13-epitorulosal - Compound Card

13-epitorulosal

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13-epitorulosal

Structure
Zoomed Structure
  • Family: Animalia - Apidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles C=C[C@](CCC1C(=C)CCC2[C@]1(C)CCC[C@]2(C)C=O)(O)C
InChI InChI=1S/C20H32O2/c1-6-19(4,22)13-10-16-15(2)8-9-17-18(3,14-21)11-7-12-20(16,17)5/h6,14,16-17,22H,1-2,7-13H2,3-5H3/t16?,17?,18-,19-,20-/m1/s1
InChIKey GLJXUJMLZHNKJU-WFAGLZIHSA-N
Formula C20H32O2
HBA 2
HBD 1
MW 304.47
Rotatable Bonds 5
TPSA 37.3
LogP 4.68
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 304.24
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Apis species Apidae Animalia 7459

Showing of synonyms

  • Siheri W, Igoli JO, et al. (2014). The isolation of antiprotozoal compounds from Libyan propolis. Phytotherapy Research,2014,28(12),1756-1760. [View] [PubMed]
Pubchem: 163091535
Nmrshiftdb2: 80013430

No compound-protein relationship available.

Structure

SMILES: C=C(C1)CCC(C12)CCCC2

Level: 0

Mol. Weight: 304.47 g/mol

Anti-leishmanial
Antitrypanosomal

Absorption

Caco-2 (logPapp)
-4.61
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.34
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.73
Plasma Protein Binding
58.52
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
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.1
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.58
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.33
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.58
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
-3.64
Rat (Acute)
3.34
Rat (Chronic Oral)
1.42
Fathead Minnow
3.94
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
330.28
Hydration Free Energy
-2.59
Log(D) at pH=7.4
4.04
Log(P)
4.03
Log S
-4.72
Log(Vapor Pressure)
-5.61
Melting Point
83.91
pKa Acid
9.09
pKa Basic
6.37
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 0.9892
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9892
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9358
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9358
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9308
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9308
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8936
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8936
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8767
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8767
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8312
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8312
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8055
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8055
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8042
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8042
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7956
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7956
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7924
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7924
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7876
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7876
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7868
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7868
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7750
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7750
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7672
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7672
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7662
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7662
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7630
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7630
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7552
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7552
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7542
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7542
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7506
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7506
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7484
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7484
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7456
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7456
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7440
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7440
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7429
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7429
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7428
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7428
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7415
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7415
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7415
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7415
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7411
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7411
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7388
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7388
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7352
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7352
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7310
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7310
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7291
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7291
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7238
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7238
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7230
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7230
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7226
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7226
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7223
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7223
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7213
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7213
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7199
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7199
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7169
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7169
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7165
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7165
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7159
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7159
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7158
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7158
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7143
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7143
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7143
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7143
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7142
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7142
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7139
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7139
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7120
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7120
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7110
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7110
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7110
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7110
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7109
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7109
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7106
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7106
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7104
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7104
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7086
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7086
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7072
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7072
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7065
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7065
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7064
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7064
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7052
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7052
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7051
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7051
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7051
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7051
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7049
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7049
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7027
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7027
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7023
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7023
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7012
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7012
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7011
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7011
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7002
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7002
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7002
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7002

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