NPASS Compound

Structure

CID323948 OpenBabel06191716172D 26 27 0 0 0 0 0 0 0 0999 V2000 -7.7942 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 7 1 0 0 0 0 3 15 2 0 0 0 0 4 8 2 0 0 0 0 4 15 1 0 0 0 0 5 9 1 0 0 0 0 5 16 2 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 17 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 19 2 0 0 0 0 12 16 1 0 0 0 0 12 20 2 0 0 0 0 13 21 2 3 0 0 0 13 23 1 0 0 0 0 14 22 2 3 0 0 0 14 24 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.14
Volume:	368.153
LogP:	2.82
LogD:	2.842
LogS:	-4.318
# Rotatable Bonds:	9
TPSA:	77.32
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.513
Synthetic Accessibility Score:	2.797
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.582
MDCK Permeability:	2.5808694772422314e-05
Pgp-inhibitor:	0.098
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.954
Plasma Protein Binding (PPB):	86.62386322021484%
Volume Distribution (VD):	1.102
Pgp-substrate:	6.483813285827637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.246
CYP1A2-substrate:	0.946
CYP2C19-inhibitor:	0.81
CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.874
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.123
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.517
CYP3A4-substrate:	0.878

ADMET: Excretion

Clearance (CL):	8.22
Half-life (T1/2):	0.622

ADMET: Toxicity

hERG Blockers:	0.522
Human Hepatotoxicity (H-HT):	0.807
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.504
Rat Oral Acute Toxicity:	0.121
Maximum Recommended Daily Dose:	0.034
Skin Sensitization:	0.067
Carcinogencity:	0.113
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.039

Download Data

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

Natural Product: NPC323948

Natural Product ID:	NPC323948
*Common Name:**	N,N'-((1Z,3Z)-1,4-Bis(4-Methoxyphenyl)Buta-1,3-Diene-2,3-Diyl)Diformamide
IUPAC Name:	N-[(1Z,3Z)-3-formamido-1,4-bis(4-methoxyphenyl)buta-1,3-dien-2-yl]formamide
Synonyms:
Standard InCHIKey:	ZRAIRHSUKMHHQT-YZLQMOBTSA-N
Standard InCHI:	InChI=1S/C20H20N2O4/c1-25-17-7-3-15(4-8-17)11-19(21-13-23)20(22-14-24)12-16-5-9-18(26-2)10-6-16/h3-14H,1-2H3,(H,21,23)(H,22,24)/b19-11-,20-12-
SMILES:	COC1=CC=C(C=C1)C=C(C(=CC2=CC=C(C=C2)OC)NC=O)NC=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813656
PubChem CID:	11462296
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO21746	Streptomyces peucetius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15977277]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO21746	Streptomyces peucetius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21746	Streptomyces peucetius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	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
IC50	12

Activity Type	# Activity
Cell Line	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT372	Cell Line	HOP-92	Homo sapiens	IC50	=	890.0	nM	PMID[515131]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	1120.0	nM	PMID[515131]
NPT399	Cell Line	SF-295	Homo sapiens	IC50	=	700.0	nM	PMID[515131]
NPT380	Cell Line	U-251	Homo sapiens	IC50	=	920.0	nM	PMID[515131]
NPT375	Cell Line	Malme-3M	Homo sapiens	IC50	=	650.0	nM	PMID[515131]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	IC50	=	980.0	nM	PMID[515131]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	IC50	=	810.0	nM	PMID[515131]
NPT398	Cell Line	UACC-62	Homo sapiens	IC50	=	750.0	nM	PMID[515131]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	840.0	nM	PMID[515131]
NPT376	Cell Line	A498	Homo sapiens	IC50	=	860.0	nM	PMID[515131]
NPT369	Cell Line	ACHN	Homo sapiens	IC50	>	2500.0	nM	PMID[515131]
NPT112	Cell Line	MOLT-4	Homo sapiens	IC50	>	2500.0	nM	PMID[515131]

