NPASS Compound

Natural Product: NPC94248

Natural Product ID	NPC94248
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Zeranol
IUPAC Name	(7R,11S)-7,15,17-trihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),15,17-trien-13-one
Synonyms	MK-188; P-1496; Ralabol; Ralgro; THFES (HM); Zeranol
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL450613
PubChem CID	2999413
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 49 50 0 0 0 0 0 0 0 0999 V2000 0.6503 3.9319 0.4034 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7043 2.6949 -0.5449 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0241 2.0026 -0.3746 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1163 0.8669 -1.3600 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3276 0.0095 -1.1553 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4808 -0.5414 0.2182 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3136 -1.2551 0.8047 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7779 -2.3725 0.0006 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6140 -3.0953 0.5719 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5871 -2.2824 0.9128 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1149 -1.4777 -0.2444 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3574 -0.7266 0.0392 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4643 -1.3871 0.5635 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6513 -0.7678 0.8145 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7798 0.5718 0.5430 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6965 1.2189 0.0302 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4545 0.5911 -0.2355 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4344 1.4720 -0.7679 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6451 1.9257 -1.9106 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3155 1.8088 -0.0837 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7156 2.5836 -0.2875 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7185 -1.4878 1.3399 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5435 -1.4761 0.1640 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3721 4.3526 0.3615 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4135 4.6671 0.1037 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8319 3.6131 1.4412 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5638 3.0726 -1.5471 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8532 2.7542 -0.5648 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1688 1.6683 0.6764 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1968 0.3722 -1.6223 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3722 1.4303 -2.3445 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2204 0.6368 -1.3592 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3151 -0.7792 -1.9352 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8533 0.2563 0.9035 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5120 -0.5625 1.1506 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7065 -1.6846 1.7812 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5277 -1.9958 -1.0329 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5878 -3.1147 -0.1590 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9119 -3.6596 1.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2975 -3.8698 -0.1685 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3989 -3.0042 1.1857 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3814 -1.6957 1.8035 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2881 -2.0925 -1.1464 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3321 -0.7426 -0.4829 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3354 -2.4418 0.7676 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7205 1.0913 0.7346 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7542 2.8169 -1.2676 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7317 -1.7183 2.3171 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3645 -2.1782 -0.5178 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 16 21 1 0 14 22 1 0 6 23 1 0 20 2 1 0 17 12 1 0 1 24 1 0 1 25 1 0 1 26 1 0 2 27 1 6 3 28 1 0 3 29 1 0 4 30 1 0 4 31 1 0 5 32 1 0 5 33 1 0 6 34 1 1 7 35 1 0 7 36 1 0 8 37 1 0 8 38 1 0 9 39 1 0 9 40 1 0 10 41 1 0 10 42 1 0 11 43 1 0 11 44 1 0 13 45 1 0 15 46 1 0 21 47 1 0 22 48 1 0 23 49 1 0 M END

Standard InCHIKey	DWTTZBARDOXEAM-GXTWGEPZSA-N
Standard InCHI	InChI=1S/C18H26O5/c1-12-6-5-9-14(19)8-4-2-3-7-13-10-15(20)11-16(21)17(13)18(22)23-12/h10-12,14,19-21H,2-9H2,1H3/t12-,14+/m0/s1
SMILES	C[C@H]1CCC[C@@H](CCCCCc2cc(cc(c2C(=O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO27821.1	Pochonia chlamydosporia	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12828470]
NPO22748	Neophaeosphaeria quadriseptata	Species	Leptosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499313]
NPO40515	Chaetomium chiversii	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499313]
NPO22748	Neophaeosphaeria quadriseptata	Species	Leptosphaeriaceae	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	Organism Name	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
Potency	88
EC50	5
IC50	8
RBA	2
Efficacy	4
ED50	1

Activity Type	# Activity
Individual protein	47
Cell line	5
Organism	5
Protein family	2
Others	49

