NPASS Compound

Structure

CID250594 OpenBabel06191716052D 52 54 0 0 1 0 0 0 0 0999 V2000 0.3133 5.9018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2716 5.4772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4867 3.1566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4867 -2.2092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6565 3.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0264 1.9473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9488 3.2391 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5001 0.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6344 -1.4211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0588 -1.1870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6699 -0.6699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9151 0.2452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8139 0.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4366 -0.2928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3565 5.2320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2415 2.2415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2415 -1.2941 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4866 3.3528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7812 2.8624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6560 2.3381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5850 0.5227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8139 -0.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9140 -0.2508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5356 0.9474 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0619 1.7678 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2941 2.2415 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2941 -1.2941 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4737 1.7678 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0619 -0.8204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4366 1.2401 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4737 -0.8204 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9474 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1114 4.3169 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 4.9935 0.4737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5356 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1565 4.0227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4511 3.5323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2900 1.6341 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3398 -0.3924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9935 -1.4211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0308 0.0920 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7318 -1.4903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7812 3.6470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7318 2.4377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8661 3.1076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7294 2.1411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9151 1.1926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4737 -1.7678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8037 4.0717 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8139 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6524 0.3427 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 2 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 34 1 0 0 0 0 12 34 1 0 0 0 0 14 35 1 0 0 0 0 14 36 1 0 0 0 0 15 33 1 0 0 0 0 16 25 1 0 0 0 0 16 26 1 0 0 0 0 17 4 1 6 0 0 0 17 27 1 0 0 0 0 17 29 1 0 0 0 0 18 37 2 0 0 0 0 18 45 1 0 0 0 0 19 38 2 0 0 0 0 19 46 1 0 0 0 0 20 39 2 0 0 0 0 20 47 1 0 0 0 0 21 40 2 0 0 0 0 21 48 1 0 0 0 0 22 41 2 0 0 0 0 22 51 1 0 0 0 0 23 42 2 0 0 0 0 23 52 1 0 0 0 0 24 25 1 0 0 0 0 24 30 1 0 0 0 0 24 36 1 1 0 0 0 25 45 1 6 0 0 0 26 28 1 0 0 0 0 26 50 1 1 0 0 0 27 31 1 0 0 0 0 27 49 1 6 0 0 0 28 32 1 0 0 0 0 28 46 1 6 0 0 0 29 36 1 0 0 0 0 29 43 2 0 0 0 0 30 35 1 1 0 0 0 30 47 1 0 0 0 0 31 34 1 0 0 0 0 31 49 1 1 0 0 0 32 34 1 0 0 0 0 32 48 1 6 0 0 0 33 44 2 0 0 0 0 33 50 1 0 0 0 0 35 13 1 1 0 0 0 35 51 1 0 0 0 0 36 52 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	738.31
Volume:	722.458
LogP:	2.904
LogD:	1.755
LogS:	-4.14
# Rotatable Bonds:	15
TPSA:	213.7
# H-Bond Aceptor:	16
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.151
Synthetic Accessibility Score:	6.104
Fsp3:	0.722
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.315
MDCK Permeability:	0.00017432052118238062
Pgp-inhibitor:	1.0
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.956
20% Bioavailability (F20%):	0.161
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.041
Plasma Protein Binding (PPB):	52.124855041503906%
Volume Distribution (VD):	1.865
Pgp-substrate:	28.85911750793457%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.011
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.828
CYP2D6-substrate:	0.026
CYP3A4-inhibitor:	0.448
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	3.404
Half-life (T1/2):	0.703

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.042
Rat Oral Acute Toxicity:	0.769
Maximum Recommended Daily Dose:	0.01
Skin Sensitization:	0.103
Carcinogencity:	0.063
Eye Corrosion:	0.931
Eye Irritation:	0.155
Respiratory Toxicity:	0.836

