NPASS Compound

Structure

CID120217 OpenBabel06191715472D 21 22 0 0 1 0 0 0 0 0999 V2000 2.5981 0.5000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 4.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 -0.8660 1.5000 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 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 8 2 0 0 0 0 5 8 1 0 0 0 0 6 15 3 0 0 0 0 7 16 1 0 0 0 0 8 9 1 0 0 0 0 9 6 1 1 0 0 0 9 20 1 0 0 0 0 10 7 1 6 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 1 0 0 0 12 13 1 0 0 0 0 12 18 1 6 0 0 0 13 14 1 0 0 0 0 13 19 1 1 0 0 0 14 20 1 6 0 0 0 14 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	295.11
Volume:	284.143
LogP:	-0.314
LogD:	-0.379
LogS:	-1.17
# Rotatable Bonds:	4
TPSA:	123.17
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.565
Synthetic Accessibility Score:	3.796
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.373
MDCK Permeability:	8.722049096832052e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.849
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.745

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.292
Plasma Protein Binding (PPB):	26.461355209350586%
Volume Distribution (VD):	0.639
Pgp-substrate:	63.2814826965332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.046
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.132
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	2.31
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.779
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.712
Rat Oral Acute Toxicity:	0.371
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.823
Carcinogencity:	0.05
Eye Corrosion:	0.015
Eye Irritation:	0.839
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC120217

Natural Product ID:	NPC120217
*Common Name:**	Prunasin
IUPAC Name:	(2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
Synonyms:	Prunasin
Standard InCHIKey:	ZKSZEJFBGODIJW-GMDXDWKASA-N
Standard InCHI:	InChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9-,10+,11+,12-,13+,14+/m0/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H](c2ccccc2)C#N)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1778417
PubChem CID:	119033
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002365] Cyanogenic 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
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39770000295]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[10670815]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978200]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11429258]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	flowers	n.a.	n.a.	PMID[12193020]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16038540]
NPO6978	Boronella koniambiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038554]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	PMID[1612412]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[17226159]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17237222]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	Malatya Fruit Research Institute	between the first and third weeks of 2005-Jul.	PMID[18038980]
NPO4083	Brevibacillus laterosporus	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[18044840]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[18566831]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	roots	n.a.	n.a.	PMID[19128156]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	exudate	n.a.	n.a.	PMID[20028108]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20674349]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21381684]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21381684]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	stem	n.a.	PMID[21381684]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21428274]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21428274]
NPO21463.1	Aruncus dioicus	Under-species	n.a.	n.a.	aerial parts	n.a.	n.a.	PMID[21546250]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22187429]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22272932]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23784883]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24400858]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24485782]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25320841]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26169681]
