NPASS Compound

Natural Product: NPC491258

Natural Product ID	NPC491258
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Omega-3 Fatty Acid
IUPAC Name	(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid;(5E,8E,11E,14E,17E)-henicosa-5,8,11,14,17-pentaenoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	133082085
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0002950] Very long-chain fatty 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 111109 0 0 0 0 0 0 0 0999 V2000 -8.1404 1.2412 -2.0824 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2270 0.3076 -1.6664 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7529 -0.8829 -0.8776 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0631 -0.4818 0.3815 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7982 -0.8279 0.5951 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1304 -0.4044 1.8852 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9402 0.4474 1.5993 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7224 0.1055 1.9841 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5557 0.9678 1.6879 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6014 0.1858 0.8613 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3829 -0.0374 1.2849 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5946 -0.8314 0.4525 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7543 0.0431 0.1512 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9542 -0.2966 0.5454 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1553 0.5701 0.2539 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0954 -0.2489 -0.5507 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3480 -0.5256 -0.1621 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2736 -1.3457 -0.9774 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4753 -0.5387 -1.3423 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1707 -0.0833 -0.0791 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3639 0.6972 -0.5163 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1706 0.1623 -1.2972 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5722 2.0011 -0.0631 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4678 -0.6045 2.9732 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1127 0.1131 2.8177 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0344 -0.8180 3.0901 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0985 -1.2112 2.2984 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8329 -0.8676 0.9257 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6975 -0.0043 0.1600 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3089 1.1407 -0.3240 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9755 1.7780 -0.2067 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4176 1.9884 -1.5407 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2938 1.4681 -1.9273 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4827 0.6143 -1.0363 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2992 -0.7470 -1.5914 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8657 -1.2604 -1.8431 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1237 -0.5455 -1.6003 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8228 -0.3939 -2.8913 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0100 -0.8459 -3.2000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8321 -1.5935 -2.2606 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0975 -0.8468 -2.0349 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5468 -0.3722 -0.9078 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7943 -0.5356 0.3536 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5054 0.8770 0.8612 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7557 0.7809 2.1189 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4606 -0.3246 2.5975 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3432 1.9080 2.8294 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7658 1.0546 -3.1127 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5958 2.2731 -2.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3292 1.3325 -1.3471 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7063 -0.1100 -2.5957 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0130 0.8320 -1.1075 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6666 -1.4510 -0.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1378 -1.5805 -1.4780 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5691 0.0973 1.1464 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2143 -1.4069 -0.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8333 -1.3002 2.4779 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8253 0.1793 2.5157 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1458 1.3739 1.0516 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5797 -0.8131 2.5231 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8470 1.8523 1.0591 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0450 1.2988 2.6201 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8987 -0.2129 -0.1016 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0181 0.3215 2.2459 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9424 -1.6600 1.0953 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1035 -1.1843 -0.4821 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6135 0.9683 -0.3972 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0696 -1.2194 1.0896 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8353 1.4706 -0.2837 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5862 0.8295 1.2571 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7483 -0.6399 -1.4993 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6160 -0.0945 0.8084 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7198 -1.6358 -1.9037 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5792 -2.2504 -0.3999 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0862 0.3991 -1.8325 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1552 -1.0322 -2.0439 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5634 -0.9649 0.4772 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5266 0.5176 0.5704 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3959 2.5307 -0.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4439 -1.5828 2.4327 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6771 -0.7208 4.0360 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2845 -0.0048 2.5225 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0988 0.6460 1.8886 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1709 0.9115 3.6484 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0270 -1.2439 4.1311 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3507 -1.9536 2.7453 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7711 -0.4692 0.8046 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7241 -1.8747 0.3533 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7345 -0.3634 -0.0516 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0671 1.7117 -0.8968 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3401 1.4347 0.5858 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2473 2.8521 0.1479 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9901 2.6295 -2.2580 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8754 1.6335 -2.9490 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8079 0.4983 -0.0163 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4977 1.1766 -0.9597 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1738 -1.3888 -1.8166 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9691 -2.2873 -2.2628 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0939 0.3647 -1.0126 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7211 -1.2580 -0.9327 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2732 0.1625 -3.6709 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4051 -0.6586 -4.1984 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3380 -1.9905 -1.4052 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1858 -2.5385 -2.8385 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7185 -0.6830 -2.9362 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5189 0.1643 -0.9151 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4058 -1.1031 1.0859 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8255 -0.9907 0.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4846 1.3718 0.9581 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8552 1.3430 0.0844 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3559 1.8863 3.8502 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 2 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 24 25 1 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 1 0 41 42 2 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 2 0 45 47 1 0 1 48 1 0 1 49 1 0 1 50 1 0 2 51 1 0 2 52 1 0 3 53 1 0 3 54 1 0 4 55 1 0 5 56 1 0 6 57 1 0 6 58 1 0 7 59 1 0 8 60 1 0 9 61 1 0 9 62 1 0 10 63 1 0 11 64 1 0 12 65 1 0 12 66 1 0 13 67 1 0 14 68 1 0 15 69 1 0 15 70 1 0 16 71 1 0 17 72 1 0 18 73 1 0 18 74 1 0 19 75 1 0 19 76 1 0 20 77 1 0 20 78 1 0 23 79 1 0 24 80 1 0 24 81 1 0 24 82 1 0 25 83 1 0 25 84 1 0 26 85 1 0 27 86 1 0 28 87 1 0 28 88 1 0 29 89 1 0 30 90 1 0 31 91 1 0 31 92 1 0 32 93 1 0 33 94 1 0 34 95 1 0 34 96 1 0 35 97 1 0 36 98 1 0 37 99 1 0 37100 1 0 38101 1 0 39102 1 0 40103 1 0 40104 1 0 41105 1 0 42106 1 0 43107 1 0 43108 1 0 44109 1 0 44110 1 0 47111 1 0 M END

