1,2-dehydro-1,10a-dihydropseudoivalin - Compound Card

1,2-dehydro-1,10a-dihydropseudoivalin

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1,2-dehydro-1,10a-dihydropseudoivalin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene
Canonical Smiles O=C[C@]1(O)CCC[C@]2([C@]1(O)C[C@@H](CC2)C(=C)C(=O)O)C
InChI InChI=1S/C15H22O5/c1-10(12(17)18)11-4-7-13(2)5-3-6-14(19,9-16)15(13,20)8-11/h9,11,19-20H,1,3-8H2,2H3,(H,17,18)/t11-,13-,14-,15-/m1/s1
InChIKey IITYBZWPSVSQLZ-NMFUWQPSSA-N
Formula C15H22O5
HBA 4
HBD 3
MW 282.34
Rotatable Bonds 3
TPSA 94.83
LogP 1.28
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 282.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria undulata Asteraceae Plantae 119186
2 Pluchea dioscoridis Asteraceae Plantae —

Showing of synonyms

  • Mahmoud AA (1997). 7-Epi-eudesmanes, eudesmanoic acids, eudesmanolides and other sesquiterpenenes from Pluchea dioscoridis. Phytochemistry,1997,45(8),1633-1638. [View]
  • Hegazy MEF, Nakamura S, et al. (2015). Rare hydroperoxyl guaianolide sesquiterpenes from Pulicaria undulata. Phytochemistry Letters,2015,12,177-181. [View]
Pubchem: 101713145
Nmrshiftdb2: 60045966

No compound-protein relationship available.

Structure

SMILES: C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 282.34 g/mol

Anti-inflammatory

Absorption

Caco-2 (logPapp)
-4.99
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.69
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.61

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.32
Plasma Protein Binding
48.85
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.51
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.09
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.63
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.56
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Toxic
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-0.7
Rat (Acute)
2.21
Rat (Chronic Oral)
2.18
Fathead Minnow
3.98
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
341.05
Hydration Free Energy
-12.14
Log(D) at pH=7.4
-0.5
Log(P)
1.54
Log S
-1.76
Log(Vapor Pressure)
-8.12
Melting Point
164.75
pKa Acid
3.45
pKa Basic
7.84
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 0.8768
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8768
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8516
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8516
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8262
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.8262
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8220
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8220
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7767
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7767
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7737
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7737
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7383
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7383
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7328
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7328
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7154
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7154
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7109
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7109
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7031
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7031

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