NPO10899	Ophioparma ventosa	Species	Ophioparmaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26934105]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[27133212]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	stem	n.a.	PMID[8945767]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5482	Gymnanthemum amygdalinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13427	Erinaceus europaeus	Species	Erinaceidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11032	Coutarea latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10452	Odontites rubra	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4795	Prunus armeniaca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27659	Tanacetum parthenifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4083	Brevibacillus laterosporus	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1776	Attalea excelsa	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2551	Plumbagella micrantha	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8671	Physalis solanaceus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7077	Canarium strictum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15178	Psychotria bahiensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5191	Penicillium cinerascens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13766	Ceanothus velutinus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7792	Coreopsis grandiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13467	Anarsia lineatella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15679	Amyris marshii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6978	Boronella koniambiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12457	Siphocampylus verticillatus	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12971	Payena lucida	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11376	Schistostephium rotundifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29535	Samadera indica	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11962	Garcinia macrophylla	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15570	Plectranthus mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5727	Hymenothrix wislizenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5482	Gymnanthemum amygdalinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11214	Rivina humilis	Species	Petiveriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16311	Rusavskia elegans	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8389	Ophryosporus floribundus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16109	Actinidia kolomikta	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11998	Ledebouria socialis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11785	Citrus hassaku	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11531	Duguetia calycina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12509	Dipterocarpus dyeri	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16625	Phalaenopsis aphrodite	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO746	Panax innovans	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13273	Maytenus loeseneri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16307	Murraya kwangsiensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10899	Ophioparma ventosa	Species	Ophioparmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15159	Podocarpus salignus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12516	Phalaris canariensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12470	Brachyspira hyodysenteriae	Species	Brachyspiraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22056.1	Streptomyces fervens	Subspecies	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO205	Lasianthus fordii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14111	Maytenus serrata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7313	Epirrhoe sperryi	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16541	Veratrum stenophyllum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12411	Eriostemon spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12030	Streptomyces yokosukanensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12858	Jacaranda chelonia	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14914	Esox saurus	Species	Esocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8681	Artemisia lactiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14442	Gouania microcarpa	Species	Gobiesocidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4671	Persea mexicana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14604	Dipteronia dyeriana	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7718	Peucedanum palustre	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15884	Dodonaea polyandra	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1723	Sideritis syriaca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2607	Ophiorrhiza blumeana	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7574	Garcinia pyrifera	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14057	