NPASS Compound

Structure

CID290550 OpenBabel06191716102D 22 24 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 -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 -3.4641 -2.0000 0.0000 C 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 7 1 0 0 0 0 2 5 1 0 0 0 0 2 9 2 0 0 0 0 3 6 2 0 0 0 0 3 8 1 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 14 1 0 0 0 0 12 14 1 0 0 0 0 13 19 2 0 0 0 0 14 20 2 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.03
Volume:	280.13
LogP:	3.238
LogD:	1.769
LogS:	-4.162
# Rotatable Bonds:	1
TPSA:	132.13
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.532
Synthetic Accessibility Score:	2.439
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.663
MDCK Permeability:	6.489183306257473e-06
Pgp-inhibitor:	0.008
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.755
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.052
Plasma Protein Binding (PPB):	96.7417984008789%
Volume Distribution (VD):	0.582
Pgp-substrate:	4.759204387664795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.351
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.035
CYP2C9-inhibitor:	0.456
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.049
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.256
CYP3A4-substrate:	0.048

ADMET: Excretion

Clearance (CL):	2.099
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.988
AMES Toxicity:	0.722
Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.409
Carcinogencity:	0.06
Eye Corrosion:	0.003
Eye Irritation:	0.669
Respiratory Toxicity:	0.076

Download Data

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

Natural Product: NPC290550

Natural Product ID:	NPC290550
*Common Name:**	Emodic Acid
IUPAC Name:	4,5,7-trihydroxy-9,10-dioxoanthracene-2-carboxylic acid
Synonyms:	Emodic Acid
Standard InCHIKey:	ZJXVNNSMRGTDBI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H8O7/c16-6-3-8-12(10(18)4-6)14(20)11-7(13(8)19)1-5(15(21)22)2-9(11)17/h1-4,16-18H,(H,21,22)
SMILES:	Oc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL290914
PubChem CID:	361510
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0001911] Anthracenecarboxylic acids and derivatives [CHEMONTID:0002424] Anthracenecarboxylic acids

*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
NPO28478	Magnolia ovata	Species	Magnoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19658431]
NPO13709	Holopus rangii	Species	Holopodidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20158243]
NPO28478	Magnolia ovata	Species	Magnoliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23157012]
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]
NPO40274	Penicillium sp. SCSIO sof101	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28509552]
NPO24699	Phlogacanthus curviflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO13709	Holopus rangii	Species	Holopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28478	Magnolia ovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO472	Penicillium restrictum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24989	Solanum cleistogamum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26465	Coreopsis tinctoria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26777	Pneumatopteris pennigera	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26401	Andrographis neesiana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23412	Uvaria afzelii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26202	Loranthus pentandrus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15746	Athelia rolfsii	Species	Atheliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24699	Phlogacanthus curviflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25352	Pluchea odora	Species	Asteraceae	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	6
Others	6
Potency	64

