NPASS Compound

Natural Product: NPC521167

Natural Product ID	NPC521167
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GAMA-TOCOPHEROL
IUPAC Name	(2~{S})-2,7,8-trimethyl-2-[(4~{S},8~{R})-4,8,12-trimethyltridecyl]chroman-6-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 78 79 0 0 0 0 0 0 0 0999 V2000 5.9921 -2.1819 -3.6035 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5932 -1.8390 -2.2120 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7485 -2.8118 -1.2509 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2494 -4.0834 -1.4870 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3701 -2.4865 0.0600 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8762 -1.2752 0.3667 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4403 -0.9317 1.7548 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0937 -0.2085 1.6636 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2064 1.0084 0.8470 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7116 2.1632 1.7701 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9922 1.5228 0.1625 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3313 0.6990 -0.8320 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6963 -0.5868 -0.6385 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4917 -0.7572 0.2359 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9269 -2.2487 0.2139 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4632 -0.3353 1.6353 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7921 -0.6260 2.3171 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9103 0.1751 1.6363 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2202 -0.0767 2.3083 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6176 -1.5416 2.2038 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2993 0.8970 2.1764 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8504 1.2722 0.8605 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9513 1.9641 -0.0809 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6077 2.3209 -1.3981 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6003 3.0429 -2.3029 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0972 1.1449 -2.1670 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2089 0.9130 -0.1749 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7135 -0.2788 -0.5923 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0855 -0.5893 -1.9022 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9268 0.4444 -2.9564 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0301 -2.1935 -4.1923 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6129 -1.3759 -4.0072 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4688 -3.1595 -3.6661 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1703 -4.2768 -1.0638 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4991 -3.2636 0.8020 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2809 -1.8623 2.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1445 -0.2985 2.3006 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3553 -0.9125 1.2964 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8406 0.1202 2.7216 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7346 2.4295 1.5160 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6782 1.8185 2.8239 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0079 3.0080 1.6904 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4065 2.4398 -0.4446 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3555 2.0107 0.9416 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1041 0.5287 -1.6900 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5751 1.3448 -1.4346 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3640 -1.4926 -0.5566 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2463 -0.8347 -1.7131 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3557 -0.2089 -0.2636 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7372 -2.7213 1.1931 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3316 -2.7738 -0.5707 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9991 -2.3527 -0.0131 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3314 0.7706 1.7619 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2894 -0.8425 2.2826 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0458 -1.6967 2.3521 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7057 -0.2632 3.3836 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0015 -0.3025 0.6199 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5838 1.1900 1.5359 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9257 -0.0160 3.4456 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3936 -1.8406 1.1387 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9666 -2.1867 2.8243 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6846 -1.7126 2.3583 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9552 1.8433 2.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1361 0.5505 2.8767 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8023 1.8431 1.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2544 0.3121 0.3951 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6374 2.9409 0.3953 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0689 1.3731 -0.3408 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4449 3.0259 -1.2408 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7201 2.8022 -3.3589 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5938 2.7038 -1.9827 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6402 4.1358 -2.1066 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2982 0.6643 -2.7805 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6790 0.4037 -1.5902 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8238 1.5360 -2.9393 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8922 0.7820 -3.3871 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3382 1.2767 -2.5267 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3143 0.0238 -3.7802 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 3 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 1 9 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 24 26 1 0 9 27 1 0 27 28 1 0 28 29 2 0 29 30 1 0 29 2 1 0 28 6 1 0 1 31 1 0 1 32 1 0 1 33 1 0 4 34 1 0 5 35 1 0 7 36 1 0 7 37 1 0 8 38 1 0 8 39 1 0 10 40 1 0 10 41 1 0 10 42 1 0 11 43 1 0 11 44 1 0 12 45 1 0 12 46 1 0 13 47 1 0 13 48 1 0 14 49 1 6 15 50 1 0 15 51 1 0 15 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 18 57 1 0 18 58 1 0 19 59 1 1 20 60 1 0 20 61 1 0 20 62 1 0 21 63 1 0 21 64 1 0 22 65 1 0 22 66 1 0 23 67 1 0 23 68 1 0 24 69 1 0 25 70 1 0 25 71 1 0 25 72 1 0 26 73 1 0 26 74 1 0 26 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 M END

Standard InCHIKey	QUEDXNHFTDJVIY-WENCSYSZSA-N
Standard InCHI	InChI=1S/C28H48O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-19-26(29)23(5)24(6)27(25)30-28/h19-22,29H,8-18H2,1-7H3/t21-,22+,28+/m1/s1
SMILES	CC1=C(O)C=C2CC[C@](C)(CCC[C@@H](C)CCC[C@H](C)CCCC(C)C)OC2=C1C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	416.37	Volume:	485.402 ? Van der Waals volume.
Dense:	0.858	LogP:	9.15 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.513 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-7.847 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	11.0
TPSA:	29.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	1.0	Rings:	2.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.37	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.786	Fsp³:	0.786
MCE-18:	53.04 ? 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:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.929	Fluc inhibitor:	0.279 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.05 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.509	Promiscuous compounds:	0.028

