NPASS Compound

Structure

CID146652 OpenBabel06191715502D 79 86 0 0 1 0 0 0 0 0999 V2000 0.5129 -3.7313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0129 -2.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1629 1.0626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1847 1.2705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1269 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7227 -0.1076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1469 -3.3653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1026 0.0615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0129 -4.5974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0129 -4.5974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9196 -1.0857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0290 -1.3278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5129 -3.7313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0779 -1.6368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1765 -0.4166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1758 -2.2549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7996 0.6796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2091 2.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6110 0.6347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5129 -3.7313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5129 -1.9993 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7752 -2.5639 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2091 3.1347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7450 0.1347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5427 0.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3837 -1.2767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1515 0.3705 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2369 -0.3497 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5184 -1.8948 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3430 3.6347 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8789 0.6347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0129 0.1347 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4770 3.1347 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0129 -0.8653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4770 2.1347 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8789 -1.3653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4938 0.3195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3348 -0.9677 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3105 -0.9166 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0129 -2.8653 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3594 -0.6076 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9831 -3.5420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0751 3.6347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8946 1.0397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3430 4.6347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8789 1.6347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1469 0.6347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6110 3.6347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1469 -1.3653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3430 1.6347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6110 1.6347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7450 -0.8653 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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8789 -2.3653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 51 1 0 0 0 0 5 51 1 0 0 0 0 7 53 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 23 2 0 0 0 0 12 16 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 34 1 0 0 0 0 14 54 1 0 0 0 0 15 52 1 0 0 0 0 16 53 1 0 0 0 0 17 26 1 0 0 0 0 17 32 1 0 0 0 0 18 31 2 0 0 0 0 18 33 1 0 0 0 0 19 56 1 0 0 0 0 20 27 1 0 0 0 0 20 72 1 0 0 