NPASS Compound

Natural Product: NPC256188

Natural Product ID	NPC256188
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Kaempferol 3-O-[Alpha-L-Rhamnopyranosyl(1->2)-Beta-D-Glucopyranosyl]-7-O-Alpha-L-Rhamnopyranoside
IUPAC Name	3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1929027
PubChem CID	10485148
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-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 92 97 0 0 0 0 0 0 0 0999 V2000 -3.2090 -4.6869 1.3704 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1076 -4.1991 2.0304 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0390 -2.6905 2.1072 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0123 -2.2095 0.7810 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3857 -0.7955 0.8972 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8153 -0.1939 -0.2269 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4464 -0.1967 -0.3408 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3859 0.7534 0.1423 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7097 0.6048 -0.0462 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2757 -0.3732 -0.6559 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4875 -1.3734 -1.1724 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1246 -1.2999 -1.0229 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6229 -2.1795 -1.4724 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0824 -2.4500 -1.8459 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2199 -3.4169 -2.3366 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4509 -2.4905 -1.9810 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2725 -1.4922 -1.4677 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6588 -0.4579 -0.8166 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6291 -1.6079 -1.6497 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6107 -0.7456 -1.1799 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9342 0.1120 -2.2475 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6263 1.2334 -1.8680 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6260 2.2506 -1.3297 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6389 0.9325 -0.7887 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0283 -0.5398 -0.9679 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8312 -1.4166 -0.6282 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7344 -1.4614 0.7582 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1578 -0.8354 -0.2539 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7541 1.7278 -0.8643 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0686 1.9332 0.8600 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8978 2.6621 1.5497 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5825 3.8192 2.2204 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7072 4.2815 2.2213 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6828 3.5904 1.5525 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3443 2.4081 0.8701 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9905 5.4489 2.9063 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8735 -0.7646 0.9970 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2963 -1.6569 2.1104 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1744 -2.1720 2.9258 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6654 -1.2125 3.8170 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9597 -2.7771 1.5526 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3189 0.5396 1.0663 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0958 0.8986 -0.0284 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6002 1.9828 -0.7454 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4744 2.3852 -1.7262 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7819 2.4700 -3.0949 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6621 1.4899 -1.9286 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4229 1.2846 -0.6468 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4466 1.3250 0.4986 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8243 0.5511 1.5743 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1055 0.0557 -0.6750 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4969 2.1202 -2.8523 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7011 -5.3774 1.9157 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1663 -4.6486 1.6397 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1683 -4.5658 3.0949 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0456 -2.3919 2.5750 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8048 -0.5253 1.7934 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4604 -4.3817 -2.0585 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8948 -3.3249 -2.5032 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2295 0.3513 -0.3933 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1792 -0.0926 -0.3994 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1611 1.6684 -2.7391 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8382 2.4016 -2.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1256 3.2099 -1.0427 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1139 1.9146 -0.4122 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1670 1.0256 0.2219 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2245 -0.6746 -2.0577 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0119 -2.4373 -0.9913 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6978 -2.3783 1.1248 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9734 -0.7866 -0.8332 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4008 1.4462 -1.5569 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9450 2.3271 1.5749 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3918 4.3481 2.7439 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7076 3.9331 1.5378 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1397 1.9191 0.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4504 5.7416 3.7136 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2522 -1.2214 0.0130 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0991 -1.1869 2.7473 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5644 -2.9939 3.6278 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0792 -1.5961 4.4892 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1302 -2.6627 0.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2384 0.0893 -0.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8620 3.4157 -1.5065 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3197 1.4937 -3.3513 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0741 3.2998 -3.0900 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6017 2.6167 -3.8334 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3924 0.5116 -2.3778 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1750 2.0852 -0.4638 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3487 2.4034 0.8306 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6305 1.0150 2.4305 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6968 -0.5910 -0.0638 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2554 2.5450 -2.4196 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 11 14 1 0 14 15 1 0 14 16 2 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 24 29 1 0 8 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 33 36 1 0 5 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 38 41 1 0 37 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 45 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 48 51 1 0 47 52 1 0 39 3 1 0 49 43 1 0 12 7 1 0 26 20 1 0 35 30 1 0 18 10 1 0 1 53 1 0 2 54 1 0 2 55 1 0 3 56 1 1 5 57 1 1 15 58 1 0 16 59 1 0 18 60 1 0 20 61 1 1 22 62 1 6 23 63 1 0 23 64 1 0 23 65 1 0 24 66 1 1 25 67 1 6 26 68 1 6 27 69 1 0 28 70 1 0 29 71 1 0 31 72 1 0 32 73 1 0 34 74 1 0 35 75 1 0 36 76 1 0 37 77 1 6 38 78 1 1 39 79 1 1 40 80 1 0 41 81 1 0 43 82 1 6 45 83 1 1 46 84 1 0 46 85 1 0 46 86 1 0 47 87 1 6 48 88 1 1 49 89 1 1 50 90 1 0 51 91 1 0 52 92 1 0 M END

