NPASS Compound

Structure

CID13575 OpenBabel06191715342D 26 27 0 0 0 0 0 0 0 0999 V2000 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 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 0.5000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 -5.1962 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 -2.5981 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 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 -6.9282 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 2.0000 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 26 1 0 0 0 0 4 10 1 0 0 0 0 4 13 2 0 0 0 0 5 8 1 0 0 0 0 5 14 2 0 0 0 0 6 9 2 0 0 0 0 6 14 1 0 0 0 0 7 11 1 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 19 1 0 0 0 0 15 22 1 0 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 20 1 0 0 0 0 17 23 2 0 0 0 0 18 24 1 0 0 0 0 19 20 2 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.16
Volume:	377.519
LogP:	4.571
LogD:	3.49
LogS:	-3.792
# Rotatable Bonds:	7
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.513
Synthetic Accessibility Score:	2.527
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.785
MDCK Permeability:	1.596885522303637e-05
Pgp-inhibitor:	0.457
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.965
30% Bioavailability (F30%):	0.89

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	98.62600708007812%
Volume Distribution (VD):	0.649
Pgp-substrate:	1.2495046854019165%

ADMET: Metabolism

CYP1A2-inhibitor:	0.934
CYP1A2-substrate:	0.805
CYP2C19-inhibitor:	0.938
CYP2C19-substrate:	0.086
CYP2C9-inhibitor:	0.893
CYP2C9-substrate:	0.944
CYP2D6-inhibitor:	0.928
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.566
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	15.373
Half-life (T1/2):	0.782

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.369
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.406
Maximum Recommended Daily Dose:	0.122
Skin Sensitization:	0.926
Carcinogencity:	0.095
Eye Corrosion:	0.003
Eye Irritation:	0.597
Respiratory Toxicity:	0.202

Download Data

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

Natural Product: NPC13575

Natural Product ID:	NPC13575
*Common Name:**	Dihydroxanthohumol
IUPAC Name:	1-[2,4-dihydroxy-6-methoxy-3-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)propan-1-one
Synonyms:	Dihydroxanthohumol
Standard InCHIKey:	SVTCZHIDEDUTBH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H24O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-6,8-9,12,22,24-25H,7,10-11H2,1-3H3
SMILES:	COc1cc(O)c(c(c1C(=O)CCc1ccc(cc1)O)O)CC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL510279
PubChem CID:	10450920
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003473] 2'-Hydroxy-dihydrochalcones

*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
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/ejlt.201100207]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1007/s11746-010-1670-2]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.foodcont.2016.09.002]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.jfca.2010.08.006]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2010.06.003]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2010.12.007]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2016.02.010]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.12691/jfnr-2-5-9]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.5219/332]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[10336650]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15217296]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679315]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252923]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499319]
NPO13478	Scorzonera pseudodivaricata	Species	Asteraceae	Eukaryota	n.a.	Mongolian	n.a.	PMID[17542634]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[17624889]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	sand-covered bottom at -10 to -15 m at Hurghada, on the Egyptian Red Sea coast	2003-JUN	PMID[18298079]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18611049]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18768384]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18942825]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19476340]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[19628108]
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20405844]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21912858]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[22111577]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	flower	n.a.	PMID[22166201]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[22538527]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23790907]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[24811150]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24948953]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25564559]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[28274428]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29154541]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30236698]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	Guangzhou, China		PMID[30563201]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30583361]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30599958]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[31159190]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[31861466]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24390.1	Juniperus rigida var. conferta	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1834	Atalantia racemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10783	Syncarpia hillii	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14578	Prorocentrum micans	Species	Prorocentraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13585	Rapanea lancifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13030	Artemisia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5930	Crambe tatarica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21830	Buddleja cordata	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12196	Buphane fischeri	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12855	Alkanna cappadocica	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1834	Atalantia racemosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12700	Diospyros eriantha	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6360	Xenoacremonium recifei	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11848	Lemaireocereus griseus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3492	Negombata magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13671	Ononis vaginalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24390.1	Juniperus rigida var. conferta	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9313	Fritillaria ningguoensis	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13478	Scorzonera pseudodivaricata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8928	Pteris semipinnata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO252	Hoffmannia strigillosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9934	Mycobacterium leprae	Species	Mycobacteriaceae	Bacteria	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
EC50	5
IC50	10
Others	1
Potency	23

