NPASS Compound

Structure

CID314693 OpenBabel06191716122D 51 53 0 0 1 0 0 0 0 0999 V2000 4.6621 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2087 -1.0038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9737 -4.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1920 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4271 -5.2038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8804 -4.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2917 -3.5022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4271 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0097 1.3400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8444 1.3400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5669 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2872 1.1590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2142 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0743 -3.6685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0924 -2.2673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5097 -3.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8444 -4.1425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2737 -2.1009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8541 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0743 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2142 -1.1083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5669 -3.9615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7798 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4271 -4.2038 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2872 -3.9615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3782 -3.0955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8541 -2.8025 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3601 -1.6942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5097 0.4740 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0924 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4489 -2.2820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3444 -3.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8229 -1.2695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2383 -0.5352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0097 -4.1425 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7798 -3.6685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5692 -3.6832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -1.1083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4793 -2.1429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3444 0.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8118 -1.1213 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 5.7201 -3.3025 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2529 1.1431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0435 -0.2262 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2176 -5.1207 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1920 -4.4776 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6737 -4.6778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3546 -1.0038 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1021 -2.9252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3988 1.1431 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 21 1 0 0 0 0 4 23 1 0 0 0 0 6 25 1 0 0 0 0 7 26 1 0 0 0 0 8 9 1 0 0 0 0 8 10 2 0 0 0 0 9 11 2 0 0 0 0 10 12 1 0 0 0 0 11 20 1 0 0 0 0 12 23 2 0 0 0 0 13 15 1 0 0 0 0 13 21 2 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 27 1 0 0 0 0 16 27 1 0 0 0 0 17 24 1 0 0 0 0 17 25 2 0 0 0 0 18 26 2 0 0 0 0 18 28 1 0 0 0 0 19 29 1 0 0 0 0 19 30 1 0 0 0 0 20 1 1 6 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 3 1 6 0 0 0 22 35 1 0 0 0 0 23 40 1 0 0 0 0 24 5 1 1 0 0 0 24 35 1 0 0 0 0 25 36 1 0 0 0 0 26 37 1 0 0 0 0 27 43 1 6 0 0 0 28 31 2 0 0 0 0 28 38 1 0 0 0 0 29 44 1 1 0 0 0 30 45 2 0 0 0 0 31 32 1 0 0 0 0 31 39 1 0 0 0 0 32 36 1 0 0 0 0 32 37 2 0 0 0 0 33 34 2 0 0 0 0 33 39 1 0 0 0 0 33 41 1 0 0 0 0 34 38 1 0 0 0 0 34 42 1 0 0 0 0 35 46 1 6 0 0 0 36 47 2 0 0 0 0 37 48 1 0 0 0 0 38 49 2 0 0 0 0 39 50 2 0 0 0 0 40 42 2 3 0 0 0 40 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	700.34
Volume:	736.285
LogP:	4.107
LogD:	2.49
LogS:	-3.704
# Rotatable Bonds:	0
TPSA:	210.64
# H-Bond Aceptor:	11
# H-Bond Donor:	9
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.055
Synthetic Accessibility Score:	6.818
Fsp3:	0.325
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.308
MDCK Permeability:	1.0857977940759156e-05
Pgp-inhibitor:	0.097
Pgp-substrate:	0.984
Human Intestinal Absorption (HIA):	0.345
20% Bioavailability (F20%):	0.883
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	93.3375015258789%
Volume Distribution (VD):	0.776
Pgp-substrate:	6.891232013702393%

ADMET: Metabolism

CYP1A2-inhibitor:	0.317
CYP1A2-substrate:	0.079
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.69
CYP2C9-substrate:	0.683
CYP2D6-inhibitor:	0.119
CYP2D6-substrate:	0.179
CYP3A4-inhibitor:	0.048
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	1.491
Half-life (T1/2):	0.303

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.455
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.345
Rat Oral Acute Toxicity:	0.195
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.932
Carcinogencity:	0.741
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.914

