(+)-(Z)-lanceol acetate - Compound Card

(+)-(Z)-lanceol acetate

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(+)-(Z)-lanceol acetate

Structure
Zoomed Structure
  • Family: Apiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Bisabolane Sesquiterpene Ester
Canonical Smiles CC(=O)OC/C(=C\CCC(=C)[C@@H]1CCC(=CC1)C)/C
InChI InChI=1S/C17H26O2/c1-13-8-10-17(11-9-13)15(3)7-5-6-14(2)12-19-16(4)18/h6,8,17H,3,5,7,9-12H2,1-2,4H3/b14-6-/t17-/m0/s1
InChIKey BSYWXGDMWUUHDZ-ZRBJYGNNSA-N
Formula C17H26O2
HBA 2
HBD 0
MW 262.39
Rotatable Bonds 6
TPSA 26.3
LogP 4.58
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 262.19
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Torilis arvensis Apiaceae Plantae 79184

Showing of synonyms

  • Saad HEA, El-Sharkawy SH, et al. (1994). (+)-(Z)-Lanceol acetate from Torilis arvensis. Phytochemistry,1994,37(2),473-475. [View]
Pubchem: 101673680
Nmrshiftdb2: 70109862

No compound-protein relationship available.

Structure

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 82.15 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.17
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
63.69
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.16
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.41
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.69
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.15
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
0.89
Rat (Acute)
1.69
Rat (Chronic Oral)
1.86
Fathead Minnow
4.46
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
303.95
Hydration Free Energy
-3.06
Log(D) at pH=7.4
3.87
Log(P)
5.56
Log S
-5.26
Log(Vapor Pressure)
-3.79
Melting Point
-11.72
pKa Acid
11.74
pKa Basic
5.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8982
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8982
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8852
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8852
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8838
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8838
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8794
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8794
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8766
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8766
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8742
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8742
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8124
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8124
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.8123
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.8123
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8024
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8024
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8001
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8001
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7862
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7862
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7805
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7805
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7783
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7783
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7778
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7778
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7708
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7708
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7699
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7699
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7672
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7672
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7660
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 2 0.7660
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7569
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7569
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7554
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7554
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7543
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7543
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7523
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7523
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7519
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7519
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7502
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7502
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7491
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7491
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7482
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7482
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7457
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7457
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7456
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7456
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7454
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7454
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7440
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7440
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7427
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7427
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7423
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7423
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7404
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 2 0.7404
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7401
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7401
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7390
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7390
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7385
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7385
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7378
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7378
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7374
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7374
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7359
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7359
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7350
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7350
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7345
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7345
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7324
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7324
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7322
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7322
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7312
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7312
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7293
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7293
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7292
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7292
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7292
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7292
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7284
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7284
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7260
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7260
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7256
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7256
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7244
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 2 0.7244
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7237
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7237
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7236
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7236
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7214
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7214
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7206
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7206
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7200
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7200
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7199
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7199
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7196
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7196
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7193
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7193
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7188
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7188
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7183
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7183
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7181
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7181
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7179
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7179
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7173
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7173
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7153
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7153
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7129
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7129
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7126
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7126
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 2 0.7124
Phospholipase A2 P00593 PA21B_BOVIN Bos taurus 2 0.7124
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7119
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7119
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7101
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7101
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7096
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7096
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7093
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7093
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 2 0.7085
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 2 0.7085
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7081
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7081
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7076
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7076
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7066
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7066
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7047
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7047
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7030
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7030
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7012
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7012

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