp-substrate:  10.348280906677246%

ADMET: Metabolism

CYP1A2-inhibitor:  0.095
CYP1A2-substrate:  0.893
CYP2C19-inhibitor:  0.801
CYP2C19-substrate:  0.822
CYP2C9-inhibitor:  0.792
CYP2C9-substrate:  0.775
CYP2D6-inhibitor:  0.063
CYP2D6-substrate:  0.89
CYP3A4-inhibitor:  0.755
CYP3A4-substrate:  0.855

ADMET: Excretion

Clearance (CL):  5.953
Half-life (T1/2):  0.248

ADMET: Toxicity

hERG Blockers:  0.079
Human Hepatotoxicity (H-HT):  0.684
Drug-inuced Liver Injury (DILI):  0.849
AMES Toxicity:  0.594
Rat Oral Acute Toxicity:  0.59
Maximum Recommended Daily Dose:  0.932
Skin Sensitization:  0.492
Carcinogencity:  0.576
Eye Corrosion:  0.003
Eye Irritation:  0.051
Respiratory Toxicity:  0.749

Download Data

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

  Natural Product: NPC152477

Natural Product ID:  NPC152477
Common Name*:   Rotenolone
IUPAC Name:   n.a.
Synonyms:   12A-Hydroxyrotenone; Rotenolone
Standard InCHIKey:  JFVKWCYZKMUTLH-AYPBNUJASA-N
Standard InCHI:  InChI=1S/C23H22O7/c1-11(2)16-7-13-15(29-16)6-5-12-21(13)30-20-10-28-17-9-19(27-4)18(26-3)8-14(17)23(20,25)22(12)24/h5-6,8-9,16,20,25H,1,7,10H2,2-4H3/t16-,20-,23-/m1/s1
SMILES:  COc1cc2c(cc1OC)OC[C@@H]1[C@@]2(O)C(=O)c2c(O1)c1C[C@@H](Oc1cc2)C(=C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL240545
PubChem CID:   68184
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0001607] Rotenoids
          • [CHEMONTID:0003528] Rotenones

