NPASS Compound

Natural Product: NPC579322

Natural Product ID	NPC579322
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~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-2-(4-methoxyphenyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-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 75 79 0 0 0 0 0 0 0 0999 V2000 -3.3937 6.1218 -2.0686 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9571 4.8699 -2.4105 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3080 3.7049 -2.0465 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1254 3.7212 -1.3581 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4679 2.5685 -0.9890 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9757 1.3111 -1.2990 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2164 0.1247 -0.9384 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7407 -1.1240 -0.9655 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0250 -1.4978 -1.3019 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0240 -1.6868 -0.2845 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0809 -3.0944 -0.1628 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8512 -3.4067 0.9254 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4613 -2.7506 2.2062 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2823 -3.1589 0.5483 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6702 -4.2577 -0.2548 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5363 -1.8884 -0.1609 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3208 -1.0856 0.6740 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3346 -1.0896 -0.5742 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4187 0.2066 -0.0042 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9001 -2.1727 -0.6020 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3217 -3.3450 -0.6091 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4009 -1.8909 -0.2357 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2408 -2.9218 0.1273 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7283 -4.2090 0.1045 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 -2.6237 0.4890 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0245 -1.3281 0.5062 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3324 -1.1916 0.8908 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9796 0.0234 0.9578 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0500 -0.0019 0.0257 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5691 1.2952 0.0151 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5024 1.3743 -1.1761 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0958 2.6152 -1.3144 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3068 1.5397 1.3136 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8690 2.6846 1.9741 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0376 0.3591 2.2552 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6203 -0.7617 1.6672 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5508 0.1665 2.3613 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9376 1.2452 2.9585 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1977 -0.3062 0.1484 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8878 -0.5927 -0.2215 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0549 0.3407 -0.5726 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1572 1.3065 -1.9876 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8328 2.4720 -2.3667 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0935 6.9440 -2.3286 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4317 6.2029 -2.6151 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1880 6.1104 -0.9796 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6859 4.6688 -1.0908 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5315 2.6663 -0.4435 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5794 -1.2817 0.6483 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7384 -4.5225 1.0747 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1199 -1.8776 2.4198 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6552 -3.4647 3.0560 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3819 -2.5048 2.2717 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8922 -3.2890 1.4897 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7934 -3.9462 -1.1926 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2104 -2.1042 -1.0413 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9821 -1.7201 1.0973 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4411 -0.9254 -1.6729 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6257 0.0734 0.9750 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5873 -4.6992 -0.7758 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1589 -3.4726 0.7696 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4043 0.9217 0.6807 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7595 2.0457 -0.1026 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2297 0.5416 -1.0837 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9000 1.1516 -2.0775 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6174 2.6178 -2.1476 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3917 1.6009 1.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5153 3.4097 1.7821 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4308 0.5393 3.2560 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2934 -1.6125 2.0563 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3525 -0.7278 2.9772 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0704 1.4664 2.5425 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5158 0.7252 0.1397 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6211 0.3923 -2.2997 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7679 2.4051 -2.9118 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 30 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 35 37 1 0 37 38 1 0 26 39 1 0 39 40 2 0 40 41 1 0 6 42 1 0 42 43 2 0 43 3 1 0 41 7 1 0 18 10 1 0 40 22 1 0 37 28 1 0 1 44 1 0 1 45 1 0 1 46 1 0 4 47 1 0 5 48 1 0 10 49 1 1 12 50 1 1 13 51 1 0 13 52 1 0 13 53 1 0 14 54 1 1 15 55 1 0 16 56 1 6 17 57 1 0 18 58 1 6 19 59 1 0 24 60 1 0 25 61 1 0 28 62 1 6 30 63 1 6 31 64 1 0 31 65 1 0 32 66 1 0 33 67 1 6 34 68 1 0 35 69 1 1 36 70 1 0 37 71 1 1 38 72 1 0 39 73 1 0 42 74 1 0 43 75 1 0 M END

