NPASS Compound

Structure

CID166115 OpenBabel06191715532D 27 29 0 0 1 0 0 0 0 0999 V2000 1.6022 -5.6708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3835 -5.9096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4586 1.3465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3272 -2.2213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0024 -4.8707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0341 0.5138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7782 -2.6635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1288 -2.8259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0096 -4.9901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0342 0.5288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3288 -0.4417 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7971 -2.4703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7110 -0.4175 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3364 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5111 -1.0174 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5903 -4.1899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5410 -2.0169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1233 -2.7214 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -4.2752 -0.7650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5831 -4.3093 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5356 -1.9124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1972 -3.2704 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 1 5 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 5 9 2 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 7 20 1 0 0 0 0 8 20 1 0 0 0 0 8 21 1 0 0 0 0 9 18 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 6 0 0 0 13 15 1 0 0 0 0 13 26 1 6 0 0 0 14 10 1 6 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 11 1 6 0 0 0 15 17 1 0 0 0 0 16 20 1 6 0 0 0 17 27 1 1 0 0 0 18 23 2 0 0 0 0 18 26 1 0 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 20 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	396.13
Volume:	383.577
LogP:	0.932
LogD:	1.182
LogS:	-2.319
# Rotatable Bonds:	4
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.327
Synthetic Accessibility Score:	5.107
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.863
MDCK Permeability:	3.192061558365822e-05
Pgp-inhibitor:	0.087
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.731
20% Bioavailability (F20%):	0.406
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	79.41571807861328%
Volume Distribution (VD):	1.731
Pgp-substrate:	12.54750919342041%

ADMET: Metabolism

CYP1A2-inhibitor:	0.345
CYP1A2-substrate:	0.278
CYP2C19-inhibitor:	0.481
CYP2C19-substrate:	0.574
CYP2C9-inhibitor:	0.729
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.054
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.841
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	4.957
Half-life (T1/2):	0.81

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.586
AMES Toxicity:	0.132
Rat Oral Acute Toxicity:	0.649
Maximum Recommended Daily Dose:	0.133
Skin Sensitization:	0.347
Carcinogencity:	0.042
Eye Corrosion:	0.043
Eye Irritation:	0.073
Respiratory Toxicity:	0.94

Download Data

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

Natural Product: NPC166115

Natural Product ID:	NPC166115
*Common Name:**	Eupalinilide E
IUPAC Name:	[(3aR,4R,6R,6aS,7R,9aR,9bR)-6-(chloromethyl)-6,7-dihydroxy-9-methyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-4-yl] (E)-2-methylbut-2-enoate
Synonyms:	Eupalinilide E
Standard InCHIKey:	RQLHOJWFBMNYHW-PBDZIAQESA-N
Standard InCHI:	InChI=1S/C20H25ClO6/c1-5-9(2)18(23)26-13-7-20(25,8-21)16-12(22)6-10(3)14(16)17-15(13)11(4)19(24)27-17/h5-6,12-17,22,25H,4,7-8H2,1-3H3/b9-5+/t12-,13-,14+,15-,16-,17-,20+/m1/s1
SMILES:	C/C=C(C)/C(=O)O[C@@H]1C[C@](CCl)([C@@H]2[C@@H](C=C(C)[C@@H]2[C@@H]2[C@@H]1C(=C)C(=O)O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463970
PubChem CID:	11188671
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
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	Whole plant	Songyang County, Zhejiang Province, China	n.a.	PMID[15387644]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO851	Eupatorium lindleyanum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO851	Eupatorium lindleyanum	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
NPT81	Cell Line	A549	Homo sapiens	IC50	=	0.028	ug.mL-1	PMID[486010]

