NPASS Compound

Structure

NPC141325 OpenBabel07101719512D 81 81 0 0 1 0 0 0 0 0999 V2000 12.0370 -1.1472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0446 1.5906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3442 -10.7055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3332 -3.9180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4842 -2.1925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9258 4.5003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3560 3.7683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3391 -7.8559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7579 -8.8493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0597 3.0069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6408 4.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4729 -9.3493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0427 -8.6173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9345 -0.9310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0854 -2.6565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3922 1.4188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2320 2.4358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7059 -9.5583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7865 4.2867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7179 -6.2886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9063 -5.2716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1242 -0.1510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2255 1.0170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4314 -9.7093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9106 -3.0117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3522 3.6812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3353 -7.9430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0635 3.0940 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0465 -8.5302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5119 -1.8373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3050 0.4226 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3192 1.4396 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6122 -9.1357 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6994 3.2905 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8987 -5.7150 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -4.8490 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9144 -2.9245 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7749 2.7749 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9088 -7.1239 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4899 2.2749 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6239 -7.6239 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5157 -1.9245 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3987 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6994 -8.1395 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6842 3.1169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2559 -6.4811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3420 -3.9093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7407 -0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1428 1.6321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7146 -7.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7407 -3.9093 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 1.1428 -6.4811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2559 1.6321 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 -0.3420 -0.9397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6239 2.7749 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.4899 -7.1239 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.5157 -2.9245 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 10.9144 -1.9245 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9088 2.2749 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7749 -7.6239 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.9430 4.0828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9630 -7.1882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3079 -4.1681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7067 -0.6809 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4357 2.3392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4557 -8.9318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7067 -4.1681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4557 4.0828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4357 -7.1882 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9630 2.3392 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9430 -8.9318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3079 -0.6809 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3987 -4.8490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6994 3.2905 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -5.7150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8987 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6994 -8.1395 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 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 26 1 0 0 0 0 8 27 1 0 0 0 0 9 27 1 0 0 0 0 10 28 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 30 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 33 1 0 0 0 0 31 16 1 1 0 0 0 32 17 1 6 0 0 0 33 18 1 6 0 0 0 34 19 1 1 0 0 0 34 46 1 0 0 0 0 34 77 1 0 0 0 0 35 20 1 1 0 0 0 35 47 1 0 0 0 0 35 76 1 0 0 0 0 36 21 1 1 0 0 0 36 48 1 0 0 0 0 36 78 1 0 0 0 0 37 25 1 6 0 0 0 37 52 1 0 0 0 0 37 61 1 0 0 0 0 38 26 1 6 0 0 0 38 53 1 0 0 0 0 38 62 1 0 0 0 0 39 27 1 6 0 0 0 39 54 1 0 0 0 0 39 63 1 0 0 0 0 40 28 1 1 0 0 0 40 55 1 0 0 0 0 40 58 1 0 0 0 0 41 29 1 1 0 0 0 41 56 1 0 0 0 0 41 59 1 0 0 0 0 42 30 1 1 0 0 0 42 57 1 0 0 0 0 42 60 1 0 0 0 0 43 31 1 6 0 0 0 43 49 1 0 0 0 0 43 79 1 0 0 0 0 44 32 1 6 0 0 0 44 50 1 0 0 0 0 44 81 1 0 0 0 0 45 33 1 6 0 0 0 45 51 1 0 0 0 0 45 80 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 61 2 3 0 0 0 49 67 1 0 0 0 0 50 62 2 3 0 0 0 50 68 1 0 0 0 0 51 63 2 3 0 0 0 51 69 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 55 73 2 0 0 0 0 55 79 1 0 0 0 0 56 74 2 0 0 0 0 56 80 1 0 0 0 0 57 75 2 0 0 0 0 57 81 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1152.68
Volume:	1178.438
LogP:	7.224
LogD:	3.784
LogS:	-3.986
# Rotatable Bonds:	12
TPSA:	339.38
# H-Bond Aceptor:	24
# H-Bond Donor:	6
# Rings:	1
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.108
Synthetic Accessibility Score:	6.998
Fsp3:	0.789
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:	-5.814
MDCK Permeability:	0.0002491813793312758
Pgp-inhibitor:	1.0
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.064
20% Bioavailability (F20%):	0.692
30% Bioavailability (F30%):	0.767

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	83.82019805908203%
Volume Distribution (VD):	0.924
Pgp-substrate:	4.194497585296631%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.016
CYP3A4-inhibitor:	0.135
CYP3A4-substrate:	0.203

