(2E,5E,10E,12R)-3,7,11,15-tetramethylhexadeca-2,5,10,14-tetraene-1,7,12-triol - Compound Card

(2E,5E,10E,12R)-3,7,11,15-tetramethylhexadeca-2,5,10,14-tetraene-1,7,12-triol

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(2E,5E,10E,12R)-3,7,11,15-tetramethylhexadeca-2,5,10,14-tetraene-1,7,12-triol

Structure
Zoomed Structure
  • Family: Sargassaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Linear Diterpene
Canonical Smiles OC/C=C(/C/C=C/C(CC/C=C(/[C@@H](CC=C(C)C)O)\C)(O)C)\C
InChI InChI=1S/C20H34O3/c1-16(2)10-11-19(22)18(4)9-7-14-20(5,23)13-6-8-17(3)12-15-21/h6,9-10,12-13,19,21-23H,7-8,11,14-15H2,1-5H3/b13-6+,17-12+,18-9+/t19-,20?/m1/s1
InChIKey KDYXTWXKNUZVRV-WPESGBQVSA-N
Formula C20H34O3
HBA 3
HBD 3
MW 322.49
Rotatable Bonds 10
TPSA 60.69
LogP 4.07
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 322.25
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: 163110384

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.19
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.43
Plasma Protein Binding
35.55
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
6.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.6
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.26
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.28
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
-1.58
Rat (Acute)
1.69
Rat (Chronic Oral)
2.08
Fathead Minnow
5.25
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
350.17
Hydration Free Energy
-6.87
Log(D) at pH=7.4
2.19
Log(P)
4.1
Log S
-3.53
Log(Vapor Pressure)
-5.88
Melting Point
48.1
pKa Acid
10.79
pKa Basic
6.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9354
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.9226
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9216
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9141
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.9058
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9051
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8967
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8871
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.8869
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8863
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8829
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.8773
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8762
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8738
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8733
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8718
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8704
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8669
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8594
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8557
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8508
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8497
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8484
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.8467
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8405
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8392
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8383
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8330
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8287
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8238
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.8150
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8142
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8136
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8125
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8105
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8078
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8043
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.8039
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7948
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7934
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7914
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7908
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7889
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7855
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 4 0.7850
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7798
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7760
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7748
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7719
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 3 0.7695
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7685
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7675
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7662
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7661
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7651
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7647
Cartilage oligomeric matrix protein P35444 COMP_RAT Rattus norvegicus 3 0.7646
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7642
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7639
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7625
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7622
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7610
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7607
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7591
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7580
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7549
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7541
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7534
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7528
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7515
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7513
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.7499
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7486
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7479
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7479
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7478
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7478
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7470
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7443
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7436
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7419
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7415
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7407
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7399
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7398
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7396
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7391
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7384
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7383
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7377
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7376
Thyroid hormone receptor alpha P04625 THA_CHICK Gallus gallus 3 0.7369
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7354
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7348
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7345
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7345
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7344
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7339
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7337
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7336
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 4 0.7322
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7305
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7290
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7289
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7284
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7284
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7280
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7272
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7254
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7244
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7226
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7224
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7210
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7210
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7185
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7179
Oxysterols receptor LXR-beta P55055 NR1H2_HUMAN Homo sapiens 3 0.7178
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7173
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7164
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7160
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 4 0.7157
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7154
Cartilage oligomeric matrix protein Q9R0G6 COMP_MOUSE Mus musculus 3 0.7149
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7146
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 4 0.7142
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7125
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7120
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7116
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7111
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7103
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7101
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7100
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7097
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7090
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7078
Nuclear receptor ROR-alpha P35398 RORA_HUMAN Homo sapiens 3 0.7077
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7059
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7056
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.7055
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7047
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7038
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7017
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7014

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