NPASS Compound

Natural Product: NPC58752

Natural Product ID	NPC58752
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	12-Methoxycarnosic Acid
IUPAC Name	(4aR,10aS)-5-hydroxy-6-methoxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid
Synonyms	Carnosic Acid 12-Methyl Ether
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1096627
PubChem CID	9974918
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

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 55 57 0 0 0 0 0 0 0 0999 V2000 4.0347 0.0737 2.4561 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3644 1.0473 1.6384 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4401 0.5895 0.7022 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1051 0.4277 1.0206 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7427 0.7462 2.3148 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1585 -0.0304 0.1001 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5240 -0.3429 -1.1795 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8810 -0.1788 -1.5047 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8052 0.2732 -0.5899 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2424 0.4473 -0.9597 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0541 -0.7701 -0.6601 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8322 1.7286 -0.4211 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3886 -0.8320 -2.2475 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6549 -1.3107 -1.5892 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1248 -0.1959 -0.6631 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2737 -0.1700 0.5641 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6532 1.0704 1.3705 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0180 1.5833 1.0570 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0101 0.4583 0.8222 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5961 -0.2110 -0.4758 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2530 -1.5453 -0.6540 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2009 0.6888 -1.5764 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4231 -1.3348 1.4540 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1597 -2.3184 1.2231 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7121 -1.3871 2.6491 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1262 0.2992 2.4761 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6968 0.1415 3.5113 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9270 -0.9395 2.0291 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3692 0.5453 3.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1915 -0.4250 -2.5267 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2233 0.5542 -2.0862 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6977 -1.0293 -1.5195 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7254 -0.6515 0.2193 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3399 -1.6215 -0.5150 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5058 1.5233 0.4433 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3937 2.2203 -1.2343 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9914 2.4214 -0.1392 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6509 0.0111 -2.9119 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0416 -1.6902 -2.8002 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5350 -2.2569 -1.0336 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4353 -1.3967 -2.3827 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8581 0.7584 -1.2172 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9388 1.9072 1.1927 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5605 0.8407 2.4758 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3645 2.2529 1.8523 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0040 2.1864 0.1177 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0888 -0.2344 1.6605 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0009 0.9371 0.6856 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1343 -1.5046 -1.3660 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6169 -2.3405 -1.0655 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6989 -1.9248 0.2959 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4687 1.5042 -1.7481 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1536 1.1128 -1.2088 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3631 0.1073 -2.5076 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0735 -1.8152 3.4931 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 4 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 10 12 1 0 7 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 16 23 1 1 23 24 2 0 23 25 1 0 9 3 1 0 20 15 1 0 16 6 1 0 1 26 1 0 1 27 1 0 1 28 1 0 5 29 1 0 8 30 1 0 10 31 1 0 11 32 1 0 11 33 1 0 11 34 1 0 12 35 1 0 12 36 1 0 12 37 1 0 13 38 1 0 13 39 1 0 14 40 1 0 14 41 1 0 15 42 1 6 17 43 1 0 17 44 1 0 18 45 1 0 18 46 1 0 19 47 1 0 19 48 1 0 21 49 1 0 21 50 1 0 21 51 1 0 22 52 1 0 22 53 1 0 22 54 1 0 25 55 1 0 M END

Standard InCHIKey	QQNSARJGBPMQDI-YCRPNKLZSA-N
Standard InCHI	InChI=1S/C21H30O4/c1-12(2)14-11-13-7-8-15-20(3,4)9-6-10-21(15,19(23)24)16(13)17(22)18(14)25-5/h11-12,15,22H,6-10H2,1-5H3,(H,23,24)/t15-,21+/m0/s1
SMILES	COc1c(O)c2c(cc1C(C)C)CC[C@@H]1[C@@]2(CCCC1(C)C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	346.21	Volume:	370.718 ? Van der Waals volume.
Dense:	0.934	LogP:	3.557 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.917 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.806 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	17.0
TPSA:	66.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	3.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.838	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.751	Fsp³:	0.667
MCE-18:	79.514 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.137	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.073 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.016 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.203	Promiscuous compounds:	0.015