☑ 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 NPC166115 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	229
0.1-0.2	1372
0.2-0.3	5333
0.3-0.4	12502
0.4-0.5	12675
0.5-0.6	7023
0.6-0.7	2868
0.7-0.8	649
0.8-0.85	24
0.85-0.9	16
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9417	High Similarity	NPC35069
0.9417	High Similarity	NPC258711
0.9231	High Similarity	NPC189338
0.9231	High Similarity	NPC95290
0.8969	High Similarity	NPC477131
0.8878	High Similarity	NPC304886
0.8785	High Similarity	NPC273242
0.8776	High Similarity	NPC470013
0.8776	High Similarity	NPC262133
0.8776	High Similarity	NPC198853
0.8776	High Similarity	NPC470010
0.8776	High Similarity	NPC323008
0.8763	High Similarity	NPC133698
0.8763	High Similarity	NPC131209
0.8725	High Similarity	NPC86077
0.8704	High Similarity	NPC121816
0.8476	Intermediate Similarity	NPC243998
0.8455	Intermediate Similarity	NPC255450
0.8455	Intermediate Similarity	NPC170692
0.8384	Intermediate Similarity	NPC475925
0.8333	Intermediate Similarity	NPC161493
0.8318	Intermediate Similarity	NPC68248
0.8317	Intermediate Similarity	NPC67584
0.8317	Intermediate Similarity	NPC52044
0.8302	Intermediate Similarity	NPC223450
0.83	Intermediate Similarity	NPC135776
0.8269	Intermediate Similarity	NPC150923
0.8265	Intermediate Similarity	NPC91248
0.8235	Intermediate Similarity	NPC213078
0.8137	Intermediate Similarity	NPC170120
0.8137	Intermediate Similarity	NPC213698
0.8119	Intermediate Similarity	NPC228451
0.8119	Intermediate Similarity	NPC125674
0.8119	Intermediate Similarity	NPC475838
0.81	Intermediate Similarity	NPC475855
0.81	Intermediate Similarity	NPC129419
0.8081	Intermediate Similarity	NPC217983
0.8081	Intermediate Similarity	NPC207114
0.8077	Intermediate Similarity	NPC221615
0.8058	Intermediate Similarity	NPC24956
0.8058	Intermediate Similarity	NPC18019
0.8039	Intermediate Similarity	NPC474338
0.8039	Intermediate Similarity	NPC127019
0.8039	Intermediate Similarity	NPC474247
0.8037	Intermediate Similarity	NPC100487
0.802	Intermediate Similarity	NPC184063
0.8	Intermediate Similarity	NPC295312
0.8	Intermediate Similarity	NPC4986
0.8	Intermediate Similarity	NPC268298
0.8	Intermediate Similarity	NPC215556
0.8	Intermediate Similarity	NPC32922
0.798	Intermediate Similarity	NPC160138
0.7941	Intermediate Similarity	NPC475912
0.7921	Intermediate Similarity	NPC301969
0.7921	Intermediate Similarity	NPC179394
0.7921	Intermediate Similarity	NPC144133
0.7921	Intermediate Similarity	NPC19087
0.7921	Intermediate Similarity	NPC216284
0.7921	Intermediate Similarity	NPC37607
0.7909	Intermediate Similarity	NPC115352
0.7905	Intermediate Similarity	NPC141191
0.7905	Intermediate Similarity	NPC187268
0.79	Intermediate Similarity	NPC79549
0.789	Intermediate Similarity	NPC26617
