NPASS Compound

Natural Product: NPC241781

Natural Product ID	NPC241781
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Quercetin 3-O-Alpha-L-Rhamnopyranosyl(1->6)-(3-O-Trans-P-Coumaroyl)-Beta-D-Galactopyranoside
IUPAC Name	[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,5-dihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-4-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL443428
PubChem CID	21576259
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-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 -1.6981 4.7183 -2.6766 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8887 4.5866 -1.1937 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6206 5.8234 -0.7158 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7293 5.7000 0.8052 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3375 4.3541 1.0841 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4537 3.2242 0.5362 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1780 3.3404 0.8522 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3537 2.4570 1.3837 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0371 1.2156 0.6382 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1272 0.3365 0.3797 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7053 -1.0259 -0.1597 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3896 -1.5557 0.7995 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4850 -0.5749 0.7306 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9800 0.5648 1.4650 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7129 -0.9097 1.3599 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8409 -0.2353 0.8930 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0391 1.0096 1.5026 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2730 1.4536 2.3880 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1190 1.7531 1.0995 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3783 3.0064 1.6632 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4711 3.7340 1.2376 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2712 3.1895 0.2635 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0116 1.9539 -0.2890 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9247 1.2132 0.1239 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6929 0.0456 -0.4086 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6571 -0.7290 -0.0570 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5202 -2.0204 -0.7350 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2293 -2.2604 -1.9052 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2050 -3.4514 -2.5712 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4490 -4.4984 -2.0905 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7278 -4.2911 -0.9204 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7719 -3.0695 -0.2637 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9716 -5.3489 -0.4461 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4015 -5.7235 -2.7442 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3708 3.9620 -0.1402 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5071 3.4786 2.6498 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6569 -2.8676 0.5236 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7689 -1.9256 -0.1077 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1192 -2.6072 -1.2682 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4888 -2.4147 -2.3348 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2231 -3.5631 -1.2892 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9020 -3.7827 -0.1807 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9994 -4.7068 -0.1232 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4583 -5.4453 -1.1729 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5213 -6.3172 -1.0480 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1791 -6.4856 0.1604 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7343 -5.7517 1.2329 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6821 -4.8960 1.0868 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2425 -7.3750 0.2329 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8839 0.0700 1.5136 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5542 3.4141 -0.8837 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5431 4.2837 0.3835 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6123 6.6673 1.2455 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8248 6.9252 -0.9930 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6652 4.9473 -3.1637 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2900 3.7557 -3.0500 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0062 5.5631 -2.8604 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9143 4.5629 -0.6644 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6087 5.9493 -1.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7101 5.8121 1.2272 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5569 4.2292 2.1432 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0129 2.3130 0.7434 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6973 2.1281 2.4401 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6007 3.0325 1.6866 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5312 1.5182 -0.3049 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7753 0.7649 -0.3929 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2248 -0.9324 -1.1411 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0856 -1.4671 1.8324 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6313 -0.1957 -0.2998 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6500 4.6856 1.6805 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6536 1.5490 -1.0509 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8313 -1.4567 -2.3052 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7673 -3.5809 -3.4638 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2267 -2.9793 0.6471 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1800 -5.6265 -1.0168 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0763 -6.5336 -2.2680 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3038 3.5517 -0.2084 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7391 3.3105 3.6001 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4941 -3.4369 1.3220 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4924 -4.0876 -2.1817 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6334 -3.2465 0.7499 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0064 -5.3757 -2.1433 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8550 -6.8848 -1.9045 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2639 -5.8981 2.1717 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3648 -4.3387 1.9556 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9269 -7.2540 0.9921 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7550 -0.3057 1.1746 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9985 3.4099 0.5041 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2514 6.2757 1.9086 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8560 7.5938 -0.2578 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 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 30 34 1 0 22 35 1 0 20 36 1 0 12 37 1 0 11 38 1 0 38 39 1 0 39 40 2 0 39 41 1 0 41 42 2 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 46 49 1 0 10 50 1 0 6 51 1 0 5 52 1 0 4 53 1 0 3 54 1 0 51 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 48 43 1 0 24 19 1 0 1 55 1 0 1 56 1 0 1 57 1 0 2 58 1 1 3 59 1 6 4 60 1 1 5 61 1 1 6 62 1 6 8 63 1 0 8 64 1 0 9 65 1 6 10 66 1 6 11 67 1 6 12 68 1 1 13 69 1 6 21 70 1 0 23 71 1 0 28 72 1 0 29 73 1 0 32 74 1 0 33 75 1 0 34 76 1 0 35 77 1 0 36 78 1 0 37 79 1 0 41 80 1 0 42 81 1 0 44 82 1 0 45 83 1 0 47 84 1 0 48 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	XMDQISLNHUQSJJ-XENQWPOYSA-N
Standard InCHI	InChI=1S/C36H36O18/c1-14-26(43)29(46)30(47)35(50-14)49-13-23-27(44)33(53-24(42)9-4-15-2-6-17(37)7-3-15)31(48)36(52-23)54-34-28(45)25-21(41)11-18(38)12-22(25)51-32(34)16-5-8-19(39)20(40)10-16/h2-12,14,23,26-27,29-31,33,35-41,43-44,46-48H,13H2,1H3/b9-4+/t14-,23+,26-,27-,29+,30+,31+,33-,35+,36-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@@H]([C@@H]([C@H]([C@@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(c(c2)O)O)O)O)O)OC(=O)/C=C/c2ccc(cc2)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.19	Volume:	703.823 ? Van der Waals volume.
Dense:	1.074	LogP:	0.958 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.11 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.776 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	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:	0.062	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.09	Fsp³:	0.333
MCE-18:	140.083 ? 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:	1
Colloidal aggregators:	0.718	Fluc inhibitor:	0.575 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.83 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.672 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.249	Promiscuous compounds:	0.591