*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
NPO32669 derris malaccensis plain Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11975515]
NPO10386 Mundulea chapelieri Species Fabaceae Eukaryota n.a. leaf n.a. PMID[15043430]
NPO10386 Mundulea chapelieri Species Fabaceae Eukaryota n.a. flower n.a. PMID[15043430]
NPO10386 Mundulea chapelieri Species Fabaceae Eukaryota bark an elevation of 850 m (171725? S; 484030? E), Toamasina, Madagascar 2002-JAN PMID[15043430]
NPO10386 Mundulea chapelieri Species Fabaceae Eukaryota n.a. bark n.a. PMID[15043430]
NPO26058 Erycibe expansa Species Convolvulaceae Eukaryota n.a. stem n.a. PMID[17077549]
NPO26058 Erycibe expansa Species Convolvulaceae Eukaryota stems n.a. n.a. PMID[17158054]
NPO6364 Pongamiopsis pervilleana Species Fabaceae Eukaryota n.a. Madagascar Dry Forest n.a. PMID[20804165]
NPO20249 Antheroporum pierrei Species Fabaceae Eukaryota n.a. leaf n.a. PMID[21452840]
NPO20249 Antheroporum pierrei Species Fabaceae Eukaryota n.a. twig n.a. PMID[21452840]
NPO14197 Patrinia scabra Species Caprifoliaceae Eukaryota Roots n.a. n.a. PMID[23002924]
NPO22730 Indigofera spicata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23895019]
NPO14197 Patrinia scabra Species Caprifoliaceae Eukaryota Roots n.a. n.a. PMID[29799195]
NPO6470 Pachyrhizus erosus Species Fabaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO6470 Pachyrhizus erosus Species Fabaceae Eukaryota Tuber n.a. n.a. Database[FooDB]
NPO6470 Pachyrhizus erosus Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5753 Glycosmis montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6147 Eupatorium riparium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26058 Erycibe expansa Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14197 Patrinia scabra Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6470 Pachyrhizus erosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6147 Eupatorium riparium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6470 Pachyrhizus erosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5753 Glycosmis montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14197 Patrinia scabra Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26058 Erycibe expansa Species Convolvulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6147 Eupatorium riparium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6470 Pachyrhizus erosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3890 Scopolia japonica Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20249 Antheroporum pierrei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2671 Pedicularis semitorta Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6364 Pongamiopsis pervilleana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5753 Glycosmis montana Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9663 Artemisia igniaria Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6470 Pachyrhizus erosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14197 Patrinia scabra Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14502 Pogonolepis muelleriana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5368 Achillea cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10386 Mundulea chapelieri Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12750 Cordia americana Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22730 Indigofera spicata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6147 Eupatorium riparium 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
NPT466 Cell Line U-937 Homo sapiens IC50 = 3600.0 nM PMID[519244]
NPT466 Cell Line U-937 Homo sapiens IC50 = 70.0 nM PMID[519244]
NPT466 Cell Line U-937 Homo sapiens IC50 = 90.0 nM PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 3.3 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 30.6 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 64.9 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 54.6 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = -2.0 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 0.8 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 2.4 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 5.5 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 95.8 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 96.9 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 96.4 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 96.0 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 98.3 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 98.7 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 98.5 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 17.2 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 21.8 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 24.4 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 29.2 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 52.2 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 50.6 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 47.6 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 53.6 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 97.3 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 97.1 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 94.9 % PMID[519244]
NPT453 Cell Line HT-1080 Homo sapiens Inhibition = 95.0 % PMID[519244]
NPT459 Individual Protein Human immunodeficiency virus type 1 reverse transcriptase Human immunodeficiency virus 1 IC50 > 200.0 ug.mL-1 PMID[519245]
NPT179 Cell Line A2780 Homo sapiens IC50 = 0.5 ug.mL-1 PMID[519246]
NPT179 Cell Line A2780 Homo sapiens IC50 = 950.0 nM PMID[519248]
NPT457 Cell Line BT-549 Homo sapiens IC50 = 1600.0 nM PMID[519248]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 2700.0 nM PMID[519248]
NPT397 Cell Line NCI-H460 Homo sapiens IC50 = 2000.0 nM PMID[519248]
NPT391 Cell Line HCC 2998 Homo sapiens IC50 = 2900.0 nM PMID[519248]
NPT730 Cell Line MC-38 Mus musculus Activity = 450.0 Zone units PMID[519249]
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 0.055 ug PMID[519249]
NPT1094 Cell Line 697 Homo sapiens IC50 = 700.0 nM PMID[519250]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 100.0 nM PMID[519250]
NPT400 Cell Line MDA-MB-435 Homo sapiens Activity = 20.0 % PMID[519250]
NPT80 Cell Line Raji Homo sapiens IC50 = 2400.0 nM PMID[519250]
NPT1094 Cell Line 697 Homo sapiens IC50 = 500.0 nM PMID[519250]
NPT80 Cell Line Raji Homo sapiens IC50 = 5600.0 nM PMID[519250]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens Inhibition = 9.87 % PMID[519251]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens Inhibition = 27.63 % PMID[519251]
NPT451 Organism Helicobacter pylori Helicobacter pylori MIC = 1.3 ug.mL-1 PMID[519247]
NPT2 Others Unspecified Ratio = 0.6 n.a. PMID[519250]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 200.0 nM PMID[519250]
NPT2 Others Unspecified CD = 0.4 uM PMID[519250]
NPT27 Others Unspecified Ratio IC50 = 1020.0 n.a. PMID[519250]
NPT27 Others Unspecified IC50 = 102000.0 nM PMID[519250]
NPT2 Others Unspecified IC50 = 130.0 nM PMID[519252]

