NPASS Compound

Natural Product: NPC526588

Natural Product ID	NPC526588
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-(1,3-benzodioxol-5-yl)-~{N}-isopentyl-penta-2,4-dienamide
IUPAC Name	5-(1,3-benzodioxol-5-yl)-~{N}-isopentyl-penta-2,4-dienamide
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 42 43 0 0 0 0 0 0 0 0999 V2000 -5.7092 -0.0186 0.1589 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2872 -0.4211 0.4788 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2682 -1.5078 1.5232 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5179 0.7651 1.0278 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4879 1.8811 0.0166 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8708 1.5380 -1.2292 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5055 1.1267 -1.2305 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9072 1.0846 -0.1456 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8568 0.7732 -2.4727 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3653 0.3808 -2.6639 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3568 0.2161 -1.6131 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5954 -0.1930 -1.8976 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6474 -0.3879 -0.9402 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8933 -0.8167 -1.3625 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9318 -1.0165 -0.4757 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7467 -0.7891 0.8736 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6293 -0.9177 1.9504 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0032 -0.2297 3.0235 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6125 -0.2174 2.6824 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5139 -0.3617 1.3151 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4904 -0.1703 0.3981 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0413 0.8425 0.7943 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3706 -0.8978 0.3669 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8106 0.2639 -0.9080 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7977 -0.8284 -0.4466 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3209 -2.0774 1.5282 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4145 -1.1195 2.5413 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0746 -2.2513 1.3410 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5420 0.4092 1.3566 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1433 1.1483 1.8808 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0274 2.7917 0.4842 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5496 2.1521 -0.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4292 1.5930 -2.1259 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4770 0.8411 -3.4055 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6797 0.1529 -3.7108 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1544 0.4081 -0.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7914 -0.3872 -2.9596 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0261 -0.9912 -2.4191 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9098 -1.3539 -0.8132 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1261 -0.8325 3.9347 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3941 0.8004 3.1069 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5418 0.1659 0.7962 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 2 3 10 11 1 0 11 12 2 3 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 13 1 0 20 16 1 0 1 22 1 0 1 23 1 0 1 24 1 0 2 25 1 0 3 26 1 0 3 27 1 0 3 28 1 0 4 29 1 0 4 30 1 0 5 31 1 0 5 32 1 0 6 33 1 0 9 34 1 0 10 35 1 0 11 36 1 0 12 37 1 0 14 38 1 0 15 39 1 0 18 40 1 0 18 41 1 0 21 42 1 0 M END

Standard InCHIKey	USDFAFZPUOHPKV-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C17H21NO3/c1-13(2)9-10-18-17(19)6-4-3-5-14-7-8-15-16(11-14)21-12-20-15/h3-8,11,13H,9-10,12H2,1-2H3,(H,18,19)
SMILES	CC(C)CCNC(=O)C=CC=CC1=CC=C2OCOC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	287.15	Volume:	307.024 ? Van der Waals volume.
Dense:	0.935	LogP:	3.793 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.512 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.213 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	13.0
TPSA:	47.56 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	2.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.646	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.413	Fsp³:	0.353
MCE-18:	22.957 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.948	Fluc inhibitor:	0.998 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.492 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.907 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.007	Promiscuous compounds:	0.011

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.838	MDCK Permeability:	-4.615
Pgp-inhibitor:	0.141	Pgp-substrate:	0.336
PAMPA:	0.799 ? 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):	0.007
20% Bioavailability (F20%):	0.115	30% Bioavailability (F30%):	0.004
50% Bioavailability (F50%):	0.815

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.725	MRP1:	0.464
Plasma Protein Binding (PPB):	98.156%	Volume Distribution (VD):	-0.217
Fu:	1.693% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.717
OATP1B3 inhibitor:	0.709	BCRP inhibitor:	0.009
BSEP inhibitor:	0.957

ADMET: Metabolism

CYP1A2-inhibitor:	0.168	CYP1A2-substrate:	0.995
CYP2C19-inhibitor:	0.966	CYP2C19-substrate:	0.549
CYP2C9-inhibitor:	0.349	CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.968	CYP2D6-substrate:	0.993
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.994
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.756
HLM stability:	0.669 ? 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):

5.081

Half-life (T1/2):

