NPASS Compound

Natural Product: NPC594550

Natural Product ID	NPC594550
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{S})-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-6-[[(2~{S},3~{R},4~{S},5~{S})-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chroman-4-one
IUPAC Name	(2~{S})-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-6-[[(2~{S},3~{R},4~{S},5~{S})-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxymethyl]-3,4,5-trihydroxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-methoxyphenyl)chroman-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 73 77 0 0 0 0 0 0 0 0999 V2000 8.9015 0.5268 -2.7402 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8288 1.4062 -2.4383 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1910 1.2346 -1.2173 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1341 2.0531 -0.8478 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5038 1.8752 0.3714 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8986 0.8916 1.2501 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1622 0.7839 2.5163 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4978 -0.3907 3.3649 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8110 -1.6324 2.9249 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3707 -2.7340 3.1646 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5293 -1.5285 2.2400 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8344 -2.6974 1.9646 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3671 -3.9219 2.3419 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6251 -2.5793 1.3168 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0822 -1.3463 0.9334 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1314 -1.3962 0.2965 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7945 -0.2650 -0.1421 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0622 -0.1195 0.4781 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4769 1.1885 0.1204 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5362 1.7447 0.9846 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6924 1.0797 1.1883 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4793 0.8338 0.1478 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8799 -0.5313 0.0505 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7202 -0.4295 -1.0811 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4766 -1.7071 -1.3215 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2700 -1.5324 -2.4347 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6096 0.7497 -0.8243 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9085 0.3852 -0.4972 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9033 1.4275 0.3403 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4510 0.9809 1.5266 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5330 1.4091 -1.3465 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3571 2.1062 -1.7919 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3918 0.0265 -1.9990 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2137 -0.8975 -1.3826 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9603 -0.4048 -1.6623 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1003 0.4292 -2.3416 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8102 -0.2414 1.2312 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0450 -0.2934 1.8874 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7812 0.8398 2.1873 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9321 0.0750 0.9129 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5567 0.2629 -0.3126 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5090 -0.5025 -2.6117 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6899 0.6592 -1.9712 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3047 0.6966 -3.7539 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8315 2.8201 -1.5411 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6769 2.5596 0.5943 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3665 1.7289 3.0967 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5789 -0.5449 3.4139 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1513 -0.2114 4.4251 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3559 -4.1289 3.3454 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0613 -3.4826 1.0898 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2964 0.7055 0.0461 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5140 1.7876 0.4568 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0816 2.0144 2.0100 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7336 2.8004 0.5605 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1897 1.1383 -0.8487 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0276 -0.2556 -1.9430 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0155 -2.0398 -0.4251 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7143 -2.4825 -1.5867 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1570 -1.2408 -2.1579 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5548 1.4524 -1.6730 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0940 0.7785 0.4075 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8527 2.5116 0.2340 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0889 0.1303 1.8398 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3414 2.0066 -1.7467 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5132 2.2722 -2.7625 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5553 0.0734 -3.0774 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6089 -1.5570 -1.9834 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8804 -1.4665 -1.9662 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6586 -0.0504 -2.7799 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4495 0.7202 0.9654 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2884 -0.7173 1.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3824 -0.3944 -0.5744 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 1 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 25 26 1 0 24 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 19 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 15 37 1 0 37 38 2 0 38 39 1 0 6 40 1 0 40 41 2 0 41 3 1 0 39 7 1 0 38 11 1 0 35 17 1 0 29 22 1 0 1 42 1 0 1 43 1 0 1 44 1 0 4 45 1 0 5 46 1 0 7 47 1 1 8 48 1 0 8 49 1 0 13 50 1 0 14 51 1 0 17 52 1 6 19 53 1 1 20 54 1 0 20 55 1 0 22 56 1 6 24 57 1 6 25 58 1 0 25 59 1 0 26 60 1 0 27 61 1 6 28 62 1 0 29 63 1 6 30 64 1 0 31 65 1 1 32 66 1 0 33 67 1 6 34 68 1 0 35 69 1 6 36 70 1 0 37 71 1 0 40 72 1 0 41 73 1 0 M END

