NPASS Compound

Structure

CID149389 OpenBabel06191715522D 42 46 0 0 1 0 0 0 0 0999 V2000 -0.8476 -4.4043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -5.3830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 -3.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9332 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 -5.8723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -4.4043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -4.4043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9332 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -5.3830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -1.4681 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6952 -1.9574 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3904 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 -3.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7808 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 -5.8723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5428 -3.4255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 2.4468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 -2.9362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -4.4043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -4.4043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 1.4681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -3.4255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 41 1 0 0 0 0 2 42 1 0 0 0 0 3 7 1 0 0 0 0 3 15 2 0 0 0 0 4 8 2 0 0 0 0 4 15 1 0 0 0 0 5 9 1 0 0 0 0 5 16 2 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 18 2 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 19 1 0 0 0 0 11 12 2 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 17 1 0 0 0 0 13 21 2 0 0 0 0 14 17 2 0 0 0 0 14 23 1 0 0 0 0 15 27 1 0 0 0 0 16 28 1 0 0 0 0 17 24 1 0 0 0 0 18 33 1 0 0 0 0 19 34 1 0 0 0 0 20 31 2 0 0 0 0 21 26 1 0 0 0 0 21 27 1 0 0 0 0 22 29 2 0 0 0 0 22 35 1 0 0 0 0 23 30 2 0 0 0 0 23 36 1 0 0 0 0 24 25 1 0 0 0 0 24 32 2 0 0 0 0 25 20 1 6 0 0 0 25 26 1 0 0 0 0 26 28 1 6 0 0 0 27 37 2 0 0 0 0 28 38 2 0 0 0 0 29 31 1 0 0 0 0 29 39 1 0 0 0 0 30 32 1 0 0 0 0 30 40 1 0 0 0 0 31 41 1 0 0 0 0 32 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	570.15
Volume:	567.601
LogP:	3.719
LogD:	2.509
LogS:	-5.346
# Rotatable Bonds:	7
TPSA:	177.14
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.103
Synthetic Accessibility Score:	3.533
Fsp3:	0.094
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.213
MDCK Permeability:	5.917309408687288e-06
Pgp-inhibitor:	0.01
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.706
20% Bioavailability (F20%):	0.548
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	98.03803253173828%
Volume Distribution (VD):	0.276
Pgp-substrate:	6.296745777130127%

ADMET: Metabolism

CYP1A2-inhibitor:	0.519
CYP1A2-substrate:	0.21
CYP2C19-inhibitor:	0.156
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.677
CYP2C9-substrate:	0.788
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.159
CYP3A4-substrate:	0.502

ADMET: Excretion

Clearance (CL):	6.914
Half-life (T1/2):	0.806

ADMET: Toxicity

hERG Blockers:	0.171
Human Hepatotoxicity (H-HT):	0.022
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.703
Rat Oral Acute Toxicity:	0.09
Maximum Recommended Daily Dose:	0.757
Skin Sensitization:	0.932
Carcinogencity:	0.057
Eye Corrosion:	0.003
Eye Irritation:	0.901
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC149389

Natural Product ID:	NPC149389
*Common Name:**	Rel-Licobichalcone
IUPAC Name:	[(1S,2S)-1-(3,4-dihydroxy-2-methoxyphenyl)-6,7-dihydroxy-3-(4-hydroxybenzoyl)-8-methoxy-1,2-dihydronaphthalen-2-yl]-(4-hydroxyphenyl)methanone
Synonyms:
Standard InCHIKey:	WJSPTHUPUYBNNI-IZZNHLLZSA-N
Standard InCHI:	InChI=1S/C32H26O10/c1-41-31-20(11-12-22(35)29(31)39)25-24-17(14-23(36)30(40)32(24)42-2)13-21(27(37)15-3-7-18(33)8-4-15)26(25)28(38)16-5-9-19(34)10-6-16/h3-14,25-26,33-36,39-40H,1-2H3/t25-,26+/m0/s1
SMILES:	COc1c(O)c(O)cc2c1[C@@H]([C@@H](C(=C2)C(=O)c1ccc(cc1)O)C(=O)c1ccc(cc1)O)c1ccc(c(c1OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2437364
PubChem CID:	11827914
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	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

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	36200.0	nM	PMID[456112]

