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Muqubilin

Family: Animalia - Podospongiidae
Kingdom: Animalia
Class: Terpenoid
- Subclass: 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+/m1/s1
InChIKey	ZJKZMXQQSDVDLA-LAJJABCHSA-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

Youssef DT, Yoshida WY, et al. (2001). Cytotoxic cyclic norterpene peroxides from a Red Sea sponge Diacarnus erythraenus. Journal of Natural Products,2001,64(10),1332-1335. [View] [PubMed]

Pubchem: 6436222

Cas: 72154-33-7

Zinc: ZINC000042875803

Nmrshiftdb2: 70089526

Chembl: CHEMBL514368

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

Cytotoxic

Absorption

Caco-2 (logPapp): -4.89
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: -2.8

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.12
Plasma Protein Binding: 81.65
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: -2.12
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: 5.52
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: -5.11
Rat (Acute): 1.97
Rat (Chronic Oral): 2.17
Fathead Minnow: 4.33
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: 387.92
Hydration Free Energy: -4.8
Log(D) at pH=7.4: 2.52
Log(P): 7.58
Log S: -5.03
Log(Vapor Pressure): -6.75
Melting Point: 74.92
pKa Acid: 5.72
pKa Basic: 6.99

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.9449
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.9449
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.9329
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.9329
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.9076
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.9076
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.9019
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.9019
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8974
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8974
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8906
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8906
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8836
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8836
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8812
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8812
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8430
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8430
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.8352
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.8352
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8298
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8298
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8239
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8239
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8231
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8231
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8149
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8149
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.8011
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.8011
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7998
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7998
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7983
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7983
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.7942
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.7942
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7894
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7894
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7836
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7836
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7829
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7829
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7775
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.7775
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7750
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7750
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7750
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7750
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7689
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7689
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7679
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7679
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7674
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7674
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.7673
Vitamin D(3) 25-hydroxylase	C4B644	CPVDH_PSEAH	Pseudonocardia autotrophica	3	0.7673
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7671
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7671
Jasmonoyl--L-amino acid synthetase JAR1	Q9SKE2	JAR1_ARATH	Arabidopsis thaliana	3	0.7627
Jasmonoyl--L-amino acid synthetase JAR1	Q9SKE2	JAR1_ARATH	Arabidopsis thaliana	3	0.7627
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7566
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7566
Cholesterol side-chain cleavage enzyme, mitochondrial	P05108	CP11A_HUMAN	Homo sapiens	3	0.7502
Cholesterol side-chain cleavage enzyme, mitochondrial	P05108	CP11A_HUMAN	Homo sapiens	3	0.7502
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7454
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7454
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7451
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7451
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7449
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7449
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7447
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7447
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7440
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7440
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7422
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7422
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7375
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7375
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7367
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7367
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7359
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7359
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7353
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7353
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7342
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7342
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7333
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7333
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7318
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7318
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7299
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7299
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7293
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7293
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7289
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7289
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7283
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7283
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7282
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7282
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7278
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7278
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	3	0.7242
Muconolactone Delta-isomerase	Q8G9L0	Q8G9L0_RHOOP	Rhodococcus opacus	3	0.7242
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7225
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7225
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7214
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7214
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7209
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7209
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7205
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7205
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7203
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7203
Carboxyethyl-arginine beta-lactam-synthase	P0DJQ7	BLS_STRCL	Streptomyces clavuligerus	2	0.7202
Carboxyethyl-arginine beta-lactam-synthase	P0DJQ7	BLS_STRCL	Streptomyces clavuligerus	2	0.7202
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7179
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7179
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7174
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7174
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7138
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7138
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7123
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7123
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7119
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7119
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7108
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7108
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7105
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7105
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7085
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7085
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7071
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7071
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7057
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7057
Endoplasmin, putative	Q8I0V4	Q8I0V4_PLAF7	Plasmodium falciparum	3	0.7054
Endoplasmin, putative	Q8I0V4	Q8I0V4_PLAF7	Plasmodium falciparum	3	0.7054
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7050
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7050
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7048
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7048
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7038
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7038
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7034
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7034
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	2	0.7022
Epoxide hydrolase	Q41415	Q41415_SOLTU	Solanum tuberosum	2	0.7022
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7019
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7019
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7010
Phospholipase A2	P00593	PA21B_BOVIN	Bos taurus	3	0.7010
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7010
Phospholipase A2	P00593	PA21B_BOVIN	Bos taurus	3	0.7010
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7003
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7003

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