NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	284.07
Volume:	282.482
LogP:	2.592
LogD:	2.776
LogS:	-3.36
# Rotatable Bonds:	1
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.7
Synthetic Accessibility Score:	2.531
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.879
MDCK Permeability:	1.32402237795759e-05
Pgp-inhibitor:	0.017
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.96
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	98.3038558959961%
Volume Distribution (VD):	0.609
Pgp-substrate:	1.940252423286438%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.314
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.676
CYP2C9-substrate:	0.839
CYP2D6-inhibitor:	0.557
CYP2D6-substrate:	0.675
CYP3A4-inhibitor:	0.851
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	15.41
Half-life (T1/2):	0.84

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.238
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.918
Rat Oral Acute Toxicity:	0.778
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.93
Carcinogencity:	0.759
Eye Corrosion:	0.005
Eye Irritation:	0.923
Respiratory Toxicity:	0.726

Download Data

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

Natural Product: NPC275053

Natural Product ID:	NPC275053
*Common Name:**	5-[2-(4-Hydroxyphenyl)Ethenyl]Benzene-1,3-Diol
IUPAC Name:	5-[2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol
Synonyms:	(Cis-Trans)-Resveratrol
Standard InCHIKey:	LUKBXSAWLPMMSZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h1-9,15-17H
SMILES:	C(=Cc1cc(cc(c1)O)O)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2019155
PubChem CID:	5056
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
NPO5650	Eupatorium glutinosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027751]
NPO1782	Piper caninum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270572]
NPO98	Leucosceptrum canum	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15524427]
NPO6522	Polyalthia evecta	Species	Annonaceae	Eukaryota	roots	n.a.	n.a.	PMID[16441071]
NPO6522	Polyalthia evecta	Species	Annonaceae	Eukaryota	n.a.	root	n.a.	PMID[16441071]
NPO9804	Cinnamosma macrocarpa	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17286431]
NPO10915	Heliotropium hirsutum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25661	Vatica rassak	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11541	Curcuma xanthorrhiza	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11541	Curcuma xanthorrhiza	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10915	Heliotropium hirsutum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25661	Vatica rassak	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14697	Ustilago esculenta	Species	Ustilaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11736	Bulla striata	Species	Bullidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14439	Marasmius oreades	Species	Marasmiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO98	Leucosceptrum canum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25661	Vatica rassak	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9804	Cinnamosma macrocarpa	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13334	Senecio toluccanus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11541	Curcuma xanthorrhiza	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11202	Maytenus imbricata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10915	Heliotropium hirsutum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1782	Piper caninum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5650	Eupatorium glutinosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15640	Sideritis chamaedryfolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6522	Polyalthia evecta	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9406	Cotula filicula	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

