NPASS Compound

Structure

CID200708 OpenBabel06191715592D 39 43 0 0 1 0 0 0 0 0999 V2000 3.5211 -0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8512 2.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 -0.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9852 2.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9852 0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 2.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 -3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2226 1.3578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 0.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8512 1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 -0.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1192 2.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2532 2.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 1.4122 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1192 1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 -3.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9230 -3.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0570 -3.0878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0570 -2.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6180 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9230 -1.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6551 -4.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3271 2.3523 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7173 0.9122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2532 3.9122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 -4.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -3.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4135 1.9456 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 0.9230 -0.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2532 0.9122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 -2.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 1 12 2 0 0 0 0 2 5 2 0 0 0 0 2 12 1 0 0 0 0 3 6 2 0 0 0 0 3 13 1 0 0 0 0 4 14 2 0 0 0 0 5 14 1 0 0 0 0 6 15 1 0 0 0 0 7 13 2 0 0 0 0 7 18 1 0 0 0 0 8 16 1 0 0 0 0 8 17 1 0 0 0 0 9 27 1 0 0 0 0 10 26 1 0 0 0 0 10 28 1 0 0 0 0 11 26 1 0 0 0 0 11 35 1 0 0 0 0 13 29 1 0 0 0 0 14 36 1 0 0 0 0 15 16 1 0 0 0 0 15 18 2 0 0 0 0 16 30 2 0 0 0 0 17 12 1 6 0 0 0 17 37 1 0 0 0 0 18 37 1 0 0 0 0 19 9 1 6 0 0 0 19 20 1 0 0 0 0 19 38 1 0 0 0 0 20 21 1 0 0 0 0 20 31 1 1 0 0 0 21 22 1 0 0 0 0 21 32 1 6 0 0 0 22 24 1 0 0 0 0 22 39 1 1 0 0 0 23 25 1 0 0 0 0 23 26 1 1 0 0 0 23 33 1 0 0 0 0 24 36 1 6 0 0 0 24 38 1 0 0 0 0 25 35 1 0 0 0 0 25 39 1 6 0 0 0 26 34 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	550.17
Volume:	511.288
LogP:	0.286
LogD:	0.242
LogS:	-4.03
# Rotatable Bonds:	7
TPSA:	204.83
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	5
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.215
Synthetic Accessibility Score:	4.655
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.523
MDCK Permeability:	2.6640118448995054e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.396
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.243
Plasma Protein Binding (PPB):	52.87254333496094%
Volume Distribution (VD):	0.354
Pgp-substrate:	21.01708221435547%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.09
CYP3A4-substrate:	0.198

ADMET: Excretion

Clearance (CL):	2.138
Half-life (T1/2):	0.586

ADMET: Toxicity

hERG Blockers:	0.192
Human Hepatotoxicity (H-HT):	0.247
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.686
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.187
Carcinogencity:	0.859
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC200708

Natural Product ID:	NPC200708
*Common Name:**	Liquiritin Apioside
IUPAC Name:	(2S)-2-[4-[(2S,3R,4S,5S,6R)-3-[(2R,3S,4S)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-7-hydroxy-2,3-dihydrochromen-4-one
Synonyms:	Liquiritin Apioside
Standard InCHIKey:	FTVKHUHJWDMWIR-FRFGAYJHSA-N
Standard InCHI:	InChI=1S/C26H30O13/c27-9-19-20(31)21(32)22(39-25-23(33)26(34,10-28)11-35-25)24(38-19)36-14-4-1-12(2-5-14)17-8-16(30)15-6-3-13(29)7-18(15)37-17/h1-7,17,19-25,27-29,31-34H,8-11H2/t17-,19+,20+,21-,22+,23+,24+,25+,26-/m0/s1
SMILES:	c1cc(ccc1[C@@H]1CC(=O)c2ccc(cc2O1)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@@H]1[C@H]([C@](CO)(CO1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL600792
PubChem CID:	46232263
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Anhui province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Gansu province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Henan province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shandong province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Shanxi province, China		DOI[10.1016/j.foodres.2020.109416]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2174/092986712800229032]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19402674]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19721258]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[19772486]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[20806783]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[21782011]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22190295]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[26838074]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27313650]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[27429639]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29741372]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	HeZe, ShanDong, China	early autumn (from August to the beginning of September	PMID[32545196]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Roots	n.a.	n.a.	PMID[32951423]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	Seeds	Xinjiang,China		PMID[33063333]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9798	Paeonia lactiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	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	1
Ki	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	18200.0	nM	PMID[486737]
NPT2	Others	Unspecified		Ki	=	20400.0	nM	PMID[486737]

