NPASS Compound

Structure

NPC473393 OpenBabel07101718292D 22 22 0 0 1 0 0 0 0 0999 V2000 -4.3301 0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8301 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8301 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8301 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8301 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3301 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8301 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3301 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 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 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 16 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 6 20 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 16 2 0 0 0 0 9 11 1 0 0 0 0 9 18 2 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 20 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 19 22 1 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.19
Volume:	345.045
LogP:	5.102
LogD:	4.037
LogS:	-5.355
# Rotatable Bonds:	8
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.374
Synthetic Accessibility Score:	3.288
Fsp3:	0.35
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:	-4.6
MDCK Permeability:	2.2416870706365444e-05
Pgp-inhibitor:	0.553
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.325
Plasma Protein Binding (PPB):	94.02909088134766%
Volume Distribution (VD):	1.205
Pgp-substrate:	10.084240913391113%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.168
CYP2C19-inhibitor:	0.899
CYP2C19-substrate:	0.616
CYP2C9-inhibitor:	0.718
CYP2C9-substrate:	0.88
CYP2D6-inhibitor:	0.85
CYP2D6-substrate:	0.057
CYP3A4-inhibitor:	0.94
CYP3A4-substrate:	0.38

ADMET: Excretion

Clearance (CL):	2.158
Half-life (T1/2):	0.128

ADMET: Toxicity

hERG Blockers:	0.581
Human Hepatotoxicity (H-HT):	0.323
Drug-inuced Liver Injury (DILI):	0.226
AMES Toxicity:	0.062
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.246
Skin Sensitization:	0.959
Carcinogencity:	0.444
Eye Corrosion:	0.076
Eye Irritation:	0.836
Respiratory Toxicity:	0.135

Download Data

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

Natural Product: NPC473393

Natural Product ID:	NPC473393
*Common Name:**	Acetylbakuchiol
IUPAC Name:	[4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenyl] acetate
Synonyms:	Acetylbakuchiol
Standard InCHIKey:	KLWKVZWSRSGVHJ-UPTIQUDWSA-N
Standard InCHI:	InChI=1S/C20H26O2/c1-6-20(5,14-7-8-16(2)3)15-13-18-9-11-19(12-10-18)22-17(4)21/h6,8-13,15H,1,7,14H2,2-5H3/b15-13+/t20-/m1/s1
SMILES:	C=C[C@@](/C=C/c1ccc(cc1)OC(=O)C)(CCC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL408851
PubChem CID:	44450293
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
IC50	12
MIC	6
Others	46

