NPASS Natural Product

Natural Product: NPC220173

Natural Product ID:	NPC220173
Common Name:	Isorhamnetin-3-O-Nehesperridin
IUPAC Name:	3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)chromen-4-one
Synonyms:	Isorhamnetin 3-O-Neohesperidoside
Molecular Formula:	C28H32O16
Standard InCHIKey:	QHLKSZBFIJJREC-SPSUIZEHSA-N
Standard InCHI:	InChI=1S/C28H32O16/c1-9-18(33)21(36)23(38)27(40-9)44-26-22(37)19(34)16(8-29)42-28(26)43-25-20(35)17-13(32)6-11(30)7-15(17)41-24(25)10-3-4-12(31)14(5-10)39-2/h3-7,9,16,18-19,21-23,26-34,36-38H,8H2,1-2H3/t9-,16+,18-,19+,21+,22-,23+,26+,27-,28-/m0/s1
Canonical SMILES:	OC[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota		TM-MC*
NPO28251	Typha orientalis	Species	Typhaceae	Eukaryota		TM-MC*
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota	Flowers	PMID[17190444]
NPO28919	Calendula officinalis	Species	Asteraceae	Eukaryota		TCMSP*
NPO9822	Typha angustifolia	Species	Typhaceae	Eukaryota		TM-MC*

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Biological Activity

Activity Type	# Activity
IC50	6
Others	10

Activity Type	# Activity
Cell Line	9
Individual Protein	2
Others	5

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	55.77	%	22137340
NPT108	Individual Protein	Estrogen receptor alpha	Homo sapiens	Activity	=	88.3	%	22137340
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	74400	nM	10.1007/s00044-013-0773-3
NPT2	Others	Unspecified		Activity	=	14.1	%	17190444
NPT2	Others	Unspecified		Activity	=	60	%	17190444
NPT2	Others	Unspecified		Activity	=	81.1	%	17190444
NPT2	Others	Unspecified		IC50	=	574	molar ratio	17190444
NPT2	Others	Unspecified		Activity	=	100	%	17190444
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	72000	nM	10.1007/s00044-013-0773-3
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	0.003	ug/ml	10.1007/s00044-013-0773-3

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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 NPC220173 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	332
0.1-0.2	1281
0.2-0.3	2744
0.3-0.4	6242
0.4-0.5	6259
0.5-0.6	3384
0.6-0.7	3642
0.7-0.8	4277
0.8-0.85	1437
0.85-0.9	763
0.9-0.95	354
0.95-1	174

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Similarity Score	Similarity Level	Natural Product ID
0.9415	High Similarity	NPC30011
0.9415	High Similarity	NPC97817
0.9415	High Similarity	NPC475179
0.9415	High Similarity	NPC64755
0.9415	High Similarity	NPC72554

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 NPC220173 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	878
0.2-0.3	1878
0.3-0.4	2656
0.4-0.5	1873
0.5-0.6	971
0.6-0.7	398
0.7-0.8	122
0.8-0.85	17
0.85-0.9	9
0.9-0.95	6
0.95-1	6

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6798	Remote Similarity	NPD5006	Approved
0.6798	Remote Similarity	NPD5005	Approved
0.6804	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD7907	Approved
0.6809	Remote Similarity	NPD5242	Approved

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Structure

CID220173 OpenBabel06191716012D 44 48 0 0 1 0 0 0 0 0999 V2000 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -6.5000 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 -2.5981 -3.5000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 -4.3301 1.5000 0.0000 C 0 0 1 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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 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 -1.7321 -5.0000 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 0.0000 1.0000 0.0000 C 0 0 2 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 -5.1962 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 2 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 -5.1962 -0.0000 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 -4.3301 -0.5000 0.0000 C 0 0 2 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 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 O 0 0 0 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 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 -1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 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 -0.8660 -1.5000 0.0000 O 0 0 0 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 2 39 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 12 1 0 0 0 0 5 10 2 0 0 0 0 5 14 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 15 2 0 0 0 0 8 29 1 0 0 0 0 9 1 1 6 0 0 0 9 18 1 0 0 0 0 9 40 1 0 0 0 0 10 24 1 0 0 0 0 11 30 1 0 0 0 0 12 14 2 0 0 0 0 12 31 1 0 0 0 0 13 17 2 0 0 0 0 13 32 1 0 0 0 0 14 39 1 0 0 0 0 15 17 1 0 0 0 0 15 41 1 0 0 0 0 16 8 1 1 0 0 0 16 19 1 0 0 0 0 16 42 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 18 33 1 1 0 0 0 19 22 1 0 0 0 0 19 34 1 6 0 0 0 20 25 1 0 0 0 0 20 35 2 0 0 0 0 21 23 1 0 0 0 0 21 36 1 6 0 0 0 22 26 1 0 0 0 0 22 37 1 1 0 0 0 23 27 1 0 0 0 0 23 38 1 6 0 0 0 24 25 2 0 0 0 0 24 41 1 0 0 0 0 25 43 1 0 0 0 0 26 28 1 0 0 0 0 26 44 1 6 0 0 0 27 40 1 0 0 0 0 27 44 1 1 0 0 0 28 42 1 0 0 0 0 28 43 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	11664505
ChEMBL	CHEMBL442566
ZINC

Physicochemical Properties

Molecular Weight:	624.17
ALogP:	-5.7305
MLogP:	2.78
XLogP:	-1.098
# Rotatable Bonds:	18
Polar Surface Area:	254.52
# H-Bond Aceptor:	11
# H-Bond Donor:	9
# Rings:	5
# Heavy Atoms:	44

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