NPASS Compound

Structure

CID77651 OpenBabel06191715412D 97103 0 0 1 0 0 0 0 0999 V2000 3.5380 -9.9736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0494 0.3430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0668 8.9994 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 2.6136 -2.4789 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 -0.8771 1.4935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5306 -8.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4116 1.1088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0593 7.9995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6609 -8.4802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4295 0.9394 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 2.6535 -7.4802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7839 -6.9867 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 1.7764 -5.9868 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 4.5221 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 -7.8493 7.4417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7917 1.7052 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 -7.8419 6.4418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9871 7.9481 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 -6.9722 5.9482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1174 7.4545 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 -1.7764 5.9868 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 -5.2403 5.9611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2329 4.9611 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 6.9415 -0.9731 0.0000 C 0 0 2 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 -1.7542 2.9870 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 -6.1100 6.4546 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 -1.7690 4.9868 0.0000 C 0 0 0 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 -4.3632 4.4676 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 1.7320 0.0095 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 1.7394 -0.9871 0.0000 C 0 0 1 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 -1.7319 -0.0128 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4861 2.9741 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 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 -2.5794 -2.5191 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 6.0691 0.5380 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 -0.8993 4.4933 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8663 1.5022 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 -3.5010 4.9740 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 -2.5320 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 -4.3410 1.4678 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 -2.6313 4.4804 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 2.5988 1.5109 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 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 8 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 24 1 0 0 0 0 13 25 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 28 1 0 0 0 0 21 30 1 0 0 0 0 22 29 1 0 0 0 0 23 26 2 0 0 0 0 23 27 1 0 0 0 0 24 33 1 0 0 0 0 25 35 1 0 0 0 0 26 31 1 0 0 0 0 27 32 2 0 0 0 0 28 34 1 0 0 0 0 29 36 1 0 0 0 0 30 37 1 0 0 0 0 31 45 2 0 0 0 0 32 45 1 0 0 0 0 34 46 1 0 0 0 0 35 48 1 0 0 0 0 36 49 1 0 0 0 0 37 50 1 0 0 0 0 38 39 2 0 0 0 0 38 45 1 0 0 0 0 39 51 1 0 0 0 0 40 72 1 0 0 0 0 41 4 1 6 0 0 0 41 52 1 0 0 0 0 41 84 1 0 0 0 0 42 5 1 1 0 0 0 42 59 1 0 0 0 0 42 86 1 0 0 0 0 43 6 1 6 0 0 0 43 60 1 0 0 0 0 43 85 1 0 0 0 0 44 7 1 6 0 0 0 44 61 1 0 0 0 0 44 87 1 0 0 0 0 46 33 1 6 0 0 0 46 88 1 0 0 0 0 47 40 1 6 0 0 0 47 53 1 0 0 0 0 47 89 1 0 0 0 0 48 73 2 0 0 0 0 48 90 1 0 0 0 0 49 74 2 0 0 0 0 49 92 1 0 0 0 0 50 75 2 0 0 0 0 50 93 1 0 0 0 0 51 76 2 0 0 0 0 51 91 1 0 0 0 0 52 55 1 0 0 0 0 52 77 1 6 0 0 0 53 54 1 0 0 0 0 53 78 1 1 0 0 0 54 56 1 0 0 0 0 54 79 1 6 0 0 0 55 63 1 0 0 0 0 55 80 1 6 0 0 0 56 67 1 0 0 0 0 56 81 1 1 0 0 0 57 59 1 0 0 0 0 57 64 1 0 0 0 0 57 82 1 1 0 0 0 58 62 1 0 0 0 0 58 68 1 0 0 0 0 58 83 1 6 0 0 0 59 94 1 6 0 0 0 60 62 1 0 0 0 0 60 90 1 1 0 0 0 61 65 1 0 0 0 0 61 95 1 1 0 0 0 62 91 1 6 0 0 0 63 69 1 0 0 0 0 63 96 1 1 0 0 0 64 70 1 0 0 0 0 64 92 1 1 0 0 0 65 66 1 0 0 0 0 65 97 1 6 0 0 0 66 71 1 0 0 0 0 66 93 1 6 0 0 0 67 89 1 0 0 0 0 67 97 1 6 0 0 0 68 85 1 0 0 0 0 68 95 1 1 0 0 0 69 84 1 6 0 0 0 69 88 1 0 0 0 0 70 86 1 6 0 0 0 70 96 1 0 0 0 0 71 87 1 0 0 0 0 71 94 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1382.76
Volume:	1384.13
LogP:	9.067
LogD:	4.842
LogS:	-4.757
# Rotatable Bonds:	31
TPSA:	359.34
# H-Bond Aceptor:	26
# H-Bond Donor:	8
# Rings:	7
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.02
Synthetic Accessibility Score:	7.632
Fsp3:	0.831
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:	-5.255
MDCK Permeability:	6.14625314483419e-05
Pgp-inhibitor:	0.917
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.931
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.626