Activity Type	# Activity
Cell Line	50
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	=	26800.0	nM	PMID[528700]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	18100.0	nM	PMID[528700]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI	=	71.0	%	PMID[528702]
NPT744	Cell Line	IMR-32	Homo sapiens	GI	=	71.0	%	PMID[528702]
NPT165	Cell Line	HeLa	Homo sapiens	GI	=	63.0	%	PMID[528702]
NPT1970	Cell Line	THP-1	Homo sapiens	GI	=	81.0	%	PMID[528702]
NPT81	Cell Line	A549	Homo sapiens	GI	=	1.0	%	PMID[528702]
NPT306	Cell Line	PC-3	Homo sapiens	GI	=	45.0	%	PMID[528702]
NPT744	Cell Line	IMR-32	Homo sapiens	GI	=	48.0	%	PMID[528702]
NPT1970	Cell Line	THP-1	Homo sapiens	GI	=	50.0	%	PMID[528702]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	56.0	%	PMID[528702]
NPT81	Cell Line	A549	Homo sapiens	GI	=	60.0	%	PMID[528702]
NPT306	Cell Line	PC-3	Homo sapiens	GI	=	60.0	%	PMID[528702]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI	=	62.0	%	PMID[528702]
NPT744	Cell Line	IMR-32	Homo sapiens	GI	=	59.0	%	PMID[528702]
NPT165	Cell Line	HeLa	Homo sapiens	GI	=	45.0	%	PMID[528702]
NPT1970	Cell Line	THP-1	Homo sapiens	GI	=	63.0	%	PMID[528702]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	31.0	%	PMID[528702]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	15.0	%	PMID[528702]
NPT1171	Cell Line	HEp-2	Homo sapiens	GI	=	52.0	%	PMID[528702]
NPT1171	Cell Line	HEp-2	Homo sapiens	GI	=	51.0	%	PMID[528702]
NPT1171	Cell Line	HEp-2	Homo sapiens	GI	=	46.0	%	PMID[528702]
NPT1171	Cell Line	HEp-2	Homo sapiens	GI	=	30.0	%	PMID[528702]
NPT1171	Cell Line	HEp-2	Homo sapiens	GI	=	14.0	%	PMID[528702]
NPT81	Cell Line	A549	Homo sapiens	GI	=	22.0	%	PMID[528702]
NPT81	Cell Line	A549	Homo sapiens	GI	=	13.0	%	PMID[528702]
NPT90	Cell Line	DU-145	Homo sapiens	GI	=	42.0	%	PMID[528702]
NPT90	Cell Line	DU-145	Homo sapiens	GI	=	29.0	%	PMID[528702]
NPT90	Cell Line	DU-145	Homo sapiens	GI	=	19.0	%	PMID[528702]
NPT1970	Cell Line	THP-1	Homo sapiens	GI	=	44.0	%	PMID[528702]
NPT1970	Cell Line	THP-1	Homo sapiens	GI	=	34.0	%	PMID[528702]
NPT306	Cell Line	PC-3	Homo sapiens	GI	=	32.0	%	PMID[528702]
NPT306	Cell Line	PC-3	Homo sapiens	GI	=	21.0	%	PMID[528702]
NPT744	Cell Line	IMR-32	Homo sapiens	GI	=	34.0	%	PMID[528702]
NPT744	Cell Line	IMR-32	Homo sapiens	GI	=	27.0	%	PMID[528702]
NPT148	Cell Line	HCT-15	Homo sapiens	GI	=	57.0	%	PMID[528702]
NPT148	Cell Line	HCT-15	Homo sapiens	GI	=	46.0	%	PMID[528702]
NPT148	Cell Line	HCT-15	Homo sapiens	GI	=	31.0	%	PMID[528702]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	18000.0	nM	PMID[528702]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	26000.0	nM	PMID[528702]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	23000.0	nM	PMID[528702]
NPT1171	Cell Line	HEp-2	Homo sapiens	IC50	=	20000.0	nM	PMID[528702]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	25000.0	nM	PMID[528702]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	40000.0	nM	PMID[528702]
NPT399	Cell Line	SF-295	Homo sapiens	IC50	=	8000.0	nM	PMID[528702]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	11000.0	nM	PMID[528702]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	44.0	%	PMID[528702]
NPT83	Cell Line	MCF7	Homo sapiens	GI	=	75.0	%	PMID[528702]
NPT81	Cell Line	A549	Homo sapiens	GI	=	72.0	%	PMID[528702]
NPT306	Cell Line	PC-3	Homo sapiens	GI	=	67.0	%	PMID[528702]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	5700.0	nM	PMID[528700]
NPT2	Others	Unspecified		IC50	=	5700.0	nM	PMID[528700]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	128.0	ug.mL-1	PMID[528701]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MBC	>	128.0	ug ml-1	PMID[528701]
NPT1129	Organism	Actinomyces viscosus	Actinomyces viscosus	MIC	=	32.0	ug.mL-1	PMID[528701]
NPT1129	Organism	Actinomyces viscosus	Actinomyces viscosus	MBC	=	64.0	ug ml-1	PMID[528701]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	MIC	=	16.0	ug.mL-1	PMID[528701]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	MBC	=	16.0	ug ml-1	PMID[528701]
NPT1484	Organism	Fusobacterium nucleatum	Fusobacterium nucleatum	MIC	>	128.0	ug.mL-1	PMID[528701]
NPT1484	Organism	Fusobacterium nucleatum	Fusobacterium nucleatum	MBC	>	128.0	ug ml-1	PMID[528701]
NPT1128	Organism	Prevotella intermedia	Prevotella intermedia	MIC	=	64.0	ug.mL-1	PMID[528701]
NPT1128	Organism	Prevotella intermedia	Prevotella intermedia	MBC	=	64.0	ug ml-1	PMID[528701]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	=	8.0	ug.mL-1	PMID[528701]
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MBC	=	8.0	ug ml-1	PMID[528701]

