(1R*,2R*,3E,7R*,8S*,9R*,11R*,12S*)-16-O-(3-hydroxy-3- methylglutaryl)-8,9-epoxydolabell-3-en-2,7,16,18-tetrol - Compound Card

(1R*,2R*,3E,7R*,8S*,9R*,11R*,12S*)-16-O-(3-hydroxy-3- methylglutaryl)-8,9-epoxydolabell-3-en-2,7,16,18-tetrol

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(1R*,2R*,3E,7R*,8S*,9R*,11R*,12S*)-16-O-(3-hydroxy-3- methylglutaryl)-8,9-epoxydolabell-3-en-2,7,16,18-tetrol

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpenoid
Canonical Smiles OC(=O)C[C@@](CC(=O)OC/C/1=C\[C@H](O)[C@@]2(C)CC[C@H]([C@@H]2C[C@@H]2[C@]([C@@H](CC1)O)(C)O2)C(O)(C)C)(O)C
InChI InChI=1S/C26H42O9/c1-23(2,32)16-8-9-25(4)17(16)11-20-26(5,35-20)18(27)7-6-15(10-19(25)28)14-34-22(31)13-24(3,33)12-21(29)30/h10,16-20,27-28,32-33H,6-9,11-14H2,1-5H3,(H,29,30)/b15-10-/t16-,17+,18-,19+,20-,24+,25+,26-/m1/s1
InChIKey OFJYPZDJODKQBK-XKCRYQAQSA-N
Formula C26H42O9
HBA 8
HBD 5
MW 498.61
Rotatable Bonds 7
TPSA 157.05
LogP 1.94
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.85
Exact Mass 498.28
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chrozophora obliqua Euphorbiaceae Plantae 316753

Showing of synonyms

  • Mohamed KM, Ohtani K, et al. (1995). 3-Hydroxy-3-methylglutaryl dolabellane diterpenes from Chrozophora obliqua. Phytochemistry,1995,39(1),151-161. [View]
Pubchem: 163002793

No compound-protein relationship available.

Structure

SMILES: C12C(O2)CCCC=CCC3C(C1)CCC3

Level: 0

Mol. Weight: 498.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.7
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.07
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.78

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.69
Plasma Protein Binding
54.64
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
Non-Inhibitor

Excretion

Clearance
11.86
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.9
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.04
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
3.99
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
-123.63
Rat (Acute)
2.86
Rat (Chronic Oral)
2.54
Fathead Minnow
3.88
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
495.67
Hydration Free Energy
-2.6
Log(D) at pH=7.4
-1.4
Log(P)
0.98
Log S
-2.85
Log(Vapor Pressure)
-11.27
Melting Point
144.95
pKa Acid
3.08
pKa Basic
5.96
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9365
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9365
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8455
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8455
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8442
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8442
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8383
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8383
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7869
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7869
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7789
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7789
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7444
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7444
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7309
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7309
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7287
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7287
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7273
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7273
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7229
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7229

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