Alpha-eudesmol-(alpha-xylopyranoside-triacetate) - Compound Card

Alpha-eudesmol-(alpha-xylopyranoside-triacetate)

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Alpha-eudesmol-(alpha-xylopyranoside-triacetate)

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Sesquiterpene Glycoside
Canonical Smiles CC(=O)C[C@H]1C(OC[C@H]([C@@H]1CC(=O)C)CC(=O)C)OC([C@@H]1CC[C@@]2([C@@H](C1)C(=CCC2)C)C)(C)C
InChI InChI=1S/C29H46O5/c1-18-9-8-11-29(7)12-10-23(16-26(18)29)28(5,6)34-27-25(15-21(4)32)24(14-20(3)31)22(17-33-27)13-19(2)30/h9,22-27H,8,10-17H2,1-7H3/t22-,23-,24+,25-,26+,27?,29-/m1/s1
InChIKey ZBPRCHQHMTWQGF-HIFMHDRMSA-N
Formula C29H46O5
HBA 5
HBD 0
MW 474.68
Rotatable Bonds 9
TPSA 69.67
LogP 6.09
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.83
Exact Mass 474.33
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Iphiona scabra Asteraceae Plantae 211591

Showing of synonyms

  • Aedel-Mogib M, Jakupovic J, et al. (1989). 10-epi-cubebolxyloside from Iphiona scabra. Phytochemistry,1989,28(8),2202-2203. [View]
Pubchem: 162912845
Nmrshiftdb2: 70003177

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCC(C2)CCC(C23)CCC=C3

Level: 1

Mol. Weight: 474.68 g/mol

Structure

SMILES: C1=CCCC(C12)CCCC2

Level: 0

Mol. Weight: 474.68 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 474.68 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.21

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.38
Plasma Protein Binding
87.98
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
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
13.12
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.06
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.43
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.06
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-89.66
Rat (Acute)
2.4
Rat (Chronic Oral)
1.75
Fathead Minnow
4.12
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
477.61
Hydration Free Energy
-2.38
Log(D) at pH=7.4
4.28
Log(P)
5.22
Log S
-5.29
Log(Vapor Pressure)
-7.66
Melting Point
99.34
pKa Acid
8.81
pKa Basic
0.86
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9073
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9073
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8540
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8540
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8438
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8438
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7994
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7994
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7861
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7861
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7842
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7842
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7674
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7674
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7582
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7582
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7442
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7442
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7397
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7397
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7336
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7336
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7271
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7271
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7240
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7240
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7235
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7235
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7203
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7203
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7189
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7189
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7189
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7189
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7158
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7158
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7125
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7125
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7117
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7117
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7110
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7110
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7105
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7105
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7078
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7078
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7069
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7069
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7062
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7062
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7048
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7048

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