NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	262.12
Volume:	261.022
LogP:	1.624
LogD:	1.484
LogS:	-3.991
# Rotatable Bonds:	0
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	5.705
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.708
MDCK Permeability:	1.540606353955809e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.089
20% Bioavailability (F20%):	0.384
30% Bioavailability (F30%):	0.181

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.679
Plasma Protein Binding (PPB):	60.78575134277344%
Volume Distribution (VD):	1.182
Pgp-substrate:	45.39647674560547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.237
CYP1A2-substrate:	0.463
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.657
CYP2C9-inhibitor:	0.054
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.249
CYP3A4-inhibitor:	0.176
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	6.076
Half-life (T1/2):	0.533

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.594
Drug-inuced Liver Injury (DILI):	0.457
AMES Toxicity:	0.587
Rat Oral Acute Toxicity:	0.921
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.917
Carcinogencity:	0.512
Eye Corrosion:	0.656
Eye Irritation:	0.886
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC124881

Natural Product ID:	NPC124881
*Common Name:**	Saharanolide A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LDGHSQJVMCMJNB-MDFWMIKMSA-N
Standard InCHI:	InChI=1S/C15H18O4/c1-7-4-5-9-8(2)13(16)18-11(9)12-14(3)6-10(19-14)15(7,12)17/h4,9-12,17H,2,5-6H2,1,3H3/t9-,10-,11+,12-,14+,15+/m0/s1
SMILES:	CC1=CC[C@H]2C(=C)C(=O)O[C@H]2[C@H]2[C@@]3(C)C[C@@H]([C@]12O)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459916
PubChem CID:	44566953
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:0001770] Guaianolides 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
NPO17270	Warionia saharae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975493]
NPO17270	Warionia saharae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17270	Warionia saharae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17270	Warionia saharae	Species	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	3.3	ug.mL-1	PMID[475119]

☑ 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 NPC124881 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	264
0.1-0.2	1510
0.2-0.3	5757
0.3-0.4	14354
0.4-0.5	11436
0.5-0.6	6757
0.6-0.7	2230
0.7-0.8	370
0.8-0.85	7
0.85-0.9	8
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9479	High Similarity	NPC70865
0.9271	High Similarity	NPC181151
0.9062	High Similarity	NPC224689
0.899	High Similarity	NPC150923
0.898	High Similarity	NPC221615
0.8969	High Similarity	NPC213078
0.8878	High Similarity	NPC161493
0.8866	High Similarity	NPC170120
0.8866	High Similarity	NPC67584
0.8866	High Similarity	NPC52044
0.8763	High Similarity	NPC323008
0.8763	High Similarity	NPC470010
0.8763	High Similarity	NPC470013
0.8763	High Similarity	NPC262133
0.8763	High Similarity	NPC127019
0.8713	High Similarity	NPC86077
0.8673	High Similarity	NPC213698
0.866	High Similarity	NPC472874
0.8646	High Similarity	NPC301969
0.8646	High Similarity	NPC37607
0.8571	High Similarity	NPC198853
0.8485	Intermediate Similarity	NPC472873
0.8462	Intermediate Similarity	NPC243998
0.8462	Intermediate Similarity	NPC223450
0.8462	Intermediate Similarity	NPC54737
0.8416	Intermediate Similarity	NPC45125
0.8384	Intermediate Similarity	NPC477131
0.8367	Intermediate Similarity	NPC131209
0.8367	Intermediate Similarity	NPC133698
0.8365	Intermediate Similarity	NPC100487
0.8333	Intermediate Similarity	NPC471381
0.8333	Intermediate Similarity	NPC186861
0.8317	Intermediate Similarity	NPC471150
0.8302	Intermediate Similarity	NPC117604
0.8283	Intermediate Similarity	NPC475912
