NPASS Natural Product

Natural Product: NPC476137

Natural Product ID:	NPC476137
Common Name:	Aspereline A
IUPAC Name:	(2S,3R)-2-[[2-[[(2S)-2-[[2-[(2-acetamido-2-methylpropanoyl)amino]-2-methylpropanoyl]amino]-3-methylbutanoyl]amino]-2-methylpropanoyl]amino]-N-[1-[[1-[[(2S)-1-[[1-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]-3-methylpentanamide
Synonyms:
Molecular Formula:	C45H80N10O11
Standard InCHIKey:	TYDXSTUVLGPNBK-LXEMEFDRSA-N
Standard InCHI:	InChI=1S/C45H80N10O11/c1-19-25(4)30(48-35(62)40(7,8)51-32(59)29(24(2)3)47-36(63)42(11,12)53-37(64)43(13,14)49-27(6)57)33(60)52-44(15,16)38(65)54-41(9,10)34(61)46-26(5)31(58)50-45(17,18)39(66)55-22-20-21-28(55)23-56/h24-26,28-30,56H,19-23H2,1-18H3,(H,46,61)(H,47,63)(H,48,62)(H,49,57)(H,50,58)(H,51,59)(H,52,60)(H,53,64)(H,54,65)/t25-,26+,28+,29+,30+/m1/s1
Canonical SMILES:	CC[C@H]([C@@H](C(=NC(C(=NC(C(=N[C@H](C(=NC(C(=O)N1CCC[C@H]1CO)(C)C)O)C)O)(C)C)O)(C)C)O)N=C(C(N=C([C@H](C(C)C)N=C(C(N=C(C(N=C(O)C)(C)C)O)(C)C)O)O)(C)C)O)C
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32776	trichoderma asperellum	Species	Hypocreaceae	Eukaryota				PMID[19514743]

Biological Activity

Activity Type	# Activity
IC50	2
Others	2

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC90	>	500	ug/ml	20709557
NPT19	Organism	Escherichia coli	Escherichia coli	IC90	>	500	ug/ml	20709557
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	100	ug/ml	DrugMatrix in vitro pharmacology data
NPT2705	Organism	Alternaria solani	Alternaria solani	IC50	>	100	ug/ml	DrugMatrix in vitro pharmacology data

