NPASS Compound

Structure

CID290276 OpenBabel06191716102D 96102 0 0 1 0 0 0 0 0999 V2000 -1.6578 10.0122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7229 0.7617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9216 -7.4931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6461 -6.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8075 1.4730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8919 -3.4933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6136 2.4789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8771 -1.4935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6652 9.0122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0851 -0.0041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9142 -6.4931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8029 8.5059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1030 0.1653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8103 7.5059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0519 6.9995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3573 -4.5103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0445 5.9996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2297 -5.0140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4916 -5.0023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0965 -4.5220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9068 5.4932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6192 -4.4986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9648 -4.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4652 -0.6005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8271 -4.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0951 -4.4547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0888 -3.5259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6116 -3.5024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8993 4.4933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8197 -3.4420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0877 -3.4548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8095 -1.5358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9556 -3.0340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7396 -2.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0297 3.9997 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9426 -1.9485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0729 -1.4549 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8326 4.5061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7764 -5.9868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9415 0.9731 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7542 -2.9870 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6062 1.4790 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8697 -0.4935 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9500 -2.9484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9482 -2.0373 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7023 4.0126 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7322 -2.0023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0223 2.9998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2106 -1.9613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0691 1.4767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5645 4.5190 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4342 4.0254 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1967 0.9731 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4416 3.0255 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4861 -2.9741 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7320 -0.0095 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6239 -3.4805 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7394 0.9871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7319 0.0128 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1967 -0.0343 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4787 -1.9742 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5914 -0.5143 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7245 1.0128 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8548 1.5063 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7690 -4.9868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5794 2.5191 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0691 -0.5380 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6090 -1.4806 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4582 -0.0223 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0074 0.9999 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8252 5.5061 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8643 -1.5056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8845 2.4934 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2181 -2.9613 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0691 2.4767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5571 5.5189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2965 4.5318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3307 1.4730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3113 2.5319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3558 -3.4677 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8623 -0.5031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8993 -4.4933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9415 -0.0343 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7468 -1.9870 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4656 0.9743 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 6.0758 -1.5337 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7097 3.0126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5988 -1.5109 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3410 -1.4678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8474 2.5063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6313 -4.4804 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8771 1.4935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6016 -0.4807 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5258 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5868 1.5192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 39 1 0 0 0 0 12 14 1 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 19 22 1 0 0 0 0 20 27 1 0 0 0 0 21 29 1 0 0 0 0 22 28 1 0 0 0 0 23 25 2 0 0 0 0 23 26 1 0 0 0 0 24 32 1 0 0 0 0 25 30 1 0 0 0 0 26 31 2 0 0 0 0 27 33 1 0 0 0 0 28 34 1 0 0 0 0 29 35 1 0 0 0 0 30 44 2 0 0 0 0 31 44 1 0 0 0 0 33 45 1 0 0 0 0 34 47 1 0 0 0 0 35 48 1 0 0 0 0 36 37 2 0 0 0 0 36 44 1 0 0 0 0 37 49 1 0 0 0 0 38 71 1 0 0 0 0 39 4 1 6 0 0 0 39 65 1 0 0 0 0 40 5 1 1 0 0 0 40 50 1 0 0 0 0 40 83 1 0 0 0 0 41 6 1 1 0 0 0 41 57 1 0 0 0 0 41 84 1 0 0 0 0 42 7 1 6 0 0 0 42 58 1 0 0 0 0 42 85 1 0 0 0 0 43 8 1 1 0 0 0 43 59 1 0 0 0 0 43 86 1 0 0 0 0 45 32 1 1 0 0 0 45 87 1 0 0 0 0 46 38 1 1 0 0 0 46 51 1 0 0 0 0 46 88 1 0 0 0 0 47 72 2 0 0 0 0 47 89 1 0 0 0 0 48 73 2 0 0 0 0 48 91 1 0 0 0 0 49 74 2 0 0 0 0 49 90 1 0 0 0 0 50 53 1 0 0 0 0 50 75 1 1 0 0 0 51 52 1 0 0 0 0 51 76 1 6 0 0 0 52 54 1 0 0 0 0 52 77 1 1 0 0 0 53 60 1 0 0 0 0 53 78 1 1 0 0 0 54 66 1 0 0 0 0 54 79 1 6 0 0 0 55 57 1 0 0 0 0 55 61 1 0 0 0 0 55 80 1 1 0 0 0 56 58 1 0 0 0 0 56 62 1 0 0 0 0 56 81 1 6 0 0 0 57 92 1 6 0 0 0 58 93 1 1 0 0 0 59 63 1 0 0 0 0 59 94 1 6 0 0 0 60 67 1 0 0 0 0 60 95 1 6 0 0 0 61 68 1 0 0 0 0 61 90 1 1 0 0 0 62 69 1 0 0 0 0 62 89 1 6 0 0 0 63 64 1 0 0 0 0 63 96 1 1 0 0 0 64 70 1 0 0 0 0 64 91 1 1 0 0 0 65 82 2 0 0 0 0 65 92 1 0 0 0 0 66 88 1 0 0 0 0 66 96 1 1 0 0 0 67 83 1 1 0 0 0 67 87 1 0 0 0 0 68 84 1 0 0 0 0 68 94 1 6 0 0 0 69 85 1 1 0 0 0 69 95 1 0 0 0 0 70 86 1 0 0 0 0 70 93 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1368.74
Volume:	1366.834
LogP:	8.348
LogD:	4.496
LogS:	-4.797
# Rotatable Bonds:	29
TPSA:	359.34
# H-Bond Aceptor:	26
# H-Bond Donor:	8
# Rings:	7
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.024
Synthetic Accessibility Score:	7.663
Fsp3:	0.829
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.348
MDCK Permeability:	0.00013523874804377556
Pgp-inhibitor:	0.948
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.772
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.203

