NPASS Compound

Natural Product: NPC475179

Natural Product ID	NPC475179
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Stenopalustroside E
IUPAC Name	[(2R,3R,4S,5R,6S)-2-[[(E)-3-[4-[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxyphenyl]prop-2-enoyl]oxymethyl]-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,5-dihydroxyoxan-4-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms	stenopalustroside E
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL500228
PubChem CID	10724604
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl glycosides

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 116122 0 0 0 0 0 0 0 0999 V2000 6.2764 -2.8287 -1.8166 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0439 -1.6901 -1.0479 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8811 -1.4208 -0.3942 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7690 -0.2458 0.3326 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5264 -0.0166 0.9964 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4835 -0.8987 0.9344 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5988 -2.0540 0.2201 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8200 -2.2806 -0.4361 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 -3.0506 0.1221 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3806 -3.1454 0.5214 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5934 -2.4205 1.2187 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7358 -3.1010 1.4035 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7092 -1.1698 1.7696 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9287 -0.7490 2.4004 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0451 -0.6341 1.4230 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8104 0.4736 0.4214 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8167 1.5388 0.2957 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2514 1.1748 0.7390 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2309 -0.2913 1.0066 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2957 -0.4460 2.0494 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4423 -0.9060 1.3457 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5921 -2.2031 0.8369 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3340 -3.2890 1.5882 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4849 -4.4622 0.9536 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8578 -4.5607 -0.2944 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9958 -5.7895 -0.9133 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3866 -5.9232 -2.2347 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6558 -4.7896 -2.9829 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5330 -3.5463 -2.4138 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1348 -3.4634 -1.0796 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9979 -2.2415 -0.4979 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2314 -1.2168 -1.1580 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7910 -2.3941 -3.1188 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5216 -7.1553 -2.8459 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9188 -3.3361 2.9871 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4268 -4.5594 3.4861 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0776 -4.6900 4.7950 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1848 -3.6387 5.6976 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6680 -2.4538 5.1821 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0322 -2.2967 3.8481 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8354 -3.7578 7.0300 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1905 1.5440 -0.2206 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0040 1.9911 -1.0467 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9439 3.3711 -1.3571 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7147 4.0719 -0.3672 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1451 3.7803 -2.6987 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1468 4.8858 -3.3196 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9473 6.2519 -3.0021 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3095 7.2010 -3.9865 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1197 8.5336 -3.8271 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5585 9.0156 -2.6817 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1838 8.1503 -1.6873 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3866 6.7949 -1.8724 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3913 10.3862 -2.5748 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6042 1.1007 0.8346 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7040 0.6636 0.4633 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8893 1.1706 0.2604 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2449 1.4374 -1.1717 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5173 2.0196 -1.2799 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9950 0.2939 0.8718 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3131 0.9622 0.6864 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3270 0.4103 -0.0678 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5400 1.0257 -0.2475 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7983 2.2611 0.3380 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7874 2.8153 1.0924 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5661 2.1890 1.2713 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0091 2.9082 0.1798 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5368 0.4366 -1.0145 O 0 0 0 0 0 0 0 0 0 0 0 0 12.3428 -0.8005 -1.6258 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7199 0.2096 2.2675 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8663 -2.6172 -2.8434 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8263 -3.7515 -1.4560 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3825 -2.9721 -1.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4171 0.9107 1.5681 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5867 -0.6438 1.4851 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9538 -3.1986 -1.0242 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9334 -4.0020 -0.4483 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0232 -4.2133 0.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1280 -1.4092 3.2540 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6874 0.2502 2.8590 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1693 -1.5612 0.8452 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6474 0.0171 -0.5872 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5815 2.4207 0.9375 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5102 1.6965 1.6967 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7305 -0.8556 0.1518 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7940 -6.6755 -0.3509 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9634 -4.8939 -4.0112 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6667 -1.9024 -2.8833 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3401 -7.7318 -2.7315 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3272 -5.4091 2.8009 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6941 -5.6082 5.2095 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7871 -1.5670 5.8223 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4149 -1.3342 3.5115 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5890 -3.7901 7.7182 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9071 1.3920 -1.1435 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3587 2.8471 -3.3797 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3489 4.7124 -4.4469 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7696 6.8715 -4.9254 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4227 9.2061 -4.6193 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7365 8.5250 -0.7834 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0495 6.1789 -1.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2161 10.9998 -2.6521 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9411 0.9061 0.1326 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0228 2.2060 0.7922 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1453 0.5499 -1.7984 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5010 2.1992 -1.5406 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4717 2.6134 -2.0735 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9758 -0.6882 0.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0955 -0.5619 -0.5239 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9520 3.7791 1.5655 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7696 2.6156 1.8649 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9088 2.4760 0.4040 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3085 -1.0724 -2.1371 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5084 -0.7446 -2.3459 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1177 -1.6032 -0.8807 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5741 0.2820 2.7277 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 2 3 10 11 1 0 11 12 2 0 11 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 1 0 19 20 1 0 19 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 29 33 1 0 27 34 1 0 23 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 38 41 1 0 18 42 1 0 17 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 46 47 2 3 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 51 54 1 0 16 55 1 0 4 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 57 60 1 0 60 61 1 0 61 62 2 0 62 63 1 0 63 64 2 0 64 65 1 0 65 66 2 0 64 67 1 0 63 68 1 0 68 69 1 0 60 70 1 0 8 3 1 0 20 15 1 0 31 22 1 0 30 25 1 0 40 35 1 0 53 48 1 0 66 61 1 0 1 71 1 0 1 72 1 0 1 73 1 0 5 74 1 0 6 75 1 0 8 76 1 0 9 77 1 0 10 78 1 0 14 79 1 0 14 80 1 0 15 81 1 0 16 82 1 0 17 83 1 0 18 84 1 0 19 85 1 0 26 86 1 0 28 87 1 0 33 88 1 0 34 89 1 0 36 90 1 0 37 91 1 0 39 92 1 0 40 93 1 0 41 94 1 0 42 95 1 0 46 96 1 0 47 97 1 0 49 98 1 0 50 99 1 0 52100 1 0 53101 1 0 54102 1 0 55103 1 0 57104 1 0 58105 1 0 58106 1 0 59107 1 0 60108 1 0 62109 1 0 65110 1 0 66111 1 0 67112 1 0 69113 1 0 69114 1 0 69115 1 0 70116 1 0 M END

