NPASS Compound

Structure

NPC162910 OpenBabel07101718242D 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 1 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 1 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 2 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:	1288.66
Volume:	1241.257
LogP:	0.35
LogD:	1.241
LogS:	-2.162
# 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:	0.044
Synthetic Accessibility Score:	7.389
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:	-5.996
MDCK Permeability:	0.00015457606059499085
Pgp-inhibitor:	0.518
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.335
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.038
Plasma Protein Binding (PPB):	69.65470886230469%
Volume Distribution (VD):	0.294
Pgp-substrate:	9.714184761047363%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.02
CYP3A4-inhibitor:	0.045
CYP3A4-substrate:	0.034

ADMET: Excretion

Clearance (CL):	-0.057
Half-life (T1/2):	0.74

ADMET: Toxicity

hERG Blockers:	0.191
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.269
AMES Toxicity:	0.074
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.097
Carcinogencity:	0.006
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC162910

Natural Product ID:	NPC162910
*Common Name:**	Sarasinoside A1
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]-1,2,3,5,6,7,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Synonyms:	Sarasinoside A1
Standard InCHIKey:	YMIDOMYJFRKBJR-ONJRYDCZSA-N
Standard InCHI:	InChI=1S/C62H100N2O26/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/h18,26,31-32,34-59,65-67,71-80H,10-17,19-24H2,1-9H3,(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:	CC(=CC(=O)C[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1CC3)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)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510197
PubChem CID:	14019702
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
NPO32754	melophlus isis	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924165]
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	4

Activity Type	# Activity
Cell Line	3
Organism	1
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	=	6.5	ug.mL-1	PMID[493377]
NPT111	Cell Line	K562	Homo sapiens	LC50	=	7400.0	nM	PMID[493379]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	7600.0	nM	PMID[493379]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	=	10.0	mm	PMID[493378]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	=	60.0	ug.mL-1	PMID[493379]

