Verticilla-4(20),7,11-triene - Compound Card

Verticilla-4(20),7,11-triene

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Verticilla-4(20),7,11-triene

Structure
Zoomed Structure
  • Family: Plantae - Burseraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C=C1CC/C=C(/C)\CCC2=C(CC[C@@H](CC1)C2(C)C)C
InChI InChI=1S/C20H32/c1-15-7-6-8-16(2)10-14-19-17(3)11-13-18(12-9-15)20(19,4)5/h8,18H,1,6-7,9-14H2,2-5H3/b16-8-/t18-/m1/s1
InChIKey SNPPNYAGNBWZCL-CTJNPYBDSA-N
Formula C20H32
HBA 0
HBD 0
MW 272.48
Rotatable Bonds 0
TPSA 0.0
LogP 6.6
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 272.25
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Boswellia species Burseraceae Plantae 173701

Showing of synonyms

  • Melese A, Dagne E. (2007). Phytochemical investigation of the resins of Boswellia species collected from Kebtele area in Agew-Awi (Gojjam). M.Sc. Thesis, Addis Ababa University, Ethiopia, 2007. [View] [PubMed]
Pubchem: 12165334

No compound-protein relationship available.

Structure

SMILES: C1CC=CCCC(=C)CCC(C2)CCC=C12

Level: 0

Mol. Weight: 272.48 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.25
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.15
Plasma Protein Binding
62.51
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
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.2
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.11
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.53
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.07
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
1.87
Rat (Acute)
1.75
Rat (Chronic Oral)
1.48
Fathead Minnow
4.42
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
324.93
Hydration Free Energy
-0.08
Log(D) at pH=7.4
4.26
Log(P)
7.94
Log S
-6.37
Log(Vapor Pressure)
-3.37
Melting Point
24.75
pKa Acid
13.18
pKa Basic
7.95
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8980
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8980
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8847
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8847
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8680
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8680
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.8301
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.8301
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8203
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8203
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8117
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.8117
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8090
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8090
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7989
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7989
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7985
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7985
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7961
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7961
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7927
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7927
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7865
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7865
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7857
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7857
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7842
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7842
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7827
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7827
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7820
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7820
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7798
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7798
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7789
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7789
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7784
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7784
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7757
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7757
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7748
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7748
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7702
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7702
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7688
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7688
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7687
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7687
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7684
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7684
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7680
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7680
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7661
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7661
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7661
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7661
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7655
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7655
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7636
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7636
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7625
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7625
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7618
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7618
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7614
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7614
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7614
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7614
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7612
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7612
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7611
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7611
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7604
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7604
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7597
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7597
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7596
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7596
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7582
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7582
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7547
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7547
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7517
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7517
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7496
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7496
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7487
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7487
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7481
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7481
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7478
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7478
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7473
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7473
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7473
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7473
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7470
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7470
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7445
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7445
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7444
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7444
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7443
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7443
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7437
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7437
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7421
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7421
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7417
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7417
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7386
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7386
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 2 0.7343
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 2 0.7343
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7315
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7315
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7313
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7313
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7311
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7311
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7293
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7293
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7291
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7291
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7283
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7283
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7277
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7277
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7261
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7261
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7256
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7256
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7253
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7253
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7224
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7224
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 3 0.7222
Endoplasmin, putative Q8I0V4 Q8I0V4_PLAF7 Plasmodium falciparum 3 0.7222
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7213
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7213
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7187
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7187
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7186
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7186
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7181
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7181
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7177
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7177
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7176
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7176
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 2 0.7155
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 2 0.7155
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7140
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7140
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7140
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7140
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7136
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7136
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7113
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7113
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7094
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7094
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7090
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7090
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7075
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 2 0.7075
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7073
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7073
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7035
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7035
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7034
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7034
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7031
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7031
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7023
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7023
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7016
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7016
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7009
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7009

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