Standard InCHIKey	YZXDIHSFJORZKY-GTCDFJJPSA-N
Standard InCHI	InChI=1S/C22H32O2.C21H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24;1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(22)23/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24);4-5,7-8,10-11,13-14,16-17H,2-3,6,9,12,15,18-20H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-;5-4+,8-7+,11-10+,14-13+,17-16+
SMILES	CCC/C=C/C/C=C/C/C=C/C/C=C/C/C=C/CCCC(=O)O.CC/C=CC/C=CC/C=CC/C=CC/C=CC/C=CCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	328.24	Volume:	388.193 ? Van der Waals volume.
Dense:	0.846	LogP:	6.843 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.81 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.684 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	7.0
TPSA:	37.3 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.367	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.199	Fsp³:	0.409
MCE-18:	0.0 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.435	Fluc inhibitor:	0.331 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.991	Promiscuous compounds:	0.539

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.981	MDCK Permeability:	-4.787
Pgp-inhibitor:	0.104	Pgp-substrate:	0.0
PAMPA:	0.014 ? 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%):	0.014	30% Bioavailability (F30%):	0.036
50% Bioavailability (F50%):	0.117

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225	MRP1:	0.999
Plasma Protein Binding (PPB):	97.832%	Volume Distribution (VD):	0.018
Fu:	2.343% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.01
OATP1B3 inhibitor:	0.264	BCRP inhibitor:	0.013
BSEP inhibitor:	0.914

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.021	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.726
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	1.0
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):

5.329

Half-life (T1/2):

