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Marrubenol

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Terpenoid
- Subclass: Furanic Labdane Diterpene

Canonical Smiles	OC[C@@]1(C)CCC[C@]2([C@H]1[C@H](O)C[C@H]([C@]2(O)CCc1cocc1)C)C
InChI	InChI=1S/C20H32O4/c1-14-11-16(22)17-18(2,13-21)7-4-8-19(17,3)20(14,23)9-5-15-6-10-24-12-15/h6,10,12,14,16-17,21-23H,4-5,7-9,11,13H2,1-3H3/t14-,16-,17+,18-,19+,20-/m1/s1
InChIKey	NZMHIKFTAXRIDL-FQFOHHTNSA-N
Formula	C₂₀H₃₂O₄
HBA	4
HBD	3
MW	336.47
Rotatable Bonds	4
TPSA	73.83
LogP	3.15
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.8
Exact Mass	336.23
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Marrubium vulgare	Lamiaceae	Plantae	41230

Showing of synonyms

El Bardai S, Morel N, et al. (2003). The vasorelaxant activity of marrubenol and marrubiin from Marrubium vulgare. Planta Medica,2003,69(1),75-77. [View] [PubMed]

Pubchem: 10449689

Cas: 560-58-7

Zinc: ZINC000028648780

Nmrshiftdb2: 70129216

Chembl: CHEMBL389065

CPRiL: 140144

SMILES: c1occc1CCC2CCCC(C23)CCCC3

Level: 1

Mol. Weight: 336.47 g/mol

SMILES: C1CCCC(C12)CCCC2

Level: 0

Mol. Weight: 336.47 g/mol

SMILES: c1ccoc1

Level: 0

Mol. Weight: 336.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.83
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.71
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.85

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.68
Plasma Protein Binding: 71.94
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: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 11.65
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -0.59
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.97
Liver Injury II: Safe
hERG Blockers: Toxic
Daphnia Maga: 5.51
Micronucleos: Safe
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Toxic
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -2.26
Rat (Acute): 3.96
Rat (Chronic Oral): 2.32
Fathead Minnow: 3.96
Respiratory Disease: Toxic
Skin Sensitisation: Safe
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 372.65
Hydration Free Energy: -8.78
Log(D) at pH=7.4: 2.54
Log(P): 2.81
Log S: -3.35
Log(Vapor Pressure): -7.72
Melting Point: 132.8
pKa Acid: 8.5
pKa Basic: 6.59

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8860
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	3	0.8860
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8434
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8434
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8163
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8163
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8113
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.8113
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7950
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7950
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7903
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7903
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7885
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7885
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.7706
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.7706
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7639
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7639
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7526
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7526
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7523
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	2	0.7523
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7516
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7516
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7497
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7497
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7484
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7484
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7428
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7428
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7392
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7392
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7362
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7362
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7359
Neocarzinostatin	P0A3R9	NCZS_STRCZ	Streptomyces carzinostaticus	3	0.7359
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7351
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7351
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7288
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	4	0.7288
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7254
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7254
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7253
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7253
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7225
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7225
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7222
Carbonic anhydrase 4	Q64444	CAH4_MOUSE	Mus musculus	2	0.7222
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7217
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7217
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7186
Rhodopsin	P02699	OPSD_BOVIN	Bos taurus	3	0.7186
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7097
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7097
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7089
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7089
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7079
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7079
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7076
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	3	0.7076
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7073
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7073
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	3	0.7022
Acetyl-CoA carboxylase 2	O00763	ACACB_HUMAN	Homo sapiens	3	0.7022
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7019
Methionine aminopeptidase 1	P53582	MAP11_HUMAN	Homo sapiens	3	0.7019

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