NPASS Compound

Structure

NPC476302 OpenBabel07101719522D 67 67 0 0 1 0 0 0 0 0999 V2000 -5.5158 -4.6450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6522 -10.7263 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2509 -11.7444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2901 -7.2812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4539 -13.8850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9643 -7.6834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7733 -7.0956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6424 -1.1189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5559 -1.5257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5795 -9.0151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3885 -8.4273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1240 -11.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2285 -10.9467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7260 -3.0392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8306 -4.0337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7325 -1.3158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6280 -2.3103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1090 -5.5586 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 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9444 -4.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6576 -10.8308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6968 -6.3676 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1339 -13.0760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3511 -3.2361 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0699 -10.0218 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6913 -6.2631 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7634 -2.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4766 -9.1082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0981 -5.3495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7524 -2.2180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8724 -7.9856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4876 -9.3173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0918 -10.4399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3292 -2.8180 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 -5.8779 -8.0902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7469 -2.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4930 -9.4218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3150 -11.3534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9170 -3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1810 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3457 -3.1315 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0753 -10.1263 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.2791 -7.0721 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2728 -12.1625 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7688 -2.5316 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.4711 -9.0037 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5103 -4.5405 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0863 -10.3354 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.3347 -2.9225 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 1.1810 -1.7226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9499 -4.2541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1284 -13.1805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 -1.5135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8888 -8.2992 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0926 -5.2450 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1646 -1.4090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4602 -8.7947 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8943 -8.4038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4960 -9.6309 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7360 -1.9044 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.7045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 5 26 1 0 0 0 0 6 40 1 0 0 0 0 7 40 1 0 0 0 0 8 41 1 0 0 0 0 9 41 1 0 0 0 0 10 42 1 0 0 0 0 11 42 1 0 0 0 0 12 43 1 0 0 0 0 13 43 1 0 0 0 0 14 44 1 0 0 0 0 15 44 1 0 0 0 0 16 45 1 0 0 0 0 17 45 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 27 1 0 0 0 0 21 55 1 0 0 0 0 22 56 1 0 0 0 0 23 57 1 0 0 0 0 25 4 1 1 0 0 0 25 30 1 0 0 0 0 26 49 2 3 0 0 0 26 58 1 0 0 0 0 27 22 1 1 0 0 0 27 55 1 0 0 0 0 28 23 1 6 0 0 0 28 31 1 0 0 0 0 28 46 1 0 0 0 0 29 24 1 1 0 0 0 29 32 1 0 0 0 0 29 47 1 0 0 0 0 30 33 1 6 0 0 0 30 48 1 0 0 0 0 31 50 2 3 0 0 0 31 59 1 0 0 0 0 32 51 2 3 0 0 0 32 60 1 0 0 0 0 33 52 2 3 0 0 0 33 61 1 0 0 0 0 34 41 1 0 0 0 0 34 46 2 3 0 0 0 34 62 1 0 0 0 0 35 40 1 0 0 0 0 35 48 2 3 0 0 0 35 63 1 0 0 0 0 36 42 1 0 0 0 0 36 47 2 3 0 0 0 36 64 1 0 0 0 0 37 43 1 0 0 0 0 37 53 2 3 0 0 0 37 65 1 0 0 0 0 38 44 1 0 0 0 0 38 54 2 3 0 0 0 38 66 1 0 0 0 0 39 45 1 0 0 0 0 39 55 1 0 0 0 0 39 67 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 $$$$

Physi-Chem Properties

Molecular Weight:	952.6
Volume:	967.405
LogP:	0.942
LogD:	0.624
LogS:	-1.671
# Rotatable Bonds:	28
TPSA:	340.12
# H-Bond Aceptor:	22
# H-Bond Donor:	11
# Rings:	1
# Heavy Atoms:	22

MedChem Properties

QED Drug-Likeness Score:	0.052
Synthetic Accessibility Score:	6.029
Fsp3:	0.778
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.271
MDCK Permeability:	0.00012699203216470778
Pgp-inhibitor:	0.892
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.946
20% Bioavailability (F20%):	0.917
30% Bioavailability (F30%):	0.805

