NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.2
Volume:	321.595
LogP:	5.583
LogD:	4.361
LogS:	-5.473
# Rotatable Bonds:	7
TPSA:	9.23
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.582
Synthetic Accessibility Score:	3.19
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.553
MDCK Permeability:	2.1133744667167775e-05
Pgp-inhibitor:	0.842
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.051
30% Bioavailability (F30%):	0.371

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	94.1615219116211%
Volume Distribution (VD):	2.002
Pgp-substrate:	6.832047462463379%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.552
CYP2C19-inhibitor:	0.951
CYP2C19-substrate:	0.818
CYP2C9-inhibitor:	0.798
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.938
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.973
CYP3A4-substrate:	0.512

ADMET: Excretion

Clearance (CL):	9.032
Half-life (T1/2):	0.087

ADMET: Toxicity

hERG Blockers:	0.616
Human Hepatotoxicity (H-HT):	0.309
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.11
Skin Sensitization:	0.95
Carcinogencity:	0.175
Eye Corrosion:	0.311
Eye Irritation:	0.96
Respiratory Toxicity:	0.041

Download Data

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

Natural Product: NPC471581

Natural Product ID:	NPC471581
*Common Name:**	O-Methylbakuchiol
IUPAC Name:	1-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]-4-methoxybenzene
Synonyms:	O-Methylbakuchiol
Standard InCHIKey:	JQPZJZUJFGLNKH-OCKXMSAZSA-N
Standard InCHI:	InChI=1S/C19H26O/c1-6-19(4,14-7-8-16(2)3)15-13-17-9-11-18(20-5)12-10-17/h6,8-13,15H,1,7,14H2,2-5H3/b15-13+/t19-/m1/s1
SMILES:	C=C[C@@](/C=C/c1ccc(cc1)OC)(CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL262630
PubChem CID:	14610678
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0000051] Aromatic monoterpenoids

*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
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18359631]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[25710081]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3069958]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[8759164]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	7
IC50	4
MIC	6
Others	34

