NPASS Compound

Structure

CID139838 OpenBabel06191715502D 28 32 0 0 1 0 0 0 0 0999 V2000 -0.2982 -4.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5862 -2.0089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3167 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3097 1.2929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0757 -3.6640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2999 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8087 -2.9838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0077 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2748 -1.6235 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0567 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7870 1.2594 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2999 0.4010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0567 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4449 2.0125 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7643 -3.2786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5955 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3645 1.6195 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2748 0.6235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2090 1.3491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9868 -4.2535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5955 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8427 -0.1996 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 -2.4974 -2.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0077 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2451 2.6123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 8 1 0 0 0 0 3 9 2 0 0 0 0 4 18 1 0 0 0 0 5 8 2 0 0 0 0 6 10 1 0 0 0 0 7 19 1 0 0 0 0 7 25 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 26 1 1 0 0 0 11 9 1 1 0 0 0 11 14 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 12 21 1 1 0 0 0 13 19 1 1 0 0 0 13 20 1 0 0 0 0 14 20 1 6 0 0 0 14 27 1 0 0 0 0 15 18 1 1 0 0 0 15 28 1 0 0 0 0 16 22 2 0 0 0 0 16 26 1 0 0 0 0 17 23 2 0 0 0 0 17 27 1 0 0 0 0 18 20 1 6 0 0 0 18 28 1 0 0 0 0 19 6 1 6 0 0 0 19 25 1 0 0 0 0 20 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	392.15
Volume:	371.47
LogP:	0.662
LogD:	0.425
LogS:	-3.215
# Rotatable Bonds:	3
TPSA:	118.12
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.383
Synthetic Accessibility Score:	5.877
Fsp3:	0.7
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:	-5.218
MDCK Permeability:	2.3891239834483713e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.095
Human Intestinal Absorption (HIA):	0.183
20% Bioavailability (F20%):	0.672
30% Bioavailability (F30%):	0.89

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.184
Plasma Protein Binding (PPB):	49.006439208984375%
Volume Distribution (VD):	1.503
Pgp-substrate:	42.645660400390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.378
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.674
CYP2C9-inhibitor:	0.114
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.5
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	3.559
Half-life (T1/2):	0.864

ADMET: Toxicity

hERG Blockers:	0.149
Human Hepatotoxicity (H-HT):	0.634
Drug-inuced Liver Injury (DILI):	0.925
AMES Toxicity:	0.193
Rat Oral Acute Toxicity:	0.393
Maximum Recommended Daily Dose:	0.463
Skin Sensitization:	0.53
Carcinogencity:	0.168
Eye Corrosion:	0.007
Eye Irritation:	0.04
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC139838

Natural Product ID:	NPC139838
*Common Name:**	Eupatoroxin
IUPAC Name:	n.a.
