NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	284.16
Volume:	277.722
LogP:	2.96
LogD:	2.83
LogS:	-4.37
# Rotatable Bonds:	0
TPSA:	57.15
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.691
Synthetic Accessibility Score:	5.804
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.737
MDCK Permeability:	4.4125783460913226e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.177
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.233
Plasma Protein Binding (PPB):	74.54756927490234%
Volume Distribution (VD):	1.731
Pgp-substrate:	17.0441837310791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.927
CYP2C9-inhibitor:	0.025
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.788
CYP3A4-inhibitor:	0.055
CYP3A4-substrate:	0.47

ADMET: Excretion

Clearance (CL):	11.033
Half-life (T1/2):	0.658

ADMET: Toxicity

hERG Blockers:	0.696
Human Hepatotoxicity (H-HT):	0.978
Drug-inuced Liver Injury (DILI):	0.837
AMES Toxicity:	0.905
Rat Oral Acute Toxicity:	0.369
Maximum Recommended Daily Dose:	0.019
Skin Sensitization:	0.361
Carcinogencity:	0.556
Eye Corrosion:	0.016
Eye Irritation:	0.134
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC200167

Natural Product ID:	NPC200167
*Common Name:**	BJDCWCLMFKKGEE-FTRRWEDQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BJDCWCLMFKKGEE-FTRRWEDQSA-N
Standard InCHI:	InChI=1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11?,12+,13-,14-,15-/m1/s1
SMILES:	O[C@H]1O[C@@H]2O[C@@]3(C)CC[C@@H]4[C@]2(C([C@H]1C)CC[C@H]4C)OO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2103734
PubChem CID:	179336
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002440] Artemisinins

*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
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387056]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Potency	25

Activity Type	# Activity
Individual Protein	4
Others	21

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	94.4	nM	PMID[559482]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	41.1	nM	PMID[559482]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	535.4	nM	PubChem BioAssay data set
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	421.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	631.0	nM	PMID[559482]
NPT2	Others	Unspecified		Potency	n.a.	1258.9	nM	PMID[559482]
NPT2	Others	Unspecified		Potency	n.a.	46.9	nM	PMID[559482]
NPT2	Others	Unspecified		Potency	n.a.	7497.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	26832.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	15089	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2113.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	749.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	4946.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	13333.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	425.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	133.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	9520.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	11883.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	118.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	14960.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	47.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1678.5	nM	PubChem BioAssay data set

