NPASS Compound

Structure

NPC125142 OpenBabel07101719132D 75 79 0 0 1 0 0 0 0 0999 V2000 -3.3660 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8301 6.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0981 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4282 7.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9545 6.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6244 6.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0981 5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5622 5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6340 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9641 4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7679 4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6962 4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5622 6.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6340 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2942 6.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3564 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8301 5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7679 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4282 6.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9545 5.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7583 6.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0000 -3.4641 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 10.4904 3.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 14.8205 4.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7583 5.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0000 -3.4641 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.4904 2.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 14.8205 3.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5000 -2.5981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6244 1.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 -1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.9545 3.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0000 -1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7583 2.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0263 5.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8923 4.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.0885 3.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0263 6.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0000 -1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7583 3.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.6865 5.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6244 4.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -4.3301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3564 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.6865 3.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6244 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9545 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8923 1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1603 4.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1603 6.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.2224 3.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.0885 4.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8923 6.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -2.5981 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 9.6244 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8923 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 8 50 1 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 22 2 0 0 0 0 13 23 1 0 0 0 0 14 22 1 0 0 0 0 15 24 2 0 0 0 0 16 23 2 0 0 0 0 17 50 1 0 0 0 0 18 51 1 0 0 0 0 19 52 1 0 0 0 0 20 24 1 0 0 0 0 20 66 1 0 0 0 0 21 67 1 0 0 0 0 25 5 1 1 0 0 0 25 30 1 0 0 0 0 25 68 1 0 0 0 0 26 6 1 1 0 0 0 26 31 1 0 0 0 0 26 69 1 0 0 0 0 27 18 1 6 0 0 0 27 32 1 0 0 0 0 27 70 1 0 0 0 0 28 19 1 6 0 0 0 28 33 1 0 0 0 0 28 71 1 0 0 0 0 29 21 1 6 0 0 0 29 34 1 0 0 0 0 29 72 1 0 0 0 0 30 35 1 0 0 0 0 30 53 1 6 0 0 0 31 43 1 0 0 0 0 31 54 1 6 0 0 0 32 36 1 0 0 0 0 32 55 1 1 0 0 0 33 38 1 0 0 0 0 33 56 1 1 0 0 0 34 37 1 0 0 0 0 34 57 1 1 0 0 0 35 39 1 0 0 0 0 35 58 1 1 0 0 0 36 40 1 0 0 0 0 36 59 1 6 0 0 0 37 41 1 0 0 0 0 37 60 1 6 0 0 0 38 44 1 0 0 0 0 38 61 1 6 0 0 0 39 45 1 0 0 0 0 39 62 1 1 0 0 0 40 47 1 0 0 0 0 40 63 1 1 0 0 0 41 48 1 0 0 0 0 41 64 1 1 0 0 0 42 43 1 0 0 0 0 42 46 1 0 0 0 0 42 65 1 1 0 0 0 43 73 1 1 0 0 0 44 49 1 0 0 0 0 44 74 1 1 0 0 0 45 67 1 6 0 0 0 45 68 1 0 0 0 0 46 66 1 6 0 0 0 46 69 1 0 0 0 0 47 70 1 0 0 0 0 47 74 1 6 0 0 0 48 72 1 0 0 0 0 48 73 1 6 0 0 0 49 71 1 0 0 0 0 49 75 1 6 0 0 0 50 7 1 1 0 0 0 50 75 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1084.53
Volume:	1039.783
LogP:	-0.35
LogD:	-0.579
LogS:	-3.077
# Rotatable Bonds:	24
TPSA:	395.75
# H-Bond Aceptor:	25
# H-Bond Donor:	15
# Rings:	5
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.041
Synthetic Accessibility Score:	6.714
Fsp3:	0.84
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:	-6.351
MDCK Permeability:	0.0005240531754679978
Pgp-inhibitor:	0.59
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.864
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.447
Plasma Protein Binding (PPB):	76.40502166748047%
Volume Distribution (VD):	-0.179
Pgp-substrate:	15.37047290802002%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.028
CYP3A4-inhibitor:	0.029
CYP3A4-substrate:	0.001

ADMET: Excretion

Clearance (CL):	0.164
Half-life (T1/2):	0.838

ADMET: Toxicity

hERG Blockers:	0.351
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.003
AMES Toxicity:	0.059
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.0
Skin Sensitization:	0.936
Carcinogencity:	0.007
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC125142

