NPASS Compound

Structure

NPC473946 OpenBabel07101718182D 26 30 0 0 1 0 0 0 0 0999 V2000 2.1877 1.4133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1278 -2.5783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1290 1.0760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4236 -2.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1278 -0.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9938 -2.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4248 0.7667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9938 -0.2651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8598 -1.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6034 -0.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4236 -1.3586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5448 -0.5545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7228 -0.6911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7194 -1.7651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8598 -0.7651 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9625 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4339 0.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1278 -1.7651 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.9938 0.7349 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 5.7259 -2.2651 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -0.0400 1.7816 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 3.3076 0.0921 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7194 -2.5783 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7259 -0.2651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2294 -2.1482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 7 1 0 0 0 0 2 4 2 0 0 0 0 2 18 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 8 2 0 0 0 0 5 18 1 0 0 0 0 6 9 2 0 0 0 0 6 18 1 0 0 0 0 7 10 1 0 0 0 0 7 17 2 0 0 0 0 8 15 1 0 0 0 0 8 19 1 0 0 0 0 9 15 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 13 2 0 0 0 0 11 12 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 22 2 0 0 0 0 13 16 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 25 1 0 0 0 0 16 26 2 0 0 0 0 17 21 1 0 0 0 0 17 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	538.85
Volume:	364.432
LogP:	4.798
LogD:	3.501
LogS:	-4.056
# Rotatable Bonds:	0
TPSA:	80.97
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.43
Synthetic Accessibility Score:	5.159
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.984
MDCK Permeability:	1.7128764739027247e-05
Pgp-inhibitor:	0.197
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.779
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.197
Plasma Protein Binding (PPB):	97.8171615600586%
Volume Distribution (VD):	1.15
Pgp-substrate:	1.2756954431533813%

ADMET: Metabolism

CYP1A2-inhibitor:	0.393
CYP1A2-substrate:	0.457
CYP2C19-inhibitor:	0.386
CYP2C19-substrate:	0.168
CYP2C9-inhibitor:	0.787
CYP2C9-substrate:	0.886
CYP2D6-inhibitor:	0.791
CYP2D6-substrate:	0.828
CYP3A4-inhibitor:	0.297
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	1.474
Half-life (T1/2):	0.427

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.167
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.997
Maximum Recommended Daily Dose:	0.063
Skin Sensitization:	0.483
Carcinogencity:	0.968
Eye Corrosion:	0.003
Eye Irritation:	0.171
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC473946

Natural Product ID:	NPC473946
*Common Name:**	VCBOKXIVCCHFSL-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VCBOKXIVCCHFSL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12Br3N3O2/c19-8-5-18(6-9(20)15(8)25)2-4-23-14-11(18)12-10-7(1-3-22-12)17(21)24-13(10)16(14)26/h2,4-6,15,23-25H,1,3H2
SMILES:	BrC1=CC2(C=CNC3=C2C2=NCCc4c2c(C3=O)[nH]c4Br)C=C(C1O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455888
PubChem CID:	11341740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001626] Phenanthrolines

*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
NPO32524	latrunculid sponges	Species	n.a.	n.a.	n.a.	South African	n.a.	PMID[15332840]

☑ 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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	222.0	nM	PMID[502087]