0.553

ADMET: Toxicity

hERG Blockers:	0.26	hERG Blockers (10um):	0.552
Human Hepatotoxicity (H-HT):	0.584	Drug-induced Liver Injury (DILI):	0.364
AMES Toxicity:	0.736	Rat Oral Acute Toxicity:	0.283
Maximum Recommended Daily Dose:	0.43	Skin Sensitization:	0.873
Carcinogencity:	0.675	Eye Corrosion:	0.015
Eye Irritation:	0.887	Respiratory Toxicity:	0.369
Drug-induced Neurotoxicity:	0.449	Ototoxicity:	0.457
Hematotoxicity:	0.317	Drug-induced Nephrotoxicity:	0.427
Genotoxicity:	0.41	RPMI-8226 Immunitoxicity:	0.076
A549 Cytotoxicity:	0.24	Hek293 Cytotoxicity:	0.28
BCF:	1.204 ? 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:	3.677 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.402 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.667 ? 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
NPO10274	Pothomorphe peltata	n.a.	n.a.	n.a.	n.a.	Dominican Republic	n.a.	PMID[11430019]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695795]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19341262]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	corms	Iquitos, Peru	2005-MAY	PMID[19341262]
NPO10666	Verbesina virginica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19485332]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22909174]
NPO12125	Pseudomonas stutzeri	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23149469]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[23506561]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	leaves	n.a.	n.a.	PMID[25127165]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25988621]
NPO13059	Abies webbiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8639	Agaricus xanthodermus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10459	Brickellia longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12488	Bupleurum rigidum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11511	Cochlearia officinalis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9950	Coelogyne nitida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6880	Crocus corsicus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO876	Didymosphaeria enalia	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11137	Dichotomanthes tristaniicarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10666	Verbesina virginica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27487	Silene banksia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12125	Pseudomonas stutzeri	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10274	Pothomorphe peltata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2840	Podocarpus minor	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23642	Penicillium tardum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO230	Palisota barteri	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7536	Mycoplasma mycoides	Species	Mycoplasmataceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9166	Monascus rubropunctatus	Species	Fellodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2393	Matsumurella chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO43	Leifsonia aquatica	Species	Microbacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO964	Homalium laurifolium	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12383	Frullania brasiliensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6428	Euphorbia wangii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12383	Frullania brasiliensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27487	Silene banksia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6428	Euphorbia wangii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4251	Photorhabdus luminescens	Species	Morganellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12383	Frullania brasiliensis	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12125	Pseudomonas stutzeri	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2393	Matsumurella chinensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6544	Carpesium longifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23642	Penicillium tardum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12488	Bupleurum rigidum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7158	Schefflera venulosa	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO876	Didymosphaeria enalia	Species	Didymosphaeriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9166	Monascus rubropunctatus	Species	Fellodistomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10274	Pothomorphe peltata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO3968	Dracontium loretense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10459	Brickellia longifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8639	Agaricus xanthodermus	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2840	Podocarpus minor	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO964	Homalium laurifolium	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9950	Coelogyne nitida	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO230	Palisota barteri	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11511	Cochlearia officinalis	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO43	Leifsonia aquatica	Species	Microbacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6880	Crocus corsicus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6648	Piper retrofractum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13059	Abies webbiana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10666	Verbesina virginica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27487	Silene banksia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11137	Dichotomanthes tristaniicarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7536	Mycoplasma mycoides	Species	Mycoplasmataceae	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	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC526588 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	20603
0.1-0.2	27515
0.2-0.3	1570
0.3-0.4	117
0.4-0.5	37
0.5-0.6	11
0.6-0.7	4
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	Natural Product ID
0.65	Remote Similarity	NPC251466
0.6271	Remote Similarity	NPC182147
0.6271	Remote Similarity	NPC207541
0.6271	Remote Similarity	NPC246133
0.5714	Remote Similarity	NPC473463
0.5455	Remote Similarity	NPC282477
0.5455	Remote Similarity	NPC284855
0.5294	Remote Similarity	NPC127326
0.5246	Remote Similarity	NPC94280
0.5172	Remote Similarity	NPC199209
0.5161	Remote Similarity	NPC255817
0.5161	Remote Similarity	NPC136330
0.5147	Remote Similarity	NPC170583
0.5082	Remote Similarity	NPC300955
0.5082	Remote Similarity	NPC469977

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC526588 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3444
0.1-0.2	5598
0.2-0.3	103
0.3-0.4	3
0.4-0.5	0
0.5-0.6	2
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
0.5357	Remote Similarity	NPD1357	Phase 4
0.5161	Remote Similarity	NPD2492	Phase 2

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