NPASS Compound

Structure

NPC471026 OpenBabel07101718202D 97103 0 0 1 0 0 0 0 0999 V2000 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 10.4042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3149 6.2057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7060 10.2306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0480 9.2909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6124 6.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9696 7.4115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9544 5.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1036 7.9115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9544 4.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0328 9.1172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1188 8.0851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6124 3.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 8.1775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 7.9115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9696 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4489 5.7057 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 7.4115 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1036 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4489 4.7057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5829 4.2057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7169 4.7057 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7169 5.7057 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4456 1.5603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3149 4.2057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5829 3.2057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5829 6.2057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 6.6454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1188 2.3264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 3.7660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 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 46 2 0 0 0 0 32 46 1 0 0 0 0 34 48 1 0 0 0 0 35 51 1 0 0 0 0 36 52 1 0 0 0 0 37 53 1 0 0 0 0 38 39 2 0 0 0 0 38 46 1 0 0 0 0 39 47 1 0 0 0 0 40 47 1 0 0 0 0 41 73 1 0 0 0 0 42 4 1 1 0 0 0 42 49 1 0 0 0 0 42 85 1 0 0 0 0 43 5 1 1 0 0 0 43 54 1 0 0 0 0 43 86 1 0 0 0 0 44 6 1 6 0 0 0 44 61 1 0 0 0 0 44 87 1 0 0 0 0 45 7 1 1 0 0 0 45 62 1 0 0 0 0 45 88 1 0 0 0 0 47 74 2 0 0 0 0 48 33 1 1 0 0 0 48 89 1 0 0 0 0 49 40 1 6 0 0 0 49 63 1 0 0 0 0 50 41 1 1 0 0 0 50 55 1 0 0 0 0 50 90 1 0 0 0 0 51 75 2 0 0 0 0 51 91 1 0 0 0 0 52 76 2 0 0 0 0 52 92 1 0 0 0 0 53 77 2 0 0 0 0 53 93 1 0 0 0 0 54 57 1 0 0 0 0 54 78 1 1 0 0 0 55 56 1 0 0 0 0 55 79 1 6 0 0 0 56 58 1 0 0 0 0 56 80 1 1 0 0 0 57 64 1 0 0 0 0 57 81 1 1 0 0 0 58 68 1 0 0 0 0 58 82 1 6 0 0 0 59 61 1 0 0 0 0 59 65 1 0 0 0 0 59 83 1 6 0 0 0 60 63 1 0 0 0 0 60 69 1 0 0 0 0 60 84 1 1 0 0 0 61 94 1 1 0 0 0 62 66 1 0 0 0 0 62 95 1 6 0 0 0 63 91 1 1 0 0 0 64 70 1 0 0 0 0 64 96 1 6 0 0 0 65 71 1 0 0 0 0 65 92 1 6 0 0 0 66 67 1 0 0 0 0 66 97 1 1 0 0 0 67 72 1 0 0 0 0 67 93 1 1 0 0 0 68 90 1 0 0 0 0 68 97 1 1 0 0 0 69 85 1 0 0 0 0 69 95 1 6 0 0 0 70 86 1 1 0 0 0 70 89 1 0 0 0 0 71 87 1 1 0 0 0 71 96 1 0 0 0 0 72 88 1 0 0 0 0 72 94 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1380.78
Volume:	1392.636
LogP:	9.251
LogD:	5.117
LogS:	-4.99
# Rotatable Bonds:	31
TPSA:	350.11
# H-Bond Aceptor:	25
# H-Bond Donor:	8
# Rings:	7
# Heavy Atoms:	25

MedChem Properties

QED Drug-Likeness Score:	0.017
Synthetic Accessibility Score:	7.705
Fsp3:	0.833
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:	-5.275
MDCK Permeability:	4.5052653149468824e-05
Pgp-inhibitor:	0.951
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.896
20% Bioavailability (F20%):	0.0
30% Bioavailability (F30%):	0.427

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	96.60588836669922%
Volume Distribution (VD):	0.606
Pgp-substrate:	3.1125690937042236%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.044
CYP2C9-inhibitor:	0.108
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.078
CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.474
CYP3A4-substrate:	0.012

