NPASS Compound

Structure

CID322301 OpenBabel06191716162D 40 41 0 0 1 0 0 0 0 0999 V2000 -6.7632 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9178 4.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0724 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 4.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0724 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0724 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9178 3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 3.4167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 1.9524 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.3816 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 0.4881 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5362 0.4881 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 1.6908 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2270 -1.4643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0724 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3816 2.9286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 2.4405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6908 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -0.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 40 1 0 0 0 0 10 12 1 0 0 0 0 10 15 2 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 18 23 1 0 0 0 0 18 33 2 0 0 0 0 19 24 1 0 0 0 0 19 34 2 0 0 0 0 20 27 2 0 0 0 0 20 28 1 0 0 0 0 21 29 2 0 0 0 0 21 32 1 0 0 0 0 22 25 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 23 30 2 0 0 0 0 24 31 1 0 0 0 0 24 32 2 0 0 0 0 25 28 2 0 0 0 0 25 30 1 0 0 0 0 26 29 1 0 0 0 0 26 31 2 0 0 0 0 27 35 1 0 0 0 0 28 36 1 0 0 0 0 29 37 1 0 0 0 0 30 38 1 0 0 0 0 31 39 1 0 0 0 0 32 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	554.29
Volume:	588.872
LogP:	7.691
LogD:	3.271
LogS:	-3.564
# Rotatable Bonds:	11
TPSA:	144.52
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.15
Synthetic Accessibility Score:	4.013
Fsp3:	0.438
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.203
MDCK Permeability:	1.1119746886834037e-05
Pgp-inhibitor:	0.859
Pgp-substrate:	0.732
Human Intestinal Absorption (HIA):	0.584
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	97.35523223876953%
Volume Distribution (VD):	1.363
Pgp-substrate:	5.03869104385376%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.713
CYP2C19-inhibitor:	0.532
CYP2C19-substrate:	0.57
CYP2C9-inhibitor:	0.663
CYP2C9-substrate:	0.978
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.086
CYP3A4-substrate:	0.235

ADMET: Excretion

Clearance (CL):	3.174
Half-life (T1/2):	0.042

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.836
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.833
Skin Sensitization:	0.93
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.608
Respiratory Toxicity:	0.145

Download Data

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

Natural Product: NPC322301

Natural Product ID:	NPC322301
*Common Name:**	1-[3-[1-[3-Acetyl-2,6-Dihydroxy-4-Methoxy-5-(3-Methylbut-2-Enyl)Phenyl]-3-Methylbutyl]-2,4,6-Trihydroxy-5-(3-Methylbut-2-Enyl)Phenyl]Ethanone
IUPAC Name:	1-[3-[1-[3-acetyl-2,6-dihydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-3-methylbutyl]-2,4,6-trihydroxy-5-(3-methylbut-2-enyl)phenyl]ethanone
Synonyms:
Standard InCHIKey:	KLFWXYAHGSXKAW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C32H42O8/c1-15(2)10-12-20-27(35)23(18(7)33)30(38)25(28(20)36)22(14-17(5)6)26-29(37)21(13-11-16(3)4)32(40-9)24(19(8)34)31(26)39/h10-11,17,22,35-39H,12-14H2,1-9H3
SMILES:	CC(=CCc1c(c(C(=O)C)c(c(C(CC(C)C)c2c(c(CC=C(C)C)c(c(C(=O)C)c2O)OC)O)c1O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488313
PubChem CID:	159969
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880321]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	bark	n.a.	PMID[22708987]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22708987]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614422]
NPO40004	Acronychia trifoliolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27797192]
NPO40004	Acronychia trifoliolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27933896]
NPO40004	Acronychia trifoliolata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31550158]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14356	Acronychia vestita	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14356	Acronychia vestita	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12980	Acronychia pedunculata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14356	Acronychia vestita	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12980	Acronychia pedunculata	Species	Rutaceae	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	68
IC50	7
Others	1

