NPASS Natural Product

Natural Product: NPC195645

Natural Product ID:	NPC195645
Common Name:	2-Epi-Discodermolide
IUPAC Name:	[(3Z,5S,6S,7S,8R,9S,11Z,13S,14S,15S,16Z,18S)-8,14,18-trihydroxy-19-[(2S,3R,4S,5S)-4-hydroxy-3,5-dimethyl-6-oxooxan-2-yl]-5,7,9,11,13,15-hexamethylnonadeca-1,3,11,16-tetraen-6-yl] carbamate
Synonyms:	2-Epi-Discodermolide
Molecular Formula:	C33H55NO8
Standard InCHIKey:	AADVCYNFEREWOS-IMXZWMQCSA-N
Standard InCHI:	InChI=1S/C33H55NO8/c1-10-11-12-20(4)31(42-33(34)40)24(8)29(37)22(6)16-18(2)15-21(5)28(36)19(3)13-14-26(35)17-27-23(7)30(38)25(9)32(39)41-27/h10-15,19-31,35-38H,1,16-17H2,2-9H3,(H2,34,40)/b12-11-,14-13-,18-15-/t19-,20-,21-,22-,23-,24-,25-,26+,27-,28-,29+,30-,31-/m0/s1
Canonical SMILES:	C=C/C=C[C@@H]([C@@H]([C@H]([C@@H]([C@H](C/C(=C[C@@H]([C@H]([C@H](/C=C[C@H](C[C@@H]1OC(=O)[C@H]([C@H]([C@H]1C)O)C)O)C)O)C)/C)C)O)C)OC(=N)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
NPO32706	discodermia sp.	Species	Theonellidae	Eukaryota				PMID[12444691]

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Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	134	nM	20329733
NPT81	Cell Line	A549	Homo sapiens	IC50	=	67	nM	18077425

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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 NPC195645 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	62
0.1-0.2	406
0.2-0.3	2185
0.3-0.4	5722
0.4-0.5	12374
0.5-0.6	6595
0.6-0.7	3354
0.7-0.8	182
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.6972	Remote Similarity	NPC231271
0.6972	Remote Similarity	NPC220964
0.6975	Remote Similarity	NPC314629
0.6981	Remote Similarity	NPC244411
0.6983	Remote Similarity	NPC13710

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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 NPC195645 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	83
0.1-0.2	611
0.2-0.3	3041
0.3-0.4	3310
0.4-0.5	1554
0.5-0.6	453
0.6-0.7	81
0.7-0.8	24
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5669	Remote Similarity	NPD6059	Approved
0.5672	Remote Similarity	NPD2613	Approved
0.5676	Remote Similarity	NPD7087	Discontinued
0.5676	Remote Similarity	NPD7515	Phase 2
0.5678	Remote Similarity	NPD8081	Approved

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Structure

NPC195645 OpenBabel07101719252D 42 42 0 0 1 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 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 -1.7321 5.0000 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 -5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 6.5000 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 0.0000 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 6.5000 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 -2.5981 -1.5000 0.0000 C 0 0 0 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 -4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 6.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 6.5000 0.0000 C 0 0 1 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 -3.4641 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 7.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 9.0000 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 -2.5981 7.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 18 1 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 19 1 0 0 0 0 14 26 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 18 1 0 0 0 0 16 22 1 0 0 0 0 17 26 1 0 0 0 0 19 3 1 1 0 0 0 19 28 1 0 0 0 0 20 4 1 6 0 0 0 20 31 1 0 0 0 0 21 5 1 6 0 0 0 21 28 1 0 0 0 0 22 6 1 6 0 0 0 22 29 1 0 0 0 0 23 7 1 1 0 0 0 23 27 1 0 0 0 0 23 30 1 0 0 0 0 24 8 1 6 0 0 0 24 29 1 0 0 0 0 24 31 1 0 0 0 0 25 9 1 1 0 0 0 25 30 1 0 0 0 0 25 32 1 0 0 0 0 26 35 1 1 0 0 0 27 17 1 6 0 0 0 27 41 1 0 0 0 0 28 36 1 6 0 0 0 29 37 1 6 0 0 0 30 38 1 1 0 0 0 31 42 1 1 0 0 0 32 39 2 0 0 0 0 32 41 1 0 0 0 0 33 34 2 0 0 0 0 33 40 1 0 0 0 0 33 42 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11124818
ChEMBL	CHEMBL453645
ZINC

Physicochemical Properties

Molecular Weight:	593.39
ALogP:	1.9202
MLogP:	4.1
XLogP:	4.72
# Rotatable Bonds:	30
Polar Surface Area:	160.53
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	1
# Heavy Atoms:	42

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