NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.12
Volume:	281.652
LogP:	0.795
LogD:	0.169
LogS:	-1.841
# Rotatable Bonds:	4
TPSA:	77.51
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.439
Synthetic Accessibility Score:	4.346
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.6
MDCK Permeability:	4.94126470584888e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.1
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.495
Plasma Protein Binding (PPB):	45.97871398925781%
Volume Distribution (VD):	0.442
Pgp-substrate:	62.482826232910156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.412
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.225
CYP2C9-inhibitor:	0.058
CYP2C9-substrate:	0.139
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.203
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	12.744
Half-life (T1/2):	0.881

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.09
Drug-inuced Liver Injury (DILI):	0.797
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.759
Maximum Recommended Daily Dose:	0.157
Skin Sensitization:	0.754
Carcinogencity:	0.181
Eye Corrosion:	0.962
Eye Irritation:	0.569
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC106510

Natural Product ID:	NPC106510
*Common Name:**	Isosecotanapartholide
IUPAC Name:	(4S,5S)-5-[(3S)-3-hydroxy-2-methyl-5-oxocyclopenten-1-yl]-3-methylidene-4-(3-oxobutyl)oxolan-2-one
Synonyms:	Isosecotanapartholide
Standard InCHIKey:	XXYRTFCLQHKIDU-MJVIPROJSA-N
Standard InCHI:	InChI=1S/C15H18O5/c1-7(16)4-5-10-8(2)15(19)20-14(10)13-9(3)11(17)6-12(13)18/h10-11,14,17H,2,4-6H2,1,3H3/t10-,11-,14-/m0/s1
SMILES:	CC(=O)CC[C@H]1C(=C)C(=O)O[C@@H]1C1=C(C)[C@H](CC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508537
PubChem CID:	13918473
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	DOI[10.1002/hlca.201300170.]
NPO3793	Artemisia rutifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(86)80021-8]
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12735688]
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23510022]
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28039	Alstonia vitiensis	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18647	Achillea falcata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24105	Artemisia iwayomogi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27802	Candida albicaus	Species	Debaryomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3793	Artemisia rutifolia	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	13000.0	nM	PMID[558528]

☑ 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 NPC106510 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	198
0.1-0.2	1239
0.2-0.3	4976
0.3-0.4	8900
0.4-0.5	15565
0.5-0.6	6807
0.6-0.7	3693
0.7-0.8	1159
0.8-0.85	140
0.85-0.9	16
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC71533
0.8977	High Similarity	NPC295312
0.881	High Similarity	NPC223904
0.8778	High Similarity	NPC261607
0.8778	High Similarity	NPC300312
0.8778	High Similarity	NPC111114
0.875	High Similarity	NPC100487
0.8681	High Similarity	NPC135776
0.8556	High Similarity	NPC474032
0.8556	High Similarity	NPC268298
0.8462	Intermediate Similarity	NPC129419
0.8427	Intermediate Similarity	NPC284902
0.8421	Intermediate Similarity	NPC141191
0.8409	Intermediate Similarity	NPC472957
0.8409	Intermediate Similarity	NPC472958
0.8367	Intermediate Similarity	NPC203659
0.8352	Intermediate Similarity	NPC32922
0.8333	Intermediate Similarity	NPC160138
0.8333	Intermediate Similarity	NPC72513
0.8333	Intermediate Similarity	NPC288876
0.8316	Intermediate Similarity	NPC169205
0.8315	Intermediate Similarity	NPC21469
0.8298	Intermediate Similarity	NPC48803
0.8298	Intermediate Similarity	NPC90121
0.8298	Intermediate Similarity	NPC275960
0.8298	Intermediate Similarity	NPC193645
0.8298	Intermediate Similarity	NPC477922
0.8298	Intermediate Similarity	NPC304886
