NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.16
Volume:	298.664
LogP:	4.642
LogD:	4.091
LogS:	-5.121
# Rotatable Bonds:	7
TPSA:	42.6
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.825
Synthetic Accessibility Score:	2.125
Fsp3:	0.412
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:	-4.778
MDCK Permeability:	1.5868583432165906e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.973
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.186
Plasma Protein Binding (PPB):	98.48377227783203%
Volume Distribution (VD):	1.306
Pgp-substrate:	1.0455821752548218%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.96
CYP2C19-substrate:	0.481
CYP2C9-inhibitor:	0.921
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.86
CYP2D6-substrate:	0.934
CYP3A4-inhibitor:	0.683
CYP3A4-substrate:	0.635

ADMET: Excretion

Clearance (CL):	8.814
Half-life (T1/2):	0.629

ADMET: Toxicity

hERG Blockers:	0.225
Human Hepatotoxicity (H-HT):	0.209
Drug-inuced Liver Injury (DILI):	0.546
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.192
Maximum Recommended Daily Dose:	0.564
Skin Sensitization:	0.861
Carcinogencity:	0.205
Eye Corrosion:	0.151
Eye Irritation:	0.931
Respiratory Toxicity:	0.584

Download Data

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

Natural Product: NPC204592

Natural Product ID:	NPC204592
*Common Name:**	4-[2-(5-Butylfuran-2-Yl)Ethyl]-2-Methoxyphenol
IUPAC Name:	4-[2-(5-butylfuran-2-yl)ethyl]-2-methoxyphenol
Synonyms:
Standard InCHIKey:	VFYKGOGEJRZWKU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H22O3/c1-3-4-5-14-9-10-15(20-14)8-6-13-7-11-16(18)17(12-13)19-2/h7,9-12,18H,3-6,8H2,1-2H3
SMILES:	CCCCc1ccc(CCc2ccc(c(c2)OC)O)o1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071438
PubChem CID:	11000257
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000262] Fatty acids and conjugates [CHEMONTID:0001989] Heterocyclic fatty acids [CHEMONTID:0001528] Furanoid fatty acids

*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
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[18177011]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271742]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20590154]
NPO19141	Aframomum melegueta	Species	Zingiberaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[22789014]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Resin, Exudate, Sap	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19141	Aframomum melegueta	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	2
Others	9

Activity Type	# Activity
Organism	2
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1107	Organism	Mycobacterium smegmatis str. MC2 155	Mycobacterium smegmatis str. MC2 155	MIC	>=	128.0	ug.mL-1	PMID[450525]
NPT1107	Organism	Mycobacterium smegmatis str. MC2 155	Mycobacterium smegmatis str. MC2 155	MIC	=	32.0	ug.mL-1	PMID[450525]
NPT2	Others	Unspecified		FC	=	8.0	n.a.	PMID[450525]
NPT2	Others	Unspecified		FC	=	2.0	n.a.	PMID[450525]
NPT2	Others	Unspecified		FC	=	4.0	n.a.	PMID[450525]
NPT2	Others	Unspecified		FC	=	16.0	n.a.	PMID[450525]
NPT2	Others	Unspecified		FICI	=	0.19	n.a.	PMID[450525]
NPT2	Others	Unspecified		RFU	=	17180.3	n.a.	PMID[450525]
NPT2	Others	Unspecified		Ratio	=	0.778	n.a.	PMID[450525]

