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(+)-sarcophine
- Family: Animalia - Alcyoniidae
- Kingdom: Animalia
-
Class: Terpenoid
- Subclass: Cembranoid Diterpene
| Canonical Smiles | C/C/1=C\CC[C@@]2(C)O[C@@H]2CC/C(=C/[C@H]2C(=C(C)C(=O)O2)CC1)/C |
|---|---|
| InChI | InChI=1S/C20H28O3/c1-13-6-5-11-20(4)18(23-20)10-8-14(2)12-17-16(9-7-13)15(3)19(21)22-17/h6,12,17-18H,5,7-11H2,1-4H3/b13-6+,14-12+/t17-,18+,20+/m0/s1 |
| InChIKey | CGAKBBMRMLAYMY-CFCZUDOTSA-N |
| Formula | C20H28O3 |
| HBA | 3 |
| HBD | 0 |
| MW | 316.44 |
| Rotatable Bonds | 0 |
| TPSA | 38.83 |
| LogP | 4.63 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 316.2 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Sarcophyton trocheliophorum | Alcyoniidae | Animalia | 205097 |
| 2 | Sarcophyton ehrenbergi | Alcyoniidae | Animalia | 358800 |
Showing of synonyms
(+)-sarcophine
Sarcophine
Sarcophin
Sarcophin A
55038-27-2
NSC 250434
Oxireno(9,10)cyclotetradeca(1,2-b)furan-9(1ah)-one, 2,3,6,7,10a,13,14,14a-octahydro-1a,5,8,12-tetramethyl-, (1aS-(1aR*,4E,10aR*,11E,14aR*))-
(1S,2E,6S,8S,11E)-3,8,12,16-tetramethyl-7,18-dioxatricyclo[13.3.0.06,8]octadeca-2,11,15-trien-17-one
(1S,2E,6S,8S,11E)-3,8,12,16-tetramethyl-7,18-dioxatricyclo(13.3.0.06,8)octadeca-2,11,15-trien-17-one
Oxireno(9,10)cyclotetradeca(1,2-b)furan-9(1aH)-one, 2,3,6,7,10a,13,14,14a-octahydro-1a,5,8,12-tetramethyl-(VAN)
Oxireno(9,10)cyclotetradeca(1,2-b)furan-9(1aH)-one, 2,3,6,7,10a,13,14,14a-octahydro-1a,5,8,12-tetramethyl-(VAN) (9CI)
(2e,11e)-3,8,12,16-tetramethyl-7,18-dioxatricyclo(13.3.0.06,8)octadeca-2,11,15-trien-17-one
(2e,11e)-3,8,12,16-tetramethyl-7,18-dioxatricyclo[13.3.0.06,8]octadeca-2,11,15-trien-17-one
CHEMBL518855
DTXSID001318397
NSC814255
NSC-814255
Oxireno(9,10)cyclotetradeca(1,2-b)furan-9(1aH)-one, 2,3,6,7,10a,13,14,14a-octahydro-1a,5,8,12-tetramethyl- (VAN)
HY-124550
CS-0086898
- 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]
- Hegazy M-EF, Mohamed TA, et al. (2013). Trochelioid A and B, new cembranoid diterpenes from the Red Sea soft coral Sarcophyton trocheliophorum. Phytochemistry Letters,2013,6,383-386. [View]
CPRiL:
131027
SMILES: C12C(O2)CCC=CCCC=3C(OC(=O)C3)C=CCC1
Level: 0
Mol. Weight: 316.44 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.98
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.39
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.15
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.36
- Plasma Protein Binding
- 37.17
- 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
- 14.48
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.56
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.15
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.77
- 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
- 0.05
- Rat (Acute)
- 1.75
- Rat (Chronic Oral)
- 1.72
- Fathead Minnow
- 4.76
- 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
- 383.94
- Hydration Free Energy
- -3.9
- Log(D) at pH=7.4
- 4.03
- Log(P)
- 4.26
- Log S
- -5.0
- Log(Vapor Pressure)
- -4.63
- Melting Point
- 62.73
- pKa Acid
- 7.6
- pKa Basic
- 5.18
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.9520 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.9520 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.8700 |
| Rhodopsin | P02699 | OPSD_BOVIN | Bos taurus | 3 | 0.8700 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8607 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8607 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8591 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8591 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8559 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8559 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8204 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8204 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.7942 |
| Methylketone synthase I | E0YCS2 | E0YCS2_SOLHA | Solanum habrochaites | 3 | 0.7942 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7896 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7896 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7774 |
| Probable NDP-rhamnosyltransferase | Q9ALM8 | Q9ALM8_SACSN | Saccharopolyspora spinosa | 3 | 0.7774 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7730 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7730 |
| Jasmonoyl--L-amino acid synthetase JAR1 | Q9SKE2 | JAR1_ARATH | Arabidopsis thaliana | 3 | 0.7663 |
| Jasmonoyl--L-amino acid synthetase JAR1 | Q9SKE2 | JAR1_ARATH | Arabidopsis thaliana | 3 | 0.7663 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7660 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7660 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7644 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7644 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7532 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7532 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7502 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7502 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7475 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7475 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 2 | 0.7441 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 2 | 0.7441 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7383 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7383 |
| FKBP-type peptidyl-prolyl cis-trans isomerase FkpA | P45523 | FKBA_ECOLI | Escherichia coli | 4 | 0.7354 |
| FKBP-type peptidyl-prolyl cis-trans isomerase FkpA | P45523 | FKBA_ECOLI | Escherichia coli | 4 | 0.7354 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7326 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7326 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7306 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7306 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7282 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7282 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7265 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7265 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7259 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7259 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7220 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7220 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7187 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7187 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7162 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7162 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7150 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7150 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7146 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7146 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7139 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7139 |
| Camphor 5-monooxygenase | P00183 | CPXA_PSEPU | Pseudomonas putida | 3 | 0.7132 |
| Camphor 5-monooxygenase | P00183 | CPXA_PSEPU | Pseudomonas putida | 3 | 0.7132 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7110 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7110 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7091 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7091 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7083 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7083 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7047 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7047 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7030 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7030 |