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.997
Plasma Protein Binding (PPB):	37.670814514160156%
Volume Distribution (VD):	0.777
Pgp-substrate:	37.6234130859375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.009
CYP2C19-inhibitor:	0.001
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.0
CYP2C9-substrate:	0.02
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.021
CYP3A4-inhibitor:	0.03
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	1.599
Half-life (T1/2):	0.577

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.852
Carcinogencity:	0.286
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.899

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC476302

Natural Product ID:	NPC476302
*Common Name:**	Aspereline E
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)-3-hydroxy-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:	Aspereline E
Standard InCHIKey:	RSDUGRUZONMYBE-KMMGOQOWSA-N
Standard InCHI:	InChI=1S/C45H80N10O12/c1-18-25(4)30(48-35(63)40(6,7)51-32(60)29(24(2)3)47-36(64)42(10,11)53-37(65)43(12,13)49-26(5)58)33(61)52-44(14,15)38(66)54-41(8,9)34(62)46-28(23-57)31(59)50-45(16,17)39(67)55-21-19-20-27(55)22-56/h24-25,27-30,56-57H,18-23H2,1-17H3,(H,46,62)(H,47,64)(H,48,63)(H,49,58)(H,50,59)(H,51,60)(H,52,61)(H,53,65)(H,54,66)/t25-,27+,28+,29+,30+/m1/s1
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)CO)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
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562942
PubChem CID:	45271730
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

