NPASS Compound

Structure

NPC141669 OpenBabel07101719192D 92100 0 0 1 0 0 0 0 0999 V2000 5.8605 0.2339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1224 1.3701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2774 2.9443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9433 -6.3725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1883 -2.8098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2079 -2.8098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2993 -0.8956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2068 0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5471 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6305 -0.3030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5074 1.8949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8924 2.4196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4904 2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.5847 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1885 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4904 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1634 1.1663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9335 2.2158 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2452 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 -5.8824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5484 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6305 1.2833 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6981 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6414 2.4510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.7357 -3.4314 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1885 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6414 -3.4314 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9433 -0.4902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8490 -1.4706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5471 -1.4706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9433 1.4706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9433 -4.4118 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7924 2.9412 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.7357 -4.4118 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.0376 -0.4902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6414 -4.4118 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9433 -1.4706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9433 2.4510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7924 -4.9020 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.8866 -4.9020 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0376 -1.4706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0376 -4.4118 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0943 -1.9608 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1885 -1.9608 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7924 0.9804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9433 -3.4314 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0376 -3.4314 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3395 -1.4706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2452 -1.4706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6981 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8490 -0.4902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8490 -0.4902 0.0000 C 0 0 2 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 -5.0943 0.9804 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 -4.9020 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.4904 3.9216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.5847 -1.9608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0376 1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2452 2.4510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2452 -6.3725 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2455 0.7586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7924 3.9216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.5847 -4.9020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8866 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4904 -4.9020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7924 -1.9608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 2.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7924 -5.8824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8866 -5.8824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8866 -1.9608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1885 -4.9020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 -1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 0.4902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4904 -1.9608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2452 -0.4902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6414 1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8866 -2.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3395 -0.4902 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7924 -2.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7924 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 -1.9608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0943 -2.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1885 -2.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 58 1 0 0 0 0 7 58 1 0 0 0 0 8 59 1 0 0 0 0 9 60 1 0 0 0 0 10 14 1 0 0 0 0 10 30 1 0 0 0 0 11 16 1 0 0 0 0 11 31 2 0 0 0 0 12 17 1 0 0 0 0 12 37 1 0 0 0 0 13 15 1 0 0 0 0 13 38 1 0 0 0 0 14 59 1 0 0 0 0 15 60 1 0 0 0 0 16 62 1 0 0 0 0 17 61 1 0 0 0 0 18 25 2 0 0 0 0 18 29 1 0 0 0 0 19 26 1 0 0 0 0 19 29 1 0 0 0 0 20 65 1 0 0 0 0 21 66 1 0 0 0 0 22 67 1 0 0 0 0 23 83 1 0 0 0 0 24 36 1 0 0 0 0 24 84 1 0 0 0 0 26 3 1 6 0 0 0 27 63 2 3 0 0 0 27 68 1 0 0 0 0 28 64 2 3 0 0 0 28 69 1 0 0 0 0 29 70 2 0 0 0 0 30 26 1 1 0 0 0 30 31 1 0 0 0 0 31 59 1 0 0 0 0 32 20 1 6 0 0 0 32 41 1 0 0 0 0 32 85 1 0 0 0 0 33 21 1 1 0 0 0 33 42 1 0 0 0 0 33 86 1 0 0 0 0 34 22 1 1 0 0 0 34 43 1 0 0 0 0 34 87 1 0 0 0 0 35 23 1 1 0 0 0 35 44 1 0 0 0 0 35 88 1 0 0 0 0 36 45 1 0 0 0 0 36 89 1 6 0 0 0 37 58 1 0 0 0 0 37 60 1 1 0 0 0 38 58 1 0 0 0 0 38 90 1 1 0 0 0 39 46 1 0 0 0 0 39 53 1 0 0 0 0 39 63 1 1 0 0 0 40 47 1 0 0 0 0 40 54 1 0 0 0 0 40 64 1 6 0 0 0 41 46 1 0 0 0 0 41 71 1 6 0 0 0 42 48 1 0 0 0 0 42 72 1 6 0 0 0 43 49 1 0 0 0 0 43 73 1 6 0 0 0 44 47 1 0 0 0 0 44 74 1 6 0 0 0 45 51 1 0 0 0 0 45 75 1 1 0 0 0 46 76 1 6 0 0 0 47 77 1 1 0 0 0 48 50 1 0 0 0 0 48 78 1 1 0 0 0 49 52 1 0 0 0 0 49 79 1 1 0 0 0 50 55 1 0 0 0 0 50 80 1 6 0 0 0 51 57 1 0 0 0 0 51 91 1 6 0 0 0 52 56 1 0 0 0 0 52 92 1 6 0 0 0 53 85 1 0 0 0 0 53 89 1 6 0 0 0 54 88 1 0 0 0 0 54 91 1 1 0 0 0 55 86 1 0 0 0 0 55 92 1 1 0 0 0 56 83 1 1 0 0 0 56 87 1 0 0 0 0 57 84 1 0 0 0 0 57 90 1 1 0 0 0 59 61 1 6 0 0 0 60 62 1 6 0 0 0 61 62 1 6 0 0 0 61 81 1 0 0 0 0 62 82 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1320.65
Volume:	1258.837
LogP:	-0.488
LogD:	-0.15
LogS:	-2.165
# Rotatable Bonds:	22
TPSA:	471.02
# H-Bond Aceptor:	30
# H-Bond Donor:	17
# Rings:	9
# Heavy Atoms:	30