Standard InCHIKey	DDELFAUOHDSZJL-CPGGTDLHSA-N
Standard InCHI	InChI=1S/C33H40O19/c1-10-19(37)23(41)26(44)31(46-10)48-14-7-15(36)18-16(8-14)49-28(12-3-5-13(35)6-4-12)29(22(18)40)51-33-30(25(43)21(39)17(9-34)50-33)52-32-27(45)24(42)20(38)11(2)47-32/h3-8,10-11,17,19-21,23-27,30-39,41-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21+,23+,24+,25-,26+,27+,30+,31-,32-,33-/m0/s1
SMILES	OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	740.22	Volume:	673.908 ? Van der Waals volume.
Dense:	1.098	LogP:	0.513 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.184 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.273 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	36.0
TPSA:	308.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.11	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.286	Fsp³:	0.545
MCE-18:	150.706 ? 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:	0.622	Fluc inhibitor:	0.285 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.702 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.517 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.319	Promiscuous compounds:	0.535

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.724	MDCK Permeability:	-4.937
Pgp-inhibitor:	0.0	Pgp-substrate:	0.948
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):	0.976
20% Bioavailability (F20%):	0.235	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.02
Plasma Protein Binding (PPB):	80.576%	Volume Distribution (VD):	-0.066
Fu:	18.103% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.149
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:	0.093
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.854
HLM stability:	0.006 ? 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):

1.07

Half-life (T1/2):

5.849

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.069
Human Hepatotoxicity (H-HT):	0.533	Drug-induced Liver Injury (DILI):	0.978
AMES Toxicity:	0.914	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	1.0
Carcinogencity:	0.005	Eye Corrosion:	0.0
Eye Irritation:	0.032	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.995
Hematotoxicity:	0.102	Drug-induced Nephrotoxicity:	0.762
Genotoxicity:	0.59	RPMI-8226 Immunitoxicity:	0.261
A549 Cytotoxicity:	0.729	Hek293 Cytotoxicity:	0.457
BCF:	0.419 ? 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:	3.012 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.687 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.709 ? 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
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	flowers	n.a.	n.a.	PMID[16180811]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	branch	n.a.	PMID[22014228]
NPO27656	Lotus edulis	Species	Fabaceae	Eukaryota	n.a.	branch	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014228]
NPO27656	Lotus edulis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014228]
NPO27656	Lotus edulis	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22014228]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39355945]
NPO27656	Lotus edulis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23510	Vicia faba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27656	Lotus edulis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23510	Vicia faba	Species	Fabaceae	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
IC50	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	IC50	=	220000.0	nM	PMID[22014228]