Activity Type	# Activity
Ki	13
Potency	2

Activity Type	# Activity
Individual Protein	13
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	=	1750.0	nM	PMID[543743]
NPT1146	Individual Protein	Carbonic anhydrase III	Homo sapiens	Ki	=	6750.0	nM	PMID[543743]
NPT1062	Individual Protein	Carbonic anhydrase IV	Homo sapiens	Ki	=	4010.0	nM	PMID[543743]
NPT1144	Individual Protein	Carbonic anhydrase VB	Homo sapiens	Ki	=	3240.0	nM	PMID[543743]
NPT1063	Individual Protein	Carbonic anhydrase VI	Homo sapiens	Ki	=	8630.0	nM	PMID[543743]
NPT3101	Individual Protein	Carbonic anhydrase XIII	Homo sapiens	Ki	=	8250.0	nM	PMID[543743]
NPT1147	Individual Protein	Carbonic anhydrase 15	Mus musculus	Ki	=	2570.0	nM	PMID[543743]
NPT1143	Individual Protein	Carbonic anhydrase VA	Homo sapiens	Ki	=	2860.0	nM	PMID[543743]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	=	2180.0	nM	PMID[543743]
NPT948	Individual Protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	9530.0	nM	PMID[543743]
NPT949	Individual Protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	8130.0	nM	PMID[543743]
NPT955	Individual Protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	8980.0	nM	PMID[543743]
NPT954	Individual Protein	Carbonic anhydrase XIV	Homo sapiens	Ki	=	1950.0	nM	PMID[543743]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	13324.4	nM	PMID[543744]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Potency	n.a.	18821.2	nM	PMID[543744]

☑ 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 NPC275053 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	396
0.1-0.2	2415
0.2-0.3	8818
0.3-0.4	10987
0.4-0.5	4769
0.5-0.6	8146
0.6-0.7	5443
0.7-0.8	1447
0.8-0.85	174
0.85-0.9	72
0.9-0.95	24
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC248573
1.0	High Similarity	NPC161571
0.9785	High Similarity	NPC291789
0.9688	High Similarity	NPC30506
0.9588	High Similarity	NPC292452
0.9479	High Similarity	NPC143659
0.9479	High Similarity	NPC100340
0.9394	High Similarity	NPC176527
0.93	High Similarity	NPC114392
0.93	High Similarity	NPC58427
0.93	High Similarity	NPC34864
0.93	High Similarity	NPC105727
0.9286	High Similarity	NPC102216
0.9286	High Similarity	NPC241891
0.9208	High Similarity	NPC202647
0.9192	High Similarity	NPC134829
0.9149	High Similarity	NPC295295
0.91	High Similarity	NPC109691
0.91	High Similarity	NPC118286
0.91	High Similarity	NPC302681
0.91	High Similarity	NPC248904
0.91	High Similarity	NPC39664
0.91	High Similarity	NPC470700
0.91	High Similarity	NPC39097
0.9091	High Similarity	NPC119860
0.9029	High Similarity	NPC268032
0.9029	High Similarity	NPC476632
0.9029	High Similarity	NPC90520
0.9029	High Similarity	NPC296920
0.9029	High Similarity	NPC4493
0.9029	High Similarity	NPC165770
0.9029	High Similarity	NPC225679
0.901	High Similarity	NPC54844
0.9	High Similarity	NPC474839
0.9	High Similarity	NPC246056
0.898	High Similarity	NPC166761
0.898	High Similarity	NPC10588
0.8958	High Similarity	NPC274678
0.8942	High Similarity	NPC43525
0.8942	High Similarity	NPC280606
0.8942	High Similarity	NPC166995
0.8922	High Similarity	NPC174981
0.8889	High Similarity	NPC284011
0.8889	High Similarity	NPC72947
0.8878	High Similarity	NPC80027
0.8857	High Similarity	NPC117846
0.8835	High Similarity	NPC19808
0.8835	High Similarity	NPC33728
