NPASS Compound

Structure

NPC469715 OpenBabel07101718192D 21 24 0 0 1 0 0 0 0 0999 V2000 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3364 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9921 2.2601 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 4.2709 0.5000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 0.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.8364 3.4487 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 2.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 1.6691 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 -1.2601 2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 1 19 1 0 0 0 0 2 7 1 0 0 0 0 2 14 1 6 0 0 0 3 4 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 8 2 0 0 0 0 4 12 1 0 0 0 0 5 9 1 0 0 0 0 5 16 1 0 0 0 0 6 11 1 0 0 0 0 6 17 1 0 0 0 0 7 11 1 6 0 0 0 7 20 1 0 0 0 0 8 13 1 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 9 21 2 0 0 0 0 10 15 2 0 0 0 0 10 17 1 0 0 0 0 10 18 1 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.89
Volume:	280.383
LogP:	1.249
LogD:	1.155
LogS:	-2.832
# Rotatable Bonds:	0
TPSA:	106.74
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.445
Synthetic Accessibility Score:	5.695
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.365
MDCK Permeability:	1.3976889931655023e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.133
Human Intestinal Absorption (HIA):	0.653
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.062

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.546
Plasma Protein Binding (PPB):	76.78429412841797%
Volume Distribution (VD):	0.964
Pgp-substrate:	25.1010799407959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.138
CYP1A2-substrate:	0.2
CYP2C19-inhibitor:	0.339
CYP2C19-substrate:	0.298
CYP2C9-inhibitor:	0.428
CYP2C9-substrate:	0.702
CYP2D6-inhibitor:	0.071
CYP2D6-substrate:	0.777
CYP3A4-inhibitor:	0.603
CYP3A4-substrate:	0.414

ADMET: Excretion

Clearance (CL):	3.545
Half-life (T1/2):	0.355

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.116
Drug-inuced Liver Injury (DILI):	0.592
AMES Toxicity:	0.824
Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.233
Carcinogencity:	0.951
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC469715

Natural Product ID:	NPC469715
*Common Name:**	HWUWOVNYRVOXGA-NJPICVDWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HWUWOVNYRVOXGA-NJPICVDWSA-N
Standard InCHI:	InChI=1S/C11H10Br2ClN5O2/c12-4-3-5(16-8(4)13)9(21)19-1-2(14)7(20)11(19)6(3)17-10(15)18-11/h2,6-7,16,20H,1H2,(H3,15,17,18)/t2-,6?,7-,11?/m0/s1
SMILES:	C1C(C(C23N1C(=O)C4=C(C2N=C(N3)N)C(=C(N4)Br)Br)O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1162336
PubChem CID:	42618900 11017120
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001093] Carboxylic acid derivatives [CHEMONTID:0000475] Carboxylic acid amides [CHEMONTID:0004817] 2-heteroaryl carboxamides

*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
NPO31051	Axinella brevistyla	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11754618]

☑ 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
NPT137	Cell Line	L1210	Mus musculus	IC50	=	2.5	ug.mL-1	PMID[486588]

