NPASS Compound

Structure

CID190457 OpenBabel06191715572D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 2.5981 -0.5000 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 -2.5981 -1.5000 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 -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 -1.7321 0.0000 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 -0.8660 -0.5000 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 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 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 8 1 0 0 0 0 2 6 1 0 0 0 0 2 10 2 0 0 0 0 3 7 2 0 0 0 0 3 9 1 0 0 0 0 4 7 1 0 0 0 0 4 11 2 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 7 17 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 13 15 1 0 0 0 0 14 20 2 0 0 0 0 15 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.05
Volume:	273.977
LogP:	2.661
LogD:	1.625
LogS:	-3.921
# Rotatable Bonds:	1
TPSA:	118.22
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	2.851
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.581
MDCK Permeability:	3.99886585000786e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.872
20% Bioavailability (F20%):	0.93
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	94.74413299560547%
Volume Distribution (VD):	0.533
Pgp-substrate:	7.741998195648193%

ADMET: Metabolism

CYP1A2-inhibitor:	0.953
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.456
CYP2C9-substrate:	0.421
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.164
CYP3A4-inhibitor:	0.115
CYP3A4-substrate:	0.022

ADMET: Excretion

Clearance (CL):	7.044
Half-life (T1/2):	0.906

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.352
AMES Toxicity:	0.428
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.94
Carcinogencity:	0.031
Eye Corrosion:	0.081
Eye Irritation:	0.924
Respiratory Toxicity:	0.728

Download Data

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

Natural Product: NPC190457

Natural Product ID:	NPC190457
*Common Name:**	Omega-Hydroxyemodin
IUPAC Name:	1,3,8-trihydroxy-6-(hydroxymethyl)anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	YQHZABGPIPECSQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O6/c16-5-6-1-8-12(10(18)2-6)15(21)13-9(14(8)20)3-7(17)4-11(13)19/h1-4,16-19H,5H2
SMILES:	OCc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL290932
PubChem CID:	361512
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO12079	Dysoxylum cumingianum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/jo00051a050]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO14520	Bassia muricata	Species	Chenopodiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[11454355]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	root	n.a.	PMID[16564530]
NPO28478	Magnolia ovata	Species	Magnoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19658431]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719093]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22512738]
NPO28478	Magnolia ovata	Species	Magnoliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23157012]
NPO31520	Polygonum multiflorum	Species	Polygonaceae	Eukaryota	roots	n.a.	n.a.	PMID[24499304]
NPO472	Penicillium restrictum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24911880]
NPO26465	Coreopsis tinctoria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25516207]
NPO13237	Teucrium yemense	Species	n.a.	n.a.	Aerial Parts	n.a.	n.a.	PMID[28581290]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29359942]
NPO40155	Helotiales sp.	Species		Eukaryota	n.a.	n.a.	n.a.	PMID[30730742]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31944695]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[7714535]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24699	Phlogacanthus curviflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317.1	Citrus aurantium var. amara	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31520	Polygonum multiflorum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15297	Aconitum seravschanicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317.1	Citrus aurantium var. amara	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26401	Andrographis neesiana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24699	