NPASS Compound

Structure

NPC138435 OpenBabel07101718182D 81 81 0 0 1 0 0 0 0 0999 V2000 2.4554 -1.6113 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.8877 -1.3604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1949 -10.9187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2014 -12.3376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8999 -10.2494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3301 -10.9814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2282 -4.2886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0773 -2.5631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4981 2.3682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9169 1.3748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6151 -10.4814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8037 -9.4879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3414 -3.8246 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1904 -5.5500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2133 2.1363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7830 2.8682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3748 0.8037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2494 -0.2133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0491 -6.9037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5751 -7.9207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6437 2.6547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3682 -0.6151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9814 -1.7830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4694 -10.7678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2886 -11.3414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9037 -10.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6547 -3.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9207 1.4619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1925 -9.5751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7678 -4.6437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2095 2.0491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4619 -0.1925 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1622 -1.2095 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1428 -6.4811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7559 -7.3471 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5566 1.6585 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5566 -9.7716 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4811 -9.2559 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6585 -3.5566 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3471 0.6428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7660 -8.7559 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.7716 -4.5566 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6321 1.1428 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6428 -0.7660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2559 -1.6321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6428 -7.3471 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 -3.5566 1.6585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5566 -9.7716 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 -8.7559 -0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3471 -8.7559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6585 -4.5566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4811 1.1428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6321 -9.2559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7716 -3.5566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7660 0.6428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -8.1131 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.5979 -5.5414 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 -5.5414 -9.5979 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4848 -2.5718 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.1131 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4619 -7.9207 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1622 -6.9037 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4694 2.6547 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6437 -10.7678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0491 -1.2095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5751 -0.1925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9207 -9.5751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6547 -4.6437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9037 2.0491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2095 -10.1622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7678 -3.4694 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1925 1.4619 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1131 -8.1131 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4848 -5.5414 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 -9.5979 -2.5718 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 25 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 27 1 0 0 0 0 9 28 1 0 0 0 0 10 28 1 0 0 0 0 11 29 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 16 31 1 0 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 25 1 0 0 0 0 32 17 1 1 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 24 1 6 0 0 0 37 49 1 0 0 0 0 37 79 1 0 0 0 0 38 26 1 6 0 0 0 38 52 1 0 0 0 0 38 61 1 0 0 0 0 39 27 1 6 0 0 0 39 53 1 0 0 0 0 39 62 1 0 0 0 0 40 28 1 6 0 0 0 40 54 1 0 0 0 0 40 63 1 0 0 0 0 41 29 1 1 0 0 0 41 55 1 0 0 0 0 41 58 1 0 0 0 0 42 30 1 1 0 0 0 42 56 1 0 0 0 0 42 59 1 0 0 0 0 43 31 1 1 0 0 0 43 57 1 0 0 0 0 43 60 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:	265.17
Volume:	286.261
LogP:	2.173
LogD:	2.08
LogS:	-2.622
# Rotatable Bonds:	8
TPSA:	49.77
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.58
Synthetic Accessibility Score:	1.939
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.622
MDCK Permeability:	1.0862103408726398e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.974
Plasma Protein Binding (PPB):	25.36747932434082%
Volume Distribution (VD):	2.066
Pgp-substrate:	68.77230072021484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.217
CYP1A2-substrate:	0.952
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.881
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.44
CYP2D6-inhibitor:	0.564
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.34

ADMET: Excretion

Clearance (CL):	10.428
Half-life (T1/2):	0.848

ADMET: Toxicity

hERG Blockers:	0.167
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.215
AMES Toxicity:	0.028
Rat Oral Acute Toxicity:	0.832
Maximum Recommended Daily Dose:	0.043
Skin Sensitization:	0.846
Carcinogencity:	0.21
Eye Corrosion:	0.031
Eye Irritation:	0.055
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC138435

