NPASS Compound

Natural Product: NPC253675

Natural Product ID	NPC253675
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DONUVZIVKLIMJU-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1922244
PubChem CID	100605
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0001908] Benzoquinolines [CHEMONTID:0000100] Phenanthridines and derivatives

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 29 33 0 0 0 0 0 0 0 0999 V2000 -2.3411 2.5418 -0.6172 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4062 1.7079 -0.3726 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2185 0.3770 -0.0319 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0176 -0.7057 0.2703 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1363 -1.7524 0.5188 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8523 -1.3248 0.3739 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9069 -0.0311 0.0394 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8079 0.7524 -0.1931 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0270 2.0668 -0.5286 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4721 0.2314 -0.0916 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5865 0.9961 -0.3196 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8415 0.4372 -0.2076 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9289 -0.9162 0.1415 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7921 -1.6655 0.3661 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5252 -1.1243 0.2590 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6246 -1.8713 0.4833 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5129 -3.0815 0.7947 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2647 -1.2809 0.2009 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0656 -0.1372 -0.0112 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1516 0.8688 -0.3543 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4843 3.5795 -0.8829 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4254 2.0543 -0.4356 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 -0.7348 0.3061 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3968 -2.7692 0.7897 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1967 2.7011 -0.7152 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5347 2.0339 -0.5877 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8408 -2.7274 0.6405 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8448 -0.3087 -0.7974 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5914 0.0827 0.9625 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 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 13 18 1 0 18 19 1 0 19 20 1 0 9 1 1 0 15 10 1 0 7 3 2 0 20 12 1 0 16 6 1 0 1 21 1 0 2 22 1 0 4 23 1 0 5 24 1 0 9 25 1 0 11 26 1 0 14 27 1 0 19 28 1 0 19 29 1 0 M END

Standard InCHIKey	DONUVZIVKLIMJU-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C16H9NO3/c18-16-12-7-14-13(19-8-20-14)6-11(12)10-3-1-2-9-4-5-17(16)15(9)10/h1-7H,8H2
SMILES	c1cc2ccn3c2c(c1)c1cc2c(cc1c3=O)OCO2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	263.06	Volume:	258.786 ? Van der Waals volume.
Dense:	1.017	LogP:	2.79 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.832 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.931 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	0.0	Rigid Bonds:	24.0
TPSA:	39.94 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.458	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.405	Fsp³:	0.062
MCE-18:	50.824 ? 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:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.8	Fluc inhibitor:	0.465 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.886 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.412 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.021	Promiscuous compounds:	0.486

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.807	MDCK Permeability:	-4.589
Pgp-inhibitor:	0.536	Pgp-substrate:	0.04
PAMPA:	0.485 ? 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):	0.014
20% Bioavailability (F20%):	0.053	30% Bioavailability (F30%):	0.058
50% Bioavailability (F50%):	0.273

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.253	MRP1:	0.594
Plasma Protein Binding (PPB):	97.207%	Volume Distribution (VD):	0.19
Fu:	2.771% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.762
OATP1B3 inhibitor:	0.962	BCRP inhibitor:	0.03
BSEP inhibitor:	0.977

ADMET: Metabolism

CYP1A2-inhibitor:	0.955	CYP1A2-substrate:	0.877
CYP2C19-inhibitor:	0.307	CYP2C19-substrate:	0.252
CYP2C9-inhibitor:	0.908	CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.99	CYP2D6-substrate:	0.98
CYP3A4-inhibitor:	0.046	CYP3A4-substrate:	0.981
CYP2B6-substrate:	0.739	CYP2C8-inhibitor:	0.526
HLM stability:	0.532 ? 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):

4.407

Half-life (T1/2):