☑ 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 NPC200708 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	392
0.1-0.2	1452
0.2-0.3	3262
0.3-0.4	8019
0.4-0.5	10263
0.5-0.6	4904
0.6-0.7	5493
0.7-0.8	6287
0.8-0.85	1973
0.85-0.9	552
0.9-0.95	88
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9801	High Similarity	NPC170475
0.9801	High Similarity	NPC149368
0.9801	High Similarity	NPC265480
0.9737	High Similarity	NPC122809
0.9735	High Similarity	NPC26195
0.9735	High Similarity	NPC39351
0.9735	High Similarity	NPC169248
0.9735	High Similarity	NPC72649
0.9735	High Similarity	NPC97052
0.9671	High Similarity	NPC206378
0.961	High Similarity	NPC472320
0.961	High Similarity	NPC271479
0.9608	High Similarity	NPC156457
0.9608	High Similarity	NPC313163
0.9608	High Similarity	NPC197896
0.9608	High Similarity	NPC161749
0.9608	High Similarity	NPC258035
0.9605	High Similarity	NPC99233
0.9603	High Similarity	NPC259767
0.9603	High Similarity	NPC88484
0.9603	High Similarity	NPC259182
0.9603	High Similarity	NPC121001
0.9548	High Similarity	NPC303913
0.9545	High Similarity	NPC308265
0.9545	High Similarity	NPC73511
0.9539	High Similarity	NPC210003
0.9539	High Similarity	NPC39360
0.9539	High Similarity	NPC83283
0.9539	High Similarity	NPC106625
0.9539	High Similarity	NPC29763
0.9539	High Similarity	NPC143851
0.9487	High Similarity	NPC150164
0.9487	High Similarity	NPC472876
0.9484	High Similarity	NPC142860
0.9484	High Similarity	NPC97285
0.9484	High Similarity	NPC246469
0.9484	High Similarity	NPC153342
0.9484	High Similarity	NPC271270
0.9481	High Similarity	NPC44931
0.9481	High Similarity	NPC473512
0.9481	High Similarity	NPC65003
0.9481	High Similarity	NPC23817
0.9481	High Similarity	NPC43638
0.9481	High Similarity	NPC129827
0.9477	High Similarity	NPC27408
0.9477	High Similarity	NPC95090
0.9423	High Similarity	NPC47923
0.9419	High Similarity	NPC22062
0.9419	High Similarity	NPC138811
0.9419	High Similarity	NPC473634
0.9416	High Similarity	NPC203500
0.9416	High Similarity	NPC323593
0.9416	High Similarity	NPC45165
0.9416	High Similarity	NPC127406
0.9416	High Similarity	NPC307938
0.9408	High Similarity	NPC23253
0.9367	High Similarity	NPC72016
0.9363	High Similarity	NPC259834
0.9363	High Similarity	NPC190450
0.9363	High Similarity	NPC44947
0.9359	High Similarity	NPC470405
0.9359	High Similarity	NPC187379
0.9359	High Similarity	NPC473623
0.9359	High Similarity	NPC471079
0.9359	High Similarity	NPC304741
0.9359	High Similarity	NPC136761
0.9355	High Similarity	NPC135391
0.9355	High Similarity	NPC6985
0.9355	High Similarity	NPC133671
0.9355	High Similarity	NPC182634
0.9355	High Similarity	NPC77672
0.9355	High Similarity	NPC60966
0.9355	High Similarity	NPC197304
0.9355	High Similarity	NPC78263
0.9355	High Similarity	NPC54802
0.9355	High Similarity	NPC288084
0.9355	High Similarity	NPC108831
0.9342	High Similarity	NPC213723
0.9317	High Similarity	NPC235575
0.9317	High Similarity	NPC261254
0.9304	High Similarity	NPC257566
0.9304	High Similarity	NPC29830
0.9304	High Similarity	NPC183672
0.9304	High Similarity	NPC124155
0.9299	High Similarity	NPC265885
0.9299	High Similarity	NPC477629
0.9299	High Similarity	NPC249281
0.9299	High Similarity	NPC270675
0.9299	High Similarity	NPC246943
0.9299	High Similarity	NPC215710
0.9299	High Similarity	NPC101636
0.9299	High Similarity	NPC64305
0.9299	High Similarity	NPC163242
0.9299	High Similarity	NPC139320
0.9299	High Similarity	NPC116458
