NPASS Compound

Structure

NPC2313 OpenBabel07101718332D 73 77 0 0 1 0 0 0 0 0999 V2000 15.2970 -3.7570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 0.7765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5617 0.3385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9783 -2.3884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3329 -0.1589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2071 -1.8910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8329 -1.0249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -1.0249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6990 -5.2570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.1631 0.7430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1225 2.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3073 1.3699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4310 -4.2570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1907 1.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2508 1.3429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2892 -3.3928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2700 1.5380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2700 -3.5879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0823 0.7873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4578 -2.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2508 -3.3928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2892 1.3429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5650 -0.7570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0012 4.1225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6990 -2.2570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4483 1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6378 -0.0442 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9022 -2.0057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8329 -1.0249 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7071 -1.0249 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.3329 -1.8910 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2071 -0.1589 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.6990 -4.2570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9659 0.2588 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 15.2970 0.2430 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4154 2.7083 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.5650 -3.7570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2247 1.2247 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.5650 0.2430 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9671 4.3813 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.5650 -2.7570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5176 1.9319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0823 -2.8372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4578 0.7873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4310 -1.2570 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7424 3.1566 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3329 -1.8910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2071 -0.1589 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 14.4310 0.7430 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6742 3.6742 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8329 -1.0249 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7071 -1.0249 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 11.8329 -2.7570 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7071 0.7071 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.6990 0.7430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2259 5.3473 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7894 -3.5443 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7507 1.4944 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8329 -2.7570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7071 0.7071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.4310 1.7430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6402 3.9331 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8329 -2.7570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3159 1.5005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.2970 -0.7570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4495 2.4495 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.4310 -2.2570 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 2.8978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6378 -2.0057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9022 -0.0442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8329 -3.7570 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 14 1 0 0 0 0 2 15 1 0 0 0 0 13 65 1 0 0 0 0 16 18 1 0 0 0 0 16 20 2 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 23 2 0 0 0 0 19 22 2 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 44 1 0 0 0 0 23 45 1 0 0 0 0 24 40 1 0 0 0 0 24 46 1 0 0 0 0 25 41 1 0 0 0 0 25 47 1 0 0 0 0 26 42 1 0 0 0 0 26 54 1 0 0 0 0 27 43 1 0 0 0 0 27 55 1 0 0 0 0 28 3 1 6 0 0 0 28 52 1 0 0 0 0 29 4 1 6 0 0 0 29 53 1 0 0 0 0 30 5 1 1 0 0 0 30 48 1 0 0 0 0 31 6 1 1 0 0 0 31 49 1 0 0 0 0 32 7 1 6 0 0 0 32 48 1 0 0 0 0 32 54 1 0 0 0 0 33 8 1 6 0 0 0 33 49 1 0 0 0 0 33 55 1 0 0 0 0 34 9 1 1 0 0 0 34 38 1 0 0 0 0 34 72 1 0 0 0 0 35 10 1 6 0 0 0 35 39 1 0 0 0 0 35 73 1 0 0 0 0 36 11 1 6 0 0 0 36 50 1 0 0 0 0 36 66 1 0 0 0 0 37 12 1 1 0 0 0 37 51 1 0 0 0 0 37 67 1 0 0 0 0 38 14 1 6 0 0 0 38 42 1 0 0 0 0 39 15 1 1 0 0 0 39 43 1 0 0 0 0 40 50 1 0 0 0 0 40 56 1 6 0 0 0 41 51 1 0 0 0 0 41 57 1 1 0 0 0 42 68 1 1 0 0 0 43 69 1 6 0 0 0 44 58 2 0 0 0 0 44 70 1 0 0 0 0 45 59 2 0 0 0 0 45 71 1 0 0 0 0 46 66 1 0 0 0 0 46 68 1 1 0 0 0 47 67 1 0 0 0 0 47 69 1 6 0 0 0 48 60 1 6 0 0 0 49 61 1 6 0 0 0 50 62 1 6 0 0 0 51 63 1 1 0 0 0 52 30 1 1 0 0 0 52 70 1 0 0 0 0 53 31 1 1 0 0 0 53 71 1 0 0 0 0 54 64 1 6 0 0 0 54 72 1 0 0 0 0 55 65 1 1 0 0 0 55 73 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1038.61
Volume:	1059.459
LogP:	5.527
LogD:	4.548
LogS:	-4.578
# Rotatable Bonds:	15
TPSA:	258.82
# H-Bond Aceptor:	18
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	18

