NPASS Compound

Natural Product: NPC537146

Natural Product ID	NPC537146
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-oxo-3-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-yl]methoxy]propanoic acid
IUPAC Name	3-oxo-3-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-2-(3-hydroxy-4-methoxy-phenyl)-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-yl]methoxy]propanoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-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 63 66 0 0 0 0 0 0 0 0999 V2000 10.0008 1.7892 -1.3406 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8192 1.0282 -0.1666 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5374 0.7476 0.2638 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4302 1.1899 -0.4715 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1521 0.9119 -0.0392 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9182 0.1834 1.1327 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5235 -0.0590 1.4816 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1298 -0.5832 2.7079 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8154 -0.7990 3.0265 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4433 -1.2750 4.1314 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8450 -0.4823 2.1014 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5072 -0.6600 2.3393 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1617 -1.1769 3.5780 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4063 -0.3243 1.3613 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0352 0.1940 0.1295 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8856 0.5362 -0.8635 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2533 0.6220 -0.9445 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8039 -0.7068 -0.8591 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1798 -0.4706 -0.6387 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7926 -1.6013 0.1073 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1775 -1.4176 0.3581 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7168 -0.3843 1.0794 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8857 0.4579 1.5574 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1431 -0.1918 1.3255 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9178 -1.3644 0.8875 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1007 -2.3124 1.6696 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4396 -1.4079 -0.3870 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8303 -0.1984 -1.9934 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3336 -1.3595 -2.5507 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8006 0.3993 -2.9326 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2191 -0.5804 -3.7084 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7956 1.2429 -2.1747 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3191 2.5246 -1.9352 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3377 0.3657 -0.0778 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2654 0.0330 0.8973 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5488 0.2171 0.6439 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9829 -0.2527 1.8495 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2622 0.0287 1.4146 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3500 -0.4185 2.1361 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6962 1.2281 -2.2217 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4001 2.7387 -1.2793 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0809 2.0959 -1.3587 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5942 1.7542 -1.3793 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3357 1.2856 -0.6504 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9127 -0.8155 3.4143 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8117 -1.4145 3.7364 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4626 -0.4637 1.5433 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7024 1.1350 -0.0371 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2395 0.4844 -0.0668 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2131 -1.8323 1.0086 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7329 -2.5382 -0.5370 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3242 0.0839 2.4060 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4805 0.6820 0.6844 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9950 -2.1608 -0.7694 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6717 0.5102 -1.8464 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8380 -1.0898 -3.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3521 1.0835 -3.6308 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8947 -1.2950 -3.8567 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9622 1.4230 -2.9434 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1013 3.1545 -2.6679 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6646 0.7674 -1.0348 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8225 -0.8307 2.7615 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2806 -0.4314 1.7587 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 2 0 22 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 19 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 15 34 1 0 34 35 2 0 35 36 1 0 6 37 1 0 37 38 2 0 38 39 1 0 38 3 1 0 36 7 1 0 35 11 1 0 32 17 1 0 1 40 1 0 1 41 1 0 1 42 1 0 4 43 1 0 5 44 1 0 8 45 1 0 13 46 1 0 14 47 1 0 17 48 1 1 19 49 1 1 20 50 1 0 20 51 1 0 24 52 1 0 24 53 1 0 27 54 1 0 28 55 1 1 29 56 1 0 30 57 1 6 31 58 1 0 32 59 1 6 33 60 1 0 34 61 1 0 37 62 1 0 39 63 1 0 M END

Standard InCHIKey	BUKAUEHHOBSSPT-XUAKBXRPSA-N
Standard InCHI	InChI=1S/C25H24O14/c1-35-15-3-2-10(4-12(15)26)16-7-14(28)21-13(27)5-11(6-17(21)38-16)37-25-24(34)23(33)22(32)18(39-25)9-36-20(31)8-19(29)30/h2-7,18,22-27,32-34H,8-9H2,1H3,(H,29,30)/t18-,22+,23+,24-,25-/m1/s1
SMILES	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[C@@H]4O[C@H](COC(=O)CC(=O)O)[C@H](O)[C@H](O)[C@H]4O)C=C3O2)C=C1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	548.12	Volume:	503.429 ? Van der Waals volume.
Dense:	1.089	LogP:	1.114 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.401 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.016 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	26.0
TPSA:	222.65 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.162	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.102	Fsp³:	0.32
MCE-18:	92.485 ? 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:	0.49	Fluc inhibitor:	0.324 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.965 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.897 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.031	Promiscuous compounds:	0.417

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.058	MDCK Permeability:	-5.367
Pgp-inhibitor:	0.0	Pgp-substrate:	0.094
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):	0.556
20% Bioavailability (F20%):	0.19	30% Bioavailability (F30%):	0.866
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.817
Plasma Protein Binding (PPB):	77.698%	Volume Distribution (VD):	-0.31
Fu:	19.709% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.022
BSEP inhibitor:	0.0

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:	0.134
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.743
HLM stability:	0.006 ? 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):

0.76

Half-life (T1/2):

