NPASS Natural Product

Natural Product: NPC238935

Natural Product ID:	NPC238935
Common Name:	3-O-Beta-D-Glucopyranosyl-28-O-Alpha-L-Rhamnopyranosyl-16Alpha-Hydrox Y-23-Deoxyprotobassic Acid
IUPAC Name:	[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl] (4aR,5R,6aR,6aS,6bR,8R,8aR,10R,11S,12aR,14bS)-5,8,11-trihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms:
Molecular Formula:	C42H68O15
Standard InCHIKey:	LZIMOIPXNDCZGQ-RFFVNIRISA-N
Standard InCHI:	InChI=1S/C42H68O15/c1-18-26(47)28(49)30(51)34(54-18)57-36(53)42-12-11-37(2,3)13-20(42)19-9-10-24-39(6)14-22(45)33(56-35-31(52)29(50)27(48)23(17-43)55-35)38(4,5)32(39)21(44)15-41(24,8)40(19,7)16-25(42)46/h9,18,20-35,43-52H,10-17H2,1-8H3/t18-,20-,21+,22-,23+,24+,25+,26-,27+,28+,29-,30+,31+,32-,33-,34-,35-,39+,40+,41+,42+/m0/s1
Canonical SMILES:	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O)C[C@]3([C@H](C2(C)C)[C@H](O)C[C@@]2([C@@H]3CC=C3[C@@]2(C)C[C@H]([C@@]2([C@H]3CC(C)(C)CC2)C(=O)O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O)C)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	Collection Location	Collection Time	Reference
NPO15083	Mussaenda macrophylla	Species	Rubiaceae	Eukaryota	Root barks			PMID[10543897]

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Biological Activity

Activity Type	# Activity
MIC	2

Activity Type	# Activity
Organism	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1127	Organism	Porphyromonas gingivalis	Porphyromonas gingivalis	MIC	=	312	ug/ml	21524573
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	>	1250	ug/ml	23368966

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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 NPC238935 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	179
0.1-0.2	957
0.2-0.3	3002
0.3-0.4	5294
0.4-0.5	9188
0.5-0.6	5701
0.6-0.7	3798
0.7-0.8	1832
0.8-0.85	417
0.85-0.9	209
0.9-0.95	197
0.95-1	115

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Similarity Score	Similarity Level	Natural Product ID
0.9352	High Similarity	NPC161717
0.9352	High Similarity	NPC79643
0.9352	High Similarity	NPC204414
0.9352	High Similarity	NPC250247
0.9352	High Similarity	NPC41061

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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 NPC238935 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1514
0.2-0.3	3671
0.3-0.4	2437
0.4-0.5	774
0.5-0.6	354
0.6-0.7	169
0.7-0.8	51
0.8-0.85	2
0.85-0.9	1
0.9-0.95	2
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6134	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.614	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6371	Approved
0.6148	Remote Similarity	NPD5223	Approved
0.6154	Remote Similarity	NPD6868	Approved

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Structure

NPC238935 OpenBabel07101719192D 57 63 0 0 1 0 0 0 0 0999 V2000 -8.0681 0.5350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0028 -4.2317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0335 -4.2317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0028 2.2932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0335 2.2932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6788 -0.9692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8394 1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8394 0.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8394 -1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3575 -2.9077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3575 -1.9385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6788 -2.9077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5181 -0.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6788 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8756 4.3615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1319 0.7858 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8394 -1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6788 -1.9385 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8394 1.4538 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3575 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0363 3.8769 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8394 -0.4846 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5181 -0.4846 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8811 1.7220 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1969 4.3615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9449 1.9729 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3575 3.8769 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2595 1.2876 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3575 2.9077 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6788 0.9692 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3575 0.9692 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5104 0.3513 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1969 2.4231 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8888 -0.0831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5181 -3.3923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5181 1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6788 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8394 -0.4846 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 -2.5181 -1.4538 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8756 5.3308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8394 2.4231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1969 -0.4846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3575 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5664 2.4074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1969 5.3308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6940 2.9091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5181 4.3615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3233 1.5384 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5181 2.4231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6380 0.8531 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4466 0.1005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0363 2.9077 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1969 1.4538 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8250 -0.3340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 37 1 0 0 0 0 3 37 1 0 0 0 0 4 38 1 0 0 0 0 5 38 1 0 0 0 0 7 40 1 0 0 0 0 9 10 1 0 0 0 0 9 19 2 0 0 0 0 10 24 1 0 0 0 0 11 12 1 0 0 0 0 11 37 1 0 0 0 0 12 42 1 0 0 0 0 13 20 1 0 0 0 0 13 37 1 0 0 0 0 14 22 1 0 0 0 0 14 39 1 0 0 0 0 15 21 1 0 0 0 0 15 41 1 0 0 0 0 16 25 1 0 0 0 0 16 40 1 0 0 0 0 17 43 1 0 0 0 0 18 1 1 1 0 0 0 18 26 1 0 0 0 0 18 54 1 0 0 0 0 19 20 1 0 0 0 0 19 40 1 0 0 0 0 20 42 1 6 0 0 0 21 32 1 0 0 0 0 21 44 1 1 0 0 0 22 33 1 0 0 0 0 22 45 1 1 0 0 0 23 17 1 1 0 0 0 23 27 1 0 0 0 0 23 55 1 0 0 0 0 24 39 1 1 0 0 0 24 41 1 0 0 0 0 25 42 1 6 0 0 0 25 46 1 0 0 0 0 26 28 1 0 0 0 0 26 47 1 6 0 0 0 27 29 1 0 0 0 0 27 48 1 6 0 0 0 28 30 1 0 0 0 0 28 49 1 1 0 0 0 29 31 1 0 0 0 0 29 50 1 1 0 0 0 30 34 1 0 0 0 0 30 51 1 1 0 0 0 31 35 1 0 0 0 0 31 52 1 6 0 0 0 32 38 1 0 0 0 0 32 39 1 1 0 0 0 33 38 1 0 0 0 0 33 56 1 1 0 0 0 34 54 1 0 0 0 0 34 57 1 6 0 0 0 35 55 1 0 0 0 0 35 56 1 1 0 0 0 36 53 2 0 0 0 0 36 57 1 0 0 0 0 39 6 1 1 0 0 0 40 41 1 1 0 0 0 41 8 1 1 0 0 0 42 36 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	21672204
ChEMBL	CHEMBL503292
ZINC

Physicochemical Properties

Molecular Weight:	812.46
ALogP:	-2.5836
MLogP:	4.43
XLogP:	3.414
# Rotatable Bonds:	24
Polar Surface Area:	256.29
# H-Bond Aceptor:	15
# H-Bond Donor:	10
# Rings:	7
# Heavy Atoms:	57

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