NPASS Compound

Structure

NPC220935 OpenBabel07101718312D 28 28 0 0 0 0 0 0 0 0999 V2000 -8.6603 -6.0000 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 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -1.7321 -1.0000 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 0.0000 -1.0000 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 0.8660 0.5000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 2 5 1 0 0 0 0 3 27 1 0 0 0 0 4 6 1 0 0 0 0 5 28 1 0 0 0 0 6 7 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 2 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 20 1 0 0 0 0 19 21 2 0 0 0 0 19 22 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 23 1 0 0 0 0 21 27 1 0 0 0 0 22 24 2 0 0 0 0 22 28 1 0 0 0 0 23 25 1 0 0 0 0 24 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.26
Volume:	434.446
LogP:	4.677
LogD:	3.848
LogS:	-3.9
# Rotatable Bonds:	15
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.267
Synthetic Accessibility Score:	2.869
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.844
MDCK Permeability:	3.1437361030839384e-05
Pgp-inhibitor:	0.117
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	101.1480941772461%
Volume Distribution (VD):	3.06
Pgp-substrate:	0.47976189851760864%

ADMET: Metabolism

CYP1A2-inhibitor:	0.584
CYP1A2-substrate:	0.911
CYP2C19-inhibitor:	0.704
CYP2C19-substrate:	0.24
CYP2C9-inhibitor:	0.587
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.662
CYP2D6-substrate:	0.946
CYP3A4-inhibitor:	0.489
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	3.639
Half-life (T1/2):	0.924

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.102
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.427
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.222
Skin Sensitization:	0.962
Carcinogencity:	0.432
Eye Corrosion:	0.004
Eye Irritation:	0.877
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC220935

Natural Product ID:	NPC220935
*Common Name:**	E565
IUPAC Name:	4-ethoxy-6-methoxy-2-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzene-1,3-diol
Synonyms:	E565; E586
Standard InCHIKey:	SUAPARZKDSPGMY-NQLNTKRDSA-N
Standard InCHI:	InChI=1S/C24H36O4/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-20-23(25)21(27-3)19-22(24(20)26)28-5-2/h4,7-8,10-11,19,25-26H,1,5-6,9,12-18H2,2-3H3/b8-7-,11-10-
SMILES:	C=CC/C=CC/C=CCCCCCCCc1c(O)c(OC)cc(c1O)OCC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456854
PubChem CID:	44559488
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542343]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	roots	n.a.	n.a.	PMID[14664512]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25172742]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9677276]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26371	Sorghum bicolor	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26371	Sorghum bicolor	Species	Poaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	200.0	nM	PMID[538485]

☑ 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 NPC220935 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	375
0.1-0.2	1558
0.2-0.3	5286
0.3-0.4	12986
0.4-0.5	4806
0.5-0.6	4663
0.6-0.7	7460
0.7-0.8	4367
0.8-0.85	742
0.85-0.9	359
0.9-0.95	93
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9675	High Similarity	NPC112596
0.9457	High Similarity	NPC134968
0.9444	High Similarity	NPC158477
0.9385	High Similarity	NPC472336
0.9385	High Similarity	NPC472334
0.9365	High Similarity	NPC19694
0.9365	High Similarity	NPC266691
0.935	High Similarity	NPC474864
0.935	High Similarity	NPC135414
0.935	High Similarity	NPC246967
0.9313	High Similarity	NPC107551
0.9313	High Similarity	NPC102904
0.9313	High Similarity	NPC474282
