NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.04
Volume:	218.571
LogP:	1.918
LogD:	1.891
LogS:	-3.214
# Rotatable Bonds:	1
TPSA:	72.81
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.651
Synthetic Accessibility Score:	2.686
Fsp3:	0.083
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.872
MDCK Permeability:	2.5673261916381307e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.392

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	82.2080307006836%
Volume Distribution (VD):	0.813
Pgp-substrate:	15.343658447265625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.886
CYP2C19-inhibitor:	0.198
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.529
CYP2C9-substrate:	0.674
CYP2D6-inhibitor:	0.774
CYP2D6-substrate:	0.441
CYP3A4-inhibitor:	0.507
CYP3A4-substrate:	0.165

ADMET: Excretion

Clearance (CL):	13.542
Half-life (T1/2):	0.779

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.788
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.171
Rat Oral Acute Toxicity:	0.911
Maximum Recommended Daily Dose:	0.058
Skin Sensitization:	0.524
Carcinogencity:	0.85
Eye Corrosion:	0.003
Eye Irritation:	0.21
Respiratory Toxicity:	0.787

Download Data

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

Natural Product: NPC281835

Natural Product ID:	NPC281835
*Common Name:**	8-Hydroxy-5-Methoxy Psoralen
IUPAC Name:	9-hydroxy-4-methoxyfuro[3,2-g]chromen-7-one
Synonyms:
Standard InCHIKey:	MVJHUMZXIJPVHV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H8O5/c1-15-10-6-2-3-8(13)17-12(6)9(14)11-7(10)4-5-16-11/h2-5,14H,1H3
SMILES:	COc1c2ccc(=O)oc2c(c2c1cco2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1934069
PubChem CID:	3083726
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0000358] Furanocoumarins [CHEMONTID:0002569] Linear furanocoumarins [CHEMONTID:0000202] Psoralens [CHEMONTID:0002832] 5-methoxypsoralens

*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
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	DOI[10.5012/bkcs.2003.24.11.1699]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	seed	n.a.	PMID[10075120]
NPO7344	Spiraea prunifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473429]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[12510838]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[15646793]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499335]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17228877]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19615910]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[21657081]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27444348]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29323912]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31464439]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[731398]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7714541]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760071]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7798964]
NPO19895	Plectranthus hereroensis	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[7931371]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964801]
NPO23356	Ascodesmis sphaerospora	Species	Ascodesmidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868168]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8471	Angelica taiwaniana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8471	Angelica taiwaniana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23588	Ursinia anthemoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30713	Angelica talwaniana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24758	Angelica dahurica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9814	Lactarius fuliginosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16614	Zanthoxylum spinosum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23588	Ursinia anthemoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17492	Amomum reticulatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23490	Dalbergia monetaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23356	Ascodesmis sphaerospora	Species	Ascodesmidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19895	Plectranthus hereroensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8471	Angelica taiwaniana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24396	Grosvenoria rimbachii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15572	Espeletiopsis purpurascens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23398	Caralluma russeliana	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7344	Spiraea prunifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23822	Polypodium aureum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24280	Helianthus californicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24038	Casimiroa edulis	Species	Rutaceae	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
Others	3

Activity Type	# Activity
Cell Line	2
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	34.6	%	PMID[500146]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	38.1	%	PMID[500146]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	>	500000.0	nM	PMID[500145]
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	Inhibition	=	8.2	%	PMID[500145]