Standard InCHIKey	WGYORXDPWQXLQS-LTYYXYBQSA-N
Standard InCHI	InChI=1S/C50H46O20/c1-63-35-20-28(10-15-32(35)55)43(59)38(23-51)66-34-16-5-26(19-36(34)64-2)7-17-40(57)65-24-39-44(60)48(69-41(58)18-6-25-3-11-29(52)12-4-25)46(62)50(68-39)70-49-45(61)42-33(56)21-31(54)22-37(42)67-47(49)27-8-13-30(53)14-9-27/h3-22,38-39,43-44,46,48,50-56,59-60,62H,23-24H2,1-2H3/b17-7+,18-6+/t38?,39-,43?,44-,46-,48+,50+/m1/s1
SMILES	COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC=C(C=C5)O)O)OC(=O)C=CC6=CC=C(C=C6)O)O)OC(CO)C(C7=CC(=C(C=C7)O)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	966.26	Volume:	933.899 ? Van der Waals volume.
Dense:	1.035	LogP:	2.417 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.272 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.951 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	46.0
TPSA:	311.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.046	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.283	Fsp³:	0.22
MCE-18:	148.705 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.994	Fluc inhibitor:	0.666 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.723 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.902 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.253	Promiscuous compounds:	0.877

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.214	MDCK Permeability:	-5.393
Pgp-inhibitor:	0.0	Pgp-substrate:	0.025
PAMPA:	0.999 ? 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):	0.187
20% Bioavailability (F20%):	0.983	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.252
Plasma Protein Binding (PPB):	89.434%	Volume Distribution (VD):	0.236
Fu:	11.866% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.318
BSEP inhibitor:	0.861

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.439	CYP2D6-substrate:	0.997
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.567 ? 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):

2.579

Half-life (T1/2):