Natural Product ID:	NPC138435
*Common Name:**	Bacillistatin 2
IUPAC Name:	(3R,6R,9S,12S,15R,18R,21S,24S,27R,30R,33S,36S)-6,18-bis[(2S)-butan-2-yl]-12,24,36-trimethyl-30-(2-methylpropyl)-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:
Standard InCHIKey:	KVJGVUIUGIEWCD-RPUMXUQMSA-N
Standard InCHI:	InChI=1S/C57H96N6O18/c1-22-32(17)44-50(68)62-39(27(7)8)53(71)77-34(19)46(64)58-41(29(11)12)55(73)79-37(24-25(3)4)49(67)61-38(26(5)6)52(70)76-35(20)47(65)59-42(30(13)14)56(74)80-45(33(18)23-2)51(69)63-40(28(9)10)54(72)78-36(21)48(66)60-43(31(15)16)57(75)81-44/h25-45H,22-24H2,1-21H3,(H,58,64)(H,59,65)(H,60,66)(H,61,67)(H,62,68)(H,63,69)/t32-,33-,34-,35-,36-,37+,38+,39+,40+,41-,42-,43-,44+,45+/m0/s1
SMILES:	CC[C@@H]([C@H]1OC(=O)[C@@H](N=C(O)[C@H](C)OC(=O)[C@H](N=C(O)[C@H](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)O)C(C)C)CC(C)C)O)C(C)C)C)C(C)C)[C@H](CC)C)C(C)C)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2448555
PubChem CID:	45268830
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	7
GI50	13
MIC	6
Others	4

Activity Type	# Activity
Cell Line	18
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	=	0.013	ug ml-1	PMID[564500]
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.00034	ug.mL-1	PMID[564500]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.00031	ug.mL-1	PMID[564500]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	0.0018	ug.mL-1	PMID[564500]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.00045	ug.mL-1	PMID[564500]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	=	0.00026	ug.mL-1	PMID[564500]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	0.00086	ug.mL-1	PMID[564500]
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.016	ug ml-1	PMID[564501]
NPT1081	Cell Line	BXPC-3	Homo sapiens	ED50	<	0.001	ug ml-1	PMID[564501]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	<	0.001	ug ml-1	PMID[564501]
NPT395	Cell Line	SF-268	Homo sapiens	ED50	<	0.001	ug ml-1	PMID[564501]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	<	0.001	ug.mL-1	PMID[564501]
NPT575	Cell Line	KM-20L2	Homo sapiens	ED50	<	0.001	ug ml-1	PMID[564501]
NPT90	Cell Line	DU-145	Homo sapiens	ED50	<	0.001	ug ml-1	PMID[564501]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	0.39	nM	PMID[564502]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	1.6	nM	PMID[564502]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	0.27	nM	PMID[564502]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	0.75	nM	PMID[564502]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	>	64.0	ug.mL-1	PMID[564500]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	>	64.0	ug.mL-1	PMID[564500]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	1.0	ug.mL-1	PMID[564500]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MBC	=	2.0	ug ml-1	PMID[564500]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MBC	=	1.0	ug ml-1	PMID[564500]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	<	0.5	ug.mL-1	PMID[564500]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MBC	<	0.5	ug ml-1	PMID[564500]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MBC	>	16.0	ug ml-1	PMID[564500]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	2.0	ug.mL-1	PMID[564500]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	0.23	nM	PMID[564502]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	0.29	nM	PMID[564502]

