(1R*,2R*,3E,7E,11R*,12S*)-2,18-O-diacetyl-16-O-(3-hydroxy-3-methylglutaryi)-dolabella-3,7-dien-2,16,18-triol - Compound Card

(1R*,2R*,3E,7E,11R*,12S*)-2,18-O-diacetyl-16-O-(3-hydroxy-3-methylglutaryi)-dolabella-3,7-dien-2,16,18-triol

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(1R*,2R*,3E,7E,11R*,12S*)-2,18-O-diacetyl-16-O-(3-hydroxy-3-methylglutaryi)-dolabella-3,7-dien-2,16,18-triol

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpenoid
Canonical Smiles CC(=O)O[C@@H]1/C=C(/CC/C=C(/CC[C@@H]2[C@]1(C)CC[C@H]2C(OC(=O)C)(C)C)\C)\COC(=O)C[C@](CC(=O)O)(O)C
InChI InChI=1S/C30H46O9/c1-19-9-8-10-22(18-37-27(35)17-29(6,36)16-26(33)34)15-25(38-20(2)31)30(7)14-13-23(24(30)12-11-19)28(4,5)39-21(3)32/h9,15,23-25,36H,8,10-14,16-18H2,1-7H3,(H,33,34)/b19-9+,22-15-/t23-,24+,25-,29+,30+/m1/s1
InChIKey ATABDKOENHIVSH-XVKLZVPUSA-N
Formula C30H46O9
HBA 8
HBD 2
MW 550.69
Rotatable Bonds 9
TPSA 136.43
LogP 4.9
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 550.31
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Chrozophora obliqua Euphorbiaceae Plantae 316753

Showing of synonyms

  • Mohamed KM, Ohtani K, et al. (1995). 3-Hydroxy-3-methylglutaryl dolabellane diterpenes from Chrozophora obliqua. Phytochemistry,1995,39(1),151-161. [View]
Pubchem: 162851070
Nmrshiftdb2: 60051709

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC=CCCC=CC2

Level: 0

Mol. Weight: 550.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.72
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.04
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.91
Plasma Protein Binding
88.95
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
7.35
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.73
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.68
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.14
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
-556.44
Rat (Acute)
2.33
Rat (Chronic Oral)
2.52
Fathead Minnow
4.59
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
495.95
Hydration Free Energy
-3.24
Log(D) at pH=7.4
1.81
Log(P)
4.52
Log S
-4.48
Log(Vapor Pressure)
-9.98
Melting Point
149.01
pKa Acid
5.6
pKa Basic
5.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9258
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9258
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9205
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9205
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8882
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8882
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8817
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8817
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8605
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8605
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8415
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8415
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8366
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8366
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8168
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8168
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8033
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8033
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7792
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7792
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7617
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7617
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7514
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7514
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7477
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7477
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7406
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7406
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7379
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7379
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7378
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7378
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7358
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7358
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7324
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7324
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7311
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7311
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7287
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7287
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7246
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7246
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7231
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7231
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7213
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7213
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7190
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7190
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7107
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7107
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7089
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7089
N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) Q91XE4 ACY3_MOUSE Mus musculus 3 0.7035
N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) Q91XE4 ACY3_MOUSE Mus musculus 3 0.7035
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7013
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7013

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