NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	334.14
Volume:	327.854
LogP:	0.974
LogD:	0.366
LogS:	-3.223
# Rotatable Bonds:	1
TPSA:	96.97
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	4.869
Fsp3:	0.667
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:	-5.306
MDCK Permeability:	1.862440876720939e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.951
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.139
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	45.49391174316406%
Volume Distribution (VD):	0.578
Pgp-substrate:	31.550199508666992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.829
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.8
CYP2C9-inhibitor:	0.012
CYP2C9-substrate:	0.241
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.192
CYP3A4-inhibitor:	0.058
CYP3A4-substrate:	0.418

ADMET: Excretion

Clearance (CL):	5.851
Half-life (T1/2):	0.354

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.614
Drug-inuced Liver Injury (DILI):	0.17
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.586
Maximum Recommended Daily Dose:	0.659
Skin Sensitization:	0.127
Carcinogencity:	0.672
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.666

Download Data

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

Natural Product: NPC478211

Natural Product ID:	NPC478211
*Common Name:**	15-Hydroxynagilactone L
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JQEZXXRPUSQBOK-XZBNMAPWSA-N
Standard InCHI:	InChI=1S/C18H22O6/c1-8(19)14-9-6-11-15-17(2,16(22)23-11)5-4-12(20)18(15,3)10(9)7-13(21)24-14/h7-8,11-12,15,19-20H,4-6H2,1-3H3/t8?,11?,12?,15?,17-,18-/m0/s1
SMILES:	CC(O)C1=C2CC3OC(=O)[C@@]4(C)CCC(O)[C@](C)(C2=CC(=O)O1)C34
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds]

*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
NPO33703	Podocarpus nagi	Species	Podocarpaceae	Eukaryota	Seeds	Aihua, Lincang, Yunnan Province, China	2103-OCT	PMID[28719204]

