NPASS Compound

Structure

CID146376 OpenBabel06191715502D 29 29 0 0 0 0 0 0 0 0999 V2000 -8.6603 -13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -13.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 1.7321 -0.0000 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 1.7321 -1.0000 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 0.8660 -1.5000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 29 1 0 0 0 0 3 4 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 20 23 2 0 0 0 0 21 24 2 0 0 0 0 21 25 1 0 0 0 0 22 24 1 0 0 0 0 22 26 2 0 0 0 0 23 25 1 0 0 0 0 23 29 1 0 0 0 0 24 27 1 0 0 0 0 25 28 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	406.31
Volume:	457.015
LogP:	8.384
LogD:	4.43
LogS:	-4.177
# Rotatable Bonds:	17
TPSA:	69.92
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.109
Synthetic Accessibility Score:	2.569
Fsp3:	0.68
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.014
MDCK Permeability:	1.3094107998767868e-05
Pgp-inhibitor:	0.146
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	100.3685073852539%
Volume Distribution (VD):	8.563
Pgp-substrate:	1.4854680299758911%

ADMET: Metabolism

CYP1A2-inhibitor:	0.323
CYP1A2-substrate:	0.216
CYP2C19-inhibitor:	0.536
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.172
CYP2C9-substrate:	0.97
CYP2D6-inhibitor:	0.625
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.198
CYP3A4-substrate:	0.027

ADMET: Excretion

Clearance (CL):	6.16
Half-life (T1/2):	0.425

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.003
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.978
Carcinogencity:	0.045
Eye Corrosion:	0.171
Eye Irritation:	0.939
Respiratory Toxicity:	0.683

Download Data

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

Natural Product: NPC146376

Natural Product ID:	NPC146376
*Common Name:**	2-Hydroxy-5-Methoxy-3-Octadecylcyclohexa-2,5-Diene-1,4-Dione
IUPAC Name:	2-hydroxy-5-methoxy-3-octadecylcyclohexa-2,5-diene-1,4-dione
Synonyms:
Standard InCHIKey:	VOJSRSKBOJBZEK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H42O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-21-24(27)22(26)20-23(29-2)25(21)28/h20,27H,3-19H2,1-2H3
SMILES:	CCCCCCCCCCCCCCCCCCC1=C(C(=O)C=C(C1=O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1975424
PubChem CID:	127797
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0002495] Quinones [CHEMONTID:0002384] Benzoquinones [CHEMONTID:0002494] P-benzoquinones

*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
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[10869197]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812212]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9834145]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2781	Iris kumaonensis	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3733	Senecio triangularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2566	0cardiopsaceae	Species	0cardiopsaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6516	Aspidosperma megalocarpon	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2781	Iris kumaonensis	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO942	Perophora namei	Species	Perophoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5561	Thenea muricata	Species	Theneidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1859	Lantana camara	Species	Verbenaceae	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
GI50	56

