NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	282.15
Volume:	281.005
LogP:	1.267
LogD:	0.971
LogS:	-2.97
# 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:	0.574
Synthetic Accessibility Score:	4.749
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:	-4.847
MDCK Permeability:	2.3290864191949368e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.849
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.8
Plasma Protein Binding (PPB):	47.67408752441406%
Volume Distribution (VD):	0.742
Pgp-substrate:	34.87651062011719%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.676
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.768
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.107
CYP3A4-inhibitor:	0.271
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	3.637
Half-life (T1/2):	0.569

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.112
AMES Toxicity:	0.432
Rat Oral Acute Toxicity:	0.91
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.399
Carcinogencity:	0.048
Eye Corrosion:	0.013
Eye Irritation:	0.195
Respiratory Toxicity:	0.761

Download Data

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

Natural Product: NPC78594

Natural Product ID:	NPC78594
*Common Name:**	Chloraeudolide
IUPAC Name:	(4aR,5R,8R,8aR,9aS)-5,8,9a-trihydroxy-3,5,8a-trimethyl-4,4a,6,7,8,9-hexahydrobenzo[f][1]benzofuran-2-one
Synonyms:	Chloraeudolide
Standard InCHIKey:	BWOFLNFAFOQHRS-BBIZWXPBSA-N
Standard InCHI:	InChI=1S/C15H22O5/c1-8-9-6-10-13(2,7-15(9,19)20-12(8)17)11(16)4-5-14(10,3)18/h10-11,16,18-19H,4-7H2,1-3H3/t10-,11-,13-,14-,15+/m1/s1
SMILES:	CC1=C2C[C@@H]3[C@@](C)(C[C@]2(O)OC1=O)[C@@H](CC[C@@]3(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1669185
PubChem CID:	50993975
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
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	DOI[10.1016/j.phytol.2016.01.005]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18451544]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	whole plants	Suiling district, Heilongjiang Province, China	2008-AUG	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	Whole plant	Suiling district, Heilongjiang Province, China	2008-AUG	PMID[21142110]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21650224]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21650224]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23738470]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[23738470]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[25275213]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	leaves	n.a.	n.a.	PMID[26238320]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28765	Miliusa balansae	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6915	Chloranthus japonicus	Species	Chloranthaceae	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	8

Activity Type	# Activity
Cell Line	8

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[462910]
NPT1997	Cell Line	OS-RC-2	Homo sapiens	IC50	<	10000.0	nM	PMID[462910]
NPT81	Cell Line	A549	Homo sapiens	IC50	<	10000.0	nM	PMID[462910]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	<	10000.0	nM	PMID[462910]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	<	10000.0	nM	PMID[462910]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[462910]
NPT515	Cell Line	SGC-7901	Homo sapiens	IC50	<	10000.0	nM	PMID[462910]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	<	10000.0	nM	PMID[462910]

