NPASS Compound

Structure

NPC298469 OpenBabel07101718192D 90 98 0 0 1 0 0 0 0 0999 V2000 -9.2274 5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5802 6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3004 2.9680 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 0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6554 2.4135 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 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6010 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9403 4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6531 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2493 5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3223 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9621 4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5263 -4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5263 -5.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6603 -6.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 -5.5000 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 6.9282 -3.0000 0.0000 C 0 0 2 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 1.7321 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2583 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 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 1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2930 5.1974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 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 60 1 0 0 0 0 7 60 1 0 0 0 0 10 13 1 0 0 0 0 10 30 2 0 0 0 0 11 12 1 0 0 0 0 11 31 1 0 0 0 0 12 32 1 0 0 0 0 13 39 1 0 0 0 0 14 16 1 0 0 0 0 14 33 2 0 0 0 0 15 17 1 0 0 0 0 15 40 1 0 0 0 0 16 61 1 0 0 0 0 17 62 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 81 1 0 0 0 0 24 38 1 0 0 0 0 24 82 1 0 0 0 0 26 3 1 6 0 0 0 26 31 1 0 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 32 1 0 0 0 0 30 33 1 0 0 0 0 31 61 1 6 0 0 0 32 61 1 6 0 0 0 33 62 1 0 0 0 0 34 20 1 1 0 0 0 34 43 1 0 0 0 0 34 83 1 0 0 0 0 35 21 1 6 0 0 0 35 44 1 0 0 0 0 35 84 1 0 0 0 0 36 22 1 6 0 0 0 36 45 1 0 0 0 0 36 85 1 0 0 0 0 37 23 1 6 0 0 0 37 46 1 0 0 0 0 37 86 1 0 0 0 0 38 47 1 0 0 0 0 38 87 1 1 0 0 0 39 60 1 0 0 0 0 39 62 1 6 0 0 0 40 60 1 0 0 0 0 40 88 1 6 0 0 0 41 48 1 0 0 0 0 41 55 1 0 0 0 0 41 63 1 6 0 0 0 42 49 1 0 0 0 0 42 56 1 0 0 0 0 42 64 1 1 0 0 0 43 48 1 0 0 0 0 43 71 1 1 0 0 0 44 50 1 0 0 0 0 44 72 1 1 0 0 0 45 51 1 0 0 0 0 45 73 1 1 0 0 0 46 49 1 0 0 0 0 46 74 1 1 0 0 0 47 53 1 0 0 0 0 47 75 1 6 0 0 0 48 76 1 1 0 0 0 49 77 1 6 0 0 0 50 52 1 0 0 0 0 50 78 1 6 0 0 0 51 54 1 0 0 0 0 51 79 1 6 0 0 0 52 57 1 0 0 0 0 52 80 1 1 0 0 0 53 59 1 0 0 0 0 53 89 1 1 0 0 0 54 58 1 0 0 0 0 54 90 1 1 0 0 0 55 83 1 0 0 0 0 55 87 1 1 0 0 0 56 86 1 0 0 0 0 56 89 1 6 0 0 0 57 84 1 0 0 0 0 57 90 1 6 0 0 0 58 81 1 6 0 0 0 58 85 1 0 0 0 0 59 82 1 0 0 0 0 59 88 1 6 0 0 0 61 8 1 6 0 0 0 62 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1286.64
Volume:	1238.62
LogP:	-0.025
LogD:	1.148
LogS:	-2.239
# Rotatable Bonds:	22
TPSA:	430.56
# H-Bond Aceptor:	28
# H-Bond Donor:	15
# Rings:	9
# Heavy Atoms:	28

MedChem Properties

QED Drug-Likeness Score:	0.054
Synthetic Accessibility Score:	7.452
Fsp3:	0.855
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:	-5.884
MDCK Permeability:	0.00011865419946843758
Pgp-inhibitor:	0.977
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.175
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	59.669456481933594%
Volume Distribution (VD):	0.29
Pgp-substrate:	9.376116752624512%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.017
CYP3A4-inhibitor:	0.034
CYP3A4-substrate:	0.049