☑ 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 NPC469715 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	424
0.1-0.2	7155
0.2-0.3	25546
0.3-0.4	4435
0.4-0.5	3539
0.5-0.6	1406
0.6-0.7	178
0.7-0.8	13
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.755	Intermediate Similarity	NPC469814
0.75	Intermediate Similarity	NPC271927
0.75	Intermediate Similarity	NPC66642
0.7296	Intermediate Similarity	NPC474696
0.7186	Intermediate Similarity	NPC469976
0.7183	Intermediate Similarity	NPC9635
0.7108	Intermediate Similarity	NPC184932
0.7108	Intermediate Similarity	NPC472861
0.7107	Intermediate Similarity	NPC73687
0.71	Intermediate Similarity	NPC476421
0.71	Intermediate Similarity	NPC28096
0.71	Intermediate Similarity	NPC227489
0.7015	Intermediate Similarity	NPC226835
0.6933	Remote Similarity	NPC475736
0.6912	Remote Similarity	NPC136441
0.6909	Remote Similarity	NPC476524
0.6854	Remote Similarity	NPC19342
0.6814	Remote Similarity	NPC80528
0.681	Remote Similarity	NPC112489
0.681	Remote Similarity	NPC46022
0.6784	Remote Similarity	NPC469717
0.678	Remote Similarity	NPC37268
0.6757	Remote Similarity	NPC476525
0.6744	Remote Similarity	NPC46811
0.673	Remote Similarity	NPC63571
0.673	Remote Similarity	NPC111566
0.6725	Remote Similarity	NPC474195
0.6698	Remote Similarity	NPC310633
0.6697	Remote Similarity	NPC19696
0.6697	Remote Similarity	NPC136957
0.6683	Remote Similarity	NPC206148
0.6682	Remote Similarity	NPC474258
0.6681	Remote Similarity	NPC474196
0.6651	Remote Similarity	NPC476413
0.6633	Remote Similarity	NPC474236
0.662	Remote Similarity	NPC476414
0.6618	Remote Similarity	NPC97106
0.6606	Remote Similarity	NPC174281
0.6606	Remote Similarity	NPC475286
0.6605	Remote Similarity	NPC243716
0.6575	Remote Similarity	NPC474389
0.6569	Remote Similarity	NPC474383
0.6542	Remote Similarity	NPC473946
0.652	Remote Similarity	NPC476418
0.6498	Remote Similarity	NPC470730
0.6498	Remote Similarity	NPC477176
0.6498	Remote Similarity	NPC477175
0.6498	Remote Similarity	NPC470729
0.6488	Remote Similarity	NPC2414
0.6484	Remote Similarity	NPC48117
0.6484	Remote Similarity	NPC329765
0.6484	Remote Similarity	NPC476526
0.6471	Remote Similarity	NPC477177
0.6471	Remote Similarity	NPC475969
0.6471	Remote Similarity	NPC474877
0.6471	Remote Similarity	NPC475859
0.6463	Remote Similarity	NPC54744
0.6459	Remote Similarity	NPC186068
0.6457	Remote Similarity	NPC469716
0.6444	Remote Similarity	NPC165743
0.6438	Remote Similarity	NPC272174
0.6434	Remote Similarity	NPC17487
0.6434	Remote Similarity	NPC201831
0.6417	Remote Similarity	NPC63279
0.6409	Remote Similarity	NPC292361
0.6408	Remote Similarity	NPC477107
0.6408	Remote Similarity	NPC477108
0.6408	Remote Similarity	NPC477109
0.64	Remote Similarity	NPC473376
0.639	Remote Similarity	NPC297642
0.6376	Remote Similarity	NPC320968
0.6376	Remote Similarity	NPC210123
0.6372	Remote Similarity	NPC476423
0.6364	Remote Similarity	NPC54214
0.636	Remote Similarity	NPC162860
0.6359	Remote Similarity	NPC274981
0.634	Remote Similarity	NPC474896
0.6338	Remote Similarity	NPC91179
0.6324	Remote Similarity	NPC27296
0.6318	Remote Similarity	NPC474180
0.6318	Remote Similarity	NPC188821
0.6314	Remote Similarity	NPC31097
0.6309	Remote Similarity	NPC238945
0.6272	Remote Similarity	NPC54420
0.6266	Remote Similarity	NPC470731
0.6266	Remote Similarity	NPC470732
0.6262	Remote Similarity	NPC473706
0.625	Remote Similarity	NPC156003
0.6245	Remote Similarity	NPC71238
0.6244	Remote Similarity	NPC217372
0.6244	Remote Similarity	NPC183662
0.6244	Remote Similarity	NPC15573
0.624	Remote Similarity	NPC263117
0.624	Remote Similarity	NPC125181
0.624	Remote Similarity	NPC242872