☑ 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 NPC152477 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
0.9875 High Similarity NPC121333
0.9874 High Similarity NPC242395
0.9748 High Similarity NPC173292
0.9693 High Similarity NPC156635
0.9688 High Similarity NPC8965
0.9686 High Similarity NPC234052
0.9625 High Similarity NPC128293
0.9568 High Similarity NPC74559
0.9565 High Similarity NPC150131
0.9563 High Similarity NPC224280
0.9563 High Similarity NPC62261
0.9515 High Similarity NPC67302
0.9506 High Similarity NPC177480
0.95 High Similarity NPC273959
0.9448 High Similarity NPC103307
0.9448 High Similarity NPC472276
0.9434 High Similarity NPC298093
0.9387 High Similarity NPC326877
0.9387 High Similarity NPC288813
0.9383 High Similarity NPC170245
0.9383 High Similarity NPC120593
0.9379 High Similarity NPC124038
0.9379 High Similarity NPC41301
0.9375 High Similarity NPC173137
0.9375 High Similarity NPC134783
0.9371 High Similarity NPC152904
0.9367 High Similarity NPC303255
0.9333 High Similarity NPC310794
0.9325 High Similarity NPC477154
0.9325 High Similarity NPC117854
0.9325 High Similarity NPC6588
0.9321 High Similarity NPC300053
0.9321 High Similarity NPC108433
0.9321 High Similarity NPC472277
0.9321 High Similarity NPC326520
0.9317 High Similarity NPC472448
0.9317 High Similarity NPC83922
0.9317 High Similarity NPC474034
0.9317 High Similarity NPC474033
0.9317 High Similarity NPC81679
0.9313 High Similarity NPC471976
0.9313 High Similarity NPC472624
0.9268 High Similarity NPC165456
0.9264 High Similarity NPC471213
0.9264 High Similarity NPC235610
0.9264 High Similarity NPC119589
0.9264 High Similarity NPC477517
0.9259 High Similarity NPC472281
0.9259 High Similarity NPC236521
0.9259 High Similarity NPC472625
0.9259 High Similarity NPC152659
0.9259 High Similarity NPC329669
0.9259 High Similarity NPC18100
0.9259 High Similarity NPC473313
0.9259 High Similarity NPC475985
0.9259 High Similarity NPC248638
0.9259 High Similarity NPC205265
0.9259 High Similarity NPC472278
0.9255 High Similarity NPC472632
0.9255 High Similarity NPC471210
0.9255 High Similarity NPC167678
0.9255 High Similarity NPC165549
0.9255 High Similarity NPC29876
0.9255 High Similarity NPC308992
0.9255 High Similarity NPC3629
0.925 High Similarity NPC55738
0.925 High Similarity NPC250214
0.925 High Similarity NPC95936
0.925 High Similarity NPC473990
0.9212 High Similarity NPC279209
0.9212 High Similarity NPC102277
0.9202 High Similarity NPC293319
0.9202 High Similarity NPC275780
0.9202 High Similarity NPC472450
0.9202 High Similarity NPC239752
0.9198 High Similarity NPC472402
0.9198 High Similarity NPC472635
0.9198 High Similarity NPC220912
0.9198 High Similarity NPC474150
0.9198 High Similarity NPC229632
0.9198 High Similarity NPC25152
0.9198 High Similarity NPC261470
0.9198 High Similarity NPC474162
0.9193 High Similarity NPC263449
0.9193 High Similarity NPC118256
0.9193 High Similarity NPC287328
0.9193 High Similarity NPC204290
0.9193 High Similarity NPC174953
0.9193 High Similarity NPC476980
0.9193 High Similarity NPC282009
0.9193 High Similarity NPC328102
0.9193 High Similarity NPC475784
0.9193 High Similarity NPC192686
0.9193 High Similarity NPC119209
0.9187 High Similarity NPC475267
0.9187 High Similarity NPC181960
0.9187 High Similarity NPC471209
0.9187 High Similarity NPC78225