Activity Type	# Activity
Cell Line	23
NON-MOLECULAR	14
Organism	12
Others	1
PROTEIN FAMILY	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	55800.0	nM	PMID[490151]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[490151]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI	=	37.0	%	PMID[490153]
NPT744	Cell Line	IMR-32	Homo sapiens	GI	=	30.0	%	PMID[490153]
NPT165	Cell Line	HeLa	Homo sapiens	GI	=	43.0	%	PMID[490153]
NPT1970	Cell Line	THP-1	Homo sapiens	GI	=	45.0	%	PMID[490153]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	37.0	%	PMID[490153]
NPT81	Cell Line	A549	Homo sapiens	GI	=	34.0	%	PMID[490153]
NPT306	Cell Line	PC-3	Homo sapiens	GI	=	31.0	%	PMID[490153]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI	=	29.0	%	PMID[490153]
NPT744	Cell Line	IMR-32	Homo sapiens	GI	=	23.0	%	PMID[490153]
NPT165	Cell Line	HeLa	Homo sapiens	GI	=	28.0	%	PMID[490153]
NPT1970	Cell Line	THP-1	Homo sapiens	GI	=	29.0	%	PMID[490153]
NPT1171	Cell Line	HEp-2	Homo sapiens	GI	=	40.0	%	PMID[490153]
NPT1171	Cell Line	HEp-2	Homo sapiens	GI	=	22.0	%	PMID[490153]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	18.0	%	PMID[490153]
NPT81	Cell Line	A549	Homo sapiens	GI	=	12.0	%	PMID[490153]
NPT306	Cell Line	PC-3	Homo sapiens	GI	=	44.0	%	PMID[490153]
NPT65	Cell Line	HepG2	Homo sapiens	EC50	>	52083.3	nM	PMID[490154]
NPT80	Cell Line	Raji	Homo sapiens	EC50	>	26041.7	nM	PMID[490154]
NPT15	Cell Line	Jurkat	Homo sapiens	EC50	>	49019.6	nM	PMID[490154]
NPT1160	Cell Line	BJ	Homo sapiens	EC50	>	36630.0	nM	PMID[490154]
NPT71	Cell Line	HEK293	Homo sapiens	EC50	>	36630.0	nM	PMID[490154]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-16.0	%	PMID[490149]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-13.0	%	PMID[490150]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	0.0	%	PMID[490149]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-10.0	%	PMID[490150]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-74.0	%	PMID[490149]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	2.0	%	PMID[490150]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-33.0	%	PMID[490149]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-29.0	%	PMID[490150]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-69.0	%	PMID[490149]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-26.0	%	PMID[490150]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-22.0	%	PMID[490149]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-35.0	%	PMID[490150]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	8700.0	nM	PMID[490151]
NPT2	Others	Unspecified		IC50	=	5700.0	nM	PMID[490151]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	>	128.0	ug.mL-1	PMID[490152]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MBC	>	128.0	ug ml-1	PMID[490152]
NPT1129	Organism	Actinomyces viscosus	Actinomyces viscosus	MIC	>	128.0	ug.mL-1	PMID[490152]
NPT1129	Organism	Actinomyces viscosus	Actinomyces viscosus	MBC	>	128.0	ug ml-1	PMID[490152]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	MIC	>	128.0	ug.mL-1	PMID[490152]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	MBC	>	128.0	ug ml-1	PMID[490152]
NPT1484	Organism	Fusobacterium nucleatum	Fusobacterium nucleatum	MIC	>	128.0	ug.mL-1	PMID[490152]
NPT1484	Organism	Fusobacterium nucleatum	Fusobacterium nucleatum	MBC	>	128.0	ug ml-1	PMID[490152]
NPT1128	Organism	Prevotella intermedia	Prevotella intermedia	MIC	>	128.0	ug.mL-1	PMID[490152]
NPT1128	Organism	Prevotella intermedia	Prevotella intermedia	MBC	>	128.0	ug ml-1	PMID[490152]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	=	32.0	ug.mL-1	PMID[490152]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MBC	=	32.0	ug ml-1	PMID[490152]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	36630.0	nM	PMID[490154]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	43478.3	nM	PMID[490154]