MedChem Properties

QED Drug-Likeness Score:	0.031
Synthetic Accessibility Score:	7.645
Fsp3:	0.887
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:	-6.476
MDCK Permeability:	0.00035190529888495803
Pgp-inhibitor:	0.053
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.865
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.383
Plasma Protein Binding (PPB):	34.758544921875%
Volume Distribution (VD):	0.122
Pgp-substrate:	21.06720542907715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.037

ADMET: Excretion

Clearance (CL):	0.186
Half-life (T1/2):	0.758

ADMET: Toxicity

hERG Blockers:	0.268
Human Hepatotoxicity (H-HT):	0.194
Drug-inuced Liver Injury (DILI):	0.261
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.036
Skin Sensitization:	0.039
Carcinogencity:	0.82
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC141669

Natural Product ID:	NPC141669
*Common Name:**	Sarasinoside R
IUPAC Name:	N-[(2S,3R,4R,5R,6R)-2-[(3R,4S,5R,6S)-5-[(2S,3R,4R,5S,6R)-3-acetamido-6-[[(2R,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]oxymethyl]-4,5-dihydroxyoxan-2-yl]oxy-6-[[(3S,5S,8S,9S,10S,14S,17R)-8,9-dihydroxy-4,4,10,14-tetramethyl-17-[(2R)-6-methyl-4-oxohept-5-en-2-yl]-1,2,3,5,6,7,11,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxy]-4-hydroxyoxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Synonyms:	Sarasinoside R
Standard InCHIKey:	JZASRPOFXGPITI-BOLCQSASSA-N
Standard InCHI:	InChI=1S/C62H100N2O28/c1-25(2)18-29(70)19-26(3)30-10-14-59(8)31(30)11-16-62(82)60(9)15-13-38(58(6,7)37(60)12-17-61(59,62)81)90-57-51(45(75)36(24-84-57)89-53-39(63-27(4)68)46(76)41(71)32(20-65)85-53)91-54-40(64-28(5)69)47(77)44(74)35(88-54)23-83-56-52(49(79)43(73)34(22-67)87-56)92-55-50(80)48(78)42(72)33(21-66)86-55/h11,18,26,30,32-57,65-67,71-82H,10,12-17,19-24H2,1-9H3,(H,63,68)(H,64,69)/t26-,30-,32-,33-,34-,35-,36-,37+,38+,39-,40-,41+,42-,43-,44-,45+,46-,47-,48+,49+,50-,51-,52-,53+,54+,55+,56-,57+,59+,60+,61+,62+/m1/s1
SMILES:	CC(=CC(=O)C[C@@H](C)[C@H]1CC[C@@]2(C)C1=CC[C@@]1([C@@]3(C)CC[C@@H](C(C)(C)[C@@H]3CC[C@]21O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)N=C(C)O)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](CO)O2)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)O)O)N=C(C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071317
PubChem CID:	60200698
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO33227	Lipastrotethya sp.	Species	n.a.	n.a.	n.a.	Micronesia	n.a.	PMID[22148280]
NPO33227	Lipastrotethya sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22742761]
NPO33227	Lipastrotethya sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[27779395]