Phlogacanthus curviflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31520	Polygonum multiflorum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28478	Magnolia ovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26465	Coreopsis tinctoria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15746	Athelia rolfsii	Species	Atheliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8386	Enceliopsis argophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13403	Gadus morhua callarias	Species	Gadidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14217	Adansonia grandidieri	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26401	Andrographis neesiana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9243	Senecio bonariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11749	Eria mollis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26777	Pneumatopteris pennigera	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9448	Dictyopteris australis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13421	Sphaerella laricina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7819.1	Epichloe festucae var. lolii	Varieties	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13237	Teucrium yemense	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO1312	Pseudococcus albizziae	Species	Pseudococcidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24699	Phlogacanthus curviflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14520	Bassia muricata	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24989	Solanum cleistogamum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO986	Rattus rattus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9752	Miliusa velutina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16590	Cytophaga hutchinsoni	Species	Cytophagaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12079	Dysoxylum cumingianum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7064	Endoconidiophora coerulescens	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2631	Aster sedifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO472	Penicillium restrictum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10688	Flacourtia jangomas	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5880	Helichrysum plicatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16050	Rhodiola viridula	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12252	Psychotria stachyoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15297	Aconitum seravschanicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13716	Aconitum tasiromontanum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4345	Caulocystis cephalornithos	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23412	Uvaria afzelii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25352	Pluchea odora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2198	Rivularia firma	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO624	Isaria fumosorosea	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1501	Senecio subdentatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13523	Neobalanocarpus heimii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22526	Justicia secunda	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10152	Artemisia parviflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11580	Onobrychis arenaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26202	Loranthus pentandrus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3214	Lavandula vera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14412	Aphyllocladus denticulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14104	Dendriopoterium menendezii	Species	Rosaceae	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
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3769	Individual Protein	Elastase 2A	Sus scrofa	Inhibition	=	4.0	%	PMID[533334]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Inhibition	=	26.0	%	PMID[533334]
NPT278	Individual Protein	Cathepsin G	Homo sapiens	Inhibition	=	22.0	%	PMID[533334]
NPT4782	Individual Protein	Accessory gene regulator protein A	Staphylococcus aureus	IC50	=	8100.0	nM	PMID[533335]
NPT2	Others	Unspecified		IC50	=	6300.0	nM	PMID[533336]

