NPASS Compound

Natural Product: NPC520801

Natural Product ID	NPC520801
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	244285-12-9
IUPAC Name	5,7-dihydroxy-6-methoxy-2-[4-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]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 55 58 0 0 0 0 0 0 0 0999 V2000 9.1603 -0.0175 -1.3548 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4610 -0.4769 -0.2050 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0779 -0.5251 -0.1805 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3839 -1.6465 -0.5870 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1139 -2.7377 -1.0262 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0168 -1.7011 -0.5653 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2776 -0.6021 -0.1228 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9834 -0.6105 -0.0858 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2386 0.4157 0.3290 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7820 0.2634 0.3162 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0225 1.2855 0.7313 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4203 1.1123 0.7086 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9997 -0.0634 0.2779 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3700 -0.1292 0.2954 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1945 -1.1773 -0.0789 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9996 -0.7924 -1.1497 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7514 0.3224 -0.8879 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1279 1.5950 -1.4181 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0028 1.4443 -2.8123 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1017 0.4440 0.5804 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2242 1.2608 0.7433 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3643 -0.9600 1.0819 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9634 -0.9593 2.3366 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0336 -1.6828 1.0871 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2176 -3.0630 1.0078 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1769 -1.0716 -0.1324 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2157 -0.9061 -0.1125 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8893 1.5441 0.7396 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2684 1.6123 0.7228 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8932 2.6465 1.0981 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9791 0.5169 0.2825 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3536 0.5457 0.2508 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0251 1.6941 0.6683 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7357 -0.5614 -2.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0019 1.0799 -1.4357 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2380 -0.2598 -1.2428 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1525 -2.8986 -2.0248 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4586 -2.5596 -0.8757 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3805 2.2252 1.0774 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9981 1.9586 1.0495 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6176 -2.0525 -0.4305 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7246 0.2067 -1.4270 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1730 1.8443 -0.9397 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8084 2.4589 -1.2762 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5163 0.5828 -2.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2859 0.8873 1.1802 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9043 2.1945 0.5771 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0014 -1.4666 0.3167 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4317 -1.8161 2.4946 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5041 -1.3795 2.0138 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3579 -3.3886 1.9196 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6118 -1.9974 -0.4722 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8674 -1.6999 -0.4357 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3328 2.4052 1.0856 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6187 1.6943 1.5025 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 4 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 13 26 1 0 26 27 2 0 9 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 32 3 1 0 31 7 1 0 27 10 1 0 24 15 1 0 1 34 1 0 1 35 1 0 1 36 1 0 5 37 1 0 6 38 1 0 11 39 1 0 12 40 1 0 15 41 1 6 17 42 1 6 18 43 1 0 18 44 1 0 19 45 1 0 20 46 1 1 21 47 1 0 22 48 1 6 23 49 1 0 24 50 1 1 25 51 1 0 26 52 1 0 27 53 1 0 28 54 1 0 33 55 1 0 M END

Standard InCHIKey	MORLNMAFXVHNAI-IWLDQSELSA-N
Standard InCHI	InChI=1S/C22H22O11/c1-30-21-12(25)7-14-16(18(21)27)11(24)6-13(32-14)9-2-4-10(5-3-9)31-22-20(29)19(28)17(26)15(8-23)33-22/h2-7,15,17,19-20,22-23,25-29H,8H2,1H3/t15-,17-,19+,20-,22-/m1/s1
SMILES	COC1=C(O)C=C2OC(C3=CC=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=C3)=CC(=O)C2=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	462.12	Volume:	430.443 ? Van der Waals volume.
Dense:	1.074	LogP:	1.349 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.674 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.24 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	24.0
TPSA:	179.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.302	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.89	Fsp³:	0.318
MCE-18:	86.966 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.613	Fluc inhibitor:	0.326 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.963 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.883 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.11	Promiscuous compounds:	0.569

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.195	MDCK Permeability:	-5.3
Pgp-inhibitor:	0.001	Pgp-substrate:	0.367
PAMPA:	0.915 ? 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):	0.29
20% Bioavailability (F20%):	0.102	30% Bioavailability (F30%):	0.938
50% Bioavailability (F50%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042	MRP1:	0.201
Plasma Protein Binding (PPB):	89.426%	Volume Distribution (VD):	-0.135
Fu:	8.462% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.326
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.021	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.009	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.405
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.994
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):

