NPASS Compound

Structure

NPC471645 OpenBabel07101719132D 47 47 0 0 1 0 0 0 0 0999 V2000 5.9408 13.3799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2755 9.9791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2545 6.6689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2334 3.3587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6784 -4.9223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1235 1.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6479 -1.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9852 13.6747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2522 12.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4747 12.0196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7416 11.3394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7206 8.0292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9642 10.3645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4536 8.7094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9431 7.0543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4326 5.3992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4115 2.0890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8460 -1.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6995 4.7190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6784 1.4088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3460 -2.6228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9010 -3.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2311 9.6843 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.2100 6.3741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1890 3.0639 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.9010 -3.9474 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.9010 0.4339 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.6479 -1.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8460 -1.7568 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.9220 3.7441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9010 0.4339 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.8460 -3.4888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8019 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4254 -2.7317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6235 -0.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3460 -4.3548 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8019 -3.5135 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4254 -0.7818 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6235 -2.7317 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8776 3.4493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8460 -3.4888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6235 -4.2954 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4254 0.7818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3264 -3.1656 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5245 -0.3479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 28 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 12 15 1 0 0 0 0 13 23 1 0 0 0 0 14 23 1 0 0 0 0 15 24 2 0 0 0 0 16 19 2 0 0 0 0 16 24 1 0 0 0 0 17 20 1 0 0 0 0 17 25 1 0 0 0 0 18 21 1 0 0 0 0 18 29 1 0 0 0 0 19 30 1 0 0 0 0 20 31 1 0 0 0 0 21 32 1 0 0 0 0 22 26 1 0 0 0 0 22 38 1 0 0 0 0 25 30 1 0 0 0 0 26 33 1 0 0 0 0 27 31 1 0 0 0 0 27 34 1 0 0 0 0 28 35 1 0 0 0 0 28 39 1 0 0 0 0 29 36 1 0 0 0 0 29 40 1 0 0 0 0 30 41 2 0 0 0 0 31 47 1 0 0 0 0 32 37 2 0 0 0 0 32 42 1 0 0 0 0 33 40 2 3 0 0 0 33 43 1 0 0 0 0 34 39 2 3 0 0 0 34 44 1 0 0 0 0 35 38 2 3 0 0 0 35 45 1 0 0 0 0 36 46 2 0 0 0 0 36 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	658.43
Volume:	704.446
LogP:	3.912
LogD:	3.33
LogS:	-3.843
# Rotatable Bonds:	17
TPSA:	174.09
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.086
Synthetic Accessibility Score:	5.495
Fsp3:	0.694
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:	-5.052
MDCK Permeability:	5.881102697458118e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.318
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.215
Plasma Protein Binding (PPB):	98.53004455566406%
Volume Distribution (VD):	0.7
Pgp-substrate:	2.274343729019165%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.125
CYP2C19-substrate:	0.147
CYP2C9-inhibitor:	0.205
CYP2C9-substrate:	0.234
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.231
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	2.355
Half-life (T1/2):	0.273

ADMET: Toxicity

hERG Blockers:	0.11
Human Hepatotoxicity (H-HT):	0.584
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.445
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.623
Carcinogencity:	0.432
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.136

