Myrrhanolide C

Details

• Internal ID: 16d0848b-8b48-4dca-9aa7-fe58fc93873f
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3aS,5S,8S)-3a-hydroxy-1,5,8-trimethyl-5,7,8,9-tetrahydro-4H-benzo[e][1]benzofuran-2,6-dione
• SMILES (Canonical): CC1CC2=C(C(CC3(C2=C(C(=O)O3)C)O)C)C(=O)C1
• SMILES (Isomeric): C[C@H]1CC2=C([C@H](C[C@]3(C2=C(C(=O)O3)C)O)C)C(=O)C1
• InChI: InChI=1S/C15H18O4/c1-7-4-10-12(11(16)5-7)8(2)6-15(18)13(10)9(3)14(17)19-15/h7-8,18H,4-6H2,1-3H3/t7-,8-,15-/m0/s1
• InChI Key: GOVDXHQBFLNYLG-VQLIFVOLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.88
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 8-epi-Myrrhanolide B
• GOVDXHQBFLNYLG-VQLIFVOLSA-N
• (3aS,5S,8S)-3a-Hydroxy-1,5,8-trimethyl-4,5,8,9-tetrahydronaphtho[2,1-b]furan-2,6(3aH,7H)-dione
• Naphtho[2,1-b]furan-2,6-dione, 3a,4,5,7,8,9-hexahydro-3a-hydroxy-1,5,8-trimethyl-, (3aS,5S,8S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9836	98.36%
Caco-2	+	0.8251	82.51%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6639	66.39%
OATP2B1 inhibitior	-	0.8577	85.77%
OATP1B1 inhibitior	+	0.9289	92.89%
OATP1B3 inhibitior	+	0.9545	95.45%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7107	71.07%
P-glycoprotein inhibitior	-	0.9116	91.16%
P-glycoprotein substrate	-	0.8044	80.44%
CYP3A4 substrate	+	0.5489	54.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8849	88.49%
CYP3A4 inhibition	-	0.7068	70.68%
CYP2C9 inhibition	-	0.8722	87.22%
CYP2C19 inhibition	-	0.9140	91.40%
CYP2D6 inhibition	-	0.9639	96.39%
CYP1A2 inhibition	-	0.7978	79.78%
CYP2C8 inhibition	-	0.9421	94.21%
CYP inhibitory promiscuity	-	0.8986	89.86%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Danger	0.4303	43.03%
Eye corrosion	-	0.9829	98.29%
Eye irritation	+	0.6859	68.59%
Skin irritation	+	0.5538	55.38%
Skin corrosion	-	0.9144	91.44%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6578	65.78%
Micronuclear	-	0.5800	58.00%
Hepatotoxicity	+	0.6117	61.17%
skin sensitisation	-	0.7560	75.60%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.8078	80.78%
Acute Oral Toxicity (c)	I	0.4038	40.38%
Estrogen receptor binding	-	0.6322	63.22%
Androgen receptor binding	-	0.4859	48.59%
Thyroid receptor binding	+	0.5789	57.89%
Glucocorticoid receptor binding	-	0.4895	48.95%
Aromatase binding	-	0.7308	73.08%
PPAR gamma	-	0.6093	60.93%
Honey bee toxicity	-	0.9225	92.25%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9789	97.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.17%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.27%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.27%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.25%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.30%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.14%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.63%	97.09%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.45%	97.14%

Plants that contains it

• Commiphora myrrha
• Lophophora williamsii
• Ophiopogon intermedius
• Porophyllum ruderale
• Traversia baccharoides

Cross-Links

• PubChem: 42636912
• NPASS: NPC262766
• LOTUS: LTS0107365
• wikiData: Q105014610