NPASS Compound

Natural Product: NPC164704

Natural Product ID	NPC164704
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-(2''-(E)-P-Coumaroylglucoside)-7-O-Beta-D-Glucoside
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-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2206211
PubChem CID	71457745
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 90 95 0 0 0 0 0 0 0 0999 V2000 1.3659 -5.1277 0.3331 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5163 -5.6819 -0.2123 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5989 -4.7122 -0.5274 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3230 -3.7225 -1.4144 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8284 -2.5310 -0.9182 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6038 -2.6144 -0.3423 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3806 -2.0896 -0.3793 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7365 -2.4446 -1.0867 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8926 -1.7622 -0.9556 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0576 -0.7428 -0.1802 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0017 -0.2916 0.5801 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1875 -0.9696 0.4648 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1407 -0.5355 1.1709 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1442 0.7912 1.4188 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0442 1.1922 2.1551 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3392 1.4632 1.5308 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4109 1.0403 0.7870 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2440 -0.0638 -0.0602 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6169 1.6833 0.8750 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0230 2.7217 1.6736 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0984 2.3376 2.4525 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3174 2.3608 1.8247 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4762 1.1057 1.0036 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7247 1.1203 0.3524 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6206 3.6214 1.0560 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4822 3.9360 0.1269 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2414 4.0480 0.9708 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4473 5.0635 1.9289 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3032 2.9061 -0.8068 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6754 4.6927 1.9739 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7951 -3.5588 -2.0094 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2200 -4.1053 -2.7038 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0892 -5.2452 -3.4919 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1301 -5.8599 -3.5837 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2056 -5.3455 -2.8990 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0318 -4.2202 -2.1317 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3443 -7.0136 -4.3562 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8340 -1.8940 0.0529 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0073 -2.9058 0.1910 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3065 -4.1696 0.7281 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2234 -5.0515 1.2422 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9218 -2.4733 1.1215 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3515 -0.6751 -0.3903 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4355 0.4616 0.4036 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0223 0.3826 1.5804 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9891 1.7187 -0.1047 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0382 2.7457 0.7244 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5515 4.0450 0.3882 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5748 5.0712 1.3089 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0595 6.3102 1.0371 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5645 6.6014 -0.2128 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5614 5.6110 -1.1636 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0608 4.3510 -0.8623 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0650 7.8824 -0.4777 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6115 -5.5027 -0.1933 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3077 -6.3358 -1.0928 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8989 -6.3933 0.5828 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4219 -5.3339 -1.0175 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8568 -1.8210 -1.8132 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2706 0.7652 2.9956 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3996 2.3385 2.2172 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0754 -0.4090 -0.6538 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1982 2.9403 2.4253 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1298 2.2614 2.6378 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5092 0.2082 1.6705 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7066 0.9402 0.2497 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5897 1.1551 -0.6142 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5957 3.5557 0.5412 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6469 4.9062 -0.4034 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4135 4.3418 0.3348 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3527 4.6579 2.8244 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6695 3.1760 -1.5102 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1683 4.3768 2.7629 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1825 -3.6560 -2.7266 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9481 -5.6603 -4.0373 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1831 -5.8415 -2.9747 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8654 -3.8174 -1.5898 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5363 -7.3601 -4.8597 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4453 -1.8591 1.0886 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4541 -3.1511 -0.7651 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5730 -3.9116 1.5121 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8520 -5.6831 1.8948 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8037 -2.4947 0.7061 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3476 1.8370 -1.1066 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6640 2.6118 1.7540 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1723 4.8668 2.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0345 7.0515 1.8284 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9621 5.8437 -2.1639 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0888 3.6241 -1.6618 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7270 8.3145 -1.3485 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 51 54 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 55 1 0 2 56 1 0 2 57 1 0 3 58 1 6 5 59 1 6 15 60 1 0 16 61 1 0 18 62 1 0 20 63 1 1 22 64 1 1 23 65 1 0 23 66 1 0 24 67 1 0 25 68 1 6 26 69 1 6 27 70 1 6 28 71 1 0 29 72 1 0 30 73 1 0 32 74 1 0 33 75 1 0 35 76 1 0 36 77 1 0 37 78 1 0 38 79 1 1 39 80 1 6 40 81 1 1 41 82 1 0 42 83 1 0 46 84 1 0 47 85 1 0 49 86 1 0 50 87 1 0 52 88 1 0 53 89 1 0 54 90 1 0 M END

Standard InCHIKey	SOPVQGCZAWJHCX-MSQUEZNUSA-N
Standard InCHI	InChI=1S/C36H36O18/c37-13-22-26(43)29(46)31(48)35(51-22)49-19-11-20(41)25-21(12-19)50-32(16-4-8-18(40)9-5-16)33(28(25)45)54-36-34(30(47)27(44)23(14-38)52-36)53-24(42)10-3-15-1-6-17(39)7-2-15/h1-12,22-23,26-27,29-31,34-41,43-44,46-48H,13-14H2/b10-3+/t22-,23-,26-,27-,29+,30+,31-,34-,35-,36+/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(cc1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.19	Volume:	703.823 ? Van der Waals volume.
Dense:	1.074	LogP:	1.132 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.438 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.775 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	38.0
TPSA:	295.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	6.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.07	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.986	Fsp³:	0.333
MCE-18:	136.667 ? 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:	0.742	Fluc inhibitor:	0.576 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.819 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.666 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.421	Promiscuous compounds:	0.569

