NPASS Compound

Natural Product: NPC307846

Natural Product ID	NPC307846
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Plumericin
IUPAC Name	n.a.
Synonyms	Plumericin; Plurnericin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL517300
PubChem CID	5281545
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

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 35 38 0 0 0 0 0 0 0 0999 V2000 5.6895 0.2990 1.4184 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4909 -0.2367 0.9121 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4371 0.5984 0.6251 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5812 1.8310 0.8275 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1699 0.0990 0.0979 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9903 -1.1917 -0.1245 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7494 -1.5604 -0.6251 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3940 -1.0492 0.0377 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2719 0.4270 0.2224 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0474 1.0087 -0.2152 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9212 1.1833 -1.7053 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3592 1.1587 -2.0535 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1964 0.9673 -0.8419 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9128 2.0990 -0.4657 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1980 1.7397 -0.0789 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1511 2.5385 0.2189 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2577 0.2813 -0.0755 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1051 -0.4604 0.6173 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0046 -1.9395 0.4844 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1821 -0.1642 -0.9996 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5656 -1.3220 -0.6532 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6935 1.4153 1.4298 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5090 -0.0193 0.7416 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9413 -0.0644 2.4246 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7976 -1.9198 0.0831 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5161 -1.5881 1.0259 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5637 0.7646 1.2403 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1763 2.0048 0.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7452 1.3100 -2.3923 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7980 1.2576 -3.0538 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8285 0.0264 1.2449 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9748 -2.3434 0.8983 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9263 -2.2449 -0.5715 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1709 -2.3175 1.0853 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5633 -0.1336 -2.0434 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 1 14 15 1 0 15 16 2 0 15 17 1 0 17 18 2 0 18 19 1 0 17 20 1 0 20 21 1 0 10 5 1 0 20 13 1 0 21 8 1 0 13 9 1 0 1 22 1 0 1 23 1 0 1 24 1 0 6 25 1 0 8 26 1 1 9 27 1 1 10 28 1 1 11 29 1 0 12 30 1 0 18 31 1 0 19 32 1 0 19 33 1 0 19 34 1 0 20 35 1 6 M END

Standard InCHIKey	VFXXNAVZODKBIW-JKXVGBJFSA-N
Standard InCHI	InChI=1S/C15H14O6/c1-3-7-11-15(21-13(7)17)5-4-8-9(12(16)18-2)6-19-14(20-11)10(8)15/h3-6,8,10-11,14H,1-2H3/b7-3+/t8-,10-,11+,14-,15+/m1/s1
SMILES	COC(=O)C1=CO[C@H]2[C@H]3[C@@H]1C=C[C@@]13OC(=O)/C(=C/C)/[C@@H]1O2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	290.08	Volume:	273.329 ? Van der Waals volume.
Dense:	1.061	LogP:	1.79 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.84 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.687 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	20.0
TPSA:	71.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	0.0	Rings:	4.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.405	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.608	Fsp³:	0.467
MCE-18:	79.455 ? 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:	0.279	Fluc inhibitor:	0.224 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.085 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.627	Promiscuous compounds:	0.218

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.167	MDCK Permeability:	-4.7
Pgp-inhibitor:	0.074	Pgp-substrate:	0.495
PAMPA:	0.266 ? 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):	0.058
20% Bioavailability (F20%):	0.784	30% Bioavailability (F30%):	0.947
50% Bioavailability (F50%):	0.886

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.326	MRP1:	0.979
Plasma Protein Binding (PPB):	85.341%	Volume Distribution (VD):	0.109
Fu:	15.874% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.476
OATP1B3 inhibitor:	0.708	BCRP inhibitor:	0.036
BSEP inhibitor:	0.835

