NPASS Compound

Structure

NPC45346 OpenBabel07101718282D 87 94 0 0 1 0 0 0 0 0999 V2000 -5.0879 8.8125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7839 8.8125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9359 1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 5.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3278 -3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1855 3.7855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2064 3.7855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8815 -2.8063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9023 -2.8063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 6.8542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9359 7.3437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 5.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 1.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6960 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -0.4896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8480 -1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 4.4062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 2.4479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7862 -2.5615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9359 8.3229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0879 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 5.3854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4798 -2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2399 -3.4271 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3879 -1.6670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5439 -1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6960 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2399 -1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3919 3.9167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2399 -4.4062 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 10.8775 -0.8190 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0879 -4.8958 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2223 -0.0913 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9359 -4.4062 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6318 -0.4896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6318 -1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7839 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7839 -1.9583 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8480 -0.4896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6960 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5439 2.4479 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5439 1.4687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7839 0.9792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 1.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3278 -0.4896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9359 -3.4271 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9359 -1.4687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6960 2.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -1.9583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5439 -0.4896 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8480 -0.4896 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6960 0.9792 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5439 -3.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7600 -2.6638 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 -0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6318 -3.4271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 4.4062 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3919 -4.8958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8513 -0.7166 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 -5.8750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4259 0.8664 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7839 -4.8958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8480 -1.4688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 -0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6318 1.4688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9359 1.4688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2399 2.4479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4798 -1.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 -2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4302 -1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 -1.9583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4798 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9359 -0.4896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7839 -2.9375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3919 0.9792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 28 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 31 1 0 0 0 0 7 58 1 0 0 0 0 8 58 1 0 0 0 0 9 59 1 0 0 0 0 10 59 1 0 0 0 0 12 61 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 28 2 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 32 2 0 0 0 0 18 37 1 0 0 0 0 19 22 1 0 0 0 0 19 36 1 0 0 0 0 20 21 1 0 0 0 0 20 38 1 0 0 0 0 21 60 1 0 0 0 0 22 61 1 0 0 0 0 23 30 2 0 0 0 0 23 39 1 0 0 0 0 24 33 1 0 0 0 0 24 58 1 0 0 0 0 25 64 1 0 0 0 0 26 65 1 0 0 0 0 27 66 1 0 0 0 0 29 54 1 0 0 0 0 31 67 2 0 0 0 0 31 79 1 0 0 0 0 32 33 1 0 0 0 0 32 62 1 0 0 0 0 33 63 1 1 0 0 0 34 25 1 1 0 0 0 34 40 1 0 0 0 0 34 80 1 0 0 0 0 35 26 1 6 0 0 0 35 41 1 0 0 0 0 35 81 1 0 0 0 0 36 59 1 0 0 0 0 36 60 1 6 0 0 0 37 60 1 6 0 0 0 37 61 1 0 0 0 0 38 59 1 0 0 0 0 38 82 1 6 0 0 0 39 68 2 0 0 0 0 39 83 1 0 0 0 0 40 42 1 0 0 0 0 40 69 1 6 0 0 0 41 43 1 0 0 0 0 41 70 1 1 0 0 0 42 44 1 0 0 0 0 42 71 1 1 0 0 0 43 55 1 0 0 0 0 43 72 1 6 0 0 0 44 56 1 0 0 0 0 44 73 1 6 0 0 0 45 46 1 0 0 0 0 45 47 1 0 0 0 0 45 84 1 1 0 0 0 46 48 1 0 0 0 0 46 79 1 6 0 0 0 47 53 1 6 0 0 0 47 85 1 0 0 0 0 48 57 1 0 0 0 0 48 86 1 1 0 0 0 49 50 1 0 0 0 0 49 62 1 1 0 0 0 49 74 1 0 0 0 0 50 63 1 1 0 0 0 50 75 1 0 0 0 0 51 52 1 0 0 0 0 51 58 1 0 0 0 0 51 83 1 6 0 0 0 52 63 1 1 0 0 0 52 87 1 0 0 0 0 53 76 2 0 0 0 0 53 77 1 0 0 0 0 54 78 2 0 0 0 0 54 87 1 0 0 0 0 55 81 1 0 0 0 0 55 84 1 1 0 0 0 56 80 1 0 0 0 0 56 86 1 1 0 0 0 57 82 1 6 0 0 0 57 85 1 0 0 0 0 60 11 1 6 0 0 0 61 62 1 1 0 0 0 62 13 1 1 0 0 0 63 27 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1238.64
Volume:	1222.262
LogP:	4.168
LogD:	1.997
LogS:	-3.662
# Rotatable Bonds:	21
TPSA:	373.88
# H-Bond Aceptor:	24
# H-Bond Donor:	11
# Rings:	8
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.031
Synthetic Accessibility Score:	7.245
Fsp3:	0.841
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:	-5.836
MDCK Permeability:	0.0003402413858566433
Pgp-inhibitor:	0.971
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.985
20% Bioavailability (F20%):	0.037
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	79.92866516113281%
Volume Distribution (VD):	0.405
Pgp-substrate:	7.611428260803223%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.087
CYP3A4-substrate:	0.025

