NPASS Compound

Natural Product: NPC567336

Natural Product ID	NPC567336
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)-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-7-[(2~{S},3~{S},4~{R},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-(4-methoxyphenyl)-3-[(2~{S},3~{S},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-7-[(2~{S},3~{S},4~{R},5~{R})-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] [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 71 75 0 0 0 0 0 0 0 0999 V2000 -6.0048 4.7052 2.3706 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6779 4.6647 2.8366 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8001 3.6828 2.3944 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4962 3.6223 2.8383 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6669 2.6358 2.3752 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0643 1.6502 1.4507 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0373 0.7305 1.0260 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3125 -0.5414 0.6033 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4801 -1.1886 0.4888 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4766 -1.4483 -0.3808 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7474 -1.2671 0.2110 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7581 -1.5523 -0.6652 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8936 -0.5216 -0.6162 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3557 -1.6763 -2.1029 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5072 -2.1239 -2.7929 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2822 -2.7464 -2.2853 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3908 -2.4276 -3.3006 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5423 -2.8631 -0.9449 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2921 -3.6954 -0.1170 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1809 -1.3165 0.2298 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2880 -2.4985 -0.1760 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0705 -0.7680 0.3127 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2056 -1.5074 -0.0471 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9820 -2.8033 -0.4847 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4660 -0.9635 0.0350 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6827 0.3085 0.4647 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8988 0.9200 0.5747 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1141 0.3363 0.2595 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9730 0.2575 1.3620 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0271 -0.5737 1.1108 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3652 -0.8264 -0.3083 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8882 -2.0772 -0.7212 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9942 0.2622 -1.2681 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4822 -0.3579 -2.4276 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9049 1.1681 -0.7612 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5447 2.1857 -0.0253 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5559 1.0463 0.8228 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2726 0.5235 0.7506 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2210 1.1982 1.0807 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3499 1.7473 1.0396 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2361 2.7429 1.4897 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5072 3.7385 2.5287 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9719 4.8691 1.2736 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5414 5.4821 2.9275 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1372 4.3536 3.5509 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6408 2.6071 2.7428 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3466 -0.7942 -1.2904 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2819 -2.5234 -0.4145 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6493 -0.8802 -1.3632 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4820 0.4490 -0.8852 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3759 -0.5577 0.3879 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0737 -0.7142 -2.5735 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7790 -1.4940 -3.4977 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7497 -3.7119 -2.5129 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4583 -2.5838 -2.9893 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5749 -3.3312 -1.0853 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0296 -3.6387 0.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6703 -3.3169 -1.0349 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2881 -1.5888 -0.2570 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0765 -0.6913 -0.1450 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9066 -0.2089 1.7177 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7814 -1.5677 1.5830 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4902 -0.9276 -0.3635 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6160 -2.1116 -1.6521 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8731 0.8453 -1.6157 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1800 -0.6591 -3.0344 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2373 1.5554 -1.5302 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9608 2.8589 -0.5895 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6720 2.0750 1.1754 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7090 1.0651 0.3005 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2515 2.7588 1.1185 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 12 14 1 0 14 15 1 0 14 16 1 0 16 17 1 0 16 18 1 0 18 19 1 0 8 20 1 0 20 21 2 0 20 22 1 0 22 23 2 0 23 24 1 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 26 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 18 10 1 0 38 22 1 0 35 28 1 0 1 42 1 0 1 43 1 0 1 44 1 0 4 45 1 0 5 46 1 0 10 47 1 6 12 48 1 1 13 49 1 0 13 50 1 0 13 51 1 0 14 52 1 6 15 53 1 0 16 54 1 6 17 55 1 0 18 56 1 6 19 57 1 0 24 58 1 0 25 59 1 0 28 60 1 6 30 61 1 0 30 62 1 0 31 63 1 1 32 64 1 0 33 65 1 6 34 66 1 0 35 67 1 6 36 68 1 0 37 69 1 0 40 70 1 0 41 71 1 0 M END

Standard InCHIKey	JCEAFPKMXHMEGO-SOOAOZJQSA-N
Standard InCHI	InChI=1S/C27H30O14/c1-10-18(30)21(33)23(35)27(38-10)41-25-20(32)17-14(28)7-13(39-26-22(34)19(31)15(29)9-37-26)8-16(17)40-24(25)11-3-5-12(36-2)6-4-11/h3-8,10,15,18-19,21-23,26-31,33-35H,9H2,1-2H3/t10-,15+,18-,19+,21+,22-,23-,26-,27-/m0/s1
SMILES	COC1=CC=C(C2=C(O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@@H]3O)C(=O)C3=C(O)C=C(O[C@@H]4OC[C@@H](O)[C@@H](O)[C@@H]4O)C=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.16	Volume:	534.737 ? Van der Waals volume.
Dense:	1.081	LogP:	1.309 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.68 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.547 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	217.97 ? 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:	0.191	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.548	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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.653	Fluc inhibitor:	0.308 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.922 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.772 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.048	Promiscuous compounds:	0.399

