NPASS Compound

Natural Product: NPC519250

Natural Product ID	NPC519250
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-[(2~{S},3~{S},4~{R})-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2~{S},3~{S},4~{S},5~{S},6~{S})-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	3-[(2~{S},3~{S},4~{R})-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2~{S},3~{S},4~{S},5~{S},6~{S})-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]

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 9.9448 0.5444 0.9016 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4109 -0.3690 -0.2124 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2645 0.2068 -0.6895 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1500 -0.4469 -0.2329 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9740 0.2590 -0.2995 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3787 0.4663 0.9379 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1060 1.2580 0.6936 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2305 0.6101 -0.1294 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1886 1.4250 -0.5901 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4046 1.9253 0.4305 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0709 1.6382 0.6406 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6001 2.2126 1.7339 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9150 1.9731 2.0023 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5239 2.5651 3.0917 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6446 1.1386 1.1881 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9540 0.8426 1.3831 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5212 1.3820 2.3825 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7065 -0.0237 0.5400 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9668 -0.1975 0.9073 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2077 0.3596 0.7554 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5010 1.2235 1.8539 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8447 1.4099 1.9108 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5256 0.4125 1.0421 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8878 0.9580 -0.1735 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6895 -0.2945 1.7086 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7266 0.5742 1.9401 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3816 -0.5845 0.7911 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3386 -1.3770 1.9400 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0220 -0.5517 -0.5035 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5816 -1.4748 -1.5063 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6605 -2.2623 -2.2068 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0924 -3.1056 -3.1964 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4276 -3.2348 -3.5629 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8543 -4.0914 -4.5666 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2964 -2.4416 -2.8486 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8747 -1.5904 -1.8526 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7338 -0.2447 -0.6705 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0401 0.5333 0.0825 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7069 0.8166 -0.1342 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7741 2.4982 -1.4834 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9813 3.6353 -1.4296 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1986 2.8384 -1.1889 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4873 4.1836 -1.5294 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4679 2.6483 0.2712 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8212 2.8660 0.4959 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1102 -1.8108 -0.8824 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3994 -1.7526 -2.2419 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2483 -2.6127 -0.2338 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6226 -3.3836 0.7726 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2369 -1.7195 0.4374 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5052 -2.3460 0.3335 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1978 0.5278 1.7222 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0110 1.5821 0.5593 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8899 0.1212 1.3081 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1783 -0.3558 -1.0058 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3172 -0.6628 0.8660 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0973 -0.4520 1.4490 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0669 1.0569 1.5850 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6295 1.3416 1.7154 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5839 0.7645 -1.2394 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0158 2.8705 2.3581 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5454 2.1453 4.0156 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3495 1.0497 -0.1201 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1508 1.2008 2.9802 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1826 2.4518 1.7153 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7469 0.6481 -0.5286 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0308 -1.0739 0.9702 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3305 -0.8562 2.5847 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3363 1.3850 2.3891 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5592 -1.1610 -0.1142 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6317 -1.1382 2.5617 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5903 -2.2016 -1.9541 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3673 -3.7157 -3.7322 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6455 -3.8333 -5.1419 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3549 -2.5260 -3.1221 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6303 -1.0014 -1.3885 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2635 0.3287 -1.0053 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7194 2.1200 -2.5328 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5995 3.8770 -2.3092 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8998 2.2296 -1.8291 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4624 4.2448 -1.7578 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9097 3.4404 0.8157 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9284 3.3167 1.3686 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1438 -2.3220 -0.7889 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5124 -2.6222 -2.6542 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6950 -3.3234 -0.9510 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4137 -2.7632 1.5003 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0657 -1.6167 1.5366 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6270 -2.6230 -0.6287 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 1 0 13 15 2 0 15 16 1 0 16 17 2 0 16 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 6 23 25 1 0 25 26 1 0 23 27 1 0 27 28 1 0 18 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 2 0 33 34 1 0 33 35 1 0 35 36 2 0 29 37 1 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 39 11 1 0 38 15 1 0 27 20 1 0 36 30 1 0 1 52 1 0 1 53 1 0 1 54 1 0 2 55 1 6 4 56 1 1 6 57 1 0 6 58 1 0 7 59 1 1 9 60 1 6 12 61 1 0 14 62 1 0 20 63 1 6 22 64 1 0 22 65 1 0 24 66 1 0 25 67 1 0 25 68 1 0 26 69 1 0 27 70 1 6 28 71 1 0 31 72 1 0 32 73 1 0 34 74 1 0 35 75 1 0 36 76 1 0 39 77 1 0 40 78 1 6 41 79 1 0 42 80 1 6 43 81 1 0 44 82 1 1 45 83 1 0 46 84 1 6 47 85 1 0 48 86 1 6 49 87 1 0 50 88 1 1 51 89 1 0 M END

