NPASS Compound

Structure

CID186128 OpenBabel06191715562D 21 24 0 0 0 0 0 0 0 0999 V2000 -3.3275 0.0746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3096 1.0334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5061 -0.4203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5366 2.3811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4703 1.4973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6668 0.0436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7138 2.8717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5240 1.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0382 2.8938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7970 2.4251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6756 -0.0221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6489 1.0024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8668 2.4032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6883 0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8097 1.4663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8401 -0.4850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8541 1.4443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0127 0.9646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8317 -1.4468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8361 -0.4754 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 14 2 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 15 1 0 0 0 0 11 14 1 0 0 0 0 11 16 2 0 0 0 0 12 15 1 0 0 0 0 13 17 2 0 0 0 0 14 17 1 0 0 0 0 15 18 2 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	272.08
Volume:	294.17
LogP:	4.039
LogD:	3.394
LogS:	-6.348
# Rotatable Bonds:	1
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.631
Synthetic Accessibility Score:	2.2
Fsp3:	0.053
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.776
MDCK Permeability:	2.020296778937336e-05
Pgp-inhibitor:	0.042
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.622
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.22
Plasma Protein Binding (PPB):	99.84151458740234%
Volume Distribution (VD):	0.418
Pgp-substrate:	0.8187310099601746%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.828
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.734
CYP2C9-substrate:	0.813
CYP2D6-inhibitor:	0.132
CYP2D6-substrate:	0.514
CYP3A4-inhibitor:	0.434
CYP3A4-substrate:	0.165

ADMET: Excretion

Clearance (CL):	5.484
Half-life (T1/2):	0.081

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.407
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.836
Rat Oral Acute Toxicity:	0.099
Maximum Recommended Daily Dose:	0.16
Skin Sensitization:	0.849
Carcinogencity:	0.848
Eye Corrosion:	0.005
Eye Irritation:	0.945
Respiratory Toxicity:	0.108

Download Data

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

Natural Product: NPC186128

Natural Product ID:	NPC186128
*Common Name:**	Anigorufone
IUPAC Name:	2-hydroxy-9-phenylphenalen-1-one
Synonyms:
Standard InCHIKey:	ACJJXELQAJQSLK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H12O2/c20-16-11-14-8-4-7-13-9-10-15(12-5-2-1-3-6-12)18(17(13)14)19(16)21/h1-11,20H
SMILES:	OC1=Cc2cccc3c2c(C1=O)c(cc3)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1163760
PubChem CID:	636472
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0002044] Phenylnaphthalenes

*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
NPO15254	Macropidia fuliginosa	Species	Haemodoraceae	Eukaryota	n.a.	Australian	n.a.	PMID[26151487]
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	flowers	n.a.	n.a.	PMID[30413343]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3783160]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16782	Andrographis viscosula	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10654	Lindera obtusiloba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5869	Anthocercis albicans	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22441	Senna spectabilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10984	Euclea crispa	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11360	Tiliacora racemosa	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18427	Axinella agnata	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17900	Iotrochota birotulata	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3096	Verbascum laxum	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10064	Diospyros canaliculata	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19091	Bacterium from	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23044	Aesculus hippocastanum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15254	Macropidia fuliginosa	Species	Haemodoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16782	Andrographis viscosula	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16548	Chenopodium formosanum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10654	Lindera obtusiloba	Species	Lauraceae	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
EC50	2
IC50	4
Others	1

Activity Type	# Activity
Cell Line	1
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	22.0	%	PMID[463103]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	>	100.0	ug.mL-1	PMID[463103]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	>	100.0	ug.mL-1	PMID[463103]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	100.0	ug.mL-1	PMID[463103]
NPT633	Organism	Leishmania donovani	Leishmania donovani	EC50	<	60.0	ug.mL-1	PMID[463104]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	EC50	<	60.0	ug.mL-1	PMID[463104]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	35000.0	nM	PMID[463106]

