NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.09
Volume:	258.799
LogP:	3.312
LogD:	2.676
LogS:	-4.284
# Rotatable Bonds:	3
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.765
Synthetic Accessibility Score:	2.425
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.505
MDCK Permeability:	2.7332680474501103e-05
Pgp-inhibitor:	0.897
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.908
30% Bioavailability (F30%):	0.744

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	91.81230163574219%
Volume Distribution (VD):	0.916
Pgp-substrate:	2.890719175338745%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.21
CYP2C19-inhibitor:	0.943
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.85
CYP2C9-substrate:	0.35
CYP2D6-inhibitor:	0.77
CYP2D6-substrate:	0.191
CYP3A4-inhibitor:	0.389
CYP3A4-substrate:	0.156

ADMET: Excretion

Clearance (CL):	7.898
Half-life (T1/2):	0.234

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.932
Drug-inuced Liver Injury (DILI):	0.523
AMES Toxicity:	0.952
Rat Oral Acute Toxicity:	0.821
Maximum Recommended Daily Dose:	0.889
Skin Sensitization:	0.89
Carcinogencity:	0.77
Eye Corrosion:	0.006
Eye Irritation:	0.953
Respiratory Toxicity:	0.238

Download Data

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

Natural Product: NPC470391

Natural Product ID:	NPC470391
*Common Name:**	Lawsone 2-Isopentenyl Ether
IUPAC Name:	2-(3-methylbut-2-enoxy)naphthalene-1,4-dione
Synonyms:	Lawsone 2-Isopentenyl Ether
Standard InCHIKey:	XFZFQASPBARVAD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O3/c1-10(2)7-8-18-14-9-13(16)11-5-3-4-6-12(11)15(14)17/h3-7,9H,8H2,1-2H3
SMILES:	CC(=CCOC1=CC(=O)c2c(C1=O)cccc2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2022661
PubChem CID:	261603
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO28542	Streptocarpus dunnii	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21174407]
NPO28542	Streptocarpus dunnii	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22472691]
NPO28542	Streptocarpus dunnii	Species	Gesneriaceae	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	8

Activity Type	# Activity
Individual Protein	7
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	0.896	n.a.	PMID[523929]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.198	n.a.	PMID[523929]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	1.764	n.a.	PMID[523929]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	2.011	n.a.	PMID[523929]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	2.66	n.a.	PMID[523929]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	3.986	n.a.	PMID[523929]
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	FC	=	7.128	n.a.	PMID[523929]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	14.0	%	PMID[523930]