Activity Type	# Activity
Cell Line	71
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	468.81	nM	PMID[568686]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	2157.74	nM	PMID[568686]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	1101.54	nM	PMID[568686]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	275.42	nM	PMID[568686]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	3076.1	nM	PMID[568686]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	190.99	nM	PMID[568686]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	767.36	nM	PMID[568686]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	1158.78	nM	PMID[568686]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	2322.74	nM	PMID[568686]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	638.26	nM	PMID[568686]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	481.95	nM	PMID[568686]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	289.73	nM	PMID[568686]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	84.33	nM	PMID[568686]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	1145.51	nM	PMID[568686]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	644.17	nM	PMID[568686]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	1402.81	nM	PMID[568686]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	729.46	nM	PMID[568686]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	703.07	nM	PMID[568686]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	384.59	nM	PMID[568686]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	4897.79	nM	PMID[568686]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	332.66	nM	PMID[568686]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	1640.59	nM	PMID[568686]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	1145.51	nM	PMID[568686]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	1028.02	nM	PMID[568686]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	1104.08	nM	PMID[568686]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	479.73	nM	PMID[568686]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	1425.61	nM	PMID[568686]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	997.7	nM	PMID[568686]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	199.99	nM	PMID[568686]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	595.66	nM	PMID[568686]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	1428.89	nM	PMID[568686]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	422.67	nM	PMID[568686]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	418.79	nM	PMID[568686]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	1442.12	nM	PMID[568686]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	1566.75	nM	PMID[568686]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	1618.08	nM	PMID[568686]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	503.5	nM	PMID[568686]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	1798.87	nM	PMID[568686]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	537.03	nM	PMID[568686]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	1686.55	nM	PMID[568686]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	399.94	nM	PMID[568686]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	325.09	nM	PMID[568686]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	322.85	nM	PMID[568686]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	1035.14	nM	PMID[568686]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	305.49	nM	PMID[568686]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	385.48	nM	PMID[568686]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	2084.49	nM	PMID[568686]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	189.67	nM	PMID[568686]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	588.84	nM	PMID[568686]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	384.59	nM	PMID[568686]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	1210.6	nM	PMID[568686]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	527.23	nM	PMID[568686]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	1940.89	nM	PMID[568686]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	521.19	nM	PMID[568686]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	1702.16	nM	PMID[568686]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	1066.6	nM	PMID[568686]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	424.62	nM	PMID[568686]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	1633.05	nM	PMID[568686]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	1698.24	nM	PMID[568686]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	1452.11	nM	PMID[568686]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	380.19	nM	PMID[568686]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	277.97	nM	PMID[568686]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	722.77	nM	PMID[568686]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	1235.95	nM	PMID[568686]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	695.02	nM	PMID[568686]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	426.58	nM	PMID[568686]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	563.64	nM	PMID[568686]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	550.81	nM	PMID[568686]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Activity	<	50.0	%	PMID[568687]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	2300.0	nM	PMID[568687]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	2700.0	nM	PMID[568687]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	6100.0	nM	PMID[568688]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	6400.0	nM	PMID[568688]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	4900.0	nM	PMID[568688]
NPT956	Individual Protein	Prostaglandin E synthase	Homo sapiens	IC50	=	1100.0	nM	PMID[568687]
NPT2	Others	Unspecified		IC50	=	4400.0	nM	PMID[568688]