☑ 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 NPC186128 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	335
0.1-0.2	1575
0.2-0.3	3601
0.3-0.4	12067
0.4-0.5	11443
0.5-0.6	10903
0.6-0.7	2431
0.7-0.8	301
0.8-0.85	31
0.85-0.9	7
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9417	High Similarity	NPC134120
0.9259	High Similarity	NPC67377
0.8868	High Similarity	NPC172483
0.885	High Similarity	NPC318173
0.8818	High Similarity	NPC143768
0.8803	High Similarity	NPC164014
0.8727	High Similarity	NPC292834
0.8704	High Similarity	NPC203732
0.8679	High Similarity	NPC274443
0.8673	High Similarity	NPC469843
0.8611	High Similarity	NPC100767
0.8585	High Similarity	NPC222390
0.8585	High Similarity	NPC244427
0.8544	High Similarity	NPC472880
0.8505	High Similarity	NPC247976
0.8435	Intermediate Similarity	NPC80605
0.8435	Intermediate Similarity	NPC323440
0.8435	Intermediate Similarity	NPC222968
0.843	Intermediate Similarity	NPC478165
0.843	Intermediate Similarity	NPC478162
0.8407	Intermediate Similarity	NPC196673
0.8403	Intermediate Similarity	NPC318067
0.8381	Intermediate Similarity	NPC156021
0.8333	Intermediate Similarity	NPC329556
0.8319	Intermediate Similarity	NPC470253
0.8304	Intermediate Similarity	NPC265513
0.8288	Intermediate Similarity	NPC318327
0.8269	Intermediate Similarity	NPC34243
0.8246	Intermediate Similarity	NPC326664
0.8246	Intermediate Similarity	NPC471721
0.819	Intermediate Similarity	NPC158157
0.8158	Intermediate Similarity	NPC93287
0.8148	Intermediate Similarity	NPC472879
0.8142	Intermediate Similarity	NPC474057
0.8136	Intermediate Similarity	NPC476645
0.8131	Intermediate Similarity	NPC49994
0.8099	Intermediate Similarity	NPC328107
0.8095	Intermediate Similarity	NPC289883
0.807	Intermediate Similarity	NPC66208
0.8058	Intermediate Similarity	NPC418308
0.8019	Intermediate Similarity	NPC172925
0.8018	Intermediate Similarity	NPC471186
0.8017	Intermediate Similarity	NPC215419
0.7982	Intermediate Similarity	NPC476993
0.7981	Intermediate Similarity	NPC19256
0.7981	Intermediate Similarity	NPC277277
0.7966	Intermediate Similarity	NPC228318
0.7965	Intermediate Similarity	NPC192577
0.7961	Intermediate Similarity	NPC267262
0.7928	Intermediate Similarity	NPC329282
0.7917	Intermediate Similarity	NPC232958
0.7913	Intermediate Similarity	NPC218855
0.7913	Intermediate Similarity	NPC471189
0.787	Intermediate Similarity	NPC239185
0.7863	Intermediate Similarity	NPC93181
0.7857	Intermediate Similarity	NPC105899
0.7851	Intermediate Similarity	NPC144547
0.7851	Intermediate Similarity	NPC472981
0.785	Intermediate Similarity	NPC260233
0.784	Intermediate Similarity	NPC428300
0.7838	Intermediate Similarity	NPC255676
0.783	Intermediate Similarity	NPC153885
0.783	Intermediate Similarity	NPC155232
0.7826	Intermediate Similarity	NPC137315
0.7818	Intermediate Similarity	NPC112552
0.781	Intermediate Similarity	NPC173413
0.7798	Intermediate Similarity	NPC134882
0.7795	Intermediate Similarity	NPC55949
0.7795	Intermediate Similarity	NPC27659
0.7788	Intermediate Similarity	NPC83409
0.7788	Intermediate Similarity	NPC185763
0.7788	Intermediate Similarity	NPC37914
0.7787	Intermediate Similarity	NPC269923
0.7787	Intermediate Similarity	NPC167323
0.7778	Intermediate Similarity	NPC219573
0.7778	Intermediate Similarity	NPC185208
0.7778	Intermediate Similarity	NPC234637
0.7778	Intermediate Similarity	NPC12695
0.7778	Intermediate Similarity	NPC130591
0.7778	Intermediate Similarity	NPC96024
0.7778	Intermediate Similarity	NPC48248
0.7769	Intermediate Similarity	NPC289432
0.7769	Intermediate Similarity	NPC988
0.7768	Intermediate Similarity	NPC249067
0.7759	Intermediate Similarity	NPC280789
0.7757	Intermediate Similarity	NPC238219
0.7752	Intermediate Similarity	NPC225051
0.7742	Intermediate Similarity	NPC142956
0.7742	Intermediate Similarity	NPC295664
0.7736	Intermediate Similarity	NPC133461
0.7736	Intermediate Similarity	NPC110704
0.7734	Intermediate Similarity	NPC72669
0.7734	Intermediate Similarity	NPC474517
0.7719	Intermediate Similarity	NPC112903
0.7717	Intermediate Similarity	NPC146647
0.7717	Intermediate Similarity	NPC34414
0.7712	Intermediate Similarity	NPC186933
0.7706	Intermediate Similarity	NPC265220