Natural Product ID:	NPC125142
*Common Name:**	Capsianoside Ii
IUPAC Name:	(2R,3R,4R,5R,6S)-2-[[(2R,3S,4S,5R,6S)-6-[(2R,3R,4R,5S,6S)-2-[(2Z,6E,10E,14S)-14-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoxy]-3,5-dihydroxy-6-methyloxan-4-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	NFBYZSYLZUMCFV-VZDZUNMMSA-N
Standard InCHI:	InChI=1S/C50H84O25/c1-8-50(7,75-49-44(38(61)33(56)28(19-52)71-49)74-47-40(63)36(59)32(55)27(18-51)70-47)17-11-16-23(3)13-9-12-22(2)14-10-15-24(4)20-66-46-42(65)43(31(54)26(6)69-46)73-48-41(64)37(60)34(57)29(72-48)21-67-45-39(62)35(58)30(53)25(5)68-45/h8,12,15-16,25-49,51-65H,1,9-11,13-14,17-21H2,2-7H3/b22-12+,23-16+,24-15-/t25-,26-,27+,28+,29+,30-,31-,32+,33+,34+,35+,36-,37-,38-,39+,40+,41+,42+,43+,44+,45+,46+,47-,48-,49-,50+/m0/s1
SMILES:	C=C[C@](C)(CC/C=C(C)/CC/C=C(C)/CC/C=C(/C)CO[C@H]1[C@@H]([C@@H]([C@H]([C@H](C)O1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@@H]([C@H]([C@H](C)O2)O)O)O)O1)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2271377
PubChem CID:	21672514
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*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
NPO16501.2	Capsicum annuum	Under-species	n.a.	n.a.	n.a.	n.a.	Granola: the 1999 growing season	DOI[10.1016/S0956-7135(03)00077-X]
NPO16501.2	Capsicum annuum	Under-species	n.a.	n.a.	seeds	n.a.	n.a.	PMID[12105963]
NPO16501.2	Capsicum annuum	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[2831703]
NPO16501.2	Capsicum annuum	Under-species	n.a.	n.a.	n.a.	n.a.		Database[FooDB]
NPO16501.2	Capsicum annuum	Under-species	n.a.	n.a.	n.a.	n.a.		Database[Phenol-Explorer]

☑ 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	19

Activity Type	# Activity
Organism	19

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	1000.0	ug.mL-1	PMID[523147]
NPT4127	Organism	Pseudomonas stutzeri	Pseudomonas stutzeri	MIC	>	1000.0	ug.mL-1	PMID[523147]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	1000.0	ug.mL-1	PMID[523147]
NPT4128	Organism	Lactobacillus fermentum	Lactobacillus fermentum	MIC	=	1000.0	ug.mL-1	PMID[523147]
NPT4129	Organism	Lactobacillus casei	Lactobacillus casei	MIC	=	1000.0	ug.mL-1	PMID[523147]
NPT1825	Organism	Lactobacillus plantarum	Lactobacillus plantarum	MIC	=	1000.0	ug.mL-1	PMID[523147]
NPT4130	Organism	Lactobacillus rhamnosus	Lactobacillus rhamnosus	MIC	=	1000.0	ug.mL-1	PMID[523147]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	1000.0	ug.mL-1	PMID[523147]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	1000.0	ug.mL-1	PMID[523147]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	1000.0	ug.mL-1	PMID[523147]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	MIC	>	1000.0	ug.mL-1	PMID[523147]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	1000.0	ug.mL-1	PMID[523147]
NPT4131	Organism	Bacillus licheniformis DSM 13=ATCC 14580	Bacillus licheniformis DSM 13=ATCC 14580	MIC	>	1000.0	ug.mL-1	PMID[523147]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	1000.0	ug.mL-1	PMID[523147]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	MIC	=	1000.0	ug.mL-1	PMID[523147]
NPT923	Organism	Rhizopus oryzae	Rhizopus oryzae	MIC	=	1000.0	ug.mL-1	PMID[523147]
NPT4132	Organism	Setophoma terrestris	Setophoma terrestris	MIC	=	1000.0	ug.mL-1	PMID[523147]
NPT3086	Organism	Penicillium expansum	Penicillium expansum	MIC	=	1000.0	ug.mL-1	PMID[523147]

