NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.19
Volume:	295.197
LogP:	5.216
LogD:	4.291
LogS:	-3.488
# Rotatable Bonds:	9
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.651
Synthetic Accessibility Score:	2.138
Fsp3:	0.625
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:	-4.833
MDCK Permeability:	1.7698414012556896e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.99

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.138
Plasma Protein Binding (PPB):	97.75031280517578%
Volume Distribution (VD):	4.277
Pgp-substrate:	2.375086784362793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.735
CYP2C19-inhibitor:	0.93
CYP2C19-substrate:	0.269
CYP2C9-inhibitor:	0.511
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.902
CYP2D6-substrate:	0.829
CYP3A4-inhibitor:	0.616
CYP3A4-substrate:	0.103

ADMET: Excretion

Clearance (CL):	8.635
Half-life (T1/2):	0.761

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.016
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.185
Maximum Recommended Daily Dose:	0.228
Skin Sensitization:	0.96
Carcinogencity:	0.053
Eye Corrosion:	0.708
Eye Irritation:	0.968
Respiratory Toxicity:	0.814

Download Data

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

Natural Product: NPC135414

Natural Product ID:	NPC135414
*Common Name:**	2-Methoxy-3-Nonylresorcinol
IUPAC Name:	4-methoxy-5-nonylbenzene-1,3-diol
Synonyms:
Standard InCHIKey:	ISOKUFVRYFVVQF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H26O3/c1-3-4-5-6-7-8-9-10-13-11-14(17)12-15(18)16(13)19-2/h11-12,17-18H,3-10H2,1-2H3
SMILES:	CCCCCCCCCc1cc(O)cc(c1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463107
PubChem CID:	11277128
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
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1021/np50063a031]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165134]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	twig	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	stem	n.a.	PMID[16254827]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22316191]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2778454]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17145	Aegiceras corniculatum	Species	Primulaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[477108]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[477108]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[477108]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[477108]

