NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.13
Volume:	278.369
LogP:	0.878
LogD:	0.572
LogS:	-2.932
# Rotatable Bonds:	0
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.645
Synthetic Accessibility Score:	4.876
Fsp3:	0.733
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:	-4.821
MDCK Permeability:	1.6661077097523957e-05
Pgp-inhibitor:	0.236
Pgp-substrate:	0.309
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.145
30% Bioavailability (F30%):	0.46

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.979
Plasma Protein Binding (PPB):	58.5738525390625%
Volume Distribution (VD):	0.755
Pgp-substrate:	48.6184196472168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.666
CYP2C19-inhibitor:	0.056
CYP2C19-substrate:	0.813
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.145
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.113
CYP3A4-substrate:	0.302

ADMET: Excretion

Clearance (CL):	5.029
Half-life (T1/2):	0.532

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.161
Drug-inuced Liver Injury (DILI):	0.185
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.257
Maximum Recommended Daily Dose:	0.894
Skin Sensitization:	0.173
Carcinogencity:	0.029
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.077

Download Data

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

Natural Product: NPC165632

Natural Product ID:	NPC165632
*Common Name:**	Linderagalactone E
IUPAC Name:	(4R,4aS,8R,8aR)-4,8,9a-trihydroxy-3,5,8a-trimethyl-4a,7,8,9-tetrahydro-4H-benzo[f][1]benzofuran-2-one
Synonyms:	Linderagalactone E
Standard InCHIKey:	ULOCCNMREXITLK-OQRLSGKASA-N
Standard InCHI:	InChI=1S/C15H20O5/c1-7-4-5-9(16)14(3)6-15(19)11(12(17)10(7)14)8(2)13(18)20-15/h4,9-10,12,16-17,19H,5-6H2,1-3H3/t9-,10-,12-,14+,15?/m1/s1
SMILES:	O=C1OC2(C(=C1C)[C@H](O)[C@@H]1[C@](C2)(C)[C@H](O)CC=C1C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078133
PubChem CID:	44254424
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
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	PMID[17999353]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[19639966]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4682	Lindera aggregata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13346	Lindera strichnifolia	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4682	Lindera aggregata	Species	Lauraceae	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
EC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	EC50	=	67500.0	nM	PMID[469909]

