NPASS Compound

Natural Product: NPC522182

Natural Product ID	NPC522182
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-2-[3-hydroxy-4-[(2~{R},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phenyl]-7-methoxy-chromen-4-one
IUPAC Name	5-hydroxy-2-[3-hydroxy-4-[(2~{R},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-phenyl]-7-methoxy-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 54 57 0 0 0 0 0 0 0 0999 V2000 6.9362 -2.8862 -1.1643 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6079 -1.6738 -0.8236 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8296 -0.5606 -0.4898 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4197 0.6393 -0.1514 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6917 1.7649 0.1852 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2887 2.9671 0.5242 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3179 1.7099 0.1899 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5844 2.8347 0.5264 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1106 3.9302 0.8354 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 2.6901 0.5055 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6361 1.4861 0.1654 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2139 1.2803 0.1273 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3394 2.2896 0.4328 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0412 2.0656 0.3891 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5686 0.8123 0.0345 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9053 0.7003 0.0226 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7470 -0.3446 -0.2667 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4711 -0.6507 0.9043 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3573 -1.6987 0.6797 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7902 -2.3836 1.9308 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4724 -1.1901 -0.1712 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8098 -2.2025 -1.0885 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1393 0.0384 -0.9525 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4616 1.2154 -0.2936 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7181 -0.0198 -1.3989 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3563 1.2593 -1.8673 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6638 -0.1627 -0.2616 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1050 -1.4264 -0.6206 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7113 0.0540 -0.2199 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4066 0.4502 -0.1459 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7122 0.5174 -0.1460 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4461 -0.5997 -0.4803 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6339 -3.7039 -1.3391 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1939 -3.0968 -0.3708 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3424 -2.6744 -2.0866 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4975 0.7130 -0.1463 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4917 3.1171 1.5055 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5872 3.5195 0.7546 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6789 3.2853 0.7158 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7220 2.8632 0.6305 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2843 -1.3036 -0.5510 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7806 -2.4484 0.0755 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0358 -3.1464 2.2050 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9183 -1.7008 2.7929 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7433 -2.9353 1.7413 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4042 -0.9925 0.4012 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4032 -1.8351 -1.8079 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7692 0.0231 -1.8822 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7612 1.3956 0.4050 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5490 -0.6993 -2.2403 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3968 1.2594 -2.1566 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8082 -2.2703 -0.1808 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3751 -0.7464 -0.4618 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9416 -1.5287 -0.7416 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 5 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 15 27 1 0 27 28 1 0 27 29 2 0 11 30 1 0 30 31 1 0 31 32 2 0 32 3 1 0 31 7 1 0 29 12 1 0 25 17 1 0 1 33 1 0 1 34 1 0 1 35 1 0 4 36 1 0 6 37 1 0 10 38 1 0 13 39 1 0 14 40 1 0 17 41 1 6 19 42 1 6 20 43 1 0 20 44 1 0 20 45 1 0 21 46 1 1 22 47 1 0 23 48 1 6 24 49 1 0 25 50 1 6 26 51 1 0 28 52 1 0 29 53 1 0 32 54 1 0 M END

Standard InCHIKey	UQDIHJADFOWJCW-LBBHLIFDSA-N
Standard InCHI	InChI=1S/C22H22O10/c1-9-19(26)20(27)21(28)22(30-9)32-15-4-3-10(5-12(15)23)16-8-14(25)18-13(24)6-11(29-2)7-17(18)31-16/h3-9,19-24,26-28H,1-2H3/t9-,19-,20+,21+,22+/m0/s1
SMILES	COC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[C@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)C(O)=C3)OC2=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	446.12	Volume:	421.653 ? Van der Waals volume.
Dense:	1.058	LogP:	1.409 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.701 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.396 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	24.0
TPSA:	159.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.393	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.885	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:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.597	Fluc inhibitor:	0.374 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.979 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.82 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.114	Promiscuous compounds:	0.56

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.912	MDCK Permeability:	-5.127
Pgp-inhibitor:	0.017	Pgp-substrate:	0.554
PAMPA:	0.933 ? 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):	0.013
20% Bioavailability (F20%):	0.114	30% Bioavailability (F30%):	0.381
50% Bioavailability (F50%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.345
Plasma Protein Binding (PPB):	87.673%	Volume Distribution (VD):	-0.06
Fu:	11.994% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.702
BSEP inhibitor:	0.867

ADMET: Metabolism

CYP1A2-inhibitor:	0.03	CYP1A2-substrate:	0.225
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.653	CYP2C9-substrate:	0.158
CYP2D6-inhibitor:	0.002	CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.046
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.821 ? 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):

