NPASS Compound

Structure

NPC61717 OpenBabel07101718312D 93101 0 0 1 0 0 0 0 0999 V2000 -3.2182 -5.7990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8493 -5.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3002 -2.9738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4301 -0.9902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4301 4.9510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2200 2.8379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2102 2.8379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3123 -1.8948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8575 -1.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9313 1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8575 1.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5726 0.4951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7151 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8575 -1.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5748 -4.1214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9313 -2.4438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2388 -0.4951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5753 -2.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5781 4.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1480 0.4951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5753 2.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1452 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8808 -5.0631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9628 -2.2379 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2877 -1.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2877 4.4559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2373 -3.3855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8575 0.4951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6568 -1.2962 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6568 0.3060 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7178 -2.4755 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7206 4.9510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.1480 1.4853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7178 3.4657 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0027 0.4951 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8575 1.4853 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5726 1.4853 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7151 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0027 -1.4853 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0027 4.4559 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8603 -2.9706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 13.7206 5.9412 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0055 1.9804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7178 4.4559 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0027 1.4853 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0027 -2.4755 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8603 4.9510 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 12.8630 6.4363 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0055 2.9706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0055 5.9412 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1452 1.9804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 11.1480 3.4657 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8603 -0.9902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0027 3.4657 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 12.0055 4.9510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2904 2.9706 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2877 1.4853 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7151 1.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7151 -0.9902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8575 0.4951 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1452 -0.9902 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1452 4.9510 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.5753 -3.9608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.4356 4.9510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0055 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2877 -2.4755 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2877 3.4657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2059 -3.5914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8603 -3.9608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.5781 6.4363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8630 1.4853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5753 4.9510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8603 1.9804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1452 -2.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8603 5.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8630 7.4265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8630 3.4657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1480 6.4363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8575 -0.4951 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9628 1.2477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4329 3.4657 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2877 0.4951 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7178 -1.4853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8630 4.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2904 1.9804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8603 2.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4301 1.9804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1452 2.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.1480 4.4559 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 9 62 1 0 0 0 0 10 83 1 0 0 0 0 11 12 1 0 0 0 0 11 30 1 0 0 0 0 12 38 1 0 0 0 0 13 14 1 0 0 0 0 13 39 1 0 0 0 0 14 62 1 0 0 0 0 15 16 1 0 0 0 0 15 61 1 0 0 0 0 16 63 1 0 0 0 0 17 25 2 0 0 0 0 17 29 1 0 0 0 0 18 26 1 0 0 0 0 18 29 1 0 0 0 0 19 31 1 0 0 0 0 19 32 1 0 0 0 0 20 66 1 0 0 0 0 21 67 1 0 0 0 0 22 68 1 0 0 0 0 23 84 1 0 0 0 0 24 37 1 0 0 0 0 24 85 1 0 0 0 0 26 3 1 6 0 0 0 26 31 1 0 0 0 0 27 64 2 3 0 0 0 27 69 1 0 0 0 0 28 65 2 3 0 0 0 28 70 1 0 0 0 0 29 71 2 0 0 0 0 30 40 2 0 0 0 0 30 63 1 0 0 0 0 31 61 1 1 0 0 0 32 40 1 0 0 0 0 32 83 1 6 0 0 0 33 20 1 6 0 0 0 33 43 1 0 0 0 0 33 86 1 0 0 0 0 34 21 1 1 0 0 0 34 44 1 0 0 0 0 34 87 1 0 0 0 0 35 22 1 1 0 0 0 35 45 1 0 0 0 0 35 88 1 0 0 0 0 36 23 1 1 0 0 0 36 46 1 0 0 0 0 36 89 1 0 0 0 0 37 47 1 0 0 0 0 37 90 1 6 0 0 0 38 60 1 0 0 0 0 38 62 1 1 0 0 0 39 60 1 0 0 0 0 39 91 1 1 0 0 0 40 61 1 0 0 0 0 41 48 1 0 0 0 0 41 55 1 0 0 0 0 41 64 1 1 0 0 0 42 49 1 0 0 0 0 42 56 1 0 0 0 0 42 65 1 6 0 0 0 43 48 1 0 0 0 0 43 72 1 6 0 0 0 44 50 1 0 0 0 0 44 73 1 6 0 0 0 45 51 1 0 0 0 0 45 74 1 6 0 0 0 46 49 1 0 0 0 0 46 75 1 6 0 0 0 47 53 1 0 0 0 0 47 76 1 1 0 0 0 48 77 1 6 0 0 0 49 78 1 1 0 0 0 50 52 1 0 0 0 0 50 79 1 1 0 0 0 51 54 1 0 0 0 0 51 80 1 1 0 0 0 52 57 1 0 0 0 0 52 81 1 6 0 0 0 53 59 1 0 0 0 0 53 92 1 6 0 0 0 54 58 1 0 0 0 0 54 93 1 6 0 0 0 55 86 1 0 0 0 0 55 90 1 6 0 0 0 56 89 1 0 0 0 0 56 92 1 1 0 0 0 57 87 1 0 0 0 0 57 93 1 1 0 0 0 58 84 1 1 0 0 0 58 88 1 0 0 0 0 59 85 1 0 0 0 0 59 91 1 1 0 0 0 61 8 1 1 0 0 0 62 63 1 6 0 0 0 63 82 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1334.66
Volume:	1276.133
LogP:	-0.148
LogD:	0.199
LogS:	-2.05
# Rotatable Bonds:	23
TPSA:	460.02
# H-Bond Aceptor:	30
# H-Bond Donor:	16
# Rings:	9
# Heavy Atoms:	30