MedChem Properties

QED Drug-Likeness Score:	0.109
Synthetic Accessibility Score:	7.596
Fsp3:	0.818
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.468
MDCK Permeability:	0.000406066159484908
Pgp-inhibitor:	1.0
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.421
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.17

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	89.69108581542969%
Volume Distribution (VD):	0.585
Pgp-substrate:	5.038909435272217%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.077
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.007
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.041
CYP3A4-inhibitor:	0.501
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	5.763
Half-life (T1/2):	0.113

ADMET: Toxicity

hERG Blockers:	0.789
Human Hepatotoxicity (H-HT):	0.497
Drug-inuced Liver Injury (DILI):	0.094
AMES Toxicity:	0.262
Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.942
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.985

Download Data

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

Natural Product: NPC2313

Natural Product ID:	NPC2313
*Common Name:**	11-O-Methylelaiophylin
IUPAC Name:	(3E,5E,7S,8S,11E,13E,15S,16S)-8-[(2S,3R,4S)-4-[(2R,4R,5R,6R)-4-[(2R,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-ethyl-2-hydroxy-6-methyloxan-2-yl]-3-hydroxypentan-2-yl]-16-[(2S,3R,4S)-4-[(2R,4R,5R,6R)-4-[(2R,4S,5S,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-ethyl-2-methoxy-6-methyloxan-2-yl]-3-hydroxypentan-2-yl]-7,15-dimethyl-1,9-dioxacyclohexadeca-3,5,11,13-tetraene-2,10-dione
Synonyms:
Standard InCHIKey:	IQUQYYTZXBLSTO-ZQQRVOIPSA-N
Standard InCHI:	InChI=1S/C55H90O18/c1-14-38-34(9)72-54(64,26-42(38)68-46-24-40(56)50(62)36(11)66-46)32(7)48(60)30(5)52-28(3)20-16-18-23-45(59)71-53(29(4)21-17-19-22-44(58)70-52)31(6)49(61)33(8)55(65-13)27-43(39(15-2)35(10)73-55)69-47-25-41(57)51(63)37(12)67-47/h16-23,28-43,46-53,56-57,60-64H,14-15,24-27H2,1-13H3/b20-16+,21-17+,22-19+,23-18+/t28-,29-,30-,31-,32-,33-,34+,35+,36-,37-,38+,39+,40-,41-,42+,43+,46-,47-,48+,49+,50+,51+,52-,53-,54+,55+/m0/s1
SMILES:	CC[C@H]1[C@H](O[C@H]2C[C@H](O)[C@@H]([C@@H](O2)C)O)C[C@](O[C@@H]1C)(O)[C@H]([C@@H]([C@@H]([C@H]1OC(=O)/C=C/C=C/[C@H](C)[C@H](OC(=O)/C=C/C=C/[C@@H]1C)[C@H]([C@H]([C@@H]([C@@]1(OC)C[C@@H](O[C@H]2C[C@H](O)[C@@H]([C@@H](O2)C)O)[C@@H]([C@H](O1)C)CC)C)O)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3086649
PubChem CID:	10558006
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO32916	Streptomyces sp. 7-145	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24164206]
NPO40219	Streptomyces sp. ICBB 9297	Strain	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26510047]

☑ 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
MIC	28

Activity Type	# Activity
NON-MOLECULAR	1
Organism	27

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3495	Organism	Morganella morganii	Morganella morganii	MIC	>	256.0	ug.mL-1	PMID[515681]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	256.0	ug.mL-1	PMID[515681]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	>	256.0	ug.mL-1	PMID[515681]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	256.0	ug.mL-1	PMID[515681]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	256.0	ug.mL-1	PMID[515681]
NPT1204	Organism	Enterococcus faecalis ATCC 29212	Enterococcus faecalis ATCC 29212	MIC	=	32.0	ug.mL-1	PMID[515681]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	2.0	ug.mL-1	PMID[515681]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	2.0	ug.mL-1	PMID[515681]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	2.0	ug.mL-1	PMID[515681]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	2.0	ug.mL-1	PMID[515681]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	=	2.0	ug.mL-1	PMID[515681]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[515681]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	1.0	ug.mL-1	PMID[515681]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.0	ug.mL-1	PMID[515681]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.56	ug.mL-1	PMID[515682]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	100.0	ug.mL-1	PMID[515682]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	100.0	ug.mL-1	PMID[515682]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[515682]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[515682]