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	96.88582611083984%
Volume Distribution (VD):	0.634
Pgp-substrate:	3.756711959838867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.04
CYP2C9-inhibitor:	0.1
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.478
CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.572
CYP3A4-substrate:	0.014

ADMET: Excretion

Clearance (CL):	1.195
Half-life (T1/2):	0.109

ADMET: Toxicity

hERG Blockers:	0.839
Human Hepatotoxicity (H-HT):	0.355
Drug-inuced Liver Injury (DILI):	0.825
AMES Toxicity:	0.103
Rat Oral Acute Toxicity:	0.6
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.962
Carcinogencity:	0.065
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.154

Download Data

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

Natural Product: NPC77651

Natural Product ID:	NPC77651
*Common Name:**	Purginoside Ii
IUPAC Name:	n.a.
Synonyms:	Purginoside II
Standard InCHIKey:	MGJQNRHGDBVBKJ-KJRQEDIZSA-N
Standard InCHI:	InChI=1S/C71H114O26/c1-8-11-14-15-17-21-30-37-50(75)93-66-65(97-67-56(81)54(79)53(78)47(40-72)89-67)61(95-68-58(83)62(91-51(76)39-38-45-31-26-23-27-32-45)60(43(6)85-68)90-48(73)35-25-13-10-3)44(7)87-71(66)94-59-42(5)86-70-64(57(59)82)92-49(74)36-29-22-19-16-18-20-28-34-46(33-24-12-9-2)88-69-63(96-70)55(80)52(77)41(4)84-69/h23,26-27,31-32,38-39,41-44,46-47,52-72,77-83H,8-22,24-25,28-30,33-37,40H2,1-7H3/b39-38+/t41-,42+,43+,44+,46+,47-,52+,53-,54+,55+,56-,57-,58-,59+,60+,61+,62+,63-,64-,65-,66-,67+,68+,69+,70+,71+/m1/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]1O)OC(=O)/C=C/c1ccccc1)OC(=O)CCCCC)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:	CHEMBL2336641
PubChem CID:	53355580
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[512627]
NPT83	Cell Line	MCF7	Homo sapiens	FC	=	1.4	n.a.	PMID[512627]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FC	=	1.4	n.a.	PMID[512627]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FC	=	1.2	n.a.	PMID[512627]

