NPASS Compound

Natural Product: NPC553311

Natural Product ID	NPC553311
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2~{R},3~{R},4~{R},5~{R},6~{R})-4,5-dihydroxy-2-methyl-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-methoxyphenyl)-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-yl]methoxy]tetrahydropyran-3-yl] acetate
IUPAC Name	[(2~{R},3~{R},4~{R},5~{R},6~{R})-4,5-dihydroxy-2-methyl-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-methoxyphenyl)-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-yl]methoxy]tetrahydropyran-3-yl] acetate
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 79 83 0 0 0 0 0 0 0 0999 V2000 -10.2008 -3.2646 2.5546 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6726 -2.1015 1.8884 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7578 -1.2722 1.2440 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1561 -0.1345 0.5836 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2516 0.6972 -0.0611 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9207 0.3851 -0.0454 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9562 1.2377 -0.7108 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3094 2.3729 -1.3740 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3113 3.1393 -1.9897 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6436 4.1687 -2.5892 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0021 2.7299 -1.9112 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9795 3.4463 -2.4990 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3342 4.5997 -3.1735 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6838 3.0109 -2.4024 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3801 1.8303 -1.7041 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0642 1.4181 -1.6247 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5230 0.3042 -1.0007 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3717 0.5851 -0.0124 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3977 -0.2388 0.2561 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6779 0.6009 0.2023 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7960 -0.1841 0.4695 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9669 0.5489 0.4347 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8629 0.1893 -0.5192 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9659 -0.5225 -0.1462 C 0 0 2 0 0 0 0 0 0 0 0 0 6.6573 -1.9525 0.2419 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.1886 0.9064 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6149 -0.6714 1.6295 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9623 -0.7311 1.6568 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6782 -1.7123 2.4864 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5791 0.0736 0.9552 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9433 1.1151 1.7248 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5048 1.4230 2.9585 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5121 0.6248 1.8414 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8285 1.5665 2.6172 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5193 -1.5335 -0.4287 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6940 -1.5931 -1.2202 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3952 -1.8921 -1.3643 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7275 -2.9027 -2.2374 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0051 -0.6167 -2.0902 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0766 -0.9265 -2.9180 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4029 1.1446 -1.1356 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7086 1.5762 -1.2284 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6879 0.8986 -0.6707 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5078 -0.7507 0.6117 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4151 -1.5704 1.2492 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4738 -2.9402 3.3078 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6388 -3.8431 1.7757 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0249 -3.8806 2.9357 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2152 0.0940 0.5833 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6785 1.5630 -0.5470 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3379 2.6909 -1.4339 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1964 4.6227 -4.1788 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8756 3.5624 -2.8576 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3407 -0.2823 -0.5239 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3173 -0.4653 1.3707 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7726 1.1267 -0.7714 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6564 1.3983 0.9755 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6656 1.6144 0.1920 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5857 -0.6196 -1.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4759 -2.3765 0.8620 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6303 -2.6098 -0.6747 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6545 -2.0773 0.6985 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5020 0.8370 0.3376 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7333 -1.4227 2.6712 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2124 -1.7979 3.5114 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7018 -2.7235 2.0016 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8389 2.0983 1.2102 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2596 2.0624 2.7937 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4047 -0.3354 2.3214 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1165 1.4032 3.5633 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6254 -2.3860 0.2755 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4819 -1.2048 -2.1060 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5023 -2.2082 -0.7920 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7971 -2.5419 -3.1561 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7898 -0.1855 -2.6985 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7476 -1.2186 -3.8200 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2268 0.2201 -0.5806 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4451 -1.0244 0.6400 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0269 -2.4542 1.7512 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 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 2 0 26 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 19 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 15 41 1 0 41 42 2 0 42 43 1 0 6 44 1 0 44 45 2 0 45 3 1 0 43 7 1 0 42 11 1 0 39 17 1 0 33 22 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 5 50 1 0 8 51 1 0 13 52 1 0 14 53 1 0 17 54 1 1 19 55 1 1 20 56 1 0 20 57 1 0 22 58 1 6 24 59 1 6 25 60 1 0 25 61 1 0 25 62 1 0 26 63 1 6 29 64 1 0 29 65 1 0 29 66 1 0 31 67 1 6 32 68 1 0 33 69 1 1 34 70 1 0 35 71 1 1 36 72 1 0 37 73 1 1 38 74 1 0 39 75 1 6 40 76 1 0 41 77 1 0 44 78 1 0 45 79 1 0 M END

