NPASS Compound

Structure

NPC472873 OpenBabel07101718312D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.0533 1.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2704 -2.5734 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6138 -4.2099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4545 -2.3952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6195 0.6922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1195 -1.4985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6320 -0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6195 0.6922 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3600 -1.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0341 -3.3025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2185 -1.0646 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9960 -0.0896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0204 -1.0646 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2389 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3930 -0.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8789 -1.5775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2430 -0.0896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0301 -3.2129 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7518 0.8584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3680 -1.1420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4198 0.4782 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4585 -2.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 2 0 0 0 0 3 10 1 0 0 0 0 5 8 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 7 16 1 0 0 0 0 8 17 1 1 0 0 0 9 11 1 0 0 0 0 9 15 1 0 0 0 0 10 18 2 0 0 0 0 10 23 1 0 0 0 0 11 6 1 1 0 0 0 11 12 1 0 0 0 0 12 5 1 1 0 0 0 12 22 1 0 0 0 0 13 16 1 1 0 0 0 13 17 1 0 0 0 0 14 17 1 6 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 16 4 1 1 0 0 0 16 23 1 0 0 0 0 17 21 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.16
Volume:	321.751
LogP:	1.138
LogD:	0.592
LogS:	-2.446
# Rotatable Bonds:	2
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.551
Synthetic Accessibility Score:	4.983
Fsp3:	0.765
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:	-4.952
MDCK Permeability:	0.00010711075447034091
Pgp-inhibitor:	0.005
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.16
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.932

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.621
Plasma Protein Binding (PPB):	54.878936767578125%
Volume Distribution (VD):	0.754
Pgp-substrate:	60.64733123779297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.429
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.075
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.139
CYP3A4-inhibitor:	0.082
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	3.309
Half-life (T1/2):	0.789

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.926
Drug-inuced Liver Injury (DILI):	0.762
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.87
Maximum Recommended Daily Dose:	0.542
Skin Sensitization:	0.514
Carcinogencity:	0.334
Eye Corrosion:	0.057
Eye Irritation:	0.191
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC472873

Natural Product ID:	NPC472873
*Common Name:**	LYXJKCKFLUJLMJ-WFWNFZGVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LYXJKCKFLUJLMJ-WFWNFZGVSA-N
Standard InCHI:	InChI=1S/C17H24O6/c1-8-5-12-11(9(2)15(20)22-12)6-13-16(4,23-10(3)18)7-14(19)17(8,13)21/h8,11-14,19,21H,2,5-7H2,1,3-4H3/t8-,11+,12+,13-,14-,16+,17-/m0/s1
SMILES:	CC(=O)O[C@]1(C)C[C@@H]([C@]2([C@H]1C[C@H]1[C@@H](C[C@@H]2C)OC(=O)C1=C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593382
PubChem CID:	n.a.
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
NPO33441	leucophyta brownii	Species	Asteraceae	Eukaryota	Resinous Exudates	n.a.	n.a.	PMID[26218649]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	27200.0	nM	PMID[566006]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	29300.0	nM	PMID[566006]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	34600.0	nM	PMID[566006]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	10500.0	nM	PMID[566006]