Activity Type	# Activity
Cell Line	56

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	45394.16	nM	PMID[465148]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	26001.6	nM	PMID[465148]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	28707.81	nM	PMID[465148]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	85506.67	nM	PMID[465148]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	80352.61	nM	PMID[465148]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	22490.55	nM	PMID[465148]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	45081.67	nM	PMID[465148]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	39994.47	nM	PMID[465148]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	64863.44	nM	PMID[465148]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[465148]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	41783.04	nM	PMID[465148]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	21134.89	nM	PMID[465148]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	34276.78	nM	PMID[465148]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	38994.2	nM	PMID[465148]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	39536.66	nM	PMID[465148]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	32433.96	nM	PMID[465148]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	61376.2	nM	PMID[465148]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	55207.74	nM	PMID[465148]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	40364.54	nM	PMID[465148]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	43752.21	nM	PMID[465148]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	51404.37	nM	PMID[465148]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	39084.09	nM	PMID[465148]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	28379.19	nM	PMID[465148]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	35237.09	nM	PMID[465148]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	53210.83	nM	PMID[465148]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[465148]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[465148]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	46665.94	nM	PMID[465148]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	26546.06	nM	PMID[465148]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	46773.51	nM	PMID[465148]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	42854.85	nM	PMID[465148]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	30619.63	nM	PMID[465148]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	38282.47	nM	PMID[465148]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	29512.09	nM	PMID[465148]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	43651.58	nM	PMID[465148]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	38459.18	nM	PMID[465148]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	41686.94	nM	PMID[465148]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[465148]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	29580.12	nM	PMID[465148]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	21677.04	nM	PMID[465148]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	88715.6	nM	PMID[465148]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	27797.13	nM	PMID[465148]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	39536.66	nM	PMID[465148]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	38815.04	nM	PMID[465148]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	36475.39	nM	PMID[465148]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	71449.63	nM	PMID[465148]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	78162.78	nM	PMID[465148]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	34276.78	nM	PMID[465148]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	71944.9	nM	PMID[465148]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	47315.13	nM	PMID[465148]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	62517.27	nM	PMID[465148]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	36391.5	nM	PMID[465148]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	88920.11	nM	PMID[465148]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	43551.19	nM	PMID[465148]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	48528.85	nM	PMID[465148]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	42953.64	nM	PMID[465148]

