NPASS Compound

Natural Product: NPC491247

Natural Product ID	NPC491247
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Omega-6 Fatty Acid
IUPAC Name	(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid;(9Z,12Z)-octadeca-9,12-dienoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	56842208
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 106104 0 0 0 0 0 0 0 0999 V2000 -6.5484 -2.2111 0.8968 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5428 -1.2557 0.1966 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6456 -0.6677 1.2148 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6737 0.3338 0.7871 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6162 0.0423 -0.1998 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9716 -0.2862 -1.5731 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5907 0.4816 -2.5784 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7889 1.7259 -2.4627 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5628 1.5125 -3.2248 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6176 1.5790 -2.7060 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8497 1.8760 -1.3057 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5884 0.6819 -0.6715 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8121 1.0350 0.7968 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5266 -0.0586 1.5199 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8855 -0.3556 0.9328 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5868 -1.4622 1.6792 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9205 -1.6907 1.0137 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7041 -0.4425 1.0803 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6418 0.4584 0.2098 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5528 -0.2837 2.1844 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3667 0.1002 -1.0937 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5346 1.2906 -1.4085 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5184 1.7589 -0.4600 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3272 0.8813 -0.1866 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6033 -0.4086 0.3837 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6310 -1.4078 0.7733 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3604 -1.4033 0.6882 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5288 -0.3129 0.1371 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7527 -0.8891 -1.0155 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4601 -0.8145 -1.0458 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2841 -0.1416 0.0639 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1603 -1.1056 0.7521 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4400 -0.9224 0.8603 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1394 0.2443 0.3232 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1488 -0.2207 -0.6802 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4341 -0.0206 -0.6181 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0511 0.7154 0.4924 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0244 -0.2213 1.1791 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1137 -0.7076 0.2906 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9658 0.3767 -0.2346 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8281 0.0452 -1.1146 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9296 1.6950 0.1220 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4672 -2.3064 0.3013 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7926 -1.8132 1.9061 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0477 -3.1921 1.0186 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9574 -1.9158 -0.4860 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1552 -0.5251 -0.3496 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3242 -0.2569 2.0374 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1466 -1.5391 1.7470 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1632 0.7313 1.7514 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2344 1.3059 0.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8141 0.8166 -0.1527 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0266 -0.8950 0.1916 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5402 -1.1871 -1.8494 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9112 0.1468 -3.5929 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3978 2.4632 -3.1323 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7322 2.1649 -1.4848 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6553 1.2854 -4.2859 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5291 1.4049 -3.3382 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0431 2.1638 -0.6654 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6368 2.7063 -1.2870 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5376 0.4837 -1.1958 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8944 -0.1848 -0.6641 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3362 2.0128 0.8907 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8003 1.1858 1.2248 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8830 -0.9533 1.5546 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6828 0.2737 2.5658 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5038 0.5804 1.0582 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8901 -0.6036 -0.1241 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7057 -1.1960 2.7554 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9979 -2.4187 1.5781 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7473 -1.9218 -0.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4636 -2.5579 1.4346 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9689 0.6236 2.3885 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1181 -0.8027 -1.6942 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4480 0.3065 -1.4300 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4277 -0.0846 -0.0080 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0705 1.1397 -2.4414 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2820 2.1425 -1.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1758 2.7997 -0.7420 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0291 1.8769 0.5642 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8327 0.7967 -1.2105 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6948 1.5244 0.5081 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3642 -0.9522 -0.3122 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2720 -0.2448 1.3081 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0591 -2.3821 1.2429 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7902 -2.3135 1.0667 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9460 0.6091 -0.1333 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7275 -0.1455 0.9640 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3068 -1.3660 -1.8176 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1533 -1.2332 -1.8746 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2962 0.5246 0.6903 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9847 0.6168 -0.4729 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6550 -2.0089 1.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0177 -1.7044 1.3931 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6750 0.7904 1.1691 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5826 1.0313 -0.1606 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7713 -0.7867 -1.5555 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0609 -0.4246 -1.4456 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4021 1.1195 1.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6647 1.5608 0.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5060 0.3881 1.9961 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5009 -1.0618 1.6552 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7439 -1.4501 0.8404 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6856 -1.2419 -0.6050 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0008 2.4443 -0.5722 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 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 21 22 1 0 22 23 1 0 23 24 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 1 0 39 40 1 0 40 41 2 0 40 42 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 0 2 47 1 0 3 48 1 0 3 49 1 0 4 50 1 0 4 51 1 0 5 52 1 0 5 53 1 0 6 54 1 0 7 55 1 0 8 56 1 0 8 57 1 0 9 58 1 0 10 59 1 0 11 60 1 0 11 61 1 0 12 62 1 0 12 63 1 0 13 64 1 0 13 65 1 0 14 66 1 0 14 67 1 0 15 68 1 0 15 69 1 0 16 70 1 0 16 71 1 0 17 72 1 0 17 73 1 0 20 74 1 0 21 75 1 0 21 76 1 0 21 77 1 0 22 78 1 0 22 79 1 0 23 80 1 0 23 81 1 0 24 82 1 0 24 83 1 0 25 84 1 0 25 85 1 0 26 86 1 0 27 87 1 0 28 88 1 0 28 89 1 0 29 90 1 0 30 91 1 0 31 92 1 0 31 93 1 0 32 94 1 0 33 95 1 0 34 96 1 0 34 97 1 0 35 98 1 0 36 99 1 0 37100 1 0 37101 1 0 38102 1 0 38103 1 0 39104 1 0 39105 1 0 42106 1 0 M END