☑ 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 NPC138435 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	161
0.1-0.2	9496
0.2-0.3	19754
0.3-0.4	11407
0.4-0.5	1456
0.5-0.6	268
0.6-0.7	102
0.7-0.8	34
0.8-0.85	8
0.85-0.9	3
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9851	High Similarity	NPC141325
0.971	High Similarity	NPC476324
0.971	High Similarity	NPC476130
0.9403	High Similarity	NPC314273
0.9403	High Similarity	NPC193280
0.8986	High Similarity	NPC476285
0.8986	High Similarity	NPC476291
0.8611	High Similarity	NPC476248
0.8451	Intermediate Similarity	NPC478256
0.8243	Intermediate Similarity	NPC472595
0.8026	Intermediate Similarity	NPC472594
0.8	Intermediate Similarity	NPC86064
0.7927	Intermediate Similarity	NPC477728
0.7867	Intermediate Similarity	NPC43219
0.7531	Intermediate Similarity	NPC246005
0.7439	Intermediate Similarity	NPC477730
0.7407	Intermediate Similarity	NPC314466
0.7349	Intermediate Similarity	NPC145748
0.7349	Intermediate Similarity	NPC155670
0.7349	Intermediate Similarity	NPC95478
0.7333	Intermediate Similarity	NPC472579
0.7273	Intermediate Similarity	NPC474403
0.7262	Intermediate Similarity	NPC227051
0.7241	Intermediate Similarity	NPC477729
0.7105	Intermediate Similarity	NPC474298
0.7105	Intermediate Similarity	NPC28348
0.7105	Intermediate Similarity	NPC474299
0.7105	Intermediate Similarity	NPC475808
0.7105	Intermediate Similarity	NPC473985
0.6951	Remote Similarity	NPC315131
0.6951	Remote Similarity	NPC315535
0.6951	Remote Similarity	NPC478017
0.6901	Remote Similarity	NPC472578
0.6829	Remote Similarity	NPC316242
0.6747	Remote Similarity	NPC473984
0.6712	Remote Similarity	NPC329564
0.6712	Remote Similarity	NPC471129
0.6712	Remote Similarity	NPC327170
0.6703	Remote Similarity	NPC270005
0.6703	Remote Similarity	NPC208537
0.6575	Remote Similarity	NPC316826
0.6575	Remote Similarity	NPC321468
0.6575	Remote Similarity	NPC473599
0.6575	Remote Similarity	NPC327748
0.6575	Remote Similarity	NPC317143
0.6538	Remote Similarity	NPC470110
0.6528	Remote Similarity	NPC317147
0.6528	Remote Similarity	NPC318260
0.6522	Remote Similarity	NPC173763
0.6522	Remote Similarity	NPC471098
0.6522	Remote Similarity	NPC62263
0.6522	Remote Similarity	NPC322946
0.6484	Remote Similarity	NPC475801
0.6484	Remote Similarity	NPC474593
0.6471	Remote Similarity	NPC80350
0.6458	Remote Similarity	NPC220234
0.6447	Remote Similarity	NPC145658
0.6413	Remote Similarity	NPC474576
0.641	Remote Similarity	NPC470109
0.64	Remote Similarity	NPC477644
0.6383	Remote Similarity	NPC470283
0.6341	Remote Similarity	NPC263281
0.6341	Remote Similarity	NPC178919
0.6338	Remote Similarity	NPC321118
0.6338	Remote Similarity	NPC316889
0.6329	Remote Similarity	NPC195165
0.6322	Remote Similarity	NPC53858
0.6322	Remote Similarity	NPC84128
0.6296	Remote Similarity	NPC477200
0.6292	Remote Similarity	NPC476523
0.6286	Remote Similarity	NPC471202
0.6286	Remote Similarity	NPC63191
0.6282	Remote Similarity	NPC470108
0.6282	Remote Similarity	NPC474402
0.6263	Remote Similarity	NPC301148
0.6263	Remote Similarity	NPC5864
0.6263	Remote Similarity	NPC124554
0.6237	Remote Similarity	NPC477538
0.6226	Remote Similarity	NPC103391
0.6226	Remote Similarity	NPC472536
0.622	Remote Similarity	NPC477641
0.622	Remote Similarity	NPC320865
0.622	Remote Similarity	NPC477643
0.6216	Remote Similarity	NPC328447
0.6173	Remote Similarity	NPC477642
0.6154	Remote Similarity	NPC41429
0.6147	Remote Similarity	NPC477237
0.6139	Remote Similarity	NPC124549
0.6067	Remote Similarity	NPC474312
0.6067	Remote Similarity	NPC47135
0.6049	Remote Similarity	NPC29598
0.6049	Remote Similarity	NPC212866
0.6047	Remote Similarity	NPC477145
0.6047	Remote Similarity	NPC37681
0.6047	Remote Similarity	NPC473741
0.604	Remote Similarity	NPC198344
0.6036	Remote Similarity	NPC477238
0.6	Remote Similarity	NPC328378
0.6	Remote Similarity	NPC320936
0.598	Remote Similarity	NPC323720
0.5962	Remote Similarity	NPC67009
0.5962	Remote Similarity	NPC171734
0.596	Remote Similarity	NPC475440
0.5926	Remote Similarity	NPC10716
0.5922	Remote Similarity	NPC475918
0.5921	Remote Similarity	NPC321536
0.5909	Remote Similarity	NPC476156
0.5909	Remote Similarity	NPC476117
0.5909	Remote Similarity	NPC476243
0.5909	Remote Similarity	NPC476137
0.5897	Remote Similarity	NPC327252
0.5897	Remote Similarity	NPC145627
0.5895	Remote Similarity	NPC476019
0.5862	Remote Similarity	NPC191774
0.5854	Remote Similarity	NPC126779
0.5851	Remote Similarity	NPC470284
0.5843	Remote Similarity	NPC476302
0.5825	Remote Similarity	NPC74035
0.5811	Remote Similarity	NPC322573
0.5804	Remote Similarity	NPC237420
0.58	Remote Similarity	NPC475758
0.5795	Remote Similarity	NPC31756
0.5789	Remote Similarity	NPC159369
0.5789	Remote Similarity	NPC39290
0.5784	Remote Similarity	NPC475149
0.5784	Remote Similarity	NPC471097
0.5769	Remote Similarity	NPC475637
0.5758	Remote Similarity	NPC473597
0.5753	Remote Similarity	NPC137327
0.5743	Remote Similarity	NPC475791
0.5743	Remote Similarity	NPC13175
0.5732	Remote Similarity	NPC306696
0.573	Remote Similarity	NPC474702
0.5726	Remote Similarity	NPC476125
0.5726	Remote Similarity	NPC476179
0.5714	Remote Similarity	NPC254541
0.5714	Remote Similarity	NPC320598
0.5694	Remote Similarity	NPC329181
0.5694	Remote Similarity	NPC319110
0.5684	Remote Similarity	NPC193386
0.5682	Remote Similarity	NPC233108
0.567	Remote Similarity	NPC315237
0.5663	Remote Similarity	NPC474812
0.5647	Remote Similarity	NPC315897
0.5641	Remote Similarity	NPC143722
0.5641	Remote Similarity	NPC470363
0.5641	Remote Similarity	NPC476241
0.5641	Remote Similarity	NPC476260
0.5634	Remote Similarity	NPC180402
0.5634	Remote Similarity	NPC87359
0.5618	Remote Similarity	NPC474833

