NPASS Compound

Natural Product: NPC215095

Natural Product ID	NPC215095
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Smilaside F
IUPAC Name	[(2S,3S,4R,5R)-2-[(2R,3R,4S,5S,6R)-3-acetyloxy-6-(acetyloxymethyl)-4,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms	smilaside F
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL500983
PubChem CID	11658000
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic 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 2D 110114 0 0 0 0 0 0 0 0999 V2000 3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2537 -10.2080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5037 -11.5070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0365 -11.1952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8797 -9.7034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4162 -8.2768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4635 -11.1952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2135 -12.4942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4635 -13.7932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7135 -12.4942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4635 -13.7932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9635 -13.7932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7135 -15.0923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2135 -15.0923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9635 -13.7932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2135 -12.4942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7135 -12.4942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4635 -13.7932 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8740 -12.1171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2443 -12.7272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4579 -11.8456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3011 -10.3538 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8282 -12.4557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0417 -11.5740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4120 -12.1841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6255 -11.3024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9959 -11.9125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1527 -13.4043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9391 -14.2860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5688 -13.6759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.5230 -14.0144 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0402 -12.9336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0439 -14.0483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7718 -14.8432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8241 -16.3423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3387 -16.1335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1467 -15.9248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0702 -17.1068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5082 -18.4976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5556 -16.8980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1486 -17.0465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4206 -16.2516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3683 -14.7525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8537 -14.9613 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4156 -16.3521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9215 -17.4621 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9010 -16.5608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9825 -17.6424 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2251 -18.2285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0490 -0.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4510 -2.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7337 -8.0139 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7990 -7.0442 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4635 -8.2116 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8797 -12.6869 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5875 -10.0152 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0511 -7.9649 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4635 -11.1952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5608 -14.9912 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1275 -16.4730 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9635 -16.3913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9635 -11.1952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9635 -11.1952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2135 -12.4942 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4841 -10.7468 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6136 -13.5944 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9850 -13.9474 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8849 -10.0822 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4688 -9.8106 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2094 -11.0308 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0959 -15.7778 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3553 -14.5575 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6798 -15.5062 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2259 -13.1249 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3606 -17.7689 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5475 -14.6481 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1300 -17.6189 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7643 -18.3834 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1673 -15.4491 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0553 -16.8719 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1523 -18.1612 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9197 -16.3040 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1632 -13.4805 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6922 -18.0462 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1098 -15.0754 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3864 -16.7696 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4679 -17.8512 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7870 -19.6193 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 2.5981 0.0000 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 1 0 6 7 2 0 7 8 1 0 8 9 2 0 8 10 1 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 15 18 1 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 26 29 1 0 14 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 39 42 1 0 14 43 1 6 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 2 0 49 51 1 0 46 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 2 0 56 58 1 0 53 59 1 0 52 60 1 0 5 61 2 0 61 62 1 0 62 63 2 0 63 64 1 0 63 3 1 0 16 12 1 0 28 23 1 0 41 36 1 0 54 44 1 0 1 65 1 0 1 66 1 0 1 67 1 0 4 68 1 0 6 69 1 0 7 70 1 0 11 71 1 0 11 72 1 0 12 73 1 1 15 74 1 1 16 75 1 6 17 76 1 0 21 77 1 0 22 78 1 0 24 79 1 0 25 80 1 0 27 81 1 0 28 82 1 0 29 83 1 0 30 84 1 0 30 85 1 0 34 86 1 0 35 87 1 0 37 88 1 0 38 89 1 0 40 90 1 0 41 91 1 0 42 92 1 0 44 93 1 6 46 94 1 1 47 95 1 0 47 96 1 0 51 97 1 0 51 98 1 0 51 99 1 0 52100 1 6 53101 1 1 54102 1 6 58103 1 0 58104 1 0 58105 1 0 59106 1 0 60107 1 0 61108 1 0 62109 1 0 64110 1 0 M END

