(1R*,2R*,3E,7R*,11R*,12S*)-16-O-(3-hydroxy-3-methyl-glutaryl)-dolabella-3,8(17)-dien- 2,7,9,16,18-pentol - Compound Card

(1R*,2R*,3E,7R*,11R*,12S*)-16-O-(3-hydroxy-3-methyl-glutaryl)-dolabella-3,8(17)-dien- 2,7,9,16,18-pentol

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(1R*,2R*,3E,7R*,11R*,12S*)-16-O-(3-hydroxy-3-methyl-glutaryl)-dolabella-3,8(17)-dien- 2,7,9,16,18-pentol

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](C(=C)[C@@H](CC1)O)O)C(O)(C)C)(O)C
InChI InChI=1S/C26H42O9/c1-15-19(27)7-6-16(14-35-23(32)13-25(4,34)12-22(30)31)10-21(29)26(5)9-8-17(24(2,3)33)18(26)11-20(15)28/h10,17-21,27-29,33-34H,1,6-9,11-14H2,2-5H3,(H,30,31)/b16-10-/t17-,18+,19-,20-,21+,25-,26+/m1/s1
InChIKey WXIOZXZWVKCFJU-DGAGHFCLSA-N
Formula C26H42O9
HBA 8
HBD 6
MW 498.61
Rotatable Bonds 7
TPSA 164.75
LogP 1.7
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 498.28
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: 162856315

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 498.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.21
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.2
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.5

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.77
Plasma Protein Binding
73.62
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
9.13
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.18
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.23
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.03
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
-89.22
Rat (Acute)
2.54
Rat (Chronic Oral)
2.69
Fathead Minnow
3.99
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
485.08
Hydration Free Energy
-2.28
Log(D) at pH=7.4
-0.79
Log(P)
0.18
Log S
-2.22
Log(Vapor Pressure)
-12.03
Melting Point
155.09
pKa Acid
3.15
pKa Basic
7.06
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 0.8929
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8929
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8787
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8787
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8036
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8036
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7565
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7565
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7315
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7315
3-hydroxy-3-methylglutaryl-coenzyme A reductase P13702 MVAA_PSEMV Pseudomonas mevalonii 3 0.7285
3-hydroxy-3-methylglutaryl-coenzyme A reductase P13702 MVAA_PSEMV Pseudomonas mevalonii 3 0.7285
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7253
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7253
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7188
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7188

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