MedChem Properties

QED Drug-Likeness Score:	0.03
Synthetic Accessibility Score:	7.68
Fsp3:	0.889
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:	-6.133
MDCK Permeability:	0.00033184318454004824
Pgp-inhibitor:	0.709
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.348
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.366
Plasma Protein Binding (PPB):	36.493568420410156%
Volume Distribution (VD):	0.045
Pgp-substrate:	20.915321350097656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.024
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.065

ADMET: Excretion

Clearance (CL):	0.056
Half-life (T1/2):	0.731

ADMET: Toxicity

hERG Blockers:	0.365
Human Hepatotoxicity (H-HT):	0.201
Drug-inuced Liver Injury (DILI):	0.493
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.278
Carcinogencity:	0.034
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.934

Download Data

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

Natural Product: NPC61717

Natural Product ID:	NPC61717
*Common Name:**	Sarasinoside I2
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,5S,9S,10S,13R,15S,17R)-9-hydroxy-15-methoxy-4,4,10,13-tetramethyl-17-[(2R)-6-methyl-4-oxohept-5-en-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
Synonyms:	Sarasinoside I2
Standard InCHIKey:	DOGGFOAHICNYOW-NESKDGBCSA-N
Standard InCHI:	InChI=1S/C63H102N2O28/c1-25(2)17-29(71)18-26(3)31-19-32(83-10)40-30-11-12-38-60(6,7)39(13-14-62(38,9)63(30,82)16-15-61(31,40)8)91-59-53(47(76)37(24-85-59)90-55-41(64-27(4)69)48(77)43(72)33(20-66)86-55)92-56-42(65-28(5)70)49(78)46(75)36(89-56)23-84-58-54(51(80)45(74)35(22-68)88-58)93-57-52(81)50(79)44(73)34(21-67)87-57/h17,26,31-39,41-59,66-68,72-82H,11-16,18-24H2,1-10H3,(H,64,69)(H,65,70)/t26-,31-,32+,33-,34-,35-,36-,37-,38+,39+,41-,42-,43+,44-,45-,46-,47+,48-,49-,50+,51+,52-,53-,54-,55+,56+,57+,58-,59+,61-,62+,63-/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)CCC2=C4[C@@](CC[C@]32O)(C)[C@H](C[C@@H]4OC)[C@@H](CC(=O)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:	CHEMBL508153
PubChem CID:	21606561
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
NPO32754	melophlus isis	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10924165]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	>	100.0	ug.mL-1	PMID[481746]

