NPASS Natural Product

Natural Product: NPC244577

Natural Product ID:	NPC244577
Common Name:	Phenyl-[(2S,3S)-3,5,7-Trihydroxy-2-Methyl-2-(4-Methylpent-3-Enyl)-3,4-Dihydrochromen-8-Yl]Methanone
IUPAC Name:	phenyl-[(2S,3S)-3,5,7-trihydroxy-2-methyl-2-(4-methylpent-3-enyl)-3,4-dihydrochromen-8-yl]methanone
Synonyms:
Molecular Formula:	C23H26O5
Standard InCHIKey:	FVSFDNITEZDVAF-CVDCTZTESA-N
Standard InCHI:	InChI=1S/C23H26O5/c1-14(2)8-7-11-23(3)19(26)12-16-17(24)13-18(25)20(22(16)28-23)21(27)15-9-5-4-6-10-15/h4-6,8-10,13,19,24-26H,7,11-12H2,1-3H3/t19-,23-/m0/s1
Canonical SMILES:	CC(=CCC[C@]1(C)Oc2c(C[C@@H]1O)c(O)cc(c2C(=O)c1ccccc1)O)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO22504	Tovomita longifolia	Species	Clusiaceae	Eukaryota	Leaves			PMID[16562847]

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Biological Activity

Activity Type	# Activity
GI50	3
MIC	2

Activity Type	# Activity
Cell Line	3
Organism	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	25	ug/ml	21044847
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	5.6	ug/ml	21044847
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	6.5	ug/ml	21044847
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	25	ug/ml	23992864
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	6.8	ug/ml	18955522

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Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC244577 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	1057
0.2-0.3	2119
0.3-0.4	4938
0.4-0.5	7656
0.5-0.6	3270
0.6-0.7	3269
0.7-0.8	4296
0.8-0.85	1714
0.85-0.9	1537
0.9-0.95	656
0.95-1	107

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Similarity Score	Similarity Level	Natural Product ID
0.9384	High Similarity	NPC67805
0.9384	High Similarity	NPC148011
0.9384	High Similarity	NPC290133
0.9384	High Similarity	NPC176229
0.9384	High Similarity	NPC187282

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Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC244577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	811
0.2-0.3	1504
0.3-0.4	2403
0.4-0.5	2140
0.5-0.6	1195
0.6-0.7	550
0.7-0.8	215
0.8-0.85	27
0.85-0.9	23
0.9-0.95	10
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7267	Intermediate Similarity	NPD7229	Phase 3
0.7267	Intermediate Similarity	NPD3972	Approved
0.7277	Intermediate Similarity	NPD7874	Approved
0.7277	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD651	Clinical (unspecified phase)

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Structure

NPC244577 OpenBabel07101718182D 28 30 0 0 1 0 0 0 0 0999 V2000 3.0872 -2.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3120 -1.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1305 -1.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 -1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6390 -1.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9659 -0.7412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3461 -1.8966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 14 2 0 0 0 0 9 15 2 0 0 0 0 10 15 1 0 0 0 0 11 23 1 0 0 0 0 12 16 1 0 0 0 0 12 19 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 18 25 1 0 0 0 0 19 23 1 1 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 27 2 0 0 0 0 22 28 1 0 0 0 0 23 3 1 6 0 0 0 23 28 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11696627
ChEMBL	CHEMBL480854
ZINC

Physicochemical Properties

Molecular Weight:	382.18
ALogP:	0.4352
MLogP:	3.44
XLogP:	4.861
# Rotatable Bonds:	11
Polar Surface Area:	86.99
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	28

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