Rel (lR, 4S, 6R)-p-menthane-3,6-diol - Compound Card

Rel (lR, 4S, 6R)-p-menthane-3,6-diol

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Rel (lR, 4S, 6R)-p-menthane-3,6-diol

Structure
Zoomed Structure
  • Family: Apiaceae, Moraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Monoterpene
Canonical Smiles CC([C@H]1C[C@@H](O)C(=C[C@@H]1O)C)C
InChI InChI=1S/C10H18O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4,6,8-12H,5H2,1-3H3/t8-,9-,10+/m1/s1
InChIKey CDEBGVXOFDWUAF-BBBLOLIVSA-N
Formula C10H18O2
HBA 2
HBD 2
MW 170.25
Rotatable Bonds 1
TPSA 40.46
LogP 1.33
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 12
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 170.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Foeniculum vulgare Apiaceae Plantae 2849586
2 Ficus thonningii Moraceae Plantae 309310

Showing of synonyms

  • Zellagui A, Gherraf N, et al. (2011). Chemical constituents from Algerian Foeniculum vulgare aerial parts and evaluation of antimicrobial activity. Journal of the Chilean Chemical Society,2011,56(3),759-763. [View]
  • Fongang Y, Bankeu J, et al. (2015). Flavonoids and other bioactive constituents from Ficus thonningii Blume (Moraceae). Phytochemistry Letters, 2015, 11, 139-145. [View]
Pubchem: 124355567
Nmrshiftdb2: 70033889

No compound-protein relationship available.

Structure

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 82.15 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.59
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.9

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.22
Plasma Protein Binding
29.42
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
7.77
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
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.66
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
2.77
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
0.06
Rat (Acute)
1.81
Rat (Chronic Oral)
1.97
Fathead Minnow
3.25
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
263.47
Hydration Free Energy
-8.02
Log(D) at pH=7.4
0.86
Log(P)
1.71
Log S
-1.3
Log(Vapor Pressure)
-2.76
Melting Point
73.27
pKa Acid
10.22
pKa Basic
5.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8872
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.8872
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8844
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8844
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8750
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8750
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8405
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8405
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8350
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8350
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8316
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8316
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8061
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8061
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8022
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8022
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7967
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7967
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7911
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7911
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7902
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7902
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7894
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7894
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7824
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7824
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7811
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7811
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7732
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7732
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7706
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7706
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7666
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7666
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7644
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7644
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7614
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7614
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7595
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7595
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7580
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7580
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7578
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7578
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7577
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 2 0.7577
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7553
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7553
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7539
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7539
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7538
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7538
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7526
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7526
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7469
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7469
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7403
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7403
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7401
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7401
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7395
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7395
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7389
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7389
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7384
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7384
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7365
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7365
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7363
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7363
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7353
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7353
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7350
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7350
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7347
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7347
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7323
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 2 0.7323
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7311
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7311
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7304
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7304
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7300
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7300
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7278
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7278
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7277
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7277
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7246
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 2 0.7246
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7217
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7217
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7212
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7212
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7207
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7207
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7202
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7202
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7202
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7202
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7166
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7166
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7124
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7124
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7120
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7120
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7113
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 2 0.7113
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7109
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7109
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7097
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7097
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7072
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7072
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7045
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7045
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7010
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7010
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7003
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7003

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