Download Data

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

Natural Product: NPC471645

Natural Product ID:	NPC471645
*Common Name:**	Fusaristatin A
IUPAC Name:	3-[6,13-dimethyl-10-methylidene-2,5,9,12-tetraoxo-14-[(5E,7E)-3,7,11-trimethyl-4-oxoheptadeca-5,7-dienyl]-1-oxa-4,8,11-triazacyclotetradec-3-yl]propanamide
Synonyms:
Standard InCHIKey:	MNMRSBPSTNMOQK-MAUBWLBLSA-N
Standard InCHI:	InChI=1S/C36H58N4O7/c1-8-9-10-11-13-23(2)14-12-15-24(3)16-19-30(41)25(4)17-20-31-27(6)34(44)39-28(7)35(45)38-22-26(5)33(43)40-29(36(46)47-31)18-21-32(37)42/h15-16,19,23,25-27,29,31H,7-14,17-18,20-22H2,1-6H3,(H2,37,42)(H,38,45)(H,39,44)(H,40,43)/b19-16+,24-15+
SMILES:	CCCCCCC(C)CCC=C(C)C=CC(=O)C(C)CCC1C(C(=O)NC(=C)C(=O)NCC(C(=O)NC(C(=O)O1)CCC(=O)N)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3086839
PubChem CID:	76327984
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21090694]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24175613]
NPO41424	Fusarium tricinctum + Bacillus subtilis 168 trpC2	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24175613]
NPO41423	Fusarium tricinctum + Bacillus subtilis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24175613]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
MIC	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	64.0	ug.mL-1	PMID[514904]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	64.0	ug.mL-1	PMID[514904]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	64.0	ug.mL-1	PMID[514904]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	>	64.0	ug.mL-1	PMID[514904]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	64.0	ug.mL-1	PMID[514904]
NPT2709	Organism	Bacillus subtilis subsp. subtilis str. 168	Bacillus subtilis subsp. subtilis str. 168	MIC	>	64.0	ug.mL-1	PMID[514904]

