NPASS Compound

Natural Product: NPC580272

Natural Product ID	NPC580272
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	7-[(2~{R},3~{S},4~{S},5~{S})-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	7-[(2~{R},3~{S},4~{S},5~{S})-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]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] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 89 94 0 0 0 0 0 0 0 0999 V2000 5.3539 4.5729 0.2925 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9129 3.1849 0.3150 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6815 2.4762 -0.8370 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2592 1.1624 -0.6144 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3591 0.5292 -1.8458 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1708 0.0667 -2.3467 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5950 -0.9746 -1.4548 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3700 -1.4642 -1.9212 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7880 -2.1640 -0.8421 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5187 -2.5803 -1.3988 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6197 -1.8747 -1.1240 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4966 -2.2036 -0.1587 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3930 -3.3755 0.7361 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1987 -3.4171 1.8760 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1951 -4.5025 2.7139 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4062 -5.6087 2.4886 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4173 -6.6951 3.3480 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6101 -5.5766 1.3689 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6135 -4.4629 0.5072 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5556 -1.4063 0.0095 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8303 -0.3386 -0.6712 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9742 0.4087 -0.3922 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2589 1.5243 -1.1058 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3747 2.2953 -0.8676 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3644 2.0903 0.0924 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4586 3.2525 0.8588 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7831 3.3272 1.2821 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0723 4.7632 1.6497 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3838 4.9335 2.0903 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6122 2.8822 0.1236 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9303 3.9505 -0.7254 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6897 1.9643 -0.6289 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1249 0.6373 -0.5282 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3675 1.8960 -2.1270 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2430 1.1717 -2.4094 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3849 1.5711 -3.4281 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9607 0.0418 -1.6812 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8450 -0.7337 -1.9094 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0385 -0.4079 -2.8228 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5685 -3.3114 -0.3951 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3608 -3.4589 1.0013 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0643 -3.1824 -0.5438 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6229 -4.4330 -0.8744 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5213 -2.2027 -1.5621 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4597 -2.6872 -2.8702 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1750 0.4400 0.3429 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3970 0.1388 -0.2503 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3722 1.1978 1.6306 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1273 0.4194 2.7580 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4837 2.4240 1.5680 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7296 3.2884 2.6341 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3002 4.6331 0.6352 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3499 4.9131 -0.7653 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0303 5.2377 0.8578 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0330 3.2775 0.4102 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1964 1.1484 -0.3111 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4034 -0.3894 -3.3442 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4659 0.9257 -2.5029 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5493 -0.7309 -0.3825 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5519 -1.4063 -0.0683 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8291 -2.5596 2.0795 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8217 -4.5216 3.5894 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0793 -7.4468 3.1992 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0286 -6.4152 1.1431 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0012 -4.4867 -0.3762 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5898 0.0463 0.4029 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1681 1.2011 0.6789 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9832 2.6769 2.1586 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3958 5.1596 2.4053 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9426 5.3922 0.7311 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9671 4.3859 1.4916 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5661 2.4030 0.4198 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1217 4.2372 -1.2283 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5993 2.2142 -1.7025 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3470 0.0191 -0.5268 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6344 2.7995 -2.6762 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9090 2.4673 -3.4285 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2871 -4.2756 -0.8477 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6336 -4.3696 1.2515 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5470 -2.9054 0.4200 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8982 -5.0998 -1.0409 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5502 -1.8794 -1.3598 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6297 -3.2079 -2.9921 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7029 -0.5261 0.6125 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8306 -0.5267 0.3506 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4276 1.5921 1.6132 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9710 0.4190 3.2884 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4441 2.0950 1.5135 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4329 3.9545 2.4275 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 16 18 1 0 18 19 2 0 12 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 23 34 2 0 34 35 1 0 35 36 1 0 35 37 2 0 37 38 1 0 38 39 2 0 9 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 4 46 1 0 46 47 1 0 46 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 50 2 1 0 44 7 1 0 38 11 1 0 19 13 1 0 37 21 1 0 32 25 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 1 4 56 1 1 6 57 1 0 6 58 1 0 7 59 1 1 9 60 1 1 14 61 1 0 15 62 1 0 17 63 1 0 18 64 1 0 19 65 1 0 22 66 1 0 25 67 1 1 27 68 1 1 28 69 1 0 28 70 1 0 29 71 1 0 30 72 1 1 31 73 1 0 32 74 1 6 33 75 1 0 34 76 1 0 36 77 1 0 40 78 1 6 41 79 1 0 42 80 1 1 43 81 1 0 44 82 1 1 45 83 1 0 46 84 1 1 47 85 1 0 48 86 1 1 49 87 1 0 50 88 1 6 51 89 1 0 M END