☑ 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 NPC281835 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	485
0.1-0.2	2221
0.2-0.3	5651
0.3-0.4	11387
0.4-0.5	5868
0.5-0.6	4211
0.6-0.7	5792
0.7-0.8	4714
0.8-0.85	1613
0.85-0.9	702
0.9-0.95	50
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9876	High Similarity	NPC233956
0.9563	High Similarity	NPC15819
0.9515	High Similarity	NPC107244
0.95	High Similarity	NPC234536
0.95	High Similarity	NPC78612
0.9455	High Similarity	NPC224165
0.9455	High Similarity	NPC53917
0.9441	High Similarity	NPC179464
0.9325	High Similarity	NPC193881
0.9325	High Similarity	NPC210460
0.9325	High Similarity	NPC67450
0.9325	High Similarity	NPC155264
0.924	High Similarity	NPC73703
0.9193	High Similarity	NPC33320
0.9157	High Similarity	NPC144288
0.9157	High Similarity	NPC51404
0.9141	High Similarity	NPC238995
0.9136	High Similarity	NPC243509
0.9085	High Similarity	NPC59295
0.9085	High Similarity	NPC263092
0.9085	High Similarity	NPC1755
0.9085	High Similarity	NPC39305
0.9085	High Similarity	NPC1706
0.908	High Similarity	NPC264293
0.908	High Similarity	NPC216092
0.9074	High Similarity	NPC16935
0.9068	High Similarity	NPC19860
0.9036	High Similarity	NPC247973
0.9036	High Similarity	NPC241820
0.903	High Similarity	NPC45449
0.903	High Similarity	NPC36320
0.9018	High Similarity	NPC169
0.8994	High Similarity	NPC155882
0.8963	High Similarity	NPC188486
0.8957	High Similarity	NPC196879
0.8951	High Similarity	NPC472461
0.8941	High Similarity	NPC164384
0.8935	High Similarity	NPC261471
0.8935	High Similarity	NPC310794
0.8935	High Similarity	NPC277510
0.8929	High Similarity	NPC131866
0.8929	High Similarity	NPC28042
0.8916	High Similarity	NPC179015
0.8916	High Similarity	NPC173149
0.8916	High Similarity	NPC38914
0.8909	High Similarity	NPC272722
0.8909	High Similarity	NPC312056
0.8909	High Similarity	NPC81679
0.8909	High Similarity	NPC84515
0.8902	High Similarity	NPC95472
0.8902	High Similarity	NPC239270
0.8902	High Similarity	NPC303210
0.8896	High Similarity	NPC270044
0.8889	High Similarity	NPC297807
0.8889	High Similarity	NPC98546
0.8862	High Similarity	NPC277480
0.8848	High Similarity	NPC14822
0.8841	High Similarity	NPC195832
0.8834	High Similarity	NPC45131
0.883	High Similarity	NPC49667
0.883	High Similarity	NPC8127
0.8824	High Similarity	NPC37606
0.8824	High Similarity	NPC72455
0.8817	High Similarity	NPC218533
0.8817	High Similarity	NPC78830
0.881	High Similarity	NPC86477
0.8805	High Similarity	NPC74539
0.8805	High Similarity	NPC304443
0.8802	High Similarity	NPC29411
0.8802	High Similarity	NPC291110
0.8802	High Similarity	NPC37183
0.8795	High Similarity	NPC261470
0.8788	High Similarity	NPC476980
0.8788	High Similarity	NPC246478
0.8788	High Similarity	NPC49009
0.8786	High Similarity	NPC97523
0.878	High Similarity	NPC269495
0.8773	High Similarity	NPC201451
0.8773	High Similarity	NPC44079
0.8773	High Similarity	NPC26227
0.8773	High Similarity	NPC39184
0.8772	High Similarity	NPC289244
0.8772	High Similarity	NPC287243
0.8765	High Similarity	NPC54098
0.8765	High Similarity	NPC125300
0.8765	High Similarity	NPC39007
0.8765	High Similarity	NPC161277
0.8765	High Similarity	NPC307286
0.8765	High Similarity	NPC230619
0.8757	High Similarity	NPC280493
0.8757	High Similarity	NPC60848
0.8743	High Similarity	NPC470459
0.8743	High Similarity	NPC65846
0.8743	High Similarity	NPC133065
0.8743	High Similarity	NPC234004
