NPASS Compound

Natural Product: NPC544624

Natural Product ID	NPC544624
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lesquerolic acid
IUPAC Name	(~{Z},14~{R})-14-hydroxyicos-11-enoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 60 0 0 0 0 0 0 0 0999 V2000 -6.9221 -2.9201 -2.0354 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5929 -1.8844 -0.9574 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3130 -2.2963 -0.2841 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8898 -1.3320 0.8195 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6815 0.0244 0.2267 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2726 1.0649 1.1985 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0063 0.8728 1.9389 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9817 -0.2705 2.7186 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7779 0.8842 1.0532 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5539 0.7163 1.8501 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4453 1.5931 1.9234 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3899 2.8464 1.1785 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4975 3.0898 0.1925 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6735 2.1288 -0.9007 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9991 0.7274 -0.6329 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2817 0.4863 0.1272 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4075 1.0568 -0.6843 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7498 0.9221 -0.1029 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2702 -0.4350 0.1729 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3671 -1.3092 -1.0610 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8955 -2.6542 -0.7364 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0846 -2.9150 -0.4620 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9719 -3.7204 -0.7409 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3154 -2.7383 -2.9542 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6169 -3.9021 -1.6443 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9916 -2.8991 -2.3128 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3982 -0.9431 -1.5445 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4318 -1.7711 -0.2742 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4712 -2.3423 -1.0078 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4257 -3.3010 0.1763 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7315 -1.2546 1.5628 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0282 -1.7892 1.3003 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7016 0.3416 -0.1551 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0653 0.0025 -0.6993 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0915 1.0949 1.9822 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3190 2.0872 0.7524 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8922 1.7381 2.6372 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2343 -0.8840 2.5440 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8717 -0.1007 0.4741 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7695 1.6328 0.2754 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3749 -0.1900 2.4629 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3367 1.3930 2.5491 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6067 3.1213 0.7717 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5387 3.6636 1.9742 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2243 4.0778 -0.3058 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4549 3.3726 0.7120 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7030 2.1324 -1.4942 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4038 2.5396 -1.6647 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2163 0.2571 -1.6539 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2133 0.0709 -0.2333 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3673 -0.6192 0.2406 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2452 0.8870 1.1572 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3941 0.6560 -1.7177 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2015 2.1556 -0.7955 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8301 1.5104 0.8481 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4861 1.4277 -0.7927 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3420 -0.2989 0.5141 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7844 -0.9667 1.0157 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0441 -0.8462 -1.8253 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4048 -1.4450 -1.5860 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1046 -4.5470 -0.1708 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 1 0 10 11 2 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 1 0 19 20 1 0 20 21 1 0 21 22 2 0 21 23 1 0 1 24 1 0 1 25 1 0 1 26 1 0 2 27 1 0 2 28 1 0 3 29 1 0 3 30 1 0 4 31 1 0 4 32 1 0 5 33 1 0 5 34 1 0 6 35 1 0 6 36 1 0 7 37 1 1 8 38 1 0 9 39 1 0 9 40 1 0 10 41 1 0 11 42 1 0 12 43 1 0 12 44 1 0 13 45 1 0 13 46 1 0 14 47 1 0 14 48 1 0 15 49 1 0 15 50 1 0 16 51 1 0 16 52 1 0 17 53 1 0 17 54 1 0 18 55 1 0 18 56 1 0 19 57 1 0 19 58 1 0 20 59 1 0 20 60 1 0 23 61 1 0 M END

Standard InCHIKey	OONXYOAWMIVMCI-KWRJMZDGSA-N
Standard InCHI	InChI=1S/C20H38O3/c1-2-3-4-13-16-19(21)17-14-11-9-7-5-6-8-10-12-15-18-20(22)23/h11,14,19,21H,2-10,12-13,15-18H2,1H3,(H,22,23)/b14-11-/t19-/m1/s1
SMILES	CCCCCC[C@@H](O)C/C=CCCCCCCCCCC(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	326.28	Volume:	375.574 ? Van der Waals volume.
Dense:	0.869	LogP:	5.648 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.427 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.384 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	17.0	Rigid Bonds:	2.0
TPSA:	57.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	0.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.26	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.71	Fsp³:	0.85
MCE-18:	2.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.136	Fluc inhibitor:	0.037 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.984	Promiscuous compounds:	0.781

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.13	MDCK Permeability:	-4.766
Pgp-inhibitor:	0.0	Pgp-substrate:	0.008
PAMPA:	0.643 ? 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):	0.01
20% Bioavailability (F20%):	0.096	30% Bioavailability (F30%):	0.334
50% Bioavailability (F50%):	0.519

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.865
Plasma Protein Binding (PPB):	95.772%	Volume Distribution (VD):	0.07
Fu:	3.536% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.029
OATP1B3 inhibitor:	0.958	BCRP inhibitor:	0.248
BSEP inhibitor:	0.982

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.249
CYP2D6-inhibitor:	0.364	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.981
CYP2B6-substrate:	0.119	CYP2C8-inhibitor:	0.985
HLM stability:	0.001 ? 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):

4.057

Half-life (T1/2):

