NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	138.07
Volume:	148.039
LogP:	1.883
LogD:	1.924
LogS:	-0.482
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.619
Synthetic Accessibility Score:	1.935
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.489
MDCK Permeability:	2.009368472499773e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.045
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.937
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	69.6148452758789%
Volume Distribution (VD):	1.245
Pgp-substrate:	23.43296241760254%

ADMET: Metabolism

CYP1A2-inhibitor:	0.868
CYP1A2-substrate:	0.871
CYP2C19-inhibitor:	0.286
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.222
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.659
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.31
CYP3A4-substrate:	0.217

ADMET: Excretion

Clearance (CL):	16.152
Half-life (T1/2):	0.91

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.383
Rat Oral Acute Toxicity:	0.743
Maximum Recommended Daily Dose:	0.065
Skin Sensitization:	0.921
Carcinogencity:	0.348
Eye Corrosion:	0.943
Eye Irritation:	0.98
Respiratory Toxicity:	0.219

Download Data

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

Natural Product: NPC80027

Natural Product ID:	NPC80027
*Common Name:**	4-Ethylresorcinol
IUPAC Name:	4-ethylbenzene-1,3-diol
Synonyms:	4-Ethylresorcinol
Standard InCHIKey:	VGMJYYDKPUPTID-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H10O2/c1-2-6-3-4-7(9)5-8(6)10/h3-5,9-10H,2H2,1H3
SMILES:	CCc1ccc(cc1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332776
PubChem CID:	17927
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0001286] Benzenediols [CHEMONTID:0000137] Resorcinols

*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
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
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]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8064299]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	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]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20553	Zingiber officinale	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8516	Dipsacus asperoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	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	2
Others	6

Activity Type	# Activity
Individual Protein	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	1900.0	nM	PMID[549485]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	1100.0	nM	PMID[549485]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Km	=	117000.0	nM	PMID[549485]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Kcat	=	6.0	/s	PMID[549485]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Kcat/Km	=	51.3	/mM/s	PMID[549485]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Activity	=	0.0	%	PMID[549484]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Activity	<	1.0	%	PMID[549484]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Activity	=	1.0	%	PMID[549484]