☑ 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	1
Others	2

Activity Type	# Activity
Cell Line	2
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	>	100000.0	nM	PMID[464311]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	14700.0	nM	PMID[464311]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[464311]

☑ 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 NPC141669 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	165
0.1-0.2	1086
0.2-0.3	4525
0.3-0.4	15225
0.4-0.5	11441
0.5-0.6	6577
0.6-0.7	2352
0.7-0.8	1264
0.8-0.85	11
0.85-0.9	26
0.9-0.95	21
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9549	High Similarity	NPC162910
0.9489	High Similarity	NPC36463
0.9489	High Similarity	NPC298005
0.9407	High Similarity	NPC298469
0.9398	High Similarity	NPC180770
0.9398	High Similarity	NPC302276
0.9338	High Similarity	NPC214821
0.9338	High Similarity	NPC298067
0.9265	High Similarity	NPC193579
0.9203	High Similarity	NPC61717
0.9203	High Similarity	NPC244380
0.9111	High Similarity	NPC265908
0.8986	High Similarity	NPC69176
0.8986	High Similarity	NPC284625
0.8913	High Similarity	NPC475584
0.8913	High Similarity	NPC475394
0.8913	High Similarity	NPC475152
0.8872	High Similarity	NPC139585
0.8849	High Similarity	NPC475892
0.8815	High Similarity	NPC280941
0.8815	High Similarity	NPC235772
0.8741	High Similarity	NPC477072
0.8667	High Similarity	NPC119794
0.8667	High Similarity	NPC73829
0.8633	High Similarity	NPC82931
0.8633	High Similarity	NPC172365
0.8633	High Similarity	NPC210729
0.8623	High Similarity	NPC243680
0.8623	High Similarity	NPC200788
0.8621	High Similarity	NPC265699
0.8621	High Similarity	NPC475527
0.8593	High Similarity	NPC475472
0.8562	High Similarity	NPC113620
0.8562	High Similarity	NPC100612
0.8562	High Similarity	NPC475599
0.8562	High Similarity	NPC174336
0.8562	High Similarity	NPC187497
0.854	High Similarity	NPC75318
0.8478	Intermediate Similarity	NPC145899
0.8467	Intermediate Similarity	NPC76999
0.8045	Intermediate Similarity	NPC197003
0.8045	Intermediate Similarity	NPC190939
0.8	Intermediate Similarity	NPC469943
0.7985	Intermediate Similarity	NPC308459
0.7955	Intermediate Similarity	NPC279638
0.7926	Intermediate Similarity	NPC476675
0.7727	Intermediate Similarity	NPC210420
0.7727	Intermediate Similarity	NPC474265
0.7721	Intermediate Similarity	NPC129393
0.7664	Intermediate Similarity	NPC476672
0.7647	Intermediate Similarity	NPC477464
0.7635	Intermediate Similarity	NPC803
0.7626	Intermediate Similarity	NPC476674
0.7626	Intermediate Similarity	NPC248202
0.7626	Intermediate Similarity	NPC473505
0.7612	Intermediate Similarity	NPC473882
0.7612	Intermediate Similarity	NPC474557
0.7612	Intermediate Similarity	NPC165439
0.7606	Intermediate Similarity	NPC201359
0.7591	Intermediate Similarity	NPC476670
0.7576	Intermediate Similarity	NPC476113