☑ 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 NPC146376 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	155
0.1-0.2	1741
0.2-0.3	8741
0.3-0.4	18309
0.4-0.5	8738
0.5-0.6	4145
0.6-0.7	776
0.7-0.8	60
0.8-0.85	7
0.85-0.9	4
0.9-0.95	13
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC125578
1.0	High Similarity	NPC263382
0.9841	High Similarity	NPC243272
0.9692	High Similarity	NPC94743
0.9692	High Similarity	NPC291062
0.9538	High Similarity	NPC94488
0.9538	High Similarity	NPC262673
0.9365	High Similarity	NPC7029
0.9265	High Similarity	NPC264178
0.9231	High Similarity	NPC474619
0.9219	High Similarity	NPC98897
0.9206	High Similarity	NPC143168
0.9206	High Similarity	NPC53109
0.9077	High Similarity	NPC16119
0.9062	High Similarity	NPC34622
0.9062	High Similarity	NPC474400
0.8906	High Similarity	NPC151728
0.8906	High Similarity	NPC57463
0.8906	High Similarity	NPC477830
0.8806	High Similarity	NPC134385
0.8571	High Similarity	NPC320421
0.8438	Intermediate Similarity	NPC473494
0.8356	Intermediate Similarity	NPC473536
0.806	Intermediate Similarity	NPC477707
0.8	Intermediate Similarity	NPC139056
0.7973	Intermediate Similarity	NPC477708
0.7857	Intermediate Similarity	NPC251429
0.7846	Intermediate Similarity	NPC200831
0.7846	Intermediate Similarity	NPC224103
0.7846	Intermediate Similarity	NPC299369
0.775	Intermediate Similarity	NPC8518
0.775	Intermediate Similarity	NPC263997
0.775	Intermediate Similarity	NPC6185
0.775	Intermediate Similarity	NPC241512
0.775	Intermediate Similarity	NPC132228
0.7703	Intermediate Similarity	NPC147438
0.7656	Intermediate Similarity	NPC317796
0.7619	Intermediate Similarity	NPC137396
0.75	Intermediate Similarity	NPC26504
0.75	Intermediate Similarity	NPC474805
0.7432	Intermediate Similarity	NPC474539
0.7403	Intermediate Similarity	NPC283087
0.7397	Intermediate Similarity	NPC469914
0.7361	Intermediate Similarity	NPC473213
0.7353	Intermediate Similarity	NPC106851
0.7353	Intermediate Similarity	NPC274927
0.7317	Intermediate Similarity	NPC77971
0.7317	Intermediate Similarity	NPC474680
0.7313	Intermediate Similarity	NPC192843
0.7308	Intermediate Similarity	NPC231739
0.7297	Intermediate Similarity	NPC477455
0.7294	Intermediate Similarity	NPC475823
0.7294	Intermediate Similarity	NPC474209
0.7262	Intermediate Similarity	NPC53454
0.726	Intermediate Similarity	NPC477452
0.725	Intermediate Similarity	NPC99308
0.725	Intermediate Similarity	NPC474085
0.725	Intermediate Similarity	NPC55869
0.7229	Intermediate Similarity	NPC472009
0.7229	Intermediate Similarity	NPC203795
0.7215	Intermediate Similarity	NPC475681
0.7188	Intermediate Similarity	NPC22329
0.7179	Intermediate Similarity	NPC471061
0.716	Intermediate Similarity	NPC47450
0.716	Intermediate Similarity	NPC103486
0.7143	Intermediate Similarity	NPC40082
0.7143	Intermediate Similarity	NPC175079
0.7143	Intermediate Similarity	NPC472007
0.7125	Intermediate Similarity	NPC108955
0.7123	Intermediate Similarity	NPC298249
0.7108	Intermediate Similarity	NPC470177
0.7108	Intermediate Similarity	NPC32037
0.7108	Intermediate Similarity	NPC90287
0.7093	Intermediate Similarity	NPC471399
0.7083	Intermediate Similarity	NPC61473
0.7073	Intermediate Similarity	NPC477786
0.7073	Intermediate Similarity	NPC105803
0.7073	Intermediate Similarity	NPC477784
0.7073	Intermediate Similarity	NPC477785
0.7067	Intermediate Similarity	NPC173321
0.7059	Intermediate Similarity	NPC281230
0.7059	Intermediate Similarity	NPC472008
0.7051	Intermediate Similarity	NPC110725
0.7031	Intermediate Similarity	NPC220191
0.7011	Intermediate Similarity	NPC146852
0.7	Intermediate Similarity	NPC122521
0.7	Intermediate Similarity	NPC174447
0.7	Intermediate Similarity	NPC229252
0.7	Intermediate Similarity	NPC143857
0.7	Intermediate Similarity	NPC235242
0.7	Intermediate Similarity	NPC251042