☑ 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 NPC162910 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	163
0.1-0.2	1068
0.2-0.3	4945
0.3-0.4	15796
0.4-0.5	11080
0.5-0.6	6348
0.6-0.7	2206
0.7-0.8	1035
0.8-0.85	5
0.85-0.9	22
0.9-0.95	22
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9847	High Similarity	NPC298469
0.9845	High Similarity	NPC180770
0.9845	High Similarity	NPC302276
0.9697	High Similarity	NPC193579
0.9549	High Similarity	NPC141669
0.9394	High Similarity	NPC265908
0.9343	High Similarity	NPC36463
0.9343	High Similarity	NPC298005
0.9333	High Similarity	NPC214821
0.9333	High Similarity	NPC298067
0.9259	High Similarity	NPC69176
0.9259	High Similarity	NPC284625
0.9197	High Similarity	NPC61717
0.9197	High Similarity	NPC244380
0.8872	High Similarity	NPC477072
0.8864	High Similarity	NPC139585
0.8806	High Similarity	NPC235772
0.8806	High Similarity	NPC280941
0.8768	High Similarity	NPC475394
0.8768	High Similarity	NPC475584
0.8768	High Similarity	NPC475152
0.8705	High Similarity	NPC475892
0.8657	High Similarity	NPC119794
0.8657	High Similarity	NPC73829
0.8623	High Similarity	NPC172365
0.8623	High Similarity	NPC82931
0.8623	High Similarity	NPC210729
0.8613	High Similarity	NPC243680
0.8613	High Similarity	NPC200788
0.8582	High Similarity	NPC475472
0.8529	High Similarity	NPC75318
0.8483	Intermediate Similarity	NPC475527
0.8483	Intermediate Similarity	NPC265699
0.8467	Intermediate Similarity	NPC145899
0.8456	Intermediate Similarity	NPC76999
0.8425	Intermediate Similarity	NPC100612
0.8425	Intermediate Similarity	NPC174336
0.8425	Intermediate Similarity	NPC113620
0.8425	Intermediate Similarity	NPC475599
0.8425	Intermediate Similarity	NPC187497
0.8045	Intermediate Similarity	NPC476675
0.7985	Intermediate Similarity	NPC469943
0.7895	Intermediate Similarity	NPC190939
0.7895	Intermediate Similarity	NPC197003
0.7862	Intermediate Similarity	NPC803
0.7836	Intermediate Similarity	NPC308459
0.7803	Intermediate Similarity	NPC279638
0.7778	Intermediate Similarity	NPC476672
0.7737	Intermediate Similarity	NPC473505
0.7704	Intermediate Similarity	NPC476670
0.7652	Intermediate Similarity	NPC251309
0.7652	Intermediate Similarity	NPC260665
0.7609	Intermediate Similarity	NPC476674
0.7594	Intermediate Similarity	NPC165439
0.7576	Intermediate Similarity	NPC474265
0.7576	Intermediate Similarity	NPC233003
0.7576	Intermediate Similarity	NPC210420
0.7574	Intermediate Similarity	NPC129393
0.7561	Intermediate Similarity	NPC476113
0.7557	Intermediate Similarity	NPC129340
0.7554	Intermediate Similarity	NPC476673
0.7519	Intermediate Similarity	NPC477074
0.7482	Intermediate Similarity	NPC248202
0.7481	Intermediate Similarity	NPC265655
0.7465	Intermediate Similarity	NPC201359
0.7464	Intermediate Similarity	NPC169816
0.7464	Intermediate Similarity	NPC15918
0.7464	Intermediate Similarity	NPC94072
0.7464	Intermediate Similarity	NPC305771
0.7463	Intermediate Similarity	NPC41061
0.7463	Intermediate Similarity	NPC293330
0.7463	Intermediate Similarity	NPC71065
0.7463	Intermediate Similarity	NPC54636
0.7463	Intermediate Similarity	NPC469782
0.7463	Intermediate Similarity	NPC473882
0.7463	Intermediate Similarity	NPC70809
0.7463	Intermediate Similarity	NPC202828
0.7463	Intermediate Similarity	NPC294453
0.7463	Intermediate Similarity	NPC76972
0.7463	Intermediate Similarity	NPC60557
0.7463	Intermediate Similarity	NPC67857
0.7463	Intermediate Similarity	NPC309907
0.7463	Intermediate Similarity	NPC298034
0.7463	Intermediate Similarity	NPC476068
0.7463	Intermediate Similarity	NPC261506
0.7463	Intermediate Similarity	NPC475140
0.7463	Intermediate Similarity	NPC471550
0.7463	Intermediate Similarity	NPC4328
0.7463	Intermediate Similarity	NPC65105
0.7463	Intermediate Similarity	NPC123199
0.7463	Intermediate Similarity	NPC474557
0.7463	Intermediate Similarity	NPC475160
0.7463	Intermediate Similarity	NPC119592
0.7463	Intermediate Similarity	NPC57484
0.7463	Intermediate Similarity	NPC74727
0.7463	Intermediate Similarity	NPC236638
0.7463	Intermediate Similarity	NPC471385
0.7463	Intermediate Similarity	NPC250247
0.7463	Intermediate Similarity	NPC305981
