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Aikupikoxide B

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

Canonical Smiles	COC(=O)[C@H]([C@@H]1CC[C@](OO1)(C)CCC1(O)C(=C)CCCC1(C)C)C
InChI	InChI=1S/C20H34O5/c1-14-8-7-10-18(3,4)20(14,22)13-12-19(5)11-9-16(24-25-19)15(2)17(21)23-6/h15-16,22H,1,7-13H2,2-6H3/t15-,16-,19+,20?/m0/s1
InChIKey	OHYYIYQJXHASNH-CAHGDOEDSA-N
Formula	C₂₀H₃₄O₅
HBA	5
HBD	1
MW	354.49
Rotatable Bonds	5
TPSA	64.99
LogP	3.94
Number Rings	2
Number Aromatic Rings	0
Heavy Atom Count	25
Formal Charge	0
Fraction CSP3	0.85
Exact Mass	354.24
Number of Lipinski Rule Violations	0

#	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: 11111009

Cas: 377088-39-6

Nmrshiftdb2: 70089529

Chembl: CHEMBL504808

No compound-protein relationship available.

SMILES: C1CCCC(C1=C)CCC2CCCOO2

Level: 1

Mol. Weight: 354.49 g/mol

SMILES: C=C1CCCCC1

Level: 0

Mol. Weight: 354.49 g/mol

SMILES: C1CCOOC1

Level: 0

Mol. Weight: 354.49 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp): -4.62
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.600
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.74

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.430
Plasma Protein Binding: 53.07
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: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.250
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.420
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.500
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.400
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: -1.870
Rat (Acute): 2.820
Rat (Chronic Oral): 1.530
Fathead Minnow: 3.920
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 344.380
Hydration Free Energy: -4.960
Log(D) at pH=7.4: 2.710
Log(P): 4.16
Log S: -4.14
Log(Vapor Pressure): -5.44
Melting Point: 81.34
pKa Acid: 8.83
pKa Basic: 5.01

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8274
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8274
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.8011
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	3	0.8011
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7932
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.7932
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7730
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7730
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7644
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7644
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7622
Cytochrome P450	Q93H81	Q93H81_STRAX	Streptomyces avermitilis	3	0.7622
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7583
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7583
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7569
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7569
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7563
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7563
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7528
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7528
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7475
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7475
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7448
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7448
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7389
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7389
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7351
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7351
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7321
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.7321
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7216
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7216
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7198
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7198
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7184
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7184
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7178
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7178
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7172
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7172
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7165
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7165
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7091
Trichodiene synthase	P13513	TRI5_FUSSP	Fusarium sporotrichioides	2	0.7091
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7081
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7081
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7068
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7068
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7063
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7063
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7061
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7061
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7046
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7046
Retinaldehyde-binding protein 1	P12271	RLBP1_HUMAN	Homo sapiens	4	0.7021
Retinaldehyde-binding protein 1	P12271	RLBP1_HUMAN	Homo sapiens	4	0.7021
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7018
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	3	0.7018

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