Methyl ester of (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

Methyl ester of (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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Methyl ester of (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 COC(=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(OC(=O)C)(C)C)(O)C
InChI InChI=1S/C31H48O9/c1-20-10-9-11-23(19-38-28(35)18-30(6,36)17-27(34)37-8)16-26(39-21(2)32)31(7)15-14-24(25(31)13-12-20)29(4,5)40-22(3)33/h10,16,24-26,36H,9,11-15,17-19H2,1-8H3/b20-10+,23-16-/t24?,25-,26-,30?,31-/m0/s1
InChIKey SHVZQDHUQDKZLR-RBWOHUBWSA-N
Formula C31H48O9
HBA 9
HBD 1
MW 564.72
Rotatable Bonds 9
TPSA 125.43
LogP 4.99
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.74
Exact Mass 564.33
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: 162861391

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC=CCCC=CC2

Level: 0

Mol. Weight: 564.72 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.860
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.700
Plasma Protein Binding
78.53
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
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
9.690
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.290
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.790
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.650
Micronucleos
Safe
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
-987.280
Rat (Acute)
2.850
Rat (Chronic Oral)
2.500
Fathead Minnow
6.290
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
444.930
Hydration Free Energy
-2.840
Log(D) at pH=7.4
3.550
Log(P)
5.11
Log S
-5.58
Log(Vapor Pressure)
-7.85
Melting Point
83.77
pKa Acid
12.05
pKa Basic
4.4
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 0.9427
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9427
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9175
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9175
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8375
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8375
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8302
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8302
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8238
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8238
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7682
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.7682
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7538
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7538
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7434
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7434
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7339
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7339
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7312
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7312
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7287
Phytohormone-binding protein G7J032 PHBP_MEDTR Medicago truncatula 4 0.7287
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.7285
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.7285
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7199
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7199
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7147
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7147
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7102
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7102
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7080
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7080
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7055
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7055

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