☑ 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 NPC323948 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	136
0.1-0.2	1795
0.2-0.3	8723
0.3-0.4	9490
0.4-0.5	7038
0.5-0.6	11539
0.6-0.7	3671
0.7-0.8	294
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9732	High Similarity	NPC41801
0.8829	High Similarity	NPC146530
0.8783	High Similarity	NPC303370
0.8707	High Similarity	NPC258992
0.85	High Similarity	NPC83279
0.8487	Intermediate Similarity	NPC256369
0.8276	Intermediate Similarity	NPC166837
0.8264	Intermediate Similarity	NPC252817
0.8182	Intermediate Similarity	NPC43275
0.8115	Intermediate Similarity	NPC263835
0.8103	Intermediate Similarity	NPC474272
0.8062	Intermediate Similarity	NPC471953
0.8015	Intermediate Similarity	NPC138365
0.8	Intermediate Similarity	NPC37302
0.8	Intermediate Similarity	NPC113457
0.7939	Intermediate Similarity	NPC29650
0.7937	Intermediate Similarity	NPC62101
0.7937	Intermediate Similarity	NPC95733
0.7895	Intermediate Similarity	NPC192596
0.7891	Intermediate Similarity	NPC186898
0.7874	Intermediate Similarity	NPC29477
0.7863	Intermediate Similarity	NPC309982
0.7863	Intermediate Similarity	NPC201959
0.7857	Intermediate Similarity	NPC211218
0.7826	Intermediate Similarity	NPC474603
0.7826	Intermediate Similarity	NPC12987
0.7807	Intermediate Similarity	NPC51633
0.7788	Intermediate Similarity	NPC100870
0.7778	Intermediate Similarity	NPC471315
0.7778	Intermediate Similarity	NPC471314
0.7759	Intermediate Similarity	NPC470393
0.7752	Intermediate Similarity	NPC251571
0.7748	Intermediate Similarity	NPC471581
0.7712	Intermediate Similarity	NPC75440
0.7706	Intermediate Similarity	NPC99886
0.7706	Intermediate Similarity	NPC259134
0.7706	Intermediate Similarity	NPC8002
0.7706	Intermediate Similarity	NPC177844
0.768	Intermediate Similarity	NPC321133
0.7674	Intermediate Similarity	NPC301713
0.7672	Intermediate Similarity	NPC38079
0.7672	Intermediate Similarity	NPC108875
0.7669	Intermediate Similarity	NPC303993
0.7652	Intermediate Similarity	NPC300166
0.7652	Intermediate Similarity	NPC274732
0.7647	Intermediate Similarity	NPC83289
0.7647	Intermediate Similarity	NPC189724
0.7647	Intermediate Similarity	NPC212850
0.7636	Intermediate Similarity	NPC71853
0.7634	Intermediate Similarity	NPC35961
0.7634	Intermediate Similarity	NPC52029
0.7634	Intermediate Similarity	NPC195749
0.7612	Intermediate Similarity	NPC237227
0.7586	Intermediate Similarity	NPC305205
0.7576	Intermediate Similarity	NPC114102
0.7568	Intermediate Similarity	NPC321956
0.7557	Intermediate Similarity	NPC155838
0.7541	Intermediate Similarity	NPC141003
0.7541	Intermediate Similarity	NPC35344
0.754	Intermediate Similarity	NPC17388
0.754	Intermediate Similarity	NPC160120
0.754	Intermediate Similarity	NPC289330
0.754	Intermediate Similarity	NPC53596