Standard InCHIKey	PWFGPIVPLXWWQL-YGMVEURLSA-N
Standard InCHI	InChI=1S/C32H38O19/c1-10-19(36)23(40)26(43)30(46-10)45-9-17-21(38)24(41)27(44)32(50-17)51-29-22(39)18-14(35)6-13(47-31-25(42)20(37)16(8-33)49-31)7-15(18)48-28(29)11-2-4-12(34)5-3-11/h2-7,10,16-17,19-21,23-27,30-38,40-44H,8-9H2,1H3/t10-,16-,17+,19-,20+,21-,23+,24-,25-,26-,27+,30+,31-,32-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(C4=CC=C(O)C=C4)OC4=CC(O[C@H]5O[C@@H](CO)[C@@H](O)[C@@H]5O)=CC(O)=C4C3=O)[C@H](O)[C@@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	726.2	Volume:	656.612 ? Van der Waals volume.
Dense:	1.106	LogP:	0.479 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.047 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.251 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	35.0
TPSA:	308.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	6.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.103	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.199	Fsp³:	0.531
MCE-18:	146.429 ? 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:	0.634	Fluc inhibitor:	0.268 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.69 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.542 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.175	Promiscuous compounds:	0.538

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.824	MDCK Permeability:	-4.922
Pgp-inhibitor:	0.0	Pgp-substrate:	0.972
PAMPA:	1.0 ? 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):	0.036
20% Bioavailability (F20%):	0.023	30% Bioavailability (F30%):	0.778
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	78.474%	Volume Distribution (VD):	-0.04
Fu:	19.163% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.15
BSEP inhibitor:	0.467

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:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.022
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.517
HLM stability:	0.048 ? 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):

0.85

Half-life (T1/2):