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.605	MDCK Permeability:	-5.164
Pgp-inhibitor:	0.0	Pgp-substrate:	0.164
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):	0.043
20% Bioavailability (F20%):	0.968	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):	85.614%	Volume Distribution (VD):	-0.017
Fu:	13.74% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.577
BSEP inhibitor:	0.547

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.873
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.733 ? 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):

1.922

Half-life (T1/2):

4.916

ADMET: Toxicity

hERG Blockers:	0.015	hERG Blockers (10um):	0.354
Human Hepatotoxicity (H-HT):	0.407	Drug-induced Liver Injury (DILI):	0.892
AMES Toxicity:	0.708	Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.381	Skin Sensitization:	1.0
Carcinogencity:	0.03	Eye Corrosion:	0.0
Eye Irritation:	0.714	Respiratory Toxicity:	0.031
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.888
Hematotoxicity:	0.009	Drug-induced Nephrotoxicity:	0.149
Genotoxicity:	0.921	RPMI-8226 Immunitoxicity:	0.1
A549 Cytotoxicity:	0.935	Hek293 Cytotoxicity:	0.847
BCF:	0.682 ? 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:	3.456 ? 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:	4.344 ? 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
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043423]
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10828	Adina racemosa	Species	Rubiaceae	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
FC	2

Activity Type	# Activity
Others	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
NPT2	Others	Unspecified	n.a.	FC	=	2.0	n.a.	PMID[25899338]