2.651

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.026
Human Hepatotoxicity (H-HT):	0.549	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.907	Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.082	Skin Sensitization:	0.998
Carcinogencity:	0.472	Eye Corrosion:	0.0
Eye Irritation:	0.677	Respiratory Toxicity:	0.097
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.685
Hematotoxicity:	0.514	Drug-induced Nephrotoxicity:	0.843
Genotoxicity:	0.987	RPMI-8226 Immunitoxicity:	0.136
A549 Cytotoxicity:	0.087	Hek293 Cytotoxicity:	0.176
BCF:	0.201 ? 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:	2.709 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.183 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.355 ? 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
NPO44865	Bryum capillare	Species	Bryaceae	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 NPC537146 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	18569
0.1-0.2	27934
0.2-0.3	2415
0.3-0.4	623
0.4-0.5	225
0.5-0.6	58
0.6-0.7	20
0.7-0.8	1
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8941	High Similarity	NPC46202
0.8523	High Similarity	NPC229409
0.8295	Intermediate Similarity	NPC64051
0.7527	Intermediate Similarity	NPC209296
0.7083	Intermediate Similarity	NPC479766
0.7079	Intermediate Similarity	NPC22832
0.701	Intermediate Similarity	NPC479765
0.6737	Remote Similarity	NPC22062
0.6737	Remote Similarity	NPC473634
0.6737	Remote Similarity	NPC138811
0.6465	Remote Similarity	NPC473623
0.6442	Remote Similarity	NPC472993
0.64	Remote Similarity	NPC270675
0.64	Remote Similarity	NPC488089
0.64	Remote Similarity	NPC195685
0.6374	Remote Similarity	NPC181712
0.6264	Remote Similarity	NPC95090
0.6264	Remote Similarity	NPC27408
0.6224	Remote Similarity	NPC210073
0.6214	Remote Similarity	NPC472994
0.617	Remote Similarity	NPC608742
0.6146	Remote Similarity	NPC211594
0.6122	Remote Similarity	NPC44931
0.6095	Remote Similarity	NPC121703
0.6042	Remote Similarity	NPC190003
0.604	Remote Similarity	NPC65711
0.6019	Remote Similarity	NPC277532
0.5957	Remote Similarity	NPC27942
0.5938	Remote Similarity	NPC311830
0.5929	Remote Similarity	NPC120952
0.5918	Remote Similarity	NPC254540
0.5904	Remote Similarity	NPC223579
0.5895	Remote Similarity	NPC611303
0.5833	Remote Similarity	NPC243930
0.5816	Remote Similarity	NPC172807
0.581	Remote Similarity	NPC101636
0.581	Remote Similarity	NPC298171
0.5806	Remote Similarity	NPC19709
0.5804	Remote Similarity	NPC198199
0.5794	Remote Similarity	NPC11468
0.5773	Remote Similarity	NPC607707
0.5745	Remote Similarity	NPC189142
0.5745	Remote Similarity	NPC77660
0.5729	Remote Similarity	NPC20505
0.5699	Remote Similarity	NPC331652
0.567	Remote Similarity	NPC601144
0.5638	Remote Similarity	NPC39360
0.5638	Remote Similarity	NPC29763
0.5638	Remote Similarity	NPC210003
0.5567	Remote Similarity	NPC282169
0.5536	Remote Similarity	NPC488087
0.5534	Remote Similarity	NPC204693
0.5532	Remote Similarity	NPC473043
0.551	Remote Similarity	NPC486578
0.551	Remote Similarity	NPC605067
0.5474	Remote Similarity	NPC261866
0.5439	Remote Similarity	NPC488086
0.5421	Remote Similarity	NPC477629
0.5408	Remote Similarity	NPC285197
0.5377	Remote Similarity	NPC483707
0.5377	Remote Similarity	NPC606657
0.5304	Remote Similarity	NPC68592
0.5278	Remote Similarity	NPC80068
0.5278	Remote Similarity	NPC475382
0.5268	Remote Similarity	NPC480796
0.5253	Remote Similarity	NPC191306
0.5221	Remote Similarity	NPC473644
0.52	Remote Similarity	NPC80188
0.5196	Remote Similarity	NPC600989
0.5185	Remote Similarity	NPC486577
0.5182	Remote Similarity	NPC253685
0.5175	Remote Similarity	NPC311850
0.5155	Remote Similarity	NPC58053
0.5149	Remote Similarity	NPC220169
0.5146	Remote Similarity	NPC251417
0.513	Remote Similarity	NPC488083
0.5096	Remote Similarity	NPC295613
0.5096	Remote Similarity	NPC473657
0.5094	Remote Similarity	NPC186816
0.5093	Remote Similarity	NPC473327
0.5086	Remote Similarity	NPC488088
0.5059	Remote Similarity	NPC29353
0.5051	Remote Similarity	NPC186807
0.5048	Remote Similarity	NPC67105
0.5047	Remote Similarity	NPC153755

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC537146 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3956
0.1-0.2	5088
0.2-0.3	93
0.3-0.4	7
0.4-0.5	4
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
0.7527	Intermediate Similarity	NPD7054	Phase 4
0.5648	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