NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	282.15
Volume:	281.005
LogP:	1.425
LogD:	1.887
LogS:	-2.127
# Rotatable Bonds:	0
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.57
Synthetic Accessibility Score:	4.886
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.032
MDCK Permeability:	1.4429244401981123e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.975
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.645
Plasma Protein Binding (PPB):	36.987857818603516%
Volume Distribution (VD):	0.846
Pgp-substrate:	36.495323181152344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.647
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.809
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.088
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.27
CYP3A4-substrate:	0.291

ADMET: Excretion

Clearance (CL):	5.452
Half-life (T1/2):	0.712

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.122
Drug-inuced Liver Injury (DILI):	0.095
AMES Toxicity:	0.278
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.489
Skin Sensitization:	0.289
Carcinogencity:	0.114
Eye Corrosion:	0.009
Eye Irritation:	0.068
Respiratory Toxicity:	0.781

Download Data

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

Natural Product: NPC472642

Natural Product ID:	NPC472642
*Common Name:**	BWULZOCTMRQREI-DBKNABFLSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BWULZOCTMRQREI-DBKNABFLSA-N
Standard InCHI:	InChI=1S/C15H22O5/c1-7-9-4-10-8(2)13(18)20-15(10,19)6-14(9,3)12(17)5-11(7)16/h7,9,11-12,16-17,19H,4-6H2,1-3H3/t7-,9-,11+,12-,14+,15-/m1/s1
SMILES:	O[C@H]1C[C@@H](O)[C@@]2([C@@H]([C@H]1C)CC1=C(C)C(=O)O[C@@]1(C2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581366
PubChem CID:	n.a.
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:0001772] Eudesmanolides, secoeudesmanolides, 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
NPO1371	Teucrium viscidum	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[23337296]
NPO1371	Teucrium viscidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24484201]
NPO1371	Teucrium viscidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25739048]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27933899]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28960981]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1371	Teucrium viscidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17346	Salvia plebeia	Species	Lamiaceae	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

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[484701]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000.0	nM	PMID[484701]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[484701]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[484702]
NPT2	Others	Unspecified		IC50	>	1000000.0	nM	PMID[484701]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[484701]