0.7463	Intermediate Similarity	NPC224381
0.7463	Intermediate Similarity	NPC161717
0.7463	Intermediate Similarity	NPC473714
0.7463	Intermediate Similarity	NPC100639
0.7463	Intermediate Similarity	NPC227551
0.7463	Intermediate Similarity	NPC204414
0.7463	Intermediate Similarity	NPC79643
0.7463	Intermediate Similarity	NPC43550
0.7426	Intermediate Similarity	NPC470513
0.7426	Intermediate Similarity	NPC470514
0.7424	Intermediate Similarity	NPC154856
0.7424	Intermediate Similarity	NPC52241
0.7424	Intermediate Similarity	NPC475317
0.741	Intermediate Similarity	NPC228701
0.741	Intermediate Similarity	NPC256983
0.7407	Intermediate Similarity	NPC472718
0.7405	Intermediate Similarity	NPC195708
0.7391	Intermediate Similarity	NPC202051
0.7391	Intermediate Similarity	NPC475182
0.7391	Intermediate Similarity	NPC476543
0.7391	Intermediate Similarity	NPC249553
0.7391	Intermediate Similarity	NPC476544
0.7391	Intermediate Similarity	NPC476545
0.7391	Intermediate Similarity	NPC182900
0.7388	Intermediate Similarity	NPC241909
0.7388	Intermediate Similarity	NPC46665
0.7388	Intermediate Similarity	NPC151543
0.7388	Intermediate Similarity	NPC309714
0.7388	Intermediate Similarity	NPC174720
0.7388	Intermediate Similarity	NPC192600
0.7388	Intermediate Similarity	NPC133818
0.7388	Intermediate Similarity	NPC219180
0.7388	Intermediate Similarity	NPC155410
0.7388	Intermediate Similarity	NPC295823
0.7388	Intermediate Similarity	NPC251263
0.7388	Intermediate Similarity	NPC473826
0.7388	Intermediate Similarity	NPC475287
0.7388	Intermediate Similarity	NPC114304
0.7388	Intermediate Similarity	NPC323341
0.7388	Intermediate Similarity	NPC114287
0.7388	Intermediate Similarity	NPC475467
0.7388	Intermediate Similarity	NPC166422
0.7372	Intermediate Similarity	NPC473401
0.7372	Intermediate Similarity	NPC477464
0.7368	Intermediate Similarity	NPC250481
0.7368	Intermediate Similarity	NPC263827
0.7368	Intermediate Similarity	NPC477073
0.7368	Intermediate Similarity	NPC292196
0.7368	Intermediate Similarity	NPC285410
0.7365	Intermediate Similarity	NPC475345
0.7357	Intermediate Similarity	NPC130229
0.7357	Intermediate Similarity	NPC473474
0.7353	Intermediate Similarity	NPC475209
0.7353	Intermediate Similarity	NPC8524
0.7353	Intermediate Similarity	NPC85154
0.7353	Intermediate Similarity	NPC470876
0.7353	Intermediate Similarity	NPC69811
0.7353	Intermediate Similarity	NPC473452
0.7353	Intermediate Similarity	NPC220160
0.7353	Intermediate Similarity	NPC185466
0.7353	Intermediate Similarity	NPC33012
0.7353	Intermediate Similarity	NPC148417
0.7353	Intermediate Similarity	NPC286457
0.7353	Intermediate Similarity	NPC110633
0.7353	Intermediate Similarity	NPC102505
0.7353	Intermediate Similarity	NPC123522
0.7353	Intermediate Similarity	NPC191827
0.7353	Intermediate Similarity	NPC475514
0.7353	Intermediate Similarity	NPC104137
0.7353	Intermediate Similarity	NPC309223
0.7353	Intermediate Similarity	NPC136768
0.7353	Intermediate Similarity	NPC471580
0.7348	Intermediate Similarity	NPC246205
0.7348	Intermediate Similarity	NPC302057
0.7338	Intermediate Similarity	NPC131824
0.7321	Intermediate Similarity	NPC475649
0.7319	Intermediate Similarity	NPC475187
0.7313	Intermediate Similarity	NPC324875
0.7313	Intermediate Similarity	NPC475504
0.7313	Intermediate Similarity	NPC104400
0.7313	Intermediate Similarity	NPC101744
0.7313	Intermediate Similarity	NPC471383
0.7313	Intermediate Similarity	NPC104071
0.7313	Intermediate Similarity	NPC79718
0.7313	Intermediate Similarity	NPC477253
0.7313	Intermediate Similarity	NPC469946
0.7313	Intermediate Similarity	NPC471967
0.7313	Intermediate Similarity	NPC276093
0.7313	Intermediate Similarity	NPC473373
0.7313	Intermediate Similarity	NPC292677
0.7313	Intermediate Similarity	NPC109079
0.7313	Intermediate Similarity	NPC130427
0.7313	Intermediate Similarity	NPC257468
0.7313	Intermediate Similarity	NPC139044
0.7313	Intermediate Similarity	NPC102439
0.7313	Intermediate Similarity	NPC475516
0.7313	Intermediate Similarity	NPC10320
0.7305	Intermediate Similarity	NPC48886
0.7305	Intermediate Similarity	NPC94881
0.7305	Intermediate Similarity	NPC265275
0.7299	Intermediate Similarity	NPC475899