☑ 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 NPC322301 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	338
0.1-0.2	1472
0.2-0.3	3359
0.3-0.4	8362
0.4-0.5	10880
0.5-0.6	4068
0.6-0.7	6421
0.7-0.8	5401
0.8-0.85	1533
0.85-0.9	745
0.9-0.95	107
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC255801
0.9704	High Similarity	NPC476508
0.9695	High Similarity	NPC16197
0.9618	High Similarity	NPC15834
0.9618	High Similarity	NPC215875
0.9466	High Similarity	NPC279566
0.9389	High Similarity	NPC186628
0.9348	High Similarity	NPC297600
0.9328	High Similarity	NPC103842
0.9323	High Similarity	NPC285054
0.927	High Similarity	NPC477956
0.9265	High Similarity	NPC153979
0.9259	High Similarity	NPC156092
0.9259	High Similarity	NPC13575
0.922	High Similarity	NPC475348
0.922	High Similarity	NPC261271
0.9214	High Similarity	NPC328623
0.9203	High Similarity	NPC265178
0.9203	High Similarity	NPC11056
0.9197	High Similarity	NPC21350
0.9191	High Similarity	NPC41461
0.9191	High Similarity	NPC25287
0.9191	High Similarity	NPC249606
0.9191	High Similarity	NPC150399
0.9191	High Similarity	NPC66349
0.9191	High Similarity	NPC1486
0.9191	High Similarity	NPC477243
0.9191	High Similarity	NPC274109
0.9191	High Similarity	NPC12165
0.9191	High Similarity	NPC477244
0.9191	High Similarity	NPC98115
0.9191	High Similarity	NPC168105
0.9191	High Similarity	NPC213603
0.9191	High Similarity	NPC477242
0.9191	High Similarity	NPC186838
0.9191	High Similarity	NPC24394
0.9161	High Similarity	NPC476509
0.9155	High Similarity	NPC152233
0.9137	High Similarity	NPC40118
0.9137	High Similarity	NPC232021
0.9137	High Similarity	NPC126534
0.913	High Similarity	NPC240305
0.913	High Similarity	NPC283429
0.913	High Similarity	NPC472366
0.9124	High Similarity	NPC472419
0.9124	High Similarity	NPC317119
0.9118	High Similarity	NPC131039
0.9111	High Similarity	NPC144051
0.9111	High Similarity	NPC28753
0.9111	High Similarity	NPC159623
0.9111	High Similarity	NPC82225
0.9111	High Similarity	NPC18877
0.9111	High Similarity	NPC294593
0.9111	High Similarity	NPC204960
0.9111	High Similarity	NPC20560
0.9104	High Similarity	NPC27490
0.9078	High Similarity	NPC282957
0.9078	High Similarity	NPC194949
0.9078	High Similarity	NPC271288
0.9065	High Similarity	NPC259166
0.9065	High Similarity	NPC172250
0.9065	High Similarity	NPC48624
0.9065	High Similarity	NPC215311
0.9065	High Similarity	NPC213659
0.9065	High Similarity	NPC204985
0.9065	High Similarity	NPC144118
0.9065	High Similarity	NPC80962
0.9065	High Similarity	NPC219917
0.9065	High Similarity	NPC477272
0.9065	High Similarity	NPC253822
0.9065	High Similarity	NPC326109
0.9058	High Similarity	NPC251681
0.9058	High Similarity	NPC243528
0.9058	High Similarity	NPC248995
0.9058	High Similarity	NPC477055
0.9058	High Similarity	NPC254168
0.9058	High Similarity	NPC471620
0.9058	High Similarity	NPC477056
0.9058	High Similarity	NPC272844
0.9058	High Similarity	NPC472368
0.9044	High Similarity	NPC286336
0.9034	High Similarity	NPC43345
0.903	High Similarity	NPC324482
0.9021	High Similarity	NPC145467
0.9014	High Similarity	NPC25844
0.9014	High Similarity	NPC477955
0.9	High Similarity	NPC282300
0.9	High Similarity	NPC52789
0.9	High Similarity	NPC470087
0.9	High Similarity	NPC268204
0.9	High Similarity	NPC321980
0.9	High Similarity	NPC469404
0.9	High Similarity	NPC470089
0.9	High Similarity	NPC26051
0.9	High Similarity	NPC55832
0.8993	High Similarity	NPC53181
