NPASS Natural Product

Natural Product: NPC100402

Natural Product ID:	NPC100402
Common Name:	Membranolide D
IUPAC Name:	(2R)-2-[(1S,3R)-1,3-dimethoxy-5-[(1S)-1,3,3-trimethylcyclohexyl]-1,3-dihydro-2-benzofuran-4-yl]propanoic acid
Synonyms:	Membranolide D
Molecular Formula:	C22H32O5
Standard InCHIKey:	GRCQGWSFSFNRFC-TWYVEXAOSA-N
Standard InCHI:	InChI=1S/C22H32O5/c1-13(18(23)24)16-15(22(4)11-7-10-21(2,3)12-22)9-8-14-17(16)20(26-6)27-19(14)25-5/h8-9,13,19-20H,7,10-12H2,1-6H3,(H,23,24)/t13-,19+,20-,22+/m1/s1
Canonical SMILES:	CO[C@@H]1O[C@@H](c2c1c([C@H](C(=O)O)C)c(cc2)[C@@]1(C)CCCC(C1)(C)C)OC
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
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota		antarctic		PMID[15270575]

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Biological Activity

Activity Type	# Activity
Others	3

Activity Type	# Activity
Organism	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	7	mm	PubChem BioAssay data set
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	6	mm	PubChem BioAssay data set
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	9	mm	19674906

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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 NPC100402 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	161
0.1-0.2	776
0.2-0.3	1491
0.3-0.4	3041
0.4-0.5	6524
0.5-0.6	11451
0.6-0.7	6628
0.7-0.8	799
0.8-0.85	15
0.85-0.9	2
0.9-0.95	0
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.7517	Intermediate Similarity	NPC29704
0.7517	Intermediate Similarity	NPC200471
0.7517	Intermediate Similarity	NPC96903
0.7517	Intermediate Similarity	NPC473088
0.7517	Intermediate Similarity	NPC469349

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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 NPC100402 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	729
0.2-0.3	1160
0.3-0.4	2487
0.4-0.5	2567
0.5-0.6	1549
0.6-0.7	462
0.7-0.8	41
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6453	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD1611	Approved
0.6454	Remote Similarity	NPD3705	Approved
0.6457	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD2798	Approved

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Structure

NPC100402 OpenBabel07101718242D 27 29 0 0 1 0 0 0 0 0999 V2000 -3.1619 3.3833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9327 -1.1510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8665 -0.9008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8728 1.9251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6761 -1.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6761 1.9024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6163 1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3247 -0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1619 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8665 0.4663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6826 1.6502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2492 0.0329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3247 2.9000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4875 -0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1619 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3247 0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4875 0.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4875 3.3833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5682 -0.7820 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5682 0.7820 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1829 -0.2173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9990 0.9667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4875 4.3500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6504 2.9000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2695 -1.7014 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2695 1.7014 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 2 21 1 0 0 0 0 3 21 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 10 1 0 0 0 0 7 11 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 21 1 0 0 0 0 12 22 1 0 0 0 0 13 1 1 1 0 0 0 13 16 1 0 0 0 0 13 18 1 0 0 0 0 14 17 2 0 0 0 0 14 19 1 0 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 6 0 0 0 19 27 1 0 0 0 0 20 26 1 6 0 0 0 20 27 1 0 0 0 0 22 4 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	10022423
ChEMBL	CHEMBL463558
ZINC

Physicochemical Properties

Molecular Weight:	376.22
ALogP:	1.5411
MLogP:	3.33
XLogP:	6.173
# Rotatable Bonds:	12
Polar Surface Area:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	27

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