Activity Type	# Activity
Cell Line	6
Individual Protein	21
NON-MOLECULAR	1
Organism	4
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	23000.0	nM	PMID[522267]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	>	95.0	%	PMID[522267]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	11220.2	nM	PMID[522268]
NPT1253	Individual Protein	Calpain 2	Sus scrofa	IC50	=	5000.36	nM	PMID[522268]
NPT54	Individual Protein	Nonstructural protein 1	Influenza A virus	Potency	=	4466.8	nM	PMID[522268]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	15848.9	nM	PMID[522268]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	44668.4	nM	PMID[522268]
NPT1254	Individual Protein	Streptokinase A	Streptococcus pyogenes serotype M1	EC50	=	2757.0	nM	PMID[522268]
NPT532	Individual Protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[522268]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	25929.0	nM	PMID[522268]
NPT1255	Individual Protein	Sentrin-specific protease 8	Homo sapiens	IC50	=	13300.0	nM	PMID[522268]
NPT1256	Individual Protein	Sentrin-specific protease 7	Homo sapiens	IC50	=	7820.0	nM	PMID[522268]
NPT1257	Individual Protein	Sentrin-specific protease 6	Homo sapiens	IC50	=	10000.0	nM	PMID[522268]
NPT65	Cell Line	HepG2	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[522268]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[522268]
NPT259	Individual Protein	Melanocortin receptor 4	Homo sapiens	EC50	>	89202.0	nM	PMID[522268]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	6513.1	nM	PMID[522268]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	3662.6	nM	PMID[522268]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[522268]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	2511.9	nM	PMID[522268]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	74410.0	nM	PMID[522269]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	14730.0	nM	PMID[522269]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	9150.0	nM	PMID[522269]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[522268]
NPT535	Individual Protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[522268]
NPT174	Organism	Streptococcus	Streptococcus	EC50	=	3046.0	nM	PMID[522268]
NPT1252	Organism	Streptococcus sp. 'group A'	Streptococcus sp. 'group A'	EC50	=	2785.0	nM	PMID[522268]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Potency	=	12589.3	nM	PMID[522268]
NPT2	Others	Unspecified		Potency	=	20596.2	nM	PMID[522268]
NPT2	Others	Unspecified		Potency	n.a.	16360.1	nM	PMID[522268]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	9285.0	nM	PMID[522268]
NPT979	Individual Protein	Caspase-3	Homo sapiens	IC50	>	100000.0	nM	PMID[522268]
NPT1258	Others	Opioid receptors; mu & delta	Homo sapiens	EC50	>	64584.0	nM	PMID[522268]
NPT2	Others	Unspecified		Potency	n.a.	7943.3	nM	PMID[522268]
NPT2	Others	Unspecified		Potency	n.a.	707.9	nM	PMID[522268]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12970.0	nM	PMID[522269]
NPT2	Others	Unspecified		Potency	n.a.	19952.6	nM	PMID[522268]
NPT2	Others	Unspecified		Potency	n.a.	17782.8	nM	PMID[522268]

☑ 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 NPC13575 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	339
0.1-0.2	1537
0.2-0.3	3953
0.3-0.4	10809
0.4-0.5	7499
0.5-0.6	3703
0.6-0.7	5919
0.7-0.8	5529
0.8-0.85	1874
0.85-0.9	958
0.9-0.95	462
0.95-1	115

