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

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

Select a section from the left sidebar

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

Structure
Zoomed Structure
  • Family: Plantae - Sargassaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Linear Diterpene
Canonical Smiles OC/C=C(/CCCC(CCC(/C(=C/CC=C(C)C)/C)O)(O)C)\C
InChI InChI=1S/C20H36O3/c1-16(2)8-6-10-18(4)19(22)11-14-20(5,23)13-7-9-17(3)12-15-21/h8,10,12,19,21-23H,6-7,9,11,13-15H2,1-5H3/b17-12+,18-10+
InChIKey TYQMTAWYPXQFLX-UJTOSYCASA-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: 171119736

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.67
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.32
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.45
Plasma Protein Binding
15.86
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
6.85
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.73
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.37
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.33
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
1.19
Rat (Acute)
1.65
Rat (Chronic Oral)
2.04
Fathead Minnow
4.9
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
352.41
Hydration Free Energy
-7.48
Log(D) at pH=7.4
2.11
Log(P)
4.06
Log S
-3.57
Log(Vapor Pressure)
-5.75
Melting Point
41.37
pKa Acid
10.65
pKa Basic
7.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9372
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9305
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9240
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.9170
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9135
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8969
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8880
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8845
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8774
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8767
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8739
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8727
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.8720
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8714
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8690
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8684
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8658
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8641
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8636
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8630
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8627
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8556
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.8555
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.8546
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8530
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8497
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8490
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8485
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8356
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8247
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8242
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8238
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8219
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8169
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8149
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8113
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8068
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8038
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8019
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7971
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7956
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7948
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7895
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7882
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7877
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 4 0.7866
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7863
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7854
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7842
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7819
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7814
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7805
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7795
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7764
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7749
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7745
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7718
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7686
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7665
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7640
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7626
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7622
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7602
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7556
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7552
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7551
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7531
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7529
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7524
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7505
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7500
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7495
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7466
Peroxisome proliferator-activated receptor alpha Q07869 PPARA_HUMAN Homo sapiens 3 0.7456
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7456
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7454
Lanosterol 14-alpha-demethylase Q385E8 Q385E8_TRYB2 Trypanosoma brucei brucei 4 0.7440
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 5 0.7421
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7421
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 2 0.7411
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7406
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7405
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7405
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7390
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7383
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7382
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 3 0.7372
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7364
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7363
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7358
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7315
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7311
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7308
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7292
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7276
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7269
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7265
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7243
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7242
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7241
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7229
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7226
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7205
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7190
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.7181
Gibberellin receptor GID1A Q9MAA7 GID1A_ARATH Arabidopsis thaliana 3 0.7177
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7161
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7160
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7156
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7141
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7134
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7128
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7108
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7087
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7077
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7067
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7041
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7037
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7035
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 3 0.7000

Download SDF