NPASS Compound

Natural Product: NPC579039

Natural Product ID	NPC579039
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{R},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-6,8-dimethoxy-2-(4-methoxyphenyl)-7-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{S},4~{R},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 82 86 0 0 0 0 0 0 0 0999 V2000 8.4388 5.0330 1.3001 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9885 3.8677 0.7663 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1761 2.7638 0.5514 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6901 1.6010 0.0267 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8588 0.4906 -0.1865 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5310 0.5331 0.1177 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6434 -0.5992 -0.0931 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1210 -1.7741 -0.6304 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2724 -2.8598 -0.8336 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6909 -3.9427 -1.3241 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9414 -2.7117 -0.4769 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0412 -3.7386 -0.6477 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4842 -4.9445 -1.1894 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7076 -3.5669 -0.2818 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8900 -4.6398 -0.4895 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2133 -4.8820 -1.7180 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2530 -2.3840 0.2549 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0736 -2.2260 0.6192 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1342 -1.7810 -0.1313 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5458 -0.4648 0.2419 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3007 0.0502 -0.8130 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4845 1.5112 -0.6989 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0890 2.0561 0.3676 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4110 1.8831 0.6218 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0169 3.1537 0.6548 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3841 3.0322 0.8218 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0470 2.1697 -0.2147 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6787 2.4867 2.1781 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5047 3.4106 3.2072 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9452 1.2134 2.4864 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6759 0.1025 2.0823 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5301 1.2143 1.9814 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6350 1.8127 2.8611 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5146 -0.7173 -1.1148 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1104 -0.2599 -2.2708 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1704 -2.2054 -1.3560 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3188 -2.9757 -1.3697 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3856 -2.5918 -0.0994 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2557 -3.9315 0.0888 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1912 -1.3950 0.4023 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8177 -0.1733 0.9322 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4010 0.8147 0.0036 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5337 -1.5106 0.0543 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3582 -0.5036 0.2341 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0387 1.7073 0.6418 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8373 2.8091 0.8590 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5234 5.3661 0.7488 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1290 5.8903 1.3076 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1287 4.8494 2.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7422 1.5769 -0.2111 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3415 -0.3754 -0.5981 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1584 -1.9196 -0.9195 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4689 -5.0161 -2.2007 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6011 -5.6149 -1.4769 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9696 -5.3367 -2.3962 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1724 -3.9157 -2.0777 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7726 -1.6213 -1.1897 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5773 -0.0866 -1.7095 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9351 1.9358 -1.6729 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4276 1.9577 -0.7489 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9046 1.3178 -0.1710 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8374 4.0390 0.7442 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0070 1.0972 -0.0046 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6882 2.4141 -1.2541 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1288 2.4490 -0.2290 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7780 2.2252 2.2007 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6196 3.8139 3.1912 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8806 1.1458 3.6108 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2753 -0.6959 2.5214 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2157 0.1638 1.8503 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7703 1.5215 3.7959 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2868 -0.7839 -0.3253 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 0.0453 -2.9652 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5456 -2.3169 -2.2344 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3944 -3.4743 -2.2097 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0456 -2.2086 0.7429 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3514 -4.1663 1.0496 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8170 1.5654 0.5701 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8318 0.3763 -0.8484 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2806 1.3200 -0.4755 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9778 1.8053 0.9074 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4385 3.7188 1.2686 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 1 0 15 16 1 0 14 17 2 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 25 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 21 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 17 40 1 0 40 41 1 0 41 42 1 0 40 43 2 0 43 44 1 0 6 45 1 0 45 46 2 0 46 3 1 0 44 7 1 0 43 11 1 0 38 19 1 0 32 24 1 0 1 47 1 0 1 48 1 0 1 49 1 0 4 50 1 0 5 51 1 0 8 52 1 0 13 53 1 0 16 54 1 0 16 55 1 0 16 56 1 0 19 57 1 6 21 58 1 6 22 59 1 0 22 60 1 0 24 61 1 6 26 62 1 1 27 63 1 0 27 64 1 0 27 65 1 0 28 66 1 6 29 67 1 0 30 68 1 1 31 69 1 0 32 70 1 6 33 71 1 0 34 72 1 1 35 73 1 0 36 74 1 6 37 75 1 0 38 76 1 1 39 77 1 0 42 78 1 0 42 79 1 0 42 80 1 0 45 81 1 0 46 82 1 0 M END

Standard InCHIKey	PAOUJIVFERPFRF-QRLVZTGASA-N
Standard InCHI	InChI=1S/C30H36O16/c1-11-18(32)21(35)23(37)29(43-11)42-10-16-19(33)22(36)24(38)30(45-16)46-28-26(40-3)20(34)17-14(31)9-15(44-25(17)27(28)41-4)12-5-7-13(39-2)8-6-12/h5-9,11,16,18-19,21-24,29-30,32-38H,10H2,1-4H3/t11-,16+,18-,19+,21+,22-,23-,24+,29+,30-/m0/s1
SMILES	COC1=CC=C(C2=CC(=O)C3=C(O)C(OC)=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(OC)=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	652.2	Volume:	604.206 ? Van der Waals volume.
Dense:	1.079	LogP:	0.918 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.48 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.378 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	30.0
TPSA:	236.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	7.0	Rings:	5.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.15	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.791	Fsp³:	0.5
MCE-18:	120.556 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.536	Fluc inhibitor:	0.251 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.707 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.643 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.034	Promiscuous compounds:	0.247

