NPASS Compound

Structure

CID108433 OpenBabel06191715462D 25 29 0 0 1 0 0 0 0 0999 V2000 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0029 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0029 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1369 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1369 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2709 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2709 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2709 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4049 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0029 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1369 -1.0000 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 2.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4049 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 9 1 0 0 0 0 5 11 2 0 0 0 0 6 10 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 8 23 1 0 0 0 0 9 16 1 0 0 0 0 9 17 2 0 0 0 0 10 12 1 0 0 0 0 10 18 2 0 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 12 24 1 0 0 0 0 13 15 2 0 0 0 0 13 22 1 0 0 0 0 14 6 1 1 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 18 1 0 0 0 0 16 21 2 0 0 0 0 17 25 1 0 0 0 0 18 25 1 0 0 0 0 19 1 1 1 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	340.09
Volume:	328.684
LogP:	3.574
LogD:	2.582
LogS:	-4.913
# Rotatable Bonds:	2
TPSA:	81.43
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	3.731
Fsp3:	0.316
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.808
MDCK Permeability:	1.7540460248710588e-05
Pgp-inhibitor:	0.07
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.061

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	88.67029571533203%
Volume Distribution (VD):	0.617
Pgp-substrate:	8.603269577026367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.819
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.578
CYP2C19-substrate:	0.225
CYP2C9-inhibitor:	0.747
CYP2C9-substrate:	0.83
CYP2D6-inhibitor:	0.082
CYP2D6-substrate:	0.634
CYP3A4-inhibitor:	0.404
CYP3A4-substrate:	0.181

ADMET: Excretion

Clearance (CL):	3.663
Half-life (T1/2):	0.736

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.968
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.738
Rat Oral Acute Toxicity:	0.811
Maximum Recommended Daily Dose:	0.622
Skin Sensitization:	0.62
Carcinogencity:	0.892
Eye Corrosion:	0.004
Eye Irritation:	0.369
Respiratory Toxicity:	0.598

Download Data

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

Natural Product: NPC108433

Natural Product ID:	NPC108433
*Common Name:**	Psorospermin
IUPAC Name:	(2R)-10-hydroxy-5-methoxy-2-[(2R)-2-methyloxiran-2-yl]-1,2-dihydrofuro[2,3-c]xanthen-6-one
Synonyms:	Psorospermin
Standard InCHIKey:	BBNDPXOGORGETN-AUUYWEPGSA-N
Standard InCHI:	InChI=1S/C19H16O6/c1-19(8-23-19)14-6-10-12(24-14)7-13(22-2)15-16(21)9-4-3-5-11(20)17(9)25-18(10)15/h3-5,7,14,20H,6,8H2,1-2H3/t14-,19-/m1/s1
SMILES:	COc1cc2O[C@H](Cc2c2c1c(=O)c1c(o2)c(O)ccc1)[C@@]1(C)CO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL369474
PubChem CID:	126451
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO12096	Psorospermum febrifugum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191562]
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21682262]
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	whole plants	Zhejiang Province, China	2008-AUG	PMID[21682262]
NPO12096	Psorospermum febrifugum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7189773]
NPO12096	Psorospermum febrifugum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12096	Psorospermum febrifugum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9680	Ajuga ciliata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15613	Clerodendrum uncinatum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4475	Erythrina costaricensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1645	Sticta pulmonaria	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10519	Angylocalyx vermeulenii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7544	Squalus wakiyae	Species	Squalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12096	Psorospermum febrifugum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15236	Leucetta avocado	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13912	Delphinium gracile	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26692	Lophium arboricola	Species	Mytilinidiaceae	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	4
IC50	17
Others	2

Activity Type	# Activity
Cell Line	22
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	1110.0	nM	PMID[497526]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	210.0	nM	PMID[497526]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1460.0	nM	PMID[497526]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	570.0	nM	PMID[497526]
NPT2505	Cell Line	NCI-H520		IC50	=	770.0	nM	PMID[497526]
NPT389	Cell Line	RPMI-8226	Homo sapiens	IC50	=	290.0	nM	PMID[497526]
NPT389	Cell Line	RPMI-8226	Homo sapiens	IC50	=	230.0	nM	PMID[497526]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	270.0	nM	PMID[497526]
NPT4241	Cell Line	Granta		IC50	=	40.0	nM	PMID[497526]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	380.0	nM	PMID[497526]
NPT2641	Cell Line	COLO 320	Homo sapiens	IC50	=	69.0	nM	PMID[497527]
NPT455	Cell Line	NCI-H522	Homo sapiens	IC50	=	450.0	nM	PMID[497527]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	640.0	nM	PMID[497527]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	210.0	nM	PMID[497527]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	710.0	nM	PMID[497527]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	380.0	nM	PMID[497527]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.6	10'-3 ug/ml	PMID[497528]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	1.0	10'-5 ug/ml	PMID[497528]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	1.2	10'-2 ug/ml	PMID[497528]
NPT168	Cell Line	P388	Mus musculus	T/C	=	158.0	%	PMID[497529]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.1	ug ml-1	PMID[497529]
NPT168	Cell Line	P388	Mus musculus	T/C	=	158.0	%	PMID[497530]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	290.0	nM	PMID[497530]

