NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.18
Volume:	307.169
LogP:	4.065
LogD:	3.8
LogS:	-3.478
# Rotatable Bonds:	6
TPSA:	32.76
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.608
Synthetic Accessibility Score:	3.778
Fsp3:	0.444
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:	-4.598
MDCK Permeability:	3.08286544168368e-05
Pgp-inhibitor:	0.624
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.156
Plasma Protein Binding (PPB):	96.0500717163086%
Volume Distribution (VD):	1.613
Pgp-substrate:	1.4888365268707275%

ADMET: Metabolism

CYP1A2-inhibitor:	0.147
CYP1A2-substrate:	0.306
CYP2C19-inhibitor:	0.406
CYP2C19-substrate:	0.57
CYP2C9-inhibitor:	0.401
CYP2C9-substrate:	0.439
CYP2D6-inhibitor:	0.77
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.912
CYP3A4-substrate:	0.441

ADMET: Excretion

Clearance (CL):	8.951
Half-life (T1/2):	0.548

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.241
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.537
Skin Sensitization:	0.928
Carcinogencity:	0.208
Eye Corrosion:	0.076
Eye Irritation:	0.202
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC62351

Natural Product ID:	NPC62351
*Common Name:**	12,13-Epoxybakuchiol
IUPAC Name:	4-[(1E,3S)-3-[2-(3,3-dimethyloxiran-2-yl)ethyl]-3-methylpenta-1,4-dienyl]phenol
Synonyms:	12,13-Epoxybakuchiol
Standard InCHIKey:	WHJYECILXDIKJA-AVNQGEAYSA-N
Standard InCHI:	InChI=1S/C18H24O2/c1-5-18(4,13-11-16-17(2,3)20-16)12-10-14-6-8-15(19)9-7-14/h5-10,12,16,19H,1,11,13H2,2-4H3/b12-10+/t16?,18-/m0/s1
SMILES:	C=C[C@@](C)(/C=C/c1ccc(cc1)O)CCC1C(C)(C)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL405046
PubChem CID:	15818782
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000037] Styrenes

*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]
NPO1470	Fructus psoraleae corylifoliae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
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	6
MIC	6
Others	19

Activity Type	# Activity
Cell Line	16
NON-MOLECULAR	8
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	>	50000.0	nM	PMID[534503]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[534503]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI	=	12.0	%	PMID[534505]
NPT744	Cell Line	IMR-32	Homo sapiens	GI	=	59.0	%	PMID[534505]
NPT165	Cell Line	HeLa	Homo sapiens	GI	=	32.0	%	PMID[534505]
NPT1970	Cell Line	THP-1	Homo sapiens	GI	=	52.0	%	PMID[534505]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	33.0	%	PMID[534505]
NPT81	Cell Line	A549	Homo sapiens	GI	=	44.0	%	PMID[534505]
NPT306	Cell Line	PC-3	Homo sapiens	GI	=	46.0	%	PMID[534505]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[534506]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[534506]
NPT65	Cell Line	HepG2	Homo sapiens	EC50	>	52083.3	nM	PMID[534507]
NPT80	Cell Line	Raji	Homo sapiens	EC50	>	22554.3	nM	PMID[534507]
NPT15	Cell Line	Jurkat	Homo sapiens	EC50	>	49019.6	nM	PMID[534507]
NPT1160	Cell Line	BJ	Homo sapiens	EC50	>	36630.0	nM	PMID[534507]
NPT71	Cell Line	HEK293	Homo sapiens	EC50	>	36630.0	nM	PMID[534507]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-30.0	%	PMID[534502]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-93.0	%	PMID[534502]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-100.0	%	PMID[534502]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-14.0	%	PMID[534502]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-99.0	%	PMID[534502]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-89.0	%	PMID[534502]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	>	50000.0	nM	PMID[534503]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[534503]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	128.0	ug.mL-1	PMID[534504]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MBC	>	128.0	ug ml-1	PMID[534504]