Standard InCHIKey	ZCDMRPMKAQLWAO-PZLFCYFRSA-N
Standard InCHI	InChI=1S/C20H32O2.C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22;1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22);6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-,16-15-;7-6-,10-9-
SMILES	CCCCC/C=CC/C=CCCCCCCCC(=O)O.CCCCC/C=CC/C=CC/C=CC/C=CCCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	304.24	Volume:	358.874 ? Van der Waals volume.
Dense:	0.848	LogP:	7.395 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.799 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.152 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	5.0
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:	0.305	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.769	Fsp³:	0.55
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:	0.297	Fluc inhibitor:	0.332 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.009 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.994	Promiscuous compounds:	0.567

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.014	MDCK Permeability:	-4.781
Pgp-inhibitor:	0.014	Pgp-substrate:	0.0
PAMPA:	0.031 ? 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):	0.005
20% Bioavailability (F20%):	0.026	30% Bioavailability (F30%):	0.142
50% Bioavailability (F50%):	0.228

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103	MRP1:	1.0
Plasma Protein Binding (PPB):	98.249%	Volume Distribution (VD):	-0.547
Fu:	1.101% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.009
OATP1B3 inhibitor:	0.402	BCRP inhibitor:	0.034
BSEP inhibitor:	0.98

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.35	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.998	CYP2D6-substrate:	0.0
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):

6.063

Half-life (T1/2):