☑ 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 NPC135414 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	355
0.1-0.2	1714
0.2-0.3	5947
0.3-0.4	13774
0.4-0.5	3775
0.5-0.6	4963
0.6-0.7	7980
0.7-0.8	3384
0.8-0.85	503
0.85-0.9	272
0.9-0.95	26
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9828	High Similarity	NPC246967
0.9664	High Similarity	NPC112596
0.9504	High Similarity	NPC266691
0.95	High Similarity	NPC245060
0.9492	High Similarity	NPC474864
0.9426	High Similarity	NPC158477
0.935	High Similarity	NPC220935
0.935	High Similarity	NPC234488
0.935	High Similarity	NPC311680
0.935	High Similarity	NPC299221
0.935	High Similarity	NPC51840
0.9333	High Similarity	NPC183446
0.9274	High Similarity	NPC474356
0.9274	High Similarity	NPC232275
0.9274	High Similarity	NPC12275
0.9274	High Similarity	NPC45715
0.9268	High Similarity	NPC58164
0.9268	High Similarity	NPC10225
0.925	High Similarity	NPC121115
0.9244	High Similarity	NPC285289
0.92	High Similarity	NPC6451
0.9113	High Similarity	NPC190144
0.9106	High Similarity	NPC252131
0.9106	High Similarity	NPC293054
0.9106	High Similarity	NPC82679
0.9106	High Similarity	NPC236760
0.9106	High Similarity	NPC324112
0.9106	High Similarity	NPC246620
0.9106	High Similarity	NPC282000
0.9106	High Similarity	NPC169474
0.9106	High Similarity	NPC236791
0.9106	High Similarity	NPC124452
0.9106	High Similarity	NPC74817
0.9106	High Similarity	NPC159968
0.9106	High Similarity	NPC216836
0.9098	High Similarity	NPC234400
0.9098	High Similarity	NPC60885
0.9091	High Similarity	NPC95168
0.9068	High Similarity	NPC474612
0.9055	High Similarity	NPC103967
0.904	High Similarity	NPC192687
0.904	High Similarity	NPC214860
0.904	High Similarity	NPC224157
0.9032	High Similarity	NPC28765
0.9032	High Similarity	NPC19694
0.9024	High Similarity	NPC18924
0.9024	High Similarity	NPC214406
0.9024	High Similarity	NPC103823
0.9024	High Similarity	NPC44748
0.9024	High Similarity	NPC28730
0.9024	High Similarity	NPC78974
0.9024	High Similarity	NPC223136
0.9008	High Similarity	NPC41562
0.8992	High Similarity	NPC20674
0.8984	High Similarity	NPC201357
0.8984	High Similarity	NPC255147
0.8984	High Similarity	NPC283009
0.8984	High Similarity	NPC261873
0.8984	High Similarity	NPC134968
0.8984	High Similarity	NPC281521
0.8968	High Similarity	NPC82503
0.8968	High Similarity	NPC147317
0.896	High Similarity	NPC45824
0.896	High Similarity	NPC212015
0.8952	High Similarity	NPC50368
0.8943	High Similarity	NPC105925
0.8943	High Similarity	NPC298757
0.8943	High Similarity	NPC57490
0.8943	High Similarity	NPC117214
0.8943	High Similarity	NPC203133
0.8943	High Similarity	NPC233410
0.8943	High Similarity	NPC472093
0.8943	High Similarity	NPC251855
0.8943	High Similarity	NPC221077
0.8943	High Similarity	NPC299584
0.8943	High Similarity	NPC265483
0.8943	High Similarity	NPC193544
0.8943	High Similarity	NPC208950
0.8943	High Similarity	NPC116907
0.8943	High Similarity	NPC475169
0.8943	High Similarity	NPC82483
0.8943	High Similarity	NPC17943
0.8934	High Similarity	NPC197757
0.8934	High Similarity	NPC228922
0.8934	High Similarity	NPC220598
0.8934	High Similarity	NPC165375
0.8926	High Similarity	NPC75713
0.8926	High Similarity	NPC49341
0.8915	High Similarity	NPC300846
0.8915	High Similarity	NPC472336
0.8915	High Similarity	NPC476639
0.8915	High Similarity	NPC472334
0.8915	High Similarity	NPC114155
0.8906	High Similarity	NPC106215
0.8898	High Similarity	NPC127624
