(3R)-8-hydroxylinalool - Compound Card

(3R)-8-hydroxylinalool

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(3R)-8-hydroxylinalool

Structure
Zoomed Structure
  • Family: Boraginaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Monoterpene
Canonical Smiles OC/C(=C/CC[C@](C=C)(O)C)/C
InChI InChI=1S/C10H18O2/c1-4-10(3,12)7-5-6-9(2)8-11/h4,6,11-12H,1,5,7-8H2,2-3H3/b9-6+/t10-/m0/s1
InChIKey NSMIMJYEKVSYMT-ZKXNXJMVSA-N
Formula C10H18O2
HBA 2
HBD 2
MW 170.25
Rotatable Bonds 5
TPSA 40.46
LogP 1.64
Number Rings 0
Number Aromatic Rings 0
Heavy Atom Count 12
Formal Charge 0
Fraction CSP3 0.6
Exact Mass 170.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Heliotropium bacciferum Boraginaceae Plantae 244092

Showing of synonyms

  • Aïssaoui H, Mencherini T, et al. (2019). Heliotropium bacciferum Forssk. (Boraginaceae) extracts: chemical constituents, antioxidant activity and cytotoxic effect in human cancer cell lines. Natural product research, 2019, 33(12), 1813-1818. [View] [PubMed]
Pubchem: 10678746

No compound-protein relationship available.

No scaffolds available.

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.45
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.57
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.08
Plasma Protein Binding
22.08
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
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
7.68
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.86
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.71
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
2.92
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
-1.6
Rat (Acute)
1.72
Rat (Chronic Oral)
1.86
Fathead Minnow
4.1
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
247.46
Hydration Free Energy
-7.58
Log(D) at pH=7.4
0.59
Log(P)
1.23
Log S
-1.12
Log(Vapor Pressure)
-2.7
Melting Point
36.44
pKa Acid
10.18
pKa Basic
6.21
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.9555
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9284
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9266
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9225
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9105
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.9045
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8961
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8956
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8948
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8941
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8935
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.8929
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8858
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8697
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8586
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8582
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.8576
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8452
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8336
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8282
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.8010
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7958
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7949
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7915
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.7909
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7895
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7859
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7845
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7837
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 2 0.7781
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7747
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7745
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7726
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7719
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7718
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7715
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7696
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7672
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7669
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7665
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7665
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7661
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7659
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7646
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7643
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7637
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7627
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7617
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7603
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7598
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7593
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7593
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7586
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7577
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7574
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7562
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7545
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7545
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7542
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7539
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7535
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7530
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7528
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7527
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7513
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 2 0.7510
Androgen receptor P19091 ANDR_MOUSE Mus musculus 3 0.7509
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7505
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7501
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7500
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7498
Gibberellin receptor GID1A Q9MAA7 GID1A_ARATH Arabidopsis thaliana 3 0.7497
Corticosteroid-binding globulin P31211 CBG_RAT Rattus norvegicus 3 0.7491
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7489
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7488
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7481
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7480
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7479
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7476
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7465
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7456
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7456
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7449
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7443
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7436
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7435
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7431
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7428
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 2 0.7427
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7421
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7412
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7411
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7407
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7407
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7392
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7391
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7391
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7385
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7385
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7384
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7377
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7366
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7365
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7364
Trichodiene synthase P13513 TRI5_FUSSP Fusarium sporotrichioides 2 0.7362
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7361
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7359
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7359
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7330
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7327
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7324
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7317
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7314
Aromatase P11511 CP19A_HUMAN Homo sapiens 2 0.7314
Androgen receptor O97775 ANDR_PANTR Pan troglodytes 3 0.7311
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7309
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7293
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7281
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7278
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7277
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 2 0.7276
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7257
Gibberellin receptor GID1 Q6L545 GID1_ORYSJ Oryza sativa subsp. japonica 3 0.7249
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7233
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7224
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7222
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7191
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7189
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7184
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7184
Cholesterol oxidase P22637 CHOD_BREST Brevibacterium sterolicum 3 0.7183
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7175
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7171
Vitamin D3 receptor A Q9PTN2 VDRA_DANRE Danio rerio 3 0.7156
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7140
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7121
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7113
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7108
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7094
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7091
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7083
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7080
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7059
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7058
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7041
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7028
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7027
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7005

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