☑ 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 NPC149389 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	1685
0.2-0.3	3860
0.3-0.4	10469
0.4-0.5	7965
0.5-0.6	3427
0.6-0.7	5233
0.7-0.8	7331
0.8-0.85	2027
0.85-0.9	270
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9161	High Similarity	NPC78505
0.908	High Similarity	NPC188079
0.8994	High Similarity	NPC37543
0.8994	High Similarity	NPC178976
0.8994	High Similarity	NPC199463
0.8981	High Similarity	NPC312338
0.8981	High Similarity	NPC149889
0.8938	High Similarity	NPC245891
0.8938	High Similarity	NPC104876
0.8931	High Similarity	NPC14561
0.8931	High Similarity	NPC77807
0.8931	High Similarity	NPC5379
0.8903	High Similarity	NPC77598
0.8896	High Similarity	NPC26386
0.8896	High Similarity	NPC157133
0.8855	High Similarity	NPC4200
0.8831	High Similarity	NPC207732
0.8827	High Similarity	NPC311740
0.8817	High Similarity	NPC120102
0.881	High Similarity	NPC216307
0.8805	High Similarity	NPC107109
0.8797	High Similarity	NPC272566
0.8795	High Similarity	NPC180768
0.878	High Similarity	NPC477840
0.8774	High Similarity	NPC471473
0.8774	High Similarity	NPC471523
0.8774	High Similarity	NPC471524
0.8765	High Similarity	NPC470342
0.8765	High Similarity	NPC84571
0.8765	High Similarity	NPC472060
0.8765	High Similarity	NPC472052
0.8758	High Similarity	NPC110419
0.875	High Similarity	NPC226656
0.875	High Similarity	NPC66508
0.8735	High Similarity	NPC475212
0.8735	High Similarity	NPC300307
0.8734	High Similarity	NPC472279
0.8734	High Similarity	NPC85131
0.8712	High Similarity	NPC472906
0.871	High Similarity	NPC105213
0.8701	High Similarity	NPC229218
0.8701	High Similarity	NPC169214
0.8701	High Similarity	NPC192597
0.8701	High Similarity	NPC141817
0.8701	High Similarity	NPC312256
0.8701	High Similarity	NPC176030
0.8696	High Similarity	NPC279605
0.8696	High Similarity	NPC470762
0.8696	High Similarity	NPC474167
0.8688	High Similarity	NPC93552
0.8683	High Similarity	NPC476365
0.8679	High Similarity	NPC306011
0.8679	High Similarity	NPC256406
0.8679	High Similarity	NPC472838
0.8679	High Similarity	NPC302783
0.8679	High Similarity	NPC473201
0.8675	High Similarity	NPC105414
0.8675	High Similarity	NPC470341
0.8675	High Similarity	NPC324522
0.8675	High Similarity	NPC472058
0.8675	High Similarity	NPC234497
0.8671	High Similarity	NPC134293
0.8667	High Similarity	NPC303174
0.8659	High Similarity	NPC476372
0.8659	High Similarity	NPC473445
0.8659	High Similarity	NPC477841
0.8659	High Similarity	NPC219927
0.8659	High Similarity	NPC476371
0.865	High Similarity	NPC188967
0.865	High Similarity	NPC474960
0.8642	High Similarity	NPC183
0.8642	High Similarity	NPC112954
0.8642	High Similarity	NPC472963
0.8642	High Similarity	NPC222689
0.8642	High Similarity	NPC35598
0.8634	High Similarity	NPC234485
0.8625	High Similarity	NPC474993
0.8625	High Similarity	NPC164912
0.8623	High Similarity	NPC476637
0.8616	High Similarity	NPC58310
0.8616	High Similarity	NPC225854
0.8616	High Similarity	NPC295977
0.8614	High Similarity	NPC224851
0.8614	High Similarity	NPC171985
0.8614	High Similarity	NPC320741
0.8608	High Similarity	NPC139364
0.8608	High Similarity	NPC203747
0.8608	High Similarity	NPC254702
0.8608	High Similarity	NPC80710
0.8608	High Similarity	NPC472841
0.8608	High Similarity	NPC474903
0.8608	High Similarity	NPC152233
0.8608	High Similarity	NPC194653
0.8606	High Similarity	NPC45943
0.8606	High Similarity	NPC291977
0.8606	High Similarity	NPC272064