ADMET: Excretion

Clearance (CL):	0.735
Half-life (T1/2):	0.745

ADMET: Toxicity

hERG Blockers:	0.172
Human Hepatotoxicity (H-HT):	0.689
Drug-inuced Liver Injury (DILI):	0.811
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.13
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC45346

Natural Product ID:	NPC45346
*Common Name:**	Symplocososide M
IUPAC Name:	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-10-[(2E)-3,7-dimethylocta-2,6-dienoyl]oxy-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-(2-methylpropanoyloxy)-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-acetyloxy-3-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms:	symplocososide M
Standard InCHIKey:	XPBNJNXKQVWGAY-SUCVEKIBSA-N
Standard InCHI:	InChI=1S/C63H98O24/c1-28(2)15-14-16-30(5)23-39(68)83-51-52(87-54(78)29(3)4)63(27-66)33(24-58(51,7)8)32-17-18-37-60(11)21-20-38(59(9,10)36(60)19-22-61(37,12)62(32,13)49(74)50(63)75)82-57-48(86-56-44(73)42(71)40(69)34(25-64)80-56)46(79-31(6)67)45(47(85-57)53(76)77)84-55-43(72)41(70)35(26-65)81-55/h15,17,23,29,33-38,40-52,55-57,64-66,69-75H,14,16,18-22,24-27H2,1-13H3,(H,76,77)/b30-23+/t33-,34+,35-,36-,37+,38-,40+,41-,42-,43+,44+,45-,46-,47-,48+,49-,50+,51-,52-,55-,56-,57+,60-,61+,62-,63-/m0/s1
SMILES:	CC(=CCC/C(=C/C(=O)O[C@H]1[C@@H]([C@@]2(CO)[C@@H](CC1(C)C)C1=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)[C@H]([C@H]2O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O1)O[C@H]1[C@@H]([C@H]([C@H](CO)O1)O)O)OC(=O)C)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)OC(=O)C(C)C)/C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL497707
PubChem CID:	16099385
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

*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
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	n.a.	n.a.	PMID[15620235]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	roots	Nanning City, Guangxi Province, People's Republic of China	1997-Jan	PMID[17190442]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8121	Symplocos chinensis	Species	Symplocaceae	Eukaryota	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	2700.0	nM	PMID[558992]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	3800.0	nM	PMID[558992]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[558992]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[558992]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	2300.0	nM	PMID[558992]

☑ 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 NPC45346 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	306
0.1-0.2	1751
0.2-0.3	4821
0.3-0.4	8400
0.4-0.5	11533
0.5-0.6	8081
0.6-0.7	4652
0.7-0.8	1968
0.8-0.85	710
0.85-0.9	288
0.9-0.95	114
0.95-1	73

