NPASS Compound

Natural Product: NPC541958

Natural Product ID	NPC541958
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-dimethoxyphenyl)-5-hydroxy-7-[(2~{S},3~{S},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(3,4-dimethoxyphenyl)-5-hydroxy-7-[(2~{S},3~{S},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[(2~{S},3~{R},4~{S},5~{S},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 80 84 0 0 0 0 0 0 0 0999 V2000 -2.5094 6.9515 0.1423 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3169 5.8468 0.4525 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7899 4.5587 0.3333 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4968 4.3834 -0.0830 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0188 3.1051 -0.1878 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7671 1.9619 0.1037 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1061 0.6704 -0.0032 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7475 -0.5319 -0.0841 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1031 -0.6702 -0.0760 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0177 -0.5880 -1.1340 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2466 -0.2680 -0.6729 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8981 -1.1922 0.0559 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2311 -0.7304 1.4946 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8709 -1.7960 2.1409 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1935 -2.5064 0.1624 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0609 -3.4960 0.6613 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7938 -2.9524 -1.2314 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0582 -4.1181 -1.1365 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0115 -1.8933 -1.9259 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7449 -1.5918 -3.1125 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9263 -1.6790 -0.1819 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4560 -2.8017 -0.2507 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4402 -1.5462 -0.1953 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2728 -2.6398 -0.2903 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6937 -3.9017 -0.3743 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6369 -2.4721 -0.3004 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2470 -1.2117 -0.2167 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6043 -1.0889 -0.2291 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3603 0.0762 -0.1537 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1520 0.2932 -1.2753 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2732 -0.4772 -1.3750 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0536 -1.8874 -1.8401 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3162 -2.5066 -1.8753 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1317 -0.4839 -0.1287 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4626 -0.1964 -0.3906 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5553 0.6178 0.7703 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3484 0.7872 1.9099 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1671 0.1378 1.1335 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3294 -1.1567 1.6792 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4103 -0.1314 -0.1229 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0167 -0.2996 -0.1125 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2375 0.7152 -0.0234 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0579 2.1594 0.5205 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5694 3.4444 0.6347 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8585 3.6909 1.0458 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7997 2.7243 1.3898 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0096 7.9136 0.3445 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1519 6.9346 -0.9217 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5989 6.9432 0.7842 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8923 5.2414 -0.3156 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0167 3.0141 -0.5250 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6615 0.2262 -1.8493 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9198 -1.4235 -0.4187 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9561 0.1091 1.4283 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3203 -0.4963 2.0444 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6609 -1.7105 3.1241 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2980 -2.4144 0.8013 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7280 -4.3846 0.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7449 -3.2252 -1.7435 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6832 -4.3426 -2.0439 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0101 -2.1494 -2.2571 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5506 -0.6512 -3.4073 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5331 -4.3157 -1.2975 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2957 -3.3176 -0.3744 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6798 0.9470 -0.1041 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9155 0.0161 -2.1685 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6804 -1.9114 -2.8969 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4098 -2.4717 -1.1519 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2621 -3.4386 -1.5570 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0089 -1.4617 0.3841 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8362 0.3651 0.3306 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5099 1.5299 0.1507 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0026 0.3377 2.7111 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7520 0.8340 1.8667 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4541 -1.5571 1.9029 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7296 0.8844 -0.0524 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7009 1.3464 0.8052 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4229 2.0516 2.1637 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7580 3.1667 1.7588 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0775 2.1016 0.4970 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 2 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 27 40 1 0 40 41 2 0 41 42 1 0 6 43 1 0 43 44 2 0 44 45 1 0 45 46 1 0 44 3 1 0 42 7 1 0 19 10 1 0 41 23 1 0 38 29 1 0 1 47 1 0 1 48 1 0 1 49 1 0 4 50 1 0 5 51 1 0 10 52 1 6 12 53 1 6 13 54 1 0 13 55 1 0 14 56 1 0 15 57 1 1 16 58 1 0 17 59 1 6 18 60 1 0 19 61 1 6 20 62 1 0 25 63 1 0 26 64 1 0 29 65 1 1 31 66 1 6 32 67 1 0 32 68 1 0 33 69 1 0 34 70 1 1 35 71 1 0 36 72 1 6 37 73 1 0 38 74 1 1 39 75 1 0 40 76 1 0 43 77 1 0 46 78 1 0 46 79 1 0 46 80 1 0 M END