☑ 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 NPC200167 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	570
0.1-0.2	5212
0.2-0.3	14930
0.3-0.4	11554
0.4-0.5	5689
0.5-0.6	4044
0.6-0.7	657
0.7-0.8	20
0.8-0.85	6
0.85-0.9	4
0.9-0.95	3
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC53868
1.0	High Similarity	NPC209666
1.0	High Similarity	NPC31046
0.9275	High Similarity	NPC5209
0.9275	High Similarity	NPC51956
0.9275	High Similarity	NPC29005
0.859	High Similarity	NPC67158
0.859	High Similarity	NPC128816
0.859	High Similarity	NPC30102
0.8421	Intermediate Similarity	NPC177343
0.8133	Intermediate Similarity	NPC166250
0.8101	Intermediate Similarity	NPC285480
0.8101	Intermediate Similarity	NPC30443
0.8101	Intermediate Similarity	NPC260977
0.8101	Intermediate Similarity	NPC45256
0.7949	Intermediate Similarity	NPC272841
0.7901	Intermediate Similarity	NPC241959
0.7895	Intermediate Similarity	NPC308489
0.7733	Intermediate Similarity	NPC471879
0.7711	Intermediate Similarity	NPC290612
0.7692	Intermediate Similarity	NPC107963
0.7619	Intermediate Similarity	NPC471410
0.7619	Intermediate Similarity	NPC471411
0.7558	Intermediate Similarity	NPC131466
0.7531	Intermediate Similarity	NPC186588
0.7531	Intermediate Similarity	NPC60568
0.7529	Intermediate Similarity	NPC43912
0.7529	Intermediate Similarity	NPC140446
0.75	Intermediate Similarity	NPC477577
0.747	Intermediate Similarity	NPC470070
0.7412	Intermediate Similarity	NPC268633
0.7412	Intermediate Similarity	NPC107603
0.7407	Intermediate Similarity	NPC170595
0.7386	Intermediate Similarity	NPC229801
0.7386	Intermediate Similarity	NPC307167
0.7386	Intermediate Similarity	NPC210759
0.7381	Intermediate Similarity	NPC474156
0.7356	Intermediate Similarity	NPC82955
0.7333	Intermediate Similarity	NPC477759
0.7333	Intermediate Similarity	NPC179823
0.7333	Intermediate Similarity	NPC477758
0.7333	Intermediate Similarity	NPC477760
0.7333	Intermediate Similarity	NPC477754
0.7333	Intermediate Similarity	NPC477761
0.7326	Intermediate Similarity	NPC472396
0.7308	Intermediate Similarity	NPC470660
0.7308	Intermediate Similarity	NPC470659
0.7303	Intermediate Similarity	NPC18724
0.7303	Intermediate Similarity	NPC470623
0.7303	Intermediate Similarity	NPC171741
0.7303	Intermediate Similarity	NPC224003
0.7303	Intermediate Similarity	NPC323231
0.7273	Intermediate Similarity	NPC261990
0.7273	Intermediate Similarity	NPC474249
0.7273	Intermediate Similarity	NPC65550
0.7273	Intermediate Similarity	NPC279329
0.725	Intermediate Similarity	NPC279575
0.7241	Intermediate Similarity	NPC281004
0.7222	Intermediate Similarity	NPC252253
0.7222	Intermediate Similarity	NPC267238
0.7222	Intermediate Similarity	NPC253611
0.7222	Intermediate Similarity	NPC309866
0.7222	Intermediate Similarity	NPC148593
0.7222	Intermediate Similarity	NPC77717
0.7222	Intermediate Similarity	NPC305418
0.7222	Intermediate Similarity	NPC45959
0.7222	Intermediate Similarity	NPC471373
0.72	Intermediate Similarity	NPC477752
0.72	Intermediate Similarity	NPC477756
0.72	Intermediate Similarity	NPC477764
0.72	Intermediate Similarity	NPC477751
0.7191	Intermediate Similarity	NPC473830
0.7191	Intermediate Similarity	NPC289361
0.7191	Intermediate Similarity	NPC204881
0.7191	Intermediate Similarity	NPC59006
0.7191	Intermediate Similarity	NPC36372
0.7191	Intermediate Similarity	NPC293609
0.7176	Intermediate Similarity	NPC18953
0.7176	Intermediate Similarity	NPC166279
0.7159	Intermediate Similarity	NPC473472
0.7159	Intermediate Similarity	NPC102725
0.7143	Intermediate Similarity	NPC471424
0.7143	Intermediate Similarity	NPC94582
0.7143	Intermediate Similarity	NPC205129
0.7143	Intermediate Similarity	NPC92196
0.7143	Intermediate Similarity	NPC189575
0.7143	Intermediate Similarity	NPC106701
0.7143	Intermediate Similarity	NPC470611
0.7143	Intermediate Similarity	NPC477494
0.7143	Intermediate Similarity	NPC471429
0.7143	Intermediate Similarity	NPC471425
0.7143	Intermediate Similarity	NPC57964
0.7111	Intermediate Similarity	NPC172838
0.7111	Intermediate Similarity	NPC277774