Apollonias barbujana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13582	Leucopaxillus giganteus	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13952	Streptomyces lavendulae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15312	Coelogorgia palmosa	Species	Coelogorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10550	Artemisia hanseniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13121	Crepidiastrum sonchifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26256	Zanthoxylum chiriquinum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15434	Rhodomicrobium vannielii	Species	Hyphomicrobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12951	Talaromyces coalescens	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO716	Greenwayodendron oliveri	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3697	Ongokea klaineana	Species	Aptandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10861	Dipsacus asper	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5750	Monomorium floricola	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11644	Prosopis ruscifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8892	Sordaria araneosa	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14747	Usnea florida	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO651	Aconitum vilmorinianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12547	Viburnum chingii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13740	Aconitum kamtschaticum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9386	Ectropis bicolor	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13087	Pteridium aquilinum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13427	Erinaceus europaeus	Species	Erinaceidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22053	Vepris pilosa	Species	Rutaceae	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

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[558648]
NPT1	Others	Radical scavenging activity		IC50	>	100000.0	nM	PMID[558648]

☑ 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 NPC120217 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	189
0.1-0.2	1118
0.2-0.3	3114
0.3-0.4	10523
0.4-0.5	12077
0.5-0.6	12421
0.6-0.7	2959
0.7-0.8	266
0.8-0.85	15
0.85-0.9	8
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9633	High Similarity	NPC266389
0.9633	High Similarity	NPC122245
0.9633	High Similarity	NPC216605
0.9238	High Similarity	NPC152384
0.9238	High Similarity	NPC37714
0.9052	High Similarity	NPC212176
0.8899	High Similarity	NPC276061
0.8899	High Similarity	NPC474148
0.8818	High Similarity	NPC264784
0.8818	High Similarity	NPC30563
0.8785	High Similarity	NPC148060
0.8783	High Similarity	NPC14950
0.8667	High Similarity	NPC262826
0.8595	High Similarity	NPC198798
0.8362	Intermediate Similarity	NPC175771
0.8349	Intermediate Similarity	NPC469527
0.8273	Intermediate Similarity	NPC47286
0.819	Intermediate Similarity	NPC157338
0.819	Intermediate Similarity	NPC313193
0.8083	Intermediate Similarity	NPC469708
0.8083	Intermediate Similarity	NPC60589
0.8051	Intermediate Similarity	NPC148055
0.8033	Intermediate Similarity	NPC476142
0.8017	Intermediate Similarity	NPC269242
0.8017	Intermediate Similarity	NPC229600
0.8017	Intermediate Similarity	NPC469412
0.8017	Intermediate Similarity	NPC198734
0.7982	Intermediate Similarity	NPC184633
0.7951	Intermediate Similarity	NPC226712
0.7903	Intermediate Similarity	NPC57607
0.7787	Intermediate Similarity	NPC469702
0.7787	Intermediate Similarity	NPC282409
0.7778	Intermediate Similarity	NPC470825
0.776	Intermediate Similarity	NPC287429
0.7724	Intermediate Similarity	NPC476448
0.7724	Intermediate Similarity	NPC469704
0.7724	Intermediate Similarity	NPC476445
0.7724	Intermediate Similarity	NPC469548
0.7724	Intermediate Similarity	NPC160854
0.7724	Intermediate Similarity	NPC201402
0.7724	Intermediate Similarity	NPC469703
0.7698	Intermediate Similarity	NPC470510
0.7692	Intermediate Similarity	NPC43584
0.7661	Intermediate Similarity	NPC469686
0.7661	Intermediate Similarity	NPC11724
0.7661	Intermediate Similarity	NPC55608
0.7661	Intermediate Similarity	NPC266045
0.7656	Intermediate Similarity	NPC301857
0.7652	Intermediate Similarity	NPC475203
0.7652	Intermediate Similarity	NPC474376
0.7652	Intermediate Similarity	NPC472315
0.7652	Intermediate Similarity	NPC472316
0.7647	Intermediate Similarity	NPC474641
0.7638	Intermediate Similarity	NPC114096
0.7627	Intermediate Similarity	NPC185840
0.7603	Intermediate Similarity	NPC301651
0.7603	Intermediate Similarity	NPC473556
0.76	Intermediate Similarity	NPC52097
0.76	Intermediate Similarity	NPC471067
0.7597	Intermediate Similarity	NPC26653
0.7597	Intermediate Similarity	NPC270849