☑ 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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC478211 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	326
0.1-0.2	1245
0.2-0.3	2745
0.3-0.4	5281
0.4-0.5	10475
0.5-0.6	8366
0.6-0.7	7945
0.7-0.8	6042
0.8-0.85	240
0.85-0.9	28
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9902	High Similarity	NPC100329
0.9902	High Similarity	NPC132790
0.9902	High Similarity	NPC247031
0.9902	High Similarity	NPC97939
0.9712	High Similarity	NPC475966
0.9706	High Similarity	NPC478210
0.9604	High Similarity	NPC478208
0.9528	High Similarity	NPC478216
0.9352	High Similarity	NPC478206
0.9352	High Similarity	NPC108581
0.9352	High Similarity	NPC478205
0.934	High Similarity	NPC478212
0.9259	High Similarity	NPC478204
0.9238	High Similarity	NPC478209
0.9038	High Similarity	NPC469607
0.8796	High Similarity	NPC474846
0.8796	High Similarity	NPC469656
0.8796	High Similarity	NPC188738
0.8796	High Similarity	NPC469655
0.875	High Similarity	NPC273005
0.875	High Similarity	NPC31058
0.875	High Similarity	NPC469606
0.8739	High Similarity	NPC98249
0.8739	High Similarity	NPC53396
0.8716	High Similarity	NPC269530
0.8661	High Similarity	NPC284707
0.8598	High Similarity	NPC230541
0.8571	High Similarity	NPC295791
0.8571	High Similarity	NPC13713
0.8571	High Similarity	NPC58662
0.8545	High Similarity	NPC472002
0.8519	High Similarity	NPC275539
0.8519	High Similarity	NPC189075
0.8505	High Similarity	NPC102352
0.8468	Intermediate Similarity	NPC469496
0.8468	Intermediate Similarity	NPC25909
0.8468	Intermediate Similarity	NPC469454
0.8468	Intermediate Similarity	NPC469463
0.8455	Intermediate Similarity	NPC304180
0.8455	Intermediate Similarity	NPC179798
0.844	Intermediate Similarity	NPC141350
0.8426	Intermediate Similarity	NPC187435
0.8426	Intermediate Similarity	NPC180744
0.8426	Intermediate Similarity	NPC67321
0.8426	Intermediate Similarity	NPC3316
0.8426	Intermediate Similarity	NPC110496
0.8426	Intermediate Similarity	NPC144854
0.8421	Intermediate Similarity	NPC475041
0.8407	Intermediate Similarity	NPC473968
0.8407	Intermediate Similarity	NPC469684
0.8396	Intermediate Similarity	NPC235369
0.839	Intermediate Similarity	NPC478207
0.8365	Intermediate Similarity	NPC474343
0.8364	Intermediate Similarity	NPC5103
0.8364	Intermediate Similarity	NPC210005
0.8364	Intermediate Similarity	NPC286880
0.8349	Intermediate Similarity	NPC154608
0.8349	Intermediate Similarity	NPC192813
0.8349	Intermediate Similarity	NPC277017
0.8333	Intermediate Similarity	NPC34768
0.8333	Intermediate Similarity	NPC127609
0.8318	Intermediate Similarity	NPC159533
0.8305	Intermediate Similarity	NPC477745
0.8304	Intermediate Similarity	NPC471204
0.8304	Intermediate Similarity	NPC56448
0.8302	Intermediate Similarity	NPC303559
0.8273	Intermediate Similarity	NPC143706
0.8273	Intermediate Similarity	NPC472534
0.8257	Intermediate Similarity	NPC302788
0.8252	Intermediate Similarity	NPC57117
0.8241	Intermediate Similarity	NPC146731
0.8241	Intermediate Similarity	NPC258532
0.8241	Intermediate Similarity	NPC296950
0.8235	Intermediate Similarity	NPC476008
0.8214	Intermediate Similarity	NPC194951
0.8214	Intermediate Similarity	NPC12046
0.8208	Intermediate Similarity	NPC47024
0.8205	Intermediate Similarity	NPC269642
0.8182	Intermediate Similarity	NPC50124
0.8182	Intermediate Similarity	NPC306265
0.8165	Intermediate Similarity	NPC181357
0.8148	Intermediate Similarity	NPC254202
0.8148	Intermediate Similarity	NPC99266
0.8142	Intermediate Similarity	NPC51978
0.8142	Intermediate Similarity	NPC157441
0.8142	Intermediate Similarity	NPC474271
0.8136	Intermediate Similarity	NPC67251
0.8136	Intermediate Similarity	NPC469789
0.8131	Intermediate Similarity	NPC471412
0.8113	Intermediate Similarity	NPC159763
0.8113	Intermediate Similarity	NPC278386
0.8113	Intermediate Similarity	NPC23364
0.8113	Intermediate Similarity	NPC124512
0.8108	Intermediate Similarity	NPC474243
0.8108	Intermediate Similarity	NPC469370
0.8103	Intermediate Similarity	NPC230513
0.8103	Intermediate Similarity	NPC475775
0.8103	Intermediate Similarity	NPC476529
0.8095	Intermediate Similarity	NPC134072
