NPASS Compound

Natural Product: NPC26500

Natural Product ID	NPC26500
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	9,12,13-Trihydroxyoctadeca-10(E),15(Z)-Dienoic Acid
IUPAC Name	(10E,15Z)-9,12,13-trihydroxyoctadeca-10,15-dienoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL469620
PubChem CID	44559173
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000504] Lineolic acids and derivatives

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 54 0 0 0 0 0 0 0 0999 V2000 -8.8248 2.1678 0.4674 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5844 1.4020 0.9711 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4368 2.2132 0.6024 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4783 1.8015 -0.1808 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4572 0.4778 -0.7727 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2895 -0.4058 -0.3956 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9464 0.1275 -0.7595 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8514 -0.7873 -0.2770 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6411 -0.5944 -0.7507 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4710 -1.4507 -0.3217 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7626 -0.7023 -0.1620 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8368 -1.6676 0.2793 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1483 -0.8667 0.4334 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2159 -1.8040 0.8677 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5675 -1.2828 1.1140 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3673 -0.6919 0.0385 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9001 0.5015 -0.6918 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6148 1.6845 0.1685 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7617 1.6641 1.4181 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1731 2.8377 -0.4507 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1535 -2.0152 0.9206 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7245 1.3379 -0.1252 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5041 -1.6710 -1.0120 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6550 1.4660 0.2701 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6033 2.6858 -0.4886 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1791 2.8810 1.2376 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6789 1.4266 2.0884 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6843 0.4097 0.5621 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3664 3.2470 1.0091 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6260 2.4761 -0.4424 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3595 -0.1264 -0.7289 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3123 0.6483 -1.9019 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3255 -0.6098 0.6930 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7866 0.1970 -1.8566 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1255 -1.5486 0.4304 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4610 0.1995 -1.4612 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6578 -2.2741 -1.0523 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0544 -0.3216 -1.1639 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7076 0.1347 0.5445 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0297 -2.4530 -0.4638 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5890 -2.0838 1.2611 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3523 -0.3362 -0.4790 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9734 -0.1532 1.2892 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8034 -2.3270 1.7964 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2880 -2.6207 0.0700 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5484 -0.5954 2.0214 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1952 -2.1541 1.5321 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4961 -1.5066 -0.7545 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4157 -0.4997 0.4163 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8380 0.8361 -1.3080 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1726 0.3428 -1.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0617 3.7267 0.0131 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2334 -2.9180 0.8359 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0111 1.8425 -0.5845 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0097 -2.2674 -0.4033 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 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 2 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 1 0 17 18 1 0 18 19 2 0 18 20 1 0 10 21 1 0 7 22 1 0 6 23 1 0 1 24 1 0 1 25 1 0 1 26 1 0 2 27 1 0 2 28 1 0 3 29 1 0 4 30 1 0 5 31 1 0 5 32 1 0 6 33 1 0 7 34 1 0 8 35 1 0 9 36 1 0 10 37 1 0 11 38 1 0 11 39 1 0 12 40 1 0 12 41 1 0 13 42 1 0 13 43 1 0 14 44 1 0 14 45 1 0 15 46 1 0 15 47 1 0 16 48 1 0 16 49 1 0 17 50 1 0 17 51 1 0 20 52 1 0 21 53 1 0 22 54 1 0 23 55 1 0 M END

Standard InCHIKey	MKYUCBXUUSZMQB-MKZMYESJSA-N
Standard InCHI	InChI=1S/C18H32O5/c1-2-3-7-11-16(20)17(21)14-13-15(19)10-8-5-4-6-9-12-18(22)23/h3,7,13-17,19-21H,2,4-6,8-12H2,1H3,(H,22,23)/b7-3-,14-13+
SMILES	CC/C=CCC(C(/C=C/C(CCCCCCCC(=O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	328.22	Volume:	355.926 ? Van der Waals volume.
Dense:	0.922	LogP:	2.705 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.354 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.737 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	3.0
TPSA:	97.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	0.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.29	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.726	Fsp³:	0.722
MCE-18:	4.0 ? 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:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.005	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.728	Promiscuous compounds:	0.205