Download Data

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

Natural Product: NPC250594

Natural Product ID:	NPC250594
*Common Name:**	QLMXVPKQTUZUIB-WXRBLWNSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QLMXVPKQTUZUIB-WXRBLWNSSA-N
Standard InCHI:	InChI=1S/C36H50O16/c1-15(2)33(44)50-26-16(3)25(45-18(5)37)24-30(47-20(7)39)35(13,51-22(9)41)14-36(24,52-23(10)42)29(43)17(4)27-31(49-27)34(11,12)32(48-21(8)40)28(26)46-19(6)38/h15,17,24-28,30-32H,3,14H2,1-2,4-13H3/t17-,24+,25+,26+,27+,28-,30-,31-,32-,35-,36-/m1/s1
SMILES:	CC(=O)O[C@H]1C(=C)[C@H](OC(=O)C(C)C)[C@@H](OC(=O)C)[C@@H](OC(=O)C)C(C)(C)[C@H]2[C@H]([C@H](C(=O)[C@@]3([C@@H]1[C@@H](OC(=O)C)[C@](C3)(C)OC(=O)C)OC(=O)C)C)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1978293
PubChem CID:	6712418
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0003677] Alpha-acyloxy carbonyl compounds [CHEMONTID:0003420] Alpha-acyloxy ketones

*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
NPO20289	Dracocephalum tanguticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19499937]
NPO20289	Dracocephalum tanguticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20932762]
NPO17973	Sinapis arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17973	Sinapis arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20289	Dracocephalum tanguticum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17973	Sinapis arvensis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23112	Rubia tinctoria	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20783	Fissistigma bracteolatum	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9653	Corynebacterium pseudotuberculosis	Species	Corynebacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21966	Funiculina quadrangularis	Species	Funiculinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20156	Bolbitis subcordata	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22534	Lonicera tatarica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21842	Musanga cecropioides	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22664	Uapaca paludosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17916	Monoon viride	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20895	Lotus suaveolens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22849	Glaucidium palmatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22613	Helichrysum sutherlandi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18416	Streptomyces fulvoviolaceus	Species	Streptomycetaceae	Bacteria	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	58

Activity Type	# Activity
Cell Line	58

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	61944.11	nM	PMID[536677]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	690.24	nM	PMID[536677]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[536677]