☑ 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 NPC2313 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	221
0.1-0.2	1341
0.2-0.3	4459
0.3-0.4	10481
0.4-0.5	12962
0.5-0.6	8720
0.6-0.7	3347
0.7-0.8	1096
0.8-0.85	53
0.85-0.9	4
0.9-0.95	2
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC57586
1.0	High Similarity	NPC475655
1.0	High Similarity	NPC475157
1.0	High Similarity	NPC471637
1.0	High Similarity	NPC154132
0.9588	High Similarity	NPC315070
0.9583	High Similarity	NPC197736
0.8866	High Similarity	NPC475332
0.875	High Similarity	NPC159698
0.8737	High Similarity	NPC476075
0.8737	High Similarity	NPC110072
0.8737	High Similarity	NPC476084
0.8646	High Similarity	NPC472196
0.8646	High Similarity	NPC238090
0.8646	High Similarity	NPC472195
0.8542	High Similarity	NPC471324
0.8542	High Similarity	NPC206679
0.8542	High Similarity	NPC114172
0.8526	High Similarity	NPC285588
0.8454	Intermediate Similarity	NPC109406
0.8454	Intermediate Similarity	NPC159092
0.8404	Intermediate Similarity	NPC208473
0.8381	Intermediate Similarity	NPC133625
0.8316	Intermediate Similarity	NPC313658
0.8316	Intermediate Similarity	NPC316138
0.8286	Intermediate Similarity	NPC193765
0.82	Intermediate Similarity	NPC288350
0.82	Intermediate Similarity	NPC173329
0.82	Intermediate Similarity	NPC255410
0.8191	Intermediate Similarity	NPC473308
0.8191	Intermediate Similarity	NPC266718
0.8182	Intermediate Similarity	NPC477348
0.8182	Intermediate Similarity	NPC256368
0.8182	Intermediate Similarity	NPC238264
0.8182	Intermediate Similarity	NPC477345
0.8172	Intermediate Similarity	NPC251026
0.8155	Intermediate Similarity	NPC201191
0.8125	Intermediate Similarity	NPC475186
0.8125	Intermediate Similarity	NPC199382
0.8125	Intermediate Similarity	NPC118077
0.8119	Intermediate Similarity	NPC120299
0.81	Intermediate Similarity	NPC300710
0.8095	Intermediate Similarity	NPC476740
0.8095	Intermediate Similarity	NPC476738
0.8085	Intermediate Similarity	NPC473315
0.8085	Intermediate Similarity	NPC142111
0.8065	Intermediate Similarity	NPC469469
0.8065	Intermediate Similarity	NPC184208
0.8065	Intermediate Similarity	NPC8538
0.8061	Intermediate Similarity	NPC202886
0.8039	Intermediate Similarity	NPC475653
0.8039	Intermediate Similarity	NPC203627
0.802	Intermediate Similarity	NPC476066
0.802	Intermediate Similarity	NPC475525
0.802	Intermediate Similarity	NPC475241
0.802	Intermediate Similarity	NPC475375
0.802	Intermediate Similarity	NPC473765
0.802	Intermediate Similarity	NPC473605
0.802	Intermediate Similarity	NPC475540
0.802	Intermediate Similarity	NPC475164
0.802	Intermediate Similarity	NPC475593
0.8	Intermediate Similarity	NPC294293
0.798	Intermediate Similarity	NPC477749
0.798	Intermediate Similarity	NPC477349
0.7965	Intermediate Similarity	NPC135369
0.7959	Intermediate Similarity	NPC477748
0.7946	Intermediate Similarity	NPC470515
0.7938	Intermediate Similarity	NPC125142
0.7925	Intermediate Similarity	NPC82251
0.7917	Intermediate Similarity	NPC471494
0.7905	Intermediate Similarity	NPC474581
0.7905	Intermediate Similarity	NPC475367
0.7905	Intermediate Similarity	NPC473816
0.7905	Intermediate Similarity	NPC309398
0.79	Intermediate Similarity	NPC320089
0.79	Intermediate Similarity	NPC320552
0.7885	Intermediate Similarity	NPC476611
0.7879	Intermediate Similarity	NPC327253
0.7879	Intermediate Similarity	NPC473311
0.7879	Intermediate Similarity	NPC177668
0.7876	Intermediate Similarity	NPC470517
0.7876	Intermediate Similarity	NPC470911
0.7876	Intermediate Similarity	NPC470915
0.7872	Intermediate Similarity	NPC315731
0.7857	Intermediate Similarity	NPC470137
0.7835	Intermediate Similarity	NPC311163
0.783	Intermediate Similarity	NPC469869
0.7822	Intermediate Similarity	NPC44682
0.7822	Intermediate Similarity	NPC163409
0.7822	Intermediate Similarity	NPC472198
0.7818	Intermediate Similarity	NPC321272
0.7818	Intermediate Similarity	NPC328074
0.7818	Intermediate Similarity	NPC317460
0.7818	Intermediate Similarity	NPC470025
0.781	Intermediate Similarity	NPC473596
0.78	Intermediate Similarity	NPC472199
0.78	Intermediate Similarity	NPC472197
0.7798	Intermediate Similarity	NPC316708
