NPASS Compound

Natural Product: NPC551296

Natural Product ID	NPC551296
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-3-[(2~{S},3~{R},4~{R},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5,7-dihydroxy-6-methoxy-2-(4-methoxyphenyl)-3-[(2~{S},3~{R},4~{R},5~{R},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)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 59 62 0 0 0 0 0 0 0 0999 V2000 -0.9669 6.8883 -0.6622 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8393 5.9883 -1.2953 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7701 4.6468 -0.9597 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5964 3.7160 -1.5435 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5068 2.3906 -1.1932 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5930 1.9019 -0.2423 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6652 0.4862 0.0552 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6818 -0.1663 0.7058 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4842 0.4332 1.1344 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6119 0.3475 0.2420 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4132 -0.6683 0.8044 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3825 -1.1146 -0.0596 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5127 -1.6924 0.7983 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5503 -2.1749 0.0282 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9558 -0.0125 -0.9244 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2759 -0.2871 -1.2079 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8368 1.2751 -0.1162 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4907 2.2680 -0.8438 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3614 1.6065 0.0455 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9853 2.1716 -1.1949 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7926 -1.5376 0.9790 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1199 -2.1210 1.5811 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9262 -2.1936 0.5626 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0624 -3.5668 0.8217 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0365 -4.1892 1.4908 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2071 -4.1956 0.3914 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3348 -5.5498 0.6503 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9160 -6.0916 1.8003 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1653 -3.4811 -0.2654 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3151 -4.1340 -0.6926 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0451 -2.1476 -0.5231 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8923 -1.4685 -0.1006 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7679 -0.1941 -0.3418 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7894 2.8408 0.3208 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8738 4.1852 -0.0294 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3048 7.9251 -0.9073 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0877 6.7131 -0.9846 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0351 6.7156 0.4291 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3054 4.0740 -2.2771 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1870 1.6975 -1.6901 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3127 -0.0669 -0.7441 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0468 -1.9220 -0.7431 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8315 -0.8456 1.4585 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1003 -2.4873 1.4454 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3965 -1.7370 0.2694 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4086 0.0625 -1.8715 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2930 -0.9385 -1.9757 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3566 1.1535 0.8403 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4563 2.3043 -0.6337 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2543 2.3784 0.8179 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4744 3.0244 -1.3261 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6715 -5.1024 1.2843 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4184 -5.3320 2.4453 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0903 -6.5064 2.4336 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5843 -6.9550 1.5826 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5745 -4.1243 -1.6911 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7926 -1.5647 -1.0415 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0947 2.5192 1.0824 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1964 4.8551 0.4680 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 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 8 21 1 0 21 22 2 0 21 23 1 0 23 24 2 0 24 25 1 0 24 26 1 0 26 27 1 0 27 28 1 0 26 29 2 0 29 30 1 0 29 31 1 0 31 32 2 0 32 33 1 0 6 34 1 0 34 35 2 0 35 3 1 0 33 7 1 0 19 10 1 0 32 23 1 0 1 36 1 0 1 37 1 0 1 38 1 0 4 39 1 0 5 40 1 0 10 41 1 6 12 42 1 6 13 43 1 0 13 44 1 0 14 45 1 0 15 46 1 6 16 47 1 0 17 48 1 1 18 49 1 0 19 50 1 1 20 51 1 0 25 52 1 0 28 53 1 0 28 54 1 0 28 55 1 0 30 56 1 0 31 57 1 0 34 58 1 0 35 59 1 0 M END

Standard InCHIKey	BNHYQVLYKVAVLP-PBIHIGPQSA-N
Standard InCHI	InChI=1S/C23H24O12/c1-31-10-5-3-9(4-6-10)20-22(35-23-19(30)18(29)15(26)13(8-24)34-23)17(28)14-12(33-20)7-11(25)21(32-2)16(14)27/h3-7,13,15,18-19,23-27,29-30H,8H2,1-2H3/t13-,15+,18-,19-,23+/m1/s1
SMILES	COC1=CC=C(C2=C(O[C@@H]3O[C@H](CO)[C@H](O)[C@@H](O)[C@H]3O)C(=O)C3=C(O)C(OC)=C(O)C=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	492.13	Volume:	456.529 ? Van der Waals volume.
Dense:	1.078	LogP:	1.503 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.849 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.098 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	24.0
TPSA:	188.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.272	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.929	Fsp³:	0.348
MCE-18:	89.71 ? 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:	0.577	Fluc inhibitor:	0.315 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.89 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.739 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.091	Promiscuous compounds:	0.639

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.129	MDCK Permeability:	-5.389
Pgp-inhibitor:	0.004	Pgp-substrate:	0.601
PAMPA:	0.938 ? 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):	0.704
20% Bioavailability (F20%):	0.555	30% Bioavailability (F30%):	0.943
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.657
Plasma Protein Binding (PPB):	90.347%	Volume Distribution (VD):	-0.17
Fu:	8.919% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.78
OATP1B3 inhibitor:	0.965	BCRP inhibitor:	0.349
BSEP inhibitor:	0.035

