Orthosphenic acid

Details

• Internal ID: c1b75aca-55da-444f-8217-33631e08caca
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,4S,5R,8S,11R,13R,14S,17R,18S,20R,21R,24R)-20,21-dihydroxy-5,8,11,14,17,24-hexamethyl-22-oxahexacyclo[19.2.1.01,18.04,17.05,14.08,13]tetracosane-11-carboxylic acid
• SMILES (Canonical): CC1C23CCC4C(C2CC(C1(OC3)O)O)(CCC5(C4(CCC6(C5CC(CC6)(C)C(=O)O)C)C)C)C
• SMILES (Isomeric): C[C@@H]1[C@@]23CC[C@H]4[C@]([C@@H]2C[C@H]([C@@]1(OC3)O)O)(CC[C@@]5([C@@]4(CC[C@@]6([C@H]5C[C@](CC6)(C)C(=O)O)C)C)C)C
• InChI: InChI=1S/C30H48O5/c1-18-29-8-7-19-26(4,20(29)15-22(31)30(18,34)35-17-29)12-14-28(6)21-16-25(3,23(32)33)10-9-24(21,2)11-13-27(19,28)5/h18-22,31,34H,7-17H2,1-6H3,(H,32,33)/t18-,19+,20+,21-,22-,24-,25-,26-,27-,28+,29+,30-/m1/s1
• InChI Key: JPAXVSRGFJVPEU-XCIUXINDSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₈O₅
• Molecular Weight: 488.70 g/mol
• Exact Mass: 488.35017463 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 6.30
• Atomic LogP (AlogP): 5.62
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 86632-20-4
• CHEMBL515079
• (1R,4S,5R,8S,11R,13R,14S,17R,18S,20R,21R,24R)-20,21-dihydroxy-5,8,11,14,17,24-hexamethyl-22-oxahexacyclo[19.2.1.01,18.04,17.05,14.08,13]tetracosane-11-carboxylic acid
• Orthophenic acid
• 2H-3,4a-(Epoxymethano)picene-11-carboxylic acid, eicosahydro-2,3-dihydroxy-4,6b,8,11,12b,14a-hexamethyl-, (2R-(2-alpha,3-beta,4-beta,4a-beta,6a-alpha,6b-beta,8a-beta,11-alpha,12a-beta,12b-alpha,14a-beta,14b-alpha))-
• SCHEMBL2396346
• CHEBI:132615
• C30H45O5
• BDBM50242237
• AKOS040763667
• C30-H45-O5
• AC-35123
• (2R,3R,5aR,7aS,7bR,9aS,12R,13aR,13bS,15aR,15bS,16R)-2,3-dihydroxy-7b,9a,12,13b,15a,16-hexamethylicosahydro-5H-3,5a-methanochryseno[2,1-c]oxepine-12-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9566	95.66%
Caco-2	-	0.6344	63.44%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7573	75.73%
OATP2B1 inhibitior	-	0.5719	57.19%
OATP1B1 inhibitior	+	0.9086	90.86%
OATP1B3 inhibitior	+	0.9454	94.54%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6292	62.92%
BSEP inhibitior	+	0.7431	74.31%
P-glycoprotein inhibitior	-	0.7014	70.14%
P-glycoprotein substrate	-	0.6189	61.89%
CYP3A4 substrate	+	0.6462	64.62%
CYP2C9 substrate	-	0.8114	81.14%
CYP2D6 substrate	-	0.8508	85.08%
CYP3A4 inhibition	-	0.7398	73.98%
CYP2C9 inhibition	-	0.8551	85.51%
CYP2C19 inhibition	-	0.8358	83.58%
CYP2D6 inhibition	-	0.9588	95.88%
CYP1A2 inhibition	-	0.7687	76.87%
CYP2C8 inhibition	-	0.6223	62.23%
CYP inhibitory promiscuity	-	0.9774	97.74%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6403	64.03%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9346	93.46%
Skin irritation	-	0.5227	52.27%
Skin corrosion	-	0.9263	92.63%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4425	44.25%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	-	0.7102	71.02%
skin sensitisation	-	0.9040	90.40%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6074	60.74%
Acute Oral Toxicity (c)	III	0.4535	45.35%
Estrogen receptor binding	+	0.6685	66.85%
Androgen receptor binding	+	0.6742	67.42%
Thyroid receptor binding	+	0.6050	60.50%
Glucocorticoid receptor binding	+	0.7002	70.02%
Aromatase binding	+	0.7357	73.57%
PPAR gamma	+	0.6118	61.18%
Honey bee toxicity	-	0.6975	69.75%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9649	96.49%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.48%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.23%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.41%	96.38%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.69%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.73%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.36%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.33%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.99%	99.23%
CHEMBL221	P23219	Cyclooxygenase-1	86.33%	90.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.09%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	86.05%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.54%	96.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	84.82%	89.34%
CHEMBL237	P41145	Kappa opioid receptor	84.67%	98.10%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.29%	93.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.11%	96.77%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.17%	82.69%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.68%	89.05%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.54%	89.50%

Plants that contains it

• Adenopeltis serrata
• Bituminaria bituminosa
• Centaurea seridis
• Chrozophora tinctoria
• Cneorum pulverulentum
• Dalbergia stipulacea
• Delphinium ajacis
• Elaeagnus commutata
• Eucalyptus flocktoniae
• Flindersia brayleyana
• Heracleum sphondylium
• Jungermannia obovata
• Kummerowia striata
• Mascarenhasia arborescens
• Maytenus woodsonii
• Meconopsis napaulensis
• Merremia umbellata
• Millettia conraui
• Orthosphenia mexicana
• Palafoxia rosea
• Pedicularis condensata
• Perityle vaseyi
• Phoebe formosana
• Piloselloides hirsuta
• Plectranthus garckeanus
• Porella swartziana
• Quercus mongolica
• Rheum webbianum
• Salacia chinensis
• Salvia coulteri
• Satureja cuneifolia
• Senecio flavus
• Sida cordifolia
• Solanum sisymbriifolium
• Thymbra spicata
• Tripterygium regelii
• Tripterygium wilfordii
• Turraeanthus mannii

Cross-Links

• PubChem: 20056194
• NPASS: NPC18536
• LOTUS: LTS0140831
• wikiData: Q104396378