☑ 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 NPC472642 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	206
0.1-0.2	1422
0.2-0.3	4590
0.3-0.4	8747
0.4-0.5	13638
0.5-0.6	7144
0.6-0.7	5731
0.7-0.8	1084
0.8-0.85	100
0.85-0.9	26
0.9-0.95	3
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC472641
0.9767	High Similarity	NPC472640
0.9545	High Similarity	NPC471915
0.9425	High Similarity	NPC78594
0.9222	High Similarity	NPC165632
0.9111	High Similarity	NPC111273
0.9101	High Similarity	NPC110022
0.8953	High Similarity	NPC253604
0.8936	High Similarity	NPC471914
0.8925	High Similarity	NPC16601
0.8842	High Similarity	NPC471938
0.8837	High Similarity	NPC32223
0.875	High Similarity	NPC471937
0.8696	High Similarity	NPC276110
0.8681	High Similarity	NPC472812
0.8652	High Similarity	NPC242448
0.8636	High Similarity	NPC131813
0.8602	High Similarity	NPC134072
0.8602	High Similarity	NPC234993
0.8571	High Similarity	NPC472811
0.8526	High Similarity	NPC324841
0.8526	High Similarity	NPC38855
0.8462	Intermediate Similarity	NPC78973
0.8454	Intermediate Similarity	NPC471208
0.8454	Intermediate Similarity	NPC474822
0.8444	Intermediate Similarity	NPC472810
0.8444	Intermediate Similarity	NPC472809
0.8421	Intermediate Similarity	NPC275086
0.8421	Intermediate Similarity	NPC325229
0.8421	Intermediate Similarity	NPC278673
0.8387	Intermediate Similarity	NPC105490
0.8387	Intermediate Similarity	NPC57117
0.8384	Intermediate Similarity	NPC471205
0.8372	Intermediate Similarity	NPC10636
0.837	Intermediate Similarity	NPC329842
0.8351	Intermediate Similarity	NPC472815
0.8351	Intermediate Similarity	NPC121423
0.8351	Intermediate Similarity	NPC109195
0.8351	Intermediate Similarity	NPC58329
0.8351	Intermediate Similarity	NPC476081
0.8351	Intermediate Similarity	NPC475038
0.8316	Intermediate Similarity	NPC51499
0.83	Intermediate Similarity	NPC38948
0.83	Intermediate Similarity	NPC325054
0.83	Intermediate Similarity	NPC181994
0.83	Intermediate Similarity	NPC300614
0.83	Intermediate Similarity	NPC90946
0.8298	Intermediate Similarity	NPC472441
0.8295	Intermediate Similarity	NPC311070
0.828	Intermediate Similarity	NPC7349
0.828	Intermediate Similarity	NPC53555
0.828	Intermediate Similarity	NPC162615
0.828	Intermediate Similarity	NPC152778
0.828	Intermediate Similarity	NPC205034
0.828	Intermediate Similarity	NPC139692
0.8265	Intermediate Similarity	NPC120009
0.8265	Intermediate Similarity	NPC45897
0.8229	Intermediate Similarity	NPC474440
0.8218	Intermediate Similarity	NPC31522
0.8218	Intermediate Similarity	NPC206618
0.8211	Intermediate Similarity	NPC242848
0.8211	Intermediate Similarity	NPC319861
0.82	Intermediate Similarity	NPC187435
0.82	Intermediate Similarity	NPC122816
0.82	Intermediate Similarity	NPC475074
0.82	Intermediate Similarity	NPC67321
0.8191	Intermediate Similarity	NPC470255
0.8191	Intermediate Similarity	NPC474554
0.8191	Intermediate Similarity	NPC474555
0.8172	Intermediate Similarity	NPC72845
0.8163	Intermediate Similarity	NPC295791
0.8163	Intermediate Similarity	NPC165250
0.8152	Intermediate Similarity	NPC470734
0.8144	Intermediate Similarity	NPC476767
0.8132	Intermediate Similarity	NPC473891
0.8125	Intermediate Similarity	NPC477719
0.8125	Intermediate Similarity	NPC477718
0.81	Intermediate Similarity	NPC51719
0.81	Intermediate Similarity	NPC218158
0.81	Intermediate Similarity	NPC34768
0.8081	Intermediate Similarity	NPC281378
0.8081	Intermediate Similarity	NPC159533
0.8081	Intermediate Similarity	NPC120321
0.8065	Intermediate Similarity	NPC310479
0.8065	Intermediate Similarity	NPC182136
0.8065	Intermediate Similarity	NPC221111
0.8065	Intermediate Similarity	NPC280149
0.8061	Intermediate Similarity	NPC11974
0.8061	Intermediate Similarity	NPC198992
0.8041	Intermediate Similarity	NPC473154
0.8023	Intermediate Similarity	NPC189206
0.8021	Intermediate Similarity	NPC473153
0.8021	Intermediate Similarity	NPC16967
0.8021	Intermediate Similarity	NPC202833
0.8021	Intermediate Similarity	NPC17578
0.8021	Intermediate Similarity	NPC240673
0.8	Intermediate Similarity	NPC161775
0.8	Intermediate Similarity	NPC191521
0.8	Intermediate Similarity	NPC102048
