NPASS Compound

Structure

NPC474258 OpenBabel07101718202D 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 1 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:	540.86
Volume:	367.068
LogP:	4.745
LogD:	3.443
LogS:	-4.565
# Rotatable Bonds:	0
TPSA:	80.64
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.358
Synthetic Accessibility Score:	5.035
Fsp3:	0.278
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:	-4.976
MDCK Permeability:	1.7039534213836305e-05
Pgp-inhibitor:	0.117
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.84
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	98.2465591430664%
Volume Distribution (VD):	1.306
Pgp-substrate:	1.1503667831420898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.529
CYP1A2-substrate:	0.473
CYP2C19-inhibitor:	0.659
CYP2C19-substrate:	0.143
CYP2C9-inhibitor:	0.879
CYP2C9-substrate:	0.916
CYP2D6-inhibitor:	0.885
CYP2D6-substrate:	0.797
CYP3A4-inhibitor:	0.374
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	2.477
Half-life (T1/2):	0.419

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.935
AMES Toxicity:	0.498
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.057
Skin Sensitization:	0.284
Carcinogencity:	0.952
Eye Corrosion:	0.003
Eye Irritation:	0.066
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC474258

Natural Product ID:	NPC474258
*Common Name:**	DMJPLPYTMWVIGK-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DMJPLPYTMWVIGK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14Br3N3O2/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/h5-6,15,23-25H,1-4H2
SMILES:	BrC1=CC2(CCNC3=C2C2=NCCc4c2c(C3=O)[nH]c4Br)C=C(C1O)Br
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464377
PubChem CID:	10578448
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	=	645.0	nM	PMID[512746]

☑ 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 NPC474258 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	274
0.1-0.2	2370
0.2-0.3	14773
0.3-0.4	18745
0.4-0.5	3636
0.5-0.6	2321
0.6-0.7	534
0.7-0.8	34
0.8-0.85	4
0.85-0.9	1
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.976	High Similarity	NPC473946
0.9277	High Similarity	NPC186068
0.9244	High Similarity	NPC473628
0.908	High Similarity	NPC475874
0.8621	High Similarity	NPC234403
0.8514	High Similarity	NPC79777
0.8316	Intermediate Similarity	NPC143075
0.8305	Intermediate Similarity	NPC182940
0.8276	Intermediate Similarity	NPC262338
0.8011	Intermediate Similarity	NPC221726
0.8011	Intermediate Similarity	NPC477414
0.8011	Intermediate Similarity	NPC225622
0.7754	Intermediate Similarity	NPC268966
0.7742	Intermediate Similarity	NPC23476
0.7742	Intermediate Similarity	NPC474259
0.7742	Intermediate Similarity	NPC477415
0.7584	Intermediate Similarity	NPC274981
0.7426	Intermediate Similarity	NPC477413
0.7416	Intermediate Similarity	NPC474492
0.7371	Intermediate Similarity	NPC471655
0.7337	Intermediate Similarity	NPC469563
0.7308	Intermediate Similarity	NPC474696
0.7278	Intermediate Similarity	NPC470680
0.7278	Intermediate Similarity	NPC100104
0.7164	Intermediate Similarity	NPC88115
0.7157	Intermediate Similarity	NPC220594
0.7157	Intermediate Similarity	NPC469562
0.7151	Intermediate Similarity	NPC271927
0.715	Intermediate Similarity	NPC106757
0.7135	Intermediate Similarity	NPC469359
0.7112	Intermediate Similarity	NPC37268
0.7065	Intermediate Similarity	NPC71132
0.7059	Intermediate Similarity	NPC80528
0.7053	Intermediate Similarity	NPC477042
0.7035	Intermediate Similarity	NPC477041
0.7035	Intermediate Similarity	NPC477044
0.7005	Intermediate Similarity	NPC6982
0.6985	Remote Similarity	NPC74153
