NPASS Compound

Natural Product: NPC26433

Natural Product ID	NPC26433
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-(Heptadecatrien-8(Z),11(Z),14(Z)-Yl)-2-Hydroxybenzoic Acid
IUPAC Name	2-[(8Z,11Z,14Z)-heptadeca-8,11,14-trienyl]-6-hydroxybenzoic acid
Synonyms	SB-202742
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL33995
PubChem CID	10067772
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0000487] Salicylic acid and derivatives [CHEMONTID:0002514] Salicylic acids

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 61 61 0 0 0 0 0 0 0 0999 V2000 5.9317 -2.7440 -0.0480 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7709 -1.5499 0.3946 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2544 -0.7696 -0.7563 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9471 0.4936 -0.9313 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0948 1.3204 -0.0370 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9209 1.8055 -0.8043 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6844 1.5075 -0.4611 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2629 0.6813 0.6865 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4082 1.4202 1.6267 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1879 1.0475 1.9073 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5304 -0.1258 1.3344 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7189 0.4018 0.5991 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2926 1.3502 -0.4646 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3417 1.9866 -1.2843 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2028 1.2356 -2.1919 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0970 0.1521 -1.6852 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0401 0.5991 -0.6262 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9383 -0.4181 -0.0757 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5427 -0.9632 1.1551 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2700 -1.9315 1.8039 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4358 -2.3996 1.2425 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8250 -1.8643 0.0332 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0951 -0.8806 -0.6357 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5604 -0.3535 -1.9034 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3040 0.6530 -1.9146 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2067 -0.9350 -3.0989 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9870 -2.3203 -0.5419 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5396 -3.5304 -0.5290 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1597 -2.4150 -0.7735 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4928 -3.1797 0.8692 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3193 -1.0056 1.2110 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6963 -2.0360 0.8492 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9040 -1.2114 -1.5330 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3335 1.0469 -1.8145 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7325 2.2497 0.2249 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9106 0.8524 0.8997 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1142 2.4402 -1.6942 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9012 1.9327 -1.1169 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1626 0.3712 1.2854 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8529 -0.2579 0.2975 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8107 2.3254 2.1163 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6012 1.6617 2.6327 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0684 -0.7103 0.6009 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1134 -0.8143 2.1250 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4033 -0.3855 0.3773 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2209 1.0506 1.3921 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4796 0.8411 -1.1279 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2678 2.1811 0.0987 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9438 2.6304 -0.5544 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8445 2.8270 -1.9041 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8098 1.9628 -2.8496 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5106 0.7874 -2.9948 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5130 -0.7288 -1.4101 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7078 -0.1309 -2.6395 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4810 1.0790 0.1899 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7305 1.3587 -1.1262 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6292 -0.6347 1.6509 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9454 -2.3478 2.7688 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0140 -3.1661 1.7532 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4501 -0.5153 -3.9890 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3919 -1.9275 -1.3824 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 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 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 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 24 26 1 0 22 27 1 0 23 18 1 0 1 28 1 0 1 29 1 0 1 30 1 0 2 31 1 0 2 32 1 0 3 33 1 0 4 34 1 0 5 35 1 0 5 36 1 0 6 37 1 0 7 38 1 0 8 39 1 0 8 40 1 0 9 41 1 0 10 42 1 0 11 43 1 0 11 44 1 0 12 45 1 0 12 46 1 0 13 47 1 0 13 48 1 0 14 49 1 0 14 50 1 0 15 51 1 0 15 52 1 0 16 53 1 0 16 54 1 0 17 55 1 0 17 56 1 0 19 57 1 0 20 58 1 0 21 59 1 0 26 60 1 0 27 61 1 0 M END

Standard InCHIKey	MBYMHCHZLAJVRK-PDBXOOCHSA-N
Standard InCHI	InChI=1S/C24H34O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-18-21-19-17-20-22(25)23(21)24(26)27/h3-4,6-7,9-10,17,19-20,25H,2,5,8,11-16,18H2,1H3,(H,26,27)/b4-3-,7-6-,10-9-
SMILES	CC/C=CC/C=CC/C=CCCCCCCCc1cccc(c1C(=O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	370.25	Volume:	423.019 ? Van der Waals volume.
Dense:	0.875	LogP:	7.92 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.834 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.49 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	10.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	1.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.279	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.738	Fsp³:	0.458
MCE-18:	7.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.617	Fluc inhibitor:	0.252 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.063 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.306 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.682	Promiscuous compounds:	0.154

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.062	MDCK Permeability:	-4.773
Pgp-inhibitor:	0.986	Pgp-substrate:	0.0
PAMPA:	0.001 ? 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):	0.005
20% Bioavailability (F20%):	0.238	30% Bioavailability (F30%):	0.843
50% Bioavailability (F50%):	0.83

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.997
Plasma Protein Binding (PPB):	98.54%	Volume Distribution (VD):	-0.382
Fu:	0.657% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.035
OATP1B3 inhibitor:	0.466	BCRP inhibitor:	0.681
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.002	CYP1A2-substrate:	0.744
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.008
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.996	CYP2D6-substrate:	0.962
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.993
CYP2B6-substrate:	0.241	CYP2C8-inhibitor:	1.0
HLM stability:	0.01 ? 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):

