NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	263.425
LogP:	3.53
LogD:	3.193
LogS:	-4.459
# Rotatable Bonds:	0
TPSA:	38.83
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.377
Synthetic Accessibility Score:	4.689
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.627
MDCK Permeability:	2.6498953957343474e-05
Pgp-inhibitor:	0.021
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.303
30% Bioavailability (F30%):	0.881

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.772
Plasma Protein Binding (PPB):	79.58749389648438%
Volume Distribution (VD):	1.362
Pgp-substrate:	21.03190803527832%

ADMET: Metabolism

CYP1A2-inhibitor:	0.209
CYP1A2-substrate:	0.369
CYP2C19-inhibitor:	0.189
CYP2C19-substrate:	0.695
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.263
CYP3A4-inhibitor:	0.615
CYP3A4-substrate:	0.275

ADMET: Excretion

Clearance (CL):	6.287
Half-life (T1/2):	0.262

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.727
Drug-inuced Liver Injury (DILI):	0.516
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.747
Carcinogencity:	0.099
Eye Corrosion:	0.33
Eye Irritation:	0.371
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC207188

Natural Product ID:	NPC207188
*Common Name:**	11Beta,13-Dihydro-Parthenolide
IUPAC Name:	n.a.
Synonyms:	11,13-Dihydroparthenolide; 11Beta,13-Dihydro-Parthenolide; 11Beta,13-Dihydroparthenolide
Standard InCHIKey:	GSVWPONNFJXHJL-IOCBBESTSA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,10-13H,4,6-8H2,1-3H3/b9-5+/t10-,11-,12-,13+,15+/m0/s1
SMILES:	C/C/1=CCC[C@]2(C)[C@@H]([C@@H]3[C@@H](CC1)[C@H](C)C(=O)O3)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL429762
PubChem CID:	13966494
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO40799	Bovine platelets	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1431933]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695795]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31009220]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21040	Ambrosia artemisiifolia	Species	Asteraceae	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	7
Others	1

Activity Type	# Activity
Cell Line	1
CELL-LINE	1
Individual Protein	2
NON-MOLECULAR	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	200.0	ug.mL-1	PMID[468035]
NPT20967	CELL-LINE	Platelet	n.a.	IC50	>	399500.0	nM	PMID[468033]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	399500.0	nM	PMID[468034]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	157.93	ug.mL-1	PMID[468035]
NPT27	Others	Unspecified		log Pe	=	-4.55	n.a.	PMID[468036]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	50003.45	nM	PMID[468037]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[468037]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	>	30000.0	nM	PMID[468037]

