NPASS Compound

Natural Product: NPC562895

Natural Product ID	NPC562895
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)-7-[(2~{S},3~{S},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},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	5-hydroxy-2-(4-methoxyphenyl)-7-[(2~{S},3~{S},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},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 74 78 0 0 0 0 0 0 0 0999 V2000 11.3270 1.9583 -1.8124 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0216 1.6696 -2.2185 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0386 1.3451 -1.2861 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7824 1.0766 -1.7711 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7786 0.7531 -0.9028 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0104 0.6927 0.4514 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9178 0.3493 1.3394 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0979 0.2694 2.7107 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9897 -0.0655 3.4742 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0639 -0.1605 4.7277 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7887 -0.2963 2.8321 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6440 -0.6345 3.5397 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7775 -0.7279 4.9311 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -0.8698 2.9166 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3226 -0.7729 1.5452 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1292 -1.0058 0.9531 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2451 -0.9823 -0.3792 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1543 0.0139 -0.6945 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4176 -0.1488 -0.1462 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3760 0.5390 -1.0886 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6941 0.4872 -0.7096 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4921 1.1501 -1.6359 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0653 2.2493 -0.9940 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7108 1.7586 0.1464 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0873 2.8136 1.1327 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9329 0.9471 -0.2523 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0558 -0.1918 0.5260 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9121 0.6435 -1.7354 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7419 -0.4572 -1.9433 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5558 0.3266 -2.2564 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3506 -1.0485 -2.1119 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8182 -1.6158 -0.0996 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1741 -1.8230 -0.0665 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1149 -2.2640 -1.2722 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6495 -3.5148 -1.5666 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6501 -2.3537 -0.9006 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5871 -3.3021 0.1471 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4468 -0.4394 0.8326 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6708 -0.2018 1.4605 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7417 0.1147 0.8019 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2657 0.9611 0.9328 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2992 1.2925 0.0590 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3485 2.9810 -1.3795 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6973 1.2536 -1.0299 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9911 1.9159 -2.6989 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5965 1.1244 -2.8545 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7694 0.5368 -1.2798 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0570 0.4561 3.1816 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3985 -0.0171 5.5424 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6056 -1.1275 3.5666 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6685 -0.7227 -0.9855 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5263 0.2625 0.8657 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0907 1.6343 -1.0288 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2039 0.1721 -2.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8095 1.5240 -2.4418 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0047 1.0540 0.6308 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1623 3.0975 1.0252 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9929 2.4499 2.1957 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5025 3.7334 1.0709 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8177 1.5884 -0.0636 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2497 -0.4562 1.0118 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3604 1.4788 -2.3313 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9085 -0.9689 -1.0978 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5803 0.5252 -3.3624 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1857 -1.4888 -2.4104 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3705 -2.1047 0.8143 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4665 -2.6330 -0.5539 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1734 -1.5690 -2.1285 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0381 -3.9190 -2.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0790 -2.6833 -1.7733 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3483 -3.6719 0.0782 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4771 -0.3348 -0.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5116 0.9292 1.9892 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2932 1.5063 0.4382 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 2 0 9 11 1 0 11 12 2 0 12 13 1 0 12 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 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 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 19 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 15 38 1 0 38 39 2 0 39 40 1 0 6 41 1 0 41 42 2 0 42 3 1 0 40 7 1 0 39 11 1 0 36 17 1 0 30 22 1 0 1 43 1 0 1 44 1 0 1 45 1 0 4 46 1 0 5 47 1 0 8 48 1 0 13 49 1 0 14 50 1 0 17 51 1 6 19 52 1 1 20 53 1 0 20 54 1 0 22 55 1 6 24 56 1 1 25 57 1 0 25 58 1 0 25 59 1 0 26 60 1 6 27 61 1 0 28 62 1 6 29 63 1 0 30 64 1 6 31 65 1 0 32 66 1 1 33 67 1 0 34 68 1 6 35 69 1 0 36 70 1 6 37 71 1 0 38 72 1 0 41 73 1 0 42 74 1 0 M END

Standard InCHIKey	YFVGIJBUXMQFOF-SAXLCNSLSA-N
Standard InCHI	InChI=1S/C28H32O14/c1-11-21(31)23(33)25(35)27(39-11)38-10-19-22(32)24(34)26(36)28(42-19)40-14-7-15(29)20-16(30)9-17(41-18(20)8-14)12-3-5-13(37-2)6-4-12/h3-9,11,19,21-29,31-36H,10H2,1-2H3/t11-,19-,21-,22+,23-,24-,25-,26-,27+,28+/m0/s1
SMILES	COC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[C@@H]4O[C@@H](CO[C@@H]5O[C@@H](C)[C@H](O)[C@H](O)[C@@H]5O)[C@@H](O)[C@H](O)[C@@H]4O)C=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	592.18	Volume:	552.033 ? Van der Waals volume.
Dense:	1.073	LogP:	1.153 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.57 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.46 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	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:	0.179	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.562	Fsp³:	0.464
MCE-18:	115.098 ? 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:	0.634	Fluc inhibitor:	0.498 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.97 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.827 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.075	Promiscuous compounds:	0.285

