NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.09
Volume:	240.23
LogP:	1.851
LogD:	1.411
LogS:	-3.853
# Rotatable Bonds:	0
TPSA:	58.02
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.632
Synthetic Accessibility Score:	2.746
Fsp3:	0.214
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.879
MDCK Permeability:	1.4152871699479874e-05
Pgp-inhibitor:	0.044
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.227

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.553
Plasma Protein Binding (PPB):	87.08895111083984%
Volume Distribution (VD):	1.043
Pgp-substrate:	6.33392858505249%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.564
CYP2C19-inhibitor:	0.546
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.649
CYP2C9-substrate:	0.837
CYP2D6-inhibitor:	0.787
CYP2D6-substrate:	0.753
CYP3A4-inhibitor:	0.26
CYP3A4-substrate:	0.167

ADMET: Excretion

Clearance (CL):	2.114
Half-life (T1/2):	0.328

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.443
Drug-inuced Liver Injury (DILI):	0.693
AMES Toxicity:	0.695
Rat Oral Acute Toxicity:	0.249
Maximum Recommended Daily Dose:	0.722
Skin Sensitization:	0.9
Carcinogencity:	0.953
Eye Corrosion:	0.012
Eye Irritation:	0.626
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC471164

Natural Product ID:	NPC471164
*Common Name:**	SQGVQVNTJFVDQL-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SQGVQVNTJFVDQL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12N2O2/c17-13-8-4-1-2-5-9(8)15-12-10-6-3-7-16(10)14(18)11(12)13/h1-2,4-5,10H,3,6-7H2,(H,15,17)
SMILES:	C1CC2C3=C(C(=O)C4=CC=CC=C4N3)C(=O)N2C1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2385866
PubChem CID:	73353435
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001716] Hydroquinolones

*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
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730261]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15973055]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18656987]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21053938]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	Moroccan	n.a.	PMID[23713692]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7766039]
NPO19366	Penicillium citrinum	Species	Aspergillaceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	>	10000.0	nM	PMID[529577]

☑ 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 NPC471164 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	555
0.1-0.2	5788
0.2-0.3	14592
0.3-0.4	15121
0.4-0.5	2506
0.5-0.6	2181
0.6-0.7	1577
0.7-0.8	320
0.8-0.85	51
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8551	High Similarity	NPC316104
0.8551	High Similarity	NPC162417
0.8358	Intermediate Similarity	NPC254698
0.8188	Intermediate Similarity	NPC209389
0.8151	Intermediate Similarity	NPC136002
0.8134	Intermediate Similarity	NPC179605
0.8134	Intermediate Similarity	NPC279385
0.8074	Intermediate Similarity	NPC103292
0.806	Intermediate Similarity	NPC291962
0.806	Intermediate Similarity	NPC177684
0.8	Intermediate Similarity	NPC161956
0.8	Intermediate Similarity	NPC112373
0.8	Intermediate Similarity	NPC258531
0.7945	Intermediate Similarity	NPC471574
0.7941	Intermediate Similarity	NPC257490
0.7826	Intermediate Similarity	NPC469529
0.7762	Intermediate Similarity	NPC207428
0.7762	Intermediate Similarity	NPC40364
0.7755	Intermediate Similarity	NPC207554
0.7754	Intermediate Similarity	NPC268534
0.7727	Intermediate Similarity	NPC295021
0.7626	Intermediate Similarity	NPC39818
0.7622	Intermediate Similarity	NPC194562
0.7568	Intermediate Similarity	NPC469560
0.755	Intermediate Similarity	NPC470822
0.7548	Intermediate Similarity	NPC117032
0.7468	Intermediate Similarity	NPC237649
0.7468	Intermediate Similarity	NPC300596
0.7424	Intermediate Similarity	NPC172170
0.7413	Intermediate Similarity	NPC322433
