NPASS Compound

Natural Product: NPC43550

Natural Product ID	NPC43550
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cernuoside A
IUPAC Name	[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL499404
PubChem CID	21668763
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 2D 222233 0 0 0 0 0 0 0 0999 V2000 12.4472 -7.1864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6972 -5.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9472 -4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7981 -3.6241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0586 -2.1469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5586 -2.1469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8086 -0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 0.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9095 -0.5130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3405 -9.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0105 -10.5705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9895 -10.5705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1386 -11.5347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9895 -12.4988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -13.9761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6595 -14.4891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8086 -13.5249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5481 -12.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8086 -10.5705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2181 -10.0574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4786 -11.5347 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8882 -12.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0372 -13.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0372 -11.0835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7768 -9.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3672 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2181 -8.1291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0372 -8.1291 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.4468 -7.6161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6968 -6.3170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.4468 -5.0180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7072 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93 3 1 0 101 95 1 0 87 8 1 0 27 14 1 0 38 32 1 0 47 42 1 0 55 49 1 0 65 58 1 0 79 72 1 0 19 14 1 0 25 20 1 0 33 23 1 0 1107 1 0 2108 1 0 2109 1 0 3110 1 6 5111 1 6 7112 1 0 7113 1 0 8114 1 6 10115 1 6 15116 1 0 15117 1 0 16118 1 0 16119 1 0 18120 1 0 18121 1 0 19122 1 1 21123 1 0 22124 1 0 22125 1 0 23126 1 6 26127 1 0 26128 1 0 27129 1 0 27130 1 0 28131 1 0 28132 1 0 28133 1 0 29134 1 0 29135 1 0 29136 1 0 30137 1 0 30138 1 0 31139 1 0 31140 1 0 32141 1 6 34142 1 0 34143 1 0 34144 1 0 35145 1 0 35146 1 0 36147 1 0 36148 1 0 37149 1 6 39150 1 0 39151 1 0 39152 1 0 40153 1 0 40154 1 0 40155 1 0 42156 1 1 44157 1 0 44158 1 0 45159 1 1 46160 1 1 47161 1 6 49162 1 1 51163 1 6 52164 1 0 52165 1 0 52166 1 0 53167 1 1 54168 1 6 55169 1 6 56170 1 0 58171 1 6 60172 1 6 61173 1 0 61174 1 0 62175 1 0 63176 1 1 64177 1 6 65178 1 1 66179 1 0 67180 1 0 68181 1 0 69182 1 0 70183 1 0 72184 1 6 74185 1 6 75186 1 0 75187 1 0 76188 1 0 77189 1 1 78190 1 6 79191 1 1 80192 1 0 81193 1 0 82194 1 0 83195 1 0 83196 1 0 83197 1 0 84198 1 0 84199 1 0 84200 1 0 85201 1 1 86202 1 6 87203 1 1 88204 1 0 89205 1 0 90206 1 0 91207 1 1 92208 1 6 93209 1 1 95210 1 1 97211 1 6 98212 1 0 98213 1 0 98214 1 0 99215 1 1 100216 1 6 101217 1 6 102218 1 0 103219 1 0 104220 1 0 105221 1 0 106222 1 0 M END

Standard InCHIKey	MGKHSBUGNYQRRH-SCBJEXJVSA-N
Standard InCHI	InChI=1S/C71H116O35/c1-26-38(75)44(81)49(86)59(95-26)103-55-32(23-74)99-58(53(90)48(55)85)93-24-33-42(79)47(84)52(89)62(100-33)106-65(92)71-18-16-66(3,4)20-29(71)28-10-11-36-68(7)14-13-37(67(5,6)35(68)12-15-70(36,9)69(28,8)17-19-71)102-64-57(43(80)34(25-94-64)101-60-50(87)45(82)40(77)30(21-72)97-60)105-63-54(91)56(39(76)27(2)96-63)104-61-51(88)46(83)41(78)31(22-73)98-61/h10,26-27,29-64,72-91H,11-25H2,1-9H3/t26-,27-,29-,30+,31+,32+,33+,34-,35-,36+,37-,38-,39-,40+,41+,42+,43-,44+,45-,46-,47-,48+,49+,50+,51+,52+,53+,54+,55+,56+,57+,58+,59-,60-,61-,62-,63-,64-,68-,69+,70+,71-/m0/s1
SMILES	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(=O)[C@@]34CCC(C[C@H]4C4=CC[C@H]5[C@@]([C@@]4(CC3)C)(C)CC[C@@H]3[C@]5(C)CC[C@@H](C3(C)C)O[C@@H]3OC[C@@H]([C@@H]([C@H]3O[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)O)O)O[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)(C)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1528.73	Volume:	1436.279 ? Van der Waals volume.
Dense:	1.064	LogP:	-0.059 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.738 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.155 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	69.0
TPSA:	550.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	35.0
H-Bond Donor:	20.0	Rings:	12.0
Heavy Atoms:	35.0