Standard InCHIKey	OTKMBDUQIZDZPW-AJDNUPHJSA-N
Standard InCHI	InChI=1S/C29H34O17/c1-40-13-4-3-10(5-14(13)41-2)26-27(46-29-25(39)23(37)20(34)17(9-31)45-29)21(35)18-12(32)6-11(7-15(18)43-26)42-28-24(38)22(36)19(33)16(8-30)44-28/h3-7,16-17,19-20,22-25,28-34,36-39H,8-9H2,1-2H3/t16-,17-,19-,20-,22+,23+,24+,25-,28-,29+/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=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O)C=C3O2)C=C1OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	654.18	Volume:	595.7 ? Van der Waals volume.
Dense:	1.098	LogP:	0.307 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.11 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.543 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	267.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.116	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.689	Fsp³:	0.483
MCE-18:	121.279 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.657	Fluc inhibitor:	0.296 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.858 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.635 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.096	Promiscuous compounds:	0.46

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.445	MDCK Permeability:	-5.262
Pgp-inhibitor:	0.0	Pgp-substrate:	0.631
PAMPA:	0.998 ? 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):	1.0
20% Bioavailability (F20%):	0.161	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.006
Plasma Protein Binding (PPB):	79.719%	Volume Distribution (VD):	-0.149
Fu:	18.712% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.603
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	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:	0.095
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.17
HLM stability:	0.028 ? 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):

1.729

Half-life (T1/2):