0.7597	Intermediate Similarity	NPC97326
0.7597	Intermediate Similarity	NPC27712
0.7583	Intermediate Similarity	NPC29607
0.7581	Intermediate Similarity	NPC476872
0.7578	Intermediate Similarity	NPC288416
0.7578	Intermediate Similarity	NPC148026
0.7547	Intermediate Similarity	NPC211237
0.754	Intermediate Similarity	NPC470907
0.754	Intermediate Similarity	NPC138798
0.754	Intermediate Similarity	NPC178449
0.754	Intermediate Similarity	NPC232454
0.7538	Intermediate Similarity	NPC472024
0.7538	Intermediate Similarity	NPC80600
0.7519	Intermediate Similarity	NPC146540
0.7519	Intermediate Similarity	NPC40377
0.75	Intermediate Similarity	NPC146673
0.75	Intermediate Similarity	NPC233923
0.75	Intermediate Similarity	NPC136962
0.75	Intermediate Similarity	NPC37115
0.7481	Intermediate Similarity	NPC475067
0.7481	Intermediate Similarity	NPC9912
0.7481	Intermediate Similarity	NPC65942
0.7481	Intermediate Similarity	NPC248307
0.7478	Intermediate Similarity	NPC280616
0.7478	Intermediate Similarity	NPC242913
0.7478	Intermediate Similarity	NPC171831
0.7462	Intermediate Similarity	NPC166040
0.7456	Intermediate Similarity	NPC154905
0.7456	Intermediate Similarity	NPC60373
0.7436	Intermediate Similarity	NPC277788
0.7424	Intermediate Similarity	NPC269421
0.7424	Intermediate Similarity	NPC254275
0.7422	Intermediate Similarity	NPC126991
0.7422	Intermediate Similarity	NPC123704
0.7422	Intermediate Similarity	NPC90318
0.7422	Intermediate Similarity	NPC12308
0.7422	Intermediate Similarity	NPC83218
0.7419	Intermediate Similarity	NPC238582
0.7419	Intermediate Similarity	NPC477803
0.7417	Intermediate Similarity	NPC265002
0.7405	Intermediate Similarity	NPC262606
0.7385	Intermediate Similarity	NPC302378
0.7364	Intermediate Similarity	NPC471157
0.7364	Intermediate Similarity	NPC252114
0.7355	Intermediate Similarity	NPC172525
0.7348	Intermediate Similarity	NPC246869
0.7348	Intermediate Similarity	NPC235294
0.7348	Intermediate Similarity	NPC478255
0.7348	Intermediate Similarity	NPC225384
0.7348	Intermediate Similarity	NPC138777
0.7348	Intermediate Similarity	NPC166168
0.7348	Intermediate Similarity	NPC46137
0.7333	Intermediate Similarity	NPC234376
0.7328	Intermediate Similarity	NPC218003
0.7328	Intermediate Similarity	NPC248355
0.7328	Intermediate Similarity	NPC307110
0.7328	Intermediate Similarity	NPC295970
0.7323	Intermediate Similarity	NPC141970
0.7323	Intermediate Similarity	NPC140561
0.7319	Intermediate Similarity	NPC63628
0.7319	Intermediate Similarity	NPC178466
0.7313	Intermediate Similarity	NPC470881
0.7313	Intermediate Similarity	NPC34456
0.7313	Intermediate Similarity	NPC187194
0.7313	Intermediate Similarity	NPC35731
0.7313	Intermediate Similarity	NPC476411
0.7308	Intermediate Similarity	NPC79715
0.7308	Intermediate Similarity	NPC231607
0.7308	Intermediate Similarity	NPC106677
0.7308	Intermediate Similarity	NPC264900
0.7308	Intermediate Similarity	NPC471881
0.7308	Intermediate Similarity	NPC45224
0.7308	Intermediate Similarity	NPC469687
0.7308	Intermediate Similarity	NPC471882
0.7308	Intermediate Similarity	NPC35288
0.7308	Intermediate Similarity	NPC173150
0.7308	Intermediate Similarity	NPC156692
0.7308	Intermediate Similarity	NPC108659
0.7299	Intermediate Similarity	NPC195814
0.7295	Intermediate Similarity	NPC142319
0.7279	Intermediate Similarity	NPC36434
0.7273	Intermediate Similarity	NPC290353
0.7273	Intermediate Similarity	NPC474491
0.7273	Intermediate Similarity	NPC42911
0.7273	Intermediate Similarity	NPC153795
0.7259	Intermediate Similarity	NPC79957
0.7252	Intermediate Similarity	NPC232880
0.7252	Intermediate Similarity	NPC225307
0.7252	Intermediate Similarity	NPC148982
0.7239	Intermediate Similarity	NPC114116
0.7239	Intermediate Similarity	NPC6836
0.7239	Intermediate Similarity	NPC25821
0.7239	Intermediate Similarity	NPC215833
0.7239	Intermediate Similarity	NPC69513
0.7231	Intermediate Similarity	NPC94179
0.7231	Intermediate Similarity	NPC61181
0.7226	Intermediate Similarity	NPC298821
0.7218	Intermediate Similarity	NPC121376
0.7209	Intermediate Similarity	NPC162925
0.7209	Intermediate Similarity	NPC87153
0.7209	Intermediate Similarity	NPC145287
0.7209	Intermediate Similarity	NPC244454
0.7206	Intermediate Similarity	NPC177035
0.7206	Intermediate Similarity	NPC199459
0.7206	Intermediate Similarity	NPC52277
0.7206	Intermediate Similarity	NPC475628
0.7206	Intermediate Similarity	NPC471345
0.7197	Intermediate Similarity	NPC477294
0.7197	Intermediate Similarity	NPC184092
0.7197	Intermediate Similarity	NPC253595
0.7197	Intermediate Similarity	NPC229784
0.7197	Intermediate Similarity	NPC469549
0.7197	Intermediate Similarity	NPC477293
0.7193	Intermediate Similarity	NPC475954
0.7185	Intermediate Similarity	NPC471029