0.8742	High Similarity	NPC226987
0.8742	High Similarity	NPC143903
0.8735	High Similarity	NPC258331
0.8735	High Similarity	NPC308992
0.8728	High Similarity	NPC183843
0.8727	High Similarity	NPC83763
0.8727	High Similarity	NPC193842
0.8727	High Similarity	NPC168616
0.8721	High Similarity	NPC24258
0.872	High Similarity	NPC43243
0.872	High Similarity	NPC98661
0.872	High Similarity	NPC245546
0.872	High Similarity	NPC247017
0.872	High Similarity	NPC266960
0.872	High Similarity	NPC49824
0.8713	High Similarity	NPC65885
0.8713	High Similarity	NPC216842
0.8713	High Similarity	NPC82217
0.8713	High Similarity	NPC476640
0.8712	High Similarity	NPC271779
0.8712	High Similarity	NPC206238
0.8712	High Similarity	NPC167091
0.8712	High Similarity	NPC292214
0.8712	High Similarity	NPC88645
0.8706	High Similarity	NPC472276
0.8704	High Similarity	NPC171010
0.8704	High Similarity	NPC225731
0.8704	High Similarity	NPC98028
0.8698	High Similarity	NPC186392
0.8698	High Similarity	NPC50394
0.8698	High Similarity	NPC470704
0.8696	High Similarity	NPC88445
0.869	High Similarity	NPC470457
0.869	High Similarity	NPC50960
0.869	High Similarity	NPC39306
0.869	High Similarity	NPC329215
0.869	High Similarity	NPC204088
0.869	High Similarity	NPC259007
0.8688	High Similarity	NPC61871
0.8688	High Similarity	NPC55557
0.8688	High Similarity	NPC30647
0.8688	High Similarity	NPC251188
0.8683	High Similarity	NPC8300
0.8683	High Similarity	NPC83922
0.8683	High Similarity	NPC193998
0.8683	High Similarity	NPC472448
0.8675	High Similarity	NPC130955
0.8675	High Similarity	NPC263449
0.8675	High Similarity	NPC328102
0.8667	High Similarity	NPC176665
0.8667	High Similarity	NPC224137
0.8667	High Similarity	NPC163524
0.8667	High Similarity	NPC78225
0.8667	High Similarity	NPC227192
0.8667	High Similarity	NPC203891
0.8667	High Similarity	NPC189179
0.8667	High Similarity	NPC101830
0.8667	High Similarity	NPC287979
0.8667	High Similarity	NPC305663
0.8667	High Similarity	NPC36852
0.8667	High Similarity	NPC93376
0.8667	High Similarity	NPC99597
0.8667	High Similarity	NPC75215
0.8667	High Similarity	NPC210084
0.8667	High Similarity	NPC476981
0.8667	High Similarity	NPC110070
0.8667	High Similarity	NPC262286
0.8663	High Similarity	NPC236327
0.8663	High Similarity	NPC290304
0.8663	High Similarity	NPC139350
0.8659	High Similarity	NPC213622
0.8659	High Similarity	NPC134287
0.8659	High Similarity	NPC20830
0.8659	High Similarity	NPC130589
0.8659	High Similarity	NPC250769
0.8659	High Similarity	NPC18954
0.8659	High Similarity	NPC295608
0.8659	High Similarity	NPC256612
0.8659	High Similarity	NPC278010
0.8659	High Similarity	NPC2928
0.8655	High Similarity	NPC174700
0.8655	High Similarity	NPC157522
0.8655	High Similarity	NPC247964
0.865	High Similarity	NPC212678
0.865	High Similarity	NPC216769
0.865	High Similarity	NPC199100
0.865	High Similarity	NPC27208
0.865	High Similarity	NPC188203
0.865	High Similarity	NPC131266
0.865	High Similarity	NPC275836
0.865	High Similarity	NPC156222
0.865	High Similarity	NPC180234
0.865	High Similarity	NPC100263
0.865	High Similarity	NPC120537
0.865	High Similarity	NPC269451
0.865	High Similarity	NPC100971
0.865	High Similarity	NPC121522
0.865	High Similarity	NPC162313
0.865	High Similarity	NPC304954
0.865	High Similarity	NPC245382
0.865	High Similarity	NPC131624
0.865	High Similarity	NPC199773
0.865	High Similarity	NPC83508
0.865	High Similarity	NPC301323
0.865	High Similarity	NPC181209

