NPASS Compound

Natural Product: NPC597499

Natural Product ID	NPC597499
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-2-(4-methoxyphenyl)-7-[(2~{S},3~{R},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})-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-(4-methoxyphenyl)-7-[(2~{S},3~{R},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})-3,4,5-trihydroxytetrahydropyran-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 72 76 0 0 0 0 0 0 0 0999 V2000 -3.3392 6.0143 -1.1193 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0066 4.8107 -1.4221 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3967 3.5804 -1.2233 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0372 2.3880 -1.5155 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4046 1.1875 -1.3068 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1313 1.1610 -0.8050 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3995 -0.0853 -0.4968 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9842 -1.3090 -0.3888 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3146 -1.5940 -0.5260 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2037 -1.6630 0.5789 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4061 -3.0445 0.9114 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3780 -3.5072 0.0499 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7246 -3.1674 0.7025 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7008 -3.3774 -0.2688 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6528 -1.7100 1.0874 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8306 -1.1095 0.6506 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5091 -0.9932 0.3775 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5333 0.3111 0.9296 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1207 -2.3820 -0.0945 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5523 -3.5558 0.0247 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2342 -2.1854 0.0747 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1068 -3.2125 0.3649 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6238 -4.5059 0.4951 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4607 -3.0198 0.5361 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9596 -1.7404 0.4105 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2881 -1.5419 0.5771 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0507 -0.3931 0.5126 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0246 -0.4182 -0.5004 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3461 0.9300 -0.7644 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2297 1.0509 -1.9642 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4093 0.3441 -1.7316 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 1.4940 0.4265 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3213 2.8477 0.2247 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2650 1.3514 1.6922 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0598 1.7034 2.7805 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8049 -0.0919 1.7909 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0315 -0.2119 2.9226 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1024 -0.7090 0.1219 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7395 -0.8991 -0.0511 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0806 0.0589 -0.3230 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5109 2.3586 -0.5214 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1070 3.5588 -0.7165 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1114 6.0343 -0.0289 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9453 6.8778 -1.4217 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3573 5.9885 -1.6460 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0551 2.4554 -1.9140 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9143 0.2751 -1.5704 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6783 -1.2086 1.4432 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3591 -2.8984 -0.8935 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3018 -4.5786 -0.1934 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9113 -3.8325 1.5660 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3362 -3.0334 -1.1161 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5871 -1.6174 2.1699 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5251 -1.7694 0.4039 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7440 -0.8911 -0.6811 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3674 0.7661 0.7354 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4311 -5.1090 -0.2964 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1263 -3.8694 0.7676 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4094 0.4777 0.2822 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4002 1.5151 -0.9217 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7034 0.6981 -2.8877 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4969 2.1026 -2.1107 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1661 -0.6171 -1.6792 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0403 0.9801 0.5664 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7399 3.2545 1.0224 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3951 2.0158 1.6356 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4696 2.0000 3.5210 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7257 -0.7139 1.8448 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9265 -1.1931 3.0946 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4308 0.3366 0.0075 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4760 2.3689 -0.1126 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5836 4.4619 -0.4807 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 13 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 8 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 22 23 1 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 29 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 25 38 1 0 38 39 2 0 39 40 1 0 6 41 1 0 41 42 2 0 42 3 1 0 40 7 1 0 17 10 1 0 39 21 1 0 36 27 1 0 1 43 1 0 1 44 1 0 1 45 1 0 4 46 1 0 5 47 1 0 10 48 1 1 12 49 1 0 12 50 1 0 13 51 1 1 14 52 1 0 15 53 1 1 16 54 1 0 17 55 1 6 18 56 1 0 23 57 1 0 24 58 1 0 27 59 1 6 29 60 1 6 30 61 1 0 30 62 1 0 31 63 1 0 32 64 1 1 33 65 1 0 34 66 1 6 35 67 1 0 36 68 1 1 37 69 1 0 38 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	GNWBRGFDRGVFBA-DALCCTHOSA-N
Standard InCHI	InChI=1S/C27H30O15/c1-37-11-4-2-10(3-5-11)24-25(42-26-22(35)18(31)14(30)9-38-26)20(33)17-13(29)6-12(7-15(17)40-24)39-27-23(36)21(34)19(32)16(8-28)41-27/h2-7,14,16,18-19,21-23,26-32,34-36H,8-9H2,1H3/t14-,16+,18-,19+,21-,22+,23+,26-,27+/m0/s1
SMILES	COC1=CC=C(C2=C(O[C@@H]3OC[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=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	1.296 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.725 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.546 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
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:	0.15	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.558	Fsp³:	0.444
MCE-18:	115.923 ? 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:	0.628	Fluc inhibitor:	0.296 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.923 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.649 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.053	Promiscuous compounds:	0.418

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.498	MDCK Permeability:	-5.149
Pgp-inhibitor:	0.0	Pgp-substrate:	0.77
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):	0.967
20% Bioavailability (F20%):	0.039	30% Bioavailability (F30%):	0.993
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.015
Plasma Protein Binding (PPB):	79.413%	Volume Distribution (VD):	-0.133
Fu:	19.248% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.56
BSEP inhibitor:	0.001