0.22

ADMET: Toxicity

hERG Blockers:	0.372	hERG Blockers (10um):	0.377
Human Hepatotoxicity (H-HT):	0.003	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.466	Rat Oral Acute Toxicity:	0.01
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	1.0
Eye Irritation:	1.0	Respiratory Toxicity:	0.962
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.028
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.244
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.014
A549 Cytotoxicity:	0.188	Hek293 Cytotoxicity:	0.004
BCF:	1.226 ? 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:	4.043 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.413 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.129 ? 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	2.97	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Ultrasound extraction; solvent n-hexane	Seeds	22.1	n.a.	n.a.	%	DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Ultrasonic extraction; solvent n-hexane	Seeds	19.5	n.a.	n.a.	%	DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Supercritical fluid extraction; solvent ethanol	Seeds	17.0-23.0	n.a.	n.a.	%	PMID[30599958]
NPO13281	Salvia hispanica	Supercritical fluid extraction; solvent CO2	Seeds	19.7	n.a.	n.a.	%	DOI[10.1016/j.supflu.2016.02.010]
NPO13281	Salvia hispanica	Supercritical fluid extraction; solvent CO2	Seeds	18.2	n.a.	n.a.	%	DOI[10.1016/j.supflu.2010.12.007]
NPO13281	Salvia hispanica	Supercritical fluid extraction; solvent CO2	Seeds	35.8	n.a.	n.a.	%	DOI[10.1016/j.supflu.2010.06.003]
NPO13281	Salvia hispanica	Supercritical fluid extraction; solvent CO2	Seeds	19.8-20.9	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Supercritical fluid extraction (with/without ultrasound and cosolvent); solvent CO2	Seeds	18.6	n.a.	n.a.	%	PMID[19628108]
NPO13281	Salvia hispanica	Subcritical fluid extraction; solvent n-propane	Seeds	17.8	n.a.	n.a.	%	DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Subcritical fluid extraction; solvent n-propane	Seeds	17.5	n.a.	n.a.	%	DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Soxhlet, Ultrasonic extraction; solvent n-hexane	Seeds	19.6	n.a.	n.a.	%	DOI[10.1016/j.jfca.2010.08.006]
NPO13281	Salvia hispanica	Soxhlet, Ultrasonic extraction; solvent isopropanol	Seeds	19.8	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Soxhlet, Ultrasonic extraction; solvent ethyl acetate	Seeds	19.4	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Soxhlet extraction; solvent n-hexane	Seeds	4	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Cold press and ultrasound; solvent Methanol	Seeds	19.2-21.7	n.a.	n.a.	%	PMID[30583361]
NPO13281	Salvia hispanica	Soxhlet extraction; solvent n-hexane	Seeds	17.98	n.a.	n.a.	%	DOI[10.1016/j.supflu.2018.06.017]
NPO13281	Salvia hispanica	Soxhlet extraction; solvent n-hexane	Seeds	16.6-19.7	n.a.	n.a.	%	DOI[10.1016/j.jfca.2010.08.006]
NPO13281	Salvia hispanica	Soxhlet extraction; solvent n-hexane	Seeds	20.1	n.a.	n.a.	%	DOI[10.1016/j.foodcont.2016.09.002]
NPO13281	Salvia hispanica	Soxhlet extraction; solvent n-hexane	Seeds	20.2-21.8	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Soxhlet extraction; solvent ethanol	Seeds	19.9	n.a.	n.a.	%	DOI[10.1016/j.supflu.2016.02.010]
NPO13281	Salvia hispanica	Screw pressing; solvent n-hexane	Seeds	4	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Screw pressing; solvent n-hexane	Seeds	2.97	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Pressurized liquid extraction; solvent n-hexane	Seeds	18.1	n.a.	n.a.	%	PMID[30236698]
NPO13281	Salvia hispanica	Pressurized liquid extraction; solvent ethanol	Seeds	17.0-23.0	n.a.	n.a.	%	PMID[30599958]
NPO13281	Salvia hispanica	Pressing	Seeds	19.1	n.a.	n.a.	%	PMID[28274428]
NPO13281	Salvia hispanica	Pressing	Seeds	16.6-17.5	n.a.	n.a.	%	DOI[10.1007/s11746-010-1670-2]
NPO13281	Salvia hispanica	Cold solvent extraction; solvent n-hexane	Seeds	4	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Cold solvent extraction; solvent n-hexane	Seeds	2.97	n.a.	n.a.	%	PMID[31861466]
NPO13281	Salvia hispanica	Cold solvent extraction; solvent n-hexane	Seeds	17.6	n.a.	n.a.	%	DOI[10.1016/j.foodcont.2016.09.002]