☑ 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 NPC207188 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	211
0.1-0.2	1612
0.2-0.3	6732
0.3-0.4	15973
0.4-0.5	8664
0.5-0.6	7139
0.6-0.7	1984
0.7-0.8	338
0.8-0.85	32
0.85-0.9	6
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9012	High Similarity	NPC50362
0.9012	High Similarity	NPC38468
0.9012	High Similarity	NPC319795
0.881	High Similarity	NPC151770
0.8488	Intermediate Similarity	NPC251385
0.8488	Intermediate Similarity	NPC49342
0.8488	Intermediate Similarity	NPC312042
0.8409	Intermediate Similarity	NPC473330
0.8409	Intermediate Similarity	NPC473316
0.8372	Intermediate Similarity	NPC166919
0.8353	Intermediate Similarity	NPC231889
0.8313	Intermediate Similarity	NPC272814
0.8276	Intermediate Similarity	NPC475748
0.8242	Intermediate Similarity	NPC208233
0.8235	Intermediate Similarity	NPC50637
0.8228	Intermediate Similarity	NPC93213
0.8202	Intermediate Similarity	NPC476267
0.8202	Intermediate Similarity	NPC57405
0.8202	Intermediate Similarity	NPC303942
0.8202	Intermediate Similarity	NPC471147
0.8111	Intermediate Similarity	NPC475659
0.809	Intermediate Similarity	NPC212486
0.8043	Intermediate Similarity	NPC279561
0.8043	Intermediate Similarity	NPC473326
0.8022	Intermediate Similarity	NPC473859
0.8022	Intermediate Similarity	NPC35498
0.8	Intermediate Similarity	NPC140543
0.8	Intermediate Similarity	NPC471491
0.7957	Intermediate Similarity	NPC288876
0.7931	Intermediate Similarity	NPC475703
0.7931	Intermediate Similarity	NPC5130
0.7912	Intermediate Similarity	NPC270013
0.7912	Intermediate Similarity	NPC14961
0.7895	Intermediate Similarity	NPC215988
0.7889	Intermediate Similarity	NPC477615
0.7872	Intermediate Similarity	NPC264477
0.7872	Intermediate Similarity	NPC477511
0.7865	Intermediate Similarity	NPC62815
0.7848	Intermediate Similarity	NPC129665
0.7831	Intermediate Similarity	NPC617
0.7826	Intermediate Similarity	NPC476315
0.7826	Intermediate Similarity	NPC279621
0.7826	Intermediate Similarity	NPC17585
0.7821	Intermediate Similarity	NPC296522
0.7821	Intermediate Similarity	NPC144511
0.7816	Intermediate Similarity	NPC475491
0.7816	Intermediate Similarity	NPC469626
0.7802	Intermediate Similarity	NPC474035
0.7802	Intermediate Similarity	NPC81386
0.7791	Intermediate Similarity	NPC470238
0.7791	Intermediate Similarity	NPC138647
0.7778	Intermediate Similarity	NPC184463
0.7778	Intermediate Similarity	NPC475861
0.7753	Intermediate Similarity	NPC307411
0.7753	Intermediate Similarity	NPC473564
0.7753	Intermediate Similarity	NPC4986
0.7753	Intermediate Similarity	NPC475971
0.7753	Intermediate Similarity	NPC474032
0.7742	Intermediate Similarity	NPC471140
0.7738	Intermediate Similarity	NPC474739
0.7722	Intermediate Similarity	NPC472955
0.7717	Intermediate Similarity	NPC107476
0.7701	Intermediate Similarity	NPC474547
0.7692	Intermediate Similarity	NPC125674
0.7692	Intermediate Similarity	NPC228451
0.7692	Intermediate Similarity	NPC475912
0.7692	Intermediate Similarity	NPC476300
0.7692	Intermediate Similarity	NPC475838
0.7683	Intermediate Similarity	NPC226242
0.7683	Intermediate Similarity	NPC235906
0.7683	Intermediate Similarity	NPC472959
0.7674	Intermediate Similarity	NPC257358
0.7674	Intermediate Similarity	NPC475622
0.7674	Intermediate Similarity	NPC108045
0.7674	Intermediate Similarity	NPC474472
0.7667	Intermediate Similarity	NPC329857
0.7667	Intermediate Similarity	NPC51004
0.7667	Intermediate Similarity	NPC469718
0.7654	Intermediate Similarity	NPC472966
0.7647	Intermediate Similarity	NPC141810
0.764	Intermediate Similarity	NPC476704
0.764	Intermediate Similarity	NPC224652
0.764	Intermediate Similarity	NPC281516
0.764	Intermediate Similarity	NPC202672
0.7629	Intermediate Similarity	NPC471143
0.7629	Intermediate Similarity	NPC477510
0.7619	Intermediate Similarity	NPC89128
0.7614	Intermediate Similarity	NPC469676
0.7609	Intermediate Similarity	NPC476716
0.7609	Intermediate Similarity	NPC474247
0.7595	Intermediate Similarity	NPC199557
0.759	Intermediate Similarity	NPC474760
0.7586	Intermediate Similarity	NPC472957
0.7586	Intermediate Similarity	NPC472958
0.7582	Intermediate Similarity	NPC20713
0.7582	Intermediate Similarity	NPC208886
0.7582	Intermediate Similarity	NPC70251