☑ 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 NPC77651 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	276
0.1-0.2	973
0.2-0.3	2441
0.3-0.4	6609
0.4-0.5	12550
0.5-0.6	14604
0.6-0.7	4558
0.7-0.8	626
0.8-0.85	29
0.85-0.9	13
0.9-0.95	1
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC28069
0.9916	High Similarity	NPC35338
0.9916	High Similarity	NPC10121
0.9916	High Similarity	NPC63404
0.9916	High Similarity	NPC204214
0.9916	High Similarity	NPC124878
0.9916	High Similarity	NPC290276
0.9916	High Similarity	NPC10883
0.9916	High Similarity	NPC198918
0.9916	High Similarity	NPC231888
0.9916	High Similarity	NPC92283
0.9915	High Similarity	NPC162925
0.9915	High Similarity	NPC87153
0.9833	High Similarity	NPC471025
0.9752	High Similarity	NPC471024
0.9587	High Similarity	NPC147032
0.9268	High Similarity	NPC471026
0.9256	High Similarity	NPC141970
0.9256	High Similarity	NPC140561
0.904	High Similarity	NPC231627
0.8968	High Similarity	NPC237182
0.8968	High Similarity	NPC226101
0.8926	High Similarity	NPC476096
0.8729	High Similarity	NPC470825
0.8676	High Similarity	NPC40085
0.8676	High Similarity	NPC264270
0.8603	High Similarity	NPC111466
0.8594	High Similarity	NPC148026
0.8571	High Similarity	NPC473881
0.8516	High Similarity	NPC114096
0.8504	High Similarity	NPC57607
0.8475	Intermediate Similarity	NPC184633
0.8462	Intermediate Similarity	NPC11025
0.8397	Intermediate Similarity	NPC289415
0.8397	Intermediate Similarity	NPC319995
0.8394	Intermediate Similarity	NPC284957
0.8359	Intermediate Similarity	NPC244454
0.8279	Intermediate Similarity	NPC474641
0.8244	Intermediate Similarity	NPC301857
0.8222	Intermediate Similarity	NPC263829
0.8211	Intermediate Similarity	NPC29607
0.8182	Intermediate Similarity	NPC43584
0.812	Intermediate Similarity	NPC17567
0.8074	Intermediate Similarity	NPC322503
0.8074	Intermediate Similarity	NPC470143
0.8058	Intermediate Similarity	NPC473755
0.8058	Intermediate Similarity	NPC475513
0.8051	Intermediate Similarity	NPC469527
0.8047	Intermediate Similarity	NPC229600
0.8027	Intermediate Similarity	NPC477467
0.7971	Intermediate Similarity	NPC65262
0.7971	Intermediate Similarity	NPC101686
0.7971	Intermediate Similarity	NPC469364
0.7959	Intermediate Similarity	NPC477470
0.7959	Intermediate Similarity	NPC477472
0.7959	Intermediate Similarity	NPC477474
0.7941	Intermediate Similarity	NPC136608
0.7941	Intermediate Similarity	NPC38420
0.7926	Intermediate Similarity	NPC235294
0.7926	Intermediate Similarity	NPC46137
0.7905	Intermediate Similarity	NPC477736
0.7887	Intermediate Similarity	NPC64195
0.7886	Intermediate Similarity	NPC30563
0.7863	Intermediate Similarity	NPC138798
0.7862	Intermediate Similarity	NPC329657
0.7852	Intermediate Similarity	NPC305162
0.7842	Intermediate Similarity	NPC475195
0.7838	Intermediate Similarity	NPC477735
0.7823	Intermediate Similarity	NPC106818
0.7817	Intermediate Similarity	NPC293154
0.7817	Intermediate Similarity	NPC247032
0.7817	Intermediate Similarity	NPC112
0.7817	Intermediate Similarity	NPC476375
0.7817	Intermediate Similarity	NPC476397
0.7817	Intermediate Similarity	NPC76406
0.7817	Intermediate Similarity	NPC476380
0.7817	Intermediate Similarity	NPC298257
0.7817	Intermediate Similarity	NPC119537
0.7817	Intermediate Similarity	NPC264632
0.7817	Intermediate Similarity	NPC96795
0.7817	Intermediate Similarity	NPC269141
0.7817	Intermediate Similarity	NPC476378
0.7817	Intermediate Similarity	NPC205864
0.7817	Intermediate Similarity	NPC476384
0.7817	Intermediate Similarity	NPC175214
0.7817	Intermediate Similarity	NPC476381
0.7815	Intermediate Similarity	NPC475437
0.7815	Intermediate Similarity	NPC475505
0.7815	Intermediate Similarity	NPC473641
0.7815	Intermediate Similarity	NPC473797
0.7815	Intermediate Similarity	NPC475300
0.7815	Intermediate Similarity	NPC475464
0.7805	Intermediate Similarity	NPC276061
0.7805	Intermediate Similarity	NPC474148
0.7803	Intermediate Similarity	NPC145287
0.7794	Intermediate Similarity	NPC246869
0.7794	Intermediate Similarity	NPC138777
0.7794	Intermediate Similarity	NPC225384
0.7793	Intermediate Similarity	NPC475218