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 NPC138435 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	87
0.1-0.2	3253
0.2-0.3	4222
0.3-0.4	1130
0.4-0.5	348
0.5-0.6	95
0.6-0.7	10
0.7-0.8	5
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
0.7568	Intermediate Similarity	NPD3724	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2689	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1453	Phase 1
0.725	Intermediate Similarity	NPD3160	Suspended
0.7067	Intermediate Similarity	NPD2263	Discontinued
0.6951	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD8394	Approved
0.6522	Remote Similarity	NPD9441	Phase 2
0.6484	Remote Similarity	NPD3716	Discontinued
0.6364	Remote Similarity	NPD1831	Phase 3
0.6338	Remote Similarity	NPD9419	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6428	Approved
0.622	Remote Similarity	NPD2256	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3187	Discontinued
0.6216	Remote Similarity	NPD9661	Approved
0.6146	Remote Similarity	NPD7844	Discontinued
0.6067	Remote Similarity	NPD7345	Approved
0.6049	Remote Similarity	NPD7840	Approved
0.604	Remote Similarity	NPD8045	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6421	Discontinued
0.5974	Remote Similarity	NPD574	Approved
0.5914	Remote Similarity	NPD4759	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD575	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD6094	Approved
0.5895	Remote Similarity	NPD6095	Approved
0.5889	Remote Similarity	NPD7643	Phase 1
0.587	Remote Similarity	NPD7760	Phase 2
0.587	Remote Similarity	NPD7759	Phase 2
0.5862	Remote Similarity	NPD4278	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4242	Approved
0.5854	Remote Similarity	NPD1815	Discontinued
0.5833	Remote Similarity	NPD6944	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD364	Discontinued
0.5811	Remote Similarity	NPD4276	Approved
0.5811	Remote Similarity	NPD4277	Approved
0.5802	Remote Similarity	NPD1429	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD9433	Approved
0.5755	Remote Similarity	NPD8305	Approved
0.5755	Remote Similarity	NPD8306	Approved
0.5732	Remote Similarity	NPD4241	Registered
0.5696	Remote Similarity	NPD5375	Phase 3
0.5684	Remote Similarity	NPD4264	Clinical (unspecified phase)
0.5647	Remote Similarity	NPD1825	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD7916	Approved
0.5636	Remote Similarity	NPD7915	Approved
0.5625	Remote Similarity	NPD1151	Approved
0.5612	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.561	Remote Similarity	NPD5380	Approved
0.56	Remote Similarity	NPD1830	Clinical (unspecified phase)

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