5.202

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.016
Human Hepatotoxicity (H-HT):	0.811	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.987	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	1.0
Carcinogencity:	0.197	Eye Corrosion:	0.0
Eye Irritation:	0.014	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.988
Hematotoxicity:	0.662	Drug-induced Nephrotoxicity:	0.933
Genotoxicity:	0.695	RPMI-8226 Immunitoxicity:	0.212
A549 Cytotoxicity:	0.77	Hek293 Cytotoxicity:	0.373
BCF:	0.343 ? 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:	2.89 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.539 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.607 ? 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
NPO53406	Calamintha grandiflora	Genus	Lamiaceae	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 NPC541958 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	22088
0.1-0.2	23882
0.2-0.3	2513
0.3-0.4	824
0.4-0.5	335
0.5-0.6	115
0.6-0.7	74
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8356	Intermediate Similarity	NPC289667
0.7821	Intermediate Similarity	NPC243930
0.7763	Intermediate Similarity	NPC297987
0.7763	Intermediate Similarity	NPC136042
0.7662	Intermediate Similarity	NPC84362
0.7439	Intermediate Similarity	NPC251417
0.7284	Intermediate Similarity	NPC116458
0.7284	Intermediate Similarity	NPC246943
0.7284	Intermediate Similarity	NPC605784
0.7284	Intermediate Similarity	NPC607707
0.7037	Intermediate Similarity	NPC611303
0.6914	Remote Similarity	NPC472459
0.6875	Remote Similarity	NPC95090
0.6875	Remote Similarity	NPC27408
0.6818	Remote Similarity	NPC64425
0.6747	Remote Similarity	NPC22832
0.6747	Remote Similarity	NPC486578
0.6667	Remote Similarity	NPC64305
0.6627	Remote Similarity	NPC285197
0.6627	Remote Similarity	NPC488071
0.6588	Remote Similarity	NPC488072
0.6585	Remote Similarity	NPC46420
0.6585	Remote Similarity	NPC24043
0.6585	Remote Similarity	NPC271692
0.6548	Remote Similarity	NPC120099
0.6548	Remote Similarity	NPC21666
0.6543	Remote Similarity	NPC249281
0.6528	Remote Similarity	NPC236769
0.6463	Remote Similarity	NPC277205
0.6463	Remote Similarity	NPC158674
0.6463	Remote Similarity	NPC37919
0.6395	Remote Similarity	NPC203050
0.6395	Remote Similarity	NPC225434
0.6327	Remote Similarity	NPC277532
0.631	Remote Similarity	NPC325555
0.631	Remote Similarity	NPC226304
0.6304	Remote Similarity	NPC35119
0.63	Remote Similarity	NPC295625
0.6279	Remote Similarity	NPC311830
0.6275	Remote Similarity	NPC470720
0.6265	Remote Similarity	NPC323593
0.6265	Remote Similarity	NPC203500
0.6265	Remote Similarity	NPC189142
0.6265	Remote Similarity	NPC77660
0.6263	Remote Similarity	NPC470716
0.6235	Remote Similarity	NPC60735
0.6235	Remote Similarity	NPC26230
0.6235	Remote Similarity	NPC609451
0.6224	Remote Similarity	NPC470715
0.6224	Remote Similarity	NPC164704
0.6207	Remote Similarity	NPC601586
0.619	Remote Similarity	NPC603655
0.6176	Remote Similarity	NPC470719
0.6176	Remote Similarity	NPC470717
0.6163	Remote Similarity	NPC101026
0.6163	Remote Similarity	NPC488077
0.6163	Remote Similarity	NPC609478
0.6146	Remote Similarity	NPC14187
0.6145	Remote Similarity	NPC261866
0.6145	Remote Similarity	NPC39360
0.6145	Remote Similarity	NPC77672
0.6145	Remote Similarity	NPC133671
0.6145	Remote Similarity	NPC135391
0.6145	Remote Similarity	NPC29763
0.6145	Remote Similarity	NPC78263
0.6145	Remote Similarity	NPC210003
0.6145	Remote Similarity	NPC250069
0.6129	Remote Similarity	NPC32641
0.6129	Remote Similarity	NPC256188
0.6129	Remote Similarity	NPC606657
0.6122	Remote Similarity	NPC48984
0.6118	Remote Similarity	NPC42773
0.6118	Remote Similarity	NPC182045
0.6118	Remote Similarity	NPC45522
0.6071	Remote Similarity	NPC145038
0.6071	Remote Similarity	NPC56077
0.6071	Remote Similarity	NPC281131
0.6071	Remote Similarity	NPC253662
0.6071	Remote Similarity	NPC179950
0.6071	Remote Similarity	NPC88789
0.6071	Remote Similarity	NPC491374
0.6023	Remote Similarity	NPC276377
0.6	Remote Similarity	NPC480466
0.6	Remote Similarity	NPC488080
0.6	Remote Similarity	NPC169977
0.5977	Remote Similarity	NPC601144
0.5952	Remote Similarity	NPC19388
0.5952	Remote Similarity	NPC58053
0.5952	Remote Similarity	NPC240431
0.5952	Remote Similarity	NPC55786
