NPASS Natural Product

Natural Product: NPC329852

Natural Product ID:	NPC329852
Common Name:	Brassicolide
IUPAC Name:	(1S,5E,9E)-2-(2-hydroxypropan-2-yl)-5,9-dimethyl-15-oxabicyclo[11.2.1]hexadeca-5,9,13(16)-trien-14-one
Synonyms:	Brassicolide
Molecular Formula:	C20H30O3
Standard InCHIKey:	VIPUZYFCPBOJJF-UNIGNBCPSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-14-7-5-8-15(2)11-12-17(20(3,4)22)18-13-16(10-6-9-14)19(21)23-18/h8-9,13,17-18,22H,5-7,10-12H2,1-4H3/b14-9+,15-8+/t17?,18-/m0/s1
Canonical SMILES:	C/C/1=CCC/C(=C/CCC2=C[C@@H](C(CC1)C(O)(C)C)OC2=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
NPO24464	Nephthea brassica	Species	Nephtheidae	Eukaryota				PMID[10579864]

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Biological Activity

Activity Type	# Activity
ED50	4

Activity Type	# Activity
Cell Line	4

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	5.81	ug/ml	15387645
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.44	ug/ml	15387645
NPT81	Cell Line	A549	Homo sapiens	ED50	>	50	ug/ml	15387645
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.4	ug/ml	15958589

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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 NPC329852 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	84
0.1-0.2	623
0.2-0.3	3342
0.3-0.4	9487
0.4-0.5	8239
0.5-0.6	5166
0.6-0.7	3136
0.7-0.8	772
0.8-0.85	34
0.85-0.9	5
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7532	Intermediate Similarity	NPC316185
0.7532	Intermediate Similarity	NPC84038
0.7534	Intermediate Similarity	NPC34883
0.7556	Intermediate Similarity	NPC242848
0.7556	Intermediate Similarity	NPC134072

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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 NPC329852 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	106
0.1-0.2	1129
0.2-0.3	3813
0.3-0.4	2876
0.4-0.5	761
0.5-0.6	357
0.6-0.7	99
0.7-0.8	20
0.8-0.85	0
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
0.5714	Remote Similarity	NPD6930	Phase 2
0.573	Remote Similarity	NPD6932	Approved
0.573	Remote Similarity	NPD5776	Phase 2
0.573	Remote Similarity	NPD6925	Approved
0.5743	Remote Similarity	NPD4755	Approved

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Structure

NPC329852 OpenBabel07101718182D 23 24 0 0 1 0 0 0 0 0999 V2000 -1.6644 2.1519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6644 -1.2023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9741 -2.4293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1517 -1.9544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4614 0.4748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0177 1.7748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3484 1.0065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3484 -0.0568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5582 1.7180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4993 1.6068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5582 -0.7683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0177 -0.8251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4614 0.4748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0289 1.4462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0289 -0.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9032 1.2431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4993 -0.6572 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9032 -0.2935 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9741 -1.4796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5366 2.0661 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9238 -1.4796 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 15 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 6 10 1 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 14 2 0 0 0 0 10 16 1 0 0 0 0 11 12 1 0 0 0 0 11 15 1 0 0 0 0 12 17 1 0 0 0 0 13 16 2 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 13 1 1 0 0 0 18 23 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	21775543
ChEMBL	CHEMBL481650
ZINC

Physicochemical Properties

Molecular Weight:	318.22
ALogP:	2.7408
MLogP:	3.33
XLogP:	4.614
# Rotatable Bonds:	6
Polar Surface Area:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	23

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