NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	278.12
Volume:	281.652
LogP:	0.727
LogD:	0.453
LogS:	-2.001
# Rotatable Bonds:	4
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.612
Synthetic Accessibility Score:	4.468
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.55
MDCK Permeability:	8.247190271504223e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.34

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.935
Plasma Protein Binding (PPB):	52.1795539855957%
Volume Distribution (VD):	0.409
Pgp-substrate:	48.89185333251953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.652
CYP2C19-inhibitor:	0.041
CYP2C19-substrate:	0.372
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.05
CYP3A4-inhibitor:	0.233
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	7.066
Half-life (T1/2):	0.501

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.944
Maximum Recommended Daily Dose:	0.8
Skin Sensitization:	0.519
Carcinogencity:	0.908
Eye Corrosion:	0.894
Eye Irritation:	0.766
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC300312

Natural Product ID:	NPC300312
*Common Name:**	Secotanapartholide B
IUPAC Name:	(4S,5S)-5-[(1S,2S)-2-hydroxy-2-methyl-5-oxocyclopent-3-en-1-yl]-3-methylidene-4-(3-oxobutyl)oxolan-2-one
Synonyms:
Standard InCHIKey:	RTOGTHJTQOMSQZ-NHULGOKLSA-N
Standard InCHI:	InChI=1S/C15H18O5/c1-8(16)4-5-10-9(2)14(18)20-13(10)12-11(17)6-7-15(12,3)19/h6-7,10,12-13,19H,2,4-5H2,1,3H3/t10-,12-,13-,15-/m0/s1
SMILES:	CC(=O)CC[C@H]1C(=C)C(=O)O[C@@H]1[C@@H]1C(=O)C=C[C@]1(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513501
PubChem CID:	10265551
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
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jep.2005.01.054]
NPO4619	Artemisia gilvescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713410]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181920]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31418264]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4619	Artemisia gilvescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28276	Artemisia argyi	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	3300.0	nM	PMID[547853]
NPT2246	Cell Line	T-cells		IC50	=	1000.0	nM	PMID[547854]

☑ 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 NPC300312 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	190
0.1-0.2	1091
0.2-0.3	4480
0.3-0.4	8859
0.4-0.5	15160
0.5-0.6	7257
0.6-0.7	4133
0.7-0.8	1349
0.8-0.85	151
0.85-0.9	23
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC111114
1.0	High Similarity	NPC261607
0.9326	High Similarity	NPC167219
0.913	High Similarity	NPC141191
0.9022	High Similarity	NPC169205
0.9011	High Similarity	NPC275960
0.9011	High Similarity	NPC193645
0.9011	High Similarity	NPC48803
0.9011	High Similarity	NPC90121
0.8913	High Similarity	NPC185553
0.8864	High Similarity	NPC72513
0.8851	High Similarity	NPC125290
0.8778	High Similarity	NPC129419
0.8778	High Similarity	NPC106510
0.8778	High Similarity	NPC71533
0.8706	High Similarity	NPC223904
0.8696	High Similarity	NPC469632
0.8681	High Similarity	NPC70595
0.8681	High Similarity	NPC284185
0.8681	High Similarity	NPC74103
0.8681	High Similarity	NPC150978
0.8681	High Similarity	NPC123177
0.8667	High Similarity	NPC268298
0.8621	High Similarity	NPC39588
0.8602	High Similarity	NPC304886
0.8587	High Similarity	NPC135776
0.8571	High Similarity	NPC253144
0.8542	High Similarity	NPC46998
0.8542	High Similarity	NPC110443
0.8542	High Similarity	NPC128733
0.8542	High Similarity	NPC474742
0.8542	High Similarity	NPC185141
0.8542	High Similarity	NPC133907
0.8469	Intermediate Similarity	NPC100487
0.8469	Intermediate Similarity	NPC203659
0.8462	Intermediate Similarity	NPC295312
0.8462	Intermediate Similarity	NPC52198
0.8462	Intermediate Similarity	NPC117405
