NPASS Compound

Natural Product: NPC559110

Natural Product ID	NPC559110
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Quercetin 7-rutinoside
IUPAC Name	2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-[(2~{S},4~{S},5~{S})-3,4,5-trihydroxy-6-[[(2~{R},4~{S},5~{R})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 73 77 0 0 0 0 0 0 0 0999 V2000 -8.6269 0.4085 -2.1012 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4887 0.0551 -1.1676 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5816 1.0850 -1.1962 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4757 0.8117 -0.3524 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4979 1.7586 -0.6738 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3556 1.1912 -1.1646 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5620 0.3521 -0.2373 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5092 -0.2661 -0.9323 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6749 -0.9673 -0.0566 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6066 -0.4763 -0.0032 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7873 -1.0792 -0.3184 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8076 -2.3790 -0.7620 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0400 -2.9383 -1.0673 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0794 -4.2590 -1.5198 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2148 -2.2070 -0.9289 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4350 -2.7553 -1.2297 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4813 -3.9418 -1.6370 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5668 -1.9755 -1.0712 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7641 -2.5719 -1.3859 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5194 -0.6818 -0.6275 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6719 0.1891 -0.4403 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9707 -0.1291 -0.6782 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0140 0.7923 -0.4625 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7630 2.0546 -0.0015 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8076 2.9701 0.2121 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4525 2.3944 0.2450 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2019 3.6752 0.7123 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4450 1.4886 0.0311 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3020 -0.2103 -0.3529 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2095 -0.9048 -0.4861 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9823 -0.3556 -0.1844 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2309 -1.0531 1.3510 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2134 -1.6194 2.1350 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5310 0.2986 1.9574 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4737 0.7536 2.7444 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8566 1.2242 0.8323 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5773 2.3064 1.2118 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9696 0.9839 1.0390 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0128 0.7697 2.0315 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0835 -0.0096 1.3001 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6731 0.3235 2.5045 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0828 -0.1443 0.2129 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.2212 0.6300 0.3833 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5818 -0.0344 -1.7581 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3975 0.1518 -3.1567 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7465 1.5109 -2.0619 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0546 -0.9158 -1.5264 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1380 -0.2318 -0.5056 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5332 0.5941 -2.0912 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6915 2.0403 -1.5031 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1272 -0.4185 0.2822 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6793 -2.0078 -0.4320 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9277 -2.9965 -0.8888 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3168 -4.9636 -0.8126 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8010 -3.1275 -2.2392 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2211 -1.1110 -1.0425 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0352 0.5085 -0.6609 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6452 2.9864 -0.3290 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8306 4.0086 1.4513 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4046 1.7672 0.2298 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9632 0.6642 0.1640 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0732 -1.7620 1.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5292 -0.9564 2.2685 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4114 0.1982 2.6189 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5364 0.2600 3.6088 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8956 1.6155 0.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3041 3.1709 0.8141 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3883 2.0212 1.1228 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2800 1.3540 2.7986 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5638 -0.9994 1.4618 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1148 1.1997 2.4119 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4413 -1.2161 0.2223 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1402 1.4940 -0.0585 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 2 0 12 13 1 0 13 14 1 0 13 15 2 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 0 18 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 2 0 20 29 1 0 29 30 1 0 30 31 2 0 9 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 4 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 42 2 1 0 36 7 1 0 31 11 1 0 30 15 1 0 28 21 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 0 4 48 1 1 6 49 1 0 6 50 1 0 7 51 1 0 9 52 1 6 12 53 1 0 14 54 1 0 19 55 1 0 22 56 1 0 23 57 1 0 25 58 1 0 27 59 1 0 28 60 1 0 31 61 1 0 32 62 1 0 33 63 1 0 34 64 1 1 35 65 1 0 36 66 1 6 37 67 1 0 38 68 1 0 39 69 1 0 40 70 1 1 41 71 1 0 42 72 1 6 43 73 1 0 M END

Standard InCHIKey	IVTMALDHFAHOGL-ICNYXEQFSA-N
Standard InCHI	InChI=1S/C27H30O16/c1-8-17(31)20(34)23(37)26(40-8)39-7-15-18(32)21(35)24(38)27(43-15)41-10-5-13(30)16-14(6-10)42-25(22(36)19(16)33)9-2-3-11(28)12(29)4-9/h2-6,8,15,17-18,20-21,23-24,26-32,34-38H,7H2,1H3/t8?,15?,17-,18+,20-,21-,23?,24?,26+,27+/m0/s1
SMILES	CC1O[C@@H](OCC2O[C@@H](OC3=CC(O)=C4C(=O)C(O)=C(C5=CC=C(O)C(O)=C5)OC4=C3)C(O)[C@@H](O)[C@@H]2O)C(O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	610.15	Volume:	552.318 ? Van der Waals volume.
Dense:	1.105	LogP:	-0.022 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.555 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.416 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	269.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.14	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.79	Fsp³:	0.444
MCE-18:	122.949 ? 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:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.648	Fluc inhibitor:	0.291 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.955 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.901 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.16	Promiscuous compounds:	0.534