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.247	MDCK Permeability:	-5.305
Pgp-inhibitor:	0.003	Pgp-substrate:	0.993
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):	0.892
20% Bioavailability (F20%):	0.553	30% Bioavailability (F30%):	0.943
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.176
Plasma Protein Binding (PPB):	83.214%	Volume Distribution (VD):	-0.025
Fu:	15.61% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.928
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.505
BSEP inhibitor:	0.091

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:	0.956
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.998
HLM stability:	0.345 ? 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):

1.542

Half-life (T1/2):

3.527

ADMET: Toxicity

hERG Blockers:	0.018	hERG Blockers (10um):	0.124
Human Hepatotoxicity (H-HT):	0.73	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.971	Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.049	Skin Sensitization:	0.998
Carcinogencity:	0.119	Eye Corrosion:	0.0
Eye Irritation:	0.1	Respiratory Toxicity:	0.02
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.93
Hematotoxicity:	0.389	Drug-induced Nephrotoxicity:	0.963
Genotoxicity:	0.435	RPMI-8226 Immunitoxicity:	0.332
A549 Cytotoxicity:	0.611	Hek293 Cytotoxicity:	0.33
BCF:	0.518 ? 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:	3.255 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.772 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.015 ? 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
NPO47602	Cassia biflora	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 NPC567336 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	14727
0.1-0.2	31235
0.2-0.3	2912
0.3-0.4	500
0.4-0.5	300
0.5-0.6	133
0.6-0.7	29
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
0.8571	High Similarity	NPC276377
0.7949	Intermediate Similarity	NPC611303
0.7692	Intermediate Similarity	NPC46420
0.7662	Intermediate Similarity	NPC249281
0.7468	Intermediate Similarity	NPC271692
0.7342	Intermediate Similarity	NPC158674
0.7215	Intermediate Similarity	NPC289667
0.7209	Intermediate Similarity	NPC150164
0.7108	Intermediate Similarity	NPC116458
0.7108	Intermediate Similarity	NPC246943
0.7079	Intermediate Similarity	NPC72016
0.7079	Intermediate Similarity	NPC606657
0.7059	Intermediate Similarity	NPC251417
0.6932	Remote Similarity	NPC186816
0.6905	Remote Similarity	NPC605784
0.6506	Remote Similarity	NPC297987
0.6354	Remote Similarity	NPC14187
0.6344	Remote Similarity	NPC32641
0.6344	Remote Similarity	NPC256188
0.6344	Remote Similarity	NPC35119
0.631	Remote Similarity	NPC136042
0.6279	Remote Similarity	NPC219904
0.6264	Remote Similarity	NPC22062
0.6264	Remote Similarity	NPC473634
0.6264	Remote Similarity	NPC138811
0.6235	Remote Similarity	NPC84362
0.6235	Remote Similarity	NPC27640
0.6163	Remote Similarity	NPC472459
0.6163	Remote Similarity	NPC59534
0.6129	Remote Similarity	NPC64425
0.6111	Remote Similarity	NPC278419
0.6111	Remote Similarity	NPC179198
0.6105	Remote Similarity	NPC142142
0.6071	Remote Similarity	NPC111929
0.6071	Remote Similarity	NPC320283
0.6071	Remote Similarity	NPC41121
0.6047	Remote Similarity	NPC181712
0.6047	Remote Similarity	NPC349108
0.604	Remote Similarity	NPC277532
0.6	Remote Similarity	NPC19709
0.6	Remote Similarity	NPC265115
0.6	Remote Similarity	NPC238376
0.596	Remote Similarity	NPC121703
0.5957	Remote Similarity	NPC240306
0.5941	Remote Similarity	NPC25523
0.5938	Remote Similarity	NPC5319
0.593	Remote Similarity	NPC95090
0.593	Remote Similarity	NPC265530
0.593	Remote Similarity	NPC27408
0.5895	Remote Similarity	NPC483414
0.5889	Remote Similarity	NPC355481
0.5882	Remote Similarity	NPC473043
0.5882	Remote Similarity	NPC331652
0.5862	Remote Similarity	NPC305811
0.5833	Remote Similarity	NPC209296
0.5814	Remote Similarity	NPC127546
0.5814	Remote Similarity	NPC57625
0.5814	Remote Similarity	NPC108831
0.5814	Remote Similarity	NPC173637
0.5814	Remote Similarity	NPC317489
0.5814	Remote Similarity	NPC223424
0.5814	Remote Similarity	NPC182634
0.5814	Remote Similarity	NPC600591
0.5811	Remote Similarity	NPC262094
0.5784	Remote Similarity	NPC480441
0.5778	Remote Similarity	NPC223747
0.5773	Remote Similarity	NPC486577