☑ 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 NPC250594 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	2647
0.2-0.3	7658
0.3-0.4	14539
0.4-0.5	8746
0.5-0.6	6188
0.6-0.7	2205
0.7-0.8	332
0.8-0.85	24
0.85-0.9	16
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9894	High Similarity	NPC471767
0.899	High Similarity	NPC105725
0.899	High Similarity	NPC471757
0.899	High Similarity	NPC78127
0.899	High Similarity	NPC49393
0.8942	High Similarity	NPC477093
0.8942	High Similarity	NPC473522
0.8942	High Similarity	NPC475277
0.8846	High Similarity	NPC475495
0.8687	High Similarity	NPC470188
0.8611	High Similarity	NPC475305
0.8532	High Similarity	NPC475401
0.8462	Intermediate Similarity	NPC470192
0.8455	Intermediate Similarity	NPC477092
0.82	Intermediate Similarity	NPC470191
0.8073	Intermediate Similarity	NPC471933
0.79	Intermediate Similarity	NPC286341
0.79	Intermediate Similarity	NPC191339
0.7885	Intermediate Similarity	NPC186861
0.787	Intermediate Similarity	NPC117604
0.785	Intermediate Similarity	NPC44004
0.785	Intermediate Similarity	NPC474101
0.7767	Intermediate Similarity	NPC477354
0.7755	Intermediate Similarity	NPC469626
0.7755	Intermediate Similarity	NPC475491
0.7714	Intermediate Similarity	NPC471381
0.77	Intermediate Similarity	NPC472872
0.77	Intermediate Similarity	NPC283409
0.7685	Intermediate Similarity	NPC291643
0.767	Intermediate Similarity	NPC475900
0.767	Intermediate Similarity	NPC163228
0.7664	Intermediate Similarity	NPC19239
0.7664	Intermediate Similarity	NPC474166
0.7658	Intermediate Similarity	NPC287311
0.7647	Intermediate Similarity	NPC470187
0.7647	Intermediate Similarity	NPC477361
0.7647	Intermediate Similarity	NPC202824
0.7636	Intermediate Similarity	NPC471934
0.7624	Intermediate Similarity	NPC65359
0.7624	Intermediate Similarity	NPC246173
0.76	Intermediate Similarity	NPC471149
0.7596	Intermediate Similarity	NPC476009
0.7596	Intermediate Similarity	NPC39859
0.7596	Intermediate Similarity	NPC91771
0.7596	Intermediate Similarity	NPC142529
0.7596	Intermediate Similarity	NPC470883
0.7596	Intermediate Similarity	NPC76862
0.7596	Intermediate Similarity	NPC158416
0.7593	Intermediate Similarity	NPC169843
0.7576	Intermediate Similarity	NPC469676
0.7549	Intermediate Similarity	NPC221282
0.7549	Intermediate Similarity	NPC20713
0.7545	Intermediate Similarity	NPC473939
0.7545	Intermediate Similarity	NPC327286
0.7545	Intermediate Similarity	NPC169888
0.7545	Intermediate Similarity	NPC55972
0.7545	Intermediate Similarity	NPC473595
0.7524	Intermediate Similarity	NPC471150
0.7524	Intermediate Similarity	NPC311904
0.7523	Intermediate Similarity	NPC103088
0.7523	Intermediate Similarity	NPC54737
0.7523	Intermediate Similarity	NPC470979
0.7523	Intermediate Similarity	NPC475802
0.7523	Intermediate Similarity	NPC470975
0.7523	Intermediate Similarity	NPC16313
0.7523	Intermediate Similarity	NPC9303
0.75	Intermediate Similarity	NPC24728
0.75	Intermediate Similarity	NPC329704
0.75	Intermediate Similarity	NPC270270
0.75	Intermediate Similarity	NPC476053
0.7477	Intermediate Similarity	NPC201718
0.7477	Intermediate Similarity	NPC59489
0.7477	Intermediate Similarity	NPC139838
0.7477	Intermediate Similarity	NPC477356
0.7477	Intermediate Similarity	NPC477511
0.7477	Intermediate Similarity	NPC15218
0.7477	Intermediate Similarity	NPC476228
0.7477	Intermediate Similarity	NPC264477
0.7476	Intermediate Similarity	NPC473273
0.7476	Intermediate Similarity	NPC308656
0.7476	Intermediate Similarity	NPC153590
0.7476	Intermediate Similarity	NPC473263
0.7476	Intermediate Similarity	NPC473234
0.7476	Intermediate Similarity	NPC60386
0.7476	Intermediate Similarity	NPC472874
0.7455	Intermediate Similarity	NPC475510
0.7455	Intermediate Similarity	NPC194620
0.7455	Intermediate Similarity	NPC474421
0.7455	Intermediate Similarity	NPC326994
0.7455	Intermediate Similarity	NPC72813
0.7455	Intermediate Similarity	NPC324327
0.7455	Intermediate Similarity	NPC475587
0.7453	Intermediate Similarity	NPC477355
0.7453	Intermediate Similarity	NPC45125
0.7453	Intermediate Similarity	NPC109556
0.7451	Intermediate Similarity	NPC475748
0.7429	Intermediate Similarity	NPC17585
0.7429	Intermediate Similarity	NPC31645
