NPASS Compound

Natural Product: NPC490208

Natural Product ID	NPC490208
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Glycolipids
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000257] Sphingolipids [CHEMONTID:0003392] Phosphosphingolipids

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 83 82 0 0 0 0 0 0 0 0999 V2000 9.1801 -1.8774 2.1548 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7310 -1.4827 1.9569 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4738 -0.2879 2.8546 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3712 0.8466 2.4819 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1215 1.3122 1.0876 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6989 1.8231 0.9786 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4132 2.3611 -0.4147 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5190 1.3892 -1.5079 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7134 0.1783 -1.5826 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2426 0.2716 -1.6989 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5679 0.8816 -0.5373 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0253 0.8991 -0.7653 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4463 1.5468 0.4764 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0389 1.6418 0.3919 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6862 1.1884 -0.6701 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1876 1.2589 -0.8092 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4834 2.0560 -1.9395 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -0.1457 -1.1368 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0647 -0.0755 -1.6386 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5084 -1.3033 -2.1180 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8071 -1.1768 -3.1533 P 0 0 0 0 0 0 0 0 0 0 0 0 -5.8548 0.1561 -3.8677 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5561 -2.3348 -4.3921 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2949 -1.4293 -2.4583 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3992 -1.0556 -1.1272 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8478 -1.2486 -0.7322 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1189 -0.9044 0.6243 N 0 0 0 0 0 4 0 0 0 0 0 0 -10.1734 -1.7996 1.1096 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6599 0.4406 0.7726 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0033 -1.0534 1.5147 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4420 -1.0669 -0.0660 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5332 -2.1579 -0.1873 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8707 -2.3664 -1.2345 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7765 -1.5231 1.2933 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5749 -1.4335 3.0905 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2124 -2.9928 2.2293 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0476 -2.3123 2.2872 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5051 -1.1879 0.9284 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4178 0.0276 2.8553 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6884 -0.5678 3.9274 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2388 1.6847 3.2172 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4471 0.5717 2.5457 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7892 2.1860 0.8330 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3144 0.5552 0.3235 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9382 1.0605 1.2076 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5809 2.6581 1.6830 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3225 3.0956 -0.5876 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5944 3.0585 -0.3664 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6270 1.0893 -1.6371 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3652 1.9561 -2.5049 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1248 -0.4837 -2.4387 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9280 -0.4310 -0.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9624 0.8004 -2.6637 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8006 -0.7545 -1.8657 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8040 1.8974 -0.2840 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6697 0.1690 0.3331 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6666 -0.1367 -0.9048 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8142 1.4675 -1.6764 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7538 0.9055 1.3326 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8840 2.5637 0.5479 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5707 2.0860 1.2078 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0798 0.7520 -1.4590 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6719 1.6697 0.0854 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7837 2.9480 -1.6982 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9645 -0.4562 -1.9963 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1513 0.6493 -2.4481 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7086 0.1835 -0.7819 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3752 -2.8081 -4.6349 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1646 0.0290 -1.0627 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7060 -1.5793 -0.4486 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4467 -0.5217 -1.3587 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2394 -2.2477 -0.9580 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1034 -1.6784 0.5264 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2900 -1.7421 2.1987 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8016 -2.8289 0.8773 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2501 0.4422 1.7128 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4113 0.5463 -0.0453 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8879 1.2139 0.7689 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6796 -2.1098 1.5729 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1791 -0.3399 1.3055 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3665 -0.7921 2.5413 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9616 -0.9612 0.8536 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3798 -2.8632 0.6434 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 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 27 30 1 0 18 31 1 0 31 32 1 0 32 33 2 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 0 2 38 1 0 3 39 1 0 3 40 1 0 4 41 1 0 4 42 1 0 5 43 1 0 5 44 1 0 6 45 1 0 6 46 1 0 7 47 1 0 7 48 1 0 8 49 1 0 8 50 1 0 9 51 1 0 9 52 1 0 10 53 1 0 10 54 1 0 11 55 1 0 11 56 1 0 12 57 1 0 12 58 1 0 13 59 1 0 13 60 1 0 14 61 1 0 15 62 1 0 16 63 1 1 17 64 1 0 18 65 1 6 19 66 1 0 19 67 1 0 23 68 1 0 25 69 1 0 25 70 1 0 26 71 1 0 26 72 1 0 28 73 1 0 28 74 1 0 28 75 1 0 29 76 1 0 29 77 1 0 29 78 1 0 30 79 1 0 30 80 1 0 30 81 1 0 31 82 1 0 32 83 1 0 M CHG 1 27 1 M END

