NPASS Compound

Natural Product: NPC12931

Natural Product ID	NPC12931
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-Octaprenylhydroquinone
IUPAC Name	2-[(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaenyl]benzene-1,4-diol
Synonyms	2-Octaprenyl-Hydroquinone; 2-Octaprenylhydroquinone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL502595
PubChem CID	5960433
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001534] Quinone and hydroquinone lipids [CHEMONTID:0002801] Prenylated hydroquinones [CHEMONTID:0001937] Polyprenyl quinols

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 118118 0 0 0 0 0 0 0 0999 V2000 -1.5725 -1.8268 3.4303 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1888 -2.6671 2.2526 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6613 -2.2909 1.0723 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5271 -1.1124 0.8795 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0173 -0.1087 -0.0981 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9870 1.0420 -0.2278 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0944 1.0780 0.4909 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1154 2.1884 0.4163 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4631 1.5961 0.0895 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5175 2.6382 0.0007 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5713 2.6288 0.8112 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6463 3.6379 0.7546 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0209 3.0948 0.7702 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4684 2.1860 -0.2602 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8215 1.7275 -1.3001 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4647 0.7807 -2.2640 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6661 -0.4761 -2.2402 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0572 -1.6172 -1.5752 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2845 -2.7391 -1.5725 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6240 -3.9144 -0.9220 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0802 -2.7305 -2.2539 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6573 -1.6180 -2.9262 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4656 -0.4931 -2.9099 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0079 0.6288 -3.6055 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.9021 1.6763 -0.1130 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4158 3.7510 -0.9917 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7059 2.1467 -1.1625 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3461 -3.8408 2.4780 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9894 -3.5850 3.0802 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8721 -2.6990 2.2411 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0520 -3.1463 1.8175 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9515 -2.2990 0.9893 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2717 -2.0803 1.7039 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2471 -1.2718 0.9540 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4633 -1.7700 0.6322 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4875 -0.9928 -0.1243 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6840 -0.9056 0.8052 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8350 -0.1898 0.2594 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2800 0.9173 0.8224 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4287 1.7347 0.3680 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0058 1.2304 -0.8925 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0495 1.4169 -2.0156 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3897 2.1167 -3.1040 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4163 2.2769 -4.1959 C 0 0 0 0 0 0 0 0 0 0 0 0 13.7401 2.7098 -3.1685 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4965 1.3525 2.0551 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7551 -3.1477 1.0618 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4643 -4.5241 2.1869 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1148 -2.2005 4.3561 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0961 -0.8347 3.2313 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6513 -1.7902 3.5621 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3705 -2.9146 0.2234 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5232 -1.4764 0.4897 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6395 -0.6443 1.8896 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0927 0.3544 0.3200 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7783 -0.5449 -1.