16-O-(4-O-acetyl)-alpha-L-arabinopyranosyl-20-O-beta-D-glucopyranosyl-6alpha,16alpha,20beta,21alpha-tetrahydroxytetrahymanol - Compound Card

16-O-(4-O-acetyl)-alpha-L-arabinopyranosyl-20-O-beta-D-glucopyranosyl-6alpha,16alpha,20beta,21alpha-tetrahydroxytetrahymanol

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16-O-(4-O-acetyl)-alpha-L-arabinopyranosyl-20-O-beta-D-glucopyranosyl-6alpha,16alpha,20beta,21alpha-tetrahydroxytetrahymanol

Structure
Zoomed Structure
  • Family: Plantae - Caryophyllaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene Glycoside
Canonical Smiles OC[C@H]1OC(O[C@@H]2CC3[C@H](C([C@H]2O)(C)C)[C@H](OC2OC[C@H]([C@H]([C@@H]2O)O)OC(=O)C)C[C@@]2([C@@H]3CC[C@H]3[C@@]2(C)C[C@@H](C2[C@]3(C)CC[C@@H](C2(C)C)O)O)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C42H70O15/c1-18(44)54-25-17-53-36(32(50)30(25)48)56-23-15-41(7)20(9-10-26-40(6)12-11-27(46)38(2,3)34(40)21(45)14-42(26,41)8)19-13-22(35(52)39(4,5)28(19)23)55-37-33(51)31(49)29(47)24(16-43)57-37/h19-37,43,45-52H,9-17H2,1-8H3/t19?,20-,21+,22-,23-,24-,25-,26-,27+,28+,29-,30-,31+,32+,33-,34?,35+,36?,37?,40-,41-,42-/m1/s1
InChIKey UZWOZRDFWPXGSK-FZKONZGJSA-N
Formula C42H70O15
HBA 15
HBD 9
MW 815.01
Rotatable Bonds 6
TPSA 245.29
LogP 0.6
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 57
Formal Charge 0
Fraction CSP3 0.98
Exact Mass 814.47
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Spergula fallax Caryophyllaceae Plantae 1423401

Showing of synonyms

  • Hamed AI, Masullo M, et al. (2014). Unusual fernane and gammacerane glycosides from the aerial parts of Spergula fallax. Journal of Natural Products,2014,77(3),657-662. [View] [PubMed]
Pubchem: 162817394
Nmrshiftdb2: 70085815

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(C2)CCC(C(C3)OC4CCCCO4)C2C(C35)CCC6C5CCC7C6CCCC7

Level: 2

Mol. Weight: 815.01 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(C2C34)CCC3C5C(CCCC5)C(C4)OC6CCCCO6

Level: 1

Mol. Weight: 815.01 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(C2C34)CCC3C5C(CC4)CCC(C5)OC6CCCCO6

Level: 1

Mol. Weight: 815.01 g/mol

Structure

SMILES: C1CCCC(CC2)C1C(C2C34)CCC3C5C(CC4)CCCC5

Level: 0

Mol. Weight: 815.01 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 815.01 g/mol

Anticancer

Absorption

Caco-2 (logPapp)
-6.45
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
24.14
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
3926.69

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
91.38
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
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
Non-Inhibitor

Excretion

Clearance
0.23
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-95.06
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.11
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.9
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-7128218.55
Rat (Acute)
4.47
Rat (Chronic Oral)
3.79
Fathead Minnow
9003.93
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
798467.81
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.48
Log(P)
2.07
Log S
-2.74
Log(Vapor Pressure)
-26158.87
Melting Point
258.94
pKa Acid
-139.49
pKa Basic
6.39
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 0.9019
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9019
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7976
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.7976
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 4 0.7740
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 4 0.7740
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7699
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7699

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