NPASS Compound

Natural Product: NPC45947

Natural Product ID	NPC45947
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DHQZOOQNUWHCML-IIRLODAESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL484254
PubChem CID	10444597
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0003671] Aryl alkyl ketones

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 36 38 0 0 0 0 0 0 0 0999 V2000 -1.0170 3.5156 -0.4311 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5705 2.0348 -0.3567 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4459 1.8290 0.6539 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2346 0.6569 0.8438 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9624 0.5695 1.8731 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4075 -0.5641 0.0330 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3924 -0.5767 -0.9937 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2756 0.5971 -1.2654 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3269 -1.8154 -1.5529 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4006 -2.4803 -0.9270 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -1.7449 0.0344 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2649 -2.3196 0.8958 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5190 -2.4688 0.1250 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1234 -3.6050 -0.0362 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1353 -1.2444 -0.5197 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6468 -0.1211 0.0441 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8955 1.3086 -0.1829 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0696 -0.5916 -1.1313 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1951 3.8235 -1.4663 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9195 3.6981 0.1541 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1387 4.1049 -0.0600 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2190 1.7864 -1.3661 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0548 2.1315 1.6522 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2119 2.6895 0.6031 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6638 1.0293 -0.2948 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7948 1.3873 -1.8338 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1815 0.1883 -1.7522 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9617 -2.1593 -2.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3413 -1.7994 1.8531 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0233 -3.3749 1.2194 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7749 -4.5530 0.3734 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0400 -3.6616 -0.6093 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0748 -1.3670 -1.0652 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2072 -0.2367 1.0649 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4674 1.4826 -1.1141 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4421 1.8509 0.6137 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 2 0 4 6 1 0 6 7 1 0 7 8 1 0 7 9 2 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 16 18 1 0 17 2 1 0 11 6 2 0 18 15 1 0 1 19 1 0 1 20 1 0 1 21 1 0 2 22 1 6 3 23 1 0 3 24 1 0 8 25 1 0 8 26 1 0 8 27 1 0 9 28 1 0 12 29 1 0 12 30 1 0 14 31 1 0 14 32 1 0 15 33 1 6 16 34 1 1 17 35 1 0 17 36 1 0 M END

Standard InCHIKey	DHQZOOQNUWHCML-IIRLODAESA-N
Standard InCHI	InChI=1S/C15H18O3/c1-8-4-11(16)14-10(3)7-17-12(14)6-9(2)15-13(5-8)18-15/h7-8,13,15H,2,4-6H2,1,3H3/t8-,13-,15-/m0/s1
SMILES	C[C@H]1CC(=O)c2c(C)coc2CC(=C)[C@H]2[C@H](C1)O2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	246.13	Volume:	258.152 ? Van der Waals volume.
Dense:	0.953	LogP:	3.296 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.174 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.44 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	18.0
TPSA:	42.74 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.522	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.813	Fsp³:	0.533
MCE-18:	59.87 ? 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:	0.429	Fluc inhibitor:	0.023 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.053 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.027 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.512	Promiscuous compounds:	0.574

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.674	MDCK Permeability:	-4.374
Pgp-inhibitor:	0.802	Pgp-substrate:	0.016
PAMPA:	0.025 ? 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%):	0.015	30% Bioavailability (F30%):	0.036
50% Bioavailability (F50%):	0.091

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.163	MRP1:	0.935
Plasma Protein Binding (PPB):	92.548%	Volume Distribution (VD):	0.285
Fu:	7.51% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.856
OATP1B3 inhibitor:	0.861	BCRP inhibitor:	0.514
BSEP inhibitor:	0.985

ADMET: Metabolism

CYP1A2-inhibitor:	0.119	CYP1A2-substrate:	0.709
CYP2C19-inhibitor:	0.828	CYP2C19-substrate:	0.491
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.912	CYP3A4-substrate:	0.935
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.873
HLM stability:	0.979 ? 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):

9.683

Half-life (T1/2):