NPT1129	Organism	Actinomyces viscosus	Actinomyces viscosus	MIC	=	64.0	ug.mL-1	PMID[534504]
NPT1129	Organism	Actinomyces viscosus	Actinomyces viscosus	MBC	=	128.0	ug ml-1	PMID[534504]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	MIC	=	128.0	ug.mL-1	PMID[534504]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	MBC	>	128.0	ug ml-1	PMID[534504]
NPT1484	Organism	Fusobacterium nucleatum	Fusobacterium nucleatum	MIC	>	128.0	ug.mL-1	PMID[534504]
NPT1484	Organism	Fusobacterium nucleatum	Fusobacterium nucleatum	MBC	>	128.0	ug ml-1	PMID[534504]
NPT1128	Organism	Prevotella intermedia	Prevotella intermedia	MIC	=	64.0	ug.mL-1	PMID[534504]
NPT1128	Organism	Prevotella intermedia	Prevotella intermedia	MBC	=	128.0	ug ml-1	PMID[534504]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	=	32.0	ug.mL-1	PMID[534504]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MBC	=	64.0	ug ml-1	PMID[534504]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	36630.0	nM	PMID[534507]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	43478.3	nM	PMID[534507]

☑ 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 NPC62351 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	225
0.1-0.2	1477
0.2-0.3	4314
0.3-0.4	13272
0.4-0.5	7929
0.5-0.6	10570
0.6-0.7	4188
0.7-0.8	671
0.8-0.85	46
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC101025
0.9286	High Similarity	NPC471578
0.9053	High Similarity	NPC270547
0.8842	High Similarity	NPC98772
0.8673	High Similarity	NPC316301
0.8673	High Similarity	NPC27323
0.866	High Similarity	NPC155908
0.8632	High Similarity	NPC184169
0.8571	High Similarity	NPC325292
0.8571	High Similarity	NPC138117
0.8558	High Similarity	NPC135464
0.8558	High Similarity	NPC92623
0.8542	High Similarity	NPC104216
0.8515	High Similarity	NPC51333
0.8515	High Similarity	NPC92730
0.8515	High Similarity	NPC78119
0.8515	High Similarity	NPC132078
0.8515	High Similarity	NPC216468
0.8505	High Similarity	NPC139946
0.8462	Intermediate Similarity	NPC154899
0.8462	Intermediate Similarity	NPC233396
0.8454	Intermediate Similarity	NPC280347
0.8454	Intermediate Similarity	NPC318325
0.8454	Intermediate Similarity	NPC123273
0.8454	Intermediate Similarity	NPC242240
0.8454	Intermediate Similarity	NPC177420
0.8431	Intermediate Similarity	NPC225506
0.8431	Intermediate Similarity	NPC213730
0.8421	Intermediate Similarity	NPC248817
0.8416	Intermediate Similarity	NPC474073
0.8416	Intermediate Similarity	NPC225464
0.84	Intermediate Similarity	NPC26244
0.84	Intermediate Similarity	NPC313650
0.8367	Intermediate Similarity	NPC55561
0.8367	Intermediate Similarity	NPC300017
0.8351	Intermediate Similarity	NPC113460
0.8351	Intermediate Similarity	NPC25493
0.835	Intermediate Similarity	NPC40258
0.835	Intermediate Similarity	NPC472585
0.835	Intermediate Similarity	NPC91461
0.835	Intermediate Similarity	NPC7686
0.8333	Intermediate Similarity	NPC122005
0.8333	Intermediate Similarity	NPC252821
0.8333	Intermediate Similarity	NPC128723
0.8333	Intermediate Similarity	NPC197783
0.8333	Intermediate Similarity	NPC171843
0.8317	Intermediate Similarity	NPC473388
0.8317	Intermediate Similarity	NPC82664
0.8317	Intermediate Similarity	NPC216520
0.8317	Intermediate Similarity	NPC292730
0.8317	Intermediate Similarity	NPC132271
0.8316	Intermediate Similarity	NPC265146
0.8316	Intermediate Similarity	NPC124436
0.83	Intermediate Similarity	NPC151715
0.83	Intermediate Similarity	NPC152415
0.8283	Intermediate Similarity	NPC304541
0.8265	Intermediate Similarity	NPC258219