0.7576	Intermediate Similarity	NPC52241
0.7576	Intermediate Similarity	NPC475317
0.7576	Intermediate Similarity	NPC154856
0.7574	Intermediate Similarity	NPC475899
0.7574	Intermediate Similarity	NPC470514
0.7574	Intermediate Similarity	NPC36831
0.7574	Intermediate Similarity	NPC470513
0.7571	Intermediate Similarity	NPC476673
0.7556	Intermediate Similarity	NPC472718
0.7554	Intermediate Similarity	NPC256983
0.7537	Intermediate Similarity	NPC260665
0.7536	Intermediate Similarity	NPC68767
0.7536	Intermediate Similarity	NPC477463
0.7536	Intermediate Similarity	NPC51099
0.7536	Intermediate Similarity	NPC293031
0.7536	Intermediate Similarity	NPC275225
0.7518	Intermediate Similarity	NPC471577
0.7518	Intermediate Similarity	NPC473401
0.75	Intermediate Similarity	NPC148417
0.75	Intermediate Similarity	NPC68175
0.75	Intermediate Similarity	NPC102015
0.75	Intermediate Similarity	NPC302057
0.75	Intermediate Similarity	NPC136768
0.75	Intermediate Similarity	NPC473474
0.75	Intermediate Similarity	NPC110633
0.7485	Intermediate Similarity	NPC475345
0.7482	Intermediate Similarity	NPC15918
0.7482	Intermediate Similarity	NPC94072
0.7482	Intermediate Similarity	NPC169816
0.7482	Intermediate Similarity	NPC305771
0.7481	Intermediate Similarity	NPC475140
0.7481	Intermediate Similarity	NPC250247
0.7481	Intermediate Similarity	NPC43550
0.7481	Intermediate Similarity	NPC471385
0.7481	Intermediate Similarity	NPC293330
0.7481	Intermediate Similarity	NPC204414
0.7481	Intermediate Similarity	NPC469782
0.7481	Intermediate Similarity	NPC65105
0.7481	Intermediate Similarity	NPC41061
0.7481	Intermediate Similarity	NPC67857
0.7481	Intermediate Similarity	NPC119592
0.7481	Intermediate Similarity	NPC102088
0.7481	Intermediate Similarity	NPC475160
0.7481	Intermediate Similarity	NPC54636
0.7481	Intermediate Similarity	NPC71065
0.7481	Intermediate Similarity	NPC76972
0.7481	Intermediate Similarity	NPC476068
0.7481	Intermediate Similarity	NPC4328
0.7481	Intermediate Similarity	NPC309907
0.7481	Intermediate Similarity	NPC202828
0.7481	Intermediate Similarity	NPC471550
0.7481	Intermediate Similarity	NPC60557
0.7481	Intermediate Similarity	NPC261506
0.7481	Intermediate Similarity	NPC123199
0.7481	Intermediate Similarity	NPC294453
0.7481	Intermediate Similarity	NPC70809
0.7481	Intermediate Similarity	NPC473714
0.7481	Intermediate Similarity	NPC298034
0.7481	Intermediate Similarity	NPC224381
0.7481	Intermediate Similarity	NPC57484
0.7481	Intermediate Similarity	NPC74727
0.7481	Intermediate Similarity	NPC305981
0.7481	Intermediate Similarity	NPC100639
0.7481	Intermediate Similarity	NPC227551
0.7481	Intermediate Similarity	NPC161717
0.7481	Intermediate Similarity	NPC236638
0.7481	Intermediate Similarity	NPC79643
0.7464	Intermediate Similarity	NPC268184
0.7464	Intermediate Similarity	NPC142151
0.7464	Intermediate Similarity	NPC475187