0.5747	Remote Similarity	NPC64305
0.5729	Remote Similarity	NPC483415
0.5714	Remote Similarity	NPC54802
0.5714	Remote Similarity	NPC197304
0.5698	Remote Similarity	NPC135599
0.5698	Remote Similarity	NPC73855
0.5698	Remote Similarity	NPC113968
0.5698	Remote Similarity	NPC328940
0.5698	Remote Similarity	NPC277174
0.5698	Remote Similarity	NPC160515
0.5698	Remote Similarity	NPC606877
0.567	Remote Similarity	NPC483416
0.567	Remote Similarity	NPC473327
0.5625	Remote Similarity	NPC46202
0.5567	Remote Similarity	NPC470443
0.5566	Remote Similarity	NPC295625
0.5556	Remote Similarity	NPC76831
0.5532	Remote Similarity	NPC480466
0.5532	Remote Similarity	NPC471079
0.5524	Remote Similarity	NPC470716
0.551	Remote Similarity	NPC473623
0.5505	Remote Similarity	NPC209550
0.5495	Remote Similarity	NPC22832
0.5481	Remote Similarity	NPC470715
0.5474	Remote Similarity	NPC173582
0.5474	Remote Similarity	NPC265885
0.5474	Remote Similarity	NPC181465
0.5474	Remote Similarity	NPC215710
0.5474	Remote Similarity	NPC67105
0.5474	Remote Similarity	NPC473438
0.5474	Remote Similarity	NPC253788
0.5465	Remote Similarity	NPC276222
0.5465	Remote Similarity	NPC274618
0.5465	Remote Similarity	NPC118284
0.5465	Remote Similarity	NPC608147
0.5455	Remote Similarity	NPC488089
0.5426	Remote Similarity	NPC480463
0.5417	Remote Similarity	NPC210073
0.5413	Remote Similarity	NPC470720
0.54	Remote Similarity	NPC475382
0.5385	Remote Similarity	NPC153758
0.5376	Remote Similarity	NPC190003
0.5361	Remote Similarity	NPC473571
0.5361	Remote Similarity	NPC110941
0.5333	Remote Similarity	NPC24043
0.5333	Remote Similarity	NPC164704
0.5326	Remote Similarity	NPC243930
0.5326	Remote Similarity	NPC120099
0.5326	Remote Similarity	NPC486578
0.5321	Remote Similarity	NPC470717
0.5315	Remote Similarity	NPC175429
0.5312	Remote Similarity	NPC44931
0.5312	Remote Similarity	NPC267680
0.5312	Remote Similarity	NPC67326
0.5312	Remote Similarity	NPC227508
0.5306	Remote Similarity	NPC126784
0.5306	Remote Similarity	NPC241423
0.5306	Remote Similarity	NPC488074
0.5294	Remote Similarity	NPC135358
0.5281	Remote Similarity	NPC348541
0.5275	Remote Similarity	NPC27942
0.5263	Remote Similarity	NPC487212
0.5258	Remote Similarity	NPC293626
0.5258	Remote Similarity	NPC203259
0.5258	Remote Similarity	NPC33054
0.5258	Remote Similarity	NPC176740
0.5258	Remote Similarity	NPC471725
0.5258	Remote Similarity	NPC134532
0.5258	Remote Similarity	NPC602582
0.5248	Remote Similarity	NPC476472
0.5248	Remote Similarity	NPC294815
0.5248	Remote Similarity	NPC470447
0.5248	Remote Similarity	NPC16194
0.5225	Remote Similarity	NPC138990
0.5217	Remote Similarity	NPC175107
0.5217	Remote Similarity	NPC285197
0.5217	Remote Similarity	NPC488071
0.5208	Remote Similarity	NPC609888
0.5204	Remote Similarity	NPC204693
0.5196	Remote Similarity	NPC221342
0.5196	Remote Similarity	NPC470445
0.5196	Remote Similarity	NPC476470
0.5192	Remote Similarity	NPC11468
0.5182	Remote Similarity	NPC470719
0.5161	Remote Similarity	NPC21666
0.5158	Remote Similarity	NPC116864
0.5158	Remote Similarity	NPC244776
0.5155	Remote Similarity	NPC39834
0.5152	Remote Similarity	NPC153755
0.5111	Remote Similarity	NPC77672
0.5111	Remote Similarity	NPC133671
0.5111	Remote Similarity	NPC135391
0.5111	Remote Similarity	NPC78263
0.5111	Remote Similarity	NPC250069
0.5106	Remote Similarity	NPC607707
0.5102	Remote Similarity	NPC65563
0.5102	Remote Similarity	NPC470949
0.5098	Remote Similarity	NPC473073
0.5094	Remote Similarity	NPC48984
0.5055	Remote Similarity	NPC277205
0.5055	Remote Similarity	NPC37919
0.5055	Remote Similarity	NPC189142
0.5055	Remote Similarity	NPC77660
0.5054	Remote Similarity	NPC60735
0.5054	Remote Similarity	NPC26230
0.5053	Remote Similarity	NPC66087
0.505	Remote Similarity	NPC482026
0.5047	Remote Similarity	NPC473644

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC567336 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4152
0.1-0.2	4891
0.2-0.3	95
0.3-0.4	6
0.4-0.5	1
0.5-0.6	3
0.6-0.7	2
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
0.6289	Remote Similarity	NPD7808	Phase 3
0.6211	Remote Similarity	NPD7251	Phase 2
0.5938	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7054	Phase 4
0.5258	Remote Similarity	NPD6797	Phase 2

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