Marmesin

Details

• Internal ID: bb141e46-98c0-4d40-b269-385d6b369188
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Furanocoumarins > Psoralens
• IUPAC Name: (2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one
• SMILES (Canonical): CC(C)(C1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O
• SMILES (Isomeric): CC(C)([C@@H]1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O
• InChI: InChI=1S/C14H14O4/c1-14(2,16)12-6-9-5-8-3-4-13(15)18-10(8)7-11(9)17-12/h3-5,7,12,16H,6H2,1-2H3/t12-/m0/s1
• InChI Key: FWYSBEAFFPBAQU-LBPRGKRZSA-N
• Popularity: 324 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄O₄
• Molecular Weight: 246.26 g/mol
• Exact Mass: 246.08920892 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.87
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 13849-08-6
• S-(+)-Marmesin
• (+)-Marmesin
• (S)-Marmesin
• (S)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one
• CHEBI:6695
• H5D33D6K5D
• NSC-340840
• (2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one
• DTXSID001030448
• (2S)-2-(1-hydroxy-1-methylethyl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one
• 7H-Furo(3,2-g)(1)benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-(+)-
• CHEBI:49080
• (2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro(3,2-g)chromen-7-one
• (S)-2-(2-hydroxypropan-2-yl)-2,3-dihydro-7H-furo(3,2-g)chromen-7-one
• (2S)-2-(1-hydroxy-1-methylethyl)-2,3-dihydro-7H-furo(3,2-g)chromen-7-one
• 7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-(+)-
• RefChem:155909
• GlyTouCan:G67558UG
• DTXCID201515535
• G67558UG
• 2-(2-Hydroxy-2-propanyl)-2,3-dihydro-7H-furo(3,2-g)chromen-7-one
• 7H-Furo(3,2-g)(1)benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-
• (7S)-marmesin
• (S)-2-(2-Hydroxypropan-2-yl)-2H-furo[3,2-g]chromen-7(3H)-one
• 7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (2S)-
• MFCD01725701
• MARMESIN, (+)-
• CHEMBL442813
• (+)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
• (S)-(+)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
• (S)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
• (+)-Marmesin;(S)-Marmesin
• CCRIS 5728
• 7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE, 2,3-DIHYDRO-2-(1-HYDROXY-1-METHYLETHYL)-, (2S)-
• S(+)-Marmesin
• NSC 340840
• Spectrum_001516
• SpecPlus_000918
• Spectrum2_000737
• Spectrum3_001642
• Spectrum4_001701
• Spectrum5_000402
• Marmesin ((+)-Marmesin)
• UNII-H5D33D6K5D
• BSPBio_003363
• KBioGR_002022
• KBioSS_001996
• DivK1c_007014
• S-(+)-Marmesin (Standard)
• SPBio_000694
• MEGxp0_001933
• orb1301517
• 2-(1-Hydroxy-1-methylethyl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one #
• SCHEMBL12062107
• SCHEMBL30977125
• HSDB 8478
• HY-N2176R
• KBio1_001958
• KBio2_001996
• KBio2_004564
• KBio2_007132
• KBio3_002583
• FWYSBEAFFPBAQU-LBPRGKRZSA-N
• HY-N2176
• BDBM50250917
• CCG-40145
• NSC340840
• NSC796156
• s3283
• AKOS021983162
• CS-7901
• FM74296
• NSC-796156
• SDCCGMLS-0066759.P001
• 7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-
• AC-35105
• DA-65255
• MS-23486
• NS00094519
• C09276
• AB00053150-02
• BRD-K36377456-001-02-0
• Q13847605
• 7H-Furo[3, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (+)-
• 7H-Furo[3, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-
• (2S)-2-(1-hydroxy-1-methyl-ethyl)-2,3-dihydrofuro[3,2-g]chromen-7-one
• 2-(2-HYDROXYPROPAN-2-YL)-2H,3H,7H-FURO[3,2-G]CHROMEN-7-ONE
• 7H-Furo[3, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (S)-(+)-
• (2S)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)-7H-furo[3,2-g][1]benzopyran-7-one
• (2S)-2-(2-HYDROXYPROPAN-2-YL)-2H,3H,7H-FURO[3,2-G]CHROMEN-7-ONE
• 7H-Furo[3,2-g][1]benzopyran-7-one, 2,3-dihydro-2-(1-hydroxy-1-methylethyl)-, (+)-
• NCGC00178117-02!(2S)-2-(2-hydroxypropan-2-yl)-2,3-dihydrofuro[3,2-g]chromen-7-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	+	0.6201	62.01%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7949	79.49%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.8861	88.61%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8951	89.51%
P-glycoprotein inhibitior	-	0.8674	86.74%
P-glycoprotein substrate	-	0.8530	85.30%
CYP3A4 substrate	-	0.5667	56.67%
CYP2C9 substrate	-	0.6506	65.06%
CYP2D6 substrate	-	0.8062	80.62%
CYP3A4 inhibition	-	0.8285	82.85%
CYP2C9 inhibition	-	0.7486	74.86%
CYP2C19 inhibition	-	0.7313	73.13%
CYP2D6 inhibition	-	0.8270	82.70%
CYP1A2 inhibition	-	0.6717	67.17%
CYP2C8 inhibition	-	0.8626	86.26%
CYP inhibitory promiscuity	-	0.9103	91.03%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5086	50.86%
Eye corrosion	-	0.9883	98.83%
Eye irritation	+	0.6051	60.51%
Skin irritation	-	0.6980	69.80%
Skin corrosion	-	0.9226	92.26%
Ames mutagenesis	+	0.9200	92.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4145	41.45%
Micronuclear	+	0.5259	52.59%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.7374	73.74%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.7512	75.12%
Acute Oral Toxicity (c)	III	0.5836	58.36%
Estrogen receptor binding	+	0.6480	64.80%
Androgen receptor binding	-	0.5390	53.90%
Thyroid receptor binding	-	0.5728	57.28%
Glucocorticoid receptor binding	-	0.7145	71.45%
Aromatase binding	+	0.6136	61.36%
PPAR gamma	+	0.7604	76.04%
Honey bee toxicity	-	0.9422	94.22%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9463	94.63%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.22%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.10%	97.25%
CHEMBL2581	P07339	Cathepsin D	93.33%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	91.92%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.69%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.09%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.81%	94.45%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	84.52%	85.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.33%	86.33%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.92%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.53%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.77%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.48%	90.71%