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476074
1.0	High Similarity	NPC134914
1.0	High Similarity	NPC264566
1.0	High Similarity	NPC172374
1.0	High Similarity	NPC262796
1.0	High Similarity	NPC475377
1.0	High Similarity	NPC329993
1.0	High Similarity	NPC478065
1.0	High Similarity	NPC475167
1.0	High Similarity	NPC173435
1.0	High Similarity	NPC301639
1.0	High Similarity	NPC478064
0.9917	High Similarity	NPC478152
0.9917	High Similarity	NPC478153
0.9917	High Similarity	NPC478150
0.9835	High Similarity	NPC478151
0.9833	High Similarity	NPC25998
0.9833	High Similarity	NPC478155
0.9832	High Similarity	NPC475281
0.9832	High Similarity	NPC329923
0.9832	High Similarity	NPC477078
0.9832	High Similarity	NPC477075
0.9752	High Similarity	NPC478154
0.975	High Similarity	NPC470913
0.975	High Similarity	NPC477077
0.975	High Similarity	NPC470912
0.975	High Similarity	NPC477079
0.975	High Similarity	NPC477076
0.9669	High Similarity	NPC477197
0.9667	High Similarity	NPC477193
0.9667	High Similarity	NPC477194
0.9667	High Similarity	NPC477192
0.9667	High Similarity	NPC477191
0.959	High Similarity	NPC46823
0.959	High Similarity	NPC178264
0.959	High Similarity	NPC277212
0.959	High Similarity	NPC30279
0.959	High Similarity	NPC192765
0.959	High Similarity	NPC473918
0.959	High Similarity	NPC71391
0.9587	High Similarity	NPC107536
0.9587	High Similarity	NPC115656
0.9587	High Similarity	NPC97918
0.9587	High Similarity	NPC141600
0.9587	High Similarity	NPC11577
0.9587	High Similarity	NPC305793
0.9587	High Similarity	NPC269484
0.9587	High Similarity	NPC280029
0.9587	High Similarity	NPC252289
0.9587	High Similarity	NPC244296
0.9587	High Similarity	NPC477196
0.9587	High Similarity	NPC472267
0.9587	High Similarity	NPC1314
0.9587	High Similarity	NPC82380
0.9587	High Similarity	NPC252657
0.9587	High Similarity	NPC273878
0.9587	High Similarity	NPC88311
0.9587	High Similarity	NPC470518
0.9587	High Similarity	NPC9470
0.9512	High Similarity	NPC225791
0.9508	High Similarity	NPC476780
0.9508	High Similarity	NPC476774
0.9508	High Similarity	NPC476775
0.9508	High Similarity	NPC271610
0.9496	High Similarity	NPC478066
0.9431	High Similarity	NPC312650
0.9431	High Similarity	NPC476776
0.9431	High Similarity	NPC477195
0.9426	High Similarity	NPC47995
0.9426	High Similarity	NPC265841
0.9339	High Similarity	NPC285091
0.928	High Similarity	NPC476778
0.928	High Similarity	NPC476777
0.9256	High Similarity	NPC470477
0.925	High Similarity	NPC235438
0.925	High Similarity	NPC107966
0.925	High Similarity	NPC249848
0.925	High Similarity	NPC40775
0.9213	High Similarity	NPC596
0.9206	High Similarity	NPC110700
0.9206	High Similarity	NPC262813
0.9206	High Similarity	NPC279915
0.92	High Similarity	NPC476779
0.9187	High Similarity	NPC470475
0.9174	High Similarity	NPC30735
0.9174	High Similarity	NPC202666
0.9174	High Similarity	NPC471961
0.9174	High Similarity	NPC14617
0.9174	High Similarity	NPC471964
0.9174	High Similarity	NPC235405
0.9174	High Similarity	NPC281148
0.9174	High Similarity	NPC262199
0.9134	High Similarity	NPC141215
0.9134	High Similarity	NPC251998
0.9134	High Similarity	NPC190065
0.9134	High Similarity	NPC471089
0.9106	High Similarity	NPC470780
0.9098	High Similarity	NPC471962
0.9098	High Similarity	NPC471963
