NPASS Compound

Natural Product: NPC541818

Natural Product ID	NPC541818
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-6-[[(2~{S},3~{R},4~{S},5~{S})-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)chromen-4-one
IUPAC Name	7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-6-[[(2~{S},3~{R},4~{S},5~{S})-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)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 72 76 0 0 0 0 0 0 0 0999 V2000 9.9273 2.6968 -0.9008 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9698 1.3122 -0.6479 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8002 0.6040 -0.4444 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5535 1.1812 -0.4986 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4170 0.3938 -0.2822 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5114 -0.9536 -0.0135 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2814 -1.7327 0.1681 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2980 -3.0650 0.5545 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1378 -3.7861 0.7224 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1135 -4.9929 1.0715 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9464 -3.1416 0.4937 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7236 -3.7534 0.6244 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7558 -5.1044 1.0184 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5501 -3.0960 0.3881 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5268 -1.7459 -0.0051 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6803 -1.1260 -0.2367 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9023 0.2030 -0.6327 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8690 0.7412 0.2033 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6046 1.6655 -0.5332 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2784 2.7278 0.2515 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1943 2.4550 1.1704 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3956 1.9375 0.9644 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6031 0.6855 1.6124 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8982 0.4030 1.1732 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5740 -0.6202 2.0596 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8769 -1.8220 2.0912 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6803 1.6995 1.2121 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7063 1.7146 2.1215 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5599 2.6810 1.6055 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5266 2.6825 2.9767 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5176 0.9163 -1.4373 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2093 1.7354 -2.3214 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7332 -0.0823 -2.2477 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9462 -1.3590 -1.6825 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2682 0.1879 -2.1014 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7755 1.2349 -2.8374 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7537 -1.1437 -0.1315 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9571 -1.8202 0.1110 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1032 -1.2042 -0.0262 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7728 -1.4865 0.0323 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9191 -0.7627 -0.1723 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1880 -1.3230 -0.1223 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8316 3.2820 0.0609 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9159 3.0100 -1.3387 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1276 2.9809 -1.6045 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4652 2.2404 -0.7075 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4482 0.8550 -0.3279 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2324 -3.5468 0.7293 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2233 -5.2851 1.8827 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4026 -3.5892 0.4940 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0604 0.7804 -0.5647 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7987 2.2237 -1.1209 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5928 3.4973 -0.5160 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4309 3.2920 0.7804 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7388 1.7363 -0.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8212 0.0196 0.1357 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7197 -0.1899 3.0698 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5946 -0.8248 1.6362 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8723 -2.1324 3.0427 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0146 1.9473 0.1631 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6107 1.7468 1.6955 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7973 3.6273 1.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7703 3.1952 3.3205 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1830 0.3004 -0.7848 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9937 1.5210 -3.2639 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0555 -0.0926 -3.3163 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9094 -1.5920 -1.6676 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7756 -0.7320 -2.5909 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5621 0.9900 -3.7705 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8221 -0.1068 -0.4285 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8840 -2.5426 0.2412 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2262 -2.3488 -0.0536 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 12 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 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 19 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 15 37 1 0 37 38 2 0 38 39 1 0 6 40 1 0 40 41 2 0 41 42 1 0 41 3 1 0 39 7 1 0 38 11 1 0 35 17 1 0 29 22 1 0 1 43 1 0 1 44 1 0 1 45 1 0 4 46 1 0 5 47 1 0 8 48 1 0 13 49 1 0 14 50 1 0 17 51 1 6 19 52 1 6 20 53 1 0 20 54 1 0 22 55 1 6 24 56 1 6 25 57 1 0 25 58 1 0 26 59 1 0 27 60 1 6 28 61 1 0 29 62 1 6 30 63 1 0 31 64 1 1 32 65 1 0 33 66 1 6 34 67 1 0 35 68 1 6 36 69 1 0 37 70 1 0 40 71 1 0 42 72 1 0 M END

Standard InCHIKey	GHYGFLACCCIQKR-GBJFMCQXSA-N
Standard InCHI	InChI=1S/C27H30O15/c1-37-15-3-2-10(4-12(15)29)16-7-14(31)20-13(30)5-11(6-17(20)40-16)39-27-25(36)23(34)22(33)19(42-27)9-38-26-24(35)21(32)18(8-28)41-26/h2-7,18-19,21-30,32-36H,8-9H2,1H3/t18-,19+,21+,22+,23-,24+,25+,26-,27+/m0/s1
SMILES	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](CO)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)C=C3O2)C=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	0.524 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.1 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.916 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	29.0
TPSA:	238.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.148	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.572	Fsp³:	0.444
MCE-18:	114.231 ? 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:	0
Colloidal aggregators:	0.654	Fluc inhibitor:	0.309 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.976 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.681 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.085	Promiscuous compounds:	0.363