0.9313	High Similarity	NPC176051
0.9313	High Similarity	NPC326797
0.9313	High Similarity	NPC276490
0.9313	High Similarity	NPC103976
0.9308	High Similarity	NPC281521
0.9308	High Similarity	NPC472337
0.9308	High Similarity	NPC201357
0.9308	High Similarity	NPC255147
0.9302	High Similarity	NPC474810
0.9297	High Similarity	NPC82503
0.9286	High Similarity	NPC216836
0.9242	High Similarity	NPC25966
0.9242	High Similarity	NPC127218
0.9242	High Similarity	NPC19869
0.9242	High Similarity	NPC319647
0.9242	High Similarity	NPC245207
0.9231	High Similarity	NPC106215
0.9219	High Similarity	NPC299221
0.9219	High Similarity	NPC311680
0.9219	High Similarity	NPC51840
0.9219	High Similarity	NPC234488
0.9219	High Similarity	NPC214860
0.9206	High Similarity	NPC476006
0.92	High Similarity	NPC183446
0.9173	High Similarity	NPC160283
0.9173	High Similarity	NPC254759
0.916	High Similarity	NPC94750
0.916	High Similarity	NPC252095
0.916	High Similarity	NPC121812
0.916	High Similarity	NPC112939
0.916	High Similarity	NPC195022
0.916	High Similarity	NPC474206
0.916	High Similarity	NPC112246
0.916	High Similarity	NPC470356
0.9154	High Similarity	NPC94236
0.9154	High Similarity	NPC37196
0.9154	High Similarity	NPC168059
0.9154	High Similarity	NPC229442
0.9154	High Similarity	NPC475840
0.9154	High Similarity	NPC269528
0.9147	High Similarity	NPC147317
0.9147	High Similarity	NPC142530
0.9141	High Similarity	NPC10225
0.9141	High Similarity	NPC45824
0.9141	High Similarity	NPC58164
0.9104	High Similarity	NPC471389
0.9098	High Similarity	NPC292882
0.9091	High Similarity	NPC227503
0.9091	High Similarity	NPC162659
0.9091	High Similarity	NPC270456
0.9091	High Similarity	NPC230734
0.9091	High Similarity	NPC16435
0.9091	High Similarity	NPC248727
0.9091	High Similarity	NPC474639
0.9091	High Similarity	NPC265433
0.9091	High Similarity	NPC306441
0.9091	High Similarity	NPC173660
0.9091	High Similarity	NPC476698
0.9084	High Similarity	NPC310854
0.9084	High Similarity	NPC317380
0.9077	High Similarity	NPC161203
0.9077	High Similarity	NPC127624
0.9077	High Similarity	NPC470752
0.9077	High Similarity	NPC474635
0.9077	High Similarity	NPC86655
0.9077	High Similarity	NPC6451
0.9077	High Similarity	NPC202762
0.9062	High Similarity	NPC63179
0.9055	High Similarity	NPC245060
0.9044	High Similarity	NPC50250
0.9037	High Similarity	NPC107161
0.903	High Similarity	NPC259519
0.9023	High Similarity	NPC211549
0.9015	High Similarity	NPC47398
0.9015	High Similarity	NPC151224
0.9015	High Similarity	NPC234333
0.9015	High Similarity	NPC61946
0.9015	High Similarity	NPC260898
0.9008	High Similarity	NPC11060
0.9	High Similarity	NPC309787
0.9	High Similarity	NPC45715
0.9	High Similarity	NPC232275
0.9	High Similarity	NPC472597
0.9	High Similarity	NPC474356
0.9	High Similarity	NPC12275
0.8984	High Similarity	NPC246620
0.8984	High Similarity	NPC282000
0.8984	High Similarity	NPC124452
0.8984	High Similarity	NPC74817
0.8984	High Similarity	NPC470699
0.8984	High Similarity	NPC236791
0.8984	High Similarity	NPC50368
0.8984	High Similarity	NPC210355
0.8984	High Similarity	NPC293054
0.8984	High Similarity	NPC159968
0.8984	High Similarity	NPC236760
0.8984	High Similarity	NPC169474
0.8984	High Similarity	NPC82679
0.8984	High Similarity	NPC324112
0.8971	High Similarity	NPC477616
0.8968	High Similarity	NPC95168
0.8968	High Similarity	NPC121115
0.8963	High Similarity	NPC247291
0.8963	High Similarity	NPC311530
0.896	High Similarity	NPC285289
0.8955	High Similarity	NPC70682
0.8955	High Similarity	NPC471388
0.8955	High Similarity	NPC260741
0.8947	High Similarity	NPC269091
0.8947	High Similarity	NPC302701
0.8943	High Similarity	NPC474612
0.8931	High Similarity	NPC35932
0.8931	High Similarity	NPC160991