Activity Type	# Activity
Cell Line	3
Individual Protein	61
Organism	2
Others	7
Protein-Protein Interaction	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3769	Individual Protein	Elastase 2A	Sus scrofa	Inhibition	=	9.0	%	PMID[529953]
NPT279	Individual Protein	Leukocyte elastase	Homo sapiens	Inhibition	=	21.0	%	PMID[529953]
NPT2682	Individual Protein	Alpha-chymotrypsin	Bos taurus	Inhibition	=	3.0	%	PMID[529953]
NPT278	Individual Protein	Cathepsin G	Homo sapiens	Inhibition	=	14.0	%	PMID[529953]
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	35481.3	nM	PMID[529955]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	=	14125.4	nM	PMID[529955]
NPT2741	Individual Protein	Pyruvate kinase	Leishmania mexicana	Potency	=	17782.8	nM	PMID[529955]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	6309.6	nM	PMID[529955]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	10000.0	nM	PMID[529956]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	25118.9	nM	PMID[529955]
NPT2628	Individual Protein	Luciferase	Photuris pennsylvanica	Potency	=	17782.8	nM	PMID[529956]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	12589.3	nM	PMID[529956]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	3981.1	nM	PMID[529955]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	7079.5	nM	PMID[529956]
NPT52	Individual Protein	Pyruvate kinase isozymes M1/M2	Homo sapiens	Potency	=	17782.8	nM	PMID[529955]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	11220.2	nM	PMID[529955]
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	39810.7	nM	PMID[529955]
NPT53	Individual Protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	10000.0	nM	PMID[529955]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	31622.8	nM	PMID[529956]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	17740.7	nM	PMID[529955]
NPT282	Individual Protein	MAP kinase ERK2	Homo sapiens	Potency	=	22387.2	nM	PMID[529955]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	14125.4	nM	PMID[529956]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	6309.6	nM	PMID[529955]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	7943.3	nM	PMID[529955]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	15848.9	nM	PMID[529956]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[529955]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[529955]
NPT63	Individual Protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[529955]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[529955]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[529956]
NPT484	Individual Protein	Luciferin 4-monooxygenase	Photinus pyralis	Potency	n.a.	21331.3	nM	PMID[529955]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	56234.1	nM	PMID[529956]
NPT534	Individual Protein	Phosphoglycerate kinase, glycosomal	Trypanosoma brucei brucei	Potency	n.a.	17782.8	nM	PMID[529955]
NPT100	Individual Protein	Glutaminase kidney isoform, mitochondrial	Homo sapiens	Potency	n.a.	17782.8	nM	PMID[529955]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[529955]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[529955]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	12995.3	nM	PMID[529955]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[529955]
NPT161	Individual Protein	Rap guanine nucleotide exchange factor 4	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[529955]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	7943.3	nM	PMID[529955]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[529955]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[529956]
NPT446	Individual Protein	Rap guanine nucleotide exchange factor 3	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[529955]
NPT4782	Individual Protein	Accessory gene regulator protein A	Staphylococcus aureus	IC50	=	30600.0	nM	PMID[529958]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	10000.0	nM	PMID[529959]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[529959]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[529959]
NPT2	Others	Unspecified		Potency	=	10000.0	nM	PMID[529956]
NPT2	Others	Unspecified		Potency	=	12589.3	nM	PMID[529955]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	22387.2	nM	PMID[529955]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	25118.9	nM	PMID[529956]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	28183.8	nM	PMID[529956]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	25118.9	nM	PMID[529955]
NPT864	Individual Protein	Lethal(3)malignant brain tumor-like protein 1	Homo sapiens	Potency	=	2511.9	nM	PMID[529955]
NPT2	Others	Unspecified		Potency	n.a.	23109.3	nM	PMID[529955]
NPT533	Protein-Protein Interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[529955]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PMID[529955]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[529955]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[529955]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[529955]
NPT2	Others	Unspecified		Potency	n.a.	11220.2	nM	PMID[529955]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	8275.3	nM	PMID[529955]
NPT821	Individual Protein	Werner syndrome ATP-dependent helicase	Homo sapiens	Potency	n.a.	63095.7	nM	PMID[529955]
NPT755	Individual Protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[529955]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	150.05	%	PMID[529957]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	72.9	%	PMID[529957]
NPT9	Individual Protein	DNA polymerase eta	Homo sapiens	Potency	n.a.	6012.0	nM	PMID[529955]
NPT2	Others	Unspecified		IC50	=	4190.0	nM	PMID[529955]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[529955]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	Potency	n.a.	29934.9	nM	PMID[529955]
NPT2	Others	Unspecified		IC50	=	4415.0	nM	PMID[529955]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	60119.8	nM	PMID[529955]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	21192.3	nM	PMID[529955]