0.7778	Intermediate Similarity	NPC179261
0.7778	Intermediate Similarity	NPC473807
0.7778	Intermediate Similarity	NPC133450
0.7766	Intermediate Similarity	NPC127295
0.7766	Intermediate Similarity	NPC163362
0.7759	Intermediate Similarity	NPC219804
0.7748	Intermediate Similarity	NPC470027
0.7748	Intermediate Similarity	NPC473159
0.7745	Intermediate Similarity	NPC170204
0.7745	Intermediate Similarity	NPC469543
0.7739	Intermediate Similarity	NPC183353
0.7739	Intermediate Similarity	NPC469812
0.7727	Intermediate Similarity	NPC17791
0.7727	Intermediate Similarity	NPC126897
0.7727	Intermediate Similarity	NPC470026
0.7727	Intermediate Similarity	NPC297945
0.7719	Intermediate Similarity	NPC470914
0.7714	Intermediate Similarity	NPC198992
0.7706	Intermediate Similarity	NPC315836
0.7706	Intermediate Similarity	NPC313668
0.77	Intermediate Similarity	NPC3952
0.7692	Intermediate Similarity	NPC471090
0.7685	Intermediate Similarity	NPC109376
0.7677	Intermediate Similarity	NPC248312
0.767	Intermediate Similarity	NPC143446
0.7664	Intermediate Similarity	NPC470768
0.7664	Intermediate Similarity	NPC231271
0.7664	Intermediate Similarity	NPC470519
0.766	Intermediate Similarity	NPC139712
0.7629	Intermediate Similarity	NPC475035
0.7627	Intermediate Similarity	NPC297950
0.7615	Intermediate Similarity	NPC392
0.7615	Intermediate Similarity	NPC177524
0.7615	Intermediate Similarity	NPC224660
0.7615	Intermediate Similarity	NPC219900
0.7615	Intermediate Similarity	NPC470024
0.7604	Intermediate Similarity	NPC477390
0.7604	Intermediate Similarity	NPC477385
0.7596	Intermediate Similarity	NPC309503
0.7596	Intermediate Similarity	NPC239547
0.7596	Intermediate Similarity	NPC155319
0.7596	Intermediate Similarity	NPC476612
0.7596	Intermediate Similarity	NPC91197
0.7596	Intermediate Similarity	NPC476613
0.7596	Intermediate Similarity	NPC278506
0.7596	Intermediate Similarity	NPC96597
0.7596	Intermediate Similarity	NPC125551
0.7593	Intermediate Similarity	NPC239961
0.7593	Intermediate Similarity	NPC172867
0.7593	Intermediate Similarity	NPC470763
0.7593	Intermediate Similarity	NPC470767
0.7589	Intermediate Similarity	NPC287075
0.7586	Intermediate Similarity	NPC170880
0.7579	Intermediate Similarity	NPC470147
0.7579	Intermediate Similarity	NPC133226
0.7576	Intermediate Similarity	NPC475037
0.7551	Intermediate Similarity	NPC470124
0.7549	Intermediate Similarity	NPC61201
0.7547	Intermediate Similarity	NPC280991
0.7525	Intermediate Similarity	NPC471569
0.7524	Intermediate Similarity	NPC65700
0.7524	Intermediate Similarity	NPC198422
0.7524	Intermediate Similarity	NPC40182
0.7521	Intermediate Similarity	NPC231888
0.7521	Intermediate Similarity	NPC10121
0.7521	Intermediate Similarity	NPC92283
0.7521	Intermediate Similarity	NPC471082
0.7521	Intermediate Similarity	NPC124878
0.7521	Intermediate Similarity	NPC10883
0.7521	Intermediate Similarity	NPC35338
0.7521	Intermediate Similarity	NPC290276
0.7521	Intermediate Similarity	NPC147032
0.7521	Intermediate Similarity	NPC474423
0.7521	Intermediate Similarity	NPC74259
0.7521	Intermediate Similarity	NPC204214
0.7521	Intermediate Similarity	NPC63404
0.7521	Intermediate Similarity	NPC198918
0.75	Intermediate Similarity	NPC220838
0.75	Intermediate Similarity	NPC472268
0.75	Intermediate Similarity	NPC476150
0.75	Intermediate Similarity	NPC472269
0.75	Intermediate Similarity	NPC87153
0.75	Intermediate Similarity	NPC45606
0.75	Intermediate Similarity	NPC472270
0.75	Intermediate Similarity	NPC476127
0.75	Intermediate Similarity	NPC23020
0.75	Intermediate Similarity	NPC162925
0.75	Intermediate Similarity	NPC112492
0.75	Intermediate Similarity	NPC306041
0.7478	Intermediate Similarity	NPC473828
0.7478	Intermediate Similarity	NPC93688
0.7478	Intermediate Similarity	NPC473617
0.7478	Intermediate Similarity	NPC109603
0.7478	Intermediate Similarity	NPC13710
0.7477	Intermediate Similarity	NPC222062
0.7477	Intermediate Similarity	NPC121423
0.7476	Intermediate Similarity	NPC469491
0.7474	Intermediate Similarity	NPC180725
0.7474	Intermediate Similarity	NPC470148
0.7474	Intermediate Similarity	NPC470149
0.7458	Intermediate Similarity	NPC308262
0.7458	Intermediate Similarity	NPC315783