0.8605	High Similarity	NPC150977
0.8599	High Similarity	NPC165389
0.8598	High Similarity	NPC87431
0.8589	High Similarity	NPC477410
0.8589	High Similarity	NPC18699
0.8589	High Similarity	NPC105584
0.8589	High Similarity	NPC324736
0.8589	High Similarity	NPC190487
0.8589	High Similarity	NPC90497
0.8589	High Similarity	NPC154304
0.8589	High Similarity	NPC55443
0.8588	High Similarity	NPC472723
0.858	High Similarity	NPC98583
0.858	High Similarity	NPC54830
0.858	High Similarity	NPC472907
0.858	High Similarity	NPC56049
0.858	High Similarity	NPC473834
0.8571	High Similarity	NPC127172
0.8571	High Similarity	NPC324447
0.8571	High Similarity	NPC101107
0.8571	High Similarity	NPC17884
0.8571	High Similarity	NPC472905
0.8571	High Similarity	NPC469550
0.8571	High Similarity	NPC19273
0.8563	High Similarity	NPC476306
0.8562	High Similarity	NPC474414
0.8562	High Similarity	NPC35
0.8562	High Similarity	NPC144283
0.8562	High Similarity	NPC118427
0.8554	High Similarity	NPC156432
0.8553	High Similarity	NPC264550
0.8553	High Similarity	NPC195763
0.8553	High Similarity	NPC38545
0.8553	High Similarity	NPC171916
0.8553	High Similarity	NPC333691
0.8553	High Similarity	NPC264289
0.8553	High Similarity	NPC69430
0.8553	High Similarity	NPC40290
0.8553	High Similarity	NPC139293
0.8553	High Similarity	NPC142876
0.8553	High Similarity	NPC200060
0.8545	High Similarity	NPC42797
0.8545	High Similarity	NPC201800
0.8545	High Similarity	NPC476247
0.8544	High Similarity	NPC475348
0.8544	High Similarity	NPC261271
0.8537	High Similarity	NPC36217
0.8537	High Similarity	NPC476373
0.8537	High Similarity	NPC161947
0.8537	High Similarity	NPC195136
0.8537	High Similarity	NPC24627
0.8537	High Similarity	NPC471973
0.8537	High Similarity	NPC53889
0.8537	High Similarity	NPC155302
0.8537	High Similarity	NPC297212
0.8535	High Similarity	NPC160777
0.8535	High Similarity	NPC73416
0.8529	High Similarity	NPC99591
0.8529	High Similarity	NPC477992
0.8529	High Similarity	NPC477991
0.8528	High Similarity	NPC299520
0.8528	High Similarity	NPC136674
0.8528	High Similarity	NPC129684
0.8528	High Similarity	NPC185526
0.8526	High Similarity	NPC471417
0.8526	High Similarity	NPC119663
0.8526	High Similarity	NPC254659
0.8526	High Similarity	NPC16353
0.8521	High Similarity	NPC186847
0.8521	High Similarity	NPC65333
0.8521	High Similarity	NPC100251
0.8521	High Similarity	NPC158226
0.8521	High Similarity	NPC472454
0.8521	High Similarity	NPC257667
0.8521	High Similarity	NPC469506
0.8521	High Similarity	NPC174700
0.8519	High Similarity	NPC152951
0.8519	High Similarity	NPC38898
0.8519	High Similarity	NPC57674
0.8519	High Similarity	NPC168247
0.8519	High Similarity	NPC472048
0.8519	High Similarity	NPC230149
0.8519	High Similarity	NPC79375
0.8519	High Similarity	NPC117992
0.8519	High Similarity	NPC37253
0.8519	High Similarity	NPC234255
0.8516	High Similarity	NPC472088
0.8516	High Similarity	NPC472087
0.8512	High Similarity	NPC107627
0.8512	High Similarity	NPC475805
0.8509	High Similarity	NPC260979
0.8509	High Similarity	NPC43345
0.8509	High Similarity	NPC472912
0.8509	High Similarity	NPC180944
0.8506	High Similarity	NPC472091
0.8506	High Similarity	NPC472090
0.8506	High Similarity	NPC472092
0.8503	High Similarity	NPC251336
0.8503	High Similarity	NPC272560
0.8503	High Similarity	NPC43319
0.8503	High Similarity	NPC43065
0.8494	Intermediate Similarity	NPC12461
0.8494	Intermediate Similarity	NPC186686
0.8491	Intermediate Similarity	NPC238279