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.399	MDCK Permeability:	-5.031
Pgp-inhibitor:	0.0	Pgp-substrate:	0.542
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):	0.859
20% Bioavailability (F20%):	0.434	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.158
Plasma Protein Binding (PPB):	80.876%	Volume Distribution (VD):	-0.146
Fu:	17.405% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.989
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.69
BSEP inhibitor:	0.028

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:	0.004
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.91
HLM stability:	0.007 ? 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):

1.519

Half-life (T1/2):

5.208

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.481
Human Hepatotoxicity (H-HT):	0.238	Drug-induced Liver Injury (DILI):	0.787
AMES Toxicity:	0.582	Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.25	Skin Sensitization:	0.426
Carcinogencity:	0.017	Eye Corrosion:	0.0
Eye Irritation:	0.24	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.986
Hematotoxicity:	0.007	Drug-induced Nephrotoxicity:	0.036
Genotoxicity:	0.653	RPMI-8226 Immunitoxicity:	0.054
A549 Cytotoxicity:	0.339	Hek293 Cytotoxicity:	0.324
BCF:	0.459 ? 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:	3.081 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.909 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.02 ? 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
NPO53409	Cleome species	Genus	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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

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

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 NPC559110 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	19517
0.1-0.2	26474
0.2-0.3	2895
0.3-0.4	526
0.4-0.5	279
0.5-0.6	109
0.6-0.7	41
0.7-0.8	1
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC67105
0.8987	High Similarity	NPC227508
0.8289	Intermediate Similarity	NPC238376
0.8193	Intermediate Similarity	NPC210073
0.7857	Intermediate Similarity	NPC275454
0.7471	Intermediate Similarity	NPC186816
0.7442	Intermediate Similarity	NPC44931
0.7375	Intermediate Similarity	NPC108831
0.7375	Intermediate Similarity	NPC182634
0.7284	Intermediate Similarity	NPC277205
0.7284	Intermediate Similarity	NPC37919
0.7126	Intermediate Similarity	NPC187379
0.6966	Remote Similarity	NPC22062
0.6966	Remote Similarity	NPC473634
0.6966	Remote Similarity	NPC138811
0.6848	Remote Similarity	NPC209296
0.6778	Remote Similarity	NPC203259
0.6778	Remote Similarity	NPC33054
0.6778	Remote Similarity	NPC176740
0.6778	Remote Similarity	NPC471725
0.6778	Remote Similarity	NPC134532
0.6778	Remote Similarity	NPC602582
0.6739	Remote Similarity	NPC65711
0.6737	Remote Similarity	NPC135358
0.6735	Remote Similarity	NPC480441
0.6559	Remote Similarity	NPC470443
0.6548	Remote Similarity	NPC19709
0.6471	Remote Similarity	NPC323593
0.6471	Remote Similarity	NPC203500
0.6452	Remote Similarity	NPC126784
0.6452	Remote Similarity	NPC241423
0.6413	Remote Similarity	NPC303913
0.6395	Remote Similarity	NPC271692
0.6354	Remote Similarity	NPC80068
0.6354	Remote Similarity	NPC473073
0.6304	Remote Similarity	NPC173582
0.6304	Remote Similarity	NPC265885
0.6304	Remote Similarity	NPC181465
0.6304	Remote Similarity	NPC215710
0.6304	Remote Similarity	NPC473438
0.6304	Remote Similarity	NPC253788
0.6238	Remote Similarity	NPC25523
0.6237	Remote Similarity	NPC233994
0.6129	Remote Similarity	NPC39834
0.6122	Remote Similarity	NPC101636
0.6111	Remote Similarity	NPC605784
0.6082	Remote Similarity	NPC142142
0.6067	Remote Similarity	NPC285197
0.6064	Remote Similarity	NPC65563
0.6064	Remote Similarity	NPC470949
0.6042	Remote Similarity	NPC211532
0.6042	Remote Similarity	NPC488364
0.6	Remote Similarity	NPC14187
0.598	Remote Similarity	NPC480796
0.5979	Remote Similarity	NPC229409
0.5977	Remote Similarity	NPC249281
0.5895	Remote Similarity	NPC156869
0.587	Remote Similarity	NPC276377
0.587	Remote Similarity	NPC190003
0.587	Remote Similarity	NPC601586