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2865 0.2455 1.1889 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7839 2.9064 -0.3412 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1215 2.6632 1.4152 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7318 0.9250 0.9515 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4121 0.9705 -0.8203 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6410 1.8393 1.5484 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4713 4.3970 -0.0441 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5341 4.2428 1.7069 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1265 2.5431 1.7595 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7471 3.9646 0.7877 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8174 2.0377 -1.4675 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3304 1.2187 -3.2818 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5325 0.6453 -2.1039 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9890 -1.5986 -1.0603 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9873 -4.6849 -1.4592 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4455 -3.6299 -2.2607 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7271 -1.5979 -3.4559 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9400 0.6255 -4.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3370 1.9520 0.8446 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7848 0.5600 -0.0886 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5445 2.0433 -0.9085 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1893 4.7285 -0.5076 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5575 3.5111 -1.6863 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3146 3.8472 -1.6108 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7781 3.1489 -0.7032 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7183 1.9918 -1.6765 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4565 2.1415 -1.9929 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1560 -4.2880 1.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9119 -4.6496 3.0141 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8437 -3.0184 4.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5252 -4.5030 3.3780 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -1.6936 1.9585 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0851 -2.7207 -0.0302 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4425 -1.3083 0.8337 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0065 -1.4595 2.6144 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6878 -3.0084 2.1194 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0402 -0.2614 0.6309 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1299 -0.0192 -0.4615 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7128 -1.5945 -1.0332 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0175 -1.9804 0.9340 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3140 -0.5738 1.7782 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3367 -0.5987 -0.5844 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0155 2.7726 0.2265 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1810 1.8613 1.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9550 1.7555 -1.1167 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2367 0.1428 -0.7540 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0492 1.0220 -2.0054 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5825 1.5440 -4.0944 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9499 3.2944 -4.2003 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9249 2.0789 -5.1747 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8314 3.4029 -2.2808 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4830 1.9059 -3.0723 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8785 3.2794 -4.1149 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8375 2.3661 2.3527 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5690 0.6085 2.8529 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4470 1.4506 1.7334 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0699 -3.2381 2.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6455 -3.5040 0.4641 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9630 -3.8814 0.8095 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4552 -4.7437 1.7274 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7580 -5.2640 1.8077 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5480 -4.6735 3.2800 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 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 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 17 18 2 0 18 19 1 0 19 20 1 0 19 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 14 25 1 0 10 26 1 0 6 27 1 0 2 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 2 3 43 44 1 0 43 45 1 0 39 46 1 0 35 47 1 0 31 48 1 0 23 17 1 0 1 49 1 0 1 50 1 0 1 51 1 0 3 52 1 0 4 53 1 0 4 54 1 0 5 55 1 0 5 56 1 0 7 57 1 0 8 58 1 0 8 59 1 0 9 60 1 0 9 61 1 0 11 62 1 0 12 63 1 0 12 64 1 0 13 65 1 0 13 66 1 0 15 67 1 0 16 68 1 0 16 69 1 0 18 70 1 0 20 71 1 0 21 72 1 0 22 73 1 0 24 74 1 0 25 75 1 0 25 76 1 0 25 77 1 0 26 78 1 0 26 79 1 0 26 80 1 0 27 81 1 0 27 82 1 0 27 83 1 0 28 84 1 0 28 85 1 0 29 86 1 0 29 87 1 0 30 88 1 0 32 89 1 0 32 90 1 0 33 91 1 0 33 92 1 0 34 93 1 0 36 94 1 0 36 95 1 0 37 96 1 0 37 97 1 0 38 98 1 0 40 99 1 0 40100 1 0 41101 1 0 41102 1 0 42103 1 0 44104 1 0 44105 1 0 44106 1 0 45107 1 0 45108 1 0 45109 1 0 46110 1 0 46111 1 0 46112 1 0 47113 1 0 47114 1 0 47115 1 0 48116 1 0 48117 1 0 48118 1 0 M END