☑ 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 NPC190457 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	402
0.1-0.2	1789
0.2-0.3	3933
0.3-0.4	10339
0.4-0.5	8689
0.5-0.6	4862
0.6-0.7	6094
0.7-0.8	5587
0.8-0.85	722
0.85-0.9	222
0.9-0.95	45
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9704	High Similarity	NPC204045
0.9704	High Similarity	NPC305845
0.9635	High Similarity	NPC471906
0.9635	High Similarity	NPC244691
0.9632	High Similarity	NPC135524
0.9624	High Similarity	NPC254847
0.9556	High Similarity	NPC143438
0.9552	High Similarity	NPC53414
0.9552	High Similarity	NPC53206
0.9552	High Similarity	NPC471905
0.9489	High Similarity	NPC73061
0.9489	High Similarity	NPC474961
0.9474	High Similarity	NPC44437
0.9416	High Similarity	NPC290550
0.9412	High Similarity	NPC242994
0.9412	High Similarity	NPC138099
0.9398	High Similarity	NPC52407
0.9398	High Similarity	NPC267205
0.9353	High Similarity	NPC48762
0.9353	High Similarity	NPC21599
0.9353	High Similarity	NPC193703
0.9343	High Similarity	NPC169452
0.9343	High Similarity	NPC181560
0.9323	High Similarity	NPC70622
0.9286	High Similarity	NPC34482
0.9275	High Similarity	NPC246638
0.9248	High Similarity	NPC93015
0.9231	High Similarity	NPC147735
0.922	High Similarity	NPC470570
0.9209	High Similarity	NPC193555
0.9191	High Similarity	NPC191976
0.9173	High Similarity	NPC147757
0.9173	High Similarity	NPC31799
0.9173	High Similarity	NPC199253
0.9173	High Similarity	NPC136588
0.9111	High Similarity	NPC314048
0.9097	High Similarity	NPC255641
0.9097	High Similarity	NPC290954
0.9071	High Similarity	NPC137649
0.9065	High Similarity	NPC183345
0.9065	High Similarity	NPC203063
0.9044	High Similarity	NPC282780
0.9044	High Similarity	NPC166480
0.9037	High Similarity	NPC478190
0.9034	High Similarity	NPC470569
0.9021	High Similarity	NPC118027
0.9021	High Similarity	NPC126767
0.9021	High Similarity	NPC37709
0.9021	High Similarity	NPC245584
0.9021	High Similarity	NPC56433
0.9021	High Similarity	NPC289042
0.9021	High Similarity	NPC190648
0.9021	High Similarity	NPC290194
0.9021	High Similarity	NPC312929
0.9007	High Similarity	NPC238629
0.9	High Similarity	NPC110810
0.9	High Similarity	NPC187843
0.8978	High Similarity	NPC161632
0.8966	High Similarity	NPC470568
0.8966	High Similarity	NPC294646
0.8958	High Similarity	NPC471907
0.8955	High Similarity	NPC99731
0.8944	High Similarity	NPC19896
0.8939	High Similarity	NPC10926
0.8913	High Similarity	NPC315275
0.8905	High Similarity	NPC474519
0.8897	High Similarity	NPC477221
0.8889	High Similarity	NPC62219
0.8881	High Similarity	NPC282923
0.8872	High Similarity	NPC8745
0.8844	High Similarity	NPC154683
0.8844	High Similarity	NPC40356
0.8836	High Similarity	NPC202595
0.8836	High Similarity	NPC280295
0.8832	High Similarity	NPC139074
0.8832	High Similarity	NPC40524
0.8832	High Similarity	NPC213485
0.8824	High Similarity	NPC205992
0.8811	High Similarity	NPC227841
0.8803	High Similarity	NPC469520
0.88	High Similarity	NPC324736
0.8797	High Similarity	NPC103540
0.8794	High Similarity	NPC156872
0.8786	High Similarity	NPC416
0.8786	High Similarity	NPC61398
0.8786	High Similarity	NPC4214
0.8786	High Similarity	NPC13715
0.8784	High Similarity	NPC208806
0.8777	High Similarity	NPC118919
0.8768	High Similarity	NPC288089
0.8741	High Similarity	NPC451542
0.8741	High Similarity	NPC174905
0.8741	High Similarity	NPC295712
0.8741	High Similarity	NPC474203
0.8741	High Similarity	NPC313047
