NPASS Compound

Natural Product: NPC141466

Natural Product ID	NPC141466
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	SPUFXPFDJYNCFD-USBIDYFYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44259174
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 94 99 0 0 0 0 0 0 0 0999 V2000 7.5789 1.5073 3.0134 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6653 2.6799 2.0830 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7460 2.4833 1.0304 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2787 1.5229 -0.0371 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9094 1.9703 -0.4800 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0045 1.8900 0.7469 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7338 2.0437 0.4427 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7199 1.2671 0.7193 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5801 -0.1134 0.1381 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6124 -1.0589 0.6654 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2853 -2.4710 0.2295 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0829 -2.4767 -0.6725 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9249 -1.7525 -0.0930 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3212 -0.5904 0.5861 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0290 -1.3454 -1.1115 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3010 -1.1650 -0.9229 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6920 0.1218 -0.5058 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1842 0.9945 -0.3474 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0180 0.3801 -0.2866 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4568 1.6401 0.1271 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7995 1.8736 0.3407 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7568 0.8981 0.1615 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2778 -0.3375 -0.2495 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9468 -0.6187 -0.4761 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5531 -1.8012 -0.8641 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.0926 -1.0912 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9743 -3.4482 -1.5192 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9794 -4.4116 -1.3501 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8536 -5.7199 -1.7594 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7019 -6.1606 -2.3721 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2961 -5.2430 -2.5514 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1556 -3.9088 -2.1300 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4863 -5.6154 -3.1614 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5549 -7.4857 -2.7935 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1094 1.0639 0.3558 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7895 2.2241 0.7454 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7709 2.6777 -0.3225 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8049 1.5994 -0.4499 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4786 1.3528 0.8579 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7489 1.9403 2.0098 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3996 3.2058 2.5619 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9454 3.4499 3.8727 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3956 1.9980 1.9435 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7078 -0.0409 1.0458 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1227 0.4321 -0.8258 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0861 2.8355 -1.5512 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5236 2.6285 0.3128 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4322 -2.1016 -1.9694 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1489 -3.3442 1.3079 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6810 -0.9894 2.0683 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4450 3.0340 1.5189 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4484 1.1071 -1.4555 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2018 1.5478 -1.0835 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0495 3.6973 0.4650 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9157 0.5683 2.5091 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2138 1.6202 3.9283 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5419 1.3513 3.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9847 3.5761 2.6894 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6443 2.0997 1.5403 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2145 0.5042 0.4032 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9394 3.0055 -0.8791 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2895 0.9964 1.3099 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6664 1.1641 1.8744 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6985 1.7901 0.5426 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6031 -0.0417 -0.9460 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5965 -0.8105 0.2454 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1308 -2.8504 -0.3711 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7771 -3.5579 -0.7662 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3459 -2.4020 0.6067 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0678 2.8700 0.6596 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9865 -1.1365 -0.4043 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9133 -4.0968 -0.8621 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6478 -6.4490 -1.6167 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9475 -3.2127 -2.3213 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6489 -5.4265 -4.1292 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6521 -8.2312 -2.0856 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0146 3.0460 0.8268 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2338 3.6452 -0.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5627 1.8608 -1.2448 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5080 1.7925 0.8210 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9487 1.1901 2.8768 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4836 3.0381 2.6528 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1420 4.0870 1.9889 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6755 3.8401 4.4198 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2359 -0.3806 0.2868 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6818 -0.1913 -1.3392 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7053 3.7530 -1.6261 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8167 3.5509 0.5796 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6798 -1.6477 -2.3807 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7752 -4.1076 1.2653 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1662 -1.8102 2.3838 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9774 0.2678 -1.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7411 1.1974 -1.9064 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7855 3.7630 -0.4778 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 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 31 33 1 0 30 34 1 0 22 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 40 43 1 0 39 44 1 0 38 45 1 0 37 46 1 0 20 47 1 0 12 48 1 0 11 49 1 0 10 50 1 0 6 51 1 0 5 52 1 0 4 53 1 0 3 54 1 0 51 2 1 0 14 9 1 0 26 16 2 0 32 27 1 0 43 36 1 0 24 19 1 0 1 55 1 0 1 56 1 0 1 57 1 0 2 58 1 0 3 59 1 1 4 60 1 1 5 61 1 0 6 62 1 1 8 63 1 0 8 64 1 0 9 65 1 0 10 66 1 6 11 67 1 0 12 68 1 0 13 69 1 1 21 70 1 0 23 71 1 0 28 72 1 0 29 73 1 0 32 74 1 0 33 75 1 0 34 76 1 0 36 77 1 1 37 78 1 0 38 79 1 6 39 80 1 6 40 81 1 0 41 82 1 0 41 83 1 0 42 84 1 0 44 85 1 0 45 86 1 0 46 87 1 0 47 88 1 0 48 89 1 0 49 90 1 0 50 91 1 0 52 92 1 0 53 93 1 0 54 94 1 0 M END