0.6976	Remote Similarity	NPC469578
0.6973	Remote Similarity	NPC2414
0.6966	Remote Similarity	NPC100726
0.695	Remote Similarity	NPC476143
0.6927	Remote Similarity	NPC472861
0.6927	Remote Similarity	NPC184932
0.6919	Remote Similarity	NPC473821
0.6915	Remote Similarity	NPC477045
0.6915	Remote Similarity	NPC469976
0.6889	Remote Similarity	NPC473878
0.6878	Remote Similarity	NPC175602
0.6851	Remote Similarity	NPC470679
0.6851	Remote Similarity	NPC217021
0.6833	Remote Similarity	NPC102664
0.6832	Remote Similarity	NPC477004
0.6829	Remote Similarity	NPC477043
0.6791	Remote Similarity	NPC115232
0.6779	Remote Similarity	NPC61038
0.6763	Remote Similarity	NPC469577
0.6763	Remote Similarity	NPC475410
0.676	Remote Similarity	NPC260041
0.6738	Remote Similarity	NPC73687
0.6733	Remote Similarity	NPC167710
0.6733	Remote Similarity	NPC78767
0.6733	Remote Similarity	NPC473814
0.6714	Remote Similarity	NPC477416
0.67	Remote Similarity	NPC47190
0.6699	Remote Similarity	NPC476252
0.6685	Remote Similarity	NPC474236
0.6683	Remote Similarity	NPC292361
0.6682	Remote Similarity	NPC469715
0.6667	Remote Similarity	NPC237414
0.6651	Remote Similarity	NPC207866
0.6649	Remote Similarity	NPC302647
0.6637	Remote Similarity	NPC475635
0.6634	Remote Similarity	NPC93390
0.6633	Remote Similarity	NPC209917
0.6604	Remote Similarity	NPC469544
0.6599	Remote Similarity	NPC110158
0.6595	Remote Similarity	NPC470507
0.6592	Remote Similarity	NPC114033
0.6592	Remote Similarity	NPC129412
0.6592	Remote Similarity	NPC58268
0.6592	Remote Similarity	NPC101130
0.6584	Remote Similarity	NPC19342
0.6571	Remote Similarity	NPC150592
0.6566	Remote Similarity	NPC133003
0.6538	Remote Similarity	NPC98715
0.6535	Remote Similarity	NPC472292
0.6528	Remote Similarity	NPC34508
0.6526	Remote Similarity	NPC110182
0.6524	Remote Similarity	NPC76982
0.6522	Remote Similarity	NPC300183
0.6522	Remote Similarity	NPC471944
0.6517	Remote Similarity	NPC324091
0.6515	Remote Similarity	NPC477003
0.6513	Remote Similarity	NPC284775
0.651	Remote Similarity	NPC471943
0.6505	Remote Similarity	NPC38736
0.6482	Remote Similarity	NPC476423
0.6474	Remote Similarity	NPC271734
0.6473	Remote Similarity	NPC13456
0.6473	Remote Similarity	NPC269203
0.6473	Remote Similarity	NPC77241
0.6473	Remote Similarity	NPC166209
0.6467	Remote Similarity	NPC124005
0.6467	Remote Similarity	NPC37548
0.6467	Remote Similarity	NPC187951
0.6465	Remote Similarity	NPC50562
0.6448	Remote Similarity	NPC129042
0.6445	Remote Similarity	NPC225821
0.6445	Remote Similarity	NPC46225
0.6443	Remote Similarity	NPC252572
0.6442	Remote Similarity	NPC9635
0.6439	Remote Similarity	NPC102592
0.6439	Remote Similarity	NPC79356
0.6439	Remote Similarity	NPC472293
0.6436	Remote Similarity	NPC299594
0.6436	Remote Similarity	NPC27296
0.6435	Remote Similarity	NPC67658
0.6432	Remote Similarity	NPC52110
0.6429	Remote Similarity	NPC157583
0.6429	Remote Similarity	NPC242556
0.6425	Remote Similarity	NPC472297
0.6425	Remote Similarity	NPC268744
0.6425	Remote Similarity	NPC475914
0.6425	Remote Similarity	NPC472296
0.6425	Remote Similarity	NPC136957
0.6425	Remote Similarity	NPC220797
0.6425	Remote Similarity	NPC474318
0.6425	Remote Similarity	NPC153123
0.6425	Remote Similarity	NPC19696
0.6425	Remote Similarity	NPC201266
0.6421	Remote Similarity	NPC214106
0.642	Remote Similarity	NPC20021
0.6419	Remote Similarity	NPC470703
0.6417	Remote Similarity	NPC209362
0.6415	Remote Similarity	NPC258062
0.6415	Remote Similarity	NPC127677
0.6406	Remote Similarity	NPC109447
0.6404	Remote Similarity	NPC292434
0.6404	Remote Similarity	NPC200397
0.6404	Remote Similarity	NPC243716