☑ 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 NPC204592 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	321
0.1-0.2	1641
0.2-0.3	4409
0.3-0.4	11684
0.4-0.5	6099
0.5-0.6	3914
0.6-0.7	8020
0.7-0.8	6150
0.8-0.85	398
0.85-0.9	52
0.9-0.95	8
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9062	High Similarity	NPC242372
0.9062	High Similarity	NPC4181
0.9062	High Similarity	NPC164778
0.9062	High Similarity	NPC257976
0.9008	High Similarity	NPC226661
0.9	High Similarity	NPC179777
0.8992	High Similarity	NPC273686
0.8992	High Similarity	NPC312404
0.8984	High Similarity	NPC114298
0.8939	High Similarity	NPC304622
0.8931	High Similarity	NPC5018
0.8931	High Similarity	NPC123722
0.8931	High Similarity	NPC16651
0.8931	High Similarity	NPC151167
0.8931	High Similarity	NPC123228
0.8931	High Similarity	NPC32163
0.8931	High Similarity	NPC276466
0.8923	High Similarity	NPC3221
0.8906	High Similarity	NPC201777
0.8872	High Similarity	NPC66905
0.8855	High Similarity	NPC84076
0.8855	High Similarity	NPC90128
0.8855	High Similarity	NPC303680
0.8779	High Similarity	NPC53305
0.8779	High Similarity	NPC257589
0.8769	High Similarity	NPC163083
0.8759	High Similarity	NPC90431
0.875	High Similarity	NPC144662
0.8731	High Similarity	NPC172673
0.8731	High Similarity	NPC298268
0.8723	High Similarity	NPC46880
0.8712	High Similarity	NPC127937
0.8712	High Similarity	NPC92207
0.8707	High Similarity	NPC268008
0.8682	High Similarity	NPC158949
0.8672	High Similarity	NPC299406
0.8643	High Similarity	NPC28398
0.8603	High Similarity	NPC239302
0.8603	High Similarity	NPC50763
0.8571	High Similarity	NPC276014
0.854	High Similarity	NPC327410
0.8521	High Similarity	NPC141817
0.8521	High Similarity	NPC192597
0.8521	High Similarity	NPC176030
0.8521	High Similarity	NPC229218
0.8521	High Similarity	NPC169214
0.8519	High Similarity	NPC241354
0.8511	High Similarity	NPC326065
0.8507	High Similarity	NPC12022
0.8507	High Similarity	NPC117237
0.8507	High Similarity	NPC203719
0.8507	High Similarity	NPC20404
0.8507	High Similarity	NPC293641
0.8507	High Similarity	NPC20287
0.85	High Similarity	NPC284409
0.8496	Intermediate Similarity	NPC87113
0.8496	Intermediate Similarity	NPC280767
0.8485	Intermediate Similarity	NPC229084
0.8485	Intermediate Similarity	NPC160900
0.8485	Intermediate Similarity	NPC474691
0.8485	Intermediate Similarity	NPC18984
0.8485	Intermediate Similarity	NPC106659
0.8478	Intermediate Similarity	NPC5310
0.8478	Intermediate Similarity	NPC300776
0.8478	Intermediate Similarity	NPC4982
0.8478	Intermediate Similarity	NPC176814
0.8478	Intermediate Similarity	NPC68779
0.8478	Intermediate Similarity	NPC471110
0.8478	Intermediate Similarity	NPC265793
