(E)-methyl-3-(5-butyl-1-hydroxy-2,3-dimethyl-4-oxocyclopent-2-enyl)acrylate - Compound Card

(E)-methyl-3-(5-butyl-1-hydroxy-2,3-dimethyl-4-oxocyclopent-2-enyl)acrylate

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(E)-methyl-3-(5-butyl-1-hydroxy-2,3-dimethyl-4-oxocyclopent-2-enyl)acrylate

Structure
Zoomed Structure
  • Family: Animalia - Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cembranoid Diterpene
Canonical Smiles CCCCC1C(=O)C(=C(C1(O)/C=C/C(=O)OC)C)C
InChI InChI=1S/C15H22O4/c1-5-6-7-12-14(17)10(2)11(3)15(12,18)9-8-13(16)19-4/h8-9,12,18H,5-7H2,1-4H3/b9-8+
InChIKey RBWCHYBHSSKRBY-CMDGGOBGSA-N
Formula C15H22O4
HBA 4
HBD 1
MW 266.34
Rotatable Bonds 5
TPSA 63.6
LogP 2.17
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 266.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sarcophyton ehrenbergi Alcyoniidae Animalia 358800

Showing of synonyms

  • Elkhateeb A, El-Beih AA, et al. (2014). New terpenes from the Egyptian soft coral Sarcophyton ehrenbergi. Marine Drugs,2014,12,1977-1986. [View] [PubMed]
Pubchem: 171118741

No compound-protein relationship available.

Structure

SMILES: O=C1C=CCC1

Level: 0

Mol. Weight: 266.34 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.43
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.43
Plasma Protein Binding
25.53
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
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
4.38
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.49
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.57
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.26
Micronucleos
Safe
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
3.96
Rat (Acute)
2.42
Rat (Chronic Oral)
1.91
Fathead Minnow
4.27
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
301.03
Hydration Free Energy
-8.38
Log(D) at pH=7.4
2.21
Log(P)
2.84
Log S
-2.54
Log(Vapor Pressure)
-4.81
Melting Point
65.9
pKa Acid
7.73
pKa Basic
4.53
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9323
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9323
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9268
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.9268
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8841
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8841
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8081
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8081
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7850
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7850
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7734
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7734
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7718
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7718
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7651
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7651
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7555
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7555
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7399
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7399
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7349
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7349
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7331
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7331
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7267
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7267
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7195
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7195

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