ADMET: Excretion

Clearance (CL):	0.013
Half-life (T1/2):	0.754

ADMET: Toxicity

hERG Blockers:	0.301
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.048
Maximum Recommended Daily Dose:	0.602
Skin Sensitization:	0.224
Carcinogencity:	0.012
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.236

Download Data

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

Natural Product: NPC298469

Natural Product ID:	NPC298469
*Common Name:**	Sarasinoside A2
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-4-hydroxy-6-[[(3S,5R,10S,13R,14R,17R)-4,4,10,13-tetramethyl-17-[(2R)-6-methyl-4-oxohept-5-en-2-yl]-1,2,3,5,6,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Synonyms:	Sarasinoside A2
Standard InCHIKey:	YHTMWNONXFONRB-ONJRYDCZSA-N
Standard InCHI:	InChI=1S/C62H98N2O26/c1-25(2)18-29(70)19-26(3)31-11-12-32-30-10-13-39-60(6,7)40(15-17-62(39,9)33(30)14-16-61(31,32)8)88-59-53(47(75)38(24-82-59)87-55-41(63-27(4)68)48(76)43(71)34(20-65)83-55)89-56-42(64-28(5)69)49(77)46(74)37(86-56)23-81-58-54(51(79)45(73)36(22-67)85-58)90-57-52(80)50(78)44(72)35(21-66)84-57/h10,14,18,26,31-32,34-59,65-67,71-80H,11-13,15-17,19-24H2,1-9H3,(H,63,68)(H,64,69)/t26-,31-,32+,34-,35-,36-,37-,38-,39+,40+,41-,42-,43+,44-,45-,46-,47+,48-,49-,50+,51+,52-,53-,54-,55+,56+,57+,58-,59+,61-,62-/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2CO[C@H]([C@@H]([C@H]2O)O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)O)O)[C@H]([C@@H]([C@H]2N=C(O)C)O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC=C2C3=CC[C@]3([C@H]2CC[C@@H]3[C@@H](CC(=O)C=C(C)C)C)C)C)[C@@H]([C@H]([C@H]1O)O)N=C(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071311
PubChem CID:	70688907
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal 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
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	=	8500.0	nM	PMID[559730]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	7600.0	nM	PMID[559730]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[559730]