Standard InCHIKey	XKDYFRZJOFUFSX-TUYASBCQSA-N
Standard InCHI	InChI=1S/C32H38O19/c1-11-19(36)22(39)24(41)29(47-11)45-8-17-20(37)23(40)25(42)30(50-17)48-14-6-15(35)18-16(7-14)49-26(12-2-4-13(34)5-3-12)27(21(18)38)51-31-28(43)32(44,9-33)10-46-31/h2-7,11,17,19-20,22-25,28-31,33-37,39-44H,8-10H2,1H3/t11-,17-,19-,20+,22+,23-,24-,25-,28+,29+,30+,31-,32+/m0/s1
SMILES	C[C@@H]1O[C@@H](OC[C@@H]2O[C@@H](OC3=CC(O)=C4C(=O)C(O[C@@H]5OC[C@](O)(CO)[C@@H]5O)=C(C5=CC=C(O)C=C5)OC4=C3)[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:	0.979 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.381 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.599 ? 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:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.332	Fsp³:	0.531
MCE-18:	150.0 ? 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:	0.61	Fluc inhibitor:	0.275 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.676 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.615 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.115	Promiscuous compounds:	0.53

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.736	MDCK Permeability:	-5.011
Pgp-inhibitor:	0.0	Pgp-substrate:	0.959
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):	0.304
20% Bioavailability (F20%):	0.816	30% Bioavailability (F30%):	0.987
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.211
Plasma Protein Binding (PPB):	82.118%	Volume Distribution (VD):	-0.051
Fu:	17.288% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.482
OATP1B3 inhibitor:	0.885	BCRP inhibitor:	0.166
BSEP inhibitor:	0.024

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:	0.726
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.259
HLM stability:	0.004 ? 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):

1.089

Half-life (T1/2):