0.7464	Intermediate Similarity	NPC144644
0.7464	Intermediate Similarity	NPC153673
0.7464	Intermediate Similarity	NPC37860
0.7464	Intermediate Similarity	NPC267694
0.7464	Intermediate Similarity	NPC110385
0.7463	Intermediate Similarity	NPC130427
0.7445	Intermediate Similarity	NPC237191
0.744	Intermediate Similarity	NPC475649
0.7431	Intermediate Similarity	NPC473805
0.7431	Intermediate Similarity	NPC473519
0.7429	Intermediate Similarity	NPC160084
0.7426	Intermediate Similarity	NPC160415
0.7426	Intermediate Similarity	NPC471384
0.7426	Intermediate Similarity	NPC161674
0.7426	Intermediate Similarity	NPC58448
0.741	Intermediate Similarity	NPC475182
0.741	Intermediate Similarity	NPC249553
0.741	Intermediate Similarity	NPC182900
0.741	Intermediate Similarity	NPC476544
0.741	Intermediate Similarity	NPC476543
0.741	Intermediate Similarity	NPC476545
0.7407	Intermediate Similarity	NPC134835
0.7407	Intermediate Similarity	NPC219180
0.7407	Intermediate Similarity	NPC309714
0.7407	Intermediate Similarity	NPC241909
0.7407	Intermediate Similarity	NPC475287
0.7407	Intermediate Similarity	NPC251309
0.7407	Intermediate Similarity	NPC46665
0.7407	Intermediate Similarity	NPC96641
0.7407	Intermediate Similarity	NPC155410
0.7407	Intermediate Similarity	NPC150400
0.7407	Intermediate Similarity	NPC133818
0.7407	Intermediate Similarity	NPC151543
0.7407	Intermediate Similarity	NPC473343
0.7407	Intermediate Similarity	NPC475467
0.7407	Intermediate Similarity	NPC258885
0.7407	Intermediate Similarity	NPC114304
0.7407	Intermediate Similarity	NPC473826
0.7407	Intermediate Similarity	NPC124296
0.7407	Intermediate Similarity	NPC295823
0.7407	Intermediate Similarity	NPC323341
0.7407	Intermediate Similarity	NPC251263
0.7407	Intermediate Similarity	NPC293038
0.7407	Intermediate Similarity	NPC192600
0.7407	Intermediate Similarity	NPC163183
0.7407	Intermediate Similarity	NPC114287
0.7407	Intermediate Similarity	NPC73318
0.7407	Intermediate Similarity	NPC174720
0.7407	Intermediate Similarity	NPC477074
0.7407	Intermediate Similarity	NPC62696
0.7407	Intermediate Similarity	NPC166422
0.7388	Intermediate Similarity	NPC285410
0.7388	Intermediate Similarity	NPC250481
0.7388	Intermediate Similarity	NPC263827
0.7372	Intermediate Similarity	NPC8524
0.7372	Intermediate Similarity	NPC475514
0.7372	Intermediate Similarity	NPC104137
0.7372	Intermediate Similarity	NPC309223
0.7372	Intermediate Similarity	NPC220160
0.7372	Intermediate Similarity	NPC475209
0.7372	Intermediate Similarity	NPC309433
0.7372	Intermediate Similarity	NPC123522
0.7372	Intermediate Similarity	NPC69811
0.7372	Intermediate Similarity	NPC471580
0.7372	Intermediate Similarity	NPC473452
0.7372	Intermediate Similarity	NPC33012
0.7372	Intermediate Similarity	NPC85154
0.7372	Intermediate Similarity	NPC477252
0.7372	Intermediate Similarity	NPC470876