☑ 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 NPC473946 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	292
0.1-0.2	2401
0.2-0.3	14657
0.3-0.4	18701
0.4-0.5	3503
0.5-0.6	2459
0.6-0.7	641
0.7-0.8	33
0.8-0.85	5
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.976	High Similarity	NPC474258
0.9306	High Similarity	NPC475874
0.9138	High Similarity	NPC473628
0.9053	High Similarity	NPC186068
0.8523	High Similarity	NPC79777
0.8523	High Similarity	NPC234403
0.8286	Intermediate Similarity	NPC262338
0.8229	Intermediate Similarity	NPC143075
0.8212	Intermediate Similarity	NPC182940
0.7957	Intermediate Similarity	NPC268966
0.7926	Intermediate Similarity	NPC221726
0.7926	Intermediate Similarity	NPC477414
0.7926	Intermediate Similarity	NPC225622
0.7754	Intermediate Similarity	NPC474259
0.7754	Intermediate Similarity	NPC477415
0.7754	Intermediate Similarity	NPC23476
0.7525	Intermediate Similarity	NPC477413
0.75	Intermediate Similarity	NPC274981
0.7486	Intermediate Similarity	NPC471655
0.743	Intermediate Similarity	NPC474492
0.7389	Intermediate Similarity	NPC100104
0.7389	Intermediate Similarity	NPC470680
0.7337	Intermediate Similarity	NPC106757
0.7264	Intermediate Similarity	NPC88115
0.7264	Intermediate Similarity	NPC469563
0.7135	Intermediate Similarity	NPC474696
0.7107	Intermediate Similarity	NPC473821
0.7087	Intermediate Similarity	NPC220594
0.7087	Intermediate Similarity	NPC469562
0.7085	Intermediate Similarity	NPC74153
0.7081	Intermediate Similarity	NPC71132
0.7079	Intermediate Similarity	NPC100726
0.7068	Intermediate Similarity	NPC477042
0.7062	Intermediate Similarity	NPC469359
0.705	Intermediate Similarity	NPC477044
0.705	Intermediate Similarity	NPC477041
0.7037	Intermediate Similarity	NPC37268
0.7021	Intermediate Similarity	NPC6982
0.7	Intermediate Similarity	NPC473878
0.6984	Remote Similarity	NPC271927
0.6984	Remote Similarity	NPC80528
0.6976	Remote Similarity	NPC175602
0.6961	Remote Similarity	NPC470679
0.6961	Remote Similarity	NPC217021
0.6931	Remote Similarity	NPC469976
0.6931	Remote Similarity	NPC477004
0.6931	Remote Similarity	NPC477045
0.6908	Remote Similarity	NPC469578
0.6898	Remote Similarity	NPC2414
0.6881	Remote Similarity	NPC476143
0.6875	Remote Similarity	NPC61038
0.6856	Remote Similarity	NPC472861
0.6856	Remote Similarity	NPC184932
0.6851	Remote Similarity	NPC102664
0.6845	Remote Similarity	NPC477043
0.6832	Remote Similarity	NPC473814
0.6832	Remote Similarity	NPC78767
0.6832	Remote Similarity	NPC167710
0.6816	Remote Similarity	NPC93390
0.6809	Remote Similarity	NPC115232
0.68	Remote Similarity	NPC47190
0.6765	Remote Similarity	NPC237414
0.6755	Remote Similarity	NPC73687
0.6745	Remote Similarity	NPC207866
0.6734	Remote Similarity	NPC209917
0.6701	Remote Similarity	NPC110158
0.67	Remote Similarity	NPC292361
0.6699	Remote Similarity	NPC469577
0.6699	Remote Similarity	NPC475410
0.6685	Remote Similarity	NPC260041
0.6667	Remote Similarity	NPC302647
0.6652	Remote Similarity	NPC475635
0.6651	Remote Similarity	NPC477416
0.6635	Remote Similarity	NPC476252
0.6635	Remote Similarity	NPC98715
0.6634	Remote Similarity	NPC472292
0.6618	Remote Similarity	NPC471944
0.6618	Remote Similarity	NPC300183
0.6616	Remote Similarity	NPC477003
0.6615	Remote Similarity	NPC284775
0.6615	Remote Similarity	NPC157583
0.6613	Remote Similarity	NPC474236
0.6613	Remote Similarity	NPC470507
0.6613	Remote Similarity	NPC209362
0.6611	Remote Similarity	NPC58268
0.6611	Remote Similarity	NPC114033
0.6611	Remote Similarity	NPC129412
0.6611	Remote Similarity	NPC101130
0.6601	Remote Similarity	NPC19342
0.6583	Remote Similarity	NPC133003
0.6576	Remote Similarity	NPC187951
0.657	Remote Similarity	NPC166209
0.657	Remote Similarity	NPC77241