☑ 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 NPC61717 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	177
0.1-0.2	1065
0.2-0.3	4021
0.3-0.4	14189
0.4-0.5	12623
0.5-0.6	7090
0.6-0.7	2406
0.7-0.8	1064
0.8-0.85	19
0.85-0.9	25
0.9-0.95	14
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC244380
0.9851	High Similarity	NPC214821
0.9851	High Similarity	NPC298067
0.9424	High Similarity	NPC36463
0.9424	High Similarity	NPC298005
0.9203	High Similarity	NPC141669
0.9197	High Similarity	NPC162910
0.9065	High Similarity	NPC298469
0.9051	High Similarity	NPC180770
0.9051	High Similarity	NPC302276
0.8958	High Similarity	NPC475527
0.8929	High Similarity	NPC284625
0.8929	High Similarity	NPC69176
0.8929	High Similarity	NPC193579
0.8897	High Similarity	NPC100612
0.8897	High Similarity	NPC174336
0.8897	High Similarity	NPC187497
0.8897	High Similarity	NPC475599
0.8897	High Similarity	NPC113620
0.8828	High Similarity	NPC265699
0.8777	High Similarity	NPC265908
0.8592	High Similarity	NPC475152
0.8592	High Similarity	NPC475584
0.8592	High Similarity	NPC475394
0.8531	High Similarity	NPC475892
0.8489	Intermediate Similarity	NPC235772
0.8489	Intermediate Similarity	NPC280941
0.8406	Intermediate Similarity	NPC139585
0.8345	Intermediate Similarity	NPC73829
0.8345	Intermediate Similarity	NPC119794
0.8322	Intermediate Similarity	NPC172365
0.8322	Intermediate Similarity	NPC210729
0.8322	Intermediate Similarity	NPC82931
0.831	Intermediate Similarity	NPC243680
0.831	Intermediate Similarity	NPC200788
0.8286	Intermediate Similarity	NPC477072
0.8273	Intermediate Similarity	NPC475472
0.8227	Intermediate Similarity	NPC75318
0.8169	Intermediate Similarity	NPC145899
0.8156	Intermediate Similarity	NPC76999
0.7956	Intermediate Similarity	NPC469943
0.7771	Intermediate Similarity	NPC475345
0.7758	Intermediate Similarity	NPC476113
0.7725	Intermediate Similarity	NPC475649
0.766	Intermediate Similarity	NPC297950
0.7626	Intermediate Similarity	NPC476675
0.7609	Intermediate Similarity	NPC190939
0.7609	Intermediate Similarity	NPC197003
0.7554	Intermediate Similarity	NPC129393
0.7552	Intermediate Similarity	NPC23020
0.7552	Intermediate Similarity	NPC220838
0.7552	Intermediate Similarity	NPC112492
0.7552	Intermediate Similarity	NPC472270
0.7552	Intermediate Similarity	NPC472268
0.7552	Intermediate Similarity	NPC45606
0.7552	Intermediate Similarity	NPC472269
0.7518	Intermediate Similarity	NPC279638
0.7517	Intermediate Similarity	NPC322904
0.7517	Intermediate Similarity	NPC233223
0.7517	Intermediate Similarity	NPC473679
0.7517	Intermediate Similarity	NPC475444
0.7517	Intermediate Similarity	NPC183816
0.7517	Intermediate Similarity	NPC196874
0.7517	Intermediate Similarity	NPC319719
0.7517	Intermediate Similarity	NPC324933