2.514

Half-life (T1/2):

2.981

ADMET: Toxicity

hERG Blockers:	0.025	hERG Blockers (10um):	0.112
Human Hepatotoxicity (H-HT):	0.655	Drug-induced Liver Injury (DILI):	0.967
AMES Toxicity:	0.918	Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.077	Skin Sensitization:	0.989
Carcinogencity:	0.365	Eye Corrosion:	0.0
Eye Irritation:	0.679	Respiratory Toxicity:	0.066
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.8
Hematotoxicity:	0.242	Drug-induced Nephrotoxicity:	0.441
Genotoxicity:	0.897	RPMI-8226 Immunitoxicity:	0.109
A549 Cytotoxicity:	0.432	Hek293 Cytotoxicity:	0.41
BCF:	0.403 ? 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:	3.111 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.377 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.636 ? 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
NPO17698	Cirsium oligophyllum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17698	Cirsium oligophyllum	Species	Asteraceae	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

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 NPC520801 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	18324
0.1-0.2	27040
0.2-0.3	2957
0.3-0.4	1028
0.4-0.5	347
0.5-0.6	104
0.6-0.7	33
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8169	Intermediate Similarity	NPC58053
0.7945	Intermediate Similarity	NPC186807
0.7671	Intermediate Similarity	NPC143851
0.7333	Intermediate Similarity	NPC95090
0.7333	Intermediate Similarity	NPC27408
0.7179	Intermediate Similarity	NPC605067
0.7051	Intermediate Similarity	NPC609451
0.7013	Intermediate Similarity	NPC105025
0.6883	Remote Similarity	NPC93337
0.675	Remote Similarity	NPC22832
0.6747	Remote Similarity	NPC603300
0.6709	Remote Similarity	NPC201292
0.6667	Remote Similarity	NPC88023
0.6667	Remote Similarity	NPC156222
0.6667	Remote Similarity	NPC309025
0.6667	Remote Similarity	NPC602805
0.6625	Remote Similarity	NPC191306
0.6582	Remote Similarity	NPC488080
0.6582	Remote Similarity	NPC45638
0.6582	Remote Similarity	NPC169977
0.6543	Remote Similarity	NPC243930
0.65	Remote Similarity	NPC42773
0.65	Remote Similarity	NPC45522
0.6463	Remote Similarity	NPC607707
0.6341	Remote Similarity	NPC101026
0.6341	Remote Similarity	NPC488077
0.6329	Remote Similarity	NPC39360
0.6329	Remote Similarity	NPC29763
0.6329	Remote Similarity	NPC210003
0.6265	Remote Similarity	NPC311830
0.6173	Remote Similarity	NPC610763
0.6145	Remote Similarity	NPC601710
0.6133	Remote Similarity	NPC470402
0.6125	Remote Similarity	NPC45618
0.6118	Remote Similarity	NPC211594
0.6098	Remote Similarity	NPC472459
0.6049	Remote Similarity	NPC64305
0.6049	Remote Similarity	NPC146792
0.6049	Remote Similarity	NPC259152
0.6049	Remote Similarity	NPC189142
0.6049	Remote Similarity	NPC77660
0.5976	Remote Similarity	NPC181712
0.5952	Remote Similarity	NPC601144
0.5934	Remote Similarity	NPC124155
0.5926	Remote Similarity	NPC261866
0.5926	Remote Similarity	NPC83283
0.5904	Remote Similarity	NPC182045
0.5854	Remote Similarity	NPC168822
0.5797	Remote Similarity	NPC293183
0.5783	Remote Similarity	NPC58716
0.5778	Remote Similarity	NPC204693
0.5775	Remote Similarity	NPC256283
0.5765	Remote Similarity	NPC284960
0.5765	Remote Similarity	NPC120099
0.5765	Remote Similarity	NPC21666
0.5765	Remote Similarity	NPC486578
0.5765	Remote Similarity	NPC609478
0.5732	Remote Similarity	NPC289667
