9R-hydroxysarcophine - Compound Card

9R-hydroxysarcophine

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9R-hydroxysarcophine

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)C(=O)O2)CC1)/C
InChI InChI=1S/C20H28O4/c1-12-5-8-15-14(3)19(22)23-16(15)11-13(2)7-10-18-20(4,24-18)17(21)9-6-12/h6,11,16-18,21H,5,7-10H2,1-4H3/b12-6+,13-11+/t16-,17-,18-,20-/m0/s1
InChIKey PLXYTNVUDOBBTD-RMDRXMPUSA-N
Formula C20H28O4
HBA 4
HBD 1
MW 332.44
Rotatable Bonds 0
TPSA 59.06
LogP 3.6
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 332.2
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: 10711640

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CCC=CCCC=3C(OC(=O)C3)C=CCC1

Level: 0

Mol. Weight: 332.44 g/mol

Antimetastatic

Absorption

Caco-2 (logPapp)
-5.05
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
-3.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.35
Plasma Protein Binding
27.71
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.08
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.33
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.02
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.56
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
-1.87
Rat (Acute)
2.17
Rat (Chronic Oral)
1.79
Fathead Minnow
4.56
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
400.23
Hydration Free Energy
-5.86
Log(D) at pH=7.4
2.99
Log(P)
3.27
Log S
-4.1
Log(Vapor Pressure)
-5.96
Melting Point
113.65
pKa Acid
7.11
pKa Basic
4.37
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9056
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9056
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8979
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8979
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8914
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8914
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8786
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8786
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8778
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8778
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8668
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8668
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8648
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8648
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8530
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8530
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8489
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8489
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8456
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8456
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8366
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8366
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8300
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8300
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8231
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8231
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 4 0.8122
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 4 0.8122
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8077
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8077
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8050
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8050
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8044
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8044
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7928
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7928
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7878
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7878
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7804
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7804
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7775
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7775
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7737
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7737
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7703
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7703
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.7688
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.7688
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7674
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 4 0.7674
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7665
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7665
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7564
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7564
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7562
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7562
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7516
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7516
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7487
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7487
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7486
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7486
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7470
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7470
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7452
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7452
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7450
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7450
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7421
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7421
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7403
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7403
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7354
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7354
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7335
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7335
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7323
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7323
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7236
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7236
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7235
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7235
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7224
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7224
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7182
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7182
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7155
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7155
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7109
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7109
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7073
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7073
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7038
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7038
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7026
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7026
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7009
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7009

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