(2E,6E,10E)-12(S)- hydroxy-3,7,11,15_tetramethylethylhexadeca-2,6,10,14-tetraenoic acid - Compound Card

(2E,6E,10E)-12(S)- hydroxy-3,7,11,15_tetramethylethylhexadeca-2,6,10,14-tetraenoic acid

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(2E,6E,10E)-12(S)- hydroxy-3,7,11,15_tetramethylethylhexadeca-2,6,10,14-tetraenoic acid

Structure
Zoomed Structure
  • Family: Plantae - Cystoseiraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Acyclic Diterpene
Canonical Smiles C/C(=C\CC/C(=C/C(=O)O)/C)/CC/C=C(/[C@H](CC=C(C)C)O)\C
InChI InChI=1S/C20H32O3/c1-15(2)12-13-19(21)18(5)11-7-9-16(3)8-6-10-17(4)14-20(22)23/h8,11-12,14,19,21H,6-7,9-10,13H2,1-5H3,(H,22,23)/b16-8+,17-14+,18-11+/t19-/m0/s1
InChIKey WUTNFDVILUENNQ-HBSSDYDPSA-N
Formula C20H32O3
HBA 2
HBD 2
MW 320.47
Rotatable Bonds 10
TPSA 57.53
LogP 5.19
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 320.24
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Bifurcaria bifurcata Cystoseiraceae Plantae 74462

Showing of synonyms

  • Semmak L, Zerzouf A, et al. (1988). Acyclic diterpenes from Bifurcaria bifurcata.. Phytochemistry, 1988, 27(7), 2347-2349. [View]
Pubchem: 12018261
Nmrshiftdb2: 60074862

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.24

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.83
Plasma Protein Binding
52.76
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
-0.83
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.2
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.22
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.93
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
0.06
Rat (Acute)
1.62
Rat (Chronic Oral)
2.28
Fathead Minnow
5.15
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
358.71
Hydration Free Energy
-6.24
Log(D) at pH=7.4
1.25
Log(P)
5.56
Log S
-3.86
Log(Vapor Pressure)
-6.83
Melting Point
114.69
pKa Acid
7.15
pKa Basic
7.27
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.9493
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9468
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9398
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.9250
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9187
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.9179
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9103
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9088
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9023
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8962
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8916
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8881
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8853
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8852
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8840
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8816
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8700
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8690
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8672
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8658
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8637
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8555
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8554
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8503
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8466
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8447
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8436
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8434
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8384
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.8378
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8377
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8342
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8317
Cellular retinoic acid-binding protein 2 P29373 RABP2_HUMAN Homo sapiens 3 0.8290
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8256
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8212
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8197
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8188
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 4 0.8120
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8076
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8039
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8038
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8017
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8012
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7948
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7941
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 4 0.7919
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7917
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7914
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7900
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7892
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7888
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7835
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7834
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7824
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7822
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7816
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7812
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7807
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7803
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7802
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7791
Hemolymph juvenile hormone binding protein Q9U556 Q9U556_BOMMO Bombyx mori 3 0.7760
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7746
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7742
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7735
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7725
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7705
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7704
4,5:9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oate hydrolase P9WNH5 HSAD_MYCTU Mycobacterium tuberculosis 3 0.7696
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7690
Japanin M1MR49 M1MR49_RHIAP Rhipicephalus appendiculatus 3 0.7686
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7682
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7655
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7644
Cartilage oligomeric matrix protein P35444 COMP_RAT Rattus norvegicus 3 0.7627
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7622
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7622
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7621
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7612
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7603
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7589
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7572
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7567
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7554
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7549
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7541
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7527
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7517
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7509
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.7503
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7501
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7494
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7493
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7492
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7473
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7472
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7459
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7443
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7442
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7442
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7438
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7438
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 4 0.7434
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7423
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7411
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 2 0.7409
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7407
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7403
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7400
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7357
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7315
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7315
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7313
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7313
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7303
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7288
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7287
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 2 0.7279
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7277
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7274
Putative cytochrome P450 120 Q59990 CP120_SYNY3 Synechocystis sp 3 0.7270
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7258
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7257
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7253
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7252
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7249
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7245
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7242
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7233
Solanesyl diphosphate synthase 3, chloroplastic/mitochondrial Q5HZ00 SPS3_ARATH Arabidopsis thaliana 2 0.7212
thiamine diphosphokinase Q82ZE3 Q82ZE3_ENTFA Enterococcus faecalis 3 0.7208
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7205
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7195
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.7187
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7171
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7171
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7150
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7148
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7102
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7095
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7091
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7079
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7078
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 3 0.7077
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 2 0.7076
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7069
Pyrrolysine--tRNA ligase Q8PWY1 PYLS_METMA Methanosarcina mazei 2 0.7058
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7044
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7043
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7021
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7017
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7016
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7012
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7005
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7004

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