☑ 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 NPC298469 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	166
0.1-0.2	1001
0.2-0.3	4317
0.3-0.4	15589
0.4-0.5	11968
0.5-0.6	6584
0.6-0.7	2155
0.7-0.8	862
0.8-0.85	4
0.85-0.9	30
0.9-0.95	16
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9848	High Similarity	NPC193579
0.9847	High Similarity	NPC162910
0.9695	High Similarity	NPC180770
0.9695	High Similarity	NPC302276
0.9407	High Similarity	NPC141669
0.9254	High Similarity	NPC265908
0.9209	High Similarity	NPC36463
0.9209	High Similarity	NPC298005
0.9197	High Similarity	NPC298067
0.9197	High Similarity	NPC214821
0.9124	High Similarity	NPC69176
0.9124	High Similarity	NPC284625
0.9065	High Similarity	NPC61717
0.9065	High Similarity	NPC244380
0.8741	High Similarity	NPC477072
0.8731	High Similarity	NPC139585
0.8676	High Similarity	NPC280941
0.8676	High Similarity	NPC235772
0.8643	High Similarity	NPC475584
0.8643	High Similarity	NPC475394
0.8643	High Similarity	NPC475152
0.8582	High Similarity	NPC475892
0.8529	High Similarity	NPC119794
0.8529	High Similarity	NPC73829
0.85	High Similarity	NPC172365
0.85	High Similarity	NPC82931
0.85	High Similarity	NPC210729
0.8489	Intermediate Similarity	NPC243680
0.8489	Intermediate Similarity	NPC200788
0.8456	Intermediate Similarity	NPC475472
0.8406	Intermediate Similarity	NPC75318
0.8367	Intermediate Similarity	NPC475527
0.8367	Intermediate Similarity	NPC265699
0.8345	Intermediate Similarity	NPC145899
0.8333	Intermediate Similarity	NPC76999
0.8311	Intermediate Similarity	NPC113620
0.8311	Intermediate Similarity	NPC187497
0.8311	Intermediate Similarity	NPC100612
0.8311	Intermediate Similarity	NPC475599
0.8311	Intermediate Similarity	NPC174336
0.7926	Intermediate Similarity	NPC476675
0.7868	Intermediate Similarity	NPC469943
0.7778	Intermediate Similarity	NPC197003
0.7778	Intermediate Similarity	NPC190939
0.7755	Intermediate Similarity	NPC803
0.7721	Intermediate Similarity	NPC308459
0.7687	Intermediate Similarity	NPC279638
0.7683	Intermediate Similarity	NPC476113
0.7664	Intermediate Similarity	NPC476672
0.7626	Intermediate Similarity	NPC473505
0.7591	Intermediate Similarity	NPC476670
0.7537	Intermediate Similarity	NPC251309
0.7537	Intermediate Similarity	NPC260665
0.7519	Intermediate Similarity	NPC292196
0.75	Intermediate Similarity	NPC476674
0.7485	Intermediate Similarity	NPC475345
0.7481	Intermediate Similarity	NPC165439
0.7464	Intermediate Similarity	NPC129393
0.7463	Intermediate Similarity	NPC210420
0.7463	Intermediate Similarity	NPC233003
0.7463	Intermediate Similarity	NPC474265
0.7447	Intermediate Similarity	NPC476673
0.7444	Intermediate Similarity	NPC129340
0.744	Intermediate Similarity	NPC475649
0.7407	Intermediate Similarity	NPC477074