0.7111	Intermediate Similarity	NPC167644
0.7111	Intermediate Similarity	NPC144790
0.7111	Intermediate Similarity	NPC149400
0.7111	Intermediate Similarity	NPC311246
0.7111	Intermediate Similarity	NPC137004
0.7111	Intermediate Similarity	NPC88962
0.7111	Intermediate Similarity	NPC473726
0.7089	Intermediate Similarity	NPC123122
0.7083	Intermediate Similarity	NPC185116
0.7079	Intermediate Similarity	NPC223143
0.7079	Intermediate Similarity	NPC473542
0.7065	Intermediate Similarity	NPC203434
0.7065	Intermediate Similarity	NPC142264
0.7065	Intermediate Similarity	NPC139271
0.7065	Intermediate Similarity	NPC476510
0.7065	Intermediate Similarity	NPC238796
0.7065	Intermediate Similarity	NPC304011
0.7065	Intermediate Similarity	NPC237071
0.7059	Intermediate Similarity	NPC474253
0.7059	Intermediate Similarity	NPC474346
0.7059	Intermediate Similarity	NPC474284
0.7059	Intermediate Similarity	NPC475820
0.7059	Intermediate Similarity	NPC213737
0.7045	Intermediate Similarity	NPC470872
0.7033	Intermediate Similarity	NPC312678
0.7033	Intermediate Similarity	NPC473774
0.7033	Intermediate Similarity	NPC178949
0.7033	Intermediate Similarity	NPC175
0.7033	Intermediate Similarity	NPC30687
0.7033	Intermediate Similarity	NPC253268
0.7033	Intermediate Similarity	NPC475436
0.7033	Intermediate Similarity	NPC473851
0.7033	Intermediate Similarity	NPC473503
0.7033	Intermediate Similarity	NPC24960
0.7033	Intermediate Similarity	NPC477224
0.7033	Intermediate Similarity	NPC191915
0.7033	Intermediate Similarity	NPC179859
0.7033	Intermediate Similarity	NPC113500
0.7033	Intermediate Similarity	NPC174024
0.7033	Intermediate Similarity	NPC151214
0.7033	Intermediate Similarity	NPC3538
0.7033	Intermediate Similarity	NPC131693
0.7033	Intermediate Similarity	NPC96736
0.7033	Intermediate Similarity	NPC291547
0.7011	Intermediate Similarity	NPC470836
0.7	Intermediate Similarity	NPC476668
0.7	Intermediate Similarity	NPC470151
0.7	Intermediate Similarity	NPC473637
0.7	Intermediate Similarity	NPC5632
0.7	Intermediate Similarity	NPC149966
0.6989	Remote Similarity	NPC477223
0.6989	Remote Similarity	NPC233649
0.6989	Remote Similarity	NPC477222
0.6989	Remote Similarity	NPC470028
0.6966	Remote Similarity	NPC20822
0.6957	Remote Similarity	NPC474399
0.6957	Remote Similarity	NPC473065
0.6957	Remote Similarity	NPC469710
0.6957	Remote Similarity	NPC473067
0.6957	Remote Similarity	NPC473064
0.6951	Remote Similarity	NPC476719
0.6951	Remote Similarity	NPC188793
0.6941	Remote Similarity	NPC2096
0.6941	Remote Similarity	NPC296734
0.6941	Remote Similarity	NPC208912
0.6932	Remote Similarity	NPC45833
0.6932	Remote Similarity	NPC62202
0.6932	Remote Similarity	NPC213658
0.6932	Remote Similarity	NPC161928
0.6932	Remote Similarity	NPC210658
0.6932	Remote Similarity	NPC110365
0.6923	Remote Similarity	NPC476669
0.6923	Remote Similarity	NPC234352
0.6923	Remote Similarity	NPC297348
0.6923	Remote Similarity	NPC249204
0.6923	Remote Similarity	NPC477451
0.6923	Remote Similarity	NPC177834
0.6923	Remote Similarity	NPC477547
0.6923	Remote Similarity	NPC141769
0.6923	Remote Similarity	NPC250393
0.6923	Remote Similarity	NPC325828
0.6923	Remote Similarity	NPC48339
0.6915	Remote Similarity	NPC471375
0.6915	Remote Similarity	NPC209798
0.6915	Remote Similarity	NPC471374
0.6914	Remote Similarity	NPC472950
0.6914	Remote Similarity	NPC472952
0.6905	Remote Similarity	NPC471216
0.6905	Remote Similarity	NPC471217
0.6897	Remote Similarity	NPC273290
0.6897	Remote Similarity	NPC232044
0.6897	Remote Similarity	NPC235402
0.6882	Remote Similarity	NPC252056
0.6882	Remote Similarity	NPC296936
0.6882	Remote Similarity	NPC473287
0.6882	Remote Similarity	NPC121453
0.6882	Remote Similarity	NPC148872
0.6882	Remote Similarity	NPC90583
0.6882	Remote Similarity	NPC472989
0.6854	Remote Similarity	NPC128475
0.6848	Remote Similarity	NPC222731
0.6848	Remote Similarity	NPC475325
0.6848	Remote Similarity	NPC217205
0.6848	Remote Similarity	NPC471464
0.6848	Remote Similarity	NPC305160
0.6848	Remote Similarity	NPC291203

