13-epi-cupressic acid - Compound Card

13-epi-cupressic acid

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13-epi-cupressic acid

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)(O)C
InChI InChI=1S/C20H32O3/c1-6-18(3,23)13-10-15-14(2)8-9-16-19(15,4)11-7-12-20(16,5)17(21)22/h6,15-16,23H,1-2,7-13H2,3-5H3,(H,21,22)/t15?,16?,18-,19-,20+/m1/s1
InChIKey LMODNMXJBXUOQF-XZJNCXDESA-N
Formula C20H32O3
HBA 2
HBD 2
MW 320.47
Rotatable Bonds 5
TPSA 57.53
LogP 4.57
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 320.24
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: 162913884
Nmrshiftdb2: 80013431

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 320.47 g/mol

Anti-leishmanial
Antitrypanosomal

Absorption

Caco-2 (logPapp)
-4.46
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.82
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.48

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.83
Plasma Protein Binding
83.65
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
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.07
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.16
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.08
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
2.24
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
-4.13
Rat (Acute)
3.26
Rat (Chronic Oral)
1.59
Fathead Minnow
3.97
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
353.42
Hydration Free Energy
-5.92
Log(D) at pH=7.4
1.5
Log(P)
3.73
Log S
-4.5
Log(Vapor Pressure)
-7.82
Melting Point
162.15
pKa Acid
5.36
pKa Basic
6.76
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 0.9945
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9945
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9539
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9539
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9115
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9115
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8981
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8981
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8915
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8915
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8710
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8710
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8295
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8295
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 3 0.8268
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 3 0.8268
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8244
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8244
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8173
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8173
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.8109
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.8109
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7864
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7864
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7790
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7790
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7710
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7710
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7705
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7705
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7698
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7698
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7668
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7668
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7665
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7665
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7553
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7553
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7537
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7537
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7512
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7512
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7430
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7430
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7399
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7399
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7383
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7383
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7368
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7368
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7365
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7365
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7279
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7279
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7273
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7273
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7237
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7237
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 4 0.7234
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 4 0.7234
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7228
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7228
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7220
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7220
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7196
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7196
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 2 0.7191
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 2 0.7191
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7136
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7136
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.7128
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.7128
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7124
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7124
Geranylgeranyl pyrophosphate synthase BTS1 Q12051 GGPPS_YEAST Saccharomyces cerevisiae 2 0.7057
Geranylgeranyl pyrophosphate synthase BTS1 Q12051 GGPPS_YEAST Saccharomyces cerevisiae 2 0.7057
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7014
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7014

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