ANPDB

Select a section from the left sidebar

(-)-9,10-epoxymuqubilin A

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

Canonical Smiles	C[C@H](C1CC[C@@](OO1)(C)CC[C@@H]1O[C@@]1(C)CCC1=C(C)CCCC1(C)C)C(=O)O
InChI	InChI=1S/C24H40O5/c1-16-8-7-12-22(3,4)18(16)9-15-24(6)20(27-24)11-14-23(5)13-10-19(28-29-23)17(2)21(25)26/h17,19-20H,7-15H2,1-6H3,(H,25,26)/t17-,19?,20+,23+,24+/m1/s1
InChIKey	QVVWUQNRKZFZHV-BUPAHJTJSA-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: 162934214

No compound-protein relationship available.

SMILES: C1CCCC=C1CCC2C(O2)CCC3CCCOO3

Level: 2

Mol. Weight: 408.58 g/mol

SMILES: O1CC1CCC2CCCOO2

Level: 1

Mol. Weight: 408.58 g/mol

SMILES: O1CC1CCC2=CCCCC2

Level: 1

Mol. Weight: 408.58 g/mol

SMILES: C1CCOOC1

Level: 0

Mol. Weight: 408.58 g/mol

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 408.58 g/mol

SMILES: C1CO1

Level: 0

Mol. Weight: 408.58 g/mol

Anticancer

Absorption

Caco-2 (logPapp): -5.12
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: -2.83

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.54
Plasma Protein Binding: 58.74
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: 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: 1.23
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.53
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 5.77
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: -15.62
Rat (Acute): 2.09
Rat (Chronic Oral): 2.0
Fathead Minnow: 3.97
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: 407.81
Hydration Free Energy: -5.1
Log(D) at pH=7.4: 1.5
Log(P): 6.3
Log S: -5.08
Log(Vapor Pressure): -6.9
Melting Point: 62.63
pKa Acid: 4.42
pKa Basic: 6.55

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9334
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9334
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8864
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8864
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8864
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8864
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8778
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8778
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8415
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	3	0.8415
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8317
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.8317
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8315
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8315
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8242
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8242
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8138
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8138
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8136
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8136
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7904
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7904
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7805
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7805
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7782
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7782
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7758
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7758
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.7745
Retinol-binding protein 2	P50120	RET2_HUMAN	Homo sapiens	3	0.7745
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7651
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7651
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7646
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7646
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7613
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7613
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7582
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7582
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7564
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7564
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7537
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7537
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7536
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7536
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7526
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.7526
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7419
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7419
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7391
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7391
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7368
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7368
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7332
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7332
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7315
Retinol-binding protein 1	P02696	RET1_RAT	Rattus norvegicus	3	0.7315
Abscisic acid receptor PYL10	Q8H1R0	PYL10_ARATH	Arabidopsis thaliana	3	0.7301
Abscisic acid receptor PYL10	Q8H1R0	PYL10_ARATH	Arabidopsis thaliana	3	0.7301
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7266
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7266
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7243
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7243
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7198
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7198
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7183
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7183
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7177
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7177
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7122
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7122
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7106
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	3	0.7106
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7080
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7080
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	2	0.7062
Gastrotropin	Q6IMW5	Q6IMW5_DANRE	Danio rerio	2	0.7062
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7033
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7033
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7025
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7025
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7008
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7008

Download SDF