0 0 21 71 1 0 0 0 0 22 73 1 0 0 0 0 24 57 2 0 0 0 0 24 71 1 0 0 0 0 25 35 1 0 0 0 0 25 54 1 6 0 0 0 26 35 1 0 0 0 0 26 58 1 6 0 0 0 27 36 1 0 0 0 0 27 59 1 6 0 0 0 28 19 1 6 0 0 0 28 37 1 0 0 0 0 28 74 1 0 0 0 0 29 21 1 1 0 0 0 29 39 1 0 0 0 0 29 76 1 0 0 0 0 30 22 1 1 0 0 0 30 38 1 0 0 0 0 30 75 1 0 0 0 0 31 51 1 0 0 0 0 31 52 1 0 0 0 0 32 52 1 6 0 0 0 32 55 1 0 0 0 0 33 55 1 6 0 0 0 33 60 1 0 0 0 0 34 51 1 0 0 0 0 34 77 1 6 0 0 0 35 53 1 1 0 0 0 36 43 1 0 0 0 0 36 61 1 1 0 0 0 37 40 1 0 0 0 0 37 62 1 1 0 0 0 38 41 1 0 0 0 0 38 63 1 6 0 0 0 39 42 1 0 0 0 0 39 64 1 6 0 0 0 40 44 1 0 0 0 0 40 65 1 6 0 0 0 41 45 1 0 0 0 0 41 66 1 1 0 0 0 42 46 1 0 0 0 0 42 67 1 1 0 0 0 43 47 1 0 0 0 0 43 68 1 6 0 0 0 44 48 1 0 0 0 0 44 69 1 1 0 0 0 45 49 1 0 0 0 0 45 70 1 6 0 0 0 46 50 1 0 0 0 0 46 78 1 6 0 0 0 47 72 1 0 0 0 0 47 73 1 1 0 0 0 48 74 1 0 0 0 0 48 78 1 6 0 0 0 49 75 1 0 0 0 0 49 79 1 1 0 0 0 50 76 1 0 0 0 0 50 77 1 1 0 0 0 52 6 1 6 0 0 0 53 55 1 6 0 0 0 54 8 1 6 0 0 0 54 79 1 0 0 0 0 55 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1134.58
Volume:	1094.44
LogP:	1.586
LogD:	1.185
LogS:	-2.796
# Rotatable Bonds:	17
TPSA:	383.36
# H-Bond Aceptor:	24
# H-Bond Donor:	14
# Rings:	8
# Heavy Atoms:	24

MedChem Properties

QED Drug-Likeness Score:	0.058
Synthetic Accessibility Score:	7.129
Fsp3:	0.909
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:	-6.119
MDCK Permeability:	0.00022842326143290848
Pgp-inhibitor:	0.999
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.643
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.101
Plasma Protein Binding (PPB):	52.83118438720703%
Volume Distribution (VD):	0.016
Pgp-substrate:	16.375967025756836%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.07
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	0.059
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.204
Human Hepatotoxicity (H-HT):	0.145
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.071
Rat Oral Acute Toxicity:	0.128
Maximum Recommended Daily Dose:	0.059
Skin Sensitization:	0.869
Carcinogencity:	0.014
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.204

Download Data

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

Natural Product: NPC146652

Natural Product ID:	NPC146652
*Common Name:**	Yesanchinoside J
IUPAC Name:	[(2R,3S,4S,5R,6R)-6-[[(3S,7S,8R,9R,10R,12R,13R,14R,17S)-7,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2S)-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-5-en-2-yl]-2,3,7,9,11,12,13,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
Synonyms:	Yesanchinoside J
Standard InCHIKey:	MBCQKXULGRJSSA-ZQPMETRHSA-N
Standard InCHI:	InChI=1S/C55H90O24/c1-23(2)11-10-14-54(8,79-49-45(70)41(66)38(63)30(75-49)22-73-47-43(68)36(61)27(59)20-72-47)25-12-16-53(7)35(25)26(58)17-32-52(6)15-13-34(51(4,5)31(52)18-33(60)55(32,53)9)77-50-46(42(67)39(64)29(76-50)21-71-24(3)57)78-48-44(69)40(65)37(62)28(19-56)74-48/h11,18,25-30,32-50,56,58-70H,10,12-17,19-22H2,1-9H3/t25-,26+,27+,28+,29+,30+,32+,33-,34-,35-,36-,37+,38+,39+,40-,41-,42-,43+,44+,45+,46+,47-,48-,49-,50-,52-,53+,54-,55-/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O)O)COC(=O)C)O[C@H]2CC[C@]3(C(=C[C@@H]([C@@]4([C@@H]3C[C@@H](O)[C@H]3[C@@]4(C)CC[C@@H]3[C@@](O[C@@H]3O[C@H](CO[C@@H]4OC[C@H]([C@@H]([C@H]4O)O)O)[C@H]([C@@H]([C@H]3O)O)O)(CCC=C(C)C)C)C)O)C2(C)C)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503717
PubChem CID:	44592855
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
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350149]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28006911]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28202328]
NPO14105.1	Panax pseudo - ginseng var. japonicus	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14105.1	Panax pseudo - ginseng var. japonicus	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28005	Panax japonicus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28005	Panax japonicus	Species	Araliaceae	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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT136	Cell Line	SK-N-SH	Homo sapiens	Activity	=	87.9	%	PMID[483240]

