NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	198.1
Volume:	226.559
LogP:	3.195
LogD:	3.451
LogS:	-3.745
# Rotatable Bonds:	4
TPSA:	9.23
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.731
Synthetic Accessibility Score:	1.253
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.395
MDCK Permeability:	5.762691216659732e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.047
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.974
30% Bioavailability (F30%):	0.018

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.732
Plasma Protein Binding (PPB):	95.34774780273438%
Volume Distribution (VD):	1.01
Pgp-substrate:	5.431797981262207%

ADMET: Metabolism

CYP1A2-inhibitor:	0.857
CYP1A2-substrate:	0.251
CYP2C19-inhibitor:	0.91
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.486
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.084
CYP3A4-inhibitor:	0.018
CYP3A4-substrate:	0.311

ADMET: Excretion

Clearance (CL):	9.153
Half-life (T1/2):	0.669

ADMET: Toxicity

hERG Blockers:	0.195
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.107
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.738
Carcinogencity:	0.636
Eye Corrosion:	0.071
Eye Irritation:	0.989
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC165212

Natural Product ID:	NPC165212
*Common Name:**	Phenylmethoxymethylbenzene
IUPAC Name:	phenylmethoxymethylbenzene
Synonyms:	1-Benzyloxymethylbenzene(Benzyl Ether)
Standard InCHIKey:	MHDVGSVTJDSBDK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H14O/c1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h1-10H,11-12H2
SMILES:	c1ccc(cc1)COCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL152299
PubChem CID:	7657
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002542] Benzylethers

*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
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Nigeria(latitude 80°N and longitude 4°E)	2005; 2006	DOI[10.1002/ejlt.201000080]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-010-0259-y]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11306-014-0638-x]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytol.2008.07.007]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Plovdiv, Plovdiv region in South Bulgaria		DOI[10.1051/CTV/20163101031]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170689]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11312782]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11408943]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12105962]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	Esuela Tecnica Superior de Ingenieros Agrónomos de Albacete	2007	PMID[19256538]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20826702]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23759170]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stalks	n.a.	n.a.	PMID[24521157]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seeds	Benedictine Pannonhalma Archabbey, Hungary		PMID[29803478]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433178]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17024	Vitis vinifera	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17024	Vitis vinifera	Species	Vitaceae	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
Potency	8

Activity Type	# Activity
Individual Protein	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT210	Individual Protein	Thyroid stimulating hormone receptor	Homo sapiens	Potency	=	39810.7	nM	PMID[537643]
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[537643]
NPT103	Individual Protein	Nuclear receptor ROR-gamma	Homo sapiens	Potency	n.a.	26603.2	nM	PMID[537643]
NPT610	Others	Molecular identity unknown		Potency	n.a.	35481.3	nM	PMID[537643]
NPT2	Others	Unspecified		Potency	n.a.	1020.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	28504.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	810.6	nM	PubChem BioAssay data set

