NPASS Compound

Natural Product: NPC470717

Natural Product ID	NPC470717
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Allivictoside F
IUPAC Name	[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-3-yl]oxy-6-(hydroxymethyl)oxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms	Allivictoside F
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2206202
PubChem CID	71459648
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 94 99 0 0 0 0 0 0 0 0999 V2000 1.4443 -6.4193 0.3527 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0998 -5.2059 0.9420 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4618 -4.0264 0.0489 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1102 -2.8750 0.6646 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7479 -1.7151 0.0977 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1531 -0.6175 0.7890 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1195 -0.1902 0.3736 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2809 0.7950 -0.5291 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5438 1.0945 -0.8587 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6064 0.5287 -0.3875 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4941 -0.4863 0.5483 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2331 -0.8535 0.9365 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0489 -1.7606 1.7754 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6344 -1.0695 1.0315 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5028 -2.1014 1.9856 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8983 -0.6804 0.6165 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0421 0.3256 -0.3142 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8849 0.8947 -0.7824 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2915 0.7045 -0.7224 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5308 0.2589 -0.3354 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1189 -0.6098 -1.2790 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1706 -1.2216 -0.6064 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.5658 -2.5451 -1.1860 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9696 -2.4328 -2.4973 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2936 -0.2147 -0.5469 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8294 0.9070 0.3635 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.4680 1.4027 -0.0158 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9108 2.1204 1.0523 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7388 1.9888 0.2826 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4786 -0.7499 -0.0500 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7919 1.5548 -1.1691 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0879 1.6136 -0.7724 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0636 2.3306 -1.4596 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7491 3.0296 -2.5989 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4342 2.9869 -3.0249 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4769 2.2699 -2.3320 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7218 3.7518 -3.2921 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1665 -1.8858 0.3889 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6853 -2.9756 -0.5811 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8441 -4.1905 -0.4481 C 0 0 2 0 0 0 0 0 0 0 0 0 2.8849 -4.9718 -1.6389 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0173 -3.1733 -0.3033 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0606 -0.8260 0.2243 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9890 -0.4647 1.2012 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9684 -1.1528 2.2460 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9378 0.6261 1.0611 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7783 0.8484 2.0628 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7818 1.8780 2.1036 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6285 2.0191 3.1845 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5986 2.9905 3.2557 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7661 3.8813 2.2259 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9337 3.7651 1.1318 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9501 2.7725 1.0706 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0888 4.6523 0.0916 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3154 4.6650 -1.0829 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7579 4.8737 2.2992 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2493 -6.8225 0.7594 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0155 -5.2552 1.1684 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6172 -5.0667 1.9259 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7785 -4.1375 -0.8473 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4117 -1.6456 -0.9535 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4475 -3.0404 1.5622 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7163 -1.2119 1.0665 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9667 1.6837 -1.5103 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4459 -0.3648 0.5795 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8303 -1.3669 0.4603 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4179 -2.9222 -0.5609 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7446 -3.2622 -1.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8768 -3.3126 -2.9515 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4037 0.2124 -1.5693 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8328 0.5878 1.4271 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5144 2.0446 -0.9324 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9631 3.1042 0.9182 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5564 2.4703 -0.5672 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1712 -0.5962 -0.7352 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3757 1.1121 0.1283 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1001 2.3433 -1.0923 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1966 3.5395 -3.9230 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5444 2.2455 -2.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2579 4.5008 -2.8555 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2768 -2.3391 1.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6066 -2.5492 -1.5880 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3906 -4.8590 0.2896 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9615 -5.3602 -1.7704 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6161 -3.1130 -1.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9854 1.2544 0.1838 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7183 0.1931 2.9558 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4915 1.2992 4.0128 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2239 3.0402 4.1286 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3180 2.7098 0.2033 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2344 4.6360 -0.7624 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5360 3.8416 -1.7878 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4903 5.6568 -1.5614 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7400 4.6355 2.2245 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 23 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 25 30 1 0 8 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 34 37 1 0 5 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 39 42 1 0 38 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 46 47 2 0 47 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 52 54 1 0 54 55 1 0 51 56 1 0 40 3 1 0 53 48 1 0 12 7 1 0 27 20 1 0 36 31 1 0 18 10 1 0 1 57 1 0 2 58 1 0 2 59 1 0 3 60 1 6 5 61 1 6 15 62 1 0 16 63 1 0 18 64 1 0 20 65 1 1 22 66 1 1 23 67 1 0 23 68 1 0 24 69 1 0 25 70 1 6 26 71 1 1 27 72 1 6 28 73 1 0 29 74 1 0 30 75 1 0 32 76 1 0 33 77 1 0 35 78 1 0 36 79 1 0 37 80 1 0 38 81 1 1 39 82 1 6 40 83 1 1 41 84 1 0 42 85 1 0 46 86 1 0 47 87 1 0 49 88 1 0 50 89 1 0 53 90 1 0 55 91 1 0 55 92 1 0 55 93 1 0 56 94 1 0 M END