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 NPC476137 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	68
0.1-0.2	11549
0.2-0.3	15455
0.3-0.4	2669
0.4-0.5	855
0.5-0.6	189
0.6-0.7	56
0.7-0.8	39
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476117
1.0	High Similarity	NPC476156
1.0	High Similarity	NPC476243
0.9865	High Similarity	NPC476302
0.9863	High Similarity	NPC31756
0.9	High Similarity	NPC477539
0.8256	Intermediate Similarity	NPC477538
0.8	Intermediate Similarity	NPC47076
0.8	Intermediate Similarity	NPC134504
0.7949	Intermediate Similarity	NPC209156
0.7922	Intermediate Similarity	NPC76297
0.7922	Intermediate Similarity	NPC214532
0.7922	Intermediate Similarity	NPC196007
0.7901	Intermediate Similarity	NPC312315
0.7816	Intermediate Similarity	NPC275715
0.7722	Intermediate Similarity	NPC161774
0.7722	Intermediate Similarity	NPC266888
0.7722	Intermediate Similarity	NPC256312
0.7711	Intermediate Similarity	NPC470783
0.7619	Intermediate Similarity	NPC84128
0.7619	Intermediate Similarity	NPC53858
0.7609	Intermediate Similarity	NPC473597
0.7556	Intermediate Similarity	NPC62263
0.7556	Intermediate Similarity	NPC471098
0.7556	Intermediate Similarity	NPC173763
0.7528	Intermediate Similarity	NPC474593
0.7528	Intermediate Similarity	NPC475801
0.7526	Intermediate Similarity	NPC241394
0.75	Intermediate Similarity	NPC84182
0.75	Intermediate Similarity	NPC128005
0.75	Intermediate Similarity	NPC126186
0.7468	Intermediate Similarity	NPC470781
0.7444	Intermediate Similarity	NPC474576
0.7423	Intermediate Similarity	NPC128303
0.7317	Intermediate Similarity	NPC470782
0.7294	Intermediate Similarity	NPC475542
0.72	Intermediate Similarity	NPC207820
0.7143	Intermediate Similarity	NPC476877
0.7105	Intermediate Similarity	NPC243964
0.7083	Intermediate Similarity	NPC475440
0.7083	Intermediate Similarity	NPC220234
0.7071	Intermediate Similarity	NPC323720
0.7045	Intermediate Similarity	NPC472351
0.7019	Intermediate Similarity	NPC63191
0.7019	Intermediate Similarity	NPC471202
0.7011	Intermediate Similarity	NPC184473
0.7	Intermediate Similarity	NPC476876
0.7	Intermediate Similarity	NPC475637
0.6907	Remote Similarity	NPC475758
0.6869	Remote Similarity	NPC475149
0.6869	Remote Similarity	NPC5864
0.6869	Remote Similarity	NPC471097
0.6869	Remote Similarity	NPC124554
0.6869	Remote Similarity	NPC301148
0.6837	Remote Similarity	NPC13175
0.6837	Remote Similarity	NPC475791
0.6824	Remote Similarity	NPC59867
0.68	Remote Similarity	NPC472578
0.6739	Remote Similarity	NPC473495
0.6733	Remote Similarity	NPC124549
0.6729	Remote Similarity	NPC296043
0.6705	Remote Similarity	NPC23984
0.6699	Remote Similarity	NPC67009
0.6667	Remote Similarity	NPC329216
0.6667	Remote Similarity	NPC476875
0.6634	Remote Similarity	NPC198344
0.6629	Remote Similarity	NPC6902
0.6588	Remote Similarity	NPC327272
0.6585	Remote Similarity	NPC472579
0.6566	Remote Similarity	NPC475188
0.6556	Remote Similarity	NPC235078
0.6545	Remote Similarity	NPC469899
0.6538	Remote Similarity	NPC296143
0.6538	Remote Similarity	NPC171734
0.6495	Remote Similarity	NPC280066
0.6486	Remote Similarity	NPC470652
0.6444	Remote Similarity	NPC246005
0.6444	Remote Similarity	NPC284456
0.6429	Remote Similarity	NPC160688
0.6429	Remote Similarity	NPC315188
0.6392	Remote Similarity	NPC301010
0.6329	Remote Similarity	NPC314510
0.6316	Remote Similarity	NPC155230
0.6316	Remote Similarity	NPC50520
0.6289	Remote Similarity	NPC315237
0.6265	Remote Similarity	NPC306696
0.6265	Remote Similarity	NPC250953
0.6261	Remote Similarity	NPC470654
0.6261	Remote Similarity	NPC470653
0.6261	Remote Similarity	NPC470650
0.619	Remote Similarity	NPC322274
0.6146	Remote Similarity	NPC322966
0.6102	Remote Similarity	NPC470651
0.6102	Remote Similarity	NPC470655
0.61	Remote Similarity	NPC469739
0.6092	Remote Similarity	NPC178919
0.6076	Remote Similarity	NPC34838
0.6076	Remote Similarity	NPC292299
0.6061	Remote Similarity	NPC38172
0.6024	Remote Similarity	NPC287693
0.602	Remote Similarity	NPC476019
0.6	Remote Similarity	NPC477145
0.6	Remote Similarity	NPC263207
0.6	Remote Similarity	NPC473741
0.5977	Remote Similarity	NPC141325
0.5955	Remote Similarity	NPC476130
0.5955	Remote Similarity	NPC476324
0.5946	Remote Similarity	NPC80350
0.5941	Remote Similarity	NPC117829
0.593	Remote Similarity	NPC478256
0.5909	Remote Similarity	NPC263281
0.5909	Remote Similarity	NPC138435
0.5909	Remote Similarity	NPC320221
0.5904	Remote Similarity	NPC128559
0.5904	Remote Similarity	NPC262615
0.5897	Remote Similarity	NPC202521
0.5893	Remote Similarity	NPC103391
0.5893	Remote Similarity	NPC472536
0.5854	Remote Similarity	NPC105297
0.5843	Remote Similarity	NPC86064
0.584	Remote Similarity	NPC141050
0.5826	Remote Similarity	NPC477237
0.5824	Remote Similarity	NPC191774
0.5824	Remote Similarity	NPC325902
0.5814	Remote Similarity	NPC212866
0.5814	Remote Similarity	NPC29598
0.5812	Remote Similarity	NPC476990
0.5798	Remote Similarity	NPC6975
0.5798	Remote Similarity	NPC46427
0.5795	Remote Similarity	NPC29326
0.576	Remote Similarity	NPC287401
0.5747	Remote Similarity	NPC476291
0.573	Remote Similarity	NPC43219
0.5726	Remote Similarity	NPC130309
0.5726	Remote Similarity	NPC477238
0.5714	Remote Similarity	NPC324506
0.5714	Remote Similarity	NPC252878
0.5698	Remote Similarity	NPC10716
0.5678	Remote Similarity	NPC200964
0.5676	Remote Similarity	NPC251122
0.5632	Remote Similarity	NPC193280
0.5632	Remote Similarity	NPC314273

