18-O-diacetyl-16-O-(3-hydroxy-3-methylglutaryl)-7-hydroperoxydolabella-3,8(17) diene-2,16,18 triol - Compound Card

18-O-diacetyl-16-O-(3-hydroxy-3-methylglutaryl)-7-hydroperoxydolabella-3,8(17) diene-2,16,18 triol

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18-O-diacetyl-16-O-(3-hydroxy-3-methylglutaryl)-7-hydroperoxydolabella-3,8(17) diene-2,16,18 triol

Structure
Zoomed Structure
  • Family: Plantae - Capparaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpenoid
Canonical Smiles OOC1CC/C(=C/C([C@@]2(C(CCC1=C)C(CC2)C(OC(=O)C)(C)C)C)OC(=O)C)/COC(=O)CC(CC(=O)OC)(O)C
InChI InChI=1S/C31H48O11/c1-19-9-11-24-23(29(4,5)41-21(3)33)13-14-31(24,7)26(40-20(2)32)15-22(10-12-25(19)42-37)18-39-28(35)17-30(6,36)16-27(34)38-8/h15,23-26,36-37H,1,9-14,16-18H2,2-8H3/b22-15-/t23?,24?,25?,26?,30?,31-/m0/s1
InChIKey DWXQHGGTYGGNFZ-ZJNLILGDSA-N
Formula C31H48O11
HBA 11
HBD 2
MW 596.71
Rotatable Bonds 10
TPSA 154.89
LogP 4.45
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 42
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 596.32
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Cleome droserifolia Capparaceae Plantae 511510

Showing of synonyms

  • Aboushoer MI, Fathy HM, et al. (2010). Terpenes and flavonoids from an Egyptian collection of Cleome droserifolia. Natural Product Research,2010,24(7),687-696. [View] [PubMed]
Pubchem: 163054778

No compound-protein relationship available.

Structure

SMILES: C1C=CCCCC(=C)CCC(C12)CCC2

Level: 0

Mol. Weight: 596.71 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.600
Plasma Protein Binding
32.6
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
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
Non-Inhibitor

Excretion

Clearance
9.190
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.020
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.780
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.620
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
-2515.490
Rat (Acute)
3.560
Rat (Chronic Oral)
2.270
Fathead Minnow
12.070
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
417.640
Hydration Free Energy
-2.920
Log(D) at pH=7.4
2.470
Log(P)
3.79
Log S
-4.48
Log(Vapor Pressure)
-8.17
Melting Point
103.11
pKa Acid
10.18
pKa Basic
3.87
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 0.8835
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8835
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8005
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8005
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7700
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7700
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7614
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7614
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7458
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7458
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7366
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7366
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7335
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7335
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7329
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7329
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7297
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7297
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7256
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7256
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7122
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7122
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7111
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7111
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7077
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7077
Avd protein A7YYL1 A7YYL1_XENTR Xenopus tropicalis 3 0.7039
Avd protein A7YYL1 A7YYL1_XENTR Xenopus tropicalis 3 0.7039
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7010
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7010
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7006
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7006

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