MedChem Properties

QED Drug-Likeness Score:	0.035	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.937	Fsp³:	0.958
MCE-18:	262.388 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.737	Fluc inhibitor:	0.127 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? 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:	0.45	Promiscuous compounds:	0.067

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.507	MDCK Permeability:	-4.979
Pgp-inhibitor:	0.0	Pgp-substrate:	0.879
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):	1.0
20% Bioavailability (F20%):	0.919	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	54.698%	Volume Distribution (VD):	-0.235
Fu:	21.989% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.075
HLM stability:	0.003 ? 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):

-1.957

Half-life (T1/2):

5.712

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.769	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.998	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.758	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.182	RPMI-8226 Immunitoxicity:	0.624
A549 Cytotoxicity:	0.989	Hek293 Cytotoxicity:	0.36
BCF:	1.236 ? 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:	3.484 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.922 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.959 ? 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
NPO18782	Pulsatilla cernua	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1248/cpb.26.1666]
NPO18782	Pulsatilla cernua	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691728]
NPO18782	Pulsatilla cernua	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18782	Pulsatilla cernua	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18782	Pulsatilla cernua	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18782	Pulsatilla cernua	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18782	Pulsatilla cernua	Species	Ranunculaceae	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	1

Activity Type	# Activity
Individual protein	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT462	Individual protein	Sucrase-isomaltase	Rattus norvegicus	IC50	=	59500.0	nM	Open TG-GATES in vivo data: Biochemistry