Plants that contains it

• Aegle marmelos
• Afraegle paniculata
• Ammi majus
• Amyris brenesii
• Amyris diatrypa
• Amyris lineata
• Anemarrhena asphodeloides
• Angelica acutiloba
• Angelica dahurica
• Angelica decursiva
• Angelica gigas
• Angelica japonica
• Angelica keiskei
• Angelica pachycarpa
• Angelica sinensis
• Antiaris toxicaria
• Asterolasia phebalioides
• Balanites aegyptiaca
• Boronia algida
• Brosimum gaudichaudii
• Broussonetia papyrifera
• Chorilaena anceps
• Chorilaena quercifolia
• Chorilaena rudis
• Citrus trifoliata
• Conchocarpus inopinatus
• Coronilla scorpioides
• Coronilla viminalis
• Dystaenia takesimana
• Esenbeckia leiocarpa
• Fatoua villosa
• Feroniella lucida
• Ficus carica
• Ficus nervosa
• Glehnia littoralis
• Hansenia weberbaueriana
• Heracleum candicans
• Hymenidium lindleyanum
• Hymenidium rivulorum
• Maquira calophylla
• Peucedanum japonicum
• Peucedanum mashanense
• Peucedanum shanianum
• Prangos bucharica
• Prangos latiloba
• Prangos lipskyi
• Prangos tschimganica
• Rosa transmorrisonensis
• Saposhnikovia divaricata
• Scaevola spinescens
• Seseli asperulum
• Tephrosia sinapou
• Thamnosma rhodesica
• Zanthoxylum ailanthoides
• Zanthoxylum ekmanii
• Zanthoxylum piasezkii
• Zanthoxylum spinosum
• Zanthoxylum syncarpum
• Zanthoxylum wutaiense
• Zanthoxylum zanthoxyloides

Cross-Links

• PubChem: 334704
• NPASS: NPC98179
• LOTUS: LTS0122295
• wikiData: Q13847605