NPASS Compound

Natural Product: NPC474093

Natural Product ID	NPC474093
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-(3' '-O-E-P-Coumaroyl)-(6' '-O-E-Feruloyl)-Beta-D-Glucopyranoside
IUPAC Name	[(2S,3R,4S,5R,6R)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-3,5-dihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-4-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL461206
PubChem CID	21672200
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003678] Flavonoid 3-O-p-coumaroyl 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 10.4580 -0.4862 -1.4103 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6635 0.0383 -0.1179 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6472 0.1143 0.8337 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4114 -0.3465 0.4707 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3677 -0.2873 1.3956 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0430 -0.7687 1.0425 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0275 -0.7285 1.8602 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6935 -1.2230 1.4796 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5259 -1.7016 0.3309 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6425 -1.1672 2.3532 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3306 -1.6067 2.0940 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7150 -0.8623 0.9369 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5856 -1.2784 0.6527 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9423 -0.8483 -0.5859 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3644 -0.7939 -0.7836 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0079 -1.7268 -1.5943 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6284 -2.8627 -1.1575 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1908 -3.6773 -2.0674 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1833 -3.4483 -3.3372 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5863 -2.3309 -3.8581 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9920 -1.4604 -2.9743 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4531 -0.4489 -3.4518 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5831 -2.0917 -5.2316 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9628 -0.9417 -5.7099 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1745 -2.9593 -6.1237 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7818 -4.0933 -5.6100 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7800 -4.3209 -4.2529 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3997 -5.0157 -6.4488 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7164 -3.2408 0.2379 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1186 -4.5298 0.5475 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2850 -4.9609 1.8407 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0499 -4.1012 2.8828 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6525 -2.8244 2.5950 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4884 -2.4012 1.2676 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2135 -4.5222 4.2007 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3274 0.4301 -1.0509 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1356 1.3738 0.0239 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7205 0.6580 1.1949 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0663 0.9850 1.3408 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8515 2.3225 0.3039 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7616 3.6707 0.0353 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3167 4.0068 -0.5004 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7997 4.6561 0.3286 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9385 4.3622 0.8831 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0119 5.2911 1.2024 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1831 4.8570 1.7757 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2212 5.7024 2.0914 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1211 7.0580 1.8364 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9599 7.5293 1.2620 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9246 6.6454 0.9532 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1734 7.9209 2.1551 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7369 0.1685 -1.9349 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6305 0.2366 2.6424 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9064 0.7004 2.9851 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9296 0.6404 2.0726 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2159 1.0841 2.3498 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3208 -1.5956 -1.2657 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3436 -0.3520 -2.0522 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5594 -0.0562 -1.8549 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1868 -0.7581 -0.4988 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9020 -1.1853 0.0300 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1584 -0.3213 2.8492 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7324 -1.3718 2.9997 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3381 -2.6881 1.9307 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3114 -1.0960 0.0334 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5910 -1.6642 -1.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9802 -1.0030 -5.9921 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1947 -2.8118 -7.1920 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2509 -5.2054 -3.8284 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3247 -6.0066 -6.1702 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3119 -5.2354 -0.2640 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6000 -5.9723 2.0286 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4654 -2.1427 3.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2016 -1.3809 1.1408 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3500 -5.4988 4.4234 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0488 1.0383 -1.6736 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9690 1.9716 -0.4512 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2487 0.8858 2.1605 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2076 1.8728 0.9662 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6036 5.6805 0.0659 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0919 3.3003 1.1299 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2956 3.8082 1.9877 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1544 5.3412 2.5507 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8576 8.5950 1.0526 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0322 7.0382 0.5066 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7873 8.1416 1.3560 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4414 0.1963 -2.8859 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8978 0.3271 3.4238 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0946 1.1073 3.9660 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6599 0.6466 3.1651 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 2 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 20 23 1 0 23 24 1 0 23 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 17 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 2 0 32 35 1 0 14 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 37 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 2 0 48 51 1 0 36 52 1 0 5 53 2 0 53 54 1 0 54 55 2 0 55 56 1 0 55 3 1 0 38 12 1 0 50 45 1 0 21 16 1 0 34 29 1 0 27 19 1 0 1 57 1 0 1 58 1 0 1 59 1 0 4 60 1 0 6 61 1 0 7 62 1 0 11 63 1 0 11 64 1 0 12 65 1 6 14 66 1 6 24 67 1 0 25 68 1 0 27 69 1 0 28 70 1 0 30 71 1 0 31 72 1 0 33 73 1 0 34 74 1 0 35 75 1 0 36 76 1 6 37 77 1 6 38 78 1 1 39 79 1 0 43 80 1 0 44 81 1 0 46 82 1 0 47 83 1 0 49 84 1 0 50 85 1 0 51 86 1 0 52 87 1 0 53 88 1 0 54 89 1 0 56 90 1 0 M END

