NPASS Compound

Structure

NPC106760 OpenBabel07101718242D 47 52 0 0 1 0 0 0 0 0999 V2000 -0.2872 3.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5500 4.5842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4285 -2.2440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3616 -1.9408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 -0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3003 0.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 -1.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5491 0.4906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8791 3.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9357 1.2363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0820 -3.5985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2469 3.6511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9034 2.9220 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8497 1.4717 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4810 -2.7022 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6994 -0.9811 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8497 0.4906 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2782 2.1282 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6325 0.3032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8954 1.4403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6994 1.9623 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4568 -2.5996 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8558 -1.7033 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2791 -0.9096 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3034 -1.0121 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1258 0.6779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6325 -1.2843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8497 0.4906 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6994 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5491 1.4717 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6586 -4.3922 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2379 1.9242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5519 0.7112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1985 2.3734 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0335 -3.3934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8316 -1.6008 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6782 -0.0133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1015 0.7805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9043 -1.9084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7267 -0.2184 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2092 -0.4906 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 5 33 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 34 1 0 0 0 0 12 13 1 0 0 0 0 12 33 1 0 0 0 0 13 36 1 0 0 0 0 14 18 1 0 0 0 0 14 23 1 0 0 0 0 15 24 1 0 0 0 0 15 25 1 0 0 0 0 16 37 1 0 0 0 0 18 17 1 1 0 0 0 18 26 1 0 0 0 0 19 26 1 0 0 0 0 19 33 1 1 0 0 0 20 16 1 6 0 0 0 20 27 1 0 0 0 0 20 45 1 0 0 0 0 21 32 1 0 0 0 0 21 35 1 6 0 0 0 22 34 1 6 0 0 0 22 35 1 0 0 0 0 23 36 1 1 0 0 0 23 38 1 0 0 0 0 24 35 1 1 0 0 0 24 47 1 0 0 0 0 25 39 2 0 0 0 0 25 40 1 0 0 0 0 26 36 1 6 0 0 0 27 28 1 0 0 0 0 27 41 1 1 0 0 0 28 29 1 0 0 0 0 28 42 1 6 0 0 0 29 30 1 0 0 0 0 29 43 1 1 0 0 0 30 45 1 0 0 0 0 30 46 1 6 0 0 0 31 44 2 0 0 0 0 31 46 1 0 0 0 0 32 47 1 0 0 0 0 33 34 1 6 0 0 0 34 6 1 6 0 0 0 35 7 1 6 0 0 0 36 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	664.38
Volume:	668.656
LogP:	2.072
LogD:	2.558
LogS:	-3.278
# Rotatable Bonds:	7
TPSA:	183.21
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.181
Synthetic Accessibility Score:	5.783
Fsp3:	0.889
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.721
MDCK Permeability:	2.8740490961354226e-05
Pgp-inhibitor:	0.603
Pgp-substrate:	0.024
Human Intestinal Absorption (HIA):	0.372
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.817

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	77.54784393310547%
Volume Distribution (VD):	0.385
Pgp-substrate:	13.248038291931152%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.132
CYP2C19-inhibitor:	0.002
CYP2C19-substrate:	0.599
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.094
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.123
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.057

ADMET: Excretion

Clearance (CL):	1.227
Half-life (T1/2):	0.804

ADMET: Toxicity

hERG Blockers:	0.094
Human Hepatotoxicity (H-HT):	0.376
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.143
Maximum Recommended Daily Dose:	0.685
Skin Sensitization:	0.197
Carcinogencity:	0.028
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC106760

Natural Product ID:	NPC106760
*Common Name:**	Acanthosessilioside E
IUPAC Name:	n.a.
Synonyms:	Acanthosessilioside E
Standard InCHIKey:	XSHGWZNYZFCBPO-NLNWDERISA-N
Standard InCHI:	InChI=1S/C36H56O11/c1-17(2)18-14-23(38)36(31(44)46-30-29(43)28(42)27(41)20(16-37)45-30)13-12-33(5)19(26(18)36)8-9-22-34(33,6)11-10-21-32(3,4)47-24(15-25(39)40)35(21,22)7/h18-24,26-30,37-38,41-43H,1,8-16H2,2-7H3,(H,39,40)/t18-,19+,20+,21-,22-,23-,24+,26+,27+,28-,29+,30-,33+,34+,35-,36+/m0/s1
SMILES:	OC[C@H]1O[C@@H](OC(=O)[C@]23CC[C@@]4([C@@H]([C@H]3[C@@H](C[C@@H]2O)C(=C)C)CC[C@H]2[C@@]4(C)CC[C@@H]3[C@]2(C)[C@@H](CC(=O)O)OC3(C)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063160
PubChem CID:	60155055
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
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	Fruits	n.a.	n.a.	PMID[22691179]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO30633	Acanthopanax sessiliflorus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	8