0.593	Remote Similarity	NPC599850
0.5914	Remote Similarity	NPC240306
0.5909	Remote Similarity	NPC88023
0.5909	Remote Similarity	NPC309025
0.59	Remote Similarity	NPC480441
0.59	Remote Similarity	NPC25523
0.5889	Remote Similarity	NPC480463
0.587	Remote Similarity	NPC150164
0.5862	Remote Similarity	NPC307938
0.5814	Remote Similarity	NPC186807
0.5814	Remote Similarity	NPC181712
0.5814	Remote Similarity	NPC73511
0.5795	Remote Similarity	NPC148710
0.573	Remote Similarity	NPC206123
0.5729	Remote Similarity	NPC5319
0.5729	Remote Similarity	NPC486577
0.5698	Remote Similarity	NPC234739
0.5696	Remote Similarity	NPC99671
0.5638	Remote Similarity	NPC186816
0.5632	Remote Similarity	NPC27640
0.5625	Remote Similarity	NPC72016
0.5618	Remote Similarity	NPC284960
0.5618	Remote Similarity	NPC605067
0.56	Remote Similarity	NPC121703
0.5568	Remote Similarity	NPC117260
0.5517	Remote Similarity	NPC8573
0.5517	Remote Similarity	NPC197896
0.5517	Remote Similarity	NPC313163
0.5506	Remote Similarity	NPC219904
0.549	Remote Similarity	NPC477895
0.5488	Remote Similarity	NPC191154
0.5455	Remote Similarity	NPC22195
0.5455	Remote Similarity	NPC21190
0.5455	Remote Similarity	NPC45638
0.5426	Remote Similarity	NPC275454
0.5422	Remote Similarity	NPC134819
0.5412	Remote Similarity	NPC288084
0.5402	Remote Similarity	NPC238376
0.54	Remote Similarity	NPC135358
0.5393	Remote Similarity	NPC27942
0.5393	Remote Similarity	NPC60966
0.5393	Remote Similarity	NPC201292
0.5385	Remote Similarity	NPC223747
0.5376	Remote Similarity	NPC473682
0.537	Remote Similarity	NPC488079
0.5354	Remote Similarity	NPC76831
0.5351	Remote Similarity	NPC223860
0.5349	Remote Similarity	NPC67037
0.5349	Remote Similarity	NPC255615
0.5341	Remote Similarity	NPC93337
0.5333	Remote Similarity	NPC168584
0.5333	Remote Similarity	NPC175107
0.5333	Remote Similarity	NPC262094
0.5333	Remote Similarity	NPC80140
0.5325	Remote Similarity	NPC176300
0.5281	Remote Similarity	NPC105025
0.5269	Remote Similarity	NPC265115
0.5263	Remote Similarity	NPC76376
0.5258	Remote Similarity	NPC488073
0.5256	Remote Similarity	NPC206604
0.5233	Remote Similarity	NPC34531
0.5229	Remote Similarity	NPC488078
0.5227	Remote Similarity	NPC110349
0.5227	Remote Similarity	NPC44558
0.5227	Remote Similarity	NPC108831
0.5227	Remote Similarity	NPC19709
0.5227	Remote Similarity	NPC143851
0.5227	Remote Similarity	NPC182634
0.5222	Remote Similarity	NPC59534
0.5222	Remote Similarity	NPC21100
0.5217	Remote Similarity	NPC602805
0.5213	Remote Similarity	NPC8856
0.5208	Remote Similarity	NPC156869
0.5204	Remote Similarity	NPC483414
0.52	Remote Similarity	NPC475382
0.5185	Remote Similarity	NPC470713
0.5169	Remote Similarity	NPC168822
0.5169	Remote Similarity	NPC265530
0.5161	Remote Similarity	NPC190003
0.5161	Remote Similarity	NPC267254
0.5161	Remote Similarity	NPC355481
0.5158	Remote Similarity	NPC29958
0.5158	Remote Similarity	NPC139320
0.5155	Remote Similarity	NPC131745
0.5143	Remote Similarity	NPC470712
0.5128	Remote Similarity	NPC270620
0.5128	Remote Similarity	NPC166753
0.5114	Remote Similarity	NPC111929
0.5114	Remote Similarity	NPC320283
0.5114	Remote Similarity	NPC473043
0.5114	Remote Similarity	NPC331652
0.5114	Remote Similarity	NPC41121
0.5111	Remote Similarity	NPC245014
0.5111	Remote Similarity	NPC305811
0.5111	Remote Similarity	NPC349108
0.5111	Remote Similarity	NPC610763
0.5109	Remote Similarity	NPC80188
0.5104	Remote Similarity	NPC471748
0.5102	Remote Similarity	NPC46202
0.5102	Remote Similarity	NPC153755
0.51	Remote Similarity	NPC142142
0.5063	Remote Similarity	NPC195202
0.5063	Remote Similarity	NPC603596
0.5056	Remote Similarity	NPC210042
0.5056	Remote Similarity	NPC127546
0.5056	Remote Similarity	NPC57625
0.5056	Remote Similarity	NPC173637
0.5056	Remote Similarity	NPC317489
0.5056	Remote Similarity	NPC223424
0.5056	Remote Similarity	NPC600591

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC541958 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5261
0.1-0.2	3802
0.2-0.3	71
0.3-0.4	10
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	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6421	Remote Similarity	NPD7808	Phase 3
0.5729	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5354	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