0.741	Intermediate Similarity	NPC226143
0.7407	Intermediate Similarity	NPC279527
0.7407	Intermediate Similarity	NPC214960
0.74	Intermediate Similarity	NPC130251
0.7394	Intermediate Similarity	NPC192533
0.7383	Intermediate Similarity	NPC122553
0.7365	Intermediate Similarity	NPC300299
0.7351	Intermediate Similarity	NPC2823
0.7351	Intermediate Similarity	NPC301760
0.7338	Intermediate Similarity	NPC324445
0.7317	Intermediate Similarity	NPC472118
0.7222	Intermediate Similarity	NPC293458
0.7212	Intermediate Similarity	NPC471943
0.7178	Intermediate Similarity	NPC113056
0.7178	Intermediate Similarity	NPC138293
0.7171	Intermediate Similarity	NPC315051
0.7169	Intermediate Similarity	NPC292265
0.716	Intermediate Similarity	NPC475094
0.7143	Intermediate Similarity	NPC187231
0.7143	Intermediate Similarity	NPC472245
0.7101	Intermediate Similarity	NPC57051
0.7099	Intermediate Similarity	NPC154478
0.7089	Intermediate Similarity	NPC473329
0.7081	Intermediate Similarity	NPC84317
0.7052	Intermediate Similarity	NPC133003
0.7037	Intermediate Similarity	NPC123241
0.7037	Intermediate Similarity	NPC222029
0.7032	Intermediate Similarity	NPC469537
0.7013	Intermediate Similarity	NPC470301
0.7007	Intermediate Similarity	NPC72473
0.7007	Intermediate Similarity	NPC307437
0.7007	Intermediate Similarity	NPC58827
0.6994	Remote Similarity	NPC21429
0.6994	Remote Similarity	NPC276085
0.6993	Remote Similarity	NPC83214
0.6989	Remote Similarity	NPC324091
0.6987	Remote Similarity	NPC130797
0.6986	Remote Similarity	NPC470343
0.6986	Remote Similarity	NPC472244
0.6982	Remote Similarity	NPC470548
0.6974	Remote Similarity	NPC471123
0.6959	Remote Similarity	NPC150863
0.6954	Remote Similarity	NPC253476
0.6951	Remote Similarity	NPC309531
0.6951	Remote Similarity	NPC472102
0.6941	Remote Similarity	NPC151635
0.6933	Remote Similarity	NPC113946
0.6913	Remote Similarity	NPC280807
0.6913	Remote Similarity	NPC314431
0.6908	Remote Similarity	NPC173295
0.6903	Remote Similarity	NPC43477
0.6897	Remote Similarity	NPC477003
0.6864	Remote Similarity	NPC318183
0.6864	Remote Similarity	NPC355
0.6854	Remote Similarity	NPC476460
0.6845	Remote Similarity	NPC224970
0.6845	Remote Similarity	NPC167724
0.6845	Remote Similarity	NPC223595
0.6839	Remote Similarity	NPC470205
0.6832	Remote Similarity	NPC66936
0.6829	Remote Similarity	NPC104345
0.6829	Remote Similarity	NPC61013
0.6818	Remote Similarity	NPC87391
0.6807	Remote Similarity	NPC469741
0.6788	Remote Similarity	NPC193410
0.6788	Remote Similarity	NPC36495
0.6784	Remote Similarity	NPC475594
0.6782	Remote Similarity	NPC197335
0.677	Remote Similarity	NPC144691
0.6767	Remote Similarity	NPC75496
0.6766	Remote Similarity	NPC189116
0.6763	Remote Similarity	NPC475761
0.6761	Remote Similarity	NPC316141
0.6752	Remote Similarity	NPC472241
0.6747	Remote Similarity	NPC68650
0.6747	Remote Similarity	NPC248117
0.6744	Remote Similarity	NPC475607
0.6743	Remote Similarity	NPC314659
0.674	Remote Similarity	NPC202812
0.6731	Remote Similarity	NPC472243
0.6728	Remote Similarity	NPC243756
0.6728	Remote Similarity	NPC154602
0.6728	Remote Similarity	NPC314223
0.6726	Remote Similarity	NPC115232
0.6726	Remote Similarity	NPC471130
0.6725	Remote Similarity	NPC161861
0.6725	Remote Similarity	NPC177261
0.6725	Remote Similarity	NPC252572
0.6724	Remote Similarity	NPC91179
0.6723	Remote Similarity	NPC135601
0.6723	Remote Similarity	NPC17273
0.6723	Remote Similarity	NPC141612
0.6707	Remote Similarity	NPC472117
0.6707	Remote Similarity	NPC214106
0.6707	Remote Similarity	NPC88970
0.6705	Remote Similarity	NPC14849
0.6705	Remote Similarity	NPC474081
0.6703	Remote Similarity	NPC472540
0.6703	Remote Similarity	NPC471944
0.6703	Remote Similarity	NPC79356
0.6703	Remote Similarity	NPC470787
0.6703	Remote Similarity	NPC472539
0.6703	Remote Similarity	NPC102592
0.6688	Remote Similarity	NPC186284
