NPASS Compound

Natural Product: NPC166689

Natural Product ID	NPC166689
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cudraflavanone D
IUPAC Name	(2S)-2-[2,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL218741
PubChem CID	44419446
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

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 59 61 0 0 0 0 0 0 0 0999 V2000 -7.1074 -2.0749 -2.1747 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8089 -0.7497 -1.5195 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5681 -0.3879 -1.3231 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0923 0.8632 -0.7004 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2249 0.6246 0.4708 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 0.7951 0.3854 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0045 0.5852 1.4548 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5916 0.1925 2.6413 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9630 0.0162 2.7530 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7731 0.2363 1.6558 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1305 0.0410 1.8413 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8430 -0.0489 3.7934 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5501 0.7466 1.4287 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0838 2.1281 1.7917 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 2.1027 1.8446 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0746 2.7160 2.7088 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1418 1.3215 0.8368 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3797 0.5075 0.0252 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -0.2259 -0.9221 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4507 -0.1555 -1.0547 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1863 0.6638 -0.2329 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6857 0.7700 -0.3434 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3724 -0.3900 0.2334 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2140 -1.1938 -0.4020 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8472 -2.3465 0.3063 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5679 -0.9782 -1.8335 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5104 1.4074 0.7219 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2476 2.2374 1.5554 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0489 -0.9212 -2.0225 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0012 0.4230 0.1433 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9781 0.0752 -1.1448 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9060 -1.8819 -2.8963 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4709 -2.8005 -1.4025 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2184 -2.5101 -2.6492 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7750 -1.0865 -1.6548 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9313 1.5247 -0.4601 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4926 1.4127 -1.4887 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3984 1.1001 -0.5441 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3958 -0.2933 3.6994 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5573 -0.1188 2.7220 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2239 -0.8719 3.8289 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1006 0.0377 2.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3808 2.8953 1.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4598 2.4269 2.7887 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4671 -0.8708 -1.5643 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0256 1.7036 0.1522 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9731 0.8858 -1.4181 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1757 -0.6222 1.2920 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1774 -3.2298 0.3464 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7869 -2.6142 -0.2097 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0802 -2.0868 1.3595 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3780 -0.1905 -1.8200 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7283 -0.6852 -2.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0261 -1.8822 -2.2546 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4554 1.8877 2.4853 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2476 -1.9007 -1.9239 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8535 -0.5646 -0.9045 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2666 0.6941 -2.0191 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7449 0.6606 -0.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 8 12 1 0 7 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 3 24 25 1 0 24 26 1 0 21 27 2 0 27 28 1 0 20 29 1 0 18 30 1 0 2 31 1 0 10 5 1 0 30 13 1 0 27 17 1 0 1 32 1 0 1 33 1 0 1 34 1 0 3 35 1 0 4 36 1 0 4 37 1 0 6 38 1 0 9 39 1 0 11 40 1 0 12 41 1 0 13 42 1 1 14 43 1 0 14 44 1 0 19 45 1 0 22 46 1 0 22 47 1 0 23 48 1 0 25 49 1 0 25 50 1 0 25 51 1 0 26 52 1 0 26 53 1 0 26 54 1 0 28 55 1 0 29 56 1 0 31 57 1 0 31 58 1 0 31 59 1 0 M END

Standard InCHIKey	XLHAGJGNSIEVFB-QFIPXVFZSA-N
Standard InCHI	InChI=1S/C25H28O6/c1-13(2)5-7-15-9-17(19(27)10-18(15)26)22-12-21(29)24-23(31-22)11-20(28)16(25(24)30)8-6-14(3)4/h5-6,9-11,22,26-28,30H,7-8,12H2,1-4H3/t22-/m0/s1
SMILES	CC(=CCc1cc(c(cc1O)O)[C@@H]1CC(=O)c2c(cc(c(CC=C(C)C)c2O)O)O1)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	424.19	Volume:	444.3 ? Van der Waals volume.
Dense:	0.955	LogP:	4.63 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.53 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.501 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	20.0
TPSA:	107.22 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.49	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.659	Fsp³:	0.32
MCE-18:	68.667 ? 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:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.937	Fluc inhibitor:	0.827 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.886 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.604 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.558	Promiscuous compounds:	0.153

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.982	MDCK Permeability:	-4.737
Pgp-inhibitor:	0.695	Pgp-substrate:	0.018
PAMPA:	0.524 ? 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):	0.358
20% Bioavailability (F20%):	0.938	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.904
Plasma Protein Binding (PPB):	93.879%	Volume Distribution (VD):	0.363
Fu:	6.698% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.989
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.993
BSEP inhibitor:	0.696

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.995	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.013	CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.513	CYP2D6-substrate:	0.739
CYP3A4-inhibitor:	0.05	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	1.0 ? 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):

2.758

Half-life (T1/2):

