NPASS Compound

Natural Product: NPC385

Natural Product ID	NPC385
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sarmentine
IUPAC Name	(2E,4E)-1-pyrrolidin-1-yldeca-2,4-dien-1-one
Synonyms	Sarmentine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2205104
PubChem CID	6440616
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000218] Pyrrolidines [CHEMONTID:0003023] N-acylpyrrolidines

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 39 39 0 0 0 0 0 0 0 0999 V2000 6.8896 0.1031 -0.1786 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3851 0.2585 -0.3802 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7927 -1.1082 -0.1630 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3166 -1.1903 -0.3193 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6412 -0.2862 0.6669 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1425 -0.3669 0.5235 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4207 0.6967 0.2241 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0585 0.5956 0.0871 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7695 1.6445 -0.2080 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1847 1.7402 -0.3792 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6688 2.9185 -0.6796 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1089 0.7142 -0.2612 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9743 -0.6845 0.0538 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4042 -1.2631 0.0889 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1586 0.0006 0.5106 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5724 0.9707 -0.4824 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3758 -0.0656 -1.1613 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3181 0.9808 0.3590 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1067 -0.7754 0.4621 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9717 1.0042 0.3311 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1545 0.5898 -1.4157 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3246 -1.8012 -0.8703 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0508 -1.4254 0.8815 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0208 -2.2514 -0.1956 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0726 -0.9297 -1.3718 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9801 0.7568 0.4682 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8706 -0.5194 1.7072 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6224 -1.3029 0.6634 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9059 1.6371 0.0796 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5238 -0.3474 0.2331 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1576 2.5731 -0.3367 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5784 -0.7576 1.1049 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3876 -1.2638 -0.6856 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6747 -1.5361 -0.9436 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5014 -2.0606 0.8239 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8026 0.2441 1.5276 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2406 -0.1175 0.4230 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7751 0.6149 -1.4934 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8213 2.0101 -0.2780 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 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 12 1 0 1 17 1 0 1 18 1 0 1 19 1 0 2 20 1 0 2 21 1 0 3 22 1 0 3 23 1 0 4 24 1 0 4 25 1 0 5 26 1 0 5 27 1 0 6 28 1 0 7 29 1 0 8 30 1 0 9 31 1 0 13 32 1 0 13 33 1 0 14 34 1 0 14 35 1 0 15 36 1 0 15 37 1 0 16 38 1 0 16 39 1 0 M END

Standard InCHIKey	BFZBGTMIBOQWBA-HRCSPUOPSA-N
Standard InCHI	InChI=1S/C14H23NO/c1-2-3-4-5-6-7-8-11-14(16)15-12-9-10-13-15/h6-8,11H,2-5,9-10,12-13H2,1H3/b7-6+,11-8+
SMILES	CCCCC/C=C/C=C/C(=O)N1CCCC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	221.18	Volume:	254.021 ? Van der Waals volume.
Dense:	0.871	LogP:	3.511 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.234 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.686 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	8.0
TPSA:	20.31 ? 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:	0.383	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.321	Fsp³:	0.643
MCE-18:	6.739 ? 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:	0.042	Fluc inhibitor:	0.685 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.035 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.358 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.492	Promiscuous compounds:	0.018

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.678	MDCK Permeability:	-4.686
Pgp-inhibitor:	0.812	Pgp-substrate:	0.119
PAMPA:	0.018 ? 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):	0.04
20% Bioavailability (F20%):	0.074	30% Bioavailability (F30%):	0.517
50% Bioavailability (F50%):	0.663

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009	MRP1:	0.314
Plasma Protein Binding (PPB):	97.399%	Volume Distribution (VD):	-0.499
Fu:	2.716% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.662
OATP1B3 inhibitor:	0.908	BCRP inhibitor:	0.124
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.489	CYP1A2-substrate:	0.984
CYP2C19-inhibitor:	0.159	CYP2C19-substrate:	0.999
CYP2C9-inhibitor:	0.943	CYP2C9-substrate:	0.408
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.156
CYP3A4-inhibitor:	0.107	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.061	CYP2C8-inhibitor:	1.0
HLM stability:	0.951 ? 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):

7.119

Half-life (T1/2):