4.84

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.055
Human Hepatotoxicity (H-HT):	0.643	Drug-induced Liver Injury (DILI):	0.901
AMES Toxicity:	0.984	Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.111	Skin Sensitization:	1.0
Carcinogencity:	0.038	Eye Corrosion:	0.0
Eye Irritation:	0.082	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.992
Hematotoxicity:	0.294	Drug-induced Nephrotoxicity:	0.886
Genotoxicity:	0.961	RPMI-8226 Immunitoxicity:	0.3
A549 Cytotoxicity:	0.851	Hek293 Cytotoxicity:	0.739
BCF:	0.383 ? 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:	2.91 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.614 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.614 ? 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
NPO63828	Silphium perfoliatum	Species	Asteraceae	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 NPC519250 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	22650
0.1-0.2	23923
0.2-0.3	2444
0.3-0.4	387
0.4-0.5	279
0.5-0.6	106
0.6-0.7	48
0.7-0.8	1
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8736	High Similarity	NPC186816
0.8621	High Similarity	NPC150164
0.7327	Intermediate Similarity	NPC25523
0.7312	Intermediate Similarity	NPC173582
0.7312	Intermediate Similarity	NPC265885
0.7312	Intermediate Similarity	NPC181465
0.7312	Intermediate Similarity	NPC215710
0.7312	Intermediate Similarity	NPC473438
0.7312	Intermediate Similarity	NPC253788
0.7292	Intermediate Similarity	NPC72016
0.7253	Intermediate Similarity	NPC276377
0.7241	Intermediate Similarity	NPC249281
0.7128	Intermediate Similarity	NPC44931
0.7079	Intermediate Similarity	NPC46420
0.7041	Intermediate Similarity	NPC142142
0.6957	Remote Similarity	NPC116458
0.6957	Remote Similarity	NPC246943
0.6875	Remote Similarity	NPC65563
0.6875	Remote Similarity	NPC470949
0.6804	Remote Similarity	NPC473571
0.6804	Remote Similarity	NPC110941
0.6771	Remote Similarity	NPC67105
0.6701	Remote Similarity	NPC203259
0.6701	Remote Similarity	NPC33054
0.6701	Remote Similarity	NPC210073
0.6701	Remote Similarity	NPC176740
0.6701	Remote Similarity	NPC471725
0.6701	Remote Similarity	NPC134532
0.6701	Remote Similarity	NPC602582
0.6667	Remote Similarity	NPC480441
0.66	Remote Similarity	NPC32641
0.66	Remote Similarity	NPC256188
0.6593	Remote Similarity	NPC297987
0.6538	Remote Similarity	NPC121703
0.65	Remote Similarity	NPC470443
0.65	Remote Similarity	NPC65711
0.6495	Remote Similarity	NPC471079
0.6436	Remote Similarity	NPC35119
0.6364	Remote Similarity	NPC303913
0.6344	Remote Similarity	NPC271692
0.6311	Remote Similarity	NPC476472
0.6311	Remote Similarity	NPC294815
0.6311	Remote Similarity	NPC473073
0.6311	Remote Similarity	NPC16194
0.6263	Remote Similarity	NPC39834
0.6263	Remote Similarity	NPC227508
0.625	Remote Similarity	NPC605784
0.6238	Remote Similarity	NPC126784
0.6238	Remote Similarity	NPC240306
0.6238	Remote Similarity	NPC241423
0.62	Remote Similarity	NPC22062
0.62	Remote Similarity	NPC473634
0.62	Remote Similarity	NPC138811
0.6168	Remote Similarity	NPC189564
0.6117	Remote Similarity	NPC209296
0.6117	Remote Similarity	NPC473327
0.6075	Remote Similarity	NPC203145
0.6055	Remote Similarity	NPC303694
0.6053	Remote Similarity	NPC209550
0.604	Remote Similarity	NPC156869
0.6019	Remote Similarity	NPC12013
0.6019	Remote Similarity	NPC11432
0.6019	Remote Similarity	NPC477613
0.5981	Remote Similarity	NPC14187
0.5943	Remote Similarity	NPC101636
0.5943	Remote Similarity	NPC221342
0.5943	Remote Similarity	NPC476470
0.5941	Remote Similarity	NPC67326
0.5922	Remote Similarity	NPC64425
0.5895	Remote Similarity	NPC158674
0.5895	Remote Similarity	NPC136042
0.5888	Remote Similarity	NPC602448
0.5876	Remote Similarity	NPC611303
0.5851	Remote Similarity	NPC111929