☑ 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 NPC470391 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	270
0.1-0.2	1334
0.2-0.3	3422
0.3-0.4	9451
0.4-0.5	11708
0.5-0.6	11242
0.6-0.7	4801
0.7-0.8	403
0.8-0.85	49
0.85-0.9	11
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9394	High Similarity	NPC112552
0.9327	High Similarity	NPC291799
0.9159	High Similarity	NPC470764
0.8962	High Similarity	NPC137315
0.8774	High Similarity	NPC192577
0.8716	High Similarity	NPC477411
0.8716	High Similarity	NPC241851
0.8716	High Similarity	NPC196075
0.8636	High Similarity	NPC474408
0.8584	High Similarity	NPC204784
0.8559	High Similarity	NPC226093
0.8558	High Similarity	NPC244427
0.8558	High Similarity	NPC222390
0.8532	High Similarity	NPC212415
0.8529	High Similarity	NPC156021
0.8505	High Similarity	NPC203732
0.8491	Intermediate Similarity	NPC209632
0.8476	Intermediate Similarity	NPC274443
0.8455	Intermediate Similarity	NPC13784
0.844	Intermediate Similarity	NPC474157
0.844	Intermediate Similarity	NPC210089
0.84	Intermediate Similarity	NPC476484
0.8396	Intermediate Similarity	NPC114594
0.8393	Intermediate Similarity	NPC135730
0.839	Intermediate Similarity	NPC236405
0.8378	Intermediate Similarity	NPC326664
0.8318	Intermediate Similarity	NPC172483
0.8304	Intermediate Similarity	NPC228936
0.8302	Intermediate Similarity	NPC60679
0.8291	Intermediate Similarity	NPC65627
0.8288	Intermediate Similarity	NPC272524
0.8257	Intermediate Similarity	NPC99846
0.8257	Intermediate Similarity	NPC269023
0.8252	Intermediate Similarity	NPC12695
0.8241	Intermediate Similarity	NPC30594
0.8241	Intermediate Similarity	NPC37622
0.8241	Intermediate Similarity	NPC119271
0.8214	Intermediate Similarity	NPC308744
0.819	Intermediate Similarity	NPC105709
0.8165	Intermediate Similarity	NPC56493
0.8151	Intermediate Similarity	NPC295664
0.8142	Intermediate Similarity	NPC474685
0.8142	Intermediate Similarity	NPC210092
0.8125	Intermediate Similarity	NPC161611
0.812	Intermediate Similarity	NPC144547
0.8095	Intermediate Similarity	NPC145052
0.8091	Intermediate Similarity	NPC17417
0.8091	Intermediate Similarity	NPC10251
0.8091	Intermediate Similarity	NPC265407
0.8091	Intermediate Similarity	NPC83628
0.807	Intermediate Similarity	NPC62138
0.8056	Intermediate Similarity	NPC31786
0.8053	Intermediate Similarity	NPC67377
0.8034	Intermediate Similarity	NPC289432
0.8034	Intermediate Similarity	NPC988
0.8018	Intermediate Similarity	NPC196246
0.8018	Intermediate Similarity	NPC174099
0.8018	Intermediate Similarity	NPC214067
0.8018	Intermediate Similarity	NPC251854
0.8018	Intermediate Similarity	NPC93084
0.8017	Intermediate Similarity	NPC81135
0.8	Intermediate Similarity	NPC92754
0.8	Intermediate Similarity	NPC276775
0.8	Intermediate Similarity	NPC103048
0.8	Intermediate Similarity	NPC249912
0.7982	Intermediate Similarity	NPC474095
0.7963	Intermediate Similarity	NPC301943
0.7963	Intermediate Similarity	NPC474365
0.7963	Intermediate Similarity	NPC89886
0.7946	Intermediate Similarity	NPC260818
0.7946	Intermediate Similarity	NPC305912
0.7946	Intermediate Similarity	NPC1082
0.7946	Intermediate Similarity	NPC167504
0.7944	Intermediate Similarity	NPC42211
0.7941	Intermediate Similarity	NPC67585
0.7941	Intermediate Similarity	NPC303967
0.7941	Intermediate Similarity	NPC110420
0.7925	Intermediate Similarity	NPC78701
0.7925	Intermediate Similarity	NPC225060
0.7925	Intermediate Similarity	NPC35448
0.7881	Intermediate Similarity	NPC232958
0.7881	Intermediate Similarity	NPC238861
0.7881	Intermediate Similarity	NPC473243
0.7881	Intermediate Similarity	NPC77000
0.7876	Intermediate Similarity	NPC270699
0.7876	Intermediate Similarity	NPC79496
0.7876	Intermediate Similarity	NPC321852
0.7876	Intermediate Similarity	NPC292834
0.7876	Intermediate Similarity	NPC82899
0.787	Intermediate Similarity	NPC45613
0.785	Intermediate Similarity	NPC146351
0.785	Intermediate Similarity	NPC118343
0.7822	Intermediate Similarity	NPC43945
0.7818	Intermediate Similarity	NPC134120
0.781	Intermediate Similarity	NPC130398
0.7788	Intermediate Similarity	NPC243355
0.7778	Intermediate Similarity	NPC70624
0.7778	Intermediate Similarity	NPC215008