0.8257	Intermediate Similarity	NPC228425
0.8252	Intermediate Similarity	NPC294741
0.8247	Intermediate Similarity	NPC23167
0.8241	Intermediate Similarity	NPC63345
0.823	Intermediate Similarity	NPC163036
0.8229	Intermediate Similarity	NPC175313
0.8208	Intermediate Similarity	NPC477814
0.82	Intermediate Similarity	NPC55903
0.82	Intermediate Similarity	NPC306884
0.82	Intermediate Similarity	NPC147284
0.82	Intermediate Similarity	NPC94139
0.82	Intermediate Similarity	NPC162314
0.82	Intermediate Similarity	NPC3358
0.82	Intermediate Similarity	NPC210497
0.8182	Intermediate Similarity	NPC300478
0.8182	Intermediate Similarity	NPC176730
0.8182	Intermediate Similarity	NPC192
0.8182	Intermediate Similarity	NPC123175
0.8148	Intermediate Similarity	NPC265211
0.8148	Intermediate Similarity	NPC306045
0.81	Intermediate Similarity	NPC306074
0.81	Intermediate Similarity	NPC45040
0.81	Intermediate Similarity	NPC204210
0.8095	Intermediate Similarity	NPC192596
0.8095	Intermediate Similarity	NPC304638
0.8077	Intermediate Similarity	NPC211885
0.8058	Intermediate Similarity	NPC77492
0.8058	Intermediate Similarity	NPC475078
0.8056	Intermediate Similarity	NPC262365
0.8056	Intermediate Similarity	NPC201959
0.8056	Intermediate Similarity	NPC317305
0.8056	Intermediate Similarity	NPC31274
0.8053	Intermediate Similarity	NPC122117
0.8041	Intermediate Similarity	NPC150837
0.8039	Intermediate Similarity	NPC286006
0.8039	Intermediate Similarity	NPC222146
0.8039	Intermediate Similarity	NPC274678
0.8039	Intermediate Similarity	NPC144682
0.8037	Intermediate Similarity	NPC53740
0.8037	Intermediate Similarity	NPC113457
0.802	Intermediate Similarity	NPC181709
0.8019	Intermediate Similarity	NPC120719
0.8	Intermediate Similarity	NPC51633
0.8	Intermediate Similarity	NPC312304
0.8	Intermediate Similarity	NPC470355
0.8	Intermediate Similarity	NPC252105
0.7982	Intermediate Similarity	NPC55617
0.7982	Intermediate Similarity	NPC62258
0.7981	Intermediate Similarity	NPC33675
0.7981	Intermediate Similarity	NPC131587
0.7981	Intermediate Similarity	NPC471576
0.7981	Intermediate Similarity	NPC299762
0.798	Intermediate Similarity	NPC19680
0.798	Intermediate Similarity	NPC27974
0.7965	Intermediate Similarity	NPC154511
0.7965	Intermediate Similarity	NPC137496
0.7965	Intermediate Similarity	NPC257540
0.7965	Intermediate Similarity	NPC474358
0.7965	Intermediate Similarity	NPC474387
0.7965	Intermediate Similarity	NPC247858
0.7963	Intermediate Similarity	NPC305603
0.7963	Intermediate Similarity	NPC474352
0.7963	Intermediate Similarity	NPC61033
0.7963	Intermediate Similarity	NPC260952
0.7944	Intermediate Similarity	NPC138942
0.7944	Intermediate Similarity	NPC47284
0.7944	Intermediate Similarity	NPC470393
0.7941	Intermediate Similarity	NPC289769
0.7941	Intermediate Similarity	NPC471581
0.7941	Intermediate Similarity	NPC128062
0.7941	Intermediate Similarity	NPC76938
0.7928	Intermediate Similarity	NPC42911
0.7928	Intermediate Similarity	NPC290353
0.7928	Intermediate Similarity	NPC153795
0.7925	Intermediate Similarity	NPC235762
0.7925	Intermediate Similarity	NPC471228
0.7925	Intermediate Similarity	NPC168829
0.7925	Intermediate Similarity	NPC196479
0.7925	Intermediate Similarity	NPC108497
0.7909	Intermediate Similarity	NPC226401
0.7909	Intermediate Similarity	NPC79793
0.7909	Intermediate Similarity	NPC174096
0.7909	Intermediate Similarity	NPC120982
0.7909	Intermediate Similarity	NPC44732
0.7909	Intermediate Similarity	NPC46844
0.7909	Intermediate Similarity	NPC147634
0.7905	Intermediate Similarity	NPC48730
0.7905	Intermediate Similarity	NPC248396
0.7905	Intermediate Similarity	NPC174911
0.7905	Intermediate Similarity	NPC129373