0.88	High Similarity	NPC24404
0.88	High Similarity	NPC302219
0.88	High Similarity	NPC222522
0.88	High Similarity	NPC94351
0.88	High Similarity	NPC71002
0.88	High Similarity	NPC168303
0.88	High Similarity	NPC313030
0.88	High Similarity	NPC53051
0.88	High Similarity	NPC242342
0.88	High Similarity	NPC85479
0.88	High Similarity	NPC106396
0.88	High Similarity	NPC146798
0.88	High Similarity	NPC249828
0.8774	High Similarity	NPC107240
0.8774	High Similarity	NPC228287
0.8774	High Similarity	NPC180508
0.875	High Similarity	NPC94045
0.8738	High Similarity	NPC63698
0.8738	High Similarity	NPC61885
0.87	High Similarity	NPC137415
0.87	High Similarity	NPC11280
0.87	High Similarity	NPC147310
0.87	High Similarity	NPC166313
0.87	High Similarity	NPC294186
0.87	High Similarity	NPC24407
0.87	High Similarity	NPC192032
0.8667	High Similarity	NPC224527
0.8646	High Similarity	NPC45040
0.8614	High Similarity	NPC168393
0.8611	High Similarity	NPC141090
0.8611	High Similarity	NPC203113
0.86	High Similarity	NPC223393
0.8586	High Similarity	NPC32674
0.8571	High Similarity	NPC475018
0.8532	High Similarity	NPC470760
0.8532	High Similarity	NPC474933
0.8532	High Similarity	NPC195466
0.8529	High Similarity	NPC218879
0.8529	High Similarity	NPC244513
0.8529	High Similarity	NPC227458
0.8519	High Similarity	NPC472893
0.8505	High Similarity	NPC261343
0.8495	Intermediate Similarity	NPC265146
0.8491	Intermediate Similarity	NPC255068
0.8485	Intermediate Similarity	NPC292730
0.8485	Intermediate Similarity	NPC132271
0.8485	Intermediate Similarity	NPC216520
0.8485	Intermediate Similarity	NPC82664
0.8469	Intermediate Similarity	NPC128062
0.8469	Intermediate Similarity	NPC151715
0.8469	Intermediate Similarity	NPC76938
0.8462	Intermediate Similarity	NPC61033
0.8462	Intermediate Similarity	NPC305603
0.8462	Intermediate Similarity	NPC158253
0.8462	Intermediate Similarity	NPC204901
0.8462	Intermediate Similarity	NPC232523
0.8455	Intermediate Similarity	NPC144343
0.8447	Intermediate Similarity	NPC37802
0.844	Intermediate Similarity	NPC115808
0.8426	Intermediate Similarity	NPC22610
0.8426	Intermediate Similarity	NPC276737
0.8404	Intermediate Similarity	NPC150837
0.8404	Intermediate Similarity	NPC175313
0.8404	Intermediate Similarity	NPC248817
0.8396	Intermediate Similarity	NPC224870
0.8384	Intermediate Similarity	NPC26244
0.8384	Intermediate Similarity	NPC32714
0.8381	Intermediate Similarity	NPC95344
0.8378	Intermediate Similarity	NPC217174
0.8378	Intermediate Similarity	NPC226629
0.8365	Intermediate Similarity	NPC201662
0.8365	Intermediate Similarity	NPC67250
0.8365	Intermediate Similarity	NPC164576
0.8365	Intermediate Similarity	NPC12640
0.8365	Intermediate Similarity	NPC99836
0.8364	Intermediate Similarity	NPC277588
0.8351	Intermediate Similarity	NPC300478
0.835	Intermediate Similarity	NPC474603
0.835	Intermediate Similarity	NPC471511
0.835	Intermediate Similarity	NPC12987
0.8349	Intermediate Similarity	NPC167934
0.8349	Intermediate Similarity	NPC246760
0.8349	Intermediate Similarity	NPC808
0.8349	Intermediate Similarity	NPC53906
0.8349	Intermediate Similarity	NPC84999
0.8333	Intermediate Similarity	NPC27974
0.8333	Intermediate Similarity	NPC23804
0.8333	Intermediate Similarity	NPC104216
0.8317	Intermediate Similarity	NPC92730
0.8316	Intermediate Similarity	NPC197783
0.8304	Intermediate Similarity	NPC247364
0.8304	Intermediate Similarity	NPC232084
0.8304	Intermediate Similarity	NPC10932
0.8304	Intermediate Similarity	NPC223451
0.8304	Intermediate Similarity	NPC61516
0.8304	Intermediate Similarity	NPC69006
0.8304	Intermediate Similarity	NPC474565
