NPASS Compound

Structure

CID6913 OpenBabel06191715332D 26 27 0 0 1 0 0 0 0 0999 V2000 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 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 -6.0622 0.5000 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 -6.9282 3.0000 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 -6.9282 2.0000 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 -3.4641 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 3.5000 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 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 3.5000 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 -7.7942 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 10 1 0 0 0 0 2 5 2 0 0 0 0 2 11 1 0 0 0 0 3 6 2 0 0 0 0 3 10 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 11 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 12 7 1 1 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 17 19 2 3 0 0 0 17 24 1 0 0 0 0 18 25 2 0 0 0 0 18 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	359.1
Volume:	351.571
LogP:	0.7
LogD:	0.296
LogS:	-1.837
# Rotatable Bonds:	7
TPSA:	147.65
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.39
Synthetic Accessibility Score:	2.727
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.883
MDCK Permeability:	7.363762506429339e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.975
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	93.12982940673828%
Volume Distribution (VD):	0.367
Pgp-substrate:	5.062405586242676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.226
CYP1A2-substrate:	0.051
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.486
CYP2C9-substrate:	0.287
CYP2D6-inhibitor:	0.107
CYP2D6-substrate:	0.209
CYP3A4-inhibitor:	0.071
CYP3A4-substrate:	0.1

ADMET: Excretion

Clearance (CL):	10.94
Half-life (T1/2):	0.959

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.573
Rat Oral Acute Toxicity:	0.026
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.919
Carcinogencity:	0.149
Eye Corrosion:	0.003
Eye Irritation:	0.428
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC6913

Natural Product ID:	NPC6913
*Common Name:**	3-(3,4-Dihydroxy-Phenyl)-2-[3-(3,4-Dihydroxy-Phenyl)-Acryloylamino]-Propionic Acid
IUPAC Name:	(2S)-3-(3,4-dihydroxyphenyl)-2-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]propanoic acid
Synonyms:
Standard InCHIKey:	GPZFXSWMDFBRGS-UXONFWTHSA-N
Standard InCHI:	InChI=1S/C18H17NO7/c20-13-4-1-10(8-15(13)22)3-6-17(24)19-12(18(25)26)7-11-2-5-14(21)16(23)9-11/h1-6,8-9,12,20-23H,7H2,(H,19,24)(H,25,26)/p-1/b6-3+/t12-/m0/s1
SMILES:	c1cc(c(cc1/C=C/C(=N[C@@H](Cc1ccc(c(c1)O)O)C(=O)O)O)O)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL241190
PubChem CID:	6506968
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0004319] Tyrosine and derivatives

*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
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)00169-2]
NPO4654	Critonia quadrangularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)81431-4]
NPO25903	Swinglea glutinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575960]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11975485]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15128023]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18068204]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21446699]
NPO16601	Styrax perkinsiae	Species	Styracaceae	Eukaryota	n.a.	bark	n.a.	PMID[26762060]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[31763840]
NPO12697	Baccharis megapotamica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3437280]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9748368]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	Testa	n.a.	n.a.	