NPASS Compound

Natural Product: NPC563654

Natural Product ID	NPC563654
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-3-[(2~{S},3~{R},4~{R},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-3-[(2~{S},3~{R},4~{R},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},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 79 83 0 0 0 0 0 0 0 0999 V2000 6.5335 5.0613 -0.4837 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6675 3.8427 0.1807 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8948 2.7349 -0.0137 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8673 2.7293 -0.9286 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0784 1.6342 -1.1431 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2720 0.4801 -0.4518 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4689 -0.7223 -0.5446 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2350 -0.7470 -1.1118 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5536 0.3356 -1.6613 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6274 1.0692 -0.8706 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6519 0.3900 -1.0061 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4850 0.7679 0.0088 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8502 0.1624 -0.2690 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7637 0.5028 0.7296 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0137 -0.0444 0.4778 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9862 0.9230 0.2856 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1940 0.4290 -0.1175 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0430 -0.0660 -1.5511 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6958 -0.7212 0.7037 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0947 -0.1945 1.9538 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6547 -1.7642 0.9689 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1101 -2.7541 1.8248 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4300 -1.0577 1.5316 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4176 -2.0004 1.6497 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6988 2.2573 0.0978 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6882 2.6143 -0.7930 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4832 3.0661 -0.1297 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3354 3.2230 0.9621 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3186 2.4538 -1.2893 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3517 3.3146 -1.5169 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5768 -1.9913 -1.1341 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4495 -2.0790 -1.6414 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1925 -3.0980 -0.5921 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6031 -4.3485 -0.5788 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3494 -4.4809 -1.1346 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2543 -5.4474 -0.0201 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4971 -5.3085 0.5293 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1350 -6.4049 1.0814 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1064 -4.0858 0.5316 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4527 -2.9955 -0.0263 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0111 -1.8359 -0.0335 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3150 0.4895 0.4739 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1189 1.5811 0.7022 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1561 1.5325 1.6490 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3570 0.3323 2.3654 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4725 5.6597 -0.4228 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3128 4.9550 -1.5671 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7322 5.7057 -0.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7233 3.6732 -1.4794 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3220 1.6781 -1.8865 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.8975 0.1911 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1368 0.3398 0.9660 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2547 0.6175 -1.2147 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8097 -0.9285 -0.4433 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9368 -0.6135 -0.4725 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9967 1.2033 -0.1569 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0284 -0.0238 -2.0438 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6875 -1.0973 -1.6144 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3808 0.6556 -2.0873 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6300 -1.1481 0.2702 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7113 0.6874 2.1244 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3916 -2.2929 0.0070 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6501 -2.3882 2.5521 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7157 -0.5916 2.4771 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7296 -2.7631 2.1702 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0625 2.4569 1.1404 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3565 3.2605 -1.4586 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7837 4.0791 -0.5000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3545 2.3999 1.4868 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3602 2.4037 -2.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8622 3.4472 -0.6912 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3179 -5.0544 -0.6285 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7354 -6.4029 -0.0416 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0194 -6.3702 1.5431 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0906 -3.9675 0.9650 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5480 -0.3960 1.0786 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7127 -0.4374 1.6503 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4454 0.0569 2.8965 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2253 0.5190 3.0527 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 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 12 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 8 31 1 0 31 32 2 0 31 33 1 0 33 34 2 0 34 35 1 0 34 36 1 0 36 37 2 0 37 38 1 0 37 39 1 0 39 40 2 0 40 41 1 0 6 42 1 0 42 43 2 0 43 44 1 0 44 45 1 0 43 3 1 0 41 7 1 0 29 10 1 0 40 33 1 0 23 15 1 0 1 46 1 0 1 47 1 0 1 48 1 0 4 49 1 0 5 50 1 0 10 51 1 1 12 52 1 1 13 53 1 0 13 54 1 0 15 55 1 6 17 56 1 6 18 57 1 0 18 58 1 0 18 59 1 0 19 60 1 6 20 61 1 0 21 62 1 6 22 63 1 0 23 64 1 1 24 65 1 0 25 66 1 1 26 67 1 0 27 68 1 6 28 69 1 0 29 70 1 6 30 71 1 0 35 72 1 0 36 73 1 0 38 74 1 0 39 75 1 0 42 76 1 0 45 77 1 0 45 78 1 0 45 79 1 0 M END