☑ 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 NPC78594 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	207
0.1-0.2	1477
0.2-0.3	4722
0.3-0.4	9359
0.4-0.5	12923
0.5-0.6	7136
0.6-0.7	5675
0.7-0.8	1066
0.8-0.85	99
0.85-0.9	19
0.9-0.95	13
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9438	High Similarity	NPC471915
0.9432	High Similarity	NPC472641
0.9432	High Similarity	NPC472640
0.9425	High Similarity	NPC472642
0.9294	High Similarity	NPC253604
0.9176	High Similarity	NPC32223
0.9032	High Similarity	NPC324841
0.9032	High Similarity	NPC16601
0.9011	High Similarity	NPC111273
0.9	High Similarity	NPC110022
0.8913	High Similarity	NPC165632
0.8901	High Similarity	NPC105490
0.8842	High Similarity	NPC471914
0.8791	High Similarity	NPC7349
0.875	High Similarity	NPC471938
0.866	High Similarity	NPC471937
0.8646	High Similarity	NPC475038
0.8646	High Similarity	NPC109195
0.8557	High Similarity	NPC474822
0.8556	High Similarity	NPC242448
0.8485	Intermediate Similarity	NPC471205
0.8478	Intermediate Similarity	NPC472811
0.8404	Intermediate Similarity	NPC276110
0.8404	Intermediate Similarity	NPC472441
0.84	Intermediate Similarity	NPC181994
0.8387	Intermediate Similarity	NPC472812
0.8367	Intermediate Similarity	NPC471208
0.8351	Intermediate Similarity	NPC11974
0.8333	Intermediate Similarity	NPC131813
0.8316	Intermediate Similarity	NPC134072
0.8316	Intermediate Similarity	NPC234993
0.83	Intermediate Similarity	NPC122816
0.8298	Intermediate Similarity	NPC57117
0.828	Intermediate Similarity	NPC329842
0.828	Intermediate Similarity	NPC473675
0.8276	Intermediate Similarity	NPC10636
0.8265	Intermediate Similarity	NPC472815
0.8265	Intermediate Similarity	NPC121423
0.8265	Intermediate Similarity	NPC162973
0.8247	Intermediate Similarity	NPC476767
0.8247	Intermediate Similarity	NPC38855
0.8218	Intermediate Similarity	NPC325054
0.8218	Intermediate Similarity	NPC38948
0.8211	Intermediate Similarity	NPC329435
0.82	Intermediate Similarity	NPC51719
0.8191	Intermediate Similarity	NPC53555
0.8182	Intermediate Similarity	NPC281378
0.8182	Intermediate Similarity	NPC160583
0.8182	Intermediate Similarity	NPC45897
0.8182	Intermediate Similarity	NPC120009
0.8172	Intermediate Similarity	NPC78973
0.8163	Intermediate Similarity	NPC471412
0.8152	Intermediate Similarity	NPC472810
0.8152	Intermediate Similarity	NPC472809
0.8144	Intermediate Similarity	NPC275086
0.8144	Intermediate Similarity	NPC278673
0.8144	Intermediate Similarity	NPC325229
0.8137	Intermediate Similarity	NPC206618
0.8137	Intermediate Similarity	NPC31522
0.8137	Intermediate Similarity	NPC322912
0.8125	Intermediate Similarity	NPC475380
0.8125	Intermediate Similarity	NPC209297
0.8119	Intermediate Similarity	NPC475074
0.8111	Intermediate Similarity	NPC102048
0.8105	Intermediate Similarity	NPC140277
0.8105	Intermediate Similarity	NPC470255
0.8081	Intermediate Similarity	NPC58329
0.8081	Intermediate Similarity	NPC476081
0.8081	Intermediate Similarity	NPC165250
0.8081	Intermediate Similarity	NPC295791
0.8061	Intermediate Similarity	NPC251680
0.8061	Intermediate Similarity	NPC471413
0.8043	Intermediate Similarity	NPC473891
0.8041	Intermediate Similarity	NPC311241
0.8041	Intermediate Similarity	NPC205143
0.8041	Intermediate Similarity	NPC199099
0.8041	Intermediate Similarity	NPC51499
