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(-)-13,14-epoxymuqubilin A

Family: Animalia - Podospongiidae
Kingdom: Animalia
Class: Terpenoid
- Subclass: Cyclic Norterpene Peroxide

Canonical Smiles	C/C(=C\CC[C@]1(C)CCC(OO1)[C@H](C(=O)O)C)/CCC12OC2(C)CCCC1(C)C
InChI	InChI=1S/C24H40O5/c1-17(10-16-24-21(3,4)12-8-14-23(24,6)28-24)9-7-13-22(5)15-11-19(27-29-22)18(2)20(25)26/h9,18-19H,7-8,10-16H2,1-6H3,(H,25,26)/b17-9+/t18-,19?,22-,23?,24?/m1/s1
InChIKey	ZJDQUUJWNSJRQH-GQVLGLMWSA-N
Formula	C₂₄H₄₀O₅
HBA	4
HBD	1
MW	408.58
Rotatable Bonds	8
TPSA	68.29
LogP	5.82
Number Rings	3
Number Aromatic Rings	0
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.88
Exact Mass	408.29
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: 162980046

No compound-protein relationship available.

SMILES: C1CCCC(O2)C12CCC=CCCC3CCCOO3

Level: 1

Mol. Weight: 408.58 g/mol

SMILES: C12C(O2)CCCC1

Level: 0

Mol. Weight: 408.58 g/mol

SMILES: C1CCOOC1

Level: 0

Mol. Weight: 408.58 g/mol

Anticancer

Absorption

Caco-2 (logPapp): -5.1
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.75
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.88

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.52
Plasma Protein Binding: 39.08
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: 8.98
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.35
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.42
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 6.02
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: Toxic
NR-TR: Safe
T. Pyriformis: -14.46
Rat (Acute): 1.99
Rat (Chronic Oral): 1.96
Fathead Minnow: 4.49
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: 405.74
Hydration Free Energy: -5.56
Log(D) at pH=7.4: 1.92
Log(P): 6.49
Log S: -5.18
Log(Vapor Pressure): -6.74
Melting Point: 66.9
pKa Acid: 4.37
pKa Basic: 6.81

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.9434
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.9434
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9087
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9087
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8964
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8964
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8936
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8936
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8931
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8931
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.8798
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.8798
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8398
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8398
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.8345
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.8345
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.8187
Protein BRASSINOSTEROID INSENSITIVE 1	O22476	BRI1_ARATH	Arabidopsis thaliana	4	0.8187
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8106
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.8106
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8029
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8029
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7993
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7993
Cellular retinoic acid-binding protein 2	P29373	RABP2_HUMAN	Homo sapiens	3	0.7886
Cellular retinoic acid-binding protein 2	P29373	RABP2_HUMAN	Homo sapiens	3	0.7886
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7866
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7866
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7806
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7806
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.7760
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.7760
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7649
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7649
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7632
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7632
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	3	0.7626
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	3	0.7626
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.7554
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.7554
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7542
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7542
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7534
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7534
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7527
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7527
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7503
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7503
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7497
Sodium-dependent dopamine transporter	Q7K4Y6	DAT_DROME	Drosophila melanogaster	2	0.7497
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7485
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7485
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7382
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7382
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7319
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7319
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7298
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7298
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7287
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7287
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7272
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7272
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7252
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7252
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7238
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.7238
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7199
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7199
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7196
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7196
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7171
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7171
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7170
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7170
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7169
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7169
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7150
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7150
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7116
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7116
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7085
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7085
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7076
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7076
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7075
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7075
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7074
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7074
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	4	0.7065
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	4	0.7065
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7056
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7056
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7048
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7048
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7034
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7034
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.7016
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.7016
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7016
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7016

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