0.9187 High Similarity NPC474836
0.9187 High Similarity NPC67876
0.9187 High Similarity NPC476981
0.9187 High Similarity NPC223787
0.9187 High Similarity NPC473272
0.9187 High Similarity NPC474208
0.9187 High Similarity NPC291508
0.9187 High Similarity NPC99597
0.9187 High Similarity NPC156057
0.9187 High Similarity NPC48208
0.9187 High Similarity NPC162869
0.9187 High Similarity NPC19097
0.9187 High Similarity NPC284820
0.9187 High Similarity NPC210084
0.9187 High Similarity NPC262286
0.9187 High Similarity NPC27337
0.9187 High Similarity NPC36852
0.9182 High Similarity NPC37392
0.9162 High Similarity NPC108202
0.9157 High Similarity NPC475825
0.9157 High Similarity NPC223375
0.9146 High Similarity NPC39091
0.9146 High Similarity NPC113093
0.9146 High Similarity NPC472449
0.9146 High Similarity NPC277480
0.9141 High Similarity NPC306321
0.9141 High Similarity NPC186686
0.9141 High Similarity NPC472582
0.9141 High Similarity NPC303460
0.9141 High Similarity NPC189473
0.9141 High Similarity NPC23298
0.9136 High Similarity NPC228383
0.9136 High Similarity NPC471211
0.9136 High Similarity NPC471499
0.9136 High Similarity NPC474186
0.9136 High Similarity NPC474038
0.9136 High Similarity NPC471212
0.9136 High Similarity NPC266314
0.9136 High Similarity NPC474187
0.9136 High Similarity NPC61010
0.9136 High Similarity NPC259456
0.913 High Similarity NPC204879
0.913 High Similarity NPC22192
0.913 High Similarity NPC195832
0.9125 High Similarity NPC255106
0.9125 High Similarity NPC474638
0.9125 High Similarity NPC278778
0.9125 High Similarity NPC472916
0.9125 High Similarity NPC68093
0.9125 High Similarity NPC291878
0.9125 High Similarity NPC235165
0.9125 High Similarity NPC195796
0.9125 High Similarity NPC138243
0.9125 High Similarity NPC191146
0.9125 High Similarity NPC470600
0.9125 High Similarity NPC35038
0.9119 High Similarity NPC203080
0.9119 High Similarity NPC472915
0.9118 High Similarity NPC473883
0.9112 High Similarity NPC104682
0.9091 High Similarity NPC158761
0.9091 High Similarity NPC247973
0.9091 High Similarity NPC14662
0.9085 High Similarity NPC37183
0.9085 High Similarity NPC470457
0.9085 High Similarity NPC50960
0.9085 High Similarity NPC473286
0.908 High Similarity NPC52204
0.908 High Similarity NPC329760
0.908 High Similarity NPC476247
0.9074 High Similarity NPC36217
0.9074 High Similarity NPC474287
0.9074 High Similarity NPC470183
0.9074 High Similarity NPC14353
0.9074 High Similarity NPC228785
0.9074 High Similarity NPC200746
0.9074 High Similarity NPC246478
0.9074 High Similarity NPC475886
0.9074 High Similarity NPC56085
0.9074 High Similarity NPC470326
0.9068 High Similarity NPC196448
0.9068 High Similarity NPC96167
0.9068 High Similarity NPC469584
0.9068 High Similarity NPC471515
0.9068 High Similarity NPC299520
0.9068 High Similarity NPC472913
0.9068 High Similarity NPC129684
0.9068 High Similarity NPC472910
0.9068 High Similarity NPC472598
0.9068 High Similarity NPC78071
0.9068 High Similarity NPC472911
0.9068 High Similarity NPC474681
0.9068 High Similarity NPC222814
0.9068 High Similarity NPC165977
0.9068 High Similarity NPC52889
0.9068 High Similarity NPC474055
0.9068 High Similarity NPC218313
0.9068 High Similarity NPC472914
0.9068 High Similarity NPC217677
0.9068 High Similarity NPC471479
0.9068 High Similarity NPC52530
0.9068 High Similarity NPC245758