0.6228	Remote Similarity	NPC471191
0.6221	Remote Similarity	NPC311282
0.6218	Remote Similarity	NPC64216
0.6217	Remote Similarity	NPC107077
0.6217	Remote Similarity	NPC223791
0.6215	Remote Similarity	NPC219336
0.621	Remote Similarity	NPC473628
0.6207	Remote Similarity	NPC471193
0.6207	Remote Similarity	NPC471194
0.6205	Remote Similarity	NPC171317
0.62	Remote Similarity	NPC260041
0.6197	Remote Similarity	NPC471192
0.619	Remote Similarity	NPC14812
0.618	Remote Similarity	NPC470703
0.6178	Remote Similarity	NPC477004
0.6173	Remote Similarity	NPC63031
0.6167	Remote Similarity	NPC214142
0.6164	Remote Similarity	NPC54981
0.6164	Remote Similarity	NPC17059
0.6157	Remote Similarity	NPC69843
0.6154	Remote Similarity	NPC50562
0.6148	Remote Similarity	NPC474357
0.6141	Remote Similarity	NPC261251
0.614	Remote Similarity	NPC165599
0.6137	Remote Similarity	NPC470702
0.6137	Remote Similarity	NPC473218
0.6135	Remote Similarity	NPC474492
0.613	Remote Similarity	NPC270918
0.6128	Remote Similarity	NPC67658
0.6123	Remote Similarity	NPC475506
0.6116	Remote Similarity	NPC77061
0.6116	Remote Similarity	NPC179701
0.6116	Remote Similarity	NPC100547
0.6109	Remote Similarity	NPC475874
0.6107	Remote Similarity	NPC267078
0.6107	Remote Similarity	NPC89987
0.6107	Remote Similarity	NPC935
0.6106	Remote Similarity	NPC470680
0.6106	Remote Similarity	NPC100104
0.6104	Remote Similarity	NPC143075
0.6102	Remote Similarity	NPC472285
0.6096	Remote Similarity	NPC155143
0.6094	Remote Similarity	NPC72956
0.6091	Remote Similarity	NPC95240
0.6091	Remote Similarity	NPC322135
0.6091	Remote Similarity	NPC223409
0.6089	Remote Similarity	NPC262898
0.6079	Remote Similarity	NPC77241
0.6079	Remote Similarity	NPC166209
0.6079	Remote Similarity	NPC269203
0.6079	Remote Similarity	NPC13456
0.6078	Remote Similarity	NPC478158
0.6075	Remote Similarity	NPC321939
0.6074	Remote Similarity	NPC124920
0.6074	Remote Similarity	NPC34580
0.6074	Remote Similarity	NPC304307
0.6074	Remote Similarity	NPC118559
0.6073	Remote Similarity	NPC133003
0.607	Remote Similarity	NPC472843
0.6068	Remote Similarity	NPC153980
0.6068	Remote Similarity	NPC6865
0.6066	Remote Similarity	NPC14288
0.6066	Remote Similarity	NPC470323
0.6061	Remote Similarity	NPC244741
0.6057	Remote Similarity	NPC245055
0.6057	Remote Similarity	NPC33064
0.6055	Remote Similarity	NPC470205
0.6049	Remote Similarity	NPC194740
0.6045	Remote Similarity	NPC476527
0.6042	Remote Similarity	NPC312942
0.6042	Remote Similarity	NPC327095
0.6041	Remote Similarity	NPC321592
0.6041	Remote Similarity	NPC54803
0.6037	Remote Similarity	NPC469896
0.6035	Remote Similarity	NPC268744
0.6035	Remote Similarity	NPC201266
0.6035	Remote Similarity	NPC220797
0.6035	Remote Similarity	NPC475914
0.6035	Remote Similarity	NPC474318
0.6035	Remote Similarity	NPC153123
0.6028	Remote Similarity	NPC161861
0.6024	Remote Similarity	NPC472207
0.6019	Remote Similarity	NPC473380
0.6019	Remote Similarity	NPC240088
0.6017	Remote Similarity	NPC476817
0.6017	Remote Similarity	NPC40455
0.6016	Remote Similarity	NPC284888
0.6015	Remote Similarity	NPC77101
0.5992	Remote Similarity	NPC19170
0.5991	Remote Similarity	NPC473640
0.5991	Remote Similarity	NPC213629
0.5985	Remote Similarity	NPC117980
0.5975	Remote Similarity	NPC282247
0.5963	Remote Similarity	NPC314281
0.5963	Remote Similarity	NPC40530
0.5963	Remote Similarity	NPC234403
0.5957	Remote Similarity	NPC82370
0.5956	Remote Similarity	NPC472295
0.5956	Remote Similarity	NPC247735
0.5956	Remote Similarity	NPC81802
0.5956	Remote Similarity	NPC269886
0.5956	Remote Similarity	NPC472210
0.5949	Remote Similarity	NPC478157
0.5948	Remote Similarity	NPC313280
0.5941	Remote Similarity	NPC281049

