NPASS Natural Product

Natural Product: NPC196243

Natural Product ID:	NPC196243
Common Name:	Oscillamide C
IUPAC Name:	(2S)-2-[[(3S,6S,9S,12S,15R)-3-benzyl-12-[(2S)-butan-2-yl]-6,9-bis[2-(4-hydroxyphenyl)ethyl]-7-methyl-2,5,8,11,14-pentaoxo-1,4,7,10,13-pentazacyclononadec-15-yl]carbamoylamino]-5-(diaminomethylideneamino)pentanoic acid
Synonyms:	Oscillamide C
Molecular Formula:	C49H68N10O10
Standard InCHIKey:	TTWROJJNRKDVPJ-FVCPQTOGSA-N
Standard InCHI:	InChI=1S/C49H68N10O10/c1-4-30(2)41-45(65)54-37(25-19-31-15-21-34(60)22-16-31)46(66)59(3)40(26-20-32-17-23-35(61)24-18-32)44(64)55-39(29-33-11-6-5-7-12-33)42(62)52-27-9-8-13-36(43(63)58-41)56-49(69)57-38(47(67)68)14-10-28-53-48(50)51/h5-7,11-12,15-18,21-24,30,36-41,60-61H,4,8-10,13-14,19-20,25-29H2,1-3H3,(H,52,62)(H,54,65)(H,55,64)(H,58,63)(H,67,68)(H4,50,51,53)(H2,56,57,69)/t30-,36+,37-,38-,39-,40-,41-/m0/s1
Canonical SMILES:	CC[C@@H]([C@@H]1N=C(O)[C@@H](CCCCN=C([C@@H](N=C([C@@H](N(C(=O)[C@@H](N=C1O)CCc1ccc(cc1)O)C)CCc1ccc(cc1)O)O)Cc1ccccc1)O)N=C(N[C@H](C(=O)O)CCCNC(=N)N)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
NPO33422	planktothrix spp.	Species	Microcoleaceae	Bacteria				PMID[11520225]

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Biological Activity

Activity Type	# Activity
IC50	2
Others	2

Activity Type	# Activity
Others	4

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Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Inhibition	=	97.3	%	18942825
NPT2	Others	Unspecified	Inhibition	=	98.4	%	10924177
NPT2	Others	Unspecified	IC50	=	1330	nM	24224843
NPT2	Others	Unspecified	IC50	=	900	nM	15969497

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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 NPC196243 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	176
0.1-0.2	930
0.2-0.3	4226
0.3-0.4	8480
0.4-0.5	11452
0.5-0.6	4954
0.6-0.7	454
0.7-0.8	162
0.8-0.85	33
0.85-0.9	11
0.9-0.95	5
0.95-1	6

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Similarity Score	Similarity Level	Natural Product ID
0.707	Intermediate Similarity	NPC283760
0.7072	Intermediate Similarity	NPC315388
0.7083	Intermediate Similarity	NPC197921
0.7099	Intermediate Similarity	NPC296712
0.7102	Intermediate Similarity	NPC56635

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 NPC196243 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	133
0.1-0.2	380
0.2-0.3	710
0.3-0.4	1493
0.4-0.5	3184
0.5-0.6	2693
0.6-0.7	516
0.7-0.8	48
0.8-0.85	1
0.85-0.9	3
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6411	Remote Similarity	NPD3803	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD5746	Approved
0.6413	Remote Similarity	NPD7011	Discontinued
0.6416	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4256	Phase 2

