NPASS Compound

Structure

NPC472874 OpenBabel07101718312D 22 25 0 0 1 0 0 0 0 0999 V2000 -2.3110 -1.3868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8526 -2.9753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6148 -3.6911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3884 0.8001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2460 -2.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5545 -1.5847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1628 -0.6075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4439 -1.5847 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9712 -3.0947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3846 -2.8320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3566 -2.4518 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4447 -2.8377 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.8894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2819 -1.0522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5498 -3.8779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8894 -0.8894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0135 -2.2031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9357 -4.6792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0517 -1.9112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3253 -3.7190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8894 0.0000 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 6 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 20 1 0 0 0 0 11 6 1 6 0 0 0 11 12 1 0 0 0 0 12 5 1 6 0 0 0 12 21 1 0 0 0 0 13 16 1 6 0 0 0 13 17 1 0 0 0 0 14 17 1 6 0 0 0 14 20 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 4 1 1 0 0 0 16 22 1 0 0 0 0 17 22 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.15
Volume:	304.404
LogP:	2.067
LogD:	1.161
LogS:	-3.715
# Rotatable Bonds:	2
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.548
Synthetic Accessibility Score:	6.115
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:	-4.768
MDCK Permeability:	5.087549288873561e-05
Pgp-inhibitor:	0.86
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.036
30% Bioavailability (F30%):	0.934

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.635
Plasma Protein Binding (PPB):	61.41172790527344%
Volume Distribution (VD):	1.425
Pgp-substrate:	55.94036102294922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.083
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.357
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.05
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.218
CYP3A4-substrate:	0.258

ADMET: Excretion

Clearance (CL):	6.846
Half-life (T1/2):	0.577

ADMET: Toxicity

hERG Blockers:	0.257
Human Hepatotoxicity (H-HT):	0.976
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.656
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.883
Carcinogencity:	0.642
Eye Corrosion:	0.473
Eye Irritation:	0.803
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC472874

Natural Product ID:	NPC472874
*Common Name:**	DXIHLNPMHHUUTE-WLULCEGHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	DXIHLNPMHHUUTE-WLULCEGHSA-N
Standard InCHI:	InChI=1S/C17H22O5/c1-8-5-12-11(9(2)15(19)21-12)6-13-16(4)7-14(20-10(3)18)17(8,13)22-16/h8,11-14H,2,5-7H2,1,3-4H3/t8-,11+,12+,13-,14-,16+,17+/m0/s1
SMILES:	CC1CC2C(CC3C14C(CC3(O4)C)OC(=O)C)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593383
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	>	65000.0	nM	PMID[490332]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	65000.0	nM	PMID[490332]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	38600.0	nM	PMID[490332]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	16300.0	nM	PMID[490332]