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 NPC2313 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1472
0.2-0.3	3828
0.3-0.4	2496
0.4-0.5	841
0.5-0.6	258
0.6-0.7	38
0.7-0.8	22
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7838	Discovery
0.7739	Intermediate Similarity	NPD8516	Approved
0.7739	Intermediate Similarity	NPD8515	Approved
0.7739	Intermediate Similarity	NPD8517	Approved
0.7727	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD6686	Approved
0.7586	Intermediate Similarity	NPD8513	Phase 3
0.7525	Intermediate Similarity	NPD46	Approved
0.7525	Intermediate Similarity	NPD6698	Approved
0.7458	Intermediate Similarity	NPD7829	Approved
0.7458	Intermediate Similarity	NPD7830	Approved
0.7436	Intermediate Similarity	NPD7503	Approved
0.735	Intermediate Similarity	NPD8377	Approved
0.735	Intermediate Similarity	NPD8294	Approved
0.7288	Intermediate Similarity	NPD8296	Approved
0.7288	Intermediate Similarity	NPD8033	Approved
0.7288	Intermediate Similarity	NPD8335	Approved
0.7288	Intermediate Similarity	NPD8380	Approved
0.7288	Intermediate Similarity	NPD8378	Approved
0.7288	Intermediate Similarity	NPD8379	Approved
0.7115	Intermediate Similarity	NPD7983	Approved
0.7034	Intermediate Similarity	NPD7327	Approved
0.7034	Intermediate Similarity	NPD7328	Approved
0.7	Intermediate Similarity	NPD8444	Approved
0.6992	Remote Similarity	NPD8448	Approved
0.6975	Remote Similarity	NPD7516	Approved
0.696	Remote Similarity	NPD8390	Approved
0.696	Remote Similarity	NPD8392	Approved
0.696	Remote Similarity	NPD8391	Approved
0.6911	Remote Similarity	NPD8451	Approved
0.6909	Remote Similarity	NPD5344	Discontinued
0.6838	Remote Similarity	NPD8133	Approved
0.6818	Remote Similarity	NPD6648	Approved
0.6765	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7641	Discontinued
0.672	Remote Similarity	NPD8074	Phase 3
0.6697	Remote Similarity	NPD7839	Suspended
0.6694	Remote Similarity	NPD8299	Approved
0.6694	Remote Similarity	NPD8340	Approved
0.6694	Remote Similarity	NPD8341	Approved
0.6694	Remote Similarity	NPD8342	Approved
0.664	Remote Similarity	NPD7507	Approved
0.6613	Remote Similarity	NPD8328	Phase 3
0.6613	Remote Similarity	NPD7642	Approved
0.6609	Remote Similarity	NPD6412	Phase 2
0.6484	Remote Similarity	NPD7319	Approved
0.6466	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7266	Discontinued
0.6283	Remote Similarity	NPD4225	Approved
0.6273	Remote Similarity	NPD5778	Approved
0.6273	Remote Similarity	NPD5779	Approved
0.6269	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.626	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7637	Suspended
0.6167	Remote Similarity	NPD6371	Approved
0.6147	Remote Similarity	NPD6101	Approved
0.6147	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7638	Approved
0.6129	Remote Similarity	NPD7505	Discontinued
0.6111	Remote Similarity	NPD4251	Approved
0.6111	Remote Similarity	NPD4250	Approved
0.6087	Remote Similarity	NPD7640	Approved
0.6087	Remote Similarity	NPD7639	Approved
0.6058	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6411	Approved