0.8741	High Similarity	NPC179898
0.8741	High Similarity	NPC293545
0.8723	High Similarity	NPC162939
0.8722	High Similarity	NPC13238
0.8714	High Similarity	NPC53001
0.8705	High Similarity	NPC283590
0.8705	High Similarity	NPC278375
0.8705	High Similarity	NPC70859
0.8705	High Similarity	NPC61153
0.8705	High Similarity	NPC130899
0.8705	High Similarity	NPC283088
0.8696	High Similarity	NPC48036
0.869	High Similarity	NPC314437
0.869	High Similarity	NPC300540
0.8686	High Similarity	NPC475042
0.8681	High Similarity	NPC10764
0.8676	High Similarity	NPC120488
0.8676	High Similarity	NPC92624
0.8676	High Similarity	NPC102829
0.8671	High Similarity	NPC257644
0.8671	High Similarity	NPC94076
0.8671	High Similarity	NPC85310
0.8671	High Similarity	NPC182255
0.8658	High Similarity	NPC470408
0.8658	High Similarity	NPC182921
0.8658	High Similarity	NPC218870
0.8658	High Similarity	NPC472211
0.8658	High Similarity	NPC474824
0.8658	High Similarity	NPC107109
0.8652	High Similarity	NPC87723
0.8647	High Similarity	NPC375356
0.8633	High Similarity	NPC474394
0.8633	High Similarity	NPC50924
0.8633	High Similarity	NPC12070
0.8633	High Similarity	NPC202225
0.863	High Similarity	NPC34802
0.863	High Similarity	NPC119767
0.8623	High Similarity	NPC175738
0.8621	High Similarity	NPC49282
0.8621	High Similarity	NPC12402
0.8621	High Similarity	NPC478019
0.8613	High Similarity	NPC259942
0.8611	High Similarity	NPC167663
0.8611	High Similarity	NPC66593
0.8611	High Similarity	NPC471682
0.8611	High Similarity	NPC84266
0.8601	High Similarity	NPC91019
0.8601	High Similarity	NPC106519
0.86	High Similarity	NPC226656
0.86	High Similarity	NPC66508
0.8593	High Similarity	NPC96915
0.8593	High Similarity	NPC160499
0.8592	High Similarity	NPC26924
0.8582	High Similarity	NPC173978
0.8582	High Similarity	NPC474110
0.8582	High Similarity	NPC68756
0.8582	High Similarity	NPC44960
0.8582	High Similarity	NPC142956
0.8582	High Similarity	NPC152525
0.8582	High Similarity	NPC305060
0.8582	High Similarity	NPC147418
0.8581	High Similarity	NPC205766
0.8571	High Similarity	NPC249272
0.8571	High Similarity	NPC91478
0.8571	High Similarity	NPC32032
0.8571	High Similarity	NPC133909
0.8571	High Similarity	NPC290803
0.8571	High Similarity	NPC2569
0.8571	High Similarity	NPC258502
0.8571	High Similarity	NPC172329
0.8571	High Similarity	NPC300274
0.8571	High Similarity	NPC80035
0.8562	High Similarity	NPC110882
0.8562	High Similarity	NPC143685
0.8562	High Similarity	NPC136878
0.8562	High Similarity	NPC85393
0.8562	High Similarity	NPC147250
0.8562	High Similarity	NPC271944
0.8561	High Similarity	NPC115458
0.8561	High Similarity	NPC225051
0.8561	High Similarity	NPC37299
0.8561	High Similarity	NPC114183
0.8561	High Similarity	NPC180261
0.8561	High Similarity	NPC294226
0.8553	High Similarity	NPC470559
0.8552	High Similarity	NPC475201
0.8551	High Similarity	NPC41847
0.8551	High Similarity	NPC471851
0.8543	High Similarity	NPC5379
0.8543	High Similarity	NPC14561
0.8543	High Similarity	NPC77807
0.8543	High Similarity	NPC474861
0.8542	High Similarity	NPC19631
0.8542	High Similarity	NPC239136
0.854	High Similarity	NPC476119
0.854	High Similarity	NPC109123
0.854	High Similarity	NPC474998
0.8533	High Similarity	NPC214632
0.8531	High Similarity	NPC315578
0.8529	High Similarity	NPC190043
0.8529	High Similarity	NPC105157
0.8529	High Similarity	NPC98254
0.8529	High Similarity	NPC30501
0.8529	High Similarity	NPC162612
0.8529	High Similarity	NPC23126