☑ 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 NPC472874 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	342
0.1-0.2	2575
0.2-0.3	8764
0.3-0.4	16298
0.4-0.5	8788
0.5-0.6	4704
0.6-0.7	978
0.7-0.8	202
0.8-0.85	40
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9341	High Similarity	NPC181151
0.9121	High Similarity	NPC224689
0.8989	High Similarity	NPC472872
0.8913	High Similarity	NPC472873
0.8764	High Similarity	NPC24728
0.8737	High Similarity	NPC186861
0.8723	High Similarity	NPC471150
0.8681	High Similarity	NPC216284
0.8667	High Similarity	NPC471149
0.8667	High Similarity	NPC79549
0.866	High Similarity	NPC124881
0.8632	High Similarity	NPC45125
0.8621	High Similarity	NPC246076
0.8587	High Similarity	NPC155215
0.8571	High Similarity	NPC215556
0.8571	High Similarity	NPC283409
0.8542	High Similarity	NPC70865
0.8542	High Similarity	NPC471381
0.8495	Intermediate Similarity	NPC258216
0.8444	Intermediate Similarity	NPC304558
0.8387	Intermediate Similarity	NPC63193
0.8387	Intermediate Similarity	NPC293001
0.8387	Intermediate Similarity	NPC133888
0.8387	Intermediate Similarity	NPC35959
0.8387	Intermediate Similarity	NPC29821
0.8387	Intermediate Similarity	NPC171360
0.8387	Intermediate Similarity	NPC57304
0.8352	Intermediate Similarity	NPC270270
0.8333	Intermediate Similarity	NPC284534
0.8333	Intermediate Similarity	NPC300082
0.8333	Intermediate Similarity	NPC204105
0.8316	Intermediate Similarity	NPC163228
0.8316	Intermediate Similarity	NPC476053
0.83	Intermediate Similarity	NPC54737
0.828	Intermediate Similarity	NPC297474
0.828	Intermediate Similarity	NPC35809
0.828	Intermediate Similarity	NPC54065
0.8261	Intermediate Similarity	NPC207114
0.8261	Intermediate Similarity	NPC217983
0.8242	Intermediate Similarity	NPC64153
0.8229	Intermediate Similarity	NPC213078
0.8211	Intermediate Similarity	NPC198853
0.8211	Intermediate Similarity	NPC127019
0.8191	Intermediate Similarity	NPC286341
0.8191	Intermediate Similarity	NPC191339
0.8191	Intermediate Similarity	NPC184063
0.8191	Intermediate Similarity	NPC133698
0.8172	Intermediate Similarity	NPC155935
0.8172	Intermediate Similarity	NPC4986
0.8152	Intermediate Similarity	NPC190753
0.8144	Intermediate Similarity	NPC474313
0.8144	Intermediate Similarity	NPC311904
0.8144	Intermediate Similarity	NPC161493
0.8132	Intermediate Similarity	NPC235792
0.8125	Intermediate Similarity	NPC67584
0.8125	Intermediate Similarity	NPC167893
0.8125	Intermediate Similarity	NPC213698
0.8119	Intermediate Similarity	NPC44004
0.8111	Intermediate Similarity	NPC245665
0.8085	Intermediate Similarity	NPC19087
0.8065	Intermediate Similarity	NPC178875
0.8065	Intermediate Similarity	NPC224652
0.8058	Intermediate Similarity	NPC59489
0.8058	Intermediate Similarity	NPC139838