0.7692	Intermediate Similarity	NPC471481
0.7686	Intermediate Similarity	NPC202015
0.7686	Intermediate Similarity	NPC204784
0.7672	Intermediate Similarity	NPC291799
0.7661	Intermediate Similarity	NPC85511
0.7658	Intermediate Similarity	NPC128248
0.7658	Intermediate Similarity	NPC133809
0.7658	Intermediate Similarity	NPC136810
0.7658	Intermediate Similarity	NPC109514
0.7642	Intermediate Similarity	NPC120545
0.7636	Intermediate Similarity	NPC75724
0.7634	Intermediate Similarity	NPC283088
0.7632	Intermediate Similarity	NPC142326
0.7632	Intermediate Similarity	NPC94751
0.7627	Intermediate Similarity	NPC241851
0.7623	Intermediate Similarity	NPC105709
0.7619	Intermediate Similarity	NPC157778
0.7619	Intermediate Similarity	NPC474106
0.7607	Intermediate Similarity	NPC471188
0.76	Intermediate Similarity	NPC173978
0.7597	Intermediate Similarity	NPC244699
0.7596	Intermediate Similarity	NPC307
0.7596	Intermediate Similarity	NPC160339
0.7589	Intermediate Similarity	NPC25458
0.7589	Intermediate Similarity	NPC320891
0.7581	Intermediate Similarity	NPC65627
0.7581	Intermediate Similarity	NPC91478
0.7581	Intermediate Similarity	NPC300274
0.7578	Intermediate Similarity	NPC276238
0.7578	Intermediate Similarity	NPC171460
0.7576	Intermediate Similarity	NPC474813
0.7576	Intermediate Similarity	NPC155211
0.757	Intermediate Similarity	NPC284475
0.757	Intermediate Similarity	NPC103346
0.7565	Intermediate Similarity	NPC211439
0.7563	Intermediate Similarity	NPC474095
0.7563	Intermediate Similarity	NPC470764
0.7563	Intermediate Similarity	NPC228936
0.7557	Intermediate Similarity	NPC50924
0.7557	Intermediate Similarity	NPC23894
0.7557	Intermediate Similarity	NPC474659
0.7545	Intermediate Similarity	NPC103048
0.7542	Intermediate Similarity	NPC13784
0.7538	Intermediate Similarity	NPC58685
0.7524	Intermediate Similarity	NPC43945
0.7524	Intermediate Similarity	NPC69057
0.7521	Intermediate Similarity	NPC475002
0.7521	Intermediate Similarity	NPC95126
0.752	Intermediate Similarity	NPC375356
0.7519	Intermediate Similarity	NPC186647
0.7519	Intermediate Similarity	NPC245923
0.75	Intermediate Similarity	NPC323420
0.75	Intermediate Similarity	NPC1682
0.75	Intermediate Similarity	NPC59677
0.75	Intermediate Similarity	NPC470252
0.75	Intermediate Similarity	NPC188844
0.75	Intermediate Similarity	NPC282923
0.75	Intermediate Similarity	NPC135730
0.75	Intermediate Similarity	NPC225079
0.7481	Intermediate Similarity	NPC53896
0.748	Intermediate Similarity	NPC254492
0.7477	Intermediate Similarity	NPC145052
0.746	Intermediate Similarity	NPC199273
0.746	Intermediate Similarity	NPC236189
0.7453	Intermediate Similarity	NPC477693
0.7453	Intermediate Similarity	NPC477704
0.7445	Intermediate Similarity	NPC478164
0.744	Intermediate Similarity	NPC176208
0.744	Intermediate Similarity	NPC307174
0.7434	Intermediate Similarity	NPC304873
0.7424	Intermediate Similarity	NPC287604
0.7424	Intermediate Similarity	NPC472262
0.7424	Intermediate Similarity	NPC161964
0.7422	Intermediate Similarity	NPC69424
0.7422	Intermediate Similarity	NPC176130
0.7422	Intermediate Similarity	NPC72667
0.7422	Intermediate Similarity	NPC78364
0.7422	Intermediate Similarity	NPC115797
0.7422	Intermediate Similarity	NPC84672
0.7422	Intermediate Similarity	NPC51448
0.7417	Intermediate Similarity	NPC474408
0.7417	Intermediate Similarity	NPC476357
0.7417	Intermediate Similarity	NPC217111
0.7417	Intermediate Similarity	NPC274839
0.7414	Intermediate Similarity	NPC470391
0.7411	Intermediate Similarity	NPC476042
0.7411	Intermediate Similarity	NPC217621
0.7407	Intermediate Similarity	NPC476484
0.7402	Intermediate Similarity	NPC123506
0.7402	Intermediate Similarity	NPC103540
0.7388	Intermediate Similarity	NPC62272
0.7388	Intermediate Similarity	NPC264022
0.7387	Intermediate Similarity	NPC289201
0.7385	Intermediate Similarity	NPC136588
0.7385	Intermediate Similarity	NPC31799
0.7385	Intermediate Similarity	NPC199253
0.7383	Intermediate Similarity	NPC325709
0.7383	Intermediate Similarity	NPC113307
0.7381	Intermediate Similarity	NPC12824
0.7373	Intermediate Similarity	NPC21162
0.7368	Intermediate Similarity	NPC80035
0.7355	Intermediate Similarity	NPC62138

