NPASS Compound

Natural Product: NPC235900

Natural Product ID	NPC235900
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Paxilline
IUPAC Name	n.a.
Synonyms	Paxilline
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL410063
PubChem CID	105008
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

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 65 70 0 0 0 0 0 0 0 0999 V2000 5.3187 -0.2067 1.5873 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3161 -0.0253 0.8726 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0078 -0.6358 1.1498 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9486 0.0809 0.8253 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2718 1.4068 0.2250 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1385 1.1142 -0.8545 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4182 0.8567 -0.3406 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2540 0.0780 -1.3466 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6044 -1.1190 -1.6005 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5762 -0.2393 -0.6832 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4723 0.8752 -2.6122 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0985 2.2158 -0.1752 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1780 1.8124 0.5233 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4615 0.3414 0.3066 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6091 -0.4471 1.0650 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3276 -0.1894 2.4306 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4735 -1.9188 0.8899 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8804 -2.3304 1.5109 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8794 -1.6075 0.7288 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7712 -0.0930 0.8078 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0988 0.3202 2.2159 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9483 0.2763 -0.0254 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4478 1.1767 -0.8734 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.6828 0.8137 -1.2323 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9739 -0.3645 -0.5840 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8833 -0.7026 0.1745 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3317 -1.7420 1.1258 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1972 -1.0083 -0.7487 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1542 -0.4664 -1.5789 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8642 0.7142 -2.2293 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6400 1.3502 -2.0589 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3823 0.1166 -1.1866 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0070 -1.6014 1.5911 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9332 1.9988 0.9282 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8766 1.8323 -0.0959 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0204 -1.8947 -1.1619 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5632 -1.1923 -0.1243 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8764 0.5718 0.0323 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4014 -0.3166 -1.4345 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5660 1.0655 -2.7717 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8856 1.8032 -2.6445 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1615 0.2287 -3.4624 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0336 2.2486 -1.2646 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2833 3.2859 0.1393 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0016 2.3818 0.0563 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0635 2.0976 1.5727 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0448 -0.6187 2.9427 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2097 -2.4731 1.4579 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5011 -2.2586 -0.1598 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8279 -2.1734 2.5814 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9816 -3.4143 1.3240 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8369 -1.9859 -0.3208 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9308 -0.5087 2.9617 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5551 1.1800 2.5952 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1831 0.5656 2.3311 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9643 2.0652 -1.2348 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7416 -2.7354 0.9213 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5583 -1.4247 2.1419 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4200 -1.9423 -0.2308 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1325 -0.9466 -1.7338 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6396 1.1231 -2.8817 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4981 2.2719 -2.6080 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6371 -0.2135 -1.5007 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1725 -0.5537 -1.5823 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5539 1.0806 -1.7531 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 8 11 1 0 5 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 25 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 14 32 1 6 7 2 1 0 20 14 1 0 26 22 2 0 15 4 1 0 27 19 1 0 31 24 1 0 3 33 1 0 5 34 1 1 7 35 1 1 9 36 1 0 10 37 1 0 10 38 1 0 10 39 1 0 11 40 1 0 11 41 1 0 11 42 1 0 12 43 1 0 12 44 1 0 13 45 1 0 13 46 1 0 16 47 1 0 17 48 1 0 17 49 1 0 18 50 1 0 18 51 1 0 19 52 1 6 21 53 1 0 21 54 1 0 21 55 1 0 23 56 1 0 27 57 1 0 27 58 1 0 28 59 1 0 29 60 1 0 30 61 1 0 31 62 1 0 32 63 1 0 32 64 1 0 32 65 1 0 M END

Standard InCHIKey	ACNHBCIZLNNLRS-UBGQALKQSA-N
Standard InCHI	InChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3/t15-,21-,23-,25+,26+,27+/m0/s1
SMILES	O=C1C=C2[C@@H](O[C@@H]1C(O)(C)C)CC[C@]1([C@@]2(O)CC[C@@H]2[C@]1(C)c1[nH]c3c(c1C2)cccc3)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	435.24	Volume:	454.548 ? Van der Waals volume.
Dense:	0.958	LogP:	2.573 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.78 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.148 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	30.0
TPSA:	82.55 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	6.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.633	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.737	Fsp³:	0.593
MCE-18:	136.953 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.163	Fluc inhibitor:	0.013 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.477 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.107 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.01	Promiscuous compounds:	0.668