0.8898	High Similarity	NPC218884
0.8898	High Similarity	NPC193067
0.8889	High Similarity	NPC126836
0.888	High Similarity	NPC154866
0.888	High Similarity	NPC63179
0.8871	High Similarity	NPC76451
0.8871	High Similarity	NPC476006
0.8852	High Similarity	NPC270326
0.8846	High Similarity	NPC103976
0.8846	High Similarity	NPC73535
0.8846	High Similarity	NPC276490
0.8846	High Similarity	NPC90615
0.8846	High Similarity	NPC272157
0.8846	High Similarity	NPC201145
0.8846	High Similarity	NPC25111
0.8846	High Similarity	NPC326797
0.8846	High Similarity	NPC107551
0.8846	High Similarity	NPC6262
0.8846	High Similarity	NPC102904
0.8846	High Similarity	NPC474282
0.8846	High Similarity	NPC176051
0.8837	High Similarity	NPC472337
0.8837	High Similarity	NPC252095
0.8833	High Similarity	NPC308217
0.8828	High Similarity	NPC37196
0.8828	High Similarity	NPC474810
0.8828	High Similarity	NPC269528
0.8828	High Similarity	NPC94236
0.8824	High Similarity	NPC52464
0.8824	High Similarity	NPC304208
0.8824	High Similarity	NPC259638
0.881	High Similarity	NPC476968
0.881	High Similarity	NPC170844
0.88	High Similarity	NPC266555
0.88	High Similarity	NPC127587
0.8793	High Similarity	NPC195873
0.879	High Similarity	NPC33654
0.878	High Similarity	NPC282496
0.878	High Similarity	NPC233526
0.878	High Similarity	NPC136319
0.8779	High Similarity	NPC245207
0.8779	High Similarity	NPC212942
0.8779	High Similarity	NPC127218
0.8779	High Similarity	NPC29868
0.8779	High Similarity	NPC19869
0.8779	High Similarity	NPC30951
0.8779	High Similarity	NPC319647
0.8779	High Similarity	NPC6369
0.8779	High Similarity	NPC25966
0.8779	High Similarity	NPC79622
0.8779	High Similarity	NPC292882
0.876	High Similarity	NPC7515
0.876	High Similarity	NPC206737
0.876	High Similarity	NPC289258
0.876	High Similarity	NPC469659
0.876	High Similarity	NPC188378
0.876	High Similarity	NPC56764
0.876	High Similarity	NPC555
0.876	High Similarity	NPC276026
0.875	High Similarity	NPC161203
0.875	High Similarity	NPC86655
0.875	High Similarity	NPC202762
0.873	High Similarity	NPC470213
0.873	High Similarity	NPC98631
0.873	High Similarity	NPC206615
0.873	High Similarity	NPC186843
0.872	High Similarity	NPC223953
0.8712	High Similarity	NPC295719
0.8712	High Similarity	NPC284464
0.8712	High Similarity	NPC165026
0.8712	High Similarity	NPC160283
0.8712	High Similarity	NPC34431
0.8712	High Similarity	NPC73505
0.8712	High Similarity	NPC259519
0.8712	High Similarity	NPC254759
0.871	High Similarity	NPC5796
0.871	High Similarity	NPC206487
0.8707	High Similarity	NPC168657
0.8702	High Similarity	NPC105493
0.8699	High Similarity	NPC71579
0.8699	High Similarity	NPC473411
0.8699	High Similarity	NPC262253
0.8692	High Similarity	NPC214853
0.8692	High Similarity	NPC260898
0.8692	High Similarity	NPC327382
0.8692	High Similarity	NPC256262
0.8692	High Similarity	NPC112939
0.8692	High Similarity	NPC240279
0.8692	High Similarity	NPC94750
0.8692	High Similarity	NPC195022
0.8692	High Similarity	NPC474206
0.8692	High Similarity	NPC234333
0.8692	High Similarity	NPC47398
0.8692	High Similarity	NPC55239
0.8692	High Similarity	NPC121812
0.8692	High Similarity	NPC112246
0.8692	High Similarity	NPC111655
0.8692	High Similarity	NPC180602
0.8692	High Similarity	NPC470356
0.8682	High Similarity	NPC168059
0.8682	High Similarity	NPC32778
0.8682	High Similarity	NPC475840
0.8682	High Similarity	NPC105554
0.8682	High Similarity	NPC229442
0.8672	High Similarity	NPC469907