5.928

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.124
Human Hepatotoxicity (H-HT):	0.471	Drug-induced Liver Injury (DILI):	0.91
AMES Toxicity:	0.688	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.012	Skin Sensitization:	0.987
Carcinogencity:	0.005	Eye Corrosion:	0.0
Eye Irritation:	0.051	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.994
Hematotoxicity:	0.044	Drug-induced Nephrotoxicity:	0.564
Genotoxicity:	0.188	RPMI-8226 Immunitoxicity:	0.217
A549 Cytotoxicity:	0.223	Hek293 Cytotoxicity:	0.193
BCF:	0.369 ? 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:	2.872 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.621 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.655 ? 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
NPO56254	Indigofera hebepetala	Species	Fabaceae	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 NPC580272 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	22052
0.1-0.2	23862
0.2-0.3	2975
0.3-0.4	448
0.4-0.5	255
0.5-0.6	108
0.6-0.7	65
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9157	High Similarity	NPC186816
0.8191	Intermediate Similarity	NPC25523
0.7882	Intermediate Similarity	NPC116458
0.7882	Intermediate Similarity	NPC246943
0.764	Intermediate Similarity	NPC173582
0.764	Intermediate Similarity	NPC265885
0.764	Intermediate Similarity	NPC181465
0.764	Intermediate Similarity	NPC215710
0.764	Intermediate Similarity	NPC473438
0.764	Intermediate Similarity	NPC253788
0.759	Intermediate Similarity	NPC249281
0.75	Intermediate Similarity	NPC297987
0.7449	Intermediate Similarity	NPC480441
0.7444	Intermediate Similarity	NPC44931
0.7412	Intermediate Similarity	NPC46420
0.7386	Intermediate Similarity	NPC276377
0.734	Intermediate Similarity	NPC142142
0.7234	Intermediate Similarity	NPC32641
0.7234	Intermediate Similarity	NPC256188
0.7174	Intermediate Similarity	NPC65563
0.7174	Intermediate Similarity	NPC470949
0.7174	Intermediate Similarity	NPC150164
0.7097	Intermediate Similarity	NPC473571
0.7097	Intermediate Similarity	NPC110941
0.7079	Intermediate Similarity	NPC605784
0.7065	Intermediate Similarity	NPC67105
0.7053	Intermediate Similarity	NPC35119
0.6989	Remote Similarity	NPC203259
0.6989	Remote Similarity	NPC33054
0.6989	Remote Similarity	NPC210073
0.6989	Remote Similarity	NPC176740
0.6989	Remote Similarity	NPC471725
0.6989	Remote Similarity	NPC134532
0.6989	Remote Similarity	NPC602582
0.6842	Remote Similarity	NPC240306
0.6771	Remote Similarity	NPC470443
0.6733	Remote Similarity	NPC189564
0.6705	Remote Similarity	NPC136042
0.6701	Remote Similarity	NPC72016
0.67	Remote Similarity	NPC14187
0.6667	Remote Similarity	NPC64425
0.6634	Remote Similarity	NPC121703
0.6634	Remote Similarity	NPC203145
0.6632	Remote Similarity	NPC156869
0.6629	Remote Similarity	NPC271692
0.6596	Remote Similarity	NPC471079
0.6591	Remote Similarity	NPC289667
0.6566	Remote Similarity	NPC476472
0.6566	Remote Similarity	NPC294815
0.6566	Remote Similarity	NPC473073
0.6566	Remote Similarity	NPC16194
0.6526	Remote Similarity	NPC39834
0.6526	Remote Similarity	NPC227508
0.6495	Remote Similarity	NPC126784
0.6495	Remote Similarity	NPC241423
0.6489	Remote Similarity	NPC251417
0.6458	Remote Similarity	NPC22062
0.6458	Remote Similarity	NPC473634
0.6458	Remote Similarity	NPC303913
0.6458	Remote Similarity	NPC138811
0.6436	Remote Similarity	NPC602448
0.6364	Remote Similarity	NPC209296
0.6364	Remote Similarity	NPC473327
0.6264	Remote Similarity	NPC84362
0.6263	Remote Similarity	NPC12013
0.6263	Remote Similarity	NPC11432
0.6263	Remote Similarity	NPC477613
0.6226	Remote Similarity	NPC277532
0.619	Remote Similarity	NPC292019
0.619	Remote Similarity	NPC202908
0.6186	Remote Similarity	NPC275454
0.6176	Remote Similarity	NPC101636
0.6162	Remote Similarity	NPC488073
0.6154	Remote Similarity	NPC158674
0.6129	Remote Similarity	NPC611303
0.6126	Remote Similarity	NPC209550
0.6122	Remote Similarity	NPC479405
0.6111	Remote Similarity	NPC111929
0.6111	Remote Similarity	NPC320283
0.6111	Remote Similarity	NPC41121
0.6067	Remote Similarity	NPC288084
0.6061	Remote Similarity	NPC479404
0.6044	Remote Similarity	NPC77672
0.6044	Remote Similarity	NPC108831
0.6044	Remote Similarity	NPC133671
0.6044	Remote Similarity	NPC135391
0.6044	Remote Similarity	NPC78263
0.6044	Remote Similarity	NPC250069
0.6044	Remote Similarity	NPC182634
0.602	Remote Similarity	NPC67326