Standard InCHIKey	QHZJEIGSGZHOHS-ZSXKYDPFSA-N
Standard InCHI	InChI=1S/C44H46O20/c1-24(45)57-21-33-38(53)40(55)41(60-25(2)46)43(61-33)64-44(23-59-36(51)17-9-26-4-12-29(47)13-5-26)42(62-37(52)19-10-27-6-14-30(48)15-7-27)39(54)34(63-44)22-58-35(50)18-11-28-8-16-31(49)32(20-28)56-3/h4-20,33-34,38-43,47-49,53-55H,21-23H2,1-3H3/b17-9+,18-11+,19-10+/t33-,34-,38-,39-,40+,41-,42+,43-,44+/m1/s1
SMILES	COc1cc(/C=C/C(=O)OC[C@H]2O[C@@]([C@H]([C@@H]2O)OC(=O)/C=C/c2ccc(cc2)O)(COC(=O)/C=C/c2ccc(cc2)O)O[C@H]2O[C@H](COC(=O)C)[C@H]([C@@H]([C@H]2OC(=O)C)O)O)ccc1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	894.26	Volume:	857.782 ? Van der Waals volume.
Dense:	1.043	LogP:	1.617 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.935 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.922 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	22.0	Rigid Bonds:	37.0
TPSA:	289.8 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.064	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.32	Fsp³:	0.341
MCE-18:	125.593 ? 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:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.993	Fluc inhibitor:	0.999 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.165 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.662 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.172	Promiscuous compounds:	0.193

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.081	MDCK Permeability:	-5.369
Pgp-inhibitor:	0.973	Pgp-substrate:	0.006
PAMPA:	0.875 ? 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):	0.136
20% Bioavailability (F20%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	81.545%	Volume Distribution (VD):	-0.379
Fu:	16.339% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.981
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.72
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.943
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.758 ? 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):

1.255

Half-life (T1/2):

2.839

ADMET: Toxicity

hERG Blockers:	0.048	hERG Blockers (10um):	0.462
Human Hepatotoxicity (H-HT):	0.523	Drug-induced Liver Injury (DILI):	0.946
AMES Toxicity:	0.924	Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.684	Skin Sensitization:	1.0
Carcinogencity:	0.02	Eye Corrosion:	0.0
Eye Irritation:	0.015	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.121	Ototoxicity:	0.777
Hematotoxicity:	0.06	Drug-induced Nephrotoxicity:	0.775
Genotoxicity:	0.935	RPMI-8226 Immunitoxicity:	0.169
A549 Cytotoxicity:	0.582	Hek293 Cytotoxicity:	0.901
BCF:	0.237 ? 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:	3.454 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.936 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.559 ? 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
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	stems	n.a.	n.a.	PMID[16252910]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25611	Smilax china	Species	Smilacaceae	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
ED50	6

Activity Type	# Activity
Cell line	5
Non-molecular	1

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
NPT91	Cell line	KB	Homo sapiens	ED50	=	9.0	ug ml-1	PMID[10654412]
NPT165	Cell line	HeLa	Homo sapiens	ED50	=	8.3	ug ml-1	PMID[10654412]
NPT579	Cell line	DLD-1	Homo sapiens	ED50	=	5.0	ug ml-1	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	ED50	=	13.0	ug ml-1	PMID[14575444]
NPT81	Cell line	A549	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[22703109]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	>	20.0	ug ml-1	PMID[16252910]

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 NPC215095 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	10771
0.1-0.2	34399
0.2-0.3	3953
0.3-0.4	577
0.4-0.5	123
0.5-0.6	17
0.6-0.7	9
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC85192
0.8068	Intermediate Similarity	NPC201148
0.7727	Intermediate Similarity	NPC125823
0.7727	Intermediate Similarity	NPC7145
0.7727	Intermediate Similarity	NPC143480
0.7444	Intermediate Similarity	NPC3460
0.7381	Intermediate Similarity	NPC45224
0.7	Intermediate Similarity	NPC216819
0.6989	Remote Similarity	NPC210611
0.6667	Remote Similarity	NPC261122
0.6591	Remote Similarity	NPC471883
0.6559	Remote Similarity	NPC192763
0.6559	Remote Similarity	NPC300262
0.625	Remote Similarity	NPC287615
0.625	Remote Similarity	NPC199311
0.6222	Remote Similarity	NPC28637
0.6044	Remote Similarity	NPC484687
0.5941	Remote Similarity	NPC28651
0.5938	Remote Similarity	NPC80732
0.5895	Remote Similarity	NPC262182
0.567	Remote Similarity	NPC83743
0.5532	Remote Similarity	NPC35288
0.5417	Remote Similarity	NPC471882
0.5263	Remote Similarity	NPC156692
0.5258	Remote Similarity	NPC226005
0.521	Remote Similarity	NPC246024
0.5158	Remote Similarity	NPC225307
0.5155	Remote Similarity	NPC472612
0.5102	Remote Similarity	NPC476869
0.5089	Remote Similarity	NPC21956
0.5051	Remote Similarity	NPC88560
0.5051	Remote Similarity	NPC471881
0.5051	Remote Similarity	NPC478887
0.5048	Remote Similarity	NPC472611

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC215095 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3973
0.1-0.2	5098
0.2-0.3	75
0.3-0.4	4
0.4-0.5	0
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