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

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 NPC43550 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	25399
0.1-0.2	20595
0.2-0.3	2569
0.3-0.4	673
0.4-0.5	381
0.5-0.6	88
0.6-0.7	56
0.7-0.8	0
0.8-0.85	14
0.85-0.9	2
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9558	High Similarity	NPC250247
0.9286	High Similarity	NPC65105
0.9204	High Similarity	NPC305981
0.9123	High Similarity	NPC261506
0.9123	High Similarity	NPC4328
0.9027	High Similarity	NPC41061
0.9027	High Similarity	NPC227551
0.8707	High Similarity	NPC236638
0.8707	High Similarity	NPC294453
0.8496	Intermediate Similarity	NPC135904
0.8475	Intermediate Similarity	NPC298034
0.8475	Intermediate Similarity	NPC71065
0.8435	Intermediate Similarity	NPC481080
0.839	Intermediate Similarity	NPC136768
0.8319	Intermediate Similarity	NPC79643
0.8261	Intermediate Similarity	NPC475160
0.8261	Intermediate Similarity	NPC473714
0.823	Intermediate Similarity	NPC60557
0.823	Intermediate Similarity	NPC67857
0.8205	Intermediate Similarity	NPC476068
0.8083	Intermediate Similarity	NPC202828
0.8083	Intermediate Similarity	NPC119592
0.8017	Intermediate Similarity	NPC123199
0.7917	Intermediate Similarity	NPC258617
0.7913	Intermediate Similarity	NPC475287
0.7886	Intermediate Similarity	NPC220160
0.7731	Intermediate Similarity	NPC488560
0.7719	Intermediate Similarity	NPC295823
0.7719	Intermediate Similarity	NPC174720
0.7719	Intermediate Similarity	NPC475467
0.7705	Intermediate Similarity	NPC293330
0.7686	Intermediate Similarity	NPC110633
0.7642	Intermediate Similarity	NPC481081
0.7607	Intermediate Similarity	NPC76972
0.7607	Intermediate Similarity	NPC469782
0.7607	Intermediate Similarity	NPC204414
0.75	Intermediate Similarity	NPC481078
0.7434	Intermediate Similarity	NPC63159
0.7355	Intermediate Similarity	NPC100639
0.7248	Intermediate Similarity	NPC48499
0.719	Intermediate Similarity	NPC165204
0.7168	Intermediate Similarity	NPC112352
0.7153	Intermediate Similarity	NPC481323
0.7153	Intermediate Similarity	NPC469778
0.7131	Intermediate Similarity	NPC155410
0.713	Intermediate Similarity	NPC148417
0.7119	Intermediate Similarity	NPC241909
0.7113	Intermediate Similarity	NPC469776
0.7107	Intermediate Similarity	NPC192600
0.7105	Intermediate Similarity	NPC104071
0.7083	Intermediate Similarity	NPC32723
0.7063	Intermediate Similarity	NPC475514
0.7047	Intermediate Similarity	NPC295941
0.7043	Intermediate Similarity	NPC102439
0.7016	Intermediate Similarity	NPC54636
0.6939	Remote Similarity	NPC135334
0.6935	Remote Similarity	NPC470218
0.6905	Remote Similarity	NPC57484
0.6892	Remote Similarity	NPC481324
0.6891	Remote Similarity	NPC481079
0.6752	Remote Similarity	NPC46665
0.6667	Remote Similarity	NPC224381
0.6644	Remote Similarity	NPC469775
0.6639	Remote Similarity	NPC475504
0.6623	Remote Similarity	NPC469777
0.6622	Remote Similarity	NPC469774
0.6615	Remote Similarity	NPC161717
0.661	Remote Similarity	NPC473459
0.6601	Remote Similarity	NPC469772
0.6591	Remote Similarity	NPC70809
0.6581	Remote Similarity	NPC223301
0.6581	Remote Similarity	NPC171544
0.6529	Remote Similarity	NPC104372
0.6525	Remote Similarity	NPC309714
0.6522	Remote Similarity	NPC475516
0.6516	Remote Similarity	NPC469773
0.6496	Remote Similarity	NPC469946
0.649	Remote Similarity	NPC100925
0.6393	Remote Similarity	NPC114484
0.6379	Remote Similarity	NPC235405
0.6364	Remote Similarity	NPC471385
0.6364	Remote Similarity	NPC222580
0.6333	Remote Similarity	NPC251768
0.6325	Remote Similarity	NPC249848
0.6325	Remote Similarity	NPC107966
0.6281	Remote Similarity	NPC235438
0.6271	Remote Similarity	NPC295371
0.6261	Remote Similarity	NPC29069
0.625	Remote Similarity	NPC30735
0.623	Remote Similarity	NPC297263
0.6202	Remote Similarity	NPC166422
0.6202	Remote Similarity	NPC251263
0.6198	Remote Similarity	NPC10607
0.6167	Remote Similarity	NPC192791