ADMET: Metabolism

CYP1A2-inhibitor:	0.022	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.582	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.005	CYP2D6-substrate:	0.006
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.006
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.987 ? 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):

2.362

Half-life (T1/2):

2.007

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.17
Human Hepatotoxicity (H-HT):	0.589	Drug-induced Liver Injury (DILI):	0.885
AMES Toxicity:	0.869	Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.092	Skin Sensitization:	0.992
Carcinogencity:	0.392	Eye Corrosion:	0.0
Eye Irritation:	0.458	Respiratory Toxicity:	0.106
Drug-induced Neurotoxicity:	0.036	Ototoxicity:	0.769
Hematotoxicity:	0.361	Drug-induced Nephrotoxicity:	0.388
Genotoxicity:	0.332	RPMI-8226 Immunitoxicity:	0.097
A549 Cytotoxicity:	0.525	Hek293 Cytotoxicity:	0.457
BCF:	0.384 ? 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:	3.149 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.598 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.772 ? 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
NPO27892	Eupatorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27892	Eupatorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27892	Eupatorium glandulosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27892	Eupatorium glandulosum	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 NPC551296 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	18701
0.1-0.2	26910
0.2-0.3	2840
0.3-0.4	878
0.4-0.5	333
0.5-0.6	122
0.6-0.7	51
0.7-0.8	0
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8592	High Similarity	NPC488080
0.8592	High Similarity	NPC169977
0.8219	Intermediate Similarity	NPC42773
0.8219	Intermediate Similarity	NPC45522
0.8	Intermediate Similarity	NPC101026
0.8	Intermediate Similarity	NPC488077
0.7973	Intermediate Similarity	NPC472459
0.7467	Intermediate Similarity	NPC64305
0.7105	Intermediate Similarity	NPC289667
0.7089	Intermediate Similarity	NPC120099
0.6941	Remote Similarity	NPC488073
0.6923	Remote Similarity	NPC305811
0.6923	Remote Similarity	NPC24043
0.675	Remote Similarity	NPC60735
0.675	Remote Similarity	NPC26230
0.6667	Remote Similarity	NPC77672
0.6667	Remote Similarity	NPC133671
0.6667	Remote Similarity	NPC135391
0.6667	Remote Similarity	NPC78263
0.6667	Remote Similarity	NPC250069
0.6667	Remote Similarity	NPC21666
0.6667	Remote Similarity	NPC609478
0.6567	Remote Similarity	NPC203891
0.6543	Remote Similarity	NPC488071
0.6506	Remote Similarity	NPC203050
0.6506	Remote Similarity	NPC488072
0.6506	Remote Similarity	NPC225434
0.6437	Remote Similarity	NPC470444
0.642	Remote Similarity	NPC325555
0.642	Remote Similarity	NPC226304
0.6375	Remote Similarity	NPC145038
0.6375	Remote Similarity	NPC56077
0.6375	Remote Similarity	NPC297987
0.6375	Remote Similarity	NPC281131
0.6375	Remote Similarity	NPC253662
0.6375	Remote Similarity	NPC179950
0.6375	Remote Similarity	NPC88789
0.6375	Remote Similarity	NPC491374
0.6265	Remote Similarity	NPC148710
0.6264	Remote Similarity	NPC470447
0.625	Remote Similarity	NPC19388
0.625	Remote Similarity	NPC240431
0.625	Remote Similarity	NPC55786
0.625	Remote Similarity	NPC473571
0.625	Remote Similarity	NPC110941
0.6173	Remote Similarity	NPC136042
0.6163	Remote Similarity	NPC251417
0.6098	Remote Similarity	NPC186807
0.6098	Remote Similarity	NPC84362
0.6098	Remote Similarity	NPC603655
0.6049	Remote Similarity	NPC58053
0.6024	Remote Similarity	NPC599850
0.6022	Remote Similarity	NPC36138
0.6022	Remote Similarity	NPC470449
0.6022	Remote Similarity	NPC470445
0.6	Remote Similarity	NPC206123
0.6	Remote Similarity	NPC126784
0.6	Remote Similarity	NPC116458
0.6	Remote Similarity	NPC241423
0.6	Remote Similarity	NPC246943
0.6	Remote Similarity	NPC488074
0.5978	Remote Similarity	NPC5319
0.5976	Remote Similarity	NPC8573
0.5976	Remote Similarity	NPC95090
0.5976	Remote Similarity	NPC27408
0.5957	Remote Similarity	NPC470450
0.5952	Remote Similarity	NPC219904
0.5914	Remote Similarity	NPC76831
0.5895	Remote Similarity	NPC470455
0.5875	Remote Similarity	NPC288084
0.5854	Remote Similarity	NPC143851
0.5814	Remote Similarity	NPC605784