0.7769	Intermediate Similarity	NPC51079
0.7768	Intermediate Similarity	NPC85493
0.7768	Intermediate Similarity	NPC474364
0.7759	Intermediate Similarity	NPC100353
0.7759	Intermediate Similarity	NPC149691
0.7745	Intermediate Similarity	NPC157778
0.7739	Intermediate Similarity	NPC11824
0.7739	Intermediate Similarity	NPC153053
0.7739	Intermediate Similarity	NPC307651
0.7727	Intermediate Similarity	NPC249067
0.7724	Intermediate Similarity	NPC51037
0.7719	Intermediate Similarity	NPC23332
0.7712	Intermediate Similarity	NPC318173
0.7706	Intermediate Similarity	NPC320891
0.7685	Intermediate Similarity	NPC325497
0.7679	Intermediate Similarity	NPC211439
0.7674	Intermediate Similarity	NPC232996
0.7672	Intermediate Similarity	NPC306740
0.7664	Intermediate Similarity	NPC270654
0.7652	Intermediate Similarity	NPC128368
0.7652	Intermediate Similarity	NPC143768
0.7642	Intermediate Similarity	NPC5472
0.7642	Intermediate Similarity	NPC476599
0.7632	Intermediate Similarity	NPC183648
0.7627	Intermediate Similarity	NPC222968
0.7627	Intermediate Similarity	NPC323440
0.7627	Intermediate Similarity	NPC80605
0.7623	Intermediate Similarity	NPC328107
0.7623	Intermediate Similarity	NPC318067
0.7623	Intermediate Similarity	NPC182646
0.7611	Intermediate Similarity	NPC40178
0.7611	Intermediate Similarity	NPC469636
0.76	Intermediate Similarity	NPC165257
0.76	Intermediate Similarity	NPC237225
0.7596	Intermediate Similarity	NPC173413
0.7593	Intermediate Similarity	NPC229242
0.7586	Intermediate Similarity	NPC196673
0.7583	Intermediate Similarity	NPC476225
0.7563	Intermediate Similarity	NPC152159
0.7559	Intermediate Similarity	NPC205360
0.7545	Intermediate Similarity	NPC188895
0.7541	Intermediate Similarity	NPC223351
0.754	Intermediate Similarity	NPC471832
0.7524	Intermediate Similarity	NPC110704
0.7524	Intermediate Similarity	NPC284475
0.7523	Intermediate Similarity	NPC203925
0.7522	Intermediate Similarity	NPC47536
0.75	Intermediate Similarity	NPC474176
0.75	Intermediate Similarity	NPC269457
0.7481	Intermediate Similarity	NPC284184
0.7481	Intermediate Similarity	NPC301341
0.748	Intermediate Similarity	NPC27659
0.7479	Intermediate Similarity	NPC471553
0.7479	Intermediate Similarity	NPC469954
0.7478	Intermediate Similarity	NPC474057
0.7476	Intermediate Similarity	NPC96625
0.7462	Intermediate Similarity	NPC217914
0.7458	Intermediate Similarity	NPC471616
0.7456	Intermediate Similarity	NPC281604
0.7453	Intermediate Similarity	NPC1682
0.7453	Intermediate Similarity	NPC188844
0.7453	Intermediate Similarity	NPC77273
0.7453	Intermediate Similarity	NPC155232
0.7451	Intermediate Similarity	NPC294134
0.744	Intermediate Similarity	NPC177925
0.7436	Intermediate Similarity	NPC279916
0.7434	Intermediate Similarity	NPC100767
0.7426	Intermediate Similarity	NPC39600
0.7419	Intermediate Similarity	NPC246166
0.7414	Intermediate Similarity	NPC212718
0.7414	Intermediate Similarity	NPC186128
0.7414	Intermediate Similarity	NPC57879
0.7414	Intermediate Similarity	NPC158282
0.7414	Intermediate Similarity	NPC474314
0.7411	Intermediate Similarity	NPC329282
0.7411	Intermediate Similarity	NPC269644
0.7405	Intermediate Similarity	NPC38158
0.7398	Intermediate Similarity	NPC164947
0.7398	Intermediate Similarity	NPC217756
0.7395	Intermediate Similarity	NPC469843
0.7395	Intermediate Similarity	NPC28951
0.7395	Intermediate Similarity	NPC325646
0.7387	Intermediate Similarity	NPC284477
0.7383	Intermediate Similarity	NPC34243
0.7383	Intermediate Similarity	NPC238219
0.7383	Intermediate Similarity	NPC23453
0.7381	Intermediate Similarity	NPC478162
0.7381	Intermediate Similarity	NPC478165
0.7381	Intermediate Similarity	NPC45537
0.7377	Intermediate Similarity	NPC50872
0.7374	Intermediate Similarity	NPC300205
0.7373	Intermediate Similarity	NPC252004
0.7368	Intermediate Similarity	NPC477408
0.7364	Intermediate Similarity	NPC476042
0.7364	Intermediate Similarity	NPC477407
0.7358	Intermediate Similarity	NPC133461
0.7344	Intermediate Similarity	NPC198305
0.7339	Intermediate Similarity	NPC228739
0.7339	Intermediate Similarity	NPC289201
0.7339	Intermediate Similarity	NPC135062
0.7333	Intermediate Similarity	NPC173443
0.7333	Intermediate Similarity	NPC45104