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.649	MDCK Permeability:	-4.953
Pgp-inhibitor:	0.0	Pgp-substrate:	0.131
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):	0.776
20% Bioavailability (F20%):	0.661	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	82.485%	Volume Distribution (VD):	0.02
Fu:	15.813% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.084
BSEP inhibitor:	0.007

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:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.348
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.027 ? 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):

1.493

Half-life (T1/2):

4.904

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.041
Human Hepatotoxicity (H-HT):	0.871	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.973	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.022	Skin Sensitization:	1.0
Carcinogencity:	0.115	Eye Corrosion:	0.0
Eye Irritation:	0.008	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.986
Hematotoxicity:	0.078	Drug-induced Nephrotoxicity:	0.842
Genotoxicity:	0.995	RPMI-8226 Immunitoxicity:	0.122
A549 Cytotoxicity:	0.761	Hek293 Cytotoxicity:	0.903
BCF:	0.499 ? 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:	3.292 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.845 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.117 ? 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	=	104.9	%	PMID[2128517]
NPT34	Cell line	BV-2	Mus musculus	IC50	=	47200.0	nM	PMID[18519713]

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 NPC164704 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	17702
0.1-0.2	27761
0.2-0.3	3204
0.3-0.4	684
0.4-0.5	320
0.5-0.6	142
0.6-0.7	25
0.7-0.8	0
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC470715
0.8969	High Similarity	NPC470717
0.8687	High Similarity	NPC470720
0.8384	Intermediate Similarity	NPC295625
0.8163	Intermediate Similarity	NPC470712
0.8152	Intermediate Similarity	NPC64425
0.8039	Intermediate Similarity	NPC470719
0.7822	Intermediate Similarity	NPC470716
0.7647	Intermediate Similarity	NPC470718
0.7264	Intermediate Similarity	NPC470713
0.7111	Intermediate Similarity	NPC297987
0.7071	Intermediate Similarity	NPC35119
0.69	Remote Similarity	NPC32641
0.69	Remote Similarity	NPC256188
0.6737	Remote Similarity	NPC116458
0.6737	Remote Similarity	NPC246943
0.663	Remote Similarity	NPC289667
0.6581	Remote Similarity	NPC223860
0.6481	Remote Similarity	NPC25523
0.6408	Remote Similarity	NPC139060
0.6383	Remote Similarity	NPC136042
0.6373	Remote Similarity	NPC240306
0.6321	Remote Similarity	NPC218161
0.6146	Remote Similarity	NPC84362
0.6105	Remote Similarity	NPC249281
0.6095	Remote Similarity	NPC210961
0.6061	Remote Similarity	NPC605784
0.6058	Remote Similarity	NPC472992
0.604	Remote Similarity	NPC251417
0.6038	Remote Similarity	NPC205824
0.6038	Remote Similarity	NPC221288
0.6038	Remote Similarity	NPC270675
0.6038	Remote Similarity	NPC194836
0.6038	Remote Similarity	NPC195685
0.6038	Remote Similarity	NPC91493
0.6038	Remote Similarity	NPC605081
0.6	Remote Similarity	NPC477628
0.5981	Remote Similarity	NPC80068
0.5981	Remote Similarity	NPC85751
0.5981	Remote Similarity	NPC19240
0.596	Remote Similarity	NPC224530
0.5943	Remote Similarity	NPC104883
0.5943	Remote Similarity	NPC488679
0.5938	Remote Similarity	NPC39360
0.5938	Remote Similarity	NPC29763
0.5938	Remote Similarity	NPC210003
0.5935	Remote Similarity	NPC249560
0.5893	Remote Similarity	NPC480441
0.5888	Remote Similarity	NPC472991
0.5882	Remote Similarity	NPC25946
0.5862	Remote Similarity	NPC162394
0.5842	Remote Similarity	NPC170052
0.5842	Remote Similarity	NPC276377
0.5842	Remote Similarity	NPC135846
0.5818	Remote Similarity	NPC14187
0.5816	Remote Similarity	NPC46420
0.5773	Remote Similarity	NPC77672
0.5773	Remote Similarity	NPC133671
0.5773	Remote Similarity	NPC135391
0.5773	Remote Similarity	NPC78263
0.5773	Remote Similarity	NPC250069
0.5728	Remote Similarity	NPC473682
0.5727	Remote Similarity	NPC483767
0.5727	Remote Similarity	NPC483769
0.5727	Remote Similarity	NPC472994
0.5727	Remote Similarity	NPC483768