0.5851	Remote Similarity	NPC320283
0.5851	Remote Similarity	NPC41121
0.5789	Remote Similarity	NPC289667
0.5789	Remote Similarity	NPC108831
0.5789	Remote Similarity	NPC182634
0.5755	Remote Similarity	NPC486577
0.5743	Remote Similarity	NPC251417
0.5728	Remote Similarity	NPC479405
0.5714	Remote Similarity	NPC277532
0.5684	Remote Similarity	NPC331652
0.5676	Remote Similarity	NPC292019
0.5676	Remote Similarity	NPC202908
0.5673	Remote Similarity	NPC479404
0.5648	Remote Similarity	NPC470449
0.5641	Remote Similarity	NPC138990
0.5631	Remote Similarity	NPC275454
0.5619	Remote Similarity	NPC488073
0.5619	Remote Similarity	NPC488074
0.5593	Remote Similarity	NPC175429
0.5556	Remote Similarity	NPC470447
0.5524	Remote Similarity	NPC129264
0.5514	Remote Similarity	NPC122467
0.551	Remote Similarity	NPC84362
0.5505	Remote Similarity	NPC298171
0.5492	Remote Similarity	NPC483159
0.5492	Remote Similarity	NPC483160
0.549	Remote Similarity	NPC116864
0.549	Remote Similarity	NPC244776
0.5472	Remote Similarity	NPC64051
0.5464	Remote Similarity	NPC238376
0.5421	Remote Similarity	NPC479403
0.5413	Remote Similarity	NPC89127
0.5385	Remote Similarity	NPC298666
0.5385	Remote Similarity	NPC187379
0.537	Remote Similarity	NPC270448
0.537	Remote Similarity	NPC606657
0.5364	Remote Similarity	NPC292929
0.5333	Remote Similarity	NPC192539
0.5327	Remote Similarity	NPC470125
0.5306	Remote Similarity	NPC127546
0.5306	Remote Similarity	NPC57625
0.5306	Remote Similarity	NPC77672
0.5306	Remote Similarity	NPC133671
0.5306	Remote Similarity	NPC19709
0.5306	Remote Similarity	NPC135391
0.5306	Remote Similarity	NPC173637
0.5306	Remote Similarity	NPC78263
0.5306	Remote Similarity	NPC317489
0.5306	Remote Similarity	NPC250069
0.5306	Remote Similarity	NPC223424
0.5306	Remote Similarity	NPC600591
0.5273	Remote Similarity	NPC85751
0.5273	Remote Similarity	NPC19240
0.5268	Remote Similarity	NPC470455
0.5254	Remote Similarity	NPC480445
0.5253	Remote Similarity	NPC323593
0.5253	Remote Similarity	NPC203500
0.5243	Remote Similarity	NPC476215
0.5234	Remote Similarity	NPC204693
0.5229	Remote Similarity	NPC473623
0.5221	Remote Similarity	NPC89052
0.5217	Remote Similarity	NPC164704
0.521	Remote Similarity	NPC474522
0.52	Remote Similarity	NPC24043
0.52	Remote Similarity	NPC27640
0.5189	Remote Similarity	NPC163242
0.5189	Remote Similarity	NPC272068
0.5185	Remote Similarity	NPC153755
0.5182	Remote Similarity	NPC270675
0.5182	Remote Similarity	NPC488089
0.5182	Remote Similarity	NPC195685
0.5179	Remote Similarity	NPC470446
0.5179	Remote Similarity	NPC135358
0.5152	Remote Similarity	NPC39360
0.5152	Remote Similarity	NPC29763
0.5152	Remote Similarity	NPC210003
0.5149	Remote Similarity	NPC59534
0.514	Remote Similarity	NPC473512
0.514	Remote Similarity	NPC65003
0.514	Remote Similarity	NPC129827
0.514	Remote Similarity	NPC605592
0.5135	Remote Similarity	NPC80068
0.5133	Remote Similarity	NPC214621
0.5133	Remote Similarity	NPC34267
0.513	Remote Similarity	NPC173837
0.5124	Remote Similarity	NPC241781
0.5094	Remote Similarity	NPC139320
0.5091	Remote Similarity	NPC229409
0.5089	Remote Similarity	NPC470445
0.5088	Remote Similarity	NPC11468
0.5052	Remote Similarity	NPC54802
0.5052	Remote Similarity	NPC197304
0.5044	Remote Similarity	NPC470450
0.5044	Remote Similarity	NPC472994
0.5041	Remote Similarity	NPC470720

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC519250 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5819
0.1-0.2	3286
0.2-0.3	37
0.3-0.4	2
0.4-0.5	2
0.5-0.6	0
0.6-0.7	3
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
0.75	Intermediate Similarity	NPD7251	Phase 2
0.6863	Remote Similarity	NPD7808	Phase 3
0.6701	Remote Similarity	NPD6797	Phase 2
0.6117	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