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 NPC241781 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	14665
0.1-0.2	30786
0.2-0.3	3508
0.3-0.4	526
0.4-0.5	168
0.5-0.6	119
0.6-0.7	57
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7944	Intermediate Similarity	NPC156785
0.7944	Intermediate Similarity	NPC162394
0.7719	Intermediate Similarity	NPC72554
0.7699	Intermediate Similarity	NPC275977
0.767	Intermediate Similarity	NPC96605
0.767	Intermediate Similarity	NPC280642
0.7458	Intermediate Similarity	NPC97817
0.7288	Intermediate Similarity	NPC249560
0.7265	Intermediate Similarity	NPC30011
0.7238	Intermediate Similarity	NPC223426
0.7129	Intermediate Similarity	NPC203259
0.7129	Intermediate Similarity	NPC33054
0.7129	Intermediate Similarity	NPC176740
0.7129	Intermediate Similarity	NPC471725
0.7129	Intermediate Similarity	NPC134532
0.7129	Intermediate Similarity	NPC602582
0.7117	Intermediate Similarity	NPC474093
0.7117	Intermediate Similarity	NPC104910
0.7103	Intermediate Similarity	NPC203145
0.7097	Intermediate Similarity	NPC33083
0.7059	Intermediate Similarity	NPC487502
0.6991	Remote Similarity	NPC474522
0.6952	Remote Similarity	NPC205824
0.6807	Remote Similarity	NPC231787
0.6729	Remote Similarity	NPC85751
0.6729	Remote Similarity	NPC19240
0.6699	Remote Similarity	NPC173582
0.6699	Remote Similarity	NPC265885
0.6699	Remote Similarity	NPC181465
0.6699	Remote Similarity	NPC215710
0.6699	Remote Similarity	NPC473438
0.6699	Remote Similarity	NPC253788
0.6697	Remote Similarity	NPC81042
0.6574	Remote Similarity	NPC89127
0.6542	Remote Similarity	NPC104883
0.6542	Remote Similarity	NPC488679
0.6518	Remote Similarity	NPC292019
0.6518	Remote Similarity	NPC202908
0.6396	Remote Similarity	NPC214621
0.6396	Remote Similarity	NPC34267
0.6389	Remote Similarity	NPC122467
0.6389	Remote Similarity	NPC473327
0.6381	Remote Similarity	NPC39834
0.6378	Remote Similarity	NPC487501
0.6372	Remote Similarity	NPC477895
0.6321	Remote Similarity	NPC156869
0.6316	Remote Similarity	NPC217520
0.6273	Remote Similarity	NPC476472
0.6273	Remote Similarity	NPC294815
0.6273	Remote Similarity	NPC16194
0.625	Remote Similarity	NPC475179
0.6226	Remote Similarity	NPC67326
0.6172	Remote Similarity	NPC487500
0.614	Remote Similarity	NPC189564
0.61	Remote Similarity	NPC127546
0.61	Remote Similarity	NPC57625
0.61	Remote Similarity	NPC173637
0.61	Remote Similarity	NPC317489
0.61	Remote Similarity	NPC223424
0.61	Remote Similarity	NPC600591
0.6095	Remote Similarity	NPC116864
0.6095	Remote Similarity	NPC244776
0.6055	Remote Similarity	NPC470125
0.6055	Remote Similarity	NPC126784
0.6055	Remote Similarity	NPC241423
0.6036	Remote Similarity	NPC101399
0.6036	Remote Similarity	NPC221288
0.6036	Remote Similarity	NPC217822
0.6036	Remote Similarity	NPC11847
0.6036	Remote Similarity	NPC198938
0.6036	Remote Similarity	NPC194836
0.6036	Remote Similarity	NPC91493
0.6036	Remote Similarity	NPC605081
0.6018	Remote Similarity	NPC218161
0.6	Remote Similarity	NPC12013
0.6	Remote Similarity	NPC473554
0.6	Remote Similarity	NPC11432
0.6	Remote Similarity	NPC477613
0.5985	Remote Similarity	NPC482521
0.5932	Remote Similarity	NPC139571
0.5897	Remote Similarity	NPC303694
0.5872	Remote Similarity	NPC605592
0.5865	Remote Similarity	NPC129217
0.5833	Remote Similarity	NPC471079
0.5826	Remote Similarity	NPC483765
0.5825	Remote Similarity	NPC52550
0.5812	Remote Similarity	NPC173837
0.5798	Remote Similarity	NPC470716
0.5798	Remote Similarity	NPC470718
0.5794	Remote Similarity	NPC95866
0.5789	Remote Similarity	NPC221342
0.5789	Remote Similarity	NPC476470
0.5763	Remote Similarity	NPC470712
0.5746	Remote Similarity	NPC482520
0.5746	Remote Similarity	NPC482519
0.5739	Remote Similarity	NPC483767
0.5739	Remote Similarity	NPC483769
0.5739	Remote Similarity	NPC483768
0.5739	Remote Similarity	NPC483766