0.7582	Intermediate Similarity	NPC12172
0.7582	Intermediate Similarity	NPC475881
0.7582	Intermediate Similarity	NPC30515
0.7579	Intermediate Similarity	NPC477512
0.7576	Intermediate Similarity	NPC70235
0.7561	Intermediate Similarity	NPC155587
0.7529	Intermediate Similarity	NPC474981
0.7529	Intermediate Similarity	NPC103634
0.7527	Intermediate Similarity	NPC36954
0.7527	Intermediate Similarity	NPC471141
0.7526	Intermediate Similarity	NPC474166
0.7526	Intermediate Similarity	NPC19239
0.75	Intermediate Similarity	NPC149725
0.75	Intermediate Similarity	NPC81419
0.75	Intermediate Similarity	NPC475310
0.75	Intermediate Similarity	NPC47958
0.75	Intermediate Similarity	NPC207186
0.75	Intermediate Similarity	NPC47880
0.75	Intermediate Similarity	NPC179746
0.75	Intermediate Similarity	NPC164598
0.75	Intermediate Similarity	NPC304509
0.75	Intermediate Similarity	NPC474339
0.75	Intermediate Similarity	NPC476270
0.7475	Intermediate Similarity	NPC477513
0.7474	Intermediate Similarity	NPC474213
0.7473	Intermediate Similarity	NPC473619
0.7473	Intermediate Similarity	NPC474761
0.7473	Intermediate Similarity	NPC476004
0.7473	Intermediate Similarity	NPC65359
0.7471	Intermediate Similarity	NPC170377
0.7471	Intermediate Similarity	NPC475842
0.7471	Intermediate Similarity	NPC231601
0.7449	Intermediate Similarity	NPC474741
0.7447	Intermediate Similarity	NPC230800
0.7444	Intermediate Similarity	NPC476707
0.7444	Intermediate Similarity	NPC476706
0.7444	Intermediate Similarity	NPC473715
0.7423	Intermediate Similarity	NPC149371
0.7423	Intermediate Similarity	NPC471148
0.7419	Intermediate Similarity	NPC66581
0.7416	Intermediate Similarity	NPC474045
0.7416	Intermediate Similarity	NPC470242
0.7416	Intermediate Similarity	NPC261253
0.7416	Intermediate Similarity	NPC284902
0.7412	Intermediate Similarity	NPC80999
0.7396	Intermediate Similarity	NPC475949
0.7391	Intermediate Similarity	NPC469627
0.7391	Intermediate Similarity	NPC473321
0.7386	Intermediate Similarity	NPC72464
0.7381	Intermediate Similarity	NPC195785
0.7381	Intermediate Similarity	NPC145898
0.7381	Intermediate Similarity	NPC15975
0.7375	Intermediate Similarity	NPC329656
0.7374	Intermediate Similarity	NPC9303
0.7374	Intermediate Similarity	NPC16313
0.7374	Intermediate Similarity	NPC475802
0.7374	Intermediate Similarity	NPC223450
0.7374	Intermediate Similarity	NPC243998
0.7363	Intermediate Similarity	NPC471222
0.7349	Intermediate Similarity	NPC324762
0.734	Intermediate Similarity	NPC474947
0.734	Intermediate Similarity	NPC471142
0.7333	Intermediate Similarity	NPC190753
0.7333	Intermediate Similarity	NPC248602
0.7333	Intermediate Similarity	NPC270270
0.7333	Intermediate Similarity	NPC179659
0.7333	Intermediate Similarity	NPC471739
0.7333	Intermediate Similarity	NPC266957
0.7333	Intermediate Similarity	NPC474765
0.7326	Intermediate Similarity	NPC200446
0.7326	Intermediate Similarity	NPC474510
0.732	Intermediate Similarity	NPC201718
0.732	Intermediate Similarity	NPC474742
0.732	Intermediate Similarity	NPC473332
0.7317	Intermediate Similarity	NPC269206
0.7317	Intermediate Similarity	NPC58956
0.7317	Intermediate Similarity	NPC107783
0.7317	Intermediate Similarity	NPC295633
0.7317	Intermediate Similarity	NPC92909
0.7312	Intermediate Similarity	NPC288240
0.7312	Intermediate Similarity	NPC162205
0.7312	Intermediate Similarity	NPC295204
0.7312	Intermediate Similarity	NPC273579
0.7303	Intermediate Similarity	NPC235792
0.7303	Intermediate Similarity	NPC475206
0.7303	Intermediate Similarity	NPC99395
0.7303	Intermediate Similarity	NPC197903
0.73	Intermediate Similarity	NPC72813
0.73	Intermediate Similarity	NPC324327
0.73	Intermediate Similarity	NPC474421
0.73	Intermediate Similarity	NPC475510
0.73	Intermediate Similarity	NPC194620
0.73	Intermediate Similarity	NPC475587
0.73	Intermediate Similarity	NPC326994
0.7294	Intermediate Similarity	NPC474341
0.7294	Intermediate Similarity	NPC218817
0.7294	Intermediate Similarity	NPC470014
0.7294	Intermediate Similarity	NPC11796
0.7294	Intermediate Similarity	NPC35574
0.7294	Intermediate Similarity	NPC469495
0.7292	Intermediate Similarity	NPC471144
0.7283	Intermediate Similarity	NPC144133
0.7283	Intermediate Similarity	NPC179394