0.8283	Intermediate Similarity	NPC81419
0.8283	Intermediate Similarity	NPC179746
0.8283	Intermediate Similarity	NPC258216
0.8265	Intermediate Similarity	NPC216284
0.8247	Intermediate Similarity	NPC79549
0.8247	Intermediate Similarity	NPC91248
0.8235	Intermediate Similarity	NPC187268
0.8229	Intermediate Similarity	NPC67493
0.8224	Intermediate Similarity	NPC139838
0.8224	Intermediate Similarity	NPC59489
0.8208	Intermediate Similarity	NPC26617
0.8182	Intermediate Similarity	NPC208886
0.8182	Intermediate Similarity	NPC155215
0.8182	Intermediate Similarity	NPC12172
0.8163	Intermediate Similarity	NPC215556
0.8163	Intermediate Similarity	NPC473564
0.8119	Intermediate Similarity	NPC270013
0.8119	Intermediate Similarity	NPC14961
0.8119	Intermediate Similarity	NPC36954
0.8119	Intermediate Similarity	NPC304886
0.81	Intermediate Similarity	NPC476300
0.8081	Intermediate Similarity	NPC51004
0.8061	Intermediate Similarity	NPC224652
0.8039	Intermediate Similarity	NPC18019
0.8039	Intermediate Similarity	NPC24956
0.8021	Intermediate Similarity	NPC156485
0.802	Intermediate Similarity	NPC474035
0.802	Intermediate Similarity	NPC81386
0.802	Intermediate Similarity	NPC474338
0.8018	Intermediate Similarity	NPC121816
0.8	Intermediate Similarity	NPC30515
0.8	Intermediate Similarity	NPC258711
0.8	Intermediate Similarity	NPC184463
0.8	Intermediate Similarity	NPC95290
0.8	Intermediate Similarity	NPC475925
0.8	Intermediate Similarity	NPC35069
0.8	Intermediate Similarity	NPC189338
0.7982	Intermediate Similarity	NPC257240
0.798	Intermediate Similarity	NPC4986
0.798	Intermediate Similarity	NPC307411
0.7961	Intermediate Similarity	NPC474313
0.7961	Intermediate Similarity	NPC311904
0.7959	Intermediate Similarity	NPC190753
0.7941	Intermediate Similarity	NPC220221
0.7941	Intermediate Similarity	NPC476053
0.7938	Intermediate Similarity	NPC284534
0.7938	Intermediate Similarity	NPC204105
0.7938	Intermediate Similarity	NPC235792
0.7938	Intermediate Similarity	NPC300082
0.7938	Intermediate Similarity	NPC165162
0.7928	Intermediate Similarity	NPC273242
0.7921	Intermediate Similarity	NPC212486
0.7921	Intermediate Similarity	NPC135776
0.79	Intermediate Similarity	NPC129419
0.79	Intermediate Similarity	NPC476004
0.79	Intermediate Similarity	NPC474761
0.79	Intermediate Similarity	NPC35809
0.789	Intermediate Similarity	NPC477102
0.7885	Intermediate Similarity	NPC473326
0.7879	Intermediate Similarity	NPC217983
0.7879	Intermediate Similarity	NPC202672
0.7879	Intermediate Similarity	NPC207114
0.7864	Intermediate Similarity	NPC279621
0.7864	Intermediate Similarity	NPC476315
0.7857	Intermediate Similarity	NPC187661
0.7843	Intermediate Similarity	NPC303942
0.7843	Intermediate Similarity	NPC57405
0.7822	Intermediate Similarity	NPC63193
0.7822	Intermediate Similarity	NPC133888
0.7822	Intermediate Similarity	NPC35959
0.7822	Intermediate Similarity	NPC57304
0.7822	Intermediate Similarity	NPC293001
0.7822	Intermediate Similarity	NPC29821
0.7822	Intermediate Similarity	NPC171360
0.7822	Intermediate Similarity	NPC184063
0.7818	Intermediate Similarity	NPC477103
0.7812	Intermediate Similarity	NPC89555
0.78	Intermediate Similarity	NPC472872
0.78	Intermediate Similarity	NPC268298
0.78	Intermediate Similarity	NPC155935
0.7798	Intermediate Similarity	NPC308191
0.7788	Intermediate Similarity	NPC255450
0.7788	Intermediate Similarity	NPC170692
0.7778	Intermediate Similarity	NPC166115
0.7778	Intermediate Similarity	NPC44004
0.7778	Intermediate Similarity	NPC160138
0.7778	Intermediate Similarity	NPC186148
0.7778	Intermediate Similarity	NPC179891
0.7768	Intermediate Similarity	NPC46269
0.7768	Intermediate Similarity	NPC106395
0.7767	Intermediate Similarity	NPC469873
0.7767	Intermediate Similarity	NPC37408
0.7767	Intermediate Similarity	NPC163228