☑ 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 NPC473393 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	266
0.1-0.2	2091
0.2-0.3	6133
0.3-0.4	12809
0.4-0.5	4766
0.5-0.6	10296
0.6-0.7	5683
0.7-0.8	578
0.8-0.85	45
0.85-0.9	19
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9588	High Similarity	NPC107101
0.949	High Similarity	NPC307425
0.93	High Similarity	NPC283546
0.9216	High Similarity	NPC151530
0.9216	High Similarity	NPC157473
0.9208	High Similarity	NPC473855
0.9118	High Similarity	NPC176971
0.9091	High Similarity	NPC471576
0.902	High Similarity	NPC128730
0.8942	High Similarity	NPC291837
0.8932	High Similarity	NPC326447
0.8878	High Similarity	NPC471581
0.8857	High Similarity	NPC259554
0.8824	High Similarity	NPC179686
0.8774	High Similarity	NPC25067
0.8774	High Similarity	NPC88868
0.8774	High Similarity	NPC231251
0.8738	High Similarity	NPC109637
0.8692	High Similarity	NPC245552
0.8654	High Similarity	NPC238115
0.8641	High Similarity	NPC192596
0.8558	High Similarity	NPC2518
0.8544	High Similarity	NPC51633
0.8532	High Similarity	NPC303522
0.8482	Intermediate Similarity	NPC159916
0.8476	Intermediate Similarity	NPC470393
0.8476	Intermediate Similarity	NPC139891
0.8469	Intermediate Similarity	NPC99886
0.8469	Intermediate Similarity	NPC259134
0.8469	Intermediate Similarity	NPC8002
0.8469	Intermediate Similarity	NPC177844
0.8455	Intermediate Similarity	NPC235250
0.844	Intermediate Similarity	NPC280760
0.8431	Intermediate Similarity	NPC175298
0.8426	Intermediate Similarity	NPC473809
0.8396	Intermediate Similarity	NPC1065
0.8384	Intermediate Similarity	NPC71853
0.8381	Intermediate Similarity	NPC108875
0.8381	Intermediate Similarity	NPC38079
0.8378	Intermediate Similarity	NPC51345
0.8333	Intermediate Similarity	NPC149545
0.8319	Intermediate Similarity	NPC293424
0.8304	Intermediate Similarity	NPC470860
0.8304	Intermediate Similarity	NPC33717
0.83	Intermediate Similarity	NPC321956
0.8269	Intermediate Similarity	NPC13755
0.8261	Intermediate Similarity	NPC180006
0.8261	Intermediate Similarity	NPC235190
0.8246	Intermediate Similarity	NPC264976
0.8246	Intermediate Similarity	NPC234956
0.823	Intermediate Similarity	NPC183154
0.823	Intermediate Similarity	NPC471498
0.823	Intermediate Similarity	NPC471503
0.823	Intermediate Similarity	NPC263754
0.8182	Intermediate Similarity	NPC233238
0.8173	Intermediate Similarity	NPC171843
0.8165	Intermediate Similarity	NPC234639
0.8158	Intermediate Similarity	NPC152306
0.8158	Intermediate Similarity	NPC96705
0.8158	Intermediate Similarity	NPC124916
0.8158	Intermediate Similarity	NPC265547
0.8148	Intermediate Similarity	NPC258171
0.8131	Intermediate Similarity	NPC288760
0.8131	Intermediate Similarity	NPC227255
0.8125	Intermediate Similarity	NPC87563
0.812	Intermediate Similarity	NPC473464
0.812	Intermediate Similarity	NPC476332
0.8113	Intermediate Similarity	NPC298224
0.8108	Intermediate Similarity	NPC199462
0.8103	Intermediate Similarity	NPC163200
0.8103	Intermediate Similarity	NPC267064
0.8091	Intermediate Similarity	NPC141068
0.8087	Intermediate Similarity	NPC281356
0.8087	Intermediate Similarity	NPC98748
0.8087	Intermediate Similarity	NPC37858
0.8087	Intermediate Similarity	NPC298796
0.8053	Intermediate Similarity	NPC296526
0.8051	Intermediate Similarity	NPC470887
0.8051	Intermediate Similarity	NPC273772
0.8051	Intermediate Similarity	NPC109675
0.8037	Intermediate Similarity	NPC38209
0.8018	Intermediate Similarity	NPC139946
0.8017	Intermediate Similarity	NPC471504
0.8017	Intermediate Similarity	NPC31314
0.8017	Intermediate Similarity	NPC473290
0.8017	Intermediate Similarity	NPC157212
0.8017	Intermediate Similarity	NPC474874
0.8017	Intermediate Similarity	NPC193193
0.8	Intermediate Similarity	NPC100870
0.8	Intermediate Similarity	NPC307039
0.8	Intermediate Similarity	NPC277460
0.8	Intermediate Similarity	NPC101503
0.7983	Intermediate Similarity	NPC89630
0.7983	Intermediate Similarity	NPC27671
0.7983	Intermediate Similarity	NPC201667
0.7983	Intermediate Similarity	NPC73413
0.7982	Intermediate Similarity	NPC128633
0.7966	Intermediate Similarity	NPC96286
0.7966	Intermediate Similarity	NPC248429