0.7793	Intermediate Similarity	NPC70236
0.7793	Intermediate Similarity	NPC476092
0.7793	Intermediate Similarity	NPC475447
0.7785	Intermediate Similarity	NPC476784
0.7778	Intermediate Similarity	NPC27712
0.777	Intermediate Similarity	NPC87403
0.777	Intermediate Similarity	NPC471345
0.7762	Intermediate Similarity	NPC471028
0.7761	Intermediate Similarity	NPC106677
0.7755	Intermediate Similarity	NPC69425
0.7754	Intermediate Similarity	NPC169398
0.7748	Intermediate Similarity	NPC165234
0.7748	Intermediate Similarity	NPC475536
0.7746	Intermediate Similarity	NPC469623
0.7746	Intermediate Similarity	NPC148080
0.7733	Intermediate Similarity	NPC477623
0.7724	Intermediate Similarity	NPC474564
0.7714	Intermediate Similarity	NPC476376
0.7703	Intermediate Similarity	NPC469398
0.7692	Intermediate Similarity	NPC469367
0.7687	Intermediate Similarity	NPC267733
0.7687	Intermediate Similarity	NPC276047
0.7676	Intermediate Similarity	NPC476377
0.7676	Intermediate Similarity	NPC47471
0.7671	Intermediate Similarity	NPC23677
0.7662	Intermediate Similarity	NPC475175
0.7662	Intermediate Similarity	NPC475531
0.7662	Intermediate Similarity	NPC475198
0.7655	Intermediate Similarity	NPC229505
0.7655	Intermediate Similarity	NPC212808
0.7647	Intermediate Similarity	NPC473443
0.7639	Intermediate Similarity	NPC296659
0.7639	Intermediate Similarity	NPC202391
0.763	Intermediate Similarity	NPC35288
0.763	Intermediate Similarity	NPC156692
0.763	Intermediate Similarity	NPC173150
0.763	Intermediate Similarity	NPC471882
0.763	Intermediate Similarity	NPC45224
0.763	Intermediate Similarity	NPC471881
0.763	Intermediate Similarity	NPC103533
0.763	Intermediate Similarity	NPC288416
0.7622	Intermediate Similarity	NPC265648
0.7622	Intermediate Similarity	NPC222433
0.7606	Intermediate Similarity	NPC475530
0.7606	Intermediate Similarity	NPC473799
0.7597	Intermediate Similarity	NPC475567
0.7597	Intermediate Similarity	NPC473468
0.7597	Intermediate Similarity	NPC473557
0.7591	Intermediate Similarity	NPC475478
0.7574	Intermediate Similarity	NPC225103
0.7569	Intermediate Similarity	NPC478250
0.7568	Intermediate Similarity	NPC470927
0.7568	Intermediate Similarity	NPC257970
0.7564	Intermediate Similarity	NPC477469
0.7564	Intermediate Similarity	NPC477473
0.7564	Intermediate Similarity	NPC477466
0.7564	Intermediate Similarity	NPC477471
0.7556	Intermediate Similarity	NPC471157
0.7556	Intermediate Similarity	NPC61181
0.7554	Intermediate Similarity	NPC114116
0.7554	Intermediate Similarity	NPC28637
0.7552	Intermediate Similarity	NPC476385
0.7552	Intermediate Similarity	NPC134405
0.7552	Intermediate Similarity	NPC80098
0.7551	Intermediate Similarity	NPC469448
0.7537	Intermediate Similarity	NPC317163
0.7536	Intermediate Similarity	NPC478255
0.7536	Intermediate Similarity	NPC281798
0.7536	Intermediate Similarity	NPC80599
0.7535	Intermediate Similarity	NPC64141
0.7535	Intermediate Similarity	NPC472350
0.7535	Intermediate Similarity	NPC62800
0.7535	Intermediate Similarity	NPC205195
0.7535	Intermediate Similarity	NPC197316
0.7535	Intermediate Similarity	NPC89105
0.7535	Intermediate Similarity	NPC68092
0.7535	Intermediate Similarity	NPC81515
0.7535	Intermediate Similarity	NPC476383
0.7535	Intermediate Similarity	NPC324262
0.7519	Intermediate Similarity	NPC52097
0.7518	Intermediate Similarity	NPC472132
0.7518	Intermediate Similarity	NPC472388
0.7517	Intermediate Similarity	NPC196063
0.7517	Intermediate Similarity	NPC296954
0.7517	Intermediate Similarity	NPC300894
0.7517	Intermediate Similarity	NPC141455
0.75	Intermediate Similarity	NPC473427
0.75	Intermediate Similarity	NPC34456
0.75	Intermediate Similarity	NPC476386
0.75	Intermediate Similarity	NPC175333
0.75	Intermediate Similarity	NPC476398
0.75	Intermediate Similarity	NPC94871
0.75	Intermediate Similarity	NPC259347
0.75	Intermediate Similarity	NPC230331
0.75	Intermediate Similarity	NPC470933
0.75	Intermediate Similarity	NPC471062
0.75	Intermediate Similarity	NPC469415
0.75	Intermediate Similarity	NPC306890
0.7484	Intermediate Similarity	NPC246024
0.7482	Intermediate Similarity	NPC159811
0.7481	Intermediate Similarity	NPC126991