3.693

ADMET: Toxicity

hERG Blockers:	0.111	hERG Blockers (10um):	0.661
Human Hepatotoxicity (H-HT):	0.298	Drug-induced Liver Injury (DILI):	0.225
AMES Toxicity:	0.653	Rat Oral Acute Toxicity:	0.076
Maximum Recommended Daily Dose:	0.982	Skin Sensitization:	0.977
Carcinogencity:	0.117	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.041
Drug-induced Neurotoxicity:	0.068	Ototoxicity:	0.964
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.343
Genotoxicity:	0.851	RPMI-8226 Immunitoxicity:	0.167
A549 Cytotoxicity:	0.684	Hek293 Cytotoxicity:	0.998
BCF:	0.779 ? 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:	3.968 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.92 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.596 ? 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
NPO12512	Stenochlaena palustris	Species	Blechnaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9917285]
NPO12512	Stenochlaena palustris	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12512	Stenochlaena palustris	Species	Blechnaceae	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

Activity Type	# Activity
MIC	4

Activity Type	# Activity
Organism	4

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
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	256.0	ug.mL-1	Open TG-GATES in vivo data: Biochemistry
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	256.0	ug.mL-1	PMID[11421731]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	256.0	ug.mL-1	PMID[11421731]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	256.0	ug.mL-1	Open TG-GATES in vivo data: Biochemistry

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 NPC475179 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	18899
0.1-0.2	27653
0.2-0.3	2679
0.3-0.4	390
0.4-0.5	182
0.5-0.6	43
0.6-0.7	7
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8214	Intermediate Similarity	NPC474093
0.8214	Intermediate Similarity	NPC104910
0.7658	Intermediate Similarity	NPC96605
0.7658	Intermediate Similarity	NPC280642
0.6696	Remote Similarity	NPC205824
0.6356	Remote Similarity	NPC85751
0.6356	Remote Similarity	NPC19240
0.626	Remote Similarity	NPC217520
0.625	Remote Similarity	NPC241781
0.6179	Remote Similarity	NPC477895
0.6116	Remote Similarity	NPC223426
0.5984	Remote Similarity	NPC218161
0.5935	Remote Similarity	NPC214621
0.5935	Remote Similarity	NPC34267
0.5865	Remote Similarity	NPC25946
0.584	Remote Similarity	NPC470416
0.5781	Remote Similarity	NPC139571
0.568	Remote Similarity	NPC81042
0.5656	Remote Similarity	NPC104883
0.5656	Remote Similarity	NPC488679
0.5645	Remote Similarity	NPC36138
0.5588	Remote Similarity	NPC21359
0.5588	Remote Similarity	NPC460984
0.5433	Remote Similarity	NPC478277
0.5433	Remote Similarity	NPC478276
0.5433	Remote Similarity	NPC478275
0.5433	Remote Similarity	NPC92815
0.5414	Remote Similarity	NPC470713
0.5373	Remote Similarity	NPC471030
0.536	Remote Similarity	NPC101399
0.536	Remote Similarity	NPC221288
0.536	Remote Similarity	NPC217822
0.536	Remote Similarity	NPC11847
0.536	Remote Similarity	NPC198938
0.536	Remote Similarity	NPC194836
0.536	Remote Similarity	NPC91493
0.536	Remote Similarity	NPC605081
0.5354	Remote Similarity	NPC483767
0.5354	Remote Similarity	NPC483769
0.5354	Remote Similarity	NPC483768
0.5354	Remote Similarity	NPC483766
0.5333	Remote Similarity	NPC488078
0.5312	Remote Similarity	NPC483765
0.5308	Remote Similarity	NPC473278
0.5242	Remote Similarity	NPC470125
0.5188	Remote Similarity	NPC470716
0.5188	Remote Similarity	NPC470718
0.5169	Remote Similarity	NPC129217
0.5152	Remote Similarity	NPC470712
0.5139	Remote Similarity	NPC249560
0.5109	Remote Similarity	NPC470720
0.5109	Remote Similarity	NPC488079
0.5038	Remote Similarity	NPC203145
0.5036	Remote Similarity	NPC156785

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC475179 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5153
0.1-0.2	3954
0.2-0.3	39
0.3-0.4	3
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