0.754	Intermediate Similarity	NPC471308
0.7538	Intermediate Similarity	NPC218323
0.752	Intermediate Similarity	NPC474040
0.752	Intermediate Similarity	NPC474214
0.7519	Intermediate Similarity	NPC214869
0.75	Intermediate Similarity	NPC213471
0.75	Intermediate Similarity	NPC82016
0.75	Intermediate Similarity	NPC9373
0.748	Intermediate Similarity	NPC228287
0.748	Intermediate Similarity	NPC180508
0.7478	Intermediate Similarity	NPC471576
0.746	Intermediate Similarity	NPC474320
0.7458	Intermediate Similarity	NPC154899
0.7458	Intermediate Similarity	NPC42383
0.7458	Intermediate Similarity	NPC233396
0.7447	Intermediate Similarity	NPC245974
0.744	Intermediate Similarity	NPC280001
0.7438	Intermediate Similarity	NPC475852
0.7438	Intermediate Similarity	NPC46844
0.7429	Intermediate Similarity	NPC247298
0.7419	Intermediate Similarity	NPC464
0.7419	Intermediate Similarity	NPC185541
0.7419	Intermediate Similarity	NPC296526
0.7417	Intermediate Similarity	NPC245115
0.7417	Intermediate Similarity	NPC96224
0.7417	Intermediate Similarity	NPC24101
0.7417	Intermediate Similarity	NPC97811
0.7398	Intermediate Similarity	NPC165106
0.7395	Intermediate Similarity	NPC92623
0.7395	Intermediate Similarity	NPC135464
0.7391	Intermediate Similarity	NPC175298
0.7381	Intermediate Similarity	NPC470626
0.7377	Intermediate Similarity	NPC266932
0.7377	Intermediate Similarity	NPC90520
0.7377	Intermediate Similarity	NPC296920
0.7373	Intermediate Similarity	NPC2518
0.7373	Intermediate Similarity	NPC241224
0.7373	Intermediate Similarity	NPC109637
0.7372	Intermediate Similarity	NPC14600
0.7372	Intermediate Similarity	NPC312770
0.7372	Intermediate Similarity	NPC160607
0.7372	Intermediate Similarity	NPC204848
0.7372	Intermediate Similarity	NPC41473
0.7368	Intermediate Similarity	NPC470706
0.736	Intermediate Similarity	NPC229147
0.736	Intermediate Similarity	NPC85292
0.736	Intermediate Similarity	NPC19290
0.736	Intermediate Similarity	NPC54507
0.7344	Intermediate Similarity	NPC207613
0.7338	Intermediate Similarity	NPC474128
0.7333	Intermediate Similarity	NPC227894
0.7333	Intermediate Similarity	NPC35543
0.7333	Intermediate Similarity	NPC251306
0.7328	Intermediate Similarity	NPC207541
0.7328	Intermediate Similarity	NPC71105
0.7328	Intermediate Similarity	NPC152186
0.7328	Intermediate Similarity	NPC182147
0.7328	Intermediate Similarity	NPC170583
0.7328	Intermediate Similarity	NPC246133
0.7323	Intermediate Similarity	NPC163036
0.7317	Intermediate Similarity	NPC165646
0.7317	Intermediate Similarity	NPC280606
0.7311	Intermediate Similarity	NPC8302
0.7302	Intermediate Similarity	NPC474933
0.7302	Intermediate Similarity	NPC311737
0.7302	Intermediate Similarity	NPC38458
0.7302	Intermediate Similarity	NPC293619
0.7295	Intermediate Similarity	NPC137685
0.7287	Intermediate Similarity	NPC312675