Standard InCHIKey	XPIXCPCSKJDZLU-HRYAKSFCSA-N
Standard InCHI	InChI=1S/C40H34O16/c1-51-28-16-21(4-13-26(28)44)6-14-31(46)52-19-30-34(48)38(55-32(47)15-5-20-2-9-23(41)10-3-20)36(50)40(54-30)56-39-35(49)33-27(45)17-25(43)18-29(33)53-37(39)22-7-11-24(42)12-8-22/h2-18,30,34,36,38,40-45,48,50H,19H2,1H3/b14-6+,15-5+/t30-,34-,36-,38+,40+/m1/s1
SMILES	COc1cc(/C=C/C(=O)OC[C@H]2O[C@@H](Oc3c(oc4c(c3=O)c(O)cc(c4)O)c3ccc(cc3)O)[C@@H]([C@H]([C@@H]2O)OC(=O)/C=C/c2ccc(cc2)O)O)ccc1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	770.18	Volume:	742.244 ? Van der Waals volume.
Dense:	1.038	LogP:	2.515 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.222 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.222 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	40.0
TPSA:	252.11 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.075	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.584	Fsp³:	0.175
MCE-18:	125.298 ? 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:	0.994	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.913 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.778 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.189	Promiscuous compounds:	0.693

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.601	MDCK Permeability:	-5.306
Pgp-inhibitor:	0.146	Pgp-substrate:	0.019
PAMPA:	0.721 ? 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):	0.0
20% Bioavailability (F20%):	0.932	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	90.425%	Volume Distribution (VD):	0.032
Fu:	9.513% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.94
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.014
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.175
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.01	CYP2D6-substrate:	0.998
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.869 ? 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):

2.354

Half-life (T1/2):

3.137

ADMET: Toxicity

hERG Blockers:	0.06	hERG Blockers (10um):	0.513
Human Hepatotoxicity (H-HT):	0.507	Drug-induced Liver Injury (DILI):	0.942
AMES Toxicity:	0.8	Rat Oral Acute Toxicity:	0.156
Maximum Recommended Daily Dose:	0.891	Skin Sensitization:	0.999
Carcinogencity:	0.184	Eye Corrosion:	0.0
Eye Irritation:	0.747	Respiratory Toxicity:	0.099
Drug-induced Neurotoxicity:	0.055	Ototoxicity:	0.282
Hematotoxicity:	0.009	Drug-induced Nephrotoxicity:	0.225
Genotoxicity:	0.99	RPMI-8226 Immunitoxicity:	0.192
A549 Cytotoxicity:	0.924	Hek293 Cytotoxicity:	0.985
BCF:	0.819 ? 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:	3.974 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.889 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.629 ? 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
NPO12512	Stenochlaena palustris	Species	Blechnaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9917285]
NPO12512	Stenochlaena palustris	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12512	Stenochlaena palustris	Species	Blechnaceae	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
MIC	4

Activity Type	# Activity
Organism	4

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
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	>	256.0	ug.mL-1	PMID[11141109]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	256.0	ug.mL-1	PMID[25055342]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	256.0	ug.mL-1	PMID[8676127]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	>	256.0	ug.mL-1	PMID[25442308]