0.716

ADMET: Toxicity

hERG Blockers:	0.072	hERG Blockers (10um):	0.211
Human Hepatotoxicity (H-HT):	0.376	Drug-induced Liver Injury (DILI):	0.01
AMES Toxicity:	0.04	Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.251	Skin Sensitization:	0.991
Carcinogencity:	0.145	Eye Corrosion:	0.985
Eye Irritation:	0.998	Respiratory Toxicity:	0.767
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.479
Hematotoxicity:	0.088	Drug-induced Nephrotoxicity:	0.549
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.142	Hek293 Cytotoxicity:	0.033
BCF:	0.989 ? 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:	4.032 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.484 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.27 ? 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
NPO52125	Lesquerella fendleri	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO63687	Lesquerella lasiocarpa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC544624 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	28016
0.1-0.2	19298
0.2-0.3	2097
0.3-0.4	270
0.4-0.5	98
0.5-0.6	50
0.6-0.7	14
0.7-0.8	2
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	NPC243532
0.7949	Intermediate Similarity	NPC606120
0.7105	Intermediate Similarity	NPC324004
0.7105	Intermediate Similarity	NPC328497
0.7027	Intermediate Similarity	NPC424
0.7027	Intermediate Similarity	NPC36061
0.7027	Intermediate Similarity	NPC69510
0.7027	Intermediate Similarity	NPC77272
0.7027	Intermediate Similarity	NPC290563
0.7027	Intermediate Similarity	NPC139029
0.7027	Intermediate Similarity	NPC281972
0.7027	Intermediate Similarity	NPC261831
0.7027	Intermediate Similarity	NPC87564
0.6818	Remote Similarity	NPC255863
0.6818	Remote Similarity	NPC136164
0.6818	Remote Similarity	NPC245947
0.6757	Remote Similarity	NPC281245
0.6579	Remote Similarity	NPC92114
0.65	Remote Similarity	NPC154245
0.65	Remote Similarity	NPC85813
0.65	Remote Similarity	NPC223697
0.65	Remote Similarity	NPC6095
0.641	Remote Similarity	NPC95145
0.641	Remote Similarity	NPC325642
0.641	Remote Similarity	NPC65174
0.6383	Remote Similarity	NPC49863
0.625	Remote Similarity	NPC321062
0.5957	Remote Similarity	NPC321838
0.5854	Remote Similarity	NPC5413
0.58	Remote Similarity	NPC605544
0.58	Remote Similarity	NPC607260
0.5745	Remote Similarity	NPC99619
0.5714	Remote Similarity	NPC52955
0.5714	Remote Similarity	NPC88966
0.5714	Remote Similarity	NPC25417
0.5714	Remote Similarity	NPC323045
0.5714	Remote Similarity	NPC26500
0.5714	Remote Similarity	NPC1813
0.5714	Remote Similarity	NPC317881
0.5714	Remote Similarity	NPC59051
0.5652	Remote Similarity	NPC477201
0.5625	Remote Similarity	NPC323477
0.551	Remote Similarity	NPC470320
0.551	Remote Similarity	NPC327112
0.5476	Remote Similarity	NPC91495
0.5476	Remote Similarity	NPC70387
0.5417	Remote Similarity	NPC251042
0.5417	Remote Similarity	NPC174447
0.5417	Remote Similarity	NPC122521
0.5405	Remote Similarity	NPC171736
0.5405	Remote Similarity	NPC301585
0.5405	Remote Similarity	NPC261080
0.5405	Remote Similarity	NPC132565
0.5405	Remote Similarity	NPC209970
0.5405	Remote Similarity	NPC216630
0.5405	Remote Similarity	NPC201844
0.5405	Remote Similarity	NPC301696
0.5405	Remote Similarity	NPC196924
0.5405	Remote Similarity	NPC307783
0.5405	Remote Similarity	NPC154186
0.5405	Remote Similarity	NPC149184
0.5405	Remote Similarity	NPC279026
0.5405	Remote Similarity	NPC113928
0.5405	Remote Similarity	NPC14227
0.5319	Remote Similarity	NPC106851
0.5319	Remote Similarity	NPC282788
0.5319	Remote Similarity	NPC274927
0.5306	Remote Similarity	NPC68343
0.5306	Remote Similarity	NPC318420
0.5306	Remote Similarity	NPC326268
0.5306	Remote Similarity	NPC328089
0.5217	Remote Similarity	NPC225929
0.5208	Remote Similarity	NPC179764
0.5192	Remote Similarity	NPC328653
0.5172	Remote Similarity	NPC318766
0.5135	Remote Similarity	NPC155263
0.5102	Remote Similarity	NPC473863

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC544624 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6246
0.1-0.2	2644
0.2-0.3	211
0.3-0.4	21
0.4-0.5	15
0.5-0.6	7
0.6-0.7	3
0.7-0.8	2
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
0.7027	Intermediate Similarity	NPD3195	Phase 2
0.7027	Intermediate Similarity	NPD3196	Approved
0.6667	Remote Similarity	NPD3194	Phase 4
0.65	Remote Similarity	NPD4266	Phase 2
0.6383	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3173	Phase 4
0.5714	Remote Similarity	NPD3172	Approved
0.551	Remote Similarity	NPD4246	Phase 2
0.5405	Remote Similarity	NPD2270	Pre-clinical
0.5405	Remote Similarity	NPD633	Phase 3
0.5405	Remote Similarity	NPD9448	Phase 2
0.5306	Remote Similarity	NPD39	Phase 4

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