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 NPC162910 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	123
0.1-0.2	746
0.2-0.3	3487
0.3-0.4	3486
0.4-0.5	883
0.5-0.6	343
0.6-0.7	65
0.7-0.8	17
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
0.7197	Intermediate Similarity	NPD6412	Phase 2
0.7192	Intermediate Similarity	NPD8450	Suspended
0.7123	Intermediate Similarity	NPD8449	Approved
0.7083	Intermediate Similarity	NPD8336	Approved
0.7083	Intermediate Similarity	NPD8337	Approved
0.7042	Intermediate Similarity	NPD8328	Phase 3
0.6986	Remote Similarity	NPD6914	Discontinued
0.6963	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD8338	Approved
0.6889	Remote Similarity	NPD8174	Phase 2
0.6887	Remote Similarity	NPD6334	Approved
0.6887	Remote Similarity	NPD6333	Approved
0.6884	Remote Similarity	NPD8133	Approved
0.6859	Remote Similarity	NPD7625	Phase 1
0.6831	Remote Similarity	NPD8294	Approved
0.6831	Remote Similarity	NPD8377	Approved
0.6783	Remote Similarity	NPD8380	Approved
0.6783	Remote Similarity	NPD8296	Approved
0.6783	Remote Similarity	NPD8378	Approved
0.6783	Remote Similarity	NPD8379	Approved
0.6783	Remote Similarity	NPD8335	Approved
0.6712	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6622	Remote Similarity	NPD7736	Approved
0.6621	Remote Similarity	NPD6370	Approved
0.6577	Remote Similarity	NPD7319	Approved
0.6554	Remote Similarity	NPD8293	Discontinued
0.6522	Remote Similarity	NPD6686	Approved
0.6503	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD6059	Approved
0.6483	Remote Similarity	NPD6054	Approved
0.6458	Remote Similarity	NPD7327	Approved
0.6458	Remote Similarity	NPD7328	Approved
0.6438	Remote Similarity	NPD7503	Approved
0.6438	Remote Similarity	NPD6909	Approved
0.6438	Remote Similarity	NPD6908	Approved
0.6424	Remote Similarity	NPD8392	Approved
0.6424	Remote Similarity	NPD8391	Approved
0.6424	Remote Similarity	NPD8390	Approved
0.6423	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD7516	Approved
0.6395	Remote Similarity	NPD8080	Discontinued
0.6351	Remote Similarity	NPD6067	Discontinued
0.6345	Remote Similarity	NPD7641	Discontinued
0.6338	Remote Similarity	NPD6882	Approved
0.6338	Remote Similarity	NPD8297	Approved
0.6327	Remote Similarity	NPD6016	Approved
0.6327	Remote Similarity	NPD8516	Approved
0.6327	Remote Similarity	NPD6015	Approved
0.6327	Remote Similarity	NPD8517	Approved
0.6327	Remote Similarity	NPD8515	Approved
0.6319	Remote Similarity	NPD6940	Discontinued
0.6312	Remote Similarity	NPD6421	Discontinued
0.6309	Remote Similarity	NPD7492	Approved
0.6284	Remote Similarity	NPD5988	Approved
0.6276	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD6009	Approved
0.6267	Remote Similarity	NPD6616	Approved
0.6259	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD8418	Phase 2
0.6242	Remote Similarity	NPD7604	Phase 2
0.6225	Remote Similarity	NPD8448	Approved
0.6225	Remote Similarity	NPD7078	Approved
0.6225	Remote Similarity	NPD8074	Phase 3
0.6224	Remote Similarity	NPD6430	Approved
0.6224	Remote Similarity	NPD6429	Approved
0.6218	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8513	Phase 3
0.62	Remote Similarity	NPD8340	Approved
0.62	Remote Similarity	NPD8299	Approved
0.62	Remote Similarity	NPD8341	Approved
0.62	Remote Similarity	NPD8342	Approved
0.6181	Remote Similarity	NPD4632	Approved
0.6159	Remote Similarity	NPD8451	Approved
0.6154	Remote Similarity	NPD8415	Approved
0.6143	Remote Similarity	NPD6402	Approved
0.6143	Remote Similarity	NPD5739	Approved
0.6143	Remote Similarity	NPD7128	Approved
0.6143	Remote Similarity	NPD6675	Approved
0.6133	Remote Similarity	NPD7829	Approved
0.6133	Remote Similarity	NPD7830	Approved
0.6127	Remote Similarity	NPD6373	Approved
0.6127	Remote Similarity	NPD6372	Approved
0.6124	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD7748	Approved
0.6103	Remote Similarity	NPD7902	Approved
0.6099	Remote Similarity	NPD8307	Discontinued
0.6078	Remote Similarity	NPD6033	Approved
0.6065	Remote Similarity	NPD7260	Phase 2
0.6061	Remote Similarity	NPD5328	Approved
0.6056	Remote Similarity	NPD6881	Approved
0.6056	Remote Similarity	NPD6899	Approved
0.6056	Remote Similarity	NPD7320	Approved
0.6054	Remote Similarity	NPD7115	Discovery
0.6043	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.6043	Remote Similarity	NPD7140	Approved
0.6043	Remote Similarity	NPD7139	Approved
