Aikupikoxide C - Compound Card

Aikupikoxide C

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Aikupikoxide C

Structure
Zoomed Structure
  • Family: Animalia - Podospongiidae
  • Kingdom: Animalia
  • Class: Terpenoid
    • Subclass: Norditerpene Cyclic Peroxide
Canonical Smiles COC(=O)C(C1CCC(OO1)(C)CCC(=O)C(CCCC(=O)C)(C)C)C
InChI InChI=1S/C20H34O6/c1-14(21)8-7-11-19(3,4)17(22)10-13-20(5)12-9-16(25-26-20)15(2)18(23)24-6/h15-16H,7-13H2,1-6H3
InChIKey OQQQVWCMVDRPGR-UHFFFAOYSA-N
Formula C20H34O6
HBA 6
HBD 0
MW 370.49
Rotatable Bonds 10
TPSA 78.9
LogP 3.8
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.85
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]
Pubchem: 56667210
Nmrshiftdb2: 70089527

No compound-protein relationship available.

Structure

SMILES: C1CCOOC1

Level: 0

Mol. Weight: 370.49 g/mol

Cytotoxic

Absorption

Caco-2 (logPapp)
-4.41
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.680
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.440
Plasma Protein Binding
31.62
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
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
9.120
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.570
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.780
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.460
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
0.570
Rat (Acute)
2.110
Rat (Chronic Oral)
1.590
Fathead Minnow
4.200
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
363.190
Hydration Free Energy
-6.260
Log(D) at pH=7.4
2.240
Log(P)
2.79
Log S
-3.7
Log(Vapor Pressure)
-5.53
Melting Point
20.62
pKa Acid
10.67
pKa Basic
3.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9781
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9781
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9290
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9290
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9252
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9252
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9219
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9219
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9029
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9029
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8930
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8930
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8928
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8928
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8869
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8869
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8818
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8818
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8784
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8784
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8765
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8765
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8738
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8738
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8708
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8708
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8648
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8648
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8609
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8609
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8523
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8523
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8357
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8357
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8348
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8348
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8331
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8331
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 4 0.8306
Peptidoglycan recognition protein 1 Q9GK12 PGRP1_CAMDR Camelus dromedarius 4 0.8306
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8294
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8294
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8277
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8277
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
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8154
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8154
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8121
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8121
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8096
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8096
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8091
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8091
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8017
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8017
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7987
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7987
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7973
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.7973
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7888
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7888
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7874
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7874
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7793
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7793
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7718
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7718
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7706
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7706
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7702
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7702
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7665
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7665
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7649
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7649
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7574
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7574
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7554
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7554
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7552
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7552
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7530
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7530
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7506
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7506
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7496
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7496
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7483
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7483
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7469
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7469
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7468
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7468
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7459
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7459
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7412
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7412
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7392
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7392
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7374
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7374
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7374
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7374
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7372
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7372
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7363
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7363
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7347
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7347
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7332
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7332
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7328
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7328
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7327
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7327
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7326
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7326
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7313
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7313
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7264
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7264
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7262
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7262
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7250
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7250
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7248
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7248
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7240
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7240
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7227
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7227
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7214
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7214
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7196
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7196
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7195
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7195
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7186
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7186
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7179
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7179
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7175
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7175
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7172
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7172
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7171
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7171
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7161
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7161
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7153
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7153
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7145
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7145
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7135
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7135
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7133
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7133
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7131
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7131
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7130
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7130
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7129
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7129
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7122
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7122
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7115
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7115
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7114
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7114
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 2 0.7113
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 2 0.7113
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7112
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7112
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7088
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7088
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7061
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7061
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7060
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7060
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7043
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7043
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 4 0.7042
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 4 0.7042
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7039
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7039
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7033
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7033
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7028
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7028
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7014
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7014
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7009
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7009

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