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Tasnemoxide A

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

Canonical Smiles	OC(=O)[C@H]([C@H]1CC[C@](OO1)(C)C/C=C/C(CCC1=C(C)CCCC1(C)C)(O)C)C
InChI	InChI=1S/C24H40O5/c1-17-9-7-12-22(3,4)19(17)10-15-23(5,27)13-8-14-24(6)16-11-20(28-29-24)18(2)21(25)26/h8,13,18,20,27H,7,9-12,14-16H2,1-6H3,(H,25,26)/b13-8+/t18-,20+,23?,24-/m0/s1
InChIKey	IOPIOUHRQRYDMU-GGYDGERUSA-N
Formula	C₂₄H₄₀O₅
HBA	4
HBD	2
MW	408.58
Rotatable Bonds	8
TPSA	75.99
LogP	5.58
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	29
Formal Charge	0
Fraction CSP3	0.79
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

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: 11189028

Cas: 655228-40-3

Nmrshiftdb2: 20025018

Chembl: CHEMBL477495

No compound-protein relationship available.

SMILES: O1OCCCC1CC=CCCCC2=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

Cytotoxic

Absorption

Caco-2 (logPapp): -5.0
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.700
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.09

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.760
Plasma Protein Binding: 72.37
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: 0.760
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.440
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.520
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.050
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: -7.110
Rat (Acute): 2.510
Rat (Chronic Oral): 2.100
Fathead Minnow: 4.100
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Toxic
SR-p53: Safe

General Properties

Boiling Point: 396.040
Hydration Free Energy: -3.850
Log(D) at pH=7.4: 1.730
Log(P): 6.17
Log S: -4.5
Log(Vapor Pressure): -7.4
Melting Point: 106.11
pKa Acid: 5.04
pKa Basic: 6.84

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.9496
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.9496
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.8890
Branched-chain-amino-acid aminotransferase, mitochondrial	O15382	BCAT2_HUMAN	Homo sapiens	3	0.8890
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8845
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8845
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8827
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.8827
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8708
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.8708
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8523
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8523
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8288
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8288
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8039
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.8039
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7875
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7875
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.7719
11-beta-hydroxysteroid dehydrogenase 1	P50172	DHI1_MOUSE	Mus musculus	3	0.7719
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7680
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7680
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7589
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7589
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7448
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7448
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7440
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7440
Phenolphthiocerol/phthiocerol polyketide synthase subunit C	P96202	PPSC_MYCTU	Mycobacterium tuberculosis	3	0.7432
Phenolphthiocerol/phthiocerol polyketide synthase subunit C	P96202	PPSC_MYCTU	Mycobacterium tuberculosis	3	0.7432
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7425
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7425
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7326
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7326
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.7312
Deacetoxycephalosporin C synthase	P18548	CEFE_STRCL	Streptomyces clavuligerus	3	0.7312
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7280
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7280
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7256
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7256
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7251
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7251
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7218
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7218
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7208
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7208
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7152
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7152
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7114
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7114
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7090
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.7090
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7073
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7073
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7068
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7068
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7059
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7059
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7057
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7057

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