ADMET: Excretion

Clearance (CL):	3.462
Half-life (T1/2):	0.107

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.02
Carcinogencity:	0.023
Eye Corrosion:	0.038
Eye Irritation:	0.054
Respiratory Toxicity:	0.124

Download Data

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

Natural Product: NPC141325

Natural Product ID:	NPC141325
*Common Name:**	Bacillistatin 1
IUPAC Name:	(3R,6R,9S,12S,15R,18R,21S,24S,27R,30R,33S,36S)-6,18,30-tris[(2S)-butan-2-yl]-12,24,36-trimethyl-3,9,15,21,27,33-hexa(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:	Bacillistatin 1
Standard InCHIKey:	NWXOLMBBOHPPQK-ACQPPXRZSA-N
Standard InCHI:	InChI=1S/C57H96N6O18/c1-22-31(16)43-49(67)61-37(25(4)5)52(70)76-35(20)47(65)59-41(29(12)13)56(74)80-45(33(18)24-3)51(69)63-39(27(8)9)54(72)78-36(21)48(66)60-42(30(14)15)57(75)81-44(32(17)23-2)50(68)62-38(26(6)7)53(71)77-34(19)46(64)58-40(28(10)11)55(73)79-43/h25-45H,22-24H2,1-21H3,(H,58,64)(H,59,65)(H,60,66)(H,61,67)(H,62,68)(H,63,69)/t31-,32-,33-,34-,35-,36-,37+,38+,39+,40-,41-,42-,43+,44+,45+/m0/s1
SMILES:	CC[C@H](C)[C@@H]1C(=N[C@H](C(C)C)C(=O)O[C@@H](C)C(=N[C@@H](C(C)C)C(=O)O[C@H]([C@@H](C)CC)C(=N[C@H](C(C)C)C(=O)O[C@@H](C)C(=N[C@@H](C(C)C)C(=O)O[C@H]([C@@H](C)CC)C(=N[C@H](C(C)C)C(=O)O[C@@H](C)C(=N[C@@H](C(C)C)C(=O)O1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2304273
PubChem CID:	45272223
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]
NPO1239	Bacillus silvestris	Species	Planococcaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25688575]
NPO1239	Bacillus silvestris	Species	Planococcaceae	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
ED50	1
GI50	12
MIC	6
Others	4

Activity Type	# Activity
Cell Line	11
NON-MOLECULAR	2
Organism	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.023	ug ml-1	PMID[483143]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.00095	ug.mL-1	PMID[483143]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.00061	ug.mL-1	PMID[483143]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	0.00045	ug.mL-1	PMID[483143]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.0023	ug.mL-1	PMID[483143]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	=	0.00087	ug.mL-1	PMID[483143]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	0.0015	ug.mL-1	PMID[483143]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	1.2	nM	PMID[483144]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	0.39	nM	PMID[483144]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.53	nM	PMID[483144]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	1.3	nM	PMID[483144]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	>	64.0	ug.mL-1	PMID[483143]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	>	64.0	ug.mL-1	PMID[483143]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	2.0	ug.mL-1	PMID[483143]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MBC	=	4.0	ug ml-1	PMID[483143]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	1.0	ug.mL-1	PMID[483143]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MBC	=	2.0	ug ml-1	PMID[483143]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	<	0.5	ug.mL-1	PMID[483143]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MBC	=	1.0	ug ml-1	PMID[483143]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	2.0	ug.mL-1	PMID[483143]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MBC	>	32.0	ug ml-1	PMID[483143]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	0.75	nM	PMID[483144]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	0.82	nM	PMID[483144]