2.647

Half-life (T1/2):

3.311

ADMET: Toxicity

hERG Blockers:	0.039	hERG Blockers (10um):	0.412
Human Hepatotoxicity (H-HT):	0.288	Drug-induced Liver Injury (DILI):	0.844
AMES Toxicity:	0.704	Rat Oral Acute Toxicity:	0.136
Maximum Recommended Daily Dose:	0.344	Skin Sensitization:	0.464
Carcinogencity:	0.219	Eye Corrosion:	0.001
Eye Irritation:	0.881	Respiratory Toxicity:	0.268
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.636
Hematotoxicity:	0.089	Drug-induced Nephrotoxicity:	0.208
Genotoxicity:	0.419	RPMI-8226 Immunitoxicity:	0.144
A549 Cytotoxicity:	0.143	Hek293 Cytotoxicity:	0.272
BCF:	0.761 ? 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:	3.583 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.695 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.017 ? 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
NPO6060	Amaranthus spinosus	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6060	Amaranthus spinosus	Species	Amaranthaceae	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 NPC522182 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	18049
0.1-0.2	27715
0.2-0.3	2936
0.3-0.4	710
0.4-0.5	283
0.5-0.6	113
0.6-0.7	39
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
0.7952	Intermediate Similarity	NPC209296
0.7922	Intermediate Similarity	NPC22832
0.7733	Intermediate Similarity	NPC19709
0.7368	Intermediate Similarity	NPC473043
0.7368	Intermediate Similarity	NPC331652
0.7342	Intermediate Similarity	NPC611303
0.7059	Intermediate Similarity	NPC22062
0.7059	Intermediate Similarity	NPC473634
0.7059	Intermediate Similarity	NPC138811
0.6962	Remote Similarity	NPC95090
0.6962	Remote Similarity	NPC27408
0.6905	Remote Similarity	NPC251417
0.6875	Remote Similarity	NPC181712
0.6857	Remote Similarity	NPC223579
0.6829	Remote Similarity	NPC486578
0.6829	Remote Similarity	NPC605067
0.6747	Remote Similarity	NPC607707
0.6667	Remote Similarity	NPC210073
0.6627	Remote Similarity	NPC243930
0.6548	Remote Similarity	NPC311830
0.6543	Remote Similarity	NPC189142
0.6543	Remote Similarity	NPC77660
0.6506	Remote Similarity	NPC191306
0.6506	Remote Similarity	NPC285197
0.6471	Remote Similarity	NPC190003
0.6465	Remote Similarity	NPC198199
0.6463	Remote Similarity	NPC46420
0.6463	Remote Similarity	NPC271692
0.6429	Remote Similarity	NPC601144
0.6386	Remote Similarity	NPC27942
0.6374	Remote Similarity	NPC606657
0.6364	Remote Similarity	NPC44931
0.6341	Remote Similarity	NPC158674
0.6275	Remote Similarity	NPC120952
0.6237	Remote Similarity	NPC475382
0.622	Remote Similarity	NPC261866
0.622	Remote Similarity	NPC39360
0.622	Remote Similarity	NPC29763
0.622	Remote Similarity	NPC210003
0.622	Remote Similarity	NPC238376
0.6196	Remote Similarity	NPC473623
0.6154	Remote Similarity	NPC46202
0.6129	Remote Similarity	NPC488089
0.6064	Remote Similarity	NPC195257
0.6044	Remote Similarity	NPC115674
0.6024	Remote Similarity	NPC249281
0.6024	Remote Similarity	NPC108831
0.6024	Remote Similarity	NPC182634
0.5979	Remote Similarity	NPC11468
0.593	Remote Similarity	NPC219904
0.587	Remote Similarity	NPC204693
0.5851	Remote Similarity	NPC229409
0.5833	Remote Similarity	NPC58053
0.5833	Remote Similarity	NPC29353
0.58	Remote Similarity	NPC473644
0.5761	Remote Similarity	NPC65003
0.5745	Remote Similarity	NPC65711
0.5743	Remote Similarity	NPC311850
0.57	Remote Similarity	NPC472993
0.5698	Remote Similarity	NPC186807
0.5682	Remote Similarity	NPC80188
0.5682	Remote Similarity	NPC608742
0.5676	Remote Similarity	NPC108406
0.567	Remote Similarity	NPC101636
0.567	Remote Similarity	NPC298171
0.5667	Remote Similarity	NPC211594
0.5638	Remote Similarity	NPC64051
0.5625	Remote Similarity	NPC270675