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC476137 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	67
0.1-0.2	1284
0.2-0.3	5503
0.3-0.4	1650
0.4-0.5	527
0.5-0.6	100
0.6-0.7	19
0.7-0.8	6
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8375	Intermediate Similarity	NPD7763	Phase 2
0.8375	Intermediate Similarity	NPD7762	Phase 2
0.8095	Intermediate Similarity	NPD7760	Phase 2
0.8095	Intermediate Similarity	NPD7759	Phase 2
0.8095	Intermediate Similarity	NPD3723	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD8038	Phase 2
0.7889	Intermediate Similarity	NPD7841	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD2683	Discontinued
0.7253	Intermediate Similarity	NPD4261	Phase 1
0.7111	Intermediate Similarity	NPD3177	Phase 3
0.7011	Intermediate Similarity	NPD1125	Discovery
0.697	Remote Similarity	NPD6122	Discontinued
0.6889	Remote Similarity	NPD5791	Phase 2
0.6882	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.679	Remote Similarity	NPD620	Approved
0.6667	Remote Similarity	NPD4815	Discontinued
0.6533	Remote Similarity	NPD1456	Approved
0.6526	Remote Similarity	NPD5792	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD322	Phase 1
0.6442	Remote Similarity	NPD6937	Approved
0.631	Remote Similarity	NPD1439	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD9425	Approved
0.6176	Remote Similarity	NPD6120	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD3713	Approved
0.6139	Remote Similarity	NPD3714	Approved
0.6139	Remote Similarity	NPD3715	Approved
0.6129	Remote Similarity	NPD9577	Approved
0.6118	Remote Similarity	NPD2220	Clinical (unspecified phase)
0.602	Remote Similarity	NPD2682	Approved
0.593	Remote Similarity	NPD9649	Approved
0.5904	Remote Similarity	NPD6437	Approved
0.5904	Remote Similarity	NPD6438	Approved
0.5882	Remote Similarity	NPD1784	Approved
0.5865	Remote Similarity	NPD5359	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD4278	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD7840	Approved
0.5812	Remote Similarity	NPD7652	Discontinued
0.58	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD265	Phase 3
0.5795	Remote Similarity	NPD266	Phase 3
0.5769	Remote Similarity	NPD4825	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD2263	Discontinued
0.5699	Remote Similarity	NPD9578	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD4829	Discontinued
0.5679	Remote Similarity	NPD9670	Phase 2
0.5679	Remote Similarity	NPD9671	Phase 2
0.5667	Remote Similarity	NPD8041	Phase 2
0.5625	Remote Similarity	NPD584	Approved
0.5625	Remote Similarity	NPD843	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD581	Approved
0.5625	Remote Similarity	NPD583	Approved