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 NPC77651 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	695
0.2-0.3	1644
0.3-0.4	3352
0.4-0.5	2337
0.5-0.6	784
0.6-0.7	98
0.7-0.8	7
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
0.8	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD7266	Discontinued
0.7415	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD8455	Phase 2
0.7177	Intermediate Similarity	NPD6647	Phase 2
0.7073	Intermediate Similarity	NPD7798	Approved
0.7063	Intermediate Similarity	NPD5048	Discontinued
0.7	Intermediate Similarity	NPD969	Suspended
0.6977	Remote Similarity	NPD2067	Discontinued
0.6923	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD5126	Approved
0.6912	Remote Similarity	NPD5125	Phase 3
0.6875	Remote Similarity	NPD6685	Approved
0.685	Remote Similarity	NPD5909	Discontinued
0.6838	Remote Similarity	NPD8516	Approved
0.6838	Remote Similarity	NPD8517	Approved
0.6838	Remote Similarity	NPD8515	Approved
0.6829	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD8312	Approved
0.6826	Remote Similarity	NPD8313	Approved
0.6822	Remote Similarity	NPD6686	Approved
0.6783	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD6010	Discontinued
0.6727	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.672	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD2629	Approved
0.6715	Remote Similarity	NPD8513	Phase 3
0.669	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7074	Phase 3
0.6687	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD7799	Discontinued
0.6667	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7808	Phase 3
0.6645	Remote Similarity	NPD6190	Approved
0.6641	Remote Similarity	NPD2182	Approved
0.6641	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5765	Approved
0.6627	Remote Similarity	NPD7054	Approved
0.6617	Remote Similarity	NPD6912	Phase 3
0.6607	Remote Similarity	NPD7685	Pre-registration
0.6607	Remote Similarity	NPD7251	Discontinued
0.6587	Remote Similarity	NPD9495	Approved
0.6571	Remote Similarity	NPD1091	Approved
0.6566	Remote Similarity	NPD7228	Approved
0.6548	Remote Similarity	NPD6797	Phase 2
0.6541	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7097	Phase 1
0.6509	Remote Similarity	NPD7240	Approved
0.6475	Remote Similarity	NPD689	Discontinued
0.6471	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4628	Phase 3
0.6463	Remote Similarity	NPD6233	Phase 2
0.6457	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD5403	Approved
0.6423	Remote Similarity	NPD6698	Approved
0.6423	Remote Similarity	NPD46	Approved
0.6423	Remote Similarity	NPD4198	Discontinued
0.6418	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD8368	Discontinued
0.641	Remote Similarity	NPD5401	Approved
0.6408	Remote Similarity	NPD6637	Approved
0.6406	Remote Similarity	NPD2066	Phase 3
0.6406	Remote Similarity	NPD1238	Approved
0.6403	Remote Similarity	NPD9545	Approved
0.64	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD1653	Approved
0.6391	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD7829	Approved
0.6383	Remote Similarity	NPD7830	Approved
0.6382	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8166	Discontinued
0.6346	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5347	Phase 2
0.6341	Remote Similarity	NPD5346	Phase 2
0.6336	Remote Similarity	NPD164	Approved
0.6324	Remote Similarity	NPD7094	Approved
0.6324	Remote Similarity	NPD6858	Approved
0.6324	Remote Similarity	NPD8133	Approved
0.6316	Remote Similarity	NPD6559	Discontinued
0.6312	Remote Similarity	NPD4380	Phase 2
0.6311	Remote Similarity	NPD1282	Approved
0.6311	Remote Similarity	NPD4793	Discontinued
0.6301	Remote Similarity	NPD8407	Phase 2
0.6296	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.629	Remote Similarity	NPD3672	Approved
0.629	Remote Similarity	NPD3673	Approved
0.629	Remote Similarity	NPD7838	Discovery
0.6284	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD6798	Discontinued
0.6282	Remote Similarity	NPD7236	Approved
0.628	Remote Similarity	NPD7075	Discontinued
0.6279	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD2626	Approved
0.6276	Remote Similarity	NPD2160	Approved
0.6276	Remote Similarity	NPD2625	Approved
0.6276	Remote Similarity	NPD2628	Approved