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	98.2095718383789%
Volume Distribution (VD):	0.516
Pgp-substrate:	2.6586368083953857%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.094
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.122
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.135
CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.573
CYP3A4-substrate:	0.02

ADMET: Excretion

Clearance (CL):	1.175
Half-life (T1/2):	0.168

ADMET: Toxicity

hERG Blockers:	0.819
Human Hepatotoxicity (H-HT):	0.863
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.111
Rat Oral Acute Toxicity:	0.579
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.955
Carcinogencity:	0.076
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.14

Download Data

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

Natural Product: NPC290276

Natural Product ID:	NPC290276
*Common Name:**	Purginoside I
IUPAC Name:	n.a.
Synonyms:	Purginoside I
Standard InCHIKey:	MFVVQPJPHUAJBA-KXXSYOAGSA-N
Standard InCHI:	InChI=1S/C70H112O26/c1-9-12-14-15-17-21-29-35-48(73)91-64-63(96-66-54(79)52(77)51(76)46(38-71)88-66)59(94-68-61(90-49(74)37-36-44-30-25-23-26-31-44)55(80)57(41(6)84-68)92-65(82)39(4)11-3)43(8)86-70(64)93-58-42(7)85-69-62(56(58)81)89-47(72)34-28-22-19-16-18-20-27-33-45(32-24-13-10-2)87-67-60(95-69)53(78)50(75)40(5)83-67/h23,25-26,30-31,36-37,39-43,45-46,50-64,66-71,75-81H,9-22,24,27-29,32-35,38H2,1-8H3/b37-36+/t39-,40+,41-,42-,43-,45-,46+,50-,51+,52-,53-,54+,55+,56+,57-,58-,59-,60+,61+,62+,63+,64+,66-,67-,68-,69-,70-/m0/s1
SMILES:	CCCCCCCCCC(=O)O[C@H]1[C@@H](O[C@H]([C@@H]([C@H]1O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1OC(=O)/C=C/c1ccccc1)O)OC(=O)[C@H](CC)C)C)O[C@H]1[C@H](C)O[C@@H]2[C@@H]([C@@H]1O)OC(=O)CCCCCCCCC[C@@H](O[C@H]1[C@H](O2)[C@@H](O)[C@H]([C@H](O1)C)O)CCCCC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2336640
PubChem CID:	53355579
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