0.5789	Remote Similarity	NPC470446
0.5783	Remote Similarity	NPC265530
0.5773	Remote Similarity	NPC470451
0.5773	Remote Similarity	NPC470416
0.5765	Remote Similarity	NPC611303
0.5758	Remote Similarity	NPC277532
0.5698	Remote Similarity	NPC486578
0.5686	Remote Similarity	NPC470713
0.5657	Remote Similarity	NPC470712
0.5652	Remote Similarity	NPC64425
0.5625	Remote Similarity	NPC183036
0.5618	Remote Similarity	NPC473682
0.561	Remote Similarity	NPC67037
0.561	Remote Similarity	NPC255615
0.5591	Remote Similarity	NPC480471
0.5591	Remote Similarity	NPC488076
0.5581	Remote Similarity	NPC168584
0.5556	Remote Similarity	NPC139320
0.5542	Remote Similarity	NPC111929
0.5542	Remote Similarity	NPC320283
0.5542	Remote Similarity	NPC41121
0.5529	Remote Similarity	NPC46420
0.5529	Remote Similarity	NPC27640
0.5517	Remote Similarity	NPC22832
0.5517	Remote Similarity	NPC605067
0.5488	Remote Similarity	NPC34531
0.5479	Remote Similarity	NPC9609
0.5465	Remote Similarity	NPC21100
0.5455	Remote Similarity	NPC223747
0.5455	Remote Similarity	NPC88023
0.5455	Remote Similarity	NPC488075
0.5455	Remote Similarity	NPC309025
0.5444	Remote Similarity	NPC278419
0.5444	Remote Similarity	NPC179198
0.5437	Remote Similarity	NPC295625
0.5435	Remote Similarity	NPC156869
0.5429	Remote Similarity	NPC470720
0.5417	Remote Similarity	NPC266960
0.5405	Remote Similarity	NPC115798
0.5402	Remote Similarity	NPC191306
0.5402	Remote Similarity	NPC175107
0.5402	Remote Similarity	NPC285197
0.5402	Remote Similarity	NPC609451
0.54	Remote Similarity	NPC48984
0.5393	Remote Similarity	NPC170052
0.5393	Remote Similarity	NPC135846
0.5392	Remote Similarity	NPC470716
0.5385	Remote Similarity	NPC480466
0.5385	Remote Similarity	NPC29958
0.5349	Remote Similarity	NPC271692
0.5347	Remote Similarity	NPC470715
0.5341	Remote Similarity	NPC243930
0.5326	Remote Similarity	NPC471748
0.5301	Remote Similarity	NPC34287
0.5294	Remote Similarity	NPC127546
0.5294	Remote Similarity	NPC249281
0.5294	Remote Similarity	NPC57625
0.5294	Remote Similarity	NPC173637
0.5294	Remote Similarity	NPC317489
0.5294	Remote Similarity	NPC223424
0.5294	Remote Similarity	NPC600591
0.5287	Remote Similarity	NPC117260
0.5281	Remote Similarity	NPC607707
0.5275	Remote Similarity	NPC480463
0.5233	Remote Similarity	NPC93337
0.5233	Remote Similarity	NPC158674
0.5222	Remote Similarity	NPC601586
0.5217	Remote Similarity	NPC603300
0.5213	Remote Similarity	NPC131745
0.5208	Remote Similarity	NPC35119
0.5208	Remote Similarity	NPC473327
0.5196	Remote Similarity	NPC164704
0.5189	Remote Similarity	NPC470717
0.5176	Remote Similarity	NPC135599
0.5176	Remote Similarity	NPC73855
0.5176	Remote Similarity	NPC113968
0.5176	Remote Similarity	NPC328940
0.5176	Remote Similarity	NPC277174
0.5176	Remote Similarity	NPC606877
0.5172	Remote Similarity	NPC105025
0.5172	Remote Similarity	NPC45638
0.5172	Remote Similarity	NPC73511
0.5165	Remote Similarity	NPC254855
0.5165	Remote Similarity	NPC94610
0.5161	Remote Similarity	NPC470405
0.5158	Remote Similarity	NPC153755
0.514	Remote Similarity	NPC488079
0.514	Remote Similarity	NPC488078
0.5135	Remote Similarity	NPC110070
0.5135	Remote Similarity	NPC163524
0.5114	Remote Similarity	NPC201292
0.5111	Remote Similarity	NPC209023
0.5111	Remote Similarity	NPC311830
0.5111	Remote Similarity	NPC602805
0.5104	Remote Similarity	NPC483414
0.5098	Remote Similarity	NPC219043
0.5096	Remote Similarity	NPC470718
0.5068	Remote Similarity	NPC472438
0.5063	Remote Similarity	NPC78809
0.5057	Remote Similarity	NPC156457
0.5057	Remote Similarity	NPC277205
0.5057	Remote Similarity	NPC37919
0.5057	Remote Similarity	NPC323593
0.5057	Remote Similarity	NPC203500
0.5056	Remote Similarity	NPC479401
0.5055	Remote Similarity	NPC469931
0.5054	Remote Similarity	NPC609888
0.5052	Remote Similarity	NPC32641
0.5052	Remote Similarity	NPC256188
0.5052	Remote Similarity	NPC606657
0.5047	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 NPC551296 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4776
0.1-0.2	4267
0.2-0.3	91
0.3-0.4	8
0.4-0.5	7
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
0.5978	Remote Similarity	NPD7804	Clinical (unspecified phase)

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