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.969	MDCK Permeability:	-4.637
Pgp-inhibitor:	0.023	Pgp-substrate:	0.651
PAMPA:	0.941 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.049	30% Bioavailability (F30%):	0.151
50% Bioavailability (F50%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.949	MRP1:	0.527
Plasma Protein Binding (PPB):	93.308%	Volume Distribution (VD):	0.261
Fu:	5.829% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.959	BCRP inhibitor:	0.96
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.977	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.973	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.004	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.146	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.306
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.002
HLM stability:	0.077 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

9.488

Half-life (T1/2):

1.787

ADMET: Toxicity

hERG Blockers:	0.217	hERG Blockers (10um):	0.389
Human Hepatotoxicity (H-HT):	0.792	Drug-induced Liver Injury (DILI):	0.35
AMES Toxicity:	0.759	Rat Oral Acute Toxicity:	0.838
Maximum Recommended Daily Dose:	0.885	Skin Sensitization:	0.988
Carcinogencity:	0.829	Eye Corrosion:	0.0
Eye Irritation:	0.057	Respiratory Toxicity:	0.778
Drug-induced Neurotoxicity:	0.274	Ototoxicity:	0.525
Hematotoxicity:	0.476	Drug-induced Nephrotoxicity:	0.931
Genotoxicity:	0.994	RPMI-8226 Immunitoxicity:	0.177
A549 Cytotoxicity:	0.11	Hek293 Cytotoxicity:	0.68
BCF:	1.58 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.026 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.68 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.99 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO2010	Viburnum ichangense	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/hlca.201100177]
NPO302	Penicillium thiersii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787428]
NPO32542	penicillium camemberti oucmdz-1492	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23886345]
NPO10069	Chaptalia nutans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8763	Erythrina herbacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO302	Penicillium thiersii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16983	Persea obovatifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23123	Taxus spicata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23322	Dentidia nankinensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3117	Aconitum legendrei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3117	Aconitum legendrei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3117	Aconitum legendrei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3117	Aconitum legendrei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6764	Dianthus japonicus	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16983	Persea obovatifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9566	Abies canadensis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10069	Chaptalia nutans	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15125.2	Taxus wallichiana var. wallichiana	Varieties	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10990	Myristica surinamensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23322	Dentidia nankinensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9135	Ligularia fauriei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11104	Diadema antillarum	Species	Diadematidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2803	Lyonetia clerkella	Species	Lyonetiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8763	Erythrina herbacea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO302	Penicillium thiersii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8958	Centella erecta	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23123	Taxus spicata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2010	Viburnum ichangense	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9915	Pieris brassicae	Species	Pieridae	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	27
EC50	3
IC50	7
Ki	2
Activity	17
CC50	1
ED50	1

Activity Type	# Activity
Individual protein	22
Cell line	11
Single protein	4
Organism	5
Protein-protein interaction	2
Tissue	6
Others	8

