Methyl-15-hydroperoxy-8alpha,14alpha,12alpha,13alpha-diepoxiabietan-13-en-19-oate - Compound Card

Methyl-15-hydroperoxy-8alpha,14alpha,12alpha,13alpha-diepoxiabietan-13-en-19-oate

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Methyl-15-hydroperoxy-8alpha,14alpha,12alpha,13alpha-diepoxiabietan-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]2[C@@]([C@@H]3O1)(O2)C(OO)(C)C)C
InChI InChI=1S/C21H32O6/c1-17(2,27-23)21-14(25-21)11-13-18(3)8-6-9-19(4,16(22)24-5)12(18)7-10-20(13)15(21)26-20/h12-15,23H,6-11H2,1-5H3/t12?,13-,14+,15-,18+,19+,20-,21+/m1/s1
InChIKey AVZHENHAPQQKBK-OLLVGXTHSA-N
Formula C21H32O6
HBA 6
HBD 1
MW 380.48
Rotatable Bonds 3
TPSA 80.82
LogP 3.33
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.95
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: 162834997
Nmrshiftdb2: 60071535

No compound-protein relationship available.

Structure

SMILES: C123C(O3)C4C(O4)CC1C5C(CC2)CCCC5

Level: 0

Mol. Weight: 380.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.06
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.590
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.170
Plasma Protein Binding
39.85
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
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.230
Organic Cation Transporter 2
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
-0.230
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
6.780
Micronucleos
Toxic
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
-13.800
Rat (Acute)
2.520
Rat (Chronic Oral)
1.400
Fathead Minnow
3.860
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
413.640
Hydration Free Energy
-5.400
Log(D) at pH=7.4
3.640
Log(P)
2.91
Log S
-4.04
Log(Vapor Pressure)
-6.22
Melting Point
129.76
pKa Acid
6.3
pKa Basic
3.49
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8287
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8287
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8185
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8185
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7993
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7993
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7948
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7948
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7828
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7828
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7814
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7814
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7754
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7754
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7657
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7657
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7489
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7489
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7463
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7463
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7433
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7433
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7401
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7401
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7375
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7375
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7281
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7281
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7242
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7242
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7208
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7208
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7107
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7107
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7077
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7077
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7070
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7070
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7059
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7059
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7056
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7056
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7054
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7054
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7052
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7052
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7050
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7050

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