Similarity Score	Similarity Level	Natural Product ID
0.9923	High Similarity	NPC168105
0.9923	High Similarity	NPC186838
0.9923	High Similarity	NPC1486
0.9923	High Similarity	NPC274109
0.9923	High Similarity	NPC477242
0.9923	High Similarity	NPC150399
0.9923	High Similarity	NPC41461
0.9923	High Similarity	NPC66349
0.9923	High Similarity	NPC249606
0.9923	High Similarity	NPC12165
0.9923	High Similarity	NPC477244
0.9923	High Similarity	NPC25287
0.9923	High Similarity	NPC477243
0.9923	High Similarity	NPC98115
0.9922	High Similarity	NPC103842
0.9847	High Similarity	NPC472419
0.9847	High Similarity	NPC317119
0.9847	High Similarity	NPC153979
0.9846	High Similarity	NPC156092
0.9846	High Similarity	NPC131039
0.9845	High Similarity	NPC20560
0.9845	High Similarity	NPC18877
0.9845	High Similarity	NPC82225
0.9845	High Similarity	NPC144051
0.9845	High Similarity	NPC28753
0.9845	High Similarity	NPC294593
0.9845	High Similarity	NPC159623
0.9845	High Similarity	NPC204960
0.9773	High Similarity	NPC251681
0.9773	High Similarity	NPC243528
0.9773	High Similarity	NPC21350
0.9769	High Similarity	NPC286336
0.9699	High Similarity	NPC472366
0.9699	High Similarity	NPC470211
0.9699	High Similarity	NPC477956
0.9692	High Similarity	NPC192304
0.9692	High Similarity	NPC312318
0.9692	High Similarity	NPC263670
0.9692	High Similarity	NPC472365
0.9692	High Similarity	NPC175098
0.9692	High Similarity	NPC337373
0.9692	High Similarity	NPC188646
0.9692	High Similarity	NPC242294
0.9692	High Similarity	NPC56031
0.9692	High Similarity	NPC27643
0.9692	High Similarity	NPC139813
0.969	High Similarity	NPC186097
0.969	High Similarity	NPC475009
0.969	High Similarity	NPC475008
0.9627	High Similarity	NPC241100
0.9627	High Similarity	NPC213659
0.9627	High Similarity	NPC215311
0.9627	High Similarity	NPC11056
0.9627	High Similarity	NPC159275
0.9627	High Similarity	NPC144118
0.9627	High Similarity	NPC80962
0.9627	High Similarity	NPC172250
0.9627	High Similarity	NPC48624
0.9627	High Similarity	NPC326109
0.9627	High Similarity	NPC259166
0.9627	High Similarity	NPC219917
0.9627	High Similarity	NPC204985
0.9624	High Similarity	NPC471620
0.9615	High Similarity	NPC212631
0.9615	High Similarity	NPC15834
0.9615	High Similarity	NPC129132
0.9615	High Similarity	NPC257756
0.9615	High Similarity	NPC205468
0.9615	High Similarity	NPC87231
0.9615	High Similarity	NPC215875
0.9556	High Similarity	NPC26238
0.9556	High Similarity	NPC470087
0.9556	High Similarity	NPC282300
0.9556	High Similarity	NPC26051
0.9556	High Similarity	NPC321980
0.9556	High Similarity	NPC55832
0.9556	High Similarity	NPC110969
0.9556	High Similarity	NPC469404
0.9556	High Similarity	NPC470089
0.9556	High Similarity	NPC268204
0.9556	High Similarity	NPC52789
0.9552	High Similarity	NPC96565
0.9552	High Similarity	NPC220062
0.9552	High Similarity	NPC217186
0.9552	High Similarity	NPC216978
0.9552	High Similarity	NPC283429
0.9552	High Similarity	NPC55018
0.9552	High Similarity	NPC301217
0.9552	High Similarity	NPC303633
0.9552	High Similarity	NPC18260
0.9552	High Similarity	NPC53181
0.9552	High Similarity	NPC78913
0.9552	High Similarity	NPC295384
0.9542	High Similarity	NPC16197
0.9538	High Similarity	NPC64359
0.9538	High Similarity	NPC128348
0.9538	High Similarity	NPC112192
0.9538	High Similarity	NPC313618
0.9538	High Similarity	NPC189106