1.757

ADMET: Toxicity

hERG Blockers:	0.034	hERG Blockers (10um):	0.54
Human Hepatotoxicity (H-HT):	0.833	Drug-induced Liver Injury (DILI):	0.715
AMES Toxicity:	0.844	Rat Oral Acute Toxicity:	0.935
Maximum Recommended Daily Dose:	0.786	Skin Sensitization:	0.991
Carcinogencity:	0.194	Eye Corrosion:	0.0
Eye Irritation:	0.639	Respiratory Toxicity:	0.997
Drug-induced Neurotoxicity:	0.709	Ototoxicity:	0.714
Hematotoxicity:	0.086	Drug-induced Nephrotoxicity:	0.942
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.297
A549 Cytotoxicity:	0.966	Hek293 Cytotoxicity:	0.836
BCF:	2.073 ? 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:	5.049 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.634 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.993 ? 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
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[15787460]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16203143]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16919944]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17608532]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950599]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	fruits	n.a.	n.a.	PMID[19113968]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[19191562]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19280148]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19285413]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19660948]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	Roots	n.a.	n.a.	PMID[25322455]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	root barks	purchased from the local herbal market, Chungbuk, Korea	2012-JUL	PMID[26227773]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30804	Cudrania tricuspidata	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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	4
Inhibition	1
Ki	1

Activity Type	# Activity
Individual protein	3
Tissue	1
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2584	Individual protein	Acyl coenzyme A:cholesterol acyltransferase 2	Homo sapiens	IC50	=	89600.0	nM	PMID[18311894]
NPT1120	Individual protein	Pancreatic triacylglycerol lipase	Sus scrofa	IC50	=	9000.0	nM	PMID[23210623]
NPT1120	Individual protein	Pancreatic triacylglycerol lipase	Sus scrofa	Inhibition	=	74.3	%	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT614	Tissue	Plasma	Rattus norvegicus	IC50	=	65600.0	nM	PMID[25978960]
NPT2	Others	Unspecified	n.a.	IC50	=	10740.0	nM	PMID[4031898]
NPT2	Others	Unspecified	n.a.	Ki	=	7160.0	nM	PMID[20585132]

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 NPC166689 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	21250
0.1-0.2	24947
0.2-0.3	3081
0.3-0.4	403
0.4-0.5	117
0.5-0.6	46
0.6-0.7	8
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
0.7667	Intermediate Similarity	NPC223500
0.7581	Intermediate Similarity	NPC223787
0.7377	Intermediate Similarity	NPC125855
0.6885	Remote Similarity	NPC1089
0.6765	Remote Similarity	NPC267375
0.6471	Remote Similarity	NPC96408
0.6471	Remote Similarity	NPC610511
0.6429	Remote Similarity	NPC185276
0.6176	Remote Similarity	NPC35038
0.6111	Remote Similarity	NPC298692
0.6	Remote Similarity	NPC290133
0.5938	Remote Similarity	NPC258630
0.5775	Remote Similarity	NPC228504
0.5694	Remote Similarity	NPC64915
0.5694	Remote Similarity	NPC213896
0.5672	Remote Similarity	NPC109223
0.5672	Remote Similarity	NPC10937
0.5641	Remote Similarity	NPC293319
0.5616	Remote Similarity	NPC470328
0.5616	Remote Similarity	NPC209614
0.5616	Remote Similarity	NPC164272
0.5616	Remote Similarity	NPC470327
0.5588	Remote Similarity	NPC285555
0.5526	Remote Similarity	NPC210459
0.5467	Remote Similarity	NPC226025
0.5467	Remote Similarity	NPC278778
0.5405	Remote Similarity	NPC488556
0.5362	Remote Similarity	NPC106976
0.5352	Remote Similarity	NPC470890
0.5333	Remote Similarity	NPC472627
0.5333	Remote Similarity	NPC58805
0.5333	Remote Similarity	NPC261063
0.5325	Remote Similarity	NPC45849
0.5325	Remote Similarity	NPC472626
0.5325	Remote Similarity	NPC195796
0.5325	Remote Similarity	NPC283234
0.5286	Remote Similarity	NPC85121
0.5286	Remote Similarity	NPC182852
0.5286	Remote Similarity	NPC608140
0.527	Remote Similarity	NPC279650
0.5263	Remote Similarity	NPC321779
0.5263	Remote Similarity	NPC488558
0.5217	Remote Similarity	NPC17170
0.5211	Remote Similarity	NPC10990
0.5195	Remote Similarity	NPC472628
0.5195	Remote Similarity	NPC488554
0.5195	Remote Similarity	NPC472630
0.5147	Remote Similarity	NPC324436
0.5147	Remote Similarity	NPC78
0.5147	Remote Similarity	NPC39329
0.5147	Remote Similarity	NPC13575
0.5147	Remote Similarity	NPC51032
0.5139	Remote Similarity	NPC200761
0.5128	Remote Similarity	NPC472631
0.5128	Remote Similarity	NPC488557
0.507	Remote Similarity	NPC485610
0.5063	Remote Similarity	NPC27337

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC166689 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3904
0.1-0.2	5198
0.2-0.3	43
0.3-0.4	3
0.4-0.5	2
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