NPASS Compound

Natural Product: NPC483892

Natural Product ID	NPC483892
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OAFIUXWWQLBAIC-ZFOLFNLISA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

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 97101 0 0 0 0 0 0 0 0999 V2000 0.1712 1.4063 -2.3773 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2349 0.9146 -0.9737 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1344 2.0354 0.0759 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0893 2.0445 0.8618 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1490 1.0230 0.6730 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0217 0.0342 -0.4383 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7255 0.6527 -1.6342 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6971 -0.1771 -2.7644 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2487 0.1207 -3.9757 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8359 1.2249 -4.1132 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1574 -0.8494 -5.1228 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7767 -1.2502 -0.1739 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0171 -2.4902 -0.4359 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6408 -3.5270 -0.6006 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5213 -2.5523 -0.5132 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2377 -1.4111 -1.5106 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5851 -0.2714 -0.6220 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1205 -0.6346 0.6728 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0093 -1.9826 0.7546 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0033 -2.4226 1.8551 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3114 -2.4286 1.2484 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4981 -1.9142 0.7578 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6684 -2.3452 1.3345 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5486 -3.1978 2.2913 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0393 -2.0088 1.0492 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7003 -3.1045 0.4229 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0016 -3.0805 0.0621 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7061 -1.9075 0.3313 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0768 -0.8891 0.9182 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7542 -0.9074 1.2869 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3138 0.3770 1.9250 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8816 0.5648 1.7978 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3314 1.9577 2.2463 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5619 2.1130 3.6797 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8681 1.7466 1.8652 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1709 1.1736 2.6914 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3629 2.1397 0.6966 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9232 2.9216 1.4345 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0892 -1.4231 -1.9468 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5317 -1.6356 -3.2249 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6690 -1.8442 -4.1166 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9660 -1.6296 -3.5932 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9498 -1.3528 -0.9999 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1868 -1.4952 -0.4216 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3178 -1.5423 0.8181 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4475 -1.6025 -1.2264 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4434 1.6525 0.5133 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4703 1.5356 1.3999 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2618 0.8234 2.4407 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7945 2.1537 1.2676 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6549 3.3798 0.7998 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7470 4.2324 1.8473 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3194 3.8637 2.9609 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3381 5.5770 1.6979 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3577 2.4048 -2.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2063 1.6899 -2.7707 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1859 0.6862 -3.1193 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3092 0.5361 -0.8572 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1189 2.9613 -0.5981 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7998 1.9990 1.9576 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2884 0.4407 1.6103 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5163 1.7031 -1.7989 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8193 0.6422 -1.3144 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2490 -0.7001 -5.7162 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0322 -0.7284 -5.8095 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1735 -1.8890 -4.7607 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1358 -1.2672 0.8665 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1466 -3.5020 -0.8335 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8891 -1.5963 -2.3602 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3679 -1.5568 2.4320 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4601 -3.0424 2.6388 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7670 -3.0888 1.4721 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4200 -3.5562 1.2364 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3287 -2.2109 2.3674 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1066 -4.0161 0.2430 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5147 -3.9136 -0.4175 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7485 -1.8743 0.0481 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8703 1.2246 1.4803 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5911 0.3355 3.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5815 0.5176 0.7388 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2714 -0.1408 2.4368 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4795 2.7332 3.8386 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7671 1.1213 4.1779 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7097 2.6110 4.2238 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6302 2.7506 0.5183 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4326 -0.6249 -3.4288 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5689 -2.3246 -2.9484 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1007 -1.8689 -4.6569 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2713 -1.3464 -2.2876 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2455 -0.9857 -0.7545 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7966 -2.6542 -1.1812 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1671 2.5030 2.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5154 1.3542 0.9484 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8024 3.0050 0.5415 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0749 5.7985 2.5210 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8996 5.6924 0.7526 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5606 6.3871 1.8117 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 6 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 6 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 18 19 1 0 19 20 1 1 19 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 35 36 2 0 35 37 1 0 33 38 1 0 16 39 1 0 39 40 1 0 40 41 2 0 40 42 1 0 12 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 5 47 1 0 47 48 1 0 48 49 2 0 48 50 1 0 4 51 1 0 51 52 1 0 52 53 2 0 52 54 1 0 17 2 1 0 30 25 1 0 37 3 1 0 17 6 1 0 19 15 1 0 1 55 1 0 1 56 1 0 1 57 1 0 2 58 1 6 3 59 1 6 4 60 1 1 5 61 1 1 7 62 1 0 7 63 1 0 11 64 1 0 11 65 1 0 11 66 1 0 12 67 1 1 15 68 1 6 16 69 1 6 20 70 1 0 20 71 1 0 20 72 1 0 21 73 1 0 21 74 1 0 26 75 1 0 27 76 1 0 28 77 1 0 31 78 1 0 31 79 1 0 32 80 1 0 32 81 1 0 34 82 1 0 34 83 1 0 34 84 1 0 38 85 1 0 42 86 1 0 42 87 1 0 42 88 1 0 46 89 1 0 46 90 1 0 46 91 1 0 50 92 1 0 50 93 1 0 50 94 1 0 54 95 1 0 54 96 1 0 54 97 1 0 M END