☑ 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 NPC108433 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	459
0.1-0.2	1906
0.2-0.3	4719
0.3-0.4	10881
0.4-0.5	6915
0.5-0.6	4126
0.6-0.7	5418
0.7-0.8	4861
0.8-0.85	2118
0.85-0.9	1114
0.9-0.95	176
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9809	High Similarity	NPC235610
0.9808	High Similarity	NPC124038
0.9745	High Similarity	NPC300053
0.9742	High Similarity	NPC472624
0.962	High Similarity	NPC472277
0.9618	High Similarity	NPC472635
0.9615	High Similarity	NPC328102
0.9613	High Similarity	NPC27337
0.9613	High Similarity	NPC291508
0.9563	High Similarity	NPC288813
0.956	High Similarity	NPC119589
0.9557	High Similarity	NPC205265
0.9557	High Similarity	NPC472281
0.9557	High Similarity	NPC18100
0.9554	High Similarity	NPC134783
0.9548	High Similarity	NPC291878
0.9548	High Similarity	NPC195796
0.9548	High Similarity	NPC278778
0.9548	High Similarity	NPC35038
0.9494	High Similarity	NPC81679
0.9494	High Similarity	NPC474034
0.9494	High Similarity	NPC474033
0.949	High Similarity	NPC119209
0.949	High Similarity	NPC192686
0.949	High Similarity	NPC118256
0.9487	High Similarity	NPC472598
0.9487	High Similarity	NPC474055
0.9484	High Similarity	NPC256925
0.9484	High Similarity	NPC470327
0.9484	High Similarity	NPC152951
0.9484	High Similarity	NPC477503
0.9484	High Similarity	NPC57674
0.9484	High Similarity	NPC168247
0.9484	High Similarity	NPC117992
0.9484	High Similarity	NPC230149
0.9484	High Similarity	NPC45849
0.9484	High Similarity	NPC200761
0.9437	High Similarity	NPC170245
0.943	High Similarity	NPC472632
0.943	High Similarity	NPC474038
0.943	High Similarity	NPC472634
0.943	High Similarity	NPC471210
0.9427	High Similarity	NPC250214
0.9427	High Similarity	NPC204879
0.9427	High Similarity	NPC95936
0.9423	High Similarity	NPC472626
0.9423	High Similarity	NPC470328
0.9423	High Similarity	NPC472455
0.9423	High Similarity	NPC209614
0.9419	High Similarity	NPC192083
0.9419	High Similarity	NPC227337
0.9419	High Similarity	NPC273462
0.9419	High Similarity	NPC18727
0.9419	High Similarity	NPC49402
0.9419	High Similarity	NPC74924
0.9419	High Similarity	NPC70433
0.9419	High Similarity	NPC33051
0.9419	High Similarity	NPC213896
0.9383	High Similarity	NPC472276
0.9375	High Similarity	NPC62261
0.9375	High Similarity	NPC326520
0.9371	High Similarity	NPC472448
0.9371	High Similarity	NPC474162
0.9371	High Similarity	NPC476247
0.9371	High Similarity	NPC83922
0.9371	High Similarity	NPC474150
0.9367	High Similarity	NPC287328
0.9367	High Similarity	NPC472630
0.9367	High Similarity	NPC174953
0.9367	High Similarity	NPC282009
0.9367	High Similarity	NPC476980
0.9367	High Similarity	NPC472631
0.9367	High Similarity	NPC475784
0.9367	High Similarity	NPC36217
0.9363	High Similarity	NPC52889
0.9363	High Similarity	NPC218313
0.9363	High Similarity	NPC99597
0.9363	High Similarity	NPC129684
0.9363	High Similarity	NPC162869
0.9363	High Similarity	NPC67876
0.9363	High Similarity	NPC156057
0.9363	High Similarity	NPC284820
0.9363	High Similarity	NPC474208
0.9363	High Similarity	NPC78225
0.9363	High Similarity	NPC210084
0.9363	High Similarity	NPC475267
0.9363	High Similarity	NPC48208
0.9363	High Similarity	NPC262286
0.9363	High Similarity	NPC474836
0.9363	High Similarity	NPC474681
0.9363	High Similarity	NPC299520
0.9363	High Similarity	NPC223787
0.9363	High Similarity	NPC471209
0.9363	High Similarity	NPC36852
0.9363	High Similarity	NPC473272