0.8993	High Similarity	NPC295384
0.8993	High Similarity	NPC217186
0.8993	High Similarity	NPC241975
0.8993	High Similarity	NPC470211
0.8993	High Similarity	NPC19476
0.8986	High Similarity	NPC23870
0.8978	High Similarity	NPC101752
0.8973	High Similarity	NPC324447
0.8971	High Similarity	NPC56031
0.8971	High Similarity	NPC242294
0.8971	High Similarity	NPC312318
0.8971	High Similarity	NPC472365
0.8971	High Similarity	NPC27643
0.8971	High Similarity	NPC470984
0.8971	High Similarity	NPC263670
0.8971	High Similarity	NPC337373
0.8971	High Similarity	NPC192304
0.8971	High Similarity	NPC139813
0.8971	High Similarity	NPC175098
0.8971	High Similarity	NPC188646
0.8966	High Similarity	NPC476551
0.8966	High Similarity	NPC476553
0.8966	High Similarity	NPC178484
0.8966	High Similarity	NPC476552
0.8963	High Similarity	NPC475009
0.8963	High Similarity	NPC475008
0.8963	High Similarity	NPC186097
0.8955	High Similarity	NPC84772
0.8951	High Similarity	NPC308200
0.8944	High Similarity	NPC471473
0.8944	High Similarity	NPC473014
0.8944	High Similarity	NPC471523
0.8944	High Similarity	NPC235217
0.8944	High Similarity	NPC476055
0.8944	High Similarity	NPC471524
0.8936	High Similarity	NPC84266
0.8929	High Similarity	NPC241100
0.8929	High Similarity	NPC159275
0.8929	High Similarity	NPC101366
0.8921	High Similarity	NPC470672
0.8921	High Similarity	NPC470671
0.8921	High Similarity	NPC474487
0.8921	High Similarity	NPC183639
0.8921	High Similarity	NPC474504
0.8921	High Similarity	NPC131130
0.8921	High Similarity	NPC219584
0.8921	High Similarity	NPC199458
0.8921	High Similarity	NPC470083
0.8913	High Similarity	NPC174999
0.8913	High Similarity	NPC156910
0.8913	High Similarity	NPC472367
0.8913	High Similarity	NPC473391
0.8913	High Similarity	NPC470989
0.8913	High Similarity	NPC476333
0.8913	High Similarity	NPC470985
0.8913	High Similarity	NPC472364
0.8912	High Similarity	NPC37253
0.8912	High Similarity	NPC79375
0.8897	High Similarity	NPC103105
0.8897	High Similarity	NPC212631
0.8897	High Similarity	NPC470988
0.8897	High Similarity	NPC129132
0.8897	High Similarity	NPC257756
0.8897	High Similarity	NPC205468
0.8897	High Similarity	NPC87231
0.8889	High Similarity	NPC250057
0.8889	High Similarity	NPC39195
0.8881	High Similarity	NPC212379
0.8881	High Similarity	NPC127059
0.8881	High Similarity	NPC470910
0.8881	High Similarity	NPC470322
0.8881	High Similarity	NPC69235
0.8881	High Similarity	NPC285630
0.8881	High Similarity	NPC181388
0.8881	High Similarity	NPC230818
0.8873	High Similarity	NPC470553
0.8873	High Similarity	NPC185276
0.8873	High Similarity	NPC245482
0.8873	High Similarity	NPC117836
0.8873	High Similarity	NPC307895
0.8873	High Similarity	NPC125894
0.8873	High Similarity	NPC51887
0.8873	High Similarity	NPC106985
0.8873	High Similarity	NPC85162
0.8873	High Similarity	NPC11700
0.8873	High Similarity	NPC476178
0.8873	High Similarity	NPC77794
0.8873	High Similarity	NPC278249
0.8873	High Similarity	NPC223812
0.8873	High Similarity	NPC81697
0.8873	High Similarity	NPC301751
0.8873	High Similarity	NPC475705
0.8873	High Similarity	NPC166138
0.8873	High Similarity	NPC107177
0.8873	High Similarity	NPC18585
0.8865	High Similarity	NPC110969
0.8865	High Similarity	NPC110038
0.8865	High Similarity	NPC49108
0.8865	High Similarity	NPC166689
0.8865	High Similarity	NPC285659
0.8865	High Similarity	NPC248372
0.8865	High Similarity	NPC156190
0.8865	High Similarity	NPC279650
0.8865	High Similarity	NPC26238