0.8298	Intermediate Similarity	NPC471142
0.8295	Intermediate Similarity	NPC318468
0.828	Intermediate Similarity	NPC295204
0.828	Intermediate Similarity	NPC288240
0.828	Intermediate Similarity	NPC475912
0.828	Intermediate Similarity	NPC273579
0.828	Intermediate Similarity	NPC200237
0.828	Intermediate Similarity	NPC162205
0.828	Intermediate Similarity	NPC81419
0.828	Intermediate Similarity	NPC179746
0.8265	Intermediate Similarity	NPC110989
0.8261	Intermediate Similarity	NPC476004
0.8261	Intermediate Similarity	NPC474761
0.8261	Intermediate Similarity	NPC77337
0.8247	Intermediate Similarity	NPC171759
0.8242	Intermediate Similarity	NPC202672
0.8242	Intermediate Similarity	NPC473715
0.8211	Intermediate Similarity	NPC477921
0.8211	Intermediate Similarity	NPC185553
0.8211	Intermediate Similarity	NPC473859
0.8211	Intermediate Similarity	NPC230800
0.8202	Intermediate Similarity	NPC96259
0.8202	Intermediate Similarity	NPC141193
0.8191	Intermediate Similarity	NPC469632
0.8191	Intermediate Similarity	NPC167219
0.8191	Intermediate Similarity	NPC474035
0.8191	Intermediate Similarity	NPC303942
0.8191	Intermediate Similarity	NPC81386
0.8191	Intermediate Similarity	NPC57405
0.8172	Intermediate Similarity	NPC473321
0.8172	Intermediate Similarity	NPC12172
0.8172	Intermediate Similarity	NPC208886
0.8172	Intermediate Similarity	NPC30515
0.8163	Intermediate Similarity	NPC225353
0.814	Intermediate Similarity	NPC108816
0.814	Intermediate Similarity	NPC93763
0.8132	Intermediate Similarity	NPC475703
0.8132	Intermediate Similarity	NPC237540
0.8125	Intermediate Similarity	NPC108475
0.8125	Intermediate Similarity	NPC170143
0.8125	Intermediate Similarity	NPC213947
0.8111	Intermediate Similarity	NPC165162
0.8111	Intermediate Similarity	NPC125290
0.8111	Intermediate Similarity	NPC470755
0.8105	Intermediate Similarity	NPC170120
0.8105	Intermediate Similarity	NPC475659
0.8105	Intermediate Similarity	NPC270013
0.8105	Intermediate Similarity	NPC36954
0.8105	Intermediate Similarity	NPC14961
0.81	Intermediate Similarity	NPC243998
0.809	Intermediate Similarity	NPC250315
0.8085	Intermediate Similarity	NPC153590
0.8085	Intermediate Similarity	NPC475838
0.8085	Intermediate Similarity	NPC469645
0.8085	Intermediate Similarity	NPC469692
0.8085	Intermediate Similarity	NPC228451
0.8085	Intermediate Similarity	NPC125674
0.8081	Intermediate Similarity	NPC475945
0.8081	Intermediate Similarity	NPC475871
0.8068	Intermediate Similarity	NPC35089
0.8068	Intermediate Similarity	NPC10276
0.8065	Intermediate Similarity	NPC473455
0.8065	Intermediate Similarity	NPC473619
0.8065	Intermediate Similarity	NPC144133
0.8065	Intermediate Similarity	NPC475855
0.8065	Intermediate Similarity	NPC51004
0.8065	Intermediate Similarity	NPC179394
0.8061	Intermediate Similarity	NPC474742
0.8061	Intermediate Similarity	NPC185141
0.8061	Intermediate Similarity	NPC133907
0.8061	Intermediate Similarity	NPC46998
0.8061	Intermediate Similarity	NPC128733
0.8061	Intermediate Similarity	NPC110443
0.8043	Intermediate Similarity	NPC476805
0.8043	Intermediate Similarity	NPC475819
0.8041	Intermediate Similarity	NPC23364
0.8041	Intermediate Similarity	NPC473326
0.8023	Intermediate Similarity	NPC116177
0.8023	Intermediate Similarity	NPC320630
0.8023	Intermediate Similarity	NPC7563
0.8022	Intermediate Similarity	NPC261721
0.8022	Intermediate Similarity	NPC67493
0.8022	Intermediate Similarity	NPC305475
0.8022	Intermediate Similarity	NPC475461
0.8022	Intermediate Similarity	NPC122502
0.8021	Intermediate Similarity	NPC91771
0.8021	Intermediate Similarity	NPC476315
0.8021	Intermediate Similarity	NPC142529
0.8	Intermediate Similarity	NPC474338
0.8	Intermediate Similarity	NPC121825
0.8	Intermediate Similarity	NPC158756
0.8	Intermediate Similarity	NPC114979
0.8	Intermediate Similarity	NPC470013
0.8	Intermediate Similarity	NPC477131
