Rotundic acid - Compound Card

Rotundic acid

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Rotundic acid

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Triterpene
Canonical Smiles OC[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2[C@](C)(O)[C@@H](CC1)C)C(=O)O)C)C
InChI InChI=1S/C30H48O5/c1-18-9-14-30(24(33)34)16-15-27(4)19(23(30)29(18,6)35)7-8-21-25(2)12-11-22(32)26(3,17-31)20(25)10-13-28(21,27)5/h7,18,20-23,31-32,35H,8-17H2,1-6H3,(H,33,34)/t18-,20-,21-,22+,23-,25+,26+,27-,28-,29-,30+/m1/s1
InChIKey YLHQFGOOMKJFLP-LTFXOGOQSA-N
Formula C30H48O5
HBA 4
HBD 4
MW 488.71
Rotatable Bonds 2
TPSA 97.99
LogP 5.18
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.9
Exact Mass 488.35
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Nauclea latifolia Rubiaceae Plantae 43573

Showing of synonyms

  • Ngnokam D, Ayafor JF, et al. (2004). Nauclefolinine: a new alkaloid from the roots of nauclea latifolia. Bulletin of The Chemical Society of Ethiopia, 2004,17, 173-176. [View]
Pubchem: 12315075
Chebi: 70684
Nmrshiftdb2: 60026457
Metabolights: MTBLC70684
Bindingdb: 50391059
CPRiL: 115967
Structure

SMILES: C1CCCC2C1CCC(C2=3)C4C(CC3)C5C(CC4)CCCC5

Level: 0

Mol. Weight: 488.71 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.55
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.83
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.82

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.19
Plasma Protein Binding
87.44
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
Inhibitor

Excretion

Clearance
2.17
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.17
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.91
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
4.91
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Toxic
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
-221.34
Rat (Acute)
2.7
Rat (Chronic Oral)
2.45
Fathead Minnow
3.86
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
502.49
Hydration Free Energy
-2.98
Log(D) at pH=7.4
2.82
Log(P)
4.26
Log S
-4.98
Log(Vapor Pressure)
-10.2
Melting Point
244.75
pKa Acid
4.97
pKa Basic
8.04
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8065

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