*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
NPO19106	Ipomoea purga	Species	Convolvulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21446661]
NPO19106	Ipomoea purga	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23273047]
NPO19106	Ipomoea purga	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2
Others	3

Activity Type	# Activity
Cell Line	3
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[543186]
NPT83	Cell Line	MCF7	Homo sapiens	FC	=	0.8	n.a.	PMID[543186]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FC	=	2.9	n.a.	PMID[543186]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FC	=	2.8	n.a.	PMID[543186]

☑ 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 NPC290276 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	275
0.1-0.2	957
0.2-0.3	2392
0.3-0.4	6390
0.4-0.5	12412
0.5-0.6	14869
0.6-0.7	4655
0.7-0.8	678
0.8-0.85	35
0.85-0.9	11
0.9-0.95	6
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC124878
1.0	High Similarity	NPC10883
1.0	High Similarity	NPC63404
1.0	High Similarity	NPC35338
1.0	High Similarity	NPC10121
1.0	High Similarity	NPC198918
1.0	High Similarity	NPC92283
1.0	High Similarity	NPC204214
1.0	High Similarity	NPC231888
0.9916	High Similarity	NPC28069
0.9916	High Similarity	NPC77651
0.9835	High Similarity	NPC471024
0.9832	High Similarity	NPC87153
0.9832	High Similarity	NPC162925
0.9752	High Similarity	NPC471025
0.9669	High Similarity	NPC147032
0.935	High Similarity	NPC471026
0.918	High Similarity	NPC141970
0.918	High Similarity	NPC140561
0.8968	High Similarity	NPC231627
0.8898	High Similarity	NPC237182
0.8898	High Similarity	NPC226101
0.8852	High Similarity	NPC476096
0.875	High Similarity	NPC40085
0.875	High Similarity	NPC264270
0.8676	High Similarity	NPC111466
0.8655	High Similarity	NPC470825
0.8527	High Similarity	NPC148026
0.8504	High Similarity	NPC473881
0.8473	Intermediate Similarity	NPC319995
0.8473	Intermediate Similarity	NPC289415
0.8467	Intermediate Similarity	NPC284957
0.845	Intermediate Similarity	NPC114096
0.8438	Intermediate Similarity	NPC57607
0.8403	Intermediate Similarity	NPC184633
0.8397	Intermediate Similarity	NPC11025
0.8295	Intermediate Similarity	NPC244454
0.8211	Intermediate Similarity	NPC474641
0.8195	Intermediate Similarity	NPC17567
0.8182	Intermediate Similarity	NPC301857
0.8162	Intermediate Similarity	NPC263829
0.8148	Intermediate Similarity	NPC470143
0.8148	Intermediate Similarity	NPC322503
0.8145	Intermediate Similarity	NPC29607
0.8129	Intermediate Similarity	NPC473755
0.8129	Intermediate Similarity	NPC475513
0.8115	Intermediate Similarity	NPC43584
0.8095	Intermediate Similarity	NPC477467
0.8043	Intermediate Similarity	NPC469364
0.8043	Intermediate Similarity	NPC101686
0.8043	Intermediate Similarity	NPC65262
0.8027	Intermediate Similarity	NPC477470
0.8027	Intermediate Similarity	NPC477472
0.8027	Intermediate Similarity	NPC477474
0.8015	Intermediate Similarity	NPC38420
0.8015	Intermediate Similarity	NPC136608