☑ 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 NPC471581 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	394
0.1-0.2	2814
0.2-0.3	7932
0.3-0.4	11303
0.4-0.5	5229
0.5-0.6	10199
0.6-0.7	4056
0.7-0.8	683
0.8-0.85	58
0.85-0.9	20
0.9-0.95	2
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC471576
0.9545	High Similarity	NPC177844
0.9545	High Similarity	NPC8002
0.9545	High Similarity	NPC99886
0.9545	High Similarity	NPC259134
0.9438	High Similarity	NPC71853
0.9333	High Similarity	NPC321956
0.8878	High Similarity	NPC473393
0.8866	High Similarity	NPC192596
0.8842	High Similarity	NPC175298
0.8842	High Similarity	NPC470161
0.8763	High Similarity	NPC51633
0.875	High Similarity	NPC100870
0.8687	High Similarity	NPC470393
0.866	High Similarity	NPC13755
0.86	High Similarity	NPC113457
0.86	High Similarity	NPC326447
0.8586	High Similarity	NPC38079
0.8586	High Similarity	NPC108875
0.8571	High Similarity	NPC300166
0.8571	High Similarity	NPC12714
0.8571	High Similarity	NPC310905
0.8515	High Similarity	NPC157473
0.8515	High Similarity	NPC151530
0.85	High Similarity	NPC473855
0.8495	Intermediate Similarity	NPC98772
0.8485	Intermediate Similarity	NPC298224
0.8485	Intermediate Similarity	NPC179686
0.8485	Intermediate Similarity	NPC305205
0.8469	Intermediate Similarity	NPC107101
0.8431	Intermediate Similarity	NPC201959
0.8416	Intermediate Similarity	NPC176971
0.8409	Intermediate Similarity	NPC124576
0.84	Intermediate Similarity	NPC292792
0.84	Intermediate Similarity	NPC109637
0.84	Intermediate Similarity	NPC241224
0.84	Intermediate Similarity	NPC283546
0.84	Intermediate Similarity	NPC474603
0.84	Intermediate Similarity	NPC38209
0.84	Intermediate Similarity	NPC2518
0.84	Intermediate Similarity	NPC12987
0.8384	Intermediate Similarity	NPC307425
0.835	Intermediate Similarity	NPC474272
0.835	Intermediate Similarity	NPC82016
0.8333	Intermediate Similarity	NPC258171
0.8317	Intermediate Similarity	NPC42383
0.8317	Intermediate Similarity	NPC128730
0.8317	Intermediate Similarity	NPC238115
0.8316	Intermediate Similarity	NPC270547
0.83	Intermediate Similarity	NPC24327
0.83	Intermediate Similarity	NPC12870
0.828	Intermediate Similarity	NPC184169
0.8269	Intermediate Similarity	NPC473809
0.8269	Intermediate Similarity	NPC475852
0.8265	Intermediate Similarity	NPC95755
0.8252	Intermediate Similarity	NPC75440
0.8235	Intermediate Similarity	NPC1065
0.82	Intermediate Similarity	NPC84325
0.819	Intermediate Similarity	NPC166837
0.8155	Intermediate Similarity	NPC251306
0.8155	Intermediate Similarity	NPC35543
0.8155	Intermediate Similarity	NPC227894
0.8152	Intermediate Similarity	NPC23837
0.8148	Intermediate Similarity	NPC312105
0.8148	Intermediate Similarity	NPC33900
0.8137	Intermediate Similarity	NPC8302
0.8113	Intermediate Similarity	NPC165646
0.8105	Intermediate Similarity	NPC280347
0.8105	Intermediate Similarity	NPC177420
0.8095	Intermediate Similarity	NPC46844
0.8095	Intermediate Similarity	NPC137685
0.8077	Intermediate Similarity	NPC245115
0.8077	Intermediate Similarity	NPC97811
0.8077	Intermediate Similarity	NPC146530
0.8077	Intermediate Similarity	NPC291837
0.8077	Intermediate Similarity	NPC309982
0.8065	Intermediate Similarity	NPC248817
0.8058	Intermediate Similarity	NPC326801
0.8037	Intermediate Similarity	NPC35344
0.8037	Intermediate Similarity	NPC165106
0.8037	Intermediate Similarity	NPC141003
0.8021	Intermediate Similarity	NPC55561
0.8019	Intermediate Similarity	NPC203924
0.8019	Intermediate Similarity	NPC55300
0.8019	Intermediate Similarity	NPC470723
0.8019	Intermediate Similarity	NPC275627
0.8	Intermediate Similarity	NPC246358
0.8	Intermediate Similarity	NPC113460
0.8	Intermediate Similarity	NPC233731
0.8	Intermediate Similarity	NPC127326
0.8	Intermediate Similarity	NPC36108
0.8	Intermediate Similarity	NPC25493
0.8	Intermediate Similarity	NPC7097
0.8	Intermediate Similarity	NPC234639
0.7981	Intermediate Similarity	NPC233320
0.7979	Intermediate Similarity	NPC197783
0.7963	Intermediate Similarity	NPC180508
0.7963	Intermediate Similarity	NPC228287
0.7961	Intermediate Similarity	NPC288760