0.8095	Intermediate Similarity	NPC234993
0.8095	Intermediate Similarity	NPC256227
0.8091	Intermediate Similarity	NPC179380
0.8091	Intermediate Similarity	NPC133422
0.8087	Intermediate Similarity	NPC284068
0.8087	Intermediate Similarity	NPC473590
0.8087	Intermediate Similarity	NPC23046
0.8077	Intermediate Similarity	NPC250075
0.807	Intermediate Similarity	NPC117712
0.8067	Intermediate Similarity	NPC476729
0.8067	Intermediate Similarity	NPC8369
0.8067	Intermediate Similarity	NPC24651
0.8056	Intermediate Similarity	NPC165250
0.8056	Intermediate Similarity	NPC162973
0.8056	Intermediate Similarity	NPC476081
0.8056	Intermediate Similarity	NPC137430
0.8053	Intermediate Similarity	NPC222834
0.8053	Intermediate Similarity	NPC302146
0.8053	Intermediate Similarity	NPC476801
0.8051	Intermediate Similarity	NPC312833
0.8037	Intermediate Similarity	NPC471413
0.8037	Intermediate Similarity	NPC476767
0.8036	Intermediate Similarity	NPC235014
0.8036	Intermediate Similarity	NPC253906
0.8034	Intermediate Similarity	NPC109607
0.8034	Intermediate Similarity	NPC107338
0.8034	Intermediate Similarity	NPC478051
0.8034	Intermediate Similarity	NPC268530
0.8034	Intermediate Similarity	NPC154491
0.8018	Intermediate Similarity	NPC88701
0.8018	Intermediate Similarity	NPC37628
0.8	Intermediate Similarity	NPC478052
0.8	Intermediate Similarity	NPC266728
0.8	Intermediate Similarity	NPC266570
0.8	Intermediate Similarity	NPC477125
0.8	Intermediate Similarity	NPC474734
0.8	Intermediate Similarity	NPC49492
0.8	Intermediate Similarity	NPC293112
0.8	Intermediate Similarity	NPC179626
0.8	Intermediate Similarity	NPC159499
0.8	Intermediate Similarity	NPC176840
0.7983	Intermediate Similarity	NPC105926
0.7983	Intermediate Similarity	NPC91693
0.7983	Intermediate Similarity	NPC18945
0.7983	Intermediate Similarity	NPC265557
0.7982	Intermediate Similarity	NPC8196
0.7982	Intermediate Similarity	NPC962
0.7982	Intermediate Similarity	NPC49451
0.7982	Intermediate Similarity	NPC264153
0.7982	Intermediate Similarity	NPC250109
0.7982	Intermediate Similarity	NPC471208
0.7981	Intermediate Similarity	NPC53555
0.7966	Intermediate Similarity	NPC159456
0.7966	Intermediate Similarity	NPC4021
0.7966	Intermediate Similarity	NPC67569
0.7965	Intermediate Similarity	NPC475668
0.7965	Intermediate Similarity	NPC473921
0.7965	Intermediate Similarity	NPC475480
0.7965	Intermediate Similarity	NPC201992
0.7963	Intermediate Similarity	NPC472637
0.7963	Intermediate Similarity	NPC81530
0.7963	Intermediate Similarity	NPC97435
0.7949	Intermediate Similarity	NPC268958
0.7949	Intermediate Similarity	NPC305260
0.7949	Intermediate Similarity	NPC42673
0.7949	Intermediate Similarity	NPC270850
0.7949	Intermediate Similarity	NPC122971
0.7946	Intermediate Similarity	NPC153239
0.7946	Intermediate Similarity	NPC27814
0.7946	Intermediate Similarity	NPC273433
0.7946	Intermediate Similarity	NPC137911
0.7946	Intermediate Similarity	NPC228477
0.7944	Intermediate Similarity	NPC216478
0.7931	Intermediate Similarity	NPC176513
0.7931	Intermediate Similarity	NPC470775
0.7931	Intermediate Similarity	NPC55296
0.7928	Intermediate Similarity	NPC143609
0.7928	Intermediate Similarity	NPC78966
0.7928	Intermediate Similarity	NPC284732
0.7925	Intermediate Similarity	NPC473153
0.7917	Intermediate Similarity	NPC172154
0.7917	Intermediate Similarity	NPC470922
0.7917	Intermediate Similarity	NPC81736
0.7913	Intermediate Similarity	NPC469877
0.7913	Intermediate Similarity	NPC470919
0.7913	Intermediate Similarity	NPC474181
0.7905	Intermediate Similarity	NPC470957
0.7905	Intermediate Similarity	NPC470958
0.7899	Intermediate Similarity	NPC23786
0.7899	Intermediate Similarity	NPC470265
0.7899	Intermediate Similarity	NPC287236
0.7895	Intermediate Similarity	NPC11252
0.7895	Intermediate Similarity	NPC474516
0.7895	Intermediate Similarity	NPC470063
0.7895	Intermediate Similarity	NPC126691
0.7895	Intermediate Similarity	NPC289312
0.7895	Intermediate Similarity	NPC236217
0.789	Intermediate Similarity	NPC58329
0.789	Intermediate Similarity	NPC136289
0.7885	Intermediate Similarity	NPC72845
0.7881	Intermediate Similarity	NPC475003