Standard InCHIKey	QZOBONFUOPKXNI-MIPSZYPSSA-N
Standard InCHI	InChI=1S/C30H34O15/c1-12-28(42-13(2)31)25(36)27(38)29(41-12)40-11-21-23(34)24(35)26(37)30(45-21)43-16-8-17(32)22-18(33)10-19(44-20(22)9-16)14-4-6-15(39-3)7-5-14/h4-10,12,21,23-30,32,34-38H,11H2,1-3H3/t12-,21-,23+,24+,25-,26-,27-,28+,29-,30-/m1/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](C)[C@H](OC(C)=O)[C@H](O)[C@H]5O)[C@H](O)[C@H](O)[C@H]4O)C=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	634.19	Volume:	592.779 ? Van der Waals volume.
Dense:	1.07	LogP:	1.405 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.785 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.121 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	31.0
TPSA:	224.04 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	6.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.176	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.669	Fsp³:	0.467
MCE-18:	117.455 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.623	Fluc inhibitor:	0.318 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.902 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.403 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.062	Promiscuous compounds:	0.237

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.148	MDCK Permeability:	-5.225
Pgp-inhibitor:	0.001	Pgp-substrate:	0.911
PAMPA:	0.996 ? 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):	0.996
20% Bioavailability (F20%):	0.971	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.821
Plasma Protein Binding (PPB):	85.946%	Volume Distribution (VD):	-0.168
Fu:	14.4% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.998
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.282
BSEP inhibitor:	0.002

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:	0.004
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.37 ? 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):

1.361

Half-life (T1/2):