0.7961	Intermediate Similarity	NPC227255
0.7959	Intermediate Similarity	NPC316301
0.7959	Intermediate Similarity	NPC27323
0.7957	Intermediate Similarity	NPC265146
0.7957	Intermediate Similarity	NPC124436
0.7944	Intermediate Similarity	NPC199462
0.7941	Intermediate Similarity	NPC62351
0.7938	Intermediate Similarity	NPC155908
0.7928	Intermediate Similarity	NPC163036
0.7925	Intermediate Similarity	NPC2682
0.7925	Intermediate Similarity	NPC183648
0.7925	Intermediate Similarity	NPC106141
0.7925	Intermediate Similarity	NPC179309
0.7925	Intermediate Similarity	NPC88868
0.7925	Intermediate Similarity	NPC231251
0.7925	Intermediate Similarity	NPC25067
0.7917	Intermediate Similarity	NPC242240
0.7917	Intermediate Similarity	NPC123273
0.7917	Intermediate Similarity	NPC318325
0.7895	Intermediate Similarity	NPC23167
0.7895	Intermediate Similarity	NPC206876
0.789	Intermediate Similarity	NPC303370
0.789	Intermediate Similarity	NPC185541
0.789	Intermediate Similarity	NPC473264
0.789	Intermediate Similarity	NPC464
0.789	Intermediate Similarity	NPC475815
0.789	Intermediate Similarity	NPC47194
0.7885	Intermediate Similarity	NPC30416
0.7872	Intermediate Similarity	NPC175313
0.787	Intermediate Similarity	NPC26524
0.787	Intermediate Similarity	NPC204120
0.785	Intermediate Similarity	NPC139617
0.785	Intermediate Similarity	NPC173746
0.785	Intermediate Similarity	NPC156840
0.785	Intermediate Similarity	NPC296920
0.785	Intermediate Similarity	NPC245552
0.785	Intermediate Similarity	NPC90520
0.785	Intermediate Similarity	NPC266932
0.785	Intermediate Similarity	NPC57879
0.785	Intermediate Similarity	NPC257124
0.785	Intermediate Similarity	NPC78918
0.785	Intermediate Similarity	NPC8547
0.785	Intermediate Similarity	NPC23332
0.7843	Intermediate Similarity	NPC471578
0.7843	Intermediate Similarity	NPC101025
0.783	Intermediate Similarity	NPC259554
0.783	Intermediate Similarity	NPC165386
0.7822	Intermediate Similarity	NPC171843
0.7818	Intermediate Similarity	NPC81067
0.7818	Intermediate Similarity	NPC54507
0.7818	Intermediate Similarity	NPC19290
0.7818	Intermediate Similarity	NPC85292
0.7818	Intermediate Similarity	NPC9341
0.7818	Intermediate Similarity	NPC258992
0.7818	Intermediate Similarity	NPC123948
0.7818	Intermediate Similarity	NPC229147
0.7818	Intermediate Similarity	NPC268317
0.7812	Intermediate Similarity	NPC104216
0.781	Intermediate Similarity	NPC186469
0.781	Intermediate Similarity	NPC194034
0.7788	Intermediate Similarity	NPC233396
0.7788	Intermediate Similarity	NPC154899
0.7778	Intermediate Similarity	NPC115379
0.7778	Intermediate Similarity	NPC98372
0.7778	Intermediate Similarity	NPC280606
0.7766	Intermediate Similarity	NPC125306
0.7757	Intermediate Similarity	NPC31279
0.7748	Intermediate Similarity	NPC185738
0.7748	Intermediate Similarity	NPC323948
0.7748	Intermediate Similarity	NPC469954
0.7748	Intermediate Similarity	NPC280001
0.7748	Intermediate Similarity	NPC25648
0.7748	Intermediate Similarity	NPC474933
0.7748	Intermediate Similarity	NPC164386
0.7745	Intermediate Similarity	NPC225506
0.7745	Intermediate Similarity	NPC253746
0.7736	Intermediate Similarity	NPC241549
0.7732	Intermediate Similarity	NPC302546
0.7732	Intermediate Similarity	NPC258219
0.7727	Intermediate Similarity	NPC296526
0.7723	Intermediate Similarity	NPC225464
0.7714	Intermediate Similarity	NPC135464
0.7714	Intermediate Similarity	NPC164576
0.7714	Intermediate Similarity	NPC92623
0.7706	Intermediate Similarity	NPC90903
0.7706	Intermediate Similarity	NPC303522
0.7706	Intermediate Similarity	NPC109241
0.77	Intermediate Similarity	NPC26244
0.7685	Intermediate Similarity	NPC139946
0.7679	Intermediate Similarity	NPC470626
0.7679	Intermediate Similarity	NPC474214
0.7679	Intermediate Similarity	NPC159916
0.7679	Intermediate Similarity	NPC131118
0.7679	Intermediate Similarity	NPC277460
0.7679	Intermediate Similarity	NPC474040
0.7679	Intermediate Similarity	NPC293424
0.7677	Intermediate Similarity	NPC138117
0.7677	Intermediate Similarity	NPC325292
0.767	Intermediate Similarity	NPC472585
0.7658	Intermediate Similarity	NPC141090
0.7653	Intermediate Similarity	NPC300017