☑ 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 NPC141325 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	182
0.1-0.2	11301
0.2-0.3	19274
0.3-0.4	10206
0.4-0.5	1302
0.5-0.6	283
0.6-0.7	93
0.7-0.8	43
0.8-0.85	2
0.85-0.9	2
0.9-0.95	2
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9851	High Similarity	NPC138435
0.9565	High Similarity	NPC476324
0.9565	High Similarity	NPC476130
0.9545	High Similarity	NPC193280
0.9545	High Similarity	NPC314273
0.9118	High Similarity	NPC476291
0.8841	High Similarity	NPC476285
0.8732	High Similarity	NPC476248
0.831	Intermediate Similarity	NPC478256
0.8108	Intermediate Similarity	NPC472595
0.7895	Intermediate Similarity	NPC472594
0.7867	Intermediate Similarity	NPC86064
0.7805	Intermediate Similarity	NPC477728
0.7733	Intermediate Similarity	NPC43219
0.7625	Intermediate Similarity	NPC246005
0.7317	Intermediate Similarity	NPC477730
0.7284	Intermediate Similarity	NPC314466
0.7229	Intermediate Similarity	NPC95478
0.7229	Intermediate Similarity	NPC155670
0.7229	Intermediate Similarity	NPC145748
0.72	Intermediate Similarity	NPC474298
0.72	Intermediate Similarity	NPC473985
0.72	Intermediate Similarity	NPC474299
0.72	Intermediate Similarity	NPC472579
0.72	Intermediate Similarity	NPC475808
0.72	Intermediate Similarity	NPC28348
0.7143	Intermediate Similarity	NPC227051
0.7143	Intermediate Similarity	NPC474403
0.7126	Intermediate Similarity	NPC477729
0.6829	Remote Similarity	NPC315131
0.6829	Remote Similarity	NPC315535
0.6829	Remote Similarity	NPC478017
0.6778	Remote Similarity	NPC208537
0.6778	Remote Similarity	NPC270005
0.6761	Remote Similarity	NPC472578
0.6707	Remote Similarity	NPC316242
0.6667	Remote Similarity	NPC316826
0.6667	Remote Similarity	NPC473599
0.6667	Remote Similarity	NPC317143
0.6627	Remote Similarity	NPC473984
0.662	Remote Similarity	NPC318260
0.6575	Remote Similarity	NPC471129
0.6575	Remote Similarity	NPC327170
0.6575	Remote Similarity	NPC329564
0.6533	Remote Similarity	NPC145658
0.6486	Remote Similarity	NPC477644
0.6438	Remote Similarity	NPC327748
0.6438	Remote Similarity	NPC321468
0.6429	Remote Similarity	NPC316889
0.6429	Remote Similarity	NPC321118
0.642	Remote Similarity	NPC178919
0.6413	Remote Similarity	NPC471098
0.6413	Remote Similarity	NPC173763
0.6413	Remote Similarity	NPC62263
0.641	Remote Similarity	NPC470110
0.6389	Remote Similarity	NPC317147
0.6377	Remote Similarity	NPC322946
0.6374	Remote Similarity	NPC475801
0.6374	Remote Similarity	NPC474593
0.6354	Remote Similarity	NPC220234
0.6324	Remote Similarity	NPC80350
0.6304	Remote Similarity	NPC474576
0.6301	Remote Similarity	NPC328447
0.6296	Remote Similarity	NPC477641
0.6296	Remote Similarity	NPC320865
0.6296	Remote Similarity	NPC477643
0.6282	Remote Similarity	NPC470109
0.6277	Remote Similarity	NPC470283
0.625	Remote Similarity	NPC477642
0.622	Remote Similarity	NPC263281
0.6207	Remote Similarity	NPC84128
0.6207	Remote Similarity	NPC53858
0.6203	Remote Similarity	NPC195165
0.619	Remote Similarity	NPC63191
0.619	Remote Similarity	NPC471202
0.618	Remote Similarity	NPC476523
0.6173	Remote Similarity	NPC477200
0.6162	Remote Similarity	NPC5864
0.6162	Remote Similarity	NPC301148
0.6162	Remote Similarity	NPC124554
0.6154	Remote Similarity	NPC470108
0.6154	Remote Similarity	NPC474402
0.6136	Remote Similarity	NPC474312
0.6132	Remote Similarity	NPC472536
0.6132	Remote Similarity	NPC103391
0.6129	Remote Similarity	NPC477538
0.6125	Remote Similarity	NPC212866
0.6125	Remote Similarity	NPC29598
0.6118	Remote Similarity	NPC477145
0.6118	Remote Similarity	NPC473741
0.6087	Remote Similarity	NPC328378
0.6055	Remote Similarity	NPC477237
0.604	Remote Similarity	NPC323720
0.604	Remote Similarity	NPC124549
0.6026	Remote Similarity	NPC41429
0.602	Remote Similarity	NPC475440
0.6	Remote Similarity	NPC10716
0.6	Remote Similarity	NPC321536
0.598	Remote Similarity	NPC475918
0.5977	Remote Similarity	NPC476137
0.5977	Remote Similarity	NPC476117
0.5977	Remote Similarity	NPC476156
0.5977	Remote Similarity	NPC476243
0.5974	Remote Similarity	NPC145627
0.5974	Remote Similarity	NPC327252
0.5955	Remote Similarity	NPC47135
0.5946	Remote Similarity	NPC477238
0.5941	Remote Similarity	NPC198344
0.593	Remote Similarity	NPC37681
0.5926	Remote Similarity	NPC126779
0.5909	Remote Similarity	NPC476302
0.589	Remote Similarity	NPC322573
0.5889	Remote Similarity	NPC320936
0.5882	Remote Similarity	NPC74035
0.5865	Remote Similarity	NPC67009
0.5865	Remote Similarity	NPC171734
0.5862	Remote Similarity	NPC31756
0.5859	Remote Similarity	NPC475758
0.5851	Remote Similarity	NPC39290
0.5851	Remote Similarity	NPC159369
0.5842	Remote Similarity	NPC471097
0.5842	Remote Similarity	NPC475149
0.5825	Remote Similarity	NPC475637
0.5816	Remote Similarity	NPC473597
0.5802	Remote Similarity	NPC306696
0.58	Remote Similarity	NPC475791
0.58	Remote Similarity	NPC13175
0.5789	Remote Similarity	NPC254541
0.5789	Remote Similarity	NPC476019
0.5789	Remote Similarity	NPC320598
0.5775	Remote Similarity	NPC319110
0.5775	Remote Similarity	NPC329181
0.5747	Remote Similarity	NPC191774
0.5745	Remote Similarity	NPC470284
0.5732	Remote Similarity	NPC474812
0.5714	Remote Similarity	NPC315897
0.5714	Remote Similarity	NPC237420
0.5714	Remote Similarity	NPC143722
0.5682	Remote Similarity	NPC474833
0.5658	Remote Similarity	NPC190385
0.5658	Remote Similarity	NPC176164
0.5658	Remote Similarity	NPC189301
0.5641	Remote Similarity	NPC476125
0.5641	Remote Similarity	NPC476179
0.5625	Remote Similarity	NPC128559
0.5618	Remote Similarity	NPC474702
0.5616	Remote Similarity	NPC189178
0.5616	Remote Similarity	NPC137327
0.5616	Remote Similarity	NPC263065
0.56	Remote Similarity	NPC325985
0.56	Remote Similarity	NPC38463

