NPASS Compound

Natural Product: NPC475443

Natural Product ID	NPC475443
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1-O-(9Z,12Z-Octadecadienoyl)-3-O-(9Z-Octadecenoyl)Glycerol
IUPAC Name	[2-hydroxy-3-[(9E,12Z)-octadeca-9,12-dienoyl]oxypropyl] (Z)-octadec-9-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL505746
PubChem CID	44584139
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 114113 0 0 0 0 0 0 0 0999 V2000 -12.7508 -1.7107 3.9524 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.2905 -0.6953 2.9435 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6755 -1.0946 1.5295 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1812 -0.0230 0.5564 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5359 -0.3676 -0.8549 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1131 0.5308 -1.9239 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7864 0.7248 -2.4517 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5589 1.0072 -1.7096 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9790 -0.1196 -0.9658 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7553 -0.5315 -1.2888 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9809 0.0833 -2.3435 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6928 0.6684 -1.7837 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8149 -0.3806 -1.1638 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5178 0.2133 -0.6322 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7145 1.2223 0.4236 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5251 1.8939 1.0047 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6960 2.7978 0.2146 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0318 2.2705 -0.9689 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5895 2.5148 -2.0891 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1257 1.5553 -0.9675 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8142 1.0366 -2.0249 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1652 -0.0482 -2.8042 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2277 -1.2426 -2.0169 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7452 -1.9754 -1.4434 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6291 -1.8071 -0.4644 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6745 -0.7558 0.1834 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6052 -2.9182 -0.1314 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6344 -2.9170 -1.2294 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3219 -1.5903 -1.3064 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0466 -1.3075 -0.0245 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7197 0.0647 -0.0790 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4585 0.2821 1.2030 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1165 1.6582 1.2133 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8728 1.8382 2.4692 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1882 2.0908 2.4118 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0434 2.2840 3.5552 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1841 1.4300 3.8145 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6027 0.3957 3.1461 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9655 -0.1424 1.9400 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8477 -0.0604 0.6993 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0923 -0.8479 0.9532 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9526 -0.7427 -0.2911 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1623 -1.3129 -1.4462 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0351 0.4468 -3.4075 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.9879 -1.7783 4.7451 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9116 -2.7098 3.5121 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.6962 -1.3641 4.4488 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1912 -0.5262 2.9803 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7611 0.2902 3.1416 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7709 -1.2150 1.4414 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1626 -2.0506 1.3118 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1874 0.2959 0.7121 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9152 0.8534 0.8034 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3063 -1.4578 -1.0709 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.6812 -0.3853 -0.8707 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5074 1.5797 -1.6037 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8611 0.3009 -2.8039 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8685 1.5492 -3.2847 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5330 -0.1632 -3.1812 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8255 1.6497 -2.2434 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9021 1.7717 -0.8796 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4886 -0.6419 -0.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2942 -1.3740 -0.7430 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4585 0.7117 -3.0776 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5878 -0.8133 -2.9753 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1222 1.2598 -2.5043 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9599 1.3962 -0.9600 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5272 -1.1543 -1.9082 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2949 -0.9025 -0.3171 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8785 0.4231 -1.4631 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0274 -0.6875 -0.1120 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2785 0.7813 1.3188 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4133 2.0516 0.1166 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9088 2.5187 1.8958 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8813 1.1303 1.5750 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 3.2194 0.8641 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2453 3.7757 -0.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8494 0.7858 -1.7950 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9497 1.9100 -2.8016 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8263 -0.2867 -3.6658 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9021 -0.8694 -1.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9588 -1.8918 -2.6088 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9932 -2.7413 0.8713 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9836 -3.8460 -0.1748 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4022 -3.7058 -0.9799 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1939 -3.2285 -2.2054 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0780 -1.5712 -2.1490 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5492 -0.8105 -1.4666 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8353 -2.0579 0.1457 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3654 -1.2617 0.8449 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9122 0.8174 -0.1608 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3745 0.0791 -0.9745 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7356 0.2176 2.0376 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2578 -0.4914 1.2876 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3291 2.4380 1.0678 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8074 1.6737 0.3385 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3867 1.7692 3.4136 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6073 2.1787 1.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3574 2.2068 4.4754 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3279 3.3883 3.6199 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8252 1.6779 4.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5420 -0.1404 3.5201 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0151 -1.3131 2.1409 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9179 -0.0190 1.7848 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0098 0.9777 0.3572 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2943 -0.5823 -0.1225 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6402 -0.5763 1.8627 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7887 -1.9123 1.0624 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9349 -1.2092 -0.1913 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1039 0.3382 -0.5105 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5439 -2.1468 -1.1027 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4880 -0.5221 -1.8383 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8238 -1.6394 -2.2550 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4223 -0.3522 -3.8756 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 1 0 7 8 1 0 8 9 1 0 9 10 2 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 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 22 44 1 0 1 45 1 0 1 46 1 0 1 47 1 0 2 48 1 0 2 49 1 0 3 50 1 0 3 51 1 0 4 52 1 0 4 53 1 0 5 54 1 0 5 55 1 0 6 56 1 0 6 57 1 0 7 58 1 0 7 59 1 0 8 60 1 0 8 61 1 0 9 62 1 0 10 63 1 0 11 64 1 0 11 65 1 0 12 66 1 0 12 67 1 0 13 68 1 0 13 69 1 0 14 70 1 0 14 71 1 0 15 72 1 0 15 73 1 0 16 74 1 0 16 75 1 0 17 76 1 0 17 77 1 0 21 78 1 0 21 79 1 0 22 80 1 0 23 81 1 0 23 82 1 0 27 83 1 0 27 84 1 0 28 85 1 0 28 86 1 0 29 87 1 0 29 88 1 0 30 89 1 0 30 90 1 0 31 91 1 0 31 92 1 0 32 93 1 0 32 94 1 0 33 95 1 0 33 96 1 0 34 97 1 0 35 98 1 0 36 99 1 0 36100 1 0 37101 1 0 38102 1 0 39103 1 0 39104 1 0 40105 1 0 40106 1 0 41107 1 0 41108 1 0 42109 1 0 42110 1 0 43111 1 0 43112 1 0 43113 1 0 44114 1 0 M END