Standard InCHIKey	QYQFHIAAHONCJP-OAKFJBMTSA-N
Standard InCHI	InChI=1S/C29H34O16/c1-10-19(32)22(35)24(37)28(42-10)41-9-17-20(33)23(36)25(38)29(44-17)45-27-21(34)18-13(31)7-12(30)8-16(18)43-26(27)11-4-5-14(39-2)15(6-11)40-3/h4-8,10,17,19-20,22-25,28-33,35-38H,9H2,1-3H3/t10-,17+,19-,20-,22-,23+,24+,25+,28+,29-/m0/s1
SMILES	COC1=CC=C(C2=C(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@@H](O)[C@H]3O)C(=O)C3=C(O)C=C(O)C=C3O2)C=C1OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	638.18	Volume:	586.91 ? Van der Waals volume.
Dense:	1.087	LogP:	0.878 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.26 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.683 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	30.0
TPSA:	247.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.146	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.701	Fsp³:	0.483
MCE-18:	121.279 ? 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:	0.6	Fluc inhibitor:	0.276 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.712 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.635 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.044	Promiscuous compounds:	0.436

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.284	MDCK Permeability:	-5.411
Pgp-inhibitor:	0.002	Pgp-substrate:	0.985
PAMPA:	0.997 ? 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):	0.756
20% Bioavailability (F20%):	0.156	30% Bioavailability (F30%):	0.931
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.171
Plasma Protein Binding (PPB):	86.38%	Volume Distribution (VD):	-0.13
Fu:	11.348% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.899
OATP1B3 inhibitor:	0.997	BCRP inhibitor:	0.963
BSEP inhibitor:	0.088

ADMET: Metabolism

CYP1A2-inhibitor:	0.01	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:	0.003
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.507
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.97 ? 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):

1.285

Half-life (T1/2):

