Sigmosceptrellin B methyl ester - Compound Card

Sigmosceptrellin B methyl ester

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Sigmosceptrellin B methyl ester

Structure
Zoomed Structure
  • Family: Animalia - Podospongiidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Cyclic Norterpene Peroxide
Canonical Smiles COC(=O)[C@@H](C1CC[C@]2(OO1)CC[C@]1([C@H](C2)CC[C@@]2([C@@H]1CCCC2=C)C)C)C
InChI InChI=1S/C24H38O4/c1-16-7-6-8-20-22(16,3)11-9-18-15-24(14-13-23(18,20)4)12-10-19(27-28-24)17(2)21(25)26-5/h17-20H,1,6-15H2,2-5H3/t17-,18+,19?,20+,22+,23+,24+/m1/s1
InChIKey ZQSPCLSXMHXWQA-TVQNRHJOSA-N
Formula C24H38O4
HBA 4
HBD 0
MW 390.56
Rotatable Bonds 2
TPSA 44.76
LogP 5.61
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.88
Exact Mass 390.28
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Diacarnus erythraenus Podospongiidae Animalia 283431

Showing of synonyms

  • Lefranc F, Nuzzo G, et al. (2013). In vitro pharmacological and toxicological effects of norterpene peroxides isolated from the Red Sea sponge Diacarnus erythraeanus on normal and cancer cells. Journal of Natural Products,2013,76(9),1541-1547. [View] [PubMed]
Pubchem: 162817149

No compound-protein relationship available.

Structure

SMILES: C1CCC(=C)C(CC2)C1C(CC3)C2CC34CCCOO4

Level: 0

Mol. Weight: 390.56 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.520
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.160
Plasma Protein Binding
66.67
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-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
11.200
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.300
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.290
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.750
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-13.130
Rat (Acute)
2.040
Rat (Chronic Oral)
1.710
Fathead Minnow
3.920
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
413.060
Hydration Free Energy
-3.860
Log(D) at pH=7.4
4.390
Log(P)
5.87
Log S
-6.26
Log(Vapor Pressure)
-6.55
Melting Point
98.65
pKa Acid
11.16
pKa Basic
6.0
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8850
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8850
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8409
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8409
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8398
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8398
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8274
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8274
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8001
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8001
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7909
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7909
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7845
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7845
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7814
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7814
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7747
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7747
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7728
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7728
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7680
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7680
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7658
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7658
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7646
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7646
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7564
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7564
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7541
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7541
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7524
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7524
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.7519
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 4 0.7519
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7493
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7493
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7423
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7423
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7401
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7401
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7352
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7352
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7321
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7321
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7205
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7205
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7202
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7202
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7107
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7107
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 3 0.7074
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 3 0.7074

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