Neoorthosiphol A

Details

• Internal ID: d45d4c92-e21e-40db-b279-920a45b98b65
• Taxonomy: Benzenoids > Phenanthrenes and derivatives > Hydrophenanthrenes
• IUPAC Name: [(2S,3S,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-6,10-diacetyloxy-5-benzoyloxy-3-ethenyl-2,7,10a-trihydroxy-2,4b,8,8-tetramethyl-1-oxo-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-yl] benzoate
• SMILES (Canonical): CC(=O)OC1CC2C(C(C(C(C2(C3C1(C(=O)C(C(C3OC(=O)C4=CC=CC=C4)C=C)(C)O)O)C)OC(=O)C5=CC=CC=C5)OC(=O)C)O)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@@]([C@@H]3[C@@]1(C(=O)[C@@]([C@H]([C@H]3OC(=O)C4=CC=CC=C4)C=C)(C)O)O)([C@H]([C@H]([C@H](C2(C)C)O)OC(=O)C)OC(=O)C5=CC=CC=C5)C
• InChI: InChI=1S/C38H44O12/c1-8-24-27(49-32(42)22-15-11-9-12-16-22)29-36(6)25(19-26(47-20(2)39)38(29,46)34(44)37(24,7)45)35(4,5)30(41)28(48-21(3)40)31(36)50-33(43)23-17-13-10-14-18-23/h8-18,24-31,41,45-46H,1,19H2,2-7H3/t24-,25-,26+,27+,28-,29+,30+,31-,36-,37-,38-/m0/s1
• InChI Key: PBUZGANPVDYQRM-FRZINCLTSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₄O₁₂
• Molecular Weight: 692.70 g/mol
• Exact Mass: 692.28327683 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.21
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

• CHEMBL525987
• AKOS040762797
• 243448-72-8
• [(2S,3S,4R,4aS,4bS,5R,6S,7S,8aS,10R,10aR)-6,10-diacetyloxy-5-benzoyloxy-3-ethenyl-2,7,10a-trihydroxy-2,4b,8,8-tetramethyl-1-oxo-4,4a,5,6,7,8a,9,10-octahydro-3H-phenanthren-4-yl] benzoate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9571	95.71%
Caco-2	-	0.8232	82.32%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7068	70.68%
OATP2B1 inhibitior	-	0.7175	71.75%
OATP1B1 inhibitior	+	0.8660	86.60%
OATP1B3 inhibitior	+	0.8639	86.39%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9392	93.92%
P-glycoprotein inhibitior	+	0.8243	82.43%
P-glycoprotein substrate	-	0.6311	63.11%
CYP3A4 substrate	+	0.6715	67.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.8352	83.52%
CYP2C19 inhibition	-	0.8623	86.23%
CYP2D6 inhibition	-	0.9083	90.83%
CYP1A2 inhibition	-	0.8021	80.21%
CYP2C8 inhibition	+	0.7267	72.67%
CYP inhibitory promiscuity	-	0.8729	87.29%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.6153	61.53%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.8921	89.21%
Skin irritation	-	0.7205	72.05%
Skin corrosion	-	0.9276	92.76%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7122	71.22%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.6839	68.39%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5897	58.97%
Acute Oral Toxicity (c)	III	0.6543	65.43%
Estrogen receptor binding	+	0.7538	75.38%
Androgen receptor binding	+	0.6498	64.98%
Thyroid receptor binding	+	0.6503	65.03%
Glucocorticoid receptor binding	+	0.7225	72.25%
Aromatase binding	+	0.5947	59.47%
PPAR gamma	+	0.7241	72.41%
Honey bee toxicity	-	0.6462	64.62%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.88%	91.49%
CHEMBL221	P23219	Cyclooxygenase-1	96.54%	90.17%
CHEMBL2581	P07339	Cathepsin D	96.35%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.92%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.24%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	92.54%	91.19%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.52%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.28%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.15%	94.62%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.56%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	89.30%	94.08%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.36%	95.50%
CHEMBL5028	O14672	ADAM10	85.87%	97.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.66%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.55%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.05%	82.69%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.99%	91.07%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	82.01%	83.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.92%	97.14%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.84%	93.00%

Plants that contains it

• Angelica ursina
• Ardisia macrocarpa
• Asplenium nidus
• Astragalus laxmannii subsp. laxmannii
• Celmisia petriei
• Cenchrus americanus
• Chlorophytum malayense
• Cirsium helenioides
• Clausena indica
• Clusia torresii
• Empetrum nigrum
• Ephedra lomatolepis
• Euonymus maackii
• Ferula assa-foetida
• Gentiana olivieri
• Handroanthus guayacan
• Jateorhiza palmata
• Lindera umbellata
• Morus notabilis
• Nicotiana gossei
• Orthosiphon aristatus
• Orthosiphon aristatus var. aristatus
• Oryza sativa
• Picradeniopsis oppositifolia
• Pinus halepensis
• Pinus thunbergii
• Populus tremula
• Primula veris
• Pterocaulon rugosum
• Rauvolfia tetraphylla
• Salvia prionitis
• Satureja montana
• Saussurea triangulata
• Senecio grandiflorus
• Senecio integerrimus
• Stephania succifera
• Stevia salicifolia
• Tetraria capillaris
• Teucrium alyssifolium
• Ulmus laciniata
• Vernonanthura serratuloides
• Zephyranthes carinata

Cross-Links

• PubChem: 10055454
• NPASS: NPC256142
• LOTUS: LTS0198478
• wikiData: Q105205467