0.7984	Intermediate Similarity	NPC229600
0.7983	Intermediate Similarity	NPC469527
0.7973	Intermediate Similarity	NPC477736
0.7939	Intermediate Similarity	NPC138798
0.7931	Intermediate Similarity	NPC329657
0.7926	Intermediate Similarity	NPC305162
0.7914	Intermediate Similarity	NPC475195
0.7905	Intermediate Similarity	NPC477735
0.7887	Intermediate Similarity	NPC293154
0.7881	Intermediate Similarity	NPC473641
0.7881	Intermediate Similarity	NPC475437
0.7881	Intermediate Similarity	NPC475464
0.7881	Intermediate Similarity	NPC473797
0.7881	Intermediate Similarity	NPC475505
0.7881	Intermediate Similarity	NPC475300
0.7879	Intermediate Similarity	NPC145287
0.7868	Intermediate Similarity	NPC235294
0.7868	Intermediate Similarity	NPC46137
0.7862	Intermediate Similarity	NPC476092
0.7862	Intermediate Similarity	NPC70236
0.7862	Intermediate Similarity	NPC475447
0.7862	Intermediate Similarity	NPC475218
0.7852	Intermediate Similarity	NPC476784
0.7832	Intermediate Similarity	NPC64195
0.7826	Intermediate Similarity	NPC169398
0.7823	Intermediate Similarity	NPC30563
0.7823	Intermediate Similarity	NPC69425
0.7815	Intermediate Similarity	NPC165234
0.7815	Intermediate Similarity	NPC475536
0.78	Intermediate Similarity	NPC477623
0.7793	Intermediate Similarity	NPC474564
0.777	Intermediate Similarity	NPC469398
0.777	Intermediate Similarity	NPC106818
0.7762	Intermediate Similarity	NPC76406
0.7762	Intermediate Similarity	NPC247032
0.7762	Intermediate Similarity	NPC175214
0.7762	Intermediate Similarity	NPC476381
0.7762	Intermediate Similarity	NPC119537
0.7762	Intermediate Similarity	NPC96795
0.7762	Intermediate Similarity	NPC476384
0.7762	Intermediate Similarity	NPC298257
0.7762	Intermediate Similarity	NPC476375
0.7762	Intermediate Similarity	NPC476378
0.7762	Intermediate Similarity	NPC264632
0.7762	Intermediate Similarity	NPC205864
0.7762	Intermediate Similarity	NPC476397
0.7762	Intermediate Similarity	NPC112
0.7762	Intermediate Similarity	NPC476380
0.7762	Intermediate Similarity	NPC469367
0.7762	Intermediate Similarity	NPC269141
0.7761	Intermediate Similarity	NPC267733
0.7761	Intermediate Similarity	NPC276047
0.7742	Intermediate Similarity	NPC276061
0.7742	Intermediate Similarity	NPC474148
0.774	Intermediate Similarity	NPC23677
0.7737	Intermediate Similarity	NPC225384
0.7737	Intermediate Similarity	NPC246869
0.7737	Intermediate Similarity	NPC138777
0.7727	Intermediate Similarity	NPC475175
0.7727	Intermediate Similarity	NPC475531
0.7727	Intermediate Similarity	NPC475198
0.7724	Intermediate Similarity	NPC212808
0.7721	Intermediate Similarity	NPC473443
0.7721	Intermediate Similarity	NPC27712
0.7718	Intermediate Similarity	NPC87403
0.7714	Intermediate Similarity	NPC471345
0.7708	Intermediate Similarity	NPC202391
0.7708	Intermediate Similarity	NPC296659
0.7708	Intermediate Similarity	NPC471028
0.7704	Intermediate Similarity	NPC106677
0.7692	Intermediate Similarity	NPC469623
0.7692	Intermediate Similarity	NPC148080
