NPASS Compound

Natural Product: NPC320642

Natural Product ID	NPC320642
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(5S,6E,8Z,11Z,14Z)-5-Hydroperoxyicosa-6,8,11,14-Tetraenoic Acid
IUPAC Name	(5S,6E,8Z,11Z,14Z)-5-hydroperoxyicosa-6,8,11,14-tetraenoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1743204
PubChem CID	5280778
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000387] Hydroperoxyeicosatetraenoic 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 56 55 0 0 0 0 0 0 0 0999 V2000 7.7389 -0.5042 -1.7187 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1650 0.1552 -0.4546 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1195 0.4961 0.5568 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3475 -0.6016 1.1698 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4614 -1.3389 0.2444 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3315 -0.4774 -0.2196 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0762 0.7265 0.2247 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9004 1.4749 -0.3479 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9928 1.7689 0.7787 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7746 1.3678 0.8530 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0615 0.5590 -0.1417 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4048 -0.7323 0.4101 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6239 -1.1019 0.4572 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7533 -0.3499 -0.0076 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9771 -0.8611 0.1041 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1885 -0.1185 -0.3652 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0528 0.1206 0.8234 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3017 0.8621 0.5012 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2586 0.2257 -0.4346 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7594 -1.0755 0.0660 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4586 -1.7566 -0.7345 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4617 -1.4905 1.3446 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7777 -0.7460 -1.4273 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5142 -0.1555 -2.5833 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8762 -1.6124 -1.7415 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4979 -0.1540 -2.5160 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7448 -0.2194 -2.0942 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0084 -0.4279 0.0425 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6123 1.1622 -0.7533 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6567 1.1155 1.3437 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4800 1.2716 0.0157 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6825 -0.2120 2.0077 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0215 -1.3792 1.6466 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9411 -2.1693 0.8537 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9006 -1.7961 -0.6391 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6466 -0.8631 -0.9950 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5883 1.2700 1.0081 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4082 0.9274 -1.1354 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3017 2.4354 -0.7779 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4030 2.3909 1.6358 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1760 1.6442 1.7461 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6057 0.4142 -1.1042 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8830 1.1454 -0.4032 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3987 -1.3820 0.7918 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8367 -2.0959 0.8960 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7235 0.6300 -0.4609 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0744 -1.8369 0.5479 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8048 0.8631 -0.7484 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2802 -0.8567 1.3526 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4801 0.7122 1.6165 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9920 1.8773 0.0945 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8125 1.1173 1.4862 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9045 0.0869 -1.4543 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1554 0.9249 -0.5568 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8559 -2.3442 1.7242 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5843 0.1681 -2.5281 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 3 7 8 1 0 8 9 1 0 9 10 2 3 10 11 1 0 11 12 1 0 12 13 2 3 13 14 1 0 14 15 2 3 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 20 22 1 0 16 23 1 0 23 24 1 0 1 25 1 0 1 26 1 0 1 27 1 0 2 28 1 0 2 29 1 0 3 30 1 0 3 31 1 0 4 32 1 0 4 33 1 0 5 34 1 0 5 35 1 0 6 36 1 0 7 37 1 0 8 38 1 0 8 39 1 0 9 40 1 0 10 41 1 0 11 42 1 0 11 43 1 0 12 44 1 0 13 45 1 0 14 46 1 0 15 47 1 0 16 48 1 0 17 49 1 0 17 50 1 0 18 51 1 0 18 52 1 0 19 53 1 0 19 54 1 0 22 55 1 0 24 56 1 0 M END

Standard InCHIKey	JNUUNUQHXIOFDA-JGKLHWIESA-N
Standard InCHI	InChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h6-7,9-10,12-14,16,19,23H,2-5,8,11,15,17-18H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1
SMILES	CCCCCC=CCC=CCC=CC=CC(CCCC(=O)O)OO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	336.23	Volume:	376.455 ? Van der Waals volume.
Dense:	0.893	LogP:	5.467 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.321 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.783 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	5.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	0.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.133	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.566	Fsp³:	0.55
MCE-18:	2.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.141	Fluc inhibitor:	0.01 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.109 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.907	Promiscuous compounds:	0.278

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.179	MDCK Permeability:	-4.957
Pgp-inhibitor:	0.0	Pgp-substrate:	0.003
PAMPA:	0.834 ? 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):	0.046
20% Bioavailability (F20%):	0.036	30% Bioavailability (F30%):	0.385
50% Bioavailability (F50%):	0.124