Standard InCHIKey	JKVVNVBAADBSQA-YJYPXAJOSA-N
Standard InCHI	InChI=1S/C28H32O15/c1-10-18(31)21(34)23(36)27(39-10)43-26-20(33)17-14(30)7-13(40-28-24(37)22(35)19(32)16(9-29)42-28)8-15(17)41-25(26)11-3-5-12(38-2)6-4-11/h3-8,10,16,18-19,21-24,27-32,34-37H,9H2,1-2H3/t10-,16+,18-,19+,21+,22-,23+,24+,27-,28+/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]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	608.17	Volume:	560.823 ? Van der Waals volume.
Dense:	1.084	LogP:	1.086 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.729 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.566 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	30.0
TPSA:	238.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.153	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.604	Fsp³:	0.464
MCE-18:	118.585 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.615	Fluc inhibitor:	0.294 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.875 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.588 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.117	Promiscuous compounds:	0.394

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.426	MDCK Permeability:	-5.16
Pgp-inhibitor:	0.0	Pgp-substrate:	0.85
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):	0.904
20% Bioavailability (F20%):	0.028	30% Bioavailability (F30%):	0.925
50% Bioavailability (F50%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.027
Plasma Protein Binding (PPB):	83.618%	Volume Distribution (VD):	-0.086
Fu:	14.888% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.483
BSEP inhibitor:	0.011

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:	0.039
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.974
HLM stability:	0.185 ? 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):

1.829

Half-life (T1/2):