3.35

ADMET: Toxicity

hERG Blockers:	0.015	hERG Blockers (10um):	0.167
Human Hepatotoxicity (H-HT):	0.42	Drug-induced Liver Injury (DILI):	0.852
AMES Toxicity:	0.923	Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.059	Skin Sensitization:	0.995
Carcinogencity:	0.14	Eye Corrosion:	0.0
Eye Irritation:	0.427	Respiratory Toxicity:	0.043
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.854
Hematotoxicity:	0.199	Drug-induced Nephrotoxicity:	0.25
Genotoxicity:	0.737	RPMI-8226 Immunitoxicity:	0.191
A549 Cytotoxicity:	0.655	Hek293 Cytotoxicity:	0.733
BCF:	0.366 ? 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:	3.121 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.635 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.786 ? 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
NPO24419	Anvillea garcinii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087618]
NPO24419	Anvillea garcinii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699183]
NPO24419	Anvillea garcinii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24419	Anvillea garcinii	Species	Asteraceae	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 NPC563654 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	15908
0.1-0.2	29694
0.2-0.3	3210
0.3-0.4	554
0.4-0.5	251
0.5-0.6	107
0.6-0.7	68
0.7-0.8	1
0.8-0.85	15
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8506	High Similarity	NPC473327
0.8315	Intermediate Similarity	NPC476472
0.8315	Intermediate Similarity	NPC294815
0.8315	Intermediate Similarity	NPC16194
0.814	Intermediate Similarity	NPC173582
0.814	Intermediate Similarity	NPC265885
0.814	Intermediate Similarity	NPC181465
0.814	Intermediate Similarity	NPC215710
0.814	Intermediate Similarity	NPC473438
0.814	Intermediate Similarity	NPC253788
0.8046	Intermediate Similarity	NPC203259
0.8046	Intermediate Similarity	NPC33054
0.8046	Intermediate Similarity	NPC176740
0.8046	Intermediate Similarity	NPC471725
0.8046	Intermediate Similarity	NPC134532
0.8046	Intermediate Similarity	NPC602582
0.7931	Intermediate Similarity	NPC39834
0.7245	Intermediate Similarity	NPC477895
0.7222	Intermediate Similarity	NPC187379
0.7097	Intermediate Similarity	NPC153755
0.7071	Intermediate Similarity	NPC173837
0.7065	Intermediate Similarity	NPC156869
0.7041	Intermediate Similarity	NPC89052
0.7033	Intermediate Similarity	NPC471079
0.7033	Intermediate Similarity	NPC609888
0.6989	Remote Similarity	NPC473571
0.6989	Remote Similarity	NPC110941
0.6957	Remote Similarity	NPC67326
0.6932	Remote Similarity	NPC219904
0.6915	Remote Similarity	NPC126784
0.6915	Remote Similarity	NPC241423
0.6842	Remote Similarity	NPC12013
0.6842	Remote Similarity	NPC11432
0.6842	Remote Similarity	NPC477613
0.6813	Remote Similarity	NPC116864
0.6813	Remote Similarity	NPC244776
0.6804	Remote Similarity	NPC89127
0.68	Remote Similarity	NPC189564
0.6778	Remote Similarity	NPC223747
0.6771	Remote Similarity	NPC122467
0.6733	Remote Similarity	NPC292019
0.6733	Remote Similarity	NPC202908
0.6702	Remote Similarity	NPC65563
0.6702	Remote Similarity	NPC470949
0.67	Remote Similarity	NPC203145
0.6632	Remote Similarity	NPC186816
0.6591	Remote Similarity	NPC265530
0.6569	Remote Similarity	NPC48984
0.6566	Remote Similarity	NPC221342
0.6566	Remote Similarity	NPC476470
0.6552	Remote Similarity	NPC111929
0.6552	Remote Similarity	NPC320283
0.6552	Remote Similarity	NPC41121
0.65	Remote Similarity	NPC602448
0.6495	Remote Similarity	NPC470443
0.6477	Remote Similarity	NPC127546
0.6477	Remote Similarity	NPC57625
0.6477	Remote Similarity	NPC173637
0.6477	Remote Similarity	NPC317489
0.6477	Remote Similarity	NPC223424
0.6477	Remote Similarity	NPC600591
0.6422	Remote Similarity	NPC192539
0.6364	Remote Similarity	NPC135599
0.6364	Remote Similarity	NPC73855
0.6364	Remote Similarity	NPC113968
0.6364	Remote Similarity	NPC328940
0.6364	Remote Similarity	NPC277174
0.6364	Remote Similarity	NPC606877
0.6346	Remote Similarity	NPC217520
0.633	Remote Similarity	NPC241781
0.6264	Remote Similarity	NPC472459
0.6226	Remote Similarity	NPC139571
0.6196	Remote Similarity	NPC175107
0.619	Remote Similarity	NPC303694
0.6147	Remote Similarity	NPC162394
0.614	Remote Similarity	NPC473554
0.6139	Remote Similarity	NPC85751
0.6139	Remote Similarity	NPC473073
0.6139	Remote Similarity	NPC471669
0.6139	Remote Similarity	NPC19240
0.6129	Remote Similarity	NPC120099
0.6122	Remote Similarity	NPC129264
0.6061	Remote Similarity	NPC488073
0.6061	Remote Similarity	NPC475366
0.6061	Remote Similarity	NPC488074