Download Data

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

Natural Product: NPC314693

Natural Product ID:	NPC314693
*Common Name:**	Naphthomycin L
IUPAC Name:	n.a.
Synonyms:	Naphthomycin L
Standard InCHIKey:	JUWFHSXVGJIUPA-UMKVKWLOSA-N
Standard InCHI:	InChI=1S/C40H48N2O9/c1-20-11-9-8-10-12-23(4)40(51)42-34-33(41)39(50)31-28(38(34)49)18-26(7)37(48)32(31)36(47)25(6)17-24(5)35(46)22(3)14-16-27(43)15-13-21(2)30(45)19-29(20)44/h8-14,16-18,20,22,24,27,29,35,43-44,46,48H,15,19,41H2,1-7H3,(H,42,51)/b10-8-,11-9+,16-14+,21-13+,23-12-,25-17+/t20-,22-,24-,27-,29-,35-/m0/s1
SMILES:	CC1C=CC=CC=C(C(=O)NC2=C(C(=O)C3=C(C2=O)C=C(C(=C3C(=O)C(=CC(C(C(C=CC(CC=C(C(=O)CC1O)C)O)C)O)C)C)O)C)N)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2172470
PubChem CID:	60201879
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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
NPO32848	Streptomyces sp. CS	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22742732]

☑ 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	5

Activity Type	# Activity
Organism	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT826	Organism	Magnaporthe oryzae	Magnaporthe oryzae	MIC	=	600.0	ug.mL-1	PMID[509042]
NPT610	Others	Molecular identity unknown		MIC	=	600.0	ug.mL-1	PMID[509042]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	MIC	=	600.0	ug.mL-1	PMID[509042]
NPT2781	Organism	Fusarium moniliforme	Gibberella moniliformis	MIC	=	300.0	ug.mL-1	PMID[509042]

