Structure

Physi-Chem Properties

Molecular Weight:  422.17
Volume:  441.663
LogP:  6.207
LogD:  3.582
LogS:  -2.649
# Rotatable Bonds:  5
TPSA:  111.13
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.415
Synthetic Accessibility Score:  3.164
Fsp3:  0.24
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:  -5.003
MDCK Permeability:  1.2720330232696142e-05
Pgp-inhibitor:  0.284
Pgp-substrate:  0.746
Human Intestinal Absorption (HIA):  0.03
20% Bioavailability (F20%):  0.967
30% Bioavailability (F30%):  0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.006
Plasma Protein Binding (PPB):  92.08686828613281%
Volume Distribution (VD):  0.773
Pgp-substrate:  7.711251735687256%

ADMET: Metabolism

CYP1A2-inhibitor:  0.867
CYP1A2-substrate:  0.171
CYP2C19-inhibitor:  0.931
CYP2C19-substrate:  0.051
CYP2C9-inhibitor:  0.853
CYP2C9-substrate:  0.919
CYP2D6-inhibitor:  0.844
CYP2D6-substrate:  0.227
CYP3A4-inhibitor:  0.273
CYP3A4-substrate:  0.072

ADMET: Excretion

Clearance (CL):  9.056
Half-life (T1/2):  0.616

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.942
Drug-inuced Liver Injury (DILI):  0.974
AMES Toxicity:  0.674
Rat Oral Acute Toxicity:  0.21
Maximum Recommended Daily Dose:  0.121
Skin Sensitization:  0.822
Carcinogencity:  0.074
Eye Corrosion:  0.003
Eye Irritation:  0.737
Respiratory Toxicity:  0.198

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  Natural Product: NPC96565

Natural Product ID:  NPC96565
Common Name*:   Kuwanon C
IUPAC Name:   2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-3,8-bis(3-methylbut-2-enyl)chromen-4-one
Synonyms:   Kuwanon C; Norartocarpin
Standard InCHIKey:  UWQYBLOHTQWSQD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C25H26O6/c1-13(2)5-8-17-20(28)12-21(29)22-23(30)18(9-6-14(3)4)24(31-25(17)22)16-10-7-15(26)11-19(16)27/h5-7,10-12,26-29H,8-9H2,1-4H3
SMILES:  CC(=CCc1c(oc2c(c1=O)c(O)cc(c2CC=C(C)C)O)c1ccc(cc1O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL518543
PubChem CID:   5481958
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001615] Flavones
          • [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. root n.a. DOI[10.1016/0031-9422(95)00135-T]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. root n.a. PMID[11395279]
NPO9402 Morus mongolica Species Moraceae Eukaryota n.a. n.a. n.a. PMID[11429996]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota whole plants n.a. n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota whole plants Shawnee National Forest, Harrisburg, IL, US n.a. PMID[11678652]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. PMID[12419367]
NPO957 Sapindus mukorossi Species Sapindaceae Eukaryota Galls n.a. n.a. PMID[16724837]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. root n.a. PMID[17396934]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. root n.a. PMID[17405024]
NPO957 Sapindus mukorossi Species Sapindaceae Eukaryota n.a. gall n.a. PMID[17827775]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota leaves Kaohsiung, Taiwan 2006-SEP PMID[18986201]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota Fruits n.a. n.a. PMID[19296617]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20815207]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. bark n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[22207282]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota Wood n.a. n.a. PMID[23113717]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[23806866]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. Konya, Turkey 2007-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota root bark University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic 2011-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota leaves Chungbuk, Korea n.a. PMID[25935644]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[25981820]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. latex n.a. PMID[27294120]