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 NPC469715 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	679
0.2-0.3	1729
0.3-0.4	2795
0.4-0.5	2983
0.5-0.6	748
0.6-0.7	15
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
0.6486	Remote Similarity	NPD7817	Phase 1
0.6404	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6287	Remote Similarity	NPD7716	Approved
0.6287	Remote Similarity	NPD7717	Approved
0.6226	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD7971	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD7970	Approved
0.6217	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD2214	Approved
0.6214	Remote Similarity	NPD2213	Approved
0.6201	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD2947	Clinical (unspecified phase)
0.6123	Remote Similarity	NPD7727	Phase 2
0.6114	Remote Similarity	NPD8115	Approved
0.6114	Remote Similarity	NPD8114	Approved
0.6104	Remote Similarity	NPD2442	Approved
0.6104	Remote Similarity	NPD2443	Approved
0.6092	Remote Similarity	NPD1996	Discontinued
0.6085	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD2408	Discontinued
0.607	Remote Similarity	NPD7772	Phase 3
0.6061	Remote Similarity	NPD8322	Phase 2
0.6043	Remote Similarity	NPD2823	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD3915	Approved
0.6009	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3918	Approved
0.6	Remote Similarity	NPD3917	Approved
0.5983	Remote Similarity	NPD5017	Discontinued
0.5975	Remote Similarity	NPD5001	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD6288	Clinical (unspecified phase)
0.5973	Remote Similarity	NPD2290	Phase 3
0.5973	Remote Similarity	NPD2289	Phase 3
0.5959	Remote Similarity	NPD6035	Phase 2
0.5956	Remote Similarity	NPD2004	Clinical (unspecified phase)
0.594	Remote Similarity	NPD1600	Suspended
0.594	Remote Similarity	NPD3968	Approved
0.5935	Remote Similarity	NPD1575	Approved
0.5935	Remote Similarity	NPD1573	Approved
0.5924	Remote Similarity	NPD3353	Approved
0.5923	Remote Similarity	NPD3410	Approved
0.5923	Remote Similarity	NPD3411	Phase 2
0.5921	Remote Similarity	NPD465	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD7459	Phase 2
0.5921	Remote Similarity	NPD1990	Phase 2
0.5921	Remote Similarity	NPD1991	Phase 2
0.5921	Remote Similarity	NPD1992	Phase 2
0.5913	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD6376	Discontinued
0.5895	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD276	Clinical (unspecified phase)
0.5885	Remote Similarity	NPD460	Discontinued
0.5882	Remote Similarity	NPD1096	Discontinued
0.5878	Remote Similarity	NPD6165	Phase 2
0.5878	Remote Similarity	NPD6164	Phase 2
0.5865	Remote Similarity	NPD8096	Phase 3
0.5865	Remote Similarity	NPD8097	Phase 3
0.5864	Remote Similarity	NPD3178	Discontinued
0.5864	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD3360	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD1506	Discontinued
0.5855	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.5837	Remote Similarity	NPD8098	Approved
0.5837	Remote Similarity	NPD8169	Discontinued
0.5833	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8271	Discontinued
0.5823	Remote Similarity	NPD7789	Approved
0.5823	Remote Similarity	NPD7790	Approved
0.5823	Remote Similarity	NPD7951	Approved
0.5823	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD7952	Approved
0.5823	Remote Similarity	NPD7791	Approved
0.5823	Remote Similarity	NPD7953	Approved
0.5823	Remote Similarity	NPD7950	Approved
0.5819	Remote Similarity	NPD4134	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD3989	Phase 3
0.5813	Remote Similarity	NPD7730	Approved
0.5813	Remote Similarity	NPD7731	Approved
0.5812	Remote Similarity	NPD7568	Phase 1
0.5812	Remote Similarity	NPD3967	Approved
0.5809	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.5808	Remote Similarity	NPD2880	Discontinued
0.5805	Remote Similarity	NPD4520	Approved
0.5801	Remote Similarity	NPD2912	Approved
0.5801	Remote Similarity	NPD4601	Approved
0.5801	Remote Similarity	NPD2911	Approved
0.5801	Remote Similarity	NPD4600	Approved
0.5796	Remote Similarity	NPD7271	Approved
0.5792	Remote Similarity	NPD3990	Phase 3
0.5791	Remote Similarity	NPD8349	Phase 1
0.5789	Remote Similarity	NPD7781	Approved
0.5789	Remote Similarity	NPD7780	Approved
0.5785	Remote Similarity	NPD5199	Approved
0.5785	Remote Similarity	NPD5198	Approved