0.5862	Remote Similarity	NPC473043
0.5862	Remote Similarity	NPC331652
0.5859	Remote Similarity	NPC476472
0.5859	Remote Similarity	NPC294815
0.5859	Remote Similarity	NPC16194
0.5843	Remote Similarity	NPC46420
0.5833	Remote Similarity	NPC204693
0.5833	Remote Similarity	NPC115674
0.5833	Remote Similarity	NPC473571
0.5833	Remote Similarity	NPC110941
0.5824	Remote Similarity	NPC486578
0.5816	Remote Similarity	NPC473623
0.5806	Remote Similarity	NPC477848
0.58	Remote Similarity	NPC287889
0.5789	Remote Similarity	NPC67326
0.5784	Remote Similarity	NPC11468
0.5758	Remote Similarity	NPC488089
0.573	Remote Similarity	NPC158674
0.573	Remote Similarity	NPC136042
0.573	Remote Similarity	NPC189142
0.573	Remote Similarity	NPC77660
0.5714	Remote Similarity	NPC87125
0.5714	Remote Similarity	NPC307938
0.5667	Remote Similarity	NPC245014
0.5667	Remote Similarity	NPC84362
0.5657	Remote Similarity	NPC122467
0.5657	Remote Similarity	NPC473327
0.5644	Remote Similarity	NPC298171
0.5618	Remote Similarity	NPC476405
0.5612	Remote Similarity	NPC488073
0.5612	Remote Similarity	NPC475366
0.5604	Remote Similarity	NPC117260
0.56	Remote Similarity	NPC486577
0.5591	Remote Similarity	NPC116458
0.5591	Remote Similarity	NPC246943
0.5567	Remote Similarity	NPC479405
0.5567	Remote Similarity	NPC150164
0.5545	Remote Similarity	NPC89127
0.5534	Remote Similarity	NPC244875
0.5534	Remote Similarity	NPC603856
0.5524	Remote Similarity	NPC292019
0.5524	Remote Similarity	NPC202908
0.551	Remote Similarity	NPC479404
0.5505	Remote Similarity	NPC298666
0.55	Remote Similarity	NPC32641
0.55	Remote Similarity	NPC256188
0.5474	Remote Similarity	NPC116864
0.5474	Remote Similarity	NPC244776
0.5472	Remote Similarity	NPC473644
0.5455	Remote Similarity	NPC488074
0.5455	Remote Similarity	NPC64051
0.5421	Remote Similarity	NPC311850
0.5417	Remote Similarity	NPC254540
0.54	Remote Similarity	NPC479403
0.5385	Remote Similarity	NPC609879
0.5376	Remote Similarity	NPC611303
0.5364	Remote Similarity	NPC198199
0.5361	Remote Similarity	NPC471079
0.5347	Remote Similarity	NPC72016
0.5347	Remote Similarity	NPC35119
0.5319	Remote Similarity	NPC181616
0.5294	Remote Similarity	NPC270675
0.5294	Remote Similarity	NPC195685
0.5288	Remote Similarity	NPC470446
0.5275	Remote Similarity	NPC127546
0.5275	Remote Similarity	NPC57625
0.5275	Remote Similarity	NPC173637
0.5275	Remote Similarity	NPC317489
0.5275	Remote Similarity	NPC223424
0.5275	Remote Similarity	NPC600591
0.5273	Remote Similarity	NPC68592
0.5263	Remote Similarity	NPC99957
0.5258	Remote Similarity	NPC8856
0.5253	Remote Similarity	NPC473512
0.5253	Remote Similarity	NPC65003
0.5248	Remote Similarity	NPC12013
0.5248	Remote Similarity	NPC11432
0.5248	Remote Similarity	NPC477613
0.5221	Remote Similarity	NPC120952
0.5217	Remote Similarity	NPC282987
0.5217	Remote Similarity	NPC297987
0.5196	Remote Similarity	NPC139060
0.5192	Remote Similarity	NPC470445
0.5189	Remote Similarity	NPC121703
0.5185	Remote Similarity	NPC303694
0.5161	Remote Similarity	NPC27640
0.5149	Remote Similarity	NPC46202
0.5149	Remote Similarity	NPC240306
0.5143	Remote Similarity	NPC472994
0.514	Remote Similarity	NPC189564
0.5109	Remote Similarity	NPC39360
0.5109	Remote Similarity	NPC29763
0.5109	Remote Similarity	NPC210003
0.5106	Remote Similarity	NPC59534
0.5106	Remote Similarity	NPC27942
0.5102	Remote Similarity	NPC251417
0.51	Remote Similarity	NPC129827
0.5049	Remote Similarity	NPC483707
0.5048	Remote Similarity	NPC221342
0.5048	Remote Similarity	NPC476470
0.5047	Remote Similarity	NPC203145
0.5047	Remote Similarity	NPC599948

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC559110 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5184
0.1-0.2	3909
0.2-0.3	44
0.3-0.4	6
0.4-0.5	2
0.5-0.6	1
0.6-0.7	3
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
0.7444	Intermediate Similarity	NPD7251	Phase 2
0.6848	Remote Similarity	NPD7054	Phase 4
0.6778	Remote Similarity	NPD6797	Phase 2
0.6429	Remote Similarity	NPD7808	Phase 3
0.5333	Remote Similarity	NPD7472	Pre-clinical

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