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.468	MDCK Permeability:	-5.26
Pgp-inhibitor:	0.0	Pgp-substrate:	0.865
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):	0.294
20% Bioavailability (F20%):	0.167	30% Bioavailability (F30%):	0.962
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.17
Plasma Protein Binding (PPB):	79.831%	Volume Distribution (VD):	-0.117
Fu:	17.314% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.243
BSEP inhibitor:	0.189

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:	0.002	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.344
HLM stability:	0.003 ? 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):

1.692

Half-life (T1/2):

4.466

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.2
Human Hepatotoxicity (H-HT):	0.417	Drug-induced Liver Injury (DILI):	0.881
AMES Toxicity:	0.841	Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.036	Skin Sensitization:	0.968
Carcinogencity:	0.084	Eye Corrosion:	0.0
Eye Irritation:	0.24	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.957
Hematotoxicity:	0.145	Drug-induced Nephrotoxicity:	0.516
Genotoxicity:	0.457	RPMI-8226 Immunitoxicity:	0.167
A549 Cytotoxicity:	0.089	Hek293 Cytotoxicity:	0.224
BCF:	0.365 ? 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:	2.847 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.464 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.575 ? 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
NPO25019	Salix caprea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25019	Salix caprea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25019	Salix caprea	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25019	Salix caprea	Species	Salicaceae	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 NPC541818 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	20649
0.1-0.2	24981
0.2-0.3	3089
0.3-0.4	720
0.4-0.5	278
0.5-0.6	90
0.6-0.7	38
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8706	High Similarity	NPC209296
0.8049	Intermediate Similarity	NPC22832
0.7614	Intermediate Similarity	NPC22062
0.7614	Intermediate Similarity	NPC473634
0.7614	Intermediate Similarity	NPC138811
0.7391	Intermediate Similarity	NPC488089
0.7283	Intermediate Similarity	NPC473623
0.7222	Intermediate Similarity	NPC210073
0.7129	Intermediate Similarity	NPC198199
0.6989	Remote Similarity	NPC65711
0.6941	Remote Similarity	NPC95090
0.6941	Remote Similarity	NPC27408
0.6923	Remote Similarity	NPC120952
0.6923	Remote Similarity	NPC44931
0.6702	Remote Similarity	NPC46202
0.6629	Remote Similarity	NPC243930
0.6556	Remote Similarity	NPC311830
0.6556	Remote Similarity	NPC607707
0.6552	Remote Similarity	NPC189142
0.6552	Remote Similarity	NPC77660
0.6477	Remote Similarity	NPC181712
0.6392	Remote Similarity	NPC229409
0.6364	Remote Similarity	NPC101636
0.6346	Remote Similarity	NPC488083
0.6264	Remote Similarity	NPC486578
0.6264	Remote Similarity	NPC601144
0.6264	Remote Similarity	NPC605067
0.625	Remote Similarity	NPC204693
0.625	Remote Similarity	NPC261866
0.625	Remote Similarity	NPC39360
0.625	Remote Similarity	NPC311850
0.625	Remote Similarity	NPC29763
0.625	Remote Similarity	NPC210003
0.6214	Remote Similarity	NPC472993
0.6211	Remote Similarity	NPC275454
0.6203	Remote Similarity	NPC223579
0.6186	Remote Similarity	NPC64051
0.6176	Remote Similarity	NPC11468
0.6162	Remote Similarity	NPC270675
0.6162	Remote Similarity	NPC195685
0.6154	Remote Similarity	NPC285197
0.6129	Remote Similarity	NPC190003
0.6075	Remote Similarity	NPC68592
0.6067	Remote Similarity	NPC19709
0.6044	Remote Similarity	NPC27942