0.8931	High Similarity	NPC7903
0.8931	High Similarity	NPC184447
0.8931	High Similarity	NPC16208
0.8923	High Similarity	NPC192687
0.8923	High Similarity	NPC229231
0.8923	High Similarity	NPC91291
0.8923	High Similarity	NPC472338
0.8923	High Similarity	NPC224157
0.8906	High Similarity	NPC28730
0.8906	High Similarity	NPC78974
0.8906	High Similarity	NPC214406
0.8906	High Similarity	NPC223136
0.8906	High Similarity	NPC103823
0.8906	High Similarity	NPC18924
0.8906	High Similarity	NPC44748
0.8906	High Similarity	NPC181361
0.8905	High Similarity	NPC45257
0.8905	High Similarity	NPC12641
0.8905	High Similarity	NPC93323
0.8905	High Similarity	NPC280092
0.8905	High Similarity	NPC63879
0.8897	High Similarity	NPC472335
0.8897	High Similarity	NPC469564
0.8897	High Similarity	NPC472332
0.8889	High Similarity	NPC270326
0.8889	High Similarity	NPC309124
0.8889	High Similarity	NPC27495
0.8889	High Similarity	NPC184797
0.8889	High Similarity	NPC22317
0.8881	High Similarity	NPC105493
0.8881	High Similarity	NPC476171
0.8872	High Similarity	NPC164787
0.8872	High Similarity	NPC473413
0.8872	High Similarity	NPC327382
0.8872	High Similarity	NPC261873
0.8872	High Similarity	NPC283009
0.8864	High Similarity	NPC105554
0.8864	High Similarity	NPC263064
0.8855	High Similarity	NPC470095
0.8855	High Similarity	NPC469613
0.8855	High Similarity	NPC469907
0.8855	High Similarity	NPC470096
0.8855	High Similarity	NPC469625
0.8855	High Similarity	NPC30043
0.8849	High Similarity	NPC227902
0.8846	High Similarity	NPC222004
0.8846	High Similarity	NPC218856
0.8846	High Similarity	NPC202582
0.8846	High Similarity	NPC470258
0.8846	High Similarity	NPC190629
0.8846	High Similarity	NPC3439
0.8846	High Similarity	NPC226788
0.8846	High Similarity	NPC210623
0.8846	High Similarity	NPC285339
0.8846	High Similarity	NPC212015
0.8846	High Similarity	NPC273295
0.8846	High Similarity	NPC170844
0.8846	High Similarity	NPC190144
0.8846	High Similarity	NPC476968
0.8837	High Similarity	NPC474670
0.8832	High Similarity	NPC47633
0.8832	High Similarity	NPC102044
0.8832	High Similarity	NPC85264
0.8828	High Similarity	NPC57490
0.8828	High Similarity	NPC475169
0.8828	High Similarity	NPC472093
0.8828	High Similarity	NPC116907
0.8828	High Similarity	NPC105925
0.8828	High Similarity	NPC221077
0.8828	High Similarity	NPC299584
0.8828	High Similarity	NPC117214
0.8828	High Similarity	NPC193544
0.8828	High Similarity	NPC298757
0.8828	High Similarity	NPC82483

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 NPC220935 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	903
0.2-0.3	2136
0.3-0.4	2722
0.4-0.5	1489
0.5-0.6	880
0.6-0.7	584
0.7-0.8	87
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8846	High Similarity	NPD3027	Phase 3
0.8788	High Similarity	NPD1612	Clinical (unspecified phase)
0.8788	High Similarity	NPD1613	Approved
0.8769	High Similarity	NPD1529	Clinical (unspecified phase)
0.8692	High Similarity	NPD1530	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD6671	Approved
0.8106	Intermediate Similarity	NPD4749	Approved
0.8088	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD1653	Approved
0.808	Intermediate Similarity	NPD228	Approved
0.8074	Intermediate Similarity	NPD4908	Phase 1
0.8054	Intermediate Similarity	NPD2801	Approved
0.7987	Intermediate Similarity	NPD1934	Approved
0.7956	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD1610	Phase 2
0.7923	Intermediate Similarity	NPD1548	Phase 1
0.7883	Intermediate Similarity	NPD4625	Phase 3
0.7868	Intermediate Similarity	NPD2861	Phase 2
0.7868	Intermediate Similarity	NPD3018	Phase 2
0.782	Intermediate Similarity	NPD1091	Approved
0.7815	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6696	Suspended