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 NPC186128 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	958
0.2-0.3	1166
0.3-0.4	3000
0.4-0.5	2484
0.5-0.6	986
0.6-0.7	170
0.7-0.8	33
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD1929	Approved
0.8333	Intermediate Similarity	NPD1930	Approved
0.8333	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.8305	Intermediate Similarity	NPD4879	Approved
0.8241	Intermediate Similarity	NPD1932	Approved
0.822	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.8174	Intermediate Similarity	NPD5951	Approved
0.8019	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.789	Intermediate Similarity	NPD2066	Phase 3
0.787	Intermediate Similarity	NPD3495	Discontinued
0.7807	Intermediate Similarity	NPD2329	Discontinued
0.7768	Intermediate Similarity	NPD1237	Approved
0.7736	Intermediate Similarity	NPD1239	Approved
0.7724	Intermediate Similarity	NPD4878	Approved
0.7717	Intermediate Similarity	NPD7008	Discontinued
0.7667	Intermediate Similarity	NPD7610	Discontinued
0.7603	Intermediate Similarity	NPD7009	Phase 2
0.757	Intermediate Similarity	NPD7609	Phase 3
0.7524	Intermediate Similarity	NPD650	Approved
0.75	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD7631	Approved
0.7402	Intermediate Similarity	NPD1470	Approved
0.7388	Intermediate Similarity	NPD5406	Approved
0.7388	Intermediate Similarity	NPD5404	Approved
0.7388	Intermediate Similarity	NPD5405	Approved
0.7388	Intermediate Similarity	NPD5408	Approved
0.7387	Intermediate Similarity	NPD1566	Phase 3
0.7387	Intermediate Similarity	NPD1565	Approved
0.7387	Intermediate Similarity	NPD1564	Approved
0.735	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD942	Approved
0.7273	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD1693	Approved
0.72	Intermediate Similarity	NPD2345	Approved
0.7182	Intermediate Similarity	NPD1508	Approved
0.7174	Intermediate Similarity	NPD7003	Approved
0.7156	Intermediate Similarity	NPD1090	Approved
0.7156	Intermediate Similarity	NPD1086	Approved
0.7156	Intermediate Similarity	NPD1089	Approved
0.7143	Intermediate Similarity	NPD1989	Approved
0.7143	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2342	Discontinued
0.7117	Intermediate Similarity	NPD1563	Approved
0.7068	Intermediate Similarity	NPD7961	Discontinued
0.7064	Intermediate Similarity	NPD800	Approved
0.7063	Intermediate Similarity	NPD5836	Discontinued
0.7049	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD6966	Discovery
0.7027	Intermediate Similarity	NPD1088	Approved
0.7016	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3764	Approved
0.6991	Remote Similarity	NPD1843	Approved
0.6981	Remote Similarity	NPD9491	Approved
0.6967	Remote Similarity	NPD7094	Approved
0.6967	Remote Similarity	NPD6858	Approved
0.6964	Remote Similarity	NPD1202	Approved
0.6957	Remote Similarity	NPD2346	Discontinued
0.6934	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2932	Approved
0.6929	Remote Similarity	NPD3019	Approved
0.6901	Remote Similarity	NPD7390	Discontinued
0.6881	Remote Similarity	NPD1087	Approved
0.687	Remote Similarity	NPD1164	Approved
0.6866	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5909	Discontinued
0.686	Remote Similarity	NPD1317	Discontinued
0.6857	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD9256	Approved
0.6847	Remote Similarity	NPD9258	Approved
0.6818	Remote Similarity	NPD4980	Approved
0.6812	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1283	Approved
0.6792	Remote Similarity	NPD226	Approved
0.6781	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD2313	Discontinued
0.6736	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1651	Approved
0.6719	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD1245	Approved
0.6718	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD3300	Phase 2
0.6713	Remote Similarity	NPD7236	Approved
0.6692	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD1238	Approved
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD8165	Discontinued
0.6667	Remote Similarity	NPD1574	Approved
0.6667	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3880	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3972	Approved
0.6636	Remote Similarity	NPD9259	Approved