0.6276	Remote Similarity	NPD2159	Approved
0.6276	Remote Similarity	NPD2627	Approved
0.6264	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD2613	Approved
0.6258	Remote Similarity	NPD5402	Approved
0.6258	Remote Similarity	NPD2575	Approved
0.6258	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7458	Discontinued
0.625	Remote Similarity	NPD8319	Approved
0.625	Remote Similarity	NPD8320	Phase 1
0.6241	Remote Similarity	NPD7503	Approved
0.6235	Remote Similarity	NPD37	Approved
0.6224	Remote Similarity	NPD4806	Approved
0.6224	Remote Similarity	NPD4807	Approved
0.622	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4965	Approved
0.622	Remote Similarity	NPD4966	Approved
0.622	Remote Similarity	NPD4967	Phase 2
0.6218	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD226	Approved
0.6216	Remote Similarity	NPD7008	Discontinued
0.6212	Remote Similarity	NPD1237	Approved
0.6202	Remote Similarity	NPD5926	Approved
0.62	Remote Similarity	NPD5120	Approved
0.62	Remote Similarity	NPD5121	Approved
0.62	Remote Similarity	NPD5119	Approved
0.6197	Remote Similarity	NPD5306	Approved
0.6197	Remote Similarity	NPD5305	Approved
0.6194	Remote Similarity	NPD1652	Phase 2
0.6188	Remote Similarity	NPD7699	Phase 2
0.6188	Remote Similarity	NPD7239	Suspended
0.6188	Remote Similarity	NPD7700	Phase 2
0.6176	Remote Similarity	NPD3818	Discontinued
0.6172	Remote Similarity	NPD1989	Approved
0.617	Remote Similarity	NPD8377	Approved
0.617	Remote Similarity	NPD8294	Approved
0.617	Remote Similarity	NPD7741	Discontinued
0.6168	Remote Similarity	NPD8127	Discontinued
0.6159	Remote Similarity	NPD230	Phase 1
0.6159	Remote Similarity	NPD6355	Discontinued
0.6159	Remote Similarity	NPD1933	Approved
0.6154	Remote Similarity	NPD8328	Phase 3
0.6154	Remote Similarity	NPD4106	Approved
0.6154	Remote Similarity	NPD4136	Approved
0.6154	Remote Similarity	NPD4135	Approved
0.6149	Remote Similarity	NPD4617	Approved
0.6149	Remote Similarity	NPD4620	Approved
0.6149	Remote Similarity	NPD5201	Approved
0.6149	Remote Similarity	NPD5203	Approved
0.6149	Remote Similarity	NPD6832	Phase 2
0.6145	Remote Similarity	NPD6234	Discontinued
0.6144	Remote Similarity	NPD7033	Discontinued
0.6139	Remote Similarity	NPD6799	Approved
0.6136	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD1929	Approved
0.6136	Remote Similarity	NPD8150	Discontinued
0.6136	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD1930	Approved
0.6135	Remote Similarity	NPD6801	Discontinued
0.6133	Remote Similarity	NPD4746	Phase 3
0.6133	Remote Similarity	NPD7961	Discontinued
0.6133	Remote Similarity	NPD3616	Approved
0.6133	Remote Similarity	NPD2571	Approved
0.6133	Remote Similarity	NPD2574	Discontinued
0.6133	Remote Similarity	NPD3088	Approved
0.6133	Remote Similarity	NPD4062	Phase 3
0.6133	Remote Similarity	NPD2570	Approved
0.6133	Remote Similarity	NPD2573	Approved
0.6133	Remote Similarity	NPD3615	Approved
0.6133	Remote Similarity	NPD3614	Approved
0.6133	Remote Similarity	NPD3090	Approved
0.6133	Remote Similarity	NPD2566	Approved
0.6133	Remote Similarity	NPD4745	Approved
0.6133	Remote Similarity	NPD3087	Approved
0.6133	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD3089	Approved
0.6127	Remote Similarity	NPD8380	Approved
0.6127	Remote Similarity	NPD8335	Approved
0.6127	Remote Similarity	NPD8378	Approved
0.6127	Remote Similarity	NPD8379	Approved
0.6127	Remote Similarity	NPD8296	Approved
0.6125	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6653	Approved
0.6116	Remote Similarity	NPD9491	Approved
0.6111	Remote Similarity	NPD8417	Discontinued
0.6111	Remote Similarity	NPD7983	Approved
0.6098	Remote Similarity	NPD7819	Suspended
0.6096	Remote Similarity	NPD5667	Approved
0.609	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD3751	Discontinued
0.608	Remote Similarity	NPD800	Approved
0.6074	Remote Similarity	NPD7411	Suspended
0.6071	Remote Similarity	NPD7199	Phase 2
0.6069	Remote Similarity	NPD7507	Approved
0.6067	Remote Similarity	NPD8361	Approved
0.6067	Remote Similarity	NPD3764	Approved
0.6067	Remote Similarity	NPD8435	Approved
0.6067	Remote Similarity	NPD8360	Approved
0.6067	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6065	Remote Similarity	NPD6002	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data