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 NPC474093 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	15572
0.1-0.2	29866
0.2-0.3	3589
0.3-0.4	504
0.4-0.5	219
0.5-0.6	57
0.6-0.7	33
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC104910
0.914	High Similarity	NPC96605
0.914	High Similarity	NPC280642
0.8214	Intermediate Similarity	NPC475179
0.7576	Intermediate Similarity	NPC205824
0.7327	Intermediate Similarity	NPC85751
0.7327	Intermediate Similarity	NPC19240
0.717	Intermediate Similarity	NPC217520
0.7117	Intermediate Similarity	NPC241781
0.7019	Intermediate Similarity	NPC218161
0.6916	Remote Similarity	NPC477895
0.6857	Remote Similarity	NPC223426
0.6822	Remote Similarity	NPC470416
0.6792	Remote Similarity	NPC214621
0.6792	Remote Similarity	NPC34267
0.6638	Remote Similarity	NPC25946
0.6635	Remote Similarity	NPC104883
0.6635	Remote Similarity	NPC488679
0.6577	Remote Similarity	NPC139571
0.6449	Remote Similarity	NPC36138
0.633	Remote Similarity	NPC478277
0.633	Remote Similarity	NPC478276
0.633	Remote Similarity	NPC478275
0.633	Remote Similarity	NPC92815
0.633	Remote Similarity	NPC81042
0.6262	Remote Similarity	NPC101399
0.6262	Remote Similarity	NPC221288
0.6262	Remote Similarity	NPC217822
0.6262	Remote Similarity	NPC11847
0.6262	Remote Similarity	NPC198938
0.6262	Remote Similarity	NPC194836
0.6262	Remote Similarity	NPC91493
0.6262	Remote Similarity	NPC605081
0.6207	Remote Similarity	NPC471030
0.6167	Remote Similarity	NPC21359
0.6167	Remote Similarity	NPC460984
0.6161	Remote Similarity	NPC473278
0.61	Remote Similarity	NPC129217
0.6091	Remote Similarity	NPC483767
0.6091	Remote Similarity	NPC483769
0.6091	Remote Similarity	NPC483768
0.6091	Remote Similarity	NPC483766
0.6036	Remote Similarity	NPC483765
0.5983	Remote Similarity	NPC470713
0.5981	Remote Similarity	NPC470125
0.5806	Remote Similarity	NPC473554
0.5688	Remote Similarity	NPC153755
0.5667	Remote Similarity	NPC156785
0.5667	Remote Similarity	NPC474522
0.5625	Remote Similarity	NPC477629
0.562	Remote Similarity	NPC470720
0.562	Remote Similarity	NPC488078
0.5603	Remote Similarity	NPC480796
0.5603	Remote Similarity	NPC472993
0.5596	Remote Similarity	NPC129264
0.5593	Remote Similarity	NPC470716
0.5591	Remote Similarity	NPC72554
0.5575	Remote Similarity	NPC260504
0.5575	Remote Similarity	NPC89809
0.5573	Remote Similarity	NPC487501
0.5565	Remote Similarity	NPC203145
0.5556	Remote Similarity	NPC470712
0.5556	Remote Similarity	NPC231787
0.5537	Remote Similarity	NPC162394
0.5504	Remote Similarity	NPC249560
0.5492	Remote Similarity	NPC488079
0.5462	Remote Similarity	NPC470718
0.5433	Remote Similarity	NPC275977
0.5429	Remote Similarity	NPC85707
0.542	Remote Similarity	NPC97817
0.541	Remote Similarity	NPC470717
0.5333	Remote Similarity	NPC159579
0.5294	Remote Similarity	NPC33083
0.5288	Remote Similarity	NPC52550
0.5278	Remote Similarity	NPC116864
0.5278	Remote Similarity	NPC244776
0.5268	Remote Similarity	NPC296018
0.5231	Remote Similarity	NPC30011
0.5191	Remote Similarity	NPC487502
0.5182	Remote Similarity	NPC471079
0.5182	Remote Similarity	NPC609888
0.5175	Remote Similarity	NPC210961
0.5175	Remote Similarity	NPC270448
0.5149	Remote Similarity	NPC54802
0.5149	Remote Similarity	NPC197304
0.5135	Remote Similarity	NPC173582
0.5135	Remote Similarity	NPC265885
0.5135	Remote Similarity	NPC181465
0.5135	Remote Similarity	NPC215710
0.5135	Remote Similarity	NPC473438
0.5135	Remote Similarity	NPC253788
0.5133	Remote Similarity	NPC7191
0.5126	Remote Similarity	NPC189564
0.5098	Remote Similarity	NPC288084
0.5086	Remote Similarity	NPC80068
0.5086	Remote Similarity	NPC476472
0.5086	Remote Similarity	NPC294815
0.5086	Remote Similarity	NPC16194
0.5047	Remote Similarity	NPC48093
0.5037	Remote Similarity	NPC487500

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474093 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4381
0.1-0.2	4702
0.2-0.3	59
0.3-0.4	7
0.4-0.5	1
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