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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpenoid
Canonical Smiles O=C(C[C@](CC(=O)O)(O)C)OC/C/1=C/[C@H](O)[C@@]2(C)CC[C@H]([C@@H]2C[C@@H]2[C@]([C@@H](CC1)O)(C)O2)C(OC(=O)C)(C)C
InChI InChI=1S/C28H44O10/c1-16(29)37-25(2,3)18-9-10-27(5)19(18)12-22-28(6,38-22)20(30)8-7-17(11-21(27)31)15-36-24(34)14-26(4,35)13-23(32)33/h11,18-22,30-31,35H,7-10,12-15H2,1-6H3,(H,32,33)/b17-11+/t18-,19+,20-,21+,22-,26+,27+,28-/m1/s1
InChIKey BHBXKBYEDRBUAQ-LTRXOBKWSA-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: 162971264

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)
-5.66
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.020
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.740
Plasma Protein Binding
59.11
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
12.430
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.600
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.140
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.540
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
-477.300
Rat (Acute)
3.050
Rat (Chronic Oral)
2.570
Fathead Minnow
3.760
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
510.750
Hydration Free Energy
-3.190
Log(D) at pH=7.4
-0.460
Log(P)
1.91
Log S
-3.37
Log(Vapor Pressure)
-10.89
Melting Point
146.5
pKa Acid
3.38
pKa Basic
5.4
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8671
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8671
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8577
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8577
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8483
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.8483
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8350
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.8350
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7753
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7753
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7707
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7707
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7518
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7518
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7502
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7502
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7491
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7491
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7393
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7393
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7265
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7265
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7233
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7233
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7230
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7230
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7201
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7201
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7160
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7160
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7094
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7094

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