0.6986	Remote Similarity	NPC137163
0.6933	Remote Similarity	NPC474060
0.6932	Remote Similarity	NPC61275
0.6923	Remote Similarity	NPC477458
0.6912	Remote Similarity	NPC477201
0.6905	Remote Similarity	NPC133652
0.6901	Remote Similarity	NPC15130
0.6901	Remote Similarity	NPC201939
0.6901	Remote Similarity	NPC473212
0.6901	Remote Similarity	NPC138056
0.6901	Remote Similarity	NPC115752
0.6901	Remote Similarity	NPC254449
0.6875	Remote Similarity	NPC475994
0.6875	Remote Similarity	NPC30321
0.6875	Remote Similarity	NPC23778
0.6875	Remote Similarity	NPC478122
0.686	Remote Similarity	NPC475001
0.686	Remote Similarity	NPC185059
0.6849	Remote Similarity	NPC176215
0.6849	Remote Similarity	NPC296436
0.6835	Remote Similarity	NPC470525
0.6835	Remote Similarity	NPC92080
0.6829	Remote Similarity	NPC286229
0.6829	Remote Similarity	NPC225515
0.6829	Remote Similarity	NPC275766
0.6818	Remote Similarity	NPC470036
0.6818	Remote Similarity	NPC174167
0.6812	Remote Similarity	NPC268185
0.6806	Remote Similarity	NPC473210
0.6806	Remote Similarity	NPC473211
0.68	Remote Similarity	NPC134593
0.6795	Remote Similarity	NPC474321
0.6795	Remote Similarity	NPC227396
0.6795	Remote Similarity	NPC160540
0.679	Remote Similarity	NPC27817
0.679	Remote Similarity	NPC471740
0.6778	Remote Similarity	NPC279313
0.6761	Remote Similarity	NPC243532
0.6757	Remote Similarity	NPC83965
0.6757	Remote Similarity	NPC197089
0.675	Remote Similarity	NPC211279
0.6744	Remote Similarity	NPC471738
0.6742	Remote Similarity	NPC263780
0.6712	Remote Similarity	NPC328089
0.6712	Remote Similarity	NPC68343
0.6711	Remote Similarity	NPC143396
0.6711	Remote Similarity	NPC10758
0.6711	Remote Similarity	NPC250928
0.6707	Remote Similarity	NPC2482
0.6707	Remote Similarity	NPC162741
0.6707	Remote Similarity	NPC74086
0.6707	Remote Similarity	NPC91332
0.6705	Remote Similarity	NPC223093
0.6705	Remote Similarity	NPC265856
0.6705	Remote Similarity	NPC166554
0.6667	Remote Similarity	NPC74410
0.6667	Remote Similarity	NPC53733
0.6667	Remote Similarity	NPC478247
0.6667	Remote Similarity	NPC478246
0.6667	Remote Similarity	NPC23170
0.6667	Remote Similarity	NPC189485
0.6667	Remote Similarity	NPC8091
0.6632	Remote Similarity	NPC179208
0.663	Remote Similarity	NPC20066
0.6629	Remote Similarity	NPC248913
0.6629	Remote Similarity	NPC26865
0.6629	Remote Similarity	NPC45579
0.6629	Remote Similarity	NPC32944
0.6629	Remote Similarity	NPC193396
0.6628	Remote Similarity	NPC261721
0.6627	Remote Similarity	NPC278459
0.6627	Remote Similarity	NPC189237
0.6627	Remote Similarity	NPC116797
0.6627	Remote Similarity	NPC474353
0.6627	Remote Similarity	NPC44963
0.6627	Remote Similarity	NPC472684
0.6625	Remote Similarity	NPC16279
0.6625	Remote Similarity	NPC256640
0.6625	Remote Similarity	NPC1254
0.6625	Remote Similarity	NPC180886
0.6625	Remote Similarity	NPC205615
0.6623	Remote Similarity	NPC318766
0.6622	Remote Similarity	NPC474329
0.6622	Remote Similarity	NPC474304
0.6618	Remote Similarity	NPC424
0.6618	Remote Similarity	NPC32467
0.6618	Remote Similarity	NPC154245
0.6618	Remote Similarity	NPC6095
0.6618	Remote Similarity	NPC25417
0.6618	Remote Similarity	NPC85813
0.6618	Remote Similarity	NPC87564
0.6618	Remote Similarity	NPC87394
0.6618	Remote Similarity	NPC261831
0.6618	Remote Similarity	NPC129710
0.6618	Remote Similarity	NPC88966
0.6618	Remote Similarity	NPC281972
0.6618	Remote Similarity	NPC290563
0.6593	Remote Similarity	NPC91408
0.6593	Remote Similarity	NPC777
0.6591	Remote Similarity	NPC142159
0.6591	Remote Similarity	NPC65615
0.6591	Remote Similarity	NPC280833
0.6591	Remote Similarity	NPC68148
0.6591	Remote Similarity	NPC95364
0.6591	Remote Similarity	NPC112454
0.6588	Remote Similarity	NPC469884
0.6588	Remote Similarity	NPC474251
0.6588	Remote Similarity	NPC469809
0.6585	Remote Similarity	NPC192329

