(1R*,2R*,3E,7E,11R*,12S*)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,7-dien-2,16,18-triol - Compound Card

(1R*,2R*,3E,7E,11R*,12S*)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,7-dien-2,16,18-triol

Select a section from the left sidebar

(1R*,2R*,3E,7E,11R*,12S*)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,7-dien-2,16,18-triol

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]2CC/C(=C/CC1)/C)C(O)(C)C)(O)C
InChI InChI=1S/C28H44O8/c1-18-8-7-9-20(17-35-25(32)16-27(5,34)15-24(30)31)14-23(36-19(2)29)28(6)13-12-21(26(3,4)33)22(28)11-10-18/h8,14,21-23,33-34H,7,9-13,15-17H2,1-6H3,(H,30,31)/b18-8+,20-14-/t21-,22+,23-,27+,28+/m1/s1
InChIKey XCJIFDKCCHFANV-XHEJPGTASA-N
Formula C28H44O8
HBA 7
HBD 3
MW 508.65
Rotatable Bonds 8
TPSA 130.36
LogP 4.33
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 36
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 508.3
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: 162892434

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC=CCCC=CC2

Level: 0

Mol. Weight: 508.65 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.74
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.04
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.86
Plasma Protein Binding
83.38
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
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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.9
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.8
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.51
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.6
Micronucleos
Toxic
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
-142.74
Rat (Acute)
2.23
Rat (Chronic Oral)
2.49
Fathead Minnow
4.08
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
481.22
Hydration Free Energy
-2.66
Log(D) at pH=7.4
0.96
Log(P)
3.6
Log S
-4.07
Log(Vapor Pressure)
-10.2
Melting Point
162.32
pKa Acid
4.74
pKa Basic
6.5
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9220
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9220
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8767
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8767
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8304
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8304
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8156
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8156
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8024
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8024
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7922
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7922
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7889
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7889
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7626
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7626
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7598
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7598
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7584
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7584
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7572
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.7572
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7561
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7561
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7463
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7463
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7455
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7455
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7430
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7430
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7398
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7398
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7388
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7388
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7343
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7343
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7289
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7289
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7231
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7231
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7182
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7182
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7147
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7147
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7056
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7056
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7054
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7054
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 3 0.7034
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 3 0.7034

Download SDF