Standard InCHIKey	SLIBKVWISCHMPI-FOPGHQQOSA-N
Standard InCHI	InChI=1S/C37H38O19/c1-50-21-10-15(2-8-19(21)41)3-9-25(43)55-35-31(48)28(45)24(14-39)54-37(35)56-34-29(46)26-20(42)11-18(51-36-32(49)30(47)27(44)23(13-38)53-36)12-22(26)52-33(34)16-4-6-17(40)7-5-16/h2-12,23-24,27-28,30-32,35-42,44-45,47-49H,13-14H2,1H3/b9-3+/t23-,24-,27-,28-,30+,31+,32-,35-,36-,37+/m1/s1
SMILES	OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)/C=C/c1ccc(c(c1)OC)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	786.2	Volume:	729.91 ? Van der Waals volume.
Dense:	1.077	LogP:	1.218 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.588 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.633 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	38.0
TPSA:	304.96 ? 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:	0.066	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.051	Fsp³:	0.351
MCE-18:	139.4 ? 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:	0.748	Fluc inhibitor:	0.547 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.901 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.667 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.205	Promiscuous compounds:	0.523

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.515	MDCK Permeability:	-5.153
Pgp-inhibitor:	0.0	Pgp-substrate:	0.166
PAMPA:	0.998 ? 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):	0.934
20% Bioavailability (F20%):	0.594	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.004
Plasma Protein Binding (PPB):	80.508%	Volume Distribution (VD):	-0.007
Fu:	17.229% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.629
BSEP inhibitor:	0.005

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:	0.165
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.01 ? 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):

1.556

Half-life (T1/2):

4.977

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.035
Human Hepatotoxicity (H-HT):	0.841	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.974	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.012	Skin Sensitization:	1.0
Carcinogencity:	0.124	Eye Corrosion:	0.0
Eye Irritation:	0.005	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.987
Hematotoxicity:	0.114	Drug-induced Nephrotoxicity:	0.887
Genotoxicity:	0.981	RPMI-8226 Immunitoxicity:	0.181
A549 Cytotoxicity:	0.783	Hek293 Cytotoxicity:	0.812
BCF:	0.498 ? 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:	3.24 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.825 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.026 ? 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
NPO3860.1	Allium victorialis	Under-species	n.a.	n.a.	Leaves	Taeback, GangWon province, Korea	2011-Jan	PMID[23149227]

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
Activity	1
IC50	1

Activity Type	# Activity
Cell line	2

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
NPT34	Cell line	BV-2	Mus musculus	Activity	=	100.0	%	PubChem BioAssay data set
NPT34	Cell line	BV-2	Mus musculus	IC50	=	20420.0	nM	PMID[1375626]

