ANPDB

Select a section from the left sidebar

(-)-muqubilin A

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

Canonical Smiles	C/C(=C\CC[C@@]1(C)CC[C@@H](OO1)[C@@H](C(=O)O)C)/CCC1=C(C)CCCC1(C)C
InChI	InChI=1S/C24H40O4/c1-17(11-12-20-18(2)10-8-14-23(20,4)5)9-7-15-24(6)16-13-21(27-28-24)19(3)22(25)26/h9,19,21H,7-8,10-16H2,1-6H3,(H,25,26)/b17-9+/t19-,21+,24-/m0/s1
InChIKey	ZJKZMXQQSDVDLA-HGMMXSCQSA-N
Formula	C₂₄H₄₀O₄
HBA	3
HBD	1
MW	392.58
Rotatable Bonds	8
TPSA	55.76
LogP	6.61
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.79
Exact Mass	392.29
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: 21600068

Zinc: ZINC000044387729

Nmrshiftdb2: 70064932

Chembl: CHEMBL463702

No compound-protein relationship available.

SMILES: C1CCCC=C1CCC=CCCC2CCCOO2

Level: 1

Mol. Weight: 392.58 g/mol

SMILES: C1CCOOC1

Level: 0

Mol. Weight: 392.58 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 392.58 g/mol

Anticancer

Absorption

Caco-2 (logPapp): -4.88
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.65
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.82

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.11
Plasma Protein Binding: 83.24
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: -2.14
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.6
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.0
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.51
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: -5.31
Rat (Acute): 1.98
Rat (Chronic Oral): 2.17
Fathead Minnow: 4.3
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: 389.57
Hydration Free Energy: -4.83
Log(D) at pH=7.4: 2.51
Log(P): 7.63
Log S: -5.05
Log(Vapor Pressure): -6.74
Melting Point: 66.85
pKa Acid: 5.72
pKa Basic: 7.02

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.9416
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.9416
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.9195
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.9195
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.9190
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.9190
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8941
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8941
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8868
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8868
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.8842
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	3	0.8842
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.8833
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	3	0.8833
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8688
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8688
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8649
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8649
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8636
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8636
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8624
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8624
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8590
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8590
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.8574
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.8574
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8414
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8414
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8331
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8331
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8277
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.8277
thiamine diphosphokinase	Q82ZE3	Q82ZE3_ENTFA	Enterococcus faecalis	3	0.8273
thiamine diphosphokinase	Q82ZE3	Q82ZE3_ENTFA	Enterococcus faecalis	3	0.8273
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8255
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8255
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8145
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8145
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8031
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8031
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7940
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7940
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7937
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7937
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	3	0.7911
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	3	0.7911
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7889
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7889
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7876
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7876
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7870
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7870
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7839
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7839
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.7823
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.7823
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7764
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7764
Beta-elicitin cryptogein	P15570	ELIB_PHYCR	Phytophthora cryptogea	4	0.7755
Beta-elicitin cryptogein	P15570	ELIB_PHYCR	Phytophthora cryptogea	4	0.7755
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7714
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7714
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7714
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7714
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7705
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.7705
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7635
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7635
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7634
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7634
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7624
Chitinase	Q54276	Q54276_SERMA	Serratia marcescens	3	0.7624
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7605
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7605
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7571
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7571
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7563
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7563
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7559
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7559
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7529
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7529
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7496
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7496
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7485
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7485
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7481
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7481
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7480
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7480
Phospholipase A2	P00593	PA21B_BOVIN	Bos taurus	3	0.7471
Phospholipase A2	P00593	PA21B_BOVIN	Bos taurus	3	0.7471
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7450
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7450
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7448
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7448
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7434
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7434
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7377
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.7377
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7376
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7376
Jasmonoyl--L-amino acid synthetase JAR1	Q9SKE2	JAR1_ARATH	Arabidopsis thaliana	3	0.7370
Jasmonoyl--L-amino acid synthetase JAR1	Q9SKE2	JAR1_ARATH	Arabidopsis thaliana	3	0.7370
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7338
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7338
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7332
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7332
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7319
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7319
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7287
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	3	0.7287
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7281
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7281
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7215
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7215
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7209
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7209
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7178
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7178
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7159
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7159
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7156
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7156
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7147
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7147
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7135
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7135
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7115
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7115
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7113
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7113
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	3	0.7090
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	3	0.7090
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7082
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7082
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	3	0.7071
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase	P19992	HSD_STREX	Streptomyces exfoliatus	3	0.7071
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7056
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7056
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7041
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7041
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7025
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7025
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7023
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7023
Cellular retinoic acid-binding protein 2	P29373	RABP2_HUMAN	Homo sapiens	3	0.7022
Cellular retinoic acid-binding protein 2	P29373	RABP2_HUMAN	Homo sapiens	3	0.7022
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	2	0.7019
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	2	0.7019
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7018
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7018
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7012
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7012
Endoplasmin, putative	Q8I0V4	Q8I0V4_PLAF7	Plasmodium falciparum	3	0.7007
Endoplasmin, putative	Q8I0V4	Q8I0V4_PLAF7	Plasmodium falciparum	3	0.7007

Download SDF