NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	296.96
Volume:	231.322
LogP:	2.324
LogD:	1.035
LogS:	-3.373
# Rotatable Bonds:	2
TPSA:	79.39
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.888
Synthetic Accessibility Score:	2.402
Fsp3:	0.091
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.829
MDCK Permeability:	1.2804110156139359e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.124
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.216

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.261
Plasma Protein Binding (PPB):	65.36685943603516%
Volume Distribution (VD):	0.556
Pgp-substrate:	24.144468307495117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.419
CYP1A2-substrate:	0.869
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.07
CYP2C9-substrate:	0.159
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.059

ADMET: Excretion

Clearance (CL):	1.568
Half-life (T1/2):	0.821

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.142
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.329
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.189
Carcinogencity:	0.048
Eye Corrosion:	0.006
Eye Irritation:	0.684
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC174576

Natural Product ID:	NPC174576
*Common Name:**	6-Bromo-8-Methoxy-4-Oxo-1H-Quinoline-2-Carboxylic Acid
IUPAC Name:	6-bromo-8-methoxy-4-oxo-1H-quinoline-2-carboxylic acid
Synonyms:
Standard InCHIKey:	YPWADPOJPOTNKI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H8BrNO4/c1-17-9-3-5(12)2-6-8(14)4-7(11(15)16)13-10(6)9/h2-4H,1H3,(H,13,14)(H,15,16)
SMILES:	COc1cc(Br)cc2c1nc(cc2O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1223674
PubChem CID:	46938558
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002552] Quinoline carboxylic acids

*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
NPO6477	Aplidium caelestis	Species	Polyclinidae	Eukaryota	n.a.	Australian	n.a.	PMID[20704301]
NPO6477	Aplidium caelestis	Species	Polyclinidae	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
Others	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	40.0	%	PMID[486135]
NPT1524	Cell Line	MM96L	Homo sapiens	Inhibition	=	54.0	%	PMID[486135]
NPT1523	Cell Line	NFF	Homo sapiens	Inhibition	=	58.0	%	PMID[486135]