☑ 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 NPC165212 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	406
0.1-0.2	2683
0.2-0.3	7053
0.3-0.4	13026
0.4-0.5	10510
0.5-0.6	7292
0.6-0.7	1522
0.7-0.8	189
0.8-0.85	12
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8875	High Similarity	NPC106313
0.8824	High Similarity	NPC119631
0.878	High Similarity	NPC58616
0.8571	High Similarity	NPC89377
0.8471	Intermediate Similarity	NPC304760
0.8372	Intermediate Similarity	NPC173443
0.8372	Intermediate Similarity	NPC220893
0.8276	Intermediate Similarity	NPC213156
0.8276	Intermediate Similarity	NPC240108
0.825	Intermediate Similarity	NPC66655
0.8152	Intermediate Similarity	NPC118343
0.8072	Intermediate Similarity	NPC117180
0.8065	Intermediate Similarity	NPC42211
0.8065	Intermediate Similarity	NPC316797
0.8043	Intermediate Similarity	NPC475954
0.8	Intermediate Similarity	NPC95429
0.7976	Intermediate Similarity	NPC103326
0.7976	Intermediate Similarity	NPC99394
0.7976	Intermediate Similarity	NPC329319
0.7976	Intermediate Similarity	NPC87299
0.7955	Intermediate Similarity	NPC199567
0.7912	Intermediate Similarity	NPC5472
0.7882	Intermediate Similarity	NPC172984
0.7875	Intermediate Similarity	NPC108218
0.7831	Intermediate Similarity	NPC170484
0.7791	Intermediate Similarity	NPC304538
0.7766	Intermediate Similarity	NPC98911
0.7766	Intermediate Similarity	NPC472318
0.7765	Intermediate Similarity	NPC475199
0.7765	Intermediate Similarity	NPC283012
0.7742	Intermediate Similarity	NPC92754
0.7742	Intermediate Similarity	NPC276775
0.7742	Intermediate Similarity	NPC325499
0.7742	Intermediate Similarity	NPC249912
0.7742	Intermediate Similarity	NPC270654
0.7738	Intermediate Similarity	NPC328178
0.7738	Intermediate Similarity	NPC121800
0.7732	Intermediate Similarity	NPC269457
0.7692	Intermediate Similarity	NPC321956
0.7692	Intermediate Similarity	NPC128645
0.7683	Intermediate Similarity	NPC175393
0.7674	Intermediate Similarity	NPC243289
0.7674	Intermediate Similarity	NPC208183
0.7667	Intermediate Similarity	NPC177844
0.7667	Intermediate Similarity	NPC99886
0.7667	Intermediate Similarity	NPC8002
0.7667	Intermediate Similarity	NPC259134
0.766	Intermediate Similarity	NPC35448
0.766	Intermediate Similarity	NPC95755
0.766	Intermediate Similarity	NPC225060
0.766	Intermediate Similarity	NPC78701
0.7653	Intermediate Similarity	NPC326801
0.7647	Intermediate Similarity	NPC133050
0.7625	Intermediate Similarity	NPC208302
0.7614	Intermediate Similarity	NPC93843
0.7604	Intermediate Similarity	NPC300166
0.7582	Intermediate Similarity	NPC71853
0.7579	Intermediate Similarity	NPC146351
0.7558	Intermediate Similarity	NPC103387
0.7558	Intermediate Similarity	NPC323103
0.7556	Intermediate Similarity	NPC9822
0.7529	Intermediate Similarity	NPC184030
0.7529	Intermediate Similarity	NPC164449
0.7528	Intermediate Similarity	NPC96625
0.7527	Intermediate Similarity	NPC130398
0.7526	Intermediate Similarity	NPC234305
0.75	Intermediate Similarity	NPC206341
0.75	Intermediate Similarity	NPC224544
0.75	Intermediate Similarity	NPC475710
0.75	Intermediate Similarity	NPC169450
0.75	Intermediate Similarity	NPC245927
0.75	Intermediate Similarity	NPC99482
0.75	Intermediate Similarity	NPC176228
0.75	Intermediate Similarity	NPC70624
0.7475	Intermediate Similarity	NPC92623
0.7475	Intermediate Similarity	NPC135464
0.7473	Intermediate Similarity	NPC185501
0.7471	Intermediate Similarity	NPC270507
0.7471	Intermediate Similarity	NPC127491
0.7471	Intermediate Similarity	NPC308619
0.7471	Intermediate Similarity	NPC324835
0.7468	Intermediate Similarity	NPC82770
0.7468	Intermediate Similarity	NPC78954
0.7468	Intermediate Similarity	NPC239931
0.7449	Intermediate Similarity	NPC85977
0.7449	Intermediate Similarity	NPC241224
0.7447	Intermediate Similarity	NPC21959
0.7426	Intermediate Similarity	NPC265211
0.7426	Intermediate Similarity	NPC306045
0.7423	Intermediate Similarity	NPC60373
0.7423	Intermediate Similarity	NPC154905
0.7419	Intermediate Similarity	NPC23453
0.7412	Intermediate Similarity	NPC167577
0.7412	Intermediate Similarity	NPC78517
0.7396	Intermediate Similarity	NPC100870
0.7396	Intermediate Similarity	NPC471576
0.7386	Intermediate Similarity	NPC168855