0.6688	Remote Similarity	NPC22082
0.6687	Remote Similarity	NPC285381
0.6687	Remote Similarity	NPC122106
0.6686	Remote Similarity	NPC328611
0.6685	Remote Similarity	NPC106118
0.6667	Remote Similarity	NPC131450
0.6667	Remote Similarity	NPC472541
0.6667	Remote Similarity	NPC55529
0.6667	Remote Similarity	NPC285192
0.6667	Remote Similarity	NPC182057
0.6667	Remote Similarity	NPC147298
0.6667	Remote Similarity	NPC472542
0.6667	Remote Similarity	NPC474041
0.6649	Remote Similarity	NPC225400
0.6648	Remote Similarity	NPC470317
0.6648	Remote Similarity	NPC473666
0.6647	Remote Similarity	NPC63047
0.6647	Remote Similarity	NPC474058
0.6647	Remote Similarity	NPC27904
0.6647	Remote Similarity	NPC475248
0.6646	Remote Similarity	NPC281094
0.6631	Remote Similarity	NPC317701
0.6629	Remote Similarity	NPC88110
0.6628	Remote Similarity	NPC242269
0.6625	Remote Similarity	NPC472242
0.6624	Remote Similarity	NPC242933
0.6614	Remote Similarity	NPC470786
0.6614	Remote Similarity	NPC471155
0.6614	Remote Similarity	NPC472538
0.661	Remote Similarity	NPC97584
0.6609	Remote Similarity	NPC284775
0.6609	Remote Similarity	NPC186669
0.6607	Remote Similarity	NPC286871
0.6607	Remote Similarity	NPC472121
0.6604	Remote Similarity	NPC308197
0.66	Remote Similarity	NPC250476
0.6599	Remote Similarity	NPC475915
0.6597	Remote Similarity	NPC313673
0.6591	Remote Similarity	NPC256452
0.6588	Remote Similarity	NPC182131
0.6588	Remote Similarity	NPC114637
0.6582	Remote Similarity	NPC316202
0.6579	Remote Similarity	NPC270241
0.6576	Remote Similarity	NPC471199
0.6571	Remote Similarity	NPC11126
0.6569	Remote Similarity	NPC38262
0.6568	Remote Similarity	NPC21174
0.6568	Remote Similarity	NPC271797
0.6564	Remote Similarity	NPC13526
0.6548	Remote Similarity	NPC315368
0.6547	Remote Similarity	NPC20322
0.6545	Remote Similarity	NPC478076
0.6541	Remote Similarity	NPC238499
0.6536	Remote Similarity	NPC231382
0.6536	Remote Similarity	NPC316746
0.6532	Remote Similarity	NPC285622
0.6531	Remote Similarity	NPC27833
0.6529	Remote Similarity	NPC233380
0.6522	Remote Similarity	NPC472293
0.6509	Remote Similarity	NPC176983
0.6509	Remote Similarity	NPC472120
0.6509	Remote Similarity	NPC472101
0.6509	Remote Similarity	NPC99632
0.6509	Remote Similarity	NPC282339
0.6509	Remote Similarity	NPC476231
0.6503	Remote Similarity	NPC242000

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 NPC471164 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	269
0.1-0.2	652
0.2-0.3	938
0.3-0.4	1977
0.4-0.5	2251
0.5-0.6	2131
0.6-0.7	827
0.7-0.8	103
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8027	Intermediate Similarity	NPD5918	Discontinued
0.7943	Intermediate Similarity	NPD486	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1124	Approved
0.7941	Intermediate Similarity	NPD1123	Approved
0.777	Intermediate Similarity	NPD6768	Approved
0.7708	Intermediate Similarity	NPD2949	Approved
0.7708	Intermediate Similarity	NPD2950	Approved
0.7676	Intermediate Similarity	NPD1781	Discontinued
0.7643	Intermediate Similarity	NPD1640	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD951	Approved
0.7616	Intermediate Similarity	NPD6017	Discontinued
0.7613	Intermediate Similarity	NPD2790	Discontinued
0.7582	Intermediate Similarity	NPD979	Approved
0.7548	Intermediate Similarity	NPD3248	Phase 1
0.7533	Intermediate Similarity	NPD6566	Discontinued
0.7518	Intermediate Similarity	NPD9541	Approved
0.7518	Intermediate Similarity	NPD9539	Approved
0.7483	Intermediate Similarity	NPD4464	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1175	Approved
0.7468	Intermediate Similarity	NPD4939	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD441	Approved
0.7466	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1619	Phase 3
0.7432	Intermediate Similarity	NPD5227	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD9540	Approved