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 NPC470391 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	948
0.2-0.3	1214
0.3-0.4	2860
0.4-0.5	2401
0.5-0.6	1172
0.6-0.7	274
0.7-0.8	29
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8532	High Similarity	NPD1609	Clinical (unspecified phase)
0.8091	Intermediate Similarity	NPD2182	Approved
0.8056	Intermediate Similarity	NPD164	Approved
0.7946	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD1238	Approved
0.7822	Intermediate Similarity	NPD650	Approved
0.7739	Intermediate Similarity	NPD1241	Discontinued
0.7727	Intermediate Similarity	NPD1237	Approved
0.7699	Intermediate Similarity	NPD2067	Discontinued
0.7672	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7524	Intermediate Similarity	NPD7609	Phase 3
0.7453	Intermediate Similarity	NPD7631	Approved
0.7419	Intermediate Similarity	NPD1876	Approved
0.7258	Intermediate Similarity	NPD3972	Approved
0.7257	Intermediate Similarity	NPD5909	Discontinued
0.7236	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1202	Approved
0.7212	Intermediate Similarity	NPD9257	Approved
0.7212	Intermediate Similarity	NPD9259	Approved
0.7179	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1929	Approved
0.7168	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD1930	Approved
0.7164	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD1282	Approved
0.7131	Intermediate Similarity	NPD9545	Approved
0.713	Intermediate Similarity	NPD1508	Approved
0.7107	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4879	Approved
0.7091	Intermediate Similarity	NPD1989	Approved
0.7059	Intermediate Similarity	NPD942	Approved
0.7054	Intermediate Similarity	NPD2066	Phase 3
0.7027	Intermediate Similarity	NPD3495	Discontinued
0.7009	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD9495	Approved
0.6944	Remote Similarity	NPD9256	Approved
0.6944	Remote Similarity	NPD9258	Approved
0.6937	Remote Similarity	NPD1843	Approved
0.693	Remote Similarity	NPD1932	Approved
0.6909	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6287	Discontinued
0.687	Remote Similarity	NPD6647	Phase 2
0.687	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD9490	Approved
0.6857	Remote Similarity	NPD3950	Discontinued
0.685	Remote Similarity	NPD4878	Approved
0.6842	Remote Similarity	NPD3142	Approved
0.6842	Remote Similarity	NPD3140	Approved
0.6829	Remote Similarity	NPD9493	Approved
0.6822	Remote Similarity	NPD1087	Approved
0.6803	Remote Similarity	NPD5951	Approved
0.68	Remote Similarity	NPD1651	Approved
0.6794	Remote Similarity	NPD6832	Phase 2
0.6789	Remote Similarity	NPD3673	Approved
0.6789	Remote Similarity	NPD3672	Approved
0.6786	Remote Similarity	NPD7236	Approved
0.6769	Remote Similarity	NPD2798	Approved
0.6769	Remote Similarity	NPD2788	Approved
0.6762	Remote Similarity	NPD9491	Approved
0.6742	Remote Similarity	NPD7008	Discontinued
0.6723	Remote Similarity	NPD2329	Discontinued
0.6719	Remote Similarity	NPD6637	Approved
0.6714	Remote Similarity	NPD3887	Approved
0.6696	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD1693	Approved
0.6696	Remote Similarity	NPD9260	Approved
0.6667	Remote Similarity	NPD2629	Approved
0.6667	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2353	Approved
0.6667	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD3748	Approved
0.6642	Remote Similarity	NPD7713	Phase 3
0.6641	Remote Similarity	NPD1281	Approved
0.6641	Remote Similarity	NPD1019	Discontinued
0.6641	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.664	Remote Similarity	NPD2347	Approved
0.6639	Remote Similarity	NPD6858	Approved
0.6639	Remote Similarity	NPD7094	Approved
0.6636	Remote Similarity	NPD1089	Approved
0.6636	Remote Similarity	NPD1086	Approved
0.6636	Remote Similarity	NPD1090	Approved
0.6635	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6799	Approved
0.6617	Remote Similarity	NPD6039	Approved
0.6615	Remote Similarity	NPD5667	Approved
0.6615	Remote Similarity	NPD2198	Approved
0.6615	Remote Similarity	NPD2199	Approved
0.6614	Remote Similarity	NPD17	Approved
0.6614	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD1563	Approved
0.6602	Remote Similarity	NPD225	Approved
0.6602	Remote Similarity	NPD227	Approved
0.6594	Remote Similarity	NPD2796	Approved
0.6593	Remote Similarity	NPD1240	Approved