0.604	Remote Similarity	NPC298171
0.6038	Remote Similarity	NPC488087
0.598	Remote Similarity	NPC472994
0.5978	Remote Similarity	NPC191306
0.5978	Remote Similarity	NPC611303
0.5941	Remote Similarity	NPC475382
0.59	Remote Similarity	NPC483707
0.5895	Remote Similarity	NPC211594
0.5876	Remote Similarity	NPC67105
0.5849	Remote Similarity	NPC473644
0.5833	Remote Similarity	NPC8856
0.5833	Remote Similarity	NPC254540
0.5825	Remote Similarity	NPC135358
0.5778	Remote Similarity	NPC473043
0.5778	Remote Similarity	NPC331652
0.5758	Remote Similarity	NPC186816
0.5752	Remote Similarity	NPC262222
0.5745	Remote Similarity	NPC80188
0.5743	Remote Similarity	NPC473327
0.5727	Remote Similarity	NPC298666
0.5714	Remote Similarity	NPC58053
0.5714	Remote Similarity	NPC227508
0.5684	Remote Similarity	NPC220169
0.567	Remote Similarity	NPC251417
0.5657	Remote Similarity	NPC479405
0.5636	Remote Similarity	NPC488086
0.5631	Remote Similarity	NPC195257
0.5612	Remote Similarity	NPC295613
0.5612	Remote Similarity	NPC473657
0.56	Remote Similarity	NPC115674
0.56	Remote Similarity	NPC479404
0.5591	Remote Similarity	NPC186807
0.5567	Remote Similarity	NPC172807
0.5545	Remote Similarity	NPC488088
0.5545	Remote Similarity	NPC475366
0.5543	Remote Similarity	NPC289667
0.55	Remote Similarity	NPC473512
0.55	Remote Similarity	NPC129827
0.549	Remote Similarity	NPC479403
0.5437	Remote Similarity	NPC606657
0.5426	Remote Similarity	NPC84362
0.5426	Remote Similarity	NPC45638
0.5413	Remote Similarity	NPC480441
0.5413	Remote Similarity	NPC25523
0.5392	Remote Similarity	NPC284277
0.5392	Remote Similarity	NPC475497
0.5376	Remote Similarity	NPC143851
0.5368	Remote Similarity	NPC201292
0.5364	Remote Similarity	NPC277532
0.5347	Remote Similarity	NPC65003
0.5319	Remote Similarity	NPC277205
0.5319	Remote Similarity	NPC37919
0.5312	Remote Similarity	NPC609451
0.5306	Remote Similarity	NPC601586
0.5288	Remote Similarity	NPC51326
0.5283	Remote Similarity	NPC235575
0.5263	Remote Similarity	NPC58716
0.5258	Remote Similarity	NPC284960
0.5258	Remote Similarity	NPC21666
0.5258	Remote Similarity	NPC608742
0.5243	Remote Similarity	NPC488073
0.5238	Remote Similarity	NPC479766
0.5234	Remote Similarity	NPC484301
0.5204	Remote Similarity	NPC88023
0.5204	Remote Similarity	NPC309025
0.5204	Remote Similarity	NPC602805
0.5196	Remote Similarity	NPC102028
0.5196	Remote Similarity	NPC303913
0.5189	Remote Similarity	NPC80068
0.5189	Remote Similarity	NPC479765
0.5189	Remote Similarity	NPC477629
0.5182	Remote Similarity	NPC480796
0.5158	Remote Similarity	NPC93337
0.5158	Remote Similarity	NPC297987
0.5158	Remote Similarity	NPC168822
0.5158	Remote Similarity	NPC136042
0.5158	Remote Similarity	NPC323593
0.5158	Remote Similarity	NPC203500
0.5146	Remote Similarity	NPC122809
0.5138	Remote Similarity	NPC121703
0.5122	Remote Similarity	NPC29353
0.5104	Remote Similarity	NPC105025
0.5102	Remote Similarity	NPC120099
0.5098	Remote Similarity	NPC15358
0.5094	Remote Similarity	NPC142142
0.5094	Remote Similarity	NPC486577
0.5093	Remote Similarity	NPC253685
0.5059	Remote Similarity	NPC177298
0.5053	Remote Similarity	NPC45618
0.505	Remote Similarity	NPC606546
0.5049	Remote Similarity	NPC156869
0.5048	Remote Similarity	NPC470443

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC541818 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5133
0.1-0.2	3935
0.2-0.3	68
0.3-0.4	8
0.4-0.5	2
0.5-0.6	2
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8706	High Similarity	NPD7054	Phase 4
0.6667	Remote Similarity	NPD7472	Pre-clinical
0.5566	Remote Similarity	NPD7808	Phase 3
0.5481	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