0.8444	Intermediate Similarity	NPC237540
0.8444	Intermediate Similarity	NPC160138
0.8427	Intermediate Similarity	NPC161957
0.8427	Intermediate Similarity	NPC21471
0.8427	Intermediate Similarity	NPC33570
0.8427	Intermediate Similarity	NPC165162
0.8427	Intermediate Similarity	NPC261380
0.8391	Intermediate Similarity	NPC325031
0.8387	Intermediate Similarity	NPC469645
0.8387	Intermediate Similarity	NPC469692
0.837	Intermediate Similarity	NPC77337
0.837	Intermediate Similarity	NPC144133
0.837	Intermediate Similarity	NPC179394
0.8367	Intermediate Similarity	NPC475945
0.8367	Intermediate Similarity	NPC110989
0.8367	Intermediate Similarity	NPC475871
0.8352	Intermediate Similarity	NPC469653
0.8352	Intermediate Similarity	NPC476805
0.8352	Intermediate Similarity	NPC469631
0.8352	Intermediate Similarity	NPC475906
0.8352	Intermediate Similarity	NPC471047
0.8352	Intermediate Similarity	NPC469628
0.8333	Intermediate Similarity	NPC475461
0.8333	Intermediate Similarity	NPC305475
0.8333	Intermediate Similarity	NPC54843
0.8333	Intermediate Similarity	NPC107787
0.8315	Intermediate Similarity	NPC114979
0.8315	Intermediate Similarity	NPC96259
0.8315	Intermediate Similarity	NPC141193
0.8315	Intermediate Similarity	NPC191476
0.8298	Intermediate Similarity	NPC121825
0.8298	Intermediate Similarity	NPC323008
0.8298	Intermediate Similarity	NPC470013
0.8298	Intermediate Similarity	NPC262133
0.8298	Intermediate Similarity	NPC470010
0.8298	Intermediate Similarity	NPC477131
0.8295	Intermediate Similarity	NPC85772
0.8283	Intermediate Similarity	NPC474741
0.8265	Intermediate Similarity	NPC225353
0.8265	Intermediate Similarity	NPC474747
0.8265	Intermediate Similarity	NPC149371
0.8261	Intermediate Similarity	NPC32922
0.8256	Intermediate Similarity	NPC93763
0.8256	Intermediate Similarity	NPC108816
0.8256	Intermediate Similarity	NPC267231
0.8247	Intermediate Similarity	NPC288876
0.8229	Intermediate Similarity	NPC213947
0.8229	Intermediate Similarity	NPC170143
0.8229	Intermediate Similarity	NPC108475
0.8229	Intermediate Similarity	NPC471462
0.8222	Intermediate Similarity	NPC78089
0.8222	Intermediate Similarity	NPC255307
0.8222	Intermediate Similarity	NPC470755
0.8218	Intermediate Similarity	NPC475960
0.8202	Intermediate Similarity	NPC250315
0.8191	Intermediate Similarity	NPC475912
0.8191	Intermediate Similarity	NPC475302
0.8182	Intermediate Similarity	NPC35089
0.8182	Intermediate Similarity	NPC475873
0.8182	Intermediate Similarity	NPC10276
0.8172	Intermediate Similarity	NPC62815
0.8172	Intermediate Similarity	NPC475855
0.8163	Intermediate Similarity	NPC47880
0.8152	Intermediate Similarity	NPC476803
0.8132	Intermediate Similarity	NPC284902
0.8132	Intermediate Similarity	NPC70555
0.8132	Intermediate Similarity	NPC104961
0.8132	Intermediate Similarity	NPC70422
0.8132	Intermediate Similarity	NPC261721
0.8125	Intermediate Similarity	NPC230800
0.8111	Intermediate Similarity	NPC158756
0.8111	Intermediate Similarity	NPC156485
0.8111	Intermediate Similarity	NPC476804
0.8111	Intermediate Similarity	NPC165287
0.8111	Intermediate Similarity	NPC472958
0.8111	Intermediate Similarity	NPC115786
0.8111	Intermediate Similarity	NPC472957
0.8105	Intermediate Similarity	NPC198853
0.8105	Intermediate Similarity	NPC474338
0.8105	Intermediate Similarity	NPC140543
0.8105	Intermediate Similarity	NPC476267
0.8105	Intermediate Similarity	NPC289004
0.81	Intermediate Similarity	NPC309190
0.809	Intermediate Similarity	NPC229825
0.809	Intermediate Similarity	NPC173609
0.809	Intermediate Similarity	NPC89555
0.8085	Intermediate Similarity	NPC131209
0.8085	Intermediate Similarity	NPC133698
0.8068	Intermediate Similarity	NPC74673
0.8068	Intermediate Similarity	NPC302426
0.8068	Intermediate Similarity	NPC69271
0.8065	Intermediate Similarity	NPC212598
