NPASS Compound

Natural Product: NPC517465

Natural Product ID	NPC517465
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{S},3~{S},4~{S},5~{R},6~{S})-2-[[(2~{R},3~{R},4~{R},5~{S})-3,4-dihydroxy-5-(hydroxymethyl)-5-[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydrofuran-2-yl]methoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
IUPAC Name	(2~{S},3~{S},4~{S},5~{R},6~{S})-2-[[(2~{R},3~{R},4~{R},5~{S})-3,4-dihydroxy-5-(hydroxymethyl)-5-[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydrofuran-2-yl]methoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
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 66 68 0 0 0 0 0 0 0 0999 V2000 6.8827 1.6389 -1.0129 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8220 1.4620 0.3629 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4471 0.9338 0.7156 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4518 1.8102 0.3309 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2595 1.0603 0.2295 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3014 1.9949 -0.1349 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7895 1.8783 -1.3981 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0971 0.5411 -1.5511 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0914 0.4735 -0.6220 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8642 -0.4490 -0.9930 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4672 -1.7912 -0.4645 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7450 -2.2558 -0.9655 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0654 0.0246 -0.5680 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1851 -0.6908 -0.8031 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6302 -1.1162 0.4740 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4489 -0.1780 1.0728 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6605 -0.6201 2.5074 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2605 -1.8737 2.5787 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8209 -0.1222 0.4257 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3161 1.1602 0.6349 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6291 -0.4432 -1.0348 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6918 -1.8229 -1.1815 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2693 0.0512 -1.5428 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1584 1.4183 -1.4408 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8423 -0.3783 -2.4936 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6452 -1.6121 -3.0961 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2952 0.5348 -2.8665 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1365 1.8282 -3.0769 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8780 0.4414 1.5271 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2034 -0.7607 1.2665 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9789 0.1208 2.4700 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1969 -1.2550 2.5771 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2905 0.7706 2.2184 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3281 -0.0641 2.6645 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3885 0.9106 -1.4580 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0448 2.3940 0.8982 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5604 0.6704 0.6209 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2514 -0.0469 0.2378 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4240 0.3238 -0.5833 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5929 1.9288 -2.1651 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0509 2.6924 -1.5665 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7927 -0.2952 -1.5881 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2130 -2.5871 -0.6702 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3499 -1.7811 0.6438 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7361 -3.2324 -1.1261 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0335 -1.6558 -1.3502 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9756 0.8316 1.1287 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6573 -0.7021 2.9791 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2102 0.1585 3.0702 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1159 -1.7657 3.0618 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 -0.8320 0.9299 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1108 1.3118 0.0566 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4548 0.0062 -1.5876 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4620 -2.3148 -0.3531 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2323 -0.2196 -2.6011 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7983 1.8198 -2.2820 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7690 0.0513 -2.9254 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2107 -2.3308 -2.7543 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9091 0.1391 -3.6982 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8372 2.0085 -2.3765 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0974 1.0795 2.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8017 -1.1352 2.0978 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6628 0.4316 3.5105 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5454 -1.6724 3.1992 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4276 1.7372 2.7115 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6617 -0.6334 1.9158 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 10 13 1 1 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 16 19 1 0 19 20 1 0 19 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 10 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 5 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 3 1 0 27 8 1 0 23 14 1 0 1 35 1 0 2 36 1 0 2 37 1 0 3 38 1 6 5 39 1 6 7 40 1 0 7 41 1 0 8 42 1 6 11 43 1 0 11 44 1 0 12 45 1 0 14 46 1 6 16 47 1 1 17 48 1 0 17 49 1 0 18 50 1 0 19 51 1 1 20 52 1 0 21 53 1 6 22 54 1 0 23 55 1 6 24 56 1 0 25 57 1 6 26 58 1 0 27 59 1 6 28 60 1 0 29 61 1 1 30 62 1 0 31 63 1 1 32 64 1 0 33 65 1 1 34 66 1 0 M END

Standard InCHIKey	NIBVDXPSJBYJFT-VBBCUDLLSA-N
Standard InCHI	InChI=1S/C18H32O16/c19-1-5-8(22)11(25)13(27)16(31-5)30-3-7-10(24)15(29)18(4-21,33-7)34-17-14(28)12(26)9(23)6(2-20)32-17/h5-17,19-29H,1-4H2/t5-,6+,7+,8-,9+,10-,11-,12-,13-,14+,15+,16-,17+,18-/m0/s1
SMILES	OC[C@@H]1O[C@H](OC[C@H]2O[C@@](CO)(O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	504.17	Volume:	434.858 ? Van der Waals volume.
Dense:	1.159	LogP:	-2.825 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-1.968 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-0.203 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	17.0
TPSA:	268.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	11.0	Rings:	3.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.146	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.988	Fsp³:	1.0
MCE-18:	69.444 ? 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:	0.33	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.316 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.004 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.517	Promiscuous compounds:	0.01

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.087	MDCK Permeability:	-4.897
Pgp-inhibitor:	0.0	Pgp-substrate:	0.805
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):	0.999
20% Bioavailability (F20%):	0.735	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.008
Plasma Protein Binding (PPB):	19.155%	Volume Distribution (VD):	-0.523
Fu:	88.123% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	0.996	BCRP inhibitor:	0.001
BSEP inhibitor:	0.0

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:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.021
HLM stability:	0.0 ? 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):

0.54

Half-life (T1/2):

3.3

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.047
Human Hepatotoxicity (H-HT):	0.497	Drug-induced Liver Injury (DILI):	0.347
AMES Toxicity:	0.758	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	0.999
Carcinogencity:	0.01	Eye Corrosion:	0.0
Eye Irritation:	0.043	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	0.998
Hematotoxicity:	0.307	Drug-induced Nephrotoxicity:	0.634
Genotoxicity:	0.004	RPMI-8226 Immunitoxicity:	0.105
A549 Cytotoxicity:	0.087	Hek293 Cytotoxicity:	0.039
BCF:	0.026 ? 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:	1.109 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	2.222 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	1.472 ? 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
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2020.112278]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21574561]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23747095]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29192771]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30792999]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36080366]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36270431]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36359928]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37898811]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38267697]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38744893]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39592251]
NPO55940	Plantago spp.	Genus	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO63959	Fraxinus spp.	Genus	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO54053	Teucrium spp.	Genus	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Shoot Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20414	Ocimum basilicum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20414	Ocimum basilicum	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 NPC517465 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	33246
0.1-0.2	12956
0.2-0.3	3134
0.3-0.4	457
0.4-0.5	50
0.5-0.6	13
0.6-0.7	0
0.7-0.8	2
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8222	Intermediate Similarity	NPC34877
0.7143	Intermediate Similarity	NPC130683
0.5893	Remote Similarity	NPC479398
0.5893	Remote Similarity	NPC479397
0.5745	Remote Similarity	NPC145112
0.54	Remote Similarity	NPC89145
0.54	Remote Similarity	NPC157514
0.54	Remote Similarity	NPC322314
0.54	Remote Similarity	NPC269166
0.5385	Remote Similarity	NPC147292
0.5349	Remote Similarity	NPC124963
0.5303	Remote Similarity	NPC487504
0.5227	Remote Similarity	NPC326533
0.5116	Remote Similarity	NPC323574
0.507	Remote Similarity	NPC487503

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC517465 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7939
0.1-0.2	1110
0.2-0.3	79
0.3-0.4	15
0.4-0.5	4
0.5-0.6	0
0.6-0.7	0
0.7-0.8	2
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
0.7143	Intermediate Similarity	NPD887	Approved
0.7143	Intermediate Similarity	NPD895	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