0.7905	Intermediate Similarity	NPC253746
0.7905	Intermediate Similarity	NPC72729
0.79	Intermediate Similarity	NPC70436
0.7895	Intermediate Similarity	NPC477136
0.7895	Intermediate Similarity	NPC200988
0.7895	Intermediate Similarity	NPC476266
0.7895	Intermediate Similarity	NPC175799
0.7895	Intermediate Similarity	NPC145023
0.7895	Intermediate Similarity	NPC610
0.789	Intermediate Similarity	NPC75440
0.7885	Intermediate Similarity	NPC201967
0.7885	Intermediate Similarity	NPC152097
0.7879	Intermediate Similarity	NPC307235
0.7879	Intermediate Similarity	NPC407
0.7876	Intermediate Similarity	NPC147179
0.7876	Intermediate Similarity	NPC474486
0.787	Intermediate Similarity	NPC155072
0.787	Intermediate Similarity	NPC310456
0.7864	Intermediate Similarity	NPC107522
0.7864	Intermediate Similarity	NPC8392
0.7864	Intermediate Similarity	NPC32714
0.7857	Intermediate Similarity	NPC286904
0.785	Intermediate Similarity	NPC323810
0.785	Intermediate Similarity	NPC38079
0.785	Intermediate Similarity	NPC474603
0.785	Intermediate Similarity	NPC475225
0.785	Intermediate Similarity	NPC288411
0.785	Intermediate Similarity	NPC108875
0.785	Intermediate Similarity	NPC12987
0.7838	Intermediate Similarity	NPC179002
0.7838	Intermediate Similarity	NPC257430
0.7838	Intermediate Similarity	NPC308689
0.7838	Intermediate Similarity	NPC187583
0.783	Intermediate Similarity	NPC110764
0.783	Intermediate Similarity	NPC80800
0.7826	Intermediate Similarity	NPC86198
0.7826	Intermediate Similarity	NPC164649
0.7826	Intermediate Similarity	NPC48342
0.7822	Intermediate Similarity	NPC47950
0.7818	Intermediate Similarity	NPC473524
0.7818	Intermediate Similarity	NPC474272
0.781	Intermediate Similarity	NPC260775
0.781	Intermediate Similarity	NPC100870
0.781	Intermediate Similarity	NPC130193
0.7807	Intermediate Similarity	NPC38893
0.7807	Intermediate Similarity	NPC477137
0.7807	Intermediate Similarity	NPC281277
0.7807	Intermediate Similarity	NPC308828
0.7807	Intermediate Similarity	NPC308311
0.7807	Intermediate Similarity	NPC219112
0.7798	Intermediate Similarity	NPC320439
0.7798	Intermediate Similarity	NPC66834
0.7788	Intermediate Similarity	NPC12656

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 NPC62351 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	214
0.1-0.2	989
0.2-0.3	1556
0.3-0.4	2996
0.4-0.5	1889
0.5-0.6	1142
0.6-0.7	330
0.7-0.8	33
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8673	High Similarity	NPD1432	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD2859	Approved
0.84	Intermediate Similarity	NPD2860	Approved
0.8333	Intermediate Similarity	NPD3020	Approved
0.8316	Intermediate Similarity	NPD111	Approved
0.83	Intermediate Similarity	NPD2933	Approved
0.83	Intermediate Similarity	NPD2934	Approved
0.8039	Intermediate Similarity	NPD1809	Phase 2
0.7905	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD844	Approved
0.783	Intermediate Similarity	NPD846	Approved
0.783	Intermediate Similarity	NPD940	Approved
0.7826	Intermediate Similarity	NPD3091	Approved
0.7727	Intermediate Similarity	NPD2684	Approved
0.7719	Intermediate Similarity	NPD7157	Approved
0.7699	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD845	Approved
0.7658	Intermediate Similarity	NPD3021	Approved
0.7658	Intermediate Similarity	NPD3022	Approved
0.7619	Intermediate Similarity	NPD288	Approved
0.757	Intermediate Similarity	NPD1242	Phase 1
0.7563	Intermediate Similarity	NPD3092	Approved
0.7544	Intermediate Similarity	NPD2229	Approved
0.7544	Intermediate Similarity	NPD2228	Approved
0.7544	Intermediate Similarity	NPD2234	Approved
0.748	Intermediate Similarity	NPD5736	Approved