☑ 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 NPC472873 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	275
0.1-0.2	1849
0.2-0.3	6446
0.3-0.4	15256
0.4-0.5	8990
0.5-0.6	6791
0.6-0.7	2504
0.7-0.8	419
0.8-0.85	79
0.85-0.9	54
0.9-0.95	30
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC471150
0.9545	High Similarity	NPC216284
0.9432	High Similarity	NPC215556
0.9355	High Similarity	NPC471381
0.9355	High Similarity	NPC186861
0.9318	High Similarity	NPC79549
0.9247	High Similarity	NPC45125
0.9222	High Similarity	NPC29821
0.9222	High Similarity	NPC63193
0.9222	High Similarity	NPC57304
0.9222	High Similarity	NPC155215
0.9222	High Similarity	NPC171360
0.9222	High Similarity	NPC293001
0.9222	High Similarity	NPC133888
0.9222	High Similarity	NPC35959
0.914	High Similarity	NPC311904
0.914	High Similarity	NPC181151
0.9121	High Similarity	NPC258216
0.9111	High Similarity	NPC297474
0.9111	High Similarity	NPC54065
0.9111	High Similarity	NPC35809
0.9101	High Similarity	NPC217983
0.9101	High Similarity	NPC207114
0.9072	High Similarity	NPC54737
0.9011	High Similarity	NPC184063
0.9	High Similarity	NPC472872
0.9	High Similarity	NPC155935
0.8977	High Similarity	NPC284534
0.8977	High Similarity	NPC300082
0.8977	High Similarity	NPC204105
0.8936	High Similarity	NPC474313
0.8936	High Similarity	NPC161493
0.8925	High Similarity	NPC213698
0.8925	High Similarity	NPC163228
0.8925	High Similarity	NPC476053
0.8913	High Similarity	NPC472874
0.8901	High Similarity	NPC19087
0.8878	High Similarity	NPC44004
0.8876	High Similarity	NPC187661
0.8854	High Similarity	NPC150923
0.883	High Similarity	NPC213078
0.883	High Similarity	NPC24956
0.883	High Similarity	NPC18019
0.8817	High Similarity	NPC127019
0.88	High Similarity	NPC139838
0.88	High Similarity	NPC59489
0.8791	High Similarity	NPC38392
0.8778	High Similarity	NPC24728
0.875	High Similarity	NPC111409
0.875	High Similarity	NPC245665
0.8723	High Similarity	NPC52044
0.8723	High Similarity	NPC67584
0.8723	High Similarity	NPC170120
0.87	High Similarity	NPC68248
0.8681	High Similarity	NPC178875
0.8681	High Similarity	NPC471149
0.8667	High Similarity	NPC56593
0.8652	High Similarity	NPC194859
0.8652	High Similarity	NPC224386
0.8636	High Similarity	NPC246076
0.8632	High Similarity	NPC91771
0.8632	High Similarity	NPC142529
0.8617	High Similarity	NPC198853
0.8602	High Similarity	NPC131209
0.8602	High Similarity	NPC133698
0.8602	High Similarity	NPC475925
0.8587	High Similarity	NPC283409
0.8571	High Similarity	NPC118601
0.8557	High Similarity	NPC70865
0.8539	High Similarity	NPC128246
0.8511	High Similarity	NPC473263
0.8511	High Similarity	NPC475788
0.8511	High Similarity	NPC473234
0.8511	High Similarity	NPC308656
0.8511	High Similarity	NPC473273
0.8511	High Similarity	NPC60386
0.8485	Intermediate Similarity	NPC124881
0.8462	Intermediate Similarity	NPC236692
0.8462	Intermediate Similarity	NPC304558
0.8462	Intermediate Similarity	NPC309757
0.8454	Intermediate Similarity	NPC221615
0.8454	Intermediate Similarity	NPC249171
0.8454	Intermediate Similarity	NPC49833
0.8421	Intermediate Similarity	NPC262133
0.8421	Intermediate Similarity	NPC323008
0.8421	Intermediate Similarity	NPC470010
0.8421	Intermediate Similarity	NPC470013
0.8421	Intermediate Similarity	NPC477131
0.8409	Intermediate Similarity	NPC156658
0.8409	Intermediate Similarity	NPC258965
0.8384	Intermediate Similarity	NPC86077
0.8381	Intermediate Similarity	NPC121816
0.837	Intermediate Similarity	NPC190753
0.837	Intermediate Similarity	NPC186148
0.837	Intermediate Similarity	NPC270270
0.8351	Intermediate Similarity	NPC304445
0.8351	Intermediate Similarity	NPC236580
0.8317	Intermediate Similarity	NPC243998
0.8316	Intermediate Similarity	NPC200237
0.8316	Intermediate Similarity	NPC153590
0.8315	Intermediate Similarity	NPC126248
0.8302	Intermediate Similarity	NPC255450
0.8302	Intermediate Similarity	NPC170692
0.83	Intermediate Similarity	NPC473148
0.8298	Intermediate Similarity	NPC301969
0.8298	Intermediate Similarity	NPC246173
0.8298	Intermediate Similarity	NPC474323