0.7517	Intermediate Similarity	NPC475177
0.7483	Intermediate Similarity	NPC803
0.747	Intermediate Similarity	NPC120667
0.747	Intermediate Similarity	NPC278272
0.7465	Intermediate Similarity	NPC473505
0.745	Intermediate Similarity	NPC290746
0.745	Intermediate Similarity	NPC79250
0.7448	Intermediate Similarity	NPC300655
0.7448	Intermediate Similarity	NPC311178
0.7448	Intermediate Similarity	NPC43589
0.7448	Intermediate Similarity	NPC222951
0.7447	Intermediate Similarity	NPC28532
0.7429	Intermediate Similarity	NPC308459
0.7376	Intermediate Similarity	NPC476672
0.7372	Intermediate Similarity	NPC260665
0.7361	Intermediate Similarity	NPC240070
0.7361	Intermediate Similarity	NPC470516
0.7361	Intermediate Similarity	NPC329784
0.7347	Intermediate Similarity	NPC316915
0.7343	Intermediate Similarity	NPC476674
0.7329	Intermediate Similarity	NPC173347
0.7329	Intermediate Similarity	NPC201359
0.7324	Intermediate Similarity	NPC474423
0.7324	Intermediate Similarity	NPC74259
0.7315	Intermediate Similarity	NPC329675
0.7305	Intermediate Similarity	NPC476670
0.7305	Intermediate Similarity	NPC268184
0.7305	Intermediate Similarity	NPC476150
0.7305	Intermediate Similarity	NPC135369
0.7305	Intermediate Similarity	NPC476127
0.7299	Intermediate Similarity	NPC474265
0.7299	Intermediate Similarity	NPC210420
0.7292	Intermediate Similarity	NPC476673
0.7286	Intermediate Similarity	NPC471548
0.7279	Intermediate Similarity	NPC231240
0.7273	Intermediate Similarity	NPC117445
0.7273	Intermediate Similarity	NPC308262
0.7273	Intermediate Similarity	NPC208193
0.7266	Intermediate Similarity	NPC146652
0.726	Intermediate Similarity	NPC476966
0.726	Intermediate Similarity	NPC232785
0.726	Intermediate Similarity	NPC125077
0.726	Intermediate Similarity	NPC188234
0.726	Intermediate Similarity	NPC477235
0.726	Intermediate Similarity	NPC471407
0.726	Intermediate Similarity	NPC276838
0.726	Intermediate Similarity	NPC140092
0.726	Intermediate Similarity	NPC329986
0.7254	Intermediate Similarity	NPC475419
0.7254	Intermediate Similarity	NPC120390
0.7254	Intermediate Similarity	NPC475590
0.7254	Intermediate Similarity	NPC474908
0.7248	Intermediate Similarity	NPC194716
0.7239	Intermediate Similarity	NPC163365
0.7234	Intermediate Similarity	NPC477464
0.7234	Intermediate Similarity	NPC470517
0.7234	Intermediate Similarity	NPC470915
0.7234	Intermediate Similarity	NPC470911
0.723	Intermediate Similarity	NPC477709
0.723	Intermediate Similarity	NPC476221
0.7222	Intermediate Similarity	NPC473474
0.7222	Intermediate Similarity	NPC248202
0.7222	Intermediate Similarity	NPC318135
0.7214	Intermediate Similarity	NPC471547
0.7214	Intermediate Similarity	NPC473405
0.7214	Intermediate Similarity	NPC20979
0.7203	Intermediate Similarity	NPC15918
0.7203	Intermediate Similarity	NPC169816