0.6019	Remote Similarity	NPC221342
0.6019	Remote Similarity	NPC476470
0.5982	Remote Similarity	NPC138990
0.5978	Remote Similarity	NPC323593
0.5978	Remote Similarity	NPC203500
0.5934	Remote Similarity	NPC331652
0.5914	Remote Similarity	NPC24043
0.587	Remote Similarity	NPC39360
0.587	Remote Similarity	NPC29763
0.587	Remote Similarity	NPC210003
0.5865	Remote Similarity	NPC470449
0.5856	Remote Similarity	NPC298666
0.5833	Remote Similarity	NPC164704
0.5825	Remote Similarity	NPC486577
0.5789	Remote Similarity	NPC192539
0.5789	Remote Similarity	NPC175429
0.5784	Remote Similarity	NPC65711
0.5784	Remote Similarity	NPC479403
0.5769	Remote Similarity	NPC470447
0.5758	Remote Similarity	NPC139320
0.5728	Remote Similarity	NPC122467
0.5714	Remote Similarity	NPC292929
0.5714	Remote Similarity	NPC116864
0.5714	Remote Similarity	NPC244776
0.5714	Remote Similarity	NPC298171
0.57	Remote Similarity	NPC163242
0.57	Remote Similarity	NPC272068
0.5699	Remote Similarity	NPC238376
0.5686	Remote Similarity	NPC488074
0.5686	Remote Similarity	NPC64051
0.566	Remote Similarity	NPC135358
0.5644	Remote Similarity	NPC65003
0.5644	Remote Similarity	NPC605592
0.5638	Remote Similarity	NPC8573
0.5638	Remote Similarity	NPC277205
0.5638	Remote Similarity	NPC37919
0.5619	Remote Similarity	NPC89127
0.5614	Remote Similarity	NPC470720
0.56	Remote Similarity	NPC480466
0.56	Remote Similarity	NPC187379
0.5588	Remote Similarity	NPC129264
0.5586	Remote Similarity	NPC470716
0.5579	Remote Similarity	NPC488080
0.5579	Remote Similarity	NPC169977
0.5577	Remote Similarity	NPC606657
0.5546	Remote Similarity	NPC483159
0.5546	Remote Similarity	NPC483160
0.5545	Remote Similarity	NPC470715
0.5534	Remote Similarity	NPC470125
0.5532	Remote Similarity	NPC127546
0.5532	Remote Similarity	NPC57625
0.5532	Remote Similarity	NPC19709
0.5532	Remote Similarity	NPC173637
0.5532	Remote Similarity	NPC317489
0.5532	Remote Similarity	NPC223424
0.5532	Remote Similarity	NPC600591
0.5526	Remote Similarity	NPC474522
0.5526	Remote Similarity	NPC470717
0.5484	Remote Similarity	NPC67037
0.5484	Remote Similarity	NPC255615
0.5474	Remote Similarity	NPC145038
0.5474	Remote Similarity	NPC56077
0.5474	Remote Similarity	NPC281131
0.5474	Remote Similarity	NPC64305
0.5474	Remote Similarity	NPC253662
0.5474	Remote Similarity	NPC179950
0.5474	Remote Similarity	NPC88789
0.5474	Remote Similarity	NPC189142
0.5474	Remote Similarity	NPC77660
0.5474	Remote Similarity	NPC491374
0.5472	Remote Similarity	NPC85751
0.5472	Remote Similarity	NPC19240
0.5463	Remote Similarity	NPC470455
0.5455	Remote Similarity	NPC476215
0.5437	Remote Similarity	NPC204693
0.5429	Remote Similarity	NPC473623
0.5429	Remote Similarity	NPC270448
0.5417	Remote Similarity	NPC27640
0.5413	Remote Similarity	NPC89052
0.5405	Remote Similarity	NPC303694
0.5385	Remote Similarity	NPC153755
0.5377	Remote Similarity	NPC270675
0.5377	Remote Similarity	NPC488089
0.5377	Remote Similarity	NPC195685
0.537	Remote Similarity	NPC470446
0.5361	Remote Similarity	NPC472459
0.5357	Remote Similarity	NPC311850
0.5327	Remote Similarity	NPC80068
0.5327	Remote Similarity	NPC471669
0.5321	Remote Similarity	NPC214621
0.5321	Remote Similarity	NPC34267
0.5315	Remote Similarity	NPC173837
0.5306	Remote Similarity	NPC307938
0.5306	Remote Similarity	NPC488071
0.5304	Remote Similarity	NPC198199
0.5304	Remote Similarity	NPC480445
0.5299	Remote Similarity	NPC241781
0.5288	Remote Similarity	NPC115674
0.5288	Remote Similarity	NPC470444
0.5283	Remote Similarity	NPC229409
0.5278	Remote Similarity	NPC470445
0.5273	Remote Similarity	NPC11468
0.5259	Remote Similarity	NPC156785
0.5248	Remote Similarity	NPC265115
0.5243	Remote Similarity	NPC470405
0.5243	Remote Similarity	NPC471748
0.5229	Remote Similarity	NPC470450
0.5229	Remote Similarity	NPC472994
0.5217	Remote Similarity	NPC68592
0.5208	Remote Similarity	NPC261866

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC580272 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5704
0.1-0.2	3391
0.2-0.3	45
0.3-0.4	3
0.4-0.5	2
0.5-0.6	1
0.6-0.7	2
0.7-0.8	2
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
0.7826	Intermediate Similarity	NPD7251	Phase 2
0.7143	Intermediate Similarity	NPD7808	Phase 3
0.6989	Remote Similarity	NPD6797	Phase 2
0.6364	Remote Similarity	NPD7054	Phase 4
0.5135	Remote Similarity	NPD7472	Pre-clinical

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