NPASS Natural Product

Natural Product: NPC231710

Natural Product ID:	NPC231710
Common Name:	(7Alpha-Hydroxy)-Morroniside
IUPAC Name:	methyl (1S,3S,4aS,8S,8aS)-3-hydroxy-1-methyl-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,4a,8,8a-hexahydropyrano[3,4-c]pyran-5-carboxylate
Synonyms:	(7Alpha-Hydroxy)-Morroniside
Molecular Formula:	C17H26O11
Standard InCHIKey:	YTZSBJLNMIQROD-VYDXWPHLSA-N
Standard InCHI:	InChI=1S/C17H26O11/c1-6-11-7(3-10(19)26-6)8(15(23)24-2)5-25-16(11)28-17-14(22)13(21)12(20)9(4-18)27-17/h5-7,9-14,16-22H,3-4H2,1-2H3/t6-,7+,9+,10-,11+,12+,13-,14+,16-,17-/m0/s1
Canonical SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C([C@@H]3[C@H]2[C@H](C)O[C@@H](C3)O)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
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	Reference
NPO10458	Pithecollobium dulce	NA	NA	NA		UNPD*
NPO10470	Pimpinella major	Species	Apiaceae	Eukaryota		UNPD*
NPO10548	Stephania viridiflavens	Species	Menispermaceae	Eukaryota		UNPD*
NPO10942	Retama sphaerocarpa	Species	Fabaceae	Eukaryota		UNPD*
NPO11907	Streptomyces nitrosporeus	Species	Streptomycetaceae	Bacteria		UNPD*
NPO14197	Patrinia scabra	Species	Caprifoliaceae	Eukaryota	Roots	PMID[23002924]
NPO14921	Anisothrix integra	Species	Asteraceae	Eukaryota		UNPD*
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota		UNPD*
NPO16539	Viguiera puruana	Species	Asteraceae	Eukaryota		UNPD*
NPO16965	Lyngbya aestuarii	Species	Oscillatoriaceae	Bacteria		UNPD*

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Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000	nM	23002924
NPT2	Others	Unspecified		IC50	>	50000	nM	23002924

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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 NPC231710 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	128
0.1-0.2	1145
0.2-0.3	3779
0.3-0.4	7655
0.4-0.5	10057
0.5-0.6	5643
0.6-0.7	2266
0.7-0.8	162
0.8-0.85	23
0.85-0.9	21
0.9-0.95	5
0.95-1	5

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Similarity Score	Similarity Level	Natural Product ID
0.7033	Intermediate Similarity	NPC110813
0.7037	Intermediate Similarity	NPC315836
0.7037	Intermediate Similarity	NPC313668
0.7041	Intermediate Similarity	NPC92974
0.7048	Intermediate Similarity	NPC151516

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 NPC231710 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	1965
0.2-0.3	4020
0.3-0.4	2041
0.4-0.5	720
0.5-0.6	230
0.6-0.7	52
0.7-0.8	1
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
0.56	Remote Similarity	NPD6015	Approved
0.56	Remote Similarity	NPD6016	Approved
0.5625	Remote Similarity	NPD7078	Approved
0.5631	Remote Similarity	NPD7154	Phase 3
0.5639	Remote Similarity	NPD8387	Clinical (unspecified phase)

Showing 1 to 5 of 124 entries

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Structure

CID231710 OpenBabel06191716032D 28 30 0 0 1 0 0 0 0 0999 V2000 2.5981 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 5.1962 0.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 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 2.5981 -0.5000 0.0000 C 0 0 1 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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 4.3301 1.5000 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 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 24 1 0 0 0 0 3 10 1 0 0 0 0 4 18 1 0 0 0 0 5 8 2 0 0 0 0 5 25 1 0 0 0 0 6 1 1 6 0 0 0 6 11 1 0 0 0 0 6 26 1 0 0 0 0 7 3 1 6 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 15 1 0 0 0 0 9 4 1 1 0 0 0 9 12 1 0 0 0 0 9 27 1 0 0 0 0 10 19 1 6 0 0 0 10 26 1 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 16 25 1 0 0 0 0 16 28 1 0 0 0 0 17 27 1 0 0 0 0 17 28 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	21593530
ChEMBL	CHEMBL2152455
ZINC

Physicochemical Properties

Molecular Weight:	406.15
ALogP:	-3.5764
MLogP:	2.12
XLogP:	-1.34
# Rotatable Bonds:	12
Polar Surface Area:	164.37
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	28

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