☑ 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 NPC290550 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	414
0.1-0.2	1916
0.2-0.3	4258
0.3-0.4	10603
0.4-0.5	8318
0.5-0.6	5059
0.6-0.7	6024
0.7-0.8	5375
0.8-0.85	550
0.85-0.9	140
0.9-0.95	39
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9504	High Similarity	NPC471907
0.9481	High Similarity	NPC254847
0.9416	High Similarity	NPC190457
0.9416	High Similarity	NPC143438
0.9412	High Similarity	NPC53206
0.9412	High Similarity	NPC471905
0.9412	High Similarity	NPC53414
0.9353	High Similarity	NPC73061
0.9353	High Similarity	NPC193555
0.9343	High Similarity	NPC4214
0.9333	High Similarity	NPC288089
0.9333	High Similarity	NPC44437
0.9275	High Similarity	NPC138099
0.9275	High Similarity	NPC242994
0.9265	High Similarity	NPC161632
0.9259	High Similarity	NPC267205
0.9259	High Similarity	NPC48036
0.9209	High Similarity	NPC181560
0.9209	High Similarity	NPC169452
0.9209	High Similarity	NPC183345
0.9143	High Similarity	NPC246638
0.9143	High Similarity	NPC305845
0.9143	High Similarity	NPC204045
0.9085	High Similarity	NPC471906
0.9085	High Similarity	NPC244691
0.9078	High Similarity	NPC135524
0.9058	High Similarity	NPC118919
0.9058	High Similarity	NPC191976
0.9014	High Similarity	NPC66593
0.9	High Similarity	NPC26924
0.8993	High Similarity	NPC471452
0.8951	High Similarity	NPC21599
0.8951	High Similarity	NPC48762
0.8951	High Similarity	NPC193703
0.8944	High Similarity	NPC474961
0.8936	High Similarity	NPC315578
0.8936	High Similarity	NPC203063
0.8929	High Similarity	NPC13715
0.8913	High Similarity	NPC282780
0.8913	High Similarity	NPC166480
0.8897	High Similarity	NPC37709
0.8889	High Similarity	NPC95537
0.8889	High Similarity	NPC41263
0.8889	High Similarity	NPC34482
0.8881	High Similarity	NPC238629
0.8867	High Similarity	NPC263483
0.8867	High Similarity	NPC197326
0.8849	High Similarity	NPC278375
0.8849	High Similarity	NPC290803
0.8841	High Similarity	NPC52407
0.8841	High Similarity	NPC180261
0.8841	High Similarity	NPC37299
0.8828	High Similarity	NPC314437
0.8828	High Similarity	NPC470570
0.8824	High Similarity	NPC99731
0.8806	High Similarity	NPC10926
0.8777	High Similarity	NPC474519
0.8768	High Similarity	NPC70622
0.8767	High Similarity	NPC56433
0.8767	High Similarity	NPC190648
0.8767	High Similarity	NPC126767
0.8767	High Similarity	NPC312929
0.8767	High Similarity	NPC245584
0.8767	High Similarity	NPC289042
0.8767	High Similarity	NPC118027
0.8759	High Similarity	NPC12402
0.875	High Similarity	NPC282923
0.8741	High Similarity	NPC8745
0.8741	High Similarity	NPC110810
0.8716	High Similarity	NPC315520
0.8716	High Similarity	NPC147735
0.8716	High Similarity	NPC294646
0.8716	High Similarity	NPC205766
0.8714	High Similarity	NPC80035
0.8707	High Similarity	NPC2569
0.8707	High Similarity	NPC172329
0.8705	High Similarity	NPC115458
0.8696	High Similarity	NPC93015
0.8696	High Similarity	NPC205992
0.869	High Similarity	NPC227841
0.869	High Similarity	NPC19896
0.8675	High Similarity	NPC474861
0.8667	High Similarity	NPC201728
0.8667	High Similarity	NPC214632
0.8667	High Similarity	NPC262671
0.8667	High Similarity	NPC103540
0.8667	High Similarity	NPC208806
0.8662	High Similarity	NPC61398
0.8662	High Similarity	NPC416
0.8652	High Similarity	NPC272268
0.8652	High Similarity	NPC158481
0.8639	High Similarity	NPC119767
0.8623	High Similarity	NPC136588
0.8623	High Similarity	NPC147757
0.8623	High Similarity	NPC31799
0.8623	High Similarity	NPC199253
0.8623	High Similarity	NPC31539
0.8621	High Similarity	NPC293545
0.8621	High Similarity	NPC313047
0.8621	High Similarity	NPC474203
0.8621	High Similarity	NPC295712
0.8621	High Similarity	NPC451542
0.8621	High Similarity	NPC174905