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 NPC149389 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	383
0.1-0.2	986
0.2-0.3	1570
0.3-0.4	2728
0.4-0.5	1864
0.5-0.6	998
0.6-0.7	454
0.7-0.8	139
0.8-0.85	21
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8727	High Similarity	NPD7473	Discontinued
0.8659	High Similarity	NPD6232	Discontinued
0.8443	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD6166	Phase 2
0.8354	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD5844	Phase 1
0.8282	Intermediate Similarity	NPD1934	Approved
0.8263	Intermediate Similarity	NPD6959	Discontinued
0.8239	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD2801	Approved
0.8232	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD3882	Suspended
0.8121	Intermediate Similarity	NPD1465	Phase 2
0.8086	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD4380	Phase 2
0.8035	Intermediate Similarity	NPD7074	Phase 3
0.8012	Intermediate Similarity	NPD1511	Approved
0.8012	Intermediate Similarity	NPD7819	Suspended
0.8012	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7390	Discontinued
0.7977	Intermediate Similarity	NPD7054	Approved
0.7963	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD3750	Approved
0.7931	Intermediate Similarity	NPD7472	Approved
0.7929	Intermediate Similarity	NPD6234	Discontinued
0.7919	Intermediate Similarity	NPD3818	Discontinued
0.7914	Intermediate Similarity	NPD1512	Approved
0.7882	Intermediate Similarity	NPD5494	Approved
0.7865	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3817	Phase 2
0.7848	Intermediate Similarity	NPD1510	Phase 2
0.7844	Intermediate Similarity	NPD37	Approved
0.7836	Intermediate Similarity	NPD7199	Phase 2
0.7834	Intermediate Similarity	NPD1607	Approved
0.7821	Intermediate Similarity	NPD1240	Approved
0.7816	Intermediate Similarity	NPD7228	Approved
0.7811	Intermediate Similarity	NPD7768	Phase 2
0.7797	Intermediate Similarity	NPD7808	Phase 3
0.7784	Intermediate Similarity	NPD7411	Suspended
0.7784	Intermediate Similarity	NPD6797	Phase 2
0.7765	Intermediate Similarity	NPD7075	Discontinued
0.7747	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD7251	Discontinued
0.7736	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD7003	Approved
0.7716	Intermediate Similarity	NPD8166	Discontinued
0.7707	Intermediate Similarity	NPD943	Approved
0.7706	Intermediate Similarity	NPD4965	Approved
0.7706	Intermediate Similarity	NPD4967	Phase 2
0.7706	Intermediate Similarity	NPD4966	Approved
0.7702	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7458	Discontinued
0.7661	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3749	Approved
0.7654	Intermediate Similarity	NPD8313	Approved
0.7654	Intermediate Similarity	NPD8312	Approved
0.7644	Intermediate Similarity	NPD3926	Phase 2
0.7625	Intermediate Similarity	NPD3748	Approved
0.7598	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1549	Phase 2
0.7588	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6801	Discontinued
0.7516	Intermediate Similarity	NPD3027	Phase 3
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.7513	Intermediate Similarity	NPD8151	Discontinued
0.747	Intermediate Similarity	NPD6799	Approved
0.7469	Intermediate Similarity	NPD2796	Approved
0.7469	Intermediate Similarity	NPD5405	Approved
0.7469	Intermediate Similarity	NPD6099	Approved
0.7469	Intermediate Similarity	NPD6100	Approved
0.7469	Intermediate Similarity	NPD5406	Approved
0.7469	Intermediate Similarity	NPD5404	Approved
0.7469	Intermediate Similarity	NPD5408	Approved
0.7468	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3226	Approved
0.7444	Intermediate Similarity	NPD6559	Discontinued
0.7438	Intermediate Similarity	NPD230	Phase 1
0.7432	Intermediate Similarity	NPD8150	Discontinued
0.7425	Intermediate Similarity	NPD2532	Approved
0.7425	Intermediate Similarity	NPD2534	Approved
0.7425	Intermediate Similarity	NPD2533	Approved
0.7416	Intermediate Similarity	NPD3751	Discontinued
0.7407	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4628	Phase 3
0.7394	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6651	Approved
0.7389	Intermediate Similarity	NPD9494	Approved
0.7368	Intermediate Similarity	NPD6780	Approved
0.7368	Intermediate Similarity	NPD6776	Approved
0.7368	Intermediate Similarity	NPD6778	Approved