0.5727	Remote Similarity	NPC483766
0.5714	Remote Similarity	NPC323593
0.5714	Remote Similarity	NPC203500
0.5714	Remote Similarity	NPC150164
0.5688	Remote Similarity	NPC76831
0.5657	Remote Similarity	NPC24043
0.5636	Remote Similarity	NPC36138
0.5596	Remote Similarity	NPC101399
0.5596	Remote Similarity	NPC217822
0.5596	Remote Similarity	NPC11847
0.5596	Remote Similarity	NPC198938
0.5586	Remote Similarity	NPC223426
0.5586	Remote Similarity	NPC484301
0.5556	Remote Similarity	NPC64305
0.5556	Remote Similarity	NPC189142
0.5556	Remote Similarity	NPC77660
0.5536	Remote Similarity	NPC214621
0.5536	Remote Similarity	NPC34267
0.5526	Remote Similarity	NPC472993
0.5514	Remote Similarity	NPC186816
0.5505	Remote Similarity	NPC72016
0.55	Remote Similarity	NPC488080
0.55	Remote Similarity	NPC169977
0.5492	Remote Similarity	NPC199172
0.549	Remote Similarity	NPC22832
0.5472	Remote Similarity	NPC163242
0.5472	Remote Similarity	NPC272068
0.5455	Remote Similarity	NPC142142
0.5447	Remote Similarity	NPC21359
0.5447	Remote Similarity	NPC460984
0.5446	Remote Similarity	NPC472459
0.5431	Remote Similarity	NPC277532
0.5429	Remote Similarity	NPC8856
0.5421	Remote Similarity	NPC65003
0.5421	Remote Similarity	NPC304741
0.5417	Remote Similarity	NPC488078
0.5405	Remote Similarity	NPC188815
0.54	Remote Similarity	NPC8573
0.54	Remote Similarity	NPC95090
0.54	Remote Similarity	NPC277205
0.54	Remote Similarity	NPC27408
0.54	Remote Similarity	NPC37919
0.5398	Remote Similarity	NPC483765
0.5392	Remote Similarity	NPC285197
0.5392	Remote Similarity	NPC611303
0.5391	Remote Similarity	NPC219043
0.5391	Remote Similarity	NPC480796
0.5391	Remote Similarity	NPC477895
0.536	Remote Similarity	NPC231787
0.5351	Remote Similarity	NPC121703
0.5345	Remote Similarity	NPC217520
0.534	Remote Similarity	NPC243930
0.534	Remote Similarity	NPC601144
0.5333	Remote Similarity	NPC254855
0.5333	Remote Similarity	NPC94610
0.5321	Remote Similarity	NPC61904
0.5321	Remote Similarity	NPC470125
0.53	Remote Similarity	NPC261866
0.5294	Remote Similarity	NPC27942
0.5289	Remote Similarity	NPC488079
0.5288	Remote Similarity	NPC311830
0.5263	Remote Similarity	NPC96605
0.5263	Remote Similarity	NPC280642
0.5259	Remote Similarity	NPC48984
0.5248	Remote Similarity	NPC145038
0.5248	Remote Similarity	NPC56077
0.5248	Remote Similarity	NPC197896
0.5248	Remote Similarity	NPC281131
0.5248	Remote Similarity	NPC313163
0.5248	Remote Similarity	NPC253662
0.5248	Remote Similarity	NPC179950
0.5248	Remote Similarity	NPC88789
0.5248	Remote Similarity	NPC491374
0.5246	Remote Similarity	NPC138990
0.5243	Remote Similarity	NPC60735
0.5243	Remote Similarity	NPC26230
0.5229	Remote Similarity	NPC470444
0.5207	Remote Similarity	NPC156785
0.5207	Remote Similarity	NPC474522
0.5203	Remote Similarity	NPC175429
0.52	Remote Similarity	NPC480470
0.5196	Remote Similarity	NPC271692
0.5192	Remote Similarity	NPC120099
0.5192	Remote Similarity	NPC80188
0.5192	Remote Similarity	NPC486578
0.5185	Remote Similarity	NPC470405
0.5172	Remote Similarity	NPC470416
0.5152	Remote Similarity	NPC288084
0.5146	Remote Similarity	NPC216496
0.513	Remote Similarity	NPC478277
0.513	Remote Similarity	NPC478276
0.513	Remote Similarity	NPC478275
0.513	Remote Similarity	NPC92815
0.513	Remote Similarity	NPC81042
0.5128	Remote Similarity	NPC473278
0.5126	Remote Similarity	NPC255799
0.5122	Remote Similarity	NPC209550
0.5096	Remote Similarity	NPC168584
0.5096	Remote Similarity	NPC307938
0.5096	Remote Similarity	NPC488071
0.5094	Remote Similarity	NPC203050
0.5094	Remote Similarity	NPC225434
0.5091	Remote Similarity	NPC122809
0.5091	Remote Similarity	NPC115674
0.5089	Remote Similarity	NPC606657
0.5088	Remote Similarity	NPC292929
0.5079	Remote Similarity	NPC35924
0.505	Remote Similarity	NPC331652
0.5048	Remote Similarity	NPC21666
0.5048	Remote Similarity	NPC609478
0.5043	Remote Similarity	NPC602448
0.504	Remote Similarity	NPC480472
0.5039	Remote Similarity	NPC30011

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC164704 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5049
0.1-0.2	4046
0.2-0.3	46
0.3-0.4	3
0.4-0.5	6
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