0.8472	Intermediate Similarity	NPC287495
0.8472	Intermediate Similarity	NPC9370
0.8462	Intermediate Similarity	NPC239608
0.8462	Intermediate Similarity	NPC46161
0.8456	Intermediate Similarity	NPC215941
0.8456	Intermediate Similarity	NPC244246
0.8456	Intermediate Similarity	NPC319282
0.8456	Intermediate Similarity	NPC275724
0.8456	Intermediate Similarity	NPC311419
0.8456	Intermediate Similarity	NPC123196
0.8456	Intermediate Similarity	NPC65935
0.8456	Intermediate Similarity	NPC137427
0.8446	Intermediate Similarity	NPC131121
0.8444	Intermediate Similarity	NPC278308
0.8417	Intermediate Similarity	NPC139519
0.8409	Intermediate Similarity	NPC286573
0.8406	Intermediate Similarity	NPC475468
0.8403	Intermediate Similarity	NPC207732
0.8397	Intermediate Similarity	NPC14007
0.8397	Intermediate Similarity	NPC189844
0.8397	Intermediate Similarity	NPC109083
0.8397	Intermediate Similarity	NPC60962
0.8397	Intermediate Similarity	NPC224814
0.8397	Intermediate Similarity	NPC225245
0.8397	Intermediate Similarity	NPC269843
0.838	Intermediate Similarity	NPC138438
0.838	Intermediate Similarity	NPC908
0.8367	Intermediate Similarity	NPC261322
0.8366	Intermediate Similarity	NPC272722
0.8366	Intermediate Similarity	NPC84515
0.8366	Intermediate Similarity	NPC312056
0.8358	Intermediate Similarity	NPC473626
0.8357	Intermediate Similarity	NPC278832
0.8357	Intermediate Similarity	NPC64157
0.8356	Intermediate Similarity	NPC472969
0.8345	Intermediate Similarity	NPC157133
0.8333	Intermediate Similarity	NPC194416
0.8333	Intermediate Similarity	NPC177291
0.8333	Intermediate Similarity	NPC50954
0.8333	Intermediate Similarity	NPC111888
0.8333	Intermediate Similarity	NPC469615
0.8333	Intermediate Similarity	NPC473090
0.8333	Intermediate Similarity	NPC180901
0.8333	Intermediate Similarity	NPC80489
0.8333	Intermediate Similarity	NPC300757
0.8322	Intermediate Similarity	NPC110419
0.8322	Intermediate Similarity	NPC304954
0.8322	Intermediate Similarity	NPC60211
0.8312	Intermediate Similarity	NPC89131
0.8311	Intermediate Similarity	NPC243891
0.831	Intermediate Similarity	NPC474784
0.8301	Intermediate Similarity	NPC188486
0.8299	Intermediate Similarity	NPC98809
0.8299	Intermediate Similarity	NPC476394
0.8298	Intermediate Similarity	NPC130976
0.8296	Intermediate Similarity	NPC213552
0.8296	Intermediate Similarity	NPC120225
0.8289	Intermediate Similarity	NPC196879
0.8289	Intermediate Similarity	NPC16935
0.8286	Intermediate Similarity	NPC208760
0.8284	Intermediate Similarity	NPC60517
0.8284	Intermediate Similarity	NPC146886
0.8284	Intermediate Similarity	NPC20443
0.8276	Intermediate Similarity	NPC91694
0.8276	Intermediate Similarity	NPC300603