Synonyms:	Eupatoroxin
Standard InCHIKey:	QUSNLLJZMPVTTC-ZDHOEGKISA-N
Standard InCHI:	InChI=1S/C20H24O8/c1-5-8(2)16(22)26-10-6-19(7-25-19)13-12(21)15-18(4,28-15)20(13,24)14-11(10)9(3)17(23)27-14/h5,10-15,21,24H,3,6-7H2,1-2,4H3/b8-5-/t10-,11-,12+,13+,14+,15-,18-,19+,20-/m1/s1
SMILES:	C/C=C(/C)C(=O)O[C@@H]1C[C@]2(CO2)[C@@H]2[C@@H]([C@@H]3[C@](C)([C@@]2([C@@H]2[C@@H]1C(=C)C(=O)O2)O)O3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL399672
PubChem CID:	5281462
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:0002046] Ambrosanolides and secoambrosanolides

*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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]
NPO26385	Eupatorium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26385	Eupatorium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26385	Eupatorium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26385	Eupatorium rotundifolium	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
ED50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.8	ug ml-1	PMID[534218]
NPT91	Cell Line	KB	Homo sapiens	pED50	=	5.15	n.a.	PMID[534218]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	7.14	umol/L	PMID[534219]

☑ 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 NPC139838 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	297
0.1-0.2	1962
0.2-0.3	6601
0.3-0.4	14302
0.4-0.5	10364
0.5-0.6	6216
0.6-0.7	2341
0.7-0.8	548
0.8-0.85	44
0.85-0.9	9
0.9-0.95	4
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC59489
0.97	High Similarity	NPC54737
0.92	High Similarity	NPC471381
0.92	High Similarity	NPC186861
0.91	High Similarity	NPC45125
0.9074	High Similarity	NPC255450
0.9074	High Similarity	NPC170692
0.9	High Similarity	NPC471150
0.8942	High Similarity	NPC243998
0.8942	High Similarity	NPC223450
0.8807	High Similarity	NPC121816
0.88	High Similarity	NPC472873
0.8762	High Similarity	NPC44004
0.8716	High Similarity	NPC273242
0.8614	High Similarity	NPC476053
0.8558	High Similarity	NPC150923
0.8544	High Similarity	NPC474213
0.8529	High Similarity	NPC24956
0.8529	High Similarity	NPC18019
0.85	High Similarity	NPC155215
0.8447	Intermediate Similarity	NPC161493
0.8416	Intermediate Similarity	NPC258216
0.8407	Intermediate Similarity	NPC475401
0.84	Intermediate Similarity	NPC216284
0.8381	Intermediate Similarity	NPC171759
0.8365	Intermediate Similarity	NPC221615
0.835	Intermediate Similarity	NPC213078
0.8333	Intermediate Similarity	NPC477092
0.8319	Intermediate Similarity	NPC475305
0.8317	Intermediate Similarity	NPC475925
0.8302	Intermediate Similarity	NPC86077
0.83	Intermediate Similarity	NPC472872
0.83	Intermediate Similarity	NPC215556
0.8288	Intermediate Similarity	NPC475851
0.8288	Intermediate Similarity	NPC475924
0.8273	Intermediate Similarity	NPC50223
0.8269	Intermediate Similarity	NPC181151
0.8257	Intermediate Similarity	NPC117604
0.8252	Intermediate Similarity	NPC163228
0.8252	Intermediate Similarity	NPC270013
0.8252	Intermediate Similarity	NPC14961
0.8252	Intermediate Similarity	NPC52044
0.8252	Intermediate Similarity	NPC213698
0.8252	Intermediate Similarity	NPC67584
0.8235	Intermediate Similarity	NPC212486
0.8224	Intermediate Similarity	NPC124881
0.82	Intermediate Similarity	NPC79549
0.819	Intermediate Similarity	NPC473326
0.8173	Intermediate Similarity	NPC476315
0.8165	Intermediate Similarity	NPC477513
0.8165	Intermediate Similarity	NPC26617
0.8155	Intermediate Similarity	NPC81386
0.8155	Intermediate Similarity	NPC127019
0.8155	Intermediate Similarity	NPC474035
0.8155	Intermediate Similarity	NPC477131
