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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Capparaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpenoid
Canonical Smiles OC(=O)CC(CC(=O)OC/C/1=C\[C@H](OC(=O)C)[C@@]2(C)CCC([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-/m0/s1
InChIKey XCJIFDKCCHFANV-QDTQZWFKSA-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 Cleome droserifolia Capparaceae Plantae 511510

Showing of synonyms

  • Fathy HM, Aboushoer MI, et al. (2008). Dolabellane diterpenes from Cleome droserifolia. Natural Product Communications,2008,3(9),1479-1482. [View]
Pubchem: 162892433

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
80.0
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
6.99
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.6
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
4.62
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
-140.2
Rat (Acute)
2.22
Rat (Chronic Oral)
2.5
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
476.02
Hydration Free Energy
-2.66
Log(D) at pH=7.4
0.98
Log(P)
3.51
Log S
-4.04
Log(Vapor Pressure)
-10.04
Melting Point
161.26
pKa Acid
4.73
pKa Basic
6.5
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 0.9254
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9254
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8353
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8353
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8262
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8262
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8111
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8111
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7983
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7983
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.7859
Ornithine transcarbamylase, mitochondrial P00480 OTC_HUMAN Homo sapiens 3 0.7859
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7831
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7831
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7713
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7713
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7704
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7704
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7528
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7528
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7288
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7288
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7264
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7264
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7012
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7012

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