9alpha-hydroxy-2-epi-16-deoxysarcophine - Compound Card

9alpha-hydroxy-2-epi-16-deoxysarcophine

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9alpha-hydroxy-2-epi-16-deoxysarcophine

Structure
Zoomed Structure
  • Family: Animalia - Alcyoniidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cembranoid Diterpene
Canonical Smiles C/C/1=C\C[C@H](O)[C@]2(C)O[C@H]2CC/C(=C/[C@@H]2C(=C(C)CO2)CC1)/C
InChI InChI=1S/C20H30O3/c1-13-5-8-16-15(3)12-22-17(16)11-14(2)7-10-19-20(4,23-19)18(21)9-6-13/h6,11,17-19,21H,5,7-10,12H2,1-4H3/b13-6+,14-11+/t17-,18+,19+,20+/m1/s1
InChIKey YCFWYGHHOGCWPB-LQROGWRGSA-N
Formula C20H30O3
HBA 3
HBD 1
MW 318.46
Rotatable Bonds 0
TPSA 41.99
LogP 4.08
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 318.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sarcophyton glaucum Alcyoniidae Animalia 70919

Showing of synonyms

  • Sawant SS, Youssef DTA, et al. (2006). Biocatalytic and antimetastatic studies of the marine cembranoids sarcophine and 2-epi-16-deoxysarcophine. Journal of Natural Products,2006,69(7),1010-1013. [View] [PubMed]
Pubchem: 11844357

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CCC=CCCC=3C(OCC3)C=CCC1

Level: 0

Mol. Weight: 318.46 g/mol

Antimetastatic

Absorption

Caco-2 (logPapp)
-5.01
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.25
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.34
Plasma Protein Binding
27.55
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
16.33
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.65
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.25
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.48
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
-1.29
Rat (Acute)
1.84
Rat (Chronic Oral)
1.65
Fathead Minnow
4.61
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
384.36
Hydration Free Energy
-5.31
Log(D) at pH=7.4
3.03
Log(P)
4.29
Log S
-4.12
Log(Vapor Pressure)
-5.31
Melting Point
90.36
pKa Acid
8.34
pKa Basic
4.64
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 0.9268
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9268
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8595
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8595
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8254
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.8254
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8156
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8156
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8106
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8106
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8093
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8093
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8054
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8054
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8053
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8053
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7906
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7906
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7897
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7897
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7791
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7791
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7778
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7778
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7701
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7701
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7669
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7669
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7649
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7649
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7641
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7641
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7639
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7639
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7630
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7630
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7615
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7615
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7599
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7599
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7507
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7507
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7430
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7430
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7391
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7391
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7266
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7266
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7229
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7229
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7208
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7208
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7190
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7190
Peroxisome proliferator-activated receptor alpha Q07869 PPARA_HUMAN Homo sapiens 3 0.7181
Peroxisome proliferator-activated receptor alpha Q07869 PPARA_HUMAN Homo sapiens 3 0.7181
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7073
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7073

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