0.7374	Intermediate Similarity	NPC154899
0.7374	Intermediate Similarity	NPC37714
0.7374	Intermediate Similarity	NPC152384
0.7374	Intermediate Similarity	NPC233396
0.7374	Intermediate Similarity	NPC475269
0.7363	Intermediate Similarity	NPC1793
0.7356	Intermediate Similarity	NPC73637
0.7356	Intermediate Similarity	NPC121478
0.7349	Intermediate Similarity	NPC189371
0.7347	Intermediate Similarity	NPC301943
0.7347	Intermediate Similarity	NPC474365
0.734	Intermediate Similarity	NPC471581
0.7333	Intermediate Similarity	NPC286608
0.7333	Intermediate Similarity	NPC169050
0.7333	Intermediate Similarity	NPC36357
0.7333	Intermediate Similarity	NPC211237
0.7333	Intermediate Similarity	NPC114327
0.7312	Intermediate Similarity	NPC45040
0.7303	Intermediate Similarity	NPC125306
0.7303	Intermediate Similarity	NPC294134
0.7303	Intermediate Similarity	NPC474354
0.73	Intermediate Similarity	NPC113457
0.73	Intermediate Similarity	NPC472316
0.73	Intermediate Similarity	NPC474376
0.73	Intermediate Similarity	NPC475203
0.73	Intermediate Similarity	NPC472315
0.7292	Intermediate Similarity	NPC470161
0.7282	Intermediate Similarity	NPC79496
0.7282	Intermediate Similarity	NPC158282
0.7273	Intermediate Similarity	NPC280616
0.7273	Intermediate Similarity	NPC38079
0.7273	Intermediate Similarity	NPC108875
0.7273	Intermediate Similarity	NPC242913
0.7273	Intermediate Similarity	NPC12987
0.7273	Intermediate Similarity	NPC148060
0.7273	Intermediate Similarity	NPC171831
0.7273	Intermediate Similarity	NPC474603
0.7255	Intermediate Similarity	NPC273837
0.7255	Intermediate Similarity	NPC474272
0.7245	Intermediate Similarity	NPC84325
0.7245	Intermediate Similarity	NPC188895
0.7245	Intermediate Similarity	NPC51633
0.7241	Intermediate Similarity	NPC303245
0.7241	Intermediate Similarity	NPC89950
0.7234	Intermediate Similarity	NPC261181
0.7234	Intermediate Similarity	NPC271440
0.7228	Intermediate Similarity	NPC277788
0.7228	Intermediate Similarity	NPC260952
0.7222	Intermediate Similarity	NPC474211
0.7216	Intermediate Similarity	NPC325497
0.7216	Intermediate Similarity	NPC203925
0.7216	Intermediate Similarity	NPC78119
0.7216	Intermediate Similarity	NPC132078
0.7216	Intermediate Similarity	NPC171843
0.7216	Intermediate Similarity	NPC216468
0.7216	Intermediate Similarity	NPC51333
0.7212	Intermediate Similarity	NPC265002
0.7212	Intermediate Similarity	NPC42911
0.7212	Intermediate Similarity	NPC290353
0.7212	Intermediate Similarity	NPC153795
0.7204	Intermediate Similarity	NPC300017
0.7204	Intermediate Similarity	NPC79917
0.72	Intermediate Similarity	NPC473855
0.72	Intermediate Similarity	NPC238115
0.72	Intermediate Similarity	NPC8302
0.72	Intermediate Similarity	NPC470393
0.7184	Intermediate Similarity	NPC183700
0.7176	Intermediate Similarity	NPC3672
0.7176	Intermediate Similarity	NPC287790
0.7174	Intermediate Similarity	NPC104216
0.7172	Intermediate Similarity	NPC192596
0.7172	Intermediate Similarity	NPC305205
0.7172	Intermediate Similarity	NPC82426
0.7172	Intermediate Similarity	NPC179686
0.7172	Intermediate Similarity	NPC89886
0.7172	Intermediate Similarity	NPC91820
0.7172	Intermediate Similarity	NPC60679
0.7159	Intermediate Similarity	NPC99240
0.7158	Intermediate Similarity	NPC128062
0.7158	Intermediate Similarity	NPC76938
0.7158	Intermediate Similarity	NPC151715
0.7157	Intermediate Similarity	NPC75440
0.7143	Intermediate Similarity	NPC13755
0.7143	Intermediate Similarity	NPC155393
0.7143	Intermediate Similarity	NPC198747
0.7143	Intermediate Similarity	NPC123175
0.7143	Intermediate Similarity	NPC246588
0.7143	Intermediate Similarity	NPC294741
0.7143	Intermediate Similarity	NPC176730
0.7143	Intermediate Similarity	NPC213730
0.7129	Intermediate Similarity	NPC119271
0.7129	Intermediate Similarity	NPC37115
0.7129	Intermediate Similarity	NPC136962
0.7128	Intermediate Similarity	NPC265521
0.7126	Intermediate Similarity	NPC309279
0.7115	Intermediate Similarity	NPC266932
0.7115	Intermediate Similarity	NPC234376
0.7113	Intermediate Similarity	NPC175298
0.7111	Intermediate Similarity	NPC265146
0.71	Intermediate Similarity	NPC114594
0.71	Intermediate Similarity	NPC109637
0.71	Intermediate Similarity	NPC283546
0.71	Intermediate Similarity	NPC130817