☑ 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 NPC471645 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	76
0.1-0.2	483
0.2-0.3	3522
0.3-0.4	21443
0.4-0.5	13180
0.5-0.6	3683
0.6-0.7	297
0.7-0.8	11
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7377	Intermediate Similarity	NPC316325
0.7217	Intermediate Similarity	NPC316250
0.719	Intermediate Similarity	NPC469865
0.7121	Intermediate Similarity	NPC314361
0.7119	Intermediate Similarity	NPC472615
0.7091	Intermediate Similarity	NPC39290
0.7091	Intermediate Similarity	NPC159369
0.7083	Intermediate Similarity	NPC473578
0.7083	Intermediate Similarity	NPC133729
0.7077	Intermediate Similarity	NPC329919
0.7077	Intermediate Similarity	NPC477793
0.7064	Intermediate Similarity	NPC472614
0.7034	Intermediate Similarity	NPC472616
0.7	Intermediate Similarity	NPC473249
0.6967	Remote Similarity	NPC21713
0.6967	Remote Similarity	NPC475608
0.696	Remote Similarity	NPC27413
0.696	Remote Similarity	NPC271621
0.696	Remote Similarity	NPC59751
0.6917	Remote Similarity	NPC315531
0.6891	Remote Similarity	NPC74035
0.6885	Remote Similarity	NPC477997
0.686	Remote Similarity	NPC475150
0.6842	Remote Similarity	NPC5418
0.6825	Remote Similarity	NPC475642
0.6797	Remote Similarity	NPC310467
0.6797	Remote Similarity	NPC473808
0.6786	Remote Similarity	NPC477729
0.6754	Remote Similarity	NPC472613
0.6746	Remote Similarity	NPC315652
0.6746	Remote Similarity	NPC7905
0.6744	Remote Similarity	NPC315915
0.6724	Remote Similarity	NPC195645
0.6724	Remote Similarity	NPC180722
0.6724	Remote Similarity	NPC175614
0.6724	Remote Similarity	NPC165332
0.672	Remote Similarity	NPC5485
0.6719	Remote Similarity	NPC169328
0.6694	Remote Similarity	NPC473252
0.6694	Remote Similarity	NPC154601
0.6641	Remote Similarity	NPC16709
0.6641	Remote Similarity	NPC315783
0.6641	Remote Similarity	NPC9714
0.6641	Remote Similarity	NPC314629
0.664	Remote Similarity	NPC1111
0.664	Remote Similarity	NPC261750
0.6639	Remote Similarity	NPC313234
0.6638	Remote Similarity	NPC189764
0.6638	Remote Similarity	NPC233273
0.6638	Remote Similarity	NPC205546
0.6638	Remote Similarity	NPC50902
0.6636	Remote Similarity	NPC227051
0.6615	Remote Similarity	NPC475383
0.6615	Remote Similarity	NPC156379
0.6615	Remote Similarity	NPC314293
0.6614	Remote Similarity	NPC30196
0.6612	Remote Similarity	NPC14537
0.6607	Remote Similarity	NPC477959
0.6589	Remote Similarity	NPC241050
0.6583	Remote Similarity	NPC72401
0.6583	Remote Similarity	NPC325339
0.6569	Remote Similarity	NPC78189
0.6565	Remote Similarity	NPC190663
0.6562	Remote Similarity	NPC6531
0.6562	Remote Similarity	NPC201968
0.6557	Remote Similarity	NPC271269
0.6557	Remote Similarity	NPC475918
0.6557	Remote Similarity	NPC201128
0.6555	Remote Similarity	NPC473224
0.6545	Remote Similarity	NPC145748
0.6545	Remote Similarity	NPC155670
0.6545	Remote Similarity	NPC95478
0.6532	Remote Similarity	NPC298484
0.6529	Remote Similarity	NPC215988
0.6529	Remote Similarity	NPC469895
0.6525	Remote Similarity	NPC476344
0.6519	Remote Similarity	NPC316205
0.6519	Remote Similarity	NPC315387
0.6518	Remote Similarity	NPC122502
0.6512	Remote Similarity	NPC296361
0.6508	Remote Similarity	NPC60432
0.6504	Remote Similarity	NPC251330
0.6496	Remote Similarity	NPC150041
0.6493	Remote Similarity	NPC204556
0.6476	Remote Similarity	NPC86064
0.6475	Remote Similarity	NPC205176
0.6475	Remote Similarity	NPC472430
0.6471	Remote Similarity	NPC234542
0.6471	Remote Similarity	NPC132931
0.6466	Remote Similarity	NPC160493
0.6462	Remote Similarity	NPC313802
0.6462	Remote Similarity	NPC477515
0.6462	Remote Similarity	NPC314268
0.6462	Remote Similarity	NPC67917
0.646	Remote Similarity	NPC86005
