NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.11
Volume:	261.435
LogP:	3.313
LogD:	3.448
LogS:	-2.802
# Rotatable Bonds:	4
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.869
Synthetic Accessibility Score:	1.943
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.866
MDCK Permeability:	1.5718933354946785e-05
Pgp-inhibitor:	0.176
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	96.99591827392578%
Volume Distribution (VD):	1.231
Pgp-substrate:	2.425935983657837%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.947
CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.619
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.967
CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.614
CYP3A4-substrate:	0.238

ADMET: Excretion

Clearance (CL):	12.801
Half-life (T1/2):	0.908

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.083
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.738
Skin Sensitization:	0.946
Carcinogencity:	0.065
Eye Corrosion:	0.571
Eye Irritation:	0.983
Respiratory Toxicity:	0.121

Download Data

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

Natural Product: NPC150624

Natural Product ID:	NPC150624
*Common Name:**	Batatasin Iv
IUPAC Name:	3-[2-(2-hydroxyphenyl)ethyl]-5-methoxyphenol
Synonyms:	Batatasin Iv
Standard InCHIKey:	IUMFLNFLJUUODE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O3/c1-18-14-9-11(8-13(16)10-14)6-7-12-4-2-3-5-15(12)17/h2-5,8-10,16-17H,6-7H2,1H3
SMILES:	COc1cc(CCc2ccccc2O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL228126
PubChem CID:	181271
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO809	Leitneria floridana	Species	Simaroubaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[11141127]
NPO20097	Thermobifida alba	Species	0cardiopsaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11430001]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15595606]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[16124773]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562827]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	roots	Phitsanulok Province, Thailand	2004-MAY	PMID[17480099]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17480099]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[21353549]
NPO24833	Dioscorea polystachya	Species	Dioscoreaceae	Eukaryota	n.a.	bark	n.a.	PMID[24689699]
NPO9419	Enterobacter cloacae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25427277]
NPO24359	Streptomyces cacaoi	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[27642865]
NPO26245	Styracaster caroli	Species	Porcellanasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8145229]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2692	Dioscorea rotundata	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2692	Dioscorea rotundata	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24833	Dioscorea polystachya	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24833	Dioscorea polystachya	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4628	Aloe deltoideodonta	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8977	0tholaena aschenborniana	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8460	Pedicularis torta	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3357	Alnus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26245	Styracaster caroli	Species	Porcellanasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2455	Thermopsis mollis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20097	Thermobifida alba	Species	0cardiopsaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7863	Dioscorea opposita	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6054	Sinularia brongersmai	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10024	Tylecodon wallichii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6828	Purpura aperta	Species	Muricidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24359	Streptomyces cacaoi	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8559	Calophyllum venulosum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9608	Lepraria citrina	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2692	Dioscorea rotundata	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27517	Crinum latifolium	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11319	Laurencia hybrida	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO809	Leitneria floridana	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9419	Enterobacter cloacae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6962	Cetraria delisei	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8807	Laurentia longiflora	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO4382	Elmerrillia papuana	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO11181	Juniperus bermudiana	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25475	Syphonota geographica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1490	Goldfussia yunnanensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO24833	Dioscorea polystachya	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13147	Euphorbia cyparissias	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9881	Petrosia hebes	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5635	Bauhinia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19605	Tara spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1103	Dioscorea japonica	Species	Dioscoreaceae	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	10
MIC	1
Others	2

Activity Type	# Activity
Cell Line	3
Individual Protein	4
NON-MOLECULAR	1
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	>	40900.0	nM	PMID[558834]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	40900.0	nM	PMID[558834]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	81800.0	nM	PMID[558834]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	>	100.0	ug.mL-1	PMID[558835]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	>	100.0	ug.mL-1	PMID[558835]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	106.1	%	PMID[558836]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	95.0	%	PMID[558836]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	204600.0	nM	PMID[558834]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	81800.0	nM	PMID[558834]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	204600.0	nM	PMID[558834]
NPT27	Others	Unspecified		IC50	>	81800.0	nM	PMID[558834]
NPT1	Others	Radical scavenging activity		IC50	>	100.0	ug.mL-1	PMID[558835]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100.0	ug.mL-1	PMID[558835]