☑ 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 NPC314693 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	234
0.1-0.2	1135
0.2-0.3	3716
0.3-0.4	11187
0.4-0.5	8527
0.5-0.6	12600
0.6-0.7	4986
0.7-0.8	301
0.8-0.85	3
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9427	High Similarity	NPC101207
0.9371	High Similarity	NPC12890
0.9012	High Similarity	NPC163924
0.9012	High Similarity	NPC54661
0.8848	High Similarity	NPC315406
0.8743	High Similarity	NPC313708
0.8141	Intermediate Similarity	NPC238108
0.7785	Intermediate Similarity	NPC236795
0.7688	Intermediate Similarity	NPC313453
0.7625	Intermediate Similarity	NPC86524
0.759	Intermediate Similarity	NPC314437
0.7578	Intermediate Similarity	NPC475957
0.7547	Intermediate Similarity	NPC52407
0.7547	Intermediate Similarity	NPC53896
0.7516	Intermediate Similarity	NPC315275
0.75	Intermediate Similarity	NPC50924
0.7485	Intermediate Similarity	NPC143685
0.7485	Intermediate Similarity	NPC162939
0.7484	Intermediate Similarity	NPC110609
0.7484	Intermediate Similarity	NPC246693
0.7484	Intermediate Similarity	NPC242358
0.747	Intermediate Similarity	NPC79627
0.747	Intermediate Similarity	NPC469854
0.747	Intermediate Similarity	NPC469856
0.7455	Intermediate Similarity	NPC471971
0.7455	Intermediate Similarity	NPC30846
0.7455	Intermediate Similarity	NPC469855
0.7455	Intermediate Similarity	NPC471972
0.7455	Intermediate Similarity	NPC193555
0.7455	Intermediate Similarity	NPC135524
0.7453	Intermediate Similarity	NPC80035
0.7438	Intermediate Similarity	NPC115458
0.7436	Intermediate Similarity	NPC15837
0.7423	Intermediate Similarity	NPC4214
0.7423	Intermediate Similarity	NPC13715
0.7421	Intermediate Similarity	NPC17083
0.7407	Intermediate Similarity	NPC474311
0.7403	Intermediate Similarity	NPC307174
0.7403	Intermediate Similarity	NPC282577
0.7403	Intermediate Similarity	NPC469973
0.7394	Intermediate Similarity	NPC305845
0.7394	Intermediate Similarity	NPC204045
0.7391	Intermediate Similarity	NPC202225
0.7384	Intermediate Similarity	NPC96160
0.7384	Intermediate Similarity	NPC4331
0.7381	Intermediate Similarity	NPC471970
0.7375	Intermediate Similarity	NPC58685
0.7362	Intermediate Similarity	NPC471452
0.7358	Intermediate Similarity	NPC199253
0.7358	Intermediate Similarity	NPC136588
0.7358	Intermediate Similarity	NPC31799
0.7349	Intermediate Similarity	NPC474961
0.7346	Intermediate Similarity	NPC283088
0.7342	Intermediate Similarity	NPC96024
0.7337	Intermediate Similarity	NPC295531
0.7333	Intermediate Similarity	NPC181560
0.7333	Intermediate Similarity	NPC315578
0.7333	Intermediate Similarity	NPC169452
0.7329	Intermediate Similarity	NPC78307
0.7329	Intermediate Similarity	NPC254603
0.7329	Intermediate Similarity	NPC477139
0.7325	Intermediate Similarity	NPC306765
0.7317	Intermediate Similarity	NPC33011
0.7312	Intermediate Similarity	NPC471851
0.7312	Intermediate Similarity	NPC93015
0.7312	Intermediate Similarity	NPC244699
0.7308	Intermediate Similarity	NPC74507
0.7308	Intermediate Similarity	NPC68756
0.7308	Intermediate Similarity	NPC199273
0.7308	Intermediate Similarity	NPC234890
0.7308	Intermediate Similarity	NPC152525
0.7305	Intermediate Similarity	NPC66593
0.7301	Intermediate Similarity	NPC272268
0.7299	Intermediate Similarity	NPC474861
0.7299	Intermediate Similarity	NPC313299
0.7297	Intermediate Similarity	NPC329790
0.7296	Intermediate Similarity	NPC474546
0.7296	Intermediate Similarity	NPC34414
0.7296	Intermediate Similarity	NPC25736
0.7296	Intermediate Similarity	NPC146647
0.7278	Intermediate Similarity	NPC72667
0.7278	Intermediate Similarity	NPC136878
0.7273	Intermediate Similarity	NPC242994
0.7273	Intermediate Similarity	NPC26924
0.7273	Intermediate Similarity	NPC138099
0.7267	Intermediate Similarity	NPC70622
0.7262	Intermediate Similarity	NPC29932
0.7262	Intermediate Similarity	NPC471906
0.7262	Intermediate Similarity	NPC244691
0.7261	Intermediate Similarity	NPC123506
0.7256	Intermediate Similarity	NPC305060
0.7251	Intermediate Similarity	NPC474310
0.725	Intermediate Similarity	NPC117609
0.725	Intermediate Similarity	NPC55949
0.725	Intermediate Similarity	NPC198305
0.7246	Intermediate Similarity	NPC239136
0.7246	Intermediate Similarity	NPC19631