0.7757	Intermediate Similarity	NPC475871
0.7757	Intermediate Similarity	NPC475945
0.7748	Intermediate Similarity	NPC474750
0.7745	Intermediate Similarity	NPC125674
0.7745	Intermediate Similarity	NPC40821
0.7745	Intermediate Similarity	NPC32862
0.7745	Intermediate Similarity	NPC272293
0.7745	Intermediate Similarity	NPC228451
0.7745	Intermediate Similarity	NPC475838
0.7736	Intermediate Similarity	NPC474742
0.7732	Intermediate Similarity	NPC250315
0.7732	Intermediate Similarity	NPC245665
0.7727	Intermediate Similarity	NPC187876
0.7723	Intermediate Similarity	NPC19087
0.7723	Intermediate Similarity	NPC206614
0.7723	Intermediate Similarity	NPC54065
0.7723	Intermediate Similarity	NPC179394
0.7723	Intermediate Similarity	NPC475855
0.7723	Intermediate Similarity	NPC473448
0.7723	Intermediate Similarity	NPC144133
0.7723	Intermediate Similarity	NPC297474
0.7723	Intermediate Similarity	NPC474323
0.7719	Intermediate Similarity	NPC36754
0.77	Intermediate Similarity	NPC178875
0.77	Intermediate Similarity	NPC473715
0.77	Intermediate Similarity	NPC153805
0.77	Intermediate Similarity	NPC58219
0.77	Intermediate Similarity	NPC177629
0.7699	Intermediate Similarity	NPC133677
0.7699	Intermediate Similarity	NPC138303
0.7699	Intermediate Similarity	NPC67290
0.7692	Intermediate Similarity	NPC98165
0.7685	Intermediate Similarity	NPC203659
0.7685	Intermediate Similarity	NPC474741
0.7679	Intermediate Similarity	NPC126691
0.7679	Intermediate Similarity	NPC76550
0.7679	Intermediate Similarity	NPC123855
0.7679	Intermediate Similarity	NPC138757
0.7677	Intermediate Similarity	NPC107787
0.7677	Intermediate Similarity	NPC64153
0.767	Intermediate Similarity	NPC474247
0.7664	Intermediate Similarity	NPC474747
0.7653	Intermediate Similarity	NPC224386
0.7653	Intermediate Similarity	NPC191476
0.7653	Intermediate Similarity	NPC194859
0.7653	Intermediate Similarity	NPC472958
0.7653	Intermediate Similarity	NPC114979
0.7653	Intermediate Similarity	NPC472957
0.7652	Intermediate Similarity	NPC161060
0.7652	Intermediate Similarity	NPC475372
0.7647	Intermediate Similarity	NPC473321
0.7642	Intermediate Similarity	NPC288876
0.7636	Intermediate Similarity	NPC10150
0.7636	Intermediate Similarity	NPC68248
0.7632	Intermediate Similarity	NPC54739
0.7624	Intermediate Similarity	NPC92974
0.7624	Intermediate Similarity	NPC474032
0.7624	Intermediate Similarity	NPC212664
0.7624	Intermediate Similarity	NPC38392
0.7624	Intermediate Similarity	NPC32922
0.7624	Intermediate Similarity	NPC295312
0.7619	Intermediate Similarity	NPC108475
0.7619	Intermediate Similarity	NPC213947
0.7619	Intermediate Similarity	NPC170143
0.76	Intermediate Similarity	NPC118601
0.76	Intermediate Similarity	NPC231889
0.76	Intermediate Similarity	NPC237540
0.76	Intermediate Similarity	NPC24728
0.7596	Intermediate Similarity	NPC475659
0.7596	Intermediate Similarity	NPC471141
0.7593	Intermediate Similarity	NPC110989
0.7593	Intermediate Similarity	NPC474775

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 NPC124881 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	2161
0.2-0.3	3891
0.3-0.4	2091
0.4-0.5	481
0.5-0.6	229
0.6-0.7	32
0.7-0.8	6
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
0.8208	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD6371	Approved
0.798	Intermediate Similarity	NPD1695	Approved
0.7327	Intermediate Similarity	NPD4249	Approved
0.7255	Intermediate Similarity	NPD4251	Approved
0.7255	Intermediate Similarity	NPD4250	Approved
0.7228	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6053	Discontinued
0.7212	Intermediate Similarity	NPD46	Approved
0.7212	Intermediate Similarity	NPD6698	Approved
0.7103	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5362	Discontinued
0.69	Remote Similarity	NPD4819	Approved