0.6404	Remote Similarity	NPC138596
0.6404	Remote Similarity	NPC98156
0.6404	Remote Similarity	NPC64661
0.6404	Remote Similarity	NPC14448
0.6404	Remote Similarity	NPC167200
0.6404	Remote Similarity	NPC195704
0.6396	Remote Similarity	NPC270009
0.639	Remote Similarity	NPC202812
0.6387	Remote Similarity	NPC206148
0.6386	Remote Similarity	NPC221873
0.6378	Remote Similarity	NPC151635
0.6378	Remote Similarity	NPC2272
0.6378	Remote Similarity	NPC123906
0.6372	Remote Similarity	NPC473218
0.6372	Remote Similarity	NPC470702
0.6372	Remote Similarity	NPC207020
0.6368	Remote Similarity	NPC473706
0.6368	Remote Similarity	NPC473320
0.6364	Remote Similarity	NPC251391
0.6364	Remote Similarity	NPC88110
0.6359	Remote Similarity	NPC179701
0.6359	Remote Similarity	NPC77061
0.6354	Remote Similarity	NPC286529
0.6354	Remote Similarity	NPC205604
0.6354	Remote Similarity	NPC209281
0.6354	Remote Similarity	NPC12831
0.6354	Remote Similarity	NPC48171
0.6354	Remote Similarity	NPC74928
0.6354	Remote Similarity	NPC3698
0.6354	Remote Similarity	NPC169308
0.6354	Remote Similarity	NPC302717
0.6354	Remote Similarity	NPC77582
0.6354	Remote Similarity	NPC129753
0.6354	Remote Similarity	NPC244087
0.6354	Remote Similarity	NPC474383
0.6354	Remote Similarity	NPC59839
0.6354	Remote Similarity	NPC97230
0.635	Remote Similarity	NPC21429
0.6349	Remote Similarity	NPC213914
0.6347	Remote Similarity	NPC269270
0.6344	Remote Similarity	NPC174489
0.6341	Remote Similarity	NPC269886
0.6341	Remote Similarity	NPC304203
0.6341	Remote Similarity	NPC472295
0.6341	Remote Similarity	NPC472210
0.6341	Remote Similarity	NPC247735
0.6341	Remote Similarity	NPC81802
0.6333	Remote Similarity	NPC328596
0.6333	Remote Similarity	NPC328318
0.6332	Remote Similarity	NPC275292
0.6332	Remote Similarity	NPC192270
0.6332	Remote Similarity	NPC243381
0.6332	Remote Similarity	NPC191415
0.633	Remote Similarity	NPC471458
0.6329	Remote Similarity	NPC174281
0.6329	Remote Similarity	NPC475286
0.6329	Remote Similarity	NPC262898
0.6327	Remote Similarity	NPC279189
0.6327	Remote Similarity	NPC200553

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 NPC474258 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	171
0.1-0.2	595
0.2-0.3	1002
0.3-0.4	2650
0.4-0.5	3373
0.5-0.6	1268
0.6-0.7	91
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
0.694	Remote Similarity	NPD2214	Approved
0.694	Remote Similarity	NPD2213	Approved
0.6701	Remote Similarity	NPD5473	Discontinued
0.6582	Remote Similarity	NPD3178	Discontinued
0.658	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6376	Discontinued
0.6468	Remote Similarity	NPD1996	Discontinued
0.6432	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5901	Discontinued
0.6364	Remote Similarity	NPD1643	Phase 3
0.6275	Remote Similarity	NPD4499	Approved
0.6257	Remote Similarity	NPD4462	Approved
0.6257	Remote Similarity	NPD4463	Approved
0.6256	Remote Similarity	NPD3961	Discontinued
0.6237	Remote Similarity	NPD4643	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD7454	Approved
0.6221	Remote Similarity	NPD7455	Approved
0.62	Remote Similarity	NPD1291	Clinical (unspecified phase)
0.6193	Remote Similarity	NPD4524	Discontinued
0.6165	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD3319	Phase 1
0.6139	Remote Similarity	NPD3318	Approved
0.6139	Remote Similarity	NPD3320	Approved
0.6136	Remote Similarity	NPD3393	Approved
0.6136	Remote Similarity	NPD3389	Approved
0.6136	Remote Similarity	NPD3394	Approved
0.6134	Remote Similarity	NPD1631	Approved
0.6126	Remote Similarity	NPD276	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6249	Phase 2