0.7394	Intermediate Similarity	NPC278272
0.7394	Intermediate Similarity	NPC120667
0.7376	Intermediate Similarity	NPC248202
0.7368	Intermediate Similarity	NPC265655
0.7361	Intermediate Similarity	NPC201359
0.7357	Intermediate Similarity	NPC305771
0.7357	Intermediate Similarity	NPC94072
0.7357	Intermediate Similarity	NPC169816
0.7357	Intermediate Similarity	NPC15918
0.7353	Intermediate Similarity	NPC471385
0.7353	Intermediate Similarity	NPC204414
0.7353	Intermediate Similarity	NPC471550
0.7353	Intermediate Similarity	NPC298034
0.7353	Intermediate Similarity	NPC54636
0.7353	Intermediate Similarity	NPC475160
0.7353	Intermediate Similarity	NPC100639
0.7353	Intermediate Similarity	NPC76972
0.7353	Intermediate Similarity	NPC123199
0.7353	Intermediate Similarity	NPC79643
0.7353	Intermediate Similarity	NPC305981
0.7353	Intermediate Similarity	NPC261506
0.7353	Intermediate Similarity	NPC476068
0.7353	Intermediate Similarity	NPC60557
0.7353	Intermediate Similarity	NPC473714
0.7353	Intermediate Similarity	NPC43550
0.7353	Intermediate Similarity	NPC70809
0.7353	Intermediate Similarity	NPC250247
0.7353	Intermediate Similarity	NPC57484
0.7353	Intermediate Similarity	NPC293330
0.7353	Intermediate Similarity	NPC469782
0.7353	Intermediate Similarity	NPC473882
0.7353	Intermediate Similarity	NPC161717
0.7353	Intermediate Similarity	NPC224381
0.7353	Intermediate Similarity	NPC41061
0.7353	Intermediate Similarity	NPC71065
0.7353	Intermediate Similarity	NPC475140
0.7353	Intermediate Similarity	NPC227551
0.7353	Intermediate Similarity	NPC4328
0.7353	Intermediate Similarity	NPC65105
0.7353	Intermediate Similarity	NPC67857
0.7353	Intermediate Similarity	NPC294453
0.7353	Intermediate Similarity	NPC309907
0.7353	Intermediate Similarity	NPC236638
0.7353	Intermediate Similarity	NPC474557
0.7353	Intermediate Similarity	NPC119592
0.7353	Intermediate Similarity	NPC202828
0.7353	Intermediate Similarity	NPC74727
0.7319	Intermediate Similarity	NPC470514
0.7319	Intermediate Similarity	NPC470513
0.7313	Intermediate Similarity	NPC475317
0.7313	Intermediate Similarity	NPC52241
0.7313	Intermediate Similarity	NPC154856
0.7305	Intermediate Similarity	NPC228701
0.7305	Intermediate Similarity	NPC256983
0.7299	Intermediate Similarity	NPC473126
0.7299	Intermediate Similarity	NPC472718
0.7293	Intermediate Similarity	NPC195708
0.7286	Intermediate Similarity	NPC202051
0.7286	Intermediate Similarity	NPC476545
0.7286	Intermediate Similarity	NPC476544
0.7286	Intermediate Similarity	NPC249553
0.7286	Intermediate Similarity	NPC475182
0.7286	Intermediate Similarity	NPC476543
0.7286	Intermediate Similarity	NPC182900
0.7279	Intermediate Similarity	NPC151543
0.7279	Intermediate Similarity	NPC475467
0.7279	Intermediate Similarity	NPC114304
0.7279	Intermediate Similarity	NPC174720
