NPASS Compound

Natural Product: NPC567451

Natural Product ID	NPC567451
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-[(2~{S},3~{S},4~{S},5~{R},6~{S})-4,5-dihydroxy-6-methyl-3-[(2~{S},3~{S},4~{S},5~{S})-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	3-[(2~{S},3~{S},4~{S},5~{R},6~{S})-4,5-dihydroxy-6-methyl-3-[(2~{S},3~{S},4~{S},5~{S})-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
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 105110 0 0 0 0 0 0 0 0999 V2000 -3.4554 -5.9898 -2.9353 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7661 -5.1513 -1.8726 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9837 -4.1300 -1.3496 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4701 -3.4096 -0.2740 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7106 -2.3728 0.2844 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4891 -2.0266 -0.1875 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7035 -0.9534 0.3735 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1263 -0.0268 1.2711 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4167 0.0552 1.7688 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3533 0.9313 1.1477 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2487 2.2131 1.6945 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8395 2.4809 2.8598 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5218 3.8505 2.6833 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8116 1.5651 3.4788 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4403 1.2476 4.7881 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9980 0.2459 2.7613 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1683 -0.6875 3.3261 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7621 0.5346 1.3052 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2479 -0.4284 0.4367 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2937 0.0135 -0.3272 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4650 -0.6470 -0.0353 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1067 -1.2659 -1.0625 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3153 -0.4743 -2.3103 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2230 -1.2869 -3.4617 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2682 0.6037 -2.4724 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0029 0.8702 -3.8107 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9934 0.0742 -1.8057 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7342 -1.1644 -2.3508 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2443 0.9223 1.7240 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5936 1.7736 2.5442 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0685 0.9037 1.2317 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9689 1.8452 1.6657 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5019 2.7690 2.5980 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2395 1.8427 1.1865 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6500 0.9085 0.2666 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8970 0.8739 -0.2420 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1091 1.4512 -0.0163 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0966 2.4563 0.9939 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3420 2.5974 1.5321 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8760 1.4426 2.3230 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1413 1.8639 2.8123 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3798 3.0104 0.5091 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3392 2.0187 0.2688 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6589 3.2356 -0.7920 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9043 4.3951 -0.6774 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8196 2.0225 -1.1896 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6773 1.1296 -1.8209 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7368 -0.0463 -0.1654 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1083 -1.1262 -1.1306 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9210 -2.1759 -0.4583 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0935 -2.5265 -0.9345 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8597 -3.5949 -0.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6811 -1.9489 -2.1511 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4441 -0.0538 0.3138 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5693 -0.9198 -0.0660 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0243 -2.7597 -1.2612 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7451 -3.7840 -1.8315 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6643 -5.5601 -3.5488 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1924 -7.0339 -2.5745 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3446 -6.1468 -3.5858 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4538 -3.6555 0.1341 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1694 -1.9014 1.1436 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0498 1.0820 0.0786 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0204 2.6891 3.6195 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7079 4.6165 2.7805 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8356 3.9350 1.6173 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3366 3.9835 3.4039 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8311 2.0192 3.5562 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9164 0.5054 5.1863 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0590 -0.1188 2.9109 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4170 -0.2821 3.8326 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4178 1.4860 1.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4890 1.0891 -0.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1525 -1.4894 -0.6734 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6935 -2.3018 -1.2870 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3376 -0.0135 -2.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8335 -0.9275 -4.1639 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6108 1.5198 -1.9233 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5846 1.5652 -4.1762 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2227 0.8250 -2.0453 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7485 -1.2067 -3.3176 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0742 2.9540 3.4081 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9093 2.6083 1.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7485 0.6644 0.4967 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2672 3.4714 2.2580 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2194 1.2006 3.2079 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1164 0.5373 1.7291 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8370 1.2229 2.5782 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8867 3.9412 0.7965 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0070 2.4727 -0.3407 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3568 3.4262 -1.6552 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6035 4.5928 0.2388 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1251 2.4017 -1.9784 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7076 1.2680 -2.8164 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2025 -1.5362 -1.6212 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7033 -0.6632 -1.9202 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5323 -2.6430 0.4287 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1674 -4.2121 0.4126 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5727 -3.0366 0.4754 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3685 -4.2617 -0.9130 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8759 -0.8631 -2.0767 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6523 -2.4204 -2.3758 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0037 -2.1204 -3.0453 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0612 -2.5475 -1.6958 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3482 -4.3325 -2.6660 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 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 8 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 35 48 1 0 48 49 1 0 49 50 1 0 50 51 2 3 51 52 1 0 51 53 1 0 48 54 2 0 54 55 1 0 6 56 1 0 56 57 2 0 57 3 1 0 55 7 1 0 18 10 1 0 27 20 1 0 54 31 1 0 46 37 1 0 1 58 1 0 1 59 1 0 1 60 1 0 4 61 1 0 5 62 1 0 10 63 1 6 12 64 1 1 13 65 1 0 13 66 1 0 13 67 1 0 14 68 1 1 15 69 1 0 16 70 1 6 17 71 1 0 18 72 1 6 20 73 1 1 22 74 1 0 22 75 1 0 23 76 1 1 24 77 1 0 25 78 1 1 26 79 1 0 27 80 1 1 28 81 1 0 33 82 1 0 34 83 1 0 37 84 1 1 39 85 1 1 40 86 1 0 40 87 1 0 41 88 1 0 42 89 1 1 43 90 1 0 44 91 1 6 45 92 1 0 46 93 1 6 47 94 1 0 49 95 1 0 49 96 1 0 50 97 1 0 52 98 1 0 52 99 1 0 52100 1 0 53101 1 0 53102 1 0 53103 1 0 56104 1 0 57105 1 0 M END