0.6114	Remote Similarity	NPD6248	Phase 2
0.61	Remote Similarity	NPD3505	Approved
0.61	Remote Similarity	NPD3506	Approved
0.6091	Remote Similarity	NPD1575	Approved
0.6091	Remote Similarity	NPD1573	Approved
0.6087	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD4600	Approved
0.6085	Remote Similarity	NPD4601	Approved
0.608	Remote Similarity	NPD482	Approved
0.6077	Remote Similarity	NPD7619	Phase 3
0.6077	Remote Similarity	NPD7618	Phase 3
0.6075	Remote Similarity	NPD6176	Phase 1
0.6073	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.607	Remote Similarity	NPD4079	Approved
0.607	Remote Similarity	NPD4076	Approved
0.6066	Remote Similarity	NPD2323	Clinical (unspecified phase)
0.6062	Remote Similarity	NPD1630	Approved
0.6058	Remote Similarity	NPD7098	Clinical (unspecified phase)
0.6054	Remote Similarity	NPD5020	Approved
0.605	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD5809	Phase 3
0.6048	Remote Similarity	NPD4848	Phase 1
0.6048	Remote Similarity	NPD2289	Phase 3
0.6048	Remote Similarity	NPD2290	Phase 3
0.6047	Remote Similarity	NPD8114	Approved
0.6047	Remote Similarity	NPD8115	Approved
0.6041	Remote Similarity	NPD2844	Phase 3
0.6033	Remote Similarity	NPD569	Clinical (unspecified phase)
0.602	Remote Similarity	NPD2753	Discontinued
0.6019	Remote Similarity	NPD4948	Discontinued
0.6019	Remote Similarity	NPD3246	Discontinued
0.6019	Remote Similarity	NPD4988	Discontinued
0.6018	Remote Similarity	NPD7716	Approved
0.6018	Remote Similarity	NPD7717	Approved
0.6009	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6009	Remote Similarity	NPD4520	Approved
0.6009	Remote Similarity	NPD4500	Approved
0.6009	Remote Similarity	NPD4501	Approved
0.5991	Remote Similarity	NPD7204	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD6017	Discontinued
0.5982	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7727	Phase 2
0.5981	Remote Similarity	NPD4922	Phase 2
0.5981	Remote Similarity	NPD7817	Phase 1
0.598	Remote Similarity	NPD2095	Phase 2
0.598	Remote Similarity	NPD2092	Phase 2
0.598	Remote Similarity	NPD2094	Phase 2
0.598	Remote Similarity	NPD5728	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.597	Remote Similarity	NPD4075	Phase 2
0.597	Remote Similarity	NPD3238	Discontinued
0.597	Remote Similarity	NPD5104	Approved
0.5963	Remote Similarity	NPD2509	Approved
0.5963	Remote Similarity	NPD2510	Approved
0.5962	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD2096	Phase 2
0.5951	Remote Similarity	NPD2091	Phase 2
0.5943	Remote Similarity	NPD6664	Approved
0.5939	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7878	Phase 2
0.5935	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.5931	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5487	Phase 1
0.5913	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD4051	Discontinued
0.5905	Remote Similarity	NPD1896	Approved
0.5902	Remote Similarity	NPD5596	Phase 2
0.5894	Remote Similarity	NPD3315	Phase 3
0.5888	Remote Similarity	NPD3425	Discontinued
0.5882	Remote Similarity	NPD2479	Phase 3
0.5882	Remote Similarity	NPD2481	Approved
0.5882	Remote Similarity	NPD4614	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.5879	Remote Similarity	NPD5021	Discontinued
0.5879	Remote Similarity	NPD1627	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD460	Discontinued
0.5874	Remote Similarity	NPD7564	Discontinued
0.5874	Remote Similarity	NPD7482	Phase 2
0.5874	Remote Similarity	NPD7483	Phase 2
0.5874	Remote Similarity	NPD1096	Discontinued
0.5872	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD3100	Discontinued
0.5864	Remote Similarity	NPD5835	Phase 3
0.5864	Remote Similarity	NPD5834	Phase 3