☑ 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 NPC146652 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	247
0.1-0.2	1800
0.2-0.3	5166
0.3-0.4	12357
0.4-0.5	9717
0.5-0.6	5974
0.6-0.7	4306
0.7-0.8	1796
0.8-0.85	590
0.85-0.9	592
0.9-0.95	151
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9259	High Similarity	NPC65167
0.9252	High Similarity	NPC302057
0.9245	High Similarity	NPC190395
0.9159	High Similarity	NPC38217
0.9159	High Similarity	NPC472988
0.9151	High Similarity	NPC309448
0.9115	High Similarity	NPC50689
0.9115	High Similarity	NPC475358
0.9115	High Similarity	NPC135369
0.9115	High Similarity	NPC473566
0.9099	High Similarity	NPC63609
0.9099	High Similarity	NPC477031
0.9091	High Similarity	NPC307642
0.9083	High Similarity	NPC114188
0.9083	High Similarity	NPC470748
0.9074	High Similarity	NPC125361
0.9074	High Similarity	NPC51925
0.9074	High Similarity	NPC154085
0.9074	High Similarity	NPC296761
0.9074	High Similarity	NPC43976
0.9065	High Similarity	NPC234160
0.9065	High Similarity	NPC208650
0.9065	High Similarity	NPC231340
0.9065	High Similarity	NPC63368
0.9065	High Similarity	NPC14946
0.9057	High Similarity	NPC470768
0.9057	High Similarity	NPC470885
0.9057	High Similarity	NPC187400
0.9057	High Similarity	NPC75608
0.9057	High Similarity	NPC221562
0.9043	High Similarity	NPC295133
0.9043	High Similarity	NPC257207
0.9027	High Similarity	NPC195560
0.9027	High Similarity	NPC473633
0.9027	High Similarity	NPC229962
0.9027	High Similarity	NPC476085
0.9018	High Similarity	NPC477807
0.9009	High Similarity	NPC477808
0.9	High Similarity	NPC472716
0.8981	High Similarity	NPC472896
0.8981	High Similarity	NPC246124
0.8981	High Similarity	NPC180183
0.8981	High Similarity	NPC159005
0.8981	High Similarity	NPC472897
0.8981	High Similarity	NPC295980
0.8981	High Similarity	NPC6931
0.8972	High Similarity	NPC152584
0.8972	High Similarity	NPC470767
0.8972	High Similarity	NPC473199
0.8972	High Similarity	NPC127801
0.8972	High Similarity	NPC472900
0.8972	High Similarity	NPC69737
0.8972	High Similarity	NPC208594
0.8972	High Similarity	NPC194842
0.8972	High Similarity	NPC472899
0.8972	High Similarity	NPC160816
0.8972	High Similarity	NPC269627
0.8972	High Similarity	NPC208477
0.8972	High Similarity	NPC472898
0.8972	High Similarity	NPC470763
0.8957	High Similarity	NPC74259
0.8957	High Similarity	NPC474423
0.8957	High Similarity	NPC43842
0.8947	High Similarity	NPC198325
0.8947	High Similarity	NPC129393
0.8947	High Similarity	NPC207243
0.8947	High Similarity	NPC233391
0.8938	High Similarity	NPC160888
0.8938	High Similarity	NPC475403
0.8938	High Similarity	NPC475357
0.8929	High Similarity	NPC279638
0.8909	High Similarity	NPC472715
0.8889	High Similarity	NPC181467
0.8889	High Similarity	NPC94272
0.8879	High Similarity	NPC202261
0.8879	High Similarity	NPC117445
0.8879	High Similarity	NPC308262
0.8879	High Similarity	NPC208193
0.8879	High Similarity	NPC106589
0.887	High Similarity	NPC475419
0.887	High Similarity	NPC474908
0.887	High Similarity	NPC120390
0.887	High Similarity	NPC475590
0.8839	High Similarity	NPC473882
0.8839	High Similarity	NPC477810
0.8824	High Similarity	NPC477235
0.8818	High Similarity	NPC472717
0.8818	High Similarity	NPC141433
0.8807	High Similarity	NPC220427
0.8803	High Similarity	NPC471090
0.8796	High Similarity	NPC242748
0.8793	High Similarity	NPC193893
0.8785	High Similarity	NPC16520
0.8785	High Similarity	NPC473198
0.8785	High Similarity	NPC189852
0.8785	High Similarity	NPC157659
0.8785	High Similarity	NPC286969
0.8785	High Similarity	NPC31907
0.8785	High Similarity	NPC472252
0.8785	High Similarity	NPC120123
0.8785	High Similarity	NPC114874
0.8785	High Similarity	NPC473020