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 NPC190457 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	400
0.1-0.2	986
0.2-0.3	1628
0.3-0.4	2896
0.4-0.5	1886
0.5-0.6	949
0.6-0.7	296
0.7-0.8	94
0.8-0.85	12
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9624	High Similarity	NPD1509	Clinical (unspecified phase)
0.8811	High Similarity	NPD7390	Discontinued
0.8797	High Similarity	NPD1470	Approved
0.8496	Intermediate Similarity	NPD1201	Approved
0.8489	Intermediate Similarity	NPD943	Approved
0.8322	Intermediate Similarity	NPD5405	Approved
0.8322	Intermediate Similarity	NPD5404	Approved
0.8322	Intermediate Similarity	NPD5408	Approved
0.8322	Intermediate Similarity	NPD5406	Approved
0.8252	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD1510	Phase 2
0.8153	Intermediate Similarity	NPD6232	Discontinued
0.8113	Intermediate Similarity	NPD7473	Discontinued
0.8112	Intermediate Similarity	NPD1607	Approved
0.8089	Intermediate Similarity	NPD6959	Discontinued
0.8	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2532	Approved
0.7974	Intermediate Similarity	NPD4380	Phase 2
0.7972	Intermediate Similarity	NPD1240	Approved
0.7959	Intermediate Similarity	NPD1549	Phase 2
0.7935	Intermediate Similarity	NPD7819	Suspended
0.791	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3226	Approved
0.773	Intermediate Similarity	NPD1164	Approved
0.7697	Intermediate Similarity	NPD1511	Approved
0.7658	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1934	Approved
0.7597	Intermediate Similarity	NPD1512	Approved
0.7584	Intermediate Similarity	NPD2935	Discontinued
0.758	Intermediate Similarity	NPD7411	Suspended
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7562	Intermediate Similarity	NPD3749	Approved
0.7533	Intermediate Similarity	NPD2346	Discontinued
0.7518	Intermediate Similarity	NPD9269	Phase 2
0.75	Intermediate Similarity	NPD3750	Approved
0.7484	Intermediate Similarity	NPD2801	Approved
0.7482	Intermediate Similarity	NPD9268	Approved
0.7467	Intermediate Similarity	NPD2796	Approved
0.7467	Intermediate Similarity	NPD1551	Phase 2
0.7457	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7075	Discontinued
0.7434	Intermediate Similarity	NPD2800	Approved
0.7432	Intermediate Similarity	NPD230	Phase 1
0.741	Intermediate Similarity	NPD3818	Discontinued
0.7394	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6166	Phase 2
0.7394	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7768	Phase 2
0.7391	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD3882	Suspended
0.7386	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5710	Approved
0.7378	Intermediate Similarity	NPD5711	Approved
0.7375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5494	Approved
0.7347	Intermediate Similarity	NPD3764	Approved
0.7337	Intermediate Similarity	NPD6559	Discontinued
0.7326	Intermediate Similarity	NPD8150	Discontinued
0.7312	Intermediate Similarity	NPD6801	Discontinued
0.7296	Intermediate Similarity	NPD6599	Discontinued
0.729	Intermediate Similarity	NPD3300	Phase 2
0.7273	Intermediate Similarity	NPD6535	Approved
0.7273	Intermediate Similarity	NPD6534	Approved
0.7267	Intermediate Similarity	NPD1465	Phase 2
0.7234	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD920	Approved
0.7208	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2344	Approved
0.7183	Intermediate Similarity	NPD3019	Approved
0.7171	Intermediate Similarity	NPD3748	Approved
0.7171	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD6779	Approved
0.7167	Intermediate Similarity	NPD6777	Approved
0.7167	Intermediate Similarity	NPD6778	Approved
0.7167	Intermediate Similarity	NPD6780	Approved
0.7167	Intermediate Similarity	NPD6782	Approved
0.7167	Intermediate Similarity	NPD6776	Approved
0.7167	Intermediate Similarity	NPD6781	Approved
0.716	Intermediate Similarity	NPD6020	Phase 2
0.716	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6651	Approved
0.7151	Intermediate Similarity	NPD7699	Phase 2
0.7151	Intermediate Similarity	NPD8313	Approved
0.7151	Intermediate Similarity	NPD7700	Phase 2
0.7151	Intermediate Similarity	NPD8312	Approved
0.7135	Intermediate Similarity	NPD8151	Discontinued
0.7134	Intermediate Similarity	NPD6799	Approved