Structure

NPC476137 OpenBabel07101719132D 66 66 0 0 1 0 0 0 0 0999 V2000 -9.5385 0.1317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4938 -4.2269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6749 -5.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5494 -0.0773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5659 -0.3909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6248 -10.2036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0051 -4.3079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0916 -3.9012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2803 2.3262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1938 1.9194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.1598 -6.8517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0553 -5.8571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1251 -10.0756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.9341 -9.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3639 0.4059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4685 -0.5886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4778 0.2900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3913 -0.1167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1317 -0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0816 -5.0359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1372 -0.8863 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5714 -0.4954 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.6193 -10.0991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0762 -4.9314 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7305 -1.7999 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1646 -1.4090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4829 -4.0179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7360 -1.9044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3903 1.2271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3128 -2.5044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6585 -5.6359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.4273 -8.1675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9671 0.6272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9006 -3.3134 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3848 1.3317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.2462 -6.4449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0206 -9.0810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5549 -0.1818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 0.3136 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -11.6639 -5.7404 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.3183 -2.6089 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -12.0260 -9.1856 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 -1.5135 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -10.8951 -3.2089 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.1482 -1.0954 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -12.8395 -7.3585 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.9726 0.5226 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 -2.0032 0.5909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.2071 -10.9081 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7524 -2.2180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4774 -3.9133 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3292 -2.8180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8025 2.0361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.7195 -1.5908 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.0652 -4.7224 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.4218 -8.0630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3739 1.5407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1810 -1.7226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 6 27 1 0 0 0 0 7 40 1 0 0 0 0 8 40 1 0 0 0 0 9 41 1 0 0 0 0 10 41 1 0 0 0 0 11 42 1 0 0 0 0 12 42 1 0 0 0 0 13 43 1 0 0 0 0 14 43 1 0 0 0 0 15 44 1 0 0 0 0 16 44 1 0 0 0 0 17 45 1 0 0 0 0 18 45 1 0 0 0 0 19 25 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 28 1 0 0 0 0 22 55 1 0 0 0 0 23 56 1 0 0 0 0 25 4 1 1 0 0 0 25 30 1 0 0 0 0 26 5 1 6 0 0 0 26 31 1 0 0 0 0 26 46 1 0 0 0 0 27 49 2 3 0 0 0 27 57 1 0 0 0 0 28 23 1 6 0 0 0 28 55 1 0 0 0 0 29 24 1 6 0 0 0 29 32 1 0 0 0 0 29 47 1 0 0 0 0 30 33 1 1 0 0 0 30 48 1 0 0 0 0 31 50 2 3 0 0 0 31 58 1 0 0 0 0 32 51 2 3 0 0 0 32 59 1 0 0 0 0 33 52 2 3 0 0 0 33 60 1 0 0 0 0 34 41 1 0 0 0 0 34 46 2 3 0 0 0 34 61 1 0 0 0 0 35 40 1 0 0 0 0 35 48 2 3 0 0 0 35 62 1 0 0 0 0 36 42 1 0 0 0 0 36 47 2 3 0 0 0 36 63 1 0 0 0 0 37 43 1 0 0 0 0 37 53 2 3 0 0 0 37 64 1 0 0 0 0 38 44 1 0 0 0 0 38 54 2 3 0 0 0 38 65 1 0 0 0 0 39 45 1 0 0 0 0 39 55 1 0 0 0 0 39 66 2 0 0 0 0 40 51 1 0 0 0 0 41 54 1 0 0 0 0 42 53 1 0 0 0 0 43 49 1 0 0 0 0 44 52 1 0 0 0 0 45 50 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	45270064
ChEMBL	CHEMBL539946
ZINC

Physicochemical Properties

Molecular Weight:	936.60
ALogP:	1.1914
MLogP:	4.1
XLogP:	3.551
# Rotatable Bonds:	51
Polar Surface Area:	333.85
# H-Bond Aceptor:	21
# H-Bond Donor:	10
# Rings:	1
# Heavy Atoms:	66

Download Data

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General Info & Identifiers & Properties
Structure MOL file
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Biological Activities
Similar NPs/Drugs