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 NPC471581 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	354
0.1-0.2	1139
0.2-0.3	1633
0.3-0.4	2727
0.4-0.5	1725
0.5-0.6	1063
0.6-0.7	413
0.7-0.8	90
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.86	High Similarity	NPD3134	Approved
0.8431	Intermediate Similarity	NPD2684	Approved
0.835	Intermediate Similarity	NPD5451	Approved
0.8333	Intermediate Similarity	NPD1358	Approved
0.8224	Intermediate Similarity	NPD7157	Approved
0.8113	Intermediate Similarity	NPD7843	Approved
0.8037	Intermediate Similarity	NPD5283	Phase 1
0.7959	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD111	Approved
0.7944	Intermediate Similarity	NPD5535	Approved
0.7944	Intermediate Similarity	NPD821	Approved
0.785	Intermediate Similarity	NPD228	Approved
0.7818	Intermediate Similarity	NPD3596	Phase 2
0.781	Intermediate Similarity	NPD290	Approved
0.7778	Intermediate Similarity	NPD2934	Approved
0.7778	Intermediate Similarity	NPD2933	Approved
0.7768	Intermediate Similarity	NPD1357	Approved
0.7748	Intermediate Similarity	NPD5536	Phase 2
0.7714	Intermediate Similarity	NPD968	Approved
0.7706	Intermediate Similarity	NPD1241	Discontinued
0.77	Intermediate Similarity	NPD2860	Approved
0.77	Intermediate Similarity	NPD2859	Approved
0.7679	Intermediate Similarity	NPD6581	Approved
0.7679	Intermediate Similarity	NPD6580	Approved
0.7652	Intermediate Similarity	NPD3972	Approved
0.7629	Intermediate Similarity	NPD9295	Approved
0.7611	Intermediate Similarity	NPD5585	Approved
0.7611	Intermediate Similarity	NPD5691	Approved
0.7611	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5327	Phase 3
0.7568	Intermediate Similarity	NPD2557	Approved
0.7544	Intermediate Similarity	NPD4626	Approved
0.7544	Intermediate Similarity	NPD2667	Approved
0.7544	Intermediate Similarity	NPD2668	Approved
0.7525	Intermediate Similarity	NPD1809	Phase 2
0.7523	Intermediate Similarity	NPD1137	Approved
0.7523	Intermediate Similarity	NPD1139	Approved
0.7478	Intermediate Similarity	NPD3847	Discontinued
0.7477	Intermediate Similarity	NPD595	Approved
0.7477	Intermediate Similarity	NPD593	Approved
0.7476	Intermediate Similarity	NPD3020	Approved
0.7475	Intermediate Similarity	NPD9365	Approved
0.7456	Intermediate Similarity	NPD1651	Approved
0.7455	Intermediate Similarity	NPD1138	Approved
0.7453	Intermediate Similarity	NPD9697	Approved
0.7411	Intermediate Similarity	NPD6671	Approved
0.7404	Intermediate Similarity	NPD3028	Approved
0.7395	Intermediate Similarity	NPD4624	Approved
0.7391	Intermediate Similarity	NPD5846	Approved
0.7391	Intermediate Similarity	NPD6516	Phase 2
0.7391	Intermediate Similarity	NPD1778	Approved
0.7387	Intermediate Similarity	NPD592	Approved
0.7387	Intermediate Similarity	NPD594	Approved
0.735	Intermediate Similarity	NPD2981	Phase 2
0.7328	Intermediate Similarity	NPD3496	Discontinued
0.7304	Intermediate Similarity	NPD3049	Approved
0.7304	Intermediate Similarity	NPD2594	Approved
0.7304	Intermediate Similarity	NPD3444	Approved
0.7304	Intermediate Similarity	NPD3445	Approved
0.7304	Intermediate Similarity	NPD2595	Approved