ADMET: Excretion

Clearance (CL):	1.244
Half-life (T1/2):	0.246

ADMET: Toxicity

hERG Blockers:	0.924
Human Hepatotoxicity (H-HT):	0.365
Drug-inuced Liver Injury (DILI):	0.896
AMES Toxicity:	0.117
Rat Oral Acute Toxicity:	0.69
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.959
Carcinogencity:	0.142
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.353

Download Data

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

Natural Product: NPC471026

Natural Product ID:	NPC471026
*Common Name:**	Purginoside Iii
IUPAC Name:	n.a.
Synonyms:	Purginoside III
Standard InCHIKey:	OOBXTPAHJCHFSP-GTRAIELPSA-N
Standard InCHI:	InChI=1S/C72H116O25/c1-8-11-14-15-17-21-30-37-53(77)93-67-66(97-68-58(82)56(80)55(79)50(41-73)90-68)62(95-69-60(84)63(91-51(75)35-25-13-10-3)49(42(4)85-69)40-47(74)39-38-46-31-26-23-27-32-46)45(7)88-72(67)94-61-44(6)87-71-65(59(61)83)92-52(76)36-29-22-19-16-18-20-28-34-48(33-24-12-9-2)89-70-64(96-71)57(81)54(78)43(5)86-70/h23,26-27,31-32,38-39,42-45,48-50,54-73,78-84H,8-22,24-25,28-30,33-37,40-41H2,1-7H3/b39-38+/t42-,43+,44-,45-,48-,49-,50+,54-,55+,56-,57-,58+,59+,60+,61-,62-,63+,64+,65+,66+,67+,68-,69-,70-,71-,72-/m0/s1
SMILES:	CCCCCCCCCC(=O)OC1C(C(C(OC1OC2C(OC3C(C2O)OC(=O)CCCCCCCCCC(OC4C(O3)C(C(C(O4)C)O)O)CCCCC)C)C)OC5C(C(C(C(O5)C)CC(=O)C=CC6=CC=CC=C6)OC(=O)CCCCC)O)OC7C(C(C(C(O7)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2336638
PubChem CID:	71717055
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[474042]
NPT83	Cell Line	MCF7	Homo sapiens	FC	=	2.1	n.a.	PMID[474042]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FC	=	1.8	n.a.	PMID[474042]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FC	=	1.2	n.a.	PMID[474042]