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 NPC256188 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	24725
0.1-0.2	21144
0.2-0.3	3097
0.3-0.4	395
0.4-0.5	252
0.5-0.6	126
0.6-0.7	48
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC32641
0.9753	High Similarity	NPC35119
0.9036	High Similarity	NPC240306
0.837	Intermediate Similarity	NPC25523
0.8072	Intermediate Similarity	NPC116458
0.8072	Intermediate Similarity	NPC246943
0.7955	Intermediate Similarity	NPC64425
0.7816	Intermediate Similarity	NPC163242
0.7816	Intermediate Similarity	NPC272068
0.7778	Intermediate Similarity	NPC249281
0.7604	Intermediate Similarity	NPC480441
0.7553	Intermediate Similarity	NPC14187
0.7528	Intermediate Similarity	NPC65003
0.75	Intermediate Similarity	NPC142142
0.747	Intermediate Similarity	NPC297987
0.7381	Intermediate Similarity	NPC46420
0.7253	Intermediate Similarity	NPC470444
0.7253	Intermediate Similarity	NPC186816
0.7241	Intermediate Similarity	NPC605784
0.7159	Intermediate Similarity	NPC170052
0.7159	Intermediate Similarity	NPC276377
0.7159	Intermediate Similarity	NPC135846
0.7143	Intermediate Similarity	NPC155877
0.7065	Intermediate Similarity	NPC115674
0.7	Intermediate Similarity	NPC473682
0.6966	Remote Similarity	NPC476215
0.6957	Remote Similarity	NPC150164
0.69	Remote Similarity	NPC164704
0.6813	Remote Similarity	NPC251417
0.6744	Remote Similarity	NPC289667
0.6735	Remote Similarity	NPC602448
0.6701	Remote Similarity	NPC473071
0.6701	Remote Similarity	NPC220173
0.6667	Remote Similarity	NPC136042
0.6591	Remote Similarity	NPC271692
0.6569	Remote Similarity	NPC470715
0.6542	Remote Similarity	NPC209550
0.6531	Remote Similarity	NPC195257
0.6522	Remote Similarity	NPC254855
0.6522	Remote Similarity	NPC94610
0.6509	Remote Similarity	NPC470717
0.6495	Remote Similarity	NPC72016
0.6452	Remote Similarity	NPC8856
0.6444	Remote Similarity	NPC611303
0.6421	Remote Similarity	NPC304741
0.6404	Remote Similarity	NPC84362
0.6392	Remote Similarity	NPC12013
0.6392	Remote Similarity	NPC11432
0.6392	Remote Similarity	NPC477613
0.6344	Remote Similarity	NPC95866
0.633	Remote Similarity	NPC175429
0.6296	Remote Similarity	NPC470720
0.625	Remote Similarity	NPC111929
0.625	Remote Similarity	NPC320283
0.625	Remote Similarity	NPC331652
0.625	Remote Similarity	NPC41121
0.6239	Remote Similarity	NPC138990
0.6214	Remote Similarity	NPC473072
0.62	Remote Similarity	NPC76831
0.618	Remote Similarity	NPC108831
0.618	Remote Similarity	NPC182634
0.6146	Remote Similarity	NPC470405
0.6111	Remote Similarity	NPC158674
0.6022	Remote Similarity	NPC224530
0.6019	Remote Similarity	NPC295625
0.6	Remote Similarity	NPC39360
0.6	Remote Similarity	NPC77672
0.6	Remote Similarity	NPC133671
0.6	Remote Similarity	NPC135391
0.6	Remote Similarity	NPC29763
0.6	Remote Similarity	NPC78263
0.6	Remote Similarity	NPC210003
0.6	Remote Similarity	NPC250069
0.598	Remote Similarity	NPC221342
0.598	Remote Similarity	NPC476470
0.5963	Remote Similarity	NPC298666
0.5934	Remote Similarity	NPC323593
0.5934	Remote Similarity	NPC203500
0.5882	Remote Similarity	NPC475382
0.5876	Remote Similarity	NPC139320
0.587	Remote Similarity	NPC24043
0.5859	Remote Similarity	NPC255157
0.5859	Remote Similarity	NPC259896
0.5849	Remote Similarity	NPC219043
0.5842	Remote Similarity	NPC122467
0.5825	Remote Similarity	NPC292929
0.5824	Remote Similarity	NPC19709
0.5824	Remote Similarity	NPC238376
0.5816	Remote Similarity	NPC173582
0.5816	Remote Similarity	NPC44931
0.5816	Remote Similarity	NPC265885
0.5816	Remote Similarity	NPC181465
0.5816	Remote Similarity	NPC215710
0.5816	Remote Similarity	NPC473438
0.5816	Remote Similarity	NPC253788
0.5766	Remote Similarity	NPC470719
0.5752	Remote Similarity	NPC192539
0.57	Remote Similarity	NPC122809
0.5688	Remote Similarity	NPC255799
0.5686	Remote Similarity	NPC606657
0.5676	Remote Similarity	NPC480445
0.566	Remote Similarity	NPC203145
