(R)-3,6-dihydro-6-((S)-1-((2S,5R)-tetrahydro-5-methyl-5-vinylfuran-2-yl)ethyl)-3,3-dimethyl-1,2-dioxine - Compound Card

(R)-3,6-dihydro-6-((S)-1-((2S,5R)-tetrahydro-5-methyl-5-vinylfuran-2-yl)ethyl)-3,3-dimethyl-1,2-dioxine

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(R)-3,6-dihydro-6-((S)-1-((2S,5R)-tetrahydro-5-methyl-5-vinylfuran-2-yl)ethyl)-3,3-dimethyl-1,2-dioxine

Structure
Zoomed Structure
  • Family: Asteraceae-Compositae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles C=C[C@]1(C)CC[C@@H](O1)C(C1OOC(C=C1)(C)C)C
InChI InChI=1S/C15H24O3/c1-6-15(5)10-8-12(16-15)11(2)13-7-9-14(3,4)18-17-13/h6-7,9,11-13H,1,8,10H2,2-5H3/t11?,12-,13?,15-/m1/s1
InChIKey RXXCFDMFXFGCML-HNQLUHSGSA-N
Formula C15H24O3
HBA 3
HBD 0
MW 252.35
Rotatable Bonds 3
TPSA 27.69
LogP 3.41
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 18
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 252.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pyrethrum santolinoides Asteraceae-Compositae Plantae 2072400

Showing of synonyms

  • Mahmoud AA, Ahmed AA, et al. (1994). 2,3-secogermacranolides and germacranolides from Pyrethrum santolionoides. Phytochemistry,1994,36(2),393-398. [View]
Pubchem: 163042006

No compound-protein relationship available.

Structure

SMILES: O1CCCC1CC2C=CCOO2

Level: 1

Mol. Weight: 170.21 g/mol

Structure

SMILES: C1=CCOOC1

Level: 0

Mol. Weight: 86.09 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 72.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.6
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.23
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.63

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.48
Plasma Protein Binding
32.98
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
12.8
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.58
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.23
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.23
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
-1.4
Rat (Acute)
2.74
Rat (Chronic Oral)
1.24
Fathead Minnow
3.8
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
263.38
Hydration Free Energy
-3.46
Log(D) at pH=7.4
2.71
Log(P)
4.02
Log S
-3.39
Log(Vapor Pressure)
-1.89
Melting Point
-1.04
pKa Acid
9.63
pKa Basic
4.78
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9519
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9519
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.9315
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.9315
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9150
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.9150
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.9014
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.9014
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8879
Retinol-binding protein 2 P50120 RET2_HUMAN Homo sapiens 3 0.8879
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8701
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.8701
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8678
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8678
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8657
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8657
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8489
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.8489
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8417
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8417
Hemolymph juvenile hormone binding protein Q9U556 Q9U556_BOMMO Bombyx mori 4 0.8363
Hemolymph juvenile hormone binding protein Q9U556 Q9U556_BOMMO Bombyx mori 4 0.8363
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8290
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8290
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8115
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.8115
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7970
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7970
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7885
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7885
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7827
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7827
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7826
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7826
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7820
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7820
Retinoic acid receptor gamma P13631 RARG_HUMAN Homo sapiens 3 0.7818
Retinoic acid receptor gamma P13631 RARG_HUMAN Homo sapiens 3 0.7818
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7785
Retinoic acid receptor RXR Q8T5C6 RXR_BIOGL Biomphalaria glabrata 3 0.7785
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7718
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7718
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7703
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7703
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7703
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7703
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7691
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7691
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7622
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7622
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7619
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7619
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7616
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7616
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7599
Retinaldehyde-binding protein 1 P12271 RLBP1_HUMAN Homo sapiens 3 0.7599
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7570
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7570
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7570
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7570
Bile acid receptor Q62735 NR1H4_RAT Rattus norvegicus 4 0.7545
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7545
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7545
Bile acid receptor Q62735 NR1H4_RAT Rattus norvegicus 4 0.7545
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7540
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7540
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7529
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7529
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7522
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7522
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7518
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7518
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7510
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7510
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7479
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7479
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7463
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7463
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7447
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7447
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7426
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7426
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7407
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7407
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7331
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7331
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7309
Beta-elicitin cryptogein P15570 ELIB_PHYCR Phytophthora cryptogea 3 0.7309
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7300
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7300
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7275
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7275
Cartilage oligomeric matrix protein P35444 COMP_RAT Rattus norvegicus 3 0.7245
Cartilage oligomeric matrix protein P35444 COMP_RAT Rattus norvegicus 3 0.7245
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7236
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7236
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7202
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7202
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7200
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7200
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7200
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7200
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.7154
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.7154
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7137
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7137
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7130
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7130
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7091
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7091
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7088
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7088
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7076
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7076
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7071
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.7071
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7039
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7039
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7037
Vitamin D3 receptor P13053 VDR_RAT Rattus norvegicus 3 0.7037

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