0.777

ADMET: Toxicity

hERG Blockers:	0.449	hERG Blockers (10um):	0.569
Human Hepatotoxicity (H-HT):	0.641	Drug-induced Liver Injury (DILI):	0.393
AMES Toxicity:	0.609	Rat Oral Acute Toxicity:	0.261
Maximum Recommended Daily Dose:	0.499	Skin Sensitization:	0.904
Carcinogencity:	0.302	Eye Corrosion:	0.31
Eye Irritation:	0.905	Respiratory Toxicity:	0.816
Drug-induced Neurotoxicity:	0.519	Ototoxicity:	0.311
Hematotoxicity:	0.324	Drug-induced Nephrotoxicity:	0.546
Genotoxicity:	0.071	RPMI-8226 Immunitoxicity:	0.094
A549 Cytotoxicity:	0.199	Hek293 Cytotoxicity:	0.448
BCF:	1.247 ? 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:	4.023 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.274 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.856 ? 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
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4039(01)00209-X]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10575373]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15467205]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[16808005]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872768]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	whole plants	Sendai, Miyagi Prefecture, Japan	2000-Sep	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17243725]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17397219]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20839888]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	whole plant	Luxi County, Yunnan Province, China	2008-OCT	PMID[21158422]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21158422]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	aerial parts	Kego Nature Reserve, Hatinh Province, Vietnam	2008-DEC	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	twig	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	Kego Nature Reserve, Hatinh Province, Vietnam	2008-DEC	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	inflorescence	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	stem	n.a.	PMID[21973101]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21973101]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22940450]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23102654]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	leaves, twigs, and fruits	Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam	2010-Jan	PMID[23301897]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23434420]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31096694]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31103896]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31621322]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31766491]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38067483]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38474459]
NPO1912	Acanthosyris paulo-alvinii	Species	Cervantesiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO992	Betula alnoides	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5657	Oocystis polymorpha	Species	Oocystaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO61	Phoebe grandis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6614	Rubus pileatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30128	Piper boehmeriaefolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6614	Rubus pileatus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3803	Ardisia japonica	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2846	Piper sarmentosum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28928	Piper nigrum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO992	Betula alnoides	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO61	Phoebe grandis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26237	Piper longum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5657	Oocystis polymorpha	Species	Oocystaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1912	Acanthosyris paulo-alvinii	Species	Cervantesiaceae	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
MIC	2
IC50	10
mortality	15

Activity Type	# Activity
Cell line	8
Organism	17
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
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[22985027]
NPT81	Cell line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[25241925]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[25241925]
NPT133	Cell line	ZR-75-1	Homo sapiens	IC50	>	40000.0	nM	PMID[25241925]
NPT134	Cell line	SK-BR-3	Homo sapiens	IC50	>	40000.0	nM	PMID[25241925]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	40000.0	nM	PMID[25241925]
NPT90	Cell line	DU-145	Homo sapiens	IC50	>	40000.0	nM	PMID[25241925]
NPT91	Cell line	KB	Homo sapiens	IC50	>	40000.0	nM	PMID[25241925]
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	50.0	ug.mL-1	PMID[22280816]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[22985027]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	40000.0	nM	PMID[25241925]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	50.0	ug.mL-1	PMID[28628823]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT122	Organism	Solanum nigrum	Solanum nigrum	mortality	=	80.0	%	PMID[20839888]
NPT125	Organism	Chenopodium album	Chenopodium album	mortality	=	80.0	%	PMID[20839888]
NPT126	Organism	Taraxacum officinale	Taraxacum officinale	mortality	=	80.0	%	PMID[20839888]
NPT130	Organism	Digitaria sanguinalis	Digitaria sanguinalis	mortality	=	80.0	%	PMID[20839888]
NPT119	Organism	Triticum aestivum	Triticum aestivum	mortality	=	80.0	%	PMID[20839888]
NPT120	Organism	Zea mays	Zea mays	mortality	=	80.0	%	PMID[20839888]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	mortality	=	80.0	%	PMID[20839888]
NPT26742	Organism	Sinapis arvensis	Sinapis arvensis	mortality	=	80.0	%	PMID[20839888]
NPT128	Organism	Cyperus difformis	Cyperus difformis	mortality	=	20.0	%	PMID[20839888]
NPT131	Organism	Convolvulus arvensis	Convolvulus arvensis	mortality	=	80.0	%	PMID[20839888]
NPT132	Organism	Amaranthus retroflexus	Amaranthus retroflexus	mortality	=	80.0	%	PMID[20839888]
NPT26740	Organism	Rumex crispus	Rumex crispus	mortality	=	80.0	%	PMID[20839888]
NPT124	Organism	Poa annua	Poa annua	mortality	=	80.0	%	PMID[20839888]
NPT26744	Organism	Leptochloa	Leptochloa	mortality	=	80.0	%	PMID[20839888]

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 NPC385 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score	Similarity Level	Natural Product ID

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC385 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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