3beta,6alpha-ditigloyloxy-5alpha,7-dihydroxy-8,9-dihydrolimonene - Compound Card

3beta,6alpha-ditigloyloxy-5alpha,7-dihydroxy-8,9-dihydrolimonene

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3beta,6alpha-ditigloyloxy-5alpha,7-dihydroxy-8,9-dihydrolimonene

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Monoterpene
Canonical Smiles OCC1=C[C@H](OC(=O)/C(=C/C)/C)[C@@H]([C@H]([C@H]1OC(=O)/C(=C/C)/C)OC(=O)C)C(C)C
InChI InChI=1S/C22H32O7/c1-8-13(5)21(25)28-17-10-16(11-23)19(29-22(26)14(6)9-2)20(27-15(7)24)18(17)12(3)4/h8-10,12,17-20,23H,11H2,1-7H3/b13-8+,14-9+/t17-,18-,19-,20+/m0/s1
InChIKey CUSTUSNKTKJKCL-VBCAGKPSSA-N
Formula C22H32O7
HBA 7
HBD 1
MW 408.49
Rotatable Bonds 7
TPSA 99.13
LogP 2.88
Number Rings 1
Number Aromatic Rings 0
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 408.21
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Sphaeranthus suaveolens Asteraceae Plantae 1548666

Showing of synonyms

  • Ahmed AA, Mahmoud AA (1997). Carvotacetone derivatives from the Egyptian plant Sphaeranthus suaveolens. Phytochemistry,1997,45(3),533-535. [View]
Pubchem: 101705718
Nmrshiftdb2: 70032258

No compound-protein relationship available.

Structure

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 408.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.57
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.61
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.35
Plasma Protein Binding
69.07
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
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.27
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.72
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.36
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-4.92
Rat (Acute)
2.4
Rat (Chronic Oral)
2.31
Fathead Minnow
4.7
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
362.67
Hydration Free Energy
-6.62
Log(D) at pH=7.4
2.63
Log(P)
3.96
Log S
-4.56
Log(Vapor Pressure)
-6.8
Melting Point
113.63
pKa Acid
9.83
pKa Basic
3.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8860
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8860
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7730
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7730
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7517
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7517
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7502
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7502
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7442
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7442
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7441
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 4 0.7441
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7404
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7404
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7266
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7266
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7083
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7083

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