NPASS Compound

Natural Product: NPC117185

Natural Product ID	NPC117185
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cucurbitacin G
IUPAC Name	(2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-17-[(2R)-2,5,6-trihydroxy-6-methyl-3-oxoheptan-2-yl]-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
Synonyms	Cucurbitacin G
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL551160
PubChem CID	441818
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001686] Cucurbitacins

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 84 87 0 0 0 0 0 0 0 0999 V2000 -6.7130 0.9014 1.4735 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9989 0.3559 0.2234 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4189 1.2620 -0.9142 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5730 0.4116 0.5129 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0084 1.5728 0.8251 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5314 1.5321 1.1088 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8813 0.8787 -0.0847 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4245 0.6980 0.2325 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1599 -0.1572 1.4158 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2739 1.9981 0.4690 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7262 1.6289 0.2551 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7499 0.3644 -0.5786 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3353 0.2065 -1.0153 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0913 1.0768 -2.1903 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1605 -1.1792 -1.2254 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5149 -1.4370 -0.6832 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7834 -2.5850 -0.3839 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5548 -0.4057 -0.4819 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2901 -0.2695 -1.8130 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6203 -0.7650 0.5021 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2995 -2.0606 0.2044 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7330 -2.1133 0.7413 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4902 -1.0396 0.0452 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4652 -1.2129 -0.6478 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2395 -3.3744 0.4985 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7777 0.5821 -1.6598 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9318 -0.5585 -2.6057 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0915 0.7817 -0.9126 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6816 1.8490 -0.9473 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7034 -0.2945 -0.1249 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9720 0.1890 0.4927 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6556 -0.8860 1.3252 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1016 -1.9641 0.3586 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8980 -0.3071 1.9662 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8433 -1.3688 2.3217 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6460 1.2242 1.3871 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5927 1.7535 -2.3744 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4457 1.5533 1.4217 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8027 0.8799 1.2810 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4239 1.9730 1.5307 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4272 0.3289 2.3614 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5482 1.5194 -1.5729 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7813 2.2261 -0.5299 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2313 0.7792 -1.4953 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5431 2.5122 0.8824 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1230 2.5540 1.2037 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3832 0.9451 2.0401 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9704 1.5982 -0.9241 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9847 -0.8134 1.7444 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0457 0.4981 2.2925 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7104 -0.8340 1.3265 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1460 2.2629 1.5544 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0738 2.8300 -0.1247 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1463 2.4955 -0.3158 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1289 -0.5243 -0.0244 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6912 0.6317 -3.0398 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9233 1.1051 -2.5988 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3440 2.1492 -2.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5437 -1.8771 -0.7171 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2233 -1.4217 -2.3275 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2308 0.8318 -2.0683 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3344 -0.5455 -1.7871 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7287 -0.7845 -2.6421 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2913 -0.8225 1.5630 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7753 -2.8691 0.8027 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3415 -2.3109 -0.8539 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7197 -1.8934 1.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7153 -3.6884 1.3114 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9322 -1.0697 -2.5216 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8920 -0.2420 -3.6868 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1819 -1.3573 -2.4835 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0170 -0.5558 0.7071 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8247 -1.2425 -0.6938 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6923 0.6069 -0.2217 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2889 -2.6638 0.1103 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0103 -2.4612 0.7428 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3971 -1.4486 -0.5816 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6177 0.0418 1.1731 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4298 -1.1007 2.5207 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6837 0.5813 2.5892 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9617 -2.3320 2.4390 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3609 1.8733 1.4914 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4724 2.0713 -2.6783 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4006 0.7222 1.9178 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 2 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 1 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 2 0 16 18 1 0 18 19 1 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 22 25 1 0 12 26 1 0 26 27 1 0 26 28 1 0 28 29 2 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 32 34 1 0 32 35 1 0 31 36 1 0 26 37 1 6 11 38 1 0 23 2 1 0 20 4 1 0 18 7 1 0 13 8 1 0 1 39 1 0 1 40 1 0 1 41 1 0 3 42 1 0 3 43 1 0 3 44 1 0 5 45 1 0 6 46 1 0 6 47 1 0 7 48 1 6 9 49 1 0 9 50 1 0 9 51 1 0 10 52 1 0 10 53 1 0 11 54 1 6 12 55 1 1 14 56 1 0 14 57 1 0 14 58 1 0 15 59 1 0 15 60 1 0 19 61 1 0 19 62 1 0 19 63 1 0 20 64 1 1 21 65 1 0 21 66 1 0 22 67 1 1 25 68 1 0 27 69 1 0 27 70 1 0 27 71 1 0 30 72 1 0 30 73 1 0 31 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 36 82 1 0 37 83 1 0 38 84 1 0 M END