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	7562.4	nM	PMID[20934342]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	11883.2	nM	PMID[10924160]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	6968.3	nM	PMID[21134751]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	30856.1	nM	PMID[19654408]
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	43585.4	nM	PMID[12662097]
NPT162	Individual protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	62105.2	nM	PubChem BioAssay data set
NPT248	Individual protein	Estrogen receptor beta	Homo sapiens	EC50	=	24.0	nM	DOI[10.6019/CHEMBL1201861]
NPT109	Individual protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	3981.1	nM	DrugMatrix in vivo data: Pathology
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	141.3	nM	PMID[22055204]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[10775404]
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[17411092]
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[14695808]
NPT154	Individual protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	35481.3	nM	PMID[19721074]
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	9200.0	nM	PMID[25305333]
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	66824.2	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[22703109]
NPT103	Individual protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	42163.2	nM	PMID[20194693]
NPT101	Individual protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[12193011]
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	59557.2	nM	Open TG-GATES in vivo data: Biochemistry
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	RBA	=	9.0	%	PMID[24708493]
NPT248	Individual protein	Estrogen receptor beta	Homo sapiens	RBA	=	12.0	%	PMID[24708493]
NPT158	Individual protein	Nuclear receptor subfamily 1 group I member 2	Rattus norvegicus	EC50	=	38400.0	nM	PMID[18154272]
NPT158	Individual protein	Nuclear receptor subfamily 1 group I member 2	Rattus norvegicus	Efficacy	=	46.8	%	PMID[20966043]
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	3548.1	nM	PMID[12027764]
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	79.4	nM	PMID[19581457]
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	35481.3	nM	PMID[20934335]
NPT540	Individual protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[16499313]
NPT540	Individual protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[18077425]
NPT94	Individual protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[20795741]
NPT54	Individual protein	Nonstructural protein 1	Influenza A virus	Potency	=	7943.3	nM	PMID[23046382]
NPT7	Individual protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	100.0	nM	PMID[15916422]
NPT93	Individual protein	Survival motor neuron protein	Homo sapiens	Potency	=	35481.3	nM	PMID[25856683]
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	891.3	nM	PMID[18434163]
NPT59	Individual protein	DNA polymerase beta	Homo sapiens	Potency	=	79432.8	nM	PMID[24689881]
NPT445	Individual protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	16136.6	nM	PMID[16933872]
NPT535	Individual protein	Parathyroid hormone receptor	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[12617583]
NPT2264	Protein family	Heat shock protein HSP90	Homo sapiens	IC50	=	2646.2	nM	PMID[21051535]
NPT2264	Protein family	Heat shock protein HSP90	Homo sapiens	IC50	=	27927.1	nM	PMID[17850214]
NPT539	Individual protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	31622.8	nM	PMID[26502160]
NPT64	Individual protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	18356.4	nM	DOI[10.6019/CHEMBL1201861]
NPT64	Individual protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	7307.8	nM	PMID[21376582]
NPT543	Individual protein	Pregnane X receptor	Homo sapiens	Efficacy	=	73.7	%	PMID[20966043]
NPT543	Individual protein	Pregnane X receptor	Homo sapiens	Efficacy	=	52.1	%	PMID[20966043]
NPT543	Individual protein	Pregnane X receptor	Homo sapiens	Efficacy	=	51.5	%	PMID[20966043]
NPT543	Individual protein	Pregnane X receptor	Homo sapiens	EC50	=	23700.0	nM	PMID[18332176]
NPT543	Individual protein	Pregnane X receptor	Homo sapiens	EC50	=	25100.0	nM	PubChem BioAssay data set
NPT543	Individual protein	Pregnane X receptor	Homo sapiens	EC50	=	4000.0	nM	PMID[18993063]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[19105653]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[19105653]
NPT395	Cell line	SF-268	Homo sapiens	IC50	>	50000.0	nM	DrugMatrix in vivo data: Hematology
NPT65	Cell line	HepG2	Homo sapiens	Potency	n.a.	12589.3	nM	PMID[25920564]
NPT189	Cell line	Vero	Chlorocebus aethiops	IC50	=	50000.0	nM	PMID[24025124]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11995.5	nM	PMID[25136754]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	19011.5	nM	PMID[17417631]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	DOI[10.6019/CHEMBL4651402]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	DOI[10.6019/CHEMBL4651402]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	69078.2	nM	PMID[12027772]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	61566	nM	PMID[24582402]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	848.5	nM	Open TG-GATES in vivo data: Hematology
NPT2	Others	Unspecified	n.a.	Potency	n.a.	175	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	6907.8	nM	PMID[24411199]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	54870.7	nM	PMID[15214779]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	9439.2	nM	PMID[19029333]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	23710.1	nM	PMID[17698618]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	54870.7	nM	PMID[17190444]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	62105.2	nM	PMID[17665951]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	29849.3	nM	PMID[25946116]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	54870.7	nM	PMID[19456120]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	24724.5	nM	PMID[18391041]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	35018.2	nM	PMID[19674905]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	69078.2	nM	PMID[19854051]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	154.6	nM	PMID[18077425]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	43967.1	nM	PMID[21816519]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	18833.6	nM	DOI[10.6019/CHEMBL1201861]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	69078.2	nM	PMID[20022253]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	21313.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	39185.7	nM	PMID[21733601]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	55351.3	nM	DOI[10.6019/CHEMBL1201861]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	26603.2	nM	PMID[25443644]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	27500.5	nM	PMID[11421735]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	16785.5	nM	PMID[18809939]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	54870.7	nM	PMID[23837878]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	43585.4	nM	PMID[9873511]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	69078.2	nM	PMID[9873632]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	43967.1	nM	PMID[23571415]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	47307.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	61566	nM	PMID[19583252]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	18833.6	nM	DrugMatrix in vitro pharmacology data
NPT2	Others	Unspecified	n.a.	Potency	n.a.	61566	nM	PMID[17958396]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	62105.2	nM	PMID[7506311]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	23710.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	43585.4	nM	PMID[15217273]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	26603.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	30856.1	nM	PMID[23398362]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	26603.2	nM	PMID[12213077]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	6968.3	nM	PMID[10579870]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	30856.1	nM	PMID[8326318]
NPT2	Others	Unspecified	n.a.	Potency	=	2592.9	nM	PMID[17696332]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	12589.3	nM	PMID[11754603]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	8912.5	nM	PMID[22652254]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	37578.0	nM	DOI[10.6019/CHEMBL1201861]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	33491.5	nM	Open TG-GATES in vivo data: Biochemistry
NPT2	Others	Unspecified	n.a.	Potency	n.a.	29092.9	nM	PMID[18597527]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	11220.2	nM	PMID[22472691]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED50	=	0.2	mg.kg-1	PMID[11170659]