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1197	Individual protein	Huntingtin	Homo sapiens	Potency	=	31622.8	nM	PubChem BioAssay data set
NPT1038	Individual protein	Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT1416	Individual protein	Neuropeptide S receptor	Homo sapiens	Potency	=	10000.0	nM	PubChem BioAssay data set
NPT1005	Individual protein	Tumor susceptibility gene 101 protein	Homo sapiens	Potency	n.a.	25118.9	nM	PubChem BioAssay data set
NPT1861	Individual protein	Mitochondrial import inner membrane translocase subunit TIM10	Saccharomyces cerevisiae S288c	IC50	=	33550.0	nM	PubChem BioAssay data set
NPT154	Individual protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT2971	Individual protein	DNA dC->dU-editing enzyme APOBEC-3F	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	2059.6	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	730.8	nM	PubChem BioAssay data set
NPT101	Individual protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	14125.4	nM	PubChem BioAssay data set
NPT160	Individual protein	TAR DNA-binding protein 43	Homo sapiens	Potency	n.a.	22387.2	nM	PubChem BioAssay data set
NPT797	Individual protein	Cytoplasmic zinc-finger protein	Caenorhabditis elegans	EC50	=	16719.0	nM	PubChem BioAssay data set
NPT21779	Single protein	Sarcoplasmic/endoplasmic reticulum calcium ATPase 3	Homo sapiens	IC50	=	5000.0	nM	PMID[32030976]
NPT795	Individual protein	Zinc finger protein mex-5	Caenorhabditis elegans	EC50	=	12272.0	nM	PubChem BioAssay data set
NPT5536	Individual protein	Sarcoplasmic/endoplasmic reticulum calcium ATP-ase	Oryctolagus cuniculus	IC50	=	5000.0	nM	PMID[32030976]
NPT21778	Single protein	Sarcoplasmic/endoplasmic reticulum calcium ATPase 2	Homo sapiens	IC50	=	5000.0	nM	PMID[32030976]
NPT51	Individual protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	17782.8	nM	PubChem BioAssay data set
NPT63	Individual protein	Bromodomain adjacent to zinc finger domain protein 2B	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	44668.4	nM	PubChem BioAssay data set
NPT755	Individual protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	16360.1	nM	PubChem BioAssay data set
NPT28321	Single protein	Oxysterol-binding protein 1	Homo sapiens	Ki	>	50000.0	nM	PMID[36916802]
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT532	Individual protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	56234.1	nM	PubChem BioAssay data set
NPT5	Individual protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT29855	Single protein	Oxysterol-binding protein 2	Homo sapiens	Ki	>	30000.0	nM	PMID[36916802]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2891	Cell line	H4	Homo sapiens	Activity	=	100.56	%	PMID[18024584]
NPT2891	Cell line	H4	Homo sapiens	Activity	=	52.37	%	PMID[18024584]
NPT2891	Cell line	H4	Homo sapiens	Activity	=	56.82	%	PMID[18024584]
NPT2891	Cell line	H4	Homo sapiens	Activity	=	119.79	%	PMID[18024584]
NPT2891	Cell line	H4	Homo sapiens	Activity	=	162.66	%	PMID[18024584]
NPT2891	Cell line	H4	Homo sapiens	Activity	=	185.52	%	PMID[18024584]
NPT2891	Cell line	H4	Homo sapiens	Activity	=	205.83	%	PMID[18024584]
NPT2891	Cell line	H4	Homo sapiens	Activity	=	112.34	%	PMID[18024584]
NPT2891	Cell line	H4	Homo sapiens	Activity	=	106.27	%	PMID[18024584]
NPT2891	Cell line	H4	Homo sapiens	Activity	=	102.35	%	PMID[18024584]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	11689.1	nM	PubChem BioAssay data set
NPT548	Tissue	Ileum	Cavia porcellus	Activity	=	121.0	%	PMID[2045816]
NPT548	Tissue	Ileum	Cavia porcellus	Activity	=	118.0	%	PMID[2045816]
NPT548	Tissue	Ileum	Cavia porcellus	Activity	=	126.0	%	PMID[2045816]
NPT548	Tissue	Ileum	Cavia porcellus	Activity	=	9.0	%	PMID[2045816]
NPT548	Tissue	Ileum	Cavia porcellus	Activity	=	11.0	%	PMID[2045816]
NPT548	Tissue	Ileum	Cavia porcellus	Activity	=	2.0	%	PMID[2045816]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Potency	=	35481.3	nM	PubChem BioAssay data set
NPT1453	Organism	Influenza A virus (A/PR/8/34(H1N1))	Influenza A virus (A/Puerto Rico/8/1934(H1N1))	IC50	=	17700.0	nM	PMID[23886345]
NPT2	Others	Unspecified	n.a.	IC50	=	42160.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	=	6513.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	EC50	>	110000.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	>	48710.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	16360.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	11220.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	CC50	>	40000.0	nM	PubChem BioAssay data set

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	25.0	mg.kg-1	PMID[2045816]

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

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 NPC235900 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	10508
0.1-0.2	37858
0.2-0.3	1272
0.3-0.4	151
0.4-0.5	39
0.5-0.6	16
0.6-0.7	4
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9079	High Similarity	NPC471284
0.775	Intermediate Similarity	NPC484479
0.7711	Intermediate Similarity	NPC96131
0.7561	Intermediate Similarity	NPC484481
0.7531	Intermediate Similarity	NPC487204
0.7381	Intermediate Similarity	NPC61813
0.7108	Intermediate Similarity	NPC123019
0.7059	Intermediate Similarity	NPC486860
0.6526	Remote Similarity	NPC486865
0.6279	Remote Similarity	NPC487205
0.6044	Remote Similarity	NPC487206
0.6023	Remote Similarity	NPC224641
0.5955	Remote Similarity	NPC487201
0.5854	Remote Similarity	NPC99428
0.573	Remote Similarity	NPC34271
0.573	Remote Similarity	NPC20697
0.5652	Remote Similarity	NPC484483
0.5591	Remote Similarity	NPC602114
0.5529	Remote Similarity	NPC165201
0.5422	Remote Similarity	NPC302191
0.5368	Remote Similarity	NPC611491
0.5222	Remote Similarity	NPC231342
0.5222	Remote Similarity	NPC609321
0.5165	Remote Similarity	NPC119700
0.5149	Remote Similarity	NPC487203
0.5098	Remote Similarity	NPC487202
0.5053	Remote Similarity	NPC18661
0.505	Remote Similarity	NPC214429

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC235900 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4280
0.1-0.2	4748
0.2-0.3	117
0.3-0.4	5
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