  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 NPC152477 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
0.9434 High Similarity NPD5494 Approved
0.9006 High Similarity NPD3882 Suspended
0.9 High Similarity NPD2393 Clinical (unspecified phase)
0.897 High Similarity NPD6166 Phase 2
0.897 High Similarity NPD6167 Clinical (unspecified phase)
0.897 High Similarity NPD6168 Clinical (unspecified phase)
0.8938 High Similarity NPD1934 Approved
0.8882 High Similarity NPD2801 Approved
0.865 High Similarity NPD7096 Clinical (unspecified phase)
0.8639 High Similarity NPD3818 Discontinued
0.8606 High Similarity NPD7075 Discontinued
0.8605 High Similarity NPD4338 Clinical (unspecified phase)
0.8598 High Similarity NPD3817 Phase 2
0.8588 High Similarity NPD5844 Phase 1
0.858 High Similarity NPD4380 Phase 2
0.8563 High Similarity NPD1247 Approved
0.8538 High Similarity NPD7074 Phase 3
0.85 High Similarity NPD4378 Clinical (unspecified phase)
0.8497 Intermediate Similarity NPD7808 Phase 3
0.8488 Intermediate Similarity NPD6797 Phase 2
0.848 Intermediate Similarity NPD7054 Approved
0.8447 Intermediate Similarity NPD1512 Approved
0.8439 Intermediate Similarity NPD7251 Discontinued
0.8434 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.843 Intermediate Similarity NPD7472 Approved
0.8373 Intermediate Similarity NPD5402 Approved
0.8372 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8364 Intermediate Similarity NPD6801 Discontinued
0.8323 Intermediate Similarity NPD1511 Approved
0.8313 Intermediate Similarity NPD7819 Suspended
0.8276 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8274 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8246 Intermediate Similarity NPD3926 Phase 2
0.8239 Intermediate Similarity NPD1549 Phase 2
0.8235 Intermediate Similarity NPD6959 Discontinued
0.8225 Intermediate Similarity NPD919 Approved
0.821 Intermediate Similarity NPD6799 Approved
0.8193 Intermediate Similarity NPD7411 Suspended
0.8187 Intermediate Similarity NPD6232 Discontinued
0.8176 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.816 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.815 Intermediate Similarity NPD7473 Discontinued
0.8133 Intermediate Similarity NPD6599 Discontinued
0.8125 Intermediate Similarity NPD6559 Discontinued
0.8113 Intermediate Similarity NPD2796 Approved
0.8095 Intermediate Similarity NPD1465 Phase 2
0.8045 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.8022 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD3751 Discontinued
0.7953 Intermediate Similarity NPD3749 Approved
0.7952 Intermediate Similarity NPD5403 Approved
0.7937 Intermediate Similarity NPD1510 Phase 2
0.7886 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7874 Intermediate Similarity NPD3787 Discontinued
0.7853 Intermediate Similarity NPD2800 Approved
0.7831 Intermediate Similarity NPD2532 Approved
0.7831 Intermediate Similarity NPD2534 Approved
0.7831 Intermediate Similarity NPD5401 Approved
0.7831 Intermediate Similarity NPD2533 Approved
0.7814 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7802 Intermediate Similarity NPD8434 Phase 2
0.7799 Intermediate Similarity NPD1240 Approved
0.7791 Intermediate Similarity NPD7768 Phase 2
0.7778 Intermediate Similarity NPD2935 Discontinued
0.7738 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD920 Approved
0.7727 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD6777 Approved
0.7725 Intermediate Similarity NPD6780 Approved
0.7725 Intermediate Similarity NPD6779 Approved
0.7725 Intermediate Similarity NPD6782 Approved
0.7725 Intermediate Similarity NPD6776 Approved
0.7725 Intermediate Similarity NPD6781 Approved
0.7725 Intermediate Similarity NPD6778 Approved
0.7702 Intermediate Similarity NPD1607 Approved
0.7688 Intermediate Similarity NPD943 Approved
0.7636 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD37 Approved
0.7614 Intermediate Similarity NPD7199 Phase 2
0.7609 Intermediate Similarity NPD8150 Discontinued
0.7604 Intermediate Similarity NPD7696 Phase 3
0.7604 Intermediate Similarity NPD7698 Approved
0.7604 Intermediate Similarity NPD7435 Discontinued
0.7604 Intermediate Similarity NPD7697 Approved
0.76 Intermediate Similarity NPD6234 Discontinued
0.7598 Intermediate Similarity NPD7228 Approved
0.759 Intermediate Similarity NPD3750 Approved
0.759 Intermediate Similarity NPD4628 Phase 3
0.7586 Intermediate Similarity NPD4967 Phase 2
0.7586 Intermediate Similarity NPD4966 Approved
0.7586 Intermediate Similarity NPD4965 Approved
0.7578 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD1613 Approved
0.7545 Intermediate Similarity NPD6190 Approved