0.8276	Intermediate Similarity	NPC469683
0.8273	Intermediate Similarity	NPC283823
0.8273	Intermediate Similarity	NPC159418
0.8267	Intermediate Similarity	NPC25127
0.8267	Intermediate Similarity	NPC474000
0.8264	Intermediate Similarity	NPC312256
0.8264	Intermediate Similarity	NPC27220
0.8261	Intermediate Similarity	NPC469480
0.8258	Intermediate Similarity	NPC36320
0.8255	Intermediate Similarity	NPC267091
0.8248	Intermediate Similarity	NPC261759
0.8239	Intermediate Similarity	NPC325625
0.8239	Intermediate Similarity	NPC62735
0.8235	Intermediate Similarity	NPC286683
0.8235	Intermediate Similarity	NPC472962
0.8235	Intermediate Similarity	NPC472961
0.8231	Intermediate Similarity	NPC86947
0.8231	Intermediate Similarity	NPC469540
0.8231	Intermediate Similarity	NPC469539
0.8227	Intermediate Similarity	NPC163029
0.8227	Intermediate Similarity	NPC324929
0.8222	Intermediate Similarity	NPC289459
0.8219	Intermediate Similarity	NPC30890
0.8212	Intermediate Similarity	NPC117992
0.8212	Intermediate Similarity	NPC168247
0.8212	Intermediate Similarity	NPC230149
0.8212	Intermediate Similarity	NPC152951
0.8212	Intermediate Similarity	NPC234255
0.8212	Intermediate Similarity	NPC57674
0.8209	Intermediate Similarity	NPC118853
0.8209	Intermediate Similarity	NPC317769
0.8209	Intermediate Similarity	NPC31344
0.8209	Intermediate Similarity	NPC244876
0.8207	Intermediate Similarity	NPC254659
0.82	Intermediate Similarity	NPC472912
0.82	Intermediate Similarity	NPC60972
0.82	Intermediate Similarity	NPC257648
0.82	Intermediate Similarity	NPC237994
0.82	Intermediate Similarity	NPC39732
0.82	Intermediate Similarity	NPC477231
0.8195	Intermediate Similarity	NPC290451
0.8195	Intermediate Similarity	NPC127389
0.8194	Intermediate Similarity	NPC472332
0.8194	Intermediate Similarity	NPC133065
0.8194	Intermediate Similarity	NPC472410
0.8194	Intermediate Similarity	NPC472335
0.8188	Intermediate Similarity	NPC477694
0.8188	Intermediate Similarity	NPC29231
0.8188	Intermediate Similarity	NPC142985
0.8188	Intermediate Similarity	NPC477705
0.8188	Intermediate Similarity	NPC195292
0.8182	Intermediate Similarity	NPC289690
0.8182	Intermediate Similarity	NPC288452
0.8182	Intermediate Similarity	NPC322021
0.8176	Intermediate Similarity	NPC474903
0.817	Intermediate Similarity	NPC228501
0.817	Intermediate Similarity	NPC195832
0.8168	Intermediate Similarity	NPC470626
0.8163	Intermediate Similarity	NPC165389
0.8163	Intermediate Similarity	NPC209278
0.8163	Intermediate Similarity	NPC39361
0.8158	Intermediate Similarity	NPC472461
0.8158	Intermediate Similarity	NPC472455
0.8158	Intermediate Similarity	NPC45131
0.8156	Intermediate Similarity	NPC152209
0.8154	Intermediate Similarity	NPC19290