☑ 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 NPC125142 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	231
0.1-0.2	2396
0.2-0.3	7798
0.3-0.4	15889
0.4-0.5	10244
0.5-0.6	3857
0.6-0.7	1648
0.7-0.8	622
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8415	Intermediate Similarity	NPC229655
0.8242	Intermediate Similarity	NPC110072
0.8235	Intermediate Similarity	NPC163362
0.8235	Intermediate Similarity	NPC127295
0.8111	Intermediate Similarity	NPC248312
0.8022	Intermediate Similarity	NPC285588
0.798	Intermediate Similarity	NPC315070
0.7938	Intermediate Similarity	NPC154132
0.7938	Intermediate Similarity	NPC475655
0.7938	Intermediate Similarity	NPC2313
0.7938	Intermediate Similarity	NPC471637
0.7938	Intermediate Similarity	NPC57586
0.7938	Intermediate Similarity	NPC475157
0.7841	Intermediate Similarity	NPC20072
0.7805	Intermediate Similarity	NPC474078
0.7766	Intermediate Similarity	NPC280390
0.7667	Intermediate Similarity	NPC266718
0.7667	Intermediate Similarity	NPC475035
0.7619	Intermediate Similarity	NPC132938
0.7619	Intermediate Similarity	NPC55652
0.7609	Intermediate Similarity	NPC118077
0.7609	Intermediate Similarity	NPC475037
0.7609	Intermediate Similarity	NPC475186
0.76	Intermediate Similarity	NPC197736
0.7579	Intermediate Similarity	NPC320089
0.7579	Intermediate Similarity	NPC320552
0.7553	Intermediate Similarity	NPC327253
0.7549	Intermediate Similarity	NPC281939
0.7529	Intermediate Similarity	NPC472174
0.7529	Intermediate Similarity	NPC472173
0.7524	Intermediate Similarity	NPC476305
0.75	Intermediate Similarity	NPC294293
0.75	Intermediate Similarity	NPC44682
0.75	Intermediate Similarity	NPC163409
0.7453	Intermediate Similarity	NPC469347
0.7453	Intermediate Similarity	NPC469348
0.7447	Intermediate Similarity	NPC104129
0.7447	Intermediate Similarity	NPC477748
0.7447	Intermediate Similarity	NPC249408
0.7429	Intermediate Similarity	NPC297945
0.7429	Intermediate Similarity	NPC157474
0.7429	Intermediate Similarity	NPC126897
0.7429	Intermediate Similarity	NPC110494
0.7423	Intermediate Similarity	NPC469543
0.7416	Intermediate Similarity	NPC100697
0.7407	Intermediate Similarity	NPC20979
0.7396	Intermediate Similarity	NPC474792
0.7396	Intermediate Similarity	NPC67398
0.7396	Intermediate Similarity	NPC91654
0.7391	Intermediate Similarity	NPC475034
0.7391	Intermediate Similarity	NPC470658
0.7374	Intermediate Similarity	NPC40182
0.7374	Intermediate Similarity	NPC198422
0.7368	Intermediate Similarity	NPC202886
0.7353	Intermediate Similarity	NPC110656
0.7353	Intermediate Similarity	NPC203354
0.7353	Intermediate Similarity	NPC473127
0.7333	Intermediate Similarity	NPC469469
0.732	Intermediate Similarity	NPC159698
0.732	Intermediate Similarity	NPC477348
0.732	Intermediate Similarity	NPC477345
0.732	Intermediate Similarity	NPC238264
0.7308	Intermediate Similarity	NPC6931
0.7308	Intermediate Similarity	NPC159005
0.7292	Intermediate Similarity	NPC477349
0.7292	Intermediate Similarity	NPC477749
0.7284	Intermediate Similarity	NPC31496
0.7284	Intermediate Similarity	NPC6848
0.7282	Intermediate Similarity	NPC173859
0.7282	Intermediate Similarity	NPC470512
0.7263	Intermediate Similarity	NPC309310
0.7255	Intermediate Similarity	NPC473124
0.7255	Intermediate Similarity	NPC123796
0.7255	Intermediate Similarity	NPC473123
0.7253	Intermediate Similarity	NPC251026
0.7238	Intermediate Similarity	NPC180459
0.7238	Intermediate Similarity	NPC285253
0.7238	Intermediate Similarity	NPC302057
0.7238	Intermediate Similarity	NPC221110
0.7238	Intermediate Similarity	NPC195116
0.7228	Intermediate Similarity	NPC285231
0.7228	Intermediate Similarity	NPC21568
0.7216	Intermediate Similarity	NPC472196
0.7216	Intermediate Similarity	NPC472195
0.7216	Intermediate Similarity	NPC238090
0.7212	Intermediate Similarity	NPC33053
0.7212	Intermediate Similarity	NPC208650
0.7212	Intermediate Similarity	NPC63368
0.7212	Intermediate Similarity	NPC14946
0.7207	Intermediate Similarity	NPC135369
0.7204	Intermediate Similarity	NPC73166
0.7204	Intermediate Similarity	NPC470124
0.7196	Intermediate Similarity	NPC42171
0.7196	Intermediate Similarity	NPC472716
0.7195	Intermediate Similarity	NPC147292
0.7188	Intermediate Similarity	NPC118078
0.7184	Intermediate Similarity	NPC148603
