19-acetoxy 14,16–14,20–15,20 triepoxy-14,15 secopregn-5-en-3,19 diol-3-O-beta-D-oleandropyranosyl-(1→4)-beta-D-canaropyranosyl-(1 → 4)-beta-D-cymaropyranosyl-(1 → 4)-beta-D-cymaropyranoside - Compound Card

19-acetoxy 14,16–14,20–15,20 triepoxy-14,15 secopregn-5-en-3,19 diol-3-O-beta-D-oleandropyranosyl-(1→4)-beta-D-canaropyranosyl-(1 → 4)-beta-D-cymaropyranosyl-(1 → 4)-beta-D-cymaropyranoside

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19-acetoxy 14,16–14,20–15,20 triepoxy-14,15 secopregn-5-en-3,19 diol-3-O-beta-D-oleandropyranosyl-(1→4)-beta-D-canaropyranosyl-(1 → 4)-beta-D-cymaropyranosyl-(1 → 4)-beta-D-cymaropyranoside

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Steroid
    • Subclass: Pregnane Glycoside
Canonical Smiles COC1CC(O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3CC[C@]3([C@@]54O[C@H]4[C@@H]3[C@](O5)(C)OC4)C)C2)COC(=O)C)OC(C1OC1CC(OC)C(C(O1)C)OC1CC(O)C(C(O1)C)OC1CC(OC)C(C(O1)C)O)C
InChI InChI=1S/C50H78O18/c1-24-42(53)34(54-8)19-40(59-24)64-43-25(2)60-38(18-33(43)52)65-44-27(4)62-41(21-36(44)56-10)66-45-26(3)61-39(20-35(45)55-9)63-30-13-16-49(23-57-28(5)51)29(17-30)11-12-32-31(49)14-15-47(6)46-37-22-58-48(46,7)68-50(32,47)67-37/h11,24-27,30-46,52-53H,12-23H2,1-10H3/t24?,25?,26?,27?,30-,31-,32+,33?,34?,35?,36?,37+,38?,39?,40?,41?,42?,43?,44?,45?,46-,47+,48+,49+,50-/m0/s1
InChIKey MOQLFQSZEMDZMA-BDYRIGDRSA-N
Formula C50H78O18
HBA 18
HBD 2
MW 967.16
Rotatable Bonds 13
TPSA 195.98
LogP 4.42
Number Rings 10
Number Aromatic Rings 0
Heavy Atom Count 68
Formal Charge 0
Fraction CSP3 0.94
Exact Mass 966.52
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Solenostemma argel Apocynaceae Plantae 219273

Showing of synonyms

  • Ounaissia K, Pertuit D, et al. (2016). New pregnane and phenolic glycosides from Solenostemma argel. Fitoterapia, 2016, 114, 98-104. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1C2OCC(O3)C2C(C134)CCC5C4CC=C6C5CCC(C6)OC(OC7)CCC7OC(OC8)CCC8OC(OC9)CCC9OC1CCCCO1

Level: 4

Mol. Weight: 967.16 g/mol

Structure

SMILES: O1C2OCC(O3)C2C(C134)CCC5C4CC=C6C5CCC(C6)OC(OC7)CCC7OC(OC8)CCC8OC9CCCCO9

Level: 3

Mol. Weight: 967.16 g/mol

Structure

SMILES: C1OCCCC1OC(OC2)CCC2OC(OC3)CCC3OC4CCCCO4

Level: 3

Mol. Weight: 967.16 g/mol

Structure

SMILES: O1C2OCC(O3)C2C(C134)CCC5C4CC=C6C5CCC(C6)OC(OC7)CCC7OC8CCCCO8

Level: 2

Mol. Weight: 967.16 g/mol

Structure

SMILES: O1CCCCC1OC2CCC(OC2)OC3CCCOC3

Level: 2

Mol. Weight: 967.16 g/mol

Structure

SMILES: O1C2OCC(O3)C2C(C134)CCC5C4CC=C6C5CCC(C6)OC7CCCCO7

Level: 1

Mol. Weight: 967.16 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 967.16 g/mol

Structure

SMILES: O1C2OCC(O3)C2C(C134)CCC5C4CC=C6C5CCCC6

Level: 0

Mol. Weight: 967.16 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 967.16 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.47
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
26141.170
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
3417078.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.380
Plasma Protein Binding
74.35
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
Inhibitor
OATP1B3
Inhibitor

Excretion

Clearance
3.850
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Toxic
Bee
Toxic
Bioconcentration Factor
-79475.840
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.440
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
4.050
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
Toxic
T. Pyriformis
-6201835041.270
Rat (Acute)
5.240
Rat (Chronic Oral)
14.750
Fathead Minnow
7828496.130
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
697532276.380
Hydration Free Energy
-2.920
Log(D) at pH=7.4
-368.780
Log(P)
4.36
Log S
-6.17
Log(Vapor Pressure)
-22969264.27
Melting Point
157.74
pKa Acid
-167284.88
pKa Basic
-1326.45
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8355
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8268
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7391
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7349
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7346
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7335
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7041
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7030

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