0.741	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2918	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD2919	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4942	Approved
0.7347	Intermediate Similarity	NPD1541	Approved
0.7347	Intermediate Similarity	NPD1527	Phase 2
0.731	Intermediate Similarity	NPD4549	Discontinued
0.7305	Intermediate Similarity	NPD5840	Discontinued
0.7279	Intermediate Similarity	NPD1920	Approved
0.7279	Intermediate Similarity	NPD1919	Approved
0.7267	Intermediate Similarity	NPD6342	Discontinued
0.7256	Intermediate Similarity	NPD2404	Discontinued
0.7256	Intermediate Similarity	NPD2413	Phase 2
0.7254	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2331	Discontinued
0.7237	Intermediate Similarity	NPD3434	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7072	Phase 2
0.7226	Intermediate Similarity	NPD1524	Phase 1
0.7218	Intermediate Similarity	NPD1064	Approved
0.7218	Intermediate Similarity	NPD1065	Approved
0.7212	Intermediate Similarity	NPD3376	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD33	Approved
0.7205	Intermediate Similarity	NPD4393	Approved
0.7188	Intermediate Similarity	NPD6855	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1079	Discontinued
0.7172	Intermediate Similarity	NPD797	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2431	Approved
0.7169	Intermediate Similarity	NPD2432	Approved
0.7161	Intermediate Similarity	NPD5933	Phase 3
0.7161	Intermediate Similarity	NPD5932	Phase 3
0.7161	Intermediate Similarity	NPD5931	Phase 3
0.7152	Intermediate Similarity	NPD2037	Approved
0.7125	Intermediate Similarity	NPD4045	Phase 2
0.7125	Intermediate Similarity	NPD4042	Phase 2
0.7124	Intermediate Similarity	NPD2010	Phase 3
0.7118	Intermediate Similarity	NPD4329	Approved
0.7118	Intermediate Similarity	NPD4330	Approved
0.7107	Intermediate Similarity	NPD1854	Approved
0.7105	Intermediate Similarity	NPD7254	Discontinued
0.7101	Intermediate Similarity	NPD3792	Approved
0.7092	Intermediate Similarity	NPD1668	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5748	Phase 2
0.7059	Intermediate Similarity	NPD3782	Discontinued
0.7048	Intermediate Similarity	NPD2454	Approved
0.7048	Intermediate Similarity	NPD2455	Approved
0.7039	Intermediate Similarity	NPD6358	Phase 2
0.7032	Intermediate Similarity	NPD5024	Approved
0.7013	Intermediate Similarity	NPD3625	Discontinued
0.7013	Intermediate Similarity	NPD1222	Discontinued
0.7	Intermediate Similarity	NPD1323	Discontinued
0.6993	Remote Similarity	NPD7142	Discontinued
0.6988	Remote Similarity	NPD4645	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD2365	Approved
0.6964	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2506	Approved
0.6948	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2820	Phase 3
0.6919	Remote Similarity	NPD3989	Phase 3
0.6917	Remote Similarity	NPD708	Approved
0.6883	Remote Similarity	NPD1626	Approved
0.6883	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3470	Approved
0.6879	Remote Similarity	NPD3471	Approved
0.6879	Remote Similarity	NPD3990	Phase 3
0.6871	Remote Similarity	NPD1663	Discontinued
0.6857	Remote Similarity	NPD5179	Approved
0.6857	Remote Similarity	NPD5180	Approved
0.6857	Remote Similarity	NPD5181	Approved
0.6852	Remote Similarity	NPD2360	Approved
0.6813	Remote Similarity	NPD5942	Approved
0.6813	Remote Similarity	NPD5941	Approved
0.6788	Remote Similarity	NPD2427	Approved
0.6784	Remote Similarity	NPD2461	Phase 1
0.677	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2397	Discontinued
0.676	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3468	Approved
0.6744	Remote Similarity	NPD2083	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD3978	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4091	Approved
0.6739	Remote Similarity	NPD1342	Approved
0.6725	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD1625	Approved