0.8041	Intermediate Similarity	NPC100912
0.8041	Intermediate Similarity	NPC475446
0.8039	Intermediate Similarity	NPC300614
0.8039	Intermediate Similarity	NPC90946
0.802	Intermediate Similarity	NPC218158
0.8	Intermediate Similarity	NPC472821
0.8	Intermediate Similarity	NPC159533
0.8	Intermediate Similarity	NPC152778
0.8	Intermediate Similarity	NPC205034
0.8	Intermediate Similarity	NPC139692
0.8	Intermediate Similarity	NPC165608
0.8	Intermediate Similarity	NPC162615
0.8	Intermediate Similarity	NPC311070
0.798	Intermediate Similarity	NPC247701
0.798	Intermediate Similarity	NPC25177
0.798	Intermediate Similarity	NPC295110
0.798	Intermediate Similarity	NPC268829
0.798	Intermediate Similarity	NPC198992
0.798	Intermediate Similarity	NPC222875
0.7979	Intermediate Similarity	NPC310479
0.7979	Intermediate Similarity	NPC182136
0.7979	Intermediate Similarity	NPC221111
0.7979	Intermediate Similarity	NPC280149
0.7961	Intermediate Similarity	NPC299590
0.7959	Intermediate Similarity	NPC72647
0.7959	Intermediate Similarity	NPC473154
0.7959	Intermediate Similarity	NPC218107
0.7959	Intermediate Similarity	NPC107806
0.7959	Intermediate Similarity	NPC474440
0.7957	Intermediate Similarity	NPC291665
0.7941	Intermediate Similarity	NPC216636
0.7941	Intermediate Similarity	NPC67321
0.7941	Intermediate Similarity	NPC319438
0.7941	Intermediate Similarity	NPC187435
0.7938	Intermediate Similarity	NPC319861
0.7938	Intermediate Similarity	NPC242848
0.7938	Intermediate Similarity	NPC473153
0.7938	Intermediate Similarity	NPC194132
0.7935	Intermediate Similarity	NPC471219
0.7931	Intermediate Similarity	NPC189206
0.7921	Intermediate Similarity	NPC161775
0.7917	Intermediate Similarity	NPC474554
0.7917	Intermediate Similarity	NPC161998
0.7917	Intermediate Similarity	NPC474555
0.7905	Intermediate Similarity	NPC42658
0.79	Intermediate Similarity	NPC472552
0.7895	Intermediate Similarity	NPC72845
0.7895	Intermediate Similarity	NPC41239
0.7895	Intermediate Similarity	NPC124374
0.7885	Intermediate Similarity	NPC177047
0.7879	Intermediate Similarity	NPC20113
0.7879	Intermediate Similarity	NPC228251
0.7879	Intermediate Similarity	NPC477716
0.7879	Intermediate Similarity	NPC161527
0.7879	Intermediate Similarity	NPC477972
0.7879	Intermediate Similarity	NPC219285
0.7879	Intermediate Similarity	NPC472644
0.7879	Intermediate Similarity	NPC477968
0.7879	Intermediate Similarity	NPC477721
0.7879	Intermediate Similarity	NPC477971
0.7872	Intermediate Similarity	NPC474396
0.7872	Intermediate Similarity	NPC470734
0.7872	Intermediate Similarity	NPC170633
0.7872	Intermediate Similarity	NPC50488
0.7857	Intermediate Similarity	NPC121402
0.7857	Intermediate Similarity	NPC132753
0.7857	Intermediate Similarity	NPC477719
0.7857	Intermediate Similarity	NPC224356
0.7857	Intermediate Similarity	NPC175351
0.7857	Intermediate Similarity	NPC477718
0.7857	Intermediate Similarity	NPC151681
0.7857	Intermediate Similarity	NPC287668
0.785	Intermediate Similarity	NPC471816
0.7849	Intermediate Similarity	NPC471796
0.7849	Intermediate Similarity	NPC166857
0.7849	Intermediate Similarity	NPC471779
0.7843	Intermediate Similarity	NPC239961
0.7843	Intermediate Similarity	NPC81630
0.7843	Intermediate Similarity	NPC477090
0.7843	Intermediate Similarity	NPC119855
0.7843	Intermediate Similarity	NPC34768
0.7843	Intermediate Similarity	NPC220217
0.7843	Intermediate Similarity	NPC471206