0.8065	Intermediate Similarity	NPC168679
0.8065	Intermediate Similarity	NPC12872
0.8043	Intermediate Similarity	NPC201658
0.8043	Intermediate Similarity	NPC475703
0.8041	Intermediate Similarity	NPC474343
0.8022	Intermediate Similarity	NPC215364
0.8021	Intermediate Similarity	NPC270013
0.8021	Intermediate Similarity	NPC14961
0.8021	Intermediate Similarity	NPC36954
0.8021	Intermediate Similarity	NPC471142
0.8021	Intermediate Similarity	NPC475659
0.802	Intermediate Similarity	NPC223450
0.802	Intermediate Similarity	NPC243998
0.8	Intermediate Similarity	NPC179746
0.8	Intermediate Similarity	NPC473390
0.8	Intermediate Similarity	NPC131669
0.8	Intermediate Similarity	NPC472755
0.8	Intermediate Similarity	NPC162205
0.8	Intermediate Similarity	NPC215294
0.8	Intermediate Similarity	NPC40746
0.8	Intermediate Similarity	NPC475947
0.8	Intermediate Similarity	NPC475838
0.8	Intermediate Similarity	NPC228451
0.8	Intermediate Similarity	NPC295204
0.8	Intermediate Similarity	NPC476300
0.8	Intermediate Similarity	NPC273579
0.8	Intermediate Similarity	NPC169575
0.8	Intermediate Similarity	NPC125674
0.8	Intermediate Similarity	NPC288240
0.8	Intermediate Similarity	NPC81419
0.798	Intermediate Similarity	NPC206079
0.798	Intermediate Similarity	NPC472753
0.798	Intermediate Similarity	NPC171759
0.798	Intermediate Similarity	NPC477950
0.7979	Intermediate Similarity	NPC476004
0.7979	Intermediate Similarity	NPC474761
0.7979	Intermediate Similarity	NPC469368
0.7979	Intermediate Similarity	NPC51004
0.7979	Intermediate Similarity	NPC312042
0.7979	Intermediate Similarity	NPC473448
0.7978	Intermediate Similarity	NPC25684
0.7978	Intermediate Similarity	NPC470241
0.7978	Intermediate Similarity	NPC24417
0.7978	Intermediate Similarity	NPC52861
0.7978	Intermediate Similarity	NPC471325
0.7978	Intermediate Similarity	NPC141810
0.7978	Intermediate Similarity	NPC281949
0.7978	Intermediate Similarity	NPC301477
0.7959	Intermediate Similarity	NPC208233
0.7959	Intermediate Similarity	NPC473326
0.7957	Intermediate Similarity	NPC202672
0.7957	Intermediate Similarity	NPC91248
0.7957	Intermediate Similarity	NPC475819
0.7957	Intermediate Similarity	NPC475902
0.7955	Intermediate Similarity	NPC469617
0.7955	Intermediate Similarity	NPC470239
0.7955	Intermediate Similarity	NPC470244
0.7955	Intermediate Similarity	NPC178277
0.7955	Intermediate Similarity	NPC89128
0.7938	Intermediate Similarity	NPC473859
0.7938	Intermediate Similarity	NPC476315
0.7935	Intermediate Similarity	NPC469910
0.7935	Intermediate Similarity	NPC309757
0.7935	Intermediate Similarity	NPC469483
0.7935	Intermediate Similarity	NPC38576
0.7935	Intermediate Similarity	NPC236692
0.7935	Intermediate Similarity	NPC279859
0.7935	Intermediate Similarity	NPC234038
0.7935	Intermediate Similarity	NPC150755
0.7931	Intermediate Similarity	NPC65603

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 NPC300312 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1592
0.2-0.3	3611
0.3-0.4	2423
0.4-0.5	895
0.5-0.6	330
0.6-0.7	107
0.7-0.8	22
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9011	High Similarity	NPD1698	Clinical (unspecified phase)
0.7979	Intermediate Similarity	NPD5785	Approved
0.7826	Intermediate Similarity	NPD5363	Approved
0.7767	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5786	Approved
0.7551	Intermediate Similarity	NPD5282	Discontinued
0.7547	Intermediate Similarity	NPD6371	Approved
0.75	Intermediate Similarity	NPD4270	Approved
0.75	Intermediate Similarity	NPD4269	Approved
0.75	Intermediate Similarity	NPD1695	Approved
0.7449	Intermediate Similarity	NPD5778	Approved
0.7449	Intermediate Similarity	NPD5779	Approved
0.7447	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1694	Approved
0.7426	Intermediate Similarity	NPD4225	Approved