0.7664	Intermediate Similarity	NPC475478
0.7662	Intermediate Similarity	NPC473468
0.7662	Intermediate Similarity	NPC473557
0.7662	Intermediate Similarity	NPC475567
0.766	Intermediate Similarity	NPC476376
0.7647	Intermediate Similarity	NPC225103
0.7628	Intermediate Similarity	NPC477471
0.7628	Intermediate Similarity	NPC477473
0.7628	Intermediate Similarity	NPC477469
0.7628	Intermediate Similarity	NPC477466
0.7622	Intermediate Similarity	NPC47471
0.7622	Intermediate Similarity	NPC476377
0.7619	Intermediate Similarity	NPC469448
0.7612	Intermediate Similarity	NPC317163
0.7609	Intermediate Similarity	NPC80599
0.7606	Intermediate Similarity	NPC62800
0.7606	Intermediate Similarity	NPC324262
0.7603	Intermediate Similarity	NPC229505
0.7591	Intermediate Similarity	NPC472388
0.7589	Intermediate Similarity	NPC472132
0.7574	Intermediate Similarity	NPC175333
0.7574	Intermediate Similarity	NPC288416
0.7574	Intermediate Similarity	NPC35288
0.7574	Intermediate Similarity	NPC103533
0.7574	Intermediate Similarity	NPC45224
0.7574	Intermediate Similarity	NPC156692
0.7574	Intermediate Similarity	NPC471882
0.7574	Intermediate Similarity	NPC471881
0.7574	Intermediate Similarity	NPC173150
0.7574	Intermediate Similarity	NPC230331
0.7569	Intermediate Similarity	NPC265648
0.7569	Intermediate Similarity	NPC222433
0.7568	Intermediate Similarity	NPC469415
0.7561	Intermediate Similarity	NPC315070
0.7556	Intermediate Similarity	NPC470816
0.7554	Intermediate Similarity	NPC159811
0.7552	Intermediate Similarity	NPC475530
0.7552	Intermediate Similarity	NPC473799
0.7533	Intermediate Similarity	NPC469422
0.7532	Intermediate Similarity	NPC295408
0.7532	Intermediate Similarity	NPC329960
0.7532	Intermediate Similarity	NPC150893
0.7521	Intermediate Similarity	NPC475157
0.7521	Intermediate Similarity	NPC2313
0.7521	Intermediate Similarity	NPC57586
0.7521	Intermediate Similarity	NPC471637
0.7521	Intermediate Similarity	NPC154132
0.7521	Intermediate Similarity	NPC475655
0.7519	Intermediate Similarity	NPC475328
0.7517	Intermediate Similarity	NPC478250
0.7517	Intermediate Similarity	NPC470927
0.7517	Intermediate Similarity	NPC257970
0.7517	Intermediate Similarity	NPC69367
0.7516	Intermediate Similarity	NPC477488
0.75	Intermediate Similarity	NPC190849
0.75	Intermediate Similarity	NPC80098
0.75	Intermediate Similarity	NPC319404
0.75	Intermediate Similarity	NPC471157
0.75	Intermediate Similarity	NPC303429
0.75	Intermediate Similarity	NPC28637
0.75	Intermediate Similarity	NPC114116
0.75	Intermediate Similarity	NPC61181
0.75	Intermediate Similarity	NPC222102
0.75	Intermediate Similarity	NPC476385
0.75	Intermediate Similarity	NPC134405
0.75	Intermediate Similarity	NPC171007
0.7483	Intermediate Similarity	NPC143246
0.7483	Intermediate Similarity	NPC472350
0.7483	Intermediate Similarity	NPC81515
0.7483	Intermediate Similarity	NPC31745
0.7483	Intermediate Similarity	NPC475539
0.7483	Intermediate Similarity	NPC476383