☑ 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 NPC150624 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	403
0.1-0.2	1888
0.2-0.3	5375
0.3-0.4	13502
0.4-0.5	3947
0.5-0.6	5005
0.6-0.7	7865
0.7-0.8	3749
0.8-0.85	668
0.85-0.9	230
0.9-0.95	46
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
0.9908	High Similarity	NPC69261
0.9908	High Similarity	NPC33270
0.9907	High Similarity	NPC808
0.9815	High Similarity	NPC276737
0.9815	High Similarity	NPC22610
0.973	High Similarity	NPC184302
0.9727	High Similarity	NPC244816
0.9727	High Similarity	NPC221549
0.9727	High Similarity	NPC50521
0.9725	High Similarity	NPC53906
0.964	High Similarity	NPC190514
0.9636	High Similarity	NPC141090
0.955	High Similarity	NPC127894
0.955	High Similarity	NPC15860
0.955	High Similarity	NPC474933
0.955	High Similarity	NPC219070
0.955	High Similarity	NPC470759
0.9545	High Similarity	NPC167934
0.9474	High Similarity	NPC476633
0.9459	High Similarity	NPC114064
0.9459	High Similarity	NPC203113
0.9459	High Similarity	NPC229147
0.9459	High Similarity	NPC85292
0.9459	High Similarity	NPC54507
0.9444	High Similarity	NPC94045
0.9444	High Similarity	NPC168657
0.9391	High Similarity	NPC77789
0.9391	High Similarity	NPC18128
0.9386	High Similarity	NPC102639
0.9375	High Similarity	NPC195466
0.9369	High Similarity	NPC464
0.9369	High Similarity	NPC185541
0.9292	High Similarity	NPC131118
0.9279	High Similarity	NPC228287
0.9279	High Similarity	NPC180508
0.9273	High Similarity	NPC280606
0.9266	High Similarity	NPC2682
0.9182	High Similarity	NPC296920
0.9182	High Similarity	NPC90520
0.9153	High Similarity	NPC105925
0.9153	High Similarity	NPC113495
0.9153	High Similarity	NPC105031
0.9145	High Similarity	NPC121115
0.9138	High Similarity	NPC75713
0.9091	High Similarity	NPC303521
0.9076	High Similarity	NPC223953
0.9076	High Similarity	NPC170485
0.9074	High Similarity	NPC164576
0.9068	High Similarity	NPC228503
0.9068	High Similarity	NPC138248
0.9052	High Similarity	NPC218753
0.9009	High Similarity	NPC255068
0.9	High Similarity	NPC246620
0.9	High Similarity	NPC236760
0.9	High Similarity	NPC473221
0.9	High Similarity	NPC324112
0.9	High Similarity	NPC159968
0.9	High Similarity	NPC124452
0.9	High Similarity	NPC236791
0.9	High Similarity	NPC74817
0.9	High Similarity	NPC293054
0.9	High Similarity	NPC282000
0.9	High Similarity	NPC82679
0.9	High Similarity	NPC169474
0.8992	High Similarity	NPC60885
0.8992	High Similarity	NPC234400
0.8992	High Similarity	NPC105718
0.8992	High Similarity	NPC278955
0.8991	High Similarity	NPC35543
0.8983	High Similarity	NPC95168
0.8983	High Similarity	NPC474160
0.8983	High Similarity	NPC136319
0.8983	High Similarity	NPC282496
0.8983	High Similarity	NPC233526
0.8926	High Similarity	NPC154866
0.8926	High Similarity	NPC266691
0.8917	High Similarity	NPC103823
0.8917	High Similarity	NPC18924
0.8917	High Similarity	NPC44748
0.8917	High Similarity	NPC214406
0.8917	High Similarity	NPC82299
0.8917	High Similarity	NPC78974
0.8917	High Similarity	NPC28730
0.8917	High Similarity	NPC223136
0.8909	High Similarity	NPC174981
0.8909	High Similarity	NPC245115
0.8909	High Similarity	NPC75440
0.8908	High Similarity	NPC270030
0.8898	High Similarity	NPC41562
0.8898	High Similarity	NPC100099
0.8898	High Similarity	NPC36016
0.8889	High Similarity	NPC102216
0.8879	High Similarity	NPC85895
0.8879	High Similarity	NPC137294
0.8852	High Similarity	NPC471519