0.7458	Intermediate Similarity	NPD1357	Approved
0.7456	Intermediate Similarity	NPD7843	Approved
0.7414	Intermediate Similarity	NPD6671	Approved
0.7395	Intermediate Similarity	NPD4059	Approved
0.7395	Intermediate Similarity	NPD3095	Discontinued
0.7387	Intermediate Similarity	NPD968	Approved
0.7387	Intermediate Similarity	NPD3134	Approved
0.7368	Intermediate Similarity	NPD228	Approved
0.7345	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD290	Approved
0.7317	Intermediate Similarity	NPD3094	Phase 2
0.7304	Intermediate Similarity	NPD821	Approved
0.7273	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3019	Approved
0.725	Intermediate Similarity	NPD2932	Approved
0.7248	Intermediate Similarity	NPD3028	Approved
0.7244	Intermediate Similarity	NPD6663	Approved
0.7232	Intermediate Similarity	NPD1445	Approved
0.7232	Intermediate Similarity	NPD1444	Approved
0.7207	Intermediate Similarity	NPD9608	Approved
0.7207	Intermediate Similarity	NPD9610	Approved
0.7193	Intermediate Similarity	NPD4750	Phase 3
0.7168	Intermediate Similarity	NPD1358	Approved
0.7158	Intermediate Similarity	NPD9087	Approved
0.7154	Intermediate Similarity	NPD6582	Phase 2
0.7154	Intermediate Similarity	NPD6583	Phase 3
0.7143	Intermediate Similarity	NPD16	Approved
0.7143	Intermediate Similarity	NPD856	Approved
0.712	Intermediate Similarity	NPD6584	Phase 3
0.7117	Intermediate Similarity	NPD9500	Approved
0.7113	Intermediate Similarity	NPD9294	Approved
0.7107	Intermediate Similarity	NPD4589	Approved
0.7107	Intermediate Similarity	NPD2667	Approved
0.7107	Intermediate Similarity	NPD2668	Approved
0.7083	Intermediate Similarity	NPD9545	Approved
0.7063	Intermediate Similarity	NPD2861	Phase 2
0.7043	Intermediate Similarity	NPD1792	Phase 2
0.7043	Intermediate Similarity	NPD5451	Approved
0.7041	Intermediate Similarity	NPD9088	Approved
0.704	Intermediate Similarity	NPD4103	Phase 2
0.704	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1793	Approved
0.7034	Intermediate Similarity	NPD1791	Approved
0.7034	Intermediate Similarity	NPD9614	Approved
0.7034	Intermediate Similarity	NPD9618	Approved
0.7016	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5327	Phase 3
0.7016	Intermediate Similarity	NPD3685	Discontinued
0.7016	Intermediate Similarity	NPD4659	Approved
0.7009	Intermediate Similarity	NPD7635	Approved
0.7008	Intermediate Similarity	NPD4908	Phase 1
0.7	Intermediate Similarity	NPD318	Approved
0.7	Intermediate Similarity	NPD317	Approved
0.6992	Remote Similarity	NPD1610	Phase 2
0.6984	Remote Similarity	NPD4624	Approved
0.6967	Remote Similarity	NPD4626	Approved
0.6967	Remote Similarity	NPD1778	Approved
0.6967	Remote Similarity	NPD1751	Approved
0.6953	Remote Similarity	NPD3027	Phase 3
0.6952	Remote Similarity	NPD9295	Approved
0.6949	Remote Similarity	NPD5283	Phase 1
0.6947	Remote Similarity	NPD6353	Approved
0.6942	Remote Similarity	NPD1548	Phase 1
0.6935	Remote Similarity	NPD2562	Approved
0.6935	Remote Similarity	NPD2561	Approved
0.6923	Remote Similarity	NPD3620	Phase 2
0.6923	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4140	Approved
0.6911	Remote Similarity	NPD3421	Phase 3
0.6911	Remote Similarity	NPD3496	Discontinued
0.6909	Remote Similarity	NPD9273	Approved
0.6899	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD2629	Approved
0.6885	Remote Similarity	NPD4093	Discontinued
0.6885	Remote Similarity	NPD5585	Approved
0.6885	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5691	Approved
0.6885	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.688	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5735	Approved
0.687	Remote Similarity	NPD2342	Discontinued
0.6864	Remote Similarity	NPD5535	Approved
