(2E,10E,12R)-3,11,15-trimethyl-7-methylenehexadeca-2,10,14-triene-1,6,12-triol - Compound Card

(2E,10E,12R)-3,11,15-trimethyl-7-methylenehexadeca-2,10,14-triene-1,6,12-triol

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(2E,10E,12R)-3,11,15-trimethyl-7-methylenehexadeca-2,10,14-triene-1,6,12-triol

Structure
Zoomed Structure
  • Family: Plantae - Sargassaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Linear Diterpene
Canonical Smiles OC/C=C(/CCC(C(=C)CC/C=C(/[C@@H](CC=C(C)C)O)\C)O)\C
InChI InChI=1S/C20H34O3/c1-15(2)9-11-19(22)17(4)7-6-8-18(5)20(23)12-10-16(3)13-14-21/h7,9,13,19-23H,5-6,8,10-12,14H2,1-4H3/b16-13+,17-7+/t19-,20?/m1/s1
InChIKey OWUDIDPKJUCMTM-YXRHDHNMSA-N
Formula C20H34O3
HBA 3
HBD 3
MW 322.49
Rotatable Bonds 11
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: 10245596

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.15
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.44
Plasma Protein Binding
27.14
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
8.2
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.46
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.86
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.09
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
-0.75
Rat (Acute)
1.93
Rat (Chronic Oral)
2.08
Fathead Minnow
5.05
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
360.85
Hydration Free Energy
-7.86
Log(D) at pH=7.4
1.88
Log(P)
3.96
Log S
-3.59
Log(Vapor Pressure)
-6.19
Melting Point
45.13
pKa Acid
10.64
pKa Basic
5.79
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9372
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.9080
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9020
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8987
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8977
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8923
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8856
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.8806
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.8777
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8777
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8766
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 3 0.8618
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8574
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8557
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8542
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8490
1,4-alpha-glucan branching enzyme GlgB A7ZSW5 GLGB_ECO24 Escherichia coli O139:H28 3 0.8447
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8364
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8341
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8259
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8238
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8093
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 3 0.8080
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8059
Beta-elicitin cinnamomin P15569 ELIB_PHYCI Phytophthora cinnamomi 3 0.7991
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7989
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7985
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 CP11A_HUMAN Homo sapiens 3 0.7984
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7932
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.7910
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7908
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7906
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7903
Sodium/potassium-transporting ATPase subunit alpha Q4H132 Q4H132_SQUAC Squalus acanthias 3 0.7899
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7890
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7885
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7842
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7834
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7824
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7806
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7759
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7759
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7730
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7727
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7726
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7726
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7706
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7699
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7691
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7687
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7680
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7679
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7667
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7661
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7657
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7644
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7626
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7622
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7612
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7603
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7564
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7543
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7537
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7536
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7536
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7533
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7521
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7516
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7508
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7501
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7500
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7486
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7480
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7475
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7469
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7467
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7460
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7431
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7426
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7413
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7408
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7401
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7387
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7366
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7362
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7355
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 2 0.7354
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7351
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7348
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7348
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7347
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7347
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7347
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7335
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7331
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7321
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7308
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7302
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7294
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7291
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7289
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7288
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7276
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7269
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7263
Lactaldehyde dehydrogenase P25553 ALDA_ECOLI Escherichia coli 3 0.7261
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7258
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7257
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7256
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7253
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7209
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7204
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7198
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7194
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7191
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 2 0.7186
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7179
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7179
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7174
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7145
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7134
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7129
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7125
Predicted acetyltransferase Q97ML2 Q97ML2_CLOAB Clostridium acetobutylicum 3 0.7110
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7109
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7109
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7097
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.7091
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7075
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 2 0.7048
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7042
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7040
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7022
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7003
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7002

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