☑ 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 NPC471026 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	277
0.1-0.2	938
0.2-0.3	2647
0.3-0.4	7077
0.4-0.5	13751
0.5-0.6	13376
0.6-0.7	4241
0.7-0.8	346
0.8-0.85	14
0.85-0.9	12
0.9-0.95	17
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.935	High Similarity	NPC204214
0.935	High Similarity	NPC10121
0.935	High Similarity	NPC92283
0.935	High Similarity	NPC35338
0.935	High Similarity	NPC10883
0.935	High Similarity	NPC231888
0.935	High Similarity	NPC124878
0.935	High Similarity	NPC63404
0.935	High Similarity	NPC290276
0.935	High Similarity	NPC198918
0.9268	High Similarity	NPC77651
0.9268	High Similarity	NPC28069
0.92	High Similarity	NPC471024
0.9187	High Similarity	NPC162925
0.9187	High Similarity	NPC87153
0.912	High Similarity	NPC471025
0.904	High Similarity	NPC147032
0.8968	High Similarity	NPC231627
0.8898	High Similarity	NPC237182
0.8898	High Similarity	NPC226101
0.8871	High Similarity	NPC140561
0.8871	High Similarity	NPC141970
0.8548	High Similarity	NPC476096
0.8504	High Similarity	NPC473881
0.8345	Intermediate Similarity	NPC40085
0.8345	Intermediate Similarity	NPC264270
0.8273	Intermediate Similarity	NPC111466
0.8258	Intermediate Similarity	NPC11025
0.8201	Intermediate Similarity	NPC284957
0.8195	Intermediate Similarity	NPC319995
0.8195	Intermediate Similarity	NPC289415
0.8154	Intermediate Similarity	NPC244454
0.806	Intermediate Similarity	NPC305162
0.8049	Intermediate Similarity	NPC470825
0.8015	Intermediate Similarity	NPC317163
0.7973	Intermediate Similarity	NPC477736
0.7973	Intermediate Similarity	NPC477467
0.797	Intermediate Similarity	NPC148026
0.7926	Intermediate Similarity	NPC17567
0.7905	Intermediate Similarity	NPC477735
0.7905	Intermediate Similarity	NPC477472
0.7905	Intermediate Similarity	NPC477474
0.7905	Intermediate Similarity	NPC477470
0.7895	Intermediate Similarity	NPC114096
0.7883	Intermediate Similarity	NPC470143
0.7883	Intermediate Similarity	NPC322503
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	NPC57607
0.7815	Intermediate Similarity	NPC165234
0.7815	Intermediate Similarity	NPC475536
0.781	Intermediate Similarity	NPC159811
0.7808	Intermediate Similarity	NPC329657
0.7805	Intermediate Similarity	NPC184633
0.7803	Intermediate Similarity	NPC138798
0.7778	Intermediate Similarity	NPC474641
0.7717	Intermediate Similarity	NPC29607
0.7703	Intermediate Similarity	NPC69425
0.766	Intermediate Similarity	NPC469364
0.766	Intermediate Similarity	NPC65262
0.766	Intermediate Similarity	NPC101686
0.7647	Intermediate Similarity	NPC301857
0.7643	Intermediate Similarity	NPC263829
0.7622	Intermediate Similarity	NPC473755
0.7622	Intermediate Similarity	NPC475513
0.7603	Intermediate Similarity	NPC212808
0.7569	Intermediate Similarity	NPC469623
0.7569	Intermediate Similarity	NPC148080
0.754	Intermediate Similarity	NPC43584
0.7517	Intermediate Similarity	NPC293154
0.7516	Intermediate Similarity	NPC477488
0.7516	Intermediate Similarity	NPC477471
0.7516	Intermediate Similarity	NPC477466
0.7516	Intermediate Similarity	NPC477469
0.7516	Intermediate Similarity	NPC477473
0.75	Intermediate Similarity	NPC136608
0.75	Intermediate Similarity	NPC38420
0.7483	Intermediate Similarity	NPC87403
0.7464	Intermediate Similarity	NPC473443
0.7464	Intermediate Similarity	NPC27712
0.7447	Intermediate Similarity	NPC169398
0.7444	Intermediate Similarity	NPC229600
0.7426	Intermediate Similarity	NPC123704
0.7419	Intermediate Similarity	NPC329960
0.7419	Intermediate Similarity	NPC150893
0.7419	Intermediate Similarity	NPC295408
0.7415	Intermediate Similarity	NPC474241
0.7413	Intermediate Similarity	NPC475195
0.7398	Intermediate Similarity	NPC469527
0.7397	Intermediate Similarity	NPC469367
0.7391	Intermediate Similarity	NPC225103
0.7386	Intermediate Similarity	NPC476784
0.7383	Intermediate Similarity	NPC23677
0.7383	Intermediate Similarity	NPC70236
0.7383	Intermediate Similarity	NPC476092
0.7383	Intermediate Similarity	NPC475447
0.7383	Intermediate Similarity	NPC475218
0.7357	Intermediate Similarity	NPC235294