Activity Type	# Activity
Cell Line	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	<	10000.0	nM	PMID[515387]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	<	10000.0	nM	PMID[515387]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	<	10000.0	nM	PMID[515387]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	<	10000.0	nM	PMID[515387]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	<	10000.0	nM	PMID[515387]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	<	10000.0	nM	PMID[515387]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	IC50	<	10000.0	nM	PMID[515387]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[515387]

☑ 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 NPC106760 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	283
0.1-0.2	2059
0.2-0.3	7039
0.3-0.4	13274
0.4-0.5	7390
0.5-0.6	5877
0.6-0.7	3941
0.7-0.8	2412
0.8-0.85	372
0.85-0.9	43
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9802	High Similarity	NPC224414
0.9712	High Similarity	NPC102619
0.9519	High Similarity	NPC272242
0.9307	High Similarity	NPC94919
0.9245	High Similarity	NPC243572
0.8972	High Similarity	NPC11035
0.8952	High Similarity	NPC287269
0.8909	High Similarity	NPC156651
0.8889	High Similarity	NPC470543
0.8868	High Similarity	NPC88744
0.8807	High Similarity	NPC73986
0.8807	High Similarity	NPC146563
0.8785	High Similarity	NPC91583
0.8785	High Similarity	NPC240125
0.8785	High Similarity	NPC51947
0.8785	High Similarity	NPC473844
0.8727	High Similarity	NPC54395
0.8713	High Similarity	NPC215570
0.8704	High Similarity	NPC27551
0.8704	High Similarity	NPC114961
0.8649	High Similarity	NPC137414
0.8649	High Similarity	NPC469820
0.8649	High Similarity	NPC469823
0.8636	High Similarity	NPC477944
0.8624	High Similarity	NPC204392
0.8624	High Similarity	NPC1876
0.8624	High Similarity	NPC275668
0.8624	High Similarity	NPC240734
0.8624	High Similarity	NPC91838
0.8621	High Similarity	NPC273962
0.8611	High Similarity	NPC8431
0.8558	High Similarity	NPC108371
0.8532	High Similarity	NPC101450
0.8522	High Similarity	NPC156789
0.8519	High Similarity	NPC295389
0.8505	High Similarity	NPC63023
0.8505	High Similarity	NPC95243
0.8496	Intermediate Similarity	NPC475632
0.8496	Intermediate Similarity	NPC469822
0.8496	Intermediate Similarity	NPC239293
0.8496	Intermediate Similarity	NPC86020
0.8468	Intermediate Similarity	NPC200944
0.8468	Intermediate Similarity	NPC73455
0.8462	Intermediate Similarity	NPC47113
0.8462	Intermediate Similarity	NPC174367
0.8455	Intermediate Similarity	NPC470311
0.8455	Intermediate Similarity	NPC285410
0.8455	Intermediate Similarity	NPC250481
0.8455	Intermediate Similarity	NPC263827
0.8455	Intermediate Similarity	NPC471251
0.8455	Intermediate Similarity	NPC274833
0.8448	Intermediate Similarity	NPC160084
0.844	Intermediate Similarity	NPC471250
0.8435	Intermediate Similarity	NPC475182
0.8411	Intermediate Similarity	NPC121566
0.8411	Intermediate Similarity	NPC223741