2.305

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.083
Human Hepatotoxicity (H-HT):	0.579	Drug-induced Liver Injury (DILI):	0.998
AMES Toxicity:	0.995	Rat Oral Acute Toxicity:	0.062
Maximum Recommended Daily Dose:	0.059	Skin Sensitization:	0.999
Carcinogencity:	0.405	Eye Corrosion:	0.0
Eye Irritation:	0.264	Respiratory Toxicity:	0.065
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.795
Hematotoxicity:	0.763	Drug-induced Nephrotoxicity:	0.784
Genotoxicity:	0.988	RPMI-8226 Immunitoxicity:	0.286
A549 Cytotoxicity:	0.95	Hek293 Cytotoxicity:	0.798
BCF:	0.408 ? 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:	3.172 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.678 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.874 ? 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
NPO58478	Thalictrum aquilegifolium	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO58982	Thalictrum przewalskii	Species	Ranunculaceae	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 NPC553311 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	16086
0.1-0.2	29651
0.2-0.3	3134
0.3-0.4	661
0.4-0.5	236
0.5-0.6	50
0.6-0.7	27
0.7-0.8	1
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC488089
0.8256	Intermediate Similarity	NPC22062
0.8256	Intermediate Similarity	NPC473634
0.8256	Intermediate Similarity	NPC138811
0.8105	Intermediate Similarity	NPC488087
0.7917	Intermediate Similarity	NPC488083
0.7889	Intermediate Similarity	NPC473623
0.7475	Intermediate Similarity	NPC488088
0.7312	Intermediate Similarity	NPC209296
0.7143	Intermediate Similarity	NPC44931
0.7097	Intermediate Similarity	NPC46202
0.7083	Intermediate Similarity	NPC101636
0.6907	Remote Similarity	NPC298171
0.6897	Remote Similarity	NPC181712
0.6882	Remote Similarity	NPC210073
0.6869	Remote Similarity	NPC11468
0.6809	Remote Similarity	NPC204693
0.6782	Remote Similarity	NPC95090
0.6782	Remote Similarity	NPC27408
0.663	Remote Similarity	NPC211594
0.6571	Remote Similarity	NPC488086
0.6429	Remote Similarity	NPC483707
0.6364	Remote Similarity	NPC262222
0.6346	Remote Similarity	NPC473644
0.6327	Remote Similarity	NPC65711
0.6286	Remote Similarity	NPC311850
0.6262	Remote Similarity	NPC68592
0.6237	Remote Similarity	NPC220169
0.6224	Remote Similarity	NPC64051
0.6146	Remote Similarity	NPC295613
0.6146	Remote Similarity	NPC473657
0.6139	Remote Similarity	NPC479765
0.6129	Remote Similarity	NPC80188
0.61	Remote Similarity	NPC229409
0.6087	Remote Similarity	NPC27942
0.604	Remote Similarity	NPC479766
0.604	Remote Similarity	NPC270675
0.604	Remote Similarity	NPC195685
0.6	Remote Similarity	NPC331652
0.598	Remote Similarity	NPC475382
0.5957	Remote Similarity	NPC22832
0.5957	Remote Similarity	NPC243930
0.5943	Remote Similarity	NPC472993
0.5938	Remote Similarity	NPC172807
0.5922	Remote Similarity	NPC470449
0.5895	Remote Similarity	NPC607707
0.5865	Remote Similarity	NPC470446
0.5865	Remote Similarity	NPC472994
0.5833	Remote Similarity	NPC190003
0.5761	Remote Similarity	NPC39360
0.5761	Remote Similarity	NPC19709
0.5761	Remote Similarity	NPC29763
0.5761	Remote Similarity	NPC210003
0.5758	Remote Similarity	NPC67105
0.5743	Remote Similarity	NPC475366
0.5714	Remote Similarity	NPC254540
0.57	Remote Similarity	NPC473512
0.57	Remote Similarity	NPC129827
0.5652	Remote Similarity	NPC473043
0.5644	Remote Similarity	NPC186816
0.5625	Remote Similarity	NPC298666
0.5625	Remote Similarity	NPC198199
0.5625	Remote Similarity	NPC608742
0.5614	Remote Similarity	NPC120952
0.56	Remote Similarity	NPC227508
0.5567	Remote Similarity	NPC311830
0.5566	Remote Similarity	NPC135358
0.5556	Remote Similarity	NPC29353
0.5532	Remote Similarity	NPC189142
0.5532	Remote Similarity	NPC77660
0.5474	Remote Similarity	NPC186807
0.5446	Remote Similarity	NPC275454
0.5437	Remote Similarity	NPC284277
0.5437	Remote Similarity	NPC475497
0.5426	Remote Similarity	NPC58053
0.5426	Remote Similarity	NPC261866
0.5392	Remote Similarity	NPC303913
0.5306	Remote Similarity	NPC601144
0.5278	Remote Similarity	NPC179862
0.5243	Remote Similarity	NPC479405
0.5234	Remote Similarity	NPC477629
0.5196	Remote Similarity	NPC187379
0.5192	Remote Similarity	NPC479404
0.5146	Remote Similarity	NPC15358
0.5104	Remote Similarity	NPC143851
0.5096	Remote Similarity	NPC65003
0.5094	Remote Similarity	NPC479403
0.5051	Remote Similarity	NPC611303
0.5047	Remote Similarity	NPC606657

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC553311 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4749
0.1-0.2	4322
0.2-0.3	68
0.3-0.4	6
0.4-0.5	1
0.5-0.6	3
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
0.7312	Intermediate Similarity	NPD7054	Phase 4
0.5607	Remote Similarity	NPD7472	Pre-clinical
0.5321	Remote Similarity	NPD7808	Phase 3
0.5234	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