Database[FooDB]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15024	Senecio rivularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15147	Ficus simplicissima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO10247	Orthosphenia mexicana	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15147	Ficus simplicissima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16289	Marrubium supinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15760	Aconitum pseudohuiliense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15024	Senecio rivularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29175	Strychnos tabascana	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14892	Flemingia congesta	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16362	Symploca hydnoides	Species	Microcoleaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11233	Pseudocyphellaria impressa	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4448	Relhania pumila	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9196	Aconitum sachalinense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7632	Rheum tanguticum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14046	Stevia mercedensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16435	Cacalia bicolor	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13872	Amanita cokeri	Species	Amanitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9823	Centrosema pascuorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11915	Lecanora planaica	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24501	Asteriscus graveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13563	Alstonia deplanchei	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16856	Solanum elaeagnifolium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26436	Citrus glauca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10247	Orthosphenia mexicana	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9107	Metalasia bolusii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15969	Alcyonium molle	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO576	Oxyanthus speciosus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17259	Thuja standishii	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15024	Senecio rivularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15147	Ficus simplicissima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4654	Critonia quadrangularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25903	Swinglea glutinosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14572	Senecio latifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21913	Verbesina rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16522	Ceratozamia fuscoviridis	Species	Zamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5468	Dacrydium fonki	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13396	Aplophyllum popovii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2372	Cryptotermes cynocephalus	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16766	Haplophyllum dauricum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13719	Salacia prinoides	Species	Sertulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16601	Styrax perkinsiae	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16289	Marrubium supinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16071	Erigeron crispus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18873.8	Salmonella enterica subsp. enterica serovar typhimurium	Subspecies	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14723	Streptomyces xantholiticus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14413	Bombus muscorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12697	Baccharis megapotamica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12438	Fomes cajanderi	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15401	Theobroma cacao	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15531	Quercus dentata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10431	Eupatorium gracile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10802	Rhinoceros sondaicus	Species	Rhinocerotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7515	Codium decorticatum	Species	Codiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15760	Aconitum pseudohuiliense	Species	Ranunculaceae	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	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT15	Cell Line	Jurkat	Homo sapiens	Inhibition	=	11.0	%	PMID[550425]
NPT2	Others	Unspecified		IC50	=	21000.0	nM	PMID[550425]
NPT35	Others	n.a.		LogP	=	0.731	n.a.	PMID[550425]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	IC50	=	5700.0	nM	PMID[550426]