0.776	Intermediate Similarity	NPD290	Approved
0.7744	Intermediate Similarity	NPD3496	Discontinued
0.7734	Intermediate Similarity	NPD7843	Approved
0.7712	Intermediate Similarity	NPD3882	Suspended
0.7704	Intermediate Similarity	NPD2983	Phase 2
0.7704	Intermediate Similarity	NPD2982	Phase 2
0.7698	Intermediate Similarity	NPD2684	Approved
0.7692	Intermediate Similarity	NPD7157	Approved
0.763	Intermediate Similarity	NPD2981	Phase 2
0.7597	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6166	Phase 2
0.7595	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1511	Approved
0.7556	Intermediate Similarity	NPD422	Phase 1
0.7556	Intermediate Similarity	NPD3705	Approved
0.754	Intermediate Similarity	NPD968	Approved
0.7538	Intermediate Similarity	NPD5283	Phase 1
0.7518	Intermediate Similarity	NPD8651	Approved
0.7516	Intermediate Similarity	NPD7074	Phase 3
0.7467	Intermediate Similarity	NPD1512	Approved
0.7465	Intermediate Similarity	NPD4060	Phase 1
0.7465	Intermediate Similarity	NPD1558	Phase 1
0.7453	Intermediate Similarity	NPD7054	Approved
0.7448	Intermediate Similarity	NPD6100	Approved
0.7448	Intermediate Similarity	NPD6099	Approved
0.7445	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3817	Phase 2
0.7415	Intermediate Similarity	NPD6674	Discontinued
0.7407	Intermediate Similarity	NPD7472	Approved
0.7391	Intermediate Similarity	NPD3818	Discontinued
0.7389	Intermediate Similarity	NPD6234	Discontinued
0.7386	Intermediate Similarity	NPD4675	Approved
0.7386	Intermediate Similarity	NPD4678	Approved
0.7365	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD4750	Phase 3
0.736	Intermediate Similarity	NPD846	Approved
0.736	Intermediate Similarity	NPD291	Approved
0.736	Intermediate Similarity	NPD940	Approved
0.7351	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD5844	Phase 1
0.7315	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1652	Phase 2
0.7296	Intermediate Similarity	NPD7199	Phase 2
0.7292	Intermediate Similarity	NPD230	Phase 1
0.7292	Intermediate Similarity	NPD447	Suspended
0.7285	Intermediate Similarity	NPD7447	Phase 1
0.7279	Intermediate Similarity	NPD3540	Phase 1
0.7279	Intermediate Similarity	NPD1375	Discontinued
0.7279	Intermediate Similarity	NPD1778	Approved
0.7279	Intermediate Similarity	NPD5763	Approved
0.7279	Intermediate Similarity	NPD5762	Approved
0.7273	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3892	Phase 2
0.7241	Intermediate Similarity	NPD6653	Approved
0.7239	Intermediate Similarity	NPD7340	Approved
0.7233	Intermediate Similarity	NPD5494	Approved
0.7231	Intermediate Similarity	NPD3021	Approved
0.7231	Intermediate Similarity	NPD3022	Approved
0.7222	Intermediate Similarity	NPD3620	Phase 2
0.7222	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1774	Approved
0.7215	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7251	Discontinued
0.7211	Intermediate Similarity	NPD3539	Phase 1
0.7208	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1357	Approved
0.7205	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2219	Phase 1
0.72	Intermediate Similarity	NPD2677	Approved
0.7197	Intermediate Similarity	NPD5402	Approved
0.7197	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD6111	Discontinued
0.7181	Intermediate Similarity	NPD5177	Phase 3
0.7179	Intermediate Similarity	NPD37	Approved
0.7178	Intermediate Similarity	NPD7228	Approved
0.7172	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5124	Phase 1
0.7171	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7808	Phase 3
0.7169	Intermediate Similarity	NPD7549	Discontinued
0.7162	Intermediate Similarity	NPD7266	Discontinued
0.7154	Intermediate Similarity	NPD9296	Approved
0.7153	Intermediate Similarity	NPD2674	Phase 3
