NPASS Compound

Natural Product: NPC543360

Natural Product ID	NPC543360
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	7-hydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-5-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	7-hydroxy-6,8-dimethoxy-2-(4-methoxyphenyl)-5-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)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 83 87 0 0 0 0 0 0 0 0999 V2000 9.5857 -0.3555 4.5811 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0269 -1.2784 3.6948 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9596 -0.9329 2.8675 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4412 -1.8901 2.0060 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3732 -1.5888 1.1596 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8016 -0.3504 1.1478 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6706 -0.0002 0.2745 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1128 -0.9384 -0.5633 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0339 -0.6452 -1.4068 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5639 -1.5326 -2.1603 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5321 0.6349 -1.3746 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4886 1.0359 -2.1573 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8555 0.1274 -3.0071 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4233 -0.4208 -2.6065 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1984 -1.4713 -1.7501 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3729 -2.0551 -1.2891 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2320 -1.0988 -0.5029 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3514 -1.7678 -0.0491 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2186 -0.9379 0.6565 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3133 -1.4435 1.9297 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2105 -0.8256 2.7555 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4626 -1.7787 3.9100 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3730 -1.1677 4.7518 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4461 -0.3038 2.1713 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9226 0.8378 2.8528 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4218 0.0308 0.7089 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7258 0.0779 0.1930 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5847 -0.9913 0.0058 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5300 -0.6882 -1.3416 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1751 -2.6096 -2.4580 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3539 -3.1479 -2.0109 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4610 -1.4972 -3.4455 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0442 -2.0964 -4.5791 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1427 -0.8600 -3.8161 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4296 0.1744 -4.7068 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0676 2.3540 -2.0701 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0163 2.8160 -2.8480 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2397 3.3858 -4.1072 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6588 3.2632 -1.2216 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2084 4.5787 -1.1604 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6994 2.8673 -0.4316 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3227 3.7691 0.4490 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8055 3.8696 1.7569 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1384 1.5544 -0.5071 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1510 1.1949 0.2545 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3367 0.5906 2.0178 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3903 0.3149 2.8611 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7257 0.6097 4.0659 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5658 -0.7721 4.9532 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9424 -0.2229 5.4848 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9003 -2.8702 2.0178 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0212 -2.3844 0.5142 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4703 -1.9509 -0.6236 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9127 0.4276 -2.0507 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1047 -2.8994 -0.6426 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6955 -0.7335 0.4001 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5684 -0.2236 -1.1225 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8366 0.0774 0.6707 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6639 0.0511 3.2204 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8162 -2.7663 3.5545 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5042 -1.8866 4.4997 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3084 -1.4218 4.5114 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2483 -1.0651 2.2895 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5853 1.2505 2.2419 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9736 1.0261 0.5417 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7763 -0.3689 -0.6684 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0186 -2.0172 0.0735 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8210 0.2073 -1.5877 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4941 -3.3510 -2.9555 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3198 -4.1519 -1.9674 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1361 -0.7289 -3.0157 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2698 -1.3409 -5.1775 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5388 -1.6609 -4.3024 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5585 0.4914 -5.0503 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3428 3.3424 -4.3269 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2513 2.8486 -4.9435 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1283 4.4388 -4.1727 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8391 4.9779 -0.3074 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3963 3.1899 2.4104 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7628 3.5105 1.7750 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7772 4.9188 2.1190 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9132 1.5723 2.0320 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7860 1.0728 3.5341 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 13 14 1 0 14 15 1 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 21 24 1 0 24 25 1 0 24 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 16 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 32 34 1 0 34 35 1 0 12 36 1 0 36 37 1 0 37 38 1 0 36 39 2 0 39 40 1 0 39 41 1 0 41 42 1 0 42 43 1 0 41 44 2 0 44 45 1 0 6 46 1 0 46 47 2 0 47 3 1 0 45 7 1 0 44 11 1 0 34 14 1 0 28 19 1 0 1 48 1 0 1 49 1 0 1 50 1 0 4 51 1 0 5 52 1 0 8 53 1 0 14 54 1 1 16 55 1 1 17 56 1 0 17 57 1 0 19 58 1 1 21 59 1 1 22 60 1 0 22 61 1 0 23 62 1 0 24 63 1 6 25 64 1 0 26 65 1 1 27 66 1 0 28 67 1 6 29 68 1 0 30 69 1 6 31 70 1 0 32 71 1 1 33 72 1 0 34 73 1 6 35 74 1 0 38 75 1 0 38 76 1 0 38 77 1 0 40 78 1 0 43 79 1 0 43 80 1 0 43 81 1 0 46 82 1 0 47 83 1 0 M END