0.8613	High Similarity	NPC179898
0.8611	High Similarity	NPC187843
0.8609	High Similarity	NPC66029
0.8601	High Similarity	NPC162939
0.8593	High Similarity	NPC13238
0.8592	High Similarity	NPC53001
0.8592	High Similarity	NPC62272
0.8591	High Similarity	NPC470568
0.8591	High Similarity	NPC255641
0.8591	High Similarity	NPC290954
0.8582	High Similarity	NPC72918
0.8582	High Similarity	NPC283088
0.8571	High Similarity	NPC147250
0.8571	High Similarity	NPC314048
0.8571	High Similarity	NPC53896
0.8562	High Similarity	NPC10764
0.8552	High Similarity	NPC257644
0.8552	High Similarity	NPC137649
0.8551	High Similarity	NPC92624
0.8543	High Similarity	NPC474824
0.8543	High Similarity	NPC470408
0.8543	High Similarity	NPC182921
0.8543	High Similarity	NPC218870
0.8542	High Similarity	NPC99441
0.8542	High Similarity	NPC96421
0.8533	High Similarity	NPC470569
0.8531	High Similarity	NPC87723
0.8523	High Similarity	NPC70764
0.8521	High Similarity	NPC223836
0.8521	High Similarity	NPC472308
0.8519	High Similarity	NPC375356
0.8514	High Similarity	NPC290194
0.8511	High Similarity	NPC474394
0.8511	High Similarity	NPC50924
0.8511	High Similarity	NPC12070
0.85	High Similarity	NPC478190
0.85	High Similarity	NPC175738
0.8493	Intermediate Similarity	NPC471682
0.8489	Intermediate Similarity	NPC17840
0.8489	Intermediate Similarity	NPC62219
0.8489	Intermediate Similarity	NPC247477
0.8489	Intermediate Similarity	NPC259942
0.8487	Intermediate Similarity	NPC318270
0.8483	Intermediate Similarity	NPC37530
0.8477	Intermediate Similarity	NPC40356
0.8477	Intermediate Similarity	NPC175978
0.8477	Intermediate Similarity	NPC154683
0.8472	Intermediate Similarity	NPC92655
0.8467	Intermediate Similarity	NPC96915
0.8467	Intermediate Similarity	NPC160499
0.8467	Intermediate Similarity	NPC280295
0.8467	Intermediate Similarity	NPC119929
0.8467	Intermediate Similarity	NPC470107
0.8462	Intermediate Similarity	NPC44960
0.8462	Intermediate Similarity	NPC474110
0.8462	Intermediate Similarity	NPC178467
0.8462	Intermediate Similarity	NPC474771
0.8462	Intermediate Similarity	NPC149372
0.8462	Intermediate Similarity	NPC147418
0.8462	Intermediate Similarity	NPC65837
0.8462	Intermediate Similarity	NPC474849
0.8456	Intermediate Similarity	NPC173978
0.8456	Intermediate Similarity	NPC142956
0.8456	Intermediate Similarity	NPC153417
0.8456	Intermediate Similarity	NPC236189
0.8451	Intermediate Similarity	NPC249272
0.8451	Intermediate Similarity	NPC258502
0.8446	Intermediate Similarity	NPC225173
0.8446	Intermediate Similarity	NPC163846
0.8446	Intermediate Similarity	NPC85393
0.8446	Intermediate Similarity	NPC271944
0.8446	Intermediate Similarity	NPC110882
0.8444	Intermediate Similarity	NPC283514
0.8444	Intermediate Similarity	NPC133909
0.8444	Intermediate Similarity	NPC91478
0.8444	Intermediate Similarity	NPC32032
0.8444	Intermediate Similarity	NPC300274
0.844	Intermediate Similarity	NPC114183
0.844	Intermediate Similarity	NPC225051
0.844	Intermediate Similarity	NPC294226
0.8431	Intermediate Similarity	NPC146211
0.8425	Intermediate Similarity	NPC291078
0.8425	Intermediate Similarity	NPC94076
0.8425	Intermediate Similarity	NPC19631
0.8425	Intermediate Similarity	NPC239136
0.8425	Intermediate Similarity	NPC182255
0.8421	Intermediate Similarity	NPC472211
0.8421	Intermediate Similarity	NPC107109
0.8418	Intermediate Similarity	NPC107009
0.8417	Intermediate Similarity	NPC109123
0.8417	Intermediate Similarity	NPC474998
0.8414	Intermediate Similarity	NPC165172
0.8414	Intermediate Similarity	NPC156872
0.8414	Intermediate Similarity	NPC168471
0.8414	Intermediate Similarity	NPC225243
0.8414	Intermediate Similarity	NPC155205
0.8406	Intermediate Similarity	NPC103356

