NPASS Natural Product

Natural Product: NPC209509

Natural Product ID:	NPC209509
Common Name:	Isaridine A
IUPAC Name:	(10S,13S,16S,19S)-10,16-dibenzyl-11,14-dimethyl-3-(2-methylpropyl)-13-propan-2-yl-4-oxa-1,8,11,14,17-pentazabicyclo[17.3.0]docosane-2,5,9,12,15,18-hexone
Synonyms:
Molecular Formula:	C39H53N5O7
Standard InCHIKey:	WLYWDCKLTCKHAK-AILSMDFESA-N
Standard InCHI:	InChI=1S/C39H53N5O7/c1-25(2)22-32-38(49)44-21-13-18-30(44)36(47)41-29(23-27-14-9-7-10-15-27)37(48)43(6)34(26(3)4)39(50)42(5)31(24-28-16-11-8-12-17-28)35(46)40-20-19-33(45)51-32/h7-12,14-17,25-26,29-32,34H,13,18-24H2,1-6H3,(H,40,46)(H,41,47)/t29-,30-,31-,32?,34-/m0/s1
Canonical SMILES:	CC(CC1OC(=O)CCN=C(O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H](N(C(=O)[C@@H](N=C([C@H]2N(C1=O)CCC2)O)Cc1ccccc1)C)C(C)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
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota				TCMID*

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Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Organism	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	230000	nM	17477570

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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 NPC209509 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	97
0.1-0.2	542
0.2-0.3	1765
0.3-0.4	9029
0.4-0.5	15783
0.5-0.6	2956
0.6-0.7	432
0.7-0.8	193
0.8-0.85	58
0.85-0.9	22
0.9-0.95	5
0.95-1	7

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Similarity Score	Similarity Level	Natural Product ID
0.7368	Intermediate Similarity	NPC299806
0.7375	Intermediate Similarity	NPC469898
0.7376	Intermediate Similarity	NPC478014
0.7376	Intermediate Similarity	NPC478015
0.7376	Intermediate Similarity	NPC478016

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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 NPC209509 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	94
0.1-0.2	289
0.2-0.3	580
0.3-0.4	1442
0.4-0.5	3732
0.5-0.6	2409
0.6-0.7	443
0.7-0.8	159
0.8-0.85	9
0.85-0.9	4
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6892	Remote Similarity	NPD5367	Discontinued
0.6894	Remote Similarity	NPD5638	Approved
0.6899	Remote Similarity	NPD1967	Approved
0.6899	Remote Similarity	NPD1968	Approved
0.6923	Remote Similarity	NPD2117	Pre-registration

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Structure

CID209509 OpenBabel06191716002D 51 54 0 0 1 0 0 0 0 0999 V2000 5.9197 2.9035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6099 2.7164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2225 -1.9713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2924 -3.3949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9785 0.0811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5374 -3.3747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5232 -5.6834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8226 -0.9797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5232 -4.7016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6729 -6.1743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9306 -0.0038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9234 -1.3741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0500 -2.0349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6729 -4.2106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8226 -5.6834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1395 0.5776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1323 -0.7926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2025 -2.5305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4633 2.6956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4814 2.6956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8406 -1.0757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6028 1.3462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9723 -4.2106 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6581 1.3462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7108 2.3220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3465 -2.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8226 -4.7016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2403 0.1832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9723 -3.2288 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4692 -1.8776 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2410 0.9518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7037 0.9518 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.3919 2.3768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4755 -1.8776 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7780 1.7737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8043 -2.5999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0039 -3.0672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9447 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0811 -0.9785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5528 2.3768 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.9408 -3.0672 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1404 -2.5999 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.8636 -0.9785 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.8592 3.2402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0557 2.4387 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4073 -3.3747 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6851 -3.9958 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9232 0.0811 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8707 -1.2195 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1667 1.7737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 42 1 0 0 0 0 6 43 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 11 16 1 0 0 0 0 12 17 2 0 0 0 0 13 18 1 0 0 0 0 13 21 1 0 0 0 0 14 27 2 0 0 0 0 15 27 1 0 0 0 0 16 28 2 0 0 0 0 17 28 1 0 0 0 0 19 20 1 0 0 0 0 19 33 1 0 0 0 0 20 40 1 0 0 0 0 21 44 1 0 0 0 0 22 25 1 0 0 0 0 22 32 1 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 29 23 1 1 0 0 0 29 37 1 0 0 0 0 29 41 1 0 0 0 0 30 18 1 1 0 0 0 30 36 1 0 0 0 0 30 44 1 0 0 0 0 31 24 1 1 0 0 0 31 35 1 0 0 0 0 31 42 1 0 0 0 0 32 38 1 0 0 0 0 32 51 1 0 0 0 0 33 45 2 0 0 0 0 33 51 1 0 0 0 0 34 26 1 1 0 0 0 34 39 1 0 0 0 0 34 43 1 0 0 0 0 35 40 2 3 0 0 0 35 46 1 0 0 0 0 36 41 2 3 0 0 0 36 47 1 0 0 0 0 37 43 1 0 0 0 0 37 48 2 0 0 0 0 38 44 1 0 0 0 0 38 49 2 0 0 0 0 39 42 1 0 0 0 0 39 50 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	12111222
ChEMBL	CHEMBL388055
ZINC

Physicochemical Properties

Molecular Weight:	703.39
ALogP:	-1.9556
MLogP:	4.43
XLogP:	8.078
# Rotatable Bonds:	15
Polar Surface Area:	152.41
# H-Bond Aceptor:	12
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	51

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