0.6031	Remote Similarity	NPD7736	Approved
0.6022	Remote Similarity	NPD6123	Approved
0.6019	Remote Similarity	NPD4249	Approved
0.6016	Remote Similarity	NPD8080	Discontinued
0.6	Remote Similarity	NPD7115	Discovery
0.6	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7500	Approved
0.6	Remote Similarity	NPD8273	Phase 1
0.5984	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD7524	Approved
0.5946	Remote Similarity	NPD5785	Approved
0.5935	Remote Similarity	NPD6430	Approved
0.5935	Remote Similarity	NPD6429	Approved
0.5935	Remote Similarity	NPD6053	Discontinued
0.5931	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD4820	Approved
0.5905	Remote Similarity	NPD4819	Approved
0.5905	Remote Similarity	NPD4822	Approved
0.5905	Remote Similarity	NPD4821	Approved
0.5896	Remote Similarity	NPD7260	Phase 2
0.5888	Remote Similarity	NPD7154	Phase 3
0.5865	Remote Similarity	NPD4268	Approved
0.5865	Remote Similarity	NPD4271	Approved
0.5833	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5826	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.582	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.581	Remote Similarity	NPD7329	Approved
0.5809	Remote Similarity	NPD8450	Suspended
0.578	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.578	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.578	Remote Similarity	NPD5363	Approved
0.5773	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5125	Phase 3
0.5769	Remote Similarity	NPD6370	Approved
0.5769	Remote Similarity	NPD5126	Approved
0.5766	Remote Similarity	NPD8415	Approved
0.5764	Remote Similarity	NPD7625	Phase 1
0.5741	Remote Similarity	NPD6695	Phase 3
0.5739	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD8449	Approved
0.5728	Remote Similarity	NPD8039	Approved
0.5725	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD8293	Discontinued
0.5702	Remote Similarity	NPD4211	Phase 1
0.5702	Remote Similarity	NPD8171	Discontinued
0.5692	Remote Similarity	NPD8267	Approved
0.5692	Remote Similarity	NPD8268	Approved
0.5692	Remote Similarity	NPD8266	Approved
0.5692	Remote Similarity	NPD8269	Approved
0.5682	Remote Similarity	NPD7492	Approved
0.568	Remote Similarity	NPD8297	Approved
0.568	Remote Similarity	NPD6882	Approved
0.568	Remote Similarity	NPD969	Suspended
0.5676	Remote Similarity	NPD7750	Discontinued
0.5672	Remote Similarity	NPD8337	Approved
0.5672	Remote Similarity	NPD8336	Approved
0.5667	Remote Similarity	NPD1407	Approved
0.5648	Remote Similarity	NPD6435	Approved
0.5648	Remote Similarity	NPD5209	Approved
0.5645	Remote Similarity	NPD6421	Discontinued
0.5645	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5644	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5639	Remote Similarity	NPD6616	Approved
0.5625	Remote Similarity	NPD6009	Approved
0.5621	Remote Similarity	NPD8455	Phase 2
0.5615	Remote Similarity	NPD6054	Approved
0.5615	Remote Similarity	NPD6319	Approved
0.5615	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5607	Remote Similarity	NPD7332	Phase 2
0.5607	Remote Similarity	NPD7514	Phase 3

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