0.9359	High Similarity	NPC226025
0.9359	High Similarity	NPC234255
0.9359	High Similarity	NPC472280
0.9359	High Similarity	NPC321779
0.9355	High Similarity	NPC473996
0.9355	High Similarity	NPC106976
0.9355	High Similarity	NPC477231
0.9355	High Similarity	NPC302950
0.9355	High Similarity	NPC236637
0.9355	High Similarity	NPC219582
0.9355	High Similarity	NPC257648
0.9321	High Similarity	NPC152477
0.9317	High Similarity	NPC173292
0.9313	High Similarity	NPC475985
0.9313	High Similarity	NPC472278
0.9313	High Similarity	NPC329669
0.9313	High Similarity	NPC473313
0.9313	High Similarity	NPC186686
0.9313	High Similarity	NPC472582
0.9313	High Similarity	NPC472625
0.9308	High Similarity	NPC29876
0.9308	High Similarity	NPC471211
0.9308	High Similarity	NPC26326
0.9308	High Similarity	NPC167678
0.9308	High Similarity	NPC266314
0.9308	High Similarity	NPC471212
0.9308	High Similarity	NPC471499
0.9304	High Similarity	NPC55738
0.9304	High Similarity	NPC473990
0.9304	High Similarity	NPC22192
0.9304	High Similarity	NPC184755
0.9304	High Similarity	NPC74178
0.9299	High Similarity	NPC6633
0.9299	High Similarity	NPC138243
0.9299	High Similarity	NPC255106
0.9299	High Similarity	NPC191146
0.9299	High Similarity	NPC235165
0.9299	High Similarity	NPC68093
0.9299	High Similarity	NPC470600
0.9299	High Similarity	NPC472916
0.9299	High Similarity	NPC133970
0.9299	High Similarity	NPC5322
0.9299	High Similarity	NPC474638
0.9295	High Similarity	NPC298692
0.929	High Similarity	NPC31363
0.929	High Similarity	NPC472636
0.929	High Similarity	NPC472580
0.9268	High Similarity	NPC310794
0.9264	High Similarity	NPC131866
0.9264	High Similarity	NPC212748
0.9259	High Similarity	NPC150131
0.9255	High Similarity	NPC293319
0.925	High Similarity	NPC261470
0.925	High Similarity	NPC201800
0.925	High Similarity	NPC472964
0.9245	High Similarity	NPC470326
0.9245	High Similarity	NPC204290
0.9245	High Similarity	NPC476283
0.9245	High Similarity	NPC472902
0.9241	High Similarity	NPC471515
0.9241	High Similarity	NPC187745
0.9241	High Similarity	NPC472911
0.9241	High Similarity	NPC180011
0.9241	High Similarity	NPC472913
0.9241	High Similarity	NPC96167
0.9241	High Similarity	NPC472914
0.9241	High Similarity	NPC136674
0.9241	High Similarity	NPC471479
0.9241	High Similarity	NPC219867
0.9241	High Similarity	NPC222814
0.9241	High Similarity	NPC161960
0.9241	High Similarity	NPC304008
0.9241	High Similarity	NPC472910
0.9241	High Similarity	NPC245758
0.9241	High Similarity	NPC476981
0.9241	High Similarity	NPC52530
0.9236	High Similarity	NPC200246
0.9236	High Similarity	NPC31018
0.9236	High Similarity	NPC255807
0.9236	High Similarity	NPC113906
0.9236	High Similarity	NPC37392
0.9236	High Similarity	NPC2928
0.9231	High Similarity	NPC477957
0.9231	High Similarity	NPC237994
0.9231	High Similarity	NPC31627
0.9231	High Similarity	NPC471982
0.9231	High Similarity	NPC39732
0.9231	High Similarity	NPC60972
0.9231	High Similarity	NPC327269
0.9231	High Similarity	NPC476238
0.9231	High Similarity	NPC472912
0.9226	High Similarity	NPC472421
0.9226	High Similarity	NPC338131
0.9226	High Similarity	NPC29231
0.9207	High Similarity	NPC121333
0.9202	High Similarity	NPC242395
0.9202	High Similarity	NPC165456
0.9198	High Similarity	NPC471213
0.9198	High Similarity	NPC128293
0.9198	High Similarity	NPC277480
0.9198	High Similarity	NPC43319
0.9193	High Similarity	NPC273959
0.9193	High Similarity	NPC41301
0.9187	High Similarity	NPC45124
0.9187	High Similarity	NPC258331

