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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Capparaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpenoid
Canonical Smiles CC(=O)O[C@H]1/C=C(/CC/C=C(/CC[C@@H]2[C@]1(C)CCC2C(OC(=O)C)(C)C)\C)\COC(=O)CC(CC(=O)O)(O)C
InChI InChI=1S/C30H46O9/c1-19-9-8-10-22(18-37-27(35)17-29(6,36)16-26(33)34)15-25(38-20(2)31)30(7)14-13-23(24(30)12-11-19)28(4,5)39-21(3)32/h9,15,23-25,36H,8,10-14,16-18H2,1-7H3,(H,33,34)/b19-9+,22-15-/t23?,24-,25-,29?,30-/m0/s1
InChIKey ATABDKOENHIVSH-HRTSRKQDSA-N
Formula C30H46O9
HBA 8
HBD 2
MW 550.69
Rotatable Bonds 9
TPSA 136.43
LogP 4.9
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 39
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 550.31
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: 162851072
Nmrshiftdb2: 70070356

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC=CCCC=CC2

Level: 0

Mol. Weight: 550.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.72
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
-2.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.91
Plasma Protein Binding
85.38
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
Inhibitor

Excretion

Clearance
7.43
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
0.68
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.16
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
-554.39
Rat (Acute)
2.33
Rat (Chronic Oral)
2.52
Fathead Minnow
4.8
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
492.0
Hydration Free Energy
-3.25
Log(D) at pH=7.4
1.7
Log(P)
4.56
Log S
-4.48
Log(Vapor Pressure)
-9.8
Melting Point
146.32
pKa Acid
5.62
pKa Basic
5.84
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 0.9475
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9475
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8839
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8839
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7923
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7923
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7885
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7885
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7790
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7790
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7746
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7746
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7511
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7511
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7413
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7413
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7326
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7326
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7298
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7298
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7248
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7248
Ficolin-2 Q15485 FCN2_HUMAN Homo sapiens 3 0.7178
Ficolin-2 Q15485 FCN2_HUMAN Homo sapiens 3 0.7178
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7174
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7174
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7127
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7127
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7019
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7019

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