0.7963	Intermediate Similarity	NPC8302
0.7963	Intermediate Similarity	NPC127676
0.7949	Intermediate Similarity	NPC322569
0.7946	Intermediate Similarity	NPC165646
0.7946	Intermediate Similarity	NPC266116
0.7944	Intermediate Similarity	NPC304638
0.7928	Intermediate Similarity	NPC46844
0.7925	Intermediate Similarity	NPC253746
0.7905	Intermediate Similarity	NPC470161
0.7905	Intermediate Similarity	NPC95755
0.7899	Intermediate Similarity	NPC472518
0.7899	Intermediate Similarity	NPC21238
0.7899	Intermediate Similarity	NPC320287
0.7899	Intermediate Similarity	NPC279379
0.7899	Intermediate Similarity	NPC315807
0.789	Intermediate Similarity	NPC113457
0.7881	Intermediate Similarity	NPC52247
0.7876	Intermediate Similarity	NPC109241
0.7876	Intermediate Similarity	NPC90903
0.7857	Intermediate Similarity	NPC55300
0.7851	Intermediate Similarity	NPC127604
0.7851	Intermediate Similarity	NPC128321
0.785	Intermediate Similarity	NPC12714
0.785	Intermediate Similarity	NPC300166
0.785	Intermediate Similarity	NPC84325
0.785	Intermediate Similarity	NPC310905
0.7833	Intermediate Similarity	NPC291899
0.7833	Intermediate Similarity	NPC221798
0.7818	Intermediate Similarity	NPC260952
0.7815	Intermediate Similarity	NPC257188
0.7815	Intermediate Similarity	NPC13007
0.7807	Intermediate Similarity	NPC294941
0.7807	Intermediate Similarity	NPC252004
0.7787	Intermediate Similarity	NPC243688
0.7787	Intermediate Similarity	NPC258567
0.7787	Intermediate Similarity	NPC194841
0.7787	Intermediate Similarity	NPC224774
0.7787	Intermediate Similarity	NPC121740
0.7778	Intermediate Similarity	NPC305205
0.7778	Intermediate Similarity	NPC69670
0.7778	Intermediate Similarity	NPC163036
0.7778	Intermediate Similarity	NPC43435
0.7769	Intermediate Similarity	NPC471828
0.7769	Intermediate Similarity	NPC471827
0.7768	Intermediate Similarity	NPC106141
0.7767	Intermediate Similarity	NPC270547
0.7748	Intermediate Similarity	NPC206341
0.7748	Intermediate Similarity	NPC201959
0.7745	Intermediate Similarity	NPC98772
0.7742	Intermediate Similarity	NPC475102
0.7742	Intermediate Similarity	NPC249425
0.7739	Intermediate Similarity	NPC220540
0.7731	Intermediate Similarity	NPC187868
0.7731	Intermediate Similarity	NPC114845
0.7731	Intermediate Similarity	NPC144418
0.7727	Intermediate Similarity	NPC326801
0.7724	Intermediate Similarity	NPC472519
0.7724	Intermediate Similarity	NPC474623
0.7724	Intermediate Similarity	NPC176590
0.7724	Intermediate Similarity	NPC469453
0.7724	Intermediate Similarity	NPC474651
0.7712	Intermediate Similarity	NPC14177
0.7712	Intermediate Similarity	NPC230951
0.7712	Intermediate Similarity	NPC247553
0.7712	Intermediate Similarity	NPC168050
0.7706	Intermediate Similarity	NPC292792
0.7706	Intermediate Similarity	NPC474603
0.7706	Intermediate Similarity	NPC12987
0.7705	Intermediate Similarity	NPC474476
0.7705	Intermediate Similarity	NPC101894
0.7699	Intermediate Similarity	NPC266932
0.7686	Intermediate Similarity	NPC111347
0.7686	Intermediate Similarity	NPC140521
0.7679	Intermediate Similarity	NPC79543
0.7679	Intermediate Similarity	NPC82016
0.7679	Intermediate Similarity	NPC474272
0.7672	Intermediate Similarity	NPC163398
0.7667	Intermediate Similarity	NPC288238
0.7667	Intermediate Similarity	NPC291189
0.7667	Intermediate Similarity	NPC69403
0.7664	Intermediate Similarity	NPC132725
0.7661	Intermediate Similarity	NPC474289
0.7658	Intermediate Similarity	NPC194034
0.7647	Intermediate Similarity	NPC471877
0.7647	Intermediate Similarity	NPC204466
0.7647	Intermediate Similarity	NPC302107
0.7647	Intermediate Similarity	NPC319378
0.7632	Intermediate Similarity	NPC115379
0.7632	Intermediate Similarity	NPC474920
0.7623	Intermediate Similarity	NPC249836
0.7623	Intermediate Similarity	NPC244495
0.7623	Intermediate Similarity	NPC170749
0.7623	Intermediate Similarity	NPC93219
0.7619	Intermediate Similarity	NPC81010
0.7619	Intermediate Similarity	NPC32977
0.7611	Intermediate Similarity	NPC183648
0.7611	Intermediate Similarity	NPC475852
0.7611	Intermediate Similarity	NPC183700
0.7611	Intermediate Similarity	NPC179309
0.7607	Intermediate Similarity	NPC122117
0.7607	Intermediate Similarity	NPC199209