0.7279	Intermediate Similarity	NPC192600
0.7279	Intermediate Similarity	NPC219180
0.7279	Intermediate Similarity	NPC323341
0.7279	Intermediate Similarity	NPC241909
0.7279	Intermediate Similarity	NPC166422
0.7279	Intermediate Similarity	NPC133818
0.7279	Intermediate Similarity	NPC155410
0.7279	Intermediate Similarity	NPC473826
0.7279	Intermediate Similarity	NPC251263
0.7279	Intermediate Similarity	NPC295823
0.7279	Intermediate Similarity	NPC309714
0.7279	Intermediate Similarity	NPC73455
0.7279	Intermediate Similarity	NPC46665
0.7279	Intermediate Similarity	NPC200944
0.7279	Intermediate Similarity	NPC114287
0.7279	Intermediate Similarity	NPC475287
0.7266	Intermediate Similarity	NPC473401
0.7266	Intermediate Similarity	NPC477464
0.7259	Intermediate Similarity	NPC250481
0.7259	Intermediate Similarity	NPC285410
0.7259	Intermediate Similarity	NPC263827
0.7259	Intermediate Similarity	NPC477073
0.7254	Intermediate Similarity	NPC473474
0.7254	Intermediate Similarity	NPC130229
0.7254	Intermediate Similarity	NPC471090
0.7246	Intermediate Similarity	NPC185466
0.7246	Intermediate Similarity	NPC85154
0.7246	Intermediate Similarity	NPC220160
0.7246	Intermediate Similarity	NPC148417
0.7246	Intermediate Similarity	NPC136768
0.7246	Intermediate Similarity	NPC286457
0.7246	Intermediate Similarity	NPC191827
0.7246	Intermediate Similarity	NPC102505
0.7246	Intermediate Similarity	NPC123522
0.7246	Intermediate Similarity	NPC69811
0.7246	Intermediate Similarity	NPC475209
0.7246	Intermediate Similarity	NPC473452
0.7246	Intermediate Similarity	NPC471580
0.7246	Intermediate Similarity	NPC104137
0.7246	Intermediate Similarity	NPC309223
0.7246	Intermediate Similarity	NPC470876
0.7246	Intermediate Similarity	NPC110633
0.7246	Intermediate Similarity	NPC33012
0.7246	Intermediate Similarity	NPC8524
0.7246	Intermediate Similarity	NPC475514
0.7239	Intermediate Similarity	NPC302057
0.7239	Intermediate Similarity	NPC246205
0.7234	Intermediate Similarity	NPC131824
0.7214	Intermediate Similarity	NPC475187
0.7206	Intermediate Similarity	NPC109079
0.7206	Intermediate Similarity	NPC276093
0.7206	Intermediate Similarity	NPC104071
0.7206	Intermediate Similarity	NPC101744
0.7206	Intermediate Similarity	NPC473373
0.7206	Intermediate Similarity	NPC79718
0.7206	Intermediate Similarity	NPC475516
0.7206	Intermediate Similarity	NPC292677
0.7206	Intermediate Similarity	NPC471383
0.7206	Intermediate Similarity	NPC10320
0.7206	Intermediate Similarity	NPC477253
0.7206	Intermediate Similarity	NPC471967
0.7206	Intermediate Similarity	NPC130427
0.7206	Intermediate Similarity	NPC104400
0.7206	Intermediate Similarity	NPC139044
0.7206	Intermediate Similarity	NPC324875
0.7206	Intermediate Similarity	NPC102439
0.7206	Intermediate Similarity	NPC161434