0.8411	Intermediate Similarity	NPC100955
0.8407	Intermediate Similarity	NPC473304
0.8393	Intermediate Similarity	NPC477580
0.8393	Intermediate Similarity	NPC116024
0.8393	Intermediate Similarity	NPC469821
0.8393	Intermediate Similarity	NPC473882
0.839	Intermediate Similarity	NPC146456
0.839	Intermediate Similarity	NPC469757
0.839	Intermediate Similarity	NPC471357
0.839	Intermediate Similarity	NPC117702
0.8378	Intermediate Similarity	NPC207845
0.8378	Intermediate Similarity	NPC472719
0.8376	Intermediate Similarity	NPC473474
0.8365	Intermediate Similarity	NPC253586
0.8364	Intermediate Similarity	NPC129340
0.8364	Intermediate Similarity	NPC475317
0.8364	Intermediate Similarity	NPC154856
0.8364	Intermediate Similarity	NPC52241
0.8349	Intermediate Similarity	NPC195708
0.8349	Intermediate Similarity	NPC230888
0.8348	Intermediate Similarity	NPC475187
0.8348	Intermediate Similarity	NPC281840
0.8348	Intermediate Similarity	NPC471406
0.8348	Intermediate Similarity	NPC108072
0.8333	Intermediate Similarity	NPC285927
0.8333	Intermediate Similarity	NPC162033
0.8333	Intermediate Similarity	NPC473199
0.8319	Intermediate Similarity	NPC88945
0.8304	Intermediate Similarity	NPC144068
0.8304	Intermediate Similarity	NPC260665
0.8291	Intermediate Similarity	NPC27363
0.8291	Intermediate Similarity	NPC256983
0.8288	Intermediate Similarity	NPC31839
0.8286	Intermediate Similarity	NPC157739
0.8276	Intermediate Similarity	NPC470478
0.8273	Intermediate Similarity	NPC218853
0.8273	Intermediate Similarity	NPC477070
0.8273	Intermediate Similarity	NPC477069
0.8273	Intermediate Similarity	NPC473570
0.8273	Intermediate Similarity	NPC265655
0.8269	Intermediate Similarity	NPC472989
0.8261	Intermediate Similarity	NPC319570
0.8261	Intermediate Similarity	NPC477071
0.8261	Intermediate Similarity	NPC161738
0.825	Intermediate Similarity	NPC471361
0.825	Intermediate Similarity	NPC251866
0.825	Intermediate Similarity	NPC89514
0.825	Intermediate Similarity	NPC284406
0.825	Intermediate Similarity	NPC70542
0.825	Intermediate Similarity	NPC86159
0.825	Intermediate Similarity	NPC9499
0.825	Intermediate Similarity	NPC219085
0.825	Intermediate Similarity	NPC6108
0.825	Intermediate Similarity	NPC469754
0.825	Intermediate Similarity	NPC471360
0.825	Intermediate Similarity	NPC471359
0.825	Intermediate Similarity	NPC469752
0.825	Intermediate Similarity	NPC197707
0.825	Intermediate Similarity	NPC471358
0.825	Intermediate Similarity	NPC471352
0.825	Intermediate Similarity	NPC469753
0.825	Intermediate Similarity	NPC469755
0.825	Intermediate Similarity	NPC10823
0.825	Intermediate Similarity	NPC469751
0.825	Intermediate Similarity	NPC180079
0.825	Intermediate Similarity	NPC17896
0.8235	Intermediate Similarity	NPC329784
0.8235	Intermediate Similarity	NPC240070
0.822	Intermediate Similarity	NPC248202
0.8218	Intermediate Similarity	NPC269267
0.8214	Intermediate Similarity	NPC48249
0.8214	Intermediate Similarity	NPC80843