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 NPC281835 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	435
0.1-0.2	1104
0.2-0.3	2211
0.3-0.4	2681
0.4-0.5	1555
0.5-0.6	782
0.6-0.7	266
0.7-0.8	85
0.8-0.85	20
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9193	High Similarity	NPD919	Approved
0.908	High Similarity	NPD1247	Approved
0.8805	High Similarity	NPD920	Approved
0.872	High Similarity	NPD3882	Suspended
0.8598	High Similarity	NPD2801	Approved
0.8562	High Similarity	NPD642	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD3817	Phase 2
0.8424	Intermediate Similarity	NPD1934	Approved
0.8395	Intermediate Similarity	NPD1512	Approved
0.8373	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD3818	Discontinued
0.8343	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD1511	Approved
0.825	Intermediate Similarity	NPD1243	Approved
0.8235	Intermediate Similarity	NPD5494	Approved
0.8225	Intermediate Similarity	NPD7075	Discontinued
0.8204	Intermediate Similarity	NPD6801	Discontinued
0.8182	Intermediate Similarity	NPD6559	Discontinued
0.8155	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD1465	Phase 2
0.815	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD6166	Phase 2
0.815	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD5844	Phase 1
0.811	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6799	Approved
0.8035	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD5402	Approved
0.7989	Intermediate Similarity	NPD3926	Phase 2
0.7921	Intermediate Similarity	NPD6797	Phase 2
0.791	Intermediate Similarity	NPD7054	Approved
0.7907	Intermediate Similarity	NPD3749	Approved
0.7877	Intermediate Similarity	NPD7251	Discontinued
0.787	Intermediate Similarity	NPD4380	Phase 2
0.787	Intermediate Similarity	NPD6599	Discontinued
0.7865	Intermediate Similarity	NPD7472	Approved
0.7865	Intermediate Similarity	NPD7074	Phase 3
0.7836	Intermediate Similarity	NPD7819	Suspended
0.7833	Intermediate Similarity	NPD7808	Phase 3
0.7821	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD447	Suspended
0.7812	Intermediate Similarity	NPD230	Phase 1
0.7784	Intermediate Similarity	NPD2532	Approved
0.7784	Intermediate Similarity	NPD2534	Approved
0.7784	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD1510	Phase 2
0.7744	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1549	Phase 2
0.773	Intermediate Similarity	NPD2935	Discontinued
0.773	Intermediate Similarity	NPD1551	Phase 2
0.7719	Intermediate Similarity	NPD7411	Suspended
0.7709	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2800	Approved
0.7683	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD8434	Phase 2
0.764	Intermediate Similarity	NPD943	Approved
0.764	Intermediate Similarity	NPD1240	Approved
0.7588	Intermediate Similarity	NPD5403	Approved
0.7574	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5401	Approved
0.7546	Intermediate Similarity	NPD1607	Approved
0.7544	Intermediate Similarity	NPD1653	Approved
0.7543	Intermediate Similarity	NPD7768	Phase 2
0.7542	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2796	Approved
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD6959	Discontinued
0.747	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD2344	Approved
0.7455	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD3750	Approved
0.7438	Intermediate Similarity	NPD9494	Approved
0.7418	Intermediate Similarity	NPD7286	Phase 2
0.7407	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD3226	Approved
0.7389	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6234	Discontinued
0.7337	Intermediate Similarity	NPD5953	Discontinued
0.7301	Intermediate Similarity	NPD2313	Discontinued
0.7294	Intermediate Similarity	NPD2309	Approved
0.7294	Intermediate Similarity	NPD6190	Approved
0.7278	Intermediate Similarity	NPD7199	Phase 2
0.7268	Intermediate Similarity	NPD3751	Discontinued
0.7246	Intermediate Similarity	NPD2799	Discontinued
0.7238	Intermediate Similarity	NPD5710	Approved
0.7238	Intermediate Similarity	NPD5711	Approved
0.7235	Intermediate Similarity	NPD4628	Phase 3