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 NPC298469 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	130
0.1-0.2	662
0.2-0.3	3201
0.3-0.4	3718
0.4-0.5	989
0.5-0.6	373
0.6-0.7	62
0.7-0.8	15
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
0.7095	Intermediate Similarity	NPD8450	Suspended
0.709	Intermediate Similarity	NPD6412	Phase 2
0.7027	Intermediate Similarity	NPD8449	Approved
0.6986	Remote Similarity	NPD8336	Approved
0.6986	Remote Similarity	NPD8337	Approved
0.6944	Remote Similarity	NPD8328	Phase 3
0.6892	Remote Similarity	NPD6914	Discontinued
0.6861	Remote Similarity	NPD8132	Clinical (unspecified phase)
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
0.6786	Remote Similarity	NPD8133	Approved
0.6772	Remote Similarity	NPD7625	Phase 1
0.6736	Remote Similarity	NPD8377	Approved
0.6736	Remote Similarity	NPD8294	Approved
0.669	Remote Similarity	NPD8378	Approved
0.669	Remote Similarity	NPD8379	Approved
0.669	Remote Similarity	NPD8296	Approved
0.669	Remote Similarity	NPD8335	Approved
0.669	Remote Similarity	NPD8380	Approved
0.6622	Remote Similarity	NPD7507	Approved
0.6575	Remote Similarity	NPD8033	Approved
0.6575	Remote Similarity	NPD7503	Approved
0.6556	Remote Similarity	NPD8392	Approved
0.6556	Remote Similarity	NPD8391	Approved
0.6556	Remote Similarity	NPD8390	Approved
0.6533	Remote Similarity	NPD7736	Approved
0.6531	Remote Similarity	NPD6370	Approved
0.649	Remote Similarity	NPD7319	Approved
0.6483	Remote Similarity	NPD7641	Discontinued
0.6467	Remote Similarity	NPD8293	Discontinued
0.6463	Remote Similarity	NPD8517	Approved
0.6463	Remote Similarity	NPD8516	Approved
0.6463	Remote Similarity	NPD8515	Approved
0.6429	Remote Similarity	NPD6686	Approved
0.6414	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6059	Approved
0.6395	Remote Similarity	NPD6054	Approved
0.637	Remote Similarity	NPD7328	Approved
0.637	Remote Similarity	NPD7327	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	NPD6909	Approved
0.6351	Remote Similarity	NPD6908	Approved
0.6333	Remote Similarity	NPD8341	Approved
0.6333	Remote Similarity	NPD8340	Approved
0.6333	Remote Similarity	NPD8342	Approved
0.6333	Remote Similarity	NPD8299	Approved
0.6331	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD7516	Approved
0.6309	Remote Similarity	NPD8080	Discontinued
0.6291	Remote Similarity	NPD8451	Approved
0.6267	Remote Similarity	NPD6067	Discontinued
0.6267	Remote Similarity	NPD7829	Approved
0.6267	Remote Similarity	NPD7830	Approved
0.625	Remote Similarity	NPD6882	Approved
0.625	Remote Similarity	NPD8297	Approved
0.6242	Remote Similarity	NPD6016	Approved
0.6242	Remote Similarity	NPD6015	Approved
0.6236	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD6940	Discontinued
0.6225	Remote Similarity	NPD7492	Approved
0.6224	Remote Similarity	NPD6421	Discontinued
0.62	Remote Similarity	NPD5988	Approved
0.6194	Remote Similarity	NPD7260	Phase 2
0.619	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6009	Approved
0.6184	Remote Similarity	NPD6616	Approved
0.6174	Remote Similarity	NPD6319	Approved
0.6159	Remote Similarity	NPD7604	Phase 2
0.6159	Remote Similarity	NPD8418	Phase 2
0.6144	Remote Similarity	NPD7078	Approved
0.6139	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6138	Remote Similarity	NPD6429	Approved
0.6138	Remote Similarity	NPD6430	Approved
0.6133	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD8444	Approved
0.6096	Remote Similarity	NPD4632	Approved
0.6076	Remote Similarity	NPD8415	Approved
0.6056	Remote Similarity	NPD6675	Approved
0.6056	Remote Similarity	NPD6402	Approved
0.6056	Remote Similarity	NPD7128	Approved
0.6056	Remote Similarity	NPD5739	Approved
0.6051	Remote Similarity	NPD6845	Suspended
0.6043	Remote Similarity	NPD6404	Discontinued
0.6042	Remote Similarity	NPD6372	Approved
0.6042	Remote Similarity	NPD6373	Approved
0.6029	Remote Similarity	NPD7748	Approved
0.6014	Remote Similarity	NPD7902	Approved
0.6014	Remote Similarity	NPD8307	Discontinued
0.6	Remote Similarity	NPD6033	Approved
0.5973	Remote Similarity	NPD7115	Discovery
0.5972	Remote Similarity	NPD6899	Approved
0.5972	Remote Similarity	NPD7320	Approved
0.5972	Remote Similarity	NPD6881	Approved
0.597	Remote Similarity	NPD5328	Approved