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

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

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
NPT2705	Organism	Alternaria solani	Alternaria solani	IC50	>	100.0	ug.mL-1	PMID[524028]
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	IC50	>	100.0	ug.mL-1	PMID[524028]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC90	>	500.0	ug.mL-1	PMID[524028]
NPT19	Organism	Escherichia coli	Escherichia coli	IC90	>	500.0	ug.mL-1	PMID[524028]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC476302 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	251
0.1-0.2	17760
0.2-0.3	20351
0.3-0.4	2983
0.4-0.5	909
0.5-0.6	271
0.6-0.7	102
0.7-0.8	58
0.8-0.85	0
0.85-0.9	6
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9865	High Similarity	NPC476137
0.9865	High Similarity	NPC476156
0.9865	High Similarity	NPC476117
0.9865	High Similarity	NPC476243
0.973	High Similarity	NPC31756
0.8889	High Similarity	NPC477539
0.8161	Intermediate Similarity	NPC477538
0.7931	Intermediate Similarity	NPC275715
0.7912	Intermediate Similarity	NPC47076
0.7912	Intermediate Similarity	NPC134504
0.7848	Intermediate Similarity	NPC209156
0.7821	Intermediate Similarity	NPC76297
0.7821	Intermediate Similarity	NPC196007
0.7821	Intermediate Similarity	NPC214532
0.7805	Intermediate Similarity	NPC312315
0.7717	Intermediate Similarity	NPC473597
0.7625	Intermediate Similarity	NPC266888
0.7625	Intermediate Similarity	NPC256312
0.7625	Intermediate Similarity	NPC161774
0.7619	Intermediate Similarity	NPC470783
0.7529	Intermediate Similarity	NPC84128
0.7529	Intermediate Similarity	NPC53858
0.7473	Intermediate Similarity	NPC62263
0.7473	Intermediate Similarity	NPC471098
0.7473	Intermediate Similarity	NPC173763
0.7449	Intermediate Similarity	NPC241394
0.7444	Intermediate Similarity	NPC475801
0.7444	Intermediate Similarity	NPC474593
0.7407	Intermediate Similarity	NPC126186
0.7403	Intermediate Similarity	NPC128005
0.7403	Intermediate Similarity	NPC84182
0.7375	Intermediate Similarity	NPC470781
0.7363	Intermediate Similarity	NPC474576
0.7347	Intermediate Similarity	NPC128303
0.7229	Intermediate Similarity	NPC470782
0.7209	Intermediate Similarity	NPC475542
0.7188	Intermediate Similarity	NPC475440
0.7188	Intermediate Similarity	NPC220234
0.7129	Intermediate Similarity	NPC207820
0.7115	Intermediate Similarity	NPC63191
0.7115	Intermediate Similarity	NPC471202
0.71	Intermediate Similarity	NPC475637
0.7071	Intermediate Similarity	NPC476877
0.7013	Intermediate Similarity	NPC243964
0.7	Intermediate Similarity	NPC323720
0.697	Remote Similarity	NPC301148
0.697	Remote Similarity	NPC5864
0.697	Remote Similarity	NPC124554
0.6966	Remote Similarity	NPC472351
0.6933	Remote Similarity	NPC472578
0.6932	Remote Similarity	NPC184473
0.6931	Remote Similarity	NPC476876
0.6837	Remote Similarity	NPC475758
0.6832	Remote Similarity	NPC124549
0.68	Remote Similarity	NPC471097
0.68	Remote Similarity	NPC475149
0.6796	Remote Similarity	NPC67009
0.6768	Remote Similarity	NPC13175
0.6768	Remote Similarity	NPC475791
0.6744	Remote Similarity	NPC59867
0.6733	Remote Similarity	NPC198344
0.6707	Remote Similarity	NPC472579
0.6667	Remote Similarity	NPC473495
0.6667	Remote Similarity	NPC296043
0.6635	Remote Similarity	NPC296143
0.6635	Remote Similarity	NPC171734
0.6629	Remote Similarity	NPC23984
0.6606	Remote Similarity	NPC329216
0.6604	Remote Similarity	NPC476875
0.6577	Remote Similarity	NPC470652
0.6556	Remote Similarity	NPC6902
0.6518	Remote Similarity	NPC315188
0.6512	Remote Similarity	NPC327272
0.65	Remote Similarity	NPC475188
0.6486	Remote Similarity	NPC469899
0.6484	Remote Similarity	NPC235078
0.6429	Remote Similarity	NPC280066
0.6392	Remote Similarity	NPC315237
0.6374	Remote Similarity	NPC284456
0.6374	Remote Similarity	NPC246005
0.6372	Remote Similarity	NPC160688
0.6348	Remote Similarity	NPC470654
0.6348	Remote Similarity	NPC470653
0.6348	Remote Similarity	NPC470650
0.6327	Remote Similarity	NPC301010
0.6261	Remote Similarity	NPC50520
0.625	Remote Similarity	NPC314510
0.625	Remote Similarity	NPC155230
0.619	Remote Similarity	NPC250953
0.619	Remote Similarity	NPC306696
0.6186	Remote Similarity	NPC470655
0.6186	Remote Similarity	NPC470651
0.6118	Remote Similarity	NPC322274
0.6082	Remote Similarity	NPC322966
0.6047	Remote Similarity	NPC478256
0.604	Remote Similarity	NPC469739
0.6023	Remote Similarity	NPC178919
0.6	Remote Similarity	NPC38172
0.6	Remote Similarity	NPC34838
0.6	Remote Similarity	NPC292299
0.5983	Remote Similarity	NPC202521
0.5982	Remote Similarity	NPC103391
0.5982	Remote Similarity	NPC472536
0.596	Remote Similarity	NPC476019
0.5955	Remote Similarity	NPC86064
0.5952	Remote Similarity	NPC287693
0.5934	Remote Similarity	NPC473741
0.5934	Remote Similarity	NPC477145
0.5934	Remote Similarity	NPC325902
0.5926	Remote Similarity	NPC263207
0.5913	Remote Similarity	NPC477237
0.5909	Remote Similarity	NPC141325
0.5897	Remote Similarity	NPC476990
0.5889	Remote Similarity	NPC476130
0.5889	Remote Similarity	NPC476324
0.5882	Remote Similarity	NPC46427
0.5882	Remote Similarity	NPC6975
0.5882	Remote Similarity	NPC117829
0.5867	Remote Similarity	NPC80350
0.5843	Remote Similarity	NPC138435
0.5843	Remote Similarity	NPC320221
0.5843	Remote Similarity	NPC43219
0.5843	Remote Similarity	NPC263281
0.5833	Remote Similarity	NPC262615
0.5833	Remote Similarity	NPC128559
0.5812	Remote Similarity	NPC477238
0.5806	Remote Similarity	NPC130309
0.5798	Remote Similarity	NPC252878
0.5794	Remote Similarity	NPC141050
0.5783	Remote Similarity	NPC105297
0.5766	Remote Similarity	NPC251122
0.5761	Remote Similarity	NPC191774
0.5747	Remote Similarity	NPC29598
0.5747	Remote Similarity	NPC212866
0.573	Remote Similarity	NPC29326
0.5714	Remote Similarity	NPC287401
0.5699	Remote Similarity	NPC478017
0.5699	Remote Similarity	NPC315131
0.5699	Remote Similarity	NPC315535
0.5682	Remote Similarity	NPC476291
0.5673	Remote Similarity	NPC313821
0.567	Remote Similarity	NPC325723
0.5657	Remote Similarity	NPC324506
0.5652	Remote Similarity	NPC329077
0.5652	Remote Similarity	NPC473819
0.5641	Remote Similarity	NPC137327
0.5632	Remote Similarity	NPC10716
0.563	Remote Similarity	NPC200964