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 NPC165212 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	1079
0.2-0.3	1298
0.3-0.4	3107
0.4-0.5	1998
0.5-0.6	982
0.6-0.7	261
0.7-0.8	24
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.825	Intermediate Similarity	NPD9294	Approved
0.8152	Intermediate Similarity	NPD1238	Approved
0.8065	Intermediate Similarity	NPD2552	Approved
0.8065	Intermediate Similarity	NPD2550	Approved
0.8065	Intermediate Similarity	NPD2549	Approved
0.8065	Intermediate Similarity	NPD2558	Approved
0.8065	Intermediate Similarity	NPD2555	Approved
0.8065	Intermediate Similarity	NPD2553	Approved
0.7979	Intermediate Similarity	NPD4189	Approved
0.7979	Intermediate Similarity	NPD4188	Approved
0.7812	Intermediate Similarity	NPD3046	Approved
0.7812	Intermediate Similarity	NPD3048	Approved
0.7812	Intermediate Similarity	NPD3047	Approved
0.7653	Intermediate Similarity	NPD3524	Approved
0.7653	Intermediate Similarity	NPD2551	Approved
0.7653	Intermediate Similarity	NPD2559	Approved
0.7653	Intermediate Similarity	NPD968	Approved
0.7653	Intermediate Similarity	NPD3526	Approved
0.7647	Intermediate Similarity	NPD9250	Approved
0.7333	Intermediate Similarity	NPD1282	Approved
0.73	Intermediate Similarity	NPD811	Approved
0.73	Intermediate Similarity	NPD810	Approved
0.73	Intermediate Similarity	NPD812	Approved
0.7282	Intermediate Similarity	NPD4571	Approved
0.7282	Intermediate Similarity	NPD4573	Approved
0.7282	Intermediate Similarity	NPD4572	Approved
0.7234	Intermediate Similarity	NPD1202	Approved
0.7212	Intermediate Similarity	NPD2497	Approved
0.7212	Intermediate Similarity	NPD2496	Approved
0.7158	Intermediate Similarity	NPD2934	Approved
0.7158	Intermediate Similarity	NPD2933	Approved
0.7143	Intermediate Similarity	NPD2988	Approved
0.7143	Intermediate Similarity	NPD2991	Approved
0.7113	Intermediate Similarity	NPD5926	Approved
0.7087	Intermediate Similarity	NPD5235	Approved
0.7087	Intermediate Similarity	NPD5237	Approved
0.7087	Intermediate Similarity	NPD5239	Approved
0.7087	Intermediate Similarity	NPD551	Approved
0.7087	Intermediate Similarity	NPD550	Approved
0.7087	Intermediate Similarity	NPD5236	Approved
0.7087	Intermediate Similarity	NPD5240	Approved
0.7087	Intermediate Similarity	NPD5451	Approved
0.7083	Intermediate Similarity	NPD1989	Approved
0.7083	Intermediate Similarity	NPD2860	Approved
0.7083	Intermediate Similarity	NPD2859	Approved
0.7059	Intermediate Similarity	NPD290	Approved
0.703	Intermediate Similarity	NPD794	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD2557	Approved
0.7	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.699	Remote Similarity	NPD2684	Approved
0.699	Remote Similarity	NPD2182	Approved
0.6989	Remote Similarity	NPD9249	Phase 1
0.6962	Remote Similarity	NPD675	Discontinued
0.6961	Remote Similarity	NPD3134	Approved
0.6944	Remote Similarity	NPD3596	Phase 2
0.6944	Remote Similarity	NPD5500	Discontinued
0.6931	Remote Similarity	NPD164	Approved
0.6931	Remote Similarity	NPD1237	Approved