0.7182	Intermediate Similarity	NPC10366
0.7174	Intermediate Similarity	NPC142111
0.7174	Intermediate Similarity	NPC473315
0.7172	Intermediate Similarity	NPC475375
0.7172	Intermediate Similarity	NPC475164
0.7172	Intermediate Similarity	NPC475241
0.7172	Intermediate Similarity	NPC473605
0.7172	Intermediate Similarity	NPC473765
0.7172	Intermediate Similarity	NPC475525
0.7172	Intermediate Similarity	NPC475593
0.7172	Intermediate Similarity	NPC476066
0.7172	Intermediate Similarity	NPC475540
0.7157	Intermediate Similarity	NPC76497
0.7157	Intermediate Similarity	NPC30289
0.7157	Intermediate Similarity	NPC256133
0.7157	Intermediate Similarity	NPC213674
0.7156	Intermediate Similarity	NPC477030
0.7156	Intermediate Similarity	NPC477029
0.7143	Intermediate Similarity	NPC180183
0.7143	Intermediate Similarity	NPC246124
0.7143	Intermediate Similarity	NPC126147
0.7143	Intermediate Similarity	NPC38376
0.7143	Intermediate Similarity	NPC80210
0.713	Intermediate Similarity	NPC307642
0.7129	Intermediate Similarity	NPC64348
0.7117	Intermediate Similarity	NPC470517
0.7117	Intermediate Similarity	NPC470915
0.7117	Intermediate Similarity	NPC470911
0.7115	Intermediate Similarity	NPC69737
0.7115	Intermediate Similarity	NPC208477
0.7115	Intermediate Similarity	NPC152584
0.7115	Intermediate Similarity	NPC138057
0.7115	Intermediate Similarity	NPC309448
0.7115	Intermediate Similarity	NPC208594
0.7115	Intermediate Similarity	NPC194842
0.7115	Intermediate Similarity	NPC127801
0.7115	Intermediate Similarity	NPC269627
0.7115	Intermediate Similarity	NPC160816
0.7113	Intermediate Similarity	NPC302584
0.7103	Intermediate Similarity	NPC473021
0.7103	Intermediate Similarity	NPC472715
0.7103	Intermediate Similarity	NPC472987
0.71	Intermediate Similarity	NPC240372
0.71	Intermediate Similarity	NPC96597
0.71	Intermediate Similarity	NPC91197
0.71	Intermediate Similarity	NPC475332
0.71	Intermediate Similarity	NPC125551
0.71	Intermediate Similarity	NPC155319
0.71	Intermediate Similarity	NPC239547
0.71	Intermediate Similarity	NPC309503
0.7097	Intermediate Similarity	NPC220167
0.7097	Intermediate Similarity	NPC473308
0.7097	Intermediate Similarity	NPC136699
0.7091	Intermediate Similarity	NPC100048
0.7091	Intermediate Similarity	NPC476690
0.7087	Intermediate Similarity	NPC162354
0.7079	Intermediate Similarity	NPC110813
0.7075	Intermediate Similarity	NPC250089
0.7075	Intermediate Similarity	NPC157530
0.7075	Intermediate Similarity	NPC14630
0.7073	Intermediate Similarity	NPC13143
0.7073	Intermediate Similarity	NPC294813
0.7071	Intermediate Similarity	NPC170204
0.7065	Intermediate Similarity	NPC477390
0.7065	Intermediate Similarity	NPC477385
0.7064	Intermediate Similarity	NPC11548
0.7059	Intermediate Similarity	NPC263756
0.7059	Intermediate Similarity	NPC117714
0.7059	Intermediate Similarity	NPC280991
0.7048	Intermediate Similarity	NPC231340
0.7048	Intermediate Similarity	NPC94272
0.7048	Intermediate Similarity	NPC181467
0.7048	Intermediate Similarity	NPC78034
0.7048	Intermediate Similarity	NPC190395
0.7048	Intermediate Similarity	NPC257964
0.7043	Intermediate Similarity	NPC297950
0.7041	Intermediate Similarity	NPC61201
0.703	Intermediate Similarity	NPC307517
0.703	Intermediate Similarity	NPC61630
0.703	Intermediate Similarity	NPC81483
0.703	Intermediate Similarity	NPC169468
0.703	Intermediate Similarity	NPC312325
0.7027	Intermediate Similarity	NPC470515
0.7021	Intermediate Similarity	NPC477747
0.7021	Intermediate Similarity	NPC477746
0.7019	Intermediate Similarity	NPC471434
0.7019	Intermediate Similarity	NPC470519
0.7019	Intermediate Similarity	NPC473734
0.7019	Intermediate Similarity	NPC231271
0.7019	Intermediate Similarity	NPC471435
0.7019	Intermediate Similarity	NPC230948
0.7019	Intermediate Similarity	NPC93352
0.701	Intermediate Similarity	NPC6414
0.701	Intermediate Similarity	NPC303451
0.7009	Intermediate Similarity	NPC222202
0.7009	Intermediate Similarity	NPC23808
0.7009	Intermediate Similarity	NPC170974
0.7009	Intermediate Similarity	NPC191439
0.7009	Intermediate Similarity	NPC269297
0.7009	Intermediate Similarity	NPC472717
0.7009	Intermediate Similarity	NPC87998
0.7009	Intermediate Similarity	NPC477811
0.7009	Intermediate Similarity	NPC224314