NPO11796 Morus australis Species Moraceae Eukaryota Root Bark n.a. n.a. PMID[27908762]
NPO28265 Morus alba Species Moraceae Eukaryota Root barks n.a. n.a. PMID[3097265]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. formosan n.a. PMID[8864236]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. formosan n.a. PMID[8864236]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. PMID[9358644]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. n.a. n.a. PMID[9358644]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. PMID[9544568]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota Latex Exudate n.a. n.a. Database[FooDB]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. Database[FooDB]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO67 Fructus mori n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO9402 Morus mongolica Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO957 Sapindus mukorossi Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26579 Artocarpus fretessi Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9402 Morus mongolica Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26579 Artocarpus fretessi Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO957 Sapindus mukorossi Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11796 Morus australis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO67 Fructus mori n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO957 Sapindus mukorossi Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9402 Morus mongolica Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5495 Broussonetia papyrifera Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9402 Morus mongolica Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17767 Artocarpus heterophyllus Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO957 Sapindus mukorossi Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11796 Morus australis Species Moraceae 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
NPT30 Individual Protein Cyclooxygenase-1 Homo sapiens IC50 = 62000.0 nM PMID[507234]
NPT31 Individual Protein Cyclooxygenase-2 Homo sapiens IC50 > 100000.0 nM PMID[507234]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens IC50 = 1700.0 nM PMID[507238]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens Ki = 3100.0 nM PMID[507238]
NPT1970 Cell Line THP-1 Homo sapiens IC50 = 1700.0 nM PMID[507239]
NPT1120 Individual Protein Pancreatic triacylglycerol lipase Sus scrofa Inhibition = 72.5 % PMID[507240]
NPT1120 Individual Protein Pancreatic triacylglycerol lipase Sus scrofa IC50 = 18600.0 nM PMID[507240]
NPT1464 Individual Protein Phosphodiesterase 4D Homo sapiens IC50 = 310.0 nM PMID[507241]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 9.6 ug.mL-1 PMID[507242]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 5.9 % PMID[507235]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 60.2 % PMID[507235]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 83.9 % PMID[507235]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 54.8 % PMID[507235]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 0.0 % PMID[507235]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 5.5 % PMID[507235]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 26.9 % PMID[507235]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 67.6 % PMID[507235]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 78.8 % PMID[507235]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens Ki = 2200.0 nM PMID[507236]
NPT740 Individual Protein Beta-secretase 1 Homo sapiens IC50 = 3400.0 nM PMID[507236]
NPT2 Others Unspecified IC50 = 17300.0 nM PMID[507237]