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 NPC207188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	2341
0.2-0.3	4100
0.3-0.4	1711
0.4-0.5	491
0.5-0.6	272
0.6-0.7	37
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9012	High Similarity	NPD1733	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD1695	Approved
0.6915	Remote Similarity	NPD6698	Approved
0.6915	Remote Similarity	NPD46	Approved
0.6863	Remote Similarity	NPD6008	Approved
0.6842	Remote Similarity	NPD7983	Approved
0.6778	Remote Similarity	NPD6435	Approved
0.6635	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5778	Approved
0.6598	Remote Similarity	NPD5779	Approved
0.6559	Remote Similarity	NPD1694	Approved
0.6556	Remote Similarity	NPD5368	Approved
0.6531	Remote Similarity	NPD5282	Discontinued
0.6484	Remote Similarity	NPD5369	Approved
0.6463	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6101	Approved
0.6449	Remote Similarity	NPD6371	Approved
0.6392	Remote Similarity	NPD7838	Discovery
0.6344	Remote Similarity	NPD7154	Phase 3
0.6327	Remote Similarity	NPD6411	Approved
0.6321	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4249	Approved
0.6316	Remote Similarity	NPD7521	Approved
0.6316	Remote Similarity	NPD7334	Approved
0.6316	Remote Similarity	NPD5330	Approved
0.6316	Remote Similarity	NPD7146	Approved
0.6316	Remote Similarity	NPD6684	Approved
0.6316	Remote Similarity	NPD6409	Approved
0.6316	Remote Similarity	NPD5786	Approved
0.625	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD4251	Approved
0.6239	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6903	Approved
0.6186	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.617	Remote Similarity	NPD5362	Discontinued
0.6147	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6686	Approved
0.61	Remote Similarity	NPD6399	Phase 3
0.6082	Remote Similarity	NPD3573	Approved
0.6078	Remote Similarity	NPD7839	Suspended
0.6064	Remote Similarity	NPD4270	Approved
0.6064	Remote Similarity	NPD4269	Approved
0.6061	Remote Similarity	NPD5207	Approved
0.6058	Remote Similarity	NPD6648	Approved
0.6055	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6001	Approved
0.6036	Remote Similarity	NPD6053	Discontinued
0.6034	Remote Similarity	NPD8516	Approved
0.6034	Remote Similarity	NPD8517	Approved
0.6034	Remote Similarity	NPD8515	Approved
0.6034	Remote Similarity	NPD8513	Phase 3
0.6022	Remote Similarity	NPD4822	Approved
0.6022	Remote Similarity	NPD4821	Approved
0.6022	Remote Similarity	NPD4820	Approved
0.6022	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD4819	Approved
0.602	Remote Similarity	NPD5737	Approved
0.602	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD7331	Phase 2
0.6	Remote Similarity	NPD5344	Discontinued
0.6	Remote Similarity	NPD8039	Approved
0.5982	Remote Similarity	NPD4632	Approved
0.598	Remote Similarity	NPD5695	Phase 3
0.5979	Remote Similarity	NPD6098	Approved
0.5979	Remote Similarity	NPD6422	Discontinued
0.5978	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD1145	Discontinued
0.5962	Remote Similarity	NPD4225	Approved
0.5962	Remote Similarity	NPD5696	Approved
0.5948	Remote Similarity	NPD6319	Approved
0.5926	Remote Similarity	NPD6675	Approved
0.5926	Remote Similarity	NPD5739	Approved
0.5926	Remote Similarity	NPD7128	Approved
0.5926	Remote Similarity	NPD6402	Approved
0.5922	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6372	Approved
0.5909	Remote Similarity	NPD6373	Approved
0.59	Remote Similarity	NPD3168	Discontinued
0.5895	Remote Similarity	NPD5209	Approved
0.5893	Remote Similarity	NPD8297	Approved
0.5882	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7341	Phase 2