0.6455	Remote Similarity	NPC474312
0.6452	Remote Similarity	NPC70235
0.6441	Remote Similarity	NPC123141
0.6441	Remote Similarity	NPC475503
0.6439	Remote Similarity	NPC80150
0.6439	Remote Similarity	NPC273185
0.6435	Remote Similarity	NPC313670
0.6429	Remote Similarity	NPC230889
0.6429	Remote Similarity	NPC29501
0.6429	Remote Similarity	NPC170375
0.6418	Remote Similarity	NPC309525
0.6406	Remote Similarity	NPC103391
0.6406	Remote Similarity	NPC472536
0.6406	Remote Similarity	NPC50694
0.6403	Remote Similarity	NPC472428
0.64	Remote Similarity	NPC329305
0.6393	Remote Similarity	NPC474563
0.6387	Remote Similarity	NPC475646
0.6381	Remote Similarity	NPC43219
0.6379	Remote Similarity	NPC314500
0.6372	Remote Similarity	NPC164393
0.6364	Remote Similarity	NPC469515
0.6349	Remote Similarity	NPC476290
0.6349	Remote Similarity	NPC127578
0.6343	Remote Similarity	NPC470650
0.6343	Remote Similarity	NPC314512
0.6343	Remote Similarity	NPC470654
0.6343	Remote Similarity	NPC470653
0.6343	Remote Similarity	NPC313333
0.6343	Remote Similarity	NPC313342
0.6343	Remote Similarity	NPC314451
0.632	Remote Similarity	NPC307903
0.632	Remote Similarity	NPC140251
0.6316	Remote Similarity	NPC478015
0.6316	Remote Similarity	NPC478014
0.6316	Remote Similarity	NPC478016
0.6308	Remote Similarity	NPC209734
0.6304	Remote Similarity	NPC120335
0.6301	Remote Similarity	NPC316249
0.6288	Remote Similarity	NPC237420
0.6279	Remote Similarity	NPC476814
0.6279	Remote Similarity	NPC476813
0.6276	Remote Similarity	NPC193753
0.6276	Remote Similarity	NPC160222
0.6276	Remote Similarity	NPC91953
0.627	Remote Similarity	NPC24389
0.626	Remote Similarity	NPC55336
0.625	Remote Similarity	NPC476269
0.625	Remote Similarity	NPC475438
0.625	Remote Similarity	NPC170377
0.625	Remote Similarity	NPC265662
0.624	Remote Similarity	NPC315426
0.6239	Remote Similarity	NPC319473
0.6239	Remote Similarity	NPC474833
0.623	Remote Similarity	NPC175531
0.6228	Remote Similarity	NPC316426
0.6228	Remote Similarity	NPC315395
0.6222	Remote Similarity	NPC469494
0.622	Remote Similarity	NPC122926
0.622	Remote Similarity	NPC113012
0.6207	Remote Similarity	NPC197921
0.6202	Remote Similarity	NPC273814
0.6195	Remote Similarity	NPC472957
0.6195	Remote Similarity	NPC472958
0.619	Remote Similarity	NPC171734
0.619	Remote Similarity	NPC471636
0.619	Remote Similarity	NPC287572
0.619	Remote Similarity	NPC207820
0.6187	Remote Similarity	NPC139585
0.6187	Remote Similarity	NPC316401
0.6186	Remote Similarity	NPC476049
0.6183	Remote Similarity	NPC476190
0.6183	Remote Similarity	NPC147707
0.6182	Remote Similarity	NPC314854
0.6182	Remote Similarity	NPC313911
0.6172	Remote Similarity	NPC12270
0.6167	Remote Similarity	NPC473291
0.6164	Remote Similarity	NPC469360
0.6161	Remote Similarity	NPC47135
0.616	Remote Similarity	NPC472433
0.6159	Remote Similarity	NPC315809
0.6159	Remote Similarity	NPC314050
0.6148	Remote Similarity	NPC316133
0.6148	Remote Similarity	NPC318445
0.6143	Remote Similarity	NPC133089
0.6142	Remote Similarity	NPC474725
0.614	Remote Similarity	NPC197903
0.614	Remote Similarity	NPC99395
0.614	Remote Similarity	NPC137033
0.6131	Remote Similarity	NPC314282
0.6126	Remote Similarity	NPC474510
0.6121	Remote Similarity	NPC227379
0.6121	Remote Similarity	NPC474471
0.6119	Remote Similarity	NPC315188
0.6111	Remote Similarity	NPC477462
0.6111	Remote Similarity	NPC475800
0.6107	Remote Similarity	NPC477554
0.6106	Remote Similarity	NPC11620
0.6103	Remote Similarity	NPC204639
0.6102	Remote Similarity	NPC472264
0.6098	Remote Similarity	NPC474873
0.6095	Remote Similarity	NPC478256
0.6091	Remote Similarity	NPC478017
0.6091	Remote Similarity	NPC315131
0.6091	Remote Similarity	NPC192006