0.7414	Intermediate Similarity	NPC475130
0.7414	Intermediate Similarity	NPC474286
0.7411	Intermediate Similarity	NPC193741
0.7411	Intermediate Similarity	NPC50223
0.7411	Intermediate Similarity	NPC477103
0.7407	Intermediate Similarity	NPC472754
0.7407	Intermediate Similarity	NPC118405
0.7404	Intermediate Similarity	NPC190294
0.7404	Intermediate Similarity	NPC473331
0.74	Intermediate Similarity	NPC304558
0.74	Intermediate Similarity	NPC238593
0.7387	Intermediate Similarity	NPC233379
0.7387	Intermediate Similarity	NPC474664
0.7387	Intermediate Similarity	NPC14862
0.7387	Intermediate Similarity	NPC308191
0.7379	Intermediate Similarity	NPC469627
0.7379	Intermediate Similarity	NPC155215
0.7379	Intermediate Similarity	NPC66504
0.7358	Intermediate Similarity	NPC87090
0.7358	Intermediate Similarity	NPC323421
0.7358	Intermediate Similarity	NPC474313
0.7358	Intermediate Similarity	NPC328562
0.7358	Intermediate Similarity	NPC471140
0.7345	Intermediate Similarity	NPC470281
0.7339	Intermediate Similarity	NPC329834
0.7339	Intermediate Similarity	NPC472755
0.7333	Intermediate Similarity	NPC472873
0.7327	Intermediate Similarity	NPC5130
0.7321	Intermediate Similarity	NPC475922
0.7321	Intermediate Similarity	NPC477102
0.7315	Intermediate Similarity	NPC27474
0.7315	Intermediate Similarity	NPC472753
0.7315	Intermediate Similarity	NPC304624
0.7315	Intermediate Similarity	NPC171759
0.7315	Intermediate Similarity	NPC474053
0.7315	Intermediate Similarity	NPC476230
0.7308	Intermediate Similarity	NPC200237
0.7308	Intermediate Similarity	NPC258216
0.7308	Intermediate Similarity	NPC475488
0.7308	Intermediate Similarity	NPC475788
0.7297	Intermediate Similarity	NPC251824
0.7297	Intermediate Similarity	NPC26617
0.7297	Intermediate Similarity	NPC474716
0.7297	Intermediate Similarity	NPC473911
0.7297	Intermediate Similarity	NPC86852
0.7297	Intermediate Similarity	NPC469558
0.7282	Intermediate Similarity	NPC329857
0.7282	Intermediate Similarity	NPC469718
0.7281	Intermediate Similarity	NPC475924
0.7281	Intermediate Similarity	NPC475851
0.7273	Intermediate Similarity	NPC477510
0.7273	Intermediate Similarity	NPC257358
0.7273	Intermediate Similarity	NPC310586
0.7273	Intermediate Similarity	NPC474741
0.7273	Intermediate Similarity	NPC128429
0.7273	Intermediate Similarity	NPC471143
0.7273	Intermediate Similarity	NPC472756
0.7273	Intermediate Similarity	NPC474472
0.7264	Intermediate Similarity	NPC113433
0.7264	Intermediate Similarity	NPC476275
0.7257	Intermediate Similarity	NPC281624
0.7257	Intermediate Similarity	NPC161816
0.7257	Intermediate Similarity	NPC473975
0.7257	Intermediate Similarity	NPC115257
0.7257	Intermediate Similarity	NPC474586
0.7257	Intermediate Similarity	NPC41551
0.7257	Intermediate Similarity	NPC473594
0.7257	Intermediate Similarity	NPC473843
0.7255	Intermediate Similarity	NPC315911
0.7241	Intermediate Similarity	NPC476711
0.7241	Intermediate Similarity	NPC476710
0.7236	Intermediate Similarity	NPC13071
0.7232	Intermediate Similarity	NPC470269
0.7228	Intermediate Similarity	NPC261253
0.7228	Intermediate Similarity	NPC137253
0.7228	Intermediate Similarity	NPC474045
0.7222	Intermediate Similarity	NPC476211
0.7222	Intermediate Similarity	NPC476320
0.7222	Intermediate Similarity	NPC477512
0.7217	Intermediate Similarity	NPC101965
0.7217	Intermediate Similarity	NPC101400
0.7212	Intermediate Similarity	NPC35959
0.7212	Intermediate Similarity	NPC293001
0.7212	Intermediate Similarity	NPC133888
0.7212	Intermediate Similarity	NPC29821
0.7212	Intermediate Similarity	NPC171360
0.7212	Intermediate Similarity	NPC63193
0.7212	Intermediate Similarity	NPC57304
0.7207	Intermediate Similarity	NPC28791
0.7207	Intermediate Similarity	NPC179891
0.7207	Intermediate Similarity	NPC314244
0.7207	Intermediate Similarity	NPC295366
0.7196	Intermediate Similarity	NPC170143
0.7196	Intermediate Similarity	NPC213947
0.7196	Intermediate Similarity	NPC86843
0.7196	Intermediate Similarity	NPC108475
0.7193	Intermediate Similarity	NPC94650
0.7193	Intermediate Similarity	NPC194619
0.7184	Intermediate Similarity	NPC151770
0.7184	Intermediate Similarity	NPC474951
0.7184	Intermediate Similarity	NPC475971
0.7182	Intermediate Similarity	NPC260809