☑ 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 NPC174576 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	448
0.1-0.2	3776
0.2-0.3	13055
0.3-0.4	3887
0.4-0.5	17388
0.5-0.6	3090
0.6-0.7	976
0.7-0.8	73
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8667	High Similarity	NPC230403
0.8513	High Similarity	NPC144381
0.785	Intermediate Similarity	NPC42591
0.7788	Intermediate Similarity	NPC184408
0.774	Intermediate Similarity	NPC280714
0.7736	Intermediate Similarity	NPC321428
0.7692	Intermediate Similarity	NPC314633
0.7635	Intermediate Similarity	NPC194040
0.7629	Intermediate Similarity	NPC118511
0.7604	Intermediate Similarity	NPC39500
0.7569	Intermediate Similarity	NPC118228
0.7526	Intermediate Similarity	NPC322644
0.7488	Intermediate Similarity	NPC193238
0.7478	Intermediate Similarity	NPC274640
0.7455	Intermediate Similarity	NPC205372
0.7447	Intermediate Similarity	NPC161801
0.7422	Intermediate Similarity	NPC179287
0.7393	Intermediate Similarity	NPC41488
0.7363	Intermediate Similarity	NPC303225
0.7352	Intermediate Similarity	NPC187501
0.7333	Intermediate Similarity	NPC144452
0.7309	Intermediate Similarity	NPC131885
0.7301	Intermediate Similarity	NPC51388
0.7277	Intermediate Similarity	NPC208084
0.7273	Intermediate Similarity	NPC146418
0.7269	Intermediate Similarity	NPC317572
0.7234	Intermediate Similarity	NPC475844
0.723	Intermediate Similarity	NPC90229
0.72	Intermediate Similarity	NPC288987
0.7198	Intermediate Similarity	NPC320394
0.7195	Intermediate Similarity	NPC87413
0.7195	Intermediate Similarity	NPC220337
0.7186	Intermediate Similarity	NPC474688
0.7186	Intermediate Similarity	NPC474701
0.7143	Intermediate Similarity	NPC66815
0.713	Intermediate Similarity	NPC140296
0.713	Intermediate Similarity	NPC232225
0.7105	Intermediate Similarity	NPC478141
0.7104	Intermediate Similarity	NPC325297
0.7095	Intermediate Similarity	NPC66083
0.7094	Intermediate Similarity	NPC182222
0.7093	Intermediate Similarity	NPC225279
0.7092	Intermediate Similarity	NPC26872
0.7091	Intermediate Similarity	NPC283117
0.7089	Intermediate Similarity	NPC148889
0.7079	Intermediate Similarity	NPC470894
0.7074	Intermediate Similarity	NPC94842
0.7059	Intermediate Similarity	NPC39679
0.7046	Intermediate Similarity	NPC41501
0.7045	Intermediate Similarity	NPC300156
0.7035	Intermediate Similarity	NPC223189
0.7029	Intermediate Similarity	NPC316224
0.7029	Intermediate Similarity	NPC160100
0.7029	Intermediate Similarity	NPC291609
0.7025	Intermediate Similarity	NPC165964
0.7022	Intermediate Similarity	NPC16066
0.7018	Intermediate Similarity	NPC174760
0.7014	Intermediate Similarity	NPC4687
0.7005	Intermediate Similarity	NPC128823
0.6996	Remote Similarity	NPC269367
0.699	Remote Similarity	NPC286195
0.699	Remote Similarity	NPC84347
0.6987	Remote Similarity	NPC124300
0.6985	Remote Similarity	NPC26850
0.6978	Remote Similarity	NPC89508
0.6971	Remote Similarity	NPC478032
0.697	Remote Similarity	NPC97746
0.6966	Remote Similarity	NPC260434
0.6964	Remote Similarity	NPC294375
0.6957	Remote Similarity	NPC216612
0.6957	Remote Similarity	NPC283152
0.6952	Remote Similarity	NPC62069
0.6929	Remote Similarity	NPC208522
0.692	Remote Similarity	NPC309845
0.6908	Remote Similarity	NPC288943
0.6906	Remote Similarity	NPC470280
0.6901	Remote Similarity	NPC310618
0.6895	Remote Similarity	NPC216369
0.6892	Remote Similarity	NPC472287
0.6892	Remote Similarity	NPC472286
0.6891	Remote Similarity	NPC477589
0.6891	Remote Similarity	NPC477587
0.6886	Remote Similarity	NPC312645
0.6886	Remote Similarity	NPC293151
0.6881	Remote Similarity	NPC177404
0.6878	Remote Similarity	NPC314940
0.6878	Remote Similarity	NPC473764
0.6878	Remote Similarity	NPC34770
0.6872	Remote Similarity	NPC207851
0.687	Remote Similarity	NPC54066
0.6867	Remote Similarity	NPC470018