Standard InCHIKey	DVGAUVZPQOOYFU-GKPDQTJPSA-N
Standard InCHI	InChI=1S/C27H32O14/c1-36-12-4-2-11(3-5-12)16-8-15(30)20-14(29)6-13(7-17(20)39-16)38-27-25(35)23(33)22(32)19(41-27)10-37-26-24(34)21(31)18(9-28)40-26/h2-7,16,18-19,21-29,31-35H,8-10H2,1H3/t16-,18-,19+,21+,22+,23-,24+,25+,26-,27+/m0/s1
SMILES	COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](CO)[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:	580.18	Volume:	537.374 ? Van der Waals volume.
Dense:	1.08	LogP:	0.874 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.499 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.399 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	29.0
TPSA:	214.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.194	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.582	Fsp³:	0.519
MCE-18:	113.171 ? 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:	0.593	Fluc inhibitor:	0.536 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.098 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.395 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.075	Promiscuous compounds:	0.329

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.625	MDCK Permeability:	-5.203
Pgp-inhibitor:	0.015	Pgp-substrate:	0.253
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):	0.043
20% Bioavailability (F20%):	0.002	30% Bioavailability (F30%):	0.815
50% Bioavailability (F50%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.022
Plasma Protein Binding (PPB):	83.896%	Volume Distribution (VD):	-0.283
Fu:	14.705% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.448
BSEP inhibitor:	0.864

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:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.103
HLM stability:	0.05 ? 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):

2.12

Half-life (T1/2):

3.738

ADMET: Toxicity

hERG Blockers:	0.042	hERG Blockers (10um):	0.194
Human Hepatotoxicity (H-HT):	0.753	Drug-induced Liver Injury (DILI):	0.936
AMES Toxicity:	0.924	Rat Oral Acute Toxicity:	0.054
Maximum Recommended Daily Dose:	0.047	Skin Sensitization:	0.973
Carcinogencity:	0.042	Eye Corrosion:	0.0
Eye Irritation:	0.08	Respiratory Toxicity:	0.044
Drug-induced Neurotoxicity:	0.021	Ototoxicity:	0.991
Hematotoxicity:	0.395	Drug-induced Nephrotoxicity:	0.98
Genotoxicity:	0.7	RPMI-8226 Immunitoxicity:	0.289
A549 Cytotoxicity:	0.334	Hek293 Cytotoxicity:	0.219
BCF:	0.428 ? 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:	3.206 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.083 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.08 ? 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
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s00217-007-0799-1]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2011.01.077]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15620261]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36560643]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39138188]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39527985]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Twig	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21349	Punica granatum	Species	Lythraceae	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 NPC594550 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	16346
0.1-0.2	28257
0.2-0.3	4197
0.3-0.4	915
0.4-0.5	104
0.5-0.6	23
0.6-0.7	7
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	Natural Product ID
0.7838	Intermediate Similarity	NPC219163
0.7711	Intermediate Similarity	NPC293629
0.759	Intermediate Similarity	NPC44328
0.759	Intermediate Similarity	NPC79056
0.7439	Intermediate Similarity	NPC271270
0.7059	Intermediate Similarity	NPC43587
0.6795	Remote Similarity	NPC97052
0.6709	Remote Similarity	NPC39351
0.6506	Remote Similarity	NPC236934
0.6364	Remote Similarity	NPC97285
0.6341	Remote Similarity	NPC29830
0.6098	Remote Similarity	NPC26195
0.6044	Remote Similarity	NPC190450
0.5957	Remote Similarity	NPC67134
0.5638	Remote Similarity	NPC105095
0.5638	Remote Similarity	NPC177731
0.5638	Remote Similarity	NPC725
0.5556	Remote Similarity	NPC6407
0.5556	Remote Similarity	NPC545184
0.5484	Remote Similarity	NPC142860
0.5484	Remote Similarity	NPC152538
0.5484	Remote Similarity	NPC246469
0.5484	Remote Similarity	NPC89088
0.5465	Remote Similarity	NPC206378
0.5435	Remote Similarity	NPC105283
0.5412	Remote Similarity	NPC170475
0.5208	Remote Similarity	NPC291124
0.5208	Remote Similarity	NPC131157
0.5152	Remote Similarity	NPC261254
0.5128	Remote Similarity	NPC23084
0.5125	Remote Similarity	NPC189589
0.5104	Remote Similarity	NPC241016
0.5062	Remote Similarity	NPC208769
0.506	Remote Similarity	NPC37074
0.5057	Remote Similarity	NPC163191
0.5055	Remote Similarity	NPC229687

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC594550 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4241
0.1-0.2	4770
0.2-0.3	121
0.3-0.4	17
0.4-0.5	0
0.5-0.6	0
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
0.759	Intermediate Similarity	NPD7074	Phase 3

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