Carnosic acid

Details

• Internal ID: 5f0d8fb9-842c-414c-a3b8-e8c64d6e2908
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid
• SMILES (Canonical): CC(C)C1=C(C(=C2C(=C1)CCC3C2(CCCC3(C)C)C(=O)O)O)O
• SMILES (Isomeric): CC(C)C1=C(C(=C2C(=C1)CC[C@@H]3[C@@]2(CCCC3(C)C)C(=O)O)O)O
• InChI: InChI=1S/C20H28O4/c1-11(2)13-10-12-6-7-14-19(3,4)8-5-9-20(14,18(23)24)15(12)17(22)16(13)21/h10-11,14,21-22H,5-9H2,1-4H3,(H,23,24)/t14-,20+/m0/s1
• InChI Key: QRYRORQUOLYVBU-VBKZILBWSA-N
• Popularity: 634 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 4.90
• Atomic LogP (AlogP): 4.32
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• 3650-09-7
• Salvin
• LI791SXT24
• CHEBI:65585
• UNII-LI791SXT24
• 11,12-dihydroxyabieta-8,11,13-trien-20-oic acid
• Carnosicacid
• 139236-75-2
• NSC694080
• (4aR,10aS)-5,6-Dihydroxy-7-isopropyl-1,1-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic Acid
• 11,12-dihydroxy-13-isopropylpodocarpa-8,11,13-trien-17-oic acid
• (4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-(propan-2-yl)-1,3,4,9,10,10a-hexahydrophenanthrene-4a(2H)-carboxylic acid
• 4a(2H)-Phenanthrenecarboxylic acid, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR-trans)-
• RoseOx
• CARNOSIC ACID (USP-RS)
• CARNOSIC ACID [USP-RS]
• Podocarpa-8,11,13-trien-17-oic acid, 11,12-dihydroxy-13-isopropyl-
• (4AR,10AS)-1,3,4,9,10,10A-HEXAHYDRO-5,6-DIHYDROXY-1,1-DIMETHYL-7-(1-METHYLETHYL)-4A(2H)-PHENANTHRENECARBOXYLIC ACID
• 4a(2H)-Phenanthrenecarboxylic acid, 1,3,4,9,10,10a-hexahydro-5,6-dihydroxy-1,1-dimethyl-7-(1-methylethyl)-, (4aR,10aS)-rel-
• Rosamox
• Carnosic-acid
• Carsonic acid
• Carnosic acid
• (4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid
• MFCD02259459
• Deoxypicrosalvinic acid
• UPCMLD-DP056
• CARNOSIC ACID [MI]
• CARNOSIC ACID [INCI]
• CHEMBL484853
• SCHEMBL9923661
• UPCMLD-DP056:001
• DTXSID20904450
• QRYRORQUOLYVBU-VBKZILBWSA-N
• BCPP000299
• Carnosic acid, analytical standard
• HY-N0644
• BDBM50371232
• s3838
• AKOS015901362
• AC-6030
• BCP9000491
• CCG-207954
• NSC-694080
• SMP2_000204
• NCGC00161623-01
• AS-31052
• NCI60_033653
• BCP0726000155
• LS-174601
• C2488
• C3477
• CS-0009671
• C21818
• CARNOSIC ACID (CONSTITUENT OF ROSEMARY)
• A918580
• Q412827
• SR-05000002202
• SR-05000002202-2
• CARNOSIC ACID (CONSTITUENT OF ROSEMARY) [DSC]
• Carnosic acid, primary pharmaceutical reference standard
• Carnosic acid from Rosmarinus officinalis, >=91%, powder
• Carnosic acid, United States Pharmacopeia (USP) Reference Standard
• (4aR,10aS)-5,6-dihydroxy-1,1-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylicacid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9852	98.52%
Caco-2	+	0.5906	59.06%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8898	88.98%
OATP2B1 inhibitior	-	0.8577	85.77%
OATP1B1 inhibitior	+	0.8616	86.16%
OATP1B3 inhibitior	+	0.9006	90.06%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7821	78.21%
BSEP inhibitior	-	0.5898	58.98%
P-glycoprotein inhibitior	-	0.8992	89.92%
P-glycoprotein substrate	-	0.7853	78.53%
CYP3A4 substrate	+	0.5902	59.02%
CYP2C9 substrate	-	0.5790	57.90%
CYP2D6 substrate	-	0.8254	82.54%
CYP3A4 inhibition	-	0.7410	74.10%
CYP2C9 inhibition	-	0.8565	85.65%
CYP2C19 inhibition	-	0.8234	82.34%
CYP2D6 inhibition	-	0.9479	94.79%
CYP1A2 inhibition	+	0.6942	69.42%
CYP2C8 inhibition	-	0.5761	57.61%
CYP inhibitory promiscuity	-	0.9485	94.85%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6566	65.66%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.7579	75.79%
Skin irritation	-	0.5780	57.80%
Skin corrosion	-	0.9379	93.79%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.7362	73.62%
Micronuclear	-	0.8900	89.00%
Hepatotoxicity	+	0.5199	51.99%
skin sensitisation	-	0.7876	78.76%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8641	86.41%
Acute Oral Toxicity (c)	III	0.7138	71.38%
Estrogen receptor binding	+	0.7414	74.14%
Androgen receptor binding	-	0.5125	51.25%
Thyroid receptor binding	+	0.7108	71.08%
Glucocorticoid receptor binding	+	0.8787	87.87%
Aromatase binding	+	0.6000	60.00%
PPAR gamma	+	0.8205	82.05%
Honey bee toxicity	-	0.9022	90.22%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	15848.9 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	14125.4 nM	Potency	via CMAUP
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	1995.3 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	9200 nM	Ki	PMID: 22531045
CHEMBL340	P08684	Cytochrome P450 3A4	4300 nM	Ki	PMID: 22531045
CHEMBL1293224	P10636	Microtubule-associated protein tau	8912.5 nM; 10000 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL5658	O14684	Prostaglandin E synthase	5000 nM	IC50	DOI: 10.1039/C5MD00278H

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.32%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.89%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	94.49%	90.71%
CHEMBL2581	P07339	Cathepsin D	94.40%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.48%	96.09%
CHEMBL233	P35372	Mu opioid receptor	93.05%	97.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.84%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.96%	97.25%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.23%	93.56%
CHEMBL340	P08684	Cytochrome P450 3A4	86.99%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.61%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.41%	99.15%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.71%	96.38%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.34%	93.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.13%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.91%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.49%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.79%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.37%	93.04%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.01%	100.00%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	80.80%	95.71%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.54%	100.00%

Plants that contains it

• Acer pictum subsp. mono
• Achyrocline bogotensis
• Alstonia yunnanensis
• Chamaemelum fuscatum
• Dalea versicolor
• Dasymaschalon dasymaschalum
• Elekmania fuertesii
• Hymenostephium cordatum
• Hyptis dilatata
• Isodon adenolomus
• Lepechinia hastata
• Lepechinia salviae
• Myristica fragrans
• Rosmarinus officinalis
• Salvia africana-lutea
• Salvia apiana
• Salvia canariensis
• Salvia columbariae
• Salvia mellifera
• Salvia munzii
• Salvia officinalis
• Salvia pachyphylla
• Salvia tomentosa
• Salvia willeana
• Scutellaria albida
• Sideritis cystosiphon
• Thymus quinquecostatus
• Thymus vulgaris
• Verbesina virgata
• Vincetoxicum hirsutum

Cross-Links

• PubChem: 65126
• NPASS: NPC293454
• ChEMBL: CHEMBL484853
• LOTUS: LTS0097375
• wikiData: Q412827