0.7885	Intermediate Similarity	NPC279621
0.7885	Intermediate Similarity	NPC230800
0.7879	Intermediate Similarity	NPC305475
0.7879	Intermediate Similarity	NPC64153
0.7879	Intermediate Similarity	NPC107787
0.7879	Intermediate Similarity	NPC187661
0.7879	Intermediate Similarity	NPC475461
0.787	Intermediate Similarity	NPC203659
0.7864	Intermediate Similarity	NPC167219
0.7822	Intermediate Similarity	NPC38392
0.781	Intermediate Similarity	NPC170143
0.781	Intermediate Similarity	NPC108475
0.781	Intermediate Similarity	NPC169205
0.781	Intermediate Similarity	NPC213947
0.78	Intermediate Similarity	NPC237540
0.7798	Intermediate Similarity	NPC54737
0.7788	Intermediate Similarity	NPC270013
0.7788	Intermediate Similarity	NPC14961
0.7788	Intermediate Similarity	NPC220221
0.7788	Intermediate Similarity	NPC36954
0.7788	Intermediate Similarity	NPC472873
0.7778	Intermediate Similarity	NPC124881
0.7778	Intermediate Similarity	NPC255307
0.7778	Intermediate Similarity	NPC110989
0.7778	Intermediate Similarity	NPC475871
0.7778	Intermediate Similarity	NPC475945
0.7778	Intermediate Similarity	NPC165162
0.7778	Intermediate Similarity	NPC78089
0.7767	Intermediate Similarity	NPC81419
0.7767	Intermediate Similarity	NPC258216
0.7767	Intermediate Similarity	NPC179746
0.7757	Intermediate Similarity	NPC171759
0.7755	Intermediate Similarity	NPC250315
0.7745	Intermediate Similarity	NPC54065
0.7745	Intermediate Similarity	NPC473448
0.7745	Intermediate Similarity	NPC297474
0.7723	Intermediate Similarity	NPC178875
0.7723	Intermediate Similarity	NPC202672
0.7714	Intermediate Similarity	NPC476315
0.7714	Intermediate Similarity	NPC185553
0.77	Intermediate Similarity	NPC67493
0.7692	Intermediate Similarity	NPC474035
0.7692	Intermediate Similarity	NPC81386
0.7685	Intermediate Similarity	NPC291500
0.7685	Intermediate Similarity	NPC197835
0.7685	Intermediate Similarity	NPC189609
0.7685	Intermediate Similarity	NPC474747
0.7685	Intermediate Similarity	NPC225353
0.7685	Intermediate Similarity	NPC303653
0.7685	Intermediate Similarity	NPC140591
0.7679	Intermediate Similarity	NPC257240
0.7677	Intermediate Similarity	NPC115786
0.7677	Intermediate Similarity	NPC476804
0.7677	Intermediate Similarity	NPC194859
0.7677	Intermediate Similarity	NPC191476
0.7677	Intermediate Similarity	NPC165287
0.7677	Intermediate Similarity	NPC224386
0.7677	Intermediate Similarity	NPC114979
0.767	Intermediate Similarity	NPC171360
0.767	Intermediate Similarity	NPC133888
0.767	Intermediate Similarity	NPC35959
0.767	Intermediate Similarity	NPC300312
0.767	Intermediate Similarity	NPC184463
0.767	Intermediate Similarity	NPC12172
0.767	Intermediate Similarity	NPC111114
0.767	Intermediate Similarity	NPC155215
0.767	Intermediate Similarity	NPC293001
0.767	Intermediate Similarity	NPC208886