0.7203	Intermediate Similarity	NPC305771
0.7203	Intermediate Similarity	NPC94072
0.72	Intermediate Similarity	NPC297058
0.72	Intermediate Similarity	NPC127656
0.7194	Intermediate Similarity	NPC70809
0.7194	Intermediate Similarity	NPC60557
0.7194	Intermediate Similarity	NPC224381
0.7194	Intermediate Similarity	NPC475163
0.7194	Intermediate Similarity	NPC305981
0.7194	Intermediate Similarity	NPC294453
0.7194	Intermediate Similarity	NPC57484
0.7194	Intermediate Similarity	NPC123199
0.7194	Intermediate Similarity	NPC4328
0.7194	Intermediate Similarity	NPC227551
0.7194	Intermediate Similarity	NPC236638
0.7194	Intermediate Similarity	NPC474557
0.7194	Intermediate Similarity	NPC471385
0.7194	Intermediate Similarity	NPC165439
0.7194	Intermediate Similarity	NPC471550
0.7194	Intermediate Similarity	NPC43550
0.7194	Intermediate Similarity	NPC473882
0.7194	Intermediate Similarity	NPC161717
0.7194	Intermediate Similarity	NPC475160
0.7194	Intermediate Similarity	NPC293330
0.7194	Intermediate Similarity	NPC469782
0.7194	Intermediate Similarity	NPC100639
0.7194	Intermediate Similarity	NPC41061
0.7194	Intermediate Similarity	NPC79643
0.7194	Intermediate Similarity	NPC475140
0.7194	Intermediate Similarity	NPC476068
0.7194	Intermediate Similarity	NPC67857
0.7194	Intermediate Similarity	NPC204414
0.7194	Intermediate Similarity	NPC71065
0.7194	Intermediate Similarity	NPC202828
0.7194	Intermediate Similarity	NPC65105
0.7194	Intermediate Similarity	NPC76972
0.7194	Intermediate Similarity	NPC309907
0.7194	Intermediate Similarity	NPC250247
0.7194	Intermediate Similarity	NPC473714
0.7194	Intermediate Similarity	NPC54636
0.7194	Intermediate Similarity	NPC119592
0.7194	Intermediate Similarity	NPC298034
0.7194	Intermediate Similarity	NPC261506
0.7192	Intermediate Similarity	NPC470476
0.7192	Intermediate Similarity	NPC311534
0.7188	Intermediate Similarity	NPC473208
0.7183	Intermediate Similarity	NPC473130
0.7183	Intermediate Similarity	NPC475187
0.7183	Intermediate Similarity	NPC72260
0.7183	Intermediate Similarity	NPC470312
0.7181	Intermediate Similarity	NPC329636
0.7163	Intermediate Similarity	NPC470514
0.7163	Intermediate Similarity	NPC45475
0.7163	Intermediate Similarity	NPC36831
0.7163	Intermediate Similarity	NPC475899
0.7163	Intermediate Similarity	NPC470515
0.7163	Intermediate Similarity	NPC470513
0.7163	Intermediate Similarity	NPC473617
0.7163	Intermediate Similarity	NPC473828
0.7162	Intermediate Similarity	NPC471855
0.7153	Intermediate Similarity	NPC256983
0.7153	Intermediate Similarity	NPC154856
0.7153	Intermediate Similarity	NPC52241
0.7153	Intermediate Similarity	NPC160084
0.7153	Intermediate Similarity	NPC27363
0.7153	Intermediate Similarity	NPC475317
0.7143	Intermediate Similarity	NPC472718