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 NPC290276 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	230
0.1-0.2	693
0.2-0.3	1660
0.3-0.4	3323
0.4-0.5	2331
0.5-0.6	803
0.6-0.7	101
0.7-0.8	9
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
0.8074	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7266	Discontinued
0.7483	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6647	Phase 2
0.7208	Intermediate Similarity	NPD8455	Phase 2
0.7016	Intermediate Similarity	NPD7798	Approved
0.7008	Intermediate Similarity	NPD5048	Discontinued
0.7	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD6685	Approved
0.6947	Remote Similarity	NPD969	Suspended
0.6929	Remote Similarity	NPD5909	Discontinued
0.6923	Remote Similarity	NPD2067	Discontinued
0.6912	Remote Similarity	NPD8515	Approved
0.6912	Remote Similarity	NPD8517	Approved
0.6912	Remote Similarity	NPD8516	Approved
0.6899	Remote Similarity	NPD6686	Approved
0.689	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD8312	Approved
0.6886	Remote Similarity	NPD8313	Approved
0.6861	Remote Similarity	NPD5126	Approved
0.6861	Remote Similarity	NPD5125	Phase 3
0.68	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD2629	Approved
0.6788	Remote Similarity	NPD8513	Phase 3
0.6761	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7799	Discontinued
0.6719	Remote Similarity	NPD5765	Approved
0.6719	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6010	Discontinued
0.6692	Remote Similarity	NPD6912	Phase 3
0.6687	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7685	Pre-registration
0.6647	Remote Similarity	NPD7074	Phase 3
0.6647	Remote Similarity	NPD7472	Approved
0.6646	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7808	Phase 3
0.6627	Remote Similarity	NPD7228	Approved
0.6601	Remote Similarity	NPD6190	Approved
0.6591	Remote Similarity	NPD2182	Approved
0.6587	Remote Similarity	NPD7054	Approved
0.6577	Remote Similarity	NPD7097	Phase 1
0.6568	Remote Similarity	NPD7240	Approved
0.6568	Remote Similarity	NPD7251	Discontinued
0.6535	Remote Similarity	NPD9495	Approved
0.6525	Remote Similarity	NPD1091	Approved
0.6509	Remote Similarity	NPD6797	Phase 2
0.6504	Remote Similarity	NPD6698	Approved
0.6504	Remote Similarity	NPD46	Approved
0.6493	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD2066	Phase 3
0.6479	Remote Similarity	NPD6637	Approved
0.6471	Remote Similarity	NPD8368	Discontinued
0.6467	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD7829	Approved
0.6454	Remote Similarity	NPD7830	Approved
0.6429	Remote Similarity	NPD4628	Phase 3
0.6429	Remote Similarity	NPD8166	Discontinued
0.6423	Remote Similarity	NPD5346	Phase 2
0.6423	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD689	Discontinued
0.6423	Remote Similarity	NPD5347	Phase 2
0.642	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6233	Phase 2
0.6397	Remote Similarity	NPD6858	Approved
0.6397	Remote Similarity	NPD7094	Approved
0.6397	Remote Similarity	NPD8133	Approved
0.6392	Remote Similarity	NPD5403	Approved
0.6377	Remote Similarity	NPD4198	Discontinued
0.6371	Remote Similarity	NPD3673	Approved
0.6371	Remote Similarity	NPD3672	Approved
0.6371	Remote Similarity	NPD7838	Discovery
0.6369	Remote Similarity	NPD5401	Approved
0.6358	Remote Similarity	NPD8407	Phase 2
0.6357	Remote Similarity	NPD9545	Approved
0.6357	Remote Similarity	NPD1238	Approved
0.6352	Remote Similarity	NPD1653	Approved
0.6346	Remote Similarity	NPD7236	Approved
0.6343	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD2613	Approved
0.6322	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD7503	Approved
0.6312	Remote Similarity	NPD7458	Discontinued
0.6306	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD8320	Phase 1
0.6304	Remote Similarity	NPD8319	Approved
0.6296	Remote Similarity	NPD37	Approved
0.6294	Remote Similarity	NPD4807	Approved
0.6294	Remote Similarity	NPD4806	Approved
0.6288	Remote Similarity	NPD164	Approved
0.6282	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.628	Remote Similarity	NPD4965	Approved
0.628	Remote Similarity	NPD4966	Approved
0.628	Remote Similarity	NPD4967	Phase 2
0.6279	Remote Similarity	NPD6559	Discontinued