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:	0.031
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.949
HLM stability:	0.351 ? 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):

1.71

Half-life (T1/2):

3.957

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.053
Human Hepatotoxicity (H-HT):	0.832	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.976	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.007	Skin Sensitization:	1.0
Carcinogencity:	0.201	Eye Corrosion:	0.0
Eye Irritation:	0.058	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.96
Hematotoxicity:	0.346	Drug-induced Nephrotoxicity:	0.893
Genotoxicity:	0.845	RPMI-8226 Immunitoxicity:	0.158
A549 Cytotoxicity:	0.577	Hek293 Cytotoxicity:	0.376
BCF:	0.392 ? 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:	3.123 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.664 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.802 ? 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
NPO47091	Asplenium bulbiferum	Species	Aspleniaceae	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 NPC597499 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	18354
0.1-0.2	27221
0.2-0.3	2985
0.3-0.4	769
0.4-0.5	331
0.5-0.6	129
0.6-0.7	46
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	Natural Product ID
0.8514	High Similarity	NPC289667
0.7692	Intermediate Similarity	NPC297987
0.7468	Intermediate Similarity	NPC136042
0.7375	Intermediate Similarity	NPC84362
0.7349	Intermediate Similarity	NPC276377
0.7284	Intermediate Similarity	NPC472459
0.7229	Intermediate Similarity	NPC116458
0.7229	Intermediate Similarity	NPC246943
0.7176	Intermediate Similarity	NPC251417
0.7037	Intermediate Similarity	NPC95090
0.7037	Intermediate Similarity	NPC27408
0.7024	Intermediate Similarity	NPC605784
0.6966	Remote Similarity	NPC64425
0.6829	Remote Similarity	NPC64305
0.6804	Remote Similarity	NPC277532
0.6786	Remote Similarity	NPC611303
0.6632	Remote Similarity	NPC14187
0.6548	Remote Similarity	NPC46420
0.6512	Remote Similarity	NPC22832
0.6506	Remote Similarity	NPC249281
0.6489	Remote Similarity	NPC76831
0.6436	Remote Similarity	NPC295625
0.64	Remote Similarity	NPC470716
0.6374	Remote Similarity	NPC150164
0.6364	Remote Similarity	NPC470715
0.6353	Remote Similarity	NPC24043
0.6353	Remote Similarity	NPC271692
0.6322	Remote Similarity	NPC243930
0.6322	Remote Similarity	NPC120099
0.6322	Remote Similarity	NPC486578
0.6277	Remote Similarity	NPC35119
0.625	Remote Similarity	NPC470720
0.6235	Remote Similarity	NPC158674
0.6207	Remote Similarity	NPC285197
0.6207	Remote Similarity	NPC488071
0.62	Remote Similarity	NPC25523
0.62	Remote Similarity	NPC164704
0.6154	Remote Similarity	NPC470717
0.6136	Remote Similarity	NPC21666
0.6118	Remote Similarity	NPC77672
0.6118	Remote Similarity	NPC133671
0.6118	Remote Similarity	NPC135391
0.6118	Remote Similarity	NPC78263
0.6118	Remote Similarity	NPC250069
0.6105	Remote Similarity	NPC32641
0.6105	Remote Similarity	NPC256188
0.6105	Remote Similarity	NPC72016
0.6105	Remote Similarity	NPC606657
0.6067	Remote Similarity	NPC607707
0.6047	Remote Similarity	NPC277205
0.6047	Remote Similarity	NPC37919
0.6047	Remote Similarity	NPC189142
0.6047	Remote Similarity	NPC77660
0.6042	Remote Similarity	NPC5319
0.604	Remote Similarity	NPC480441
0.6023	Remote Similarity	NPC60735
0.6023	Remote Similarity	NPC26230
0.6	Remote Similarity	NPC470719
0.5977	Remote Similarity	NPC181712
0.5977	Remote Similarity	NPC488080
0.5977	Remote Similarity	NPC169977
0.5957	Remote Similarity	NPC186816
0.5955	Remote Similarity	NPC148710
0.5955	Remote Similarity	NPC609478
0.5941	Remote Similarity	NPC48984
0.593	Remote Similarity	NPC261866
0.593	Remote Similarity	NPC39360
0.593	Remote Similarity	NPC29763
0.593	Remote Similarity	NPC210003
0.5909	Remote Similarity	NPC42773
0.5909	Remote Similarity	NPC45522
0.5909	Remote Similarity	NPC325555
0.5909	Remote Similarity	NPC226304
0.59	Remote Similarity	NPC121703
0.5895	Remote Similarity	NPC240306
0.5889	Remote Similarity	NPC311830
0.5862	Remote Similarity	NPC145038
0.5862	Remote Similarity	NPC56077
0.5862	Remote Similarity	NPC281131
0.5862	Remote Similarity	NPC253662
