(2E,10E,12R)-3,7,11,15-tetramethylhexadeca-2,10,14-triene-1,7,12-triol - Compound Card

(2E,10E,12R)-3,7,11,15-tetramethylhexadeca-2,10,14-triene-1,7,12-triol

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(2E,10E,12R)-3,7,11,15-tetramethylhexadeca-2,10,14-triene-1,7,12-triol

Structure
Zoomed Structure
  • Family: Plantae - Sargassaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Linear Diterpene
Canonical Smiles OC/C=C(/CCCC(CC/C=C(/[C@@H](CC=C(C)C)O)\C)(O)C)\C
InChI InChI=1S/C20H36O3/c1-16(2)10-11-19(22)18(4)9-7-14-20(5,23)13-6-8-17(3)12-15-21/h9-10,12,19,21-23H,6-8,11,13-15H2,1-5H3/b17-12+,18-9+/t19-,20?/m1/s1
InChIKey SJHOVDRDQMNUHW-OETXVDTOSA-N
Formula C20H36O3
HBA 3
HBD 3
MW 324.51
Rotatable Bonds 11
TPSA 60.69
LogP 4.29
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 324.27
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Bifurcaria bifurcata Sargassaceae Plantae 74462

Showing of synonyms

  • El Hattab M, Ben Mesaoud M, et al. (2008). Trihydroxylated linear diterpenes from the brown alga Bifurcaria bifurcata (Fucales, Phaeophyta).. Biochemical Systematics and Ecology, 2008, 36(5-6), 484-489. [View]
Pubchem: 10336397

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.22
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.58

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.37
Plasma Protein Binding
27.73
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.35
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.72
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.27
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.15
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
-1.2
Rat (Acute)
1.64
Rat (Chronic Oral)
2.04
Fathead Minnow
4.86
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
353.38
Hydration Free Energy
-6.34
Log(D) at pH=7.4
2.0
Log(P)
4.31
Log S
-3.4
Log(Vapor Pressure)
-5.92
Melting Point
38.39
pKa Acid
11.17
pKa Basic
7.31
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.9529
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9484
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9395
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.9386
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9353
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9353
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9339
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9262
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.9253
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9183
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.9154
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9148
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9130
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9078
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.9002
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8980
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8864
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8799
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.8732
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8726
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8724
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8691
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8664
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8643
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8642
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8622
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8609
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8585
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8571
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8536
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8506
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8453
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8397
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8377
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8346
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8318
Cartilage oligomeric matrix protein P35444 COMP_RAT Rattus norvegicus 3 0.8293
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.8265
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8258
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8221
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8213
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8196
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8173
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8172
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8171
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8147
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8137
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8136
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8123
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.8111
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8103
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8096
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8081
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8060
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8039
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8038
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.8030
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.8023
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8015
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7997
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7990
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7982
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7962
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7961
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7932
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7918
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7907
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7905
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7859
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7858
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7842
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7827
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7826
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7793
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7749
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7749
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7715
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7694
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7688
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7684
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7676
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7671
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7652
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7643
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7637
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7636
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7627
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7625
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7621
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7616
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7604
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7579
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7576
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7569
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7552
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7512
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7480
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7457
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 4 0.7454
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7435
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7406
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7386
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7384
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7384
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7374
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7367
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7356
Nuclear receptor coactivator 2 Q15596 NCOA2_HUMAN Homo sapiens 3 0.7339
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 4 0.7325
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7323
Peroxisome proliferator-activated receptor alpha Q07869 PPARA_HUMAN Homo sapiens 3 0.7319
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7303
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7298
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7293
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7285
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7264
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7261
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7246
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7242
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7229
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7228
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7222
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7218
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7218
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7207
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7200
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7192
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7191
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7172
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7169
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7149
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7145
Cartilage oligomeric matrix protein Q9R0G6 COMP_MOUSE Mus musculus 3 0.7144
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 3 0.7129
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7128
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7119
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7112
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7107
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7107
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7105
Hemolymph juvenile hormone binding protein Q9U556 Q9U556_BOMMO Bombyx mori 3 0.7097
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7095
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7092
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7063
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7061
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7059
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7058
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7047
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 3 0.7042
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7039
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7039
7alpha-hydroxysteroid dehydrogenase P0AET8 HDHA_ECOLI Escherichia coli 4 0.7024

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