0.9098	High Similarity	NPC247315
0.9098	High Similarity	NPC23275
0.9091	High Similarity	NPC213952
0.9091	High Similarity	NPC471965
0.9083	High Similarity	NPC236657
0.9083	High Similarity	NPC118440
0.9062	High Similarity	NPC140045
0.9062	High Similarity	NPC295885
0.9032	High Similarity	NPC470476
0.9024	High Similarity	NPC470218
0.9016	High Similarity	NPC257211
0.9008	High Similarity	NPC302887
0.9008	High Similarity	NPC301449
0.9008	High Similarity	NPC86222
0.9008	High Similarity	NPC222580
0.9008	High Similarity	NPC114484
0.9008	High Similarity	NPC171544
0.9008	High Similarity	NPC223301
0.9008	High Similarity	NPC62725
0.9008	High Similarity	NPC104372
0.9008	High Similarity	NPC187618
0.9008	High Similarity	NPC22956
0.9008	High Similarity	NPC159309
0.9008	High Similarity	NPC297263
0.9008	High Similarity	NPC31838
0.9008	High Similarity	NPC64715
0.9008	High Similarity	NPC11242
0.9008	High Similarity	NPC75417
0.9	High Similarity	NPC214484
0.9	High Similarity	NPC6377
0.9	High Similarity	NPC309780
0.9	High Similarity	NPC180550
0.9	High Similarity	NPC39211
0.9	High Similarity	NPC208381
0.9	High Similarity	NPC472949
0.9	High Similarity	NPC114441
0.9	High Similarity	NPC11551
0.9	High Similarity	NPC473884
0.9	High Similarity	NPC470914
0.9	High Similarity	NPC475171
0.9	High Similarity	NPC35405
0.9	High Similarity	NPC157868
0.9	High Similarity	NPC469945
0.8992	High Similarity	NPC224121
0.8952	High Similarity	NPC470516
0.8943	High Similarity	NPC33068
0.8934	High Similarity	NPC131469
0.8934	High Similarity	NPC313110
0.8934	High Similarity	NPC4749
0.8934	High Similarity	NPC475591
0.8934	High Similarity	NPC162574
0.8934	High Similarity	NPC236870
0.8934	High Similarity	NPC10607
0.8934	High Similarity	NPC21691
0.8934	High Similarity	NPC80986
0.8934	High Similarity	NPC187290
0.8917	High Similarity	NPC286347
0.8889	High Similarity	NPC311178
0.8889	High Similarity	NPC43589
0.8889	High Similarity	NPC300655
0.8889	High Similarity	NPC222951
0.8871	High Similarity	NPC469947
0.8871	High Similarity	NPC181066
0.8871	High Similarity	NPC284449
0.8862	High Similarity	NPC2370
0.8862	High Similarity	NPC44716
0.8862	High Similarity	NPC283417
0.8862	High Similarity	NPC302543
0.8862	High Similarity	NPC200049
0.8862	High Similarity	NPC258617
0.8852	High Similarity	NPC31193
0.8852	High Similarity	NPC242840
0.8843	High Similarity	NPC192791
0.8843	High Similarity	NPC122971
0.8833	High Similarity	NPC473405
0.8819	High Similarity	NPC475444
0.8819	High Similarity	NPC196874
0.8819	High Similarity	NPC473679
0.8819	High Similarity	NPC319719
0.8819	High Similarity	NPC475177
0.8819	High Similarity	NPC233223
0.8819	High Similarity	NPC183816
0.8819	High Similarity	NPC322904
0.8819	High Similarity	NPC324933
0.879	High Similarity	NPC470922
0.879	High Similarity	NPC160452
0.877	High Similarity	NPC473645
0.877	High Similarity	NPC294112
0.877	High Similarity	NPC107338
0.877	High Similarity	NPC109607
0.876	High Similarity	NPC471548
0.876	High Similarity	NPC105800
0.876	High Similarity	NPC232237
0.873	High Similarity	NPC220838
0.873	High Similarity	NPC45606
0.872	High Similarity	NPC475368
0.871	High Similarity	NPC67251
0.8699	High Similarity	NPC476204
0.8699	High Similarity	NPC170084
0.8689	High Similarity	NPC475775
0.8689	High Similarity	NPC207738

