NPASS Compound

Natural Product: NPC470068

Natural Product ID	NPC470068
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Alpha-Acetoxyl-21,24R-Epoxyapotirucall-14-Ene-7Alpha,23R,25-Triol
IUPAC Name	[(3R,5R,7R,8R,9R,10S,13S,17R)-7-hydroxy-17-[(3S,5R,6S)-5-hydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-4,4,8,10,13-pentamethyl-2,3,5,6,7,9,11,12,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1668622
PubChem CID	53323606
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 90 94 0 0 0 0 0 0 0 0999 V2000 -8.1277 2.9717 -1.2265 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3347 2.1109 -0.2789 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8514 1.6392 0.7663 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0066 1.8059 -0.5227 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2040 0.9986 0.3315 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1578 1.8705 0.9210 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7445 1.6001 0.5435 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3929 0.1246 0.4752 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3390 -0.4460 -0.5513 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.7716 -0.2421 -0.3314 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4483 -0.2936 -1.7186 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3389 -1.4870 0.3721 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9518 -1.8897 -0.7973 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5748 -1.9686 -1.4228 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5558 -1.3382 -0.5032 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0397 0.0264 -0.1454 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0745 0.6576 0.5755 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0863 1.1270 -0.4745 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4394 0.1372 -1.5072 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7614 -1.1799 -1.1805 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5526 -2.1593 -1.6044 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7930 -1.6585 -2.2408 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8374 -0.2535 -1.6988 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9036 -0.1137 -0.7060 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4035 1.1678 -0.2222 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3828 1.3872 1.1452 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0136 0.4387 1.9061 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0264 -0.9308 1.2795 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6913 -1.0303 0.5179 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0201 -1.1457 0.3708 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3034 0.8899 2.4758 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0328 2.0137 3.2911 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3542 1.2943 1.4973 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8950 -0.1572 3.3970 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9696 0.5702 -2.9165 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4559 -2.2811 0.6918 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7119 -1.2669 -2.6213 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5358 -0.4463 1.8312 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0237 3.3649 -0.7502 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2761 2.3951 -2.1427 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4290 3.8251 -1.4796 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9044 0.7143 1.1755 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1955 1.8786 2.0534 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3322 2.9643 0.6762 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4827 2.0234 -0.4691 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1043 2.1630 1.2543 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0638 0.0853 -1.5154 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6233 -1.3433 -2.0252 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3635 0.3198 -1.6865 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7263 0.1487 -2.4340 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1196 -2.4024 -0.1900 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4587 -1.3463 0.2965 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1198 -1.5162 1.4361 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6605 -2.2497 -1.6026 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1001 -2.5394 0.0530 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3713 -3.0370 -1.6205 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1792 0.5655 -1.1264 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1766 1.5391 1.1933 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6454 -0.0481 1.2219 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4957 1.9534 -0.9953 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8840 1.5419 0.1419 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3393 -3.2473 -1.5095 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6959 -1.7160 -3.3478 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6819 -2.2510 -1.8989 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2051 0.3121 -2.6448 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7987 -0.6320 -1.1919 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5100 1.3274 -0.4890 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9756 2.1044 -0.6547 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3251 0.3163 2.8049 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0149 -1.7538 2.0116 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9510 -0.6364 1.2059 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5637 -2.0752 0.2143 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1538 -2.1112 0.2557 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5664 2.7978 3.0204 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0470 2.2901 1.0836 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5041 0.6342 0.6489 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2978 1.5075 2.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3716 -0.0535 4.3798 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6907 -1.1708 3.0123 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9513 0.0649 3.5610 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8410 0.9876 -3.5049 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7497 -0.3738 -3.4530 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2141 1.3262 -2.9094 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5009 -2.8605 0.5031 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2375 -3.0563 0.6969 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2978 -1.7834 1.6447 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8669 -1.9173 -3.3407 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4719 -0.0059 2.2889 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6702 -1.5261 1.8979 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7170 -0.0409 2.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 10 12 1 0 9 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 2 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 28 29 1 0 28 30 1 0 27 31 1 0 31 32 1 0 31 33 1 0 31 34 1 0 19 35 1 6 15 36 1 1 14 37 1 0 8 38 1 1 10 5 1 0 20 15 1 0 29 24 1 0 16 8 1 0 23 19 1 0 1 39 1 0 1 40 1 0 1 41 1 0 5 42 1 1 6 43 1 0 6 44 1 0 7 45 1 0 7 46 1 0 9 47 1 6 11 48 1 0 11 49 1 0 11 50 1 0 12 51 1 0 12 52 1 0 12 53 1 0 13 54 1 0 13 55 1 0 14 56 1 6 16 57 1 6 17 58 1 0 17 59 1 0 18 60 1 0 18 61 1 0 21 62 1 0 22 63 1 0 22 64 1 0 23 65 1 6 24 66 1 6 25 67 1 0 25 68 1 0 27 69 1 1 28 70 1 1 29 71 1 0 29 72 1 0 30 73 1 0 32 74 1 0 33 75 1 0 33 76 1 0 33 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 35 81 1 0 35 82 1 0 35 83 1 0 36 84 1 0 36 85 1 0 36 86 1 0 37 87 1 0 38 88 1 0 38 89 1 0 38 90 1 0 M END

