NPASS Compound

Structure

NPC193280 OpenBabel07101719202D 78 78 0 0 1 0 0 0 0 0999 V2000 -1.7168 -12.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0087 -12.6752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9400 -2.0999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9465 -0.6811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6776 -1.6981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4096 -3.2678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7080 -9.3847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4400 -7.8149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9096 -8.9829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9162 -10.4017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2528 1.7434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9783 1.5925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9567 -11.9662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3755 -10.9727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7696 -5.3094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6186 -7.0348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3585 0.6514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7887 1.3834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3319 -11.6470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2264 -4.9542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3489 -0.0229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8977 -12.2526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0337 -1.6773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5905 -2.6943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6209 -8.3885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0033 -9.4055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0720 1.1698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3793 -11.0599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1960 -6.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3623 0.5643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9093 -10.7407 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2302 -5.0414 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7753 -0.8420 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9848 -11.2564 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2146 -2.2509 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6842 -3.1169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7146 -7.9659 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1842 -8.8319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9848 0.1736 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8057 -10.2407 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1998 -6.0414 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9397 -0.3420 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7753 -10.2407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2302 -6.0414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9093 -0.3420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9397 -10.7407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1998 -5.0414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8057 -0.8420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9848 -11.2564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7146 -3.1169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1842 -2.2509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2146 -8.8319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6842 -7.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9848 0.1736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5414 -9.5979 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0566 -7.0262 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9696 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -11.0828 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.0262 -4.0566 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5718 -1.4848 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.3489 -11.0599 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2264 -6.1285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3319 0.5643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3623 -11.6470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1960 -4.9542 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3793 -0.0229 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0720 -12.2526 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6209 -2.6943 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0033 -1.6773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0337 -9.4055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5905 -8.3885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8977 1.1698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9696 -11.0828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0566 -4.0566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5414 -1.4848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5718 -9.5979 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0262 -7.0262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 8 25 1 0 0 0 0 9 26 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 30 1 0 0 0 0 31 19 1 1 0 0 0 31 43 1 0 0 0 0 31 73 1 0 0 0 0 32 20 1 1 0 0 0 32 44 1 0 0 0 0 32 74 1 0 0 0 0 33 21 1 1 0 0 0 33 45 1 0 0 0 0 33 75 1 0 0 0 0 34 22 1 6 0 0 0 34 49 1 0 0 0 0 34 58 1 0 0 0 0 35 23 1 6 0 0 0 35 50 1 0 0 0 0 35 60 1 0 0 0 0 36 24 1 6 0 0 0 36 51 1 0 0 0 0 36 59 1 0 0 0 0 37 25 1 1 0 0 0 37 52 1 0 0 0 0 37 56 1 0 0 0 0 38 26 1 1 0 0 0 38 53 1 0 0 0 0 38 55 1 0 0 0 0 39 27 1 1 0 0 0 39 54 1 0 0 0 0 39 57 1 0 0 0 0 40 28 1 6 0 0 0 40 46 1 0 0 0 0 40 76 1 0 0 0 0 41 29 1 6 0 0 0 41 47 1 0 0 0 0 41 77 1 0 0 0 0 42 30 1 6 0 0 0 42 48 1 0 0 0 0 42 78 1 0 0 0 0 43 55 2 3 0 0 0 43 61 1 0 0 0 0 44 56 2 3 0 0 0 44 62 1 0 0 0 0 45 57 2 3 0 0 0 45 63 1 0 0 0 0 46 58 2 3 0 0 0 46 64 1 0 0 0 0 47 59 2 3 0 0 0 47 65 1 0 0 0 0 48 60 2 3 0 0 0 48 66 1 0 0 0 0 49 67 2 0 0 0 0 49 73 1 0 0 0 0 50 68 2 0 0 0 0 50 74 1 0 0 0 0 51 69 2 0 0 0 0 51 75 1 0 0 0 0 52 70 2 0 0 0 0 52 76 1 0 0 0 0 53 71 2 0 0 0 0 53 77 1 0 0 0 0 54 72 2 0 0 0 0 54 78 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1110.63
Volume:	1126.55
LogP:	6.148
LogD:	2.58
LogS:	-4.019
# Rotatable Bonds:	9
TPSA:	339.38
# H-Bond Aceptor:	24
# H-Bond Donor:	6
# Rings:	1
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.14
Synthetic Accessibility Score:	6.69
Fsp3:	0.778
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:	-6.049
MDCK Permeability:	0.00024985260097309947
Pgp-inhibitor:	1.0
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.191
20% Bioavailability (F20%):	0.261
30% Bioavailability (F30%):	0.537