4.622

ADMET: Toxicity

hERG Blockers:	0.015	hERG Blockers (10um):	0.086
Human Hepatotoxicity (H-HT):	0.64	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.943	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.006	Skin Sensitization:	0.994
Carcinogencity:	0.084	Eye Corrosion:	0.0
Eye Irritation:	0.017	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.979
Hematotoxicity:	0.192	Drug-induced Nephrotoxicity:	0.796
Genotoxicity:	0.527	RPMI-8226 Immunitoxicity:	0.145
A549 Cytotoxicity:	0.2	Hek293 Cytotoxicity:	0.233
BCF:	0.402 ? 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:	3.182 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.764 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.882 ? 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
NPO47091	Asplenium bulbiferum	Species	Aspleniaceae	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 NPC579322 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	18436
0.1-0.2	27064
0.2-0.3	2989
0.3-0.4	811
0.4-0.5	294
0.5-0.6	105
0.6-0.7	72
0.7-0.8	1
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC289667
0.8553	High Similarity	NPC116458
0.8553	High Similarity	NPC246943
0.8462	Intermediate Similarity	NPC251417
0.8312	Intermediate Similarity	NPC605784
0.8052	Intermediate Similarity	NPC611303
0.7895	Intermediate Similarity	NPC297987
0.7792	Intermediate Similarity	NPC46420
0.7763	Intermediate Similarity	NPC249281
0.7662	Intermediate Similarity	NPC136042
0.7564	Intermediate Similarity	NPC84362
0.7564	Intermediate Similarity	NPC271692
0.7468	Intermediate Similarity	NPC472459
0.7436	Intermediate Similarity	NPC158674
0.7356	Intermediate Similarity	NPC35119
0.7215	Intermediate Similarity	NPC95090
0.7215	Intermediate Similarity	NPC27408
0.7159	Intermediate Similarity	NPC32641
0.7159	Intermediate Similarity	NPC256188
0.7126	Intermediate Similarity	NPC64425
0.7108	Intermediate Similarity	NPC276377
0.7079	Intermediate Similarity	NPC5319
0.7	Intermediate Similarity	NPC64305
0.6966	Remote Similarity	NPC606657
0.6897	Remote Similarity	NPC150164
0.6774	Remote Similarity	NPC14187
0.6771	Remote Similarity	NPC277532
0.6742	Remote Similarity	NPC240306
0.6667	Remote Similarity	NPC22832
0.6667	Remote Similarity	NPC480466
0.6667	Remote Similarity	NPC25523
0.6629	Remote Similarity	NPC186816
0.6593	Remote Similarity	NPC72016
0.6552	Remote Similarity	NPC480463
0.6506	Remote Similarity	NPC24043
0.6495	Remote Similarity	NPC480441
0.6471	Remote Similarity	NPC243930
0.6471	Remote Similarity	NPC120099
0.6471	Remote Similarity	NPC486578
0.64	Remote Similarity	NPC295625
0.6364	Remote Similarity	NPC470716
0.6353	Remote Similarity	NPC219904
0.6353	Remote Similarity	NPC285197
0.6353	Remote Similarity	NPC488071
0.6327	Remote Similarity	NPC470715
0.631	Remote Similarity	NPC27640
0.6279	Remote Similarity	NPC21666
0.6265	Remote Similarity	NPC77672
0.6265	Remote Similarity	NPC133671
0.6265	Remote Similarity	NPC135391
0.6265	Remote Similarity	NPC78263
0.6265	Remote Similarity	NPC250069
0.6214	Remote Similarity	NPC470720
0.6207	Remote Similarity	NPC607707
0.619	Remote Similarity	NPC277205
0.619	Remote Similarity	NPC37919
0.619	Remote Similarity	NPC189142
0.619	Remote Similarity	NPC77660
0.618	Remote Similarity	NPC278419
0.618	Remote Similarity	NPC179198
0.6163	Remote Similarity	NPC60735
0.6163	Remote Similarity	NPC26230
0.6162	Remote Similarity	NPC164704
0.6145	Remote Similarity	NPC111929
0.6145	Remote Similarity	NPC320283
0.6145	Remote Similarity	NPC41121
0.6118	Remote Similarity	NPC488080
0.6118	Remote Similarity	NPC169977
0.6117	Remote Similarity	NPC470717
0.6105	Remote Similarity	NPC475382
0.6092	Remote Similarity	NPC148710
0.6092	Remote Similarity	NPC609478
0.6071	Remote Similarity	NPC261866
0.6071	Remote Similarity	NPC39360
0.6071	Remote Similarity	NPC19709
0.6071	Remote Similarity	NPC29763
0.6071	Remote Similarity	NPC210003
0.6071	Remote Similarity	NPC238376
0.6047	Remote Similarity	NPC42773
0.6047	Remote Similarity	NPC59534
0.6047	Remote Similarity	NPC45522
0.6047	Remote Similarity	NPC325555
0.6047	Remote Similarity	NPC226304
0.6047	Remote Similarity	NPC599850
0.6023	Remote Similarity	NPC311830
0.6	Remote Similarity	NPC145038
0.6	Remote Similarity	NPC56077
0.6	Remote Similarity	NPC281131
0.6	Remote Similarity	NPC253662
0.6	Remote Similarity	NPC265530