0.6923	Remote Similarity	NPD111	Approved
0.6893	Remote Similarity	NPD1358	Approved
0.6887	Remote Similarity	NPD5535	Approved
0.6882	Remote Similarity	NPD531	Approved
0.6881	Remote Similarity	NPD2485	Approved
0.6881	Remote Similarity	NPD2484	Approved
0.6869	Remote Similarity	NPD3020	Approved
0.6863	Remote Similarity	NPD9697	Approved
0.6857	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4198	Discontinued
0.6848	Remote Similarity	NPD9259	Approved
0.6848	Remote Similarity	NPD9257	Approved
0.6822	Remote Similarity	NPD1241	Discontinued
0.6822	Remote Similarity	NPD5283	Phase 1
0.6818	Remote Similarity	NPD7042	Phase 3
0.6818	Remote Similarity	NPD1894	Discontinued
0.6818	Remote Similarity	NPD1182	Approved
0.6818	Remote Similarity	NPD6581	Approved
0.6818	Remote Similarity	NPD4016	Approved
0.6818	Remote Similarity	NPD6580	Approved
0.6818	Remote Similarity	NPD9490	Approved
0.6818	Remote Similarity	NPD2106	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1548	Phase 1
0.6809	Remote Similarity	NPD689	Discontinued
0.68	Remote Similarity	NPD1616	Discontinued
0.68	Remote Similarity	NPD3028	Approved
0.6792	Remote Similarity	NPD969	Suspended
0.6771	Remote Similarity	NPD9251	Approved
0.6771	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD9612	Approved
0.6768	Remote Similarity	NPD9495	Approved
0.6768	Remote Similarity	NPD9611	Approved
0.6768	Remote Similarity	NPD9609	Approved
0.6762	Remote Similarity	NPD9713	Approved
0.6757	Remote Similarity	NPD3444	Approved
0.6757	Remote Similarity	NPD3443	Approved
0.6757	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD3445	Approved
0.6757	Remote Similarity	NPD3049	Approved
0.6757	Remote Similarity	NPD6382	Discontinued
0.6757	Remote Similarity	NPD5585	Approved
0.6731	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6729	Remote Similarity	NPD821	Approved
0.6729	Remote Similarity	NPD7843	Approved
0.6705	Remote Similarity	NPD227	Approved
0.6705	Remote Similarity	NPD225	Approved
0.6703	Remote Similarity	NPD9491	Approved
0.6701	Remote Similarity	NPD845	Approved
0.6698	Remote Similarity	NPD2201	Approved
0.6696	Remote Similarity	NPD2556	Approved
0.6696	Remote Similarity	NPD4594	Approved
0.6696	Remote Similarity	NPD5126	Approved
0.6696	Remote Similarity	NPD5125	Phase 3
0.6696	Remote Similarity	NPD2554	Approved
0.6696	Remote Similarity	NPD5846	Approved
0.6696	Remote Similarity	NPD6516	Phase 2
0.6696	Remote Similarity	NPD4593	Approved
0.6667	Remote Similarity	NPD9365	Approved
0.6667	Remote Similarity	NPD1239	Approved
0.6667	Remote Similarity	NPD4658	Approved
0.6667	Remote Similarity	NPD592	Approved
0.6667	Remote Similarity	NPD7741	Discontinued
0.6667	Remote Similarity	NPD594	Approved
0.6667	Remote Similarity	NPD4656	Approved
0.6637	Remote Similarity	NPD3898	Approved
0.6637	Remote Similarity	NPD3897	Approved
0.6637	Remote Similarity	NPD3895	Approved
0.6637	Remote Similarity	NPD3896	Approved
0.6636	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD1242	Phase 1
0.6633	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2595	Approved