0.6864	Remote Similarity	NPD9379	Approved
0.6864	Remote Similarity	NPD9377	Approved
0.686	Remote Similarity	NPD9616	Approved
0.686	Remote Similarity	NPD9615	Approved
0.686	Remote Similarity	NPD9613	Approved
0.685	Remote Similarity	NPD3690	Phase 2
0.685	Remote Similarity	NPD3691	Phase 2
0.6846	Remote Similarity	NPD6407	Approved
0.6846	Remote Similarity	NPD6405	Approved
0.6833	Remote Similarity	NPD255	Approved
0.6833	Remote Similarity	NPD4198	Discontinued
0.6833	Remote Similarity	NPD256	Approved
0.6829	Remote Similarity	NPD9381	Approved
0.6829	Remote Similarity	NPD9384	Approved
0.6829	Remote Similarity	NPD5846	Approved
0.6829	Remote Similarity	NPD6516	Phase 2
0.6825	Remote Similarity	NPD8651	Approved
0.6825	Remote Similarity	NPD6696	Suspended
0.6822	Remote Similarity	NPD7095	Approved
0.6814	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD5304	Approved
0.6803	Remote Similarity	NPD316	Approved
0.6803	Remote Similarity	NPD7741	Discontinued
0.6803	Remote Similarity	NPD5303	Approved
0.68	Remote Similarity	NPD2233	Approved
0.68	Remote Similarity	NPD2231	Phase 2
0.68	Remote Similarity	NPD2230	Approved
0.68	Remote Similarity	NPD2232	Approved
0.68	Remote Similarity	NPD2235	Phase 2
0.6794	Remote Similarity	NPD4060	Phase 1
0.6777	Remote Similarity	NPD3596	Phase 2
0.6774	Remote Similarity	NPD3847	Discontinued
0.6774	Remote Similarity	NPD3143	Discontinued
0.6772	Remote Similarity	NPD1135	Approved
0.6772	Remote Similarity	NPD1129	Approved
0.6772	Remote Similarity	NPD1131	Approved
0.6772	Remote Similarity	NPD1133	Approved
0.6772	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1134	Approved
0.6765	Remote Similarity	NPD9089	Approved
0.675	Remote Similarity	NPD475	Phase 2
0.6746	Remote Similarity	NPD9622	Approved
0.6746	Remote Similarity	NPD4749	Approved
0.6724	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD2195	Approved
0.6719	Remote Similarity	NPD2194	Approved
0.6718	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7743	Approved
0.6716	Remote Similarity	NPD7742	Approved
0.6695	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD2286	Discontinued
0.6667	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9365	Approved
0.6667	Remote Similarity	NPD3636	Approved
0.6667	Remote Similarity	NPD2238	Phase 2
0.6667	Remote Similarity	NPD826	Approved
0.6667	Remote Similarity	NPD3635	Approved
0.6667	Remote Similarity	NPD4208	Discontinued
0.6667	Remote Similarity	NPD1894	Discontinued
0.6667	Remote Similarity	NPD6581	Approved
0.6667	Remote Similarity	NPD6580	Approved
0.6667	Remote Similarity	NPD9093	Approved
0.6667	Remote Similarity	NPD7330	Discontinued
0.6667	Remote Similarity	NPD825	Approved
0.6667	Remote Similarity	NPD1241	Discontinued
0.6667	Remote Similarity	NPD3070	Discontinued
0.6667	Remote Similarity	NPD3637	Approved
0.6641	Remote Similarity	NPD987	Approved
0.6641	Remote Similarity	NPD6798	Discontinued
0.664	Remote Similarity	NPD3023	Approved
0.664	Remote Similarity	NPD3026	Approved
0.664	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD9493	Approved
0.6636	Remote Similarity	NPD9296	Approved
0.6617	Remote Similarity	NPD6355	Discontinued
0.6615	Remote Similarity	NPD2605	Approved
0.6615	Remote Similarity	NPD2606	Approved
0.6614	Remote Similarity	NPD4359	Approved
0.6614	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD1755	Approved
0.6613	Remote Similarity	NPD3025	Approved
0.6613	Remote Similarity	NPD3024	Approved
0.6613	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD4628	Phase 3
0.6594	Remote Similarity	NPD8166	Discontinued
0.6591	Remote Similarity	NPD4248	Discontinued
0.6589	Remote Similarity	NPD9621	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