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 NPC204592 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	310
0.1-0.2	989
0.2-0.3	1446
0.3-0.4	2629
0.4-0.5	1886
0.5-0.6	1130
0.6-0.7	613
0.7-0.8	140
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8507	High Similarity	NPD9494	Approved
0.8485	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8278	Intermediate Similarity	NPD3882	Suspended
0.8112	Intermediate Similarity	NPD2344	Approved
0.8079	Intermediate Similarity	NPD1934	Approved
0.8047	Intermediate Similarity	NPD228	Approved
0.8026	Intermediate Similarity	NPD2801	Approved
0.7955	Intermediate Similarity	NPD5536	Phase 2
0.7908	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2309	Approved
0.7887	Intermediate Similarity	NPD447	Suspended
0.7823	Intermediate Similarity	NPD4628	Phase 3
0.7812	Intermediate Similarity	NPD3818	Discontinued
0.7786	Intermediate Similarity	NPD1241	Discontinued
0.7785	Intermediate Similarity	NPD1511	Approved
0.7692	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6166	Phase 2
0.7688	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1512	Approved
0.7677	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD2935	Discontinued
0.7632	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD1876	Approved
0.7619	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3972	Approved
0.7603	Intermediate Similarity	NPD2799	Discontinued
0.7584	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4110	Phase 3
0.7538	Intermediate Similarity	NPD2684	Approved
0.7519	Intermediate Similarity	NPD5283	Phase 1
0.7517	Intermediate Similarity	NPD6355	Discontinued
0.7517	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD230	Phase 1
0.7516	Intermediate Similarity	NPD3926	Phase 2
0.7516	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD7074	Phase 3
0.7484	Intermediate Similarity	NPD919	Approved
0.7483	Intermediate Similarity	NPD3027	Phase 3
0.7451	Intermediate Similarity	NPD6273	Approved
0.7448	Intermediate Similarity	NPD1240	Approved
0.7439	Intermediate Similarity	NPD7054	Approved
0.7438	Intermediate Similarity	NPD5494	Approved
0.7431	Intermediate Similarity	NPD6798	Discontinued
0.7419	Intermediate Similarity	NPD824	Approved
0.7419	Intermediate Similarity	NPD3455	Phase 2
0.7417	Intermediate Similarity	NPD2354	Approved
0.741	Intermediate Similarity	NPD6559	Discontinued
0.741	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1933	Approved
0.7394	Intermediate Similarity	NPD2798	Approved
0.7394	Intermediate Similarity	NPD7472	Approved
0.7391	Intermediate Similarity	NPD1247	Approved
0.7386	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2163	Approved
0.7372	Intermediate Similarity	NPD9545	Approved
0.7361	Intermediate Similarity	NPD7095	Approved
0.7357	Intermediate Similarity	NPD9717	Approved
0.7357	Intermediate Similarity	NPD1608	Approved
0.7351	Intermediate Similarity	NPD3750	Approved
0.7351	Intermediate Similarity	NPD8166	Discontinued
0.7347	Intermediate Similarity	NPD1607	Approved
0.7342	Intermediate Similarity	NPD1465	Phase 2
0.7333	Intermediate Similarity	NPD1549	Phase 2
0.7329	Intermediate Similarity	NPD943	Approved
0.7329	Intermediate Similarity	NPD4060	Phase 1
0.7324	Intermediate Similarity	NPD1203	Approved
0.7324	Intermediate Similarity	NPD2797	Approved
0.732	Intermediate Similarity	NPD6799	Approved
0.7319	Intermediate Similarity	NPD1357	Approved
0.7319	Intermediate Similarity	NPD1651	Approved
0.7315	Intermediate Similarity	NPD2796	Approved
0.7313	Intermediate Similarity	NPD7843	Approved
0.7312	Intermediate Similarity	NPD7075	Discontinued
0.731	Intermediate Similarity	NPD3764	Approved
0.731	Intermediate Similarity	NPD2313	Discontinued
0.7296	Intermediate Similarity	NPD2296	Approved
0.7292	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7157	Approved
0.7267	Intermediate Similarity	NPD1471	Phase 3
0.7267	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2346	Discontinued
0.7261	Intermediate Similarity	NPD7028	Phase 2
0.7261	Intermediate Similarity	NPD4380	Phase 2
0.726	Intermediate Similarity	NPD4062	Phase 3
0.726	Intermediate Similarity	NPD6233	Phase 2
0.7254	Intermediate Similarity	NPD1283	Approved
0.7248	Intermediate Similarity	NPD1510	Phase 2
0.7248	Intermediate Similarity	NPD4308	Phase 3
0.7246	Intermediate Similarity	NPD1894	Discontinued
0.7246	Intermediate Similarity	NPD6797	Phase 2
0.7246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD1481	Phase 2
0.7233	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5844	Phase 1