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 NPC478211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	796
0.2-0.3	1713
0.3-0.4	2518
0.4-0.5	2163
0.5-0.6	1136
0.6-0.7	438
0.7-0.8	104
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8113	Intermediate Similarity	NPD4225	Approved
0.787	Intermediate Similarity	NPD7639	Approved
0.787	Intermediate Similarity	NPD7640	Approved
0.7788	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7638	Approved
0.7699	Intermediate Similarity	NPD6686	Approved
0.7627	Intermediate Similarity	NPD7115	Discovery
0.7565	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7507	Approved
0.7411	Intermediate Similarity	NPD7632	Discontinued
0.7391	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8513	Phase 3
0.7373	Intermediate Similarity	NPD4632	Approved
0.7368	Intermediate Similarity	NPD6008	Approved
0.7304	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6053	Discontinued
0.7244	Intermediate Similarity	NPD7319	Approved
0.7236	Intermediate Similarity	NPD8515	Approved
0.7236	Intermediate Similarity	NPD7503	Approved
0.7236	Intermediate Similarity	NPD8517	Approved
0.7236	Intermediate Similarity	NPD8516	Approved
0.7156	Intermediate Similarity	NPD5779	Approved
0.7156	Intermediate Similarity	NPD5778	Approved
0.7154	Intermediate Similarity	NPD6319	Approved
0.713	Intermediate Similarity	NPD46	Approved
0.713	Intermediate Similarity	NPD6698	Approved
0.7069	Intermediate Similarity	NPD7128	Approved
0.7069	Intermediate Similarity	NPD5739	Approved
0.7069	Intermediate Similarity	NPD6675	Approved
0.7069	Intermediate Similarity	NPD6402	Approved
0.7064	Intermediate Similarity	NPD7983	Approved
0.7054	Intermediate Similarity	NPD7902	Approved
0.7049	Intermediate Similarity	NPD6009	Approved
0.7034	Intermediate Similarity	NPD6372	Approved
0.7034	Intermediate Similarity	NPD6373	Approved
0.7019	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5344	Discontinued
0.7009	Intermediate Similarity	NPD5697	Approved
0.7009	Intermediate Similarity	NPD5701	Approved
0.7	Intermediate Similarity	NPD8297	Approved
0.7	Intermediate Similarity	NPD7260	Phase 2
0.7	Intermediate Similarity	NPD6399	Phase 3
0.6984	Remote Similarity	NPD8328	Phase 3
0.6981	Remote Similarity	NPD1694	Approved
0.6975	Remote Similarity	NPD6371	Approved
0.696	Remote Similarity	NPD5983	Phase 2
0.6953	Remote Similarity	NPD8074	Phase 3
0.6949	Remote Similarity	NPD7320	Approved
0.6949	Remote Similarity	NPD6881	Approved
0.6949	Remote Similarity	NPD6899	Approved
0.6949	Remote Similarity	NPD6011	Approved
0.6947	Remote Similarity	NPD6845	Suspended
0.6937	Remote Similarity	NPD7748	Approved
0.693	Remote Similarity	NPD6648	Approved
0.6929	Remote Similarity	NPD7492	Approved
0.6917	Remote Similarity	NPD6650	Approved
0.6917	Remote Similarity	NPD6649	Approved
0.6917	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD3618	Phase 1
0.6911	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7515	Phase 2
0.6909	Remote Similarity	NPD6411	Approved
0.6891	Remote Similarity	NPD6012	Approved
0.6891	Remote Similarity	NPD6014	Approved
0.6891	Remote Similarity	NPD6013	Approved
0.6891	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5328	Approved
0.688	Remote Similarity	NPD6054	Approved
0.688	Remote Similarity	NPD6059	Approved
0.6875	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6616	Approved
0.6864	Remote Similarity	NPD6412	Phase 2
0.6855	Remote Similarity	NPD7327	Approved
0.6855	Remote Similarity	NPD7328	Approved
0.685	Remote Similarity	NPD7604	Phase 2
0.6842	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7290	Approved
0.6833	Remote Similarity	NPD7102	Approved
0.6833	Remote Similarity	NPD6883	Approved
0.6825	Remote Similarity	NPD8033	Approved
0.6825	Remote Similarity	NPD6016	Approved
0.6825	Remote Similarity	NPD6015	Approved
0.6822	Remote Similarity	NPD8293	Discontinued
0.6822	Remote Similarity	NPD7078	Approved
0.6818	Remote Similarity	NPD7838	Discovery
0.6814	Remote Similarity	NPD4697	Phase 3
0.681	Remote Similarity	NPD5211	Phase 2
0.68	Remote Similarity	NPD7516	Approved
0.6786	Remote Similarity	NPD7900	Approved
0.6786	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD8130	Phase 1
0.6777	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6869	Approved
0.6777	Remote Similarity	NPD6617	Approved
0.6777	Remote Similarity	NPD6847	Approved