2.745

Half-life (T1/2):

0.669

ADMET: Toxicity

hERG Blockers:	0.335	hERG Blockers (10um):	0.403
Human Hepatotoxicity (H-HT):	0.023	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.594	Rat Oral Acute Toxicity:	0.053
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	1.0
Eye Irritation:	1.0	Respiratory Toxicity:	0.995
Drug-induced Neurotoxicity:	0.014	Ototoxicity:	0.066
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.697
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.02
A549 Cytotoxicity:	0.412	Hek293 Cytotoxicity:	0.004
BCF:	1.21 ? 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:	4.593 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.011 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.184 ? 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
NPO1454	Spondias mombin	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064298]
NPO6707	Cosmopterix victor	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8223	Gnaphalium polycaulon	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9081	Lecidea aglaeotera	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1454	Spondias mombin	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9081	Lecidea aglaeotera	Species	Lecideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8223	Gnaphalium polycaulon	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6707	Cosmopterix victor	Species	Cosmopterigidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1454	Spondias mombin	Species	Anacardiaceae	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	12
MIC	15

Activity Type	# Activity
Individual protein	10
Organism	15
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT650	Individual protein	Beta-lactamase pse-1	Escherichia coli	IC50	=	10000.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80506-0]
NPT651	Individual protein	Beta-lactamase OXA-1	Escherichia coli	IC50	=	80000.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80506-0]
NPT654	Individual protein	Beta-lactamase	Enterobacter cloacae	IC50	=	17000.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80506-0]
NPT655	Individual protein	Beta-lactamase	Proteus mirabilis	IC50	=	110000.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80506-0]
NPT654	Individual protein	Beta-lactamase	Enterobacter cloacae	IC50	=	16.5	ug.mL-1	PMID[8064298]
NPT655	Individual protein	Beta-lactamase	Proteus mirabilis	IC50	=	111.3	ug.mL-1	PMID[8064298]
NPT652	Individual protein	Beta-lactamase TEM	Escherichia coli	IC50	=	5000.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80506-0]
NPT652	Individual protein	Beta-lactamase TEM	Escherichia coli	IC50	=	5.0	ug.mL-1	PMID[8064298]
NPT653	Individual protein	Beta-lactamase	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)	IC50	=	41000.0	ug.mL-1	DOI[10.1016/S0960-894X(01)80506-0]
NPT653	Individual protein	Beta-lactamase	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)	IC50	=	40.5	ug.mL-1	PMID[8064298]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT172	Organism	Proteus mirabilis	Proteus mirabilis	MIC	>	256.0	ug.mL-1	PMID[8064298]
NPT1033	Organism	Enterobacter cloacae	Enterobacter cloacae	MIC	>	256.0	ug.mL-1	PMID[8064298]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	2.0	ug.mL-1	PMID[8064298]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	256.0	ug.mL-1	PMID[8064298]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4.0	ug.mL-1	PMID[8064298]
NPT1228	Organism	Streptococcus pyogenes	Streptococcus pyogenes	MIC	=	2.0	ug.mL-1	PMID[8064298]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	256.0	ug.mL-1	PMID[8064298]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	256.0	ug.mL-1	PMID[8064298]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8.0	ug.mL-1	PMID[8064298]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[8064298]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[8064298]
NPT1863	Organism	Staphylococcus saprophyticus	Staphylococcus saprophyticus	MIC	=	2.0	ug.mL-1	PMID[8064298]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	2.0	ug.mL-1	PMID[8064298]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	0.25	ug.mL-1	PMID[8064298]
NPT2	Others	Unspecified	n.a.	IC50	=	10.1	ug.mL-1	PMID[8064298]
NPT2	Others	Unspecified	n.a.	IC50	=	79.7	ug.mL-1	PMID[8064298]
NPT1248	Organism	Serratia marcescens	Serratia marcescens	MIC	>	256.0	ug.mL-1	PMID[8064298]

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 NPC26433 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	20785
0.1-0.2	27094
0.2-0.3	1771
0.3-0.4	155
0.4-0.5	29
0.5-0.6	0
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	9
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.92	High Similarity	NPC115188
0.92	High Similarity	NPC159760
0.92	High Similarity	NPC301987
0.8824	High Similarity	NPC184579
0.8824	High Similarity	NPC233165
0.8776	High Similarity	NPC238531
0.8776	High Similarity	NPC178395
0.86	High Similarity	NPC244994
0.86	High Similarity	NPC222876
0.86	High Similarity	NPC292665
0.86	High Similarity	NPC179092
0.8571	High Similarity	NPC483452
0.7963	Intermediate Similarity	NPC167055
0.74	Intermediate Similarity	NPC483451
0.74	Intermediate Similarity	NPC227450
0.74	Intermediate Similarity	NPC272454
0.74	Intermediate Similarity	NPC35856
0.74	Intermediate Similarity	NPC609957
0.7119	Intermediate Similarity	NPC240744
0.6852	Remote Similarity	NPC605990
0.6667	Remote Similarity	NPC244351
0.6667	Remote Similarity	NPC483453
0.6034	Remote Similarity	NPC17840
0.6034	Remote Similarity	NPC247477

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC26433 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3420
0.1-0.2	5444
0.2-0.3	277
0.3-0.4	9
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