NPASS Natural Product

Natural Product: NPC475891

Natural Product ID:	NPC475891
Common Name:	Nitidulin
IUPAC Name:	3-methoxy-6-[(3S)-8-methyl-8-(4-methylpent-3-enyl)-3,4-dihydro-2H-pyrano[2,3-f]chromen-3-yl]benzene-1,2-diol
Synonyms:	Nitidulin
Molecular Formula:	C26H30O5
Standard InCHIKey:	GRHKVSQNMXZXME-QOBPCVTDSA-N
Standard InCHI:	InChI=1S/C26H30O5/c1-16(2)6-5-12-26(3)13-11-20-21(31-26)9-7-17-14-18(15-30-25(17)20)19-8-10-22(29-4)24(28)23(19)27/h6-11,13,18,27-28H,5,12,14-15H2,1-4H3/t18-,26?/m1/s1
Canonical SMILES:	COc1ccc(c(c1O)O)[C@H]1COc2c(C1)ccc1c2C=CC(O1)(C)CCC=C(C)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
NPO401	Berchemia discolor	Species	Rhamnaceae	Eukaryota		Tanzania		PMID[17125241]

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Biological Activity

Activity Type	# Activity
ED50	4
Others	3

Activity Type	# Activity
Cell Line	7

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	4.2	ug/ml	10346942
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	3.5	ug/ml	15646539
NPT858	Cell Line	LNCaP	Homo sapiens	GI	=	54	%	12713394
NPT858	Cell Line	LNCaP	Homo sapiens	Inhibition	=	49	%	23252603
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	4.1	ug/ml	15646539
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	9.7	nM	25856683
NPT858	Cell Line	LNCaP	Homo sapiens	GI	=	0	%	25856683

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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 NPC475891 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	307
0.1-0.2	1195
0.2-0.3	2603
0.3-0.4	6845
0.4-0.5	6432
0.5-0.6	2297
0.6-0.7	3994
0.7-0.8	5154
0.8-0.85	1272
0.85-0.9	599
0.9-0.95	176
0.95-1	15

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Similarity Score	Similarity Level	Natural Product ID
0.8971	High Similarity	NPC220825
0.8971	High Similarity	NPC103799
0.8971	High Similarity	NPC232275
0.8971	High Similarity	NPC268266
0.8978	High Similarity	NPC85435

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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 NPC475891 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	895
0.2-0.3	1565
0.3-0.4	2691
0.4-0.5	1820
0.5-0.6	979
0.6-0.7	701
0.7-0.8	199
0.8-0.85	9
0.85-0.9	5
0.9-0.95	3
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.702	Intermediate Similarity	NPD3268	Approved
0.7024	Intermediate Similarity	NPD1247	Approved
0.7024	Intermediate Similarity	NPD8127	Discontinued
0.7025	Intermediate Similarity	NPD6190	Approved
0.7029	Intermediate Similarity	NPD7090	Clinical (unspecified phase)

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Structure

NPC475891 OpenBabel07101718292D 31 34 0 0 1 0 0 0 0 0999 V2000 3.0872 -2.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8625 -4.0872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4483 -2.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4142 -2.4142 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 5.1962 3.0000 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 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2588 -1.9659 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 3.4641 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 2.1213 -3.1213 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 4.3301 1.5000 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 0.8660 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 6.0622 1.5000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 3 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 7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 26 1 0 0 0 0 4 29 1 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 16 2 0 0 0 0 7 9 2 0 0 0 0 7 17 1 0 0 0 0 8 10 2 0 0 0 0 8 19 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 26 1 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 14 18 1 0 0 0 0 15 18 1 0 0 0 0 15 30 1 0 0 0 0 17 25 2 0 0 0 0 18 19 1 1 0 0 0 19 23 2 0 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 21 31 1 0 0 0 0 22 24 2 0 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 25 30 1 0 0 0 0 26 31 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	16126781
ChEMBL	CHEMBL518081
ZINC

Physicochemical Properties

Molecular Weight:	422.21
ALogP:	1.4359
MLogP:	3.77
XLogP:	4.908
# Rotatable Bonds:	11
Polar Surface Area:	68.15
# H-Bond Aceptor:	0
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	31

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