0.586	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD2915	Discontinued
0.5857	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD3918	Approved
0.5856	Remote Similarity	NPD3917	Approved
0.5856	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.585	Remote Similarity	NPD1326	Approved
0.585	Remote Similarity	NPD1325	Approved
0.5845	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5065	Approved
0.5842	Remote Similarity	NPD4883	Approved
0.5837	Remote Similarity	NPD4334	Discontinued
0.5833	Remote Similarity	NPD1587	Approved
0.5833	Remote Similarity	NPD6995	Phase 1
0.5826	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD3379	Phase 2
0.5826	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD3380	Phase 3
0.5826	Remote Similarity	NPD3947	Discontinued
0.5825	Remote Similarity	NPD7401	Clinical (unspecified phase)
0.5822	Remote Similarity	NPD1871	Approved
0.5818	Remote Similarity	NPD8399	Phase 1
0.5818	Remote Similarity	NPD8423	Phase 2
0.5818	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.5817	Remote Similarity	NPD4940	Approved
0.5815	Remote Similarity	NPD6242	Discontinued
0.5814	Remote Similarity	NPD7308	Discontinued
0.5812	Remote Similarity	NPD1270	Approved
0.5811	Remote Similarity	NPD3915	Approved
0.5806	Remote Similarity	NPD3773	Approved
0.5806	Remote Similarity	NPD3774	Approved
0.5806	Remote Similarity	NPD3775	Approved
0.5806	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.5805	Remote Similarity	NPD5898	Approved
0.5805	Remote Similarity	NPD5899	Approved
0.5805	Remote Similarity	NPD5897	Approved
0.5804	Remote Similarity	NPD6481	Clinical (unspecified phase)
0.5803	Remote Similarity	NPD5965	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6206	Phase 1
0.5792	Remote Similarity	NPD750	Phase 2
0.5792	Remote Similarity	NPD1600	Suspended
0.5787	Remote Similarity	NPD2912	Approved
0.5787	Remote Similarity	NPD484	Approved
0.5787	Remote Similarity	NPD2911	Approved
0.5781	Remote Similarity	NPD4374	Clinical (unspecified phase)
0.5779	Remote Similarity	NPD1568	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD6770	Approved
0.5769	Remote Similarity	NPD5075	Discontinued
0.5767	Remote Similarity	NPD7946	Pre-registration
0.5767	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.5767	Remote Similarity	NPD6261	Phase 3
0.5766	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.5764	Remote Similarity	NPD1586	Approved
0.5764	Remote Similarity	NPD4128	Approved
0.5762	Remote Similarity	NPD6068	Discontinued
0.5756	Remote Similarity	NPD8386	Phase 2
0.5755	Remote Similarity	NPD4315	Phase 2
0.5753	Remote Similarity	NPD8282	Approved
0.5753	Remote Similarity	NPD8283	Approved
0.5753	Remote Similarity	NPD56	Approved
0.5753	Remote Similarity	NPD8098	Approved
0.5751	Remote Similarity	NPD2172	Phase 1
0.575	Remote Similarity	NPD6446	Discontinued
0.5742	Remote Similarity	NPD5444	Phase 1
0.5742	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD6137	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD2565	Phase 2
0.5735	Remote Similarity	NPD2564	Approved
0.5735	Remote Similarity	NPD2381	Approved
0.5735	Remote Similarity	NPD2380	Approved
0.5735	Remote Similarity	NPD2382	Approved
0.5734	Remote Similarity	NPD7187	Phase 2
0.5733	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD5140	Approved
0.5729	Remote Similarity	NPD5138	Approved
0.5728	Remote Similarity	NPD4348	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD7568	Phase 1
0.5727	Remote Similarity	NPD7010	Phase 3
0.5721	Remote Similarity	NPD1343	Approved
0.5721	Remote Similarity	NPD721	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