0.6636	Remote Similarity	NPD9257	Approved
0.6617	Remote Similarity	NPD1593	Approved
0.6615	Remote Similarity	NPD3026	Approved
0.6615	Remote Similarity	NPD3023	Approved
0.6604	Remote Similarity	NPD9490	Approved
0.6599	Remote Similarity	NPD7239	Suspended
0.6596	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5157	Phase 1
0.6591	Remote Similarity	NPD5159	Phase 2
0.6591	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD3025	Approved
0.6589	Remote Similarity	NPD3024	Approved
0.6587	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2629	Approved
0.6587	Remote Similarity	NPD1246	Approved
0.6583	Remote Similarity	NPD164	Approved
0.6581	Remote Similarity	NPD9495	Approved
0.6577	Remote Similarity	NPD4793	Discontinued
0.6573	Remote Similarity	NPD3750	Approved
0.6569	Remote Similarity	NPD7713	Phase 3
0.6567	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD6287	Discontinued
0.6565	Remote Similarity	NPD1281	Approved
0.656	Remote Similarity	NPD7635	Approved
0.6554	Remote Similarity	NPD3226	Approved
0.6538	Remote Similarity	NPD2286	Discontinued
0.6535	Remote Similarity	NPD3317	Approved
0.6525	Remote Similarity	NPD7798	Approved
0.6509	Remote Similarity	NPD225	Approved
0.6509	Remote Similarity	NPD227	Approved
0.6504	Remote Similarity	NPD2182	Approved
0.6489	Remote Similarity	NPD3881	Discontinued
0.648	Remote Similarity	NPD9508	Approved
0.6463	Remote Similarity	NPD6273	Approved
0.6462	Remote Similarity	NPD6994	Approved
0.6462	Remote Similarity	NPD6993	Approved
0.646	Remote Similarity	NPD5347	Phase 2
0.646	Remote Similarity	NPD5346	Phase 2
0.6454	Remote Similarity	NPD2799	Discontinued
0.6454	Remote Similarity	NPD3748	Approved
0.6443	Remote Similarity	NPD7458	Discontinued
0.6439	Remote Similarity	NPD5618	Discontinued
0.6429	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD4199	Phase 3
0.641	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD4198	Discontinued
0.6389	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD2846	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2344	Approved
0.6364	Remote Similarity	NPD1471	Phase 3
0.6345	Remote Similarity	NPD8166	Discontinued
0.6338	Remote Similarity	NPD4308	Phase 3
0.6336	Remote Similarity	NPD4105	Approved
0.6336	Remote Similarity	NPD4102	Approved
0.6336	Remote Similarity	NPD1855	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD7714	Approved
0.6331	Remote Similarity	NPD7715	Approved
0.6325	Remote Similarity	NPD6049	Phase 2
0.6325	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD3772	Phase 3
0.632	Remote Similarity	NPD664	Approved
0.6316	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1888	Phase 1
0.629	Remote Similarity	NPD9267	Approved
0.629	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.629	Remote Similarity	NPD9264	Approved
0.629	Remote Similarity	NPD9263	Approved
0.6286	Remote Similarity	NPD4445	Approved
0.6286	Remote Similarity	NPD4453	Approved
0.6286	Remote Similarity	NPD4452	Approved
0.6284	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD2648	Phase 3
0.6281	Remote Similarity	NPD2193	Phase 2
0.6277	Remote Similarity	NPD7084	Phase 3
0.6259	Remote Similarity	NPD6766	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3020	Approved
0.625	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7720	Phase 2
0.6241	Remote Similarity	NPD4106	Approved
0.6241	Remote Similarity	NPD4136	Approved
0.6241	Remote Similarity	NPD4135	Approved
0.624	Remote Similarity	NPD9266	Approved
0.624	Remote Similarity	NPD74	Approved
0.6239	Remote Similarity	NPD4695	Discontinued
0.6231	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.623	Remote Similarity	NPD6647	Phase 2
0.6225	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD1875	Phase 1
0.6216	Remote Similarity	NPD3971	Phase 1
0.6214	Remote Similarity	NPD6663	Approved
0.6198	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD1616	Discontinued
0.6197	Remote Similarity	NPD1607	Approved
0.6197	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD7058	Phase 2
0.6194	Remote Similarity	NPD7057	Phase 3
0.619	Remote Similarity	NPD2067	Discontinued
0.619	Remote Similarity	NPD2309	Approved
0.6186	Remote Similarity	NPD9260	Approved
0.6183	Remote Similarity	NPD6065	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