0.8852	High Similarity	NPC190144
0.8852	High Similarity	NPC471518
0.8843	High Similarity	NPC53781
0.8843	High Similarity	NPC266555
0.8843	High Similarity	NPC46978
0.8833	High Similarity	NPC82483
0.8833	High Similarity	NPC131397
0.8833	High Similarity	NPC251855
0.8833	High Similarity	NPC472093
0.8833	High Similarity	NPC476254
0.8833	High Similarity	NPC265483
0.8833	High Similarity	NPC208950
0.8833	High Similarity	NPC17943
0.8833	High Similarity	NPC203133
0.8833	High Similarity	NPC233410
0.8833	High Similarity	NPC57490
0.8833	High Similarity	NPC475169
0.8833	High Similarity	NPC116907
0.8833	High Similarity	NPC298757
0.8833	High Similarity	NPC221077
0.8833	High Similarity	NPC117214
0.8833	High Similarity	NPC299584
0.8833	High Similarity	NPC193544
0.8829	High Similarity	NPC82016
0.8829	High Similarity	NPC19808
0.8829	High Similarity	NPC33728
0.8824	High Similarity	NPC84086
0.8824	High Similarity	NPC76465
0.8824	High Similarity	NPC197757
0.8824	High Similarity	NPC38761
0.8824	High Similarity	NPC228922
0.8814	High Similarity	NPC54972
0.8814	High Similarity	NPC193364
0.8814	High Similarity	NPC212965
0.8803	High Similarity	NPC8283
0.8803	High Similarity	NPC258979
0.8803	High Similarity	NPC93398
0.8793	High Similarity	NPC63010
0.8793	High Similarity	NPC74821
0.878	High Similarity	NPC299221
0.878	High Similarity	NPC224157
0.878	High Similarity	NPC234488
0.878	High Similarity	NPC311680
0.878	High Similarity	NPC254000
0.878	High Similarity	NPC51840
0.878	High Similarity	NPC192687
0.878	High Similarity	NPC126836
0.877	High Similarity	NPC215300
0.877	High Similarity	NPC63179
0.877	High Similarity	NPC28765
0.877	High Similarity	NPC38017
0.876	High Similarity	NPC283049
0.876	High Similarity	NPC50315
0.876	High Similarity	NPC230479
0.876	High Similarity	NPC26879
0.875	High Similarity	NPC197351
0.875	High Similarity	NPC5796
0.875	High Similarity	NPC86502
0.875	High Similarity	NPC140521
0.875	High Similarity	NPC206487
0.875	High Similarity	NPC106914
0.875	High Similarity	NPC246648
0.875	High Similarity	NPC134195
0.8739	High Similarity	NPC120638
0.8739	High Similarity	NPC74137
0.8739	High Similarity	NPC474864
0.8739	High Similarity	NPC57199
0.8729	High Similarity	NPC166759
0.8718	High Similarity	NPC295259
0.8718	High Similarity	NPC226629
0.8716	High Similarity	NPC241891
0.871	High Similarity	NPC474356
0.871	High Similarity	NPC282508
0.871	High Similarity	NPC471517
0.871	High Similarity	NPC15543
0.871	High Similarity	NPC12275
0.871	High Similarity	NPC45715
0.871	High Similarity	NPC473309
0.871	High Similarity	NPC472590
0.8704	High Similarity	NPC100340
0.8704	High Similarity	NPC143659
0.8699	High Similarity	NPC96719
0.8699	High Similarity	NPC16577
0.8699	High Similarity	NPC469951
0.8699	High Similarity	NPC58164
0.8699	High Similarity	NPC212015
0.8699	High Similarity	NPC10225
0.8699	High Similarity	NPC222108
0.8699	High Similarity	NPC469963
0.8696	High Similarity	NPC232165
0.8689	High Similarity	NPC252131
0.8689	High Similarity	NPC127587
0.8689	High Similarity	NPC242032
0.8678	High Similarity	NPC249836
0.8678	High Similarity	NPC17809
0.8678	High Similarity	NPC293801
0.8678	High Similarity	NPC188022
0.8678	High Similarity	NPC102540
0.8678	High Similarity	NPC285040
0.8678	High Similarity	NPC103420
0.8673	High Similarity	NPC224527
0.8673	High Similarity	NPC165770
0.8673	High Similarity	NPC4493
0.8673	High Similarity	NPC476632
0.8673	High Similarity	NPC225679