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference
-	Rattus norvegicus	LEL	=	0.03	mg/day	ToxVal

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC94248 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	10506
0.1-0.2	36138
0.2-0.3	2948
0.3-0.4	205
0.4-0.5	38
0.5-0.6	17
0.6-0.7	1
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC212693
0.8039	Intermediate Similarity	NPC70380
0.7321	Intermediate Similarity	NPC191835
0.7091	Intermediate Similarity	NPC105456
0.7091	Intermediate Similarity	NPC139634
0.6842	Remote Similarity	NPC608268
0.5873	Remote Similarity	NPC261729
0.5873	Remote Similarity	NPC485855
0.5645	Remote Similarity	NPC609527
0.5645	Remote Similarity	NPC610163
0.5645	Remote Similarity	NPC611086
0.5625	Remote Similarity	NPC51106
0.5469	Remote Similarity	NPC472035
0.5469	Remote Similarity	NPC609495
0.5345	Remote Similarity	NPC609111
0.5323	Remote Similarity	NPC1704
0.5323	Remote Similarity	NPC67650
0.5238	Remote Similarity	NPC53649
0.5185	Remote Similarity	NPC219892
0.5185	Remote Similarity	NPC235115
0.5077	Remote Similarity	NPC764
0.5077	Remote Similarity	NPC475974
0.5077	Remote Similarity	NPC487444

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC94248 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4066
0.1-0.2	5009
0.2-0.3	74
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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