NPASS Natural Product

Natural Product: NPC169990

Natural Product ID:	NPC169990
Common Name:	Adenaflorine D
IUPAC Name:	1-[8,10-dihydroxy-2,2-dimethyl-5-(3-methylbut-2-enoxy)-7-(3-methylbut-2-enyl)benzo[h]chromen-9-yl]ethanone
Synonyms:	Adenaflorine D
Molecular Formula:	C27H32O5
Standard InCHIKey:	HTWXIQRLVLRJGN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H32O5/c1-15(2)8-9-18-20-14-21(31-13-11-16(3)4)19-10-12-27(6,7)32-26(19)23(20)25(30)22(17(5)28)24(18)29/h8,10-12,14,29-30H,9,13H2,1-7H3
Canonical SMILES:	CC(=CCOc1cc2c(CC=C(C)C)c(O)c(c(c2c2c1C=CC(O2)(C)C)O)C(=O)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
NPO17605	Adenaria floribunda	Species	Lythraceae	Eukaryota				PMID[15043429]

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Biological Activity

Activity Type	# Activity
GI50	3

Activity Type	# Activity
Cell Line	3

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT395	Cell Line	SF-268	Homo sapiens	GI50	>	10	ug/ml	17223562
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	9.3	ug/ml	19902967
NPT83	Cell Line	MCF7	Homo sapiens	GI50	>	10	ug/ml	10425143

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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 NPC169990 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	285
0.1-0.2	1263
0.2-0.3	2073
0.3-0.4	5390
0.4-0.5	7644
0.5-0.6	2759
0.6-0.7	3869
0.7-0.8	4230
0.8-0.85	1794
0.85-0.9	1275
0.9-0.95	287
0.95-1	20

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Similarity Score	Similarity Level	Natural Product ID
0.906	High Similarity	NPC131579
0.906	High Similarity	NPC236766
0.906	High Similarity	NPC319752
0.906	High Similarity	NPC216538
0.906	High Similarity	NPC235217

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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 NPC169990 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	934
0.2-0.3	1381
0.3-0.4	2418
0.4-0.5	2117
0.5-0.6	1193
0.6-0.7	554
0.7-0.8	185
0.8-0.85	43
0.85-0.9	19
0.9-0.95	2
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7219	Intermediate Similarity	NPD6844	Discontinued
0.7222	Intermediate Similarity	NPD2654	Approved
0.7225	Intermediate Similarity	NPD7584	Approved
0.7226	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD1729	Discontinued

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Structure

NPC169990 OpenBabel07101719252D 32 34 0 0 0 0 0 0 0 0999 V2000 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 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 0.0000 2.0000 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 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 -2.5981 0.5000 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 -2.5981 -1.5000 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 -3.4641 -1.0000 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 -0.8660 0.5000 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 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -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 -1.7321 3.0000 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 27 1 0 0 0 0 7 27 1 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 12 2 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 12 27 1 0 0 0 0 13 31 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 17 22 1 0 0 0 0 17 28 2 0 0 0 0 18 20 1 0 0 0 0 18 24 2 0 0 0 0 19 21 2 0 0 0 0 19 26 1 0 0 0 0 20 23 1 0 0 0 0 21 31 1 0 0 0 0 22 24 1 0 0 0 0 22 25 2 0 0 0 0 23 25 1 0 0 0 0 23 26 2 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 32 1 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	10433170
ChEMBL	CHEMBL516531
ZINC

Physicochemical Properties

Molecular Weight:	436.22
ALogP:	3.0244
MLogP:	3.88
XLogP:	4.926
# Rotatable Bonds:	15
Polar Surface Area:	75.99
# H-Bond Aceptor:	1
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	32

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