NPASS Natural Product

Natural Product: NPC309692

Natural Product ID:	NPC309692
Common Name:	Chrotacumine B
IUPAC Name:	[(3S,4R)-4-(5,7-dihydroxy-2-methyl-4-oxochromen-8-yl)-1-methylpiperidin-3-yl] (E)-2-methylbut-2-enoate
Synonyms:
Molecular Formula:	C21H25NO6
Standard InCHIKey:	DSBBHVSUDLJUOE-ZKYNRCFLSA-N
Standard InCHI:	InChI=1S/C21H25NO6/c1-5-11(2)21(26)28-17-10-22(4)7-6-13(17)18-15(24)9-16(25)19-14(23)8-12(3)27-20(18)19/h5,8-9,13,17,24-25H,6-7,10H2,1-4H3/b11-5+/t13-,17+/m0/s1
Canonical SMILES:	C/C=C(/C(=O)O[C@@H]1CN(C)CC[C@@H]1c1c(O)cc(c2c1oc(C)cc2=O)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
NPO654	Dysoxylum acutangulum	Species	Meliaceae	Eukaryota				PMID[19757855]

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Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000	nM	20576574

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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 NPC309692 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	193
0.1-0.2	850
0.2-0.3	2455
0.3-0.4	5889
0.4-0.5	7143
0.5-0.6	4009
0.6-0.7	5962
0.7-0.8	4082
0.8-0.85	300
0.85-0.9	2
0.9-0.95	2
0.95-1	2

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Similarity Score	Similarity Level	Natural Product ID
0.807	Intermediate Similarity	NPC474738
0.807	Intermediate Similarity	NPC475797
0.807	Intermediate Similarity	NPC78554
0.807	Intermediate Similarity	NPC474609
0.807	Intermediate Similarity	NPC469936

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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 NPC309692 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	558
0.2-0.3	1225
0.3-0.4	2070
0.4-0.5	2412
0.5-0.6	1627
0.6-0.7	893
0.7-0.8	210
0.8-0.85	10
0.85-0.9	3
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.705	Intermediate Similarity	NPD7698	Approved
0.705	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD7697	Approved
0.7059	Intermediate Similarity	NPD3050	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5676	Approved

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Structure

NPC309692 OpenBabel07101718222D 28 30 0 0 1 0 0 0 0 0999 V2000 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 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 -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 0.0000 -3.0000 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 -3.4641 -4.0000 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 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 -3.4641 -0.0000 0.0000 N 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 -1.7321 -3.0000 0.0000 O 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 -2.5000 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 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 22 1 0 0 0 0 5 11 2 0 0 0 0 6 7 1 0 0 0 0 6 13 1 0 0 0 0 7 22 1 0 0 0 0 8 12 2 0 0 0 0 8 14 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 10 22 1 0 0 0 0 11 21 1 0 0 0 0 12 27 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 6 0 0 0 14 19 1 0 0 0 0 14 23 2 0 0 0 0 15 18 1 0 0 0 0 15 24 1 0 0 0 0 16 19 2 0 0 0 0 16 25 1 0 0 0 0 17 28 1 6 0 0 0 18 20 2 0 0 0 0 19 20 1 0 0 0 0 20 27 1 0 0 0 0 21 26 2 0 0 0 0 21 28 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	44557028
ChEMBL	CHEMBL1078719
ZINC

Physicochemical Properties

Molecular Weight:	387.17
ALogP:	-0.2279
MLogP:	3
XLogP:	1.404
# Rotatable Bonds:	10
Polar Surface Area:	96.3
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	28

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