Pregn-5-ene-3,14-beta-dihydroxy-7,20-dione 3-O-beta-glucopyranoside - Compound Card

Pregn-5-ene-3,14-beta-dihydroxy-7,20-dione 3-O-beta-glucopyranoside

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Pregn-5-ene-3,14-beta-dihydroxy-7,20-dione 3-O-beta-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Pregnane Glycoside
Canonical Smiles OCC1O[C@@](O)(O[C@H]2CCC3(C(=CC(=O)C4C3CCC3([C@]4(O)CC[C@H]3C(=O)C)C)C2)C)[C@H](C([C@@H]1O)O)O
InChI InChI=1S/C27H40O10/c1-13(29)16-6-9-26(34)20-17(5-8-25(16,26)3)24(2)7-4-15(10-14(24)11-18(20)30)36-27(35)23(33)22(32)21(31)19(12-28)37-27/h11,15-17,19-23,28,31-35H,4-10,12H2,1-3H3/t15-,16-,17?,19?,20?,21+,22?,23-,24?,25?,26-,27-/m0/s1
InChIKey VYJAFDVONWEVMX-PTEHHMTLSA-N
Formula C27H40O10
HBA 10
HBD 6
MW 524.61
Rotatable Bonds 4
TPSA 173.98
LogP -0.05
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 524.26
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Solenostemma argel Apocynaceae Plantae 219273

Showing of synonyms

  • Kamel MS, Ohtani K, et al. (2000). Monoterpene and pregnane glucosides from Solenostemma argel. Phytochemistry,2000,53(8),937-940. [View] [PubMed]
Pubchem: 162817502
Nmrshiftdb2: 70086612

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC3C2C(=O)C=C4C3CCC(C4)OC5CCCCO5

Level: 1

Mol. Weight: 524.61 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2C(=O)C=C4C3CCCC4

Level: 0

Mol. Weight: 524.61 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 524.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.23
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.18
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.16

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
71.71
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
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
-0.15
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.98
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
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
4.86
Micronucleos
Toxic
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
-697.94
Rat (Acute)
3.93
Rat (Chronic Oral)
3.23
Fathead Minnow
3.24
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
529.23
Hydration Free Energy
-3.0
Log(D) at pH=7.4
0.9
Log(P)
-0.56
Log S
-1.98
Log(Vapor Pressure)
-13.67
Melting Point
204.33
pKa Acid
4.63
pKa Basic
7.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9002
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9002
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7692
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7692
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7488
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7488
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7247
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7247
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7224
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.7224
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7214
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7214
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7155
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7155
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7121
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7121
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7104
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7104
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7046
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7046
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7030
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7030

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