0.5862	Remote Similarity	NPC179950
0.5862	Remote Similarity	NPC323593
0.5862	Remote Similarity	NPC88789
0.5862	Remote Similarity	NPC203500
0.5862	Remote Similarity	NPC491374
0.5824	Remote Similarity	NPC203050
0.5824	Remote Similarity	NPC488072
0.5824	Remote Similarity	NPC225434
0.5795	Remote Similarity	NPC186807
0.5795	Remote Similarity	NPC73511
0.5747	Remote Similarity	NPC19388
0.5747	Remote Similarity	NPC58053
0.5747	Remote Similarity	NPC240431
0.5747	Remote Similarity	NPC55786
0.5733	Remote Similarity	NPC262094
0.573	Remote Similarity	NPC599850
0.5714	Remote Similarity	NPC486577
0.5682	Remote Similarity	NPC234739
0.5652	Remote Similarity	NPC601586
0.5647	Remote Similarity	NPC54802
0.5647	Remote Similarity	NPC197304
0.5638	Remote Similarity	NPC480466
0.5618	Remote Similarity	NPC603655
0.5614	Remote Similarity	NPC223860
0.5604	Remote Similarity	NPC101026
0.5604	Remote Similarity	NPC488077
0.5604	Remote Similarity	NPC601144
0.5567	Remote Similarity	NPC46202
0.5545	Remote Similarity	NPC135358
0.5532	Remote Similarity	NPC480463
0.5521	Remote Similarity	NPC22062
0.5521	Remote Similarity	NPC473634
0.5521	Remote Similarity	NPC138811
0.5506	Remote Similarity	NPC8573
0.5495	Remote Similarity	NPC307938
0.5481	Remote Similarity	NPC219043
0.5474	Remote Similarity	NPC471079
0.5435	Remote Similarity	NPC80188
0.5417	Remote Similarity	NPC470405
0.5417	Remote Similarity	NPC275454
0.5408	Remote Similarity	NPC488073
0.5402	Remote Similarity	NPC288084
0.5402	Remote Similarity	NPC276222
0.5402	Remote Similarity	NPC274618
0.5402	Remote Similarity	NPC118284
0.5402	Remote Similarity	NPC608147
0.54	Remote Similarity	NPC142142
0.5385	Remote Similarity	NPC60966
0.5376	Remote Similarity	NPC220169
0.5361	Remote Similarity	NPC304741
0.5361	Remote Similarity	NPC156869
0.5347	Remote Similarity	NPC475382
0.5333	Remote Similarity	NPC197896
0.5333	Remote Similarity	NPC313163
0.5326	Remote Similarity	NPC168584
0.5326	Remote Similarity	NPC219904
0.5321	Remote Similarity	NPC470713
0.53	Remote Similarity	NPC473623
0.5294	Remote Similarity	NPC292929
0.5294	Remote Similarity	NPC191154
0.5283	Remote Similarity	NPC470712
0.5275	Remote Similarity	NPC22195
0.5275	Remote Similarity	NPC27640
0.5275	Remote Similarity	NPC21190
0.5269	Remote Similarity	NPC605067
0.5258	Remote Similarity	NPC67326
0.5253	Remote Similarity	NPC488074
0.5248	Remote Similarity	NPC488089
0.5233	Remote Similarity	NPC134819
0.5222	Remote Similarity	NPC143851
0.5217	Remote Similarity	NPC59534
0.5217	Remote Similarity	NPC27942
0.5213	Remote Similarity	NPC206123
0.5208	Remote Similarity	NPC473682
0.5208	Remote Similarity	NPC278419
0.5208	Remote Similarity	NPC179198
0.5169	Remote Similarity	NPC67037
0.5169	Remote Similarity	NPC255615
0.5161	Remote Similarity	NPC175107
0.5161	Remote Similarity	NPC80140
0.5161	Remote Similarity	NPC609451
0.5158	Remote Similarity	NPC190003
0.5155	Remote Similarity	NPC139320
0.5152	Remote Similarity	NPC255157
0.5152	Remote Similarity	NPC259896
0.5152	Remote Similarity	NPC131745
0.5149	Remote Similarity	NPC209296
0.5125	Remote Similarity	NPC153758
0.5111	Remote Similarity	NPC111929
0.5111	Remote Similarity	NPC320283
0.5111	Remote Similarity	NPC41121
0.5109	Remote Similarity	NPC45638
0.5109	Remote Similarity	NPC349108
0.5104	Remote Similarity	NPC265115
0.5093	Remote Similarity	NPC311850
0.5089	Remote Similarity	NPC488078
0.5056	Remote Similarity	NPC34531
0.5055	Remote Similarity	NPC44558
0.5055	Remote Similarity	NPC19709
0.5055	Remote Similarity	NPC238376
0.5054	Remote Similarity	NPC117260
0.5054	Remote Similarity	NPC201292
0.5052	Remote Similarity	NPC8856
0.505	Remote Similarity	NPC483414
0.5046	Remote Similarity	NPC488083
0.5044	Remote Similarity	NPC209550
0.5044	Remote Similarity	NPC138990

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC597499 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4727
0.1-0.2	4318
0.2-0.3	92
0.3-0.4	6
0.4-0.5	3
0.5-0.6	3
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
0.6042	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD7808	Phase 3
0.5657	Remote Similarity	NPD7251	Phase 2
0.5149	Remote Similarity	NPD7054	Phase 4

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