0.767	Intermediate Similarity	NPC29821
0.767	Intermediate Similarity	NPC57304
0.767	Intermediate Similarity	NPC30515
0.767	Intermediate Similarity	NPC63193
0.767	Intermediate Similarity	NPC261607
0.7664	Intermediate Similarity	NPC288876
0.7664	Intermediate Similarity	NPC70865
0.7653	Intermediate Similarity	NPC89555
0.7647	Intermediate Similarity	NPC155935
0.7647	Intermediate Similarity	NPC212664
0.7642	Intermediate Similarity	NPC474313
0.7642	Intermediate Similarity	NPC471462
0.7642	Intermediate Similarity	NPC477949
0.7632	Intermediate Similarity	NPC209058
0.7629	Intermediate Similarity	NPC276356
0.7624	Intermediate Similarity	NPC118601
0.7619	Intermediate Similarity	NPC193645
0.7619	Intermediate Similarity	NPC48803
0.7619	Intermediate Similarity	NPC90121
0.7619	Intermediate Similarity	NPC476053
0.7619	Intermediate Similarity	NPC163228
0.7619	Intermediate Similarity	NPC275960
0.76	Intermediate Similarity	NPC300082
0.76	Intermediate Similarity	NPC284534
0.76	Intermediate Similarity	NPC215364
0.76	Intermediate Similarity	NPC235792
0.76	Intermediate Similarity	NPC204105
0.7596	Intermediate Similarity	NPC212486
0.7596	Intermediate Similarity	NPC476300
0.7593	Intermediate Similarity	NPC474742
0.7589	Intermediate Similarity	NPC59489
0.7589	Intermediate Similarity	NPC139838
0.7586	Intermediate Similarity	NPC475323
0.7576	Intermediate Similarity	NPC169575
0.7576	Intermediate Similarity	NPC40746
0.7576	Intermediate Similarity	NPC128246
0.7576	Intermediate Similarity	NPC131669
0.7576	Intermediate Similarity	NPC473390
0.7573	Intermediate Similarity	NPC476004
0.7573	Intermediate Similarity	NPC51004
0.7573	Intermediate Similarity	NPC62815
0.7573	Intermediate Similarity	NPC474761
0.7573	Intermediate Similarity	NPC71533
0.7573	Intermediate Similarity	NPC106510
0.7573	Intermediate Similarity	NPC469368
0.7573	Intermediate Similarity	NPC35809
0.757	Intermediate Similarity	NPC473326
0.7565	Intermediate Similarity	NPC471380
0.7549	Intermediate Similarity	NPC476805
0.7545	Intermediate Similarity	NPC474741
0.7544	Intermediate Similarity	NPC76550
0.7544	Intermediate Similarity	NPC123855
0.7525	Intermediate Similarity	NPC50637
0.7525	Intermediate Similarity	NPC309757
0.7525	Intermediate Similarity	NPC236692
0.7525	Intermediate Similarity	NPC150755
0.7525	Intermediate Similarity	NPC470242
0.7525	Intermediate Similarity	NPC284902
0.7524	Intermediate Similarity	NPC303942
0.7524	Intermediate Similarity	NPC57405
0.7522	Intermediate Similarity	NPC471884
0.75	Intermediate Similarity	NPC96259
0.75	Intermediate Similarity	NPC473321
0.75	Intermediate Similarity	NPC472958
0.75	Intermediate Similarity	NPC141193
0.75	Intermediate Similarity	NPC156485
0.75	Intermediate Similarity	NPC212363
0.75	Intermediate Similarity	NPC472957

