(lR*,2R*,3E,7R*,11R*,12S*)-3,8(17)-dolabelladiene-2,7,16,18-tetrol-7-O-beta-D-glucopyranoside - Compound Card

(lR*,2R*,3E,7R*,11R*,12S*)-3,8(17)-dolabelladiene-2,7,16,18-tetrol-7-O-beta-D-glucopyranoside

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(lR*,2R*,3E,7R*,11R*,12S*)-3,8(17)-dolabelladiene-2,7,16,18-tetrol-7-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Dolabellane Diterpene Glycoside
Canonical Smiles OC/C/1=C\[C@H](O)[C@@]2(C)CC[C@H]([C@]2(C)CCC(=C)[C@@H](CC1)COC1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O)C(O)(C)C
InChI InChI=1S/C28H48O9/c1-16-8-10-27(4)20(26(2,3)35)9-11-28(27,5)21(31)12-17(13-29)6-7-18(16)15-36-25-24(34)23(33)22(32)19(14-30)37-25/h12,18-25,29-35H,1,6-11,13-15H2,2-5H3/b17-12-/t18-,19+,20-,21-,22+,23-,24+,25?,27-,28+/m0/s1
InChIKey FTGMZEJCVXCZJJ-MAMHPLCBSA-N
Formula C28H48O9
HBA 9
HBD 7
MW 528.68
Rotatable Bonds 6
TPSA 160.07
LogP 1.02
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.86
Exact Mass 528.33
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Chrozophora obliqua Euphorbiaceae Plantae 316753

Showing of synonyms

  • Mohamed KM, Ohtani K, et al. (1994). Dolabellane diterpene glucosides from Chrozophora obliqua. Phytochemistry,1994,37(2),495-500. [View] [PubMed]
Pubchem: 162817258

No compound-protein relationship available.

Structure

SMILES: C1CCC(C12)CCC(=C)C(CCC=CC2)COC3CCCCO3

Level: 1

Mol. Weight: 528.68 g/mol

Structure

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

Level: 0

Mol. Weight: 528.68 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 528.68 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.77
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.24
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.3

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.9
Plasma Protein Binding
77.19
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
3.0
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.45
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.44
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.41
Micronucleos
Safe
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
-423.11
Rat (Acute)
3.94
Rat (Chronic Oral)
3.18
Fathead Minnow
3.33
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
542.44
Hydration Free Energy
-3.16
Log(D) at pH=7.4
1.65
Log(P)
0.96
Log S
-2.32
Log(Vapor Pressure)
-13.58
Melting Point
175.1
pKa Acid
7.13
pKa Basic
6.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9275
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9275
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9177
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9177
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8952
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8952
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8848
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8848
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.8735
Gastrotropin Q6IMW5 Q6IMW5_DANRE Danio rerio 3 0.8735
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8636
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 3 0.8636
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8496
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8496
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8162
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8162
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8063
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8063
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7959
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7959
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7890
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7890
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7828
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7828
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7792
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7792
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7747
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7747
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7739
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7739
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7731
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7731
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7714
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7714
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.7688
Lactose operon repressor P03023 LACI_ECOLI Escherichia coli 3 0.7688
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7664
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7664
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7654
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7654
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7641
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7641
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7569
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7569
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7524
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7524
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7484
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7484
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7465
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7465
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7461
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7461
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7460
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7460
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7389
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7389
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7321
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 3 0.7321
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7264
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7264
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7259
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7259
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7214
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7214
Uncharacterized PhzA/B-like protein PA3332 Q9HYR3 Y3332_PSEAE Pseudomonas aeruginosa 4 0.7195
Uncharacterized PhzA/B-like protein PA3332 Q9HYR3 Y3332_PSEAE Pseudomonas aeruginosa 4 0.7195
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7100
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7100
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7087
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7087
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7008
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7008

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