0.8148	Intermediate Similarity	NPC100487
0.8148	Intermediate Similarity	NPC474741
0.8137	Intermediate Similarity	NPC35959
0.8137	Intermediate Similarity	NPC70251
0.8137	Intermediate Similarity	NPC475881
0.8137	Intermediate Similarity	NPC29821
0.8137	Intermediate Similarity	NPC63193
0.8137	Intermediate Similarity	NPC57304
0.8137	Intermediate Similarity	NPC133888
0.8137	Intermediate Similarity	NPC171360
0.8137	Intermediate Similarity	NPC293001
0.8125	Intermediate Similarity	NPC189338
0.8125	Intermediate Similarity	NPC258711
0.8125	Intermediate Similarity	NPC95290
0.8125	Intermediate Similarity	NPC35069
0.8113	Intermediate Similarity	NPC70865
0.8108	Intermediate Similarity	NPC193741
0.8108	Intermediate Similarity	NPC41551
0.81	Intermediate Similarity	NPC270270
0.8095	Intermediate Similarity	NPC213947
0.8095	Intermediate Similarity	NPC311904
0.8095	Intermediate Similarity	NPC108475
0.8095	Intermediate Similarity	NPC474313
0.8095	Intermediate Similarity	NPC170143
0.8077	Intermediate Similarity	NPC36954
0.8077	Intermediate Similarity	NPC170120
0.8058	Intermediate Similarity	NPC476300
0.8058	Intermediate Similarity	NPC472874
0.8058	Intermediate Similarity	NPC81419
0.8058	Intermediate Similarity	NPC179746
0.8058	Intermediate Similarity	NPC475912
0.8056	Intermediate Similarity	NPC475945
0.8056	Intermediate Similarity	NPC475871
0.8039	Intermediate Similarity	NPC54065
0.8039	Intermediate Similarity	NPC35809
0.8039	Intermediate Similarity	NPC297474
0.8036	Intermediate Similarity	NPC475495
0.802	Intermediate Similarity	NPC178875
0.802	Intermediate Similarity	NPC217983
0.802	Intermediate Similarity	NPC207114
0.8	Intermediate Similarity	NPC476009
0.8	Intermediate Similarity	NPC91771
0.8	Intermediate Similarity	NPC142529
0.8	Intermediate Similarity	NPC64153
0.8	Intermediate Similarity	NPC279621
0.8	Intermediate Similarity	NPC470242
0.8	Intermediate Similarity	NPC126156
0.7982	Intermediate Similarity	NPC203659
0.7981	Intermediate Similarity	NPC470010
0.7981	Intermediate Similarity	NPC323008
0.7981	Intermediate Similarity	NPC262133
0.7981	Intermediate Similarity	NPC470013
0.7981	Intermediate Similarity	NPC198853
0.7965	Intermediate Similarity	NPC475277
0.7965	Intermediate Similarity	NPC477093
0.7965	Intermediate Similarity	NPC473522
0.7963	Intermediate Similarity	NPC80144
0.7963	Intermediate Similarity	NPC474747
0.7961	Intermediate Similarity	NPC184463
0.7961	Intermediate Similarity	NPC30515
0.7961	Intermediate Similarity	NPC208886
0.7961	Intermediate Similarity	NPC131209
0.7961	Intermediate Similarity	NPC184063
0.7961	Intermediate Similarity	NPC133698
0.7961	Intermediate Similarity	NPC12172
0.7949	Intermediate Similarity	NPC143755
0.7946	Intermediate Similarity	NPC477103
0.7944	Intermediate Similarity	NPC288876
0.7941	Intermediate Similarity	NPC92974
0.7941	Intermediate Similarity	NPC155935
0.7928	Intermediate Similarity	NPC68248
0.7921	Intermediate Similarity	NPC190753
0.7921	Intermediate Similarity	NPC186148
0.7921	Intermediate Similarity	NPC118601
0.7905	Intermediate Similarity	NPC304886
0.7905	Intermediate Similarity	NPC220221
0.79	Intermediate Similarity	NPC204105
0.79	Intermediate Similarity	NPC300082
0.79	Intermediate Similarity	NPC284534
0.789	Intermediate Similarity	NPC110989
0.7885	Intermediate Similarity	NPC135776
0.7876	Intermediate Similarity	NPC474750
0.787	Intermediate Similarity	NPC201718
0.787	Intermediate Similarity	NPC476270
0.787	Intermediate Similarity	NPC474742
0.787	Intermediate Similarity	NPC67296
0.787	Intermediate Similarity	NPC477950
0.7869	Intermediate Similarity	NPC475371