☑ 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 NPC96565 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC303633
1.0 High Similarity NPC55018
1.0 High Similarity NPC220062
1.0 High Similarity NPC301217
1.0 High Similarity NPC216978
0.9925 High Similarity NPC172986
0.9925 High Similarity NPC201395
0.9925 High Similarity NPC159275
0.9925 High Similarity NPC270883
0.9925 High Similarity NPC241100
0.9925 High Similarity NPC261227
0.9852 High Similarity NPC282300
0.9852 High Similarity NPC147688
0.9852 High Similarity NPC156590
0.9852 High Similarity NPC118840
0.9852 High Similarity NPC205006
0.9852 High Similarity NPC110969
0.9852 High Similarity NPC64908
0.9851 High Similarity NPC18260
0.9851 High Similarity NPC217186
0.9851 High Similarity NPC53181
0.9851 High Similarity NPC78913
0.9779 High Similarity NPC59739
0.9779 High Similarity NPC200694
0.9779 High Similarity NPC78803
0.9779 High Similarity NPC217083
0.9779 High Similarity NPC226636
0.9779 High Similarity NPC62840
0.9779 High Similarity NPC293852
0.9779 High Similarity NPC11561
0.9779 High Similarity NPC214236
0.9779 High Similarity NPC299080
0.9778 High Similarity NPC235239
0.9778 High Similarity NPC150522
0.9778 High Similarity NPC305355
0.9778 High Similarity NPC69769
0.9778 High Similarity NPC475680
0.9774 High Similarity NPC13408
0.9708 High Similarity NPC190637
0.9708 High Similarity NPC24821
0.9708 High Similarity NPC212932
0.9708 High Similarity NPC11700
0.9708 High Similarity NPC38219
0.9708 High Similarity NPC9117
0.9708 High Similarity NPC293053
0.9708 High Similarity NPC219915
0.9706 High Similarity NPC14871
0.9706 High Similarity NPC103362
0.9638 High Similarity NPC273538
0.9638 High Similarity NPC234629
0.9638 High Similarity NPC319752
0.9638 High Similarity NPC216538
0.9638 High Similarity NPC326500
0.9638 High Similarity NPC311741
0.9635 High Similarity NPC182852
0.9635 High Similarity NPC32739
0.9635 High Similarity NPC296917
0.9635 High Similarity NPC66515
0.9635 High Similarity NPC78
0.9635 High Similarity NPC166482
0.9635 High Similarity NPC148757
0.9635 High Similarity NPC144499
0.9635 High Similarity NPC324134
0.9635 High Similarity NPC473042
0.9635 High Similarity NPC107572
0.9635 High Similarity NPC125855
0.9635 High Similarity NPC76372
0.9635 High Similarity NPC36181
0.9635 High Similarity NPC37496
0.9635 High Similarity NPC166934
0.9635 High Similarity NPC306829
0.9635 High Similarity NPC194432
0.9635 High Similarity NPC227579
0.9635 High Similarity NPC10937
0.9635 High Similarity NPC220998
0.9635 High Similarity NPC177354
0.9635 High Similarity NPC324436
0.9635 High Similarity NPC76338
0.9635 High Similarity NPC167624
0.9635 High Similarity NPC228504
0.9635 High Similarity NPC1089
0.9635 High Similarity NPC40833
0.9635 High Similarity NPC161506
0.9635 High Similarity NPC265040
0.9635 High Similarity NPC223500
0.9635 High Similarity NPC328164
0.9635 High Similarity NPC64915
0.963 High Similarity NPC470669
0.963 High Similarity NPC470668
0.9627 High Similarity NPC29353
0.9627 High Similarity NPC473887
0.9627 High Similarity NPC174999
0.9627 High Similarity NPC231772
0.9627 High Similarity NPC194281
0.9627 High Similarity NPC234133
0.9627 High Similarity NPC124784
0.9627 High Similarity NPC127447
0.9627 High Similarity NPC47815