0.8214	Intermediate Similarity	NPC1046
0.8214	Intermediate Similarity	NPC233003
0.8214	Intermediate Similarity	NPC130427
0.8214	Intermediate Similarity	NPC474265
0.8214	Intermediate Similarity	NPC471245
0.8214	Intermediate Similarity	NPC210420
0.8198	Intermediate Similarity	NPC255655
0.8198	Intermediate Similarity	NPC124053
0.8198	Intermediate Similarity	NPC242611
0.8198	Intermediate Similarity	NPC98633
0.8197	Intermediate Similarity	NPC146857
0.8197	Intermediate Similarity	NPC116075
0.8197	Intermediate Similarity	NPC247190
0.8197	Intermediate Similarity	NPC469749
0.8197	Intermediate Similarity	NPC32793
0.819	Intermediate Similarity	NPC473645
0.819	Intermediate Similarity	NPC58267
0.819	Intermediate Similarity	NPC470312
0.819	Intermediate Similarity	NPC267694
0.819	Intermediate Similarity	NPC144644
0.819	Intermediate Similarity	NPC142151
0.819	Intermediate Similarity	NPC153673
0.819	Intermediate Similarity	NPC110385
0.819	Intermediate Similarity	NPC473555
0.819	Intermediate Similarity	NPC471770
0.819	Intermediate Similarity	NPC263674
0.819	Intermediate Similarity	NPC278939
0.819	Intermediate Similarity	NPC261372
0.819	Intermediate Similarity	NPC37860
0.8182	Intermediate Similarity	NPC38217
0.8182	Intermediate Similarity	NPC472988
0.8182	Intermediate Similarity	NPC473517
0.8182	Intermediate Similarity	NPC295980
0.8182	Intermediate Similarity	NPC258323
0.8174	Intermediate Similarity	NPC105800
0.8174	Intermediate Similarity	NPC232237
0.8167	Intermediate Similarity	NPC311534
0.8165	Intermediate Similarity	NPC165405
0.8165	Intermediate Similarity	NPC26798
0.8158	Intermediate Similarity	NPC472718
0.8158	Intermediate Similarity	NPC244127
0.8158	Intermediate Similarity	NPC477031
0.8151	Intermediate Similarity	NPC469750
0.8151	Intermediate Similarity	NPC250556
0.8148	Intermediate Similarity	NPC213190
0.8142	Intermediate Similarity	NPC285086
0.8142	Intermediate Similarity	NPC475208
0.8142	Intermediate Similarity	NPC471252
0.8142	Intermediate Similarity	NPC178981
0.8142	Intermediate Similarity	NPC238935
0.8142	Intermediate Similarity	NPC132668
0.8142	Intermediate Similarity	NPC251309
0.8136	Intermediate Similarity	NPC41129
0.8131	Intermediate Similarity	NPC477172
0.8131	Intermediate Similarity	NPC31346
0.813	Intermediate Similarity	NPC329636
0.8125	Intermediate Similarity	NPC477073
0.8125	Intermediate Similarity	NPC122339
0.8125	Intermediate Similarity	NPC114188
0.8125	Intermediate Similarity	NPC270586
0.8125	Intermediate Similarity	NPC329953
0.8125	Intermediate Similarity	NPC473062
0.8125	Intermediate Similarity	NPC469824
0.8125	Intermediate Similarity	NPC292196
0.812	Intermediate Similarity	NPC275225
0.812	Intermediate Similarity	NPC182900
0.812	Intermediate Similarity	NPC476543
0.812	Intermediate Similarity	NPC293031
0.812	Intermediate Similarity	NPC51099
0.812	Intermediate Similarity	NPC476545
0.812	Intermediate Similarity	NPC68767
0.812	Intermediate Similarity	NPC249553