☑ 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 NPC6913 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	195
0.1-0.2	1056
0.2-0.3	5481
0.3-0.4	12444
0.4-0.5	6227
0.5-0.6	13031
0.6-0.7	3854
0.7-0.8	381
0.8-0.85	11
0.85-0.9	13
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.8855	High Similarity	NPC16031
0.8855	High Similarity	NPC145888
0.8855	High Similarity	NPC161593
0.8797	High Similarity	NPC45191
0.8661	High Similarity	NPC122009
0.8647	High Similarity	NPC325651
0.8594	High Similarity	NPC268572
0.8594	High Similarity	NPC319950
0.8593	High Similarity	NPC88667
0.8593	High Similarity	NPC244866
0.8583	High Similarity	NPC283468
0.8496	Intermediate Similarity	NPC321561
0.8433	Intermediate Similarity	NPC296712
0.8397	Intermediate Similarity	NPC27581
0.8258	Intermediate Similarity	NPC142577
0.8258	Intermediate Similarity	NPC474862
0.8248	Intermediate Similarity	NPC326966
0.8235	Intermediate Similarity	NPC478147
0.8203	Intermediate Similarity	NPC142599
0.8182	Intermediate Similarity	NPC284078
0.8112	Intermediate Similarity	NPC66518
0.8088	Intermediate Similarity	NPC476353
0.8058	Intermediate Similarity	NPC214869
0.8031	Intermediate Similarity	NPC222084
0.8029	Intermediate Similarity	NPC251571
0.7985	Intermediate Similarity	NPC472271
0.7973	Intermediate Similarity	NPC153644
0.7939	Intermediate Similarity	NPC277394
0.7939	Intermediate Similarity	NPC61062
0.7939	Intermediate Similarity	NPC299252
0.7939	Intermediate Similarity	NPC106551
0.7939	Intermediate Similarity	NPC281686
0.7939	Intermediate Similarity	NPC188867
0.7914	Intermediate Similarity	NPC52029
0.7914	Intermediate Similarity	NPC195749
0.7914	Intermediate Similarity	NPC35961
0.7899	Intermediate Similarity	NPC477839
0.7887	Intermediate Similarity	NPC6570
0.7879	Intermediate Similarity	NPC38458
0.7879	Intermediate Similarity	NPC311737
0.7874	Intermediate Similarity	NPC24101
0.7874	Intermediate Similarity	NPC96224
0.7857	Intermediate Similarity	NPC114102
0.7846	Intermediate Similarity	NPC148969
0.7842	Intermediate Similarity	NPC155838
0.781	Intermediate Similarity	NPC85565
0.7808	Intermediate Similarity	NPC106183
0.7803	Intermediate Similarity	NPC82963
0.7801	Intermediate Similarity	NPC470392
0.7778	Intermediate Similarity	NPC41473
0.7778	Intermediate Similarity	NPC312770
0.7778	Intermediate Similarity	NPC160607
0.7778	Intermediate Similarity	NPC204848
0.7778	Intermediate Similarity	NPC14600
0.777	Intermediate Similarity	NPC153990
0.7761	Intermediate Similarity	NPC239697
0.7727	Intermediate Similarity	NPC4665
0.7724	Intermediate Similarity	NPC299583
0.7714	Intermediate Similarity	NPC271808
0.7704	Intermediate Similarity	NPC34634
0.7704	Intermediate Similarity	NPC265454
0.7698	Intermediate Similarity	NPC301713
0.7692	Intermediate Similarity	NPC163674
0.7681	Intermediate Similarity	NPC288945
0.7655	Intermediate Similarity	NPC471283
0.7647	Intermediate Similarity	NPC98305
0.7643	Intermediate Similarity	NPC186898
0.7634	Intermediate Similarity	NPC146422
0.7612	Intermediate Similarity	NPC200988
0.7612	Intermediate Similarity	NPC610
0.7612	Intermediate Similarity	NPC145023
0.7612	Intermediate Similarity	NPC175799
0.7597	Intermediate Similarity	NPC56635
0.7597	Intermediate Similarity	NPC153690
0.7594	Intermediate Similarity	NPC317254
0.7584	Intermediate Similarity	NPC16188
0.7576	Intermediate Similarity	NPC309808
0.7574	Intermediate Similarity	NPC252817
0.7557	Intermediate Similarity	NPC297657
0.7556	Intermediate Similarity	NPC317784
0.7556	Intermediate Similarity	NPC63126
0.7556	Intermediate Similarity	NPC142638
0.7556	Intermediate Similarity	NPC86198
0.7554	Intermediate Similarity	NPC471927
0.7554	Intermediate Similarity	NPC4974
0.7552	Intermediate Similarity	NPC328070
0.7536	Intermediate Similarity	NPC86900
0.7535	Intermediate Similarity	NPC241354
0.7534	Intermediate Similarity	NPC48202
0.7534	Intermediate Similarity	NPC471201
0.7519	Intermediate Similarity	NPC142297
0.7519	Intermediate Similarity	NPC118202
0.7518	Intermediate Similarity	NPC56634
0.7518	Intermediate Similarity	NPC326079
0.7518	Intermediate Similarity	NPC236520
0.7518	Intermediate Similarity	NPC294361
0.7516	Intermediate Similarity	NPC478189
0.75	Intermediate Similarity	NPC109371
0.75	Intermediate Similarity	NPC51698
0.75	Intermediate Similarity	NPC470215