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 NPC150624 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	1040
0.2-0.3	1529
0.3-0.4	2719
0.4-0.5	1724
0.5-0.6	1043
0.6-0.7	598
0.7-0.8	106
0.8-0.85	12
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8814	High Similarity	NPD1610	Phase 2
0.8793	High Similarity	NPD1548	Phase 1
0.8699	High Similarity	NPD4625	Phase 3
0.8667	High Similarity	NPD4749	Approved
0.8618	High Similarity	NPD4908	Phase 1
0.8548	High Similarity	NPD3027	Phase 3
0.848	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8468	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8455	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD940	Approved
0.8364	Intermediate Similarity	NPD846	Approved
0.8346	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD1613	Approved
0.8333	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4750	Phase 3
0.8273	Intermediate Similarity	NPD1242	Phase 1
0.822	Intermediate Similarity	NPD6671	Approved
0.8197	Intermediate Similarity	NPD422	Phase 1
0.8095	Intermediate Similarity	NPD2861	Phase 2
0.8095	Intermediate Similarity	NPD3018	Phase 2
0.8065	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8062	Intermediate Similarity	NPD1240	Approved
0.7939	Intermediate Similarity	NPD1607	Approved
0.792	Intermediate Similarity	NPD2982	Phase 2
0.792	Intermediate Similarity	NPD2983	Phase 2
0.7913	Intermediate Similarity	NPD968	Approved
0.7909	Intermediate Similarity	NPD844	Approved
0.7907	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6099	Approved
0.7895	Intermediate Similarity	NPD6100	Approved
0.7881	Intermediate Similarity	NPD228	Approved
0.784	Intermediate Similarity	NPD2981	Phase 2
0.782	Intermediate Similarity	NPD1510	Phase 2
0.7769	Intermediate Similarity	NPD709	Approved
0.775	Intermediate Similarity	NPD5283	Phase 1
0.7748	Intermediate Similarity	NPD2859	Approved
0.7748	Intermediate Similarity	NPD2860	Approved
0.7699	Intermediate Similarity	NPD3020	Approved
0.7698	Intermediate Similarity	NPD2232	Approved
0.7698	Intermediate Similarity	NPD2230	Approved
0.7698	Intermediate Similarity	NPD1608	Approved
0.7698	Intermediate Similarity	NPD2233	Approved
0.7692	Intermediate Similarity	NPD290	Approved
0.7679	Intermediate Similarity	NPD288	Approved
0.7664	Intermediate Similarity	NPD3892	Phase 2
0.7658	Intermediate Similarity	NPD2933	Approved
0.7658	Intermediate Similarity	NPD2934	Approved
0.7652	Intermediate Similarity	NPD2238	Phase 2
0.7632	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1091	Approved
0.76	Intermediate Similarity	NPD4626	Approved
0.76	Intermediate Similarity	NPD1778	Approved
0.7597	Intermediate Similarity	NPD6584	Phase 3
0.7578	Intermediate Similarity	NPD6696	Suspended
0.7574	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7447	Phase 1
0.7571	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD5451	Approved
0.7536	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD4060	Phase 1
0.7519	Intermediate Similarity	NPD2797	Approved
0.7518	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD7213	Phase 3
0.75	Intermediate Similarity	NPD7212	Phase 2
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7479	Intermediate Similarity	NPD2684	Approved
0.746	Intermediate Similarity	NPD17	Approved
0.7445	Intermediate Similarity	NPD3540	Phase 1
0.7417	Intermediate Similarity	NPD3021	Approved
0.7417	Intermediate Similarity	NPD3022	Approved
0.7411	Intermediate Similarity	NPD845	Approved
0.741	Intermediate Similarity	NPD3750	Approved
0.7407	Intermediate Similarity	NPD4097	Suspended
0.7402	Intermediate Similarity	NPD3496	Discontinued
0.7397	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1651	Approved
0.7377	Intermediate Similarity	NPD7635	Approved
0.7376	Intermediate Similarity	NPD1511	Approved
0.7372	Intermediate Similarity	NPD2796	Approved
0.7372	Intermediate Similarity	NPD3539	Phase 1
0.7364	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6583	Phase 3
0.7364	Intermediate Similarity	NPD1669	Approved
0.7364	Intermediate Similarity	NPD6582	Phase 2
0.7348	Intermediate Similarity	NPD596	Approved
0.7348	Intermediate Similarity	NPD600	Approved
0.7345	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD2557	Approved
0.7338	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD1934	Approved
0.7323	Intermediate Similarity	NPD2668	Approved
0.7323	Intermediate Similarity	NPD2667	Approved
0.7317	Intermediate Similarity	NPD1398	Phase 1
0.7308	Intermediate Similarity	NPD1283	Approved
