Hexanocucurbitacin I 2-O-beta-D-glucopyranoside - Compound Card

Hexanocucurbitacin I 2-O-beta-D-glucopyranoside

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Hexanocucurbitacin I 2-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Cucurbitaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavone
Canonical Smiles OCC1OC(OC2=C[C@@H]3C(=CCC4[C@@]3(C)C(=O)C[C@]3([C@@]4(C)C[C@H]([C@@H]3C(=O)C)O)C)C(C2=O)(C)C)C(C(C1O)O)O
InChI InChI=1S/C30H42O10/c1-13(32)21-16(33)10-28(4)19-8-7-14-15(30(19,6)20(34)11-29(21,28)5)9-17(25(38)27(14,2)3)39-26-24(37)23(36)22(35)18(12-31)40-26/h7,9,15-16,18-19,21-24,26,31,33,35-37H,8,10-12H2,1-6H3/t15-,16-,18?,19?,21+,22?,23?,24?,26?,28+,29-,30+/m1/s1
InChIKey ZRNZYSQTUUUEOQ-FAVZMQCRSA-N
Formula C30H42O10
HBA 10
HBD 5
MW 562.66
Rotatable Bonds 4
TPSA 170.82
LogP 0.82
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 562.28
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Citrullus colocynthis Cucurbitaceae Plantae 252529

Showing of synonyms

  • Yoshikawa M, Morikawa T, et al. (2007). Bioactive Saponins and Glycosides. XXVII. 1) Structures of New Cucurbitane-Type Triterpene Glycosides and Antiallergic Constituents from Citrullus colocynthis. Chemical & pharmaceutical bulletin, 2007, 55(3), 428-34. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3C=C(C(=O)C4)OC5CCCCO5

Level: 1

Mol. Weight: 562.66 g/mol

Structure

SMILES: C1CCC(C12)CC(=O)C3C2CC=C4C3C=CC(=O)C4

Level: 0

Mol. Weight: 562.66 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 562.66 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.66
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.92
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.88
Plasma Protein Binding
93.84
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.88
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.2
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.74
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.68
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-2139.88
Rat (Acute)
4.15
Rat (Chronic Oral)
3.49
Fathead Minnow
6.95
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
478.39
Hydration Free Energy
-2.88
Log(D) at pH=7.4
2.19
Log(P)
0.36
Log S
-3.12
Log(Vapor Pressure)
-10.8
Melting Point
242.57
pKa Acid
4.48
pKa Basic
2.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8855
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8432
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7920
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7539
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7364
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7326
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7252

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