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 NPC473393 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	1108
0.2-0.3	1578
0.3-0.4	2746
0.4-0.5	1792
0.5-0.6	1070
0.6-0.7	505
0.7-0.8	81
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8962	High Similarity	NPD5535	Approved
0.8932	High Similarity	NPD3134	Approved
0.8667	High Similarity	NPD1358	Approved
0.8476	Intermediate Similarity	NPD9697	Approved
0.8246	Intermediate Similarity	NPD5585	Approved
0.8241	Intermediate Similarity	NPD2684	Approved
0.8053	Intermediate Similarity	NPD7157	Approved
0.8017	Intermediate Similarity	NPD1778	Approved
0.7949	Intermediate Similarity	NPD3496	Discontinued
0.7946	Intermediate Similarity	NPD7843	Approved
0.7931	Intermediate Similarity	NPD5691	Approved
0.7899	Intermediate Similarity	NPD4359	Approved
0.7881	Intermediate Similarity	NPD422	Phase 1
0.7876	Intermediate Similarity	NPD1241	Discontinued
0.7845	Intermediate Similarity	NPD1894	Discontinued
0.7823	Intermediate Similarity	NPD8032	Phase 2
0.7805	Intermediate Similarity	NPD7095	Approved
0.7788	Intermediate Similarity	NPD821	Approved
0.776	Intermediate Similarity	NPD4140	Approved
0.7712	Intermediate Similarity	NPD4626	Approved
0.7679	Intermediate Similarity	NPD5451	Approved
0.7658	Intermediate Similarity	NPD290	Approved
0.7647	Intermediate Similarity	NPD3847	Discontinued
0.7623	Intermediate Similarity	NPD2797	Approved
0.7583	Intermediate Similarity	NPD1611	Approved
0.7583	Intermediate Similarity	NPD1535	Discovery
0.7581	Intermediate Similarity	NPD2614	Approved
0.7568	Intermediate Similarity	NPD968	Approved
0.7563	Intermediate Similarity	NPD17	Approved
0.7521	Intermediate Similarity	NPD3596	Phase 2
0.7521	Intermediate Similarity	NPD9717	Approved
0.7521	Intermediate Similarity	NPD1481	Phase 2
0.752	Intermediate Similarity	NPD5163	Phase 2
0.752	Intermediate Similarity	NPD5746	Approved
0.748	Intermediate Similarity	NPD3267	Approved
0.748	Intermediate Similarity	NPD987	Approved
0.748	Intermediate Similarity	NPD3266	Approved
0.746	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6798	Discontinued
0.7459	Intermediate Similarity	NPD5327	Phase 3
0.7458	Intermediate Similarity	NPD5536	Phase 2
0.744	Intermediate Similarity	NPD6832	Phase 2
0.744	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6671	Approved
0.7417	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5283	Phase 1
0.7402	Intermediate Similarity	NPD5745	Approved
0.7402	Intermediate Similarity	NPD4870	Approved
0.7402	Intermediate Similarity	NPD6233	Phase 2
0.7402	Intermediate Similarity	NPD4062	Phase 3
0.7398	Intermediate Similarity	NPD3225	Approved
0.7395	Intermediate Similarity	NPD6580	Approved
0.7395	Intermediate Similarity	NPD6581	Approved
0.7377	Intermediate Similarity	NPD3972	Approved
0.7377	Intermediate Similarity	NPD1608	Approved
0.7364	Intermediate Similarity	NPD2653	Approved
0.736	Intermediate Similarity	NPD2237	Approved
0.7344	Intermediate Similarity	NPD4060	Phase 1
0.7333	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9365	Approved
0.7333	Intermediate Similarity	NPD1357	Approved