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 NPC166115 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	191
0.1-0.2	1875
0.2-0.3	3910
0.3-0.4	2284
0.4-0.5	573
0.5-0.6	261
0.6-0.7	51
0.7-0.8	4
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
0.8	Intermediate Similarity	NPD1695	Approved
0.789	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6371	Approved
0.7619	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD6053	Discontinued
0.7075	Intermediate Similarity	NPD6698	Approved
0.7075	Intermediate Similarity	NPD46	Approved
0.7059	Intermediate Similarity	NPD5362	Discontinued
0.7019	Intermediate Similarity	NPD4249	Approved
0.6952	Remote Similarity	NPD4250	Approved
0.6952	Remote Similarity	NPD4251	Approved
0.6916	Remote Similarity	NPD5785	Approved
0.6893	Remote Similarity	NPD7154	Phase 3
0.6881	Remote Similarity	NPD5282	Discontinued
0.6762	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5363	Approved
0.6762	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD7838	Discovery
0.6637	Remote Similarity	NPD4225	Approved
0.6637	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6686	Approved
0.6602	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4819	Approved
0.6602	Remote Similarity	NPD4821	Approved
0.6602	Remote Similarity	NPD4822	Approved
0.6602	Remote Similarity	NPD4820	Approved
0.6583	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7639	Approved
0.6579	Remote Similarity	NPD7640	Approved
0.6545	Remote Similarity	NPD7983	Approved
0.6522	Remote Similarity	NPD5344	Discontinued
0.6508	Remote Similarity	NPD5983	Phase 2
0.6491	Remote Similarity	NPD7638	Approved
0.6486	Remote Similarity	NPD5778	Approved
0.6486	Remote Similarity	NPD5779	Approved
0.648	Remote Similarity	NPD7100	Approved
0.6476	Remote Similarity	NPD4270	Approved
0.6476	Remote Similarity	NPD4269	Approved
0.6452	Remote Similarity	NPD7115	Discovery
0.6415	Remote Similarity	NPD5331	Approved
0.6415	Remote Similarity	NPD5332	Approved
0.6408	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4271	Approved
0.6408	Remote Similarity	NPD4268	Approved
0.64	Remote Similarity	NPD6313	Approved
0.64	Remote Similarity	NPD6335	Approved
0.64	Remote Similarity	NPD6314	Approved
0.6389	Remote Similarity	NPD5786	Approved
0.6381	Remote Similarity	NPD4790	Discontinued
0.6381	Remote Similarity	NPD5369	Approved
0.6364	Remote Similarity	NPD5956	Approved
0.6349	Remote Similarity	NPD7101	Approved
0.6341	Remote Similarity	NPD4632	Approved
0.6321	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6435	Approved
0.6316	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6336	Discontinued
0.6303	Remote Similarity	NPD6008	Approved
0.6296	Remote Similarity	NPD1694	Approved
0.6293	Remote Similarity	NPD6648	Approved
0.6286	Remote Similarity	NPD4252	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.6212	Remote Similarity	NPD6033	Approved
0.6195	Remote Similarity	NPD6399	Phase 3
0.619	Remote Similarity	NPD6009	Approved
0.6183	Remote Similarity	NPD7507	Approved
0.6179	Remote Similarity	NPD5215	Approved
0.6148	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD5368	Approved
0.6124	Remote Similarity	NPD8516	Approved
0.6124	Remote Similarity	NPD8517	Approved
0.6124	Remote Similarity	NPD8515	Approved
0.6124	Remote Similarity	NPD8513	Phase 3
0.6121	Remote Similarity	NPD6083	Phase 2
0.6121	Remote Similarity	NPD6084	Phase 2
0.6116	Remote Similarity	NPD5697	Approved
0.6111	Remote Similarity	NPD6868	Approved
0.6098	Remote Similarity	NPD5169	Approved
0.6098	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6094	Remote Similarity	NPD4522	Approved
0.6087	Remote Similarity	NPD5695	Phase 3
0.6068	Remote Similarity	NPD5696	Approved
0.6066	Remote Similarity	NPD6899	Approved
0.6066	Remote Similarity	NPD7320	Approved
0.6066	Remote Similarity	NPD6881	Approved
0.6055	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.605	Remote Similarity	NPD7632	Discontinued
0.6048	Remote Similarity	NPD6649	Approved
0.6048	Remote Similarity	NPD1719	Phase 1
0.6048	Remote Similarity	NPD6650	Approved
0.6048	Remote Similarity	NPD5216	Approved
0.6048	Remote Similarity	NPD5127	Approved
0.6048	Remote Similarity	NPD5217	Approved
0.6045	Remote Similarity	NPD7319	Approved
0.6034	Remote Similarity	NPD7839	Suspended
0.6033	Remote Similarity	NPD7128	Approved