0.8304	Intermediate Similarity	NPC472071
0.8302	Intermediate Similarity	NPC186385
0.8302	Intermediate Similarity	NPC299568
0.8302	Intermediate Similarity	NPC82016
0.83	Intermediate Similarity	NPC473388
0.8298	Intermediate Similarity	NPC124436
0.8273	Intermediate Similarity	NPC150624
0.8269	Intermediate Similarity	NPC239291
0.8241	Intermediate Similarity	NPC473521
0.8235	Intermediate Similarity	NPC294741
0.8235	Intermediate Similarity	NPC213730
0.823	Intermediate Similarity	NPC248363
0.823	Intermediate Similarity	NPC166759
0.823	Intermediate Similarity	NPC102639
0.823	Intermediate Similarity	NPC24125
0.8229	Intermediate Similarity	NPC184169
0.8229	Intermediate Similarity	NPC23167
0.8224	Intermediate Similarity	NPC242178
0.8218	Intermediate Similarity	NPC201967
0.8218	Intermediate Similarity	NPC156313
0.8218	Intermediate Similarity	NPC109955
0.8218	Intermediate Similarity	NPC225464
0.8214	Intermediate Similarity	NPC191866
0.82	Intermediate Similarity	NPC107522
0.82	Intermediate Similarity	NPC313650
0.8198	Intermediate Similarity	NPC244816
0.8198	Intermediate Similarity	NPC470759
0.8198	Intermediate Similarity	NPC50521
0.8198	Intermediate Similarity	NPC221549
0.8198	Intermediate Similarity	NPC33270
0.8198	Intermediate Similarity	NPC69261
0.8198	Intermediate Similarity	NPC15860
0.8198	Intermediate Similarity	NPC219070
0.8198	Intermediate Similarity	NPC127894
0.819	Intermediate Similarity	NPC54765
0.8182	Intermediate Similarity	NPC464
0.8182	Intermediate Similarity	NPC185541
0.8173	Intermediate Similarity	NPC327811
0.8173	Intermediate Similarity	NPC12278
0.8173	Intermediate Similarity	NPC254965
0.8172	Intermediate Similarity	NPC270094
0.8165	Intermediate Similarity	NPC263753
0.8163	Intermediate Similarity	NPC192
0.8163	Intermediate Similarity	NPC312304
0.8163	Intermediate Similarity	NPC300017
0.8158	Intermediate Similarity	NPC237667
0.8158	Intermediate Similarity	NPC476633
0.8155	Intermediate Similarity	NPC91461
0.8155	Intermediate Similarity	NPC12221
0.8155	Intermediate Similarity	NPC7686
0.8155	Intermediate Similarity	NPC40258
0.8144	Intermediate Similarity	NPC25493
0.8144	Intermediate Similarity	NPC113460
0.8144	Intermediate Similarity	NPC19680
0.8137	Intermediate Similarity	NPC51333

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 NPC275053 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	382
0.1-0.2	1098
0.2-0.3	1593
0.3-0.4	2994
0.4-0.5	1758
0.5-0.6	960
0.6-0.7	305
0.7-0.8	49
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1242	Phase 1
0.87	High Similarity	NPD940	Approved
0.87	High Similarity	NPD846	Approved
0.8469	Intermediate Similarity	NPD2933	Approved
0.8469	Intermediate Similarity	NPD2934	Approved
0.8384	Intermediate Similarity	NPD2859	Approved
0.8384	Intermediate Similarity	NPD2860	Approved
0.8317	Intermediate Similarity	NPD3020	Approved
0.8302	Intermediate Similarity	NPD4750	Phase 3
0.8298	Intermediate Similarity	NPD111	Approved
0.8172	Intermediate Similarity	NPD9089	Approved
0.8065	Intermediate Similarity	NPD9093	Approved
0.7965	Intermediate Similarity	NPD1548	Phase 1
0.7963	Intermediate Similarity	NPD3022	Approved
0.7963	Intermediate Similarity	NPD3021	Approved
0.7921	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD1610	Phase 2
0.7843	Intermediate Similarity	NPD844	Approved
0.7767	Intermediate Similarity	NPD288	Approved
0.7714	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD9094	Approved
0.7623	Intermediate Similarity	NPD3027	Phase 3
0.7603	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2342	Discontinued
0.744	Intermediate Similarity	NPD943	Approved