0.7843	Intermediate Similarity	NPC472818
0.7822	Intermediate Similarity	NPC97487
0.7822	Intermediate Similarity	NPC120321
0.7822	Intermediate Similarity	NPC196471
0.7822	Intermediate Similarity	NPC187302
0.7822	Intermediate Similarity	NPC189588
0.7822	Intermediate Similarity	NPC10232
0.7812	Intermediate Similarity	NPC99653
0.7812	Intermediate Similarity	NPC472303
0.7802	Intermediate Similarity	NPC321385
0.7802	Intermediate Similarity	NPC476927
0.78	Intermediate Similarity	NPC477717
0.78	Intermediate Similarity	NPC472554
0.7789	Intermediate Similarity	NPC209816
0.7789	Intermediate Similarity	NPC220216
0.7789	Intermediate Similarity	NPC477782
0.7788	Intermediate Similarity	NPC475030
0.7778	Intermediate Similarity	NPC170303
0.7767	Intermediate Similarity	NPC472820
0.7766	Intermediate Similarity	NPC106332
0.7766	Intermediate Similarity	NPC93411
0.7755	Intermediate Similarity	NPC154526
0.7755	Intermediate Similarity	NPC472363
0.7755	Intermediate Similarity	NPC202833
0.7755	Intermediate Similarity	NPC16967
0.7755	Intermediate Similarity	NPC93245
0.7755	Intermediate Similarity	NPC29952
0.7755	Intermediate Similarity	NPC240673
0.7755	Intermediate Similarity	NPC472362
0.7755	Intermediate Similarity	NPC17578
0.7753	Intermediate Similarity	NPC110373
0.7753	Intermediate Similarity	NPC5908
0.7753	Intermediate Similarity	NPC80471
0.7745	Intermediate Similarity	NPC472819
0.7742	Intermediate Similarity	NPC474062
0.7742	Intermediate Similarity	NPC329692
0.7732	Intermediate Similarity	NPC119562
0.7732	Intermediate Similarity	NPC279410
0.7732	Intermediate Similarity	NPC472416
0.7732	Intermediate Similarity	NPC191521

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 NPC78594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1799
0.2-0.3	3874
0.3-0.4	2214
0.4-0.5	666
0.5-0.6	259
0.6-0.7	148
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
0.8061	Intermediate Similarity	NPD7639	Approved
0.8061	Intermediate Similarity	NPD7640	Approved
0.7961	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD7638	Approved
0.79	Intermediate Similarity	NPD7632	Discontinued
0.7714	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4225	Approved
0.7545	Intermediate Similarity	NPD7327	Approved
0.7545	Intermediate Similarity	NPD7328	Approved
0.7524	Intermediate Similarity	NPD6686	Approved
0.7477	Intermediate Similarity	NPD7516	Approved
0.7429	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5344	Discontinued
0.7257	Intermediate Similarity	NPD8294	Approved
0.7257	Intermediate Similarity	NPD8377	Approved
0.7193	Intermediate Similarity	NPD8033	Approved
0.7193	Intermediate Similarity	NPD8378	Approved
0.7193	Intermediate Similarity	NPD8296	Approved
0.7193	Intermediate Similarity	NPD8380	Approved
0.7193	Intermediate Similarity	NPD8379	Approved
0.7193	Intermediate Similarity	NPD8335	Approved
0.7128	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7507	Approved
0.7019	Intermediate Similarity	NPD6648	Approved
0.6979	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7319	Approved
0.6897	Remote Similarity	NPD7503	Approved
0.6762	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1694	Approved
0.6699	Remote Similarity	NPD7748	Approved
0.6697	Remote Similarity	NPD6675	Approved
0.6697	Remote Similarity	NPD7128	Approved
0.6697	Remote Similarity	NPD6402	Approved
0.6697	Remote Similarity	NPD5739	Approved
0.6696	Remote Similarity	NPD7115	Discovery