0.7226	Intermediate Similarity	NPD5049	Phase 3
0.7222	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3022	Approved
0.7218	Intermediate Similarity	NPD3021	Approved
0.7211	Intermediate Similarity	NPD3142	Approved
0.7211	Intermediate Similarity	NPD1613	Approved
0.7211	Intermediate Similarity	NPD3620	Phase 2
0.7211	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3140	Approved
0.7211	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1558	Phase 1
0.7205	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7251	Discontinued
0.7192	Intermediate Similarity	NPD3268	Approved
0.7192	Intermediate Similarity	NPD411	Approved
0.719	Intermediate Similarity	NPD3887	Approved
0.7188	Intermediate Similarity	NPD5978	Approved
0.7188	Intermediate Similarity	NPD5977	Approved
0.7172	Intermediate Similarity	NPD6832	Phase 2
0.7171	Intermediate Similarity	NPD1243	Approved
0.7163	Intermediate Similarity	NPD1535	Discovery
0.7161	Intermediate Similarity	NPD4662	Approved
0.7161	Intermediate Similarity	NPD4661	Approved
0.7161	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6234	Discontinued
0.716	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7808	Phase 3
0.7153	Intermediate Similarity	NPD6671	Approved
0.7153	Intermediate Similarity	NPD5647	Approved
0.7152	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2353	Approved
0.7152	Intermediate Similarity	NPD6599	Discontinued
0.7152	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD2674	Phase 3
0.7143	Intermediate Similarity	NPD4626	Approved
0.7135	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6232	Discontinued
0.7125	Intermediate Similarity	NPD7819	Suspended
0.7124	Intermediate Similarity	NPD7003	Approved
0.7114	Intermediate Similarity	NPD6653	Approved
0.7108	Intermediate Similarity	NPD7473	Discontinued
0.7107	Intermediate Similarity	NPD6386	Approved
0.7107	Intermediate Similarity	NPD6385	Approved
0.7107	Intermediate Similarity	NPD6873	Phase 2
0.7105	Intermediate Similarity	NPD2424	Discontinued
0.7105	Intermediate Similarity	NPD4534	Discontinued
0.7105	Intermediate Similarity	NPD5958	Discontinued
0.7101	Intermediate Similarity	NPD7685	Pre-registration
0.7101	Intermediate Similarity	NPD9493	Approved
0.7099	Intermediate Similarity	NPD3749	Approved
0.7092	Intermediate Similarity	NPD3496	Discontinued
0.7089	Intermediate Similarity	NPD2649	Approved
0.7089	Intermediate Similarity	NPD7458	Discontinued
0.7089	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2651	Approved
0.7078	Intermediate Similarity	NPD6190	Approved
0.7073	Intermediate Similarity	NPD8127	Discontinued
0.7073	Intermediate Similarity	NPD7199	Phase 2
0.707	Intermediate Similarity	NPD3869	Phase 3
0.707	Intermediate Similarity	NPD3873	Phase 3
0.7068	Intermediate Similarity	NPD1358	Approved
0.7063	Intermediate Similarity	NPD6280	Approved
0.7063	Intermediate Similarity	NPD6801	Discontinued
0.7063	Intermediate Similarity	NPD6279	Approved
0.7047	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3705	Approved
0.7042	Intermediate Similarity	NPD1281	Approved
0.7034	Intermediate Similarity	NPD6584	Phase 3
0.7032	Intermediate Similarity	NPD7440	Discontinued
0.7032	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8032	Phase 2
0.7021	Intermediate Similarity	NPD1778	Approved
0.702	Intermediate Similarity	NPD3748	Approved
0.7011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7411	Suspended
0.7	Intermediate Similarity	NPD7038	Approved
0.7	Intermediate Similarity	NPD7039	Approved
0.6993	Remote Similarity	NPD9269	Phase 2
0.6993	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3134	Approved
0.6988	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD4357	Discontinued
0.6986	Remote Similarity	NPD2861	Phase 2
0.6981	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD3226	Approved
0.698	Remote Similarity	NPD825	Approved
0.698	Remote Similarity	NPD4307	Phase 2
0.698	Remote Similarity	NPD826	Approved
0.6975	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD5402	Approved
0.6975	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4476	Approved
0.6974	Remote Similarity	NPD1551	Phase 2
0.6974	Remote Similarity	NPD4477	Approved
0.6974	Remote Similarity	NPD2161	Phase 2
0.6972	Remote Similarity	NPD3847	Discontinued
0.697	Remote Similarity	NPD2821	Approved
0.6962	Remote Similarity	NPD5403	Approved
0.6962	Remote Similarity	NPD920	Approved
0.6959	Remote Similarity	NPD3144	Approved
0.6959	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3145	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