Standard InCHIKey	GREDRAMJRDQWEJ-DEDKAWTBSA-N
Standard InCHI	InChI=1S/C39H70O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-35-37(40)36-44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11,13,17-20,37,40H,3-10,12,14-16,21-36H2,1-2H3/b13-11-,19-17+,20-18-
SMILES	CCCCCCCC/C=CCCCCCCCC(=O)OCC(COC(=O)CCCCCCC/C=C/C/C=CCCCCC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	618.52	Volume:	713.869 ? Van der Waals volume.
Dense:	0.866	LogP:	11.322 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.803 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-8.452 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	35.0	Rigid Bonds:	5.0
TPSA:	72.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.045	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.275	Fsp³:	0.795
MCE-18:	3.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.653	Fluc inhibitor:	0.161 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.849	Promiscuous compounds:	0.236

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.061	MDCK Permeability:	-4.624
Pgp-inhibitor:	0.01	Pgp-substrate:	0.0
PAMPA:	0.0 ? 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):	0.001
20% Bioavailability (F20%):	0.938	30% Bioavailability (F30%):	0.988
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	99.215%	Volume Distribution (VD):	-0.285
Fu:	0.168% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.235
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.057	CYP2C9-substrate:	0.994
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.125 ? 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):

5.003

Half-life (T1/2):

0.792

ADMET: Toxicity

hERG Blockers:	0.719	hERG Blockers (10um):	0.916
Human Hepatotoxicity (H-HT):	0.326	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.082	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.138	Skin Sensitization:	1.0
Carcinogencity:	0.034	Eye Corrosion:	0.087
Eye Irritation:	0.54	Respiratory Toxicity:	0.535
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.563
Hematotoxicity:	0.003	Drug-induced Nephrotoxicity:	0.765
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.075
A549 Cytotoxicity:	0.956	Hek293 Cytotoxicity:	0.477
BCF:	-0.467 ? 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:	4.393 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.871 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	1.823 ? 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
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11858758]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18781	Hyoscyamus niger	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18781	Hyoscyamus niger	Species	Solanaceae	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	1

Activity Type	# Activity
Cell line	1

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
NPT858	Cell line	LNCaP	Homo sapiens	IC50	>	100000.0	nM	DrugMatrix in vitro pharmacology data

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 NPC475443 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	16452
0.1-0.2	29782
0.2-0.3	3051
0.3-0.4	428
0.4-0.5	84
0.5-0.6	22
0.6-0.7	15
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473829
0.9118	High Similarity	NPC277597
0.8158	Intermediate Similarity	NPC330426
0.8158	Intermediate Similarity	NPC127091
0.8158	Intermediate Similarity	NPC22101
0.8	Intermediate Similarity	NPC473772
0.75	Intermediate Similarity	NPC28779
0.7436	Intermediate Similarity	NPC321919
0.7368	Intermediate Similarity	NPC104537
0.725	Intermediate Similarity	NPC271921
0.6667	Remote Similarity	NPC128061
0.6579	Remote Similarity	NPC10316
0.6579	Remote Similarity	NPC200845
0.6486	Remote Similarity	NPC39633
0.6444	Remote Similarity	NPC473559
0.6444	Remote Similarity	NPC324981
0.6279	Remote Similarity	NPC54925
0.62	Remote Similarity	NPC178758
0.62	Remote Similarity	NPC192326
0.62	Remote Similarity	NPC322769
0.619	Remote Similarity	NPC476654
0.619	Remote Similarity	NPC476655
0.619	Remote Similarity	NPC476656
0.6154	Remote Similarity	NPC223677
0.6038	Remote Similarity	NPC317263
0.5789	Remote Similarity	NPC488257
0.5789	Remote Similarity	NPC469937
0.5789	Remote Similarity	NPC94699
0.5789	Remote Similarity	NPC320588
0.5789	Remote Similarity	NPC53463
0.5778	Remote Similarity	NPC48218
0.5778	Remote Similarity	NPC141481
0.5778	Remote Similarity	NPC464342
0.5682	Remote Similarity	NPC209327
0.5676	Remote Similarity	NPC309606
0.5641	Remote Similarity	NPC139545
0.5581	Remote Similarity	NPC81896
0.5556	Remote Similarity	NPC273508
0.5476	Remote Similarity	NPC148192
0.5455	Remote Similarity	NPC489083
0.5435	Remote Similarity	NPC42526
0.54	Remote Similarity	NPC474321
0.525	Remote Similarity	NPC71761
0.5128	Remote Similarity	NPC26253
0.5111	Remote Similarity	NPC143857
0.5111	Remote Similarity	NPC229252
0.5085	Remote Similarity	NPC21693

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475443 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6166
0.1-0.2	2808
0.2-0.3	135
0.3-0.4	34
0.4-0.5	5
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
0.5641	Remote Similarity	NPD5343	Phase 4
0.5366	Remote Similarity	NPD6096	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