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 NPC141669 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	129
0.1-0.2	763
0.2-0.3	3350
0.3-0.4	3542
0.4-0.5	905
0.5-0.6	373
0.6-0.7	72
0.7-0.8	16
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
0.7211	Intermediate Similarity	NPD8450	Suspended
0.7143	Intermediate Similarity	NPD8449	Approved
0.709	Intermediate Similarity	NPD6412	Phase 2
0.7063	Intermediate Similarity	NPD8328	Phase 3
0.7029	Intermediate Similarity	NPD8133	Approved
0.6987	Remote Similarity	NPD7625	Phase 1
0.6985	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6914	Discontinued
0.6871	Remote Similarity	NPD8336	Approved
0.6871	Remote Similarity	NPD8337	Approved
0.6853	Remote Similarity	NPD8377	Approved
0.6853	Remote Similarity	NPD8294	Approved
0.6806	Remote Similarity	NPD8296	Approved
0.6806	Remote Similarity	NPD8335	Approved
0.6806	Remote Similarity	NPD8378	Approved
0.6806	Remote Similarity	NPD8033	Approved
0.6806	Remote Similarity	NPD8380	Approved
0.6806	Remote Similarity	NPD8379	Approved
0.68	Remote Similarity	NPD8338	Approved
0.6797	Remote Similarity	NPD6333	Approved
0.6797	Remote Similarity	NPD6334	Approved
0.6788	Remote Similarity	NPD8174	Phase 2
0.6735	Remote Similarity	NPD7507	Approved
0.6644	Remote Similarity	NPD6370	Approved
0.6644	Remote Similarity	NPD7736	Approved
0.6643	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7319	Approved
0.6577	Remote Similarity	NPD8293	Discontinued
0.6556	Remote Similarity	NPD8392	Approved
0.6556	Remote Similarity	NPD8391	Approved
0.6556	Remote Similarity	NPD8390	Approved
0.6552	Remote Similarity	NPD7516	Approved
0.6547	Remote Similarity	NPD6686	Approved
0.6531	Remote Similarity	NPD8080	Discontinued
0.6507	Remote Similarity	NPD6059	Approved
0.6507	Remote Similarity	NPD6054	Approved
0.6483	Remote Similarity	NPD7328	Approved
0.6483	Remote Similarity	NPD7327	Approved
0.6463	Remote Similarity	NPD8517	Approved
0.6463	Remote Similarity	NPD7503	Approved
0.6463	Remote Similarity	NPD6908	Approved
0.6463	Remote Similarity	NPD8516	Approved
0.6463	Remote Similarity	NPD8515	Approved
0.6463	Remote Similarity	NPD6909	Approved
0.642	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.637	Remote Similarity	NPD7641	Discontinued
0.6364	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD6882	Approved
0.6358	Remote Similarity	NPD8074	Phase 3
0.6358	Remote Similarity	NPD8448	Approved
0.6351	Remote Similarity	NPD8513	Phase 3
0.6351	Remote Similarity	NPD6016	Approved
0.6351	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD6015	Approved
0.6338	Remote Similarity	NPD6421	Discontinued
0.6333	Remote Similarity	NPD8299	Approved
0.6333	Remote Similarity	NPD8341	Approved
0.6333	Remote Similarity	NPD8342	Approved
0.6333	Remote Similarity	NPD8340	Approved
0.6333	Remote Similarity	NPD7492	Approved
0.6331	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD5988	Approved
0.6301	Remote Similarity	NPD6009	Approved
0.6291	Remote Similarity	NPD8451	Approved
0.6291	Remote Similarity	NPD6616	Approved
0.6286	Remote Similarity	NPD5357	Phase 1
0.6284	Remote Similarity	NPD6319	Approved
0.6267	Remote Similarity	NPD6067	Discontinued
0.6267	Remote Similarity	NPD7604	Phase 2
0.625	Remote Similarity	NPD6430	Approved
0.625	Remote Similarity	NPD7078	Approved
0.625	Remote Similarity	NPD6429	Approved
0.6242	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD6940	Discontinued
0.6207	Remote Similarity	NPD4632	Approved
0.619	Remote Similarity	NPD7115	Discovery
0.6181	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD8415	Approved
0.617	Remote Similarity	NPD7128	Approved
0.617	Remote Similarity	NPD6402	Approved
0.617	Remote Similarity	NPD5739	Approved
0.617	Remote Similarity	NPD6675	Approved
0.6159	Remote Similarity	NPD8418	Phase 2
0.6159	Remote Similarity	NPD7829	Approved
0.6159	Remote Similarity	NPD7830	Approved
0.6154	Remote Similarity	NPD6373	Approved
0.6154	Remote Similarity	NPD6372	Approved
0.6148	Remote Similarity	NPD7748	Approved
0.6133	Remote Similarity	NPD6921	Approved
0.6131	Remote Similarity	NPD7902	Approved
0.6127	Remote Similarity	NPD8307	Discontinued
0.612	Remote Similarity	NPD8407	Phase 2
0.6104	Remote Similarity	NPD6033	Approved
0.6084	Remote Similarity	NPD6899	Approved
0.6084	Remote Similarity	NPD6881	Approved
0.6084	Remote Similarity	NPD7320	Approved
0.6069	Remote Similarity	NPD6650	Approved