0.8	Intermediate Similarity	NPC469697
0.8	Intermediate Similarity	NPC24861
0.798	Intermediate Similarity	NPC472552
0.7979	Intermediate Similarity	NPC473675
0.7979	Intermediate Similarity	NPC124374
0.7961	Intermediate Similarity	NPC177047
0.7959	Intermediate Similarity	NPC477721
0.7959	Intermediate Similarity	NPC477716
0.7959	Intermediate Similarity	NPC47024
0.7959	Intermediate Similarity	NPC251680
0.7959	Intermediate Similarity	NPC472644
0.7957	Intermediate Similarity	NPC474396
0.7957	Intermediate Similarity	NPC50488
0.7957	Intermediate Similarity	NPC314727
0.7941	Intermediate Similarity	NPC306265
0.7938	Intermediate Similarity	NPC287668
0.7938	Intermediate Similarity	NPC151681
0.7938	Intermediate Similarity	NPC121402
0.7938	Intermediate Similarity	NPC224356
0.7938	Intermediate Similarity	NPC132753
0.7938	Intermediate Similarity	NPC205143
0.7938	Intermediate Similarity	NPC199099
0.7938	Intermediate Similarity	NPC175351
0.7938	Intermediate Similarity	NPC475709
0.7935	Intermediate Similarity	NPC471779
0.7935	Intermediate Similarity	NPC166857
0.7921	Intermediate Similarity	NPC472818
0.7921	Intermediate Similarity	NPC81630
0.7917	Intermediate Similarity	NPC329435
0.79	Intermediate Similarity	NPC165608
0.79	Intermediate Similarity	NPC196471
0.79	Intermediate Similarity	NPC97487
0.79	Intermediate Similarity	NPC10232
0.79	Intermediate Similarity	NPC187302
0.79	Intermediate Similarity	NPC189588
0.7895	Intermediate Similarity	NPC99653
0.7895	Intermediate Similarity	NPC472303
0.7889	Intermediate Similarity	NPC321385
0.7889	Intermediate Similarity	NPC79945
0.7879	Intermediate Similarity	NPC471075
0.7879	Intermediate Similarity	NPC471412
0.7879	Intermediate Similarity	NPC477717
0.7879	Intermediate Similarity	NPC472554
0.7872	Intermediate Similarity	NPC209816
0.7872	Intermediate Similarity	NPC220216
0.7872	Intermediate Similarity	NPC477782
0.7865	Intermediate Similarity	NPC170303
0.7864	Intermediate Similarity	NPC299590
0.7864	Intermediate Similarity	NPC322912
0.7864	Intermediate Similarity	NPC475030
0.7857	Intermediate Similarity	NPC159763
0.7857	Intermediate Similarity	NPC278386
0.7857	Intermediate Similarity	NPC216478
0.7857	Intermediate Similarity	NPC218107
0.7857	Intermediate Similarity	NPC124512
0.7849	Intermediate Similarity	NPC472378
0.7849	Intermediate Similarity	NPC291665
0.7849	Intermediate Similarity	NPC93411
0.7849	Intermediate Similarity	NPC474629
0.7843	Intermediate Similarity	NPC179380
0.7843	Intermediate Similarity	NPC472820
0.7841	Intermediate Similarity	NPC110373
0.7841	Intermediate Similarity	NPC80471
0.7841	Intermediate Similarity	NPC5908
0.7835	Intermediate Similarity	NPC221801
0.7835	Intermediate Similarity	NPC471765
0.7835	Intermediate Similarity	NPC154526
0.7835	Intermediate Similarity	NPC472362
0.7835	Intermediate Similarity	NPC162346
0.7835	Intermediate Similarity	NPC320231
0.7835	Intermediate Similarity	NPC472363
0.7835	Intermediate Similarity	NPC209297
0.7835	Intermediate Similarity	NPC284194
0.7835	Intermediate Similarity	NPC475380
0.7835	Intermediate Similarity	NPC211810
0.7826	Intermediate Similarity	NPC474062
0.7826	Intermediate Similarity	NPC329692
0.7822	Intermediate Similarity	NPC472819
0.7812	Intermediate Similarity	NPC140277
0.7812	Intermediate Similarity	NPC298973
0.7812	Intermediate Similarity	NPC161998
0.7812	Intermediate Similarity	NPC104925
0.7812	Intermediate Similarity	NPC225474
0.7812	Intermediate Similarity	NPC148000
0.7812	Intermediate Similarity	NPC469596
0.7812	Intermediate Similarity	NPC182826
0.7812	Intermediate Similarity	NPC105375
0.781	Intermediate Similarity	NPC42658
0.78	Intermediate Similarity	NPC238397
0.78	Intermediate Similarity	NPC471363
0.78	Intermediate Similarity	NPC162973
0.7789	Intermediate Similarity	NPC41239
0.7789	Intermediate Similarity	NPC477783
0.7789	Intermediate Similarity	NPC472814
0.7789	Intermediate Similarity	NPC177037
0.7789	Intermediate Similarity	NPC289479
0.7789	Intermediate Similarity	NPC249034
0.7788	Intermediate Similarity	NPC472666
0.7778	Intermediate Similarity	NPC477968
0.7778	Intermediate Similarity	NPC219285
0.7778	Intermediate Similarity	NPC477972