0.5959	Remote Similarity	NPD6650	Approved
0.5959	Remote Similarity	NPD8130	Phase 1
0.5959	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5959	Remote Similarity	NPD6649	Approved
0.5957	Remote Similarity	NPD7140	Approved
0.5957	Remote Similarity	NPD7139	Approved
0.5957	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD8407	Phase 2
0.5944	Remote Similarity	NPD5357	Phase 1
0.593	Remote Similarity	NPD8417	Discontinued
0.5903	Remote Similarity	NPD8140	Approved
0.5903	Remote Similarity	NPD5701	Approved
0.5903	Remote Similarity	NPD5697	Approved
0.5899	Remote Similarity	NPD4755	Approved
0.589	Remote Similarity	NPD8087	Discontinued
0.589	Remote Similarity	NPD7290	Approved
0.589	Remote Similarity	NPD6883	Approved
0.589	Remote Similarity	NPD7102	Approved
0.589	Remote Similarity	NPD4634	Approved
0.5882	Remote Similarity	NPD6079	Approved
0.5882	Remote Similarity	NPD7515	Phase 2
0.587	Remote Similarity	NPD8368	Discontinued
0.5867	Remote Similarity	NPD7500	Approved
0.5865	Remote Similarity	NPD3618	Phase 1
0.5865	Remote Similarity	NPD5279	Phase 3
0.5857	Remote Similarity	NPD7638	Approved
0.5855	Remote Similarity	NPD8347	Approved
0.5855	Remote Similarity	NPD8346	Approved
0.5855	Remote Similarity	NPD8345	Approved
0.585	Remote Similarity	NPD6847	Approved
0.585	Remote Similarity	NPD6617	Approved
0.585	Remote Similarity	NPD6869	Approved
0.5844	Remote Similarity	NPD7642	Approved
0.5844	Remote Similarity	NPD7122	Discontinued
0.5839	Remote Similarity	NPD4202	Approved
0.5839	Remote Similarity	NPD6399	Phase 3
0.5839	Remote Similarity	NPD8171	Discontinued
0.5833	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8393	Approved
0.5822	Remote Similarity	NPD8306	Approved
0.5822	Remote Similarity	NPD6013	Approved
0.5822	Remote Similarity	NPD6014	Approved
0.5822	Remote Similarity	NPD6012	Approved
0.5822	Remote Similarity	NPD8305	Approved
0.5817	Remote Similarity	NPD8266	Approved
0.5817	Remote Similarity	NPD8267	Approved
0.5817	Remote Similarity	NPD6921	Approved
0.5817	Remote Similarity	NPD5983	Phase 2
0.5817	Remote Similarity	NPD8268	Approved
0.5817	Remote Similarity	NPD8269	Approved
0.5816	Remote Similarity	NPD5285	Approved
0.5816	Remote Similarity	NPD7640	Approved
0.5816	Remote Similarity	NPD4700	Approved
0.5816	Remote Similarity	NPD5286	Approved
0.5816	Remote Similarity	NPD4696	Approved
0.5816	Remote Similarity	NPD7639	Approved
0.5809	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD8276	Approved
0.5804	Remote Similarity	NPD8275	Approved
0.5798	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD7900	Approved
0.5786	Remote Similarity	NPD6083	Phase 2
0.5786	Remote Similarity	NPD6084	Phase 2
0.5772	Remote Similarity	NPD8298	Phase 2
0.5769	Remote Similarity	NPD6336	Discontinued
0.5755	Remote Similarity	NPD5695	Phase 3
0.5753	Remote Similarity	NPD6011	Approved
0.5743	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5737	Remote Similarity	NPD8435	Approved
0.5737	Remote Similarity	NPD8360	Approved
0.5737	Remote Similarity	NPD8361	Approved
0.5734	Remote Similarity	NPD5211	Phase 2
0.5734	Remote Similarity	NPD8085	Approved
0.5734	Remote Similarity	NPD8083	Approved
0.5734	Remote Similarity	NPD5226	Approved
0.5734	Remote Similarity	NPD8086	Approved
0.5734	Remote Similarity	NPD8084	Approved
0.5734	Remote Similarity	NPD8082	Approved
0.5734	Remote Similarity	NPD8138	Approved
0.5734	Remote Similarity	NPD5225	Approved
0.5734	Remote Similarity	NPD5224	Approved
0.5734	Remote Similarity	NPD8139	Approved
0.5734	Remote Similarity	NPD4633	Approved
0.5725	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5724	Remote Similarity	NPD4768	Approved
0.5724	Remote Similarity	NPD6008	Approved
0.5724	Remote Similarity	NPD7333	Discontinued
0.5724	Remote Similarity	NPD4767	Approved
0.5714	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4786	Approved
0.5714	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4697	Phase 3
0.5714	Remote Similarity	NPD5222	Approved
0.5714	Remote Similarity	NPD5221	Approved
0.5714	Remote Similarity	NPD6941	Approved
0.5694	Remote Similarity	NPD5175	Approved
0.5694	Remote Similarity	NPD5174	Approved
0.5694	Remote Similarity	NPD1407	Approved
0.5677	Remote Similarity	NPD6436	Phase 3

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