0.9568 High Similarity NPC124729
0.9568 High Similarity NPC83357
0.9568 High Similarity NPC5820
0.9568 High Similarity NPC20488
0.9568 High Similarity NPC154217
0.9568 High Similarity NPC214774
0.9568 High Similarity NPC301276
0.9568 High Similarity NPC142405
0.9568 High Similarity NPC176229
0.9568 High Similarity NPC178343
0.9568 High Similarity NPC476088
0.9568 High Similarity NPC312973
0.9568 High Similarity NPC88964
0.9568 High Similarity NPC267375
0.9568 High Similarity NPC475052
0.9568 High Similarity NPC306488
0.9568 High Similarity NPC246948
0.9568 High Similarity NPC111786
0.9568 High Similarity NPC67805
0.9568 High Similarity NPC474161
0.9568 High Similarity NPC470647
0.9568 High Similarity NPC195621
0.9568 High Similarity NPC54577
0.9565 High Similarity NPC143896
0.9565 High Similarity NPC91560
0.9565 High Similarity NPC278249
0.9565 High Similarity NPC478086
0.9565 High Similarity NPC87609
0.9565 High Similarity NPC316816
0.9565 High Similarity NPC223812
0.9565 High Similarity NPC470296
0.9565 High Similarity NPC75049
0.9565 High Similarity NPC39329
0.9565 High Similarity NPC188632
0.9565 High Similarity NPC185276
0.9565 High Similarity NPC149026
0.9565 High Similarity NPC214166
0.9565 High Similarity NPC107177
0.9565 High Similarity NPC257097
0.9565 High Similarity NPC166138
0.9565 High Similarity NPC18585
0.9565 High Similarity NPC310130
0.9565 High Similarity NPC158874
0.9565 High Similarity NPC169591
0.9565 High Similarity NPC175504
0.9565 High Similarity NPC68104
0.9565 High Similarity NPC77794
0.9565 High Similarity NPC81697
0.9565 High Similarity NPC112791
0.9565 High Similarity NPC125894
0.9565 High Similarity NPC106985
0.9565 High Similarity NPC196459
0.9565 High Similarity NPC221432
0.9565 High Similarity NPC85162
0.9565 High Similarity NPC150408
0.9565 High Similarity NPC94794
0.9565 High Similarity NPC164980
0.9562 High Similarity NPC110038
0.9562 High Similarity NPC3188
0.9562 High Similarity NPC258630
0.9562 High Similarity NPC17170
0.9562 High Similarity NPC96408
0.9562 High Similarity NPC324386
0.9562 High Similarity NPC4743
0.9562 High Similarity NPC156190
0.9562 High Similarity NPC279650
0.9562 High Similarity NPC312391
0.9562 High Similarity NPC213322
0.9562 High Similarity NPC248372
0.9562 High Similarity NPC166689
0.9559 High Similarity NPC23257
0.9556 High Similarity NPC250266
0.9556 High Similarity NPC266597
0.9556 High Similarity NPC228661
0.9552 High Similarity NPC13575
0.9549 High Similarity NPC274121
0.9549 High Similarity NPC78540
0.9549 High Similarity NPC50898
0.9549 High Similarity NPC213216
0.9549 High Similarity NPC108113
0.9549 High Similarity NPC93756
0.95 High Similarity NPC23728
0.95 High Similarity NPC166757
0.95 High Similarity NPC296998
0.95 High Similarity NPC79469
0.95 High Similarity NPC110303
0.95 High Similarity NPC104406
0.95 High Similarity NPC14001
0.95 High Similarity NPC237635
0.95 High Similarity NPC24673
0.95 High Similarity NPC473077
0.95 High Similarity NPC97716
0.95 High Similarity NPC201731
0.95 High Similarity NPC283234
0.9496 High Similarity NPC257236
0.9496 High Similarity NPC236766
0.9496 High Similarity NPC473015
0.9496 High Similarity NPC131568
0.9496 High Similarity NPC473013
0.9496 High Similarity NPC278175
0.9496 High Similarity NPC196137
0.9496 High Similarity NPC235217

