7beta-acetoxy-8alpha-hydroxydeepoxysarcophine - Compound Card

7beta-acetoxy-8alpha-hydroxydeepoxysarcophine

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7beta-acetoxy-8alpha-hydroxydeepoxysarcophine

Structure
Zoomed Structure
  • Family: Animalia - Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cembranoid Diterpene
Canonical Smiles CC(=O)O[C@H]1CC/C(=C/[C@@H]2OC(=O)C(=C2CC/C(=C/CC[C@@]1(C)O)/C)C)/C
InChI InChI=1S/C22H32O5/c1-14-7-6-12-22(5,25)20(26-17(4)23)11-9-15(2)13-19-18(10-8-14)16(3)21(24)27-19/h7,13,19-20,25H,6,8-12H2,1-5H3/b14-7+,15-13+/t19-,20-,22+/m0/s1
InChIKey GLGCSFHERWMYPP-ULVNOOPDSA-N
Formula C22H32O5
HBA 5
HBD 1
MW 376.49
Rotatable Bonds 1
TPSA 72.83
LogP 4.16
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 376.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sarcophyton glaucum Alcyoniidae Animalia 70919

Showing of synonyms

  • Hegazy M-EF, El-Beih AA, et al. (2011). Cytotoxic cembranoids from the Red Sea soft coral Sarcophyton glaucum. Natural Product Communications,2011,6(12),1809-1812. [View] [PubMed]
Pubchem: 21725059
Nmrshiftdb2: 70081522

No compound-protein relationship available.

Structure

SMILES: C1C(=O)OC(C=12)C=CCCCCCCC=CCC2

Level: 0

Mol. Weight: 376.49 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.64
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.59
Plasma Protein Binding
64.43
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.42
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.26
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.26
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.78
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
-2.89
Rat (Acute)
2.13
Rat (Chronic Oral)
1.9
Fathead Minnow
4.6
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
392.85
Hydration Free Energy
-5.5
Log(D) at pH=7.4
2.91
Log(P)
4.33
Log S
-4.71
Log(Vapor Pressure)
-6.33
Melting Point
123.4
pKa Acid
10.37
pKa Basic
5.45
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9205
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9205
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8885
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8885
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8867
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8867
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8781
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8781
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8656
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8656
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8456
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8456
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8392
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.8392
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8340
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8340
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8261
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8261
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8161
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8161
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7985
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7985
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7934
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7934
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7861
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.7861
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7843
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7843
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7778
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7778
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7667
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7667
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7608
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7608
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7591
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7591
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7542
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7542
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7359
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7359
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7349
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7349
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7336
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7336
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7295
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7295
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7271
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7271
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7260
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7260
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7259
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7259
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7244
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7244
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7230
Regulatory protein SdiA P07026 SDIA_ECOLI Escherichia coli 3 0.7230
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7218
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7218
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7187
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7187
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7158
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7158
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7144
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7144
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7104
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7104
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7097
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7097
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7091
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7091
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7027
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7027
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7016
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7016
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7003
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7003

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