Standard InCHIKey	PDOZWYOOYIYRHV-MQZHJVRCSA-N
Standard InCHI	InChI=1S/C30H36O17/c1-40-12-6-4-11(5-7-12)14-8-13(32)17-25(44-14)27(41-2)24(39)28(42-3)26(17)47-30-23(38)21(36)19(34)16(46-30)10-43-29-22(37)20(35)18(33)15(9-31)45-29/h4-8,15-16,18-23,29-31,33-39H,9-10H2,1-3H3/t15-,16+,18-,19-,20+,21+,22-,23-,29-,30+/m1/s1
SMILES	COC1=CC=C(C2=CC(=O)C3=C(O[C@@H]4O[C@@H](CO[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)C(OC)=C(O)C(OC)=C3O2)C=C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	668.2	Volume:	612.996 ? Van der Waals volume.
Dense:	1.09	LogP:	0.506 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.231 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.232 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	30.0
TPSA:	256.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.118	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.814	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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.54	Fluc inhibitor:	0.242 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.728 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.599 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.038	Promiscuous compounds:	0.222

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.268	MDCK Permeability:	-5.361
Pgp-inhibitor:	0.0	Pgp-substrate:	0.62
PAMPA:	0.995 ? 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):	0.736
20% Bioavailability (F20%):	0.136	30% Bioavailability (F30%):	0.879
50% Bioavailability (F50%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.185
Plasma Protein Binding (PPB):	84.109%	Volume Distribution (VD):	-0.24
Fu:	15.882% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.308
BSEP inhibitor:	0.009

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.003
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.253 ? 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):

1.725

Half-life (T1/2):

3.735

ADMET: Toxicity

hERG Blockers:	0.024	hERG Blockers (10um):	0.081
Human Hepatotoxicity (H-HT):	0.676	Drug-induced Liver Injury (DILI):	0.988
AMES Toxicity:	0.913	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.013	Skin Sensitization:	0.998
Carcinogencity:	0.216	Eye Corrosion:	0.0
Eye Irritation:	0.019	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.007	Ototoxicity:	0.97
Hematotoxicity:	0.341	Drug-induced Nephrotoxicity:	0.713
Genotoxicity:	0.303	RPMI-8226 Immunitoxicity:	0.152
A549 Cytotoxicity:	0.339	Hek293 Cytotoxicity:	0.323
BCF:	0.28 ? 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:	3.056 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.729 ? 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
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 NPC543360 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	20171
0.1-0.2	25250
0.2-0.3	3291
0.3-0.4	890
0.4-0.5	213
0.5-0.6	34
0.6-0.7	6
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
0.6146	Remote Similarity	NPC204693
0.6042	Remote Similarity	NPC22062
0.6042	Remote Similarity	NPC473634
0.6042	Remote Similarity	NPC138811
0.6	Remote Similarity	NPC295613
0.6	Remote Similarity	NPC473657
0.596	Remote Similarity	NPC483707
0.5743	Remote Similarity	NPC488089
0.5652	Remote Similarity	NPC186807
0.5644	Remote Similarity	NPC473623
0.5625	Remote Similarity	NPC211594
0.5604	Remote Similarity	NPC58053
0.5556	Remote Similarity	NPC473512
0.5556	Remote Similarity	NPC129827
0.5543	Remote Similarity	NPC95090
0.5543	Remote Similarity	NPC27408
0.5446	Remote Similarity	NPC475366
0.5413	Remote Similarity	NPC311850
0.5364	Remote Similarity	NPC488083
0.534	Remote Similarity	NPC209296
0.5294	Remote Similarity	NPC488073
0.5294	Remote Similarity	NPC284277
0.5294	Remote Similarity	NPC475497
0.5283	Remote Similarity	NPC135358
0.5268	Remote Similarity	NPC68592
0.5248	Remote Similarity	NPC102028
0.5238	Remote Similarity	NPC189589
0.5234	Remote Similarity	NPC244875
0.5213	Remote Similarity	NPC259152
0.5204	Remote Similarity	NPC61791
0.5176	Remote Similarity	NPC208769
0.5158	Remote Similarity	NPC610763
0.5149	Remote Similarity	NPC44931
0.5149	Remote Similarity	NPC275454
0.5146	Remote Similarity	NPC46202
0.5128	Remote Similarity	NPC262222
0.5106	Remote Similarity	NPC143851
0.505	Remote Similarity	NPC187379
0.505	Remote Similarity	NPC603300
0.5047	Remote Similarity	NPC287889

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC543360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4958
0.1-0.2	4092
0.2-0.3	86
0.3-0.4	7
0.4-0.5	5
0.5-0.6	2
0.6-0.7	0
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
0.5472	Remote Similarity	NPD7472	Pre-clinical
0.534	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