0.657	Remote Similarity	NPC269203
0.657	Remote Similarity	NPC13456
0.6557	Remote Similarity	NPC129042
0.6546	Remote Similarity	NPC34508
0.6543	Remote Similarity	NPC76982
0.6542	Remote Similarity	NPC110182
0.6542	Remote Similarity	NPC469715
0.6542	Remote Similarity	NPC469544
0.654	Remote Similarity	NPC225821
0.654	Remote Similarity	NPC46225
0.6538	Remote Similarity	NPC9635
0.6537	Remote Similarity	NPC472293
0.6537	Remote Similarity	NPC102592
0.6537	Remote Similarity	NPC79356
0.6535	Remote Similarity	NPC324091
0.6528	Remote Similarity	NPC471943
0.6524	Remote Similarity	NPC38736
0.6522	Remote Similarity	NPC220797
0.6522	Remote Similarity	NPC474318
0.6522	Remote Similarity	NPC153123
0.6522	Remote Similarity	NPC472296
0.6522	Remote Similarity	NPC201266
0.6522	Remote Similarity	NPC472297
0.6522	Remote Similarity	NPC268744
0.6522	Remote Similarity	NPC475914
0.6512	Remote Similarity	NPC470703
0.6509	Remote Similarity	NPC127677
0.6509	Remote Similarity	NPC258062
0.6507	Remote Similarity	NPC328596
0.6507	Remote Similarity	NPC328318
0.6497	Remote Similarity	NPC150592
0.6492	Remote Similarity	NPC206148
0.6492	Remote Similarity	NPC271734
0.6489	Remote Similarity	NPC74357
0.6488	Remote Similarity	NPC202812
0.6486	Remote Similarity	NPC123906
0.6486	Remote Similarity	NPC124005
0.6486	Remote Similarity	NPC37548
0.6481	Remote Similarity	NPC50562
0.6471	Remote Similarity	NPC251391
0.6471	Remote Similarity	NPC216550
0.6465	Remote Similarity	NPC207020
0.6465	Remote Similarity	NPC473218
0.6465	Remote Similarity	NPC470702
0.6462	Remote Similarity	NPC252572
0.6456	Remote Similarity	NPC179701
0.6455	Remote Similarity	NPC213914
0.6455	Remote Similarity	NPC299594
0.6452	Remote Similarity	NPC67658
0.6448	Remote Similarity	NPC242556
0.6442	Remote Similarity	NPC136957
0.6442	Remote Similarity	NPC19696
0.6441	Remote Similarity	NPC20021
0.644	Remote Similarity	NPC214106
0.6439	Remote Similarity	NPC304203
0.6438	Remote Similarity	NPC269270
0.6432	Remote Similarity	NPC191415
0.6432	Remote Similarity	NPC174489
0.6432	Remote Similarity	NPC243381
0.6432	Remote Similarity	NPC275292
0.6425	Remote Similarity	NPC195704
0.6425	Remote Similarity	NPC262898
0.6425	Remote Similarity	NPC109447
0.6425	Remote Similarity	NPC292434
0.6425	Remote Similarity	NPC64661
0.6425	Remote Similarity	NPC167200
0.6425	Remote Similarity	NPC14448
0.6425	Remote Similarity	NPC200397
0.6425	Remote Similarity	NPC138596
0.6425	Remote Similarity	NPC98156
0.6422	Remote Similarity	NPC476460
0.6422	Remote Similarity	NPC243716
0.6418	Remote Similarity	NPC476423
0.6416	Remote Similarity	NPC279189
0.6416	Remote Similarity	NPC200553
0.6414	Remote Similarity	NPC276540
0.6414	Remote Similarity	NPC233050
0.6414	Remote Similarity	NPC270009
0.6409	Remote Similarity	NPC14686
0.6404	Remote Similarity	NPC162002
0.6404	Remote Similarity	NPC221873
0.6402	Remote Similarity	NPC271862
0.64	Remote Similarity	NPC159125
0.64	Remote Similarity	NPC102755
0.6398	Remote Similarity	NPC2272
0.6396	Remote Similarity	NPC151635
0.6389	Remote Similarity	NPC87856
0.6389	Remote Similarity	NPC151976
0.6387	Remote Similarity	NPC473320
0.6387	Remote Similarity	NPC473706
0.6386	Remote Similarity	NPC63571
0.6383	Remote Similarity	NPC281094
0.6382	Remote Similarity	NPC88110
0.6377	Remote Similarity	NPC77061
0.6376	Remote Similarity	NPC26641
0.6374	Remote Similarity	NPC302717
0.6374	Remote Similarity	NPC77582
0.6374	Remote Similarity	NPC129753
0.6374	Remote Similarity	NPC244087
0.6374	Remote Similarity	NPC59839
0.6374	Remote Similarity	NPC97230
0.6374	Remote Similarity	NPC286529
0.6374	Remote Similarity	NPC205604
0.6374	Remote Similarity	NPC209281
0.6374	Remote Similarity	NPC48171
0.6374	Remote Similarity	NPC74928
0.6374	Remote Similarity	NPC3698