0.6864	Remote Similarity	NPC470586
0.6864	Remote Similarity	NPC279189
0.6863	Remote Similarity	NPC41717
0.6856	Remote Similarity	NPC247803
0.6853	Remote Similarity	NPC322482
0.6852	Remote Similarity	NPC475190
0.6844	Remote Similarity	NPC470020
0.6842	Remote Similarity	NPC74969
0.6842	Remote Similarity	NPC3207
0.6838	Remote Similarity	NPC74575
0.6833	Remote Similarity	NPC477588
0.6833	Remote Similarity	NPC477586
0.6833	Remote Similarity	NPC477585
0.6833	Remote Similarity	NPC477590
0.6831	Remote Similarity	NPC58209
0.6828	Remote Similarity	NPC250448
0.6827	Remote Similarity	NPC8467
0.6822	Remote Similarity	NPC242928
0.682	Remote Similarity	NPC15801
0.6816	Remote Similarity	NPC116573
0.6816	Remote Similarity	NPC304183
0.6816	Remote Similarity	NPC45190
0.6812	Remote Similarity	NPC169402
0.6809	Remote Similarity	NPC246381
0.6809	Remote Similarity	NPC194740
0.6803	Remote Similarity	NPC218388
0.6802	Remote Similarity	NPC476098
0.6802	Remote Similarity	NPC165599
0.6798	Remote Similarity	NPC146976
0.6798	Remote Similarity	NPC116238
0.6798	Remote Similarity	NPC227824
0.6797	Remote Similarity	NPC150239
0.6793	Remote Similarity	NPC49547
0.6786	Remote Similarity	NPC249583
0.6784	Remote Similarity	NPC474428
0.6779	Remote Similarity	NPC312872
0.6778	Remote Similarity	NPC162002
0.6777	Remote Similarity	NPC474798
0.6771	Remote Similarity	NPC132539
0.6769	Remote Similarity	NPC67658
0.6766	Remote Similarity	NPC257851
0.6765	Remote Similarity	NPC284888
0.6765	Remote Similarity	NPC329631
0.6758	Remote Similarity	NPC141454
0.6754	Remote Similarity	NPC236668
0.6753	Remote Similarity	NPC292958
0.6753	Remote Similarity	NPC74360
0.6753	Remote Similarity	NPC298436
0.675	Remote Similarity	NPC472061
0.6749	Remote Similarity	NPC208364
0.6743	Remote Similarity	NPC276517
0.6736	Remote Similarity	NPC33064
0.6736	Remote Similarity	NPC39370
0.6729	Remote Similarity	NPC204385
0.6726	Remote Similarity	NPC475774
0.6723	Remote Similarity	NPC473186
0.6723	Remote Similarity	NPC200553
0.6721	Remote Similarity	NPC181081
0.6721	Remote Similarity	NPC473800
0.6712	Remote Similarity	NPC98685
0.6711	Remote Similarity	NPC472098
0.6711	Remote Similarity	NPC244741
0.6711	Remote Similarity	NPC270918
0.6711	Remote Similarity	NPC203168
0.6709	Remote Similarity	NPC95240
0.6708	Remote Similarity	NPC166712
0.6708	Remote Similarity	NPC470017
0.6701	Remote Similarity	NPC85443
0.6698	Remote Similarity	NPC206186
0.6696	Remote Similarity	NPC8022
0.6696	Remote Similarity	NPC470799
0.6696	Remote Similarity	NPC219664
0.6695	Remote Similarity	NPC261251
0.6695	Remote Similarity	NPC124920
0.6695	Remote Similarity	NPC34580
0.6695	Remote Similarity	NPC118559
0.6695	Remote Similarity	NPC304307
0.6683	Remote Similarity	NPC252590
0.6682	Remote Similarity	NPC241025
0.6681	Remote Similarity	NPC287208
0.6681	Remote Similarity	NPC476287
0.668	Remote Similarity	NPC26641
0.668	Remote Similarity	NPC470022
0.6667	Remote Similarity	NPC100547
0.6667	Remote Similarity	NPC146724
0.6667	Remote Similarity	NPC44161
0.6667	Remote Similarity	NPC97902
0.6654	Remote Similarity	NPC132385
0.6653	Remote Similarity	NPC321592
0.6653	Remote Similarity	NPC214142
0.6653	Remote Similarity	NPC54803
0.6653	Remote Similarity	NPC200888
0.6653	Remote Similarity	NPC473188
0.6652	Remote Similarity	NPC472099
0.6652	Remote Similarity	NPC472284
0.6652	Remote Similarity	NPC477979
0.6652	Remote Similarity	NPC306376
0.6652	Remote Similarity	NPC469439
0.6652	Remote Similarity	NPC50562
0.6642	Remote Similarity	NPC207620
0.664	Remote Similarity	NPC173250
0.6639	Remote Similarity	NPC223409
0.6639	Remote Similarity	NPC322135
0.6638	Remote Similarity	NPC310211
0.6638	Remote Similarity	NPC38237
0.6638	Remote Similarity	NPC46561
0.6638	Remote Similarity	NPC122436
0.6638	Remote Similarity	NPC308137
0.6633	Remote Similarity	NPC257142