0.7864	Intermediate Similarity	NPC37607
0.7864	Intermediate Similarity	NPC475748
0.7864	Intermediate Similarity	NPC51004
0.7864	Intermediate Similarity	NPC301969
0.7864	Intermediate Similarity	NPC19087
0.7857	Intermediate Similarity	NPC115352
0.7857	Intermediate Similarity	NPC477102
0.785	Intermediate Similarity	NPC249171
0.785	Intermediate Similarity	NPC49833
0.785	Intermediate Similarity	NPC208233
0.7843	Intermediate Similarity	NPC58219
0.7843	Intermediate Similarity	NPC177629
0.7843	Intermediate Similarity	NPC471149
0.7843	Intermediate Similarity	NPC202672
0.7838	Intermediate Similarity	NPC197813
0.7838	Intermediate Similarity	NPC148270
0.7838	Intermediate Similarity	NPC80338
0.783	Intermediate Similarity	NPC98165
0.783	Intermediate Similarity	NPC473859
0.7826	Intermediate Similarity	NPC265290
0.7826	Intermediate Similarity	NPC305044
0.7822	Intermediate Similarity	NPC187661
0.7822	Intermediate Similarity	NPC236692
0.7822	Intermediate Similarity	NPC309757
0.781	Intermediate Similarity	NPC303942
0.781	Intermediate Similarity	NPC474247
0.781	Intermediate Similarity	NPC473316
0.781	Intermediate Similarity	NPC57405
0.781	Intermediate Similarity	NPC473330
0.7798	Intermediate Similarity	NPC320019
0.7798	Intermediate Similarity	NPC324017
0.7798	Intermediate Similarity	NPC225353
0.7798	Intermediate Similarity	NPC471148
0.7788	Intermediate Similarity	NPC257240
0.7778	Intermediate Similarity	NPC161060
0.7767	Intermediate Similarity	NPC4986
0.7767	Intermediate Similarity	NPC38392
0.7767	Intermediate Similarity	NPC283409
0.7767	Intermediate Similarity	NPC307411
0.7757	Intermediate Similarity	NPC236580
0.7757	Intermediate Similarity	NPC304445
0.7748	Intermediate Similarity	NPC470980
0.7748	Intermediate Similarity	NPC170432
0.7745	Intermediate Similarity	NPC231889
0.7745	Intermediate Similarity	NPC24728
0.7739	Intermediate Similarity	NPC101400
0.7739	Intermediate Similarity	NPC101965
0.7736	Intermediate Similarity	NPC37408
0.7736	Intermediate Similarity	NPC224689
0.7736	Intermediate Similarity	NPC475900
0.7736	Intermediate Similarity	NPC475659
0.7736	Intermediate Similarity	NPC471141
0.7727	Intermediate Similarity	NPC123505
0.7727	Intermediate Similarity	NPC474775
0.7727	Intermediate Similarity	NPC473148
0.7724	Intermediate Similarity	NPC13071
0.7723	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 NPC139838 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	2589
0.2-0.3	3905
0.3-0.4	1629
0.4-0.5	431
0.5-0.6	209
0.6-0.7	42
0.7-0.8	4
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
0.8165	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD6371	Approved
0.7767	Intermediate Similarity	NPD1695	Approved
0.7524	Intermediate Similarity	NPD46	Approved
0.7524	Intermediate Similarity	NPD6698	Approved
0.75	Intermediate Similarity	NPD6053	Discontinued
0.7248	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7838	Discovery
0.6981	Remote Similarity	NPD4249	Approved
0.693	Remote Similarity	NPD5344	Discontinued
0.6929	Remote Similarity	NPD7507	Approved
0.6916	Remote Similarity	NPD4251	Approved
0.6916	Remote Similarity	NPD4250	Approved
0.6838	Remote Similarity	NPD6008	Approved
0.6818	Remote Similarity	NPD7983	Approved
0.68	Remote Similarity	NPD6319	Approved
0.6769	Remote Similarity	NPD7319	Approved
0.6762	Remote Similarity	NPD6435	Approved
0.6729	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5785	Approved
0.6723	Remote Similarity	NPD6686	Approved
0.6698	Remote Similarity	NPD5362	Discontinued
0.6694	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD7492	Approved