0.8785	High Similarity	NPC155010
0.8785	High Similarity	NPC131479
0.8785	High Similarity	NPC8039
0.8785	High Similarity	NPC245280
0.8785	High Similarity	NPC211879
0.8783	High Similarity	NPC107607
0.8783	High Similarity	NPC72260
0.8783	High Similarity	NPC268184
0.8774	High Similarity	NPC470434
0.8772	High Similarity	NPC472080
0.8772	High Similarity	NPC218093
0.8761	High Similarity	NPC207637
0.875	High Similarity	NPC251309
0.875	High Similarity	NPC144068
0.875	High Similarity	NPC476671
0.875	High Similarity	NPC477074
0.8739	High Similarity	NPC197231
0.8739	High Similarity	NPC475247
0.8739	High Similarity	NPC476547
0.8739	High Similarity	NPC473021
0.8739	High Similarity	NPC294129
0.8739	High Similarity	NPC477032
0.8739	High Similarity	NPC472987
0.8739	High Similarity	NPC124677
0.8739	High Similarity	NPC477028
0.8727	High Similarity	NPC224098
0.8727	High Similarity	NPC249265
0.8727	High Similarity	NPC477809
0.8727	High Similarity	NPC250089
0.8727	High Similarity	NPC14630
0.8727	High Similarity	NPC470433
0.8727	High Similarity	NPC300557
0.8727	High Similarity	NPC208383
0.8727	High Similarity	NPC171073
0.8727	High Similarity	NPC102016
0.8727	High Similarity	NPC194207
0.8727	High Similarity	NPC218571
0.8727	High Similarity	NPC150372
0.8727	High Similarity	NPC248746
0.8727	High Similarity	NPC46190
0.8727	High Similarity	NPC232054
0.8727	High Similarity	NPC309278
0.8727	High Similarity	NPC84956
0.8727	High Similarity	NPC6806
0.8727	High Similarity	NPC95051
0.8727	High Similarity	NPC475333
0.8727	High Similarity	NPC157530
0.8727	High Similarity	NPC244086
0.8727	High Similarity	NPC475550
0.8727	High Similarity	NPC22779
0.8727	High Similarity	NPC73243
0.8716	High Similarity	NPC33053
0.8707	High Similarity	NPC173555
0.8707	High Similarity	NPC40749
0.8707	High Similarity	NPC314535
0.8707	High Similarity	NPC475219
0.8707	High Similarity	NPC231518
0.8704	High Similarity	NPC273879
0.8704	High Similarity	NPC85593
0.8704	High Similarity	NPC165033
0.8704	High Similarity	NPC476361
0.8704	High Similarity	NPC93352
0.8704	High Similarity	NPC173583
0.8704	High Similarity	NPC31430
0.8704	High Similarity	NPC476360
0.8696	High Similarity	NPC470897
0.8696	High Similarity	NPC291820
0.8696	High Similarity	NPC469756
0.8696	High Similarity	NPC236973
0.8696	High Similarity	NPC81222
0.8696	High Similarity	NPC30483
0.8696	High Similarity	NPC32177
0.8696	High Similarity	NPC292467
0.8696	High Similarity	NPC55532
0.8692	High Similarity	NPC159036
0.8692	High Similarity	NPC288694
0.8692	High Similarity	NPC154452
0.8692	High Similarity	NPC272015
0.8692	High Similarity	NPC312553
0.8692	High Similarity	NPC136816
0.8684	High Similarity	NPC203862
0.8684	High Similarity	NPC68175
0.8684	High Similarity	NPC471547
0.8684	High Similarity	NPC20979
0.8679	High Similarity	NPC64348
0.8679	High Similarity	NPC469942
0.8673	High Similarity	NPC167183
0.8673	High Similarity	NPC11548
0.8673	High Similarity	NPC220293
0.8673	High Similarity	NPC469821
0.8673	High Similarity	NPC32707
0.8661	High Similarity	NPC210420
0.8661	High Similarity	NPC263359
0.8661	High Similarity	NPC244431
0.8661	High Similarity	NPC233003
0.8661	High Similarity	NPC474265
0.8661	High Similarity	NPC32361
0.8661	High Similarity	NPC210569

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 NPC146652 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	215
0.1-0.2	1975
0.2-0.3	4042
0.3-0.4	1943
0.4-0.5	523
0.5-0.6	300
0.6-0.7	118
0.7-0.8	21
0.8-0.85	3
0.85-0.9	7
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8783	High Similarity	NPD8377	Approved
0.8783	High Similarity	NPD8294	Approved
0.8707	High Similarity	NPD8296	Approved
0.8707	High Similarity	NPD8379	Approved
0.8707	High Similarity	NPD8335	Approved
0.8707	High Similarity	NPD8378	Approved
0.8707	High Similarity	NPD8380	Approved
0.8707	High Similarity	NPD8033	Approved
0.8291	Intermediate Similarity	NPD7327	Approved
0.8291	Intermediate Similarity	NPD7328	Approved