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 NPC108433 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	976
0.2-0.3	1922
0.3-0.4	2707
0.4-0.5	1730
0.5-0.6	963
0.6-0.7	307
0.7-0.8	101
0.8-0.85	21
0.85-0.9	14
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9419	High Similarity	NPD2393	Clinical (unspecified phase)
0.9355	High Similarity	NPD1934	Approved
0.9177	High Similarity	NPD3882	Suspended
0.9051	High Similarity	NPD2801	Approved
0.9024	High Similarity	NPD3818	Discontinued
0.9006	High Similarity	NPD5494	Approved
0.8902	High Similarity	NPD6168	Clinical (unspecified phase)
0.8902	High Similarity	NPD6167	Clinical (unspecified phase)
0.8902	High Similarity	NPD6166	Phase 2
0.8742	High Similarity	NPD4380	Phase 2
0.8718	High Similarity	NPD1511	Approved
0.8704	High Similarity	NPD4868	Clinical (unspecified phase)
0.869	High Similarity	NPD7074	Phase 3
0.865	High Similarity	NPD7075	Discontinued
0.8631	High Similarity	NPD7054	Approved
0.8608	High Similarity	NPD1512	Approved
0.858	High Similarity	NPD7096	Clinical (unspecified phase)
0.858	High Similarity	NPD7472	Approved
0.8544	High Similarity	NPD4378	Clinical (unspecified phase)
0.8528	High Similarity	NPD3817	Phase 2
0.8516	High Similarity	NPD1549	Phase 2
0.8452	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6797	Phase 2
0.8372	Intermediate Similarity	NPD7251	Discontinued
0.8372	Intermediate Similarity	NPD6559	Discontinued
0.8354	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8324	Intermediate Similarity	NPD7808	Phase 3
0.8313	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD5844	Phase 1
0.8303	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD7473	Discontinued
0.8293	Intermediate Similarity	NPD6801	Discontinued
0.8274	Intermediate Similarity	NPD1247	Approved
0.8269	Intermediate Similarity	NPD2796	Approved
0.8232	Intermediate Similarity	NPD7411	Suspended
0.8208	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD1510	Phase 2
0.8198	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD6959	Discontinued
0.8155	Intermediate Similarity	NPD919	Approved
0.8137	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD1465	Phase 2
0.807	Intermediate Similarity	NPD3926	Phase 2
0.8065	Intermediate Similarity	NPD943	Approved
0.8065	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD2800	Approved
0.7988	Intermediate Similarity	NPD3749	Approved
0.7976	Intermediate Similarity	NPD5402	Approved
0.7975	Intermediate Similarity	NPD2532	Approved
0.7975	Intermediate Similarity	NPD2534	Approved
0.7975	Intermediate Similarity	NPD2533	Approved
0.7962	Intermediate Similarity	NPD1607	Approved
0.7952	Intermediate Similarity	NPD6599	Discontinued
0.7949	Intermediate Similarity	NPD1613	Approved
0.7949	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD920	Approved
0.7877	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6234	Discontinued
0.7829	Intermediate Similarity	NPD3751	Discontinued
0.7824	Intermediate Similarity	NPD7768	Phase 2
0.7812	Intermediate Similarity	NPD2935	Discontinued
0.7806	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD230	Phase 1
0.7778	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5403	Approved
0.7758	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD3027	Phase 3
0.7754	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD7685	Pre-registration
0.7747	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD3787	Discontinued
0.7673	Intermediate Similarity	NPD447	Suspended
0.7669	Intermediate Similarity	NPD1243	Approved
0.7663	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2344	Approved
0.7651	Intermediate Similarity	NPD5401	Approved
0.7647	Intermediate Similarity	NPD37	Approved
0.7644	Intermediate Similarity	NPD7199	Phase 2
0.7636	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7228	Approved
0.7622	Intermediate Similarity	NPD3750	Approved
0.7622	Intermediate Similarity	NPD4628	Phase 3
0.7616	Intermediate Similarity	NPD4966	Approved
0.7616	Intermediate Similarity	NPD4967	Phase 2
0.7616	Intermediate Similarity	NPD4965	Approved
0.7611	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD5953	Discontinued
0.7593	Intermediate Similarity	NPD1551	Phase 2