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.259	MDCK Permeability:	-5.248
Pgp-inhibitor:	0.0	Pgp-substrate:	0.994
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):	0.986
20% Bioavailability (F20%):	0.991	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.899
Plasma Protein Binding (PPB):	87.574%	Volume Distribution (VD):	-0.064
Fu:	12.741% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.807
OATP1B3 inhibitor:	0.978	BCRP inhibitor:	0.075
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.004	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:	0.052
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.726
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.438 ? 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):

1.314

Half-life (T1/2):

2.785

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.109
Human Hepatotoxicity (H-HT):	0.569	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.99	Rat Oral Acute Toxicity:	0.084
Maximum Recommended Daily Dose:	0.078	Skin Sensitization:	1.0
Carcinogencity:	0.425	Eye Corrosion:	0.0
Eye Irritation:	0.385	Respiratory Toxicity:	0.268
Drug-induced Neurotoxicity:	0.011	Ototoxicity:	0.838
Hematotoxicity:	0.783	Drug-induced Nephrotoxicity:	0.844
Genotoxicity:	0.924	RPMI-8226 Immunitoxicity:	0.4
A549 Cytotoxicity:	0.979	Hek293 Cytotoxicity:	0.786
BCF:	0.395 ? 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:	3.157 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.61 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.836 ? 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
NPO9064	Cirsium arvense	Species	Asteraceae	Eukaryota	n.a.	fruit	n.a.	PMID[22396124]
NPO9064	Cirsium arvense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO64154	Mentha aquatica L.	Genus	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12524	Teucridium parvifolium	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO59496	Melandrum firmum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9064	Cirsium arvense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19021	Linaria vulgaris	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12524	Teucridium parvifolium	Species	Lamiaceae	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 NPC562895 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	16645
0.1-0.2	28680
0.2-0.3	3439
0.3-0.4	655
0.4-0.5	274
0.5-0.6	93
0.6-0.7	46
0.7-0.8	0
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC22062
1.0	High Similarity	NPC473634
1.0	High Similarity	NPC138811
0.8795	High Similarity	NPC209296
0.8642	High Similarity	NPC44931
0.8353	Intermediate Similarity	NPC473623
0.8313	Intermediate Similarity	NPC210073
0.8256	Intermediate Similarity	NPC488089
0.8214	Intermediate Similarity	NPC204693
0.8	Intermediate Similarity	NPC11468
0.7553	Intermediate Similarity	NPC473644
0.75	Intermediate Similarity	NPC46202
0.7474	Intermediate Similarity	NPC311850
0.7317	Intermediate Similarity	NPC181712
0.7283	Intermediate Similarity	NPC101636
0.7245	Intermediate Similarity	NPC68592
0.7195	Intermediate Similarity	NPC95090
0.7195	Intermediate Similarity	NPC27408
0.7174	Intermediate Similarity	NPC475382
0.6966	Remote Similarity	NPC67105
0.6951	Remote Similarity	NPC331652
0.69	Remote Similarity	NPC488086
0.6869	Remote Similarity	NPC488087
0.6827	Remote Similarity	NPC262222
0.6818	Remote Similarity	NPC211594
0.6813	Remote Similarity	NPC186816
0.6778	Remote Similarity	NPC227508
0.6774	Remote Similarity	NPC483707
0.6739	Remote Similarity	NPC475366
0.6737	Remote Similarity	NPC298171
0.67	Remote Similarity	NPC488083
0.6667	Remote Similarity	NPC198199
0.6667	Remote Similarity	NPC19709
0.6667	Remote Similarity	NPC65711
0.6559	Remote Similarity	NPC64051
0.6548	Remote Similarity	NPC473043
0.6505	Remote Similarity	NPC298666
0.6484	Remote Similarity	NPC295613
0.6484	Remote Similarity	NPC473657
0.6476	Remote Similarity	NPC120952
0.6437	Remote Similarity	NPC27942
0.6421	Remote Similarity	NPC229409
0.6354	Remote Similarity	NPC270675
0.6354	Remote Similarity	NPC195685
0.6344	Remote Similarity	NPC303913
0.6327	Remote Similarity	NPC135358
0.6304	Remote Similarity	NPC187379
0.6292	Remote Similarity	NPC22832
0.6292	Remote Similarity	NPC243930
0.6238	Remote Similarity	NPC472993