0.75	Intermediate Similarity	NPC263386
0.75	Intermediate Similarity	NPC470214
0.75	Intermediate Similarity	NPC70084
0.75	Intermediate Similarity	NPC234069
0.75	Intermediate Similarity	NPC141791
0.75	Intermediate Similarity	NPC32064
0.7483	Intermediate Similarity	NPC132771
0.7483	Intermediate Similarity	NPC296898
0.7483	Intermediate Similarity	NPC275538
0.7483	Intermediate Similarity	NPC257390
0.7481	Intermediate Similarity	NPC278652
0.7466	Intermediate Similarity	NPC473052
0.7466	Intermediate Similarity	NPC313694
0.7466	Intermediate Similarity	NPC473055
0.7466	Intermediate Similarity	NPC242159
0.7456	Intermediate Similarity	NPC174122
0.7456	Intermediate Similarity	NPC64140
0.7451	Intermediate Similarity	NPC182119
0.7442	Intermediate Similarity	NPC231705
0.7432	Intermediate Similarity	NPC33011
0.7432	Intermediate Similarity	NPC323123
0.7432	Intermediate Similarity	NPC91953
0.7431	Intermediate Similarity	NPC130595
0.7431	Intermediate Similarity	NPC93882
0.7431	Intermediate Similarity	NPC198388
0.7426	Intermediate Similarity	NPC85276
0.7422	Intermediate Similarity	NPC471511
0.7415	Intermediate Similarity	NPC322526
0.7405	Intermediate Similarity	NPC254833
0.7405	Intermediate Similarity	NPC228343
0.7405	Intermediate Similarity	NPC258056
0.7391	Intermediate Similarity	NPC470849
0.7391	Intermediate Similarity	NPC470848
0.7379	Intermediate Similarity	NPC5419
0.7379	Intermediate Similarity	NPC61
0.7379	Intermediate Similarity	NPC25581
0.7379	Intermediate Similarity	NPC285078
0.7379	Intermediate Similarity	NPC18074
0.7379	Intermediate Similarity	NPC313737
0.7379	Intermediate Similarity	NPC6854
0.7376	Intermediate Similarity	NPC280767
0.7376	Intermediate Similarity	NPC257589
0.7376	Intermediate Similarity	NPC318965
0.7376	Intermediate Similarity	NPC53305
0.7372	Intermediate Similarity	NPC283760
0.7365	Intermediate Similarity	NPC219233
0.7365	Intermediate Similarity	NPC211468
0.7365	Intermediate Similarity	NPC170170
0.7365	Intermediate Similarity	NPC197921
0.7351	Intermediate Similarity	NPC125852
0.7348	Intermediate Similarity	NPC226401
0.7348	Intermediate Similarity	NPC474149
0.7348	Intermediate Similarity	NPC79793
0.7348	Intermediate Similarity	NPC120982
0.7348	Intermediate Similarity	NPC147634
0.7348	Intermediate Similarity	NPC174096
0.7346	Intermediate Similarity	NPC89831
0.7344	Intermediate Similarity	NPC178902
0.7338	Intermediate Similarity	NPC202198
0.7338	Intermediate Similarity	NPC194416
0.7338	Intermediate Similarity	NPC147654
0.7338	Intermediate Similarity	NPC322332
0.7338	Intermediate Similarity	NPC177291
0.7329	Intermediate Similarity	NPC155209
0.7329	Intermediate Similarity	NPC168799
0.7329	Intermediate Similarity	NPC218530
0.7329	Intermediate Similarity	NPC471749
0.7324	Intermediate Similarity	NPC210950
0.7324	Intermediate Similarity	NPC84076
0.7324	Intermediate Similarity	NPC303680
0.7324	Intermediate Similarity	NPC199738
0.7324	Intermediate Similarity	NPC127937
0.7324	Intermediate Similarity	NPC92207
0.7324	Intermediate Similarity	NPC90128
0.7323	Intermediate Similarity	NPC223393
0.7321	Intermediate Similarity	NPC138083
0.732	Intermediate Similarity	NPC115144
0.732	Intermediate Similarity	NPC277857
0.7319	Intermediate Similarity	NPC115627
0.7319	Intermediate Similarity	NPC169207
0.7319	Intermediate Similarity	NPC118522
0.7315	Intermediate Similarity	NPC477837
0.7315	Intermediate Similarity	NPC469360
0.7315	Intermediate Similarity	NPC477838
0.731	Intermediate Similarity	NPC318799
0.7308	Intermediate Similarity	NPC188677
0.7308	Intermediate Similarity	NPC294902
0.7308	Intermediate Similarity	NPC1786
0.7308	Intermediate Similarity	NPC70843
0.7308	Intermediate Similarity	NPC1075
0.7303	Intermediate Similarity	NPC5462
0.7299	Intermediate Similarity	NPC275519
0.7293	Intermediate Similarity	NPC227553
0.7293	Intermediate Similarity	NPC187583
0.7293	Intermediate Similarity	NPC179002
0.7293	Intermediate Similarity	NPC257430
0.7292	Intermediate Similarity	NPC470706
0.7287	Intermediate Similarity	NPC261573
0.7287	Intermediate Similarity	NPC8931
0.7287	Intermediate Similarity	NPC120693

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 NPC6913 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	547
0.2-0.3	972
0.3-0.4	2058
0.4-0.5	2763
0.5-0.6	2028
0.6-0.7	557