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 NPC250594 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	381
0.1-0.2	3300
0.2-0.3	3523
0.3-0.4	1287
0.4-0.5	384
0.5-0.6	230
0.6-0.7	44
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7297	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6371	Approved
0.686	Remote Similarity	NPD6319	Approved
0.6857	Remote Similarity	NPD1695	Approved
0.6796	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6008	Approved
0.6696	Remote Similarity	NPD1700	Approved
0.6695	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7492	Approved
0.6638	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7736	Approved
0.6587	Remote Similarity	NPD6616	Approved
0.6585	Remote Similarity	NPD6059	Approved
0.6585	Remote Similarity	NPD6054	Approved
0.6581	Remote Similarity	NPD6372	Approved
0.6581	Remote Similarity	NPD6373	Approved
0.6574	Remote Similarity	NPD7983	Approved
0.6535	Remote Similarity	NPD7078	Approved
0.6505	Remote Similarity	NPD6435	Approved
0.65	Remote Similarity	NPD8133	Approved
0.6481	Remote Similarity	NPD46	Approved
0.6481	Remote Similarity	NPD6698	Approved
0.6481	Remote Similarity	NPD5785	Approved
0.648	Remote Similarity	NPD6370	Approved
0.6471	Remote Similarity	NPD6650	Approved
0.6471	Remote Similarity	NPD6649	Approved
0.6466	Remote Similarity	NPD5739	Approved
0.6466	Remote Similarity	NPD7128	Approved
0.6466	Remote Similarity	NPD6675	Approved
0.6466	Remote Similarity	NPD6402	Approved
0.6422	Remote Similarity	NPD5693	Phase 1
0.6417	Remote Similarity	NPD6053	Discontinued
0.6415	Remote Similarity	NPD5786	Approved
0.6408	Remote Similarity	NPD5369	Approved
0.64	Remote Similarity	NPD6016	Approved
0.64	Remote Similarity	NPD6015	Approved
0.6396	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD7320	Approved
0.6356	Remote Similarity	NPD6881	Approved
0.6356	Remote Similarity	NPD6899	Approved
0.6349	Remote Similarity	NPD5988	Approved
0.6341	Remote Similarity	NPD7115	Discovery
0.6333	Remote Similarity	NPD8130	Phase 1
0.6311	Remote Similarity	NPD5368	Approved
0.6308	Remote Similarity	NPD7319	Approved
0.6306	Remote Similarity	NPD5282	Discontinued
0.6299	Remote Similarity	NPD7604	Phase 2
0.6283	Remote Similarity	NPD6084	Phase 2
0.6283	Remote Similarity	NPD6083	Phase 2
0.6281	Remote Similarity	NPD6882	Approved
0.6271	Remote Similarity	NPD5697	Approved
0.6271	Remote Similarity	NPD5701	Approved
0.6262	Remote Similarity	NPD6098	Approved
0.625	Remote Similarity	NPD7290	Approved
0.625	Remote Similarity	NPD7102	Approved
0.625	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD5695	Phase 3
0.6239	Remote Similarity	NPD6904	Approved
0.6239	Remote Similarity	NPD6673	Approved
0.6239	Remote Similarity	NPD6080	Approved
0.623	Remote Similarity	NPD4632	Approved
0.6228	Remote Similarity	NPD5696	Approved
0.621	Remote Similarity	NPD6009	Approved
0.6202	Remote Similarity	NPD7507	Approved
0.6198	Remote Similarity	NPD6847	Approved
0.6198	Remote Similarity	NPD6869	Approved
0.6198	Remote Similarity	NPD6617	Approved
0.6198	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4270	Approved
0.619	Remote Similarity	NPD4269	Approved
0.6182	Remote Similarity	NPD7838	Discovery
0.6172	Remote Similarity	NPD8328	Phase 3
0.6167	Remote Similarity	NPD6012	Approved
0.6167	Remote Similarity	NPD6014	Approved
0.6167	Remote Similarity	NPD6013	Approved
0.6147	Remote Similarity	NPD5737	Approved
0.6147	Remote Similarity	NPD6672	Approved
0.6142	Remote Similarity	NPD5983	Phase 2
0.6142	Remote Similarity	NPD6921	Approved
0.6134	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6050	Approved
0.6116	Remote Similarity	NPD4634	Approved
0.6107	Remote Similarity	NPD6033	Approved
0.6083	Remote Similarity	NPD6011	Approved
0.608	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD6336	Discontinued
0.6071	Remote Similarity	NPD6399	Phase 3
0.6066	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD4251	Approved
0.6055	Remote Similarity	NPD4250	Approved
0.6036	Remote Similarity	NPD5692	Phase 3
0.6019	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5363	Approved
0.6016	Remote Similarity	NPD8517	Approved
0.6016	Remote Similarity	NPD8515	Approved
0.6016	Remote Similarity	NPD8513	Phase 3