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 NPC472642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1747
0.2-0.3	3853
0.3-0.4	2245
0.4-0.5	711
0.5-0.6	256
0.6-0.7	149
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7959	Intermediate Similarity	NPD7640	Approved
0.7959	Intermediate Similarity	NPD7639	Approved
0.7864	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7638	Approved
0.7857	Intermediate Similarity	NPD4225	Approved
0.78	Intermediate Similarity	NPD7632	Discontinued
0.7619	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD6686	Approved
0.7455	Intermediate Similarity	NPD7328	Approved
0.7455	Intermediate Similarity	NPD7327	Approved
0.7387	Intermediate Similarity	NPD7516	Approved
0.7333	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD8296	Approved
0.7257	Intermediate Similarity	NPD8380	Approved
0.7257	Intermediate Similarity	NPD8379	Approved
0.7257	Intermediate Similarity	NPD8378	Approved
0.7257	Intermediate Similarity	NPD8335	Approved
0.7234	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD5344	Discontinued
0.7168	Intermediate Similarity	NPD8294	Approved
0.7168	Intermediate Similarity	NPD8377	Approved
0.7105	Intermediate Similarity	NPD8033	Approved
0.7071	Intermediate Similarity	NPD7637	Suspended
0.7009	Intermediate Similarity	NPD7507	Approved
0.6975	Remote Similarity	NPD7319	Approved
0.6923	Remote Similarity	NPD6648	Approved
0.6875	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7503	Approved
0.6804	Remote Similarity	NPD1694	Approved
0.6771	Remote Similarity	NPD6695	Phase 3
0.6765	Remote Similarity	NPD7748	Approved
0.6759	Remote Similarity	NPD6675	Approved
0.6759	Remote Similarity	NPD7128	Approved
0.6759	Remote Similarity	NPD6402	Approved
0.6759	Remote Similarity	NPD5739	Approved
0.6754	Remote Similarity	NPD7115	Discovery
0.6733	Remote Similarity	NPD7515	Phase 2
0.6731	Remote Similarity	NPD7902	Approved
0.6727	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5697	Approved
0.6697	Remote Similarity	NPD5701	Approved
0.6696	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD6881	Approved
0.6636	Remote Similarity	NPD7320	Approved
0.6636	Remote Similarity	NPD6899	Approved
0.6577	Remote Similarity	NPD6013	Approved
0.6577	Remote Similarity	NPD6373	Approved
0.6577	Remote Similarity	NPD6372	Approved
0.6577	Remote Similarity	NPD6012	Approved
0.6577	Remote Similarity	NPD6014	Approved
0.6566	Remote Similarity	NPD3618	Phase 1
0.6545	Remote Similarity	NPD6412	Phase 2
0.6526	Remote Similarity	NPD6929	Approved
0.6518	Remote Similarity	NPD7290	Approved
0.6518	Remote Similarity	NPD6883	Approved
0.6518	Remote Similarity	NPD7102	Approved
0.6509	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5779	Approved
0.6505	Remote Similarity	NPD5778	Approved
0.6505	Remote Similarity	NPD6399	Phase 3
0.65	Remote Similarity	NPD7750	Discontinued
0.65	Remote Similarity	NPD7524	Approved
0.6491	Remote Similarity	NPD8133	Approved
0.6486	Remote Similarity	NPD6011	Approved
0.6486	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5211	Phase 2
0.6471	Remote Similarity	NPD6698	Approved
0.6471	Remote Similarity	NPD46	Approved
0.6471	Remote Similarity	NPD7838	Discovery
0.6466	Remote Similarity	NPD6009	Approved
0.646	Remote Similarity	NPD6869	Approved
0.646	Remote Similarity	NPD8130	Phase 1
0.646	Remote Similarity	NPD6650	Approved
0.646	Remote Similarity	NPD6649	Approved
0.646	Remote Similarity	NPD6617	Approved
0.646	Remote Similarity	NPD6847	Approved
0.6458	Remote Similarity	NPD6930	Phase 2
0.6458	Remote Similarity	NPD6931	Approved
0.6458	Remote Similarity	NPD7525	Registered
0.6442	Remote Similarity	NPD7900	Approved
0.6442	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6084	Phase 2
0.6415	Remote Similarity	NPD4755	Approved
0.6415	Remote Similarity	NPD6083	Phase 2
0.6408	Remote Similarity	NPD8034	Phase 2
0.6408	Remote Similarity	NPD8035	Phase 2
0.6404	Remote Similarity	NPD8297	Approved
0.6381	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5328	Approved
0.6373	Remote Similarity	NPD6051	Approved
0.6364	Remote Similarity	NPD7492	Approved
0.6364	Remote Similarity	NPD5141	Approved
0.6354	Remote Similarity	NPD7645	Phase 2
0.6348	Remote Similarity	NPD4632	Approved
0.6346	Remote Similarity	NPD4202	Approved