0.9538	High Similarity	NPC164236
0.9538	High Similarity	NPC308037
0.9538	High Similarity	NPC309717
0.9538	High Similarity	NPC262359
0.9538	High Similarity	NPC66384
0.9535	High Similarity	NPC84772
0.9485	High Similarity	NPC1089
0.9485	High Similarity	NPC125855
0.9485	High Similarity	NPC182852
0.9485	High Similarity	NPC107572
0.9485	High Similarity	NPC306829
0.9485	High Similarity	NPC11561
0.9485	High Similarity	NPC32739
0.9485	High Similarity	NPC76372
0.9485	High Similarity	NPC161506
0.9485	High Similarity	NPC226636
0.9485	High Similarity	NPC166482
0.9485	High Similarity	NPC37496
0.9485	High Similarity	NPC167624
0.9485	High Similarity	NPC220998
0.9485	High Similarity	NPC76338
0.9485	High Similarity	NPC296917
0.9485	High Similarity	NPC227579
0.9485	High Similarity	NPC78
0.9485	High Similarity	NPC324436
0.9485	High Similarity	NPC324134
0.9485	High Similarity	NPC194432
0.9485	High Similarity	NPC223500
0.9485	High Similarity	NPC328164
0.9485	High Similarity	NPC10937
0.9485	High Similarity	NPC265040
0.9485	High Similarity	NPC166934
0.9485	High Similarity	NPC228504
0.9485	High Similarity	NPC177354
0.9485	High Similarity	NPC297600
0.9485	High Similarity	NPC148757
0.9485	High Similarity	NPC66515
0.9485	High Similarity	NPC40833
0.9485	High Similarity	NPC64915
0.9481	High Similarity	NPC270883
0.9481	High Similarity	NPC261227
0.9481	High Similarity	NPC150522
0.9481	High Similarity	NPC101366
0.9481	High Similarity	NPC69769
0.9481	High Similarity	NPC253822
0.9481	High Similarity	NPC265178
0.9481	High Similarity	NPC172986
0.9478	High Similarity	NPC472368
0.9478	High Similarity	NPC201395
0.9478	High Similarity	NPC124269
0.9474	High Similarity	NPC24394
0.9474	High Similarity	NPC473391
0.9474	High Similarity	NPC472367
0.9474	High Similarity	NPC472364
0.9474	High Similarity	NPC476333
0.9474	High Similarity	NPC213603
0.9474	High Similarity	NPC174999
0.947	High Similarity	NPC164136
0.9462	High Similarity	NPC324482
0.9457	High Similarity	NPC230818
0.9416	High Similarity	NPC39329
0.9416	High Similarity	NPC125894
0.9416	High Similarity	NPC107177
0.9416	High Similarity	NPC310130
0.9416	High Similarity	NPC257097
0.9416	High Similarity	NPC68104
0.9416	High Similarity	NPC169591
0.9416	High Similarity	NPC278249
0.9416	High Similarity	NPC166138
0.9416	High Similarity	NPC221432
0.9416	High Similarity	NPC117836
0.9416	High Similarity	NPC150408
0.9416	High Similarity	NPC106985
0.9416	High Similarity	NPC81697
0.9416	High Similarity	NPC85162
0.9416	High Similarity	NPC51887
0.9416	High Similarity	NPC164980
0.9416	High Similarity	NPC475705
0.9416	High Similarity	NPC301751
0.9416	High Similarity	NPC476178
0.9416	High Similarity	NPC143896
0.9416	High Similarity	NPC75049
0.9416	High Similarity	NPC214166
0.9416	High Similarity	NPC77794
0.9416	High Similarity	NPC245482
0.9416	High Similarity	NPC149026
0.9416	High Similarity	NPC91560
0.9416	High Similarity	NPC316816
0.9416	High Similarity	NPC478086
0.9416	High Similarity	NPC185276
0.9416	High Similarity	NPC223812
0.9416	High Similarity	NPC18585
0.9416	High Similarity	NPC175504
0.9412	High Similarity	NPC324386
0.9412	High Similarity	NPC96408
0.9412	High Similarity	NPC279650
0.9412	High Similarity	NPC248372
0.9412	High Similarity	NPC40118
0.9412	High Similarity	NPC166689
0.9412	High Similarity	NPC156590
0.9412	High Similarity	NPC126534