ADMET: Metabolism

CYP1A2-inhibitor:	0.522	CYP1A2-substrate:	0.515
CYP2C19-inhibitor:	0.091	CYP2C19-substrate:	0.149
CYP2C9-inhibitor:	0.324	CYP2C9-substrate:	0.162
CYP2D6-inhibitor:	0.115	CYP2D6-substrate:	0.381
CYP3A4-inhibitor:	0.136	CYP3A4-substrate:	0.876
CYP2B6-substrate:	0.02	CYP2C8-inhibitor:	0.926
HLM stability:	0.829 ? 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):

9.34

Half-life (T1/2):

1.818

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.185
Human Hepatotoxicity (H-HT):	0.546	Drug-induced Liver Injury (DILI):	0.923
AMES Toxicity:	0.942	Rat Oral Acute Toxicity:	0.733
Maximum Recommended Daily Dose:	0.705	Skin Sensitization:	0.999
Carcinogencity:	0.893	Eye Corrosion:	0.006
Eye Irritation:	0.705	Respiratory Toxicity:	0.353
Drug-induced Neurotoxicity:	0.808	Ototoxicity:	0.558
Hematotoxicity:	0.799	Drug-induced Nephrotoxicity:	0.913
Genotoxicity:	0.994	RPMI-8226 Immunitoxicity:	0.234
A549 Cytotoxicity:	0.562	Hek293 Cytotoxicity:	0.499
BCF:	0.984 ? 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:	3.726 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.094 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.651 ? 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
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	bark	Indonesia	n.a.	PMID[1965200]
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25832441]
NPO40011	Allamanda schottii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3379414]
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38783072]
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39349567]
NPO40860	Himatanthus fallax	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9428163]
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9428163]
NPO17707	Dioscorea villosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3990	Acacia salicina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3446	Acanthaster planci	Species	Acanthasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16254	Backhousia angustifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6746	Blighia welwitschii	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17373.1	Cunninghamia lanceolata var. konishii	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18768	Haliclona tubifera	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2591	Io fluvialis	Species	Pleuroceridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16377	Juniperus ashei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9524	Kalanchoe blossfeldiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21319	Odontella aurita	Species	Eupodiscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20294	Paramuricea chamaeleon	Species	Paramuriceidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21254	Paullinia cupana	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18031	Russula vesca	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15966	Sassafras officinalis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23695	Setosphaeria turcica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10438	Tanacetum nubigenum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1624	Yersinia enterocolitica	Species	Yersiniaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21254	Paullinia cupana	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21254	Paullinia cupana	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18031	Russula vesca	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16254	Backhousia angustifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15966	Sassafras officinalis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23695	Setosphaeria turcica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12734	Plumeria rubra	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3990	Acacia salicina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10438	Tanacetum nubigenum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2591	Io fluvialis	Species	Pleuroceridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9524	Kalanchoe blossfeldiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16377	Juniperus ashei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18768	Haliclona tubifera	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6746	Blighia welwitschii	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21254	Paullinia cupana	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17373.1	Cunninghamia lanceolata var. konishii	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17707	Dioscorea villosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21319	Odontella aurita	Species	Eupodiscaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1624	Yersinia enterocolitica	Species	Yersiniaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20294	Paramuricea chamaeleon	Species	Paramuriceidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5188	Allamanda cathartica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3446	Acanthaster planci	Species	Acanthasteridae	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	4
ED50	8
Inhibition	1
IC12	2
GI50	64
Activity	1