☑ 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 NPC80027 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	288
0.1-0.2	2091
0.2-0.3	7501
0.3-0.4	12521
0.4-0.5	4819
0.5-0.6	8243
0.6-0.7	5503
0.7-0.8	1430
0.8-0.85	187
0.85-0.9	103
0.9-0.95	9
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9381	High Similarity	NPC119860
0.9286	High Similarity	NPC474839
0.92	High Similarity	NPC61885
0.92	High Similarity	NPC63698
0.9192	High Similarity	NPC248904
0.9091	High Similarity	NPC292452
0.9072	High Similarity	NPC166761
0.899	High Similarity	NPC244513
0.899	High Similarity	NPC102216
0.899	High Similarity	NPC227458
0.899	High Similarity	NPC30506
0.899	High Similarity	NPC218879
0.8932	High Similarity	NPC225679
0.8932	High Similarity	NPC165770
0.8932	High Similarity	NPC476632
0.8932	High Similarity	NPC4493
0.8922	High Similarity	NPC202647
0.8913	High Similarity	NPC407
0.8913	High Similarity	NPC307235
0.8913	High Similarity	NPC23167
0.8911	High Similarity	NPC232523
0.8911	High Similarity	NPC204901
0.8911	High Similarity	NPC158253
0.89	High Similarity	NPC37802
0.8889	High Similarity	NPC168303
0.8889	High Similarity	NPC313030
0.8889	High Similarity	NPC249828
0.8889	High Similarity	NPC71002
0.8889	High Similarity	NPC85479
0.8889	High Similarity	NPC146798
0.8889	High Similarity	NPC302219
0.8889	High Similarity	NPC222522
0.8889	High Similarity	NPC242342
0.8889	High Similarity	NPC106396
0.8889	High Similarity	NPC24404
0.8889	High Similarity	NPC94351
0.8889	High Similarity	NPC53051
0.8878	High Similarity	NPC10588
0.8878	High Similarity	NPC275053
0.8878	High Similarity	NPC248573
0.8878	High Similarity	NPC161571
0.8854	High Similarity	NPC313650
0.8846	High Similarity	NPC166995
0.8846	High Similarity	NPC43525
0.8842	High Similarity	NPC295295
0.8835	High Similarity	NPC224870
0.8835	High Similarity	NPC475018
0.8824	High Similarity	NPC174981
0.8817	High Similarity	NPC113460
0.8817	High Similarity	NPC25493
0.8812	High Similarity	NPC201662
0.8812	High Similarity	NPC99836
0.8812	High Similarity	NPC12640
0.8804	High Similarity	NPC155393
0.8804	High Similarity	NPC197783
0.8788	High Similarity	NPC72947
0.8788	High Similarity	NPC137415
0.8788	High Similarity	NPC147310
0.8788	High Similarity	NPC192032
0.8788	High Similarity	NPC284011
0.8788	High Similarity	NPC24407
0.8788	High Similarity	NPC166313
0.8788	High Similarity	NPC143659
0.8788	High Similarity	NPC11280
0.8788	High Similarity	NPC294186
0.8788	High Similarity	NPC100340
0.8762	High Similarity	NPC117846
0.875	High Similarity	NPC128062
0.8738	High Similarity	NPC33728
0.8738	High Similarity	NPC19808
0.8737	High Similarity	NPC204210
0.8723	High Similarity	NPC318325
0.8723	High Similarity	NPC177420
0.8723	High Similarity	NPC258219
0.8723	High Similarity	NPC123273
0.8723	High Similarity	NPC242240
0.8723	High Similarity	NPC280347
0.8696	High Similarity	NPC286904
0.8696	High Similarity	NPC175313
0.8696	High Similarity	NPC248817
0.8679	High Similarity	NPC107240
0.8673	High Similarity	NPC291789
0.8667	High Similarity	NPC473521
0.866	High Similarity	NPC8392
0.8646	High Similarity	NPC138117
0.8646	High Similarity	NPC325292
0.8632	High Similarity	NPC47950
0.8632	High Similarity	NPC300017
0.8632	High Similarity	NPC55561
0.8632	High Similarity	NPC300478
0.8614	High Similarity	NPC241891
0.8598	High Similarity	NPC464
0.8598	High Similarity	NPC185541
0.8587	High Similarity	NPC265146
0.8587	High Similarity	NPC124436
0.8586	High Similarity	NPC128723
0.8585	High Similarity	NPC263753
0.8571	High Similarity	NPC224527
0.8558	High Similarity	NPC186385
0.8558	High Similarity	NPC299568
0.8544	High Similarity	NPC61033
0.8544	High Similarity	NPC305603
0.8542	High Similarity	NPC304541
0.8542	High Similarity	NPC45040
0.8542	High Similarity	NPC306074
0.8529	High Similarity	NPC134829