0.7152	Intermediate Similarity	NPD4965	Approved
0.7152	Intermediate Similarity	NPD4966	Approved
0.7152	Intermediate Similarity	NPD4967	Phase 2
0.7152	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD1398	Phase 1
0.7143	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1465	Phase 2
0.7132	Intermediate Similarity	NPD7534	Approved
0.7132	Intermediate Similarity	NPD7533	Approved
0.7107	Intermediate Similarity	NPD7075	Discontinued
0.7105	Intermediate Similarity	NPD7213	Phase 3
0.7105	Intermediate Similarity	NPD7212	Phase 2
0.7083	Intermediate Similarity	NPD8053	Approved
0.7083	Intermediate Similarity	NPD8054	Approved
0.7075	Intermediate Similarity	NPD4536	Approved
0.7075	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4538	Approved
0.7071	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD596	Approved
0.7063	Intermediate Similarity	NPD600	Approved
0.7059	Intermediate Similarity	NPD4123	Phase 3
0.7055	Intermediate Similarity	NPD6355	Discontinued
0.7051	Intermediate Similarity	NPD4380	Phase 2
0.7048	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD6584	Phase 3
0.7039	Intermediate Similarity	NPD7124	Phase 2
0.7037	Intermediate Similarity	NPD6232	Discontinued
0.7034	Intermediate Similarity	NPD840	Approved
0.7034	Intermediate Similarity	NPD839	Approved
0.7034	Intermediate Similarity	NPD6233	Phase 2
0.7034	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3686	Approved
0.7032	Intermediate Similarity	NPD3687	Approved
0.7025	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7095	Approved
0.7013	Intermediate Similarity	NPD52	Approved
0.7013	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7526	Approved
0.7012	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD2231	Phase 2
0.7	Intermediate Similarity	NPD2424	Discontinued
0.7	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1549	Phase 2
0.7	Intermediate Similarity	NPD2235	Phase 2
0.6993	Remote Similarity	NPD6799	Approved
0.6993	Remote Similarity	NPD9494	Approved
0.6993	Remote Similarity	NPD4357	Discontinued
0.6987	Remote Similarity	NPD3111	Phase 1
0.6987	Remote Similarity	NPD4005	Discontinued
0.6986	Remote Similarity	NPD2238	Phase 2
0.6981	Remote Similarity	NPD2560	Approved
0.6981	Remote Similarity	NPD2563	Approved
0.698	Remote Similarity	NPD1551	Phase 2
0.698	Remote Similarity	NPD2161	Phase 2
0.698	Remote Similarity	NPD6032	Approved
0.698	Remote Similarity	NPD2935	Discontinued
0.6975	Remote Similarity	NPD1247	Approved
0.6966	Remote Similarity	NPD3144	Approved
0.6966	Remote Similarity	NPD6798	Discontinued
0.6966	Remote Similarity	NPD3145	Approved
0.696	Remote Similarity	NPD844	Approved
0.6959	Remote Similarity	NPD7906	Approved
0.6954	Remote Similarity	NPD4236	Phase 3
0.6954	Remote Similarity	NPD3060	Approved
0.6954	Remote Similarity	NPD4237	Approved
0.694	Remote Similarity	NPD821	Approved
0.6939	Remote Similarity	NPD5735	Approved
0.6934	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5536	Phase 2
0.6933	Remote Similarity	NPD6004	Phase 3
0.6933	Remote Similarity	NPD6002	Phase 3
0.6933	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6005	Phase 3
0.6933	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD1611	Approved
0.6923	Remote Similarity	NPD3690	Phase 2
0.6923	Remote Similarity	NPD3691	Phase 2
0.6918	Remote Similarity	NPD5773	Approved
0.6918	Remote Similarity	NPD5772	Approved
0.6918	Remote Similarity	NPD7819	Suspended
0.6913	Remote Similarity	NPD5960	Phase 3
0.6913	Remote Similarity	NPD7033	Discontinued
0.6913	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5588	Approved
0.6913	Remote Similarity	NPD1510	Phase 2
0.6913	Remote Similarity	NPD6028	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