0.6772	Remote Similarity	NPD5988	Approved
0.6772	Remote Similarity	NPD6370	Approved
0.6769	Remote Similarity	NPD7736	Approved
0.6757	Remote Similarity	NPD6079	Approved
0.6757	Remote Similarity	NPD7637	Suspended
0.6754	Remote Similarity	NPD4755	Approved
0.6746	Remote Similarity	NPD8377	Approved
0.6746	Remote Similarity	NPD8294	Approved
0.6744	Remote Similarity	NPD6336	Discontinued
0.6727	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6101	Approved
0.6723	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6882	Approved
0.6695	Remote Similarity	NPD5141	Approved
0.6694	Remote Similarity	NPD4634	Approved
0.6693	Remote Similarity	NPD8335	Approved
0.6693	Remote Similarity	NPD6921	Approved
0.6693	Remote Similarity	NPD8380	Approved
0.6693	Remote Similarity	NPD8296	Approved
0.6693	Remote Similarity	NPD8379	Approved
0.6693	Remote Similarity	NPD8378	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5221	Approved
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD5222	Approved
0.6638	Remote Similarity	NPD4696	Approved
0.6638	Remote Similarity	NPD5285	Approved
0.6638	Remote Similarity	NPD5286	Approved
0.6638	Remote Similarity	NPD4700	Approved
0.6637	Remote Similarity	NPD5282	Discontinued
0.6609	Remote Similarity	NPD5173	Approved
0.6607	Remote Similarity	NPD8035	Phase 2
0.6607	Remote Similarity	NPD8034	Phase 2
0.6581	Remote Similarity	NPD5223	Approved
0.6577	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6274	Approved
0.6549	Remote Similarity	NPD4202	Approved
0.6545	Remote Similarity	NPD7524	Approved
0.6545	Remote Similarity	NPD3573	Approved
0.6542	Remote Similarity	NPD3667	Approved
0.6525	Remote Similarity	NPD5225	Approved
0.6525	Remote Similarity	NPD5224	Approved
0.6525	Remote Similarity	NPD5226	Approved
0.6525	Remote Similarity	NPD4633	Approved
0.6518	Remote Similarity	NPD5785	Approved
0.6515	Remote Similarity	NPD6033	Approved
0.6514	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6317	Approved
0.6471	Remote Similarity	NPD4754	Approved
0.6471	Remote Similarity	NPD5174	Approved
0.6471	Remote Similarity	NPD5175	Approved
0.6466	Remote Similarity	NPD6083	Phase 2
0.6466	Remote Similarity	NPD6084	Phase 2
0.6462	Remote Similarity	NPD6067	Discontinued
0.646	Remote Similarity	NPD5281	Approved
0.646	Remote Similarity	NPD5284	Approved
0.6457	Remote Similarity	NPD6335	Approved
0.6457	Remote Similarity	NPD6314	Approved
0.6457	Remote Similarity	NPD6313	Approved
0.6455	Remote Similarity	NPD7521	Approved
0.6455	Remote Similarity	NPD5330	Approved
0.6455	Remote Similarity	NPD6684	Approved
0.6455	Remote Similarity	NPD7146	Approved
0.6455	Remote Similarity	NPD7334	Approved
0.6455	Remote Similarity	NPD5279	Phase 3
0.6455	Remote Similarity	NPD6409	Approved
0.6455	Remote Similarity	NPD4249	Approved
0.6435	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6868	Approved
0.6422	Remote Similarity	NPD3665	Phase 1
0.6422	Remote Similarity	NPD3666	Approved
0.6422	Remote Similarity	NPD3133	Approved
0.6422	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4786	Approved
0.641	Remote Similarity	NPD5696	Approved
0.6406	Remote Similarity	NPD7101	Approved
0.6406	Remote Similarity	NPD7100	Approved
0.6396	Remote Similarity	NPD4250	Approved
0.6396	Remote Similarity	NPD4251	Approved
0.6364	Remote Similarity	NPD4767	Approved
0.6364	Remote Similarity	NPD4768	Approved
0.6364	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD4695	Discontinued
0.6339	Remote Similarity	NPD6903	Approved
0.6339	Remote Similarity	NPD6672	Approved
0.6339	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5737	Approved
0.633	Remote Similarity	NPD7154	Phase 3
0.633	Remote Similarity	NPD6110	Phase 1
0.633	Remote Similarity	NPD6695	Phase 3
0.6316	Remote Similarity	NPD5693	Phase 1
0.6308	Remote Similarity	NPD6909	Approved
0.6308	Remote Similarity	NPD6908	Approved
0.6306	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5695	Phase 3
0.6273	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.626	Remote Similarity	NPD5128	Approved
0.626	Remote Similarity	NPD4730	Approved
0.626	Remote Similarity	NPD4729	Approved
0.6259	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7839	Suspended
0.6228	Remote Similarity	NPD5207	Approved
0.6216	Remote Similarity	NPD1696	Phase 3
0.6207	Remote Similarity	NPD4628	Phase 3

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