0.7357	Intermediate Similarity	NPC46137
0.7357	Intermediate Similarity	NPC80599
0.7355	Intermediate Similarity	NPC262826
0.7353	Intermediate Similarity	NPC145287
0.7347	Intermediate Similarity	NPC202391
0.7347	Intermediate Similarity	NPC64195
0.7347	Intermediate Similarity	NPC296659
0.7342	Intermediate Similarity	NPC102465
0.7342	Intermediate Similarity	NPC469420
0.7339	Intermediate Similarity	NPC19136
0.7339	Intermediate Similarity	NPC47286
0.7338	Intermediate Similarity	NPC477623
0.7338	Intermediate Similarity	NPC472388
0.7333	Intermediate Similarity	NPC96599
0.7325	Intermediate Similarity	NPC477491
0.732	Intermediate Similarity	NPC469417
0.7315	Intermediate Similarity	NPC474564
0.7315	Intermediate Similarity	NPC470330
0.731	Intermediate Similarity	NPC77493
0.7303	Intermediate Similarity	NPC469398
0.7303	Intermediate Similarity	NPC469456
0.7303	Intermediate Similarity	NPC106818
0.7297	Intermediate Similarity	NPC477737
0.7285	Intermediate Similarity	NPC240592
0.7285	Intermediate Similarity	NPC117346
0.7279	Intermediate Similarity	NPC119537
0.7279	Intermediate Similarity	NPC476378
0.7279	Intermediate Similarity	NPC264632
0.7279	Intermediate Similarity	NPC205864
0.7279	Intermediate Similarity	NPC478250
0.7279	Intermediate Similarity	NPC476397
0.7279	Intermediate Similarity	NPC298257
0.7279	Intermediate Similarity	NPC76406
0.7279	Intermediate Similarity	NPC175214
0.7279	Intermediate Similarity	NPC476375
0.7279	Intermediate Similarity	NPC476381
0.7279	Intermediate Similarity	NPC476380
0.7279	Intermediate Similarity	NPC96795
0.7279	Intermediate Similarity	NPC476384
0.7279	Intermediate Similarity	NPC112
0.7279	Intermediate Similarity	NPC269141
0.7279	Intermediate Similarity	NPC247032
0.7278	Intermediate Similarity	NPC475531
0.7278	Intermediate Similarity	NPC475198
0.7278	Intermediate Similarity	NPC475175
0.7266	Intermediate Similarity	NPC30563
0.726	Intermediate Similarity	NPC79908
0.726	Intermediate Similarity	NPC80098
0.7254	Intermediate Similarity	NPC114116
0.7248	Intermediate Similarity	NPC474268
0.7248	Intermediate Similarity	NPC475539
0.7248	Intermediate Similarity	NPC119773
0.7248	Intermediate Similarity	NPC143246
0.7246	Intermediate Similarity	NPC276047
0.7246	Intermediate Similarity	NPC267733
0.7246	Intermediate Similarity	NPC473423
0.7241	Intermediate Similarity	NPC220936
0.7241	Intermediate Similarity	NPC324262
0.7241	Intermediate Similarity	NPC62800
0.7241	Intermediate Similarity	NPC474250
0.7241	Intermediate Similarity	NPC31745
0.7241	Intermediate Similarity	NPC473440
0.7237	Intermediate Similarity	NPC475379
0.7234	Intermediate Similarity	NPC138777
0.7234	Intermediate Similarity	NPC225384
0.7234	Intermediate Similarity	NPC209851
0.7234	Intermediate Similarity	NPC246869
0.723	Intermediate Similarity	NPC471028
0.7222	Intermediate Similarity	NPC471345
0.7222	Intermediate Similarity	NPC472132
0.7215	Intermediate Similarity	NPC473557
0.7215	Intermediate Similarity	NPC473468
0.7215	Intermediate Similarity	NPC475567
0.7214	Intermediate Similarity	NPC469549
0.7203	Intermediate Similarity	NPC34456
0.7195	Intermediate Similarity	NPC475613
0.7195	Intermediate Similarity	NPC176246
0.7194	Intermediate Similarity	NPC106677
0.719	Intermediate Similarity	NPC5115
0.7188	Intermediate Similarity	NPC474148
0.7188	Intermediate Similarity	NPC68592
0.7188	Intermediate Similarity	NPC276061
0.7188	Intermediate Similarity	NPC262222
0.7188	Intermediate Similarity	NPC298666
0.7183	Intermediate Similarity	NPC15850
0.7181	Intermediate Similarity	NPC475528
0.7178	Intermediate Similarity	NPC124828
0.7174	Intermediate Similarity	NPC470818
0.7174	Intermediate Similarity	NPC476033
0.7174	Intermediate Similarity	NPC79608
0.7172	Intermediate Similarity	NPC476376
0.7171	Intermediate Similarity	NPC69367
0.7171	Intermediate Similarity	NPC182350
0.7165	Intermediate Similarity	NPC20485
0.7163	Intermediate Similarity	NPC470122
0.7163	Intermediate Similarity	NPC469705
0.7163	Intermediate Similarity	NPC475478
0.7163	Intermediate Similarity	NPC469519