0.7304	Intermediate Similarity	NPD3443	Approved
0.7288	Intermediate Similarity	NPD2983	Phase 2
0.7288	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6542	Approved
0.7288	Intermediate Similarity	NPD2429	Approved
0.7288	Intermediate Similarity	NPD6583	Phase 3
0.7288	Intermediate Similarity	NPD3685	Discontinued
0.7288	Intermediate Similarity	NPD6543	Approved
0.7288	Intermediate Similarity	NPD6582	Phase 2
0.7288	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2428	Approved
0.7288	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD2982	Phase 2
0.7288	Intermediate Similarity	NPD6540	Phase 3
0.7288	Intermediate Similarity	NPD4359	Approved
0.7288	Intermediate Similarity	NPD6539	Approved
0.7265	Intermediate Similarity	NPD3705	Approved
0.7257	Intermediate Similarity	NPD6387	Discontinued
0.7255	Intermediate Similarity	NPD9296	Approved
0.7241	Intermediate Similarity	NPD2554	Approved
0.7241	Intermediate Similarity	NPD2556	Approved
0.7227	Intermediate Similarity	NPD8651	Approved
0.7227	Intermediate Similarity	NPD6538	Approved
0.7227	Intermediate Similarity	NPD6541	Approved
0.7227	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD1182	Approved
0.7217	Intermediate Similarity	NPD1894	Discontinued
0.7217	Intermediate Similarity	NPD2486	Discontinued
0.7217	Intermediate Similarity	NPD1548	Phase 1
0.7184	Intermediate Similarity	NPD844	Approved
0.717	Intermediate Similarity	NPD846	Approved
0.717	Intermediate Similarity	NPD940	Approved
0.7157	Intermediate Similarity	NPD845	Approved
0.7156	Intermediate Similarity	NPD5374	Approved
0.7156	Intermediate Similarity	NPD5373	Approved
0.7155	Intermediate Similarity	NPD6382	Discontinued
0.7154	Intermediate Similarity	NPD7294	Phase 1
0.7143	Intermediate Similarity	NPD1669	Approved
0.7143	Intermediate Similarity	NPD4129	Approved
0.7119	Intermediate Similarity	NPD1281	Approved
0.7107	Intermediate Similarity	NPD7018	Phase 2
0.7107	Intermediate Similarity	NPD3690	Phase 2
0.7107	Intermediate Similarity	NPD7905	Discontinued
0.7107	Intermediate Similarity	NPD6584	Phase 3
0.7107	Intermediate Similarity	NPD3691	Phase 2
0.7105	Intermediate Similarity	NPD709	Approved
0.7097	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1876	Approved
0.7075	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7095	Approved
0.7059	Intermediate Similarity	NPD2233	Approved
0.7059	Intermediate Similarity	NPD2232	Approved
0.7059	Intermediate Similarity	NPD2230	Approved
0.7049	Intermediate Similarity	NPD4993	Discontinued
0.7049	Intermediate Similarity	NPD3018	Phase 2
0.704	Intermediate Similarity	NPD4140	Approved
0.704	Intermediate Similarity	NPD3110	Approved
0.704	Intermediate Similarity	NPD3109	Approved
0.7034	Intermediate Similarity	NPD3294	Phase 2
0.7025	Intermediate Similarity	NPD1820	Approved
0.7025	Intermediate Similarity	NPD1817	Approved
0.7025	Intermediate Similarity	NPD3567	Approved
0.7025	Intermediate Similarity	NPD3568	Approved
0.7025	Intermediate Similarity	NPD1819	Approved
0.7025	Intermediate Similarity	NPD1818	Approved
0.7009	Intermediate Similarity	NPD291	Approved
0.6992	Remote Similarity	NPD4908	Phase 1
