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

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

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(1R*,2R*,3E,7R*,8S*,9R*,11R*,12S*)-2-O-acetyl-16-O-(3-hydroxy-3-methylgiutaryl)-8,9-epoxydolabeli-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](OC(=O)C)[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/C28H44O10/c1-16(29)37-21-11-17(15-36-24(33)14-26(4,35)13-23(31)32)7-8-20(30)28(6)22(38-28)12-19-18(25(2,3)34)9-10-27(19,21)5/h11,18-22,30,34-35H,7-10,12-15H2,1-6H3,(H,31,32)/b17-11-/t18-,19+,20-,21-,22-,26-,27+,28-/m1/s1
InChIKey YTCUGHMXPWVBIQ-QCHLLHSISA-N
Formula C28H44O10
HBA 9
HBD 4
MW 540.65
Rotatable Bonds 8
TPSA 163.12
LogP 2.51
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.82
Exact Mass 540.29
Number of Lipinski Rule Violations 1
# 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: 163013062

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 540.65 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.59
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.95
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
56.63
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
12.21
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.65
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.36
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.67
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
-463.43
Rat (Acute)
2.93
Rat (Chronic Oral)
2.61
Fathead Minnow
3.79
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
494.88
Hydration Free Energy
-3.18
Log(D) at pH=7.4
-1.03
Log(P)
1.27
Log S
-3.49
Log(Vapor Pressure)
-10.79
Melting Point
153.71
pKa Acid
3.67
pKa Basic
5.43
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 0.9495
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9495
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8717
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8717
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8352
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8352
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 3 0.8069
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 3 0.8069
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.8064
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.8064
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7991
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7991
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7903
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7903
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7730
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 4 0.7730
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7699
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7699
3-hydroxy-3-methylglutaryl-coenzyme A reductase P13702 MVAA_PSEMV Pseudomonas mevalonii 3 0.7328
3-hydroxy-3-methylglutaryl-coenzyme A reductase P13702 MVAA_PSEMV Pseudomonas mevalonii 3 0.7328
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7309
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.7309
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7291
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7291
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7248
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7248
N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) Q91XE4 ACY3_MOUSE Mus musculus 3 0.7130
N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) Q91XE4 ACY3_MOUSE Mus musculus 3 0.7130
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7122
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7122
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7039
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7039

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