0.7544 Intermediate Similarity NPD3226 Approved
0.7541 Intermediate Similarity NPD8313 Approved
0.7541 Intermediate Similarity NPD8312 Approved
0.7538 Intermediate Similarity NPD7701 Phase 2
0.7531 Intermediate Similarity NPD447 Suspended
0.753 Intermediate Similarity NPD1243 Approved
0.7515 Intermediate Similarity NPD2344 Approved
0.7515 Intermediate Similarity NPD2346 Discontinued
0.75 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD2799 Discontinued
0.7486 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD7871 Phase 2
0.7474 Intermediate Similarity NPD7870 Phase 2
0.747 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.746 Intermediate Similarity NPD6534 Approved
0.746 Intermediate Similarity NPD6535 Approved
0.7456 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7438 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7435 Intermediate Similarity NPD7700 Phase 2
0.7435 Intermediate Similarity NPD7699 Phase 2
0.7432 Intermediate Similarity NPD7685 Pre-registration
0.7423 Intermediate Similarity NPD230 Phase 1
0.7394 Intermediate Similarity NPD3748 Approved
0.7394 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD3027 Phase 3
0.7389 Intermediate Similarity NPD2403 Approved
0.7384 Intermediate Similarity NPD1653 Approved
0.7382 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD5953 Discontinued
0.7375 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD5710 Approved
0.7374 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD7874 Approved
0.7374 Intermediate Similarity NPD5711 Approved
0.7363 Intermediate Similarity NPD7286 Phase 2
0.7349 Intermediate Similarity NPD6100 Approved
0.7349 Intermediate Similarity NPD6099 Approved
0.7349 Intermediate Similarity NPD1551 Phase 2
0.7346 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD2313 Discontinued
0.7337 Intermediate Similarity NPD7240 Approved
0.7337 Intermediate Similarity NPD2309 Approved
0.7337 Intermediate Similarity NPD7783 Phase 2
0.7337 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD7801 Approved
0.7323 Intermediate Similarity NPD8151 Discontinued
0.7317 Intermediate Similarity NPD1933 Approved
0.7314 Intermediate Similarity NPD6844 Discontinued
0.731 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD6823 Phase 2
0.7278 Intermediate Similarity NPD7229 Phase 3
0.7278 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD4360 Phase 2
0.7277 Intermediate Similarity NPD4363 Phase 3
0.7268 Intermediate Similarity NPD7907 Approved
0.7262 Intermediate Similarity NPD2424 Discontinued
0.7255 Intermediate Similarity NPD4665 Approved
0.7255 Intermediate Similarity NPD4111 Phase 1
0.7251 Intermediate Similarity NPD7390 Discontinued
0.7241 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7238 Intermediate Similarity NPD5242 Approved
0.7231 Intermediate Similarity NPD2494 Approved
0.7231 Intermediate Similarity NPD2493 Approved
0.7222 Intermediate Similarity NPD7584 Approved
0.7222 Intermediate Similarity NPD4908 Phase 1
0.7215 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD6355 Discontinued
0.7204 Intermediate Similarity NPD7549 Discontinued
0.7202 Intermediate Similarity NPD1471 Phase 3
0.7202 Intermediate Similarity NPD2975 Approved
0.7202 Intermediate Similarity NPD2974 Approved
0.7202 Intermediate Similarity NPD2973 Approved
0.7195 Intermediate Similarity NPD6233 Phase 2
0.7186 Intermediate Similarity NPD7033 Discontinued
0.7176 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7175 Intermediate Similarity NPD8455 Phase 2
0.7175 Intermediate Similarity NPD5761 Phase 2
0.7175 Intermediate Similarity NPD5760 Phase 2
0.7169 Intermediate Similarity NPD6651 Approved
0.716 Intermediate Similarity NPD9494 Approved
0.716 Intermediate Similarity NPD2861 Phase 2
0.7159 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3452 Approved
0.7143 Intermediate Similarity NPD3450 Approved
0.7143 Intermediate Similarity NPD7458 Discontinued
0.7135 Intermediate Similarity NPD5353 Approved
0.7134 Intermediate Similarity NPD6798 Discontinued
0.7127 Intermediate Similarity NPD8127 Discontinued
0.7121 Intermediate Similarity NPD8320 Phase 1
0.7121 Intermediate Similarity NPD4583 Approved
0.7121 Intermediate Similarity NPD4582 Approved
0.7121 Intermediate Similarity NPD8319 Approved
0.712 Intermediate Similarity NPD2163 Approved
0.711 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7108 Intermediate Similarity NPD5124 Phase 1
0.7108 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD4580 Approved
0.7073 Intermediate Similarity NPD4625 Phase 3
0.7071 Intermediate Similarity NPD4004 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