0.8043	Intermediate Similarity	NPC187661
0.8041	Intermediate Similarity	NPC24956
0.8041	Intermediate Similarity	NPC18019
0.8021	Intermediate Similarity	NPC470010
0.8021	Intermediate Similarity	NPC262133
0.8021	Intermediate Similarity	NPC470013
0.8021	Intermediate Similarity	NPC477131
0.8021	Intermediate Similarity	NPC323008
0.8	Intermediate Similarity	NPC86077
0.8	Intermediate Similarity	NPC131209
0.7979	Intermediate Similarity	NPC38392
0.7961	Intermediate Similarity	NPC68248
0.7957	Intermediate Similarity	NPC186148
0.7957	Intermediate Similarity	NPC118601
0.7938	Intermediate Similarity	NPC52044
0.7938	Intermediate Similarity	NPC170120
0.7917	Intermediate Similarity	NPC473263
0.7917	Intermediate Similarity	NPC308656
0.7917	Intermediate Similarity	NPC473234
0.7917	Intermediate Similarity	NPC473273
0.7917	Intermediate Similarity	NPC60386
0.7912	Intermediate Similarity	NPC111409
0.79	Intermediate Similarity	NPC150923
0.7895	Intermediate Similarity	NPC206614
0.7895	Intermediate Similarity	NPC474323
0.7879	Intermediate Similarity	NPC221615
0.7872	Intermediate Similarity	NPC91248
0.7872	Intermediate Similarity	NPC58219
0.7872	Intermediate Similarity	NPC177629
0.7857	Intermediate Similarity	NPC91771
0.7857	Intermediate Similarity	NPC142529
0.7849	Intermediate Similarity	NPC56593
0.7849	Intermediate Similarity	NPC162071
0.7826	Intermediate Similarity	NPC224386
0.7826	Intermediate Similarity	NPC194859
0.7812	Intermediate Similarity	NPC475925
0.7789	Intermediate Similarity	NPC92974
0.7778	Intermediate Similarity	NPC474981
0.7778	Intermediate Similarity	NPC156658
0.7778	Intermediate Similarity	NPC258965
0.7767	Intermediate Similarity	NPC223450
0.7767	Intermediate Similarity	NPC243998
0.7766	Intermediate Similarity	NPC5130
0.7757	Intermediate Similarity	NPC273242
0.7755	Intermediate Similarity	NPC475900
0.7732	Intermediate Similarity	NPC475788
0.7732	Intermediate Similarity	NPC153590
0.7717	Intermediate Similarity	NPC474472
0.7717	Intermediate Similarity	NPC128429
0.7717	Intermediate Similarity	NPC54468
0.7717	Intermediate Similarity	NPC128246
0.7717	Intermediate Similarity	NPC257358
0.7714	Intermediate Similarity	NPC115352
0.7708	Intermediate Similarity	NPC37607
0.7708	Intermediate Similarity	NPC301969
0.7701	Intermediate Similarity	NPC320537
0.7701	Intermediate Similarity	NPC143979
0.77	Intermediate Similarity	NPC49833
0.77	Intermediate Similarity	NPC249171
0.7692	Intermediate Similarity	NPC47635
0.7692	Intermediate Similarity	NPC26617
0.7685	Intermediate Similarity	NPC121816
0.7677	Intermediate Similarity	NPC476009
0.766	Intermediate Similarity	NPC236692
0.766	Intermediate Similarity	NPC238593
0.766	Intermediate Similarity	NPC470242
0.766	Intermediate Similarity	NPC309757
0.766	Intermediate Similarity	NPC67493