0.5652	Remote Similarity	NPC127546
0.5652	Remote Similarity	NPC57625
0.5652	Remote Similarity	NPC173637
0.5652	Remote Similarity	NPC317489
0.5652	Remote Similarity	NPC223424
0.5652	Remote Similarity	NPC600591
0.5619	Remote Similarity	NPC253685
0.5612	Remote Similarity	NPC239549
0.5607	Remote Similarity	NPC189564
0.56	Remote Similarity	NPC605592
0.5596	Remote Similarity	NPC311850
0.5591	Remote Similarity	NPC64305
0.5591	Remote Similarity	NPC277205
0.5591	Remote Similarity	NPC37919
0.5591	Remote Similarity	NPC189142
0.5591	Remote Similarity	NPC77660
0.5556	Remote Similarity	NPC48984
0.5556	Remote Similarity	NPC480466
0.5546	Remote Similarity	NPC223860
0.5545	Remote Similarity	NPC470716
0.5536	Remote Similarity	NPC198199
0.5534	Remote Similarity	NPC482026
0.5532	Remote Similarity	NPC27640
0.5532	Remote Similarity	NPC488080
0.5532	Remote Similarity	NPC169977
0.5514	Remote Similarity	NPC89052
0.5514	Remote Similarity	NPC121703
0.5505	Remote Similarity	NPC470712
0.55	Remote Similarity	NPC67105
0.5495	Remote Similarity	NPC288084
0.5484	Remote Similarity	NPC348541
0.5474	Remote Similarity	NPC216496
0.5474	Remote Similarity	NPC472459
0.5446	Remote Similarity	NPC65563
0.5446	Remote Similarity	NPC210073
0.5446	Remote Similarity	NPC470949
0.5446	Remote Similarity	NPC488739
0.5437	Remote Similarity	NPC483414
0.5426	Remote Similarity	NPC145038
0.5426	Remote Similarity	NPC8573
0.5426	Remote Similarity	NPC56077
0.5426	Remote Similarity	NPC281131
0.5426	Remote Similarity	NPC253662
0.5426	Remote Similarity	NPC179950
0.5426	Remote Similarity	NPC88789
0.5426	Remote Similarity	NPC491374
0.5392	Remote Similarity	NPC473571
0.5392	Remote Similarity	NPC110941
0.5385	Remote Similarity	NPC25946
0.5376	Remote Similarity	NPC473043
0.537	Remote Similarity	NPC25724
0.5364	Remote Similarity	NPC303694
0.5347	Remote Similarity	NPC471748
0.534	Remote Similarity	NPC61904
0.5327	Remote Similarity	NPC135358
0.5319	Remote Similarity	NPC261866
0.5315	Remote Similarity	NPC277532
0.5312	Remote Similarity	NPC59534
0.531	Remote Similarity	NPC68592
0.531	Remote Similarity	NPC488734
0.531	Remote Similarity	NPC488735
0.531	Remote Similarity	NPC488732
0.531	Remote Similarity	NPC488738
0.5306	Remote Similarity	NPC223747
0.5304	Remote Similarity	NPC480444
0.5294	Remote Similarity	NPC203259
0.5294	Remote Similarity	NPC33054
0.5294	Remote Similarity	NPC176740
0.5294	Remote Similarity	NPC471725
0.5294	Remote Similarity	NPC134532
0.5294	Remote Similarity	NPC602582
0.5283	Remote Similarity	NPC89127
0.5263	Remote Similarity	NPC197896
0.5263	Remote Similarity	NPC95090
0.5263	Remote Similarity	NPC313163
0.5263	Remote Similarity	NPC27408
0.5259	Remote Similarity	NPC120952
0.5258	Remote Similarity	NPC307938
0.5258	Remote Similarity	NPC219904
0.5258	Remote Similarity	NPC285197
0.5258	Remote Similarity	NPC488071
0.5253	Remote Similarity	NPC66087
0.5248	Remote Similarity	NPC29958
0.5213	Remote Similarity	NPC135599
0.5213	Remote Similarity	NPC73855
0.5213	Remote Similarity	NPC113968
0.5213	Remote Similarity	NPC328940
0.5213	Remote Similarity	NPC277174
0.5213	Remote Similarity	NPC606877
0.5208	Remote Similarity	NPC305811
0.5204	Remote Similarity	NPC22832
0.5204	Remote Similarity	NPC601144
0.5189	Remote Similarity	NPC5319
0.5182	Remote Similarity	NPC488075
0.5155	Remote Similarity	NPC27942
0.5155	Remote Similarity	NPC599850
0.5152	Remote Similarity	NPC136761

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC256188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6108
0.1-0.2	2976
0.2-0.3	57
0.3-0.4	2
0.4-0.5	2
0.5-0.6	4
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
0.604	Remote Similarity	NPD7251	Phase 2
0.566	Remote Similarity	NPD7808	Phase 3
0.5294	Remote Similarity	NPD6797	Phase 2
0.5189	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5094	Remote Similarity	NPD7054	Phase 4

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