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 NPC146376 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	2525
0.2-0.3	4170
0.3-0.4	1735
0.4-0.5	364
0.5-0.6	193
0.6-0.7	18
0.7-0.8	2
0.8-0.85	0
0.85-0.9	1
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9206	High Similarity	NPD2664	Clinical (unspecified phase)
0.9077	High Similarity	NPD3704	Approved
0.9077	High Similarity	NPD6108	Clinical (unspecified phase)
0.8611	High Similarity	NPD4756	Discovery
0.7846	Intermediate Similarity	NPD8779	Phase 3
0.7465	Intermediate Similarity	NPD7331	Phase 2
0.7342	Intermediate Similarity	NPD4695	Discontinued
0.7083	Intermediate Similarity	NPD7341	Phase 2
0.6765	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD3197	Phase 1
0.6707	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6110	Phase 1
0.6618	Remote Similarity	NPD3196	Approved
0.6618	Remote Similarity	NPD3194	Approved
0.6618	Remote Similarity	NPD4266	Approved
0.6618	Remote Similarity	NPD3195	Phase 2
0.6591	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5282	Discontinued
0.6471	Remote Similarity	NPD3172	Approved
0.6463	Remote Similarity	NPD3617	Approved
0.6322	Remote Similarity	NPD5329	Approved
0.6292	Remote Similarity	NPD6672	Approved
0.6292	Remote Similarity	NPD5737	Approved
0.6279	Remote Similarity	NPD7154	Phase 3
0.6277	Remote Similarity	NPD6084	Phase 2
0.6277	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD5279	Phase 3
0.625	Remote Similarity	NPD5690	Phase 2
0.6237	Remote Similarity	NPD5695	Phase 3
0.6222	Remote Similarity	NPD4753	Phase 2
0.6207	Remote Similarity	NPD4197	Approved
0.6176	Remote Similarity	NPD28	Approved
0.6176	Remote Similarity	NPD29	Approved
0.6163	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD1696	Phase 3
0.6136	Remote Similarity	NPD5363	Approved
0.6067	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD4694	Approved
0.6067	Remote Similarity	NPD5280	Approved
0.6064	Remote Similarity	NPD5210	Approved
0.6064	Remote Similarity	NPD4629	Approved
0.6047	Remote Similarity	NPD5369	Approved
0.6044	Remote Similarity	NPD6673	Approved
0.6044	Remote Similarity	NPD6080	Approved
0.6044	Remote Similarity	NPD6904	Approved
0.6042	Remote Similarity	NPD5696	Approved
0.6023	Remote Similarity	NPD3666	Approved
0.6023	Remote Similarity	NPD3133	Approved
0.6023	Remote Similarity	NPD4786	Approved
0.6023	Remote Similarity	NPD3665	Phase 1
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5221	Approved
0.5978	Remote Similarity	NPD6698	Approved
0.5978	Remote Similarity	NPD46	Approved
0.5978	Remote Similarity	NPD5785	Approved
0.5977	Remote Similarity	NPD4223	Phase 3
0.5977	Remote Similarity	NPD4221	Approved
0.5977	Remote Similarity	NPD3667	Approved
0.5957	Remote Similarity	NPD7748	Approved
0.5938	Remote Similarity	NPD5173	Approved
0.5914	Remote Similarity	NPD6079	Approved
0.5914	Remote Similarity	NPD6050	Approved
0.5914	Remote Similarity	NPD7515	Phase 2
0.5909	Remote Similarity	NPD5362	Discontinued
0.5909	Remote Similarity	NPD9090	Phase 3
0.5889	Remote Similarity	NPD3618	Phase 1
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD3173	Approved
0.5882	Remote Similarity	NPD6899	Approved
0.587	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.587	Remote Similarity	NPD5328	Approved
0.587	Remote Similarity	NPD6101	Approved
0.5851	Remote Similarity	NPD6399	Phase 3
0.5842	Remote Similarity	NPD6402	Approved
