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Cascarillone

Family: Lamiaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Neo-Clerodane Diterpene

Canonical Smiles	O=C1CC[C@@H]2[C@@]([C@H]1C)(C)CC[C@@H]([C@@]2(C)CCc1ccoc1)C
InChI	InChI=1S/C20H30O2/c1-14-7-10-20(4)15(2)17(21)5-6-18(20)19(14,3)11-8-16-9-12-22-13-16/h9,12-15,18H,5-8,10-11H2,1-4H3/t14-,15-,18-,19+,20-/m0/s1
InChIKey	CPHCLMZVTCAVOA-GYWCDFCBSA-N
Formula	C₂₀H₃₀O₂
HBA	2
HBD	0
MW	302.46
Rotatable Bonds	3
TPSA	30.21
LogP	5.27
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	22
Formal Charge	0
Fraction CSP3	0.75
Exact Mass	302.22
Number of Lipinski Rule Violations	1

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Stachys rosea	Lamiaceae	Plantae	53171

Showing of synonyms

Fazio C, Passannanti S, et al. (1992). Neo-clerodane diterpenoids from Stachys rosea. Phytochemistry, 1992, 31(9), 3147-3149. [View]

Pubchem: 101600184

No compound-protein relationship available.

SMILES: c1occc1CCC2CCCC(C23)CC(=O)CC3

Level: 1

Mol. Weight: 246.35 g/mol

SMILES: C1C(=O)CCC(C12)CCCC2

Level: 0

Mol. Weight: 152.24 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 68.07 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.79
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.5
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.59

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.12
Plasma Protein Binding: 75.9
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 12.78
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.35
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.04
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.74
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 0.03
Rat (Acute): 2.04
Rat (Chronic Oral): 1.82
Fathead Minnow: 3.91
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 363.46
Hydration Free Energy: -3.96
Log(D) at pH=7.4: 4.2
Log(P): 4.77
Log S: -4.59
Log(Vapor Pressure): -6.3
Melting Point: 92.91
pKa Acid: 10.44
pKa Basic: 6.81

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	3	0.9165
Integrin alpha-L	P20701	ITAL_HUMAN	Homo sapiens	3	0.9140
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.9064
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.8911
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8825
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8568
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8442
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.8368
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8348
Probable NDP-rhamnosyltransferase	Q9ALM8	Q9ALM8_SACSN	Saccharopolyspora spinosa	3	0.8212
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8203
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.8198
Sterol 14alpha-demethylase	P9WPP9	CP51_MYCTU	Mycobacterium tuberculosis	3	0.8185
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8138
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.8069
3-ketosteroid dehydrogenase	Q9RA02	Q9RA02_RHOER	Rhodococcus erythropolis	2	0.8062
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.8036
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8030
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.8017
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7996
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7993
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7968
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7949
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7878
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7876
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7872
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7825
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7785
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	2	0.7766
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7764
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7761
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7741
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7725
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7725
ActVA 6 protein	Q53908	Q53908_STRCH	Streptomyces coelicolor	2	0.7709
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7697
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7688
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7665
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7660
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7653
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7639
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7639
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7618
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7615
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7606
Retinol dehydratase	Q26490	Q26490_SPOFR	Spodoptera frugiperda	3	0.7594
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7589
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7588
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	3	0.7588
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	3	0.7587
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	2	0.7581
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7576
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7558
Steroid 17-alpha-hydroxylase/17,20 lyase	P05093	CP17A_HUMAN	Homo sapiens	2	0.7553
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7551
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	2	0.7544
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7544
Glucocorticoid receptor	P04150	GCR_HUMAN	Homo sapiens	4	0.7543
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	3	0.7517
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7495
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	2	0.7479
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7467
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7461
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	3	0.7452
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7422
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7402
Phytohormone-binding protein CSBP	A0A1S3THR8	PHBP_VIGRR	Vigna radiata var. radiata	2	0.7398
Heat shock protein 83	P12861	HSP83_TRYBB	Trypanosoma brucei brucei	3	0.7388
Retinoic acid receptor RXR	Q8T5C6	RXR_BIOGL	Biomphalaria glabrata	3	0.7384
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	3	0.7368
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	2	0.7367
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7366
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7361
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	2	0.7356
17-beta-hydroxysteroid dehydrogenase 14	Q9BPX1	DHB14_HUMAN	Homo sapiens	2	0.7353
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7351
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7350
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7346
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7341
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7341
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7340
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7338
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7335
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7320
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7320
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	2	0.7317
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	2	0.7310
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7284
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7284
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	2	0.7283
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7275
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7270
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	3	0.7267
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7257
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7250
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7247
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	2	0.7235
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7231
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7219
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	2	0.7216
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7213
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7185
Phenazine biosynthesis protein A/B	Q396C9	Q396C9_BURL3	Burkholderia lata	2	0.7178
Nuclear receptor ROR-beta	P45446	RORB_RAT	Rattus norvegicus	2	0.7173
Cellular retinol-binding protein type II	Q8UVG6	Q8UVG6_DANRE	Danio rerio	3	0.7160
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7151
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7150
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7146
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	2	0.7137
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7135
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7130
Retinol-binding protein 1	P09455	RET1_HUMAN	Homo sapiens	3	0.7127
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7125
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7102
C-C chemokine receptor type 5	P51681	CCR5_HUMAN	Homo sapiens	3	0.7090
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7072
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7072
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	2	0.7054
Beta-lactoglobulin	P02754	LACB_BOVIN	Bos taurus	2	0.7054
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7051
Abscisic acid receptor PYL10	Q8H1R0	PYL10_ARATH	Arabidopsis thaliana	3	0.7036
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7022
Cellular retinoic acid-binding protein 2	P29373	RABP2_HUMAN	Homo sapiens	2	0.7001

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