0.7185	Intermediate Similarity	NPC34293
0.7185	Intermediate Similarity	NPC48863
0.7185	Intermediate Similarity	NPC107478
0.7185	Intermediate Similarity	NPC287597
0.7185	Intermediate Similarity	NPC251981
0.7185	Intermediate Similarity	NPC169398
0.7185	Intermediate Similarity	NPC87696
0.7185	Intermediate Similarity	NPC13745
0.7185	Intermediate Similarity	NPC886
0.7176	Intermediate Similarity	NPC103533
0.7176	Intermediate Similarity	NPC476873
0.7174	Intermediate Similarity	NPC123761
0.7164	Intermediate Similarity	NPC252833
0.7164	Intermediate Similarity	NPC162093
0.7164	Intermediate Similarity	NPC85799
0.7164	Intermediate Similarity	NPC470270
0.7164	Intermediate Similarity	NPC165686
0.7164	Intermediate Similarity	NPC26080
0.7164	Intermediate Similarity	NPC299144
0.7164	Intermediate Similarity	NPC303422
0.7154	Intermediate Similarity	NPC28069
0.7154	Intermediate Similarity	NPC77651
0.7153	Intermediate Similarity	NPC78363
0.7153	Intermediate Similarity	NPC470413

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 NPC120217 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	721
0.2-0.3	1316
0.3-0.4	3194
0.4-0.5	2258
0.5-0.6	1305
0.6-0.7	194
0.7-0.8	2
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7951	Intermediate Similarity	NPD1091	Approved
0.7934	Intermediate Similarity	NPD5126	Approved
0.7934	Intermediate Similarity	NPD5125	Phase 3
0.7627	Intermediate Similarity	NPD969	Suspended
0.7113	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9532	Phase 3
0.6978	Remote Similarity	NPD7266	Discontinued
0.6885	Remote Similarity	NPD9713	Approved
0.686	Remote Similarity	NPD290	Approved
0.6822	Remote Similarity	NPD5723	Approved
0.6809	Remote Similarity	NPD2424	Discontinued
0.6797	Remote Similarity	NPD7741	Discontinued
0.678	Remote Similarity	NPD2555	Approved
0.678	Remote Similarity	NPD2549	Approved
0.678	Remote Similarity	NPD2550	Approved
0.678	Remote Similarity	NPD2558	Approved
0.678	Remote Similarity	NPD2553	Approved
0.678	Remote Similarity	NPD2552	Approved
0.6723	Remote Similarity	NPD4189	Approved
0.6723	Remote Similarity	NPD4188	Approved
0.6696	Remote Similarity	NPD531	Approved
0.6694	Remote Similarity	NPD794	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD4198	Discontinued
0.6667	Remote Similarity	NPD2684	Approved
0.6643	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD3847	Discontinued
0.6639	Remote Similarity	NPD3524	Approved
0.6639	Remote Similarity	NPD810	Approved
0.6639	Remote Similarity	NPD812	Approved
0.6639	Remote Similarity	NPD811	Approved
0.6639	Remote Similarity	NPD3526	Approved
0.6621	Remote Similarity	NPD5058	Phase 3
0.6617	Remote Similarity	NPD7876	Discontinued
0.6617	Remote Similarity	NPD3685	Discontinued
0.6612	Remote Similarity	NPD3048	Approved
0.6612	Remote Similarity	NPD3046	Approved
0.6612	Remote Similarity	NPD3047	Approved
0.661	Remote Similarity	NPD9495	Approved
0.6604	Remote Similarity	NPD9294	Approved
0.6594	Remote Similarity	NPD4404	Approved
0.6591	Remote Similarity	NPD3705	Approved
0.6587	Remote Similarity	NPD7843	Approved
0.6569	Remote Similarity	NPD3027	Phase 3
0.6547	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD1613	Approved
0.6547	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6674	Discontinued
0.651	Remote Similarity	NPD1653	Approved
0.6504	Remote Similarity	NPD2551	Approved
0.6504	Remote Similarity	NPD2559	Approved
0.6491	Remote Similarity	NPD689	Discontinued
0.6489	Remote Similarity	NPD1357	Approved
0.6489	Remote Similarity	NPD770	Discontinued
0.6484	Remote Similarity	NPD2629	Approved
0.6471	Remote Similarity	NPD5926	Approved
0.6471	Remote Similarity	NPD9609	Approved
0.6471	Remote Similarity	NPD9611	Approved
0.6471	Remote Similarity	NPD9612	Approved
0.6457	Remote Similarity	NPD821	Approved
0.6452	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD3179	Approved
0.6449	Remote Similarity	NPD3180	Approved
0.6446	Remote Similarity	NPD855	Approved
0.6446	Remote Similarity	NPD854	Approved
0.6434	Remote Similarity	NPD7157	Approved
0.6423	Remote Similarity	NPD5048	Discontinued
0.6418	Remote Similarity	NPD2235	Phase 2
0.6418	Remote Similarity	NPD2231	Phase 2
0.6414	Remote Similarity	NPD1652	Phase 2
0.6412	Remote Similarity	NPD1182	Approved
0.6408	Remote Similarity	NPD41	Approved
0.6408	Remote Similarity	NPD4538	Approved
0.6408	Remote Similarity	NPD4536	Approved
0.6408	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5886	Approved
0.6405	Remote Similarity	NPD8455	Phase 2
0.6397	Remote Similarity	NPD2625	Approved
0.6397	Remote Similarity	NPD2628	Approved
0.6397	Remote Similarity	NPD2159	Approved
0.6397	Remote Similarity	NPD2627	Approved
0.6397	Remote Similarity	NPD2626	Approved
0.6397	Remote Similarity	NPD2160	Approved
0.6395	Remote Similarity	NPD5756	Phase 2