0.6585	Remote Similarity	NPD4632	Approved
0.6574	Remote Similarity	NPD5363	Approved
0.6571	Remote Similarity	NPD4821	Approved
0.6571	Remote Similarity	NPD4819	Approved
0.6571	Remote Similarity	NPD5368	Approved
0.6571	Remote Similarity	NPD4820	Approved
0.6571	Remote Similarity	NPD4822	Approved
0.6571	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6648	Approved
0.6538	Remote Similarity	NPD6616	Approved
0.6535	Remote Similarity	NPD6054	Approved
0.6514	Remote Similarity	NPD5786	Approved
0.6504	Remote Similarity	NPD8297	Approved
0.6489	Remote Similarity	NPD7078	Approved
0.6484	Remote Similarity	NPD6015	Approved
0.6484	Remote Similarity	NPD6016	Approved
0.6484	Remote Similarity	NPD8033	Approved
0.6466	Remote Similarity	NPD4225	Approved
0.6466	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD7736	Approved
0.6434	Remote Similarity	NPD6370	Approved
0.6434	Remote Similarity	NPD5988	Approved
0.6423	Remote Similarity	NPD6649	Approved
0.6423	Remote Similarity	NPD6650	Approved
0.6406	Remote Similarity	NPD6059	Approved
0.6393	Remote Similarity	NPD6373	Approved
0.6393	Remote Similarity	NPD6372	Approved
0.6389	Remote Similarity	NPD7154	Phase 3
0.6381	Remote Similarity	NPD4271	Approved
0.6381	Remote Similarity	NPD4268	Approved
0.6378	Remote Similarity	NPD7327	Approved
0.6378	Remote Similarity	NPD7328	Approved
0.6364	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5697	Approved
0.6364	Remote Similarity	NPD8293	Discontinued
0.6357	Remote Similarity	NPD8515	Approved
0.6357	Remote Similarity	NPD8517	Approved
0.6357	Remote Similarity	NPD8513	Phase 3
0.6357	Remote Similarity	NPD8516	Approved
0.6355	Remote Similarity	NPD5369	Approved
0.6333	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7516	Approved
0.6325	Remote Similarity	NPD7638	Approved
0.6311	Remote Similarity	NPD7320	Approved
0.6311	Remote Similarity	NPD6881	Approved
0.6311	Remote Similarity	NPD6899	Approved
0.6299	Remote Similarity	NPD6009	Approved
0.6296	Remote Similarity	NPD4269	Approved
0.6296	Remote Similarity	NPD4270	Approved
0.6281	Remote Similarity	NPD6675	Approved
0.6281	Remote Similarity	NPD5739	Approved
0.6281	Remote Similarity	NPD7128	Approved
0.6281	Remote Similarity	NPD6402	Approved
0.6279	Remote Similarity	NPD8294	Approved
0.6279	Remote Similarity	NPD8377	Approved
0.6271	Remote Similarity	NPD7640	Approved
0.6271	Remote Similarity	NPD7639	Approved
0.6261	Remote Similarity	NPD5282	Discontinued
0.626	Remote Similarity	NPD6012	Approved
0.626	Remote Similarity	NPD7642	Approved
0.626	Remote Similarity	NPD6014	Approved
0.626	Remote Similarity	NPD7604	Phase 2
0.626	Remote Similarity	NPD6013	Approved
0.624	Remote Similarity	NPD6882	Approved
0.6239	Remote Similarity	NPD5331	Approved
0.6239	Remote Similarity	NPD5332	Approved
0.6231	Remote Similarity	NPD5983	Phase 2
0.6231	Remote Similarity	NPD8378	Approved
0.6231	Remote Similarity	NPD7503	Approved
0.6231	Remote Similarity	NPD8296	Approved
0.6231	Remote Similarity	NPD8380	Approved
0.6231	Remote Similarity	NPD8335	Approved
0.6231	Remote Similarity	NPD8379	Approved
0.623	Remote Similarity	NPD5701	Approved
0.623	Remote Similarity	NPD6412	Phase 2
0.621	Remote Similarity	NPD7102	Approved
0.621	Remote Similarity	NPD6883	Approved
0.621	Remote Similarity	NPD7290	Approved
0.621	Remote Similarity	NPD4634	Approved
0.6204	Remote Similarity	NPD4790	Discontinued
0.619	Remote Similarity	NPD8133	Approved
0.6179	Remote Similarity	NPD6011	Approved
0.6174	Remote Similarity	NPD5778	Approved
0.6174	Remote Similarity	NPD5779	Approved
0.616	Remote Similarity	NPD6847	Approved