0.705

ADMET: Toxicity

hERG Blockers:	0.401	hERG Blockers (10um):	0.629
Human Hepatotoxicity (H-HT):	0.785	Drug-induced Liver Injury (DILI):	0.982
AMES Toxicity:	0.93	Rat Oral Acute Toxicity:	0.593
Maximum Recommended Daily Dose:	0.768	Skin Sensitization:	0.372
Carcinogencity:	0.948	Eye Corrosion:	0.0
Eye Irritation:	0.537	Respiratory Toxicity:	0.934
Drug-induced Neurotoxicity:	0.974	Ototoxicity:	0.692
Hematotoxicity:	0.791	Drug-induced Nephrotoxicity:	0.855
Genotoxicity:	0.955	RPMI-8226 Immunitoxicity:	0.212
A549 Cytotoxicity:	0.534	Hek293 Cytotoxicity:	0.715
BCF:	1.753 ? 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:	4.224 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.699 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.316 ? 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
NPO13176	Garcinia densivenia	Species	Clusiaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/S0031-9422(00)83950-3]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441066]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[16441066]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19653666]
NPO12711	Ligularia altaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20073490]
NPO40778	Alkaloid lycorine	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22019045]
NPO22157	Datura wrightii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23252848]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24253739]
NPO4576	Corynandra viscosa	Species	Cleomaceae	Eukaryota	n.a.	leaf	n.a.	PMID[28135851]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	Thai	n.a.	PMID[3430167]
NPO1412	Artemisia juncea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9144	Atriplex parvifolia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11000	Eupatorium laevigatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9485	Haplopappus deserticola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19776	Hesperocyparis arizonica	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11473	Viburnum lantana	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4316	Ananas sativus	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4020	Dorstenia turbinata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5924	Brunsvigia josephinae	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10319	Calycodendron milnei	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4576	Corynandra viscosa	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9612	Dryopteris dilatata	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12711	Ligularia altaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25680	Ramalina siliquosa	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10281	Fritillaria roylei	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11658	Alternanthera philoxeroides	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14342	Chrysobalanus icaco	Species	Chrysobalanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21442	Elaeocarpus sphaericus	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2381	Phacelocarpus peperocarpos	Species	Phacelocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13259	Commiphora wightii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18449	Salvia yunnanensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22054	Cinchona officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1383.1	Murraya paniculata var. omphalocarpa	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22157	Datura wrightii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14727	Streptomyces phaeochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12363	Dermocybe sanguinea	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17715	Flindersia bourjotiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18449	Salvia yunnanensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11658	Alternanthera philoxeroides	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22054	Cinchona officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14342	Chrysobalanus icaco	Species	Chrysobalanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18449	Salvia yunnanensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1383.1	Murraya paniculata var. omphalocarpa	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22054	Cinchona officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11658	Alternanthera philoxeroides	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13259	Commiphora wightii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14342	Chrysobalanus icaco	Species	Chrysobalanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4576	Corynandra viscosa	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9485	Haplopappus deserticola	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9144	Atriplex parvifolia	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13659	Helichrysum asperum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12711	Ligularia altaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23036	Angelica hirsutiflora	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17715	Flindersia bourjotiana	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4617	Tanacetum cinerariifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18476	Lophopetalum toxicum	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10319	Calycodendron milnei	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21442	Elaeocarpus sphaericus	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4020	Dorstenia turbinata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20170	Anthoceros punctatus	Species	Anthocerotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13772	Didemnum proliferum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5924	Brunsvigia josephinae	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9612	Dryopteris dilatata	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3630	Crotalaria crispata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23120	Clausena suffruticosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22157	Datura wrightii	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22054	Cinchona officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4576	Corynandra viscosa	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1412	Artemisia juncea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22009	Lupinus holosericeus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19776	Hesperocyparis arizonica	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1383.1	Murraya paniculata var. omphalocarpa	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11000	Eupatorium laevigatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13027	Eucalyptus torelliana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4316	Ananas sativus	Species	Bromeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7031	Salvia keerlii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11473	Viburnum lantana	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17378	Percis semifasciata	Species	Agonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25680	Ramalina siliquosa	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1828	Searsia leptodictya	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13259	Commiphora wightii	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17956	Fagus glauca	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14342	Chrysobalanus icaco	Species	Chrysobalanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11265	Coryphantha cornifera	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12363	Dermocybe sanguinea	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10281	Fritillaria roylei	Species	Liliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14727	Streptomyces phaeochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11658	Alternanthera philoxeroides	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13176	Garcinia densivenia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8546	Corydalis chaerophylla	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2381	Phacelocarpus peperocarpos	Species	Phacelocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27248	Artemisia pygmaea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18449	Salvia yunnanensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11841	Psorothamnus arborescens	Species	Fabaceae	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
GI50	8
IZ	2
IC50	2

Activity Type	# Activity
Cell line	6
Organism	4
Non-molecular	2

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	GI50	=	27000.0	nM	PMID[22019045]
NPT169	Cell line	B16-F10	Mus musculus	GI50	=	34000.0	nM	PMID[22019045]
NPT1125	Cell line	T98G	Homo sapiens	GI50	=	96000.0	nM	PMID[22019045]
NPT81	Cell line	A549	Homo sapiens	GI50	=	96000.0	nM	PMID[22019045]
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	>	100000.0	nM	PMID[22019045]
NPT306	Cell line	PC-3	Homo sapiens	GI50	>	100000.0	nM	PMID[22019045]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	8.4	ug.mL-1	PMID[31515186]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	19000.0	nM	PMID[22019045]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI50	=	27000.0	nM	PMID[22019045]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	90.0	ug.mL-1	PMID[31515186]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	7.0	mm	PMID[29033234]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	7.0	mm	PMID[29033234]

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 NPC253675 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	38500
0.1-0.2	10846
0.2-0.3	482
0.3-0.4	23
0.4-0.5	5
0.5-0.6	1
0.6-0.7	1
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
0.6667	Remote Similarity	NPC479868
0.5179	Remote Similarity	NPC254957

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC253675 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6623
0.1-0.2	2513
0.2-0.3	13
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