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 NPC106760 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	273
0.1-0.2	2429
0.2-0.3	4067
0.3-0.4	1508
0.4-0.5	412
0.5-0.6	278
0.6-0.7	142
0.7-0.8	35
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD8133	Approved
0.8257	Intermediate Similarity	NPD6412	Phase 2
0.825	Intermediate Similarity	NPD7319	Approved
0.8167	Intermediate Similarity	NPD7736	Approved
0.8151	Intermediate Similarity	NPD7507	Approved
0.8073	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7934	Intermediate Similarity	NPD8293	Discontinued
0.7881	Intermediate Similarity	NPD8294	Approved
0.7881	Intermediate Similarity	NPD8377	Approved
0.7863	Intermediate Similarity	NPD7327	Approved
0.7863	Intermediate Similarity	NPD7328	Approved
0.7815	Intermediate Similarity	NPD8380	Approved
0.7815	Intermediate Similarity	NPD8379	Approved
0.7815	Intermediate Similarity	NPD8296	Approved
0.7815	Intermediate Similarity	NPD8378	Approved
0.7815	Intermediate Similarity	NPD8335	Approved
0.7815	Intermediate Similarity	NPD8033	Approved
0.7797	Intermediate Similarity	NPD7516	Approved
0.775	Intermediate Similarity	NPD6370	Approved
0.7699	Intermediate Similarity	NPD6686	Approved
0.7642	Intermediate Similarity	NPD8171	Discontinued
0.7632	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD7492	Approved
0.7583	Intermediate Similarity	NPD6059	Approved
0.7583	Intermediate Similarity	NPD6054	Approved
0.7561	Intermediate Similarity	NPD6616	Approved
0.7541	Intermediate Similarity	NPD8328	Phase 3
0.75	Intermediate Similarity	NPD7078	Approved
0.7383	Intermediate Similarity	NPD8035	Phase 2
0.7383	Intermediate Similarity	NPD8034	Phase 2
0.7377	Intermediate Similarity	NPD6015	Approved
0.7377	Intermediate Similarity	NPD7503	Approved
0.7377	Intermediate Similarity	NPD6016	Approved
0.7317	Intermediate Similarity	NPD5988	Approved
0.7295	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD8297	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD6084	Phase 2
0.7054	Intermediate Similarity	NPD6083	Phase 2
0.7049	Intermediate Similarity	NPD6009	Approved
0.7031	Intermediate Similarity	NPD6033	Approved
0.699	Remote Similarity	NPD6928	Phase 2
0.6984	Remote Similarity	NPD6067	Discontinued
0.696	Remote Similarity	NPD8515	Approved
0.696	Remote Similarity	NPD8513	Phase 3
0.696	Remote Similarity	NPD8517	Approved
0.696	Remote Similarity	NPD8516	Approved
0.6952	Remote Similarity	NPD4788	Approved
0.6949	Remote Similarity	NPD7320	Approved
0.6949	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4632	Approved
0.6923	Remote Similarity	NPD6402	Approved
0.6923	Remote Similarity	NPD5956	Approved
0.6923	Remote Similarity	NPD7128	Approved
0.6923	Remote Similarity	NPD6675	Approved
0.6923	Remote Similarity	NPD5739	Approved
0.6891	Remote Similarity	NPD6373	Approved
0.6891	Remote Similarity	NPD6372	Approved
0.6847	Remote Similarity	NPD6399	Phase 3
0.6842	Remote Similarity	NPD7638	Approved
0.6838	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6940	Discontinued
0.6807	Remote Similarity	NPD6899	Approved
0.6807	Remote Similarity	NPD6881	Approved
0.6789	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD7640	Approved
0.6783	Remote Similarity	NPD7639	Approved
0.678	Remote Similarity	NPD6008	Approved
0.6777	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD6650	Approved
0.6777	Remote Similarity	NPD8130	Phase 1
0.6777	Remote Similarity	NPD6649	Approved
0.6774	Remote Similarity	NPD7115	Discovery
0.6726	Remote Similarity	NPD5695	Phase 3
0.6723	Remote Similarity	NPD5701	Approved
0.6723	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5697	Approved
0.6696	Remote Similarity	NPD5696	Approved
0.6694	Remote Similarity	NPD6883	Approved
0.6694	Remote Similarity	NPD4634	Approved
0.6694	Remote Similarity	NPD7290	Approved
0.6694	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD3702	Approved
0.6641	Remote Similarity	NPD8336	Approved
0.6641	Remote Similarity	NPD8337	Approved
0.6639	Remote Similarity	NPD6617	Approved
0.6639	Remote Similarity	NPD6869	Approved
0.6639	Remote Similarity	NPD6847	Approved
0.6636	Remote Similarity	NPD6903	Approved
0.6635	Remote Similarity	NPD6697	Approved
0.6635	Remote Similarity	NPD6114	Approved
0.6635	Remote Similarity	NPD6115	Approved
0.6635	Remote Similarity	NPD6118	Approved
0.6612	Remote Similarity	NPD6014	Approved
