(1R,5S,8R,10S,11R)-11-hydroxy-1-isoprenyl-8-methyl-3,6-dioxo-5,8-epoxycyclotetradec-12-ene 10,12-carbolactone - Compound Card

(1R,5S,8R,10S,11R)-11-hydroxy-1-isoprenyl-8-methyl-3,6-dioxo-5,8-epoxycyclotetradec-12-ene 10,12-carbolactone

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(1R,5S,8R,10S,11R)-11-hydroxy-1-isoprenyl-8-methyl-3,6-dioxo-5,8-epoxycyclotetradec-12-ene 10,12-carbolactone

Structure
Zoomed Structure
  • Family: Animalia - Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cembranolide
Canonical Smiles O=C1C[C@@H](C/C=C/2\C(=O)O[C@@H](C[C@]3(O[C@@H](C1)C(=O)C3)C)[C@@H]2O)C(=C)C
InChI InChI=1S/C19H24O6/c1-10(2)11-4-5-13-17(22)16(24-18(13)23)9-19(3)8-14(21)15(25-19)7-12(20)6-11/h5,11,15-17,22H,1,4,6-9H2,2-3H3/b13-5-/t11-,15+,16+,17-,19+/m1/s1
InChIKey OFFWLZVJUHOBDO-YGPPWILHSA-N
Formula C19H24O6
HBA 6
HBD 1
MW 348.4
Rotatable Bonds 1
TPSA 89.9
LogP 1.65
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.63
Exact Mass 348.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sinularia gardineri Alcyoniidae Animalia 668426

Showing of synonyms

  • Khalid A. El Sayed and Mark T. Hamann (1996). A new norcembranoid dimer from the Red Sea soft coral Sinularia gardineri. Journal of Natural Products,1996,59(7),687-689. [View] [PubMed]
Pubchem: 162852312
Nmrshiftdb2: 60052477

No compound-protein relationship available.

Structure

SMILES: C12=CCCCC(=O)CC3C(=O)CC(O3)CC(C2)OC1=O

Level: 0

Mol. Weight: 348.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.63
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.6
Plasma Protein Binding
46.88
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.96
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.5
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.03
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.02
Micronucleos
Toxic
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
-2.62
Rat (Acute)
2.98
Rat (Chronic Oral)
1.86
Fathead Minnow
3.91
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
406.01
Hydration Free Energy
-7.74
Log(D) at pH=7.4
1.06
Log(P)
1.0
Log S
-2.53
Log(Vapor Pressure)
-8.22
Melting Point
162.62
pKa Acid
6.12
pKa Basic
2.61
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7452
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7452
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7376
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7376
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7280
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7280

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