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 NPC471026 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	707
0.2-0.3	1893
0.3-0.4	3436
0.4-0.5	2136
0.5-0.6	661
0.6-0.7	80
0.7-0.8	3
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
0.7941	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD6647	Phase 2
0.7016	Intermediate Similarity	NPD7798	Approved
0.7008	Intermediate Similarity	NPD5048	Discontinued
0.7007	Intermediate Similarity	NPD7266	Discontinued
0.6953	Remote Similarity	NPD6685	Approved
0.6885	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD8516	Approved
0.6788	Remote Similarity	NPD8517	Approved
0.6788	Remote Similarity	NPD8515	Approved
0.6772	Remote Similarity	NPD8455	Phase 2
0.6719	Remote Similarity	NPD5765	Approved
0.6692	Remote Similarity	NPD6912	Phase 3
0.6691	Remote Similarity	NPD8328	Phase 3
0.6686	Remote Similarity	NPD8312	Approved
0.6686	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6627	Remote Similarity	NPD7799	Discontinued
0.6617	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD2066	Phase 3
0.6587	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD7685	Pre-registration
0.6548	Remote Similarity	NPD7074	Phase 3
0.6548	Remote Similarity	NPD7472	Approved
0.6544	Remote Similarity	NPD2629	Approved
0.6543	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD2067	Discontinued
0.6529	Remote Similarity	NPD7808	Phase 3
0.6528	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6858	Approved
0.6519	Remote Similarity	NPD7094	Approved
0.6494	Remote Similarity	NPD6190	Approved
0.6488	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD7054	Approved
0.6471	Remote Similarity	NPD6010	Discontinued
0.6471	Remote Similarity	NPD7251	Discontinued
0.6471	Remote Similarity	NPD8368	Discontinued
0.6462	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7641	Discontinued
0.6444	Remote Similarity	NPD969	Suspended
0.6423	Remote Similarity	NPD5346	Phase 2
0.6423	Remote Similarity	NPD5347	Phase 2
0.642	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD7961	Discontinued
0.6412	Remote Similarity	NPD6797	Phase 2
0.6412	Remote Similarity	NPD5909	Discontinued
0.6406	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD6686	Approved
0.6383	Remote Similarity	NPD5126	Approved
0.6383	Remote Similarity	NPD5125	Phase 3
0.6371	Remote Similarity	NPD3673	Approved
0.6371	Remote Similarity	NPD3672	Approved
0.6358	Remote Similarity	NPD8407	Phase 2
0.6336	Remote Similarity	NPD1930	Approved
0.6336	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD1929	Approved
0.6331	Remote Similarity	NPD7228	Approved
0.6327	Remote Similarity	NPD2613	Approved
0.6322	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD8320	Phase 1
0.6304	Remote Similarity	NPD8319	Approved
0.6284	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD9495	Approved
0.6279	Remote Similarity	NPD7240	Approved
0.626	Remote Similarity	NPD1932	Approved
0.626	Remote Similarity	NPD4793	Discontinued
0.625	Remote Similarity	NPD7097	Phase 1
0.6243	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD7236	Approved
0.6224	Remote Similarity	NPD7829	Approved
0.6224	Remote Similarity	NPD7830	Approved
0.6222	Remote Similarity	NPD2329	Discontinued
0.6222	Remote Similarity	NPD2182	Approved
0.6222	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4628	Phase 3
0.6211	Remote Similarity	NPD7458	Discontinued
0.62	Remote Similarity	NPD4746	Phase 3
0.62	Remote Similarity	NPD3090	Approved
0.62	Remote Similarity	NPD2571	Approved
0.62	Remote Similarity	NPD3087	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	NPD3088	Approved
0.62	Remote Similarity	NPD2566	Approved
0.62	Remote Similarity	NPD3614	Approved
0.62	Remote Similarity	NPD2574	Discontinued
0.62	Remote Similarity	NPD2570	Approved
0.62	Remote Similarity	NPD2573	Approved
0.62	Remote Similarity	NPD4745	Approved
0.62	Remote Similarity	NPD3616	Approved
0.6194	Remote Similarity	NPD6412	Phase 2
0.6193	Remote Similarity	NPD8150	Discontinued
0.6193	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7983	Approved
0.6176	Remote Similarity	NPD1317	Discontinued
0.6173	Remote Similarity	NPD8417	Discontinued
0.6173	Remote Similarity	NPD4380	Phase 2
