(1S,7S)-1-((2R,3S,5S)-tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-carboxylic acid - Compound Card

(1S,7S)-1-((2R,3S,5S)-tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-carboxylic acid

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(1S,7S)-1-((2R,3S,5S)-tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-yloxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-carboxylic acid

Structure
Zoomed Structure
  • Family: Plantae - Acanthaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Iridoid Glycoside
Canonical Smiles C=C1[C@@H]2CC[C@@H]3[C@]([C@H]1O)(C2)CC[C@H]1[C@@]3(C)CCC[C@@]1(C)C(=O)O
InChI InChI=1S/C20H30O3/c1-12-13-5-6-15-18(2)8-4-9-19(3,17(22)23)14(18)7-10-20(15,11-13)16(12)21/h13-16,21H,1,4-11H2,2-3H3,(H,22,23)/t13-,14+,15+,16+,18-,19-,20-/m1/s1
InChIKey GVGJRXSJJHLPGZ-DZAVYMGKSA-N
Formula C20H30O3
HBA 2
HBD 2
MW 318.46
Rotatable Bonds 1
TPSA 57.53
LogP 4.01
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 318.22
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Thunbergia grandiflora Acanthaceae Plantae 504049

Showing of synonyms

  • Ismail LD, El-Azlzi MM, et al. (1996). Iridoid glycosides from Thunbergia grandiflora. Phytochemistry,1996,42(4),1223-1225. [View] [PubMed]
Pubchem: 159930
Chebi: 141145
Nmrshiftdb2: 60018845

No compound-protein relationship available.

Structure

SMILES: C=C(C1)C(C2)CCC(C123)C4C(CC3)CCCC4

Level: 0

Mol. Weight: 318.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.62
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.14
Plasma Protein Binding
80.71
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
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.99
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.61
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
-0.12
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
3.36
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-3.17
Rat (Acute)
2.4
Rat (Chronic Oral)
2.05
Fathead Minnow
3.84
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
396.48
Hydration Free Energy
-4.01
Log(D) at pH=7.4
1.39
Log(P)
3.52
Log S
-4.65
Log(Vapor Pressure)
-8.26
Melting Point
208.25
pKa Acid
4.49
pKa Basic
8.04
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8772
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8772
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.8407
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.8407
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8368
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8368
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7674
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7674
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7595
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7595
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7323
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7323
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7012
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7012

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