NPASS Natural Product

Natural Product: NPC476394

Natural Product ID:	NPC476394
Common Name:	3-O-Methyl Isoamericanoic Acid A
IUPAC Name:	(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxine-6-carboxylic acid
Synonyms:
Molecular Formula:	C17H16O7
Standard InCHIKey:	HMMMZZGULXPBRP-HZPDHXFCSA-N
Standard InCHI:	InChI=1S/C17H16O7/c1-22-13-6-9(2-4-11(13)19)16-15(8-18)23-12-5-3-10(17(20)21)7-14(12)24-16/h2-7,15-16,18-19H,8H2,1H3,(H,20,21)/t15-,16-/m1/s1
Canonical SMILES:	OC[C@H]1Oc2ccc(cc2O[C@@H]1c1ccc(c(c1)OC)O)C(=O)O
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
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark			PMID[19646881]

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Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio	=	1.7		18616221

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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 NPC476394 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	234
0.1-0.2	982
0.2-0.3	2160
0.3-0.4	4857
0.4-0.5	7442
0.5-0.6	3272
0.6-0.7	3346
0.7-0.8	5825
0.8-0.85	2042
0.85-0.9	668
0.9-0.95	51
0.95-1	10

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Similarity Score	Similarity Level	Natural Product ID
0.8723	High Similarity	NPC285776
0.8725	High Similarity	NPC262282
0.8725	High Similarity	NPC30890
0.8725	High Similarity	NPC287275
0.8726	High Similarity	NPC472964

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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 NPC476394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	787
0.2-0.3	1509
0.3-0.4	2325
0.4-0.5	2152
0.5-0.6	1191
0.6-0.7	691
0.7-0.8	215
0.8-0.85	33
0.85-0.9	10
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7125	Intermediate Similarity	NPD6674	Discontinued
0.7125	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7177	Discontinued
0.7134	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4536	Approved

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Structure

NPC476394 OpenBabel07101718292D 24 26 0 0 1 0 0 0 0 0999 V2000 -4.3301 1.5000 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 -2.5981 -1.5000 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 -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 -1.7321 2.0000 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 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 22 1 0 0 0 0 2 4 2 0 0 0 0 2 9 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 10 17 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 14 2 0 0 0 0 12 23 1 0 0 0 0 13 22 1 0 0 0 0 14 24 1 0 0 0 0 15 8 1 1 0 0 0 15 16 1 0 0 0 0 15 23 1 0 0 0 0 16 9 1 6 0 0 0 16 24 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	46226513
ChEMBL	CHEMBL594777
ZINC

Physicochemical Properties

Molecular Weight:	332.09
ALogP:	-1.6096
MLogP:	2.56
XLogP:	1.168
# Rotatable Bonds:	8
Polar Surface Area:	105.45
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	24

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