0.6172	Remote Similarity	NPD1693	Approved
0.6167	Remote Similarity	NPD226	Approved
0.616	Remote Similarity	NPD800	Approved
0.6159	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7699	Phase 2
0.6154	Remote Similarity	NPD7700	Phase 2
0.6149	Remote Similarity	NPD7239	Suspended
0.6145	Remote Similarity	NPD7075	Discontinued
0.6143	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.614	Remote Similarity	NPD3818	Discontinued
0.6138	Remote Similarity	NPD6637	Approved
0.6131	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD9545	Approved
0.6124	Remote Similarity	NPD8361	Approved
0.6124	Remote Similarity	NPD8360	Approved
0.6124	Remote Similarity	NPD8435	Approved
0.6124	Remote Similarity	NPD1989	Approved
0.6118	Remote Similarity	NPD4686	Approved
0.6118	Remote Similarity	NPD4684	Phase 3
0.6118	Remote Similarity	NPD4685	Phase 3
0.6115	Remote Similarity	NPD8166	Discontinued
0.6111	Remote Similarity	NPD1086	Approved
0.6111	Remote Similarity	NPD1090	Approved
0.6111	Remote Similarity	NPD1089	Approved
0.6103	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6101	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5403	Approved
0.6084	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6069	Remote Similarity	NPD3132	Approved
0.6069	Remote Similarity	NPD2612	Approved
0.6069	Remote Similarity	NPD2609	Approved
0.6069	Remote Similarity	NPD2608	Approved
0.6069	Remote Similarity	NPD4216	Approved
0.6069	Remote Similarity	NPD4217	Approved
0.6069	Remote Similarity	NPD4807	Approved
0.6069	Remote Similarity	NPD4806	Approved
0.6069	Remote Similarity	NPD3131	Approved
0.6069	Remote Similarity	NPD4218	Approved
0.6069	Remote Similarity	NPD1091	Approved
0.6069	Remote Similarity	NPD3603	Phase 3
0.6069	Remote Similarity	NPD2610	Approved
0.6069	Remote Similarity	NPD4215	Approved
0.6069	Remote Similarity	NPD2611	Approved
0.6066	Remote Similarity	NPD9491	Approved
0.6062	Remote Similarity	NPD5401	Approved
0.6053	Remote Similarity	NPD5121	Approved
0.6053	Remote Similarity	NPD5119	Approved
0.6053	Remote Similarity	NPD5120	Approved
0.6047	Remote Similarity	NPD3751	Discontinued
0.6045	Remote Similarity	NPD1237	Approved
0.6043	Remote Similarity	NPD8133	Approved
0.6042	Remote Similarity	NPD5306	Approved
0.6042	Remote Similarity	NPD5305	Approved
0.6039	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD5402	Approved
0.6016	Remote Similarity	NPD1088	Approved
0.6014	Remote Similarity	NPD2628	Approved
0.6014	Remote Similarity	NPD2159	Approved
0.6014	Remote Similarity	NPD2626	Approved
0.6014	Remote Similarity	NPD2160	Approved
0.6014	Remote Similarity	NPD2625	Approved
0.6014	Remote Similarity	NPD2627	Approved
0.6013	Remote Similarity	NPD230	Phase 1
0.6013	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6013	Remote Similarity	NPD2575	Approved
0.6011	Remote Similarity	NPD8434	Phase 2
0.6	Remote Similarity	NPD6559	Discontinued
0.6	Remote Similarity	NPD37	Approved
0.6	Remote Similarity	NPD3787	Discontinued
0.6	Remote Similarity	NPD2652	Approved
0.6	Remote Similarity	NPD2650	Approved
0.6	Remote Similarity	NPD6801	Discontinued
0.6	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8151	Discontinued
0.6	Remote Similarity	NPD7305	Phase 1
0.6	Remote Similarity	NPD6799	Approved
0.5989	Remote Similarity	NPD6534	Approved
0.5989	Remote Similarity	NPD6535	Approved
0.5989	Remote Similarity	NPD7435	Discontinued
0.5988	Remote Similarity	NPD4965	Approved
0.5988	Remote Similarity	NPD4967	Phase 2
0.5988	Remote Similarity	NPD4966	Approved
0.5988	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.5987	Remote Similarity	NPD6233	Phase 2
0.5986	Remote Similarity	NPD8448	Approved
0.5984	Remote Similarity	NPD46	Approved
0.5984	Remote Similarity	NPD6698	Approved
0.5973	Remote Similarity	NPD8391	Approved
0.5973	Remote Similarity	NPD8392	Approved
0.5973	Remote Similarity	NPD8390	Approved
0.5972	Remote Similarity	NPD5981	Approved
0.5972	Remote Similarity	NPD8444	Approved
0.5964	Remote Similarity	NPD7819	Suspended
0.596	Remote Similarity	NPD4738	Phase 2
0.5959	Remote Similarity	NPD8299	Approved
0.5959	Remote Similarity	NPD8342	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