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 NPC45346 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	1925
0.2-0.3	3871
0.3-0.4	2006
0.4-0.5	613
0.5-0.6	286
0.6-0.7	138
0.7-0.8	28
0.8-0.85	15
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9174	High Similarity	NPD8328	Phase 3
0.8833	High Similarity	NPD8295	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD8517	Approved
0.811	Intermediate Similarity	NPD8513	Phase 3
0.811	Intermediate Similarity	NPD8515	Approved
0.811	Intermediate Similarity	NPD8516	Approved
0.8092	Intermediate Similarity	NPD7319	Approved
0.8015	Intermediate Similarity	NPD7736	Approved
0.8	Intermediate Similarity	NPD7507	Approved
0.7969	Intermediate Similarity	NPD8033	Approved
0.7891	Intermediate Similarity	NPD8377	Approved
0.7891	Intermediate Similarity	NPD8294	Approved
0.7869	Intermediate Similarity	NPD6686	Approved
0.784	Intermediate Similarity	NPD8133	Approved
0.7829	Intermediate Similarity	NPD8296	Approved
0.7829	Intermediate Similarity	NPD8335	Approved
0.7829	Intermediate Similarity	NPD8378	Approved
0.7829	Intermediate Similarity	NPD8380	Approved
0.7829	Intermediate Similarity	NPD8379	Approved
0.7805	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD8293	Discontinued
0.7674	Intermediate Similarity	NPD7516	Approved
0.7634	Intermediate Similarity	NPD6370	Approved
0.7597	Intermediate Similarity	NPD7327	Approved
0.7597	Intermediate Similarity	NPD7328	Approved
0.7519	Intermediate Similarity	NPD7492	Approved
0.7481	Intermediate Similarity	NPD6054	Approved
0.7481	Intermediate Similarity	NPD6059	Approved
0.7463	Intermediate Similarity	NPD6616	Approved
0.744	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD7503	Approved
0.7407	Intermediate Similarity	NPD7078	Approved
0.7402	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6412	Phase 2
0.7355	Intermediate Similarity	NPD4225	Approved
0.7348	Intermediate Similarity	NPD6319	Approved
0.7293	Intermediate Similarity	NPD6015	Approved
0.7293	Intermediate Similarity	NPD6016	Approved
0.7279	Intermediate Similarity	NPD8074	Phase 3
0.7252	Intermediate Similarity	NPD7115	Discovery
0.7239	Intermediate Similarity	NPD5988	Approved
0.7213	Intermediate Similarity	NPD7638	Approved
0.7209	Intermediate Similarity	NPD6882	Approved
0.7209	Intermediate Similarity	NPD8297	Approved
0.7154	Intermediate Similarity	NPD7640	Approved
0.7154	Intermediate Similarity	NPD7639	Approved
0.7131	Intermediate Similarity	NPD7902	Approved
0.7121	Intermediate Similarity	NPD6009	Approved
0.7109	Intermediate Similarity	NPD6372	Approved
0.7109	Intermediate Similarity	NPD6373	Approved
0.7109	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7748	Approved
0.7008	Intermediate Similarity	NPD5739	Approved
0.7008	Intermediate Similarity	NPD6402	Approved
0.7008	Intermediate Similarity	NPD6675	Approved
0.7008	Intermediate Similarity	NPD7128	Approved
0.7	Intermediate Similarity	NPD6650	Approved
0.7	Intermediate Similarity	NPD6649	Approved
0.6978	Remote Similarity	NPD6033	Approved
0.6912	Remote Similarity	NPD6921	Approved
0.6899	Remote Similarity	NPD6881	Approved
0.6899	Remote Similarity	NPD7320	Approved
0.6899	Remote Similarity	NPD6899	Approved
0.6894	Remote Similarity	NPD4632	Approved
0.6885	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7900	Approved
0.687	Remote Similarity	NPD8130	Phase 1
0.686	Remote Similarity	NPD7515	Phase 2
0.6822	Remote Similarity	NPD5701	Approved
0.6822	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5697	Approved
0.6822	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD7102	Approved
0.6794	Remote Similarity	NPD6883	Approved
0.6794	Remote Similarity	NPD7290	Approved
0.6742	Remote Similarity	NPD6847	Approved
0.6742	Remote Similarity	NPD6617	Approved
0.6742	Remote Similarity	NPD6869	Approved
0.6727	Remote Similarity	NPD7799	Discontinued
0.6718	Remote Similarity	NPD6012	Approved
0.6718	Remote Similarity	NPD6014	Approved
0.6718	Remote Similarity	NPD6013	Approved
0.6712	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD5983	Phase 2
0.6641	Remote Similarity	NPD7632	Discontinued
0.6641	Remote Similarity	NPD6011	Approved
0.6639	Remote Similarity	NPD46	Approved
0.6639	Remote Similarity	NPD6698	Approved
0.6617	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6008	Approved