0.6279	Remote Similarity	NPD5926	Approved
0.6273	Remote Similarity	NPD4380	Phase 2
0.6268	Remote Similarity	NPD5305	Approved
0.6268	Remote Similarity	NPD5306	Approved
0.6267	Remote Similarity	NPD5120	Approved
0.6267	Remote Similarity	NPD5121	Approved
0.6267	Remote Similarity	NPD5119	Approved
0.626	Remote Similarity	NPD1282	Approved
0.626	Remote Similarity	NPD4793	Discontinued
0.6258	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7239	Suspended
0.6243	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD7075	Discontinued
0.6242	Remote Similarity	NPD6798	Discontinued
0.6241	Remote Similarity	NPD8377	Approved
0.6241	Remote Similarity	NPD8294	Approved
0.6241	Remote Similarity	NPD7741	Discontinued
0.6233	Remote Similarity	NPD2628	Approved
0.6233	Remote Similarity	NPD2159	Approved
0.6233	Remote Similarity	NPD2627	Approved
0.6233	Remote Similarity	NPD2626	Approved
0.6233	Remote Similarity	NPD2160	Approved
0.6233	Remote Similarity	NPD2625	Approved
0.6228	Remote Similarity	NPD8127	Discontinued
0.6225	Remote Similarity	NPD6355	Discontinued
0.6224	Remote Similarity	NPD8328	Phase 3
0.6221	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5402	Approved
0.6218	Remote Similarity	NPD2575	Approved
0.6218	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD1930	Approved
0.6212	Remote Similarity	NPD1929	Approved
0.6205	Remote Similarity	NPD6234	Discontinued
0.62	Remote Similarity	NPD4746	Phase 3
0.62	Remote Similarity	NPD2571	Approved
0.62	Remote Similarity	NPD3615	Approved
0.62	Remote Similarity	NPD3089	Approved
0.62	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.62	Remote Similarity	NPD4745	Approved
0.62	Remote Similarity	NPD3088	Approved
0.62	Remote Similarity	NPD2566	Approved
0.62	Remote Similarity	NPD3087	Approved
0.62	Remote Similarity	NPD3614	Approved
0.62	Remote Similarity	NPD7961	Discontinued
0.62	Remote Similarity	NPD3090	Approved
0.62	Remote Similarity	NPD2574	Discontinued
0.62	Remote Similarity	NPD2570	Approved
0.62	Remote Similarity	NPD2573	Approved
0.62	Remote Similarity	NPD3616	Approved
0.6197	Remote Similarity	NPD8296	Approved
0.6197	Remote Similarity	NPD8335	Approved
0.6197	Remote Similarity	NPD8380	Approved
0.6197	Remote Similarity	NPD8379	Approved
0.6197	Remote Similarity	NPD8378	Approved
0.6193	Remote Similarity	NPD8150	Discontinued
0.6193	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7983	Approved
0.6184	Remote Similarity	NPD6653	Approved
0.6182	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD7008	Discontinued
0.6173	Remote Similarity	NPD8417	Discontinued
0.6167	Remote Similarity	NPD226	Approved
0.6165	Remote Similarity	NPD1237	Approved
0.616	Remote Similarity	NPD800	Approved
0.6154	Remote Similarity	NPD1652	Phase 2
0.6154	Remote Similarity	NPD7699	Phase 2
0.6154	Remote Similarity	NPD7700	Phase 2
0.614	Remote Similarity	NPD3818	Discontinued
0.6138	Remote Similarity	NPD7507	Approved
0.6131	Remote Similarity	NPD7199	Phase 2
0.6129	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6004	Phase 3
0.6129	Remote Similarity	NPD6005	Phase 3
0.6129	Remote Similarity	NPD6002	Phase 3
0.6124	Remote Similarity	NPD8361	Approved
0.6124	Remote Similarity	NPD8360	Approved
0.6124	Remote Similarity	NPD8435	Approved
0.6124	Remote Similarity	NPD1989	Approved
0.6122	Remote Similarity	NPD2797	Approved
0.6118	Remote Similarity	NPD1933	Approved
0.6118	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD4686	Approved
0.6118	Remote Similarity	NPD230	Phase 1
0.6118	Remote Similarity	NPD4684	Phase 3
0.6118	Remote Similarity	NPD5124	Phase 1
0.6118	Remote Similarity	NPD4685	Phase 3
0.6115	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4106	Approved
0.6111	Remote Similarity	NPD1090	Approved
0.6111	Remote Similarity	NPD4135	Approved
0.6111	Remote Similarity	NPD1086	Approved
0.6111	Remote Similarity	NPD1089	Approved
0.6111	Remote Similarity	NPD4136	Approved
0.6107	Remote Similarity	NPD4620	Approved
0.6107	Remote Similarity	NPD5201	Approved
0.6107	Remote Similarity	NPD4617	Approved
0.6107	Remote Similarity	NPD5203	Approved
0.6107	Remote Similarity	NPD6832	Phase 2

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