NPASS Compound

Natural Product: NPC184579

Natural Product ID	NPC184579
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Anacardic Acid
IUPAC Name	2-hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzoic acid
Synonyms	6-(Pentadecenyl)Salicylic Acid; 6-Pentadecylsalicylic Acid; Anacardic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL455368
PubChem CID	9875131
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0000487] Salicylic acid and derivatives [CHEMONTID:0002514] Salicylic acids

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 55 55 0 0 0 0 0 0 0 0999 V2000 7.0582 2.6910 -0.0136 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9296 2.6894 -0.7021 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8288 1.7112 -0.4303 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1576 0.7988 0.6695 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2411 -0.5193 0.5566 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0272 -1.2772 -0.6534 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9629 -2.2299 -0.8013 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0239 -2.5023 0.0573 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7297 -1.9778 1.3755 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3380 -1.3422 1.4125 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3237 -2.3912 1.0906 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0621 -1.7703 1.1522 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2570 -0.6442 0.1727 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6976 -0.1683 0.3738 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9928 0.9650 -0.5812 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4054 1.3689 -0.3711 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5893 2.4786 0.4659 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8348 2.9101 0.7660 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9111 2.2356 0.2317 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7420 1.1540 -0.5851 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4586 0.6986 -0.9036 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3242 -0.4195 -1.8004 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3640 -1.0196 -2.2539 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1347 -0.9264 -2.2385 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8173 0.4564 -1.1367 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2370 1.9787 0.7839 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8284 3.4103 -0.2383 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7787 3.4114 -1.4909 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4681 1.1976 -1.3086 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9663 2.3572 -0.0675 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3560 1.2117 1.6804 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5530 -1.0455 1.4895 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0600 -0.6244 -1.5919 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0149 -1.8777 -0.8355 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9764 -2.7881 -1.7924 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3191 -3.3095 -0.2993 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5883 -2.9020 2.0458 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4505 -1.3821 1.9035 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2133 -0.9038 2.4034 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2699 -0.5306 0.6568 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4587 -2.8833 0.1115 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3165 -3.2192 1.8406 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2337 -1.3428 2.1710 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8394 -2.5327 0.9408 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1103 -0.9353 -0.8735 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5736 0.2131 0.3710 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4410 -0.9414 0.2883 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7480 0.1984 1.4446 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3312 1.8511 -0.3489 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7638 0.6306 -1.6023 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7430 2.9858 0.8684 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0424 3.7663 1.4104 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9360 2.5439 0.4445 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9626 -1.1675 -3.2271 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1600 -0.3398 -0.6308 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 2 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 20 25 1 0 21 16 1 0 1 26 1 0 1 27 1 0 2 28 1 0 3 29 1 0 3 30 1 0 4 31 1 0 5 32 1 0 6 33 1 0 6 34 1 0 7 35 1 0 8 36 1 0 9 37 1 0 9 38 1 0 10 39 1 0 10 40 1 0 11 41 1 0 11 42 1 0 12 43 1 0 12 44 1 0 13 45 1 0 13 46 1 0 14 47 1 0 14 48 1 0 15 49 1 0 15 50 1 0 17 51 1 0 18 52 1 0 19 53 1 0 24 54 1 0 25 55 1 0 M END

Standard InCHIKey	QUVGEKPNSCFQIR-UTOQUPLUSA-N
Standard InCHI	InChI=1S/C22H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h2,4-5,7-8,15,17-18,23H,1,3,6,9-14,16H2,(H,24,25)/b5-4-,8-7-
SMILES	C=CC/C=CC/C=CCCCCCCCc1cccc(c1C(=O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	342.22	Volume:	388.427 ? Van der Waals volume.
Dense:	0.881	LogP:	7.15 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.721 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.946 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	10.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	1.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.339	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.708	Fsp³:	0.409
MCE-18:	7.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.472	Fluc inhibitor:	0.074 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.091 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.275 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.723	Promiscuous compounds:	0.163

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.056	MDCK Permeability:	-4.733
Pgp-inhibitor:	0.969	Pgp-substrate:	0.0
PAMPA:	0.004 ? 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):	0.004
20% Bioavailability (F20%):	0.157	30% Bioavailability (F30%):	0.772
50% Bioavailability (F50%):	0.824

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005	MRP1:	0.973
Plasma Protein Binding (PPB):	98.397%	Volume Distribution (VD):	-0.273
Fu:	0.92% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.441
OATP1B3 inhibitor:	0.526	BCRP inhibitor:	0.827
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.015
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.985	CYP2D6-substrate:	0.823
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.012	CYP2C8-inhibitor:	1.0
HLM stability:	0.026 ? 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):