1.308

ADMET: Toxicity

hERG Blockers:	0.093	hERG Blockers (10um):	0.369
Human Hepatotoxicity (H-HT):	0.682	Drug-induced Liver Injury (DILI):	0.953
AMES Toxicity:	0.914	Rat Oral Acute Toxicity:	0.701
Maximum Recommended Daily Dose:	0.814	Skin Sensitization:	0.945
Carcinogencity:	0.864	Eye Corrosion:	0.264
Eye Irritation:	0.945	Respiratory Toxicity:	0.67
Drug-induced Neurotoxicity:	0.881	Ototoxicity:	0.503
Hematotoxicity:	0.439	Drug-induced Nephrotoxicity:	0.679
Genotoxicity:	0.942	RPMI-8226 Immunitoxicity:	0.198
A549 Cytotoxicity:	0.545	Hek293 Cytotoxicity:	0.52
BCF:	1.654 ? 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:	3.781 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.226 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.755 ? 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
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	roots	northern Saudi desert	n.a.	PMID[10924184]
NPO6831	Commiphora opobalsamum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18177010]
NPO8286	Porophyllum ruderale	Species	Asteraceae	Eukaryota	n.a.	Along the Valencian coast, Spain	2020-Jun&Jul	PMID[35161358]
NPO7730	Commiphora myrrha	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38675598]
NPO11719	Lamellomorpha strongylata	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9644054]
NPO24891	Elmerina caryae	Species	Aporpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6831	Commiphora opobalsamum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6022	Cytisus supinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4463	Cytisus canariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29336	Corynandra chelidonii	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3693	Calpurnia aurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10085	Aspergillus varians	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9883	Allium giganteum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7730	Commiphora myrrha	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9036	Dipteryx lacunifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8985	Gazania rigens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4964	Traversia baccharoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14610	Ophiopogon intermedius	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4236	Microscleroderma spirophora	Species	Scleritodermidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13613	Lophophora williamsii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11719	Lamellomorpha strongylata	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8286	Porophyllum ruderale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25831	Siphonoglossa sessilis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5284	Ramalina hierrensis	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5886	Fossombronia alaskana	Species	Fossombroniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9639	Prunus puddum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8810	Pinus austriaca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1586	Gorgonocephalus chilensis	Species	Gorgonocephalidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8297	Hydnellum caeruleum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2328	Lagochilus setulosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7730	Commiphora myrrha	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13613	Lophophora williamsii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13613	Lophophora williamsii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8297	Hydnellum caeruleum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7730	Commiphora myrrha	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7730	Commiphora myrrha	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4236	Microscleroderma spirophora	Species	Scleritodermidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7260	Angelica genuflexa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8985	Gazania rigens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24891	Elmerina caryae	Species	Aporpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5284	Ramalina hierrensis	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11719	Lamellomorpha strongylata	Species	Vulcanellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1586	Gorgonocephalus chilensis	Species	Gorgonocephalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8810	Pinus austriaca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29336	Corynandra chelidonii	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO817	Dictamnus angustifolius	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9036	Dipteryx lacunifera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2328	Lagochilus setulosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4463	Cytisus canariensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9639	Prunus puddum	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6022	Cytisus supinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25831	Siphonoglossa sessilis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13613	Lophophora williamsii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4964	Traversia baccharoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3693	Calpurnia aurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9883	Allium giganteum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11707	Ruta chalepensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14610	Ophiopogon intermedius	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8286	Porophyllum ruderale	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6831	Commiphora opobalsamum	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5886	Fossombronia alaskana	Species	Fossombroniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8297	Hydnellum caeruleum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10085	Aspergillus varians	Species	Aspergillaceae	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
IC50	1

Activity Type	# Activity
Cell line	1

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
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	40000.0	nM	PMID[11720534]

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 NPC45947 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	18873
0.1-0.2	30678
0.2-0.3	286
0.3-0.4	19
0.4-0.5	2
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC45947 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3757
0.1-0.2	5357
0.2-0.3	36
0.3-0.4	0
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