NPASS Compound

Natural Product: NPC246463

Natural Product ID	NPC246463
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	IBKHAIJVZGYPDV-MTGIANMYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14757896
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides

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 66 69 0 0 0 0 0 0 0 0999 V2000 1.9344 1.7040 4.9432 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6456 1.7050 4.4124 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3973 1.4198 3.0662 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8930 1.4335 2.5726 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1246 1.1523 1.2373 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0911 0.8518 0.3816 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3395 0.5762 -1.0402 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6777 -0.1238 -1.1826 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7480 0.7648 -0.6158 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0764 0.1162 -0.5074 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0693 0.6042 0.3271 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3030 0.0658 0.4683 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5936 -1.0601 -0.2801 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6571 -1.5792 -1.1231 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3905 -0.9964 -1.2386 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9323 -2.7085 -1.8874 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9724 -3.2449 -2.7584 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8534 -1.6737 -0.1928 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2566 0.5856 1.3207 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9732 1.7382 2.1031 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4018 1.1544 0.7028 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9076 -0.4288 -2.5267 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2451 0.8239 0.8459 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4124 1.1150 2.1877 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1938 0.5324 0.0157 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4941 0.2986 -0.2410 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9038 -1.1693 0.0561 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4283 -1.0869 0.1524 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8887 -0.7952 -1.2667 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2989 0.5667 -1.6426 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6992 0.7638 -3.1009 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0871 0.7325 -3.1479 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9493 0.5878 -1.4894 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2778 -0.7411 -1.3494 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9891 -2.2207 0.6893 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3580 -1.5983 1.2628 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9309 1.7215 6.0666 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4554 0.7654 4.6254 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5704 2.5330 4.5373 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7334 1.6639 3.2045 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4878 -0.0182 -1.4925 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3602 1.5500 -1.6247 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6363 -1.0199 -0.5357 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7790 1.6734 -1.2989 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8061 1.4899 0.9096 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6934 -1.4709 -1.9104 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6210 -2.4012 -3.4212 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1184 -3.6632 -2.1888 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4045 -4.0748 -3.3696 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7177 -1.2115 -0.4924 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2238 1.4476 2.8794 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4830 2.4768 1.4491 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9369 2.0914 2.5244 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0632 -0.2720 -3.0125 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4300 1.1152 2.6308 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1261 0.8360 0.5595 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6632 -1.7800 -0.8178 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6367 -0.1725 0.7440 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4553 -1.5383 -1.9641 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8463 1.3186 -1.0226 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3333 -0.1369 -3.6711 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2989 1.6800 -3.5539 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4601 0.6026 -4.0590 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5986 -0.6839 -0.4077 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4388 -1.9319 1.5554 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9033 -1.2085 2.0024 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 13 18 1 0 12 19 1 0 19 20 1 0 9 21 1 0 8 22 1 0 6 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 30 33 1 0 29 34 1 0 28 35 1 0 27 36 1 0 24 3 1 0 33 26 1 0 21 5 1 0 15 10 1 0 1 37 1 0 1 38 1 0 1 39 1 0 4 40 1 0 7 41 1 0 7 42 1 0 8 43 1 1 9 44 1 6 11 45 1 0 15 46 1 0 17 47 1 0 17 48 1 0 17 49 1 0 18 50 1 0 20 51 1 0 20 52 1 0 20 53 1 0 22 54 1 0 24 55 1 0 26 56 1 1 27 57 1 6 28 58 1 1 29 59 1 6 30 60 1 1 31 61 1 0 31 62 1 0 32 63 1 0 34 64 1 0 35 65 1 0 36 66 1 0 M END

Standard InCHIKey	IBKHAIJVZGYPDV-MTGIANMYSA-N
Standard InCHI	InChI=1S/C24H30O12/c1-31-11-6-14-12(15(7-11)35-24-22(30)21(29)20(28)18(9-25)36-24)8-13(26)23(34-14)10-4-16(32-2)19(27)17(5-10)33-3/h4-7,13,18,20-30H,8-9H2,1-3H3/t13-,18+,20+,21-,22+,23+,24+/m0/s1
SMILES	COc1cc2c(C[C@@H]([C@@H](c3cc(c(c(c3)OC)O)OC)O2)O)c(c1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	510.17	Volume:	479.098 ? Van der Waals volume.
Dense:	1.065	LogP:	0.658 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.331 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.148 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	23.0
TPSA:	176.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	6.0	Rings:	4.0
Heavy Atoms:	12.0