0.7124	Intermediate Similarity	NPD6099	Approved
0.7124	Intermediate Similarity	NPD6100	Approved
0.7118	Intermediate Similarity	NPD7074	Phase 3
0.7117	Intermediate Similarity	NPD5402	Approved
0.7117	Intermediate Similarity	NPD3817	Phase 2
0.7114	Intermediate Similarity	NPD2313	Discontinued
0.7101	Intermediate Similarity	NPD3751	Discontinued
0.7099	Intermediate Similarity	NPD37	Approved
0.7097	Intermediate Similarity	NPD1243	Approved
0.7076	Intermediate Similarity	NPD5953	Discontinued
0.7076	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2932	Approved
0.7059	Intermediate Similarity	NPD74	Approved
0.7059	Intermediate Similarity	NPD7054	Approved
0.7059	Intermediate Similarity	NPD2799	Discontinued
0.7059	Intermediate Similarity	NPD9266	Approved
0.7051	Intermediate Similarity	NPD7003	Approved
0.7049	Intermediate Similarity	NPD7696	Phase 3
0.7049	Intermediate Similarity	NPD7698	Approved
0.7049	Intermediate Similarity	NPD7697	Approved
0.7049	Intermediate Similarity	NPD7435	Discontinued
0.7045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6212	Phase 3
0.7022	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6213	Phase 3
0.7021	Intermediate Similarity	NPD9493	Approved
0.7019	Intermediate Similarity	NPD7458	Discontinued
0.7018	Intermediate Similarity	NPD7472	Approved
0.7011	Intermediate Similarity	NPD7870	Phase 2
0.7011	Intermediate Similarity	NPD7871	Phase 2
0.7011	Intermediate Similarity	NPD8320	Phase 1
0.7011	Intermediate Similarity	NPD8319	Approved
0.7007	Intermediate Similarity	NPD4750	Phase 3
0.7006	Intermediate Similarity	NPD1247	Approved
0.7006	Intermediate Similarity	NPD2309	Approved
0.7006	Intermediate Similarity	NPD6190	Approved
0.6994	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9264	Approved
0.6985	Remote Similarity	NPD9267	Approved
0.6985	Remote Similarity	NPD2342	Discontinued
0.6985	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9263	Approved
0.6977	Remote Similarity	NPD6797	Phase 2
0.697	Remote Similarity	NPD4967	Phase 2
0.697	Remote Similarity	NPD4965	Approved
0.697	Remote Similarity	NPD4966	Approved
0.6968	Remote Similarity	NPD1471	Phase 3
0.6959	Remote Similarity	NPD7286	Phase 2
0.6943	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4628	Phase 3
0.6939	Remote Similarity	NPD1283	Approved
0.6936	Remote Similarity	NPD7251	Discontinued
0.6935	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9545	Approved
0.6917	Remote Similarity	NPD1242	Phase 1
0.6898	Remote Similarity	NPD7701	Phase 2
0.6897	Remote Similarity	NPD7808	Phase 3
0.6894	Remote Similarity	NPD5403	Approved
0.6892	Remote Similarity	NPD1203	Approved
0.6886	Remote Similarity	NPD919	Approved
0.6886	Remote Similarity	NPD6234	Discontinued
0.6885	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5951	Approved
0.6875	Remote Similarity	NPD1651	Approved
0.6875	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5401	Approved
0.6864	Remote Similarity	NPD7229	Phase 3
0.6849	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2798	Approved
0.6835	Remote Similarity	NPD3400	Discontinued
0.6825	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7874	Approved
0.6824	Remote Similarity	NPD3926	Phase 2
0.6821	Remote Similarity	NPD4625	Phase 3
0.6811	Remote Similarity	NPD6823	Phase 2
0.6803	Remote Similarity	NPD3972	Approved
0.6791	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7801	Approved
0.6781	Remote Similarity	NPD3023	Approved
0.6781	Remote Similarity	NPD3026	Approved
0.6779	Remote Similarity	NPD3094	Phase 2
0.6776	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD1237	Approved
0.6765	Remote Similarity	NPD3787	Discontinued
0.6761	Remote Similarity	NPD9281	Approved
0.6759	Remote Similarity	NPD3024	Approved
0.6759	Remote Similarity	NPD3025	Approved
0.6741	Remote Similarity	NPD940	Approved
0.6741	Remote Similarity	NPD846	Approved
0.6738	Remote Similarity	NPD7635	Approved
0.6735	Remote Similarity	NPD1610	Phase 2
0.6735	Remote Similarity	NPD1281	Approved
0.6732	Remote Similarity	NPD6663	Approved
0.673	Remote Similarity	NPD8166	Discontinued
0.6728	Remote Similarity	NPD6273	Approved
0.6711	Remote Similarity	NPD1876	Approved
0.6707	Remote Similarity	NPD8438	Clinical (unspecified phase)

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