Standard InCHIKey	OAFIUXWWQLBAIC-ZFOLFNLISA-N
Standard InCHI	InChI=1S/C36H43NO17/c1-16-26-27(49-18(3)39)30(52-21(6)42)35(15-47-17(2)38)29(51-20(5)41)25(43)24-28(50-19(4)40)36(16,35)54-34(24,8)14-48-31(44)22-10-9-13-37-23(22)11-12-33(7,46)32(45)53-26/h9-10,13,16,24,26-30,46H,11-12,14-15H2,1-8H3/t16-,24-,26-,27+,28-,29-,30+,33?,34+,35-,36-/m0/s1
SMILES	C[C@H]1[C@H]2[C@H]([C@H]([C@]3(COC(=O)C)[C@H](C(=O)[C@H]4[C@@H]([C@@]13O[C@]4(C)COC(=O)c1cccnc1CCC(C)(C(=O)O2)O)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	761.25	Volume:	719.859 ? Van der Waals volume.
Dense:	1.057	LogP:	0.159 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.677 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.22 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	38.0
TPSA:	243.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	1.0	Rings:	5.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.306	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.584	Fsp³:	0.639
MCE-18:	196.881 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.382	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.038 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.014	Promiscuous compounds:	0.4

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.157	MDCK Permeability:	-4.664
Pgp-inhibitor:	0.745	Pgp-substrate:	0.225
PAMPA:	0.973 ? 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):	0.0
20% Bioavailability (F20%):	0.004	30% Bioavailability (F30%):	0.075
50% Bioavailability (F50%):	0.721

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	1.0
Plasma Protein Binding (PPB):	43.603%	Volume Distribution (VD):	-0.352
Fu:	48.916% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.0
BSEP inhibitor:	0.896

ADMET: Metabolism

CYP1A2-inhibitor:	0.029	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:	0.114	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.959
HLM stability:	0.074 ? 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):

0.894

Half-life (T1/2):

1.549

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.021
Human Hepatotoxicity (H-HT):	0.654	Drug-induced Liver Injury (DILI):	0.97
AMES Toxicity:	0.994	Rat Oral Acute Toxicity:	0.628
Maximum Recommended Daily Dose:	0.716	Skin Sensitization:	1.0
Carcinogencity:	0.624	Eye Corrosion:	0.0
Eye Irritation:	0.021	Respiratory Toxicity:	0.113
Drug-induced Neurotoxicity:	0.184	Ototoxicity:	0.788
Hematotoxicity:	0.966	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.655
A549 Cytotoxicity:	0.207	Hek293 Cytotoxicity:	0.04
BCF:	0.47 ? 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:	3.043 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.654 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.266 ? 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
NPO40564	Maytenus oblongata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28186749]

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
-	Aedes aegypti	LD50	>	10.0	uM	PMID[28186749]

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 NPC483892 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	15855
0.1-0.2	32854
0.2-0.3	996
0.3-0.4	79
0.4-0.5	36
0.5-0.6	25
0.6-0.7	8
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8723	High Similarity	NPC483893
0.8333	Intermediate Similarity	NPC483894
0.7019	Intermediate Similarity	NPC253482
0.6698	Remote Similarity	NPC475648
0.6634	Remote Similarity	NPC146824
0.619	Remote Similarity	NPC475362
0.6111	Remote Similarity	NPC13603
0.6	Remote Similarity	NPC473689
0.6	Remote Similarity	NPC292416
0.6	Remote Similarity	NPC600607
0.6	Remote Similarity	NPC611166
0.5946	Remote Similarity	NPC601643
0.5922	Remote Similarity	NPC250807
0.5922	Remote Similarity	NPC57797
0.5922	Remote Similarity	NPC35208
0.5804	Remote Similarity	NPC475406
0.5769	Remote Similarity	NPC473850
0.5526	Remote Similarity	NPC600583
0.5505	Remote Similarity	NPC475601
0.5455	Remote Similarity	NPC53255
0.5455	Remote Similarity	NPC85879
0.5391	Remote Similarity	NPC244839
0.5357	Remote Similarity	NPC122968
0.5357	Remote Similarity	NPC328186
0.5357	Remote Similarity	NPC228377
0.5273	Remote Similarity	NPC473833
0.5259	Remote Similarity	NPC237702
0.5259	Remote Similarity	NPC600546
0.5214	Remote Similarity	NPC319880
0.5214	Remote Similarity	NPC320324
0.5175	Remote Similarity	NPC316841
0.5169	Remote Similarity	NPC38959
0.5138	Remote Similarity	NPC76565
0.5138	Remote Similarity	NPC601313
0.5126	Remote Similarity	NPC471979
0.5042	Remote Similarity	NPC327904

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC483892 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3748
0.1-0.2	5356
0.2-0.3	46
0.3-0.4	0
0.4-0.5	0
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