0.7323	Intermediate Similarity	NPD3268	Approved
0.7317	Intermediate Similarity	NPD3685	Discontinued
0.7295	Intermediate Similarity	NPD1281	Approved
0.729	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2933	Approved
0.729	Intermediate Similarity	NPD2934	Approved
0.7288	Intermediate Similarity	NPD2557	Approved
0.7287	Intermediate Similarity	NPD6355	Discontinued
0.728	Intermediate Similarity	NPD1019	Discontinued
0.7273	Intermediate Similarity	NPD6516	Phase 2
0.7273	Intermediate Similarity	NPD5846	Approved
0.7255	Intermediate Similarity	NPD111	Approved
0.7241	Intermediate Similarity	NPD228	Approved
0.7222	Intermediate Similarity	NPD2860	Approved
0.7222	Intermediate Similarity	NPD454	Approved
0.7222	Intermediate Similarity	NPD2859	Approved
0.7218	Intermediate Similarity	NPD4534	Discontinued
0.72	Intermediate Similarity	NPD1203	Approved
0.72	Intermediate Similarity	NPD6362	Approved
0.719	Intermediate Similarity	NPD1651	Approved
0.7188	Intermediate Similarity	NPD1296	Phase 2
0.7179	Intermediate Similarity	NPD769	Approved
0.7177	Intermediate Similarity	NPD6583	Phase 3
0.7177	Intermediate Similarity	NPD6582	Phase 2
0.7176	Intermediate Similarity	NPD7097	Phase 1
0.7167	Intermediate Similarity	NPD7644	Approved
0.7154	Intermediate Similarity	NPD4340	Discontinued
0.7143	Intermediate Similarity	NPD5647	Approved
0.7132	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD2799	Discontinued
0.712	Intermediate Similarity	NPD8651	Approved
0.712	Intermediate Similarity	NPD1283	Approved
0.7119	Intermediate Similarity	NPD592	Approved
0.7119	Intermediate Similarity	NPD594	Approved
0.7111	Intermediate Similarity	NPD4110	Phase 3
0.7111	Intermediate Similarity	NPD4628	Phase 3
0.7111	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1182	Approved
0.7107	Intermediate Similarity	NPD9545	Approved
0.7107	Intermediate Similarity	NPD2486	Discontinued
0.7107	Intermediate Similarity	NPD1548	Phase 1
0.7094	Intermediate Similarity	NPD1139	Approved
0.7094	Intermediate Similarity	NPD1137	Approved
0.7077	Intermediate Similarity	NPD4307	Phase 2
0.7077	Intermediate Similarity	NPD2979	Phase 3
0.7073	Intermediate Similarity	NPD3447	Discontinued
0.7068	Intermediate Similarity	NPD2240	Approved
0.7068	Intermediate Similarity	NPD4476	Approved
0.7068	Intermediate Similarity	NPD2239	Approved
0.7068	Intermediate Similarity	NPD4477	Approved
0.7068	Intermediate Similarity	NPD2862	Discontinued
0.7054	Intermediate Similarity	NPD1048	Approved
0.7054	Intermediate Similarity	NPD7294	Phase 1
0.7049	Intermediate Similarity	NPD3444	Approved
0.7049	Intermediate Similarity	NPD2595	Approved
0.7049	Intermediate Similarity	NPD3049	Approved
0.7049	Intermediate Similarity	NPD3445	Approved
0.7049	Intermediate Similarity	NPD3443	Approved
0.7049	Intermediate Similarity	NPD6382	Discontinued
0.7049	Intermediate Similarity	NPD2594	Approved
0.704	Intermediate Similarity	NPD6543	Approved
0.704	Intermediate Similarity	NPD2428	Approved
0.704	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD6542	Approved
0.704	Intermediate Similarity	NPD6540	Phase 3
0.704	Intermediate Similarity	NPD6539	Approved