0.6705	Remote Similarity	NPD4092	Approved
0.6705	Remote Similarity	NPD3994	Approved
0.6705	Remote Similarity	NPD8241	Phase 2
0.6705	Remote Similarity	NPD3995	Approved
0.6705	Remote Similarity	NPD3991	Approved
0.6705	Remote Similarity	NPD3993	Approved
0.6705	Remote Similarity	NPD3996	Approved
0.6705	Remote Similarity	NPD3992	Approved
0.669	Remote Similarity	NPD851	Approved
0.669	Remote Similarity	NPD853	Approved
0.669	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5131	Approved
0.6688	Remote Similarity	NPD4461	Discontinued
0.6688	Remote Similarity	NPD2791	Discontinued
0.6687	Remote Similarity	NPD6629	Discontinued
0.6686	Remote Similarity	NPD3522	Approved
0.6686	Remote Similarity	NPD7662	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD3246	Discontinued
0.6667	Remote Similarity	NPD3481	Approved
0.6667	Remote Similarity	NPD3790	Phase 2
0.6667	Remote Similarity	NPD3079	Approved
0.6667	Remote Similarity	NPD5504	Discontinued
0.6667	Remote Similarity	NPD3076	Approved
0.6667	Remote Similarity	NPD3997	Approved
0.6667	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3884	Discontinued
0.6667	Remote Similarity	NPD3078	Approved
0.6667	Remote Similarity	NPD3998	Approved
0.6667	Remote Similarity	NPD3999	Approved
0.6667	Remote Similarity	NPD4043	Approved
0.6667	Remote Similarity	NPD941	Approved
0.6667	Remote Similarity	NPD4046	Approved
0.6667	Remote Similarity	NPD3077	Approved
0.6646	Remote Similarity	NPD1189	Approved
0.6646	Remote Similarity	NPD6513	Approved
0.6646	Remote Similarity	NPD6512	Approved
0.6645	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD2754	Discontinued
0.6629	Remote Similarity	NPD7014	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8630	Approved
0.6621	Remote Similarity	NPD922	Approved
0.662	Remote Similarity	NPD3387	Approved
0.6612	Remote Similarity	NPD4848	Phase 1
0.6609	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD2369	Discontinued
0.6608	Remote Similarity	NPD5186	Approved
0.6608	Remote Similarity	NPD5183	Approved
0.6607	Remote Similarity	NPD7220	Approved
0.6604	Remote Similarity	NPD4430	Phase 2
0.6604	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5526	Phase 2
0.66	Remote Similarity	NPD1321	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD4988	Discontinued
0.6584	Remote Similarity	NPD1956	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD1410	Phase 1
0.6576	Remote Similarity	NPD7572	Phase 2
0.6575	Remote Similarity	NPD3304	Phase 2
0.6562	Remote Similarity	NPD4347	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD1544	Phase 1
0.6552	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD480	Approved
0.6547	Remote Similarity	NPD1054	Approved
0.6545	Remote Similarity	NPD737	Phase 2
0.6545	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD813	Approved
0.6543	Remote Similarity	NPD1802	Approved
0.6543	Remote Similarity	NPD7088	Discontinued
0.6543	Remote Similarity	NPD1801	Approved
0.6538	Remote Similarity	NPD7786	Discontinued
0.6536	Remote Similarity	NPD1190	Approved
0.6532	Remote Similarity	NPD5997	Discontinued
0.6532	Remote Similarity	NPD3377	Discontinued
0.6532	Remote Similarity	NPD3868	Phase 1
0.6529	Remote Similarity	NPD3850	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD1025	Discontinued
0.6517	Remote Similarity	NPD4412	Phase 2
0.6503	Remote Similarity	NPD4888	Discontinued
0.65	Remote Similarity	NPD2129	Approved
0.649	Remote Similarity	NPD1593	Approved
0.6486	Remote Similarity	NPD3828	Approved
0.6484	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD1344	Phase 2
0.648	Remote Similarity	NPD6557	Phase 2
0.648	Remote Similarity	NPD3413	Approved
0.648	Remote Similarity	NPD3414	Approved
0.6479	Remote Similarity	NPD3865	Approved
0.6477	Remote Similarity	NPD2869	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2470	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