0.5842	Remote Similarity	NPD7128	Approved
0.5842	Remote Similarity	NPD6675	Approved
0.5842	Remote Similarity	NPD5739	Approved
0.5833	Remote Similarity	NPD4697	Phase 3
0.5816	Remote Similarity	NPD5285	Approved
0.5816	Remote Similarity	NPD5286	Approved
0.5816	Remote Similarity	NPD4696	Approved
0.5811	Remote Similarity	NPD6109	Phase 1
0.5806	Remote Similarity	NPD5692	Phase 3
0.5795	Remote Similarity	NPD4269	Approved
0.5795	Remote Similarity	NPD4270	Approved
0.5795	Remote Similarity	NPD6435	Approved
0.5784	Remote Similarity	NPD5697	Approved
0.5773	Remote Similarity	NPD4755	Approved
0.5773	Remote Similarity	NPD7902	Approved
0.5769	Remote Similarity	NPD7102	Approved
0.5769	Remote Similarity	NPD6883	Approved
0.5769	Remote Similarity	NPD7290	Approved
0.5761	Remote Similarity	NPD4518	Approved
0.5758	Remote Similarity	NPD5223	Approved
0.5747	Remote Similarity	NPD5368	Approved
0.5747	Remote Similarity	NPD4252	Approved
0.5745	Remote Similarity	NPD5693	Phase 1
0.5745	Remote Similarity	NPD5694	Approved
0.5745	Remote Similarity	NPD6411	Approved
0.5735	Remote Similarity	NPD622	Approved
0.5728	Remote Similarity	NPD6011	Approved
0.5728	Remote Similarity	NPD7320	Approved
0.5727	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7146	Approved
0.5714	Remote Similarity	NPD6684	Approved
0.5714	Remote Similarity	NPD6409	Approved
0.5714	Remote Similarity	NPD6869	Approved
0.5714	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD4690	Approved
0.5714	Remote Similarity	NPD8039	Approved
0.5714	Remote Similarity	NPD4688	Approved
0.5714	Remote Similarity	NPD4689	Approved
0.5714	Remote Similarity	NPD4138	Approved
0.5714	Remote Similarity	NPD6649	Approved
0.5714	Remote Similarity	NPD5786	Approved
0.5714	Remote Similarity	NPD8130	Phase 1
0.5714	Remote Similarity	NPD4693	Phase 3
0.5714	Remote Similarity	NPD6617	Approved
0.5714	Remote Similarity	NPD5330	Approved
0.5714	Remote Similarity	NPD5205	Approved
0.5714	Remote Similarity	NPD7521	Approved
0.5714	Remote Similarity	NPD6422	Discontinued
0.5714	Remote Similarity	NPD4519	Discontinued
0.5714	Remote Similarity	NPD6098	Approved
0.5714	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD7334	Approved
0.5714	Remote Similarity	NPD4623	Approved
0.57	Remote Similarity	NPD5224	Approved
0.57	Remote Similarity	NPD5211	Phase 2
0.57	Remote Similarity	NPD5226	Approved
0.57	Remote Similarity	NPD4633	Approved
0.57	Remote Similarity	NPD5225	Approved
0.5698	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD5778	Approved
0.5684	Remote Similarity	NPD5779	Approved
0.5684	Remote Similarity	NPD5133	Approved
0.5673	Remote Similarity	NPD6012	Approved
0.5673	Remote Similarity	NPD6373	Approved
0.5673	Remote Similarity	NPD6372	Approved
0.5673	Remote Similarity	NPD6013	Approved
0.5673	Remote Similarity	NPD6014	Approved
0.567	Remote Similarity	NPD7614	Phase 1
0.5667	Remote Similarity	NPD3668	Phase 3
0.566	Remote Similarity	NPD8297	Approved
0.566	Remote Similarity	NPD6882	Approved
0.5658	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4700	Approved
0.5644	Remote Similarity	NPD5175	Approved
0.5644	Remote Similarity	NPD5174	Approved
0.5631	Remote Similarity	NPD5701	Approved
0.5625	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5618	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.561	Remote Similarity	NPD4691	Approved
0.5604	Remote Similarity	NPD1694	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