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 NPC491247 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	38507
0.1-0.2	9804
0.2-0.3	1162
0.3-0.4	200
0.4-0.5	65
0.5-0.6	41
0.6-0.7	40
0.7-0.8	0
0.8-0.85	15
0.85-0.9	0
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9355	High Similarity	NPC154245
0.9355	High Similarity	NPC85813
0.9355	High Similarity	NPC223697
0.9355	High Similarity	NPC59051
0.9355	High Similarity	NPC6095
0.9032	High Similarity	NPC321062
0.9032	High Similarity	NPC91495
0.8438	Intermediate Similarity	NPC5413
0.8387	Intermediate Similarity	NPC424
0.8387	Intermediate Similarity	NPC36061
0.8387	Intermediate Similarity	NPC69510
0.8387	Intermediate Similarity	NPC77272
0.8387	Intermediate Similarity	NPC290563
0.8387	Intermediate Similarity	NPC139029
0.8387	Intermediate Similarity	NPC281972
0.8387	Intermediate Similarity	NPC261831
0.8387	Intermediate Similarity	NPC87564
0.8182	Intermediate Similarity	NPC52955
0.8182	Intermediate Similarity	NPC88966
0.8182	Intermediate Similarity	NPC25417
0.8182	Intermediate Similarity	NPC1813
0.8065	Intermediate Similarity	NPC281245
0.7879	Intermediate Similarity	NPC70387
0.7812	Intermediate Similarity	NPC92114
0.7576	Intermediate Similarity	NPC95145
0.7576	Intermediate Similarity	NPC325642
0.7576	Intermediate Similarity	NPC65174
0.7059	Intermediate Similarity	NPC149821
0.7	Intermediate Similarity	NPC323597
0.7	Intermediate Similarity	NPC211752
0.7	Intermediate Similarity	NPC323498
0.697	Remote Similarity	NPC117572
0.6744	Remote Similarity	NPC322461
0.6591	Remote Similarity	NPC605544
0.6591	Remote Similarity	NPC607260
0.6571	Remote Similarity	NPC207292
0.65	Remote Similarity	NPC477201
0.6452	Remote Similarity	NPC171736
0.6452	Remote Similarity	NPC301585
0.6452	Remote Similarity	NPC261080
0.6452	Remote Similarity	NPC132565
0.6452	Remote Similarity	NPC209970
0.6452	Remote Similarity	NPC216630
0.6452	Remote Similarity	NPC201844
0.6452	Remote Similarity	NPC301696
0.6452	Remote Similarity	NPC196924
0.6452	Remote Similarity	NPC307783
0.6452	Remote Similarity	NPC154186
0.6452	Remote Similarity	NPC149184
0.6452	Remote Similarity	NPC279026
0.6452	Remote Similarity	NPC113928
0.6452	Remote Similarity	NPC14227
0.6444	Remote Similarity	NPC329249
0.6279	Remote Similarity	NPC325977
0.6279	Remote Similarity	NPC320642
0.6279	Remote Similarity	NPC327112
0.6279	Remote Similarity	NPC329550
0.619	Remote Similarity	NPC243532
0.6136	Remote Similarity	NPC328311
0.6136	Remote Similarity	NPC323045
0.6136	Remote Similarity	NPC317881
0.6129	Remote Similarity	NPC155263
0.6098	Remote Similarity	NPC106851
0.6098	Remote Similarity	NPC282788
0.6098	Remote Similarity	NPC274927
0.6047	Remote Similarity	NPC320305
0.6047	Remote Similarity	NPC317583
0.6047	Remote Similarity	NPC68343
0.6047	Remote Similarity	NPC321838
0.6047	Remote Similarity	NPC328089
0.6	Remote Similarity	NPC606120
0.5952	Remote Similarity	NPC179764
0.5946	Remote Similarity	NPC87394
0.5946	Remote Similarity	NPC48162
0.5946	Remote Similarity	NPC224227
0.5882	Remote Similarity	NPC180534
0.5882	Remote Similarity	NPC611531
0.5814	Remote Similarity	NPC251042
0.5814	Remote Similarity	NPC255863
0.5814	Remote Similarity	NPC473863
0.5814	Remote Similarity	NPC174447
0.5814	Remote Similarity	NPC136164
0.5814	Remote Similarity	NPC122521
0.5814	Remote Similarity	NPC245947
0.5745	Remote Similarity	NPC92558
0.5682	Remote Similarity	NPC318420
0.5682	Remote Similarity	NPC326268
0.561	Remote Similarity	NPC323436
0.561	Remote Similarity	NPC487561
0.561	Remote Similarity	NPC327388
0.561	Remote Similarity	NPC225929
0.5556	Remote Similarity	NPC34416
0.5484	Remote Similarity	NPC214610
0.5484	Remote Similarity	NPC118968
0.5484	Remote Similarity	NPC183424
0.5484	Remote Similarity	NPC294085
0.5455	Remote Similarity	NPC318814
0.5455	Remote Similarity	NPC320669
0.5405	Remote Similarity	NPC8219
0.5312	Remote Similarity	NPC175342
0.5263	Remote Similarity	NPC18712
0.5263	Remote Similarity	NPC74845
0.5161	Remote Similarity	NPC268826
0.5135	Remote Similarity	NPC262968
0.5128	Remote Similarity	NPC294548
0.5128	Remote Similarity	NPC324004
0.5128	Remote Similarity	NPC328497
0.5128	Remote Similarity	NPC602547
0.5122	Remote Similarity	NPC40082
0.5111	Remote Similarity	NPC187777
0.5106	Remote Similarity	NPC49863
0.5098	Remote Similarity	NPC322457

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC491247 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6913
0.1-0.2	2023
0.2-0.3	163
0.3-0.4	23
0.4-0.5	9
0.5-0.6	7
0.6-0.7	6
0.7-0.8	0
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9355	High Similarity	NPD4266	Phase 2
0.8438	Intermediate Similarity	NPD3173	Phase 4
0.8387	Intermediate Similarity	NPD3195	Phase 2
0.8387	Intermediate Similarity	NPD3196	Approved
0.8182	Intermediate Similarity	NPD3172	Approved
0.8158	Intermediate Similarity	NPD39	Phase 4
0.697	Remote Similarity	NPD4222	Phase 3
0.6842	Remote Similarity	NPD3194	Phase 4
0.6452	Remote Similarity	NPD2270	Pre-clinical
0.6452	Remote Similarity	NPD633	Phase 3
0.6452	Remote Similarity	NPD9448	Phase 2
0.6279	Remote Similarity	NPD4246	Phase 2
0.5882	Remote Similarity	NPD622	Pre-clinical
0.5484	Remote Similarity	NPD9655	Phase 4
0.5263	Remote Similarity	NPD3174	Discontinued
0.5135	Remote Similarity	NPD28	Approved
0.5135	Remote Similarity	NPD29	Phase 4
0.5128	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5106	Remote Similarity	NPD4247	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