Standard InCHIKey	SPUFXPFDJYNCFD-USBIDYFYSA-N
Standard InCHI	InChI=1S/C33H40O21/c1-9-19(38)23(42)26(45)31(49-9)48-8-17-21(40)25(44)28(47)33(53-17)54-30-22(41)18-14(37)5-11(50-32-27(46)24(43)20(39)16(7-34)52-32)6-15(18)51-29(30)10-2-3-12(35)13(36)4-10/h2-6,9,16-17,19-21,23-28,31-40,42-47H,7-8H2,1H3/t9?,16?,17?,19-,20-,21+,23-,24-,25?,26?,27?,28?,31+,32+,33-/m0/s1
SMILES	CC1[C@@H]([C@@H](C([C@H](OCC2[C@H](C(C([C@@H](O2)Oc2c(=O)c3c(cc(cc3oc2c2ccc(c(c2)O)O)O[C@H]2C([C@H]([C@H](C(CO)O2)O)O)O)O)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	772.21	Volume:	691.488 ? Van der Waals volume.
Dense:	1.117	LogP:	-0.98 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.225 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.292 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	348.58 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	13.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.092	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.394	Fsp³:	0.545
MCE-18:	154.294 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.644	Fluc inhibitor:	0.214 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.867 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.651 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.23	Promiscuous compounds:	0.345

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.664	MDCK Permeability:	-5.01
Pgp-inhibitor:	0.0	Pgp-substrate:	0.999
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):	0.976
20% Bioavailability (F20%):	0.977	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.06
Plasma Protein Binding (PPB):	72.225%	Volume Distribution (VD):	-0.201
Fu:	25.991% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.186
OATP1B3 inhibitor:	0.968	BCRP inhibitor:	0.012
BSEP inhibitor:	0.0

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:	0.015
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.463
HLM stability:	0.001 ? 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):

0.812

Half-life (T1/2):