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 NPC471645 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	74
0.1-0.2	312
0.2-0.3	2337
0.3-0.4	4414
0.4-0.5	1777
0.5-0.6	205
0.6-0.7	28
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7377	Intermediate Similarity	NPD7500	Approved
0.725	Intermediate Similarity	NPD7116	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7739	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6413	Approved
0.7	Intermediate Similarity	NPD7746	Phase 1
0.7	Intermediate Similarity	NPD7747	Phase 1
0.6953	Remote Similarity	NPD7623	Phase 3
0.6953	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6421	Discontinued
0.6772	Remote Similarity	NPD7641	Discontinued
0.6724	Remote Similarity	NPD7839	Suspended
0.6716	Remote Similarity	NPD6914	Discontinued
0.6641	Remote Similarity	NPD7829	Approved
0.6641	Remote Similarity	NPD7830	Approved
0.6609	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6094	Approved
0.6579	Remote Similarity	NPD6095	Approved
0.6529	Remote Similarity	NPD2258	Approved
0.6529	Remote Similarity	NPD2259	Approved
0.6489	Remote Similarity	NPD8444	Approved
0.6429	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7983	Approved
0.6349	Remote Similarity	NPD6420	Discontinued
0.6343	Remote Similarity	NPD8299	Approved
0.6343	Remote Similarity	NPD8340	Approved
0.6343	Remote Similarity	NPD8341	Approved
0.6343	Remote Similarity	NPD8342	Approved
0.6308	Remote Similarity	NPD7505	Discontinued
0.6303	Remote Similarity	NPD4228	Discovery
0.6232	Remote Similarity	NPD8391	Approved
0.6232	Remote Similarity	NPD8390	Approved
0.6232	Remote Similarity	NPD8392	Approved
0.6176	Remote Similarity	NPD8451	Approved
0.6172	Remote Similarity	NPD1719	Phase 1
0.6165	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD7345	Approved
0.6148	Remote Similarity	NPD7642	Approved
0.6131	Remote Similarity	NPD8448	Approved
0.6091	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6935	Phase 3
0.6061	Remote Similarity	NPD6936	Clinical (unspecified phase)
0.605	Remote Similarity	NPD5778	Approved
0.605	Remote Similarity	NPD5779	Approved
0.6032	Remote Similarity	NPD4211	Phase 1
0.6	Remote Similarity	NPD8394	Approved
0.5946	Remote Similarity	NPD3732	Approved
0.5942	Remote Similarity	NPD4816	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD8273	Phase 1
0.594	Remote Similarity	NPD1348	Approved
0.5931	Remote Similarity	NPD6333	Approved
0.5931	Remote Similarity	NPD6334	Approved
0.5926	Remote Similarity	NPD2217	Approved
0.5926	Remote Similarity	NPD2218	Phase 2
0.5918	Remote Similarity	NPD6077	Discontinued
0.5903	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD8074	Phase 3
0.5896	Remote Similarity	NPD6918	Phase 1
0.5887	Remote Similarity	NPD6404	Discontinued
0.5882	Remote Similarity	NPD7838	Discovery
0.5877	Remote Similarity	NPD6435	Approved
0.585	Remote Similarity	NPD6852	Discontinued
0.5839	Remote Similarity	NPD8080	Discontinued
0.5833	Remote Similarity	NPD8415	Approved
0.5826	Remote Similarity	NPD7154	Phase 3
0.5811	Remote Similarity	NPD6865	Phase 2
0.5811	Remote Similarity	NPD6864	Phase 2
0.5798	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD6101	Approved
0.5782	Remote Similarity	NPD8173	Phase 2
0.5782	Remote Similarity	NPD8172	Phase 2
0.5781	Remote Similarity	NPD5357	Phase 1
0.5781	Remote Similarity	NPD1040	Phase 2
0.5764	Remote Similarity	NPD4738	Phase 2
0.575	Remote Similarity	NPD6698	Approved
0.575	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.575	Remote Similarity	NPD46	Approved
0.5745	Remote Similarity	NPD8337	Approved
0.5745	Remote Similarity	NPD8336	Approved
0.5734	Remote Similarity	NPD7260	Phase 2
0.5726	Remote Similarity	NPD5363	Approved
0.5725	Remote Similarity	NPD2838	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD1376	Discontinued
0.5704	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD6411	Approved
0.5702	Remote Similarity	NPD5368	Approved
0.5694	Remote Similarity	NPD8338	Approved
0.5691	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5688	Remote Similarity	NPD6944	Clinical (unspecified phase)
0.568	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD5786	Approved
0.5662	Remote Similarity	NPD7756	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD2252	Approved
0.5656	Remote Similarity	NPD2251	Approved
0.5652	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6908	Approved
0.5652	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD6909	Approved
0.5652	Remote Similarity	NPD5981	Approved
0.5646	Remote Similarity	NPD8265	Approved
0.562	Remote Similarity	NPD2132	Phase 3
0.562	Remote Similarity	NPD5785	Approved

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