0.5732	Remote Similarity	NPC110349
0.5714	Remote Similarity	NPC222936
0.5714	Remote Similarity	NPC241498
0.5696	Remote Similarity	NPC183036
0.5694	Remote Similarity	NPC255350
0.5638	Remote Similarity	NPC256760
0.5591	Remote Similarity	NPC483707
0.5581	Remote Similarity	NPC148710
0.5581	Remote Similarity	NPC80188
0.5543	Remote Similarity	NPC488073
0.5543	Remote Similarity	NPC472992
0.5529	Remote Similarity	NPC475942
0.5529	Remote Similarity	NPC21100
0.5529	Remote Similarity	NPC117260
0.5474	Remote Similarity	NPC475382
0.5465	Remote Similarity	NPC60735
0.5465	Remote Similarity	NPC26230
0.5465	Remote Similarity	NPC285197
0.5417	Remote Similarity	NPC100887
0.5417	Remote Similarity	NPC145379
0.5412	Remote Similarity	NPC305811
0.5412	Remote Similarity	NPC24043
0.5412	Remote Similarity	NPC73511
0.5393	Remote Similarity	NPC172807
0.5349	Remote Similarity	NPC27942
0.5341	Remote Similarity	NPC220169
0.5333	Remote Similarity	NPC472607
0.5326	Remote Similarity	NPC22062
0.5326	Remote Similarity	NPC473634
0.5326	Remote Similarity	NPC138811
0.5312	Remote Similarity	NPC477629
0.5294	Remote Similarity	NPC258035
0.5294	Remote Similarity	NPC156457
0.5294	Remote Similarity	NPC106700
0.5287	Remote Similarity	NPC488071
0.5281	Remote Similarity	NPC203050
0.5281	Remote Similarity	NPC488072
0.5281	Remote Similarity	NPC225434
0.5281	Remote Similarity	NPC601586
0.5278	Remote Similarity	NPC284552
0.527	Remote Similarity	NPC83508
0.5269	Remote Similarity	NPC257566
0.5238	Remote Similarity	NPC331652
0.5233	Remote Similarity	NPC84362
0.5233	Remote Similarity	NPC602537
0.5233	Remote Similarity	NPC603655
0.5227	Remote Similarity	NPC606560
0.5222	Remote Similarity	NPC4390
0.5213	Remote Similarity	NPC46202
0.5208	Remote Similarity	NPC472991
0.5181	Remote Similarity	NPC34287
0.5176	Remote Similarity	NPC77672
0.5176	Remote Similarity	NPC133671
0.5176	Remote Similarity	NPC135391
0.5176	Remote Similarity	NPC78263
0.5176	Remote Similarity	NPC250069
0.5172	Remote Similarity	NPC325555
0.5172	Remote Similarity	NPC226304
0.5169	Remote Similarity	NPC307518
0.5165	Remote Similarity	NPC8856
0.5165	Remote Similarity	NPC254540
0.5161	Remote Similarity	NPC607513
0.5158	Remote Similarity	NPC477628
0.5116	Remote Similarity	NPC145038
0.5116	Remote Similarity	NPC56077
0.5116	Remote Similarity	NPC281131
0.5116	Remote Similarity	NPC253662
0.5116	Remote Similarity	NPC179950
0.5116	Remote Similarity	NPC277205
0.5116	Remote Similarity	NPC37919
0.5116	Remote Similarity	NPC323593
0.5116	Remote Similarity	NPC88789
0.5116	Remote Similarity	NPC203500
0.5116	Remote Similarity	NPC491374
0.5114	Remote Similarity	NPC224462
0.5114	Remote Similarity	NPC479401
0.5106	Remote Similarity	NPC470444
0.5106	Remote Similarity	NPC131745
0.5104	Remote Similarity	NPC473623
0.5062	Remote Similarity	NPC213622
0.5059	Remote Similarity	NPC45165
0.5059	Remote Similarity	NPC135345
0.5057	Remote Similarity	NPC472385
0.5056	Remote Similarity	NPC229729
0.5056	Remote Similarity	NPC197285
0.5052	Remote Similarity	NPC488089
0.5049	Remote Similarity	NPC311850

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC520801 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4666
0.1-0.2	4369
0.2-0.3	96
0.3-0.4	12
0.4-0.5	6
0.5-0.6	1
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
0.5694	Remote Similarity	NPD2801	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