0.616	Remote Similarity	NPC80986
0.6154	Remote Similarity	NPC191827
0.6115	Remote Similarity	NPC480422
0.6111	Remote Similarity	NPC31838
0.608	Remote Similarity	NPC301449
0.608	Remote Similarity	NPC601290
0.6077	Remote Similarity	NPC219180
0.6066	Remote Similarity	NPC159309
0.6066	Remote Similarity	NPC86222
0.6063	Remote Similarity	NPC75287
0.605	Remote Similarity	NPC150400
0.6034	Remote Similarity	NPC214484
0.6016	Remote Similarity	NPC475591
0.6016	Remote Similarity	NPC236870
0.6	Remote Similarity	NPC471384
0.6	Remote Similarity	NPC39211
0.6	Remote Similarity	NPC470911
0.5984	Remote Similarity	NPC160415
0.5984	Remote Similarity	NPC187290
0.5968	Remote Similarity	NPC257468
0.5968	Remote Similarity	NPC609763
0.5935	Remote Similarity	NPC101744
0.5935	Remote Similarity	NPC173859
0.5935	Remote Similarity	NPC148603
0.5935	Remote Similarity	NPC480475
0.5926	Remote Similarity	NPC470876
0.5917	Remote Similarity	NPC473373
0.5873	Remote Similarity	NPC281148
0.5833	Remote Similarity	NPC475209
0.582	Remote Similarity	NPC161674
0.582	Remote Similarity	NPC76497
0.5797	Remote Similarity	NPC309223
0.5797	Remote Similarity	NPC302543
0.5781	Remote Similarity	NPC488564
0.5758	Remote Similarity	NPC323341
0.5758	Remote Similarity	NPC133818
0.5745	Remote Similarity	NPC102505
0.5745	Remote Similarity	NPC488514
0.5743	Remote Similarity	NPC472268
0.5735	Remote Similarity	NPC286457
0.5714	Remote Similarity	NPC123796
0.5682	Remote Similarity	NPC123522
0.568	Remote Similarity	NPC40775
0.5676	Remote Similarity	NPC297950
0.5669	Remote Similarity	NPC134835
0.5659	Remote Similarity	NPC69811
0.5635	Remote Similarity	NPC68175
0.563	Remote Similarity	NPC90856
0.5625	Remote Similarity	NPC33012
0.5612	Remote Similarity	NPC135849
0.561	Remote Similarity	NPC470512
0.561	Remote Similarity	NPC157868
0.5581	Remote Similarity	NPC324875
0.5581	Remote Similarity	NPC292677
0.5577	Remote Similarity	NPC472269
0.5573	Remote Similarity	NPC470915
0.5565	Remote Similarity	NPC473343
0.5563	Remote Similarity	NPC45606
0.5556	Remote Similarity	NPC164389
0.5556	Remote Similarity	NPC8524
0.5556	Remote Similarity	NPC471550
0.5547	Remote Similarity	NPC21691
0.5538	Remote Similarity	NPC96641
0.5538	Remote Similarity	NPC163183
0.553	Remote Similarity	NPC185466
0.5528	Remote Similarity	NPC173583
0.5512	Remote Similarity	NPC139044
0.5512	Remote Similarity	NPC470515
0.551	Remote Similarity	NPC475368
0.5507	Remote Similarity	NPC13998
0.5504	Remote Similarity	NPC73318
0.5496	Remote Similarity	NPC36831
0.5489	Remote Similarity	NPC610204
0.5478	Remote Similarity	NPC237503
0.5474	Remote Similarity	NPC85154
0.5462	Remote Similarity	NPC323359
0.544	Remote Similarity	NPC213674
0.5439	Remote Similarity	NPC167383
0.5426	Remote Similarity	NPC471435
0.5426	Remote Similarity	NPC471434
0.5426	Remote Similarity	NPC469821
0.5425	Remote Similarity	NPC220838
0.542	Remote Similarity	NPC480473
0.542	Remote Similarity	NPC480474
0.5403	Remote Similarity	NPC58448
0.5385	Remote Similarity	NPC478559
0.5385	Remote Similarity	NPC478560
0.5379	Remote Similarity	NPC104137
0.5379	Remote Similarity	NPC475486
0.5379	Remote Similarity	NPC26626
0.5379	Remote Similarity	NPC473826
0.5378	Remote Similarity	NPC128925
0.5373	Remote Similarity	NPC268184
0.5369	Remote Similarity	NPC489208
0.5333	Remote Similarity	NPC151543
0.5317	Remote Similarity	NPC263756
0.5312	Remote Similarity	NPC305267
0.531	Remote Similarity	NPC480417
0.5308	Remote Similarity	NPC64715
0.5308	Remote Similarity	NPC601659
0.5306	Remote Similarity	NPC477464
0.529	Remote Similarity	NPC47995
0.5286	Remote Similarity	NPC473452
0.5286	Remote Similarity	NPC480418
0.5267	Remote Similarity	NPC78034

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC43550 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7855
0.1-0.2	1237
0.2-0.3	50
0.3-0.4	8
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