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 NPC13575 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	967
0.2-0.3	1451
0.3-0.4	2593
0.4-0.5	1953
0.5-0.6	1235
0.6-0.7	457
0.7-0.8	138
0.8-0.85	35
0.85-0.9	11
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9538	High Similarity	NPD1240	Approved
0.9394	High Similarity	NPD1607	Approved
0.9348	High Similarity	NPD4378	Clinical (unspecified phase)
0.9254	High Similarity	NPD1510	Phase 2
0.9118	High Similarity	NPD1552	Clinical (unspecified phase)
0.9118	High Similarity	NPD1550	Clinical (unspecified phase)
0.9071	High Similarity	NPD7410	Clinical (unspecified phase)
0.9051	High Similarity	NPD1549	Phase 2
0.8889	High Similarity	NPD4380	Phase 2
0.8836	High Similarity	NPD2393	Clinical (unspecified phase)
0.8828	High Similarity	NPD7411	Suspended
0.8824	High Similarity	NPD6651	Approved
0.8776	High Similarity	NPD8443	Clinical (unspecified phase)
0.8768	High Similarity	NPD2796	Approved
0.8658	High Similarity	NPD7075	Discontinued
0.8633	High Similarity	NPD2935	Discontinued
0.8601	High Similarity	NPD6799	Approved
0.8581	High Similarity	NPD7096	Clinical (unspecified phase)
0.8581	High Similarity	NPD7819	Suspended
0.8514	High Similarity	NPD6801	Discontinued
0.8514	High Similarity	NPD1934	Approved
0.8511	High Similarity	NPD970	Clinical (unspecified phase)
0.8472	Intermediate Similarity	NPD1511	Approved
0.8456	Intermediate Similarity	NPD2801	Approved
0.8451	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD2800	Approved
0.8394	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD6599	Discontinued
0.8356	Intermediate Similarity	NPD1512	Approved
0.8344	Intermediate Similarity	NPD7768	Phase 2
0.8344	Intermediate Similarity	NPD3882	Suspended
0.8323	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD6232	Discontinued
0.8289	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD2533	Approved
0.8288	Intermediate Similarity	NPD2534	Approved
0.8288	Intermediate Similarity	NPD2532	Approved
0.8269	Intermediate Similarity	NPD7473	Discontinued
0.8264	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD3750	Approved
0.8247	Intermediate Similarity	NPD6959	Discontinued
0.8239	Intermediate Similarity	NPD1551	Phase 2
0.8194	Intermediate Similarity	NPD1243	Approved
0.8169	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD2799	Discontinued
0.8165	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD943	Approved
0.8089	Intermediate Similarity	NPD6166	Phase 2
0.8089	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD2654	Approved
0.8063	Intermediate Similarity	NPD5953	Discontinued
0.8056	Intermediate Similarity	NPD2344	Approved
0.8054	Intermediate Similarity	NPD920	Approved
0.8052	Intermediate Similarity	NPD3749	Approved
0.805	Intermediate Similarity	NPD7286	Phase 2
0.8039	Intermediate Similarity	NPD3817	Phase 2
0.8029	Intermediate Similarity	NPD1203	Approved
0.8027	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD7390	Discontinued
0.7971	Intermediate Similarity	NPD2798	Approved
0.7963	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD5494	Approved
0.7941	Intermediate Similarity	NPD3972	Approved
0.7933	Intermediate Similarity	NPD5403	Approved
0.7919	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3748	Approved
0.7888	Intermediate Similarity	NPD7074	Phase 3
0.7875	Intermediate Similarity	NPD3818	Discontinued
0.7872	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD2313	Discontinued
0.7857	Intermediate Similarity	NPD6832	Phase 2
0.7838	Intermediate Similarity	NPD2309	Approved
0.7826	Intermediate Similarity	NPD7054	Approved
0.782	Intermediate Similarity	NPD9493	Approved
0.781	Intermediate Similarity	NPD9717	Approved
0.78	Intermediate Similarity	NPD5401	Approved
0.7791	Intermediate Similarity	NPD6559	Discontinued
0.7778	Intermediate Similarity	NPD7472	Approved
0.777	Intermediate Similarity	NPD4628	Phase 3
0.7756	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD3268	Approved
0.774	Intermediate Similarity	NPD6099	Approved
0.774	Intermediate Similarity	NPD6100	Approved
0.7737	Intermediate Similarity	NPD422	Phase 1
0.7737	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6797	Phase 2
0.773	Intermediate Similarity	NPD4908	Phase 1
0.7712	Intermediate Similarity	NPD3226	Approved
0.7704	Intermediate Similarity	NPD9545	Approved
0.7704	Intermediate Similarity	NPD1548	Phase 1
0.7697	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD7251	Discontinued