0.5625	Remote Similarity	NPC195685
0.5618	Remote Similarity	NPC116458
0.5618	Remote Similarity	NPC246943
0.5618	Remote Similarity	NPC220169
0.5618	Remote Similarity	NPC605784
0.5604	Remote Similarity	NPC8856
0.5604	Remote Similarity	NPC254540
0.5577	Remote Similarity	NPC68592
0.5567	Remote Similarity	NPC256760
0.5556	Remote Similarity	NPC276377
0.5556	Remote Similarity	NPC601586
0.5529	Remote Similarity	NPC160515
0.5526	Remote Similarity	NPC177298
0.5526	Remote Similarity	NPC195202
0.5517	Remote Similarity	NPC58716
0.5517	Remote Similarity	NPC45638
0.5506	Remote Similarity	NPC606560
0.5465	Remote Similarity	NPC289667
0.5465	Remote Similarity	NPC143851
0.5455	Remote Similarity	NPC137062
0.5455	Remote Similarity	NPC472994
0.5455	Remote Similarity	NPC201292
0.5405	Remote Similarity	NPC127447
0.5393	Remote Similarity	NPC20505
0.5393	Remote Similarity	NPC609451
0.5368	Remote Similarity	NPC186816
0.5341	Remote Similarity	NPC84362
0.5333	Remote Similarity	NPC48479
0.5333	Remote Similarity	NPC234133
0.5333	Remote Similarity	NPC609478
0.5326	Remote Similarity	NPC4390
0.5326	Remote Similarity	NPC172807
0.5326	Remote Similarity	NPC600989
0.5325	Remote Similarity	NPC160951
0.5319	Remote Similarity	NPC67105
0.5306	Remote Similarity	NPC479766
0.5287	Remote Similarity	NPC45618
0.5287	Remote Similarity	NPC476405
0.5287	Remote Similarity	NPC348541
0.5283	Remote Similarity	NPC488086
0.5281	Remote Similarity	NPC59534
0.5281	Remote Similarity	NPC21100
0.5275	Remote Similarity	NPC88023
0.5275	Remote Similarity	NPC309025
0.5275	Remote Similarity	NPC602805
0.5273	Remote Similarity	NPC262222
0.5263	Remote Similarity	NPC150164
0.5238	Remote Similarity	NPC488087
0.5238	Remote Similarity	NPC488083
0.5234	Remote Similarity	NPC298666
0.5227	Remote Similarity	NPC93337
0.5227	Remote Similarity	NPC168822
0.5227	Remote Similarity	NPC265530
0.5227	Remote Similarity	NPC146792
0.5227	Remote Similarity	NPC277205
0.5227	Remote Similarity	NPC37919
0.5208	Remote Similarity	NPC257566
0.5204	Remote Similarity	NPC32641
0.5204	Remote Similarity	NPC256188
0.5204	Remote Similarity	NPC483707
0.5204	Remote Similarity	NPC72016
0.5204	Remote Similarity	NPC35119
0.5204	Remote Similarity	NPC473327
0.5195	Remote Similarity	NPC200740
0.5195	Remote Similarity	NPC270620
0.5195	Remote Similarity	NPC212678
0.5169	Remote Similarity	NPC27640
0.5169	Remote Similarity	NPC105025
0.5169	Remote Similarity	NPC349108
0.5165	Remote Similarity	NPC284960
0.5165	Remote Similarity	NPC21666
0.5165	Remote Similarity	NPC601710
0.5158	Remote Similarity	NPC227508
0.5155	Remote Similarity	NPC240306
0.5155	Remote Similarity	NPC475366
0.5152	Remote Similarity	NPC142142
0.5149	Remote Similarity	NPC484301
0.5149	Remote Similarity	NPC135358
0.5132	Remote Similarity	NPC33265
0.5128	Remote Similarity	NPC52005
0.5109	Remote Similarity	NPC223747
0.5106	Remote Similarity	NPC487212
0.51	Remote Similarity	NPC479765
0.5056	Remote Similarity	NPC297987
0.5056	Remote Similarity	NPC136042
0.5056	Remote Similarity	NPC323593
0.5056	Remote Similarity	NPC203500
0.5055	Remote Similarity	NPC282169
0.5055	Remote Similarity	NPC60735
0.5055	Remote Similarity	NPC26230
0.5054	Remote Similarity	NPC267254
0.5051	Remote Similarity	NPC124155
0.5046	Remote Similarity	NPC470719

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC522182 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4549
0.1-0.2	4506
0.2-0.3	80
0.3-0.4	8
0.4-0.5	4
0.5-0.6	2
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
0.7952	Intermediate Similarity	NPD7054	Phase 4
0.5979	Remote Similarity	NPD7472	Pre-clinical
0.5049	Remote Similarity	NPD7808	Phase 3

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