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.189	MDCK Permeability:	-4.917
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.964 ? 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):	0.999
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.028
Plasma Protein Binding (PPB):	86.086%	Volume Distribution (VD):	-0.312
Fu:	13.369% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.728
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.014
BSEP inhibitor:	0.004

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.988	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.001	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	0.319
HLM stability:	0.007 ? 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):

4.794

Half-life (T1/2):

1.061

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.139
Human Hepatotoxicity (H-HT):	0.385	Drug-induced Liver Injury (DILI):	0.021
AMES Toxicity:	0.215	Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.202	Skin Sensitization:	0.638
Carcinogencity:	0.085	Eye Corrosion:	0.008
Eye Irritation:	0.692	Respiratory Toxicity:	0.87
Drug-induced Neurotoxicity:	0.042	Ototoxicity:	0.951
Hematotoxicity:	0.024	Drug-induced Nephrotoxicity:	0.467
Genotoxicity:	0.005	RPMI-8226 Immunitoxicity:	0.032
A549 Cytotoxicity:	0.003	Hek293 Cytotoxicity:	0.012
BCF:	0.656 ? 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:	3.329 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.843 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.603 ? 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
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0014-5793(03)00033-4]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ac991142i]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1034/j.1399-3054.2003.00030.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.274.1.397]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M302362200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M314195200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M411109200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.103.022368]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11005203]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12637544]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12805618]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14600382]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14745019]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15280363]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15820655]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15834012]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15844959]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1684022]
NPO32690	salsola tetrandra	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989538]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17611796]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057039]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18235971]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318836]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19521717]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19731587]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21193570]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21194489]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21395888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800258]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23370715]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23950498]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[24163311]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24285094]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[25457500]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[25894905]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[27363486]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27432888]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[28358502]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37726667]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38543013]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39382805]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8278506]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9658577]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	leaf	n.a.	Database[Article]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3813	Chaenomeles speciosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	Database[MetaboLights]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3813	Chaenomeles speciosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12133	Corchorus olitorius	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3813	Chaenomeles speciosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3813	Chaenomeles speciosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3813	Chaenomeles speciosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3936	Malva sylvestris	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26327	Chaenomeles sinensis	Species	Rosaceae	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	5
MBC	3

Activity Type	# Activity
Organism	8

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
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MBC	=	500.0	ug ml-1	PMID[16989538]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	400.0	ug.mL-1	PMID[16989538]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	700.0	ug.mL-1	PMID[16989538]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	>	700.0	ug ml-1	PMID[16989538]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	700.0	ug.mL-1	PMID[16989538]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	500.0	ug.mL-1	PMID[16989538]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MBC	>	700.0	ug ml-1	PMID[16989538]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	600.0	ug.mL-1	PMID[16989538]

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 NPC26500 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	27949
0.1-0.2	20459
0.2-0.3	1217
0.3-0.4	122
0.4-0.5	90
0.5-0.6	12
0.6-0.7	4
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
0.75	Intermediate Similarity	NPC99619
0.6122	Remote Similarity	NPC470320
0.6042	Remote Similarity	NPC255863
0.6042	Remote Similarity	NPC136164
0.6042	Remote Similarity	NPC245947
0.5918	Remote Similarity	NPC325627
0.58	Remote Similarity	NPC322186
0.5714	Remote Similarity	NPC243532
0.56	Remote Similarity	NPC323477
0.5532	Remote Similarity	NPC606120
0.5385	Remote Similarity	NPC49863
0.5294	Remote Similarity	NPC321838
0.5263	Remote Similarity	NPC192006
0.5192	Remote Similarity	NPC327112
0.5185	Remote Similarity	NPC328653
0.5111	Remote Similarity	NPC324004
0.5111	Remote Similarity	NPC328497

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC26500 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6175
0.1-0.2	2769
0.2-0.3	173
0.3-0.4	14
0.4-0.5	16
0.5-0.6	2
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
0.5385	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5192	Remote Similarity	NPD4246	Phase 2

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