0.5785	Remote Similarity	NPD534	Phase 2
0.5785	Remote Similarity	NPD537	Phase 2
0.5785	Remote Similarity	NPD6557	Phase 2
0.5783	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.5781	Remote Similarity	NPD5807	Phase 2
0.5779	Remote Similarity	NPD6995	Phase 1
0.5774	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD1587	Approved
0.5771	Remote Similarity	NPD6665	Discontinued
0.5769	Remote Similarity	NPD5426	Phase 3
0.5768	Remote Similarity	NPD2787	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7824	Approved
0.5763	Remote Similarity	NPD7232	Discontinued
0.5747	Remote Similarity	NPD1643	Phase 3
0.5745	Remote Similarity	NPD2008	Discontinued
0.5745	Remote Similarity	NPD7001	Phase 3
0.574	Remote Similarity	NPD7482	Phase 2
0.574	Remote Similarity	NPD7483	Phase 2
0.5738	Remote Similarity	NPD5510	Approved
0.5736	Remote Similarity	NPD5461	Discontinued
0.5734	Remote Similarity	NPD4524	Discontinued
0.5733	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD3246	Discontinued
0.5727	Remote Similarity	NPD3991	Approved
0.5727	Remote Similarity	NPD3994	Approved
0.5727	Remote Similarity	NPD3996	Approved
0.5727	Remote Similarity	NPD3993	Approved
0.5727	Remote Similarity	NPD3995	Approved
0.5727	Remote Similarity	NPD3992	Approved
0.5726	Remote Similarity	NPD8160	Phase 2
0.5726	Remote Similarity	NPD1571	Phase 2
0.5721	Remote Similarity	NPD7619	Phase 3
0.5721	Remote Similarity	NPD7618	Phase 3
0.572	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.5708	Remote Similarity	NPD482	Approved
0.5708	Remote Similarity	NPD1657	Approved
0.5708	Remote Similarity	NPD3243	Approved
0.5702	Remote Similarity	NPD3380	Phase 3
0.5702	Remote Similarity	NPD8272	Phase 2
0.5702	Remote Similarity	NPD3379	Phase 2
0.5702	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD3247	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD5643	Phase 2
0.5701	Remote Similarity	NPD3999	Approved
0.5701	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD3997	Approved
0.5701	Remote Similarity	NPD3998	Approved
0.5697	Remote Similarity	NPD6210	Phase 3
0.5691	Remote Similarity	NPD6753	Phase 1
0.5691	Remote Similarity	NPD6752	Phase 1
0.569	Remote Similarity	NPD7470	Discontinued
0.569	Remote Similarity	NPD3425	Discontinued
0.5684	Remote Similarity	NPD3773	Approved
0.5684	Remote Similarity	NPD3775	Approved
0.5684	Remote Similarity	NPD6802	Phase 3
0.5684	Remote Similarity	NPD3774	Approved
0.5682	Remote Similarity	NPD4091	Approved
0.5678	Remote Similarity	NPD3507	Phase 2
0.5676	Remote Similarity	NPD4558	Phase 2
0.5674	Remote Similarity	NPD1631	Approved
0.5673	Remote Similarity	NPD4854	Phase 3
0.5672	Remote Similarity	NPD7941	Phase 3
0.5671	Remote Similarity	NPD6664	Approved
0.567	Remote Similarity	NPD721	Approved
0.5665	Remote Similarity	NPD4501	Approved
0.5665	Remote Similarity	NPD4500	Approved
0.5658	Remote Similarity	NPD1658	Discontinued
0.5657	Remote Similarity	NPD1572	Phase 2
0.5656	Remote Similarity	NPD4092	Approved
0.5656	Remote Similarity	NPD7865	Approved
0.5656	Remote Similarity	NPD4155	Approved
0.5647	Remote Similarity	NPD1982	Phase 1
0.5647	Remote Similarity	NPD2893	Phase 3
0.5647	Remote Similarity	NPD7946	Pre-registration
0.5645	Remote Similarity	NPD8289	Discontinued
0.5639	Remote Similarity	NPD1284	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD1586	Approved
0.5636	Remote Similarity	NPD3522	Approved
0.5633	Remote Similarity	NPD1896	Approved
0.5633	Remote Similarity	NPD6579	Phase 2
0.5631	Remote Similarity	NPD8386	Phase 2
0.563	Remote Similarity	NPD2510	Approved
0.563	Remote Similarity	NPD7666	Phase 3
0.563	Remote Similarity	NPD6487	Approved
0.563	Remote Similarity	NPD2509	Approved
0.563	Remote Similarity	NPD6486	Approved
0.563	Remote Similarity	NPD7665	Phase 2
0.5628	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD4070	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD6173	Approved
0.5625	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.5622	Remote Similarity	NPD7308	Discontinued
0.5619	Remote Similarity	NPD706	Phase 1
0.5619	Remote Similarity	NPD5820	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD7688	Phase 1
0.5617	Remote Similarity	NPD3497	Clinical (unspecified phase)
0.5615	Remote Similarity	NPD6470	Phase 3
0.5612	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.5611	Remote Similarity	NPD4385	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data