0.8261	Intermediate Similarity	NPD8133	Approved
0.8235	Intermediate Similarity	NPD7503	Approved
0.822	Intermediate Similarity	NPD7516	Approved
0.7823	Intermediate Similarity	NPD7507	Approved
0.7787	Intermediate Similarity	NPD8517	Approved
0.7787	Intermediate Similarity	NPD8515	Approved
0.7787	Intermediate Similarity	NPD8516	Approved
0.7759	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD8328	Phase 3
0.7642	Intermediate Similarity	NPD8513	Phase 3
0.7638	Intermediate Similarity	NPD7319	Approved
0.7603	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6412	Phase 2
0.7521	Intermediate Similarity	NPD6686	Approved
0.7333	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD8171	Discontinued
0.7287	Intermediate Similarity	NPD7736	Approved
0.7273	Intermediate Similarity	NPD8450	Suspended
0.7217	Intermediate Similarity	NPD7639	Approved
0.7217	Intermediate Similarity	NPD7640	Approved
0.7209	Intermediate Similarity	NPD8293	Discontinued
0.7197	Intermediate Similarity	NPD8449	Approved
0.7177	Intermediate Similarity	NPD7115	Discovery
0.713	Intermediate Similarity	NPD7638	Approved
0.7031	Intermediate Similarity	NPD6370	Approved
0.7	Intermediate Similarity	NPD7524	Approved
0.6992	Remote Similarity	NPD6882	Approved
0.6992	Remote Similarity	NPD8297	Approved
0.6975	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7492	Approved
0.6905	Remote Similarity	NPD6009	Approved
0.6901	Remote Similarity	NPD7625	Phase 1
0.6881	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6059	Approved
0.6875	Remote Similarity	NPD6319	Approved
0.6875	Remote Similarity	NPD6054	Approved
0.687	Remote Similarity	NPD6616	Approved
0.6842	Remote Similarity	NPD6399	Phase 3
0.6838	Remote Similarity	NPD4225	Approved
0.6822	Remote Similarity	NPD7525	Registered
0.6818	Remote Similarity	NPD7078	Approved
0.68	Remote Similarity	NPD4632	Approved
0.6789	Remote Similarity	NPD6695	Phase 3
0.6777	Remote Similarity	NPD7128	Approved
0.6777	Remote Similarity	NPD5739	Approved
0.6777	Remote Similarity	NPD6675	Approved
0.6777	Remote Similarity	NPD6402	Approved
0.6754	Remote Similarity	NPD7637	Suspended
0.6748	Remote Similarity	NPD6372	Approved
0.6748	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD6373	Approved
0.6723	Remote Similarity	NPD5344	Discontinued
0.6696	Remote Similarity	NPD7750	Discontinued
0.6696	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD8074	Phase 3
0.6692	Remote Similarity	NPD6016	Approved
0.6692	Remote Similarity	NPD6015	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6641	Remote Similarity	NPD5988	Approved
0.664	Remote Similarity	NPD8130	Phase 1
0.664	Remote Similarity	NPD6650	Approved
0.664	Remote Similarity	NPD6649	Approved
0.6638	Remote Similarity	NPD7748	Approved
0.661	Remote Similarity	NPD7902	Approved
0.6609	Remote Similarity	NPD8035	Phase 2
0.6609	Remote Similarity	NPD8034	Phase 2
0.6591	Remote Similarity	NPD6067	Discontinued
0.6585	Remote Similarity	NPD5701	Approved
0.6585	Remote Similarity	NPD5697	Approved
0.6579	Remote Similarity	NPD6051	Approved
0.6574	Remote Similarity	NPD7645	Phase 2
0.656	Remote Similarity	NPD7102	Approved
0.656	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.656	Remote Similarity	NPD6883	Approved
0.656	Remote Similarity	NPD7290	Approved
0.6514	Remote Similarity	NPD6931	Approved
0.6514	Remote Similarity	NPD6930	Phase 2
0.6509	Remote Similarity	NPD6942	Approved
0.6509	Remote Similarity	NPD7339	Approved
0.6508	Remote Similarity	NPD6869	Approved
0.6508	Remote Similarity	NPD6847	Approved
0.6508	Remote Similarity	NPD6617	Approved
0.6504	Remote Similarity	NPD6008	Approved
0.648	Remote Similarity	NPD6013	Approved
0.648	Remote Similarity	NPD6012	Approved
0.648	Remote Similarity	NPD6014	Approved
0.6471	Remote Similarity	NPD6083	Phase 2
0.6471	Remote Similarity	NPD6084	Phase 2
0.6466	Remote Similarity	NPD7515	Phase 2
0.6466	Remote Similarity	NPD7604	Phase 2
0.6439	Remote Similarity	NPD5983	Phase 2