0.7287	Intermediate Similarity	NPC113865
0.7287	Intermediate Similarity	NPC184651
0.7287	Intermediate Similarity	NPC343720
0.7287	Intermediate Similarity	NPC54872
0.7287	Intermediate Similarity	NPC470212
0.7287	Intermediate Similarity	NPC473853
0.7287	Intermediate Similarity	NPC324571
0.7287	Intermediate Similarity	NPC262156
0.728	Intermediate Similarity	NPC47194
0.728	Intermediate Similarity	NPC51345
0.728	Intermediate Similarity	NPC475815
0.728	Intermediate Similarity	NPC473264
0.7273	Intermediate Similarity	NPC251466
0.7273	Intermediate Similarity	NPC156944
0.7266	Intermediate Similarity	NPC314113
0.7266	Intermediate Similarity	NPC474565
0.7266	Intermediate Similarity	NPC117780
0.7266	Intermediate Similarity	NPC165133
0.7266	Intermediate Similarity	NPC95614
0.7266	Intermediate Similarity	NPC232316
0.7266	Intermediate Similarity	NPC477837
0.7266	Intermediate Similarity	NPC242885
0.7266	Intermediate Similarity	NPC227217
0.7266	Intermediate Similarity	NPC477838
0.7266	Intermediate Similarity	NPC56214
0.7265	Intermediate Similarity	NPC13755
0.7259	Intermediate Similarity	NPC470392
0.7258	Intermediate Similarity	NPC26524
0.7252	Intermediate Similarity	NPC300955
0.725	Intermediate Similarity	NPC231705
0.725	Intermediate Similarity	NPC326447
0.7244	Intermediate Similarity	NPC131118
0.7241	Intermediate Similarity	NPC470161
0.7236	Intermediate Similarity	NPC55300
0.7231	Intermediate Similarity	NPC85488
0.7231	Intermediate Similarity	NPC71090
0.7227	Intermediate Similarity	NPC283546
0.7222	Intermediate Similarity	NPC203113
0.7222	Intermediate Similarity	NPC82963
0.7222	Intermediate Similarity	NPC141090
0.7222	Intermediate Similarity	NPC81067
0.7222	Intermediate Similarity	NPC123948
0.7222	Intermediate Similarity	NPC9341
0.7218	Intermediate Similarity	NPC157740
0.7218	Intermediate Similarity	NPC41331
0.7218	Intermediate Similarity	NPC153990
0.7218	Intermediate Similarity	NPC172403
0.7218	Intermediate Similarity	NPC99798
0.7218	Intermediate Similarity	NPC291449
0.7218	Intermediate Similarity	NPC191302
0.7217	Intermediate Similarity	NPC26244
0.7214	Intermediate Similarity	NPC195814
0.7209	Intermediate Similarity	NPC166759
0.7209	Intermediate Similarity	NPC224814
0.7209	Intermediate Similarity	NPC14007
0.7209	Intermediate Similarity	NPC109083
0.7209	Intermediate Similarity	NPC269843
0.7209	Intermediate Similarity	NPC189844
0.7209	Intermediate Similarity	NPC60962
0.7203	Intermediate Similarity	NPC7686
0.7203	Intermediate Similarity	NPC12714
0.7203	Intermediate Similarity	NPC40258
0.7203	Intermediate Similarity	NPC91461
0.7203	Intermediate Similarity	NPC310905
0.7197	Intermediate Similarity	NPC320242
0.7197	Intermediate Similarity	NPC476249
0.7194	Intermediate Similarity	NPC299583
0.7194	Intermediate Similarity	NPC296898