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133	MRP1:	0.93
Plasma Protein Binding (PPB):	97.534%	Volume Distribution (VD):	-0.448
Fu:	2.327% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.173
OATP1B3 inhibitor:	0.898	BCRP inhibitor:	0.006
BSEP inhibitor:	0.141

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.664	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.996	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.003 ? 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):

6.42

Half-life (T1/2):

0.539

ADMET: Toxicity

hERG Blockers:	0.179	hERG Blockers (10um):	0.245
Human Hepatotoxicity (H-HT):	0.246	Drug-induced Liver Injury (DILI):	0.049
AMES Toxicity:	0.768	Rat Oral Acute Toxicity:	0.088
Maximum Recommended Daily Dose:	0.167	Skin Sensitization:	1.0
Carcinogencity:	0.205	Eye Corrosion:	0.364
Eye Irritation:	0.915	Respiratory Toxicity:	0.655
Drug-induced Neurotoxicity:	0.017	Ototoxicity:	0.551
Hematotoxicity:	0.082	Drug-induced Nephrotoxicity:	0.325
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.056
A549 Cytotoxicity:	0.027	Hek293 Cytotoxicity:	0.135
BCF:	0.961 ? 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:	3.758 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.061 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.852 ? 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
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	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
Potency	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT698	Individual protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	8436.8	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC320642 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	30901
0.1-0.2	17463
0.2-0.3	1222
0.3-0.4	173
0.4-0.5	51
0.5-0.6	32
0.6-0.7	11
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8372	Intermediate Similarity	NPC328311
0.8222	Intermediate Similarity	NPC329249
0.75	Intermediate Similarity	NPC318420
0.75	Intermediate Similarity	NPC326268
0.675	Remote Similarity	NPC321062
0.6735	Remote Similarity	NPC92558
0.6585	Remote Similarity	NPC154245
0.6585	Remote Similarity	NPC85813
0.6585	Remote Similarity	NPC223697
0.6585	Remote Similarity	NPC6095
0.6341	Remote Similarity	NPC91495
0.6341	Remote Similarity	NPC5413
0.619	Remote Similarity	NPC59051
0.6122	Remote Similarity	NPC323045
0.6122	Remote Similarity	NPC317881
0.5952	Remote Similarity	NPC70387
0.5918	Remote Similarity	NPC329550
0.5882	Remote Similarity	NPC605544
0.5882	Remote Similarity	NPC607260
0.5854	Remote Similarity	NPC424
0.5854	Remote Similarity	NPC36061
0.5854	Remote Similarity	NPC69510
0.5854	Remote Similarity	NPC77272
0.5854	Remote Similarity	NPC290563
0.5854	Remote Similarity	NPC139029
0.5854	Remote Similarity	NPC281972
0.5854	Remote Similarity	NPC261831
0.5854	Remote Similarity	NPC87564
0.5814	Remote Similarity	NPC52955
0.5814	Remote Similarity	NPC88966
0.5814	Remote Similarity	NPC25417
0.5814	Remote Similarity	NPC1813
0.5714	Remote Similarity	NPC317583
0.5714	Remote Similarity	NPC95145
0.5714	Remote Similarity	NPC325642
0.5714	Remote Similarity	NPC65174
0.5686	Remote Similarity	NPC322461
0.561	Remote Similarity	NPC281245
0.56	Remote Similarity	NPC327112
0.551	Remote Similarity	NPC323597
0.551	Remote Similarity	NPC211752
0.551	Remote Similarity	NPC323498
0.55	Remote Similarity	NPC319021
0.5476	Remote Similarity	NPC92114
0.5349	Remote Similarity	NPC149821
0.5294	Remote Similarity	NPC325977
0.5156	Remote Similarity	NPC319473

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC320642 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6529
0.1-0.2	2442
0.2-0.3	140
0.3-0.4	24
0.4-0.5	7
0.5-0.6	6
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	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6585	Remote Similarity	NPD4266	Phase 2
0.6341	Remote Similarity	NPD3173	Phase 4
0.5854	Remote Similarity	NPD3195	Phase 2
0.5854	Remote Similarity	NPD3196	Approved
0.5814	Remote Similarity	NPD3172	Approved
0.5652	Remote Similarity	NPD3194	Phase 4
0.56	Remote Similarity	NPD4246	Phase 2
0.54	Remote Similarity	NPD39	Phase 4

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