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	80.59110260009766%
Volume Distribution (VD):	0.932
Pgp-substrate:	5.209464073181152%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.015
CYP3A4-inhibitor:	0.101
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	2.725
Half-life (T1/2):	0.129

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.014
Carcinogencity:	0.009
Eye Corrosion:	0.005
Eye Irritation:	0.039
Respiratory Toxicity:	0.156

Download Data

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

Natural Product: NPC193280

Natural Product ID:	NPC193280
*Common Name:**	Valinomycin
IUPAC Name:	(3S,6S,9R,12R,15S,18S,21R,24R,27S,30S,33R,36R)-6,18,30-trimethyl-3,9,12,15,21,24,27,33,36-nona(propan-2-yl)-1,7,13,19,25,31-hexaoxa-4,10,16,22,28,34-hexazacyclohexatriacontane-2,5,8,11,14,17,20,23,26,29,32,35-dodecone
Synonyms:	Valino; Valinomycin
Standard InCHIKey:	FCFNRCROJUBPLU-DNDCDFAISA-N
Standard InCHI:	InChI=1S/C54H90N6O18/c1-22(2)34-49(67)73-31(19)43(61)55-38(26(9)10)53(71)77-41(29(15)16)47(65)59-36(24(5)6)51(69)75-33(21)45(63)57-39(27(11)12)54(72)78-42(30(17)18)48(66)60-35(23(3)4)50(68)74-32(20)44(62)56-37(25(7)8)52(70)76-40(28(13)14)46(64)58-34/h22-42H,1-21H3,(H,55,61)(H,56,62)(H,57,63)(H,58,64)(H,59,65)(H,60,66)/t31-,32-,33-,34+,35+,36+,37-,38-,39-,40+,41+,42+/m0/s1
SMILES:	C[C@@H]1OC(=O)[C@H](N=C(O)[C@H](OC(=O)[C@@H](N=C(O)[C@H](C)OC(=O)[C@H](N=C(O)[C@H](OC(=O)[C@@H](N=C([C@@H](OC(=O)[C@H](N=C([C@H](OC(=O)[C@@H](N=C1O)C(C)C)C(C)C)O)C(C)C)C)O)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C)C(C)C
Synthetic Gene Cluster:	BGC0001341;
ChEMBL Identifier:	CHEMBL223643
PubChem CID:	3000706
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO33228	bacillus silvestris	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19216517]
NPO33228	bacillus silvestris	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19226154]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
EC50	1
ED50	1
GI50	6
IC50	17
MIC	3
Others	43

