NPASS Natural Product

Natural Product: NPC77263

Natural Product ID:	NPC77263
Common Name:	Certonardosterol Q4
IUPAC Name:	(3S,4R,5S,6S,9R,10R,13R,17R)-3,4,6-trihydroxy-17-[(2R,6S)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,3,4,5,6,7,9,11,12,16,17-dodecahydrocyclopenta[a]phenanthren-15-one
Synonyms:	certonardosterol Q4
Molecular Formula:	C27H44O5
Standard InCHIKey:	JOAPSFJTOPVEGH-MHEGHELOSA-N
Standard InCHI:	InChI=1S/C27H44O5/c1-15(14-28)6-5-7-16(2)19-13-22(31)23-17-12-21(30)24-25(32)20(29)9-11-26(24,3)18(17)8-10-27(19,23)4/h15-16,18-21,24-25,28-30,32H,5-14H2,1-4H3/t15-,16+,18-,19+,20-,21-,24-,25-,26+,27+/m0/s1
Canonical SMILES:	OC[C@H](CCC[C@H]([C@H]1CC(=O)C2=C3[C@H](CC[C@]12C)[C@@]1(C)CC[C@@H]([C@@H]([C@@H]1[C@H](C3)O)O)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
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota				PMID[15497935]

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Biological Activity

Activity Type	# Activity
ED50	5

Activity Type	# Activity
Cell Line	5

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	4.1	ug/ml	26241103
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	3.4	ug/ml	26241103
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	4.2	ug/ml	26241103
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	2.9	ug/ml	26241103
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.8	ug/ml	8450319

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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 NPC77263 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	133
0.1-0.2	871
0.2-0.3	2992
0.3-0.4	6430
0.4-0.5	9914
0.5-0.6	4045
0.6-0.7	4338
0.7-0.8	1961
0.8-0.85	180
0.85-0.9	22
0.9-0.95	0
0.95-1	3

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Similarity Score	Similarity Level	Natural Product ID
0.8	Intermediate Similarity	NPC472824
0.8	Intermediate Similarity	NPC166607
0.8	Intermediate Similarity	NPC180950
0.8	Intermediate Similarity	NPC53565
0.8	Intermediate Similarity	NPC271195

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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 NPC77263 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	143
0.1-0.2	1504
0.2-0.3	3760
0.3-0.4	2549
0.4-0.5	714
0.5-0.6	157
0.6-0.7	184
0.7-0.8	136
0.8-0.85	13
0.85-0.9	1
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6754	Remote Similarity	NPD6314	Approved
0.6759	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6673	Approved
0.6768	Remote Similarity	NPD6080	Approved
0.6768	Remote Similarity	NPD6904	Approved

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Structure

NPC77263 OpenBabel07101719522D 32 35 0 0 1 0 0 0 0 0999 V2000 -4.1161 6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 3.5032 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 -2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 2.9680 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 1.7321 -0.0000 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 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 0 0 0 0 0 0 0 0 0 0 -4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7633 5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7852 5.6132 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8581 2.7601 0.0000 C 0 0 2 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 1 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 2 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 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 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 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0724 6.7722 0.0000 O 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 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -0.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 27 1 0 0 0 0 11 26 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 28 1 0 0 0 0 15 1 1 1 0 0 0 16 2 1 1 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 23 2 0 0 0 0 18 26 1 6 0 0 0 19 27 1 6 0 0 0 20 25 1 0 0 0 0 20 29 1 6 0 0 0 21 24 1 0 0 0 0 21 30 1 1 0 0 0 22 23 1 0 0 0 0 22 31 2 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 6 0 0 0 25 32 1 6 0 0 0 26 3 1 6 0 0 0 27 4 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	21589763
ChEMBL	CHEMBL456740
ZINC

Physicochemical Properties

Molecular Weight:	448.32
ALogP:	-1.4153
MLogP:	3.88
XLogP:	3.75
# Rotatable Bonds:	14
Polar Surface Area:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	32

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