(IR*,2R*,3E,11R*,12S*)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryi)-2,16,18-trihydroxy-dolabella-3,8(l 7)-dien-7-one - Compound Card

(IR*,2R*,3E,11R*,12S*)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryi)-2,16,18-trihydroxy-dolabella-3,8(l 7)-dien-7-one

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(IR*,2R*,3E,11R*,12S*)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryi)-2,16,18-trihydroxy-dolabella-3,8(l 7)-dien-7-one

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpenoid
Canonical Smiles OC(=O)CC(CC(=O)OC/C/1=C\C(OC(=O)C)[C@@]2(C)CC[C@H]([C@@H]2CCC(=C)C(=O)CC1)C(O)(C)C)(O)C
InChI InChI=1S/C28H42O9/c1-17-7-9-21-20(26(3,4)34)11-12-28(21,6)23(37-18(2)29)13-19(8-10-22(17)30)16-36-25(33)15-27(5,35)14-24(31)32/h13,20-21,23,34-35H,1,7-12,14-16H2,2-6H3,(H,31,32)/b19-13-/t20-,21+,23?,27?,28+/m1/s1
InChIKey UEGOATROGDUXGQ-IXZKVKMXSA-N
Formula C28H42O9
HBA 8
HBD 3
MW 522.64
Rotatable Bonds 8
TPSA 147.43
LogP 3.51
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.71
Exact Mass 522.28
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: 162891864
Nmrshiftdb2: 60051704

No compound-protein relationship available.

Structure

SMILES: C1C=CCCC(=O)C(=C)CCC(C12)CCC2

Level: 0

Mol. Weight: 522.64 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.81
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.97
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.82
Plasma Protein Binding
80.15
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
7.31
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.16
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.8
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.74
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
-216.32
Rat (Acute)
2.7
Rat (Chronic Oral)
2.48
Fathead Minnow
4.05
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
492.04
Hydration Free Energy
-3.02
Log(D) at pH=7.4
0.47
Log(P)
2.15
Log S
-3.46
Log(Vapor Pressure)
-10.5
Melting Point
151.34
pKa Acid
4.51
pKa Basic
4.81
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9260
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.9260
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9218
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9218
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8888
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8888
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8569
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8569
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8449
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8449
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8413
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8413
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8203
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8203
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8139
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8139
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8139
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8139
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8103
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8103
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8002
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8002
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7781
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7781
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7773
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7773
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7756
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7756
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7643
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7643
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7635
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7635
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7619
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7619
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7498
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7498
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7389
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7389
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7257
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7257
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7242
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7242
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7240
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7240
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7236
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7236
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7200
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7200
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7165
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7165
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7134
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7134
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7091
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7091
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 3 0.7036
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 3 0.7036
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7014
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7014

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