0.69	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4820	Approved
0.69	Remote Similarity	NPD4822	Approved
0.69	Remote Similarity	NPD4821	Approved
0.6893	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7838	Discovery
0.6887	Remote Similarity	NPD5785	Approved
0.6863	Remote Similarity	NPD7154	Phase 3
0.6838	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD7983	Approved
0.6757	Remote Similarity	NPD4225	Approved
0.6731	Remote Similarity	NPD5363	Approved
0.6724	Remote Similarity	NPD6686	Approved
0.67	Remote Similarity	NPD4268	Approved
0.67	Remote Similarity	NPD4271	Approved
0.6637	Remote Similarity	NPD5344	Discontinued
0.6607	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6435	Approved
0.6602	Remote Similarity	NPD4269	Approved
0.6602	Remote Similarity	NPD4270	Approved
0.6557	Remote Similarity	NPD7115	Discovery
0.6545	Remote Similarity	NPD5282	Discontinued
0.6538	Remote Similarity	NPD5331	Approved
0.6538	Remote Similarity	NPD5332	Approved
0.6535	Remote Similarity	NPD7507	Approved
0.6509	Remote Similarity	NPD5786	Approved
0.6505	Remote Similarity	NPD5369	Approved
0.6505	Remote Similarity	NPD4790	Discontinued
0.641	Remote Similarity	NPD6008	Approved
0.6408	Remote Similarity	NPD5368	Approved
0.6408	Remote Similarity	NPD4252	Approved
0.6404	Remote Similarity	NPD6648	Approved
0.6404	Remote Similarity	NPD7640	Approved
0.6404	Remote Similarity	NPD7639	Approved
0.64	Remote Similarity	NPD6319	Approved
0.6385	Remote Similarity	NPD7319	Approved
0.6349	Remote Similarity	NPD8033	Approved
0.6349	Remote Similarity	NPD8513	Phase 3
0.6349	Remote Similarity	NPD8517	Approved
0.6349	Remote Similarity	NPD8515	Approved
0.6349	Remote Similarity	NPD8516	Approved
0.6328	Remote Similarity	NPD7492	Approved
0.6316	Remote Similarity	NPD7638	Approved
0.6311	Remote Similarity	NPD4632	Approved
0.6306	Remote Similarity	NPD5778	Approved
0.6306	Remote Similarity	NPD5779	Approved
0.6279	Remote Similarity	NPD6616	Approved
0.627	Remote Similarity	NPD6054	Approved
0.6262	Remote Similarity	NPD1694	Approved
0.625	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.624	Remote Similarity	NPD7328	Approved
0.624	Remote Similarity	NPD7327	Approved
0.6231	Remote Similarity	NPD7078	Approved
0.622	Remote Similarity	NPD6016	Approved
0.622	Remote Similarity	NPD6015	Approved
0.6218	Remote Similarity	NPD6412	Phase 2
0.6214	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5695	Phase 3
0.619	Remote Similarity	NPD7516	Approved
0.6183	Remote Similarity	NPD7736	Approved
0.6174	Remote Similarity	NPD5696	Approved
0.6172	Remote Similarity	NPD6370	Approved
0.6172	Remote Similarity	NPD5988	Approved
0.6161	Remote Similarity	NPD6399	Phase 3
0.6142	Remote Similarity	NPD8294	Approved
0.6142	Remote Similarity	NPD6059	Approved
0.6142	Remote Similarity	NPD8377	Approved
0.6132	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD8293	Discontinued
0.6107	Remote Similarity	NPD8074	Phase 3
0.6098	Remote Similarity	NPD8297	Approved
0.6094	Remote Similarity	NPD8380	Approved
0.6094	Remote Similarity	NPD8296	Approved
0.6094	Remote Similarity	NPD8379	Approved
0.6094	Remote Similarity	NPD8335	Approved
0.6094	Remote Similarity	NPD8378	Approved
0.6094	Remote Similarity	NPD7503	Approved
0.6087	Remote Similarity	NPD6084	Phase 2
0.6087	Remote Similarity	NPD6083	Phase 2
0.6083	Remote Similarity	NPD5697	Approved
0.6071	Remote Similarity	NPD7637	Suspended
0.6033	Remote Similarity	NPD6881	Approved
0.6033	Remote Similarity	NPD7320	Approved
0.6033	Remote Similarity	NPD6899	Approved
0.6032	Remote Similarity	NPD6009	Approved
0.6016	Remote Similarity	NPD6650	Approved
0.6016	Remote Similarity	NPD6649	Approved
0.6	Remote Similarity	NPD7524	Approved
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6402	Approved