0.9299	High Similarity	NPC253788
0.9299	High Similarity	NPC173582
0.9299	High Similarity	NPC170052
0.9299	High Similarity	NPC476215
0.9299	High Similarity	NPC473438
0.9299	High Similarity	NPC181465
0.9299	High Similarity	NPC210961
0.9299	High Similarity	NPC195685
0.9299	High Similarity	NPC276377
0.9299	High Similarity	NPC135846
0.9299	High Similarity	NPC477628
0.9299	High Similarity	NPC472994
0.9299	High Similarity	NPC297987
0.9295	High Similarity	NPC111929
0.9295	High Similarity	NPC470607
0.9295	High Similarity	NPC472459
0.9295	High Similarity	NPC43761
0.9295	High Similarity	NPC41121
0.9295	High Similarity	NPC320283
0.929	High Similarity	NPC261866
0.929	High Similarity	NPC473657
0.929	High Similarity	NPC295613
0.9255	High Similarity	NPC212748
0.925	High Similarity	NPC45400
0.9241	High Similarity	NPC475382
0.9241	High Similarity	NPC240306
0.9241	High Similarity	NPC298171
0.9241	High Similarity	NPC131745
0.9241	High Similarity	NPC93215
0.9236	High Similarity	NPC306978
0.9231	High Similarity	NPC470606
0.9216	High Similarity	NPC106025
0.9216	High Similarity	NPC214454
0.9216	High Similarity	NPC477240
0.9216	High Similarity	NPC191154
0.9211	High Similarity	NPC199335
0.9193	High Similarity	NPC229687
0.9187	High Similarity	NPC5778
0.9187	High Similarity	NPC70441
0.9187	High Similarity	NPC236934
0.9182	High Similarity	NPC471286
0.9182	High Similarity	NPC80068
0.9182	High Similarity	NPC311850
0.9182	High Similarity	NPC66087
0.9182	High Similarity	NPC179198
0.9182	High Similarity	NPC278419
0.9182	High Similarity	NPC168822
0.9182	High Similarity	NPC121703
0.9182	High Similarity	NPC473644
0.9177	High Similarity	NPC224530
0.9177	High Similarity	NPC259957
0.9177	High Similarity	NPC85707
0.9177	High Similarity	NPC48093
0.9177	High Similarity	NPC216496
0.9177	High Similarity	NPC282169
0.9177	High Similarity	NPC470125
0.9177	High Similarity	NPC129217
0.9177	High Similarity	NPC159579
0.9167	High Similarity	NPC17521
0.9161	High Similarity	NPC268950
0.9161	High Similarity	NPC108706
0.9161	High Similarity	NPC211158
0.9161	High Similarity	NPC78021
0.9161	High Similarity	NPC87304
0.9156	High Similarity	NPC190217
0.9156	High Similarity	NPC134819
0.9145	High Similarity	NPC23084
0.9145	High Similarity	NPC218685
0.9136	High Similarity	NPC44558
0.9136	High Similarity	NPC231194
0.9136	High Similarity	NPC34287
0.9136	High Similarity	NPC471416
0.9136	High Similarity	NPC51326
0.913	High Similarity	NPC160156
0.913	High Similarity	NPC149244
0.913	High Similarity	NPC92565
0.913	High Similarity	NPC229729
0.913	High Similarity	NPC48640
0.9125	High Similarity	NPC19240
0.9125	High Similarity	NPC135358
0.9125	High Similarity	NPC139060
0.9125	High Similarity	NPC205824
0.9125	High Similarity	NPC475979
0.9125	High Similarity	NPC76831
0.9125	High Similarity	NPC287889
0.9125	High Similarity	NPC165720
0.9125	High Similarity	NPC85751
0.9125	High Similarity	NPC129264
0.9125	High Similarity	NPC292929
0.9125	High Similarity	NPC289667
0.9119	High Similarity	NPC189142
0.9119	High Similarity	NPC27942
0.9119	High Similarity	NPC77660
0.9119	High Similarity	NPC127782
0.9119	High Similarity	NPC300537
0.9103	High Similarity	NPC470604
0.9103	High Similarity	NPC470603
0.9103	High Similarity	NPC477958
0.9103	High Similarity	NPC470605
0.9097	High Similarity	NPC473996
0.9097	High Similarity	NPC475790
0.9096	High Similarity	NPC469371
0.9091	High Similarity	NPC241196
0.908	High Similarity	NPC245452
0.908	High Similarity	NPC67134