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.761	MDCK Permeability:	-4.774
Pgp-inhibitor:	0.724	Pgp-substrate:	0.001
PAMPA:	0.046 ? 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):	0.003
20% Bioavailability (F20%):	0.074	30% Bioavailability (F30%):	0.091
50% Bioavailability (F50%):	0.86

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.998
Plasma Protein Binding (PPB):	95.805%	Volume Distribution (VD):	-0.424
Fu:	4.185% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.981	BCRP inhibitor:	0.023
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.01
CYP2C19-inhibitor:	0.875	CYP2C19-substrate:	0.024
CYP2C9-inhibitor:	0.977	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.024	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.388	CYP3A4-substrate:	0.001
CYP2B6-substrate:	0.046	CYP2C8-inhibitor:	0.181
HLM stability:	0.115 ? 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):

3.816

Half-life (T1/2):

1.115

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.085
Human Hepatotoxicity (H-HT):	0.59	Drug-induced Liver Injury (DILI):	0.321
AMES Toxicity:	0.235	Rat Oral Acute Toxicity:	0.37
Maximum Recommended Daily Dose:	0.533	Skin Sensitization:	0.862
Carcinogencity:	0.611	Eye Corrosion:	0.064
Eye Irritation:	0.835	Respiratory Toxicity:	0.939
Drug-induced Neurotoxicity:	0.022	Ototoxicity:	0.649
Hematotoxicity:	0.635	Drug-induced Nephrotoxicity:	0.903
Genotoxicity:	0.139	RPMI-8226 Immunitoxicity:	0.04
A549 Cytotoxicity:	0.045	Hek293 Cytotoxicity:	0.112
BCF:	1.457 ? 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:	4.09 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.425 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.914 ? 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
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10096857]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23507152]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33321838]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36432812]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36987013]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37176852]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37751472]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37836118]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37836125]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6098	Salvia officinalis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28520	Heliotropium subulatum	Species	Heliotropiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28354	Tragacantha stipulosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6095	Xanthoparmelia verruculifera	Species	Parmeliaceae	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	6
Inhibition	32

Activity Type	# Activity
Cell line	4
Organism	33
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
NPT171	Cell line	MRC5	Homo sapiens	IC50	=	54900.0	nM	PMID[20359186]
NPT196	Cell line	AGS	Homo sapiens	IC50	=	45200.0	nM	PMID[20359186]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	43500.0	nM	PMID[20359186]
NPT839	Cell line	L6	Rattus norvegicus	IC50	=	17300.0	nM	PMID[25462275]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	750.0	nM	PMID[25462275]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	750.0	nM	PMID[27318121]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	Inhibition	=	4.0	%	PMID[33378620]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	Inhibition	=	81.0	%	PMID[33378620]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	Inhibition	=	74.1	%	PMID[33378620]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	Inhibition	=	6.7	%	PMID[33378620]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Inhibition	=	31.9	%	PMID[33378620]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Inhibition	=	72.0	%	PMID[33378620]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	71.6	%	PMID[33378620]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	81.2	%	PMID[33378620]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	3.2	%	PMID[33378620]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	68.6	%	PMID[33378620]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	43.2	%	PMID[33378620]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	Inhibition	=	0.0	%	PMID[33378620]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	66.3	%	PMID[33378620]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	67.2	%	PMID[33378620]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	96.1	%	PMID[33378620]

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 NPC58752 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	14430
0.1-0.2	33185
0.2-0.3	2187
0.3-0.4	44
0.4-0.5	8
0.5-0.6	0
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC608735
0.6885	Remote Similarity	NPC293454
0.6667	Remote Similarity	NPC213122

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC58752 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2937
0.1-0.2	6001
0.2-0.3	211
0.3-0.4	1
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