  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 NPC96565 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
0.9638 High Similarity NPD4378 Clinical (unspecified phase)
0.9496 High Similarity NPD7410 Clinical (unspecified phase)
0.927 High Similarity NPD1550 Clinical (unspecified phase)
0.927 High Similarity NPD1552 Clinical (unspecified phase)
0.9203 High Similarity NPD1549 Phase 2
0.9124 High Similarity NPD1510 Phase 2
0.9111 High Similarity NPD1240 Approved
0.9058 High Similarity NPD2796 Approved
0.898 High Similarity NPD2393 Clinical (unspecified phase)
0.8978 High Similarity NPD1607 Approved
0.8973 High Similarity NPD7411 Suspended
0.8919 High Similarity NPD8443 Clinical (unspecified phase)
0.8904 High Similarity NPD4380 Phase 2
0.8881 High Similarity NPD1511 Approved
0.88 High Similarity NPD7075 Discontinued
0.8784 High Similarity NPD6801 Discontinued
0.8759 High Similarity NPD1512 Approved
0.8725 High Similarity NPD7819 Suspended
0.8725 High Similarity NPD7096 Clinical (unspecified phase)
0.8725 High Similarity NPD2801 Approved
0.8671 High Similarity NPD3750 Approved
0.8658 High Similarity NPD1934 Approved
0.8621 High Similarity NPD6799 Approved
0.8601 High Similarity NPD7421 Clinical (unspecified phase)
0.8601 High Similarity NPD2800 Approved
0.8553 High Similarity NPD4381 Clinical (unspecified phase)
0.8487 Intermediate Similarity NPD7768 Phase 2
0.8472 Intermediate Similarity NPD1243 Approved
0.8462 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.844 Intermediate Similarity NPD6651 Approved
0.8418 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8417 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8403 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.84 Intermediate Similarity NPD6599 Discontinued
0.8387 Intermediate Similarity NPD6959 Discontinued
0.8366 Intermediate Similarity NPD3882 Suspended
0.8322 Intermediate Similarity NPD3748 Approved
0.8322 Intermediate Similarity NPD2799 Discontinued
0.8312 Intermediate Similarity NPD3749 Approved
0.8301 Intermediate Similarity NPD3817 Phase 2
0.8286 Intermediate Similarity NPD2313 Discontinued
0.8264 Intermediate Similarity NPD2935 Discontinued
0.8264 Intermediate Similarity NPD1551 Phase 2
0.8228 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8228 Intermediate Similarity NPD6166 Phase 2
0.8228 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.821 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.8207 Intermediate Similarity NPD2344 Approved
0.82 Intermediate Similarity NPD5403 Approved
0.82 Intermediate Similarity NPD920 Approved
0.8188 Intermediate Similarity NPD1203 Approved
0.8176 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8156 Intermediate Similarity NPD3268 Approved
0.8125 Intermediate Similarity NPD3818 Discontinued
0.8101 Intermediate Similarity NPD6232 Discontinued
0.8089 Intermediate Similarity NPD5494 Approved
0.8086 Intermediate Similarity NPD5953 Discontinued
0.8075 Intermediate Similarity NPD7286 Phase 2
0.8075 Intermediate Similarity NPD7054 Approved
0.8069 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8067 Intermediate Similarity NPD5401 Approved
0.8067 Intermediate Similarity NPD2534 Approved
0.8067 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8067 Intermediate Similarity NPD2532 Approved
0.8067 Intermediate Similarity NPD2533 Approved
0.8063 Intermediate Similarity NPD7473 Discontinued
0.8058 Intermediate Similarity NPD2797 Approved
0.8041 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8029 Intermediate Similarity NPD422 Phase 1
0.8028 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD7074 Phase 3
0.8025 Intermediate Similarity NPD7472 Approved
0.8014 Intermediate Similarity NPD6099 Approved
0.8014 Intermediate Similarity NPD6100 Approved
0.8 Intermediate Similarity NPD1548 Phase 1
0.8 Intermediate Similarity NPD2798 Approved
0.7987 Intermediate Similarity NPD2309 Approved
0.7975 Intermediate Similarity NPD6797 Phase 2
0.7974 Intermediate Similarity NPD3226 Approved
0.7971 Intermediate Similarity NPD9717 Approved
0.7945 Intermediate Similarity NPD7033 Discontinued
0.7927 Intermediate Similarity NPD6559 Discontinued
0.7927 Intermediate Similarity NPD7251 Discontinued
0.7917 Intermediate Similarity NPD943 Approved
0.7899 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7898 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7887 Intermediate Similarity NPD6832 Phase 2
0.7887 Intermediate Similarity NPD4908 Phase 1
0.7881 Intermediate Similarity NPD7390 Discontinued
0.7879 Intermediate Similarity NPD7808 Phase 3
0.7857 Intermediate Similarity NPD3225 Approved