0.616	Remote Similarity	NPD8130	Phase 1
0.616	Remote Similarity	NPD6869	Approved
0.616	Remote Similarity	NPD6617	Approved
0.6136	Remote Similarity	NPD7829	Approved
0.6136	Remote Similarity	NPD7830	Approved
0.6119	Remote Similarity	NPD8074	Phase 3
0.6111	Remote Similarity	NPD4252	Approved
0.6102	Remote Similarity	NPD6084	Phase 2
0.6102	Remote Similarity	NPD6083	Phase 2
0.6083	Remote Similarity	NPD1700	Approved
0.6071	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5695	Phase 3
0.6058	Remote Similarity	NPD7260	Phase 2
0.605	Remote Similarity	NPD5696	Approved
0.6048	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6045	Remote Similarity	NPD8273	Phase 1
0.6045	Remote Similarity	NPD6336	Discontinued
0.6033	Remote Similarity	NPD5211	Phase 2
0.6014	Remote Similarity	NPD6845	Suspended
0.6	Remote Similarity	NPD5285	Approved
0.6	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD4696	Approved
0.5985	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5969	Remote Similarity	NPD6274	Approved
0.5966	Remote Similarity	NPD4755	Approved
0.5956	Remote Similarity	NPD6033	Approved
0.5935	Remote Similarity	NPD5141	Approved
0.5932	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD4633	Approved
0.5902	Remote Similarity	NPD5224	Approved
0.5902	Remote Similarity	NPD5225	Approved
0.5902	Remote Similarity	NPD5226	Approved
0.5897	Remote Similarity	NPD6399	Phase 3
0.5882	Remote Similarity	NPD7839	Suspended
0.5878	Remote Similarity	NPD7641	Discontinued
0.587	Remote Similarity	NPD5956	Approved
0.5868	Remote Similarity	NPD4700	Approved
0.5856	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD5174	Approved
0.5854	Remote Similarity	NPD5175	Approved
0.5847	Remote Similarity	NPD6001	Approved
0.5841	Remote Similarity	NPD1694	Approved
0.5833	Remote Similarity	NPD7100	Approved
0.5833	Remote Similarity	NPD7101	Approved
0.582	Remote Similarity	NPD5223	Approved
0.5812	Remote Similarity	NPD5693	Phase 1
0.5812	Remote Similarity	NPD5284	Approved
0.5812	Remote Similarity	NPD7637	Suspended
0.5812	Remote Similarity	NPD5281	Approved
0.5809	Remote Similarity	NPD8451	Approved
0.5802	Remote Similarity	NPD6317	Approved
0.5798	Remote Similarity	NPD4629	Approved
0.5798	Remote Similarity	NPD5210	Approved
0.5794	Remote Similarity	NPD4729	Approved
0.5794	Remote Similarity	NPD4730	Approved
0.5776	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6101	Approved
0.5776	Remote Similarity	NPD4753	Phase 2
0.5772	Remote Similarity	NPD7632	Discontinued
0.5766	Remote Similarity	NPD8448	Approved
0.576	Remote Similarity	NPD4768	Approved
0.576	Remote Similarity	NPD4767	Approved
0.5758	Remote Similarity	NPD6314	Approved
0.5758	Remote Similarity	NPD6313	Approved
0.5758	Remote Similarity	NPD6335	Approved
0.5755	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD8268	Approved
0.5746	Remote Similarity	NPD8266	Approved
0.5746	Remote Similarity	NPD8269	Approved
0.5746	Remote Similarity	NPD8267	Approved
0.5739	Remote Similarity	NPD7524	Approved
0.5726	Remote Similarity	NPD5207	Approved
0.5714	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5209	Approved
0.5703	Remote Similarity	NPD5249	Phase 3
0.5703	Remote Similarity	NPD5250	Approved
0.5703	Remote Similarity	NPD5251	Approved
0.5703	Remote Similarity	NPD5248	Approved
0.5703	Remote Similarity	NPD5247	Approved
0.569	Remote Similarity	NPD6903	Approved
0.5686	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6411	Approved
0.5669	Remote Similarity	NPD5128	Approved
0.5664	Remote Similarity	NPD6110	Phase 1

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