0.6	Remote Similarity	NPC179950
0.6	Remote Similarity	NPC323593
0.6	Remote Similarity	NPC88789
0.6	Remote Similarity	NPC203500
0.6	Remote Similarity	NPC491374
0.5978	Remote Similarity	NPC22062
0.5978	Remote Similarity	NPC473634
0.5978	Remote Similarity	NPC138811
0.5962	Remote Similarity	NPC470719
0.5955	Remote Similarity	NPC203050
0.5955	Remote Similarity	NPC488072
0.5955	Remote Similarity	NPC225434
0.5952	Remote Similarity	NPC473043
0.5952	Remote Similarity	NPC331652
0.593	Remote Similarity	NPC186807
0.593	Remote Similarity	NPC305811
0.593	Remote Similarity	NPC181712
0.593	Remote Similarity	NPC349108
0.593	Remote Similarity	NPC73511
0.589	Remote Similarity	NPC262094
0.5889	Remote Similarity	NPC265115
0.5882	Remote Similarity	NPC127546
0.5882	Remote Similarity	NPC19388
0.5882	Remote Similarity	NPC58053
0.5882	Remote Similarity	NPC240431
0.5882	Remote Similarity	NPC57625
0.5882	Remote Similarity	NPC55786
0.5882	Remote Similarity	NPC108831
0.5882	Remote Similarity	NPC173637
0.5882	Remote Similarity	NPC317489
0.5882	Remote Similarity	NPC223424
0.5882	Remote Similarity	NPC182634
0.5882	Remote Similarity	NPC600591
0.5859	Remote Similarity	NPC121703
0.5843	Remote Similarity	NPC223747
0.5833	Remote Similarity	NPC142142
0.5816	Remote Similarity	NPC135358
0.5814	Remote Similarity	NPC234739
0.5789	Remote Similarity	NPC483414
0.5778	Remote Similarity	NPC267254
0.5778	Remote Similarity	NPC355481
0.5778	Remote Similarity	NPC601586
0.5765	Remote Similarity	NPC135599
0.5765	Remote Similarity	NPC73855
0.5765	Remote Similarity	NPC113968
0.5765	Remote Similarity	NPC328940
0.5765	Remote Similarity	NPC277174
0.5765	Remote Similarity	NPC160515
0.5765	Remote Similarity	NPC606877
0.5747	Remote Similarity	NPC603655
0.573	Remote Similarity	NPC101026
0.573	Remote Similarity	NPC488077
0.573	Remote Similarity	NPC601144
0.567	Remote Similarity	NPC486577
0.5632	Remote Similarity	NPC8573
0.5625	Remote Similarity	NPC483415
0.5618	Remote Similarity	NPC307938
0.5612	Remote Similarity	NPC76831
0.5567	Remote Similarity	NPC483416
0.5567	Remote Similarity	NPC209296
0.5556	Remote Similarity	NPC138990
0.5556	Remote Similarity	NPC80188
0.5542	Remote Similarity	NPC134819
0.5529	Remote Similarity	NPC288084
0.5506	Remote Similarity	NPC60966
0.5505	Remote Similarity	NPC175429
0.5495	Remote Similarity	NPC220169
0.5481	Remote Similarity	NPC311850
0.5455	Remote Similarity	NPC197896
0.5455	Remote Similarity	NPC313163
0.5444	Remote Similarity	NPC168584
0.5426	Remote Similarity	NPC139320
0.5422	Remote Similarity	NPC191154
0.5417	Remote Similarity	NPC115674
0.5417	Remote Similarity	NPC131745
0.5413	Remote Similarity	NPC209550
0.5408	Remote Similarity	NPC473327
0.5393	Remote Similarity	NPC22195
0.5393	Remote Similarity	NPC21190
0.5385	Remote Similarity	NPC605067
0.5368	Remote Similarity	NPC267680
0.5368	Remote Similarity	NPC163242
0.5368	Remote Similarity	NPC272068
0.5361	Remote Similarity	NPC46202
0.5341	Remote Similarity	NPC348541
0.5341	Remote Similarity	NPC143851
0.5327	Remote Similarity	NPC68592
0.5326	Remote Similarity	NPC206123
0.5319	Remote Similarity	NPC473682
0.5319	Remote Similarity	NPC487212
0.5312	Remote Similarity	NPC293626
0.5312	Remote Similarity	NPC65003
0.5306	Remote Similarity	NPC470443
0.5304	Remote Similarity	NPC223860
0.53	Remote Similarity	NPC195257
0.5287	Remote Similarity	NPC67037
0.5287	Remote Similarity	NPC255615
0.5278	Remote Similarity	NPC470713
0.5275	Remote Similarity	NPC80140
0.5275	Remote Similarity	NPC609451
0.5258	Remote Similarity	NPC470444
0.5256	Remote Similarity	NPC153758
0.5253	Remote Similarity	NPC124155
0.5253	Remote Similarity	NPC473623
0.5238	Remote Similarity	NPC470712
0.5222	Remote Similarity	NPC45638
0.5208	Remote Similarity	NPC173582
0.5208	Remote Similarity	NPC265885
0.5208	Remote Similarity	NPC181465
0.5208	Remote Similarity	NPC471748

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC579322 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4813
0.1-0.2	4238
0.2-0.3	84
0.3-0.4	8
0.4-0.5	2
0.5-0.6	2
0.6-0.7	1
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7079	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7808	Phase 3
0.5938	Remote Similarity	NPD7251	Phase 2
0.5567	Remote Similarity	NPD7054	Phase 4

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data