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 NPC473946 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	606
0.2-0.3	945
0.3-0.4	2588
0.4-0.5	3270
0.5-0.6	1448
0.6-0.7	116
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6774	Remote Similarity	NPD2213	Approved
0.6774	Remote Similarity	NPD2214	Approved
0.6718	Remote Similarity	NPD5473	Discontinued
0.6599	Remote Similarity	NPD3178	Discontinued
0.6598	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.656	Remote Similarity	NPD1996	Discontinued
0.6533	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5901	Discontinued
0.6509	Remote Similarity	NPD6376	Discontinued
0.6465	Remote Similarity	NPD1643	Phase 3
0.6355	Remote Similarity	NPD3961	Discontinued
0.63	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD4499	Approved
0.6277	Remote Similarity	NPD4462	Approved
0.6277	Remote Similarity	NPD4463	Approved
0.6262	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7454	Approved
0.6239	Remote Similarity	NPD7455	Approved
0.6237	Remote Similarity	NPD1631	Approved
0.6232	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6227	Remote Similarity	NPD3393	Approved
0.6227	Remote Similarity	NPD3394	Approved
0.6227	Remote Similarity	NPD3389	Approved
0.6224	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4848	Phase 1
0.622	Remote Similarity	NPD2290	Phase 3
0.622	Remote Similarity	NPD2289	Phase 3
0.6212	Remote Similarity	NPD4524	Discontinued
0.62	Remote Similarity	NPD3506	Approved
0.62	Remote Similarity	NPD3505	Approved
0.62	Remote Similarity	NPD2753	Discontinued
0.6195	Remote Similarity	NPD4988	Discontinued
0.6193	Remote Similarity	NPD1575	Approved
0.6193	Remote Similarity	NPD1573	Approved
0.6184	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD482	Approved
0.6175	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD7619	Phase 3
0.6172	Remote Similarity	NPD7618	Phase 3
0.6169	Remote Similarity	NPD4079	Approved
0.6169	Remote Similarity	NPD4076	Approved
0.6168	Remote Similarity	NPD6176	Phase 1
0.6166	Remote Similarity	NPD1630	Approved
0.6162	Remote Similarity	NPD5020	Approved
0.6161	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD3319	Phase 1
0.6158	Remote Similarity	NPD3318	Approved
0.6158	Remote Similarity	NPD3320	Approved
0.615	Remote Similarity	NPD3238	Discontinued
0.615	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5809	Phase 3
0.6146	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD6249	Phase 2
0.6132	Remote Similarity	NPD6248	Phase 2
0.6117	Remote Similarity	NPD3246	Discontinued
0.6106	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6103	Remote Similarity	NPD4601	Approved
0.6103	Remote Similarity	NPD4600	Approved
0.6101	Remote Similarity	NPD4520	Approved
0.6096	Remote Similarity	NPD6017	Discontinued
0.6094	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD2094	Phase 2
0.6078	Remote Similarity	NPD2095	Phase 2
0.6078	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD2092	Phase 2
0.6077	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD4922	Phase 2
0.6073	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.607	Remote Similarity	NPD4075	Phase 2
0.607	Remote Similarity	NPD5104	Approved
0.6065	Remote Similarity	NPD8114	Approved
0.6065	Remote Similarity	NPD8115	Approved
0.6062	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD2844	Phase 3
0.6055	Remote Similarity	NPD2509	Approved
0.6055	Remote Similarity	NPD2510	Approved
0.6054	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD2096	Phase 2
0.6049	Remote Similarity	NPD2091	Phase 2
0.6048	Remote Similarity	NPD460	Discontinued
0.6039	Remote Similarity	NPD4948	Discontinued
0.6038	Remote Similarity	NPD6664	Approved
0.6035	Remote Similarity	NPD7716	Approved
0.6035	Remote Similarity	NPD7717	Approved
0.6029	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD4500	Approved
0.6028	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD4501	Approved
0.6026	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7817	Phase 1
0.6	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4051	Discontinued
0.6	Remote Similarity	NPD1270	Approved
0.6	Remote Similarity	NPD7727	Phase 2