0.8298	Intermediate Similarity	NPC37607
0.8298	Intermediate Similarity	NPC206614
0.8286	Intermediate Similarity	NPC273242
0.8283	Intermediate Similarity	NPC171759
0.828	Intermediate Similarity	NPC91248
0.828	Intermediate Similarity	NPC177629
0.828	Intermediate Similarity	NPC58219
0.8261	Intermediate Similarity	NPC64153
0.8261	Intermediate Similarity	NPC67493
0.8261	Intermediate Similarity	NPC470242
0.8252	Intermediate Similarity	NPC115352
0.8247	Intermediate Similarity	NPC476009
0.8229	Intermediate Similarity	NPC473331
0.8211	Intermediate Similarity	NPC286341
0.8211	Intermediate Similarity	NPC191339
0.82	Intermediate Similarity	NPC80144
0.8191	Intermediate Similarity	NPC92974
0.8172	Intermediate Similarity	NPC201658
0.8163	Intermediate Similarity	NPC108475
0.8163	Intermediate Similarity	NPC170143
0.8163	Intermediate Similarity	NPC213947
0.8163	Intermediate Similarity	NPC261372
0.8163	Intermediate Similarity	NPC58267
0.8163	Intermediate Similarity	NPC263674
0.8152	Intermediate Similarity	NPC235792
0.8144	Intermediate Similarity	NPC475900
0.8144	Intermediate Similarity	NPC304886
0.8144	Intermediate Similarity	NPC224689
0.8137	Intermediate Similarity	NPC223450
0.81	Intermediate Similarity	NPC67296
0.8085	Intermediate Similarity	NPC224652
0.8085	Intermediate Similarity	NPC202672
0.8065	Intermediate Similarity	NPC162071
0.8065	Intermediate Similarity	NPC474949
0.8065	Intermediate Similarity	NPC475019
0.8061	Intermediate Similarity	NPC474297
0.8058	Intermediate Similarity	NPC197813
0.8058	Intermediate Similarity	NPC80338
0.8058	Intermediate Similarity	NPC148270
0.8058	Intermediate Similarity	NPC26617
0.8043	Intermediate Similarity	NPC156485
0.8021	Intermediate Similarity	NPC12172
0.8021	Intermediate Similarity	NPC184463
0.8021	Intermediate Similarity	NPC208886
0.8	Intermediate Similarity	NPC193741
0.8	Intermediate Similarity	NPC168679
0.8	Intermediate Similarity	NPC4986
0.8	Intermediate Similarity	NPC12872
0.7961	Intermediate Similarity	NPC170432
0.7959	Intermediate Similarity	NPC167893
0.7957	Intermediate Similarity	NPC329749
0.7941	Intermediate Similarity	NPC475928
0.7938	Intermediate Similarity	NPC470187
0.7938	Intermediate Similarity	NPC475912
0.7938	Intermediate Similarity	NPC212486
0.7938	Intermediate Similarity	NPC81419
0.7938	Intermediate Similarity	NPC135776
0.7938	Intermediate Similarity	NPC179746
0.7879	Intermediate Similarity	NPC126156
0.7872	Intermediate Similarity	NPC476015
0.7872	Intermediate Similarity	NPC474762
0.7864	Intermediate Similarity	NPC100487
0.7857	Intermediate Similarity	NPC190294
0.785	Intermediate Similarity	NPC35069
0.785	Intermediate Similarity	NPC258711
0.785	Intermediate Similarity	NPC475924
0.785	Intermediate Similarity	NPC475851
0.7849	Intermediate Similarity	NPC474780
0.7843	Intermediate Similarity	NPC474747
0.7835	Intermediate Similarity	NPC30515
0.7835	Intermediate Similarity	NPC70251
0.7835	Intermediate Similarity	NPC475881
0.7812	Intermediate Similarity	NPC173926
0.7812	Intermediate Similarity	NPC307411
0.781	Intermediate Similarity	NPC117604
0.781	Intermediate Similarity	NPC110701
0.7802	Intermediate Similarity	NPC476625
0.7802	Intermediate Similarity	NPC51507
0.78	Intermediate Similarity	NPC477949
0.7788	Intermediate Similarity	NPC127235
0.7788	Intermediate Similarity	NPC166115
0.7778	Intermediate Similarity	NPC14961
0.7778	Intermediate Similarity	NPC37408
0.7778	Intermediate Similarity	NPC270013
0.7778	Intermediate Similarity	NPC36954
0.7767	Intermediate Similarity	NPC37240
0.7767	Intermediate Similarity	NPC221421
0.7767	Intermediate Similarity	NPC475945
0.7767	Intermediate Similarity	NPC475871
0.7767	Intermediate Similarity	NPC474775
0.7766	Intermediate Similarity	NPC149725
0.7766	Intermediate Similarity	NPC304509
0.7766	Intermediate Similarity	NPC47958

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 NPC472873 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	2594
0.2-0.3	3873
0.3-0.4	1621
0.4-0.5	436
0.5-0.6	256
0.6-0.7	39
0.7-0.8	8
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8058	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1695	Approved