0.7838 Intermediate Similarity NPD2346 Discontinued
0.7834 Intermediate Similarity NPD5402 Approved
0.7823 Intermediate Similarity NPD4308 Phase 3
0.7801 Intermediate Similarity NPD3266 Approved
0.7801 Intermediate Similarity NPD3267 Approved
0.78 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.78 Intermediate Similarity NPD4628 Phase 3
0.7799 Intermediate Similarity NPD919 Approved
0.7771 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD1610 Phase 2
0.7744 Intermediate Similarity NPD5844 Phase 1
0.774 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD5124 Phase 1
0.7733 Intermediate Similarity NPD4363 Phase 3
0.7733 Intermediate Similarity NPD4360 Phase 2
0.7733 Intermediate Similarity NPD2654 Approved
0.7708 Intermediate Similarity NPD4625 Phase 3
0.7702 Intermediate Similarity NPD1247 Approved
0.7688 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD4361 Phase 2
0.7655 Intermediate Similarity NPD1296 Phase 2
0.7644 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD4288 Approved
0.7607 Intermediate Similarity NPD3926 Phase 2
0.759 Intermediate Similarity NPD1729 Discontinued
0.7589 Intermediate Similarity NPD1608 Approved
0.7589 Intermediate Similarity NPD3972 Approved
0.7551 Intermediate Similarity NPD4307 Phase 2
0.7547 Intermediate Similarity NPD1465 Phase 2
0.7518 Intermediate Similarity NPD1201 Approved
0.7517 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1933 Approved
0.75 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD9545 Approved
0.7468 Intermediate Similarity NPD6585 Discontinued
0.7464 Intermediate Similarity NPD9493 Approved
0.7448 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7439 Intermediate Similarity NPD5710 Approved
0.7439 Intermediate Similarity NPD5711 Approved
0.7431 Intermediate Similarity NPD1164 Approved
0.7431 Intermediate Similarity NPD1470 Approved
0.7421 Intermediate Similarity NPD5890 Approved
0.7421 Intermediate Similarity NPD5889 Approved
0.7417 Intermediate Similarity NPD5406 Approved
0.7417 Intermediate Similarity NPD5405 Approved
0.7417 Intermediate Similarity NPD5408 Approved
0.7417 Intermediate Similarity NPD5404 Approved
0.7415 Intermediate Similarity NPD3764 Approved
0.7415 Intermediate Similarity NPD411 Approved
0.7415 Intermediate Similarity NPD6798 Discontinued
0.7413 Intermediate Similarity NPD4749 Approved
0.7405 Intermediate Similarity NPD7458 Discontinued
0.7391 Intermediate Similarity NPD2296 Approved
0.7383 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD447 Suspended
0.7376 Intermediate Similarity NPD17 Approved
0.7372 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD1241 Discontinued
0.7368 Intermediate Similarity NPD1471 Phase 3
0.7343 Intermediate Similarity NPD1481 Phase 2
0.7338 Intermediate Similarity NPD7003 Approved
0.7333 Intermediate Similarity NPD7229 Phase 3
0.7325 Intermediate Similarity NPD5049 Phase 3
0.7318 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD1613 Approved
0.7315 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD4287 Approved
0.7296 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7294 Intermediate Similarity NPD6104 Discontinued
0.729 Intermediate Similarity NPD2354 Approved
0.7279 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1535 Discovery
0.7268 Intermediate Similarity NPD7584 Approved
0.7267 Intermediate Similarity NPD230 Phase 1
0.7262 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD1019 Discontinued
0.7255 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD7213 Phase 3
0.7197 Intermediate Similarity NPD7212 Phase 2
0.719 Intermediate Similarity NPD4476 Approved
0.719 Intermediate Similarity NPD4477 Approved
0.7181 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD5535 Approved
0.7169 Intermediate Similarity NPD7199 Phase 2
0.7161 Intermediate Similarity NPD1652 Phase 2
0.716 Intermediate Similarity NPD6844 Discontinued
0.716 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD6355 Discontinued
0.7152 Intermediate Similarity NPD4662 Approved
0.7152 Intermediate Similarity NPD4661 Approved
0.7152 Intermediate Similarity NPD7447 Phase 1
0.7143 Intermediate Similarity NPD2403 Approved
0.7143 Intermediate Similarity NPD2353 Approved
0.7143 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD6233 Phase 2
0.7123 Intermediate Similarity NPD1876 Approved
0.7114 Intermediate Similarity NPD3027 Phase 3
0.7113 Intermediate Similarity NPD1894 Discontinued
0.711 Intermediate Similarity NPD8313 Approved
0.711 Intermediate Similarity NPD8312 Approved
0.7097 Intermediate Similarity NPD2424 Discontinued
0.7095 Intermediate Similarity NPD2861 Phase 2

  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