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 NPC200708 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	333
0.1-0.2	815
0.2-0.3	1692
0.3-0.4	2644
0.4-0.5	2070
0.5-0.6	1079
0.6-0.7	337
0.7-0.8	146
0.8-0.85	29
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9608	High Similarity	NPD4381	Clinical (unspecified phase)
0.913	High Similarity	NPD3818	Discontinued
0.9074	High Similarity	NPD7804	Clinical (unspecified phase)
0.9018	High Similarity	NPD7074	Phase 3
0.8968	High Similarity	NPD4380	Phase 2
0.8957	High Similarity	NPD7054	Approved
0.8902	High Similarity	NPD7472	Approved
0.8848	High Similarity	NPD6797	Phase 2
0.8795	High Similarity	NPD6559	Discontinued
0.8795	High Similarity	NPD7251	Discontinued
0.8743	High Similarity	NPD7808	Phase 3
0.8742	High Similarity	NPD1549	Phase 2
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8634	High Similarity	NPD7075	Discontinued
0.8631	High Similarity	NPD4338	Clinical (unspecified phase)
0.8545	High Similarity	NPD6166	Phase 2
0.8545	High Similarity	NPD6168	Clinical (unspecified phase)
0.8545	High Similarity	NPD6167	Clinical (unspecified phase)
0.85	High Similarity	NPD1934	Approved
0.85	High Similarity	NPD6801	Discontinued
0.8447	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7411	Suspended
0.8418	Intermediate Similarity	NPD5403	Approved
0.8408	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6799	Approved
0.8301	Intermediate Similarity	NPD1510	Phase 2
0.8291	Intermediate Similarity	NPD5401	Approved
0.8291	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD2796	Approved
0.8232	Intermediate Similarity	NPD3882	Suspended
0.8193	Intermediate Similarity	NPD5494	Approved
0.8182	Intermediate Similarity	NPD3749	Approved
0.8171	Intermediate Similarity	NPD5402	Approved
0.8158	Intermediate Similarity	NPD1240	Approved
0.8148	Intermediate Similarity	NPD6599	Discontinued
0.8113	Intermediate Similarity	NPD1511	Approved
0.811	Intermediate Similarity	NPD7819	Suspended
0.811	Intermediate Similarity	NPD2801	Approved
0.8081	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD3817	Phase 2
0.8052	Intermediate Similarity	NPD1607	Approved
0.8046	Intermediate Similarity	NPD8312	Approved
0.8046	Intermediate Similarity	NPD8313	Approved
0.8036	Intermediate Similarity	NPD6959	Discontinued
0.8034	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD1512	Approved
0.8	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD7584	Approved
0.7925	Intermediate Similarity	NPD3750	Approved
0.7907	Intermediate Similarity	NPD3751	Discontinued
0.7892	Intermediate Similarity	NPD8455	Phase 2
0.7853	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD4628	Phase 3
0.7812	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7768	Phase 2
0.7785	Intermediate Similarity	NPD1551	Phase 2
0.7784	Intermediate Similarity	NPD1465	Phase 2
0.7778	Intermediate Similarity	NPD3787	Discontinued
0.7759	Intermediate Similarity	NPD5844	Phase 1
0.775	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6780	Approved
0.773	Intermediate Similarity	NPD6779	Approved
0.773	Intermediate Similarity	NPD6781	Approved
0.773	Intermediate Similarity	NPD6778	Approved
0.773	Intermediate Similarity	NPD6782	Approved
0.773	Intermediate Similarity	NPD6777	Approved
0.773	Intermediate Similarity	NPD6776	Approved
0.7719	Intermediate Similarity	NPD7199	Phase 2
0.7701	Intermediate Similarity	NPD7228	Approved
0.7697	Intermediate Similarity	NPD1653	Approved
0.7677	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2800	Approved
0.7636	Intermediate Similarity	NPD920	Approved
0.7627	Intermediate Similarity	NPD7685	Pre-registration
0.7622	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD3748	Approved
0.761	Intermediate Similarity	NPD7033	Discontinued
0.7607	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD7698	Approved
0.7606	Intermediate Similarity	NPD7696	Phase 3
0.7606	Intermediate Similarity	NPD7697	Approved
0.7606	Intermediate Similarity	NPD7435	Discontinued
0.7592	Intermediate Similarity	NPD8151	Discontinued
0.7572	Intermediate Similarity	NPD6232	Discontinued
0.7568	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1091	Approved
0.7543	Intermediate Similarity	NPD7473	Discontinued
0.7539	Intermediate Similarity	NPD7585	Approved
0.7539	Intermediate Similarity	NPD7701	Phase 2
0.7532	Intermediate Similarity	NPD1933	Approved
0.7531	Intermediate Similarity	NPD1243	Approved
0.7529	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2344	Approved