0.6992	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD5735	Approved
0.6975	Remote Similarity	NPD422	Phase 1
0.6975	Remote Similarity	NPD1610	Phase 2
0.6967	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.696	Remote Similarity	NPD8032	Phase 2
0.6952	Remote Similarity	NPD288	Approved
0.6949	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD1283	Approved
0.6942	Remote Similarity	NPD2922	Phase 1
0.6935	Remote Similarity	NPD3180	Approved
0.6935	Remote Similarity	NPD3164	Approved
0.6935	Remote Similarity	NPD3165	Approved
0.6935	Remote Similarity	NPD3167	Approved
0.6935	Remote Similarity	NPD5163	Phase 2
0.6935	Remote Similarity	NPD3166	Approved
0.6935	Remote Similarity	NPD3027	Phase 3
0.6935	Remote Similarity	NPD3179	Approved
0.6935	Remote Similarity	NPD5746	Approved
0.6929	Remote Similarity	NPD6353	Approved
0.6929	Remote Similarity	NPD4097	Suspended
0.6917	Remote Similarity	NPD2235	Phase 2
0.6917	Remote Similarity	NPD1840	Phase 2
0.6917	Remote Similarity	NPD2231	Phase 2
0.6916	Remote Similarity	NPD1242	Phase 1
0.6911	Remote Similarity	NPD2861	Phase 2
0.6905	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD3620	Phase 2
0.6903	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4098	Discontinued
0.6881	Remote Similarity	NPD9610	Approved
0.6881	Remote Similarity	NPD9608	Approved
0.688	Remote Similarity	NPD6798	Discontinued
0.688	Remote Similarity	NPD5109	Approved
0.688	Remote Similarity	NPD5111	Phase 2
0.688	Remote Similarity	NPD5718	Phase 2
0.688	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.688	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.688	Remote Similarity	NPD3144	Approved
0.688	Remote Similarity	NPD3145	Approved
0.688	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.688	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.688	Remote Similarity	NPD5110	Phase 2
0.6875	Remote Similarity	NPD6895	Approved
0.6875	Remote Similarity	NPD6896	Approved
0.6875	Remote Similarity	NPD3022	Approved
0.6875	Remote Similarity	NPD3021	Approved
0.685	Remote Similarity	NPD3657	Discovery
0.6833	Remote Similarity	NPD1535	Discovery
0.6833	Remote Similarity	NPD1091	Approved
0.6829	Remote Similarity	NPD2987	Approved
0.6829	Remote Similarity	NPD2990	Approved
0.6825	Remote Similarity	NPD6233	Phase 2
0.6825	Remote Similarity	NPD2674	Phase 3
0.6825	Remote Similarity	NPD4062	Phase 3
0.6825	Remote Similarity	NPD7265	Discontinued
0.6825	Remote Similarity	NPD5745	Approved
0.6825	Remote Similarity	NPD4870	Approved
0.6814	Remote Similarity	NPD2673	Approved
0.6814	Remote Similarity	NPD2671	Approved
0.6807	Remote Similarity	NPD17	Approved
0.6803	Remote Similarity	NPD6696	Suspended
0.6803	Remote Similarity	NPD196	Phase 1
0.68	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6179	Discontinued
0.6783	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.678	Remote Similarity	NPD9545	Approved
0.678	Remote Similarity	NPD3091	Approved
0.6777	Remote Similarity	NPD1481	Phase 2
0.6774	Remote Similarity	NPD9494	Approved
0.6774	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD9087	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