0.8	Intermediate Similarity	NPC191476
0.8	Intermediate Similarity	NPC470010
0.8	Intermediate Similarity	NPC474247
0.8	Intermediate Similarity	NPC323008
0.8	Intermediate Similarity	NPC262133
0.8	Intermediate Similarity	NPC140543
0.798	Intermediate Similarity	NPC149371
0.798	Intermediate Similarity	NPC474747
0.7979	Intermediate Similarity	NPC20713
0.7979	Intermediate Similarity	NPC184463
0.7979	Intermediate Similarity	NPC131209
0.7978	Intermediate Similarity	NPC173609
0.7957	Intermediate Similarity	NPC307411
0.7957	Intermediate Similarity	NPC87306
0.7941	Intermediate Similarity	NPC475960
0.7938	Intermediate Similarity	NPC471462
0.7935	Intermediate Similarity	NPC118601
0.7935	Intermediate Similarity	NPC186148
0.7931	Intermediate Similarity	NPC196653
0.7931	Intermediate Similarity	NPC471465
0.7921	Intermediate Similarity	NPC223450
0.7917	Intermediate Similarity	NPC214694
0.7917	Intermediate Similarity	NPC52044
0.7917	Intermediate Similarity	NPC213698
0.7912	Intermediate Similarity	NPC137033
0.7912	Intermediate Similarity	NPC215364
0.7912	Intermediate Similarity	NPC255307
0.7912	Intermediate Similarity	NPC261380
0.79	Intermediate Similarity	NPC472755
0.7895	Intermediate Similarity	NPC473234
0.7895	Intermediate Similarity	NPC60386
0.7895	Intermediate Similarity	NPC473273
0.7895	Intermediate Similarity	NPC212486
0.7895	Intermediate Similarity	NPC308656
0.7895	Intermediate Similarity	NPC473263
0.7895	Intermediate Similarity	NPC475302
0.7895	Intermediate Similarity	NPC476300
0.7889	Intermediate Similarity	NPC40746
0.7889	Intermediate Similarity	NPC39588
0.7889	Intermediate Similarity	NPC169575
0.7879	Intermediate Similarity	NPC47880
0.7879	Intermediate Similarity	NPC201718
0.7879	Intermediate Similarity	NPC150923
0.7872	Intermediate Similarity	NPC301969
0.7872	Intermediate Similarity	NPC19087
0.7872	Intermediate Similarity	NPC37607
0.7872	Intermediate Similarity	NPC62815
0.7865	Intermediate Similarity	NPC24417
0.7864	Intermediate Similarity	NPC38154
0.7857	Intermediate Similarity	NPC187268
0.7857	Intermediate Similarity	NPC471144
0.7849	Intermediate Similarity	NPC227379
0.7849	Intermediate Similarity	NPC58219
0.7849	Intermediate Similarity	NPC177629
0.7849	Intermediate Similarity	NPC178875
0.7849	Intermediate Similarity	NPC474471
0.7849	Intermediate Similarity	NPC153805
0.7849	Intermediate Similarity	NPC91248
0.7849	Intermediate Similarity	NPC476803
0.7841	Intermediate Similarity	NPC470239
0.7841	Intermediate Similarity	NPC470244
0.7835	Intermediate Similarity	NPC279621
0.7835	Intermediate Similarity	NPC126156
0.7826	Intermediate Similarity	NPC477010
0.7826	Intermediate Similarity	NPC112685
0.7826	Intermediate Similarity	NPC164393
0.7826	Intermediate Similarity	NPC469910
0.7826	Intermediate Similarity	NPC470242
0.7822	Intermediate Similarity	NPC474741
0.7812	Intermediate Similarity	NPC473331
0.7812	Intermediate Similarity	NPC476267
0.7812	Intermediate Similarity	NPC127019
0.7812	Intermediate Similarity	NPC53685
0.7812	Intermediate Similarity	NPC90453
0.7812	Intermediate Similarity	NPC198853
0.7802	Intermediate Similarity	NPC476804
0.7802	Intermediate Similarity	NPC212363
0.7802	Intermediate Similarity	NPC474780

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 NPC106510 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	189
0.1-0.2	1874
0.2-0.3	3695
0.3-0.4	2243
0.4-0.5	756
0.5-0.6	326
0.6-0.7	49
0.7-0.8	16
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
0.8298	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD5785	Approved
0.7717	Intermediate Similarity	NPD5363	Approved
0.767	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5786	Approved
0.7619	Intermediate Similarity	NPD6371	Approved
0.7527	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7983	Approved
0.7391	Intermediate Similarity	NPD4269	Approved
0.7391	Intermediate Similarity	NPD4270	Approved
