NPASS Natural Product

Natural Product: NPC89549

Natural Product ID:	NPC89549
Common Name:	Clausenawalline B
IUPAC Name:	2,6-dihydroxy-5-(2-hydroxy-9H-carbazol-3-yl)-7-methoxy-1-(3-methylbut-2-enyl)-9H-carbazole-3-carbaldehyde
Synonyms:	Clausenawalline B
Molecular Formula:	C31H26N2O5
Standard InCHIKey:	VLOVIIQGYCTHED-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C31H26N2O5/c1-15(2)8-9-18-29-21(10-16(14-34)30(18)36)27-24(33-29)13-26(38-3)31(37)28(27)20-11-19-17-6-4-5-7-22(17)32-23(19)12-25(20)35/h4-8,10-14,32-33,35-37H,9H2,1-3H3
Canonical SMILES:	COc1cc2[nH]c3c(c2c(c1O)c1cc2c(cc1O)[nH]c1c2cccc1)cc(c(c3CC=C(C)C)O)C=O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO23710	Otholobium pubescens	Species	Fabaceae	Eukaryota	UNPD*
NPO24890	Iris sanguinea	Species	Iridaceae	Eukaryota	UNPD*
NPO25073	Saccharina latissima	Species	Laminariaceae	Eukaryota	UNPD*
NPO25248	Gloydius blomhoffii	Species	Viperidae	Eukaryota	UNPD*
NPO27349	Rhododendron edgeworthii	Species	Ericaceae	Eukaryota	UNPD*
NPO27603	Populus candicans	Species	Salicaceae	Eukaryota	UNPD*
NPO28427	Gutenbergia marginata	Species	Asteraceae	Eukaryota	UNPD*
NPO28500	Griselinia scandens	Species	Griseliniaceae	Eukaryota	UNPD*
NPO28544	Podocalyx loranthoides	Species	Picrodendraceae	Eukaryota	UNPD*
NPO28639	Trixis grisebachii	Species	Asteraceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
MIC	4

Activity Type	# Activity
Organism	4

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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	MIC	=	16	ug/ml	22482432
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	8	ug/ml	22482432
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	128	ug/ml	22482432
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	128	ug/ml	22482432

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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 NPC89549 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	429
0.1-0.2	1928
0.2-0.3	7699
0.3-0.4	5118
0.4-0.5	7158
0.5-0.6	7164
0.6-0.7	1117
0.7-0.8	245
0.8-0.85	25
0.85-0.9	6
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.719	Intermediate Similarity	NPC469592
0.7194	Intermediate Similarity	NPC295228
0.7197	Intermediate Similarity	NPC90185
0.7197	Intermediate Similarity	NPC185197
0.7198	Intermediate Similarity	NPC205934

Showing 1 to 5 of 200 entries

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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 NPC89549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	713
0.2-0.3	1137
0.3-0.4	1756
0.4-0.5	2674
0.5-0.6	1960
0.6-0.7	546
0.7-0.8	74
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
0.6527	Remote Similarity	NPD2565	Phase 2
0.6535	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4429	Discontinued
0.6535	Remote Similarity	NPD3354	Phase 2

Showing 1 to 5 of 200 entries

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Structure

CID89549 OpenBabel06191715422D 38 43 0 0 0 0 0 0 0 0999 V2000 2.3414 -5.1350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6472 -5.4951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8262 -2.0360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3637 4.8370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6205 5.5061 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1557 3.8589 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6695 5.1971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1824 -3.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9255 -3.1787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3018 -0.2442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2047 1.7227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7844 1.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8371 -1.8269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9960 0.1159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3903 -4.8260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2529 -0.5532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2047 3.5498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7176 -2.2005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7980 2.6363 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6169 0.9137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5587 -0.9134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4615 4.2190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1966 2.7408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.7224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3776 1.0183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4249 -1.0179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4359 -0.8088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0236 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7666 -1.8915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4608 -1.5314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0182 -0.1043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4045 3.7190 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0994 -2.3915 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9471 -0.1931 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9654 0.2092 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4118 -1.8404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6060 0.7047 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4194 -1.1224 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 38 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 17 2 0 0 0 0 7 22 2 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 18 1 0 0 0 0 10 16 1 0 0 0 0 10 21 2 0 0 0 0 11 19 2 0 0 0 0 11 20 1 0 0 0 0 12 23 2 0 0 0 0 12 25 1 0 0 0 0 13 24 2 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 34 2 0 0 0 0 16 30 2 0 0 0 0 17 19 1 0 0 0 0 17 22 1 0 0 0 0 18 29 2 0 0 0 0 18 30 1 0 0 0 0 19 23 1 0 0 0 0 20 25 2 0 0 0 0 20 28 1 0 0 0 0 21 27 1 0 0 0 0 21 29 1 0 0 0 0 22 32 1 0 0 0 0 23 32 1 0 0 0 0 24 27 1 0 0 0 0 24 33 1 0 0 0 0 25 35 1 0 0 0 0 26 31 2 0 0 0 0 26 38 1 0 0 0 0 27 28 2 0 0 0 0 28 31 1 0 0 0 0 29 33 1 0 0 0 0 30 36 1 0 0 0 0 31 37 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	60165158
ChEMBL	CHEMBL2037031
ZINC

Physicochemical Properties

Molecular Weight:	506.18
ALogP:	-0.5885
MLogP:	4.1
XLogP:	4.908
# Rotatable Bonds:	11
Polar Surface Area:	118.57
# H-Bond Aceptor:	3
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	38

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