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 NPC323948 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	112
0.1-0.2	719
0.2-0.3	1106
0.3-0.4	1820
0.4-0.5	2892
0.5-0.6	1747
0.6-0.7	667
0.7-0.8	87
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
0.832	Intermediate Similarity	NPD4993	Discontinued
0.7857	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD2922	Phase 1
0.7737	Intermediate Similarity	NPD5481	Discontinued
0.7717	Intermediate Similarity	NPD1669	Approved
0.7717	Intermediate Similarity	NPD3685	Discontinued
0.768	Intermediate Similarity	NPD2667	Approved
0.768	Intermediate Similarity	NPD2668	Approved
0.7642	Intermediate Similarity	NPD3596	Phase 2
0.7619	Intermediate Similarity	NPD3847	Discontinued
0.7603	Intermediate Similarity	NPD821	Approved
0.7578	Intermediate Similarity	NPD6582	Phase 2
0.7578	Intermediate Similarity	NPD6583	Phase 3
0.7563	Intermediate Similarity	NPD2684	Approved
0.7561	Intermediate Similarity	NPD709	Approved
0.752	Intermediate Similarity	NPD6580	Approved
0.752	Intermediate Similarity	NPD6581	Approved
0.75	Intermediate Similarity	NPD5451	Approved
0.7481	Intermediate Similarity	NPD2407	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7843	Approved
0.7419	Intermediate Similarity	NPD2557	Approved
0.7405	Intermediate Similarity	NPD6584	Phase 3
0.7402	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD5283	Phase 1
0.7388	Intermediate Similarity	NPD7477	Discontinued
0.7368	Intermediate Similarity	NPD5163	Phase 2
0.7333	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD2595	Approved
0.7323	Intermediate Similarity	NPD2594	Approved
0.7317	Intermediate Similarity	NPD5535	Approved
0.7308	Intermediate Similarity	NPD4129	Approved
0.7297	Intermediate Similarity	NPD3559	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3556	Approved
0.7297	Intermediate Similarity	NPD3557	Approved
0.7297	Intermediate Similarity	NPD3558	Approved
0.7297	Intermediate Similarity	NPD3560	Approved
0.7286	Intermediate Similarity	NPD6364	Approved
0.7286	Intermediate Similarity	NPD44	Approved
0.7281	Intermediate Similarity	NPD2934	Approved
0.7281	Intermediate Similarity	NPD2933	Approved
0.728	Intermediate Similarity	NPD7157	Approved
0.7259	Intermediate Similarity	NPD5745	Approved
0.7252	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD968	Approved
0.725	Intermediate Similarity	NPD3134	Approved
0.7246	Intermediate Similarity	NPD4108	Discontinued
0.7239	Intermediate Similarity	NPD6179	Discontinued
0.7239	Intermediate Similarity	NPD3179	Approved
0.7239	Intermediate Similarity	NPD3180	Approved
0.7231	Intermediate Similarity	NPD2233	Approved
0.7231	Intermediate Similarity	NPD2230	Approved
0.7231	Intermediate Similarity	NPD2232	Approved
0.7226	Intermediate Similarity	NPD3052	Approved
0.7226	Intermediate Similarity	NPD3054	Approved
0.7217	Intermediate Similarity	NPD2859	Approved
0.7217	Intermediate Similarity	NPD2860	Approved
0.7203	Intermediate Similarity	NPD2752	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1817	Approved
0.7197	Intermediate Similarity	NPD1820	Approved
0.7197	Intermediate Similarity	NPD1232	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3567	Approved
0.7197	Intermediate Similarity	NPD1819	Approved
0.7197	Intermediate Similarity	NPD1818	Approved
0.7197	Intermediate Similarity	NPD3568	Approved
0.719	Intermediate Similarity	NPD1358	Approved
0.7188	Intermediate Similarity	NPD3443	Approved
0.7188	Intermediate Similarity	NPD3444	Approved
0.7188	Intermediate Similarity	NPD6382	Discontinued
0.7188	Intermediate Similarity	NPD3445	Approved
0.7188	Intermediate Similarity	NPD3049	Approved
0.7185	Intermediate Similarity	NPD1039	Discontinued
0.7185	Intermediate Similarity	NPD5718	Phase 2
0.7185	Intermediate Similarity	NPD5110	Phase 2
0.7185	Intermediate Similarity	NPD3145	Approved
0.7185	Intermediate Similarity	NPD5111	Phase 2
0.7185	Intermediate Similarity	NPD3144	Approved
0.7185	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD5109	Approved
0.7176	Intermediate Similarity	NPD2429	Approved
0.7176	Intermediate Similarity	NPD6539	Approved
0.7176	Intermediate Similarity	NPD2428	Approved
0.7176	Intermediate Similarity	NPD6540	Phase 3
0.7176	Intermediate Similarity	NPD6542	Approved
0.7176	Intermediate Similarity	NPD6543	Approved
0.7165	Intermediate Similarity	NPD5536	Phase 2
0.7163	Intermediate Similarity	NPD2459	Approved
0.7163	Intermediate Similarity	NPD2460	Phase 3
0.7163	Intermediate Similarity	NPD2458	Approved
0.7143	Intermediate Similarity	NPD6387	Discontinued
0.7133	Intermediate Similarity	NPD3281	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2554	Approved