0.6429	Remote Similarity	NPD4786	Approved
0.6429	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6929	Approved
0.64	Remote Similarity	NPD6011	Approved
0.64	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD6033	Approved
0.6393	Remote Similarity	NPD5211	Phase 2
0.6378	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6336	Discontinued
0.6364	Remote Similarity	NPD7514	Phase 3
0.6364	Remote Similarity	NPD6648	Approved
0.6356	Remote Similarity	NPD7900	Approved
0.6356	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4755	Approved
0.6328	Remote Similarity	NPD6053	Discontinued
0.6325	Remote Similarity	NPD7087	Discontinued
0.632	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD4634	Approved
0.6296	Remote Similarity	NPD6933	Approved
0.6296	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5328	Approved
0.629	Remote Similarity	NPD5141	Approved
0.6271	Remote Similarity	NPD4202	Approved
0.625	Remote Similarity	NPD3667	Approved
0.6239	Remote Similarity	NPD6925	Approved
0.6239	Remote Similarity	NPD7838	Discovery
0.6239	Remote Similarity	NPD5776	Phase 2
0.6239	Remote Similarity	NPD46	Approved
0.6239	Remote Similarity	NPD6698	Approved
0.623	Remote Similarity	NPD5286	Approved
0.623	Remote Similarity	NPD4696	Approved
0.623	Remote Similarity	NPD4700	Approved
0.623	Remote Similarity	NPD5285	Approved
0.6228	Remote Similarity	NPD6893	Approved
0.6216	Remote Similarity	NPD7332	Phase 2
0.6216	Remote Similarity	NPD6928	Phase 2
0.6195	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD3669	Approved
0.6186	Remote Similarity	NPD7983	Approved
0.6186	Remote Similarity	NPD6079	Approved
0.6183	Remote Similarity	NPD6274	Approved
0.6182	Remote Similarity	NPD7145	Approved
0.6179	Remote Similarity	NPD4159	Approved
0.6174	Remote Similarity	NPD3618	Phase 1
0.6167	Remote Similarity	NPD5695	Phase 3
0.6165	Remote Similarity	NPD7101	Approved
0.6165	Remote Similarity	NPD7100	Approved
0.6161	Remote Similarity	NPD6902	Approved
0.6148	Remote Similarity	NPD5696	Approved
0.6134	Remote Similarity	NPD5779	Approved
0.6134	Remote Similarity	NPD5778	Approved
0.6129	Remote Similarity	NPD5224	Approved
0.6129	Remote Similarity	NPD4633	Approved
0.6129	Remote Similarity	NPD5226	Approved
0.6129	Remote Similarity	NPD5225	Approved
0.6111	Remote Similarity	NPD6926	Approved
0.6111	Remote Similarity	NPD6924	Approved
0.6111	Remote Similarity	NPD4767	Approved
0.6111	Remote Similarity	NPD4768	Approved
0.6091	Remote Similarity	NPD6932	Approved
0.609	Remote Similarity	NPD6335	Approved
0.608	Remote Similarity	NPD5174	Approved
0.608	Remote Similarity	NPD5175	Approved
0.6077	Remote Similarity	NPD6429	Approved
0.6077	Remote Similarity	NPD6430	Approved
0.6074	Remote Similarity	NPD6908	Approved
0.6074	Remote Similarity	NPD6909	Approved
0.6068	Remote Similarity	NPD6672	Approved
0.6068	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5737	Approved
0.6061	Remote Similarity	NPD6940	Discontinued
0.6058	Remote Similarity	NPD8342	Approved
0.6058	Remote Similarity	NPD8340	Approved
0.6058	Remote Similarity	NPD8299	Approved
0.6058	Remote Similarity	NPD8341	Approved
0.605	Remote Similarity	NPD6411	Approved
0.6048	Remote Similarity	NPD5223	Approved
0.6047	Remote Similarity	NPD6371	Approved
0.6043	Remote Similarity	NPD8336	Approved
0.6043	Remote Similarity	NPD8337	Approved
0.6034	Remote Similarity	NPD6684	Approved
0.6034	Remote Similarity	NPD5330	Approved
0.6034	Remote Similarity	NPD7521	Approved
0.6034	Remote Similarity	NPD7334	Approved
0.6034	Remote Similarity	NPD6409	Approved
0.6034	Remote Similarity	NPD7146	Approved
0.6033	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6898	Phase 1
0.6017	Remote Similarity	NPD4753	Phase 2
0.6016	Remote Similarity	NPD4729	Approved
0.6016	Remote Similarity	NPD4730	Approved
0.6015	Remote Similarity	NPD6317	Approved
0.5984	Remote Similarity	NPD5221	Approved
0.5984	Remote Similarity	NPD5220	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