0.6612	Remote Similarity	NPD6013	Approved
0.6612	Remote Similarity	NPD6012	Approved
0.6606	Remote Similarity	NPD7334	Approved
0.6606	Remote Similarity	NPD6684	Approved
0.6606	Remote Similarity	NPD6409	Approved
0.6606	Remote Similarity	NPD5330	Approved
0.6606	Remote Similarity	NPD7521	Approved
0.6606	Remote Similarity	NPD7146	Approved
0.6589	Remote Similarity	NPD7604	Phase 2
0.6585	Remote Similarity	NPD6053	Discontinued
0.6579	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4753	Phase 2
0.6567	Remote Similarity	NPD8449	Approved
0.6562	Remote Similarity	NPD5983	Phase 2
0.6538	Remote Similarity	NPD6116	Phase 1
0.6529	Remote Similarity	NPD6011	Approved
0.6519	Remote Similarity	NPD8450	Suspended
0.6504	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD7748	Approved
0.6489	Remote Similarity	NPD6336	Discontinued
0.6475	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7902	Approved
0.6466	Remote Similarity	NPD4755	Approved
0.646	Remote Similarity	NPD7637	Suspended
0.6455	Remote Similarity	NPD6098	Approved
0.6442	Remote Similarity	NPD6117	Approved
0.6441	Remote Similarity	NPD1700	Approved
0.6434	Remote Similarity	NPD6921	Approved
0.6429	Remote Similarity	NPD6904	Approved
0.6429	Remote Similarity	NPD6673	Approved
0.6429	Remote Similarity	NPD6080	Approved
0.6423	Remote Similarity	NPD6371	Approved
0.6422	Remote Similarity	NPD3665	Phase 1
0.6422	Remote Similarity	NPD3666	Approved
0.6422	Remote Similarity	NPD3133	Approved
0.6422	Remote Similarity	NPD4786	Approved
0.6408	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4202	Approved
0.6387	Remote Similarity	NPD7632	Discontinued
0.6378	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5777	Approved
0.6356	Remote Similarity	NPD5285	Approved
0.6356	Remote Similarity	NPD5286	Approved
0.6356	Remote Similarity	NPD4700	Approved
0.6356	Remote Similarity	NPD4696	Approved
0.6339	Remote Similarity	NPD6672	Approved
0.6339	Remote Similarity	NPD5737	Approved
0.633	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.633	Remote Similarity	NPD3669	Approved
0.6319	Remote Similarity	NPD7625	Phase 1
0.6316	Remote Similarity	NPD5284	Approved
0.6316	Remote Similarity	NPD7983	Approved
0.6316	Remote Similarity	NPD7515	Phase 2
0.6316	Remote Similarity	NPD6411	Approved
0.6316	Remote Similarity	NPD5281	Approved
0.6316	Remote Similarity	NPD8074	Phase 3
0.6299	Remote Similarity	NPD6274	Approved
0.6293	Remote Similarity	NPD5210	Approved
0.6293	Remote Similarity	NPD7991	Discontinued
0.6293	Remote Similarity	NPD4629	Approved
0.629	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4522	Approved
0.6279	Remote Similarity	NPD7100	Approved
0.6279	Remote Similarity	NPD7101	Approved
0.6275	Remote Similarity	NPD4244	Approved
0.6275	Remote Similarity	NPD4245	Approved
0.6271	Remote Similarity	NPD4225	Approved
0.625	Remote Similarity	NPD5225	Approved
0.625	Remote Similarity	NPD5226	Approved
0.625	Remote Similarity	NPD7524	Approved
0.625	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD5224	Approved
0.625	Remote Similarity	NPD4633	Approved
0.6239	Remote Similarity	NPD4223	Phase 3
0.6239	Remote Similarity	NPD3667	Approved
0.6239	Remote Similarity	NPD4221	Approved
0.623	Remote Similarity	NPD4767	Approved
0.623	Remote Similarity	NPD4768	Approved
0.6228	Remote Similarity	NPD46	Approved
0.6228	Remote Similarity	NPD6698	Approved
0.6228	Remote Similarity	NPD5207	Approved
0.6226	Remote Similarity	NPD7799	Discontinued
0.6216	Remote Similarity	NPD5329	Approved
0.6207	Remote Similarity	NPD5282	Discontinued
0.6207	Remote Similarity	NPD6001	Approved
0.6207	Remote Similarity	NPD7900	Approved
0.6207	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD7525	Registered
0.6204	Remote Similarity	NPD8338	Approved
0.6202	Remote Similarity	NPD6335	Approved
0.6198	Remote Similarity	NPD5174	Approved
0.6198	Remote Similarity	NPD5175	Approved
0.6195	Remote Similarity	NPD5208	Approved
0.6183	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD6908	Approved
0.6183	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD6909	Approved
0.6176	Remote Similarity	NPD3698	Phase 2
0.6174	Remote Similarity	NPD5693	Phase 1
0.6174	Remote Similarity	NPD6050	Approved
0.6168	Remote Similarity	NPD4238	Approved
0.6168	Remote Similarity	NPD4802	Phase 2
0.6167	Remote Similarity	NPD5223	Approved

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