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 NPC135414 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	986
0.2-0.3	2092
0.3-0.4	2752
0.4-0.5	1479
0.5-0.6	911
0.6-0.7	502
0.7-0.8	73
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.881	High Similarity	NPD3027	Phase 3
0.8504	High Similarity	NPD1530	Clinical (unspecified phase)
0.8475	Intermediate Similarity	NPD228	Approved
0.8438	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1613	Approved
0.8049	Intermediate Similarity	NPD6671	Approved
0.8047	Intermediate Similarity	NPD4749	Approved
0.7939	Intermediate Similarity	NPD3018	Phase 2
0.7863	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD4750	Phase 3
0.7769	Intermediate Similarity	NPD2983	Phase 2
0.7769	Intermediate Similarity	NPD2982	Phase 2
0.7761	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD2801	Approved
0.7742	Intermediate Similarity	NPD5283	Phase 1
0.7712	Intermediate Similarity	NPD846	Approved
0.7712	Intermediate Similarity	NPD940	Approved
0.7692	Intermediate Similarity	NPD2981	Phase 2
0.7687	Intermediate Similarity	NPD4625	Phase 3
0.7655	Intermediate Similarity	NPD1653	Approved
0.7634	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD1610	Phase 2
0.7612	Intermediate Similarity	NPD4908	Phase 1
0.7578	Intermediate Similarity	NPD1548	Phase 1
0.7576	Intermediate Similarity	NPD6696	Suspended
0.7568	Intermediate Similarity	NPD1934	Approved
0.7541	Intermediate Similarity	NPD290	Approved
0.7537	Intermediate Similarity	NPD2861	Phase 2
0.7518	Intermediate Similarity	NPD3620	Phase 2
0.7518	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9296	Approved
0.7481	Intermediate Similarity	NPD3705	Approved
0.748	Intermediate Similarity	NPD2684	Approved
0.7479	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD2674	Phase 3
0.7419	Intermediate Similarity	NPD3022	Approved
0.7419	Intermediate Similarity	NPD3021	Approved
0.7405	Intermediate Similarity	NPD3496	Discontinued
0.74	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD1357	Approved
0.7361	Intermediate Similarity	NPD2219	Phase 1
0.7357	Intermediate Similarity	NPD6111	Discontinued
0.7348	Intermediate Similarity	NPD1091	Approved
0.7348	Intermediate Similarity	NPD422	Phase 1
0.7343	Intermediate Similarity	NPD5177	Phase 3
0.7324	Intermediate Similarity	NPD3540	Phase 1
0.732	Intermediate Similarity	NPD6234	Discontinued
0.7317	Intermediate Similarity	NPD968	Approved
0.7303	Intermediate Similarity	NPD3882	Suspended
0.7303	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD844	Approved
0.7266	Intermediate Similarity	NPD1558	Phase 1
0.726	Intermediate Similarity	NPD1511	Approved
0.7254	Intermediate Similarity	NPD6099	Approved
0.7254	Intermediate Similarity	NPD6100	Approved
0.7254	Intermediate Similarity	NPD3539	Phase 1
0.7246	Intermediate Similarity	NPD3144	Approved
0.7246	Intermediate Similarity	NPD3145	Approved
0.7244	Intermediate Similarity	NPD7843	Approved
0.7239	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD596	Approved
0.7226	Intermediate Similarity	NPD600	Approved
0.7219	Intermediate Similarity	NPD37	Approved
0.7214	Intermediate Similarity	NPD230	Phase 1
0.7209	Intermediate Similarity	NPD7157	Approved
0.7197	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4626	Approved
0.7197	Intermediate Similarity	NPD6166	Phase 2
0.7197	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1242	Phase 1
0.7188	Intermediate Similarity	NPD1398	Phase 1
0.7164	Intermediate Similarity	NPD2233	Approved
0.7164	Intermediate Similarity	NPD2232	Approved
0.7164	Intermediate Similarity	NPD2230	Approved
0.7162	Intermediate Similarity	NPD1512	Approved
0.7154	Intermediate Similarity	NPD7340	Approved
0.7153	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD2238	Phase 2
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7133	Intermediate Similarity	NPD2935	Discontinued
0.7123	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5536	Phase 2
0.7092	Intermediate Similarity	NPD447	Suspended
0.7083	Intermediate Similarity	NPD288	Approved
0.7078	Intermediate Similarity	NPD4965	Approved
0.7078	Intermediate Similarity	NPD4967	Phase 2
0.7078	Intermediate Similarity	NPD4966	Approved
0.7071	Intermediate Similarity	NPD840	Approved
0.7071	Intermediate Similarity	NPD839	Approved
0.707	Intermediate Similarity	NPD6232	Discontinued