2.928

Half-life (T1/2):

0.737

ADMET: Toxicity

hERG Blockers:	0.122	hERG Blockers (10um):	0.374
Human Hepatotoxicity (H-HT):	0.054	Drug-induced Liver Injury (DILI):	0.006
AMES Toxicity:	0.328	Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.015	Skin Sensitization:	1.0
Carcinogencity:	0.01	Eye Corrosion:	1.0
Eye Irritation:	1.0	Respiratory Toxicity:	0.987
Drug-induced Neurotoxicity:	0.037	Ototoxicity:	0.105
Hematotoxicity:	0.003	Drug-induced Nephrotoxicity:	0.296
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.024
A549 Cytotoxicity:	0.368	Hek293 Cytotoxicity:	0.064
BCF:	1.411 ? 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:	4.552 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.931 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.289 ? 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
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[8021657]
NPO13016	Viscaria viscosa	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12510	Aronia arbutifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13070	Clibadium mexiae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1744	Discaria serratifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11636	Ideopsis similis	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO998	Justicia hayatai	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9180	Pyrostegia venusta	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	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	Leaf	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3580	Rana amurensis	Species	Ranidae	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]
NPO13070	Clibadium mexiae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12510	Aronia arbutifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11636	Ideopsis similis	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13016	Viscaria viscosa	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8896	Anacardium occidentale	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO998	Justicia hayatai	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9180	Pyrostegia venusta	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1744	Discaria serratifolia	Species	Rhamnaceae	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	19
Kcat	1
Kcat/Km	1
Inhibition	12
ID50	2
Activity	6
Ki	4
MIC	2
MBC	2