0.7212	Intermediate Similarity	NPD1613	Approved
0.7212	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1203	Approved
0.7195	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD37	Approved
0.7165	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD2346	Discontinued
0.7151	Intermediate Similarity	NPD4965	Approved
0.7151	Intermediate Similarity	NPD4966	Approved
0.7151	Intermediate Similarity	NPD4967	Phase 2
0.7143	Intermediate Similarity	NPD3748	Approved
0.7125	Intermediate Similarity	NPD9269	Phase 2
0.7125	Intermediate Similarity	NPD9717	Approved
0.7117	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7228	Approved
0.7074	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1933	Approved
0.7063	Intermediate Similarity	NPD422	Phase 1
0.7059	Intermediate Similarity	NPD1471	Phase 3
0.7056	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3787	Discontinued
0.7049	Intermediate Similarity	NPD7229	Phase 3
0.7041	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7435	Discontinued
0.7031	Intermediate Similarity	NPD4287	Approved
0.703	Intermediate Similarity	NPD3027	Phase 3
0.7024	Intermediate Similarity	NPD6651	Approved
0.7021	Intermediate Similarity	NPD7685	Pre-registration
0.7016	Intermediate Similarity	NPD8150	Discontinued
0.7011	Intermediate Similarity	NPD5242	Approved
0.7005	Intermediate Similarity	NPD1729	Discontinued
0.6989	Remote Similarity	NPD2163	Approved
0.6989	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD411	Approved
0.6986	Remote Similarity	NPD7907	Approved
0.6973	Remote Similarity	NPD2403	Approved
0.6971	Remote Similarity	NPD4665	Approved
0.6971	Remote Similarity	NPD4111	Phase 1
0.697	Remote Similarity	NPD6780	Approved
0.697	Remote Similarity	NPD6777	Approved
0.697	Remote Similarity	NPD6778	Approved
0.697	Remote Similarity	NPD6781	Approved
0.697	Remote Similarity	NPD6776	Approved
0.697	Remote Similarity	NPD6782	Approved
0.697	Remote Similarity	NPD6779	Approved
0.697	Remote Similarity	NPD6832	Phase 2
0.6947	Remote Similarity	NPD8313	Approved
0.6947	Remote Similarity	NPD8312	Approved
0.6936	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5353	Approved
0.6905	Remote Similarity	NPD4060	Phase 1
0.6878	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7783	Phase 2
0.6875	Remote Similarity	NPD9268	Approved
0.6875	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6355	Discontinued
0.6863	Remote Similarity	NPD8151	Discontinued
0.6851	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1019	Discontinued
0.6845	Remote Similarity	NPD6233	Phase 2
0.6842	Remote Similarity	NPD4308	Phase 3
0.6842	Remote Similarity	NPD7033	Discontinued
0.684	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6385	Approved
0.6833	Remote Similarity	NPD6386	Approved
0.6829	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7874	Approved
0.6813	Remote Similarity	NPD2296	Approved
0.6813	Remote Similarity	NPD9545	Approved
0.681	Remote Similarity	NPD1608	Approved
0.6806	Remote Similarity	NPD7549	Discontinued
0.68	Remote Similarity	NPD2354	Approved
0.6786	Remote Similarity	NPD6798	Discontinued
0.6786	Remote Similarity	NPD3268	Approved
0.6786	Remote Similarity	NPD1296	Phase 2
0.6782	Remote Similarity	NPD7698	Approved
0.6782	Remote Similarity	NPD7696	Phase 3
0.6782	Remote Similarity	NPD1652	Phase 2
0.6782	Remote Similarity	NPD7697	Approved
0.678	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6808	Phase 2
0.6768	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5124	Phase 1
0.6758	Remote Similarity	NPD5761	Phase 2
0.6758	Remote Similarity	NPD5760	Phase 2
0.6749	Remote Similarity	NPD7870	Phase 2
0.6749	Remote Similarity	NPD7871	Phase 2
0.6742	Remote Similarity	NPD5049	Phase 3
0.6742	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7701	Phase 2
0.6723	Remote Similarity	NPD7390	Discontinued
0.6722	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7458	Discontinued
0.672	Remote Similarity	NPD8127	Discontinued
0.6717	Remote Similarity	NPD6535	Approved
0.6717	Remote Similarity	NPD6534	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