Standard InCHIKey	DJEFMARUYRITFP-JRIYAETESA-N
Standard InCHI	InChI=1S/C32H52O6/c1-18(33)38-26-12-14-31(7)23-11-13-30(6)20(19-15-21(34)27(37-17-19)29(4,5)36)9-10-22(30)32(23,8)25(35)16-24(31)28(26,2)3/h10,19-21,23-27,34-36H,9,11-17H2,1-8H3/t19-,20-,21-,23-,24+,25-,26-,27+,30+,31-,32+/m1/s1
SMILES	CC(=O)O[C@@H]1CC[C@]2([C@H](C1(C)C)C[C@H]([C@@]1([C@@H]2CC[C@@]2(C1=CC[C@@H]2[C@H]1CO[C@@H]([C@@H](C1)O)C(O)(C)C)C)C)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	532.38	Volume:	566.714 ? Van der Waals volume.
Dense:	0.939	LogP:	3.472 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.576 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.905 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	27.0
TPSA:	96.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.349	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.303	Fsp³:	0.906
MCE-18:	106.23 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.838	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.247	Promiscuous compounds:	0.42

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.369	MDCK Permeability:	-4.992
Pgp-inhibitor:	0.998	Pgp-substrate:	0.317
PAMPA:	0.306 ? 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%):	0.796	30% Bioavailability (F30%):	0.427
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007	MRP1:	0.978
Plasma Protein Binding (PPB):	78.295%	Volume Distribution (VD):	-0.341
Fu:	14.478% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.041
BSEP inhibitor:	0.987

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.027	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.159
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.252 ? 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):

7.908

Half-life (T1/2):

0.99

ADMET: Toxicity

hERG Blockers:	0.038	hERG Blockers (10um):	0.205
Human Hepatotoxicity (H-HT):	0.651	Drug-induced Liver Injury (DILI):	0.614
AMES Toxicity:	0.805	Rat Oral Acute Toxicity:	0.588
Maximum Recommended Daily Dose:	0.646	Skin Sensitization:	0.997
Carcinogencity:	0.853	Eye Corrosion:	0.002
Eye Irritation:	0.183	Respiratory Toxicity:	0.649
Drug-induced Neurotoxicity:	0.252	Ototoxicity:	0.506
Hematotoxicity:	0.712	Drug-induced Nephrotoxicity:	0.63
Genotoxicity:	0.95	RPMI-8226 Immunitoxicity:	0.089
A549 Cytotoxicity:	0.873	Hek293 Cytotoxicity:	0.747
BCF:	1.039 ? 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:	3.605 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.402 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.595 ? 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
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943621]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Yunnan, China	2007-May	PMID[21288727]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32208696]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	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
IC50	2

Activity Type	# Activity
Cell line	2

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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	>	50000.0	nM	PMID[20451377]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	73500.0	nM	PMID[19700322]

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 NPC470068 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	18846
0.1-0.2	24044
0.2-0.3	6669
0.3-0.4	249
0.4-0.5	32
0.5-0.6	5
0.6-0.7	10
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
0.7714	Intermediate Similarity	NPC470054
0.7465	Intermediate Similarity	NPC470067
0.641	Remote Similarity	NPC470060
0.641	Remote Similarity	NPC470059
0.6282	Remote Similarity	NPC470064
0.6282	Remote Similarity	NPC470043
0.6203	Remote Similarity	NPC470056
0.6133	Remote Similarity	NPC470063
0.6076	Remote Similarity	NPC470055
0.6053	Remote Similarity	NPC470053
0.6	Remote Similarity	NPC470058
0.6	Remote Similarity	NPC470057
0.5976	Remote Similarity	NPC470062
0.5976	Remote Similarity	NPC470061
0.5844	Remote Similarity	NPC470066
0.5238	Remote Similarity	NPC218853
0.5063	Remote Similarity	NPC480956

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470068 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6496
0.1-0.2	2545
0.2-0.3	109
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