0.5882	Remote Similarity	NPD7492	Approved
0.5882	Remote Similarity	NPD7900	Approved
0.5876	Remote Similarity	NPD5363	Approved
0.5876	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6412	Phase 2
0.5872	Remote Similarity	NPD5701	Approved
0.5872	Remote Similarity	NPD5697	Approved
0.5865	Remote Similarity	NPD6084	Phase 2
0.5865	Remote Similarity	NPD6083	Phase 2
0.5859	Remote Similarity	NPD5208	Approved
0.5851	Remote Similarity	NPD4252	Approved
0.5833	Remote Similarity	NPD6616	Approved
0.5826	Remote Similarity	NPD6009	Approved
0.5826	Remote Similarity	NPD7115	Discovery
0.5818	Remote Similarity	NPD6881	Approved
0.5818	Remote Similarity	NPD7320	Approved
0.5818	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD6899	Approved
0.5812	Remote Similarity	NPD6059	Approved
0.5812	Remote Similarity	NPD6054	Approved
0.581	Remote Similarity	NPD7638	Approved
0.581	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD4271	Approved
0.5806	Remote Similarity	NPD4268	Approved
0.5804	Remote Similarity	NPD6649	Approved
0.5804	Remote Similarity	NPD6650	Approved
0.58	Remote Similarity	NPD6080	Approved
0.58	Remote Similarity	NPD6673	Approved
0.58	Remote Similarity	NPD6904	Approved
0.5798	Remote Similarity	NPD7604	Phase 2
0.5785	Remote Similarity	NPD7078	Approved
0.5785	Remote Similarity	NPD8293	Discontinued
0.5785	Remote Similarity	NPD8074	Phase 3
0.5766	Remote Similarity	NPD6012	Approved
0.5766	Remote Similarity	NPD6014	Approved
0.5766	Remote Similarity	NPD6013	Approved
0.5765	Remote Similarity	NPD3197	Phase 1
0.5763	Remote Similarity	NPD6016	Approved
0.5763	Remote Similarity	NPD5983	Phase 2
0.5763	Remote Similarity	NPD6015	Approved
0.5755	Remote Similarity	NPD7640	Approved
0.5755	Remote Similarity	NPD7639	Approved
0.5743	Remote Similarity	NPD5785	Approved
0.5743	Remote Similarity	NPD5692	Phase 3
0.5738	Remote Similarity	NPD7736	Approved
0.5729	Remote Similarity	NPD3667	Approved
0.5728	Remote Similarity	NPD7748	Approved
0.5714	Remote Similarity	NPD7290	Approved
0.5714	Remote Similarity	NPD5988	Approved
0.5714	Remote Similarity	NPD6370	Approved
0.5714	Remote Similarity	NPD6883	Approved
0.5714	Remote Similarity	NPD7102	Approved
0.5714	Remote Similarity	NPD7902	Approved
0.5702	Remote Similarity	NPD7507	Approved
0.5701	Remote Similarity	NPD1700	Approved
0.5686	Remote Similarity	NPD5694	Approved
0.5686	Remote Similarity	NPD5693	Phase 1
0.5686	Remote Similarity	NPD7637	Suspended
0.5686	Remote Similarity	NPD6050	Approved
0.5676	Remote Similarity	NPD6011	Approved
0.567	Remote Similarity	NPD5332	Approved
0.567	Remote Similarity	NPD6110	Phase 1
0.567	Remote Similarity	NPD5331	Approved
0.5667	Remote Similarity	NPD8328	Phase 3
0.5664	Remote Similarity	NPD6617	Approved
0.5664	Remote Similarity	NPD6869	Approved
0.5664	Remote Similarity	NPD6847	Approved
0.5664	Remote Similarity	NPD8130	Phase 1
0.5657	Remote Similarity	NPD3618	Phase 1
0.5648	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD5328	Approved
0.5641	Remote Similarity	NPD28	Approved
0.5641	Remote Similarity	NPD29	Approved
0.5641	Remote Similarity	NPD7641	Discontinued
0.5625	Remote Similarity	NPD4790	Discontinued
0.5625	Remote Similarity	NPD1780	Approved
0.5625	Remote Similarity	NPD1779	Approved
0.5625	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD857	Phase 3
0.5614	Remote Similarity	NPD6882	Approved
0.5612	Remote Similarity	NPD3665	Phase 1
0.5612	Remote Similarity	NPD3666	Approved
0.5612	Remote Similarity	NPD3668	Phase 3
0.5612	Remote Similarity	NPD3133	Approved
0.5612	Remote Similarity	NPD4786	Approved
0.56	Remote Similarity	NPD7524	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data