0.704	Intermediate Similarity	NPD2429	Approved
0.704	Intermediate Similarity	NPD4129	Approved
0.7034	Intermediate Similarity	NPD1138	Approved
0.7027	Intermediate Similarity	NPD3020	Approved
0.7023	Intermediate Similarity	NPD5124	Phase 1
0.7023	Intermediate Similarity	NPD4618	Approved
0.7023	Intermediate Similarity	NPD4622	Approved
0.7023	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD3705	Approved
0.7015	Intermediate Similarity	NPD5865	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7083	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6584	Phase 3
0.7008	Intermediate Similarity	NPD3691	Phase 2
0.7008	Intermediate Similarity	NPD3690	Phase 2
0.7	Intermediate Similarity	NPD6387	Discontinued
0.6992	Remote Similarity	NPD2554	Approved
0.6992	Remote Similarity	NPD2667	Approved
0.6992	Remote Similarity	NPD2668	Approved
0.6992	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD2556	Approved
0.6984	Remote Similarity	NPD6541	Approved
0.6984	Remote Similarity	NPD6538	Approved
0.6984	Remote Similarity	NPD196	Phase 1
0.6981	Remote Similarity	NPD9295	Approved
0.6978	Remote Similarity	NPD6273	Approved
0.697	Remote Similarity	NPD6653	Approved
0.6964	Remote Similarity	NPD3028	Approved
0.6953	Remote Similarity	NPD4993	Discontinued
0.6952	Remote Similarity	NPD1282	Approved
0.6947	Remote Similarity	NPD3140	Approved
0.6947	Remote Similarity	NPD3142	Approved
0.6935	Remote Similarity	NPD3294	Phase 2
0.6929	Remote Similarity	NPD1820	Approved
0.6929	Remote Similarity	NPD1817	Approved
0.6929	Remote Similarity	NPD1819	Approved
0.6929	Remote Similarity	NPD1818	Approved
0.6929	Remote Similarity	NPD3567	Approved
0.6929	Remote Similarity	NPD3568	Approved
0.6923	Remote Similarity	NPD411	Approved
0.6917	Remote Similarity	NPD5689	Approved
0.6917	Remote Similarity	NPD5688	Approved
0.6912	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD1652	Phase 2
0.6909	Remote Similarity	NPD1809	Phase 2
0.6905	Remote Similarity	NPD1421	Approved
0.6905	Remote Similarity	NPD1420	Approved
0.6903	Remote Similarity	NPD291	Approved
0.6899	Remote Similarity	NPD4908	Phase 1
0.6899	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5374	Approved
0.6897	Remote Similarity	NPD5373	Approved
0.6894	Remote Similarity	NPD1933	Approved
0.6894	Remote Similarity	NPD447	Suspended
0.6894	Remote Similarity	NPD5735	Approved
0.6889	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2353	Approved
0.6884	Remote Similarity	NPD6667	Approved
0.6884	Remote Similarity	NPD6666	Approved
0.688	Remote Similarity	NPD1610	Phase 2
0.688	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1091	Approved
0.6875	Remote Similarity	NPD4624	Approved
0.6875	Remote Similarity	NPD7018	Phase 2
0.6866	Remote Similarity	NPD7033	Discontinued
0.6866	Remote Similarity	NPD3748	Approved
0.6866	Remote Similarity	NPD4308	Phase 3
0.686	Remote Similarity	NPD709	Approved
0.685	Remote Similarity	NPD7258	Clinical (unspecified phase)
0.685	Remote Similarity	NPD6696	Suspended
0.685	Remote Similarity	NPD1876	Approved
0.6846	Remote Similarity	NPD3166	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