Colocynthoside B - Compound Card

Colocynthoside B

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Colocynthoside B

Structure
Zoomed Structure
  • Family: Plantae - Cucurbitaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles OC[C@H]1O[C@@H](OC2=C[C@@H]3C(=CC[C@@H]4[C@@]3(C)C(=O)C[C@]3([C@@]4(C)C[C@@H]4[C@@H]3[C@@](C)(O)C[C@H](O4)/C=C(/CO)\C)C)C(C2=O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O
InChI InChI=1S/C42H62O15/c1-18(16-43)11-20-13-41(7,52)34-24(54-20)14-39(5)26-10-9-21-22(42(26,8)27(45)15-40(34,39)6)12-23(35(51)38(21,3)4)55-37-33(31(49)29(47)25(17-44)56-37)57-36-32(50)30(48)28(46)19(2)53-36/h9,11-12,19-20,22,24-26,28-34,36-37,43-44,46-50,52H,10,13-17H2,1-8H3/b18-11+/t19-,20+,22+,24+,25+,26-,28-,29+,30+,31-,32+,33+,34-,36-,37+,39-,40+,41-,42-/m0/s1
InChIKey BEQDSDZQSKPXIG-VKIDFJQWSA-N
Formula C42H62O15
HBA 15
HBD 8
MW 806.94
Rotatable Bonds 7
TPSA 242.13
LogP 0.57
Number Rings 7
Number Aromatic Rings 0
Heavy Atom Count 57
Formal Charge 0
Fraction CSP3 0.81
Exact Mass 806.41
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Citrullus colocynthis Cucurbitaceae Plantae 252529

Showing of synonyms

  • Yoshikawa M, Morikawa T, et al. (2007). Bioactive Saponins and Glycosides. XXVII. 1) Structures of New Cucurbitane-Type Triterpene Glycosides and Antiallergic Constituents from Citrullus colocynthis. Chemical & pharmaceutical bulletin, 2007, 55(3), 428-34. [View] [PubMed]
Pubchem: 16216649
Nmrshiftdb2: 70002372

No compound-protein relationship available.

Structure

SMILES: C1CCOC(C1C23)CC2C4C(C(=O)C3)C5C(=CC4)CC(=O)C(=C5)OC(OCCC6)C6OC7CCCCO7

Level: 2

Mol. Weight: 806.94 g/mol

Structure

SMILES: C1CCOC(C1C23)CC2C4C(C(=O)C3)C5C(=CC4)CC(=O)C(=C5)OC6CCCCO6

Level: 1

Mol. Weight: 806.94 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 806.94 g/mol

Structure

SMILES: C1CCOC(C1C23)CC2C4C(C(=O)C3)C5C(=CC4)CC(=O)C=C5

Level: 0

Mol. Weight: 806.94 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 806.94 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.28
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
28.150
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
4444.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.860
Plasma Protein Binding
95.9
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
2.700
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-106.930
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.800
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.610
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Toxic
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-8066030.680
Rat (Acute)
3.880
Rat (Chronic Oral)
4.330
Fathead Minnow
10187.790
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
903756.450
Hydration Free Energy
-2.920
Log(D) at pH=7.4
2.760
Log(P)
0.88
Log S
-3.54
Log(Vapor Pressure)
-29631.64
Melting Point
255.19
pKa Acid
-164.49
pKa Basic
4.25
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8392
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7840
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.7591
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7462
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7146

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