0.6589	Remote Similarity	NPD9717	Approved
0.6581	Remote Similarity	NPD9261	Approved
0.6577	Remote Similarity	NPD1239	Approved
0.6567	Remote Similarity	NPD3764	Approved
0.6565	Remote Similarity	NPD3266	Approved
0.6565	Remote Similarity	NPD1470	Approved
0.6565	Remote Similarity	NPD3267	Approved
0.6555	Remote Similarity	NPD3134	Approved
0.6552	Remote Similarity	NPD7239	Suspended
0.6547	Remote Similarity	NPD2346	Discontinued
0.6547	Remote Similarity	NPD2344	Approved
0.6545	Remote Similarity	NPD800	Approved
0.6535	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5926	Approved
0.6519	Remote Similarity	NPD7961	Discontinued
0.6518	Remote Similarity	NPD1088	Approved
0.6512	Remote Similarity	NPD1201	Approved
0.65	Remote Similarity	NPD1358	Approved
0.65	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD1607	Approved
0.6489	Remote Similarity	NPD1283	Approved
0.6484	Remote Similarity	NPD5306	Approved
0.6484	Remote Similarity	NPD5305	Approved
0.648	Remote Similarity	NPD4198	Discontinued
0.6479	Remote Similarity	NPD2354	Approved
0.6471	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD9494	Approved
0.6463	Remote Similarity	NPD6599	Discontinued
0.6462	Remote Similarity	NPD1608	Approved
0.6457	Remote Similarity	NPD1894	Discontinued
0.6454	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6010	Discontinued
0.6444	Remote Similarity	NPD2313	Discontinued
0.6439	Remote Similarity	NPD1203	Approved
0.6435	Remote Similarity	NPD1566	Phase 3
0.6435	Remote Similarity	NPD1565	Approved
0.6435	Remote Similarity	NPD1564	Approved
0.6434	Remote Similarity	NPD4106	Approved
0.6434	Remote Similarity	NPD4135	Approved
0.6434	Remote Similarity	NPD4136	Approved
0.6423	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD226	Approved
0.6412	Remote Similarity	NPD5159	Phase 2
0.6412	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD5157	Phase 1
0.6408	Remote Similarity	NPD4628	Phase 3
0.6408	Remote Similarity	NPD3750	Approved
0.6406	Remote Similarity	NPD5691	Approved
0.6403	Remote Similarity	NPD2799	Discontinued
0.6403	Remote Similarity	NPD1510	Phase 2
0.6393	Remote Similarity	NPD1756	Approved
0.6393	Remote Similarity	NPD1317	Discontinued
0.6393	Remote Similarity	NPD1752	Approved
0.6387	Remote Similarity	NPD3047	Approved
0.6387	Remote Similarity	NPD3048	Approved
0.6387	Remote Similarity	NPD3046	Approved
0.6385	Remote Similarity	NPD4806	Approved
0.6385	Remote Similarity	NPD4807	Approved
0.6383	Remote Similarity	NPD2897	Discontinued
0.6383	Remote Similarity	NPD1549	Phase 2
0.6383	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD2607	Approved
0.6364	Remote Similarity	NPD9264	Approved
0.6364	Remote Similarity	NPD9263	Approved
0.6364	Remote Similarity	NPD2309	Approved
0.6364	Remote Similarity	NPD9267	Approved
0.635	Remote Similarity	NPD4307	Phase 2
0.635	Remote Similarity	NPD2979	Phase 3
0.6349	Remote Similarity	NPD3317	Approved
0.6345	Remote Similarity	NPD5401	Approved
0.6333	Remote Similarity	NPD9697	Approved
0.6328	Remote Similarity	NPD7009	Phase 2
0.6327	Remote Similarity	NPD957	Approved
0.6325	Remote Similarity	NPD7798	Approved
0.6324	Remote Similarity	NPD6798	Discontinued
0.6324	Remote Similarity	NPD3268	Approved
0.6316	Remote Similarity	NPD2797	Approved
0.6316	Remote Similarity	NPD552	Approved
0.6316	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD553	Approved
0.6316	Remote Similarity	NPD9567	Approved
0.6312	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD74	Approved
0.6311	Remote Similarity	NPD9266	Approved
0.6304	Remote Similarity	NPD1933	Approved
0.6304	Remote Similarity	NPD6355	Discontinued
0.6301	Remote Similarity	NPD6273	Approved
0.6296	Remote Similarity	NPD7055	Discontinued
0.6296	Remote Similarity	NPD3971	Phase 1
0.6294	Remote Similarity	NPD7003	Approved
0.6294	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.629	Remote Similarity	NPD969	Suspended
0.6284	Remote Similarity	NPD3226	Approved
0.6284	Remote Similarity	NPD2651	Approved
0.6284	Remote Similarity	NPD2649	Approved
0.6279	Remote Similarity	NPD4105	Approved
0.6279	Remote Similarity	NPD4102	Approved
0.6279	Remote Similarity	NPD5585	Approved
0.6277	Remote Similarity	NPD4062	Phase 3
0.6277	Remote Similarity	NPD6233	Phase 2

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