NPASS Compound

Natural Product: NPC280782

Natural Product ID	NPC280782
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hemslecin A
IUPAC Name	[(6R)-6-hydroxy-2-methyl-5-oxo-6-[(2S,3S,8S,9R,10R,13R,14S,16R,17R)-2,3,16-trihydroxy-4,4,9,13,14-pentamethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]heptan-2-yl] acetate
Synonyms	Hemslecin A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2332392
PubChem CID	181183
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 90 93 0 0 0 0 0 0 0 0999 V2000 5.6502 3.2712 -1.5081 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2522 1.9291 -1.6451 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4518 1.8072 -2.0392 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5647 0.7822 -1.3617 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1302 -0.4984 -1.4898 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3519 -0.6479 -0.5880 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6862 -0.5684 -2.9224 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1837 -1.6302 -1.3448 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4455 -1.7934 -0.0860 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5053 -0.7260 0.3164 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3057 0.1788 -0.4560 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8162 -0.7644 1.6489 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3056 0.3744 2.4789 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3956 -1.1081 1.6372 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9115 -1.1217 3.0844 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3503 -0.2663 3.0595 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8758 -0.6573 1.6951 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2028 -2.1144 1.7539 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0604 0.1756 1.2719 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2266 -0.1080 2.2150 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3676 0.7292 1.6994 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6814 0.5550 0.4165 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8527 -0.4391 -0.3065 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2447 -0.6858 -1.7225 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5408 -0.1489 -2.1821 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4598 0.4181 -1.1684 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8190 1.3176 -0.1523 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4780 2.6820 -0.6361 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9041 1.5166 0.9349 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1656 -0.5722 -0.4861 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3733 0.8506 -3.1753 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4207 0.0142 -0.1623 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3662 1.3015 -0.9657 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4542 -0.9566 -0.7447 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8929 -1.7717 -1.5386 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0140 -1.0298 -0.4545 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3621 -0.3825 0.8664 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6849 1.0319 0.6230 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6299 -2.4291 3.5008 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3903 -1.9201 2.2871 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3632 3.5025 -0.4538 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7720 3.4147 -2.1661 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3903 4.0362 -1.7942 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0889 -0.2136 0.4008 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4837 -1.7377 -0.4361 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2523 -0.2305 -1.0403 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3449 -1.4823 -3.4511 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3878 0.3228 -3.5107 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7943 -0.5799 -2.9377 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4579 -1.5815 -2.1913 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7365 -2.5971 -1.5300 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9217 -2.7892 -0.1179 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2143 -1.9585 0.7385 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8001 1.1814 1.8546 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1847 0.0509 3.1149 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6214 0.8388 3.1684 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3828 -2.1732 1.2377 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6435 -0.7643 3.8081 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0081 -0.6137 3.8833 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1175 0.7979 3.1535 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0806 -2.4029 1.1323 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5725 -2.3282 2.8042 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4244 -2.8158 1.4304 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8193 1.2336 1.4710 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9534 0.3119 3.2045 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5027 -1.1696 2.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9046 1.4267 2.3146 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0639 -1.3747 0.2669 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2836 -1.8105 -1.8673 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4765 -0.3792 -2.4776 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1468 -0.9339 -2.7383 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2291 1.0289 -1.7029 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3083 3.3742 -0.4198 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1637 2.7146 -1.7004 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6107 3.0545 -0.0411 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9800 0.6057 1.5525 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8334 1.7317 0.3719 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6150 2.4109 1.5376 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7709 -1.0294 -1.1075 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0408 0.3923 -4.0059 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4074 2.1273 -0.2088 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3425 1.3773 -1.4031 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1515 1.4343 -1.6955 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3010 -2.0984 -0.4273 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5340 -0.5642 -1.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8238 1.1529 -0.4943 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1166 1.7804 0.7930 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5448 1.4586 1.1734 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3139 -3.0441 3.0818 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2937 -1.6835 2.6150 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 5 7 1 0 5 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 10 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 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 27 29 1 0 26 30 1 0 25 31 1 0 23 32 1 0 32 33 1 6 32 34 1 0 34 35 2 0 34 36 1 0 36 37 1 0 37 38 1 6 15 39 1 0 12 40 1 1 37 14 1 0 37 17 1 0 32 19 1 0 27 22 1 0 1 41 1 0 1 42 1 0 1 43 1 0 6 44 1 0 6 45 1 0 6 46 1 0 7 47 1 0 7 48 1 0 7 49 1 0 8 50 1 0 8 51 1 0 9 52 1 0 9 53 1 0 13 54 1 0 13 55 1 0 13 56 1 0 14 57 1 6 15 58 1 1 16 59 1 0 16 60 1 0 18 61 1 0 18 62 1 0 18 63 1 0 19 64 1 6 20 65 1 0 20 66 1 0 21 67 1 0 23 68 1 1 24 69 1 0 24 70 1 0 25 71 1 6 26 72 1 6 28 73 1 0 28 74 1 0 28 75 1 0 29 76 1 0 29 77 1 0 29 78 1 0 30 79 1 0 31 80 1 0 33 81 1 0 33 82 1 0 33 83 1 0 36 84 1 0 36 85 1 0 38 86 1 0 38 87 1 0 38 88 1 0 39 89 1 0 40 90 1 0 M END