0.7132	Intermediate Similarity	NPD6516	Phase 2
0.7132	Intermediate Similarity	NPD1423	Approved
0.7132	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2674	Phase 3
0.7132	Intermediate Similarity	NPD5846	Approved
0.7132	Intermediate Similarity	NPD2556	Approved
0.7132	Intermediate Similarity	NPD7265	Discontinued
0.7121	Intermediate Similarity	NPD6538	Approved
0.7121	Intermediate Similarity	NPD6541	Approved
0.7111	Intermediate Similarity	NPD3167	Approved
0.7111	Intermediate Similarity	NPD3164	Approved
0.7111	Intermediate Similarity	NPD3166	Approved
0.7111	Intermediate Similarity	NPD3165	Approved
0.7111	Intermediate Similarity	NPD5746	Approved
0.7111	Intermediate Similarity	NPD1024	Discontinued
0.7109	Intermediate Similarity	NPD1182	Approved
0.7109	Intermediate Similarity	NPD2486	Discontinued
0.7101	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD2235	Phase 2
0.7099	Intermediate Similarity	NPD2231	Phase 2
0.7092	Intermediate Similarity	NPD4597	Approved
0.7092	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4598	Approved
0.708	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3421	Phase 3
0.7077	Intermediate Similarity	NPD3294	Phase 2
0.7071	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD595	Approved
0.7063	Intermediate Similarity	NPD593	Approved
0.7049	Intermediate Similarity	NPD290	Approved
0.7045	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD5289	Phase 2
0.7037	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD3020	Approved
0.7034	Intermediate Similarity	NPD4123	Phase 3
0.7034	Intermediate Similarity	NPD3985	Discontinued
0.7015	Intermediate Similarity	NPD3690	Phase 2
0.7015	Intermediate Similarity	NPD2990	Approved
0.7015	Intermediate Similarity	NPD2987	Approved
0.7015	Intermediate Similarity	NPD3691	Phase 2
0.7015	Intermediate Similarity	NPD7905	Discontinued
0.7015	Intermediate Similarity	NPD7018	Phase 2
0.7014	Intermediate Similarity	NPD5756	Phase 2
0.7007	Intermediate Similarity	NPD840	Approved
0.7007	Intermediate Similarity	NPD4003	Phase 3
0.7007	Intermediate Similarity	NPD839	Approved
0.6978	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3028	Approved
0.697	Remote Similarity	NPD1840	Phase 2
0.696	Remote Similarity	NPD228	Approved
0.6959	Remote Similarity	NPD5811	Approved
0.6957	Remote Similarity	NPD2238	Phase 2
0.6954	Remote Similarity	NPD6063	Approved
0.694	Remote Similarity	NPD1794	Approved
0.694	Remote Similarity	NPD4098	Discontinued
0.694	Remote Similarity	NPD3827	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1770	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7131	Phase 3
0.6934	Remote Similarity	NPD7294	Phase 1
0.6934	Remote Similarity	NPD3374	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6896	Approved
0.6929	Remote Similarity	NPD6895	Approved
0.6923	Remote Similarity	NPD4162	Approved
0.6923	Remote Similarity	NPD3060	Approved
0.6923	Remote Similarity	NPD4236	Phase 3
0.6923	Remote Similarity	NPD4237	Approved
0.6917	Remote Similarity	NPD2982	Phase 2
0.6917	Remote Similarity	NPD2983	Phase 2
0.6912	Remote Similarity	NPD2614	Approved
0.6903	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3656	Approved
0.6899	Remote Similarity	NPD254	Approved
0.6894	Remote Similarity	NPD776	Approved
0.6889	Remote Similarity	NPD7451	Discontinued
0.6887	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6380	Phase 1
0.6879	Remote Similarity	NPD2155	Approved
0.6879	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3693	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2154	Approved
0.6879	Remote Similarity	NPD2156	Approved
0.6875	Remote Similarity	NPD6331	Phase 2
0.6875	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3236	Phase 3
0.6867	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7438	Suspended
0.6861	Remote Similarity	NPD3027	Phase 3
0.6857	Remote Similarity	NPD2157	Approved
0.6853	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7153	Discontinued
0.685	Remote Similarity	NPD2234	Approved
0.685	Remote Similarity	NPD2228	Approved
0.685	Remote Similarity	NPD594	Approved
0.685	Remote Similarity	NPD592	Approved
0.685	Remote Similarity	NPD2229	Approved
0.6849	Remote Similarity	NPD6087	Phase 1
0.6849	Remote Similarity	NPD4357	Discontinued
0.6846	Remote Similarity	NPD1548	Phase 1
0.6846	Remote Similarity	NPD1894	Discontinued
0.6842	Remote Similarity	NPD5967	Approved
0.6842	Remote Similarity	NPD2562	Approved
0.6842	Remote Similarity	NPD2981	Phase 2
0.6842	Remote Similarity	NPD2561	Approved
0.6838	Remote Similarity	NPD2040	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5266	Clinical (unspecified phase)

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