0.6016	Remote Similarity	NPD8516	Approved
0.6	Remote Similarity	NPD4821	Approved
0.6	Remote Similarity	NPD4822	Approved
0.6	Remote Similarity	NPD4252	Approved
0.6	Remote Similarity	NPD4819	Approved
0.6	Remote Similarity	NPD4820	Approved
0.6	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD5694	Approved
0.5982	Remote Similarity	NPD8034	Phase 2
0.5982	Remote Similarity	NPD8035	Phase 2
0.5981	Remote Similarity	NPD5362	Discontinued
0.597	Remote Similarity	NPD7260	Phase 2
0.5965	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD6684	Approved
0.5963	Remote Similarity	NPD4249	Approved
0.5963	Remote Similarity	NPD7521	Approved
0.5963	Remote Similarity	NPD7146	Approved
0.5963	Remote Similarity	NPD7334	Approved
0.5963	Remote Similarity	NPD6409	Approved
0.5963	Remote Similarity	NPD5330	Approved
0.595	Remote Similarity	NPD6686	Approved
0.5929	Remote Similarity	NPD5779	Approved
0.5929	Remote Similarity	NPD5778	Approved
0.5891	Remote Similarity	NPD8033	Approved
0.5888	Remote Similarity	NPD5209	Approved
0.5873	Remote Similarity	NPD6274	Approved
0.5868	Remote Similarity	NPD6412	Phase 2
0.5862	Remote Similarity	NPD4755	Approved
0.5859	Remote Similarity	NPD7100	Approved
0.5859	Remote Similarity	NPD7101	Approved
0.5856	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6903	Approved
0.5841	Remote Similarity	NPD7637	Suspended
0.5841	Remote Similarity	NPD6411	Approved
0.5833	Remote Similarity	NPD7154	Phase 3
0.5812	Remote Similarity	NPD7638	Approved
0.581	Remote Similarity	NPD4802	Phase 2
0.581	Remote Similarity	NPD4271	Approved
0.581	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.581	Remote Similarity	NPD4268	Approved
0.581	Remote Similarity	NPD4238	Approved
0.5809	Remote Similarity	NPD6845	Suspended
0.5804	Remote Similarity	NPD6051	Approved
0.5798	Remote Similarity	NPD8301	Approved
0.5798	Remote Similarity	NPD8300	Approved
0.5798	Remote Similarity	NPD5211	Phase 2
0.5789	Remote Similarity	NPD8074	Phase 3
0.5781	Remote Similarity	NPD6335	Approved
0.5778	Remote Similarity	NPD5956	Approved
0.5776	Remote Similarity	NPD7839	Suspended
0.5772	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6908	Approved
0.5769	Remote Similarity	NPD8267	Approved
0.5769	Remote Similarity	NPD6909	Approved
0.5769	Remote Similarity	NPD8266	Approved
0.5769	Remote Similarity	NPD8269	Approved
0.5769	Remote Similarity	NPD8268	Approved
0.5769	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD4700	Approved
0.5763	Remote Similarity	NPD5286	Approved
0.5763	Remote Similarity	NPD5285	Approved
0.5763	Remote Similarity	NPD7640	Approved
0.5763	Remote Similarity	NPD4696	Approved
0.5763	Remote Similarity	NPD7639	Approved
0.5755	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD5959	Approved
0.5725	Remote Similarity	NPD8080	Discontinued
0.5703	Remote Similarity	NPD6317	Approved
0.5702	Remote Similarity	NPD5141	Approved
0.5692	Remote Similarity	NPD8377	Approved
0.5692	Remote Similarity	NPD8294	Approved
0.569	Remote Similarity	NPD5654	Approved
0.5682	Remote Similarity	NPD7642	Approved
0.5678	Remote Similarity	NPD4225	Approved
0.5678	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD8448	Approved
0.5667	Remote Similarity	NPD4633	Approved
0.5667	Remote Similarity	NPD5224	Approved
0.5667	Remote Similarity	NPD5225	Approved
0.5667	Remote Similarity	NPD5226	Approved
0.5664	Remote Similarity	NPD6101	Approved
0.5664	Remote Similarity	NPD4753	Phase 2
0.5664	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5659	Remote Similarity	NPD7328	Approved
0.5659	Remote Similarity	NPD6314	Approved
0.5659	Remote Similarity	NPD6313	Approved
0.5659	Remote Similarity	NPD7327	Approved
0.5656	Remote Similarity	NPD4768	Approved
0.5656	Remote Similarity	NPD4767	Approved
0.5649	Remote Similarity	NPD8379	Approved
0.5649	Remote Similarity	NPD8335	Approved
0.5649	Remote Similarity	NPD8444	Approved
0.5649	Remote Similarity	NPD8378	Approved
0.5649	Remote Similarity	NPD8380	Approved
0.5649	Remote Similarity	NPD8296	Approved
0.563	Remote Similarity	NPD8336	Approved
0.563	Remote Similarity	NPD6648	Approved
0.563	Remote Similarity	NPD8337	Approved
0.562	Remote Similarity	NPD5175	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