Standard InCHIKey	LKYNAQSYQLFTCM-GYXNDICUSA-N
Standard InCHI	InChI=1S/C32H50O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,19-22,25-26,34-35,38-39H,11-16H2,1-9H3/t19-,20+,21-,22+,25+,26-,29+,30-,31+,32+/m1/s1
SMILES	CC(=O)OC(C)(C)CCC(=O)[C@@](C)([C@H]1[C@@H](C[C@@]2(C)[C@@H]3CC=C4[C@@H](C[C@@H]([C@H](C4(C)C)O)O)[C@]3(C)C(=O)C[C@]12C)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	562.35	Volume:	587.578 ? Van der Waals volume.
Dense:	0.957	LogP:	2.313 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.707 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.941 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	23.0
TPSA:	141.36 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	4.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.285	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.427	Fsp³:	0.844
MCE-18:	98.983 ? 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:	0.728	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.25	Promiscuous compounds:	0.704

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.998	MDCK Permeability:	-4.574
Pgp-inhibitor:	0.04	Pgp-substrate:	0.035
PAMPA:	0.986 ? 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):	0.006
20% Bioavailability (F20%):	0.097	30% Bioavailability (F30%):	0.414
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.131	MRP1:	0.985
Plasma Protein Binding (PPB):	79.791%	Volume Distribution (VD):	-0.052
Fu:	21.366% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.429
BSEP inhibitor:	0.982

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.538
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.015
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.923	CYP3A4-substrate:	0.989
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.58 ? 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):

7.758

Half-life (T1/2):

1.383

ADMET: Toxicity

hERG Blockers:	0.012	hERG Blockers (10um):	0.137
Human Hepatotoxicity (H-HT):	0.305	Drug-induced Liver Injury (DILI):	0.159
AMES Toxicity:	0.509	Rat Oral Acute Toxicity:	0.288
Maximum Recommended Daily Dose:	0.533	Skin Sensitization:	0.883
Carcinogencity:	0.525	Eye Corrosion:	0.0
Eye Irritation:	0.054	Respiratory Toxicity:	0.314
Drug-induced Neurotoxicity:	0.075	Ototoxicity:	0.646
Hematotoxicity:	0.492	Drug-induced Nephrotoxicity:	0.864
Genotoxicity:	0.968	RPMI-8226 Immunitoxicity:	0.366
A549 Cytotoxicity:	0.085	Hek293 Cytotoxicity:	0.239
BCF:	0.452 ? 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:	3.123 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.64 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.834 ? 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
NPO33474	hemsleya penxianensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717151]
NPO33474	hemsleya penxianensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
Ratio CC50/IC50	3
IC50	6

Activity Type	# Activity
Cell line	2
Organism	3
Others	3
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
NPT323	Cell line	SW-620	Homo sapiens	IC50	=	1.11	ug.mL-1	PMID[26231157]
NPT407	Cell line	COLO 205	Homo sapiens	IC50	=	1.09	ug.mL-1	PMID[18227183]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	11.53	ug.mL-1	PMID[24717151]
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	=	11200.0	nM	DrugMatrix in vitro pharmacology data
NPT963	Organism	Hepatitis B virus	Hepatitis B virus	IC50	>	66200.0	nM	PMID[23327905]
NPT2	Others	Unspecified	n.a.	Ratio CC50/IC50	=	5.8	n.a.	PMID[10743948]
NPT2	Others	Unspecified	n.a.	Ratio CC50/IC50	<	1.0	n.a.	PMID[19734910]

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 NPC280782 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	18862
0.1-0.2	28864
0.2-0.3	2052
0.3-0.4	41
0.4-0.5	16
0.5-0.6	10
0.6-0.7	5
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
0.7727	Intermediate Similarity	NPC191892
0.7714	Intermediate Similarity	NPC196528
0.7222	Intermediate Similarity	NPC257457
0.7222	Intermediate Similarity	NPC311554
0.6757	Remote Similarity	NPC304495
0.6714	Remote Similarity	NPC214644
0.6119	Remote Similarity	NPC110149
0.6047	Remote Similarity	NPC486351
0.6027	Remote Similarity	NPC165873
0.5974	Remote Similarity	NPC486346
0.5811	Remote Similarity	NPC49371
0.5811	Remote Similarity	NPC479419
0.55	Remote Similarity	NPC100267
0.55	Remote Similarity	NPC475524
0.55	Remote Similarity	NPC482855
0.5395	Remote Similarity	NPC117185
0.5375	Remote Similarity	NPC484814
0.5375	Remote Similarity	NPC471854
0.5119	Remote Similarity	NPC486347

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC280782 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7012
0.1-0.2	2101
0.2-0.3	37
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