0.6042	Remote Similarity	NPD6649	Approved
0.6042	Remote Similarity	NPD6650	Approved
0.6042	Remote Similarity	NPD8130	Phase 1
0.6042	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6028	Remote Similarity	NPD5357	Phase 1
0.6	Remote Similarity	NPD8444	Approved
0.5986	Remote Similarity	NPD8140	Approved
0.5986	Remote Similarity	NPD5701	Approved
0.5986	Remote Similarity	NPD5697	Approved
0.5985	Remote Similarity	NPD4755	Approved
0.5972	Remote Similarity	NPD6883	Approved
0.5972	Remote Similarity	NPD8087	Discontinued
0.5972	Remote Similarity	NPD4634	Approved
0.5972	Remote Similarity	NPD7290	Approved
0.5972	Remote Similarity	NPD7102	Approved
0.597	Remote Similarity	NPD6079	Approved
0.597	Remote Similarity	NPD7515	Phase 2
0.5954	Remote Similarity	NPD3618	Phase 1
0.5942	Remote Similarity	NPD7638	Approved
0.5933	Remote Similarity	NPD8346	Approved
0.5933	Remote Similarity	NPD8347	Approved
0.5933	Remote Similarity	NPD8345	Approved
0.5931	Remote Similarity	NPD6847	Approved
0.5931	Remote Similarity	NPD6869	Approved
0.5931	Remote Similarity	NPD6617	Approved
0.5926	Remote Similarity	NPD4202	Approved
0.5926	Remote Similarity	NPD6399	Phase 3
0.5926	Remote Similarity	NPD8171	Discontinued
0.5924	Remote Similarity	NPD6845	Suspended
0.5921	Remote Similarity	NPD7122	Discontinued
0.5921	Remote Similarity	NPD7642	Approved
0.5915	Remote Similarity	NPD8393	Approved
0.5903	Remote Similarity	NPD6014	Approved
0.5903	Remote Similarity	NPD8305	Approved
0.5903	Remote Similarity	NPD6012	Approved
0.5903	Remote Similarity	NPD8306	Approved
0.5903	Remote Similarity	NPD6013	Approved
0.5899	Remote Similarity	NPD6404	Discontinued
0.5899	Remote Similarity	NPD4696	Approved
0.5899	Remote Similarity	NPD5285	Approved
0.5899	Remote Similarity	NPD5286	Approved
0.5899	Remote Similarity	NPD4700	Approved
0.5899	Remote Similarity	NPD7640	Approved
0.5899	Remote Similarity	NPD7639	Approved
0.5896	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD6921	Approved
0.5894	Remote Similarity	NPD8266	Approved
0.5894	Remote Similarity	NPD5983	Phase 2
0.5894	Remote Similarity	NPD8267	Approved
0.5894	Remote Similarity	NPD8268	Approved
0.5894	Remote Similarity	NPD8269	Approved
0.5887	Remote Similarity	NPD8275	Approved
0.5887	Remote Similarity	NPD8276	Approved
0.5882	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7900	Approved
0.587	Remote Similarity	NPD6083	Phase 2
0.587	Remote Similarity	NPD6084	Phase 2
0.585	Remote Similarity	NPD8298	Phase 2
0.5844	Remote Similarity	NPD6336	Discontinued
0.5839	Remote Similarity	NPD5695	Phase 3
0.5838	Remote Similarity	NPD8407	Phase 2
0.5833	Remote Similarity	NPD6011	Approved
0.5822	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5224	Approved
0.5816	Remote Similarity	NPD5225	Approved
0.5816	Remote Similarity	NPD8086	Approved
0.5816	Remote Similarity	NPD5211	Phase 2
0.5816	Remote Similarity	NPD8139	Approved
0.5816	Remote Similarity	NPD5226	Approved
0.5816	Remote Similarity	NPD8085	Approved
0.5816	Remote Similarity	NPD8084	Approved
0.5816	Remote Similarity	NPD8138	Approved
0.5816	Remote Similarity	NPD8083	Approved
0.5816	Remote Similarity	NPD4633	Approved
0.5816	Remote Similarity	NPD8082	Approved
0.5814	Remote Similarity	NPD8417	Discontinued
0.5809	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD6008	Approved
0.5804	Remote Similarity	NPD4768	Approved
0.5804	Remote Similarity	NPD4767	Approved
0.5802	Remote Similarity	NPD4786	Approved
0.5797	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD5222	Approved
0.5797	Remote Similarity	NPD4697	Phase 3
0.5797	Remote Similarity	NPD5221	Approved
0.5793	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5793	Remote Similarity	NPD6941	Approved
0.5775	Remote Similarity	NPD5174	Approved
0.5775	Remote Similarity	NPD1407	Approved
0.5775	Remote Similarity	NPD5175	Approved
0.5761	Remote Similarity	NPD8368	Discontinued
0.5755	Remote Similarity	NPD5173	Approved
0.5753	Remote Similarity	NPD6420	Discontinued
0.5752	Remote Similarity	NPD6436	Phase 3
0.5745	Remote Similarity	NPD5223	Approved
0.5735	Remote Similarity	NPD8034	Phase 2
0.5735	Remote Similarity	NPD8035	Phase 2
0.5734	Remote Similarity	NPD8081	Approved
0.5734	Remote Similarity	NPD5141	Approved
0.5733	Remote Similarity	NPD7500	Approved
0.5732	Remote Similarity	NPD8384	Approved
0.5724	Remote Similarity	NPD4730	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