Standard InCHIKey	LRYZPFWEZHSTHD-HEFFAWAOSA-O
Standard InCHI	InChI=1S/C24H49N2O6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(28)23(25-22-27)21-32-33(29,30)31-20-19-26(2,3)4/h17-18,22-24,28H,5-16,19-21H2,1-4H3,(H-,25,27,29,30)/p+1/b18-17+/t23-,24+/m0/s1
SMILES	CCCCCCCCCCCCCC=C[C@@H](O)[C@H](COP(=O)(O)OCC[N+](C)(C)C)NC=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	493.34	Volume:	514.268 ? Van der Waals volume.
Dense:	0.959	LogP:	2.819 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.326 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.873 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	23.0	Rigid Bonds:	3.0
TPSA:	105.09 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	3.0	Rings:	0.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.063	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.018	Fsp³:	0.875
MCE-18:	8.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.604	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.06	Promiscuous compounds:	0.126

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.402	MDCK Permeability:	-4.798
Pgp-inhibitor:	0.001	Pgp-substrate:	0.022
PAMPA:	0.001 ? 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):	0.976
20% Bioavailability (F20%):	0.995	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.002
Plasma Protein Binding (PPB):	97.177%	Volume Distribution (VD):	0.226
Fu:	3.461% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.397
BSEP inhibitor:	0.97

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.211
CYP2C19-inhibitor:	0.665	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.928
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.003
HLM stability:	0.0 ? 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):

3.836

Half-life (T1/2):

1.115

ADMET: Toxicity

hERG Blockers:	0.051	hERG Blockers (10um):	0.162
Human Hepatotoxicity (H-HT):	0.135	Drug-induced Liver Injury (DILI):	0.016
AMES Toxicity:	0.004	Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.996	Skin Sensitization:	0.998
Carcinogencity:	0.629	Eye Corrosion:	0.851
Eye Irritation:	0.988	Respiratory Toxicity:	0.998
Drug-induced Neurotoxicity:	0.393	Ototoxicity:	0.078
Hematotoxicity:	0.01	Drug-induced Nephrotoxicity:	0.983
Genotoxicity:	0.501	RPMI-8226 Immunitoxicity:	0.107
A549 Cytotoxicity:	0.01	Hek293 Cytotoxicity:	0.435
BCF:	0.822 ? 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:	4.531 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.031 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.212 ? 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
NPO29007	Brassica juncea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1155/2014/726070]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota	Seeds	Cornell Univeristy, Ithaca		PMID[17439238]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota	Seeds	Petone, New Zealand		PMID[17439238]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota	Seeds	Randolph, WI		PMID[17439238]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota	Seeds	Shenandoah, IA		PMID[17439238]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota	Seeds	n.a.		PMID[17439238]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota	Seeds	Warminster, PA		PMID[17439238]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota	Seeds	Onehunga, New Zealand,		PMID[17439238]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota	Seeds	Cornell University, Geneva, NY		PMID[17439238]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota	Seeds	Winslow, ME		PMID[17439238]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	Whole Plant	Dongshan, Nanjing, Jiangsu Province, China	2012-NOV	PMID[25314138]
NPO29007	Brassica juncea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25700090]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota	Fruits	Wolkowo, Poland	2016-Oct	PMID[31487816]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38192648]
NPO42011	Sechium edule	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29007	Brassica juncea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO42011	Sechium edule	Species	Cucurbitaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO42011	Sechium edule	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29007	Brassica juncea	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29007	Brassica juncea	Species	Brassicaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO29007	Brassica juncea	Species	Brassicaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO42011	Sechium edule	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO42011	Sechium edule	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO42011	Sechium edule	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29007	Brassica juncea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29007	Brassica juncea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20837	Ipomoea aquatica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29007	Brassica juncea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29007	Brassica juncea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29007	Brassica juncea	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO441	Cucurbita maxima	Species	Cucurbitaceae	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
NPO20837	Ipomoea aquatica	Raw	Plant	3362.8	792.1	5933.5	mg/100g	Database [DUKE]
NPO29007	Brassica juncea	Other	Plant	1914	322.5	3505.5	mg/100g	Database [DUKE]
NPO42011	Sechium edule	Other (raw)	Leaf	2375.5	714.5	4036.5	mg/100g	Database [DUKE]
NPO441	Cucurbita maxima	Raw	Plant	1966.25	427	3505.5	mg/100g	Database [DUKE]

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

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

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 NPC490208 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	21517
0.1-0.2	27395
0.2-0.3	902
0.3-0.4	41
0.4-0.5	4
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC490208 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6177
0.1-0.2	2878
0.2-0.3	89
0.3-0.4	3
0.4-0.5	2
0.5-0.6	1
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
0.5789	Remote Similarity	NPD6949	Clinical (unspecified phase)

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