NPASS Compound

Natural Product: NPC241265

Natural Product ID	NPC241265
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-O-(Beta-D-Glucopyranosyl)-1-O-Octanoyl-Beta-D-Glucopyranose
IUPAC Name	[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl] octanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL227838
PubChem CID	16680920
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

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 68 69 0 0 0 0 0 0 0 0999 V2000 7.7621 -3.5820 0.7920 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8002 -2.5742 0.1863 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8241 -2.2061 1.2607 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8323 -1.1918 0.7220 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0475 -1.7159 -0.4479 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0936 -0.6809 -0.9363 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0825 -0.2357 0.0841 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1852 0.7905 -0.5172 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3569 1.1368 -1.6969 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1544 1.3838 0.1887 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6638 2.3470 -0.4249 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1161 1.9208 -0.4654 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9192 2.9920 -1.1411 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1895 4.2783 -1.3437 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0851 4.5567 -0.4084 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5115 5.6614 0.5691 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4532 6.0717 1.3531 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6324 3.5102 0.3436 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6671 4.3275 -2.6587 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1101 3.1449 -0.4338 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2986 0.6856 -1.0648 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8085 -0.2661 -0.2127 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1753 -0.7611 -0.6253 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7119 -1.4663 0.6056 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7922 -2.6196 0.8847 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3776 -2.4178 0.5731 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8813 -3.6267 -0.2405 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5053 -3.6101 -0.3301 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9716 -1.3076 -0.0619 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9961 -2.9647 2.2426 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0277 -1.8802 0.3837 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0413 0.2405 -0.9856 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2463 -3.0883 1.6566 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5353 -3.8716 0.0308 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2596 -4.5269 1.0798 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4098 -1.7070 -0.1307 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3266 -3.0722 -0.6683 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2662 -3.1163 1.5940 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3225 -1.8132 2.1681 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3613 -0.2560 0.4972 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1325 -0.9663 1.5552 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4740 -2.6176 -0.1187 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7480 -1.9677 -1.2757 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5469 -1.1208 -1.8111 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6522 0.1970 -1.3246 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4403 -1.1223 0.3125 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5043 0.0947 1.0335 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3688 2.5374 -1.4857 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4401 1.8277 0.5917 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2080 2.5975 -2.1482 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9438 5.0994 -1.3115 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1881 4.9942 -0.9385 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9932 6.5007 0.0066 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3191 5.2150 1.1917 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3019 5.4646 1.1698 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7879 4.7841 -2.6686 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7133 3.8117 -0.8038 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9475 0.2347 0.7890 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1210 -1.5294 -1.4241 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6493 -0.7686 1.4675 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2272 -3.4981 0.3201 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7894 -2.4970 1.5382 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2602 -4.5594 0.2223 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3947 -3.5419 -1.2224 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1122 -4.3281 0.2254 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7570 -2.5089 2.6357 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5095 -1.1263 -0.0117 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0007 0.3042 -1.9935 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 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 0 14 19 1 0 13 20 1 0 12 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 27 28 1 0 26 29 1 0 25 30 1 0 24 31 1 0 23 32 1 0 18 11 1 0 29 22 1 0 1 33 1 0 1 34 1 0 1 35 1 0 2 36 1 0 2 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 5 42 1 0 5 43 1 0 6 44 1 0 6 45 1 0 7 46 1 0 7 47 1 0 11 48 1 6 12 49 1 1 13 50 1 6 14 51 1 6 15 52 1 6 16 53 1 0 16 54 1 0 17 55 1 0 19 56 1 0 20 57 1 0 22 58 1 1 23 59 1 6 24 60 1 1 25 61 1 6 26 62 1 1 27 63 1 0 27 64 1 0 28 65 1 0 30 66 1 0 31 67 1 0 32 68 1 0 M END