0.8529	High Similarity	NPC471350
0.8526	High Similarity	NPC70436
0.8519	High Similarity	NPC54507
0.8519	High Similarity	NPC85292
0.8519	High Similarity	NPC229147
0.8511	High Similarity	NPC184169
0.8485	Intermediate Similarity	NPC77492
0.8469	Intermediate Similarity	NPC26244
0.8447	Intermediate Similarity	NPC39664
0.8447	Intermediate Similarity	NPC118286
0.8447	Intermediate Similarity	NPC109691
0.8447	Intermediate Similarity	NPC470700
0.8447	Intermediate Similarity	NPC39097
0.8447	Intermediate Similarity	NPC302681
0.8421	Intermediate Similarity	NPC104216
0.8421	Intermediate Similarity	NPC27974
0.84	Intermediate Similarity	NPC252821
0.84	Intermediate Similarity	NPC122005
0.8396	Intermediate Similarity	NPC268032
0.8384	Intermediate Similarity	NPC473388
0.8367	Intermediate Similarity	NPC27323
0.8367	Intermediate Similarity	NPC151715
0.8367	Intermediate Similarity	NPC245187
0.8367	Intermediate Similarity	NPC316301
0.8367	Intermediate Similarity	NPC152415
0.8365	Intermediate Similarity	NPC54844
0.8365	Intermediate Similarity	NPC176527
0.8364	Intermediate Similarity	NPC131118
0.8364	Intermediate Similarity	NPC144343
0.8351	Intermediate Similarity	NPC270547
0.8351	Intermediate Similarity	NPC231150
0.8351	Intermediate Similarity	NPC155908
0.835	Intermediate Similarity	NPC246056
0.8349	Intermediate Similarity	NPC203113
0.8333	Intermediate Similarity	NPC118288
0.8333	Intermediate Similarity	NPC168393
0.8333	Intermediate Similarity	NPC276111
0.8333	Intermediate Similarity	NPC98772
0.8317	Intermediate Similarity	NPC225506
0.8317	Intermediate Similarity	NPC130103
0.83	Intermediate Similarity	NPC152097
0.83	Intermediate Similarity	NPC260000
0.8288	Intermediate Similarity	NPC161617
0.8288	Intermediate Similarity	NPC217174
0.8286	Intermediate Similarity	NPC114392
0.8286	Intermediate Similarity	NPC34864
0.8286	Intermediate Similarity	NPC105727
0.8286	Intermediate Similarity	NPC58427
0.8283	Intermediate Similarity	NPC144682
0.8283	Intermediate Similarity	NPC274678
0.8273	Intermediate Similarity	NPC470760
0.8273	Intermediate Similarity	NPC277588
0.8265	Intermediate Similarity	NPC29373
0.8265	Intermediate Similarity	NPC181709
0.8265	Intermediate Similarity	NPC271440
0.8261	Intermediate Similarity	NPC270094
0.8257	Intermediate Similarity	NPC84999
0.8257	Intermediate Similarity	NPC246760
0.8257	Intermediate Similarity	NPC808
0.8241	Intermediate Similarity	NPC261343
0.8241	Intermediate Similarity	NPC319803
0.8241	Intermediate Similarity	NPC23804
0.8224	Intermediate Similarity	NPC90520
0.8224	Intermediate Similarity	NPC296920
0.8218	Intermediate Similarity	NPC280869
0.8218	Intermediate Similarity	NPC260775
0.8218	Intermediate Similarity	NPC92730
0.8214	Intermediate Similarity	NPC223451
0.82	Intermediate Similarity	NPC259512
0.82	Intermediate Similarity	NPC312132
0.8198	Intermediate Similarity	NPC40649
0.8198	Intermediate Similarity	NPC209486
0.8198	Intermediate Similarity	NPC74821
0.8182	Intermediate Similarity	NPC150624
0.8182	Intermediate Similarity	NPC141090
0.8182	Intermediate Similarity	NPC289769
0.8182	Intermediate Similarity	NPC115808
0.8173	Intermediate Similarity	NPC99557
0.8173	Intermediate Similarity	NPC138942
0.8173	Intermediate Similarity	NPC219286
0.8173	Intermediate Similarity	NPC303141
0.8155	Intermediate Similarity	NPC168829
0.8155	Intermediate Similarity	NPC470202
0.8152	Intermediate Similarity	NPC4154
0.8148	Intermediate Similarity	NPC280606
0.8142	Intermediate Similarity	NPC102639
0.8142	Intermediate Similarity	NPC24125
0.8137	Intermediate Similarity	NPC248396
0.8137	Intermediate Similarity	NPC48730
0.8137	Intermediate Similarity	NPC70677
0.8137	Intermediate Similarity	NPC72729
0.8137	Intermediate Similarity	NPC129373
0.8137	Intermediate Similarity	NPC213730
0.8137	Intermediate Similarity	NPC130756