0.27

ADMET: Toxicity

hERG Blockers:	0.621	hERG Blockers (10um):	0.428
Human Hepatotoxicity (H-HT):	0.0	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.968	Rat Oral Acute Toxicity:	0.016
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	1.0
Eye Irritation:	1.0	Respiratory Toxicity:	1.0
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.001
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.052
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.002
A549 Cytotoxicity:	0.025	Hek293 Cytotoxicity:	0.0
BCF:	1.372 ? 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:	4.182 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.502 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.733 ? 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
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/ejlt.201100207]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1007/s11746-010-1670-2]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.foodcont.2016.09.002]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.jfca.2010.08.006]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2010.06.003]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2010.12.007]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2016.02.010]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.12691/jfnr-2-5-9]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		DOI[10.5219/332]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[19628108]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[22538527]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[24811150]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[28274428]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30236698]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	Guangzhou, China		PMID[30563201]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30583361]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[30599958]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[31159190]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	Seeds	n.a.		PMID[31861466]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36613240]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13281	Salvia hispanica	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13281	Salvia hispanica	Species	Lamiaceae	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
NPO13281	Salvia hispanica	Soxhlet extraction; solvent n-hexane	Seeds	3.5	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Ultrasound extraction; solvent n-hexane	Seeds	59.6	n.a.	n.a.	%	DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Ultrasonic extraction; solvent n-hexane	Seeds	51.5	n.a.	n.a.	%	DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Ultrasonic extraction; solvent n-hexane	Seeds	46.4	n.a.	n.a.	%	DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Supercritical fluid extraction; solvent ethanol	Seeds	65-68	n.a.	n.a.	%	PMID[30599958]
NPO13281	Salvia hispanica	Supercritical fluid extraction; solvent CO2	Seeds	62.3	n.a.	n.a.	%	DOI[10.1016/j.supflu.2016.02.010]
NPO13281	Salvia hispanica	Supercritical fluid extraction; solvent CO2	Seeds	66	n.a.	n.a.	%	DOI[10.1016/j.supflu.2010.12.007]
NPO13281	Salvia hispanica	Supercritical fluid extraction; solvent CO2	Seeds	63.4	n.a.	n.a.	%	DOI[10.1016/j.supflu.2010.06.003]
NPO13281	Salvia hispanica	Supercritical fluid extraction; solvent CO2	Seeds	52.5-55.9	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Supercritical fluid extraction (with/without ultrasound and cosolvent); solvent CO2	Seeds	68.3	n.a.	n.a.	%	PMID[19628108]
NPO13281	Salvia hispanica	Subcritical fluid extraction; solvent n-propane	Seeds	47.3	n.a.	n.a.	%	DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Subcritical fluid extraction; solvent n-propane	Seeds	46.2	n.a.	n.a.	%	DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Soxhlet, Ultrasonic extraction; solvent n-hexane	Seeds	62.4	n.a.	n.a.	%	DOI[10.1016/j.jfca.2010.08.006]
NPO13281	Salvia hispanica	Soxhlet, Ultrasonic extraction; solvent isopropanol	Seeds	62.9	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Soxhlet, Ultrasonic extraction; solvent ethyl acetate	Seeds	62.4	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Cold press and ultrasound; solvent Methanol	Seeds	66.8-687	n.a.	n.a.	%	PMID[30583361]
NPO13281	Salvia hispanica	Soxhlet extraction; solvent n-hexane	Seeds	48.66	n.a.	n.a.	%	DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Soxhlet extraction; solvent n-hexane	Seeds	48.52	n.a.	n.a.	%	DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Soxhlet extraction; solvent n-hexane	Seeds	65.6-69.3	n.a.	n.a.	%	DOI[10.1016/j.jfca.2010.08.006]
NPO13281	Salvia hispanica	Soxhlet extraction; solvent n-hexane	Seeds	62.8	n.a.	n.a.	%	DOI[10.1016/j.foodcont.2016.09.002]
NPO13281	Salvia hispanica	Soxhlet extraction; solvent n-hexane	Seeds	54.4	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Soxhlet extraction; solvent ethanol	Seeds	64.1	n.a.	n.a.	%	DOI[10.1016/j.supflu.2016.02.010]
NPO13281	Salvia hispanica	Screw pressing; solvent n-hexane	Seeds	3.5	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Pressurized liquid extraction; solvent n-hexane	Seeds	65.5	n.a.	n.a.	%	PMID[30236698]
NPO13281	Salvia hispanica	Pressurized liquid extraction; solvent ethanol	Seeds	65-68	n.a.	n.a.	%	PMID[30599958]
NPO13281	Salvia hispanica	Pressing	Seeds	67.9	n.a.	n.a.	%	PMID[28274428]
NPO13281	Salvia hispanica	Pressing	Seeds	64.5-69.3	n.a.	n.a.	%	DOI[10.1007/s11746-010-1670-2]
NPO13281	Salvia hispanica	Cold solvent extraction; solvent n-hexane	Seeds	3.5	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Cold solvent extraction; solvent n-hexane	Seeds	67.9	n.a.	n.a.	%	DOI[10.1016/j.foodcont.2016.09.002]
NPO13281	Salvia hispanica	Cold press and ultrasound; solvent Methanol	Seeds	66.8-68.7	n.a.	n.a.	%	PMID[30583361]

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 NPC491258 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	41079
0.1-0.2	8011
0.2-0.3	550
0.3-0.4	133
0.4-0.5	46
0.5-0.6	19
0.6-0.7	8
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8065	Intermediate Similarity	NPC117572
0.7419	Intermediate Similarity	NPC270796
0.6857	Remote Similarity	NPC91495
0.6667	Remote Similarity	NPC59051
0.6571	Remote Similarity	NPC149821
0.6389	Remote Similarity	NPC70387
0.6216	Remote Similarity	NPC52955
0.6216	Remote Similarity	NPC88966
0.6216	Remote Similarity	NPC25417
0.6216	Remote Similarity	NPC1813
0.5946	Remote Similarity	NPC321062
0.5946	Remote Similarity	NPC5413
0.5789	Remote Similarity	NPC154245
0.5789	Remote Similarity	NPC85813
0.5789	Remote Similarity	NPC223697
0.5789	Remote Similarity	NPC6095
0.561	Remote Similarity	NPC323436
0.561	Remote Similarity	NPC327388
0.5455	Remote Similarity	NPC323597
0.5455	Remote Similarity	NPC211752
0.5455	Remote Similarity	NPC323498
0.5333	Remote Similarity	NPC320305
0.5333	Remote Similarity	NPC321838
0.5263	Remote Similarity	NPC207292
0.5217	Remote Similarity	NPC325977
0.5217	Remote Similarity	NPC327112
0.5135	Remote Similarity	NPC281245
0.5128	Remote Similarity	NPC48162
0.5106	Remote Similarity	NPC328311

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC491258 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7198
0.1-0.2	1787
0.2-0.3	130
0.3-0.4	22
0.4-0.5	4
0.5-0.6	3
0.6-0.7	1
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8065	Intermediate Similarity	NPD4222	Phase 3
0.7692	Intermediate Similarity	NPD39	Phase 4
0.7419	Intermediate Similarity	NPD5326	Phase 3
0.6216	Remote Similarity	NPD3172	Approved
0.5946	Remote Similarity	NPD3173	Phase 4
0.5789	Remote Similarity	NPD4266	Phase 2
0.5217	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