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 NPC125142 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	2490
0.2-0.3	4283
0.3-0.4	1641
0.4-0.5	421
0.5-0.6	91
0.6-0.7	15
0.7-0.8	13
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
0.7429	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD8516	Approved
0.6991	Remote Similarity	NPD8517	Approved
0.6991	Remote Similarity	NPD8515	Approved
0.6914	Remote Similarity	NPD6123	Approved
0.6863	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8513	Phase 3
0.6754	Remote Similarity	NPD8377	Approved
0.6754	Remote Similarity	NPD8294	Approved
0.6696	Remote Similarity	NPD8378	Approved
0.6696	Remote Similarity	NPD8380	Approved
0.6696	Remote Similarity	NPD8379	Approved
0.6696	Remote Similarity	NPD8335	Approved
0.6696	Remote Similarity	NPD8296	Approved
0.6552	Remote Similarity	NPD8033	Approved
0.6518	Remote Similarity	NPD8133	Approved
0.6514	Remote Similarity	NPD6686	Approved
0.65	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7503	Approved
0.6337	Remote Similarity	NPD6698	Approved
0.6337	Remote Similarity	NPD46	Approved
0.6337	Remote Similarity	NPD7838	Discovery
0.6293	Remote Similarity	NPD7328	Approved
0.6293	Remote Similarity	NPD7327	Approved
0.6283	Remote Similarity	NPD6429	Approved
0.6283	Remote Similarity	NPD6430	Approved
0.6239	Remote Similarity	NPD7516	Approved
0.6173	Remote Similarity	NPD7346	Approved
0.6049	Remote Similarity	NPD888	Phase 3
0.6049	Remote Similarity	NPD892	Phase 3
0.6049	Remote Similarity	NPD890	Clinical (unspecified phase)
0.6049	Remote Similarity	NPD891	Phase 3
0.6049	Remote Similarity	NPD893	Approved
0.6016	Remote Similarity	NPD8448	Approved
0.6	Remote Similarity	NPD8391	Approved
0.6	Remote Similarity	NPD8390	Approved
0.6	Remote Similarity	NPD8392	Approved
0.5982	Remote Similarity	NPD6412	Phase 2
0.5962	Remote Similarity	NPD7983	Approved
0.5935	Remote Similarity	NPD8451	Approved
0.5935	Remote Similarity	NPD7507	Approved
0.5926	Remote Similarity	NPD2269	Approved
0.5902	Remote Similarity	NPD7829	Approved
0.5902	Remote Similarity	NPD8328	Phase 3
0.5902	Remote Similarity	NPD7830	Approved
0.59	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD8074	Phase 3
0.5877	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD7329	Approved
0.5868	Remote Similarity	NPD8444	Approved
0.5818	Remote Similarity	NPD5344	Discontinued
0.5802	Remote Similarity	NPD904	Phase 3
0.5802	Remote Similarity	NPD905	Approved
0.5794	Remote Similarity	NPD7319	Approved
0.5736	Remote Similarity	NPD8450	Suspended
0.5726	Remote Similarity	NPD8340	Approved
0.5726	Remote Similarity	NPD8342	Approved
0.5726	Remote Similarity	NPD8341	Approved
0.5726	Remote Similarity	NPD8299	Approved
0.5667	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5663	Remote Similarity	NPD895	Approved
0.5663	Remote Similarity	NPD889	Approved
0.5663	Remote Similarity	NPD894	Approved
0.5663	Remote Similarity	NPD887	Approved
0.5659	Remote Similarity	NPD8449	Approved
0.5607	Remote Similarity	NPD8171	Discontinued

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