0.744	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1613	Approved
0.7417	Intermediate Similarity	NPD2983	Phase 2
0.7417	Intermediate Similarity	NPD2982	Phase 2
0.7411	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD4908	Phase 1
0.7395	Intermediate Similarity	NPD422	Phase 1
0.7383	Intermediate Similarity	NPD3028	Approved
0.7364	Intermediate Similarity	NPD968	Approved
0.7358	Intermediate Similarity	NPD9273	Approved
0.7345	Intermediate Similarity	NPD228	Approved
0.7339	Intermediate Similarity	NPD4625	Phase 3
0.7333	Intermediate Similarity	NPD1809	Phase 2
0.7333	Intermediate Similarity	NPD2981	Phase 2
0.7323	Intermediate Similarity	NPD2568	Approved
0.7321	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1792	Phase 2
0.7312	Intermediate Similarity	NPD9087	Approved
0.7308	Intermediate Similarity	NPD845	Approved
0.7281	Intermediate Similarity	NPD9379	Approved
0.7281	Intermediate Similarity	NPD9377	Approved
0.7281	Intermediate Similarity	NPD7635	Approved
0.728	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4749	Approved
0.7248	Intermediate Similarity	NPD9500	Approved
0.7227	Intermediate Similarity	NPD2286	Discontinued
0.7217	Intermediate Similarity	NPD2234	Approved
0.7217	Intermediate Similarity	NPD2228	Approved
0.7217	Intermediate Similarity	NPD2229	Approved
0.7207	Intermediate Similarity	NPD1445	Approved
0.7207	Intermediate Similarity	NPD1444	Approved
0.7203	Intermediate Similarity	NPD3091	Approved
0.719	Intermediate Similarity	NPD9269	Phase 2
0.7188	Intermediate Similarity	NPD9088	Approved
0.7182	Intermediate Similarity	NPD9610	Approved
0.7182	Intermediate Similarity	NPD9608	Approved
0.7177	Intermediate Similarity	NPD3018	Phase 2
0.7155	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4093	Discontinued
0.7143	Intermediate Similarity	NPD9268	Approved
0.7143	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD3092	Approved
0.7107	Intermediate Similarity	NPD1201	Approved
0.7083	Intermediate Similarity	NPD9381	Approved
0.7083	Intermediate Similarity	NPD9384	Approved
0.7083	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3019	Approved
0.7083	Intermediate Similarity	NPD4059	Approved
0.7083	Intermediate Similarity	NPD2932	Approved
0.7077	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD2861	Phase 2
0.7031	Intermediate Similarity	NPD1240	Approved
0.7031	Intermediate Similarity	NPD1555	Discontinued
0.7016	Intermediate Similarity	NPD3094	Phase 2
0.6992	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.696	Remote Similarity	NPD859	Approved
0.696	Remote Similarity	NPD858	Approved
0.696	Remote Similarity	NPD599	Approved
0.696	Remote Similarity	NPD602	Approved
0.696	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6671	Approved
0.6947	Remote Similarity	NPD1510	Phase 2
0.6942	Remote Similarity	NPD1751	Approved
0.6935	Remote Similarity	NPD5310	Approved
0.6935	Remote Similarity	NPD5311	Approved
0.6923	Remote Similarity	NPD1607	Approved
0.6923	Remote Similarity	NPD5283	Phase 1
0.6911	Remote Similarity	NPD2562	Approved
0.6911	Remote Similarity	NPD2561	Approved
0.6907	Remote Similarity	NPD9294	Approved
0.688	Remote Similarity	NPD1470	Approved
0.688	Remote Similarity	NPD3055	Approved
0.688	Remote Similarity	NPD3053	Approved
0.688	Remote Similarity	NPD1164	Approved
0.6875	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD9618	Approved
0.6864	Remote Similarity	NPD9614	Approved
0.6855	Remote Similarity	NPD9622	Approved
0.6855	Remote Similarity	NPD4659	Approved
0.6846	Remote Similarity	NPD230	Phase 1
0.6833	Remote Similarity	NPD16	Approved