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 NPC61717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	133
0.1-0.2	764
0.2-0.3	3178
0.3-0.4	3603
0.4-0.5	1035
0.5-0.6	354
0.6-0.7	64
0.7-0.8	19
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
0.7183	Intermediate Similarity	NPD8377	Approved
0.7183	Intermediate Similarity	NPD8294	Approved
0.7179	Intermediate Similarity	NPD7625	Phase 1
0.7133	Intermediate Similarity	NPD8379	Approved
0.7133	Intermediate Similarity	NPD8378	Approved
0.7133	Intermediate Similarity	NPD8296	Approved
0.7133	Intermediate Similarity	NPD8380	Approved
0.7133	Intermediate Similarity	NPD8335	Approved
0.7122	Intermediate Similarity	NPD8133	Approved
0.7059	Intermediate Similarity	NPD6412	Phase 2
0.7055	Intermediate Similarity	NPD7507	Approved
0.7014	Intermediate Similarity	NPD8033	Approved
0.698	Remote Similarity	NPD6914	Discontinued
0.6954	Remote Similarity	NPD8450	Suspended
0.6913	Remote Similarity	NPD7319	Approved
0.6887	Remote Similarity	NPD8449	Approved
0.6884	Remote Similarity	NPD6686	Approved
0.6806	Remote Similarity	NPD7327	Approved
0.6806	Remote Similarity	NPD7328	Approved
0.6803	Remote Similarity	NPD8328	Phase 3
0.6781	Remote Similarity	NPD7503	Approved
0.6759	Remote Similarity	NPD7516	Approved
0.6755	Remote Similarity	NPD8390	Approved
0.6755	Remote Similarity	NPD8391	Approved
0.6755	Remote Similarity	NPD8392	Approved
0.6733	Remote Similarity	NPD8337	Approved
0.6733	Remote Similarity	NPD8336	Approved
0.6667	Remote Similarity	NPD6334	Approved
0.6667	Remote Similarity	NPD6333	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD8338	Approved
0.6596	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD8448	Approved
0.6556	Remote Similarity	NPD8074	Phase 3
0.6554	Remote Similarity	NPD8513	Phase 3
0.6538	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD8174	Phase 2
0.6513	Remote Similarity	NPD7736	Approved
0.651	Remote Similarity	NPD6370	Approved
0.6503	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.649	Remote Similarity	NPD8451	Approved
0.6447	Remote Similarity	NPD8293	Discontinued
0.6434	Remote Similarity	NPD6421	Discontinued
0.6424	Remote Similarity	NPD8341	Approved
0.6424	Remote Similarity	NPD8342	Approved
0.6424	Remote Similarity	NPD8299	Approved
0.6424	Remote Similarity	NPD8340	Approved
0.6404	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD7115	Discovery
0.6377	Remote Similarity	NPD7639	Approved
0.6377	Remote Similarity	NPD7640	Approved
0.6376	Remote Similarity	NPD6059	Approved
0.6376	Remote Similarity	NPD6054	Approved
0.6369	Remote Similarity	NPD8415	Approved
0.6358	Remote Similarity	NPD7830	Approved
0.6358	Remote Similarity	NPD7829	Approved
0.6345	Remote Similarity	NPD6430	Approved
0.6345	Remote Similarity	NPD6429	Approved
0.6333	Remote Similarity	NPD6909	Approved
0.6333	Remote Similarity	NPD6908	Approved
0.6304	Remote Similarity	NPD7638	Approved
0.6291	Remote Similarity	NPD8080	Discontinued
0.6284	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7642	Approved
0.625	Remote Similarity	NPD6067	Discontinued
0.6233	Remote Similarity	NPD8297	Approved
0.6233	Remote Similarity	NPD6882	Approved
0.6225	Remote Similarity	NPD6015	Approved
0.6225	Remote Similarity	NPD8444	Approved
0.6225	Remote Similarity	NPD6016	Approved
0.6209	Remote Similarity	NPD7492	Approved
0.6197	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD5988	Approved
0.6174	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6009	Approved
0.6169	Remote Similarity	NPD6616	Approved
0.6159	Remote Similarity	NPD6319	Approved
0.6144	Remote Similarity	NPD7604	Phase 2
0.6138	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7641	Discontinued
0.6129	Remote Similarity	NPD7078	Approved
0.6118	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6921	Approved
0.6108	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD8407	Phase 2
0.6081	Remote Similarity	NPD4632	Approved
0.6076	Remote Similarity	NPD7260	Phase 2
0.6067	Remote Similarity	NPD7500	Approved
0.6042	Remote Similarity	NPD6675	Approved
0.6042	Remote Similarity	NPD6402	Approved
0.6042	Remote Similarity	NPD7128	Approved
0.6042	Remote Similarity	NPD5739	Approved
0.6033	Remote Similarity	NPD8368	Discontinued
0.6029	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD6372	Approved
0.6027	Remote Similarity	NPD6373	Approved