0.7368	Intermediate Similarity	NPD6777	Approved
0.7368	Intermediate Similarity	NPD6781	Approved
0.7368	Intermediate Similarity	NPD6782	Approved
0.7368	Intermediate Similarity	NPD6779	Approved
0.7362	Intermediate Similarity	NPD2935	Discontinued
0.7358	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7240	Approved
0.7348	Intermediate Similarity	NPD7685	Pre-registration
0.7342	Intermediate Similarity	NPD4908	Phase 1
0.7342	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8127	Discontinued
0.7306	Intermediate Similarity	NPD7871	Phase 2
0.7306	Intermediate Similarity	NPD7870	Phase 2
0.7278	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1613	Approved
0.7267	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1470	Approved
0.7254	Intermediate Similarity	NPD7697	Approved
0.7254	Intermediate Similarity	NPD7435	Discontinued
0.7254	Intermediate Similarity	NPD7698	Approved
0.7254	Intermediate Similarity	NPD7696	Phase 3
0.7246	Intermediate Similarity	NPD6190	Approved
0.7243	Intermediate Similarity	NPD8434	Phase 2
0.7241	Intermediate Similarity	NPD5402	Approved
0.7235	Intermediate Similarity	NPD5403	Approved
0.7222	Intermediate Similarity	NPD7177	Discontinued
0.7219	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD919	Approved
0.7194	Intermediate Similarity	NPD7701	Phase 2
0.7191	Intermediate Similarity	NPD3787	Discontinued
0.7184	Intermediate Similarity	NPD8455	Phase 2
0.7176	Intermediate Similarity	NPD6273	Approved
0.7172	Intermediate Similarity	NPD7801	Approved
0.7165	Intermediate Similarity	NPD7680	Approved
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3764	Approved
0.7135	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD1247	Approved
0.7126	Intermediate Similarity	NPD2800	Approved
0.7121	Intermediate Similarity	NPD7874	Approved
0.7121	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5401	Approved
0.7115	Intermediate Similarity	NPD1201	Approved
0.711	Intermediate Similarity	NPD7028	Phase 2
0.7108	Intermediate Similarity	NPD2344	Approved
0.7105	Intermediate Similarity	NPD6534	Approved
0.7105	Intermediate Similarity	NPD6535	Approved
0.7095	Intermediate Similarity	NPD7229	Phase 3
0.7089	Intermediate Similarity	NPD1876	Approved
0.7083	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7700	Phase 2
0.7083	Intermediate Similarity	NPD7699	Phase 2
0.7081	Intermediate Similarity	NPD4625	Phase 3
0.707	Intermediate Similarity	NPD3972	Approved
0.7063	Intermediate Similarity	NPD3018	Phase 2
0.7056	Intermediate Similarity	NPD5242	Approved
0.7055	Intermediate Similarity	NPD3620	Phase 2
0.7055	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD1551	Phase 2
0.7047	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4288	Approved
0.7043	Intermediate Similarity	NPD8053	Approved
0.7043	Intermediate Similarity	NPD8054	Approved
0.7041	Intermediate Similarity	NPD8319	Approved
0.7041	Intermediate Similarity	NPD8320	Phase 1
0.7031	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6823	Phase 2
0.7013	Intermediate Similarity	NPD5536	Phase 2
0.7011	Intermediate Similarity	NPD5953	Discontinued
0.7006	Intermediate Similarity	NPD2346	Discontinued
0.7	Intermediate Similarity	NPD2798	Approved
0.6994	Remote Similarity	NPD1653	Approved
0.6988	Remote Similarity	NPD2799	Discontinued
0.6981	Remote Similarity	NPD1283	Approved
0.6962	Remote Similarity	NPD9269	Phase 2
0.6959	Remote Similarity	NPD4357	Discontinued
0.6951	Remote Similarity	NPD4060	Phase 1
0.6949	Remote Similarity	NPD5978	Approved
0.6949	Remote Similarity	NPD5977	Approved
0.6941	Remote Similarity	NPD2309	Approved
0.6935	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7549	Discontinued
0.6933	Remote Similarity	NPD3268	Approved
0.6923	Remote Similarity	NPD1651	Approved
0.6918	Remote Similarity	NPD2983	Phase 2
0.6918	Remote Similarity	NPD2982	Phase 2
0.6918	Remote Similarity	NPD4749	Approved
0.6915	Remote Similarity	NPD7783	Phase 2
0.6915	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD447	Suspended
0.6906	Remote Similarity	NPD5710	Approved
0.6906	Remote Similarity	NPD5711	Approved
0.6901	Remote Similarity	NPD3300	Phase 2
0.6899	Remote Similarity	NPD1610	Phase 2
0.6894	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7667	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data