(1R*,2R*,3E,11R*,12S*)-2,18-O-diacetyb16-O-(3-hydroxy-3-methylglutaryl)-2,16,18-trihydroxydolabella-3,8(17)-dien-7-one - Compound Card

(1R*,2R*,3E,11R*,12S*)-2,18-O-diacetyb16-O-(3-hydroxy-3-methylglutaryl)-2,16,18-trihydroxydolabella-3,8(17)-dien-7-one

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(1R*,2R*,3E,11R*,12S*)-2,18-O-diacetyb16-O-(3-hydroxy-3-methylglutaryl)-2,16,18-trihydroxydolabella-3,8(17)-dien-7-one

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpenoid
Canonical Smiles CC(=O)O[C@@H]1/C=C(\COC(=O)C[C@](CC(=O)O)(O)C)/CC[C@H](C(=C)CC[C@@H]2[C@]1(C)CC[C@H]2C(OC(=O)C)(C)C)O
InChI InChI=1S/C30H46O10/c1-18-8-10-23-22(28(4,5)40-20(3)32)12-13-30(23,7)25(39-19(2)31)14-21(9-11-24(18)33)17-38-27(36)16-29(6,37)15-26(34)35/h14,22-25,33,37H,1,8-13,15-17H2,2-7H3,(H,34,35)/b21-14-/t22-,23+,24-,25-,29+,30+/m1/s1
InChIKey UWSRZFDTVZTDHY-OXWVLZIVSA-N
Formula C30H46O10
HBA 9
HBD 3
MW 566.69
Rotatable Bonds 9
TPSA 156.66
LogP 3.87
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 40
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 566.31
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: 162969004

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 566.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.92
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.94
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.41

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.8
Plasma Protein Binding
83.05
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
8.49
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.99
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.72
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.15
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
-849.52
Rat (Acute)
2.86
Rat (Chronic Oral)
2.39
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
490.33
Hydration Free Energy
-3.18
Log(D) at pH=7.4
1.0
Log(P)
2.97
Log S
-3.54
Log(Vapor Pressure)
-10.52
Melting Point
143.24
pKa Acid
5.02
pKa Basic
5.25
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 0.9388
Branched-chain-amino-acid aminotransferase, mitochondrial O15382 BCAT2_HUMAN Homo sapiens 3 0.9388
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9120
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9120
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8921
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.8921
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8438
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8438
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8376
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.8376
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8296
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8296
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8012
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8012
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7866
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7866
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7567
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7567
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7442
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7442
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7405
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7405
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7247
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7247
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7233
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7233
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7188
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7188
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7182
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7182
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7166
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7166
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7159
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7159
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7155
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7155
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7124
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7124
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7031
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7031

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