0.5991	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.5991	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.599	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.599	Remote Similarity	NPD3315	Phase 3
0.5981	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.598	Remote Similarity	NPD2481	Approved
0.598	Remote Similarity	NPD2479	Phase 3
0.5973	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.5971	Remote Similarity	NPD7564	Discontinued
0.5971	Remote Similarity	NPD7482	Phase 2
0.5971	Remote Similarity	NPD1096	Discontinued
0.5971	Remote Similarity	NPD7483	Phase 2
0.5969	Remote Similarity	NPD3100	Discontinued
0.5963	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.596	Remote Similarity	NPD2915	Discontinued
0.596	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.596	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD7878	Phase 2
0.5955	Remote Similarity	NPD1600	Suspended
0.5953	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.5945	Remote Similarity	NPD5487	Phase 1
0.5941	Remote Similarity	NPD4883	Approved
0.5941	Remote Similarity	NPD5065	Approved
0.5936	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.5933	Remote Similarity	NPD4334	Discontinued
0.5933	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD1587	Approved
0.593	Remote Similarity	NPD6446	Discontinued
0.5924	Remote Similarity	NPD1896	Approved
0.5922	Remote Similarity	NPD5596	Phase 2
0.5921	Remote Similarity	NPD6995	Phase 1
0.5917	Remote Similarity	NPD3947	Discontinued
0.5917	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD4940	Approved
0.5909	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.5904	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.5903	Remote Similarity	NPD6242	Discontinued
0.5902	Remote Similarity	NPD5898	Approved
0.5902	Remote Similarity	NPD5899	Approved
0.5902	Remote Similarity	NPD5897	Approved
0.59	Remote Similarity	NPD1343	Approved
0.59	Remote Similarity	NPD7287	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5021	Discontinued
0.5899	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD3773	Approved
0.5899	Remote Similarity	NPD3774	Approved
0.5899	Remote Similarity	NPD3775	Approved
0.5894	Remote Similarity	NPD721	Approved
0.5893	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD750	Phase 2
0.589	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6206	Phase 1
0.5888	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.588	Remote Similarity	NPD484	Approved
0.5877	Remote Similarity	NPD2336	Approved
0.5874	Remote Similarity	NPD3917	Approved
0.5874	Remote Similarity	NPD3918	Approved
0.5874	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD1326	Approved
0.5871	Remote Similarity	NPD1325	Approved
0.5869	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD5075	Discontinued
0.5862	Remote Similarity	NPD1586	Approved
0.5862	Remote Similarity	NPD4128	Approved
0.586	Remote Similarity	NPD6261	Phase 3
0.5859	Remote Similarity	NPD5400	Approved
0.5857	Remote Similarity	NPD7234	Approved
0.5857	Remote Similarity	NPD7233	Approved
0.5856	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD2172	Phase 1
0.5845	Remote Similarity	NPD3379	Phase 2
0.5845	Remote Similarity	NPD6987	Phase 1
0.5845	Remote Similarity	NPD3380	Phase 3
0.5841	Remote Similarity	NPD1871	Approved
0.5837	Remote Similarity	NPD8423	Phase 2
0.5837	Remote Similarity	NPD5444	Phase 1
0.5837	Remote Similarity	NPD8399	Phase 1
0.5833	Remote Similarity	NPD7308	Discontinued
0.5833	Remote Similarity	NPD3425	Discontinued
0.583	Remote Similarity	NPD3915	Approved
0.5829	Remote Similarity	NPD5088	Discontinued
0.5826	Remote Similarity	NPD7187	Phase 2
0.5822	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD4638	Approved
0.5821	Remote Similarity	NPD4640	Approved
0.5821	Remote Similarity	NPD4639	Approved
0.5819	Remote Similarity	NPD4845	Discontinued
0.5818	Remote Similarity	NPD7568	Phase 1
0.5818	Remote Similarity	NPD7010	Phase 3
0.5818	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD5834	Phase 3
0.5811	Remote Similarity	NPD5835	Phase 3
0.5806	Remote Similarity	NPD198	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD2144	Approved
0.5804	Remote Similarity	NPD8093	Discontinued
0.5803	Remote Similarity	NPD1183	Approved
0.5801	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD2071	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