Activity Type	# Activity
Cell Line	39
CELL-LINE	1
Individual Protein	10
Organism	17
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT137	Cell Line	L1210	Mus musculus	Log CR	=	0.59	n.a.	PMID[478555]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	1.0	nM	PMID[478556]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1.0	nM	PMID[478556]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	1.0	nM	PMID[478556]
NPT323	Cell Line	SW-620	Homo sapiens	IC50	=	0.1	nM	PMID[478556]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	500.0	nM	PMID[478556]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	35.0	%	PMID[478556]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	60.0	%	PMID[478556]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	24.0	%	PMID[478556]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	42.0	%	PMID[478556]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	63.0	%	PMID[478556]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	12.0	%	PMID[478556]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	23.0	%	PMID[478556]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	49.0	%	PMID[478556]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	62.0	%	PMID[478556]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	19.0	%	PMID[478556]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	Activity	=	18.0	%	PMID[478556]
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	67500.0	nM	PMID[478557]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.12	ug ml-1	PMID[478559]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.0019	ug.mL-1	PMID[478559]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.001	ug.mL-1	PMID[478559]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	0.0027	ug.mL-1	PMID[478559]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.0025	ug.mL-1	PMID[478559]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	=	0.0008	ug.mL-1	PMID[478559]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	0.0035	ug.mL-1	PMID[478559]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	16.65	%	PMID[478569]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	56.07	%	PMID[478570]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	25.79	%	PMID[478570]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	18.15	%	PMID[478570]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	16.0	%	PMID[478570]
NPT76	Cell Line	C6	Rattus norvegicus	Ratio IC50	=	3.0	n.a.	PMID[478570]
NPT65	Cell Line	HepG2	Homo sapiens	Ratio IC50	=	3.0	n.a.	PMID[478570]
NPT179	Cell Line	A2780	Homo sapiens	Ratio IC50	=	3.0	n.a.	PMID[478570]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	2180.0	nM	PMID[478570]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1770.0	nM	PMID[478570]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	0.8	nM	PMID[478570]
NPT76	Cell Line	C6	Rattus norvegicus	IC50	=	0.4	nM	PMID[478570]
NPT65	Cell Line	HepG2	Homo sapiens	Activity	=	40.3	%	PMID[478571]
NPT612	Individual Protein	Canalicular multispecific organic anion transporter 1	Homo sapiens	IC50	>	133000.0	nM	PMID[478577]
NPT1249	Individual Protein	Canalicular multispecific organic anion transporter 2	Homo sapiens	IC50	>	133000.0	nM	PMID[478577]
NPT1028	Individual Protein	Multidrug resistance-associated protein 4	Homo sapiens	IC50	>	133000.0	nM	PMID[478577]
NPT35	Others	n.a.		LogD	=	3.24	n.a.	PMID[478555]
NPT1515	Organism	SARS coronavirus	SARS coronavirus	EC50	=	1630.0	nM	PMID[478557]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	41.4	n.a.	PMID[478557]
NPT1515	Organism	SARS coronavirus	SARS coronavirus	Inhibition	<	25.0	%	PMID[478557]
NPT1515	Organism	SARS coronavirus	SARS coronavirus	Inhibition	=	50.0	%	PMID[478557]
NPT1515	Organism	SARS coronavirus	SARS coronavirus	Inhibition	=	25.0	%	PMID[478557]
NPT1018	Organism	Trypanosoma brucei	Trypanosoma brucei	Activity	=	97.3	%	PMID[478558]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	Activity	=	70.0	%	PMID[478560]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	FC	>=	2.0	n.a.	PMID[478561]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC	=	0.4	ug.mL-1	PMID[478561]
NPT1108	Organism	Mycobacterium bovis BCG	Mycobacterium bovis BCG	MIC	=	0.2	ug.mL-1	PMID[478561]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	Activity	<	40.0	%	PMID[478562]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Activity	<	40.0	%	PMID[478562]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Km	=	1000.0	nM	PMID[478565]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	7200.0	nM	PMID[478566]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	IC50	=	3200.0	nM	PMID[478567]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-1.5	%	PMID[478569]
NPT27	Others	Unspecified		Survival	=	50.0	%	PMID[478570]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	1600.0	nM	PMID[478575]
NPT713	Individual Protein	Bile salt export pump	Homo sapiens	IC50	=	1560.0	nM	PMID[478577]
NPT2	Others	Unspecified		Ratio CC50/EC50	=	80.0	n.a.	PMID[478578]
NPT22224	CELL-LINE	Vero C1008	Chlorocebus sabaeus	CC50	=	68000.0	nM	PMID[478578]
NPT24755	ORGANISM	SARS-CoV	Severe acute respiratory syndrome-related coronavirus	IC50	=	850.0	nM	PMID[478578]

