(IR*,2R*,3E,7R*,9R*,11R*,12S*)-3,8(17)-dolabelladiene-2.7,9,16,18-pentol - Compound Card

(IR*,2R*,3E,7R*,9R*,11R*,12S*)-3,8(17)-dolabelladiene-2.7,9,16,18-pentol

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(IR*,2R*,3E,7R*,9R*,11R*,12S*)-3,8(17)-dolabelladiene-2.7,9,16,18-pentol

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@@H]2C[C@H](C(=C)[C@@H](CC1)O)O)C(O)(C)C
InChI InChI=1S/C20H34O5/c1-12-16(22)6-5-13(11-21)9-18(24)20(4)8-7-14(19(2,3)25)15(20)10-17(12)23/h9,14-18,21-25H,1,5-8,10-11H2,2-4H3/b13-9-/t14-,15+,16-,17-,18+,20+/m1/s1
InChIKey COVRWLXLMRYMHF-UGEMETIESA-N
Formula C20H34O5
HBA 5
HBD 5
MW 354.49
Rotatable Bonds 2
TPSA 101.15
LogP 1.53
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.8
Exact Mass 354.24
Number of Lipinski Rule Violations 0
# 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: 163010338

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 354.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.92
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.02
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.52
Plasma Protein Binding
49.69
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
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
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.06
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.57
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.27
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.01
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
-5.2
Rat (Acute)
3.83
Rat (Chronic Oral)
2.44
Fathead Minnow
3.63
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
421.27
Hydration Free Energy
-12.24
Log(D) at pH=7.4
0.45
Log(P)
0.4
Log S
-2.02
Log(Vapor Pressure)
-8.63
Melting Point
153.66
pKa Acid
7.31
pKa Basic
6.97
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9014
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9014
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8840
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.8840
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8691
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8691
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8529
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8529
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8351
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8351
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8301
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8301
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8111
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.8111
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7933
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7933
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7860
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7860
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7852
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7852
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7602
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7602
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7543
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7543
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7458
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7458
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7432
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7432
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7313
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7313
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7144
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7144
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7067
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7067
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7067
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7067
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7059
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7059

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