☑ 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 NPC165632 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	184
0.1-0.2	1201
0.2-0.3	4057
0.3-0.4	6575
0.4-0.5	15347
0.5-0.6	7469
0.6-0.7	6185
0.7-0.8	1467
0.8-0.85	175
0.85-0.9	35
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC472641
0.9231	High Similarity	NPC472640
0.9222	High Similarity	NPC472642
0.9053	High Similarity	NPC16601
0.9032	High Similarity	NPC471915
0.8969	High Similarity	NPC471938
0.8913	High Similarity	NPC78594
0.8878	High Similarity	NPC471937
0.8866	High Similarity	NPC58329
0.8866	High Similarity	NPC471914
0.883	High Similarity	NPC276110
0.8817	High Similarity	NPC472812
0.8791	High Similarity	NPC242448
0.871	High Similarity	NPC472811
0.8673	High Similarity	NPC472552
0.866	High Similarity	NPC38855
0.866	High Similarity	NPC324841
0.8646	High Similarity	NPC205143
0.8632	High Similarity	NPC111273
0.8617	High Similarity	NPC110022
0.8614	High Similarity	NPC38948
0.8614	High Similarity	NPC181994
0.8602	High Similarity	NPC78973
0.8586	High Similarity	NPC120009
0.8586	High Similarity	NPC45897
0.8571	High Similarity	NPC472554
0.8571	High Similarity	NPC131813
0.8557	High Similarity	NPC275086
0.8557	High Similarity	NPC325229
0.8557	High Similarity	NPC216478
0.8542	High Similarity	NPC202833
0.8542	High Similarity	NPC234993
0.8542	High Similarity	NPC134072
0.8529	High Similarity	NPC206618
0.8526	High Similarity	NPC105490
0.8526	High Similarity	NPC57117
0.8515	High Similarity	NPC471205
0.8511	High Similarity	NPC124374
0.8495	Intermediate Similarity	NPC470734
0.8495	Intermediate Similarity	NPC314727
0.8485	Intermediate Similarity	NPC475038
0.8485	Intermediate Similarity	NPC109195
0.8485	Intermediate Similarity	NPC471363
0.8485	Intermediate Similarity	NPC476081
0.8485	Intermediate Similarity	NPC238397
0.8469	Intermediate Similarity	NPC472644
0.8462	Intermediate Similarity	NPC253604
0.8454	Intermediate Similarity	NPC287668
0.8454	Intermediate Similarity	NPC51499
0.8431	Intermediate Similarity	NPC470024
0.8421	Intermediate Similarity	NPC53555
0.8421	Intermediate Similarity	NPC205034
0.8421	Intermediate Similarity	NPC152778
0.8421	Intermediate Similarity	NPC7349
0.8421	Intermediate Similarity	NPC99653
0.8421	Intermediate Similarity	NPC162615
0.8404	Intermediate Similarity	NPC220216
0.8404	Intermediate Similarity	NPC221111
0.8404	Intermediate Similarity	NPC280149
0.84	Intermediate Similarity	NPC23584
0.84	Intermediate Similarity	NPC7644
0.84	Intermediate Similarity	NPC7613
0.84	Intermediate Similarity	NPC127933
0.84	Intermediate Similarity	NPC475889
0.84	Intermediate Similarity	NPC134270
0.8387	Intermediate Similarity	NPC472810
0.8387	Intermediate Similarity	NPC472809
0.8387	Intermediate Similarity	NPC472378
0.8384	Intermediate Similarity	NPC198992
0.837	Intermediate Similarity	NPC471219
0.8367	Intermediate Similarity	NPC278673
0.8367	Intermediate Similarity	NPC474440
0.8352	Intermediate Similarity	NPC32223
0.8351	Intermediate Similarity	NPC221801
0.8351	Intermediate Similarity	NPC284194
0.8351	Intermediate Similarity	NPC471765
0.8351	Intermediate Similarity	NPC211810
0.8333	Intermediate Similarity	NPC475074
0.8333	Intermediate Similarity	NPC67321
0.8333	Intermediate Similarity	NPC187435
0.8333	Intermediate Similarity	NPC298973
0.8333	Intermediate Similarity	NPC109376
0.8333	Intermediate Similarity	NPC470255
0.8333	Intermediate Similarity	NPC104925
0.8317	Intermediate Similarity	NPC473207
0.8317	Intermediate Similarity	NPC81567
0.8317	Intermediate Similarity	NPC201880
0.8317	Intermediate Similarity	NPC264867
0.8317	Intermediate Similarity	NPC470321
0.8316	Intermediate Similarity	NPC473675
0.8316	Intermediate Similarity	NPC329842
0.8316	Intermediate Similarity	NPC72845
0.83	Intermediate Similarity	NPC472815
0.83	Intermediate Similarity	NPC11956
0.83	Intermediate Similarity	NPC295791
0.83	Intermediate Similarity	NPC121423
0.8298	Intermediate Similarity	NPC246028
0.8298	Intermediate Similarity	NPC261320
0.8283	Intermediate Similarity	NPC161527
0.8283	Intermediate Similarity	NPC219285
0.8283	Intermediate Similarity	NPC477972