0.7069	Intermediate Similarity	NPD9295	Approved
0.7059	Intermediate Similarity	NPD2922	Phase 1
0.7055	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5089	Approved
0.7039	Intermediate Similarity	NPD5090	Approved
0.7032	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4357	Discontinued
0.7021	Intermediate Similarity	NPD1240	Approved
0.702	Intermediate Similarity	NPD4005	Discontinued
0.7019	Intermediate Similarity	NPD7074	Phase 3
0.7013	Intermediate Similarity	NPD3817	Phase 2
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7228	Approved
0.7	Intermediate Similarity	NPD3818	Discontinued
0.6992	Remote Similarity	NPD291	Approved
0.6986	Remote Similarity	NPD3060	Approved
0.6986	Remote Similarity	NPD6674	Discontinued
0.6983	Remote Similarity	NPD9094	Approved
0.698	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7635	Approved
0.6974	Remote Similarity	NPD4675	Approved
0.6974	Remote Similarity	NPD4678	Approved
0.6966	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7124	Phase 2
0.6957	Remote Similarity	NPD7054	Approved
0.6957	Remote Similarity	NPD5844	Phase 1
0.6948	Remote Similarity	NPD1465	Phase 2
0.694	Remote Similarity	NPD1778	Approved
0.6937	Remote Similarity	NPD7473	Discontinued
0.6934	Remote Similarity	NPD8651	Approved
0.6923	Remote Similarity	NPD1607	Approved
0.6918	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7472	Approved
0.6901	Remote Similarity	NPD943	Approved
0.6899	Remote Similarity	NPD7199	Phase 2
0.689	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1652	Phase 2
0.6871	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD5691	Approved
0.6863	Remote Similarity	NPD4380	Phase 2
0.686	Remote Similarity	NPD2859	Approved
0.686	Remote Similarity	NPD2860	Approved
0.6849	Remote Similarity	NPD1375	Discontinued
0.6849	Remote Similarity	NPD7266	Discontinued
0.6849	Remote Similarity	NPD5763	Approved
0.6849	Remote Similarity	NPD5762	Approved
0.6835	Remote Similarity	NPD5494	Approved
0.6835	Remote Similarity	NPD6584	Phase 3
0.6833	Remote Similarity	NPD845	Approved
0.6829	Remote Similarity	NPD3020	Approved
0.6828	Remote Similarity	NPD1510	Phase 2
0.6824	Remote Similarity	NPD3892	Phase 2
0.6822	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD709	Approved
0.6815	Remote Similarity	NPD9381	Approved
0.6815	Remote Similarity	NPD4055	Discovery
0.6815	Remote Similarity	NPD9384	Approved
0.6813	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6653	Approved
0.6806	Remote Similarity	NPD4097	Suspended
0.68	Remote Similarity	NPD1774	Approved
0.68	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5402	Approved
0.6795	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7549	Discontinued
0.6788	Remote Similarity	NPD2231	Phase 2
0.6788	Remote Similarity	NPD2235	Phase 2
0.6788	Remote Similarity	NPD9269	Phase 2
0.6786	Remote Similarity	NPD2237	Approved
0.6781	Remote Similarity	NPD2161	Phase 2
0.6779	Remote Similarity	NPD2677	Approved
0.6777	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD2933	Approved
0.6777	Remote Similarity	NPD2934	Approved
0.6776	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6797	Phase 2
0.6763	Remote Similarity	NPD2797	Approved
0.6761	Remote Similarity	NPD5111	Phase 2
0.6761	Remote Similarity	NPD5110	Phase 2
0.6761	Remote Similarity	NPD5109	Approved
0.6759	Remote Similarity	NPD4538	Approved
0.6759	Remote Similarity	NPD4536	Approved
0.6759	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4236	Phase 3
0.6757	Remote Similarity	NPD4237	Approved
0.6755	Remote Similarity	NPD7447	Phase 1
0.6755	Remote Similarity	NPD2532	Approved
0.6755	Remote Similarity	NPD2533	Approved
0.6755	Remote Similarity	NPD2534	Approved
0.6755	Remote Similarity	NPD1424	Approved
0.6744	Remote Similarity	NPD5451	Approved
0.6739	Remote Similarity	NPD9622	Approved
0.6738	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD5124	Phase 1
0.6736	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2978	Approved
0.6731	Remote Similarity	NPD4585	Approved
0.6731	Remote Similarity	NPD2977	Approved
0.6727	Remote Similarity	NPD7251	Discontinued
0.6721	Remote Similarity	NPD1809	Phase 2
0.6718	Remote Similarity	NPD9379	Approved
0.6718	Remote Similarity	NPD821	Approved
0.6718	Remote Similarity	NPD1138	Approved
0.6718	Remote Similarity	NPD9377	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