0.7629	Intermediate Similarity	NPC208886
0.7629	Intermediate Similarity	NPC12172
0.7615	Intermediate Similarity	NPC255450
0.7615	Intermediate Similarity	NPC170692
0.7604	Intermediate Similarity	NPC151770
0.76	Intermediate Similarity	NPC304445
0.76	Intermediate Similarity	NPC213947
0.76	Intermediate Similarity	NPC170143
0.76	Intermediate Similarity	NPC108475
0.76	Intermediate Similarity	NPC236580
0.7582	Intermediate Similarity	NPC276356
0.7579	Intermediate Similarity	NPC231889
0.7579	Intermediate Similarity	NPC201658
0.7576	Intermediate Similarity	NPC304886
0.7573	Intermediate Similarity	NPC473148
0.7551	Intermediate Similarity	NPC200237
0.7551	Intermediate Similarity	NPC135776
0.7551	Intermediate Similarity	NPC179746
0.7551	Intermediate Similarity	NPC81419
0.7549	Intermediate Similarity	NPC471767
0.7549	Intermediate Similarity	NPC171759
0.7526	Intermediate Similarity	NPC475748
0.7524	Intermediate Similarity	NPC470192
0.75	Intermediate Similarity	NPC126248
0.75	Intermediate Similarity	NPC113433
0.7476	Intermediate Similarity	NPC250594
0.7476	Intermediate Similarity	NPC78127
0.7476	Intermediate Similarity	NPC80144
0.7476	Intermediate Similarity	NPC471757
0.7475	Intermediate Similarity	NPC473330
0.7475	Intermediate Similarity	NPC281775
0.7475	Intermediate Similarity	NPC473316
0.7475	Intermediate Similarity	NPC473331
0.7474	Intermediate Similarity	NPC50637
0.7474	Intermediate Similarity	NPC476015
0.7474	Intermediate Similarity	NPC475019
0.7474	Intermediate Similarity	NPC107787
0.7474	Intermediate Similarity	NPC474949
0.7474	Intermediate Similarity	NPC474762
0.7449	Intermediate Similarity	NPC184463
0.7447	Intermediate Similarity	NPC156485
0.7447	Intermediate Similarity	NPC470238
0.7447	Intermediate Similarity	NPC115786
0.7447	Intermediate Similarity	NPC138647
0.7444	Intermediate Similarity	NPC208223
0.7429	Intermediate Similarity	NPC291643
0.7426	Intermediate Similarity	NPC58267
0.7426	Intermediate Similarity	NPC261372
0.7426	Intermediate Similarity	NPC263674
0.7423	Intermediate Similarity	NPC307411
0.7391	Intermediate Similarity	NPC6823
0.7391	Intermediate Similarity	NPC73052
0.7391	Intermediate Similarity	NPC290508
0.7391	Intermediate Similarity	NPC74673
0.7391	Intermediate Similarity	NPC293418
0.7391	Intermediate Similarity	NPC69271
0.7379	Intermediate Similarity	NPC67296
0.7374	Intermediate Similarity	NPC476300
0.7374	Intermediate Similarity	NPC470187
0.7374	Intermediate Similarity	NPC212486
0.7374	Intermediate Similarity	NPC475912
0.7368	Intermediate Similarity	NPC78089
0.7368	Intermediate Similarity	NPC329749
0.7368	Intermediate Similarity	NPC304509
0.7368	Intermediate Similarity	NPC149725
0.7368	Intermediate Similarity	NPC47958
0.7358	Intermediate Similarity	NPC197813
0.7358	Intermediate Similarity	NPC148270