0.6325	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5776	Phase 2
0.6316	Remote Similarity	NPD6925	Approved
0.6311	Remote Similarity	NPD6616	Approved
0.6306	Remote Similarity	NPD6008	Approved
0.6303	Remote Similarity	NPD6054	Approved
0.6303	Remote Similarity	NPD6319	Approved
0.6303	Remote Similarity	NPD6059	Approved
0.63	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5286	Approved
0.6296	Remote Similarity	NPD4700	Approved
0.6296	Remote Similarity	NPD5285	Approved
0.6296	Remote Similarity	NPD4696	Approved
0.6289	Remote Similarity	NPD7514	Phase 3
0.6289	Remote Similarity	NPD7332	Phase 2
0.6281	Remote Similarity	NPD8328	Phase 3
0.6261	Remote Similarity	NPD6053	Discontinued
0.626	Remote Similarity	NPD7078	Approved
0.626	Remote Similarity	NPD8293	Discontinued
0.625	Remote Similarity	NPD6115	Approved
0.625	Remote Similarity	NPD6016	Approved
0.625	Remote Similarity	NPD6079	Approved
0.625	Remote Similarity	NPD6015	Approved
0.625	Remote Similarity	NPD7087	Discontinued
0.625	Remote Similarity	NPD7145	Approved
0.625	Remote Similarity	NPD6118	Approved
0.625	Remote Similarity	NPD6697	Approved
0.625	Remote Similarity	NPD6114	Approved
0.6239	Remote Similarity	NPD4159	Approved
0.6239	Remote Similarity	NPD6274	Approved
0.6238	Remote Similarity	NPD6684	Approved
0.6238	Remote Similarity	NPD7521	Approved
0.6238	Remote Similarity	NPD7334	Approved
0.6238	Remote Similarity	NPD7146	Approved
0.6238	Remote Similarity	NPD6409	Approved
0.6238	Remote Similarity	NPD5330	Approved
0.6228	Remote Similarity	NPD6371	Approved
0.6226	Remote Similarity	NPD5695	Phase 3
0.6224	Remote Similarity	NPD6902	Approved
0.621	Remote Similarity	NPD7736	Approved
0.6204	Remote Similarity	NPD5696	Approved
0.62	Remote Similarity	NPD3665	Phase 1
0.62	Remote Similarity	NPD3133	Approved
0.62	Remote Similarity	NPD3666	Approved
0.6198	Remote Similarity	NPD6370	Approved
0.6198	Remote Similarity	NPD5988	Approved
0.6182	Remote Similarity	NPD5224	Approved
0.6182	Remote Similarity	NPD5225	Approved
0.6182	Remote Similarity	NPD5226	Approved
0.6182	Remote Similarity	NPD4633	Approved
0.6176	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5221	Approved
0.6168	Remote Similarity	NPD4697	Phase 3
0.6168	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5222	Approved
0.6162	Remote Similarity	NPD3667	Approved
0.6154	Remote Similarity	NPD5785	Approved
0.6146	Remote Similarity	NPD6116	Phase 1
0.6139	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD6893	Approved
0.6126	Remote Similarity	NPD5175	Approved
0.6126	Remote Similarity	NPD5174	Approved
0.6122	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD6672	Approved
0.6117	Remote Similarity	NPD6903	Approved
0.6117	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5737	Approved
0.6116	Remote Similarity	NPD5983	Phase 2
0.6111	Remote Similarity	NPD5173	Approved
0.6095	Remote Similarity	NPD5693	Phase 1
0.6095	Remote Similarity	NPD6411	Approved
0.6091	Remote Similarity	NPD5223	Approved
0.6087	Remote Similarity	NPD4634	Approved
0.6083	Remote Similarity	NPD7101	Approved
0.6083	Remote Similarity	NPD7100	Approved
0.6078	Remote Similarity	NPD4249	Approved
0.6061	Remote Similarity	NPD6898	Phase 1
0.6058	Remote Similarity	NPD4753	Phase 2
0.605	Remote Similarity	NPD6317	Approved
0.6042	Remote Similarity	NPD6117	Approved
0.6042	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4786	Approved
0.6034	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4250	Approved
0.6019	Remote Similarity	NPD3573	Approved
0.6019	Remote Similarity	NPD4251	Approved
0.6018	Remote Similarity	NPD4767	Approved
0.6018	Remote Similarity	NPD4768	Approved
0.6016	Remote Similarity	NPD6067	Discontinued
0.6016	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD6314	Approved
0.6	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD6313	Approved
0.6	Remote Similarity	NPD3168	Discontinued
0.5984	Remote Similarity	NPD8513	Phase 3
0.5984	Remote Similarity	NPD8517	Approved
0.5984	Remote Similarity	NPD8516	Approved
0.5984	Remote Similarity	NPD6909	Approved
0.5984	Remote Similarity	NPD8515	Approved
0.5984	Remote Similarity	NPD6908	Approved
0.5982	Remote Similarity	NPD4754	Approved
0.598	Remote Similarity	NPD1696	Phase 3
0.5979	Remote Similarity	NPD6932	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