Standard InCHIKey	PKTOHQWFHRKNMN-SYVJZRHHSA-N
Standard InCHI	InChI=1S/C20H36O12/c1-2-3-4-5-6-7-12(23)31-20-18(16(27)14(25)11(9-22)30-20)32-19-17(28)15(26)13(24)10(8-21)29-19/h10-11,13-22,24-28H,2-9H2,1H3/t10-,11-,13-,14-,15+,16+,17-,18-,19+,20+/m1/s1
SMILES	CCCCCCCC(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	468.22	Volume:	440.21 ? Van der Waals volume.
Dense:	1.064	LogP:	0.18 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.878 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.764 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	13.0
TPSA:	195.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	7.0	Rings:	2.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.125	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.271	Fsp³:	0.95
MCE-18:	42.718 ? 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:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.504	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.017 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.352	Promiscuous compounds:	0.222

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.578	MDCK Permeability:	-4.838
Pgp-inhibitor:	0.0	Pgp-substrate:	0.821
PAMPA:	0.993 ? 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%):	0.679	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.032	MRP1:	0.249
Plasma Protein Binding (PPB):	73.33%	Volume Distribution (VD):	-0.415
Fu:	21.945% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.015
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.014	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:	0.971
HLM stability:	0.001 ? 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):

1.564

Half-life (T1/2):

1.826

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.05
Human Hepatotoxicity (H-HT):	0.734	Drug-induced Liver Injury (DILI):	0.86
AMES Toxicity:	0.914	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.169	Eye Corrosion:	0.0
Eye Irritation:	0.357	Respiratory Toxicity:	0.006
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.983
Hematotoxicity:	0.447	Drug-induced Nephrotoxicity:	0.916
Genotoxicity:	0.006	RPMI-8226 Immunitoxicity:	0.123
A549 Cytotoxicity:	0.528	Hek293 Cytotoxicity:	0.073
BCF:	0.5 ? 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:	3.262 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.81 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.859 ? 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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36014413]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4323	Morinda citrifolia	Species	Rubiaceae	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

Activity Type	# Activity
Activity	4
Inhibition	1
ID50	1

Activity Type	# Activity
Cell line	1
Organism	5

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
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[17190444]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	15.3	%	PMID[17698631]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	56.4	%	PMID[26317881]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	85.7	%	PMID[21868221]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Activity	=	100.0	%	PMID[2657065]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ID50	=	0.79	mg	PMID[16499322]

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 NPC241265 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	20620
0.1-0.2	23861
0.2-0.3	4240
0.3-0.4	970
0.4-0.5	136
0.5-0.6	23
0.6-0.7	2
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC76881
0.8077	Intermediate Similarity	NPC163812
0.7885	Intermediate Similarity	NPC250619
0.6792	Remote Similarity	NPC285003
0.6604	Remote Similarity	NPC12040
0.5926	Remote Similarity	NPC206601
0.5909	Remote Similarity	NPC478729
0.5789	Remote Similarity	NPC488690
0.5652	Remote Similarity	NPC475425
0.5571	Remote Similarity	NPC477328
0.5571	Remote Similarity	NPC477330
0.5517	Remote Similarity	NPC206823
0.5507	Remote Similarity	NPC477350
0.5493	Remote Similarity	NPC477329
0.527	Remote Similarity	NPC604005
0.527	Remote Similarity	NPC605014
0.5238	Remote Similarity	NPC488689
0.52	Remote Similarity	NPC477331
0.52	Remote Similarity	NPC477332
0.5192	Remote Similarity	NPC606861
0.5192	Remote Similarity	NPC607126
0.5135	Remote Similarity	NPC22742
0.5135	Remote Similarity	NPC477349
0.5135	Remote Similarity	NPC477346
0.5132	Remote Similarity	NPC477326
0.5132	Remote Similarity	NPC600446
0.5132	Remote Similarity	NPC605013
0.5075	Remote Similarity	NPC156089

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC241265 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6868
0.1-0.2	2121
0.2-0.3	130
0.3-0.4	28
0.4-0.5	3
0.5-0.6	0
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
		NPD

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