0.8283	Intermediate Similarity	NPC473219
0.8283	Intermediate Similarity	NPC470761
0.8283	Intermediate Similarity	NPC47024
0.8283	Intermediate Similarity	NPC476767
0.8283	Intermediate Similarity	NPC20113
0.8283	Intermediate Similarity	NPC228251
0.8283	Intermediate Similarity	NPC477971
0.8283	Intermediate Similarity	NPC477968
0.8269	Intermediate Similarity	NPC177047
0.8265	Intermediate Similarity	NPC473244
0.8252	Intermediate Similarity	NPC224660
0.8252	Intermediate Similarity	NPC325054
0.8247	Intermediate Similarity	NPC472441
0.8242	Intermediate Similarity	NPC311070
0.8242	Intermediate Similarity	NPC472377
0.8235	Intermediate Similarity	NPC252296
0.8235	Intermediate Similarity	NPC82251
0.8235	Intermediate Similarity	NPC111952
0.8235	Intermediate Similarity	NPC218158
0.8235	Intermediate Similarity	NPC172867
0.8235	Intermediate Similarity	NPC51719
0.8229	Intermediate Similarity	NPC139692
0.8218	Intermediate Similarity	NPC159533
0.8218	Intermediate Similarity	NPC281378
0.8218	Intermediate Similarity	NPC474822
0.8218	Intermediate Similarity	NPC471208
0.8218	Intermediate Similarity	NPC120321
0.8211	Intermediate Similarity	NPC48732
0.8211	Intermediate Similarity	NPC470817
0.8211	Intermediate Similarity	NPC281942
0.8211	Intermediate Similarity	NPC182136
0.8211	Intermediate Similarity	NPC232426
0.8211	Intermediate Similarity	NPC310479
0.82	Intermediate Similarity	NPC11974
0.82	Intermediate Similarity	NPC472643
0.819	Intermediate Similarity	NPC17791
0.8182	Intermediate Similarity	NPC473154
0.8173	Intermediate Similarity	NPC475586
0.8173	Intermediate Similarity	NPC31522
0.8163	Intermediate Similarity	NPC473153
0.8163	Intermediate Similarity	NPC16967
0.8163	Intermediate Similarity	NPC242848
0.8155	Intermediate Similarity	NPC122816
0.8155	Intermediate Similarity	NPC88013
0.8155	Intermediate Similarity	NPC143609
0.8155	Intermediate Similarity	NPC184512
0.8155	Intermediate Similarity	NPC125423
0.8152	Intermediate Similarity	NPC102048
0.8144	Intermediate Similarity	NPC469697
0.8144	Intermediate Similarity	NPC161998
0.8144	Intermediate Similarity	NPC191521
0.8144	Intermediate Similarity	NPC472360
0.8144	Intermediate Similarity	NPC472416
0.8125	Intermediate Similarity	NPC141831
0.8125	Intermediate Similarity	NPC477574
0.8119	Intermediate Similarity	NPC469606
0.8119	Intermediate Similarity	NPC165250
0.8119	Intermediate Similarity	NPC31058
0.8119	Intermediate Similarity	NPC273005
0.8113	Intermediate Similarity	NPC317460
0.8113	Intermediate Similarity	NPC321272
0.8113	Intermediate Similarity	NPC470025
0.8113	Intermediate Similarity	NPC328074
0.8111	Intermediate Similarity	NPC10636
0.8105	Intermediate Similarity	NPC50488
0.8105	Intermediate Similarity	NPC470819
0.8105	Intermediate Similarity	NPC474396
0.81	Intermediate Similarity	NPC477716
0.81	Intermediate Similarity	NPC476299
0.81	Intermediate Similarity	NPC474012
0.81	Intermediate Similarity	NPC477721
0.81	Intermediate Similarity	NPC251680
0.8095	Intermediate Similarity	NPC316708
0.8085	Intermediate Similarity	NPC471796
0.8085	Intermediate Similarity	NPC473891
0.8085	Intermediate Similarity	NPC471779
0.8081	Intermediate Similarity	NPC477718
0.8081	Intermediate Similarity	NPC98112
0.8081	Intermediate Similarity	NPC477719
0.8081	Intermediate Similarity	NPC472188
0.8081	Intermediate Similarity	NPC91695
0.8081	Intermediate Similarity	NPC120446
0.8081	Intermediate Similarity	NPC70145
0.8077	Intermediate Similarity	NPC217921
0.8077	Intermediate Similarity	NPC128795
0.8077	Intermediate Similarity	NPC300614
0.8077	Intermediate Similarity	NPC311223
0.8077	Intermediate Similarity	NPC306265
0.8077	Intermediate Similarity	NPC135015
0.8077	Intermediate Similarity	NPC50124
0.8077	Intermediate Similarity	NPC48548
0.8077	Intermediate Similarity	NPC90946
0.8065	Intermediate Similarity	NPC119001
0.8065	Intermediate Similarity	NPC42586
0.8065	Intermediate Similarity	NPC473251
0.8061	Intermediate Similarity	NPC471786
0.8061	Intermediate Similarity	NPC472189
0.8061	Intermediate Similarity	NPC37603
0.8061	Intermediate Similarity	NPC471372