Activity Type	# Activity
Individual protein	1
Cell line	68
Non-molecular	5
Organism	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[1710653]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell line	HT-1080	Homo sapiens	ED50	=	0.2	ug ml-1	PMID[1965200]
NPT91	Cell line	KB	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[1965200]
NPT168	Cell line	P388	Mus musculus	ED50	=	1.2	ug ml-1	PMID[1965200]
NPT726	Cell line	M109	Mus musculus	IC50	=	100.0	ug.mL-1	PMID[9428163]
NPT886	Cell line	NIH3T3	Mus musculus	GI50	=	430600.0	nM	PMID[19199646]
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	=	275600.0	nM	PMID[19199646]
NPT1773	Cell line	ME-180	Homo sapiens	GI50	>	430000.0	nM	PMID[19199646]
NPT90	Cell line	DU-145	Homo sapiens	GI50	>	430000.0	nM	PMID[19199646]
NPT83	Cell line	MCF7	Homo sapiens	GI50	>	430000.0	nM	PMID[19199646]
NPT139	Cell line	HT-29	Homo sapiens	GI50	>	430000.0	nM	PMID[19199646]
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	1976.97	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	916.22	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	3118.89	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	1614.36	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	240.44	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	2118.36	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	2344.23	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	1927.52	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	837.53	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	651.63	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	860.99	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	459.2	nM	PubChem BioAssay data set
NPT378	Cell line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	676.08	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	6382.63	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	2703.96	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	594.29	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	3655.95	nM	PubChem BioAssay data set
NPT572	Cell line	DMS-273	Homo sapiens	GI50	n.a.	2317.39	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	3564.51	nM	PubChem BioAssay data set
NPT573	Cell line	M19-MEL	Homo sapiens	GI50	n.a.	726.11	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	431.52	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	2275.1	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	353.18	nM	PubChem BioAssay data set
NPT574	Cell line	XF498	Homo sapiens	GI50	n.a.	1380.38	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	2365.92	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	422.67	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	335.74	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	1517.05	nM	PubChem BioAssay data set
NPT168	Cell line	P388	Mus musculus	GI50	n.a.	104.71	nM	PubChem BioAssay data set
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	n.a.	2167.7	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	1435.49	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	2679.17	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	3467.37	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	3341.95	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	671.43	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	450.82	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	1279.38	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	1303.17	nM	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	GI50	n.a.	831.76	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	3926.45	nM	PubChem BioAssay data set
NPT576	Cell line	DMS-114	Homo sapiens	GI50	n.a.	1122.02	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	2084.49	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	1135.01	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	814.7	nM	PubChem BioAssay data set
NPT552	Cell line	P388/ADR	Mus musculus	GI50	n.a.	85.31	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	2460.37	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	1193.99	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	591.56	nM	PubChem BioAssay data set
NPT578	Cell line	SNB-78	Homo sapiens	GI50	n.a.	1940.89	nM	PubChem BioAssay data set
NPT579	Cell line	DLD-1	Homo sapiens	GI50	n.a.	431.52	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	341.19	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	2177.71	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	2437.81	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	1004.62	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	549.54	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	1004.62	nM	PubChem BioAssay data set
NPT732	Cell line	HOP-18	Homo sapiens	GI50	n.a.	4666.59	nM	PubChem BioAssay data set
NPT738	Cell line	SN12K1	Homo sapiens	GI50	n.a.	1088.93	nM	PubChem BioAssay data set
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	2.6	ug ml-1	PMID[3379414]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	Inhibition	=	44.0	%	PMID[3379414]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	2.8	ug ml-1	PMID[1965200]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.4	ug ml-1	PMID[1965200]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.2	ug ml-1	PMID[1965200]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	0.1	ug ml-1	PMID[1965200]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	74.0	ug ml-1	PMID[9428163]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	241.2	uM	PMID[19199646]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	Activity	=	5.0	uM	PMID[19199646]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	4100.0	nM	PMID[30342363]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	7200.0	nM	PMID[30342363]

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
-	Artemia	LC50	=	1.7	ppm	PMID[3379414]

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 NPC307846 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	27061
0.1-0.2	22443
0.2-0.3	305
0.3-0.4	41
0.4-0.5	3
0.5-0.6	2
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC305157
0.6032	Remote Similarity	NPC210330
0.6	Remote Similarity	NPC473428
0.5507	Remote Similarity	NPC76211
0.5167	Remote Similarity	NPC475960

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC307846 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7784
0.1-0.2	1366
0.2-0.3	0
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