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:	4.261	Fsp³:	0.5
MCE-18:	93.0 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.514	Fluc inhibitor:	0.054 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.161 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.23 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.138	Promiscuous compounds:	0.198

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.168	MDCK Permeability:	-5.346
Pgp-inhibitor:	0.012	Pgp-substrate:	0.26
PAMPA:	0.147 ? 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):	0.284
20% Bioavailability (F20%):	0.01	30% Bioavailability (F30%):	0.722
50% Bioavailability (F50%):	0.866

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.065	MRP1:	0.389
Plasma Protein Binding (PPB):	84.07%	Volume Distribution (VD):	-0.258
Fu:	17.357% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.565
BSEP inhibitor:	0.081

ADMET: Metabolism

CYP1A2-inhibitor:	0.458	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.98	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.015	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.078
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):

3.556

Half-life (T1/2):

5.029

ADMET: Toxicity

hERG Blockers:	0.056	hERG Blockers (10um):	0.149
Human Hepatotoxicity (H-HT):	0.745	Drug-induced Liver Injury (DILI):	0.864
AMES Toxicity:	0.769	Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.096	Skin Sensitization:	0.971
Carcinogencity:	0.272	Eye Corrosion:	0.0
Eye Irritation:	0.032	Respiratory Toxicity:	0.029
Drug-induced Neurotoxicity:	0.03	Ototoxicity:	0.972
Hematotoxicity:	0.444	Drug-induced Nephrotoxicity:	0.827
Genotoxicity:	0.149	RPMI-8226 Immunitoxicity:	0.192
A549 Cytotoxicity:	0.272	Hek293 Cytotoxicity:	0.308
BCF:	0.371 ? 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:	2.918 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.501 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.613 ? 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
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38783072]
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39349567]
NPO17373.1	Cunninghamia lanceolata var. konishii	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3990	Acacia salicina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3446	Acanthaster planci	Species	Acanthasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16254	Backhousia angustifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6746	Blighia welwitschii	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10438	Tanacetum nubigenum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17707	Dioscorea villosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18768	Haliclona tubifera	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2591	Io fluvialis	Species	Pleuroceridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16377	Juniperus ashei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9524	Kalanchoe blossfeldiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18031	Russula vesca	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15966	Sassafras officinalis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23695	Setosphaeria turcica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2591	Io fluvialis	Species	Pleuroceridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3446	Acanthaster planci	Species	Acanthasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18031	Russula vesca	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16254	Backhousia angustifolia	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15966	Sassafras officinalis	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23695	Setosphaeria turcica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17030	Calvatia lilacina	Species	Lycoperdaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3990	Acacia salicina	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10438	Tanacetum nubigenum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9524	Kalanchoe blossfeldiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13182	Achillea wilhelmsii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16377	Juniperus ashei	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18768	Haliclona tubifera	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6746	Blighia welwitschii	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17373.1	Cunninghamia lanceolata var. konishii	Varieties	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17707	Dioscorea villosa	Species	Dioscoreaceae	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

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

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 NPC246463 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	23751
0.1-0.2	21761
0.2-0.3	3425
0.3-0.4	678
0.4-0.5	221
0.5-0.6	15
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	Natural Product ID
0.5806	Remote Similarity	NPC192810
0.5676	Remote Similarity	NPC216129
0.5676	Remote Similarity	NPC130449
0.5676	Remote Similarity	NPC248132
0.55	Remote Similarity	NPC605526
0.5373	Remote Similarity	NPC306441
0.5316	Remote Similarity	NPC206378
0.52	Remote Similarity	NPC604892
0.5156	Remote Similarity	NPC217854
0.5143	Remote Similarity	NPC23084
0.5128	Remote Similarity	NPC604833
0.5072	Remote Similarity	NPC215833
0.5063	Remote Similarity	NPC76128
0.5063	Remote Similarity	NPC163191
0.506	Remote Similarity	NPC236934

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC246463 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5899
0.1-0.2	3156
0.2-0.3	81
0.3-0.4	13
0.4-0.5	1
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