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 NPC165632 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1497
0.2-0.3	3657
0.3-0.4	2439
0.4-0.5	967
0.5-0.6	260
0.6-0.7	156
0.7-0.8	13
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
0.81	Intermediate Similarity	NPD7639	Approved
0.81	Intermediate Similarity	NPD7640	Approved
0.8	Intermediate Similarity	NPD7638	Approved
0.8	Intermediate Similarity	NPD4225	Approved
0.7766	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6686	Approved
0.767	Intermediate Similarity	NPD5344	Discontinued
0.7664	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD7328	Approved
0.7589	Intermediate Similarity	NPD7327	Approved
0.7522	Intermediate Similarity	NPD7516	Approved
0.7431	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7632	Discontinued
0.7404	Intermediate Similarity	NPD6648	Approved
0.7391	Intermediate Similarity	NPD8033	Approved
0.7391	Intermediate Similarity	NPD8379	Approved
0.7391	Intermediate Similarity	NPD8380	Approved
0.7391	Intermediate Similarity	NPD8378	Approved
0.7391	Intermediate Similarity	NPD8296	Approved
0.7391	Intermediate Similarity	NPD8335	Approved
0.7304	Intermediate Similarity	NPD8294	Approved
0.7304	Intermediate Similarity	NPD8377	Approved
0.7228	Intermediate Similarity	NPD7637	Suspended
0.7188	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7507	Approved
0.7107	Intermediate Similarity	NPD7319	Approved
0.7094	Intermediate Similarity	NPD7503	Approved
0.7043	Intermediate Similarity	NPD7115	Discovery
0.7041	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5778	Approved
0.699	Remote Similarity	NPD5779	Approved
0.6981	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1694	Approved
0.6961	Remote Similarity	NPD6698	Approved
0.6961	Remote Similarity	NPD46	Approved
0.6961	Remote Similarity	NPD7838	Discovery
0.6939	Remote Similarity	NPD6695	Phase 3
0.6923	Remote Similarity	NPD7748	Approved
0.6909	Remote Similarity	NPD6675	Approved
0.6909	Remote Similarity	NPD7128	Approved
0.6909	Remote Similarity	NPD6402	Approved
0.6909	Remote Similarity	NPD5739	Approved
0.6893	Remote Similarity	NPD7515	Phase 2
0.6887	Remote Similarity	NPD7902	Approved
0.6847	Remote Similarity	NPD5697	Approved
0.6847	Remote Similarity	NPD5701	Approved
0.6847	Remote Similarity	NPD6412	Phase 2
0.6842	Remote Similarity	NPD6053	Discontinued
0.6842	Remote Similarity	NPD6882	Approved
0.6827	Remote Similarity	NPD6399	Phase 3
0.6786	Remote Similarity	NPD7320	Approved
0.6786	Remote Similarity	NPD6899	Approved
0.6786	Remote Similarity	NPD6881	Approved
0.6757	Remote Similarity	NPD6008	Approved
0.6752	Remote Similarity	NPD6009	Approved
0.6733	Remote Similarity	NPD3618	Phase 1
0.6726	Remote Similarity	NPD6014	Approved
0.6726	Remote Similarity	NPD6373	Approved
0.6726	Remote Similarity	NPD6013	Approved
0.6726	Remote Similarity	NPD6372	Approved
0.6726	Remote Similarity	NPD6012	Approved
0.6701	Remote Similarity	NPD6929	Approved
0.6698	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6371	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6639	Remote Similarity	NPD7492	Approved
0.6638	Remote Similarity	NPD4632	Approved
0.6637	Remote Similarity	NPD6011	Approved
0.6636	Remote Similarity	NPD5211	Phase 2
0.6633	Remote Similarity	NPD6930	Phase 2
0.6633	Remote Similarity	NPD6931	Approved
0.6609	Remote Similarity	NPD6847	Approved
0.6609	Remote Similarity	NPD6649	Approved
0.6609	Remote Similarity	NPD6869	Approved
0.6609	Remote Similarity	NPD6650	Approved
0.6609	Remote Similarity	NPD6617	Approved
0.6609	Remote Similarity	NPD8130	Phase 1
0.6604	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7900	Approved
0.6585	Remote Similarity	NPD6616	Approved
0.6583	Remote Similarity	NPD6319	Approved
0.6583	Remote Similarity	NPD6059	Approved
0.6583	Remote Similarity	NPD6054	Approved
0.6579	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4755	Approved
0.6574	Remote Similarity	NPD6083	Phase 2
0.6574	Remote Similarity	NPD6084	Phase 2
0.6571	Remote Similarity	NPD6411	Approved
0.6569	Remote Similarity	NPD4249	Approved
0.6557	Remote Similarity	NPD8328	Phase 3
0.6552	Remote Similarity	NPD8297	Approved
0.6542	Remote Similarity	NPD5695	Phase 3
0.6538	Remote Similarity	NPD6051	Approved
0.6538	Remote Similarity	NPD5328	Approved