4.986

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.346
Human Hepatotoxicity (H-HT):	0.516	Drug-induced Liver Injury (DILI):	0.904
AMES Toxicity:	0.848	Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.106	Skin Sensitization:	0.959
Carcinogencity:	0.01	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.999
Hematotoxicity:	0.014	Drug-induced Nephrotoxicity:	0.095
Genotoxicity:	0.792	RPMI-8226 Immunitoxicity:	0.101
A549 Cytotoxicity:	0.741	Hek293 Cytotoxicity:	0.638
BCF:	0.416 ? 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:	2.911 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.874 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.798 ? 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
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	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 NPC141466 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	22788
0.1-0.2	22781
0.2-0.3	3218
0.3-0.4	548
0.4-0.5	240
0.5-0.6	98
0.6-0.7	74
0.7-0.8	2
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8587	High Similarity	NPC480441
0.8313	Intermediate Similarity	NPC605784
0.8276	Intermediate Similarity	NPC186816
0.7927	Intermediate Similarity	NPC136042
0.7812	Intermediate Similarity	NPC25523
0.7766	Intermediate Similarity	NPC14187
0.764	Intermediate Similarity	NPC67105
0.7556	Intermediate Similarity	NPC203259
0.7556	Intermediate Similarity	NPC33054
0.7556	Intermediate Similarity	NPC210073
0.7556	Intermediate Similarity	NPC176740
0.7556	Intermediate Similarity	NPC471725
0.7556	Intermediate Similarity	NPC134532
0.7556	Intermediate Similarity	NPC156869
0.7556	Intermediate Similarity	NPC602582
0.75	Intermediate Similarity	NPC470443
0.7471	Intermediate Similarity	NPC116458
0.7471	Intermediate Similarity	NPC246943
0.7412	Intermediate Similarity	NPC84362
0.7412	Intermediate Similarity	NPC271692
0.7263	Intermediate Similarity	NPC473073
0.7204	Intermediate Similarity	NPC488073
0.7204	Intermediate Similarity	NPC126784
0.7204	Intermediate Similarity	NPC241423
0.7093	Intermediate Similarity	NPC297987
0.7033	Intermediate Similarity	NPC251417
0.7	Intermediate Similarity	NPC292019
0.7	Intermediate Similarity	NPC202908
0.6882	Remote Similarity	NPC173582
0.6882	Remote Similarity	NPC44931
0.6882	Remote Similarity	NPC265885
0.6882	Remote Similarity	NPC181465
0.6882	Remote Similarity	NPC215710
0.6882	Remote Similarity	NPC275454
0.6882	Remote Similarity	NPC473438
0.6882	Remote Similarity	NPC227508
0.6882	Remote Similarity	NPC253788
0.6782	Remote Similarity	NPC289667
0.6782	Remote Similarity	NPC249281
0.6702	Remote Similarity	NPC39834
0.6701	Remote Similarity	NPC32641
0.6701	Remote Similarity	NPC256188
0.6701	Remote Similarity	NPC35119
0.6633	Remote Similarity	NPC142142
0.6632	Remote Similarity	NPC65563
0.6632	Remote Similarity	NPC470949
0.663	Remote Similarity	NPC276377
0.6629	Remote Similarity	NPC46420
0.6526	Remote Similarity	NPC67326
0.6517	Remote Similarity	NPC277205
0.6517	Remote Similarity	NPC158674
0.6517	Remote Similarity	NPC37919
0.6465	Remote Similarity	NPC486577
0.6458	Remote Similarity	NPC22062
0.6458	Remote Similarity	NPC473634
0.6458	Remote Similarity	NPC138811
0.6458	Remote Similarity	NPC150164
0.6421	Remote Similarity	NPC480466
0.6408	Remote Similarity	NPC189564
0.64	Remote Similarity	NPC476472
0.64	Remote Similarity	NPC294815
0.64	Remote Similarity	NPC16194
0.6392	Remote Similarity	NPC473571
0.6392	Remote Similarity	NPC110941
0.6364	Remote Similarity	NPC209296
0.6364	Remote Similarity	NPC473327
0.6333	Remote Similarity	NPC145038
0.6333	Remote Similarity	NPC56077
0.6333	Remote Similarity	NPC281131
0.6333	Remote Similarity	NPC253662
0.6333	Remote Similarity	NPC179950
0.6333	Remote Similarity	NPC88789
0.6333	Remote Similarity	NPC189142
0.6333	Remote Similarity	NPC77660
0.6333	Remote Similarity	NPC491374
0.6327	Remote Similarity	NPC240306
0.6327	Remote Similarity	NPC64425
0.6311	Remote Similarity	NPC203145
0.6304	Remote Similarity	NPC488071
0.6304	Remote Similarity	NPC611303
0.6263	Remote Similarity	NPC65711
0.6226	Remote Similarity	NPC277532
0.6222	Remote Similarity	NPC238376
0.6211	Remote Similarity	NPC116864
0.6211	Remote Similarity	NPC244776
0.62	Remote Similarity	NPC122467
0.6162	Remote Similarity	NPC488074
0.6117	Remote Similarity	NPC602448
0.6087	Remote Similarity	NPC27640
0.6078	Remote Similarity	NPC89127
0.6044	Remote Similarity	NPC127546