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 NPC472874 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	3173
0.2-0.3	3868
0.3-0.4	1250
0.4-0.5	317
0.5-0.6	150
0.6-0.7	9
0.7-0.8	2
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
0.8172	Intermediate Similarity	NPD1695	Approved
0.7692	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6371	Approved
0.6731	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6053	Discontinued
0.66	Remote Similarity	NPD4249	Approved
0.6535	Remote Similarity	NPD4250	Approved
0.6535	Remote Similarity	NPD4251	Approved
0.6505	Remote Similarity	NPD46	Approved
0.6505	Remote Similarity	NPD6698	Approved
0.6486	Remote Similarity	NPD6008	Approved
0.6337	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.63	Remote Similarity	NPD5362	Discontinued
0.62	Remote Similarity	NPD6435	Approved
0.619	Remote Similarity	NPD5785	Approved
0.619	Remote Similarity	NPD7838	Discovery
0.6168	Remote Similarity	NPD5282	Discontinued
0.6162	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD4821	Approved
0.6162	Remote Similarity	NPD4822	Approved
0.6162	Remote Similarity	NPD4820	Approved
0.6162	Remote Similarity	NPD4819	Approved
0.6139	Remote Similarity	NPD7154	Phase 3
0.61	Remote Similarity	NPD5369	Approved
0.6087	Remote Similarity	NPD6686	Approved
0.6068	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.604	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD1694	Approved
0.6019	Remote Similarity	NPD5363	Approved
0.6	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD5368	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7983	Approved
0.5981	Remote Similarity	NPD5693	Phase 1
0.5966	Remote Similarity	NPD8133	Approved
0.5965	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4271	Approved
0.596	Remote Similarity	NPD4268	Approved
0.5952	Remote Similarity	NPD7507	Approved
0.5952	Remote Similarity	NPD6616	Approved
0.5946	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD4225	Approved
0.5935	Remote Similarity	NPD6319	Approved
0.5935	Remote Similarity	NPD6054	Approved
0.5906	Remote Similarity	NPD7078	Approved
0.5893	Remote Similarity	NPD6648	Approved
0.5888	Remote Similarity	NPD5207	Approved
0.5887	Remote Similarity	NPD6016	Approved
0.5887	Remote Similarity	NPD6015	Approved
0.5882	Remote Similarity	NPD4269	Approved
0.5882	Remote Similarity	NPD4270	Approved
0.5859	Remote Similarity	NPD7736	Approved
0.5849	Remote Similarity	NPD6903	Approved
0.5847	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5344	Discontinued
0.5841	Remote Similarity	NPD1700	Approved
0.584	Remote Similarity	NPD5988	Approved
0.584	Remote Similarity	NPD6370	Approved
0.5833	Remote Similarity	NPD4632	Approved
0.5825	Remote Similarity	NPD5332	Approved
0.5825	Remote Similarity	NPD5331	Approved
0.582	Remote Similarity	NPD7115	Discovery
0.5818	Remote Similarity	NPD5695	Phase 3
0.5814	Remote Similarity	NPD7319	Approved
0.581	Remote Similarity	NPD7334	Approved
0.581	Remote Similarity	NPD5786	Approved
0.581	Remote Similarity	NPD6684	Approved
0.581	Remote Similarity	NPD7146	Approved
0.581	Remote Similarity	NPD6409	Approved
0.581	Remote Similarity	NPD5330	Approved
0.581	Remote Similarity	NPD7521	Approved
0.5806	Remote Similarity	NPD6059	Approved
0.5804	Remote Similarity	NPD7638	Approved
0.5804	Remote Similarity	NPD5696	Approved
0.5784	Remote Similarity	NPD4790	Discontinued
0.5781	Remote Similarity	NPD8293	Discontinued
0.578	Remote Similarity	NPD6399	Phase 3
0.5763	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.576	Remote Similarity	NPD8033	Approved
0.5752	Remote Similarity	NPD7639	Approved
0.5752	Remote Similarity	NPD7640	Approved
0.575	Remote Similarity	NPD8297	Approved
0.5728	Remote Similarity	NPD5209	Approved
0.5727	Remote Similarity	NPD6001	Approved
0.5726	Remote Similarity	NPD5697	Approved
0.5726	Remote Similarity	NPD6412	Phase 2
0.5714	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD6084	Phase 2
0.5701	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD6009	Approved
0.5688	Remote Similarity	NPD8035	Phase 2
0.5688	Remote Similarity	NPD8034	Phase 2
0.5686	Remote Similarity	NPD4252	Approved
0.5678	Remote Similarity	NPD6881	Approved
0.5678	Remote Similarity	NPD7320	Approved
0.5678	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6899	Approved
0.5667	Remote Similarity	NPD6650	Approved
0.5667	Remote Similarity	NPD6649	Approved
0.5648	Remote Similarity	NPD6673	Approved
0.5648	Remote Similarity	NPD6051	Approved
0.5648	Remote Similarity	NPD6080	Approved
0.5648	Remote Similarity	NPD6904	Approved
0.5645	Remote Similarity	NPD7328	Approved
0.5645	Remote Similarity	NPD7327	Approved
0.5641	Remote Similarity	NPD7128	Approved
0.5641	Remote Similarity	NPD6675	Approved
0.5641	Remote Similarity	NPD5739	Approved
0.5641	Remote Similarity	NPD6402	Approved
0.5636	Remote Similarity	NPD5779	Approved
0.5636	Remote Similarity	NPD5778	Approved
0.5635	Remote Similarity	NPD8515	Approved
0.5635	Remote Similarity	NPD8269	Approved
0.5635	Remote Similarity	NPD5983	Phase 2
0.5635	Remote Similarity	NPD8268	Approved
0.5635	Remote Similarity	NPD8517	Approved
0.5635	Remote Similarity	NPD8516	Approved
0.5635	Remote Similarity	NPD8513	Phase 3
0.5635	Remote Similarity	NPD8267	Approved
0.5635	Remote Similarity	NPD8266	Approved
0.563	Remote Similarity	NPD6014	Approved
0.563	Remote Similarity	NPD6372	Approved
0.563	Remote Similarity	NPD6013	Approved
0.563	Remote Similarity	NPD6373	Approved
0.563	Remote Similarity	NPD6012	Approved
0.56	Remote Similarity	NPD7516	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