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 NPC290550 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	986
0.2-0.3	1717
0.3-0.4	2883
0.4-0.5	1898
0.5-0.6	866
0.6-0.7	287
0.7-0.8	97
0.8-0.85	10
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9481	High Similarity	NPD1509	Clinical (unspecified phase)
0.869	High Similarity	NPD7390	Discontinued
0.8667	High Similarity	NPD1470	Approved
0.8592	High Similarity	NPD5408	Approved
0.8592	High Similarity	NPD5406	Approved
0.8592	High Similarity	NPD5405	Approved
0.8592	High Similarity	NPD5404	Approved
0.837	Intermediate Similarity	NPD1201	Approved
0.8369	Intermediate Similarity	NPD943	Approved
0.828	Intermediate Similarity	NPD6232	Discontinued
0.8278	Intermediate Similarity	NPD3226	Approved
0.8239	Intermediate Similarity	NPD7473	Discontinued
0.8138	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2532	Approved
0.8013	Intermediate Similarity	NPD2533	Approved
0.8013	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD1164	Approved
0.7973	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7819	Suspended
0.7891	Intermediate Similarity	NPD1510	Phase 2
0.7877	Intermediate Similarity	NPD1607	Approved
0.7821	Intermediate Similarity	NPD7411	Suspended
0.7799	Intermediate Similarity	NPD3749	Approved
0.7794	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD9269	Phase 2
0.7785	Intermediate Similarity	NPD2346	Discontinued
0.7764	Intermediate Similarity	NPD6959	Discontinued
0.7754	Intermediate Similarity	NPD9268	Approved
0.7748	Intermediate Similarity	NPD3750	Approved
0.774	Intermediate Similarity	NPD1240	Approved
0.7718	Intermediate Similarity	NPD2935	Discontinued
0.7662	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1549	Phase 2
0.7603	Intermediate Similarity	NPD3764	Approved
0.7597	Intermediate Similarity	NPD1511	Approved
0.7562	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD1512	Approved
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7483	Intermediate Similarity	NPD1551	Phase 2
0.7469	Intermediate Similarity	NPD7075	Discontinued
0.7451	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD230	Phase 1
0.7417	Intermediate Similarity	NPD3748	Approved
0.7407	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7768	Phase 2
0.7394	Intermediate Similarity	NPD5711	Approved
0.7394	Intermediate Similarity	NPD5710	Approved
0.7391	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD2313	Discontinued
0.7338	Intermediate Similarity	NPD1243	Approved
0.7338	Intermediate Similarity	NPD2800	Approved
0.7333	Intermediate Similarity	NPD74	Approved
0.7333	Intermediate Similarity	NPD9266	Approved
0.7329	Intermediate Similarity	NPD1934	Approved
0.7312	Intermediate Similarity	NPD6599	Discontinued
0.7303	Intermediate Similarity	NPD2799	Discontinued
0.7303	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2801	Approved
0.7259	Intermediate Similarity	NPD9263	Approved
0.7259	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD9264	Approved
0.7259	Intermediate Similarity	NPD9267	Approved
0.7241	Intermediate Similarity	NPD8150	Discontinued
0.7233	Intermediate Similarity	NPD920	Approved
0.7222	Intermediate Similarity	NPD6801	Discontinued
0.7215	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3300	Phase 2
0.7179	Intermediate Similarity	NPD7003	Approved
0.7179	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD9493	Approved
0.7152	Intermediate Similarity	NPD6799	Approved
0.7152	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6559	Discontinued
0.7143	Intermediate Similarity	NPD5951	Approved
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2796	Approved
0.7143	Intermediate Similarity	NPD1203	Approved
0.7134	Intermediate Similarity	NPD3817	Phase 2
0.7133	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3818	Discontinued
0.7097	Intermediate Similarity	NPD2344	Approved
0.7097	Intermediate Similarity	NPD1471	Phase 3
0.7093	Intermediate Similarity	NPD5953	Discontinued
0.7091	Intermediate Similarity	NPD3882	Suspended
0.7089	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3019	Approved