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.13	MDCK Permeability:	-5.348
Pgp-inhibitor:	0.0	Pgp-substrate:	0.811
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):	0.924
20% Bioavailability (F20%):	0.331	30% Bioavailability (F30%):	0.949
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.605
Plasma Protein Binding (PPB):	87.994%	Volume Distribution (VD):	-0.164
Fu:	11.498% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.073
BSEP inhibitor:	0.013

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:	0.004
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.396
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.164 ? 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):

1.465

Half-life (T1/2):

3.581

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.113
Human Hepatotoxicity (H-HT):	0.496	Drug-induced Liver Injury (DILI):	0.985
AMES Toxicity:	0.915	Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.04	Skin Sensitization:	0.985
Carcinogencity:	0.159	Eye Corrosion:	0.0
Eye Irritation:	0.026	Respiratory Toxicity:	0.013
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.931
Hematotoxicity:	0.42	Drug-induced Nephrotoxicity:	0.771
Genotoxicity:	0.641	RPMI-8226 Immunitoxicity:	0.38
A549 Cytotoxicity:	0.53	Hek293 Cytotoxicity:	0.541
BCF:	0.322 ? 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:	3.141 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.691 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.856 ? 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
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775221]
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26817	Lysionotus pauciflorus	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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 NPC579039 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	17081
0.1-0.2	28685
0.2-0.3	3157
0.3-0.4	652
0.4-0.5	212
0.5-0.6	59
0.6-0.7	7
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	Natural Product ID
0.7816	Intermediate Similarity	NPC204693
0.7303	Intermediate Similarity	NPC22062
0.7303	Intermediate Similarity	NPC473634
0.7303	Intermediate Similarity	NPC138811
0.6484	Remote Similarity	NPC211594
0.6458	Remote Similarity	NPC483707
0.6458	Remote Similarity	NPC209296
0.6289	Remote Similarity	NPC473623
0.6277	Remote Similarity	NPC44931
0.6061	Remote Similarity	NPC488089
0.6042	Remote Similarity	NPC210073
0.5922	Remote Similarity	NPC11468
0.5918	Remote Similarity	NPC475366
0.5833	Remote Similarity	NPC295613
0.5833	Remote Similarity	NPC187379
0.5833	Remote Similarity	NPC473657
0.5789	Remote Similarity	NPC172807
0.5755	Remote Similarity	NPC473644
0.5696	Remote Similarity	NPC176775
0.5579	Remote Similarity	NPC99957
0.5567	Remote Similarity	NPC254540
0.5556	Remote Similarity	NPC311850
0.55	Remote Similarity	NPC473571
0.55	Remote Similarity	NPC110941
0.549	Remote Similarity	NPC473327
0.5484	Remote Similarity	NPC186807
0.5446	Remote Similarity	NPC46202
0.5446	Remote Similarity	NPC126784
0.5446	Remote Similarity	NPC241423
0.5435	Remote Similarity	NPC58053
0.5405	Remote Similarity	NPC68592
0.54	Remote Similarity	NPC473512
0.54	Remote Similarity	NPC129827
0.54	Remote Similarity	NPC475155
0.5333	Remote Similarity	NPC101636
0.53	Remote Similarity	NPC67105
0.5243	Remote Similarity	NPC470443
0.5238	Remote Similarity	NPC475382
0.5238	Remote Similarity	NPC473073
0.5196	Remote Similarity	NPC186816
0.5158	Remote Similarity	NPC181712
0.5149	Remote Similarity	NPC173582
0.5149	Remote Similarity	NPC15358
0.5149	Remote Similarity	NPC265885
0.5149	Remote Similarity	NPC181465
0.5149	Remote Similarity	NPC215710
0.5149	Remote Similarity	NPC473438
0.5149	Remote Similarity	NPC227508
0.5149	Remote Similarity	NPC253788
0.5146	Remote Similarity	NPC284277
0.5146	Remote Similarity	NPC475497
0.5133	Remote Similarity	NPC488086
0.5128	Remote Similarity	NPC262222
0.5098	Remote Similarity	NPC203259
0.5098	Remote Similarity	NPC65563
0.5098	Remote Similarity	NPC33054
0.5098	Remote Similarity	NPC470949
0.5098	Remote Similarity	NPC176740
0.5098	Remote Similarity	NPC471725
0.5098	Remote Similarity	NPC134532
0.5098	Remote Similarity	NPC602582
0.5094	Remote Similarity	NPC476472
0.5094	Remote Similarity	NPC294815
0.5094	Remote Similarity	NPC16194
0.5089	Remote Similarity	NPC488087
0.5057	Remote Similarity	NPC469622
0.5056	Remote Similarity	NPC479450
0.5053	Remote Similarity	NPC95090
0.5053	Remote Similarity	NPC27408
0.5049	Remote Similarity	NPC257566

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC579039 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4655
0.1-0.2	4414
0.2-0.3	71
0.3-0.4	3
0.4-0.5	3
0.5-0.6	3
0.6-0.7	1
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
0.6458	Remote Similarity	NPD7054	Phase 4
0.5769	Remote Similarity	NPD7472	Pre-clinical
0.5098	Remote Similarity	NPD6797	Phase 2
0.5046	Remote Similarity	NPD7808	Phase 3

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