☑ 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 NPC193280 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	265
0.1-0.2	16001
0.2-0.3	18758
0.3-0.4	6353
0.4-0.5	972
0.5-0.6	236
0.6-0.7	77
0.7-0.8	24
0.8-0.85	1
0.85-0.9	3
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC314273
0.9545	High Similarity	NPC141325
0.9403	High Similarity	NPC138435
0.913	High Similarity	NPC476324
0.913	High Similarity	NPC476130
0.8676	High Similarity	NPC476285
0.8676	High Similarity	NPC476291
0.831	Intermediate Similarity	NPC476248
0.7922	Intermediate Similarity	NPC246005
0.7887	Intermediate Similarity	NPC478256
0.7703	Intermediate Similarity	NPC472595
0.75	Intermediate Similarity	NPC472594
0.7467	Intermediate Similarity	NPC86064
0.7439	Intermediate Similarity	NPC477728
0.7333	Intermediate Similarity	NPC43219
0.7125	Intermediate Similarity	NPC314466
0.7073	Intermediate Similarity	NPC145748
0.7073	Intermediate Similarity	NPC95478
0.7073	Intermediate Similarity	NPC155670
0.7027	Intermediate Similarity	NPC474299
0.7027	Intermediate Similarity	NPC475808
0.7027	Intermediate Similarity	NPC474298
0.7027	Intermediate Similarity	NPC28348
0.7027	Intermediate Similarity	NPC473985
0.6988	Remote Similarity	NPC227051
0.6974	Remote Similarity	NPC474403
0.6957	Remote Similarity	NPC473599
0.6951	Remote Similarity	NPC477730
0.68	Remote Similarity	NPC472579
0.6782	Remote Similarity	NPC477729
0.6716	Remote Similarity	NPC321118
0.6716	Remote Similarity	NPC316889
0.6667	Remote Similarity	NPC315535
0.6667	Remote Similarity	NPC315131
0.6667	Remote Similarity	NPC478017
0.6629	Remote Similarity	NPC208537
0.6629	Remote Similarity	NPC270005
0.6571	Remote Similarity	NPC328447
0.6543	Remote Similarity	NPC316242
0.6463	Remote Similarity	NPC473984
0.6389	Remote Similarity	NPC471129
0.6364	Remote Similarity	NPC328378
0.6364	Remote Similarity	NPC29598
0.6364	Remote Similarity	NPC212866
0.6351	Remote Similarity	NPC145658
0.6338	Remote Similarity	NPC472578
0.6301	Remote Similarity	NPC477644
0.625	Remote Similarity	NPC317143
0.625	Remote Similarity	NPC316826
0.625	Remote Similarity	NPC327748
0.625	Remote Similarity	NPC321468
0.6234	Remote Similarity	NPC470110
0.6234	Remote Similarity	NPC10716
0.6222	Remote Similarity	NPC474593
0.6222	Remote Similarity	NPC475801
0.6197	Remote Similarity	NPC317147
0.6197	Remote Similarity	NPC318260
0.6176	Remote Similarity	NPC322946
0.6164	Remote Similarity	NPC329564
0.6164	Remote Similarity	NPC327170
0.6154	Remote Similarity	NPC474576
0.6125	Remote Similarity	NPC320865
0.6125	Remote Similarity	NPC477641
0.6125	Remote Similarity	NPC477643
0.6119	Remote Similarity	NPC80350
0.6104	Remote Similarity	NPC470109
0.6087	Remote Similarity	NPC471098
0.6087	Remote Similarity	NPC62263
0.6087	Remote Similarity	NPC173763
0.6076	Remote Similarity	NPC477642
0.6049	Remote Similarity	NPC178919
0.6049	Remote Similarity	NPC263281
0.6042	Remote Similarity	NPC220234
0.6026	Remote Similarity	NPC195165
0.6023	Remote Similarity	NPC476523
0.5978	Remote Similarity	NPC477538
0.5977	Remote Similarity	NPC474312
0.5974	Remote Similarity	NPC474402
0.5974	Remote Similarity	NPC470108
0.5957	Remote Similarity	NPC470283
0.5905	Remote Similarity	NPC63191
0.5905	Remote Similarity	NPC471202
0.5876	Remote Similarity	NPC475440
0.5862	Remote Similarity	NPC84128
0.5862	Remote Similarity	NPC53858
0.5859	Remote Similarity	NPC124554
0.5859	Remote Similarity	NPC5864
0.5859	Remote Similarity	NPC301148
0.5849	Remote Similarity	NPC472536
0.5849	Remote Similarity	NPC103391
0.5844	Remote Similarity	NPC41429
0.5842	Remote Similarity	NPC475918
0.5823	Remote Similarity	NPC306696
0.5811	Remote Similarity	NPC321536
0.5802	Remote Similarity	NPC477200
0.58	Remote Similarity	NPC198344
0.5797	Remote Similarity	NPC326283
0.5797	Remote Similarity	NPC321394
0.5789	Remote Similarity	NPC145627
0.5789	Remote Similarity	NPC327252
0.578	Remote Similarity	NPC477237
0.5765	Remote Similarity	NPC37681
0.5765	Remote Similarity	NPC473741
0.5765	Remote Similarity	NPC477145
0.575	Remote Similarity	NPC126779
0.5743	Remote Similarity	NPC124549
0.5743	Remote Similarity	NPC323720
0.5743	Remote Similarity	NPC74035
0.5735	Remote Similarity	NPC227850
0.5714	Remote Similarity	NPC327250
0.5714	Remote Similarity	NPC475758
0.5699	Remote Similarity	NPC39290
0.5699	Remote Similarity	NPC159369
0.5698	Remote Similarity	NPC31756
0.5694	Remote Similarity	NPC327831
0.5694	Remote Similarity	NPC322573
0.5676	Remote Similarity	NPC477238
0.5672	Remote Similarity	NPC297220
0.5657	Remote Similarity	NPC475791
0.5657	Remote Similarity	NPC13175
0.5641	Remote Similarity	NPC128559
0.5634	Remote Similarity	NPC329495
0.5632	Remote Similarity	NPC476117
0.5632	Remote Similarity	NPC476243
0.5632	Remote Similarity	NPC476156
0.5632	Remote Similarity	NPC476137
0.5618	Remote Similarity	NPC47135
0.56	Remote Similarity	NPC320598
0.56	Remote Similarity	NPC254541

