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

16-O-alpha-L-arabinopyranosyl-20-O-beta-D-glucopyranosyl-6alpha,16alpha,20beta,21alpha-tetrahydroxytetrahymanol

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16-O-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]4CC[C@H]5[C@@]([C@]4(C)C[C@H]([C@H]3C([C@H]2O)(C)C)OC2OC[C@H]([C@H]([C@@H]2O)O)O)(C)C[C@@H](C2[C@]5(C)CC[C@@H](C2(C)C)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C40H68O14/c1-36(2)25(44)10-11-38(5)24-9-8-18-17-12-21(52-35-31(49)29(47)28(46)23(15-41)54-35)33(50)37(3,4)26(17)22(53-34-30(48)27(45)20(43)16-51-34)14-39(18,6)40(24,7)13-19(42)32(36)38/h17-35,41-50H,8-16H2,1-7H3/t17?,18-,19+,20-,21-,22-,23-,24-,25+,26+,27-,28-,29+,30+,31-,32?,33+,34?,35?,38-,39-,40-/m1/s1
InChIKey NFVZLFIQCMHYIF-FXBGQQRRSA-N
Formula C40H68O14
HBA 14
HBD 10
MW 772.97
Rotatable Bonds 5
TPSA 239.22
LogP 0.03
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 54
Formal Charge 0
Fraction CSP3 1.0
Exact Mass 772.46
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: 162975267
Nmrshiftdb2: 70085814

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 772.97 g/mol

Structure

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

Level: 1

Mol. Weight: 772.97 g/mol

Structure

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

Level: 1

Mol. Weight: 772.97 g/mol

Structure

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

Level: 0

Mol. Weight: 772.97 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 772.97 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.46
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
2.2
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1058.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.75
Plasma Protein Binding
88.65
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
0.07
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-24.81
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.84
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.12
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
-1921818.58
Rat (Acute)
4.25
Rat (Chronic Oral)
3.98
Fathead Minnow
2432.03
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
213194.82
Hydration Free Energy
-2.92
Log(D) at pH=7.4
3.22
Log(P)
1.46
Log S
-2.69
Log(Vapor Pressure)
-6893.8
Melting Point
267.0
pKa Acid
-12.42
pKa Basic
6.92
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 0.8196
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8196
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7763
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7763
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7237
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7237
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7205
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7205

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