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 NPC80027 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	1087
0.2-0.3	1730
0.3-0.4	2892
0.4-0.5	1723
0.5-0.6	995
0.6-0.7	315
0.7-0.8	57
0.8-0.85	12
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9787	High Similarity	NPD846	Approved
0.9787	High Similarity	NPD940	Approved
0.8878	High Similarity	NPD1242	Phase 1
0.8587	High Similarity	NPD111	Approved
0.8558	High Similarity	NPD4750	Phase 3
0.8557	High Similarity	NPD2934	Approved
0.8557	High Similarity	NPD2933	Approved
0.8469	Intermediate Similarity	NPD2859	Approved
0.8469	Intermediate Similarity	NPD2860	Approved
0.8367	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.8283	Intermediate Similarity	NPD844	Approved
0.8283	Intermediate Similarity	NPD1809	Phase 2
0.8265	Intermediate Similarity	NPD845	Approved
0.8261	Intermediate Similarity	NPD9089	Approved
0.8218	Intermediate Similarity	NPD3020	Approved
0.82	Intermediate Similarity	NPD288	Approved
0.8198	Intermediate Similarity	NPD1548	Phase 1
0.8152	Intermediate Similarity	NPD9093	Approved
0.8137	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD422	Phase 1
0.7941	Intermediate Similarity	NPD9273	Approved
0.7913	Intermediate Similarity	NPD1610	Phase 2
0.7755	Intermediate Similarity	NPD9094	Approved
0.7736	Intermediate Similarity	NPD9610	Approved
0.7736	Intermediate Similarity	NPD9608	Approved
0.7706	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4908	Phase 1
0.7545	Intermediate Similarity	NPD3022	Approved
0.7545	Intermediate Similarity	NPD3021	Approved
0.748	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD4749	Approved
0.7459	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3028	Approved
0.7411	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD228	Approved
0.7391	Intermediate Similarity	NPD9087	Approved
0.7377	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1476	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD290	Approved
0.7364	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD1240	Approved
0.7355	Intermediate Similarity	NPD1129	Approved
0.7355	Intermediate Similarity	NPD1135	Approved
0.7355	Intermediate Similarity	NPD1131	Approved
0.7355	Intermediate Similarity	NPD1134	Approved
0.7355	Intermediate Similarity	NPD1133	Approved
0.7328	Intermediate Similarity	NPD318	Approved
0.7328	Intermediate Similarity	NPD856	Approved
0.7328	Intermediate Similarity	NPD317	Approved
0.7328	Intermediate Similarity	NPD16	Approved
0.7297	Intermediate Similarity	NPD9266	Approved
0.7297	Intermediate Similarity	NPD74	Approved
0.7281	Intermediate Similarity	NPD2234	Approved
0.7281	Intermediate Similarity	NPD2228	Approved
0.7281	Intermediate Similarity	NPD2229	Approved
0.7281	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1444	Approved
0.7273	Intermediate Similarity	NPD1445	Approved
0.7263	Intermediate Similarity	NPD9088	Approved
0.7258	Intermediate Similarity	NPD4625	Phase 3
0.7258	Intermediate Similarity	NPD3027	Phase 3
0.7244	Intermediate Similarity	NPD1607	Approved
0.7241	Intermediate Similarity	NPD9493	Approved
0.7222	Intermediate Similarity	NPD1613	Approved
0.7222	Intermediate Similarity	NPD1555	Discontinued
0.7222	Intermediate Similarity	NPD468	Phase 1
0.7222	Intermediate Similarity	NPD943	Approved
0.7222	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD9264	Approved
0.7207	Intermediate Similarity	NPD2342	Discontinued
0.7207	Intermediate Similarity	NPD9267	Approved
0.7207	Intermediate Similarity	NPD9263	Approved
0.72	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD9379	Approved
0.7193	Intermediate Similarity	NPD7635	Approved
0.7193	Intermediate Similarity	NPD9377	Approved
0.7168	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD9294	Approved
0.7155	Intermediate Similarity	NPD6671	Approved
0.7155	Intermediate Similarity	NPD256	Approved
0.7155	Intermediate Similarity	NPD255	Approved
0.7154	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2684	Approved
0.7143	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5304	Approved
0.7119	Intermediate Similarity	NPD1759	Phase 1
0.7119	Intermediate Similarity	NPD5303	Approved
0.7119	Intermediate Similarity	NPD9545	Approved
0.7117	Intermediate Similarity	NPD968	Approved
0.708	Intermediate Similarity	NPD1792	Phase 2
0.7063	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD821	Approved
