Methyl-15-hydroperoxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate - Compound Card

Methyl-15-hydroperoxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate

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Methyl-15-hydroperoxy-8alpha,12alpha-epidioxiabiet-13-en-19-oate

Structure
Zoomed Structure
  • Family: Plantae - Cupressaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Diterpenoid
Canonical Smiles COC(=O)[C@@]1(C)CCC[C@]2(C1CC[C@]13[C@@H]2C[C@H](OO1)C(=C3)C(OO)(C)C)C
InChI InChI=1S/C21H32O6/c1-18(2,26-23)13-12-21-10-7-15-19(3,16(21)11-14(13)25-27-21)8-6-9-20(15,4)17(22)24-5/h12,14-16,23H,6-11H2,1-5H3/t14-,15?,16+,19-,20-,21-/m0/s1
InChIKey JTMNVWQNMNACAS-SKTKMLTQSA-N
Formula C21H32O6
HBA 6
HBD 1
MW 380.48
Rotatable Bonds 3
TPSA 74.22
LogP 4.05
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 380.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Juniperus phoenicea Cupressaceae Plantae 61308

Showing of synonyms

  • Barrero AF, Quılez del Moral JF, et al. (2004). Oxygenated diterpenes and other constituents from Moroccan Juniperus phoenicea and Juniperus thurifera var. africana. Phytochemistry,2004,65,2507-2515. [View] [PubMed]
Pubchem: 163093185
Nmrshiftdb2: 60071538

No compound-protein relationship available.

Structure

SMILES: C1=CC(OO2)CC(C123)C4C(CC3)CCCC4

Level: 0

Mol. Weight: 380.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.56
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.560
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.710
Plasma Protein Binding
64.85
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
11.140
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.640
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.750
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.650
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
Safe
T. Pyriformis
-7.060
Rat (Acute)
2.510
Rat (Chronic Oral)
1.930
Fathead Minnow
3.920
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
393.610
Hydration Free Energy
-5.610
Log(D) at pH=7.4
2.960
Log(P)
3.76
Log S
-4.79
Log(Vapor Pressure)
-6.38
Melting Point
146.13
pKa Acid
9.42
pKa Basic
4.93
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8731
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8731
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8589
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8589
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8571
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8571
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8530
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8530
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8434
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8434
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8277
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8277
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8046
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8046
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7973
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7973
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7934
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7934
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7921
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7921
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7914
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 4 0.7914
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7885
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7885
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7880
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7880
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7823
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7823
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7804
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7804
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7799
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7799
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7764
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7764
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7677
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7677
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7660
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7660
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7604
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7604
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7595
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7595
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7543
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7543
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7533
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7533
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7524
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7524
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7505
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7505
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7498
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7498
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7409
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7409
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7384
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7384
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7383
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7383
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7374
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7374
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7330
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7330
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7315
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7315
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7298
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7298
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7259
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7259
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7246
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7246
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7240
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7240
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7194
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7194
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7193
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7193
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7166
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7166
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7156
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7156
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7149
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7149
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7062
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7062
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7038
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7038
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7037
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7037

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