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476302 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	87
0.1-0.2	2329
0.2-0.3	5103
0.3-0.4	1204
0.4-0.5	331
0.5-0.6	72
0.6-0.7	14
0.7-0.8	8
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8272	Intermediate Similarity	NPD7763	Phase 2
0.8272	Intermediate Similarity	NPD7762	Phase 2
0.8022	Intermediate Similarity	NPD8038	Phase 2
0.8	Intermediate Similarity	NPD3723	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7760	Phase 2
0.8	Intermediate Similarity	NPD7759	Phase 2
0.8	Intermediate Similarity	NPD7841	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD2683	Discontinued
0.7363	Intermediate Similarity	NPD4261	Phase 1
0.7222	Intermediate Similarity	NPD3177	Phase 3
0.6932	Remote Similarity	NPD1125	Discovery
0.69	Remote Similarity	NPD6122	Discontinued
0.6813	Remote Similarity	NPD5791	Phase 2
0.6809	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD620	Approved
0.6591	Remote Similarity	NPD4815	Discontinued
0.6458	Remote Similarity	NPD5792	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD1456	Approved
0.6413	Remote Similarity	NPD3733	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD322	Phase 1
0.6381	Remote Similarity	NPD6937	Approved
0.6235	Remote Similarity	NPD1439	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD9425	Approved
0.6117	Remote Similarity	NPD6120	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD3715	Approved
0.6078	Remote Similarity	NPD3713	Approved
0.6078	Remote Similarity	NPD3714	Approved
0.6064	Remote Similarity	NPD9577	Approved
0.6047	Remote Similarity	NPD2220	Clinical (unspecified phase)
0.596	Remote Similarity	NPD2682	Approved
0.5882	Remote Similarity	NPD2263	Discontinued
0.5862	Remote Similarity	NPD9649	Approved
0.5833	Remote Similarity	NPD6437	Approved
0.5833	Remote Similarity	NPD6438	Approved
0.5825	Remote Similarity	NPD1784	Approved
0.581	Remote Similarity	NPD5359	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD7652	Discontinued
0.5761	Remote Similarity	NPD4278	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD7840	Approved
0.5747	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.573	Remote Similarity	NPD265	Phase 3
0.573	Remote Similarity	NPD266	Phase 3
0.5714	Remote Similarity	NPD4825	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD3189	Approved
0.5673	Remote Similarity	NPD3190	Approved
0.5673	Remote Similarity	NPD3191	Approved
0.5638	Remote Similarity	NPD9578	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD4829	Discontinued
0.562	Remote Similarity	NPD8041	Phase 2
0.561	Remote Similarity	NPD9671	Phase 2
0.561	Remote Similarity	NPD9670	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data