0.6532	Remote Similarity	NPD8293	Discontinued
0.6532	Remote Similarity	NPD7078	Approved
0.6531	Remote Similarity	NPD7645	Phase 2
0.6529	Remote Similarity	NPD6015	Approved
0.6529	Remote Similarity	NPD8516	Approved
0.6529	Remote Similarity	NPD6016	Approved
0.6529	Remote Similarity	NPD8517	Approved
0.6529	Remote Similarity	NPD8515	Approved
0.6529	Remote Similarity	NPD8513	Phase 3
0.6518	Remote Similarity	NPD5141	Approved
0.6509	Remote Similarity	NPD4202	Approved
0.6505	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4250	Approved
0.6505	Remote Similarity	NPD4251	Approved
0.65	Remote Similarity	NPD3667	Approved
0.6496	Remote Similarity	NPD8133	Approved
0.6495	Remote Similarity	NPD6925	Approved
0.6495	Remote Similarity	NPD5776	Phase 2
0.6491	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.648	Remote Similarity	NPD7736	Approved
0.6476	Remote Similarity	NPD3168	Discontinued
0.6476	Remote Similarity	NPD5785	Approved
0.6475	Remote Similarity	NPD6370	Approved
0.6475	Remote Similarity	NPD5988	Approved
0.6466	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7525	Registered
0.6465	Remote Similarity	NPD7332	Phase 2
0.6465	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7514	Phase 3
0.6458	Remote Similarity	NPD8264	Approved
0.6455	Remote Similarity	NPD5286	Approved
0.6455	Remote Similarity	NPD4700	Approved
0.6455	Remote Similarity	NPD5285	Approved
0.6455	Remote Similarity	NPD4696	Approved
0.6429	Remote Similarity	NPD7145	Approved
0.6415	Remote Similarity	NPD6079	Approved
0.6415	Remote Similarity	NPD7087	Discontinued
0.6408	Remote Similarity	NPD7146	Approved
0.6408	Remote Similarity	NPD6409	Approved
0.6408	Remote Similarity	NPD7334	Approved
0.6408	Remote Similarity	NPD5330	Approved
0.6408	Remote Similarity	NPD7521	Approved
0.6408	Remote Similarity	NPD6684	Approved
0.64	Remote Similarity	NPD6902	Approved
0.6393	Remote Similarity	NPD5983	Phase 2
0.6392	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD6274	Approved
0.6381	Remote Similarity	NPD6101	Approved
0.6381	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD3133	Approved
0.6373	Remote Similarity	NPD4786	Approved
0.6373	Remote Similarity	NPD3665	Phase 1
0.6373	Remote Similarity	NPD3666	Approved
0.6364	Remote Similarity	NPD5696	Approved
0.6339	Remote Similarity	NPD5224	Approved
0.6339	Remote Similarity	NPD4633	Approved
0.6339	Remote Similarity	NPD5226	Approved
0.6339	Remote Similarity	NPD5225	Approved
0.6333	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.633	Remote Similarity	NPD5221	Approved
0.633	Remote Similarity	NPD5222	Approved
0.633	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.633	Remote Similarity	NPD4697	Phase 3
0.6311	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6893	Approved
0.6311	Remote Similarity	NPD1696	Phase 3
0.63	Remote Similarity	NPD4819	Approved
0.63	Remote Similarity	NPD4822	Approved
0.63	Remote Similarity	NPD4820	Approved
0.63	Remote Similarity	NPD4821	Approved
0.6296	Remote Similarity	NPD5282	Discontinued
0.629	Remote Similarity	NPD7604	Phase 2
0.629	Remote Similarity	NPD6067	Discontinued
0.6289	Remote Similarity	NPD7339	Approved
0.6289	Remote Similarity	NPD6942	Approved
0.6286	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6672	Approved
0.6286	Remote Similarity	NPD6903	Approved
0.6286	Remote Similarity	NPD5737	Approved
0.6283	Remote Similarity	NPD5175	Approved
0.6283	Remote Similarity	NPD5174	Approved
0.6275	Remote Similarity	NPD7154	Phase 3
0.6273	Remote Similarity	NPD5173	Approved
0.627	Remote Similarity	NPD8074	Phase 3
0.6263	Remote Similarity	NPD4271	Approved
0.6263	Remote Similarity	NPD4268	Approved
0.6262	Remote Similarity	NPD7983	Approved
0.6262	Remote Similarity	NPD8034	Phase 2
0.6262	Remote Similarity	NPD5693	Phase 1
0.6262	Remote Similarity	NPD8035	Phase 2
0.6261	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5279	Phase 3
0.625	Remote Similarity	NPD5223	Approved
0.6239	Remote Similarity	NPD4634	Approved
0.6238	Remote Similarity	NPD6898	Phase 1
0.623	Remote Similarity	NPD7100	Approved
0.623	Remote Similarity	NPD7101	Approved
0.6226	Remote Similarity	NPD4753	Phase 2
0.6226	Remote Similarity	NPD1695	Approved
0.6198	Remote Similarity	NPD6317	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