Seco-tiaminic acid B - Compound Card

Seco-tiaminic acid B

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Seco-tiaminic acid B

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Terpene
    • Subclass: Triterpene
Canonical Smiles OC(=O)CC[C@@]1(C)[C@@H](CC=C2[C@@H]1CC[C@@]1([C@]2(C)CC[C@H]1C1CC(=O)C(=C1)C(C)C)C)C(=C)C
InChI InChI=1S/C30H44O3/c1-18(2)21-16-20(17-26(21)31)23-10-14-30(7)25-9-8-22(19(3)4)28(5,13-12-27(32)33)24(25)11-15-29(23,30)6/h9,16,18,20,22-24H,3,8,10-15,17H2,1-2,4-7H3,(H,32,33)/t20?,22-,23-,24-,28-,29-,30+/m0/s1
InChIKey HATOVUGQFOVVPH-LGYSGVKBSA-N
Formula C30H44O3
HBA 2
HBD 1
MW 452.68
Rotatable Bonds 6
TPSA 54.37
LogP 7.38
Number Rings 4
Number Aromatic Rings 0
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 452.33
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Entandrophragma congoënse Meliaceae Plantae 2590899

Showing of synonyms

  • Happi GM, Talontsi FM, et al. (2018). seco-Tiaminic acids B and C: Identification of two novel 3,4-seco-tirucallane triterpenoids isolated from the root of Entandrophragma congoënse (Meliaceae).. Fitoterapia,2018, 124, 17-22. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O=C1C=CC(C1)C2CCC(C23)C=4C(CC3)CCCC4

Level: 1

Mol. Weight: 452.68 g/mol

Structure

SMILES: C1CCC(C12)CCC3C2=CCCC3

Level: 0

Mol. Weight: 452.68 g/mol

Structure

SMILES: O=C1C=CCC1

Level: 0

Mol. Weight: 452.68 g/mol

Anti-plasmodial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.17
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.87
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
2.32
Plasma Protein Binding
101.43
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
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
Inhibitor

Excretion

Clearance
-0.06
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.52
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.02
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.05
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
Toxic
T. Pyriformis
-95.88
Rat (Acute)
2.61
Rat (Chronic Oral)
1.71
Fathead Minnow
3.94
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
474.27
Hydration Free Energy
-2.71
Log(D) at pH=7.4
4.3
Log(P)
7.16
Log S
-5.76
Log(Vapor Pressure)
-9.03
Melting Point
178.6
pKa Acid
7.1
pKa Basic
5.88
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8755
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8611
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.8438
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 4 0.8402
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8124
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8019
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7893
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7667
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7429
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7378
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7194
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7169
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7104
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7095
Bacteriorhodopsin P02945 BACR_HALSA Halobacterium salinarum 3 0.7086
Vitamin D(3) 25-hydroxylase C4B644 CPVDH_PSEAH Pseudonocardia autotrophica 3 0.7061
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7050
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7024
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7015
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7011

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