0.7-0.8	67
0.8-0.85	6
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8855	High Similarity	NPD9569	Approved
0.8593	High Similarity	NPD259	Phase 1
0.8582	High Similarity	NPD9537	Phase 1
0.8582	High Similarity	NPD9536	Phase 1
0.8496	Intermediate Similarity	NPD258	Approved
0.8496	Intermediate Similarity	NPD257	Approved
0.8467	Intermediate Similarity	NPD555	Phase 2
0.8261	Intermediate Similarity	NPD826	Approved
0.8261	Intermediate Similarity	NPD825	Approved
0.8227	Intermediate Similarity	NPD9570	Approved
0.8176	Intermediate Similarity	NPD3455	Phase 2
0.8071	Intermediate Similarity	NPD275	Approved
0.8071	Intermediate Similarity	NPD274	Approved
0.7939	Intermediate Similarity	NPD9568	Approved
0.7914	Intermediate Similarity	NPD3136	Phase 2
0.7883	Intermediate Similarity	NPD3053	Approved
0.7883	Intermediate Similarity	NPD3055	Approved
0.782	Intermediate Similarity	NPD1759	Phase 1
0.7794	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6867	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6866	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD3400	Discontinued
0.7744	Intermediate Similarity	NPD1758	Phase 1
0.7724	Intermediate Similarity	NPD7450	Phase 2
0.7681	Intermediate Similarity	NPD5310	Approved
0.7681	Intermediate Similarity	NPD5311	Approved
0.7676	Intermediate Similarity	NPD5729	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD9379	Approved
0.7634	Intermediate Similarity	NPD9377	Approved
0.7594	Intermediate Similarity	NPD255	Approved
0.7594	Intermediate Similarity	NPD256	Approved
0.75	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3059	Approved
0.75	Intermediate Similarity	NPD3062	Approved
0.75	Intermediate Similarity	NPD6346	Approved
0.75	Intermediate Similarity	NPD3061	Approved
0.7483	Intermediate Similarity	NPD6682	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD9622	Approved
0.7436	Intermediate Similarity	NPD7495	Discontinued
0.7436	Intermediate Similarity	NPD8019	Approved
0.7431	Intermediate Similarity	NPD2674	Phase 3
0.7405	Intermediate Similarity	NPD3021	Approved
0.7405	Intermediate Similarity	NPD3022	Approved
0.7397	Intermediate Similarity	NPD5314	Approved
0.7361	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5137	Approved
0.7338	Intermediate Similarity	NPD7523	Phase 3
0.7324	Intermediate Similarity	NPD7451	Discontinued
0.7319	Intermediate Similarity	NPD9384	Approved
0.7319	Intermediate Similarity	NPD9381	Approved
0.7315	Intermediate Similarity	NPD7978	Discontinued
0.731	Intermediate Similarity	NPD1130	Approved
0.731	Intermediate Similarity	NPD1132	Approved
0.731	Intermediate Similarity	NPD1136	Approved
0.7279	Intermediate Similarity	NPD817	Approved
0.7279	Intermediate Similarity	NPD823	Approved
0.7248	Intermediate Similarity	NPD1519	Approved
0.7248	Intermediate Similarity	NPD1537	Approved
0.7248	Intermediate Similarity	NPD1538	Phase 1
0.7241	Intermediate Similarity	NPD601	Approved
0.7241	Intermediate Similarity	NPD598	Approved
0.7241	Intermediate Similarity	NPD597	Approved
0.7241	Intermediate Similarity	NPD3144	Approved
0.7241	Intermediate Similarity	NPD3145	Approved
0.7218	Intermediate Similarity	NPD3644	Approved
0.7218	Intermediate Similarity	NPD3642	Approved
0.7218	Intermediate Similarity	NPD3643	Approved
0.7183	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD196	Phase 1
0.7163	Intermediate Similarity	NPD5108	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1523	Approved
0.7133	Intermediate Similarity	NPD1522	Approved
0.7117	Intermediate Similarity	NPD2821	Approved
0.7114	Intermediate Similarity	NPD1536	Approved
0.7103	Intermediate Similarity	NPD2614	Approved
0.7097	Intermediate Similarity	NPD4739	Approved
0.709	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD9620	Approved
0.7083	Intermediate Similarity	NPD9619	Approved
0.7083	Intermediate Similarity	NPD9621	Approved
0.7078	Intermediate Similarity	NPD3845	Phase 1
0.7078	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2234	Approved
0.7059	Intermediate Similarity	NPD2229	Approved
0.7059	Intermediate Similarity	NPD2228	Approved
0.7055	Intermediate Similarity	NPD6746	Phase 2
0.7051	Intermediate Similarity	NPD6390	Discontinued
0.7032	Intermediate Similarity	NPD2420	Approved
0.7032	Intermediate Similarity	NPD2421	Approved
