Lupeol arachidate - Compound Card

Lupeol arachidate

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Lupeol arachidate

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene Ester
Canonical Smiles CCCCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C(C1(C)C)CC[C@@]1(C2CC[C@]2([C@@]1(C)CC[C@@]1(C2[C@@H](CC1)C(=C)C)C)C)C)C
InChI InChI=1S/C51H90O2/c1-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-28-44(52)53-43-32-34-48(7)41(46(43,4)5)30-35-49(8)42(48)31-36-50(9)45-40(39(2)3)29-33-47(45,6)37-38-51(49,50)10/h40-43,45H,2,11-38H2,1,3-10H3/t40-,41?,42?,43-,45?,47+,48-,49+,50+,51-/m0/s1
InChIKey LEFHNQCURVKAOS-NGSCONLUSA-N
Formula C51H90O2
HBA 2
HBD 0
MW 735.28
Rotatable Bonds 20
TPSA 26.3
LogP 16.01
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 53
Formal Charge 0
Fraction CSP3 0.94
Exact Mass 734.69
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Periploca laevigata Apocynaceae Plantae 413294

Showing of synonyms

  • Ben nejma A, Besbes M, et al. (2013). Isolation and structure elucidation of acetylcholinesterase lipophilic lupeol derivatives inhibitors from the latex of the Tunisian Periploca laevigata. Arabian Journal of Chemistry,2013,in press. [View]
Pubchem: 162817544
Nmrshiftdb2: 70106786

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2CCC4C3CCC5C4CCCC5

Level: 0

Mol. Weight: 735.28 g/mol

Anti-acetylcholinesterase

Absorption

Caco-2 (logPapp)
-4.64
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
1.34
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
803.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.51
Plasma Protein Binding
107.81
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
1.94
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-18.1
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.32
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.31
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-1464812.64
Rat (Acute)
2.52
Rat (Chronic Oral)
2.3
Fathead Minnow
1855.25
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
163746.71
Hydration Free Energy
-2.92
Log(D) at pH=7.4
11.32
Log(P)
17.89
Log S
-8.12
Log(Vapor Pressure)
-5302.82
Melting Point
120.32
pKa Acid
-3.81
pKa Basic
5.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9403
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9403
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8662
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8662
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8133
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8133
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8015
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8015
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7899
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7899
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7880
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7880
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7860
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7860
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7847
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7847
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7831
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7831
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7768
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7768
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7689
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7689
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7617
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7617
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7578
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7578
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7464
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7464
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7461
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7461
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7428
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7428
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7419
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7419
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7384
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7384
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7335
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7335
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7324
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7324
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7289
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7289
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7228
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7228
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7219
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7219
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7191
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7191
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7182
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7182
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7156
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7156
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7139
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7139
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7129
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7129
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7121
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7121
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7119
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7119
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7082
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7082
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7063
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7063
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7055
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7055
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7047
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7047
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7032
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7032
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7030
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7030

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