0.7308	Intermediate Similarity	NPD3225	Approved
0.7299	Intermediate Similarity	NPD7033	Discontinued
0.7287	Intermediate Similarity	NPD2235	Phase 2
0.7287	Intermediate Similarity	NPD2231	Phase 2
0.7286	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2801	Approved
0.7273	Intermediate Similarity	NPD1512	Approved
0.7266	Intermediate Similarity	NPD3847	Discontinued
0.7259	Intermediate Similarity	NPD1558	Phase 1
0.725	Intermediate Similarity	NPD2342	Discontinued
0.7244	Intermediate Similarity	NPD3443	Approved
0.7244	Intermediate Similarity	NPD5691	Approved
0.7244	Intermediate Similarity	NPD3445	Approved
0.7244	Intermediate Similarity	NPD3444	Approved
0.7239	Intermediate Similarity	NPD3268	Approved
0.7236	Intermediate Similarity	NPD1138	Approved
0.7236	Intermediate Similarity	NPD5535	Approved
0.7236	Intermediate Similarity	NPD821	Approved
0.7236	Intermediate Similarity	NPD7843	Approved
0.7214	Intermediate Similarity	NPD5177	Phase 3
0.7209	Intermediate Similarity	NPD1611	Approved
0.7207	Intermediate Similarity	NPD9295	Approved
0.7203	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7157	Approved
0.72	Intermediate Similarity	NPD6387	Discontinued
0.7197	Intermediate Similarity	NPD4624	Approved
0.7192	Intermediate Similarity	NPD4380	Phase 2
0.7185	Intermediate Similarity	NPD839	Approved
0.7185	Intermediate Similarity	NPD840	Approved
0.7181	Intermediate Similarity	NPD3882	Suspended
0.7176	Intermediate Similarity	NPD8651	Approved
0.7163	Intermediate Similarity	NPD7466	Approved
0.7162	Intermediate Similarity	NPD7819	Suspended
0.7154	Intermediate Similarity	NPD1139	Approved
0.7154	Intermediate Similarity	NPD1137	Approved
0.7153	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1712	Approved
0.7143	Intermediate Similarity	NPD7340	Approved
0.7133	Intermediate Similarity	NPD4357	Discontinued
0.7131	Intermediate Similarity	NPD1792	Phase 2
0.713	Intermediate Similarity	NPD1809	Phase 2
0.7121	Intermediate Similarity	NPD1203	Approved
0.7114	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD3049	Approved
0.7109	Intermediate Similarity	NPD5585	Approved
0.7109	Intermediate Similarity	NPD1357	Approved
0.7101	Intermediate Similarity	NPD2200	Suspended
0.7095	Intermediate Similarity	NPD37	Approved
0.7092	Intermediate Similarity	NPD1652	Phase 2
0.709	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5536	Phase 2
0.7077	Intermediate Similarity	NPD1281	Approved
0.7071	Intermediate Similarity	NPD5763	Approved
0.7071	Intermediate Similarity	NPD5762	Approved
0.7068	Intermediate Similarity	NPD2798	Approved
0.7068	Intermediate Similarity	NPD3691	Phase 2
0.7068	Intermediate Similarity	NPD3690	Phase 2
0.7067	Intermediate Similarity	NPD7768	Phase 2
0.7067	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7124	Phase 2
0.7059	Intermediate Similarity	NPD6232	Discontinued
0.7055	Intermediate Similarity	NPD1653	Approved
0.7054	Intermediate Similarity	NPD6516	Phase 2
0.7054	Intermediate Similarity	NPD5846	Approved
0.705	Intermediate Similarity	NPD3748	Approved
0.7045	Intermediate Similarity	NPD2922	Phase 1
0.7039	Intermediate Similarity	NPD6746	Phase 2
0.7037	Intermediate Similarity	NPD1024	Discontinued
0.7037	Intermediate Similarity	NPD7095	Approved
0.7037	Intermediate Similarity	NPD9089	Approved
0.7031	Intermediate Similarity	NPD1182	Approved
0.7027	Intermediate Similarity	NPD7411	Suspended
0.7027	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1445	Approved
0.7025	Intermediate Similarity	NPD1444	Approved
0.702	Intermediate Similarity	NPD7075	Discontinued
0.702	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD6799	Approved
0.7014	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7041	Phase 2
0.7008	Intermediate Similarity	NPD9493	Approved
0.7008	Intermediate Similarity	NPD3596	Phase 2
0.7007	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3620	Phase 2
0.7007	Intermediate Similarity	NPD943	Approved
0.7007	Intermediate Similarity	NPD4005	Discontinued
0.7	Intermediate Similarity	NPD6032	Approved
0.7	Intermediate Similarity	NPD111	Approved
0.6985	Remote Similarity	NPD6798	Discontinued
0.6985	Remote Similarity	NPD1296	Phase 2
0.6984	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4538	Approved
0.6978	Remote Similarity	NPD6111	Discontinued
0.6978	Remote Similarity	NPD4536	Approved
0.6978	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6234	Discontinued
0.6972	Remote Similarity	NPD3060	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