0.7007	Intermediate Similarity	NPD9614	Approved
0.7007	Intermediate Similarity	NPD9618	Approved
0.7006	Intermediate Similarity	NPD7131	Phase 3
0.7	Intermediate Similarity	NPD1520	Approved
0.7	Intermediate Similarity	NPD1521	Approved
0.7	Intermediate Similarity	NPD4093	Discontinued
0.6993	Remote Similarity	NPD1755	Approved
0.6993	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6297	Approved
0.6981	Remote Similarity	NPD6502	Phase 2
0.6974	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2978	Approved
0.6957	Remote Similarity	NPD2977	Approved
0.6957	Remote Similarity	NPD7972	Discontinued
0.6939	Remote Similarity	NPD9718	Approved
0.6937	Remote Similarity	NPD6386	Approved
0.6937	Remote Similarity	NPD6385	Approved
0.6933	Remote Similarity	NPD2568	Approved
0.6929	Remote Similarity	NPD5303	Approved
0.6929	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD5304	Approved
0.6923	Remote Similarity	NPD2562	Approved
0.6923	Remote Similarity	NPD6624	Discontinued
0.6923	Remote Similarity	NPD2561	Approved
0.6918	Remote Similarity	NPD4005	Discontinued
0.6908	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5241	Discontinued
0.6901	Remote Similarity	NPD3421	Phase 3
0.6894	Remote Similarity	NPD9608	Approved
0.6894	Remote Similarity	NPD9610	Approved
0.6889	Remote Similarity	NPD1792	Phase 2
0.6883	Remote Similarity	NPD3060	Approved
0.6879	Remote Similarity	NPD4123	Phase 3
0.6879	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4659	Approved
0.6875	Remote Similarity	NPD1669	Approved
0.6867	Remote Similarity	NPD7608	Discontinued
0.6867	Remote Similarity	NPD7315	Approved
0.6849	Remote Similarity	NPD2194	Approved
0.6849	Remote Similarity	NPD2195	Approved
0.6839	Remote Similarity	NPD6331	Phase 2
0.6839	Remote Similarity	NPD8166	Discontinued
0.6839	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6851	Approved
0.6821	Remote Similarity	NPD6853	Approved
0.6821	Remote Similarity	NPD2653	Approved
0.6818	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2217	Approved
0.6809	Remote Similarity	NPD2218	Phase 2
0.6806	Remote Similarity	NPD9269	Phase 2
0.6805	Remote Similarity	NPD3909	Discontinued
0.68	Remote Similarity	NPD943	Approved
0.6797	Remote Similarity	NPD2934	Approved
0.6797	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2933	Approved
0.6795	Remote Similarity	NPD6190	Approved
0.6795	Remote Similarity	NPD302	Approved
0.6791	Remote Similarity	NPD1444	Approved
0.6791	Remote Similarity	NPD1445	Approved
0.679	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5445	Approved
0.6783	Remote Similarity	NPD3847	Discontinued
0.6781	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD4103	Phase 2
0.6779	Remote Similarity	NPD4621	Approved
0.6779	Remote Similarity	NPD4619	Approved
0.6772	Remote Similarity	NPD3536	Discontinued
0.6763	Remote Similarity	NPD7280	Phase 3
0.6763	Remote Similarity	NPD7281	Phase 3
0.6761	Remote Similarity	NPD4105	Approved
0.6761	Remote Similarity	NPD4102	Approved
0.6757	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7554	Discontinued
0.675	Remote Similarity	NPD3687	Approved
0.675	Remote Similarity	NPD3686	Approved
0.6748	Remote Similarity	NPD5773	Approved
0.6748	Remote Similarity	NPD5772	Approved
0.6744	Remote Similarity	NPD2860	Approved
0.6744	Remote Similarity	NPD7038	Approved
0.6744	Remote Similarity	NPD2859	Approved
0.6744	Remote Similarity	NPD7039	Approved
0.6731	Remote Similarity	NPD4110	Phase 3
0.6731	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7526	Approved
0.673	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7303	Discontinued
0.673	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.673	Remote Similarity	NPD52	Approved
0.6728	Remote Similarity	NPD6873	Phase 2
0.6727	Remote Similarity	NPD2098	Approved
0.6725	Remote Similarity	NPD5557	Phase 1
0.6718	Remote Similarity	NPD3020	Approved
0.6716	Remote Similarity	NPD1040	Phase 2
0.6713	Remote Similarity	NPD3019	Approved
0.6713	Remote Similarity	NPD2932	Approved
0.6711	Remote Similarity	NPD5156	Approved
0.6711	Remote Similarity	NPD5155	Approved
0.6711	Remote Similarity	NPD4738	Phase 2
0.6711	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7153	Discontinued
0.6708	Remote Similarity	NPD3111	Phase 1
0.6689	Remote Similarity	NPD3636	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