Sigmosceptrellin B - Compound Card

Sigmosceptrellin B

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Sigmosceptrellin B

Structure
Zoomed Structure
  • Family: Animalia - Podospongiidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Norditerpene Cyclic Peroxide
Canonical Smiles C[C@@H]([C@H]1CC[C@](OO1)(C)CC[C@H]1[C@H](C)CC[C@@]2([C@@H]1CCCC2=C)C)C(=O)O
InChI InChI=1S/C23H38O4/c1-15-9-14-23(5)16(2)7-6-8-19(23)18(15)10-12-22(4)13-11-20(26-27-22)17(3)21(24)25/h15,17-20H,2,6-14H2,1,3-5H3,(H,24,25)/t15-,17+,18+,19-,20-,22+,23+/m1/s1
InChIKey VRMMLZKUQZCNHU-UQILNWLDSA-N
Formula C23H38O4
HBA 3
HBD 1
MW 378.55
Rotatable Bonds 5
TPSA 55.76
LogP 5.77
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.87
Exact Mass 378.28
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Diacarnus erythraenus Podospongiidae Animalia 283431
2 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]
  • Youssef DT (2004). Tasnemoxides A-C, new cytotoxic cyclic norsesterterpene peroxides from the Red Sea sponge Diacarnus erythraenus. Journal of Natural Products,2004,67(1),112-114. [View] [PubMed]
Pubchem: 44584775
Nmrshiftdb2: 70046109
CPRiL: 431645
Structure

SMILES: C=C1CCCC(C12)C(CCC2)CCC3CCCOO3

Level: 1

Mol. Weight: 378.55 g/mol

Structure

SMILES: C=C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 378.55 g/mol

Structure

SMILES: C1CCOOC1

Level: 0

Mol. Weight: 378.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.93
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.63
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.77

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.09
Plasma Protein Binding
77.83
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.33
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.14
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.25
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.0
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
-7.54
Rat (Acute)
2.46
Rat (Chronic Oral)
2.27
Fathead Minnow
3.92
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
400.19
Hydration Free Energy
-3.96
Log(D) at pH=7.4
2.82
Log(P)
6.45
Log S
-5.36
Log(Vapor Pressure)
-7.34
Melting Point
118.55
pKa Acid
5.3
pKa Basic
7.45
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9238
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9238
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8795
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8795
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.8710
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.8710
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8692
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8692
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8660
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8660
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8550
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8550
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8465
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8465
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8292
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8292
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8145
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8145
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8116
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8116
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7815
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7815
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7809
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7809
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7690
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7690
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7677
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7677
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7649
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7649
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7570
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7570
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7558
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7558
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7552
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7552
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7532
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7532
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7504
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7504
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7485
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7485
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7439
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7439
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7400
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7400
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7357
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7357
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7322
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7322
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7304
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7304
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7254
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7254
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7236
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7236
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7221
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7221
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7172
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7172
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7149
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7149
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7145
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7145
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7117
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7117
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7090
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7090
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7081
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7081
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7049
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7049

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