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 NPC174576 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	789
0.2-0.3	1128
0.3-0.4	1663
0.4-0.5	3194
0.5-0.6	1734
0.6-0.7	339
0.7-0.8	22
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
0.7512	Intermediate Similarity	NPD5416	Discontinued
0.7489	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD7395	Discontinued
0.7429	Intermediate Similarity	NPD5512	Phase 3
0.7383	Intermediate Similarity	NPD2779	Approved
0.7376	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD5429	Discontinued
0.7282	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1505	Phase 2
0.7243	Intermediate Similarity	NPD2778	Approved
0.7189	Intermediate Similarity	NPD6991	Approved
0.7186	Intermediate Similarity	NPD1467	Approved
0.7186	Intermediate Similarity	NPD1466	Phase 3
0.7181	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3263	Phase 3
0.7156	Intermediate Similarity	NPD4429	Discontinued
0.7149	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD7853	Phase 2
0.7105	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD2951	Discontinued
0.7059	Intermediate Similarity	NPD7672	Approved
0.7059	Intermediate Similarity	NPD7671	Approved
0.7048	Intermediate Similarity	NPD6974	Phase 3
0.7039	Intermediate Similarity	NPD1867	Approved
0.7018	Intermediate Similarity	NPD7180	Phase 3
0.7009	Intermediate Similarity	NPD5866	Approved
0.6996	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD5022	Discontinued
0.6983	Remote Similarity	NPD3259	Approved
0.6983	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD3945	Discontinued
0.6974	Remote Similarity	NPD3258	Approved
0.6944	Remote Similarity	NPD6550	Discontinued
0.6929	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.692	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD6716	Phase 1
0.6897	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD772	Phase 3
0.6872	Remote Similarity	NPD3257	Approved
0.6872	Remote Similarity	NPD1638	Discovery
0.687	Remote Similarity	NPD5850	Phase 3
0.6858	Remote Similarity	NPD7069	Discontinued
0.6856	Remote Similarity	NPD5632	Approved
0.6849	Remote Similarity	NPD3006	Discontinued
0.6846	Remote Similarity	NPD7022	Phase 2
0.6835	Remote Similarity	NPD6988	Phase 1
0.6824	Remote Similarity	NPD3925	Approved
0.6814	Remote Similarity	NPD4502	Phase 2
0.6803	Remote Similarity	NPD3328	Phase 2
0.678	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5482	Discontinued
0.6743	Remote Similarity	NPD6590	Discontinued
0.6734	Remote Similarity	NPD8463	Approved
0.6723	Remote Similarity	NPD5640	Discontinued
0.6722	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD9690	Approved
0.6696	Remote Similarity	NPD3392	Approved
0.6695	Remote Similarity	NPD4328	Approved
0.6694	Remote Similarity	NPD5488	Discontinued
0.6682	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD6962	Phase 2
0.6681	Remote Similarity	NPD3243	Approved
0.668	Remote Similarity	NPD4368	Phase 2
0.6667	Remote Similarity	NPD2792	Approved
0.6667	Remote Similarity	NPD3074	Discontinued
0.6667	Remote Similarity	NPD3326	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9705	Discontinued
0.6667	Remote Similarity	NPD112	Approved
0.6667	Remote Similarity	NPD7417	Discontinued
0.6624	Remote Similarity	NPD7994	Phase 2
0.6622	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4203	Approved
0.662	Remote Similarity	NPD4204	Approved
0.6613	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD5443	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.659	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2821	Approved
0.6582	Remote Similarity	NPD7603	Discontinued
0.658	Remote Similarity	NPD4897	Phase 2
0.6575	Remote Similarity	NPD9243	Approved
0.6569	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD3354	Phase 2
0.6564	Remote Similarity	NPD7222	Phase 2
0.6557	Remote Similarity	NPD6159	Phase 2
0.6556	Remote Similarity	NPD4460	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4373	Phase 2
0.6545	Remote Similarity	NPD6495	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD5805	Approved
0.6535	Remote Similarity	NPD7467	Discontinued
0.6525	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5050	Approved
0.6516	Remote Similarity	NPD4418	Discontinued