Standard InCHIKey	ABNDMUIXCBUBLO-REQJDAJISA-N
Standard InCHI	InChI=1S/C30H46O8/c1-25(2)15-9-10-19-27(5)13-18(32)23(30(8,38)21(34)12-20(33)26(3,4)37)28(27,6)14-22(35)29(19,7)16(15)11-17(31)24(25)36/h9,16-20,23,31-33,37-38H,10-14H2,1-8H3/t16-,17+,18-,19+,20?,23+,27+,28-,29+,30+/m1/s1
SMILES	CC1(C)C2=CC[C@H]3[C@]4(C)C[C@H]([C@@H]([C@@]4(C)CC(=O)[C@@]3(C)[C@@H]2C[C@@H](C1=O)O)[C@](C)(C(=O)CC(C(C)(C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	534.32	Volume:	552.986 ? Van der Waals volume.
Dense:	0.966	LogP:	1.183 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.75 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.276 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	152.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	5.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.336	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.434	Fsp³:	0.833
MCE-18:	98.909 ? 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:	0.465	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? 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:	0.317	Promiscuous compounds:	0.392

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.037	MDCK Permeability:	-4.821
Pgp-inhibitor:	0.0	Pgp-substrate:	0.475
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):	0.005
20% Bioavailability (F20%):	0.11	30% Bioavailability (F30%):	0.184
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.969
Plasma Protein Binding (PPB):	89.462%	Volume Distribution (VD):	0.171
Fu:	12.125% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.119
BSEP inhibitor:	0.973

ADMET: Metabolism

CYP1A2-inhibitor:	0.152	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:	0.004
CYP3A4-inhibitor:	0.983	CYP3A4-substrate:	0.003
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.625
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):

8.589

Half-life (T1/2):

1.647

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.029
Human Hepatotoxicity (H-HT):	0.499	Drug-induced Liver Injury (DILI):	0.239
AMES Toxicity:	0.393	Rat Oral Acute Toxicity:	0.184
Maximum Recommended Daily Dose:	0.868	Skin Sensitization:	0.905
Carcinogencity:	0.778	Eye Corrosion:	0.0
Eye Irritation:	0.03	Respiratory Toxicity:	0.775
Drug-induced Neurotoxicity:	0.048	Ototoxicity:	0.879
Hematotoxicity:	0.64	Drug-induced Nephrotoxicity:	0.968
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.152
A549 Cytotoxicity:	0.078	Hek293 Cytotoxicity:	0.261
BCF:	0.435 ? 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:	3.091 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.499 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.674 ? 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
NPO13846	Crinodendron hookerianum	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8800	Cucumis angolensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13846	Crinodendron hookerianum	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8800	Cucumis angolensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13846	Crinodendron hookerianum	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14700	Citrullus sp.	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13846	Crinodendron hookerianum	Species	Elaeocarpaceae	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	1
Non-molecular	1

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
NPT170	Cell line	SK-MEL-28	Homo sapiens	IC50	=	1280.0	nM	PMID[25599949]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	1370.0	nM	PMID[25599949]

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 NPC117185 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	22869
0.1-0.2	25790
0.2-0.3	1118
0.3-0.4	39
0.4-0.5	15
0.5-0.6	14
0.6-0.7	6
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8033	Intermediate Similarity	NPC49371
0.8033	Intermediate Similarity	NPC479419
0.746	Intermediate Similarity	NPC311612
0.7206	Intermediate Similarity	NPC196528
0.6923	Remote Similarity	NPC479420
0.6714	Remote Similarity	NPC100267
0.6714	Remote Similarity	NPC475524
0.6667	Remote Similarity	NPC58370
0.6667	Remote Similarity	NPC43285
0.6032	Remote Similarity	NPC488647
0.5968	Remote Similarity	NPC479417
0.5942	Remote Similarity	NPC191892
0.5634	Remote Similarity	NPC488646
0.5571	Remote Similarity	NPC87351
0.5493	Remote Similarity	NPC488644
0.5493	Remote Similarity	NPC214644
0.5467	Remote Similarity	NPC486346
0.5455	Remote Similarity	NPC239273
0.5395	Remote Similarity	NPC280782
0.5301	Remote Similarity	NPC1980
0.5301	Remote Similarity	NPC141196
0.5278	Remote Similarity	NPC474720
0.5128	Remote Similarity	NPC475294
0.5068	Remote Similarity	NPC185

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC117185 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7610
0.1-0.2	1532
0.2-0.3	8
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