(1R*,2R*,3E,7R*,IlR*,12S*)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,8(17)-dien-2,7,16,18-tetrol - Compound Card

(1R*,2R*,3E,7R*,IlR*,12S*)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,8(17)-dien-2,7,16,18-tetrol

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(1R*,2R*,3E,7R*,IlR*,12S*)-2-O-acetyl-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,8(17)-dien-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]2CCC(=C)[C@H](CC1)O)C(O)(C)C)(O)C
InChI InChI=1S/C28H44O9/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/h13,20-23,30,34-35H,1,7-12,14-16H2,2-6H3,(H,31,32)/b19-13-/t20-,21-,22+,23-,27+,28+/m1/s1
InChIKey MKGUELHKGOBNJC-OGIAISHBSA-N
Formula C28H44O9
HBA 8
HBD 4
MW 524.65
Rotatable Bonds 8
TPSA 150.59
LogP 3.3
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 524.3
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: 163031412

No compound-protein relationship available.

Structure

SMILES: C1C=CCCCC(=C)CCC(C12)CCC2

Level: 0

Mol. Weight: 524.65 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.0
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
-2.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.79
Plasma Protein Binding
78.25
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
7.85
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.08
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
3.96
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
-221.07
Rat (Acute)
2.76
Rat (Chronic Oral)
2.32
Fathead Minnow
4.06
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
484.12
Hydration Free Energy
-3.08
Log(D) at pH=7.4
0.05
Log(P)
2.07
Log S
-3.1
Log(Vapor Pressure)
-10.89
Melting Point
153.37
pKa Acid
4.31
pKa Basic
5.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8165
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8165
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8079
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8079
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7991
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7991
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7899
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7899
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.7845
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.7845
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7787
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7787
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7356
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7356
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7285
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7285
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7260
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7260
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7249
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.7249
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7202
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7202
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7176
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7176
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7173
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7173
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7105
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7105
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7104
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7104
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7077
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7077
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7050
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7050
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7045
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7045

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