Showing 1 to 5 of 200 entries

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Structure

NPC196243 OpenBabel07101719512D 69 72 0 0 1 0 0 0 0 0999 V2000 -3.9886 -5.0135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3437 -5.0791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9694 0.2455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0521 -5.3641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3467 4.7920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3467 3.7920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2128 5.2920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9722 -0.9966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8896 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2139 -6.1093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2128 3.2920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0788 4.7920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7267 -1.9660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4325 -5.1335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5844 -3.1711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2802 -1.5849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1625 4.0066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1098 2.5566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5586 -1.7754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3804 2.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5002 -3.5728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1959 -1.9866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9996 4.5536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9470 3.1036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7529 -2.3677 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4355 1.4627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4879 0.9158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2595 -6.4078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9448 3.2920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2802 -4.7284 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4744 -2.1771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2175 3.0082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0788 3.7920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3060 -2.9805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8919 4.1020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1798 -2.8032 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1629 -1.9660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3869 -4.8350 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9448 2.2920 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4017 0.9158 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4448 -3.7421 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9312 2.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3906 -3.4174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0790 1.6515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4990 -3.4174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0826 -0.9966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1227 -5.5123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0864 -7.6821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8699 -3.1819 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8677 -8.6579 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3506 -7.0049 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.8106 1.6515 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.0408 -7.3836 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7099 -2.8032 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9585 2.1274 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.9155 -3.4804 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.6056 -3.8592 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4448 -3.7421 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 5.2217 -3.3822 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7290 4.6490 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2559 3.0733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8666 -4.2968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4648 2.4406 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0230 -4.2968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0792 -1.0792 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9040 -6.4881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0771 -5.2138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0886 -2.2061 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 3 59 1 0 0 0 0 4 30 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 11 1 0 0 0 0 7 12 2 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 27 1 0 0 0 0 10 14 1 0 0 0 0 10 28 1 0 0 0 0 11 33 2 0 0 0 0 12 33 1 0 0 0 0 13 36 1 0 0 0 0 15 21 1 0 0 0 0 15 31 2 0 0 0 0 16 22 2 0 0 0 0 16 31 1 0 0 0 0 17 23 1 0 0 0 0 17 32 2 0 0 0 0 18 24 2 0 0 0 0 18 32 1 0 0 0 0 19 25 1 0 0 0 0 19 31 1 0 0 0 0 20 26 1 0 0 0 0 20 32 1 0 0 0 0 21 34 2 0 0 0 0 22 34 1 0 0 0 0 23 35 2 0 0 0 0 24 35 1 0 0 0 0 27 52 1 0 0 0 0 28 53 1 0 0 0 0 29 33 1 0 0 0 0 30 2 1 1 0 0 0 34 60 1 0 0 0 0 35 61 1 0 0 0 0 36 43 1 0 0 0 0 36 56 1 6 0 0 0 37 25 1 6 0 0 0 37 46 1 0 0 0 0 37 54 1 0 0 0 0 38 14 1 1 0 0 0 38 47 1 0 0 0 0 38 57 1 0 0 0 0 39 29 1 6 0 0 0 39 42 1 0 0 0 0 39 55 1 0 0 0 0 40 26 1 6 0 0 0 40 44 1 0 0 0 0 40 59 1 0 0 0 0 41 30 1 6 0 0 0 41 45 1 0 0 0 0 41 58 1 0 0 0 0 42 52 2 3 0 0 0 42 62 1 0 0 0 0 43 58 2 3 0 0 0 43 63 1 0 0 0 0 44 55 2 3 0 0 0 44 64 1 0 0 0 0 45 54 2 3 0 0 0 45 65 1 0 0 0 0 46 59 1 0 0 0 0 46 66 2 0 0 0 0 47 67 2 0 0 0 0 47 68 1 0 0 0 0 48 50 2 0 0 0 0 48 51 1 0 0 0 0 48 53 1 0 0 0 0 49 56 2 3 0 0 0 49 57 1 0 0 0 0 49 69 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11051314
ChEMBL	CHEMBL453427
ZINC

Physicochemical Properties

Molecular Weight:	956.51
ALogP:	-5.639
MLogP:	4.65
XLogP:	5.586
# Rotatable Bonds:	31
Polar Surface Area:	334.95
# H-Bond Aceptor:	18
# H-Bond Donor:	12
# Rings:	4
# Heavy Atoms:	69

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Structure MOL file
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