0.6044	Remote Similarity	NPC64305
0.602	Remote Similarity	NPC605592
0.6019	Remote Similarity	NPC223426
0.6	Remote Similarity	NPC156785
0.6	Remote Similarity	NPC203050
0.6	Remote Similarity	NPC225434
0.6	Remote Similarity	NPC474522
0.6	Remote Similarity	NPC476215
0.598	Remote Similarity	NPC470447
0.598	Remote Similarity	NPC220173
0.5962	Remote Similarity	NPC214621
0.5962	Remote Similarity	NPC34267
0.5962	Remote Similarity	NPC81042
0.5941	Remote Similarity	NPC37668
0.5941	Remote Similarity	NPC270448
0.5938	Remote Similarity	NPC95866
0.5922	Remote Similarity	NPC287889
0.5922	Remote Similarity	NPC470449
0.5922	Remote Similarity	NPC470445
0.5914	Remote Similarity	NPC325555
0.5914	Remote Similarity	NPC226304
0.59	Remote Similarity	NPC470125
0.5882	Remote Similarity	NPC142142
0.5865	Remote Similarity	NPC470446
0.5859	Remote Similarity	NPC22062
0.5859	Remote Similarity	NPC473634
0.5859	Remote Similarity	NPC138811
0.5854	Remote Similarity	NPC603596
0.5851	Remote Similarity	NPC60735
0.5851	Remote Similarity	NPC26230
0.58	Remote Similarity	NPC204693
0.5789	Remote Similarity	NPC609478
0.5784	Remote Similarity	NPC209296
0.5769	Remote Similarity	NPC292929
0.5766	Remote Similarity	NPC480445
0.5761	Remote Similarity	NPC77672
0.5761	Remote Similarity	NPC133671
0.5761	Remote Similarity	NPC135391
0.5761	Remote Similarity	NPC78263
0.5761	Remote Similarity	NPC250069
0.5758	Remote Similarity	NPC163242
0.5758	Remote Similarity	NPC272068
0.5758	Remote Similarity	NPC67105
0.57	Remote Similarity	NPC155877
0.5699	Remote Similarity	NPC145038
0.5699	Remote Similarity	NPC56077
0.5699	Remote Similarity	NPC281131
0.5699	Remote Similarity	NPC253662
0.5699	Remote Similarity	NPC179950
0.5699	Remote Similarity	NPC88789
0.5699	Remote Similarity	NPC491374
0.5673	Remote Similarity	NPC76831
0.5664	Remote Similarity	NPC480444
0.5656	Remote Similarity	NPC487500
0.5641	Remote Similarity	NPC487499
0.5638	Remote Similarity	NPC46420
0.561	Remote Similarity	NPC487501
0.56	Remote Similarity	NPC227508
0.5596	Remote Similarity	NPC25523
0.5591	Remote Similarity	NPC19388
0.5591	Remote Similarity	NPC240431
0.5591	Remote Similarity	NPC55786
0.5583	Remote Similarity	NPC487502
0.5567	Remote Similarity	NPC88023
0.5567	Remote Similarity	NPC209023
0.5567	Remote Similarity	NPC309025
0.5536	Remote Similarity	NPC488734
0.5536	Remote Similarity	NPC488735
0.5536	Remote Similarity	NPC488739
0.5536	Remote Similarity	NPC488732
0.5536	Remote Similarity	NPC488738
0.5521	Remote Similarity	NPC159579
0.5521	Remote Similarity	NPC611303
0.5514	Remote Similarity	NPC470455
0.5505	Remote Similarity	NPC219043
0.55	Remote Similarity	NPC139320
0.5495	Remote Similarity	NPC54802
0.5495	Remote Similarity	NPC197304
0.5474	Remote Similarity	NPC305811
0.5474	Remote Similarity	NPC271692
0.5462	Remote Similarity	NPC275977
0.5455	Remote Similarity	NPC480441
0.5446	Remote Similarity	NPC44931
0.5446	Remote Similarity	NPC471748
0.5439	Remote Similarity	NPC488740
0.5439	Remote Similarity	NPC488736
0.5439	Remote Similarity	NPC488733
0.5437	Remote Similarity	NPC296018
0.5437	Remote Similarity	NPC154741
0.5435	Remote Similarity	NPC288084
0.5435	Remote Similarity	NPC276222
0.5435	Remote Similarity	NPC274618
0.5435	Remote Similarity	NPC118284
0.5435	Remote Similarity	NPC608147
0.5417	Remote Similarity	NPC216496
0.5413	Remote Similarity	NPC470451
0.5392	Remote Similarity	NPC210073
0.5376	Remote Similarity	NPC67037
0.5376	Remote Similarity	NPC255615
0.5372	Remote Similarity	NPC72554
0.5368	Remote Similarity	NPC158674
0.5361	Remote Similarity	NPC182121
0.5347	Remote Similarity	NPC29958
0.5345	Remote Similarity	NPC488737
0.5333	Remote Similarity	NPC231787
0.5327	Remote Similarity	NPC36138
0.5321	Remote Similarity	NPC121703
0.5312	Remote Similarity	NPC27640
0.5294	Remote Similarity	NPC470405
0.5288	Remote Similarity	NPC284277
0.5288	Remote Similarity	NPC475497
0.5285	Remote Similarity	NPC249560
0.5269	Remote Similarity	NPC34531
0.5263	Remote Similarity	NPC249281
0.5246	Remote Similarity	NPC30011

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC563654 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4792
0.1-0.2	4290
0.2-0.3	55
0.3-0.4	7
0.4-0.5	1
0.5-0.6	2
0.6-0.7	1
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8046	Intermediate Similarity	NPD6797	Phase 2
0.7216	Intermediate Similarity	NPD7808	Phase 3
0.6139	Remote Similarity	NPD7251	Phase 2
0.5784	Remote Similarity	NPD7054	Phase 4
0.5182	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