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 NPC141325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	90
0.1-0.2	3553
0.2-0.3	4009
0.3-0.4	1057
0.4-0.5	329
0.5-0.6	97
0.6-0.7	11
0.7-0.8	4
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
0.7436	Intermediate Similarity	NPD2689	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3724	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD3160	Suspended
0.7308	Intermediate Similarity	NPD1453	Phase 1
0.6933	Remote Similarity	NPD2263	Discontinued
0.6829	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.663	Remote Similarity	NPD8394	Approved
0.6556	Remote Similarity	NPD3716	Discontinued
0.6429	Remote Similarity	NPD9419	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD9441	Phase 2
0.6316	Remote Similarity	NPD6428	Approved
0.6301	Remote Similarity	NPD9661	Approved
0.6296	Remote Similarity	NPD2256	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD1831	Phase 3
0.6211	Remote Similarity	NPD7844	Discontinued
0.6207	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD7840	Approved
0.61	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD3187	Discontinued
0.6067	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD574	Approved
0.5978	Remote Similarity	NPD4759	Clinical (unspecified phase)
0.5974	Remote Similarity	NPD575	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6095	Approved
0.5957	Remote Similarity	NPD6094	Approved
0.5955	Remote Similarity	NPD7345	Approved
0.5955	Remote Similarity	NPD7643	Phase 1
0.5926	Remote Similarity	NPD1815	Discontinued
0.5926	Remote Similarity	NPD4242	Approved
0.5905	Remote Similarity	NPD6421	Discontinued
0.5904	Remote Similarity	NPD6944	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD364	Discontinued
0.589	Remote Similarity	NPD4276	Approved
0.589	Remote Similarity	NPD4277	Approved
0.5875	Remote Similarity	NPD1429	Clinical (unspecified phase)
0.5867	Remote Similarity	NPD9433	Approved
0.5802	Remote Similarity	NPD4241	Registered
0.5769	Remote Similarity	NPD5375	Phase 3
0.5761	Remote Similarity	NPD7760	Phase 2
0.5761	Remote Similarity	NPD7759	Phase 2
0.5747	Remote Similarity	NPD4278	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1825	Clinical (unspecified phase)
0.5696	Remote Similarity	NPD1151	Approved
0.5679	Remote Similarity	NPD5380	Approved
0.566	Remote Similarity	NPD8305	Approved
0.566	Remote Similarity	NPD8306	Approved
0.5658	Remote Similarity	NPD9023	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD3192	Approved
0.5641	Remote Similarity	NPD3193	Approved
0.5616	Remote Similarity	NPD9204	Approved
0.5616	Remote Similarity	NPD9205	Approved
0.5604	Remote Similarity	NPD4829	Discontinued
0.56	Remote Similarity	NPD8038	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