0.6044	Remote Similarity	NPC57625
0.6044	Remote Similarity	NPC19709
0.6044	Remote Similarity	NPC173637
0.6044	Remote Similarity	NPC317489
0.6044	Remote Similarity	NPC223424
0.6044	Remote Similarity	NPC600591
0.604	Remote Similarity	NPC72016
0.6022	Remote Similarity	NPC42773
0.6022	Remote Similarity	NPC45522
0.6022	Remote Similarity	NPC599850
0.6	Remote Similarity	NPC121703
0.5962	Remote Similarity	NPC470446
0.5962	Remote Similarity	NPC135358
0.596	Remote Similarity	NPC479405
0.596	Remote Similarity	NPC303913
0.596	Remote Similarity	NPC605592
0.5929	Remote Similarity	NPC192539
0.5918	Remote Similarity	NPC471079
0.59	Remote Similarity	NPC115674
0.59	Remote Similarity	NPC479404
0.5865	Remote Similarity	NPC470445
0.5859	Remote Similarity	NPC471748
0.5851	Remote Similarity	NPC59534
0.5833	Remote Similarity	NPC303694
0.5806	Remote Similarity	NPC323593
0.5806	Remote Similarity	NPC203500
0.58	Remote Similarity	NPC155877
0.5784	Remote Similarity	NPC479403
0.5758	Remote Similarity	NPC29958
0.5752	Remote Similarity	NPC488078
0.5745	Remote Similarity	NPC305811
0.5728	Remote Similarity	NPC229409
0.5728	Remote Similarity	NPC606657
0.5714	Remote Similarity	NPC223860
0.5714	Remote Similarity	NPC101636
0.5714	Remote Similarity	NPC298666
0.5714	Remote Similarity	NPC265115
0.5699	Remote Similarity	NPC39360
0.5699	Remote Similarity	NPC77672
0.5699	Remote Similarity	NPC133671
0.5699	Remote Similarity	NPC135391
0.5699	Remote Similarity	NPC29763
0.5699	Remote Similarity	NPC78263
0.5699	Remote Similarity	NPC210003
0.5699	Remote Similarity	NPC250069
0.5657	Remote Similarity	NPC480463
0.5652	Remote Similarity	NPC67037
0.5652	Remote Similarity	NPC255615
0.5636	Remote Similarity	NPC311850
0.5631	Remote Similarity	NPC12013
0.5631	Remote Similarity	NPC11432
0.5631	Remote Similarity	NPC477613
0.5619	Remote Similarity	NPC471669
0.5619	Remote Similarity	NPC473071
0.5579	Remote Similarity	NPC24043
0.5575	Remote Similarity	NPC198199
0.5565	Remote Similarity	NPC209550
0.5565	Remote Similarity	NPC241781
0.5545	Remote Similarity	NPC164704
0.5532	Remote Similarity	NPC19388
0.5532	Remote Similarity	NPC240431
0.5532	Remote Similarity	NPC55786
0.5532	Remote Similarity	NPC108831
0.5532	Remote Similarity	NPC182634
0.55	Remote Similarity	NPC8856
0.5487	Remote Similarity	NPC68592
0.5481	Remote Similarity	NPC483414
0.5481	Remote Similarity	NPC483415
0.5474	Remote Similarity	NPC64305
0.5464	Remote Similarity	NPC285197
0.5455	Remote Similarity	NPC190003
0.5446	Remote Similarity	NPC470716
0.5446	Remote Similarity	NPC187379
0.5437	Remote Similarity	NPC204693
0.5431	Remote Similarity	NPC120952
0.5431	Remote Similarity	NPC138990
0.5429	Remote Similarity	NPC483416
0.5429	Remote Similarity	NPC37668
0.5429	Remote Similarity	NPC473623
0.5426	Remote Similarity	NPC111929
0.5426	Remote Similarity	NPC320283
0.5426	Remote Similarity	NPC473043
0.5426	Remote Similarity	NPC331652
0.5426	Remote Similarity	NPC41121
0.5421	Remote Similarity	NPC292929
0.5421	Remote Similarity	NPC221342
0.5421	Remote Similarity	NPC476470
0.5408	Remote Similarity	NPC601144
0.5405	Remote Similarity	NPC470715
0.54	Remote Similarity	NPC254855
0.54	Remote Similarity	NPC94610
0.54	Remote Similarity	NPC95866
0.5391	Remote Similarity	NPC156785
0.5391	Remote Similarity	NPC162394
0.5377	Remote Similarity	NPC488089
0.537	Remote Similarity	NPC223426
0.5368	Remote Similarity	NPC261866
0.5364	Remote Similarity	NPC470451
0.5361	Remote Similarity	NPC472459
0.5354	Remote Similarity	NPC311830
0.5345	Remote Similarity	NPC470720
0.534	Remote Similarity	NPC65003
0.5321	Remote Similarity	NPC81042
0.5312	Remote Similarity	NPC482520
0.5312	Remote Similarity	NPC95090
0.5312	Remote Similarity	NPC27408
0.5312	Remote Similarity	NPC482519
0.5306	Remote Similarity	NPC60735
0.5306	Remote Similarity	NPC307938

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC141466 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5767
0.1-0.2	3315
0.2-0.3	58
0.3-0.4	3
0.4-0.5	1
0.5-0.6	2
0.6-0.7	1
0.7-0.8	2
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8636	High Similarity	NPD7251	Phase 2
0.7556	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD7808	Phase 3
0.6364	Remote Similarity	NPD7054	Phase 4
0.5135	Remote Similarity	NPD7472	Pre-clinical
0.5093	Remote Similarity	NPD7804	Clinical (unspecified phase)

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