0.7515	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD2532	Approved
0.7515	Intermediate Similarity	NPD2534	Approved
0.7515	Intermediate Similarity	NPD2533	Approved
0.7513	Intermediate Similarity	NPD7783	Phase 2
0.7513	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6234	Discontinued
0.7487	Intermediate Similarity	NPD7583	Approved
0.7486	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4965	Approved
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7474	Intermediate Similarity	NPD7871	Phase 2
0.7474	Intermediate Similarity	NPD7870	Phase 2
0.7472	Intermediate Similarity	NPD5953	Discontinued
0.7469	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1613	Approved
0.7468	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1203	Approved
0.746	Intermediate Similarity	NPD6823	Phase 2
0.7459	Intermediate Similarity	NPD6535	Approved
0.7459	Intermediate Similarity	NPD6534	Approved
0.7458	Intermediate Similarity	NPD7286	Phase 2
0.7455	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2935	Discontinued
0.744	Intermediate Similarity	NPD7458	Discontinued
0.7436	Intermediate Similarity	NPD6832	Phase 2
0.7433	Intermediate Similarity	NPD7699	Phase 2
0.7433	Intermediate Similarity	NPD7700	Phase 2
0.7429	Intermediate Similarity	NPD3926	Phase 2
0.7418	Intermediate Similarity	NPD8434	Phase 2
0.741	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7266	Discontinued
0.7399	Intermediate Similarity	NPD919	Approved
0.7375	Intermediate Similarity	NPD6651	Approved
0.7371	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7874	Approved
0.7358	Intermediate Similarity	NPD943	Approved
0.7342	Intermediate Similarity	NPD2313	Discontinued
0.7337	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2309	Approved
0.7333	Intermediate Similarity	NPD7240	Approved
0.7333	Intermediate Similarity	NPD7801	Approved
0.7325	Intermediate Similarity	NPD4908	Phase 1
0.7314	Intermediate Similarity	NPD1247	Approved
0.7312	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5124	Phase 1
0.7308	Intermediate Similarity	NPD2798	Approved
0.7292	Intermediate Similarity	NPD8319	Approved
0.7292	Intermediate Similarity	NPD8320	Phase 1
0.7284	Intermediate Similarity	NPD2799	Discontinued
0.7273	Intermediate Similarity	NPD4360	Phase 2
0.7273	Intermediate Similarity	NPD4363	Phase 3
0.7243	Intermediate Similarity	NPD4287	Approved
0.7239	Intermediate Similarity	NPD6099	Approved
0.7239	Intermediate Similarity	NPD6100	Approved
0.7235	Intermediate Similarity	NPD3226	Approved
0.7233	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6798	Discontinued
0.7229	Intermediate Similarity	NPD6190	Approved
0.7215	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1652	Phase 2
0.7208	Intermediate Similarity	NPD1610	Phase 2
0.7191	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1548	Phase 1
0.7169	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2424	Discontinued
0.7151	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7930	Approved
0.7135	Intermediate Similarity	NPD8150	Discontinued
0.7135	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6213	Phase 3
0.7128	Intermediate Similarity	NPD6212	Phase 3
0.7128	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3268	Approved
0.7125	Intermediate Similarity	NPD3764	Approved
0.7117	Intermediate Similarity	NPD7097	Phase 1
0.7108	Intermediate Similarity	NPD2654	Approved
0.7101	Intermediate Similarity	NPD4662	Approved
0.7101	Intermediate Similarity	NPD4661	Approved
0.7099	Intermediate Similarity	NPD6355	Discontinued
0.7099	Intermediate Similarity	NPD230	Phase 1
0.7091	Intermediate Similarity	NPD2346	Discontinued
0.7083	Intermediate Similarity	NPD5058	Phase 3
0.7081	Intermediate Similarity	NPD6233	Phase 2
0.7079	Intermediate Similarity	NPD5711	Approved
0.7079	Intermediate Similarity	NPD5710	Approved
0.7073	Intermediate Similarity	NPD4308	Phase 3
0.707	Intermediate Similarity	NPD3225	Approved
0.7063	Intermediate Similarity	NPD3027	Phase 3
0.7053	Intermediate Similarity	NPD4361	Phase 2
0.7053	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7390	Discontinued
0.7033	Intermediate Similarity	NPD1729	Discontinued
0.7029	Intermediate Similarity	NPD4288	Approved
0.7025	Intermediate Similarity	NPD2797	Approved
0.7024	Intermediate Similarity	NPD2354	Approved
0.7024	Intermediate Similarity	NPD3887	Approved
0.7011	Intermediate Similarity	NPD6844	Discontinued

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