0.6385	Remote Similarity	NPD5292	Approved
0.6385	Remote Similarity	NPD5291	Approved
0.6378	Remote Similarity	NPD4572	Approved
0.6378	Remote Similarity	NPD4571	Approved
0.6378	Remote Similarity	NPD4573	Approved
0.6371	Remote Similarity	NPD968	Approved
0.637	Remote Similarity	NPD2575	Approved
0.6364	Remote Similarity	NPD5588	Approved
0.6364	Remote Similarity	NPD5960	Phase 3
0.6364	Remote Similarity	NPD4108	Discontinued
0.6358	Remote Similarity	NPD7007	Discovery
0.635	Remote Similarity	NPD558	Phase 2
0.635	Remote Similarity	NPD7247	Discontinued
0.6349	Remote Similarity	NPD556	Approved
0.6349	Remote Similarity	NPD550	Approved
0.6349	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD551	Approved
0.6327	Remote Similarity	NPD2677	Approved
0.632	Remote Similarity	NPD6406	Approved
0.6316	Remote Similarity	NPD5305	Approved
0.6316	Remote Similarity	NPD5306	Approved
0.6299	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD2201	Approved
0.6296	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD1840	Phase 2
0.6288	Remote Similarity	NPD1548	Phase 1
0.6284	Remote Similarity	NPD3122	Phase 3
0.6282	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD1819	Approved
0.6277	Remote Similarity	NPD1820	Approved
0.6277	Remote Similarity	NPD1817	Approved
0.6277	Remote Similarity	NPD1818	Approved
0.6277	Remote Similarity	NPD1794	Approved
0.6276	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD1375	Discontinued
0.6269	Remote Similarity	NPD4106	Approved
0.6269	Remote Similarity	NPD4135	Approved
0.6269	Remote Similarity	NPD4136	Approved
0.626	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.626	Remote Similarity	NPD744	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD4110	Phase 3
0.6259	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1774	Approved
0.6241	Remote Similarity	NPD6233	Phase 2
0.624	Remote Similarity	NPD6685	Approved
0.6235	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD4433	Discontinued
0.6232	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4480	Approved
0.6222	Remote Similarity	NPD4806	Approved
0.6222	Remote Similarity	NPD4807	Approved
0.6222	Remote Similarity	NPD1610	Phase 2
0.622	Remote Similarity	NPD5239	Approved
0.622	Remote Similarity	NPD5240	Approved
0.622	Remote Similarity	NPD5235	Approved
0.622	Remote Similarity	NPD5237	Approved
0.622	Remote Similarity	NPD2067	Discontinued
0.622	Remote Similarity	NPD5236	Approved
0.6214	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.621	Remote Similarity	NPD315	Approved
0.621	Remote Similarity	NPD310	Approved
0.621	Remote Similarity	NPD309	Approved
0.621	Remote Similarity	NPD314	Approved
0.621	Remote Similarity	NPD311	Approved
0.621	Remote Similarity	NPD10	Approved
0.6204	Remote Similarity	NPD5667	Approved
0.6204	Remote Similarity	NPD8651	Approved
0.6202	Remote Similarity	NPD1138	Approved
0.6202	Remote Similarity	NPD2497	Approved
0.6202	Remote Similarity	NPD2496	Approved
0.62	Remote Similarity	NPD3985	Discontinued
0.6197	Remote Similarity	NPD2238	Phase 2
0.6194	Remote Similarity	NPD6516	Phase 2
0.6194	Remote Similarity	NPD2978	Approved
0.6194	Remote Similarity	NPD2977	Approved
0.6194	Remote Similarity	NPD9384	Approved
0.6194	Remote Similarity	NPD9381	Approved
0.6194	Remote Similarity	NPD5846	Approved
0.6194	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1358	Approved
0.619	Remote Similarity	NPD4237	Approved
0.619	Remote Similarity	NPD4236	Phase 3
0.6187	Remote Similarity	NPD2861	Phase 2
0.6187	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD7097	Phase 1
0.6179	Remote Similarity	NPD291	Approved
0.6176	Remote Similarity	NPD7249	Approved
0.6176	Remote Similarity	NPD7250	Approved
0.6174	Remote Similarity	NPD5295	Discontinued
0.6174	Remote Similarity	NPD1282	Approved
0.617	Remote Similarity	NPD1048	Approved
0.6164	Remote Similarity	NPD521	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD2415	Discontinued
0.6148	Remote Similarity	NPD3896	Approved
0.6148	Remote Similarity	NPD1238	Approved
0.6148	Remote Similarity	NPD3895	Approved
0.6148	Remote Similarity	NPD3897	Approved
0.6148	Remote Similarity	NPD3898	Approved
0.6143	Remote Similarity	NPD4617	Approved
0.6143	Remote Similarity	NPD4620	Approved
0.6143	Remote Similarity	NPD5201	Approved
0.6143	Remote Similarity	NPD2613	Approved
0.6143	Remote Similarity	NPD5203	Approved
0.6143	Remote Similarity	NPD4908	Phase 1
0.6142	Remote Similarity	NPD2182	Approved
0.6129	Remote Similarity	NPD5765	Approved
0.6129	Remote Similarity	NPD3681	Approved
0.6129	Remote Similarity	NPD3683	Approved
0.6129	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4231	Approved
0.6129	Remote Similarity	NPD4229	Approved
0.6129	Remote Similarity	NPD4656	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