0.5739	Remote Similarity	NPC602448
0.5727	Remote Similarity	NPC65563
0.5727	Remote Similarity	NPC470949
0.5714	Remote Similarity	NPC21359
0.5714	Remote Similarity	NPC460984
0.5714	Remote Similarity	NPC175107
0.5702	Remote Similarity	NPC471669
0.5686	Remote Similarity	NPC111929
0.5686	Remote Similarity	NPC320283
0.5686	Remote Similarity	NPC41121
0.5676	Remote Similarity	NPC129264
0.5676	Remote Similarity	NPC473571
0.5676	Remote Similarity	NPC110941
0.5669	Remote Similarity	NPC487499
0.5664	Remote Similarity	NPC37668
0.5652	Remote Similarity	NPC36138
0.5641	Remote Similarity	NPC89052
0.561	Remote Similarity	NPC488740
0.561	Remote Similarity	NPC488736
0.561	Remote Similarity	NPC488733
0.5586	Remote Similarity	NPC155877
0.5575	Remote Similarity	NPC245452
0.5575	Remote Similarity	NPC470443
0.5565	Remote Similarity	NPC480444
0.5556	Remote Similarity	NPC478277
0.5556	Remote Similarity	NPC478276
0.5556	Remote Similarity	NPC478275
0.5556	Remote Similarity	NPC92815
0.5536	Remote Similarity	NPC186816
0.552	Remote Similarity	NPC488737
0.5487	Remote Similarity	NPC154741
0.547	Remote Similarity	NPC470446
0.5431	Remote Similarity	NPC473073
0.5431	Remote Similarity	NPC477629
0.5429	Remote Similarity	NPC145038
0.5429	Remote Similarity	NPC56077
0.5429	Remote Similarity	NPC281131
0.5429	Remote Similarity	NPC253662
0.5429	Remote Similarity	NPC179950
0.5429	Remote Similarity	NPC88789
0.5429	Remote Similarity	NPC491374
0.5421	Remote Similarity	NPC219904
0.5413	Remote Similarity	NPC476215
0.5391	Remote Similarity	NPC270448
0.5391	Remote Similarity	NPC25946
0.5385	Remote Similarity	NPC135599
0.5385	Remote Similarity	NPC73855
0.5385	Remote Similarity	NPC113968
0.5385	Remote Similarity	NPC328940
0.5385	Remote Similarity	NPC277174
0.5385	Remote Similarity	NPC606877
0.5357	Remote Similarity	NPC471748
0.5351	Remote Similarity	NPC488073
0.5351	Remote Similarity	NPC153755
0.5351	Remote Similarity	NPC488074
0.534	Remote Similarity	NPC276222
0.534	Remote Similarity	NPC274618
0.534	Remote Similarity	NPC118284
0.534	Remote Similarity	NPC608147
0.5321	Remote Similarity	NPC223747
0.5289	Remote Similarity	NPC473278
0.5288	Remote Similarity	NPC67037
0.5288	Remote Similarity	NPC255615
0.528	Remote Similarity	NPC480445
0.5278	Remote Similarity	NPC159579
0.5268	Remote Similarity	NPC187379
0.5268	Remote Similarity	NPC29958
0.5259	Remote Similarity	NPC483416
0.5254	Remote Similarity	NPC470445
0.5234	Remote Similarity	NPC192539
0.5221	Remote Similarity	NPC196127
0.5221	Remote Similarity	NPC163242
0.5221	Remote Similarity	NPC272068
0.5217	Remote Similarity	NPC296018
0.5207	Remote Similarity	NPC470416
0.52	Remote Similarity	NPC488734
0.52	Remote Similarity	NPC488735
0.52	Remote Similarity	NPC488739
0.52	Remote Similarity	NPC488732
0.52	Remote Similarity	NPC488738
0.5159	Remote Similarity	NPC470713
0.514	Remote Similarity	NPC265530
0.513	Remote Similarity	NPC255157
0.513	Remote Similarity	NPC35167
0.513	Remote Similarity	NPC259896
0.5126	Remote Similarity	NPC292929
0.5126	Remote Similarity	NPC470449
0.5093	Remote Similarity	NPC305811
0.5091	Remote Similarity	NPC85707
0.5089	Remote Similarity	NPC254855
0.5089	Remote Similarity	NPC94610
0.5047	Remote Similarity	NPC77672
0.5047	Remote Similarity	NPC133671
0.5047	Remote Similarity	NPC135391
0.5047	Remote Similarity	NPC78263
0.5047	Remote Similarity	NPC250069
0.5046	Remote Similarity	NPC216496
0.5042	Remote Similarity	NPC135831

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC241781 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4494
0.1-0.2	4601
0.2-0.3	45
0.3-0.4	6
0.4-0.5	2
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
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
0.7129	Intermediate Similarity	NPD6797	Phase 2
0.5565	Remote Similarity	NPD7251	Phase 2

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