0.6069	Remote Similarity	NPD6649	Approved
0.6069	Remote Similarity	NPD8130	Phase 1
0.6053	Remote Similarity	NPD7642	Approved
0.6044	Remote Similarity	NPD8368	Discontinued
0.6042	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD8444	Approved
0.6014	Remote Similarity	NPD5697	Approved
0.6014	Remote Similarity	NPD8140	Approved
0.6014	Remote Similarity	NPD5701	Approved
0.6014	Remote Similarity	NPD4755	Approved
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD7102	Approved
0.6	Remote Similarity	NPD7290	Approved
0.6	Remote Similarity	NPD7515	Phase 2
0.6	Remote Similarity	NPD8087	Discontinued
0.6	Remote Similarity	NPD6883	Approved
0.597	Remote Similarity	NPD5328	Approved
0.5968	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.596	Remote Similarity	NPD8346	Approved
0.596	Remote Similarity	NPD8347	Approved
0.596	Remote Similarity	NPD8345	Approved
0.5959	Remote Similarity	NPD6847	Approved
0.5959	Remote Similarity	NPD6617	Approved
0.5959	Remote Similarity	NPD6869	Approved
0.5957	Remote Similarity	NPD7139	Approved
0.5957	Remote Similarity	NPD7140	Approved
0.5957	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD6399	Phase 3
0.5956	Remote Similarity	NPD4202	Approved
0.5944	Remote Similarity	NPD6008	Approved
0.5944	Remote Similarity	NPD8393	Approved
0.5931	Remote Similarity	NPD8306	Approved
0.5931	Remote Similarity	NPD6013	Approved
0.5931	Remote Similarity	NPD8305	Approved
0.5931	Remote Similarity	NPD6014	Approved
0.5931	Remote Similarity	NPD6012	Approved
0.593	Remote Similarity	NPD8417	Discontinued
0.5929	Remote Similarity	NPD4700	Approved
0.5929	Remote Similarity	NPD5286	Approved
0.5929	Remote Similarity	NPD5285	Approved
0.5929	Remote Similarity	NPD4696	Approved
0.5928	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD5983	Phase 2
0.5921	Remote Similarity	NPD8268	Approved
0.5921	Remote Similarity	NPD8266	Approved
0.5921	Remote Similarity	NPD8267	Approved
0.5921	Remote Similarity	NPD8269	Approved
0.5915	Remote Similarity	NPD8275	Approved
0.5915	Remote Similarity	NPD8276	Approved
0.5912	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD7900	Approved
0.5904	Remote Similarity	NPD8360	Approved
0.5904	Remote Similarity	NPD8361	Approved
0.5904	Remote Similarity	NPD8435	Approved
0.5899	Remote Similarity	NPD6083	Phase 2
0.5899	Remote Similarity	NPD6084	Phase 2
0.589	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5886	Remote Similarity	NPD7260	Phase 2
0.5882	Remote Similarity	NPD6079	Approved
0.5882	Remote Similarity	NPD6436	Phase 3
0.5876	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.5871	Remote Similarity	NPD6336	Discontinued
0.5865	Remote Similarity	NPD3618	Phase 1
0.5862	Remote Similarity	NPD6011	Approved
0.5857	Remote Similarity	NPD7638	Approved
0.585	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5845	Remote Similarity	NPD8082	Approved
0.5845	Remote Similarity	NPD8139	Approved
0.5845	Remote Similarity	NPD8084	Approved
0.5845	Remote Similarity	NPD5226	Approved
0.5845	Remote Similarity	NPD8138	Approved
0.5845	Remote Similarity	NPD8085	Approved
0.5845	Remote Similarity	NPD5225	Approved
0.5845	Remote Similarity	NPD8083	Approved
0.5845	Remote Similarity	NPD5211	Phase 2
0.5845	Remote Similarity	NPD5224	Approved
0.5845	Remote Similarity	NPD8086	Approved
0.5845	Remote Similarity	NPD4633	Approved
0.5844	Remote Similarity	NPD7122	Discontinued
0.5839	Remote Similarity	NPD8171	Discontinued
0.5833	Remote Similarity	NPD4786	Approved
0.5833	Remote Similarity	NPD4767	Approved
0.5833	Remote Similarity	NPD4768	Approved
0.5816	Remote Similarity	NPD7640	Approved
0.5816	Remote Similarity	NPD7639	Approved
0.5809	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD5175	Approved
0.5804	Remote Similarity	NPD5174	Approved
0.5804	Remote Similarity	NPD1407	Approved
0.5775	Remote Similarity	NPD5223	Approved
0.5772	Remote Similarity	NPD8298	Phase 2
0.5764	Remote Similarity	NPD5141	Approved
0.5764	Remote Similarity	NPD8081	Approved
0.5762	Remote Similarity	NPD7500	Approved
0.5753	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD4730	Approved
0.5753	Remote Similarity	NPD4729	Approved
0.575	Remote Similarity	NPD6845	Suspended
0.5735	Remote Similarity	NPD4753	Phase 2
0.5725	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5723	Remote Similarity	NPD5956	Approved
0.5722	Remote Similarity	NPD8485	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