0.6222	Remote Similarity	NPC607707
0.617	Remote Similarity	NPC65003
0.6162	Remote Similarity	NPC472994
0.6154	Remote Similarity	NPC488088
0.6154	Remote Similarity	NPC190003
0.6111	Remote Similarity	NPC80188
0.6092	Remote Similarity	NPC39360
0.6092	Remote Similarity	NPC29763
0.6092	Remote Similarity	NPC210003
0.6087	Remote Similarity	NPC172807
0.6044	Remote Similarity	NPC220169
0.602	Remote Similarity	NPC142142
0.602	Remote Similarity	NPC479766
0.6	Remote Similarity	NPC473512
0.6	Remote Similarity	NPC129827
0.596	Remote Similarity	NPC195257
0.596	Remote Similarity	NPC479765
0.5938	Remote Similarity	NPC115674
0.5934	Remote Similarity	NPC608742
0.5921	Remote Similarity	NPC29353
0.5918	Remote Similarity	NPC473327
0.5895	Remote Similarity	NPC275454
0.587	Remote Similarity	NPC311830
0.5865	Remote Similarity	NPC480441
0.5865	Remote Similarity	NPC25523
0.5851	Remote Similarity	NPC254540
0.5843	Remote Similarity	NPC189142
0.5843	Remote Similarity	NPC77660
0.5824	Remote Similarity	NPC611303
0.5816	Remote Similarity	NPC470443
0.5778	Remote Similarity	NPC186807
0.573	Remote Similarity	NPC58053
0.573	Remote Similarity	NPC261866
0.5714	Remote Similarity	NPC284277
0.5714	Remote Similarity	NPC475497
0.567	Remote Similarity	NPC475155
0.5612	Remote Similarity	NPC257566
0.5612	Remote Similarity	NPC473571
0.5612	Remote Similarity	NPC110941
0.5604	Remote Similarity	NPC46420
0.5604	Remote Similarity	NPC271692
0.5591	Remote Similarity	NPC601144
0.5567	Remote Similarity	NPC173582
0.5567	Remote Similarity	NPC265885
0.5567	Remote Similarity	NPC181465
0.5567	Remote Similarity	NPC215710
0.5567	Remote Similarity	NPC473438
0.5567	Remote Similarity	NPC253788
0.5556	Remote Similarity	NPC126784
0.5556	Remote Similarity	NPC108831
0.5556	Remote Similarity	NPC241423
0.5556	Remote Similarity	NPC238376
0.5556	Remote Similarity	NPC182634
0.5532	Remote Similarity	NPC99957
0.551	Remote Similarity	NPC203259
0.551	Remote Similarity	NPC479405
0.551	Remote Similarity	NPC33054
0.551	Remote Similarity	NPC176740
0.551	Remote Similarity	NPC471725
0.551	Remote Similarity	NPC134532
0.551	Remote Similarity	NPC602582
0.5495	Remote Similarity	NPC158674
0.549	Remote Similarity	NPC476472
0.549	Remote Similarity	NPC294815
0.549	Remote Similarity	NPC16194
0.549	Remote Similarity	NPC477629
0.5455	Remote Similarity	NPC479404
0.5408	Remote Similarity	NPC15358
0.5408	Remote Similarity	NPC39834
0.5385	Remote Similarity	NPC249281
0.5385	Remote Similarity	NPC143851
0.5361	Remote Similarity	NPC8856
0.5354	Remote Similarity	NPC65563
0.5354	Remote Similarity	NPC470949
0.5347	Remote Similarity	NPC479403
0.534	Remote Similarity	NPC473073
0.5333	Remote Similarity	NPC244875
0.5312	Remote Similarity	NPC276377
0.5294	Remote Similarity	NPC606657
0.5275	Remote Similarity	NPC160515
0.5263	Remote Similarity	NPC181616
0.5229	Remote Similarity	NPC277532
0.5217	Remote Similarity	NPC289667
0.5204	Remote Similarity	NPC251417
0.5192	Remote Similarity	NPC80068
0.5189	Remote Similarity	NPC14187
0.5176	Remote Similarity	NPC469622
0.5146	Remote Similarity	NPC32641
0.5146	Remote Similarity	NPC256188
0.5143	Remote Similarity	NPC287889
0.514	Remote Similarity	NPC121703
0.5125	Remote Similarity	NPC127447
0.5111	Remote Similarity	NPC248739
0.5109	Remote Similarity	NPC14606
0.5109	Remote Similarity	NPC114740
0.5104	Remote Similarity	NPC486578
0.5098	Remote Similarity	NPC240306
0.5096	Remote Similarity	NPC486577
0.5094	Remote Similarity	NPC179862
0.5062	Remote Similarity	NPC234133
0.506	Remote Similarity	NPC195202
0.506	Remote Similarity	NPC223579
0.5052	Remote Similarity	NPC116458
0.5052	Remote Similarity	NPC246943
0.5052	Remote Similarity	NPC605784
0.505	Remote Similarity	NPC102028
0.505	Remote Similarity	NPC150164
0.5046	Remote Similarity	NPC480796

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC562895 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4539
0.1-0.2	4507
0.2-0.3	90
0.3-0.4	7
0.4-0.5	2
0.5-0.6	1
0.6-0.7	3
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	Drug ID	Developmental Stage
0.8795	High Similarity	NPD7054	Phase 4
0.6531	Remote Similarity	NPD7472	Pre-clinical
0.6364	Remote Similarity	NPD7808	Phase 3
0.6289	Remote Similarity	NPD7251	Phase 2
0.551	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