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.016	MDCK Permeability:	-4.704
Pgp-inhibitor:	0.0	Pgp-substrate:	0.002
PAMPA:	0.024 ? 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):	0.0
20% Bioavailability (F20%):	0.011	30% Bioavailability (F30%):	0.676
50% Bioavailability (F50%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.996	MRP1:	0.976
Plasma Protein Binding (PPB):	93.32%	Volume Distribution (VD):	0.244
Fu:	7.633% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.097
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.442	CYP2C9-substrate:	0.086
CYP2D6-inhibitor:	0.025	CYP2D6-substrate:	0.732
CYP3A4-inhibitor:	0.986	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	1.0
HLM stability:	0.999 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

4.307

Half-life (T1/2):

0.547

ADMET: Toxicity

hERG Blockers:	0.332	hERG Blockers (10um):	0.723
Human Hepatotoxicity (H-HT):	0.724	Drug-induced Liver Injury (DILI):	0.019
AMES Toxicity:	0.321	Rat Oral Acute Toxicity:	0.19
Maximum Recommended Daily Dose:	0.165	Skin Sensitization:	0.999
Carcinogencity:	0.631	Eye Corrosion:	0.716
Eye Irritation:	0.975	Respiratory Toxicity:	0.788
Drug-induced Neurotoxicity:	0.016	Ototoxicity:	0.529
Hematotoxicity:	0.192	Drug-induced Nephrotoxicity:	0.264
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.126
A549 Cytotoxicity:	0.811	Hek293 Cytotoxicity:	0.244
BCF:	2.358 ? 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:	5.606 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.797 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	7.099 ? 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
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s00217-007-0799-1]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2011.01.077]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0014-5793(03)00033-4]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ac991142i]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1034/j.1399-3054.2003.00030.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.274.1.397]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M302362200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M314195200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M411109200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.103.022368]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11005203]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12637544]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12805618]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14745019]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15280363]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15620261]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15820655]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15834012]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15844959]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1684022]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17611796]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057039]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18235971]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318836]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19521717]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21193570]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21194489]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21395888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800258]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23370715]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23950498]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[24163311]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24285094]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[25457500]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[27363486]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27432888]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36560643]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39138188]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39527985]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8278506]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO45500	Rosmarinus officinalis L.	Genus	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO47500	Delphinium ajacis L.	Genus	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO50284	Elaeis guineensis Jacq.	Genus	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO43780	Coriandrum sativum L.	Genus	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO54537	Nicotiana tabacum L.	Genus	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO50353	Bixa orellana L.	Genus	Bixaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO44442	Oryza sativa L.	Genus	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO43508	Carum carvi L.	Genus	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO46843	Calophyllum inophyllum L.	Genus	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO53457	Gevuina avellana Mol.	Genus	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO57885	Zea mays L.	Genus	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO56140	Aesculus hippocastanum Hort.	Genus	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO46802	Amaranthus hypochondriacus L.	Genus	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO51793	Avena sativa L.	Genus	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO60041	Cocos nucifera L.	Genus	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO43635	Litchi chinensis Sonn.	Genus	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO57580	Juglans regia L.	Genus	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO51497	Vitis vinifera L.	Genus	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO61721	Vaccinium macrocarpon Aiton	Genus	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO63328	Foeniculum vulgare L.	Genus	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO56122	Hordeum vulgare L.	Genus	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO47968	Hevea brasiliensis Mull.Arg.	Genus	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Twig	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	Leaf Diffusate	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO993	Phaseolus coccineus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21349	Punica granatum	Species	Lythraceae	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

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 NPC521167 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	22114
0.1-0.2	26081
0.2-0.3	1595
0.3-0.4	53
0.4-0.5	6
0.5-0.6	3
0.6-0.7	3
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC48623
1.0	High Similarity	NPC168707
0.7222	Intermediate Similarity	NPC187993
0.7222	Intermediate Similarity	NPC238176
0.6852	Remote Similarity	NPC126759
0.6852	Remote Similarity	NPC242580
0.6852	Remote Similarity	NPC236070
0.5902	Remote Similarity	NPC45663
0.5517	Remote Similarity	NPC238075
0.507	Remote Similarity	NPC609806

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC521167 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4337
0.1-0.2	4757
0.2-0.3	49
0.3-0.4	3
0.4-0.5	2
0.5-0.6	1
0.6-0.7	1
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
0.6852	Remote Similarity	NPD7340	Approved
0.5517	Remote Similarity	NPD7644	Approved

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