0.6696	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7515	Phase 2
0.6637	Remote Similarity	NPD6882	Approved
0.6636	Remote Similarity	NPD5701	Approved
0.6636	Remote Similarity	NPD5697	Approved
0.6633	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD4632	Approved
0.6579	Remote Similarity	NPD8133	Approved
0.6577	Remote Similarity	NPD6899	Approved
0.6577	Remote Similarity	NPD6011	Approved
0.6577	Remote Similarity	NPD6881	Approved
0.6577	Remote Similarity	NPD7320	Approved
0.6577	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7525	Registered
0.6545	Remote Similarity	NPD6008	Approved
0.6531	Remote Similarity	NPD6695	Phase 3
0.6518	Remote Similarity	NPD6373	Approved
0.6518	Remote Similarity	NPD6014	Approved
0.6518	Remote Similarity	NPD6013	Approved
0.6518	Remote Similarity	NPD6372	Approved
0.6518	Remote Similarity	NPD6012	Approved
0.65	Remote Similarity	NPD3618	Phase 1
0.6486	Remote Similarity	NPD6412	Phase 2
0.6471	Remote Similarity	NPD6051	Approved
0.646	Remote Similarity	NPD7290	Approved
0.646	Remote Similarity	NPD7102	Approved
0.646	Remote Similarity	NPD6883	Approved
0.6446	Remote Similarity	NPD7492	Approved
0.6442	Remote Similarity	NPD6399	Phase 3
0.6442	Remote Similarity	NPD4202	Approved
0.6422	Remote Similarity	NPD5211	Phase 2
0.6408	Remote Similarity	NPD46	Approved
0.6408	Remote Similarity	NPD7838	Discovery
0.6408	Remote Similarity	NPD6698	Approved
0.6404	Remote Similarity	NPD8130	Phase 1
0.6404	Remote Similarity	NPD6869	Approved
0.6404	Remote Similarity	NPD6847	Approved
0.6404	Remote Similarity	NPD6649	Approved
0.6404	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6650	Approved
0.6404	Remote Similarity	NPD6617	Approved
0.6393	Remote Similarity	NPD6616	Approved
0.6387	Remote Similarity	NPD6054	Approved
0.6387	Remote Similarity	NPD6059	Approved
0.6387	Remote Similarity	NPD6319	Approved
0.6381	Remote Similarity	NPD7900	Approved
0.6381	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6084	Phase 2
0.6355	Remote Similarity	NPD4755	Approved
0.6355	Remote Similarity	NPD6083	Phase 2
0.6348	Remote Similarity	NPD8297	Approved
0.6348	Remote Similarity	NPD6053	Discontinued
0.6346	Remote Similarity	NPD8034	Phase 2
0.6346	Remote Similarity	NPD8035	Phase 2
0.6341	Remote Similarity	NPD7078	Approved
0.6341	Remote Similarity	NPD8293	Discontinued
0.6333	Remote Similarity	NPD6015	Approved
0.6333	Remote Similarity	NPD5983	Phase 2
0.6333	Remote Similarity	NPD6016	Approved
0.6316	Remote Similarity	NPD6371	Approved
0.6311	Remote Similarity	NPD5328	Approved
0.6306	Remote Similarity	NPD5141	Approved
0.629	Remote Similarity	NPD7736	Approved
0.6286	Remote Similarity	NPD5778	Approved
0.6286	Remote Similarity	NPD5779	Approved
0.6281	Remote Similarity	NPD6370	Approved
0.6281	Remote Similarity	NPD5988	Approved
0.6275	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7750	Discontinued
0.6275	Remote Similarity	NPD7524	Approved
0.6271	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD4696	Approved
0.6239	Remote Similarity	NPD5285	Approved
0.6239	Remote Similarity	NPD5286	Approved
0.6239	Remote Similarity	NPD4700	Approved
0.6238	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.623	Remote Similarity	NPD7604	Phase 2
0.623	Remote Similarity	NPD8328	Phase 3
0.6224	Remote Similarity	NPD6931	Approved
0.6224	Remote Similarity	NPD6930	Phase 2
0.619	Remote Similarity	NPD5693	Phase 1