0.6597	Remote Similarity	NPD7260	Phase 2
0.6596	Remote Similarity	NPD6336	Discontinued
0.6571	Remote Similarity	NPD7830	Approved
0.6571	Remote Similarity	NPD7829	Approved
0.6571	Remote Similarity	NPD6067	Discontinued
0.6549	Remote Similarity	NPD8448	Approved
0.6536	Remote Similarity	NPD7625	Phase 1
0.6531	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8080	Discontinued
0.6479	Remote Similarity	NPD8451	Approved
0.6463	Remote Similarity	NPD8415	Approved
0.6457	Remote Similarity	NPD6083	Phase 2
0.6457	Remote Similarity	NPD6084	Phase 2
0.6457	Remote Similarity	NPD4755	Approved
0.6453	Remote Similarity	NPD8407	Phase 2
0.6452	Remote Similarity	NPD8035	Phase 2
0.6452	Remote Similarity	NPD8034	Phase 2
0.6452	Remote Similarity	NPD6411	Approved
0.6452	Remote Similarity	NPD7983	Approved
0.6444	Remote Similarity	NPD6053	Discontinued
0.6438	Remote Similarity	NPD6845	Suspended
0.6434	Remote Similarity	NPD5344	Discontinued
0.6423	Remote Similarity	NPD6274	Approved
0.6418	Remote Similarity	NPD6371	Approved
0.6414	Remote Similarity	NPD8391	Approved
0.6414	Remote Similarity	NPD8390	Approved
0.6414	Remote Similarity	NPD8392	Approved
0.6403	Remote Similarity	NPD7101	Approved
0.6403	Remote Similarity	NPD7100	Approved
0.64	Remote Similarity	NPD6399	Phase 3
0.64	Remote Similarity	NPD5778	Approved
0.64	Remote Similarity	NPD5779	Approved
0.6385	Remote Similarity	NPD5211	Phase 2
0.6378	Remote Similarity	NPD4697	Phase 3
0.6374	Remote Similarity	NPD8368	Discontinued
0.6357	Remote Similarity	NPD5286	Approved
0.6357	Remote Similarity	NPD5285	Approved
0.6357	Remote Similarity	NPD4700	Approved
0.6357	Remote Similarity	NPD4696	Approved
0.6331	Remote Similarity	NPD6335	Approved
0.6312	Remote Similarity	NPD8444	Approved
0.6312	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD6909	Approved
0.6312	Remote Similarity	NPD6908	Approved
0.6304	Remote Similarity	NPD6868	Approved
0.6301	Remote Similarity	NPD5956	Approved
0.6299	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6294	Remote Similarity	NPD8342	Approved
0.6294	Remote Similarity	NPD8340	Approved
0.6294	Remote Similarity	NPD8299	Approved
0.6294	Remote Similarity	NPD8341	Approved
0.629	Remote Similarity	NPD5328	Approved
0.629	Remote Similarity	NPD6101	Approved
0.629	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD5141	Approved
0.6279	Remote Similarity	NPD5696	Approved
0.627	Remote Similarity	NPD8171	Discontinued
0.626	Remote Similarity	NPD5225	Approved
0.626	Remote Similarity	NPD5224	Approved
0.626	Remote Similarity	NPD4633	Approved
0.626	Remote Similarity	NPD5226	Approved
0.6259	Remote Similarity	NPD6317	Approved
0.625	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5222	Approved
0.6241	Remote Similarity	NPD4767	Approved
0.6241	Remote Similarity	NPD4768	Approved
0.624	Remote Similarity	NPD7838	Discovery
0.6224	Remote Similarity	NPD7642	Approved
0.622	Remote Similarity	NPD5282	Discontinued
0.6214	Remote Similarity	NPD6314	Approved
0.6214	Remote Similarity	NPD6313	Approved
0.6212	Remote Similarity	NPD5175	Approved
0.6212	Remote Similarity	NPD5174	Approved
0.621	Remote Similarity	NPD5737	Approved
0.621	Remote Similarity	NPD6672	Approved
0.6202	Remote Similarity	NPD5173	Approved
0.6199	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6079	Approved
0.6183	Remote Similarity	NPD5223	Approved
0.6179	Remote Similarity	NPD3618	Phase 1
0.6174	Remote Similarity	NPD8450	Suspended
0.6172	Remote Similarity	NPD5695	Phase 3
0.6164	Remote Similarity	NPD8336	Approved
0.6164	Remote Similarity	NPD8337	Approved
0.616	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD4730	Approved
0.6148	Remote Similarity	NPD4729	Approved
0.6145	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD7645	Phase 2
0.6129	Remote Similarity	NPD3573	Approved
0.6124	Remote Similarity	NPD8435	Approved
0.6124	Remote Similarity	NPD7839	Suspended
0.6107	Remote Similarity	NPD6648	Approved
0.6107	Remote Similarity	NPD8449	Approved
0.6107	Remote Similarity	NPD8338	Approved
0.6098	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD1694	Approved
0.609	Remote Similarity	NPD4754	Approved
0.6087	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6081	Remote Similarity	NPD6914	Discontinued
0.608	Remote Similarity	NPD7513	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