Standard InCHIKey	RFUXBANISHMTPU-LQOKPSQISA-N
Standard InCHI	InChI=1S/C46H70O2/c1-36(2)17-10-18-37(3)19-11-20-38(4)21-12-22-39(5)23-13-24-40(6)25-14-26-41(7)27-15-28-42(8)29-16-30-43(9)31-32-44-35-45(47)33-34-46(44)48/h17,19,21,23,25,27,29,31,33-35,47-48H,10-16,18,20,22,24,26,28,30,32H2,1-9H3/b37-19+,38-21+,39-23+,40-25+,41-27+,42-29+,43-31+
SMILES	C/C(=CCC/C(=C/CC/C(=C/CC/C(=C/Cc1cc(O)ccc1O)/C)/C)/C)/CC/C=C(/CC/C=C(/CC/C=C(/CCC=C(C)C)C)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	654.54	Volume:	784.195 ? Van der Waals volume.
Dense:	0.835	LogP:	15.749 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	7.177 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-11.786 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	23.0	Rigid Bonds:	14.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	1.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.091	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.457	Fsp³:	0.522
MCE-18:	14.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	0.054 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.0 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.063 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.666	Promiscuous compounds:	0.051

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.917	MDCK Permeability:	-4.782
Pgp-inhibitor:	1.0	Pgp-substrate:	0.0
PAMPA:	0.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.0
50% Bioavailability (F50%):	0.446

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.939
Plasma Protein Binding (PPB):	96.431%	Volume Distribution (VD):	0.232
Fu:	2.398% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.231
CYP2C9-inhibitor:	0.997	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.931
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.873
HLM stability:	1.0 ? 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):

10.14

Half-life (T1/2):

0.873

ADMET: Toxicity

hERG Blockers:	0.267	hERG Blockers (10um):	0.842
Human Hepatotoxicity (H-HT):	0.937	Drug-induced Liver Injury (DILI):	0.008
AMES Toxicity:	0.005	Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.725	Skin Sensitization:	1.0
Carcinogencity:	0.004	Eye Corrosion:	0.0
Eye Irritation:	0.158	Respiratory Toxicity:	0.998
Drug-induced Neurotoxicity:	0.235	Ototoxicity:	0.741
Hematotoxicity:	0.241	Drug-induced Nephrotoxicity:	0.794
Genotoxicity:	0.708	RPMI-8226 Immunitoxicity:	0.121
A549 Cytotoxicity:	0.945	Hek293 Cytotoxicity:	0.766
BCF:	1.24 ? 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:	6.939 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	8.648 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	9.333 ? 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
NPO4561	Cantharellus cibarius	Species	Cantharellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22342624]
NPO4561	Cantharellus cibarius	Species	Cantharellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3178	Dalbergia latifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO812	Populus heterophylla	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4561	Cantharellus cibarius	Species	Cantharellaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4561	Cantharellus cibarius	Species	Cantharellaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO812	Populus heterophylla	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO812	Populus heterophylla	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO812	Populus heterophylla	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3178	Dalbergia latifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4561	Cantharellus cibarius	Species	Cantharellaceae	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
-	Gambusia affinis	LC50	>	100.0	ppm	DOI[10.1021/np50123a018]
-	Artemia salina	LC50	=	0.98	ppm	DOI[10.1021/np50123a018]

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 NPC12931 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	24934
0.1-0.2	22010
0.2-0.3	2408
0.3-0.4	370
0.4-0.5	95
0.5-0.6	23
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC260775
1.0	High Similarity	NPC130756
1.0	High Similarity	NPC70677
0.9474	High Similarity	NPC152097
0.7556	Intermediate Similarity	NPC98392
0.72	Intermediate Similarity	NPC155072
0.6889	Remote Similarity	NPC477685
0.6667	Remote Similarity	NPC609473
0.6296	Remote Similarity	NPC228609
0.6087	Remote Similarity	NPC12640
0.6042	Remote Similarity	NPC76400
0.5849	Remote Similarity	NPC320439
0.5849	Remote Similarity	NPC474890
0.5849	Remote Similarity	NPC273282
0.5849	Remote Similarity	NPC4493
0.566	Remote Similarity	NPC483761
0.566	Remote Similarity	NPC166995
0.56	Remote Similarity	NPC489529
0.549	Remote Similarity	NPC99836
0.5424	Remote Similarity	NPC116513
0.5424	Remote Similarity	NPC197513
0.5306	Remote Similarity	NPC479914
0.5283	Remote Similarity	NPC144343
0.5283	Remote Similarity	NPC246967
0.5273	Remote Similarity	NPC474810
0.5273	Remote Similarity	NPC484189
0.5263	Remote Similarity	NPC282855
0.5263	Remote Similarity	NPC26013
0.5246	Remote Similarity	NPC62867
0.5246	Remote Similarity	NPC177962
0.52	Remote Similarity	NPC269414
0.5179	Remote Similarity	NPC24125
0.5098	Remote Similarity	NPC201662
0.5085	Remote Similarity	NPC267846

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC12931 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6584
0.1-0.2	2475
0.2-0.3	85
0.3-0.4	5
0.4-0.5	1
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	Drug ID	Developmental Stage
		NPD

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