NPASS Natural Product

Natural Product: NPC149966

Natural Product ID:	NPC149966
Common Name:	Certonardoside I
IUPAC Name:	(3S,4R,5S,6S,8R,9S,10R,13R,14S,15R,17R)-17-[(2R,5S)-5-[(2R,3R,4S,5R)-4-hydroxy-3-[(2S,3R,4S,5R)-4-hydroxy-3,5-dimethoxyoxan-2-yl]oxy-5-(hydroxymethyl)oxolan-2-yl]oxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,4,6,15-tetrol
Synonyms:	Certonardoside I
Molecular Formula:	C39H68O13
Standard InCHIKey:	NYZYTLFOAUNRRR-YOXBRCCASA-N
Standard InCHI:	InChI=1S/C39H68O13/c1-18(2)26(50-37-35(32(45)27(16-40)51-37)52-36-34(48-7)33(46)28(47-6)17-49-36)9-8-19(3)22-15-25(43)29-20-14-24(42)30-31(44)23(41)11-13-38(30,4)21(20)10-12-39(22,29)5/h18-37,40-46H,8-17H2,1-7H3/t19-,20-,21+,22-,23+,24+,25-,26+,27-,28-,29-,30+,31+,32+,33+,34-,35-,36+,37-,38-,39-/m1/s1
Canonical SMILES:	OC[C@H]1O[C@H]([C@@H]([C@H]1O)O[C@@H]1OC[C@H]([C@@H]([C@H]1OC)O)OC)O[C@H](C(C)C)CC[C@H]([C@H]1C[C@H]([C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H]([C@@H]2[C@]1(C)CC[C@@H]([C@@H]2O)O)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
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota				PMID[12444692]

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Biological Activity

Activity Type	# Activity
EC50	7
Others	3

Activity Type	# Activity
Cell Line	3
Organism	7

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1141	Organism	Human herpesvirus 2	Human herpesvirus 2	EC50	>	100	ug/ml	20350944
NPT165	Cell Line	HeLa	Homo sapiens	CC50	=	59.9	ug/ml	19581457
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	>	100	ug/ml	22901896
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	EC50	>	100	ug/ml	20624681
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	>	42.5	ug/ml	22801644
NPT25	Cell Line	MT4	Homo sapiens	CC50	=	42.5	ug/ml	20329733
NPT2516	Organism	Vesicular stomatitis Indiana virus	Vesicular stomatitis Indiana virus	EC50	>	59.9	ug/ml	12542345
NPT3119	Organism	Human coxsackievirus B3	Human coxsackievirus B3	EC50	>	59.9	ug/ml	10.6019/CHEMBL1201861
NPT3795	Organism	Human immunodeficiency virus 2	Human immunodeficiency virus 2	EC50	>	42.5	ug/ml	PubChem BioAssay data set
NPT4337	Organism	Encephalomyocarditis virus	Encephalomyocarditis virus	EC50	>	59.9	ug/ml	23249297

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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 NPC149966 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	266
0.1-0.2	2533
0.2-0.3	6729
0.3-0.4	10004
0.4-0.5	5004
0.5-0.6	3239
0.6-0.7	2017
0.7-0.8	775
0.8-0.85	137
0.85-0.9	49
0.9-0.95	103
0.95-1	33

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Similarity Score	Similarity Level	Natural Product ID
0.8367	Intermediate Similarity	NPC213190
0.8384	Intermediate Similarity	NPC215408
0.8387	Intermediate Similarity	NPC224003
0.8387	Intermediate Similarity	NPC171741
0.8387	Intermediate Similarity	NPC470623

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 NPC149966 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	3763
0.2-0.3	3458
0.3-0.4	966
0.4-0.5	365
0.5-0.6	236
0.6-0.7	55
0.7-0.8	16
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5647	Remote Similarity	NPD2269	Approved
0.5657	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD8418	Phase 2
0.5673	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD6373	Approved

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Structure

NPC149966 OpenBabel07101718332D 52 57 0 0 1 0 0 0 0 0999 V2000 1.0563 2.5385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6962 0.8443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0006 -0.0422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6807 1.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 -4.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0388 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9000 2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1346 0.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7326 -1.0422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2685 0.9578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8666 -0.5422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8666 2.4578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9321 3.5405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 -3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3872 1.7953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 2.4190 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0006 1.9578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0006 0.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5254 2.6270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.5987 -0.5422 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7326 1.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9266 3.4360 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5909 2.0032 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0388 -3.0981 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1346 2.4578 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7326 0.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5987 0.4578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5388 -2.2321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0388 -1.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0388 -1.3660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8666 0.4578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2685 1.9578 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7045 -2.5823 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4647 -1.0422 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5987 2.4578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5958 4.1791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4647 0.9578 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5388 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -3.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5388 -2.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 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 -2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 6 47 1 0 0 0 0 7 48 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 39 1 0 0 0 0 13 38 1 0 0 0 0 14 24 1 0 0 0 0 15 22 1 0 0 0 0 15 25 1 0 0 0 0 16 40 1 0 0 0 0 17 28 1 0 0 0 0 17 49 1 0 0 0 0 18 26 1 0 0 0 0 19 3 1 1 0 0 0 19 22 1 0 0 0 0 20 14 1 1 0 0 0 20 21 1 0 0 0 0 20 29 1 0 0 0 0 21 38 1 6 0 0 0 22 39 1 6 0 0 0 23 31 1 0 0 0 0 23 41 1 6 0 0 0 24 30 1 0 0 0 0 24 42 1 1 0 0 0 25 29 1 0 0 0 0 25 43 1 6 0 0 0 26 9 1 1 0 0 0 26 50 1 0 0 0 0 27 16 1 6 0 0 0 27 32 1 0 0 0 0 27 51 1 0 0 0 0 28 33 1 0 0 0 0 28 47 1 1 0 0 0 29 39 1 6 0 0 0 30 31 1 0 0 0 0 30 38 1 6 0 0 0 31 44 1 6 0 0 0 32 35 1 0 0 0 0 32 45 1 6 0 0 0 33 34 1 0 0 0 0 33 46 1 6 0 0 0 34 36 1 0 0 0 0 34 48 1 1 0 0 0 35 37 1 0 0 0 0 35 52 1 1 0 0 0 36 49 1 0 0 0 0 36 52 1 6 0 0 0 37 50 1 6 0 0 0 37 51 1 0 0 0 0 38 4 1 6 0 0 0 39 5 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	505377
ChEMBL	CHEMBL452695
ZINC

Physicochemical Properties

Molecular Weight:	744.47
ALogP:	-3.1021
MLogP:	4.32
XLogP:	2.948
# Rotatable Bonds:	26
Polar Surface Area:	196.99
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	52

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