0.7419	Intermediate Similarity	NPD7154	Phase 3
0.7419	Intermediate Similarity	NPD5362	Discontinued
0.7391	Intermediate Similarity	NPD5369	Approved
0.7312	Intermediate Similarity	NPD5209	Approved
0.7283	Intermediate Similarity	NPD4252	Approved
0.7172	Intermediate Similarity	NPD7983	Approved
0.7143	Intermediate Similarity	NPD7115	Discovery
0.7143	Intermediate Similarity	NPD6101	Approved
0.7143	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6435	Approved
0.7	Intermediate Similarity	NPD6411	Approved
0.6947	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4820	Approved
0.6915	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD4822	Approved
0.6915	Remote Similarity	NPD4819	Approved
0.6915	Remote Similarity	NPD5368	Approved
0.6915	Remote Similarity	NPD4821	Approved
0.69	Remote Similarity	NPD46	Approved
0.69	Remote Similarity	NPD6698	Approved
0.6893	Remote Similarity	NPD7839	Suspended
0.6882	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD4249	Approved
0.6786	Remote Similarity	NPD6053	Discontinued
0.6771	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4250	Approved
0.6768	Remote Similarity	NPD4251	Approved
0.6735	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7838	Discovery
0.6702	Remote Similarity	NPD4268	Approved
0.6702	Remote Similarity	NPD4271	Approved
0.6701	Remote Similarity	NPD5332	Approved
0.6701	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD4790	Discontinued
0.6636	Remote Similarity	NPD5697	Approved
0.6634	Remote Similarity	NPD5370	Suspended
0.661	Remote Similarity	NPD8517	Approved
0.661	Remote Similarity	NPD8513	Phase 3
0.661	Remote Similarity	NPD8516	Approved
0.661	Remote Similarity	NPD8515	Approved
0.6604	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6899	Approved
0.6577	Remote Similarity	NPD6881	Approved
0.6549	Remote Similarity	NPD6650	Approved
0.6549	Remote Similarity	NPD6649	Approved
0.6549	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6012	Approved
0.6518	Remote Similarity	NPD6014	Approved
0.6518	Remote Similarity	NPD6013	Approved
0.6505	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7637	Suspended
0.6481	Remote Similarity	NPD5344	Discontinued
0.6477	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5695	Phase 3
0.646	Remote Similarity	NPD7290	Approved
0.646	Remote Similarity	NPD7102	Approved
0.646	Remote Similarity	NPD6883	Approved
0.6449	Remote Similarity	NPD5696	Approved
0.6442	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD7320	Approved
0.6429	Remote Similarity	NPD6686	Approved
0.6429	Remote Similarity	NPD6011	Approved
0.6422	Remote Similarity	NPD5211	Phase 2
0.6421	Remote Similarity	NPD4756	Discovery
0.6404	Remote Similarity	NPD6617	Approved
0.6404	Remote Similarity	NPD7331	Phase 2
0.6404	Remote Similarity	NPD8130	Phase 1
0.6404	Remote Similarity	NPD6847	Approved
0.6404	Remote Similarity	NPD6869	Approved
0.6396	Remote Similarity	NPD6008	Approved
0.6396	Remote Similarity	NPD6402	Approved
0.6396	Remote Similarity	NPD5739	Approved
0.6396	Remote Similarity	NPD6675	Approved
0.6396	Remote Similarity	NPD7128	Approved
0.6389	Remote Similarity	NPD6648	Approved
0.6389	Remote Similarity	NPD7639	Approved
0.6389	Remote Similarity	NPD7640	Approved
0.6372	Remote Similarity	NPD6373	Approved
0.6372	Remote Similarity	NPD6372	Approved
0.6355	Remote Similarity	NPD6084	Phase 2
0.6355	Remote Similarity	NPD6083	Phase 2
0.6348	Remote Similarity	NPD8297	Approved
0.6348	Remote Similarity	NPD6882	Approved
0.6341	Remote Similarity	NPD8074	Phase 3
0.6339	Remote Similarity	NPD5701	Approved
0.6337	Remote Similarity	NPD4519	Discontinued
0.6337	Remote Similarity	NPD4623	Approved
0.6311	Remote Similarity	NPD7492	Approved
0.6306	Remote Similarity	NPD5141	Approved
0.63	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7638	Approved
0.6292	Remote Similarity	NPD7341	Phase 2
