NPASS Compound

Natural Product: NPC38209

Natural Product ID	NPC38209
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1-(4-Methoxyphenyl)Acetone
IUPAC Name	1-(4-methoxyphenyl)propan-2-one
Synonyms	1-(4-Methoxyphenyl)Acetone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL473366
PubChem CID	31231
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

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 24 24 0 0 0 0 0 0 0 0999 V2000 -4.2724 0.3925 -0.1591 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8301 0.1856 -0.3915 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3861 0.2747 -1.5089 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9397 -0.1280 0.7364 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5370 -0.3062 0.3524 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0238 -1.5058 -0.0131 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3529 -1.6211 -0.3669 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1672 -0.5116 -0.3619 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6156 0.7009 0.0037 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2853 0.8013 0.3550 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5121 -0.6271 -0.7197 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3179 0.5480 -0.7004 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7027 1.1547 -0.8721 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8632 -0.5404 -0.2729 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3995 0.7504 0.8861 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3498 -1.0624 1.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0037 0.6496 1.5234 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5794 -2.3878 -0.0280 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7342 -2.6111 -0.6481 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2902 1.5510 -0.0052 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0633 1.7904 0.6279 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3273 0.2801 -1.1144 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8617 1.3077 -1.3820 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4386 0.9148 0.3206 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 8 11 1 0 11 12 1 0 10 5 1 0 1 13 1 0 1 14 1 0 1 15 1 0 4 16 1 0 4 17 1 0 6 18 1 0 7 19 1 0 9 20 1 0 10 21 1 0 12 22 1 0 12 23 1 0 12 24 1 0 M END

Standard InCHIKey	WFWKNGZODAOLEO-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C10H12O2/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6H,7H2,1-2H3
SMILES	CC(=O)Cc1ccc(cc1)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	164.08	Volume:	179.994 ? Van der Waals volume.
Dense:	0.912	LogP:	1.76 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.829 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.051 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	7.0
TPSA:	26.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	1.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.681	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.468	Fsp³:	0.3
MCE-18:	6.0 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.02	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.055 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.998	Promiscuous compounds:	0.013

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.463	MDCK Permeability:	-4.193
Pgp-inhibitor:	0.085	Pgp-substrate:	0.152
PAMPA:	0.308 ? 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):	0.305
20% Bioavailability (F20%):	0.063	30% Bioavailability (F30%):	0.082
50% Bioavailability (F50%):	0.557

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.329	MRP1:	0.692
Plasma Protein Binding (PPB):	70.893%	Volume Distribution (VD):	0.028
Fu:	25.518% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.393
OATP1B3 inhibitor:	0.611	BCRP inhibitor:	0.109
BSEP inhibitor:	0.808

ADMET: Metabolism

CYP1A2-inhibitor:	0.979	CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.996	CYP2C19-substrate:	0.12
CYP2C9-inhibitor:	0.704	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.132	CYP2D6-substrate:	0.749
CYP3A4-inhibitor:	0.982	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.003	CYP2C8-inhibitor:	0.632
HLM stability:	0.892 ? 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):

10.201

Half-life (T1/2):

0.799

ADMET: Toxicity

hERG Blockers:	0.089	hERG Blockers (10um):	0.487
Human Hepatotoxicity (H-HT):	0.388	Drug-induced Liver Injury (DILI):	0.433
AMES Toxicity:	0.41	Rat Oral Acute Toxicity:	0.323
Maximum Recommended Daily Dose:	0.106	Skin Sensitization:	0.832
Carcinogencity:	0.467	Eye Corrosion:	0.901
Eye Irritation:	0.988	Respiratory Toxicity:	0.671
Drug-induced Neurotoxicity:	0.573	Ototoxicity:	0.165
Hematotoxicity:	0.448	Drug-induced Nephrotoxicity:	0.22
Genotoxicity:	0.252	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.045	Hek293 Cytotoxicity:	0.084
BCF:	0.344 ? 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:	2.877 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.712 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.125 ? 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
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94055-X]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.3390/70200245]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[12350140]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[12762796]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	bark	n.a.	PMID[15283458]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387657]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[15577257]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[1955882]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24617303]
NPO54641	Foeniculum vulgare subsp. vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30632261]
NPO54641	Foeniculum vulgare subsp. vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33410338]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36432786]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37379658]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37446712]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38790803]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[8021657]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9051910]
NPO6519	Calocera viscosa	Species	Dacrymycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18379	Satureja atropatana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14465	Ramalina terebrata	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13368	Monomorium delagoense	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7027	Metapenaeus macleayi	Species	Penaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16137	Mappia foetida	Species	Icacinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16626	Leucetta microrhaphis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10773	Dalbergia rubiginosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10551	Acanthopanax ricinifolius	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13970	Caryopteris mongholica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13368	Monomorium delagoense	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13970	Caryopteris mongholica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10551	Acanthopanax ricinifolius	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12693	Mesembryanthemum tortuosum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18379	Satureja atropatana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7027	Metapenaeus macleayi	Species	Penaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4626	Pimpinella anisum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6519	Calocera viscosa	Species	Dacrymycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12181	Albizia julibrissin	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16137	Mappia foetida	Species	Icacinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10773	Dalbergia rubiginosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13274	Illicium verum	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5911	Anchusa officinalis	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16626	Leucetta microrhaphis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14465	Ramalina terebrata	Species	Ramalinaceae	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
NPO4626	Pimpinella anisum	Other	Seed	73.1	73.1	73.1	mg/100g	Database [DUKE]
NPO54641	Foeniculum vulgare subsp. vulgare	Oil	n.a.	11.8	n.a.	n.a.	%	PMID[30632261]
NPO54641	Foeniculum vulgare subsp. vulgare	Oil	n.a.	18.2	n.a.	n.a.	%	PMID[30632261]

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
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	43000.0	nM	PMID[19251422]

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
-	Rattus norvegicus	LD50	=	3330.0	mg/kg	ToxVal
-	Mus musculus	LD50	=	2.467195705	mg/kg	TOXRIC
-	Oryctolagus cuniculus	LD50	>	5000.0	mg/kg	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 NPC38209 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	22790
0.1-0.2	22736
0.2-0.3	3941
0.3-0.4	328
0.4-0.5	48
0.5-0.6	8
0.6-0.7	5
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
0.6429	Remote Similarity	NPC321956
0.6333	Remote Similarity	NPC298224
0.6071	Remote Similarity	NPC71853
0.6	Remote Similarity	NPC97811
0.6	Remote Similarity	NPC605225
0.5667	Remote Similarity	NPC42383
0.5556	Remote Similarity	NPC285679
0.5484	Remote Similarity	NPC1065
0.5357	Remote Similarity	NPC183648
0.5312	Remote Similarity	NPC469954
0.5185	Remote Similarity	NPC57879
0.5185	Remote Similarity	NPC177844
0.5143	Remote Similarity	NPC233410

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC38209 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3447
0.1-0.2	5062
0.2-0.3	607
0.3-0.4	33
0.4-0.5	1
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