0.732	Intermediate Similarity	NPD46	Approved
0.732	Intermediate Similarity	NPD6698	Approved
0.7312	Intermediate Similarity	NPD5362	Discontinued
0.7216	Intermediate Similarity	NPD1695	Approved
0.7174	Intermediate Similarity	NPD4252	Approved
0.7172	Intermediate Similarity	NPD5778	Approved
0.7172	Intermediate Similarity	NPD5779	Approved
0.7128	Intermediate Similarity	NPD7154	Phase 3
0.71	Intermediate Similarity	NPD5282	Discontinued
0.7097	Intermediate Similarity	NPD5369	Approved
0.7083	Intermediate Similarity	NPD4249	Approved
0.7021	Intermediate Similarity	NPD5209	Approved
0.701	Intermediate Similarity	NPD4250	Approved
0.701	Intermediate Similarity	NPD4251	Approved
0.699	Remote Similarity	NPD4225	Approved
0.6961	Remote Similarity	NPD7839	Suspended
0.6847	Remote Similarity	NPD6053	Discontinued
0.6842	Remote Similarity	NPD6435	Approved
0.6827	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD1694	Approved
0.6804	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7838	Discovery
0.67	Remote Similarity	NPD5370	Suspended
0.6632	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD5368	Approved
0.6604	Remote Similarity	NPD7640	Approved
0.6604	Remote Similarity	NPD7639	Approved
0.6598	Remote Similarity	NPD5332	Approved
0.6598	Remote Similarity	NPD5331	Approved
0.6596	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4790	Discontinued
0.6535	Remote Similarity	NPD6101	Approved
0.6535	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD8516	Approved
0.6525	Remote Similarity	NPD8513	Phase 3
0.6525	Remote Similarity	NPD8517	Approved
0.6525	Remote Similarity	NPD8515	Approved
0.6509	Remote Similarity	NPD7638	Approved
0.6495	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6686	Approved
0.6466	Remote Similarity	NPD7115	Discovery
0.646	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4819	Approved
0.6458	Remote Similarity	NPD4822	Approved
0.6458	Remote Similarity	NPD4821	Approved
0.6458	Remote Similarity	NPD4820	Approved
0.6455	Remote Similarity	NPD6008	Approved
0.6421	Remote Similarity	NPD4268	Approved
0.6421	Remote Similarity	NPD4271	Approved
0.6408	Remote Similarity	NPD7637	Suspended
0.6408	Remote Similarity	NPD6411	Approved
0.6327	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4756	Discovery
0.6281	Remote Similarity	NPD7642	Approved
0.6263	Remote Similarity	NPD6110	Phase 1
0.626	Remote Similarity	NPD8074	Phase 3
0.6239	Remote Similarity	NPD5344	Discontinued
0.623	Remote Similarity	NPD7492	Approved
0.6222	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7632	Discontinued
0.618	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD6616	Approved
0.6167	Remote Similarity	NPD6054	Approved
0.6167	Remote Similarity	NPD6319	Approved
0.616	Remote Similarity	NPD7319	Approved
0.6148	Remote Similarity	NPD7829	Approved
0.6148	Remote Similarity	NPD7830	Approved
0.6129	Remote Similarity	NPD7078	Approved
0.6116	Remote Similarity	NPD6015	Approved
0.6116	Remote Similarity	NPD6016	Approved
0.6111	Remote Similarity	NPD7331	Phase 2
0.6106	Remote Similarity	NPD5697	Approved
0.608	Remote Similarity	NPD7736	Approved
0.6068	Remote Similarity	NPD4632	Approved
0.6066	Remote Similarity	NPD5988	Approved
0.6066	Remote Similarity	NPD6370	Approved
0.6053	Remote Similarity	NPD6899	Approved
0.6053	Remote Similarity	NPD6881	Approved
0.6053	Remote Similarity	NPD7320	Approved
0.6053	Remote Similarity	NPD6011	Approved
0.605	Remote Similarity	NPD7500	Approved
0.6048	Remote Similarity	NPD7507	Approved
0.6038	Remote Similarity	NPD6399	Phase 3
0.6034	Remote Similarity	NPD6650	Approved
0.6034	Remote Similarity	NPD6649	Approved
0.6033	Remote Similarity	NPD6059	Approved
0.6018	Remote Similarity	NPD5739	Approved
0.6018	Remote Similarity	NPD6675	Approved
0.6018	Remote Similarity	NPD7128	Approved
0.6018	Remote Similarity	NPD6402	Approved
0.6016	Remote Similarity	NPD6845	Suspended
0.6	Remote Similarity	NPD7341	Phase 2