0.7076	Intermediate Similarity	NPD6020	Phase 2
0.7075	Intermediate Similarity	NPD1283	Approved
0.7069	Intermediate Similarity	NPD8312	Approved
0.7069	Intermediate Similarity	NPD8313	Approved
0.7066	Intermediate Similarity	NPD5494	Approved
0.7062	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8151	Discontinued
0.7037	Intermediate Similarity	NPD7458	Discontinued
0.7032	Intermediate Similarity	NPD6099	Approved
0.7032	Intermediate Similarity	NPD6100	Approved
0.703	Intermediate Similarity	NPD5402	Approved
0.7021	Intermediate Similarity	NPD9281	Approved
0.7012	Intermediate Similarity	NPD37	Approved
0.7	Intermediate Similarity	NPD6166	Phase 2
0.7	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6534	Approved
0.7	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6535	Approved
0.6994	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7286	Phase 2
0.6973	Remote Similarity	NPD7435	Discontinued
0.6966	Remote Similarity	NPD2932	Approved
0.6963	Remote Similarity	NPD9261	Approved
0.6952	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6651	Approved
0.6944	Remote Similarity	NPD9545	Approved
0.6935	Remote Similarity	NPD8320	Phase 1
0.6935	Remote Similarity	NPD8319	Approved
0.6928	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1247	Approved
0.6918	Remote Similarity	NPD6190	Approved
0.6918	Remote Similarity	NPD2309	Approved
0.6914	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD411	Approved
0.6908	Remote Similarity	NPD3268	Approved
0.6906	Remote Similarity	NPD4750	Phase 3
0.6905	Remote Similarity	NPD919	Approved
0.6905	Remote Similarity	NPD6234	Discontinued
0.6902	Remote Similarity	NPD6781	Approved
0.6902	Remote Similarity	NPD6778	Approved
0.6902	Remote Similarity	NPD6782	Approved
0.6902	Remote Similarity	NPD6780	Approved
0.6902	Remote Similarity	NPD6777	Approved
0.6902	Remote Similarity	NPD6779	Approved
0.6902	Remote Similarity	NPD6776	Approved
0.6886	Remote Similarity	NPD4966	Approved
0.6886	Remote Similarity	NPD4965	Approved
0.6886	Remote Similarity	NPD4967	Phase 2
0.6885	Remote Similarity	NPD7700	Phase 2
0.6885	Remote Similarity	NPD7699	Phase 2
0.6884	Remote Similarity	NPD2342	Discontinued
0.6883	Remote Similarity	NPD447	Suspended
0.6882	Remote Similarity	NPD7229	Phase 3
0.6879	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD4287	Approved
0.6871	Remote Similarity	NPD1281	Approved
0.6867	Remote Similarity	NPD2798	Approved
0.6859	Remote Similarity	NPD4308	Phase 3
0.6855	Remote Similarity	NPD4628	Phase 3
0.6849	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7074	Phase 3
0.6826	Remote Similarity	NPD4288	Approved
0.6824	Remote Similarity	NPD9717	Approved
0.6821	Remote Similarity	NPD3751	Discontinued
0.6815	Remote Similarity	NPD1242	Phase 1
0.6811	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5403	Approved
0.6797	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD7697	Approved
0.6791	Remote Similarity	NPD7698	Approved
0.6791	Remote Similarity	NPD7696	Phase 3
0.679	Remote Similarity	NPD5401	Approved
0.679	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7054	Approved
0.6758	Remote Similarity	NPD6212	Phase 3
0.6758	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6213	Phase 3
0.6755	Remote Similarity	NPD7870	Phase 2
0.6755	Remote Similarity	NPD7871	Phase 2
0.6754	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7874	Approved
0.6753	Remote Similarity	NPD6663	Approved
0.675	Remote Similarity	NPD3400	Discontinued
0.675	Remote Similarity	NPD8166	Discontinued
0.6743	Remote Similarity	NPD7472	Approved
0.6735	Remote Similarity	NPD4626	Approved
0.6732	Remote Similarity	NPD4625	Phase 3
0.6724	Remote Similarity	NPD7177	Discontinued
0.6724	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5736	Approved
0.6711	Remote Similarity	NPD1608	Approved
0.6705	Remote Similarity	NPD6797	Phase 2
0.6689	Remote Similarity	NPD3266	Approved
0.6689	Remote Similarity	NPD3267	Approved
0.6689	Remote Similarity	NPD3026	Approved
0.6689	Remote Similarity	NPD3023	Approved
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD7251	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