Aikupikoxide D - Compound Card

Aikupikoxide D

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Aikupikoxide D

Structure
Zoomed Structure
  • Family: Animalia - Podospongiidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Norditerpene Cyclic Peroxide
Canonical Smiles COC(=O)[C@H]([C@@H]1CC[C@](OO1)(C)CCC(=O)C(=C)CCCC(O)(C)C)C
InChI InChI=1S/C20H34O6/c1-14(8-7-11-19(3,4)23)16(21)9-12-20(5)13-10-17(25-26-20)15(2)18(22)24-6/h15,17,23H,1,7-13H2,2-6H3/t15-,17-,20-/m0/s1
InChIKey VQXVFFWQWCQNFB-KNBMTAEXSA-N
Formula C20H34O6
HBA 6
HBD 1
MW 370.49
Rotatable Bonds 10
TPSA 82.06
LogP 3.51
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 370.24
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]

No compound-protein relationship available.

Structure

SMILES: C1CCOOC1

Level: 0

Mol. Weight: 370.49 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.52
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
-2.61

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.440
Plasma Protein Binding
53.69
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
7.450
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.230
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.660
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.600
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
-1.910
Rat (Acute)
2.570
Rat (Chronic Oral)
1.530
Fathead Minnow
3.950
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
357.960
Hydration Free Energy
-6.350
Log(D) at pH=7.4
2.010
Log(P)
3.24
Log S
-3.5
Log(Vapor Pressure)
-6.09
Melting Point
49.57
pKa Acid
9.58
pKa Basic
4.16
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 0.9526
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9526
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9345
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9345
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9077
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9077
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9030
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9030
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8973
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8973
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8967
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8967
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8901
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8901
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8620
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8620
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8596
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8596
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8521
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8521
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8323
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8323
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8288
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8288
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8157
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8157
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8064
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8064
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8019
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8019
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8012
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8012
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7949
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7949
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7948
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7948
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7928
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7928
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7918
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7918
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7888
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7888
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7868
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7868
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7867
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7867
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7859
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7859
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7838
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7838
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7836
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7836
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7816
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7816
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7806
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7806
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7764
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7764
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7764
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7764
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7713
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7713
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7678
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7678
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7637
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7637
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7617
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7617
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7611
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7611
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7609
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7609
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7601
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7601
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7581
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7581
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7576
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7576
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7475
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7475
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7469
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7469
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7469
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7469
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7450
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7450
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7434
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7434
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7432
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7432
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7431
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7431
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7423
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7423
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7414
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7414
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7380
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7380
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7377
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7377
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7362
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7362
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7354
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7354
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7339
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7339
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7330
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7330
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7287
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7287
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7278
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7278
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7272
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7272
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7270
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7270
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7266
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7266
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7242
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7242
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7239
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7239
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7237
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7237
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7237
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7237
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7235
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7235
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7232
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7232
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7225
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7225
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7218
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7218
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7214
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7214
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7169
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7169
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7151
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7151
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7149
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7149
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7145
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7145
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7140
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7140
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7140
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7140
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7132
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7132
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7128
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7128
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7123
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7123
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7110
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7110
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7102
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7102
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7079
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7079
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7077
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7077
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7041
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7041
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7040
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7040
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7034
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7034
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7029
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7029
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7016
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7016
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7011
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7011
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7009
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7009
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7001
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7001

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