0.619	Remote Similarity	NPD6079	Approved
0.6186	Remote Similarity	NPD6114	Approved
0.6186	Remote Similarity	NPD6274	Approved
0.6186	Remote Similarity	NPD6697	Approved
0.6186	Remote Similarity	NPD6115	Approved
0.6186	Remote Similarity	NPD6118	Approved
0.6182	Remote Similarity	NPD5223	Approved
0.6176	Remote Similarity	NPD7146	Approved
0.6176	Remote Similarity	NPD7521	Approved
0.6176	Remote Similarity	NPD5330	Approved
0.6176	Remote Similarity	NPD6684	Approved
0.6176	Remote Similarity	NPD7334	Approved
0.6176	Remote Similarity	NPD6409	Approved
0.6168	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5695	Phase 3
0.6147	Remote Similarity	NPD5696	Approved
0.6139	Remote Similarity	NPD3133	Approved
0.6139	Remote Similarity	NPD3666	Approved
0.6139	Remote Similarity	NPD3665	Phase 1
0.6134	Remote Similarity	NPD6317	Approved
0.6129	Remote Similarity	NPD6336	Discontinued
0.6126	Remote Similarity	NPD5224	Approved
0.6126	Remote Similarity	NPD4633	Approved
0.6126	Remote Similarity	NPD5226	Approved
0.6126	Remote Similarity	NPD5225	Approved
0.6122	Remote Similarity	NPD7645	Phase 2
0.6122	Remote Similarity	NPD6929	Approved
0.6121	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD3573	Approved
0.6111	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4697	Phase 3
0.6111	Remote Similarity	NPD5222	Approved
0.6111	Remote Similarity	NPD5221	Approved
0.61	Remote Similarity	NPD3667	Approved
0.6098	Remote Similarity	NPD6067	Discontinued
0.6095	Remote Similarity	NPD5785	Approved
0.6095	Remote Similarity	NPD3168	Discontinued
0.6083	Remote Similarity	NPD6313	Approved
0.6083	Remote Similarity	NPD6335	Approved
0.6083	Remote Similarity	NPD6314	Approved
0.6082	Remote Similarity	NPD6116	Phase 1
0.6078	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD1696	Phase 3
0.6071	Remote Similarity	NPD5175	Approved
0.6071	Remote Similarity	NPD4754	Approved
0.6071	Remote Similarity	NPD5174	Approved
0.6066	Remote Similarity	NPD8513	Phase 3
0.6066	Remote Similarity	NPD8517	Approved
0.6066	Remote Similarity	NPD8515	Approved
0.6066	Remote Similarity	NPD8516	Approved
0.6061	Remote Similarity	NPD7332	Phase 2
0.6061	Remote Similarity	NPD7514	Phase 3
0.6058	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD6672	Approved
0.6058	Remote Similarity	NPD6903	Approved
0.6058	Remote Similarity	NPD5737	Approved
0.6055	Remote Similarity	NPD5173	Approved
0.6038	Remote Similarity	NPD7087	Discontinued
0.6036	Remote Similarity	NPD4159	Approved
0.6034	Remote Similarity	NPD4634	Approved
0.6033	Remote Similarity	NPD7100	Approved
0.6033	Remote Similarity	NPD7101	Approved
0.6032	Remote Similarity	NPD6033	Approved
0.6019	Remote Similarity	NPD4519	Discontinued
0.6019	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4623	Approved
0.6019	Remote Similarity	NPD4249	Approved
0.6019	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4753	Phase 2
0.5985	Remote Similarity	NPD7625	Phase 1
0.598	Remote Similarity	NPD4786	Approved
0.5979	Remote Similarity	NPD6117	Approved
0.5979	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD4768	Approved
0.5965	Remote Similarity	NPD4767	Approved
0.5962	Remote Similarity	NPD4251	Approved
0.5962	Remote Similarity	NPD4250	Approved
0.5938	Remote Similarity	NPD6924	Approved
0.5938	Remote Similarity	NPD6926	Approved
0.5935	Remote Similarity	NPD6909	Approved
0.5935	Remote Similarity	NPD6908	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