0.6833	Remote Similarity	NPD317	Approved
0.6833	Remote Similarity	NPD856	Approved
0.6833	Remote Similarity	NPD318	Approved
0.6825	Remote Similarity	NPD6584	Phase 3
0.6822	Remote Similarity	NPD6405	Approved
0.6822	Remote Similarity	NPD6407	Approved
0.6818	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD709	Approved
0.6803	Remote Similarity	NPD4589	Approved
0.6803	Remote Similarity	NPD3095	Discontinued
0.6788	Remote Similarity	NPD1511	Approved
0.6783	Remote Similarity	NPD74	Approved
0.6783	Remote Similarity	NPD9266	Approved
0.6777	Remote Similarity	NPD5303	Approved
0.6777	Remote Similarity	NPD9545	Approved
0.6777	Remote Similarity	NPD1182	Approved
0.6777	Remote Similarity	NPD5304	Approved
0.6777	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1608	Approved
0.6769	Remote Similarity	NPD3062	Approved
0.6769	Remote Similarity	NPD3061	Approved
0.6769	Remote Similarity	NPD1558	Phase 1
0.6769	Remote Similarity	NPD3059	Approved
0.675	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1981	Approved
0.6748	Remote Similarity	NPD3421	Phase 3
0.6748	Remote Similarity	NPD1983	Approved
0.6748	Remote Similarity	NPD1980	Approved
0.6746	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD4103	Phase 2
0.6724	Remote Similarity	NPD5451	Approved
0.6723	Remote Similarity	NPD1793	Approved
0.6723	Remote Similarity	NPD1791	Approved
0.6723	Remote Similarity	NPD497	Approved
0.6721	Remote Similarity	NPD1357	Approved
0.6716	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD290	Approved
0.6696	Remote Similarity	NPD9264	Approved
0.6696	Remote Similarity	NPD9267	Approved
0.6696	Remote Similarity	NPD9263	Approved
0.6694	Remote Similarity	NPD9613	Approved
0.6694	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5536	Phase 2
0.6694	Remote Similarity	NPD1535	Discovery
0.6694	Remote Similarity	NPD9616	Approved
0.6694	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD9615	Approved
0.6693	Remote Similarity	NPD9620	Approved
0.6693	Remote Similarity	NPD9621	Approved
0.6693	Remote Similarity	NPD9619	Approved
0.6691	Remote Similarity	NPD1512	Approved
0.6691	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD7390	Discontinued
0.6667	Remote Similarity	NPD256	Approved
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD5314	Approved
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4357	Discontinued
0.6667	Remote Similarity	NPD255	Approved
0.6642	Remote Similarity	NPD5404	Approved
0.6642	Remote Similarity	NPD5405	Approved
0.6642	Remote Similarity	NPD1551	Phase 2
0.6642	Remote Similarity	NPD6100	Approved
0.6642	Remote Similarity	NPD5406	Approved
0.6642	Remote Similarity	NPD5408	Approved
0.6642	Remote Similarity	NPD6099	Approved
0.6641	Remote Similarity	NPD468	Phase 1
0.6641	Remote Similarity	NPD5736	Approved
0.6641	Remote Similarity	NPD2238	Phase 2
0.664	Remote Similarity	NPD1481	Phase 2
0.6639	Remote Similarity	NPD498	Approved
0.6639	Remote Similarity	NPD316	Approved
0.6639	Remote Similarity	NPD496	Approved
0.6639	Remote Similarity	NPD495	Approved
0.6638	Remote Similarity	NPD2684	Approved
0.6615	Remote Similarity	NPD3764	Approved
0.6615	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD1131	Approved
0.6614	Remote Similarity	NPD1129	Approved
0.6614	Remote Similarity	NPD1133	Approved
0.6614	Remote Similarity	NPD1134	Approved
0.6614	Remote Similarity	NPD1135	Approved
0.6612	Remote Similarity	NPD9568	Approved
0.6612	Remote Similarity	NPD9493	Approved
0.661	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD9295	Approved
0.6593	Remote Similarity	NPD7266	Discontinued

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