0.6033	Remote Similarity	NPD6402	Approved
0.6033	Remote Similarity	NPD5739	Approved
0.6033	Remote Similarity	NPD6675	Approved
0.6032	Remote Similarity	NPD5167	Approved
0.6019	Remote Similarity	NPD5209	Approved
0.6016	Remote Similarity	NPD6373	Approved
0.6016	Remote Similarity	NPD6012	Approved
0.6016	Remote Similarity	NPD6372	Approved
0.6016	Remote Similarity	NPD6014	Approved
0.6016	Remote Similarity	NPD6013	Approved
0.5985	Remote Similarity	NPD7492	Approved
0.5984	Remote Similarity	NPD6614	Approved
0.5984	Remote Similarity	NPD5701	Approved
0.5968	Remote Similarity	NPD7290	Approved
0.5968	Remote Similarity	NPD7102	Approved
0.5968	Remote Similarity	NPD6883	Approved
0.5963	Remote Similarity	NPD6695	Phase 3
0.594	Remote Similarity	NPD6616	Approved
0.5935	Remote Similarity	NPD6011	Approved
0.5935	Remote Similarity	NPD5128	Approved
0.5929	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD6101	Approved
0.5923	Remote Similarity	NPD6054	Approved
0.5923	Remote Similarity	NPD6319	Approved
0.592	Remote Similarity	NPD8130	Phase 1
0.592	Remote Similarity	NPD6617	Approved
0.592	Remote Similarity	NPD6869	Approved
0.592	Remote Similarity	NPD6847	Approved
0.5917	Remote Similarity	NPD5091	Approved
0.5917	Remote Similarity	NPD5211	Phase 2
0.5909	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD8074	Phase 3
0.5896	Remote Similarity	NPD7078	Approved
0.5891	Remote Similarity	NPD7328	Approved
0.5891	Remote Similarity	NPD7327	Approved
0.5878	Remote Similarity	NPD6016	Approved
0.5878	Remote Similarity	NPD6015	Approved
0.5878	Remote Similarity	NPD8033	Approved
0.5873	Remote Similarity	NPD8297	Approved
0.5873	Remote Similarity	NPD6882	Approved
0.5859	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD6412	Phase 2
0.5852	Remote Similarity	NPD7736	Approved
0.5846	Remote Similarity	NPD7516	Approved
0.5833	Remote Similarity	NPD6370	Approved
0.5833	Remote Similarity	NPD5988	Approved
0.5826	Remote Similarity	NPD5693	Phase 1
0.5826	Remote Similarity	NPD5281	Approved
0.5826	Remote Similarity	NPD5284	Approved
0.5826	Remote Similarity	NPD6411	Approved
0.5821	Remote Similarity	NPD8273	Phase 1
0.582	Remote Similarity	NPD5141	Approved
0.5812	Remote Similarity	NPD5654	Approved
0.5812	Remote Similarity	NPD5210	Approved
0.5812	Remote Similarity	NPD4629	Approved
0.5812	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD5168	Approved
0.5802	Remote Similarity	NPD8294	Approved
0.5802	Remote Similarity	NPD6059	Approved
0.5802	Remote Similarity	NPD8377	Approved
0.5789	Remote Similarity	NPD4753	Phase 2
0.5778	Remote Similarity	NPD8293	Discontinued
0.5766	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD8378	Approved
0.5758	Remote Similarity	NPD8296	Approved
0.5758	Remote Similarity	NPD8379	Approved
0.5758	Remote Similarity	NPD7503	Approved
0.5758	Remote Similarity	NPD8380	Approved
0.5758	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD8335	Approved
0.5752	Remote Similarity	NPD7750	Discontinued
0.5752	Remote Similarity	NPD7524	Approved
0.575	Remote Similarity	NPD4696	Approved
0.575	Remote Similarity	NPD5285	Approved
0.575	Remote Similarity	NPD5286	Approved
0.5745	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD5207	Approved
0.5736	Remote Similarity	NPD6274	Approved
0.5725	Remote Similarity	NPD7260	Phase 2
0.5714	Remote Similarity	NPD5959	Approved
0.5714	Remote Similarity	NPD4755	Approved
0.5714	Remote Similarity	NPD7902	Approved
0.5702	Remote Similarity	NPD6903	Approved
0.5702	Remote Similarity	NPD6672	Approved
0.5702	Remote Similarity	NPD5737	Approved
0.5701	Remote Similarity	NPD4756	Discovery
0.5688	Remote Similarity	NPD7332	Phase 2
0.5688	Remote Similarity	NPD6931	Approved
0.5688	Remote Similarity	NPD6930	Phase 2
0.5683	Remote Similarity	NPD6845	Suspended
0.5676	Remote Similarity	NPD6110	Phase 1
0.5672	Remote Similarity	NPD7642	Approved
0.5672	Remote Similarity	NPD7604	Phase 2
0.5669	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD6684	Approved
0.5664	Remote Similarity	NPD5279	Phase 3
0.5664	Remote Similarity	NPD7146	Approved
0.5664	Remote Similarity	NPD7521	Approved
0.5664	Remote Similarity	NPD3618	Phase 1
0.5664	Remote Similarity	NPD7334	Approved
0.5664	Remote Similarity	NPD6409	Approved
0.5664	Remote Similarity	NPD5330	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