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 NPC200167 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	601
0.1-0.2	4650
0.2-0.3	2840
0.3-0.4	626
0.4-0.5	333
0.5-0.6	86
0.6-0.7	5
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1811	Approved
1.0	High Similarity	NPD1810	Approved
0.9275	High Similarity	NPD2686	Approved
0.9275	High Similarity	NPD2254	Approved
0.9275	High Similarity	NPD2687	Approved
0.859	High Similarity	NPD3670	Clinical (unspecified phase)
0.859	High Similarity	NPD3669	Approved
0.8101	Intermediate Similarity	NPD1779	Approved
0.8101	Intermediate Similarity	NPD1780	Approved
0.7162	Intermediate Similarity	NPD371	Approved
0.6923	Remote Similarity	NPD8171	Discontinued
0.6706	Remote Similarity	NPD6928	Phase 2
0.6625	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.64	Remote Similarity	NPD3710	Phase 2
0.625	Remote Similarity	NPD890	Clinical (unspecified phase)
0.625	Remote Similarity	NPD892	Phase 3
0.625	Remote Similarity	NPD893	Approved
0.625	Remote Similarity	NPD891	Phase 3
0.625	Remote Similarity	NPD888	Phase 3
0.6238	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD385	Approved
0.6087	Remote Similarity	NPD384	Approved
0.6	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5972	Remote Similarity	NPD905	Approved
0.5972	Remote Similarity	NPD904	Phase 3
0.5942	Remote Similarity	NPD386	Approved
0.5942	Remote Similarity	NPD388	Approved
0.5926	Remote Similarity	NPD8133	Approved
0.5897	Remote Similarity	NPD6123	Approved
0.5811	Remote Similarity	NPD894	Approved
0.5811	Remote Similarity	NPD889	Approved
0.5811	Remote Similarity	NPD887	Approved
0.5811	Remote Similarity	NPD895	Approved
0.581	Remote Similarity	NPD6412	Phase 2
0.5789	Remote Similarity	NPD2267	Suspended
0.5766	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7991	Discontinued
0.5752	Remote Similarity	NPD8294	Approved
0.5752	Remote Similarity	NPD8377	Approved
0.5733	Remote Similarity	NPD7346	Approved
0.573	Remote Similarity	NPD6114	Approved
0.573	Remote Similarity	NPD6115	Approved
0.573	Remote Similarity	NPD6118	Approved
0.573	Remote Similarity	NPD6697	Approved
0.5714	Remote Similarity	NPD7327	Approved
0.5714	Remote Similarity	NPD7328	Approved
0.5702	Remote Similarity	NPD8379	Approved
0.5702	Remote Similarity	NPD8378	Approved
0.5702	Remote Similarity	NPD8033	Approved
0.5702	Remote Similarity	NPD8335	Approved
0.5702	Remote Similarity	NPD8380	Approved
0.5702	Remote Similarity	NPD8296	Approved
0.5696	Remote Similarity	NPD1145	Discontinued
0.5676	Remote Similarity	NPD2269	Approved
0.5664	Remote Similarity	NPD7516	Approved
0.5652	Remote Similarity	NPD367	Approved
0.5618	Remote Similarity	NPD6116	Phase 1
0.5607	Remote Similarity	NPD6686	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