Activity Type	# Activity
Individual protein	41
Cell line	1
Organism	4
Others	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1432	Individual protein	Serine/threonine-protein kinase Aurora-A	Homo sapiens	Kcat	=	281.5	/s	PMID[18215015]
NPT1432	Individual protein	Serine/threonine-protein kinase Aurora-A	Homo sapiens	Kcat/Km	=	6.99	/s/mM	PMID[18215015]
NPT1079	Individual protein	Histone acetyltransferase p300	Homo sapiens	IC50	=	5000.0	nM	PMID[22100137]
NPT1079	Individual protein	Histone acetyltransferase p300	Homo sapiens	IC50	>	1000000.0	nM	PMID[19114310]
NPT1080	Individual protein	Histone acetyltransferase PCAF	Homo sapiens	IC50	=	667050.0	nM	PMID[19114310]
NPT1079	Individual protein	Histone acetyltransferase p300	Homo sapiens	Activity	=	53.1	%	PMID[19144517]
NPT1834	Individual protein	CREB-binding protein	Homo sapiens	Activity	=	44.0	%	PMID[19144517]
NPT1080	Individual protein	Histone acetyltransferase PCAF	Homo sapiens	Activity	=	52.1	%	PMID[19144517]
NPT1080	Individual protein	Histone acetyltransferase PCAF	Homo sapiens	IC50	=	1000000.0	nM	PMID[20655754]
NPT1080	Individual protein	Histone acetyltransferase PCAF	Homo sapiens	Inhibition	=	40.0	%	PMID[22100137]
NPT1489	Individual protein	Glyceraldehyde-3-phosphate dehydrogenase, glycosomal	Trypanosoma cruzi	IC50	=	28000.0	nM	PMID[18789702]
NPT1489	Individual protein	Glyceraldehyde-3-phosphate dehydrogenase, glycosomal	Trypanosoma cruzi	Ki	=	4000.0	nM	PMID[18789702]
NPT1489	Individual protein	Glyceraldehyde-3-phosphate dehydrogenase, glycosomal	Trypanosoma cruzi	Ki	=	6000.0	nM	PMID[18789702]
NPT1489	Individual protein	Glyceraldehyde-3-phosphate dehydrogenase, glycosomal	Trypanosoma cruzi	Ki	=	2000.0	nM	PMID[18789702]
NPT1834	Individual protein	CREB-binding protein	Homo sapiens	Inhibition	=	62.0	%	PMID[21292492]
NPT1080	Individual protein	Histone acetyltransferase PCAF	Homo sapiens	Inhibition	<=	20.0	%	PMID[22100137]
NPT1079	Individual protein	Histone acetyltransferase p300	Homo sapiens	Inhibition	<=	20.0	%	PMID[22100137]
NPT1080	Individual protein	Histone acetyltransferase PCAF	Homo sapiens	IC50	=	8500.0	nM	PMID[22100137]
NPT1079	Individual protein	Histone acetyltransferase p300	Homo sapiens	Inhibition	=	40.0	%	PMID[22100137]
NPT2653	Individual protein	Histone acetyltransferase KAT8	Homo sapiens	IC50	=	43000.0	nM	PMID[22100137]
NPT650	Individual protein	Beta-lactamase pse-1	Escherichia coli	IC50	=	1100.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80506-0]
NPT651	Individual protein	Beta-lactamase OXA-1	Escherichia coli	IC50	=	25000.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80506-0]
NPT654	Individual protein	Beta-lactamase	Enterobacter cloacae	IC50	=	1400.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80506-0]
NPT655	Individual protein	Beta-lactamase	Proteus mirabilis	IC50	=	31000.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80506-0]
NPT89	Individual protein	Seed lipoxygenase-1	Glycine max	IC50	>	250000.0	nM	DOI[10.1021/np50114a025]
NPT652	Individual protein	Beta-lactamase TEM	Escherichia coli	IC50	=	800.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80506-0]
NPT4248	Individual protein	Histone acetyltransferase KAT5	Homo sapiens	IC50	=	9000.0	nM	PMID[19114310]
NPT4248	Individual protein	Histone acetyltransferase KAT5	Homo sapiens	IC50	=	374590.0	nM	PMID[19114310]
NPT4248	Individual protein	Histone acetyltransferase KAT5	Homo sapiens	Inhibition	>	76.0	%	PMID[22100137]
NPT4248	Individual protein	Histone acetyltransferase KAT5	Homo sapiens	IC50	=	64000.0	nM	PMID[22100137]
NPT4248	Individual protein	Histone acetyltransferase KAT5	Homo sapiens	Inhibition	>	50.0	%	PMID[22100137]
NPT653	Individual protein	Beta-lactamase	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)	IC50	=	7200.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80506-0]
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	Inhibition	=	15.0	%	PMID[8021657]
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	Inhibition	=	45.0	%	PMID[8021657]
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	ID50	=	4.2	mM	PMID[8021657]
NPT43	Individual protein	Tyrosinase	Agaricus bisporus	ID50	=	1.1	mM	PMID[8021657]
NPT443	Individual protein	Histone acetyltransferase GCN5	Homo sapiens	Activity	=	112.6	%	PMID[19144517]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell line	U-937	Homo sapiens	Activity	=	15.0	%	PMID[17154519]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	1.56	ug.mL-1	PMID[17959274]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MBC	=	0.78	ug ml-1	PMID[17959274]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MBC	=	6.25	ug ml-1	PMID[17959274]
NPT2	Others	Unspecified	n.a.	Activity	=	62.0	%	PMID[18434144]
NPT167	Organism	Propionibacterium acnes	Propionibacterium acnes	MIC	=	0.78	ug.mL-1	PMID[8158169]
NPT2	Others	Unspecified	n.a.	IC50	=	297230.0	nM	PMID[19114310]
NPT2	Others	Unspecified	n.a.	Inhibition	=	15.0	%	PMID[19144517]

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 NPC184579 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	24180
0.1-0.2	24208
0.2-0.3	1312
0.3-0.4	106
0.4-0.5	27
0.5-0.6	3
0.6-0.7	4
0.7-0.8	0
0.8-0.85	7
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC233165
0.8824	High Similarity	NPC115188
0.8824	High Similarity	NPC159760
0.8824	High Similarity	NPC301987
0.8824	High Similarity	NPC26433
0.84	Intermediate Similarity	NPC238531
0.84	Intermediate Similarity	NPC178395
0.8235	Intermediate Similarity	NPC244994
0.8235	Intermediate Similarity	NPC222876
0.8235	Intermediate Similarity	NPC292665
0.8235	Intermediate Similarity	NPC179092
0.82	Intermediate Similarity	NPC483452
0.7636	Intermediate Similarity	NPC167055
0.7059	Intermediate Similarity	NPC483451
0.7059	Intermediate Similarity	NPC227450
0.7059	Intermediate Similarity	NPC272454
0.7059	Intermediate Similarity	NPC35856
0.7059	Intermediate Similarity	NPC609957
0.6833	Remote Similarity	NPC240744
0.6667	Remote Similarity	NPC244351
0.6667	Remote Similarity	NPC483453
0.6545	Remote Similarity	NPC605990
0.5763	Remote Similarity	NPC17840
0.5763	Remote Similarity	NPC247477
0.5263	Remote Similarity	NPC192

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC184579 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4116
0.1-0.2	4828
0.2-0.3	202
0.3-0.4	4
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