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 NPC470717 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	19497
0.1-0.2	25930
0.2-0.3	3174
0.3-0.4	785
0.4-0.5	312
0.5-0.6	122
0.6-0.7	20
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9691	High Similarity	NPC470720
0.9381	High Similarity	NPC295625
0.9	High Similarity	NPC470719
0.8969	High Similarity	NPC164704
0.8586	High Similarity	NPC470715
0.8173	Intermediate Similarity	NPC470713
0.7653	Intermediate Similarity	NPC64425
0.7358	Intermediate Similarity	NPC470712
0.7064	Intermediate Similarity	NPC470716
0.7064	Intermediate Similarity	NPC470718
0.6667	Remote Similarity	NPC297987
0.6667	Remote Similarity	NPC35119
0.6667	Remote Similarity	NPC25946
0.6509	Remote Similarity	NPC32641
0.6509	Remote Similarity	NPC256188
0.6337	Remote Similarity	NPC116458
0.6337	Remote Similarity	NPC246943
0.6321	Remote Similarity	NPC240306
0.626	Remote Similarity	NPC223860
0.6224	Remote Similarity	NPC289667
0.6198	Remote Similarity	NPC21359
0.6198	Remote Similarity	NPC460984
0.6195	Remote Similarity	NPC480796
0.6195	Remote Similarity	NPC472993
0.6186	Remote Similarity	NPC488078
0.614	Remote Similarity	NPC25523
0.6116	Remote Similarity	NPC199172
0.61	Remote Similarity	NPC84362
0.605	Remote Similarity	NPC488079
0.6	Remote Similarity	NPC136042
0.5965	Remote Similarity	NPC470416
0.5935	Remote Similarity	NPC480470
0.5849	Remote Similarity	NPC251417
0.5784	Remote Similarity	NPC46420
0.5772	Remote Similarity	NPC480472
0.5766	Remote Similarity	NPC139060
0.5743	Remote Similarity	NPC249281
0.5714	Remote Similarity	NPC605784
0.5702	Remote Similarity	NPC218161
0.5701	Remote Similarity	NPC473682
0.568	Remote Similarity	NPC35924
0.5631	Remote Similarity	NPC24043
0.5619	Remote Similarity	NPC224530
0.5593	Remote Similarity	NPC480441
0.5524	Remote Similarity	NPC611303
0.5517	Remote Similarity	NPC14187
0.5514	Remote Similarity	NPC170052
0.5514	Remote Similarity	NPC276377
0.5514	Remote Similarity	NPC135846
0.5487	Remote Similarity	NPC210961
0.5481	Remote Similarity	NPC488080
0.5481	Remote Similarity	NPC169977
0.5472	Remote Similarity	NPC22832
0.5446	Remote Similarity	NPC472992
0.5439	Remote Similarity	NPC205824
0.5439	Remote Similarity	NPC221288
0.5439	Remote Similarity	NPC142142
0.5439	Remote Similarity	NPC270675
0.5439	Remote Similarity	NPC194836
0.5439	Remote Similarity	NPC195685
0.5439	Remote Similarity	NPC91493
0.5439	Remote Similarity	NPC605081
0.5437	Remote Similarity	NPC39360
0.5437	Remote Similarity	NPC77672
0.5437	Remote Similarity	NPC133671
0.5437	Remote Similarity	NPC135391
0.5437	Remote Similarity	NPC29763
0.5437	Remote Similarity	NPC78263
0.5437	Remote Similarity	NPC210003
0.5437	Remote Similarity	NPC250069
0.5431	Remote Similarity	NPC483767
0.5431	Remote Similarity	NPC483769
0.5431	Remote Similarity	NPC483768
0.5431	Remote Similarity	NPC483766
0.5429	Remote Similarity	NPC472459
0.5421	Remote Similarity	NPC311830
0.542	Remote Similarity	NPC249560
0.5417	Remote Similarity	NPC277532
0.541	Remote Similarity	NPC474093
0.541	Remote Similarity	NPC104910
0.5405	Remote Similarity	NPC150164
0.5398	Remote Similarity	NPC477628
0.5391	Remote Similarity	NPC80068
0.5391	Remote Similarity	NPC85751
0.5391	Remote Similarity	NPC76831
0.5391	Remote Similarity	NPC19240
0.5385	Remote Similarity	NPC323593
0.5385	Remote Similarity	NPC203500
0.5378	Remote Similarity	NPC219043
0.537	Remote Similarity	NPC203050
0.537	Remote Similarity	NPC225434
0.536	Remote Similarity	NPC138990
0.5351	Remote Similarity	NPC104883
0.5351	Remote Similarity	NPC488679
0.5345	Remote Similarity	NPC36138
0.5339	Remote Similarity	NPC121703
0.5333	Remote Similarity	NPC217520
0.5327	Remote Similarity	NPC120099
0.5327	Remote Similarity	NPC486578
0.5323	Remote Similarity	NPC162394
0.5304	Remote Similarity	NPC472991
0.5254	Remote Similarity	NPC214621
0.5254	Remote Similarity	NPC34267
0.5254	Remote Similarity	NPC483765
0.525	Remote Similarity	NPC48984
0.5238	Remote Similarity	NPC64305
0.5238	Remote Similarity	NPC95090
0.5238	Remote Similarity	NPC27408
0.5234	Remote Similarity	NPC285197
0.5229	Remote Similarity	NPC488072
0.5229	Remote Similarity	NPC601586
0.5221	Remote Similarity	NPC470444
0.5221	Remote Similarity	NPC186816
0.5217	Remote Similarity	NPC72016
0.5217	Remote Similarity	NPC606657
0.5197	Remote Similarity	NPC175429
0.5189	Remote Similarity	NPC271692
0.5185	Remote Similarity	NPC243930
0.5185	Remote Similarity	NPC21666
0.5185	Remote Similarity	NPC601144
0.5185	Remote Similarity	NPC609478
0.5179	Remote Similarity	NPC163242
0.5179	Remote Similarity	NPC272068
0.5169	Remote Similarity	NPC484301
0.5169	Remote Similarity	NPC472994
0.5133	Remote Similarity	NPC304741
0.5128	Remote Similarity	NPC220173
0.5124	Remote Similarity	NPC477895
0.5122	Remote Similarity	NPC139571
0.5118	Remote Similarity	NPC209550
0.5115	Remote Similarity	NPC473554
0.5094	Remote Similarity	NPC8573
0.5094	Remote Similarity	NPC277205
0.5094	Remote Similarity	NPC37919
0.5094	Remote Similarity	NPC189142
0.5094	Remote Similarity	NPC77660
0.5093	Remote Similarity	NPC168584
0.5093	Remote Similarity	NPC60735
0.5093	Remote Similarity	NPC26230
0.5093	Remote Similarity	NPC488071
0.5046	Remote Similarity	NPC101026
0.5046	Remote Similarity	NPC80188
0.5046	Remote Similarity	NPC488077
0.5045	Remote Similarity	NPC254855
0.5045	Remote Similarity	NPC94610
0.5043	Remote Similarity	NPC101399
0.5043	Remote Similarity	NPC61904
0.5043	Remote Similarity	NPC217822
0.5043	Remote Similarity	NPC11847
0.5043	Remote Similarity	NPC198938
0.5042	Remote Similarity	NPC223426
0.5036	Remote Similarity	NPC487501

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5079
0.1-0.2	4010
0.2-0.3	52
0.3-0.4	4
0.4-0.5	5
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