0.7664	Intermediate Similarity	NPD6371	Approved
0.7364	Intermediate Similarity	NPD6053	Discontinued
0.732	Intermediate Similarity	NPD4249	Approved
0.7255	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD4251	Approved
0.7245	Intermediate Similarity	NPD4250	Approved
0.7041	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD46	Approved
0.703	Intermediate Similarity	NPD6698	Approved
0.701	Intermediate Similarity	NPD5362	Discontinued
0.6907	Remote Similarity	NPD6435	Approved
0.6875	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4821	Approved
0.6875	Remote Similarity	NPD4819	Approved
0.6875	Remote Similarity	NPD4822	Approved
0.6875	Remote Similarity	NPD4820	Approved
0.6869	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5785	Approved
0.6804	Remote Similarity	NPD5369	Approved
0.6701	Remote Similarity	NPD5368	Approved
0.67	Remote Similarity	NPD5363	Approved
0.6699	Remote Similarity	NPD7838	Discovery
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6566	Remote Similarity	NPD4270	Approved
0.6566	Remote Similarity	NPD4269	Approved
0.6552	Remote Similarity	NPD8133	Approved
0.6549	Remote Similarity	NPD6686	Approved
0.6522	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD6008	Approved
0.6509	Remote Similarity	NPD5282	Discontinued
0.6504	Remote Similarity	NPD7507	Approved
0.65	Remote Similarity	NPD6319	Approved
0.65	Remote Similarity	NPD5331	Approved
0.65	Remote Similarity	NPD5332	Approved
0.6476	Remote Similarity	NPD7983	Approved
0.6471	Remote Similarity	NPD5786	Approved
0.6465	Remote Similarity	NPD4790	Discontinued
0.6429	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD7492	Approved
0.6422	Remote Similarity	NPD4225	Approved
0.6422	Remote Similarity	NPD7638	Approved
0.641	Remote Similarity	NPD4632	Approved
0.6387	Remote Similarity	NPD7115	Discovery
0.6371	Remote Similarity	NPD6616	Approved
0.6364	Remote Similarity	NPD7639	Approved
0.6364	Remote Similarity	NPD4252	Approved
0.6364	Remote Similarity	NPD7640	Approved
0.6364	Remote Similarity	NPD6054	Approved
0.6349	Remote Similarity	NPD7319	Approved
0.633	Remote Similarity	NPD6083	Phase 2
0.633	Remote Similarity	NPD6084	Phase 2
0.632	Remote Similarity	NPD7078	Approved
0.6316	Remote Similarity	NPD6412	Phase 2
0.6316	Remote Similarity	NPD5697	Approved
0.6311	Remote Similarity	NPD6015	Approved
0.6311	Remote Similarity	NPD8033	Approved
0.6311	Remote Similarity	NPD6016	Approved
0.6306	Remote Similarity	NPD5344	Discontinued
0.6296	Remote Similarity	NPD5695	Phase 3
0.6273	Remote Similarity	NPD5696	Approved
0.6273	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.627	Remote Similarity	NPD7736	Approved
0.6262	Remote Similarity	NPD6399	Phase 3
0.6261	Remote Similarity	NPD7320	Approved
0.6261	Remote Similarity	NPD6899	Approved
0.6261	Remote Similarity	NPD6881	Approved
0.626	Remote Similarity	NPD5988	Approved
0.626	Remote Similarity	NPD6370	Approved
0.6239	Remote Similarity	NPD6650	Approved
0.6239	Remote Similarity	NPD6649	Approved
0.623	Remote Similarity	NPD6059	Approved
0.6228	Remote Similarity	NPD6675	Approved
0.6228	Remote Similarity	NPD5739	Approved
0.6228	Remote Similarity	NPD6402	Approved
0.6228	Remote Similarity	NPD7128	Approved
0.6207	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6014	Approved
0.6207	Remote Similarity	NPD6013	Approved
0.6207	Remote Similarity	NPD6372	Approved
0.6207	Remote Similarity	NPD6012	Approved
0.6207	Remote Similarity	NPD6373	Approved
0.6198	Remote Similarity	NPD7328	Approved
0.6198	Remote Similarity	NPD7327	Approved
0.619	Remote Similarity	NPD8293	Discontinued
0.6186	Remote Similarity	NPD8297	Approved
0.6176	Remote Similarity	NPD4788	Approved
0.6174	Remote Similarity	NPD5701	Approved
0.6168	Remote Similarity	NPD8034	Phase 2
0.6168	Remote Similarity	NPD8035	Phase 2
0.6162	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7102	Approved
0.6154	Remote Similarity	NPD7290	Approved
0.6154	Remote Similarity	NPD6883	Approved
0.6154	Remote Similarity	NPD4634	Approved
0.6148	Remote Similarity	NPD7516	Approved
0.6121	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6011	Approved