0.5984	Remote Similarity	NPD6014	Approved
0.5984	Remote Similarity	NPD6012	Approved
0.5984	Remote Similarity	NPD6372	Approved
0.5984	Remote Similarity	NPD6013	Approved
0.5984	Remote Similarity	NPD6373	Approved
0.5969	Remote Similarity	NPD5983	Phase 2
0.595	Remote Similarity	NPD5701	Approved
0.595	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD7290	Approved
0.5935	Remote Similarity	NPD7102	Approved
0.5935	Remote Similarity	NPD4634	Approved
0.5935	Remote Similarity	NPD6883	Approved
0.5929	Remote Similarity	NPD5284	Approved
0.5929	Remote Similarity	NPD5693	Phase 1
0.5929	Remote Similarity	NPD5281	Approved
0.592	Remote Similarity	NPD8133	Approved
0.5917	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5913	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD8273	Phase 1
0.5902	Remote Similarity	NPD6011	Approved
0.5887	Remote Similarity	NPD6869	Approved
0.5887	Remote Similarity	NPD2204	Approved
0.5887	Remote Similarity	NPD8130	Phase 1
0.5887	Remote Similarity	NPD6847	Approved
0.5887	Remote Similarity	NPD6617	Approved
0.5882	Remote Similarity	NPD7632	Discontinued
0.5882	Remote Similarity	NPD5211	Phase 2
0.5878	Remote Similarity	NPD7604	Phase 2
0.5872	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7839	Suspended
0.5862	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD5956	Approved
0.5852	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5207	Approved
0.584	Remote Similarity	NPD6882	Approved
0.5833	Remote Similarity	NPD5209	Approved
0.5827	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD7260	Phase 2
0.5804	Remote Similarity	NPD6903	Approved
0.5798	Remote Similarity	NPD1700	Approved
0.5789	Remote Similarity	NPD6336	Discontinued
0.5785	Remote Similarity	NPD5141	Approved
0.578	Remote Similarity	NPD6110	Phase 1
0.578	Remote Similarity	NPD6695	Phase 3
0.5776	Remote Similarity	NPD5210	Approved
0.5776	Remote Similarity	NPD4629	Approved
0.5772	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD7521	Approved
0.5766	Remote Similarity	NPD7334	Approved
0.5766	Remote Similarity	NPD6684	Approved
0.5766	Remote Similarity	NPD6409	Approved
0.5766	Remote Similarity	NPD5330	Approved
0.5766	Remote Similarity	NPD7146	Approved
0.5766	Remote Similarity	NPD6845	Suspended
0.5758	Remote Similarity	NPD7642	Approved
0.5752	Remote Similarity	NPD4753	Phase 2
0.5752	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5752	Remote Similarity	NPD6051	Approved
0.5752	Remote Similarity	NPD6101	Approved
0.5725	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5286	Approved
0.5714	Remote Similarity	NPD4696	Approved
0.5714	Remote Similarity	NPD5285	Approved
0.5704	Remote Similarity	NPD6033	Approved
0.5703	Remote Similarity	NPD6274	Approved
0.5691	Remote Similarity	NPD6685	Approved
0.569	Remote Similarity	NPD6001	Approved
0.5688	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.568	Remote Similarity	NPD6421	Discontinued
0.5678	Remote Similarity	NPD4755	Approved
0.5672	Remote Similarity	NPD8451	Approved
0.5664	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6411	Approved
0.5639	Remote Similarity	NPD6067	Discontinued
0.5639	Remote Similarity	NPD7829	Approved
0.5639	Remote Similarity	NPD7830	Approved
0.5635	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.563	Remote Similarity	NPD8448	Approved
0.562	Remote Similarity	NPD5225	Approved
0.562	Remote Similarity	NPD5224	Approved
0.562	Remote Similarity	NPD5226	Approved
0.562	Remote Similarity	NPD4633	Approved
0.5615	Remote Similarity	NPD7641	Discontinued
0.5614	Remote Similarity	NPD6904	Approved
0.5614	Remote Similarity	NPD6080	Approved
0.5614	Remote Similarity	NPD6673	Approved
0.5614	Remote Similarity	NPD5370	Suspended
0.5603	Remote Similarity	NPD4202	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