0.759	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7286	Phase 2
0.7576	Intermediate Similarity	NPD6190	Approved
0.7574	Intermediate Similarity	NPD3226	Approved
0.7557	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2346	Discontinued
0.7541	Intermediate Similarity	NPD8434	Phase 2
0.7531	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD9494	Approved
0.7515	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD6099	Approved
0.7485	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD8312	Approved
0.7473	Intermediate Similarity	NPD8313	Approved
0.747	Intermediate Similarity	NPD2309	Approved
0.7453	Intermediate Similarity	NPD1933	Approved
0.741	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6651	Approved
0.7394	Intermediate Similarity	NPD2424	Discontinued
0.7384	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6781	Approved
0.7382	Intermediate Similarity	NPD6778	Approved
0.7382	Intermediate Similarity	NPD6779	Approved
0.7382	Intermediate Similarity	NPD6776	Approved
0.7382	Intermediate Similarity	NPD6780	Approved
0.7382	Intermediate Similarity	NPD6782	Approved
0.7382	Intermediate Similarity	NPD6777	Approved
0.7375	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD8150	Discontinued
0.7333	Intermediate Similarity	NPD7584	Approved
0.7317	Intermediate Similarity	NPD3748	Approved
0.7317	Intermediate Similarity	NPD7033	Discontinued
0.7316	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7229	Phase 3
0.7302	Intermediate Similarity	NPD4363	Phase 3
0.7302	Intermediate Similarity	NPD4360	Phase 2
0.7278	Intermediate Similarity	NPD7390	Discontinued
0.7268	Intermediate Similarity	NPD7435	Discontinued
0.7263	Intermediate Similarity	NPD5242	Approved
0.7259	Intermediate Similarity	NPD8151	Discontinued
0.7257	Intermediate Similarity	NPD5353	Approved
0.725	Intermediate Similarity	NPD4908	Phase 1
0.7235	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2403	Approved
0.7205	Intermediate Similarity	NPD4625	Phase 3
0.72	Intermediate Similarity	NPD5760	Phase 2
0.72	Intermediate Similarity	NPD5761	Phase 2
0.7192	Intermediate Similarity	NPD4111	Phase 1
0.7179	Intermediate Similarity	NPD7697	Approved
0.7179	Intermediate Similarity	NPD7696	Phase 3
0.7179	Intermediate Similarity	NPD7698	Approved
0.7174	Intermediate Similarity	NPD7240	Approved
0.7173	Intermediate Similarity	NPD4361	Phase 2
0.7173	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1203	Approved
0.7168	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD2493	Approved
0.7165	Intermediate Similarity	NPD2494	Approved
0.7158	Intermediate Similarity	NPD1729	Discontinued
0.7143	Intermediate Similarity	NPD4583	Approved
0.7143	Intermediate Similarity	NPD4582	Approved
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD6844	Discontinued
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7134	Intermediate Similarity	NPD1610	Phase 2
0.7134	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5124	Phase 1
0.7128	Intermediate Similarity	NPD6823	Phase 2
0.7126	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7907	Approved
0.7121	Intermediate Similarity	NPD7701	Phase 2
0.712	Intermediate Similarity	NPD6535	Approved
0.712	Intermediate Similarity	NPD6534	Approved
0.712	Intermediate Similarity	NPD3823	Discontinued
0.7119	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4665	Approved
0.71	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7783	Phase 2
0.7092	Intermediate Similarity	NPD4004	Approved
0.7092	Intermediate Similarity	NPD4002	Approved
0.709	Intermediate Similarity	NPD4287	Approved
0.7089	Intermediate Similarity	NPD9269	Phase 2
0.7086	Intermediate Similarity	NPD6386	Approved
0.7086	Intermediate Similarity	NPD6385	Approved
0.7081	Intermediate Similarity	NPD2861	Phase 2
0.7077	Intermediate Similarity	NPD3450	Approved
0.7077	Intermediate Similarity	NPD3452	Approved
0.7076	Intermediate Similarity	NPD4357	Discontinued
0.7069	Intermediate Similarity	NPD7458	Discontinued
0.7056	Intermediate Similarity	NPD8127	Discontinued
0.7055	Intermediate Similarity	NPD3764	Approved
0.7055	Intermediate Similarity	NPD6798	Discontinued

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