NPASS Natural Product

Natural Product: NPC221091

Natural Product ID:	NPC221091
Common Name:	Clinopodic Acid E
IUPAC Name:	(2R,3R)-6-[(E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxine-3-carboxylic acid
Synonyms:	Clinopodic Acid E
Molecular Formula:	C27H22O12
Standard InCHIKey:	KPKHMGUZUPELJC-ZPOOTWMUSA-N
Standard InCHI:	InChI=1S/C27H22O12/c28-16-5-1-14(9-18(16)30)11-22(26(33)34)37-23(32)8-3-13-2-7-20-21(10-13)39-25(27(35)36)24(38-20)15-4-6-17(29)19(31)12-15/h1-10,12,22,24-25,28-31H,11H2,(H,33,34)(H,35,36)/b8-3+/t22-,24-,25-/m1/s1
Canonical SMILES:	O=C(O[C@@H](C(=O)O)Cc1ccc(c(c1)O)O)/C=C/c1ccc2c(c1)O[C@H]([C@H](O2)c1ccc(c(c1)O)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
NPO13475.1	Clinopodium chinense	Under-species	NA	NA				PMID[19711986]

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Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT40	Individual Protein	72 kDa type IV collagenase	Rattus norvegicus	IC50	>	100000	nM	19114678

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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 NPC221091 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	286
0.1-0.2	1053
0.2-0.3	2313
0.3-0.4	5280
0.4-0.5	7281
0.5-0.6	3116
0.6-0.7	4185
0.7-0.8	5912
0.8-0.85	1282
0.85-0.9	168
0.9-0.95	10
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.8481	Intermediate Similarity	NPC476410
0.8481	Intermediate Similarity	NPC284127
0.8481	Intermediate Similarity	NPC172202
0.8483	Intermediate Similarity	NPC475468
0.8485	Intermediate Similarity	NPC296018

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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 NPC221091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	806
0.2-0.3	1543
0.3-0.4	2486
0.4-0.5	2008
0.5-0.6	1213
0.6-0.7	646
0.7-0.8	147
0.8-0.85	23
0.85-0.9	5
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6918	Remote Similarity	NPD1241	Discontinued
0.6918	Remote Similarity	NPD1607	Approved
0.6918	Remote Similarity	NPD5283	Phase 1
0.6928	Remote Similarity	NPD5049	Phase 3
0.6931	Remote Similarity	NPD3450	Approved

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Structure

NPC221091 OpenBabel07101718182D 39 42 0 0 1 0 0 0 0 0999 V2000 6.0622 -3.5000 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 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 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 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 6.9282 -2.0000 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 6.9282 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 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 6.0622 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 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 5.1962 -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 6.9282 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -5.0000 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 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 5 2 0 0 0 0 1 14 1 0 0 0 0 2 7 2 0 0 0 0 2 13 1 0 0 0 0 3 8 2 0 0 0 0 3 13 1 0 0 0 0 4 6 2 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 20 1 0 0 0 0 8 23 1 0 0 0 0 9 14 2 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 10 21 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 16 18 2 0 0 0 0 16 28 1 0 0 0 0 17 19 2 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 21 2 0 0 0 0 20 38 1 0 0 0 0 21 39 1 0 0 0 0 22 11 1 6 0 0 0 22 26 1 0 0 0 0 22 37 1 0 0 0 0 23 32 2 0 0 0 0 23 37 1 0 0 0 0 24 15 1 6 0 0 0 24 25 1 0 0 0 0 24 38 1 0 0 0 0 25 27 1 6 0 0 0 25 39 1 0 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 27 35 2 0 0 0 0 27 36 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44537885
ChEMBL	CHEMBL1081512
ZINC

Physicochemical Properties

Molecular Weight:	538.11
ALogP:	-2.6612
MLogP:	3.11
XLogP:	2.782
# Rotatable Bonds:	15
Polar Surface Area:	200.28
# H-Bond Aceptor:	6
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	39

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