0.6116	Remote Similarity	NPD6009	Approved
0.6111	Remote Similarity	NPD5779	Approved
0.6111	Remote Similarity	NPD5778	Approved
0.6102	Remote Similarity	NPD6617	Approved
0.6102	Remote Similarity	NPD6847	Approved
0.6102	Remote Similarity	NPD8130	Phase 1
0.6102	Remote Similarity	NPD6869	Approved
0.6098	Remote Similarity	NPD8294	Approved
0.6098	Remote Similarity	NPD8377	Approved
0.6067	Remote Similarity	NPD3198	Approved
0.605	Remote Similarity	NPD6882	Approved
0.6048	Remote Similarity	NPD5983	Phase 2
0.6048	Remote Similarity	NPD8378	Approved
0.6048	Remote Similarity	NPD8516	Approved
0.6048	Remote Similarity	NPD8517	Approved
0.6048	Remote Similarity	NPD8296	Approved
0.6048	Remote Similarity	NPD8380	Approved
0.6048	Remote Similarity	NPD8379	Approved
0.6048	Remote Similarity	NPD8335	Approved
0.6048	Remote Similarity	NPD8515	Approved
0.6048	Remote Similarity	NPD8513	Phase 3
0.6048	Remote Similarity	NPD7503	Approved
0.6019	Remote Similarity	NPD5693	Phase 1
0.6019	Remote Similarity	NPD5284	Approved
0.6019	Remote Similarity	NPD7637	Suspended
0.6019	Remote Similarity	NPD5281	Approved
0.6018	Remote Similarity	NPD1700	Approved
0.6017	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5210	Approved
0.6	Remote Similarity	NPD4802	Phase 2
0.6	Remote Similarity	NPD4238	Approved
0.6	Remote Similarity	NPD4629	Approved
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4753	Phase 2
0.5965	Remote Similarity	NPD5211	Phase 2
0.5965	Remote Similarity	NPD7632	Discontinued
0.5962	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7604	Phase 2
0.5943	Remote Similarity	NPD7524	Approved
0.5929	Remote Similarity	NPD5285	Approved
0.5929	Remote Similarity	NPD6648	Approved
0.5929	Remote Similarity	NPD4696	Approved
0.5929	Remote Similarity	NPD5286	Approved
0.5926	Remote Similarity	NPD5207	Approved
0.5923	Remote Similarity	NPD5956	Approved
0.5922	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.592	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD1694	Approved
0.5905	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6274	Approved
0.5897	Remote Similarity	NPD6685	Approved
0.5893	Remote Similarity	NPD4755	Approved
0.5888	Remote Similarity	NPD6903	Approved
0.5865	Remote Similarity	NPD6695	Phase 3
0.5862	Remote Similarity	NPD5141	Approved
0.5859	Remote Similarity	NPD6336	Discontinued
0.5849	Remote Similarity	NPD7334	Approved
0.5849	Remote Similarity	NPD7521	Approved
0.5849	Remote Similarity	NPD7146	Approved
0.5849	Remote Similarity	NPD6684	Approved
0.5849	Remote Similarity	NPD5330	Approved
0.5849	Remote Similarity	NPD6409	Approved
0.5833	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6101	Approved
0.5833	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD5226	Approved
0.5826	Remote Similarity	NPD4633	Approved
0.5826	Remote Similarity	NPD5225	Approved
0.5826	Remote Similarity	NPD5224	Approved
0.5818	Remote Similarity	NPD4202	Approved
0.5814	Remote Similarity	NPD8074	Phase 3
0.581	Remote Similarity	NPD3665	Phase 1
0.581	Remote Similarity	NPD3133	Approved
0.581	Remote Similarity	NPD3666	Approved
0.5802	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD8269	Approved
0.5794	Remote Similarity	NPD8267	Approved
0.5794	Remote Similarity	NPD8268	Approved
0.5794	Remote Similarity	NPD8266	Approved
0.5789	Remote Similarity	NPD4700	Approved
0.5776	Remote Similarity	NPD5174	Approved
0.5776	Remote Similarity	NPD5175	Approved
0.5769	Remote Similarity	NPD6033	Approved
0.5766	Remote Similarity	NPD6001	Approved
0.5763	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.576	Remote Similarity	NPD7101	Approved
0.576	Remote Similarity	NPD7100	Approved
0.576	Remote Similarity	NPD4522	Approved
0.5741	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD5223	Approved
0.5736	Remote Similarity	NPD8273	Phase 1
0.5727	Remote Similarity	NPD6411	Approved
0.5726	Remote Similarity	NPD6317	Approved
0.5714	Remote Similarity	NPD6845	Suspended
0.5703	Remote Similarity	NPD6067	Discontinued
0.57	Remote Similarity	NPD3702	Approved
0.5688	Remote Similarity	NPD6904	Approved
0.5688	Remote Similarity	NPD6673	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