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 NPC322301 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	984
0.2-0.3	1601
0.3-0.4	2675
0.4-0.5	1966
0.5-0.6	1096
0.6-0.7	369
0.7-0.8	110
0.8-0.85	21
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9111	High Similarity	NPD6651	Approved
0.8912	High Similarity	NPD8443	Clinical (unspecified phase)
0.8824	High Similarity	NPD1240	Approved
0.8811	High Similarity	NPD4378	Clinical (unspecified phase)
0.8705	High Similarity	NPD1510	Phase 2
0.8696	High Similarity	NPD1607	Approved
0.8681	High Similarity	NPD7410	Clinical (unspecified phase)
0.8592	High Similarity	NPD2800	Approved
0.8591	High Similarity	NPD7819	Suspended
0.8514	High Similarity	NPD4380	Phase 2
0.8451	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD2533	Approved
0.8425	Intermediate Similarity	NPD2532	Approved
0.8425	Intermediate Similarity	NPD2534	Approved
0.8421	Intermediate Similarity	NPD7075	Discontinued
0.8392	Intermediate Similarity	NPD1549	Phase 2
0.8392	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7411	Suspended
0.828	Intermediate Similarity	NPD7473	Discontinued
0.8252	Intermediate Similarity	NPD2796	Approved
0.8235	Intermediate Similarity	NPD7768	Phase 2
0.8224	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD6959	Discontinued
0.8125	Intermediate Similarity	NPD2935	Discontinued
0.8089	Intermediate Similarity	NPD6232	Discontinued
0.8063	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1934	Approved
0.8039	Intermediate Similarity	NPD6801	Discontinued
0.7987	Intermediate Similarity	NPD1511	Approved
0.7987	Intermediate Similarity	NPD2801	Approved
0.7987	Intermediate Similarity	NPD6799	Approved
0.7949	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD2799	Discontinued
0.7931	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD6599	Discontinued
0.7905	Intermediate Similarity	NPD3750	Approved
0.7887	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD3882	Suspended
0.7881	Intermediate Similarity	NPD1512	Approved
0.7867	Intermediate Similarity	NPD7390	Discontinued
0.7838	Intermediate Similarity	NPD1243	Approved
0.7838	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD6166	Phase 2
0.7764	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD6099	Approved
0.7755	Intermediate Similarity	NPD1551	Phase 2
0.7755	Intermediate Similarity	NPD6100	Approved
0.775	Intermediate Similarity	NPD5710	Approved
0.775	Intermediate Similarity	NPD5711	Approved
0.7744	Intermediate Similarity	NPD5953	Discontinued
0.7736	Intermediate Similarity	NPD5494	Approved
0.773	Intermediate Similarity	NPD2798	Approved
0.7722	Intermediate Similarity	NPD3749	Approved
0.7707	Intermediate Similarity	NPD3817	Phase 2
0.7703	Intermediate Similarity	NPD2344	Approved
0.7683	Intermediate Similarity	NPD7074	Phase 3
0.7655	Intermediate Similarity	NPD943	Approved
0.7639	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7054	Approved
0.7622	Intermediate Similarity	NPD7286	Phase 2
0.76	Intermediate Similarity	NPD2654	Approved
0.7597	Intermediate Similarity	NPD920	Approved
0.7576	Intermediate Similarity	NPD7472	Approved
0.7568	Intermediate Similarity	NPD3748	Approved
0.7566	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3818	Discontinued
0.755	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7808	Phase 3
0.7517	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.75	Intermediate Similarity	NPD7458	Discontinued
0.75	Intermediate Similarity	NPD4908	Phase 1
0.7485	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD7251	Discontinued
0.7484	Intermediate Similarity	NPD5403	Approved
0.7468	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3972	Approved
0.7434	Intermediate Similarity	NPD4628	Phase 3
0.7425	Intermediate Similarity	NPD6797	Phase 2
0.7413	Intermediate Similarity	NPD1203	Approved
0.7397	Intermediate Similarity	NPD3268	Approved
0.7378	Intermediate Similarity	NPD3926	Phase 2
0.7376	Intermediate Similarity	NPD1610	Phase 2
0.7372	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5124	Phase 1
0.7365	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD5401	Approved