0.6013	Remote Similarity	NPD8266	Approved
0.6013	Remote Similarity	NPD8267	Approved
0.6013	Remote Similarity	NPD8268	Approved
0.6013	Remote Similarity	NPD8269	Approved
0.6	Remote Similarity	NPD8307	Discontinued
0.6	Remote Similarity	NPD6940	Discontinued
0.5987	Remote Similarity	NPD6033	Approved
0.5986	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD8360	Approved
0.5979	Remote Similarity	NPD8361	Approved
0.5959	Remote Similarity	NPD7320	Approved
0.5959	Remote Similarity	NPD6899	Approved
0.5959	Remote Similarity	NPD6881	Approved
0.5957	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD8130	Phase 1
0.5946	Remote Similarity	NPD6649	Approved
0.5946	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6650	Approved
0.5944	Remote Similarity	NPD5211	Phase 2
0.5944	Remote Similarity	NPD7632	Discontinued
0.5939	Remote Similarity	NPD8384	Approved
0.5938	Remote Similarity	NPD6845	Suspended
0.5931	Remote Similarity	NPD5357	Phase 1
0.5915	Remote Similarity	NPD8418	Phase 2
0.5903	Remote Similarity	NPD1407	Approved
0.5899	Remote Similarity	NPD7748	Approved
0.5895	Remote Similarity	NPD8435	Approved
0.589	Remote Similarity	NPD5697	Approved
0.589	Remote Similarity	NPD8140	Approved
0.589	Remote Similarity	NPD5701	Approved
0.5887	Remote Similarity	NPD7902	Approved
0.5887	Remote Similarity	NPD4755	Approved
0.5878	Remote Similarity	NPD4634	Approved
0.5878	Remote Similarity	NPD8087	Discontinued
0.5878	Remote Similarity	NPD6420	Discontinued
0.5878	Remote Similarity	NPD7290	Approved
0.5878	Remote Similarity	NPD6883	Approved
0.5878	Remote Similarity	NPD7102	Approved
0.5862	Remote Similarity	NPD5141	Approved
0.586	Remote Similarity	NPD8273	Phase 1
0.5845	Remote Similarity	NPD4225	Approved
0.5844	Remote Similarity	NPD8346	Approved
0.5844	Remote Similarity	NPD8347	Approved
0.5844	Remote Similarity	NPD8345	Approved
0.5839	Remote Similarity	NPD6847	Approved
0.5839	Remote Similarity	NPD6869	Approved
0.5839	Remote Similarity	NPD6617	Approved
0.5833	Remote Similarity	NPD7141	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7139	Approved
0.5833	Remote Similarity	NPD7140	Approved
0.5827	Remote Similarity	NPD4202	Approved
0.5822	Remote Similarity	NPD8393	Approved
0.5822	Remote Similarity	NPD6640	Phase 3
0.5814	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.5811	Remote Similarity	NPD6012	Approved
0.5811	Remote Similarity	NPD8305	Approved
0.5811	Remote Similarity	NPD8306	Approved
0.5811	Remote Similarity	NPD6014	Approved
0.5811	Remote Similarity	NPD6013	Approved
0.5806	Remote Similarity	NPD5983	Phase 2
0.5804	Remote Similarity	NPD5286	Approved
0.5804	Remote Similarity	NPD5285	Approved
0.5804	Remote Similarity	NPD4700	Approved
0.5804	Remote Similarity	NPD4696	Approved
0.5795	Remote Similarity	NPD8485	Approved
0.5793	Remote Similarity	NPD8276	Approved
0.5793	Remote Similarity	NPD8275	Approved
0.5782	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD6084	Phase 2
0.5775	Remote Similarity	NPD6083	Phase 2
0.5771	Remote Similarity	NPD8414	Discontinued
0.5769	Remote Similarity	NPD7623	Phase 3
0.5769	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5759	Remote Similarity	NPD6336	Discontinued
0.5755	Remote Similarity	NPD7515	Phase 2
0.575	Remote Similarity	NPD8319	Approved
0.575	Remote Similarity	NPD8320	Phase 1
0.5743	Remote Similarity	NPD6011	Approved
0.5743	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD8417	Discontinued
0.5736	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.5735	Remote Similarity	NPD3618	Phase 1
0.5735	Remote Similarity	NPD7801	Approved
0.5734	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD5328	Approved
0.5724	Remote Similarity	NPD8085	Approved
0.5724	Remote Similarity	NPD8083	Approved
0.5724	Remote Similarity	NPD5226	Approved
0.5724	Remote Similarity	NPD8138	Approved
0.5724	Remote Similarity	NPD5224	Approved
0.5724	Remote Similarity	NPD8086	Approved
0.5724	Remote Similarity	NPD8139	Approved
0.5724	Remote Similarity	NPD8084	Approved
0.5724	Remote Similarity	NPD8082	Approved
0.5724	Remote Similarity	NPD5225	Approved
0.5724	Remote Similarity	NPD4633	Approved
0.5723	Remote Similarity	NPD7746	Phase 1
0.5723	Remote Similarity	NPD7747	Phase 1
0.5714	Remote Similarity	NPD6008	Approved
0.5714	Remote Similarity	NPD4768	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