0.6275	Remote Similarity	NPD3573	Approved
0.626	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD6054	Approved
0.625	Remote Similarity	NPD5207	Approved
0.625	Remote Similarity	NPD6319	Approved
0.6239	Remote Similarity	NPD4696	Approved
0.6239	Remote Similarity	NPD5285	Approved
0.6239	Remote Similarity	NPD5286	Approved
0.6238	Remote Similarity	NPD1696	Phase 3
0.623	Remote Similarity	NPD7642	Approved
0.6226	Remote Similarity	NPD7748	Approved
0.6216	Remote Similarity	NPD6647	Phase 2
0.6214	Remote Similarity	NPD6903	Approved
0.6211	Remote Similarity	NPD8039	Approved
0.621	Remote Similarity	NPD7078	Approved
0.6204	Remote Similarity	NPD7902	Approved
0.6198	Remote Similarity	NPD6016	Approved
0.6198	Remote Similarity	NPD6015	Approved
0.6198	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5693	Phase 1
0.619	Remote Similarity	NPD5281	Approved
0.619	Remote Similarity	NPD5284	Approved
0.619	Remote Similarity	NPD6079	Approved
0.6176	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5330	Approved
0.6176	Remote Similarity	NPD6684	Approved
0.6176	Remote Similarity	NPD7521	Approved
0.6176	Remote Similarity	NPD7334	Approved
0.6176	Remote Similarity	NPD6409	Approved
0.6176	Remote Similarity	NPD7146	Approved
0.6168	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4629	Approved
0.6168	Remote Similarity	NPD5210	Approved
0.616	Remote Similarity	NPD7736	Approved
0.6154	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD5988	Approved
0.6148	Remote Similarity	NPD6370	Approved
0.614	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4633	Approved
0.6126	Remote Similarity	NPD5226	Approved
0.6126	Remote Similarity	NPD5224	Approved
0.6126	Remote Similarity	NPD5225	Approved
0.6111	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7319	Approved
0.6111	Remote Similarity	NPD5222	Approved
0.6111	Remote Similarity	NPD5221	Approved
0.6087	Remote Similarity	NPD6413	Approved
0.6071	Remote Similarity	NPD5175	Approved
0.6071	Remote Similarity	NPD5174	Approved
0.6061	Remote Similarity	NPD4695	Discontinued
0.6058	Remote Similarity	NPD6672	Approved
0.6058	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5737	Approved
0.6055	Remote Similarity	NPD5173	Approved
0.6055	Remote Similarity	NPD4755	Approved
0.605	Remote Similarity	NPD6274	Approved
0.6038	Remote Similarity	NPD7515	Phase 2
0.6036	Remote Similarity	NPD5223	Approved
0.6034	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD4634	Approved
0.6033	Remote Similarity	NPD7100	Approved
0.6033	Remote Similarity	NPD7101	Approved
0.6019	Remote Similarity	NPD6422	Discontinued
0.6019	Remote Similarity	NPD3618	Phase 1
0.6017	Remote Similarity	NPD4632	Approved
0.6016	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD7507	Approved
0.6	Remote Similarity	NPD6317	Approved
0.5984	Remote Similarity	NPD6059	Approved
0.5983	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD2204	Approved
0.598	Remote Similarity	NPD3133	Approved
0.598	Remote Similarity	NPD3666	Approved
0.598	Remote Similarity	NPD3665	Phase 1
0.5978	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5968	Remote Similarity	NPD7830	Approved
0.5968	Remote Similarity	NPD7829	Approved
0.5963	Remote Similarity	NPD4697	Phase 3
0.5952	Remote Similarity	NPD8293	Discontinued
0.595	Remote Similarity	NPD6313	Approved
0.595	Remote Similarity	NPD6314	Approved
0.595	Remote Similarity	NPD6335	Approved
0.5948	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4700	Approved
0.5941	Remote Similarity	NPD3667	Approved
0.5926	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6001	Approved
0.5926	Remote Similarity	NPD7900	Approved
0.5917	Remote Similarity	NPD6868	Approved
0.5888	Remote Similarity	NPD5694	Approved
0.5882	Remote Similarity	NPD6110	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