0.7246	Intermediate Similarity	NPC73061
0.7246	Intermediate Similarity	NPC469520
0.7239	Intermediate Similarity	NPC258502
0.7235	Intermediate Similarity	NPC478018
0.7233	Intermediate Similarity	NPC48248
0.7233	Intermediate Similarity	NPC3009
0.7222	Intermediate Similarity	NPC225051
0.7222	Intermediate Similarity	NPC314048
0.7219	Intermediate Similarity	NPC34482
0.7219	Intermediate Similarity	NPC478019
0.7216	Intermediate Similarity	NPC326084
0.7215	Intermediate Similarity	NPC231774
0.7215	Intermediate Similarity	NPC71610
0.7215	Intermediate Similarity	NPC254492
0.7215	Intermediate Similarity	NPC3224
0.7212	Intermediate Similarity	NPC46242
0.7212	Intermediate Similarity	NPC473479
0.7212	Intermediate Similarity	NPC51531
0.7212	Intermediate Similarity	NPC297797
0.7212	Intermediate Similarity	NPC87723
0.7212	Intermediate Similarity	NPC165191
0.7212	Intermediate Similarity	NPC289358
0.7212	Intermediate Similarity	NPC28592
0.7212	Intermediate Similarity	NPC5014
0.7212	Intermediate Similarity	NPC50615
0.7212	Intermediate Similarity	NPC473779
0.7212	Intermediate Similarity	NPC469857
0.7212	Intermediate Similarity	NPC477849
0.7212	Intermediate Similarity	NPC149773
0.7212	Intermediate Similarity	NPC173980
0.7212	Intermediate Similarity	NPC23667
0.7212	Intermediate Similarity	NPC114333
0.7212	Intermediate Similarity	NPC91887
0.7212	Intermediate Similarity	NPC42384
0.7212	Intermediate Similarity	NPC245760
0.7212	Intermediate Similarity	NPC157284
0.7209	Intermediate Similarity	NPC315520
0.7208	Intermediate Similarity	NPC285829
0.7208	Intermediate Similarity	NPC206778
0.7205	Intermediate Similarity	NPC41847
0.7205	Intermediate Similarity	NPC328070
0.7205	Intermediate Similarity	NPC85342
0.7197	Intermediate Similarity	NPC310540
0.7197	Intermediate Similarity	NPC142956
0.7195	Intermediate Similarity	NPC322526
0.7195	Intermediate Similarity	NPC471201
0.7188	Intermediate Similarity	NPC99731
0.7188	Intermediate Similarity	NPC171460
0.7186	Intermediate Similarity	NPC471444
0.7184	Intermediate Similarity	NPC218870
0.7184	Intermediate Similarity	NPC182921
0.7184	Intermediate Similarity	NPC314987
0.7184	Intermediate Similarity	NPC474824
0.7184	Intermediate Similarity	NPC470408
0.7178	Intermediate Similarity	NPC282780
0.7178	Intermediate Similarity	NPC474519
0.7178	Intermediate Similarity	NPC166480
0.7176	Intermediate Similarity	NPC271944
0.7176	Intermediate Similarity	NPC110882
0.7176	Intermediate Similarity	NPC470570
0.7176	Intermediate Similarity	NPC85393
0.7175	Intermediate Similarity	NPC323965
0.7175	Intermediate Similarity	NPC475449
0.717	Intermediate Similarity	NPC176130
0.717	Intermediate Similarity	NPC78364
0.717	Intermediate Similarity	NPC69424
0.717	Intermediate Similarity	NPC84672
0.7169	Intermediate Similarity	NPC190457
0.7169	Intermediate Similarity	NPC294330
0.7169	Intermediate Similarity	NPC477408
0.716	Intermediate Similarity	NPC193703
0.716	Intermediate Similarity	NPC48762
0.716	Intermediate Similarity	NPC309430
0.716	Intermediate Similarity	NPC21599
0.716	Intermediate Similarity	NPC476444
0.7159	Intermediate Similarity	NPC317580
0.7158	Intermediate Similarity	NPC291305
0.7152	Intermediate Similarity	NPC53001
0.7152	Intermediate Similarity	NPC471905
0.7152	Intermediate Similarity	NPC53414
0.7152	Intermediate Similarity	NPC53206
0.7151	Intermediate Similarity	NPC477221
0.7143	Intermediate Similarity	NPC318270
0.7143	Intermediate Similarity	NPC477209
0.7143	Intermediate Similarity	NPC248068
0.7143	Intermediate Similarity	NPC85310
0.7143	Intermediate Similarity	NPC108129
0.7134	Intermediate Similarity	NPC290803
0.7134	Intermediate Similarity	NPC473052
0.7134	Intermediate Similarity	NPC473055
0.7129	Intermediate Similarity	NPC313582
0.7128	Intermediate Similarity	NPC70340
0.7126	Intermediate Similarity	NPC37992
0.7126	Intermediate Similarity	NPC32749
0.7126	Intermediate Similarity	NPC471853
0.7126	Intermediate Similarity	NPC42262
0.7126	Intermediate Similarity	NPC147542
0.7126	Intermediate Similarity	NPC473527
0.7126	Intermediate Similarity	NPC327916
0.7126	Intermediate Similarity	NPC220496
0.7126	Intermediate Similarity	NPC241349
0.7125	Intermediate Similarity	NPC237225
0.7125	Intermediate Similarity	NPC282923