Standard InCHIKey	OCZZCFAOOWZSRX-AYKLIUONSA-N
Standard InCHI	InChI=1S/C38H48O19/c1-14(2)5-10-18-21(53-37-31(49)28(46)26(44)22(12-39)54-37)11-19(40)23-27(45)34(32(55-33(18)23)16-6-8-17(50-4)9-7-16)56-38-35(29(47)24(42)15(3)52-38)57-36-30(48)25(43)20(41)13-51-36/h5-9,11,15,20,22,24-26,28-31,35-44,46-49H,10,12-13H2,1-4H3/t15-,20-,22-,24-,25-,26+,28-,29-,30-,31+,35-,36-,37+,38-/m0/s1
SMILES	COC1=CC=C(C2=C(O[C@@H]3O[C@@H](C)[C@H](O)[C@H](O)[C@@H]3O[C@@H]3OC[C@H](O)[C@H](O)[C@@H]3O)C(=O)C3=C(O)C=C(O[C@@H]4O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(CC=C(C)C)=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	808.28	Volume:	757.751 ? Van der Waals volume.
Dense:	1.067	LogP:	1.38 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.923 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.584 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	37.0
TPSA:	297.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.099	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.495	Fsp³:	0.553
MCE-18:	150.864 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.697	Fluc inhibitor:	0.31 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.747 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.636 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.036	Promiscuous compounds:	0.167

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.543	MDCK Permeability:	-5.213
Pgp-inhibitor:	0.0	Pgp-substrate:	0.994
PAMPA:	1.0 ? 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):	0.988
20% Bioavailability (F20%):	0.987	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.694
Plasma Protein Binding (PPB):	67.949%	Volume Distribution (VD):	-0.12
Fu:	31.256% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.958
OATP1B3 inhibitor:	0.929	BCRP inhibitor:	0.098
BSEP inhibitor:	0.0

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:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.772
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.96 ? 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):

0.703

Half-life (T1/2):

3.329

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.028
Human Hepatotoxicity (H-HT):	0.711	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	1.0
Carcinogencity:	0.053	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.016
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.996
Hematotoxicity:	0.926	Drug-induced Nephrotoxicity:	0.991
Genotoxicity:	0.943	RPMI-8226 Immunitoxicity:	0.428
A549 Cytotoxicity:	0.995	Hek293 Cytotoxicity:	0.801
BCF:	0.683 ? 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:	3.518 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.405 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.494 ? 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
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12081149]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[22051934]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	aerial parts	herbal garden of Chungbuk National University, Cheongju, Korea	2012-Oct	PMID[24963714]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8699184]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	Database[Article]
NPO63912	Epimedium diphyllum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13357	Vancouveria hexandra	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13357	Vancouveria hexandra	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	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 NPC567451 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	13350
0.1-0.2	31115
0.2-0.3	4474
0.3-0.4	687
0.4-0.5	207
0.5-0.6	21
0.6-0.7	2
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7879	Intermediate Similarity	NPC5319
0.6476	Remote Similarity	NPC131745
0.6182	Remote Similarity	NPC76831
0.5862	Remote Similarity	NPC48984
0.5794	Remote Similarity	NPC278419
0.5794	Remote Similarity	NPC179198
0.5546	Remote Similarity	NPC25523
0.547	Remote Similarity	NPC14187
0.5439	Remote Similarity	NPC35119
0.5417	Remote Similarity	NPC480441
0.5333	Remote Similarity	NPC219043
0.5304	Remote Similarity	NPC32641
0.5304	Remote Similarity	NPC256188
0.5276	Remote Similarity	NPC192539
0.5263	Remote Similarity	NPC240306
0.5221	Remote Similarity	NPC304741
0.5169	Remote Similarity	NPC292929
0.513	Remote Similarity	NPC64425
0.5094	Remote Similarity	NPC289667
0.5093	Remote Similarity	NPC472459
0.5043	Remote Similarity	NPC255157
0.5043	Remote Similarity	NPC482026
0.5043	Remote Similarity	NPC259896
0.5041	Remote Similarity	NPC470715

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC567451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3873
0.1-0.2	5204
0.2-0.3	65
0.3-0.4	4
0.4-0.5	3
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
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
0.7879	Intermediate Similarity	NPD7804	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