0.6607	Remote Similarity	NPD2594	Approved
0.6602	Remote Similarity	NPD5909	Discontinued
0.6579	Remote Similarity	NPD4480	Approved
0.6579	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD3381	Discontinued
0.6579	Remote Similarity	NPD1610	Phase 2
0.6569	Remote Similarity	NPD855	Approved
0.6569	Remote Similarity	NPD4818	Approved
0.6569	Remote Similarity	NPD854	Approved
0.6569	Remote Similarity	NPD4817	Approved
0.6566	Remote Similarity	NPD844	Approved
0.6562	Remote Similarity	NPD3673	Approved
0.6562	Remote Similarity	NPD9256	Approved
0.6562	Remote Similarity	NPD9258	Approved
0.6562	Remote Similarity	NPD3672	Approved
0.6552	Remote Similarity	NPD9716	Approved
0.6549	Remote Similarity	NPD5723	Approved
0.6545	Remote Similarity	NPD709	Approved
0.6545	Remote Similarity	NPD7157	Approved
0.6545	Remote Similarity	NPD6387	Discontinued
0.6542	Remote Similarity	NPD4025	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7798	Approved
0.6531	Remote Similarity	NPD1563	Approved
0.6522	Remote Similarity	NPD7250	Approved
0.6522	Remote Similarity	NPD7249	Approved
0.6522	Remote Similarity	NPD1840	Phase 2
0.6518	Remote Similarity	NPD2486	Discontinued
0.6505	Remote Similarity	NPD3680	Approved
0.6505	Remote Similarity	NPD3682	Approved
0.6505	Remote Similarity	NPD4229	Approved
0.6505	Remote Similarity	NPD4231	Approved
0.65	Remote Similarity	NPD288	Approved
0.6486	Remote Similarity	NPD5291	Approved
0.6486	Remote Similarity	NPD5292	Approved
0.6486	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD226	Approved
0.6481	Remote Similarity	NPD1139	Approved
0.6481	Remote Similarity	NPD228	Approved
0.6481	Remote Similarity	NPD1137	Approved
0.6476	Remote Similarity	NPD5704	Approved
0.6476	Remote Similarity	NPD5705	Approved
0.6476	Remote Similarity	NPD5706	Approved
0.6466	Remote Similarity	NPD2429	Approved
0.6466	Remote Similarity	NPD6583	Phase 3
0.6466	Remote Similarity	NPD4359	Approved
0.6466	Remote Similarity	NPD6539	Approved
0.6466	Remote Similarity	NPD6543	Approved
0.6466	Remote Similarity	NPD2428	Approved
0.6466	Remote Similarity	NPD7876	Discontinued
0.6466	Remote Similarity	NPD6540	Phase 3
0.6466	Remote Similarity	NPD6542	Approved
0.6466	Remote Similarity	NPD6582	Phase 2
0.6466	Remote Similarity	NPD6025	Phase 1
0.6465	Remote Similarity	NPD3772	Phase 3
0.6465	Remote Similarity	NPD688	Clinical (unspecified phase)
0.646	Remote Similarity	NPD1651	Approved
0.6455	Remote Similarity	NPD2629	Approved
0.6449	Remote Similarity	NPD2067	Discontinued
0.6442	Remote Similarity	NPD10	Approved
0.6442	Remote Similarity	NPD311	Approved
0.6442	Remote Similarity	NPD315	Approved
0.6442	Remote Similarity	NPD309	Approved
0.6442	Remote Similarity	NPD314	Approved
0.6442	Remote Similarity	NPD310	Approved
0.6435	Remote Similarity	NPD6287	Discontinued
0.6429	Remote Similarity	NPD5536	Phase 2
0.6429	Remote Similarity	NPD2347	Approved
0.6422	Remote Similarity	NPD1138	Approved
0.6421	Remote Similarity	NPD9538	Approved
0.6421	Remote Similarity	NPD1087	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