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 NPC314693 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	661
0.2-0.3	1038
0.3-0.4	2221
0.4-0.5	3009
0.5-0.6	1762
0.6-0.7	270
0.7-0.8	23
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
0.7403	Intermediate Similarity	NPD5026	Approved
0.7403	Intermediate Similarity	NPD5028	Approved
0.7403	Intermediate Similarity	NPD36	Approved
0.7403	Intermediate Similarity	NPD4954	Approved
0.7403	Intermediate Similarity	NPD4955	Approved
0.7403	Intermediate Similarity	NPD5034	Approved
0.7363	Intermediate Similarity	NPD5035	Approved
0.7348	Intermediate Similarity	NPD5030	Phase 2
0.7337	Intermediate Similarity	NPD5037	Approved
0.7337	Intermediate Similarity	NPD5038	Approved
0.7337	Intermediate Similarity	NPD8150	Discontinued
0.7305	Intermediate Similarity	NPD3300	Phase 2
0.7283	Intermediate Similarity	NPD5036	Approved
0.7273	Intermediate Similarity	NPD5968	Phase 3
0.7184	Intermediate Similarity	NPD8469	Approved
0.7158	Intermediate Similarity	NPD5029	Approved
0.7158	Intermediate Similarity	NPD5031	Approved
0.7158	Intermediate Similarity	NPD5027	Approved
0.7143	Intermediate Similarity	NPD4956	Approved
0.712	Intermediate Similarity	NPD5032	Approved
0.7108	Intermediate Similarity	NPD8366	Approved
0.7091	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5039	Approved
0.7053	Intermediate Similarity	NPD6213	Phase 3
0.7053	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6212	Phase 3
0.7	Intermediate Similarity	NPD7801	Approved
0.6982	Remote Similarity	NPD3400	Discontinued
0.6971	Remote Similarity	NPD8491	Approved
0.6948	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7282	Approved
0.6937	Remote Similarity	NPD1470	Approved
0.6895	Remote Similarity	NPD6836	Approved
0.6885	Remote Similarity	NPD5033	Approved
0.6881	Remote Similarity	NPD7301	Phase 3
0.6865	Remote Similarity	NPD5190	Phase 2
0.6851	Remote Similarity	NPD3286	Discontinued
0.6837	Remote Similarity	NPD4914	Approved
0.6821	Remote Similarity	NPD7699	Phase 2
0.6821	Remote Similarity	NPD7700	Phase 2
0.6821	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8151	Discontinued
0.6811	Remote Similarity	NPD4603	Phase 2
0.6768	Remote Similarity	NPD4387	Approved
0.6768	Remote Similarity	NPD4386	Approved
0.6768	Remote Similarity	NPD6823	Phase 2
0.6763	Remote Similarity	NPD7390	Discontinued
0.6753	Remote Similarity	NPD6534	Approved
0.6753	Remote Similarity	NPD6535	Approved
0.6751	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD5404	Approved
0.6746	Remote Similarity	NPD5405	Approved
0.6746	Remote Similarity	NPD5408	Approved
0.6746	Remote Similarity	NPD5406	Approved
0.6706	Remote Similarity	NPD7978	Discontinued
0.6702	Remote Similarity	NPD5637	Discontinued
0.6687	Remote Similarity	NPD1201	Approved
0.6667	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3136	Phase 2
0.6667	Remote Similarity	NPD3226	Approved
0.6667	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7696	Phase 3
0.665	Remote Similarity	NPD7698	Approved
0.665	Remote Similarity	NPD7697	Approved
0.6649	Remote Similarity	NPD3823	Discontinued
0.6631	Remote Similarity	NPD6020	Phase 2
0.6618	Remote Similarity	NPD7874	Approved
0.6618	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7870	Phase 2
0.6617	Remote Similarity	NPD8320	Phase 1
0.6617	Remote Similarity	NPD7871	Phase 2
0.6617	Remote Similarity	NPD8319	Approved
0.6616	Remote Similarity	NPD5544	Approved
0.6616	Remote Similarity	NPD7565	Approved
0.6613	Remote Similarity	NPD7473	Discontinued
0.6611	Remote Similarity	NPD7819	Suspended
0.6605	Remote Similarity	NPD8067	Phase 3
0.6604	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7302	Phase 3
0.6601	Remote Similarity	NPD7300	Phase 3
0.6599	Remote Similarity	NPD4915	Approved
0.6587	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6777	Approved
0.6583	Remote Similarity	NPD6781	Approved
0.6583	Remote Similarity	NPD6778	Approved
0.6583	Remote Similarity	NPD6782	Approved
0.6583	Remote Similarity	NPD6780	Approved
0.6583	Remote Similarity	NPD6776	Approved
0.6583	Remote Similarity	NPD6779	Approved
0.658	Remote Similarity	NPD6835	Approved
0.6566	Remote Similarity	NPD4975	Approved
0.6566	Remote Similarity	NPD4974	Approved