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 NPC193280 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	4414
0.2-0.3	3339
0.3-0.4	882
0.4-0.5	268
0.5-0.6	81
0.6-0.7	14
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
0.7273	Intermediate Similarity	NPD2689	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3160	Suspended
0.7143	Intermediate Similarity	NPD1453	Phase 1
0.7027	Intermediate Similarity	NPD3724	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD9419	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD9661	Approved
0.6533	Remote Similarity	NPD2263	Discontinued
0.6484	Remote Similarity	NPD8394	Approved
0.6404	Remote Similarity	NPD3716	Discontinued
0.6364	Remote Similarity	NPD7840	Approved
0.6176	Remote Similarity	NPD9441	Phase 2
0.617	Remote Similarity	NPD6428	Approved
0.6154	Remote Similarity	NPD1815	Discontinued
0.6154	Remote Similarity	NPD6094	Approved
0.6154	Remote Similarity	NPD6095	Approved
0.6143	Remote Similarity	NPD4277	Approved
0.6143	Remote Similarity	NPD4276	Approved
0.6133	Remote Similarity	NPD364	Discontinued
0.6125	Remote Similarity	NPD2256	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD7844	Discontinued
0.6	Remote Similarity	NPD5375	Phase 3
0.596	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD1151	Approved
0.5867	Remote Similarity	NPD574	Approved
0.5867	Remote Similarity	NPD3193	Approved
0.5867	Remote Similarity	NPD3192	Approved
0.5862	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD1831	Phase 3
0.5824	Remote Similarity	NPD4759	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD9677	Phase 3
0.5797	Remote Similarity	NPD9678	Approved
0.5797	Remote Similarity	NPD329	Discontinued
0.5789	Remote Similarity	NPD575	Clinical (unspecified phase)
0.575	Remote Similarity	NPD4242	Approved
0.5732	Remote Similarity	NPD6944	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD3187	Discontinued
0.573	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD1429	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD9433	Approved
0.5625	Remote Similarity	NPD4241	Registered
0.5619	Remote Similarity	NPD6421	Discontinued
0.5618	Remote Similarity	NPD7345	Approved
0.5618	Remote Similarity	NPD7643	Phase 1
0.5616	Remote Similarity	NPD9659	Approved
0.5604	Remote Similarity	NPD7759	Phase 2
0.5604	Remote Similarity	NPD7760	Phase 2

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