0.7351	Intermediate Similarity	NPD2346	Discontinued
0.732	Intermediate Similarity	NPD7003	Approved
0.7314	Intermediate Similarity	NPD4363	Phase 3
0.7314	Intermediate Similarity	NPD4360	Phase 2
0.7305	Intermediate Similarity	NPD5844	Phase 1
0.7299	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD2797	Approved
0.7292	Intermediate Similarity	NPD1164	Approved
0.7286	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5408	Approved
0.7285	Intermediate Similarity	NPD5404	Approved
0.7285	Intermediate Similarity	NPD5405	Approved
0.7285	Intermediate Similarity	NPD5406	Approved
0.7273	Intermediate Similarity	NPD4361	Phase 2
0.7273	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD5402	Approved
0.7254	Intermediate Similarity	NPD1201	Approved
0.7239	Intermediate Similarity	NPD919	Approved
0.7235	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1876	Approved
0.7219	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD1465	Phase 2
0.7203	Intermediate Similarity	NPD9717	Approved
0.7203	Intermediate Similarity	NPD1608	Approved
0.7194	Intermediate Similarity	NPD9493	Approved
0.7188	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1470	Approved
0.7152	Intermediate Similarity	NPD1247	Approved
0.7143	Intermediate Similarity	NPD37	Approved
0.7134	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD422	Phase 1
0.7133	Intermediate Similarity	NPD230	Phase 1
0.7133	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7229	Phase 3
0.7105	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7033	Discontinued
0.7103	Intermediate Similarity	NPD1283	Approved
0.7095	Intermediate Similarity	NPD4625	Phase 3
0.7093	Intermediate Similarity	NPD8312	Approved
0.7093	Intermediate Similarity	NPD8313	Approved
0.7092	Intermediate Similarity	NPD9545	Approved
0.7092	Intermediate Similarity	NPD1548	Phase 1
0.7086	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1729	Discontinued
0.7055	Intermediate Similarity	NPD3267	Approved
0.7055	Intermediate Similarity	NPD3266	Approved
0.7047	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD3764	Approved
0.7042	Intermediate Similarity	NPD1651	Approved
0.7041	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4749	Approved
0.703	Intermediate Similarity	NPD6234	Discontinued
0.7025	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2403	Approved
0.702	Intermediate Similarity	NPD6355	Discontinued
0.7012	Intermediate Similarity	NPD4965	Approved
0.7012	Intermediate Similarity	NPD4967	Phase 2
0.7012	Intermediate Similarity	NPD4966	Approved
0.6993	Remote Similarity	NPD17	Approved
0.6993	Remote Similarity	NPD4308	Phase 3
0.6989	Remote Similarity	NPD8151	Discontinued
0.698	Remote Similarity	NPD3027	Phase 3
0.6971	Remote Similarity	NPD8434	Phase 2
0.6971	Remote Similarity	NPD8150	Discontinued
0.6962	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4288	Approved
0.6951	Remote Similarity	NPD2296	Approved
0.6946	Remote Similarity	NPD7199	Phase 2
0.6914	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1471	Phase 3
0.6903	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6004	Phase 3
0.6903	Remote Similarity	NPD6005	Phase 3
0.6903	Remote Similarity	NPD6002	Phase 3
0.6902	Remote Similarity	NPD7698	Approved
0.6902	Remote Similarity	NPD7697	Approved
0.6902	Remote Similarity	NPD7696	Phase 3
0.6897	Remote Similarity	NPD1281	Approved
0.6893	Remote Similarity	NPD4287	Approved
0.689	Remote Similarity	NPD8455	Phase 2
0.6882	Remote Similarity	NPD7584	Approved
0.6879	Remote Similarity	NPD6104	Discontinued
0.6875	Remote Similarity	NPD4626	Approved
0.6871	Remote Similarity	NPD3225	Approved
0.6865	Remote Similarity	NPD7871	Phase 2
0.6865	Remote Similarity	NPD7870	Phase 2
0.6864	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4060	Phase 1
0.6842	Remote Similarity	NPD7228	Approved
0.6839	Remote Similarity	NPD4477	Approved
0.6839	Remote Similarity	NPD4476	Approved
0.6831	Remote Similarity	NPD6781	Approved
0.6831	Remote Similarity	NPD6778	Approved
0.6831	Remote Similarity	NPD6782	Approved
0.6831	Remote Similarity	NPD6776	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