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD7641	Discontinued
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD8293	Discontinued
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD6012	Approved
0.6	Remote Similarity	NPD6373	Approved
0.5984	Remote Similarity	NPD8444	Approved
0.5982	Remote Similarity	NPD6647	Phase 2
0.598	Remote Similarity	NPD1696	Phase 3
0.5965	Remote Similarity	NPD5701	Approved
0.5963	Remote Similarity	NPD6083	Phase 2
0.5963	Remote Similarity	NPD6084	Phase 2
0.5962	Remote Similarity	NPD6903	Approved
0.5954	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD7290	Approved
0.5948	Remote Similarity	NPD7102	Approved
0.5948	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6883	Approved
0.5938	Remote Similarity	NPD8039	Approved
0.5938	Remote Similarity	NPD7260	Phase 2
0.5926	Remote Similarity	NPD5695	Phase 3
0.5922	Remote Similarity	NPD7146	Approved
0.5922	Remote Similarity	NPD6409	Approved
0.5922	Remote Similarity	NPD7521	Approved
0.5922	Remote Similarity	NPD5330	Approved
0.5922	Remote Similarity	NPD6422	Discontinued
0.5922	Remote Similarity	NPD6684	Approved
0.5922	Remote Similarity	NPD7334	Approved
0.5917	Remote Similarity	NPD6009	Approved
0.5913	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD5696	Approved
0.5897	Remote Similarity	NPD6847	Approved
0.5897	Remote Similarity	NPD8130	Phase 1
0.5897	Remote Similarity	NPD6869	Approved
0.5897	Remote Similarity	NPD6617	Approved
0.5893	Remote Similarity	NPD5211	Phase 2
0.5882	Remote Similarity	NPD3666	Approved
0.5882	Remote Similarity	NPD3133	Approved
0.5882	Remote Similarity	NPD3665	Phase 1
0.5877	Remote Similarity	NPD5048	Discontinued
0.5854	Remote Similarity	NPD8268	Approved
0.5854	Remote Similarity	NPD8269	Approved
0.5854	Remote Similarity	NPD8266	Approved
0.5854	Remote Similarity	NPD8267	Approved
0.5854	Remote Similarity	NPD5983	Phase 2
0.5854	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD8297	Approved
0.5847	Remote Similarity	NPD6882	Approved
0.5833	Remote Similarity	NPD7748	Approved
0.5826	Remote Similarity	NPD6412	Phase 2
0.5818	Remote Similarity	NPD7902	Approved
0.5812	Remote Similarity	NPD4634	Approved
0.581	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD8451	Approved
0.5794	Remote Similarity	NPD6079	Approved
0.5794	Remote Similarity	NPD5693	Phase 1
0.5794	Remote Similarity	NPD7515	Phase 2
0.5789	Remote Similarity	NPD5141	Approved
0.578	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD3618	Phase 1
0.5769	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD2204	Approved
0.5763	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD3704	Approved
0.576	Remote Similarity	NPD7604	Phase 2
0.576	Remote Similarity	NPD8328	Phase 3
0.5758	Remote Similarity	NPD4802	Phase 2
0.5758	Remote Similarity	NPD4238	Approved
0.5755	Remote Similarity	NPD5328	Approved
0.5748	Remote Similarity	NPD8448	Approved
0.5736	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD4697	Phase 3
0.5727	Remote Similarity	NPD5221	Approved
0.5727	Remote Similarity	NPD5222	Approved
0.5727	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8340	Approved
0.5714	Remote Similarity	NPD8341	Approved
0.5714	Remote Similarity	NPD8299	Approved
0.5714	Remote Similarity	NPD5286	Approved
0.5714	Remote Similarity	NPD4696	Approved
0.5714	Remote Similarity	NPD5285	Approved
0.5714	Remote Similarity	NPD8342	Approved
0.5703	Remote Similarity	NPD6033	Approved
0.5702	Remote Similarity	NPD6274	Approved
0.5701	Remote Similarity	NPD5207	Approved
0.569	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5686	Remote Similarity	NPD3667	Approved
0.568	Remote Similarity	NPD8080	Discontinued
0.5676	Remote Similarity	NPD5173	Approved
0.5676	Remote Similarity	NPD4755	Approved
0.5669	Remote Similarity	NPD6336	Discontinued
0.5669	Remote Similarity	NPD8273	Phase 1

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