0.6564	Remote Similarity	NPD5937	Approved
0.6552	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7584	Approved
0.6534	Remote Similarity	NPD2532	Approved
0.6534	Remote Similarity	NPD2533	Approved
0.6534	Remote Similarity	NPD2534	Approved
0.6533	Remote Similarity	NPD5608	Approved
0.6533	Remote Similarity	NPD5609	Approved
0.6515	Remote Similarity	NPD4388	Approved
0.6513	Remote Similarity	NPD7283	Approved
0.6512	Remote Similarity	NPD2346	Discontinued
0.6492	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD5194	Approved
0.6482	Remote Similarity	NPD5196	Approved
0.6482	Remote Similarity	NPD5197	Approved
0.648	Remote Similarity	NPD3455	Phase 2
0.6471	Remote Similarity	NPD6894	Phase 1
0.6465	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD8059	Phase 3
0.646	Remote Similarity	NPD2932	Approved
0.6453	Remote Similarity	NPD2935	Discontinued
0.6452	Remote Similarity	NPD5710	Approved
0.6452	Remote Similarity	NPD5711	Approved
0.6452	Remote Similarity	NPD6232	Discontinued
0.645	Remote Similarity	NPD8285	Discontinued
0.645	Remote Similarity	NPD943	Approved
0.6439	Remote Similarity	NPD7701	Phase 2
0.6422	Remote Similarity	NPD6807	Phase 3
0.6409	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7435	Discontinued
0.6402	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6959	Discontinued
0.6396	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2799	Discontinued
0.6395	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD4931	Phase 2
0.6379	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD6844	Discontinued
0.6373	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5610	Approved
0.6359	Remote Similarity	NPD7654	Discontinued
0.6358	Remote Similarity	NPD7450	Phase 2
0.6358	Remote Similarity	NPD3019	Approved
0.6355	Remote Similarity	NPD8163	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD8162	Phase 2
0.6354	Remote Similarity	NPD4380	Phase 2
0.6354	Remote Similarity	NPD6104	Discontinued
0.6353	Remote Similarity	NPD825	Approved
0.6353	Remote Similarity	NPD826	Approved
0.635	Remote Similarity	NPD5543	Approved
0.635	Remote Similarity	NPD8485	Approved
0.635	Remote Similarity	NPD5195	Discontinued
0.6346	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7783	Phase 2
0.6346	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD7972	Discontinued
0.6337	Remote Similarity	NPD3553	Approved
0.6337	Remote Similarity	NPD3554	Approved
0.6337	Remote Similarity	NPD3555	Approved
0.6337	Remote Similarity	NPD3552	Approved
0.6333	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD1164	Approved
0.6322	Remote Similarity	NPD2344	Approved
0.6319	Remote Similarity	NPD2672	Discontinued
0.6318	Remote Similarity	NPD4668	Phase 2
0.6316	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7177	Discontinued
0.6313	Remote Similarity	NPD3819	Phase 2
0.6312	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD8166	Discontinued
0.6304	Remote Similarity	NPD7318	Phase 3
0.6304	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD1755	Approved
0.6302	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD2651	Approved
0.6298	Remote Similarity	NPD7458	Discontinued
0.6298	Remote Similarity	NPD2649	Approved
0.6294	Remote Similarity	NPD8360	Approved
0.6294	Remote Similarity	NPD8361	Approved
0.6293	Remote Similarity	NPD8461	Discontinued
0.6292	Remote Similarity	NPD8165	Discontinued
0.6289	Remote Similarity	NPD8313	Approved
0.6289	Remote Similarity	NPD8312	Approved
0.6287	Remote Similarity	NPD258	Approved
0.6287	Remote Similarity	NPD257	Approved
0.6286	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD3589	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4097	Suspended
0.6279	Remote Similarity	NPD1607	Approved
0.6279	Remote Similarity	NPD6651	Approved
0.6278	Remote Similarity	NPD7523	Phase 3
0.6277	Remote Similarity	NPD7315	Approved
0.6274	Remote Similarity	NPD8404	Phase 2
0.6264	Remote Similarity	NPD9570	Approved
0.6263	Remote Similarity	NPD5200	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6256	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2209	Approved
0.625	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2211	Approved
0.625	Remote Similarity	NPD255	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