0.7671	Intermediate Similarity	NPD7033	Discontinued
0.7658	Intermediate Similarity	NPD919	Approved
0.7643	Intermediate Similarity	NPD1164	Approved
0.7643	Intermediate Similarity	NPD2797	Approved
0.7636	Intermediate Similarity	NPD7808	Phase 3
0.7625	Intermediate Similarity	NPD5710	Approved
0.7625	Intermediate Similarity	NPD5711	Approved
0.7609	Intermediate Similarity	NPD1201	Approved
0.7609	Intermediate Similarity	NPD1610	Phase 2
0.7607	Intermediate Similarity	NPD5844	Phase 1
0.7597	Intermediate Similarity	NPD7458	Discontinued
0.758	Intermediate Similarity	NPD5402	Approved
0.7578	Intermediate Similarity	NPD3926	Phase 2
0.7568	Intermediate Similarity	NPD2346	Discontinued
0.7562	Intermediate Similarity	NPD1247	Approved
0.7561	Intermediate Similarity	NPD1729	Discontinued
0.7533	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD7003	Approved
0.753	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD4360	Phase 2
0.75	Intermediate Similarity	NPD4363	Phase 3
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD5405	Approved
0.7466	Intermediate Similarity	NPD230	Phase 1
0.7466	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD5124	Phase 1
0.7457	Intermediate Similarity	NPD4361	Phase 2
0.7457	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3225	Approved
0.7447	Intermediate Similarity	NPD1876	Approved
0.7432	Intermediate Similarity	NPD4308	Phase 3
0.7432	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4625	Phase 3
0.7431	Intermediate Similarity	NPD3027	Phase 3
0.7429	Intermediate Similarity	NPD1608	Approved
0.7414	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3266	Approved
0.7394	Intermediate Similarity	NPD3267	Approved
0.7391	Intermediate Similarity	NPD1651	Approved
0.7386	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD3764	Approved
0.7379	Intermediate Similarity	NPD1296	Phase 2
0.7347	Intermediate Similarity	NPD1933	Approved
0.7347	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1241	Discontinued
0.7324	Intermediate Similarity	NPD1283	Approved
0.7305	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1465	Phase 2
0.7287	Intermediate Similarity	NPD940	Approved
0.7287	Intermediate Similarity	NPD846	Approved
0.7286	Intermediate Similarity	NPD3847	Discontinued
0.7283	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6104	Discontinued
0.726	Intermediate Similarity	NPD6798	Discontinued
0.726	Intermediate Similarity	NPD411	Approved
0.7254	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2296	Approved
0.725	Intermediate Similarity	NPD4288	Approved
0.7241	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD447	Suspended
0.7226	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1019	Discontinued
0.7219	Intermediate Similarity	NPD1471	Phase 3
0.7219	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD9266	Approved
0.7218	Intermediate Similarity	NPD74	Approved
0.7214	Intermediate Similarity	NPD4626	Approved
0.7214	Intermediate Similarity	NPD17	Approved
0.7195	Intermediate Similarity	NPD7229	Phase 3
0.7191	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1481	Phase 2
0.7179	Intermediate Similarity	NPD5049	Phase 3
0.7172	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD9494	Approved
0.717	Intermediate Similarity	NPD5889	Approved
0.717	Intermediate Similarity	NPD5890	Approved
0.7162	Intermediate Similarity	NPD4307	Phase 2
0.7162	Intermediate Similarity	NPD1613	Approved
0.7162	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4476	Approved
0.7152	Intermediate Similarity	NPD4477	Approved
0.7143	Intermediate Similarity	NPD9264	Approved
0.7143	Intermediate Similarity	NPD2354	Approved
0.7143	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9267	Approved
0.7143	Intermediate Similarity	NPD9263	Approved
0.7133	Intermediate Similarity	NPD4749	Approved
0.7126	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD37	Approved
0.7115	Intermediate Similarity	NPD4661	Approved
0.7115	Intermediate Similarity	NPD4662	Approved
0.7114	Intermediate Similarity	NPD6355	Discontinued
0.7113	Intermediate Similarity	NPD1281	Approved
0.7113	Intermediate Similarity	NPD1535	Discovery
0.7108	Intermediate Similarity	NPD2403	Approved
0.7107	Intermediate Similarity	NPD6585	Discontinued
0.7103	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1894	Discontinued
0.7069	Intermediate Similarity	NPD4287	Approved
0.7069	Intermediate Similarity	NPD8397	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