0.7034	Intermediate Similarity	NPD1758	Phase 1
0.7016	Intermediate Similarity	NPD858	Approved
0.7016	Intermediate Similarity	NPD859	Approved
0.7016	Intermediate Similarity	NPD599	Approved
0.7016	Intermediate Similarity	NPD602	Approved
0.7	Intermediate Similarity	NPD9381	Approved
0.7	Intermediate Similarity	NPD9500	Approved
0.7	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4589	Approved
0.7	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1510	Phase 2
0.7	Intermediate Similarity	NPD9384	Approved
0.6977	Remote Similarity	NPD2568	Approved
0.6975	Remote Similarity	NPD3091	Approved
0.6967	Remote Similarity	NPD2561	Approved
0.6967	Remote Similarity	NPD9269	Phase 2
0.6967	Remote Similarity	NPD2562	Approved
0.696	Remote Similarity	NPD3018	Phase 2
0.6949	Remote Similarity	NPD9568	Approved
0.6935	Remote Similarity	NPD1164	Approved
0.6923	Remote Similarity	NPD475	Phase 2
0.6923	Remote Similarity	NPD9614	Approved
0.6923	Remote Similarity	NPD9618	Approved
0.6917	Remote Similarity	NPD4235	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD9268	Approved
0.6911	Remote Similarity	NPD4659	Approved
0.6911	Remote Similarity	NPD9622	Approved
0.6911	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7843	Approved
0.6894	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD1201	Approved
0.6885	Remote Similarity	NPD3092	Approved
0.6885	Remote Similarity	NPD1091	Approved
0.6875	Remote Similarity	NPD6407	Approved
0.6875	Remote Similarity	NPD6405	Approved
0.686	Remote Similarity	NPD4059	Approved
0.686	Remote Similarity	NPD3019	Approved
0.686	Remote Similarity	NPD4626	Approved
0.686	Remote Similarity	NPD2932	Approved
0.6847	Remote Similarity	NPD9261	Approved
0.6846	Remote Similarity	NPD1772	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1549	Phase 2
0.6833	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD9295	Approved
0.6825	Remote Similarity	NPD2861	Phase 2
0.6807	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3143	Discontinued
0.68	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4103	Phase 2
0.68	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3094	Phase 2
0.6794	Remote Similarity	NPD3553	Approved
0.6794	Remote Similarity	NPD3552	Approved
0.6794	Remote Similarity	NPD3555	Approved
0.6794	Remote Similarity	NPD3554	Approved
0.6783	Remote Similarity	NPD5451	Approved
0.678	Remote Similarity	NPD1791	Approved
0.678	Remote Similarity	NPD1793	Approved
0.678	Remote Similarity	NPD9281	Approved
0.6777	Remote Similarity	NPD4093	Discontinued
0.6774	Remote Similarity	NPD2983	Phase 2
0.6774	Remote Similarity	NPD2982	Phase 2
0.6769	Remote Similarity	NPD230	Phase 1
0.6769	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD5124	Phase 1
0.675	Remote Similarity	NPD9613	Approved
0.675	Remote Similarity	NPD9615	Approved
0.675	Remote Similarity	NPD9616	Approved
0.6746	Remote Similarity	NPD9620	Approved
0.6746	Remote Similarity	NPD9621	Approved
0.6746	Remote Similarity	NPD9619	Approved
0.6741	Remote Similarity	NPD3750	Approved
0.6723	Remote Similarity	NPD7157	Approved
0.6723	Remote Similarity	NPD709	Approved
0.6721	Remote Similarity	NPD1751	Approved
0.6721	Remote Similarity	NPD2286	Discontinued
0.6715	Remote Similarity	NPD7213	Phase 3
0.6715	Remote Similarity	NPD7212	Phase 2
0.6694	Remote Similarity	NPD316	Approved
0.6694	Remote Similarity	NPD3070	Discontinued
0.6694	Remote Similarity	NPD7330	Discontinued
0.6694	Remote Similarity	NPD2981	Phase 2
0.6694	Remote Similarity	NPD9717	Approved
0.6692	Remote Similarity	NPD6100	Approved
0.6692	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD3134	Approved
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3421	Phase 3
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD1296	Phase 2
0.6667	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7447	Phase 1
0.6667	Remote Similarity	NPD1652	Phase 2
0.6667	Remote Similarity	NPD1470	Approved
0.664	Remote Similarity	NPD6583	Phase 3
0.664	Remote Similarity	NPD6582	Phase 2
0.6639	Remote Similarity	NPD497	Approved
0.6618	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD3690	Phase 2
0.6614	Remote Similarity	NPD3691	Phase 2
0.6613	Remote Similarity	NPD1535	Discovery
0.661	Remote Similarity	NPD5535	Approved
0.661	Remote Similarity	NPD1138	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