0.6515	Remote Similarity	NPD7031	Phase 1
0.6504	Remote Similarity	NPD1483	Discontinued
0.6502	Remote Similarity	NPD5891	Approved
0.6502	Remote Similarity	NPD3250	Phase 1
0.65	Remote Similarity	NPD4952	Phase 3
0.6494	Remote Similarity	NPD5857	Phase 3
0.6478	Remote Similarity	NPD5420	Discontinued
0.6476	Remote Similarity	NPD4039	Approved
0.6476	Remote Similarity	NPD4122	Approved
0.6476	Remote Similarity	NPD32	Approved
0.6476	Remote Similarity	NPD4035	Approved
0.6476	Remote Similarity	NPD4033	Approved
0.6476	Remote Similarity	NPD4034	Approved
0.6476	Remote Similarity	NPD4038	Approved
0.6476	Remote Similarity	NPD4037	Approved
0.6476	Remote Similarity	NPD4036	Approved
0.6476	Remote Similarity	NPD31	Approved
0.6473	Remote Similarity	NPD2175	Phase 3
0.6473	Remote Similarity	NPD2177	Approved
0.6473	Remote Similarity	NPD2176	Approved
0.6473	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD6874	Approved
0.6468	Remote Similarity	NPD3875	Discontinued
0.6466	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5003	Discontinued
0.6456	Remote Similarity	NPD1856	Discontinued
0.645	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7796	Approved
0.6446	Remote Similarity	NPD7797	Approved
0.6444	Remote Similarity	NPD484	Approved
0.6441	Remote Similarity	NPD1996	Discontinued
0.6441	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD6242	Discontinued
0.6441	Remote Similarity	NPD8479	Phase 2
0.644	Remote Similarity	NPD8102	Discontinued
0.6438	Remote Similarity	NPD408	Approved
0.6434	Remote Similarity	NPD5450	Discontinued
0.6432	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6432	Remote Similarity	NPD5513	Phase 2
0.6432	Remote Similarity	NPD5479	Discontinued
0.6419	Remote Similarity	NPD7452	Approved
0.6419	Remote Similarity	NPD7453	Approved
0.6414	Remote Similarity	NPD5506	Approved
0.6414	Remote Similarity	NPD5507	Approved
0.6409	Remote Similarity	NPD2564	Approved
0.6409	Remote Similarity	NPD2565	Phase 2
0.6408	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD2081	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD9695	Approved
0.6387	Remote Similarity	NPD8356	Approved
0.6376	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD5530	Phase 1
0.6376	Remote Similarity	NPD4889	Approved
0.6372	Remote Similarity	NPD3920	Phase 2
0.6368	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1898	Discontinued
0.6364	Remote Similarity	NPD1631	Approved
0.636	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.636	Remote Similarity	NPD7548	Discontinued
0.636	Remote Similarity	NPD5817	Discontinued
0.6351	Remote Similarity	NPD6569	Phase 2
0.6349	Remote Similarity	NPD3986	Discontinued
0.6349	Remote Similarity	NPD8430	Approved
0.6348	Remote Similarity	NPD6290	Phase 2
0.6344	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD3477	Phase 2
0.6339	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD5860	Discontinued
0.6336	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5316	Approved
0.6333	Remote Similarity	NPD4890	Phase 2
0.6333	Remote Similarity	NPD1168	Approved
0.6331	Remote Similarity	NPD6790	Phase 1
0.633	Remote Similarity	NPD7546	Discontinued
0.6329	Remote Similarity	NPD2785	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD8091	Phase 3
0.6322	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6318	Remote Similarity	NPD6209	Approved
0.6303	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD5469	Phase 3
0.63	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD5293	Phase 2
0.6296	Remote Similarity	NPD5924	Discontinued
0.629	Remote Similarity	NPD7885	Phase 2
0.629	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.629	Remote Similarity	NPD7886	Phase 2
0.6285	Remote Similarity	NPD8101	Phase 3
0.6283	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD712	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6278	Remote Similarity	NPD9689	Approved
0.6274	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5256	Discontinued
0.6272	Remote Similarity	NPD7727	Phase 2
0.627	Remote Similarity	NPD7868	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD4894	Discontinued
0.6267	Remote Similarity	NPD9510	Approved
0.6261	Remote Similarity	NPD1213	Phase 3

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