NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.12
Volume:	267.305
LogP:	3.58
LogD:	4.088
LogS:	-4.307
# Rotatable Bonds:	6
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.751
Synthetic Accessibility Score:	1.453
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.582
MDCK Permeability:	4.2078074329765514e-05
Pgp-inhibitor:	0.02
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.612

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.645
Plasma Protein Binding (PPB):	96.24515533447266%
Volume Distribution (VD):	0.743
Pgp-substrate:	3.4161648750305176%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.977
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.921
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.1
CYP2D6-substrate:	0.095
CYP3A4-inhibitor:	0.474
CYP3A4-substrate:	0.522

ADMET: Excretion

Clearance (CL):	14.019
Half-life (T1/2):	0.827

ADMET: Toxicity

hERG Blockers:	0.167
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.671
AMES Toxicity:	0.29
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.845
Carcinogencity:	0.581
Eye Corrosion:	0.055
Eye Irritation:	0.944
Respiratory Toxicity:	0.029

Download Data

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

Natural Product: NPC9822

Natural Product ID:	NPC9822
*Common Name:**	2-Phenylethyl 2-Phenylacetate
IUPAC Name:	2-phenylethyl 2-phenylacetate
Synonyms:
Standard InCHIKey:	ZOZIRNMDEZKZHM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H16O2/c17-16(13-15-9-5-2-6-10-15)18-12-11-14-7-3-1-4-8-14/h1-10H,11-13H2
SMILES:	c1ccc(cc1)CCOC(=O)Cc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3183441
PubChem CID:	7601
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives

*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
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13857	Mentha canadensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23256	Mentha arvensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13857	Mentha canadensis	Species	Lamiaceae	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	6

Activity Type	# Activity
Individual Protein	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	489.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54482.7	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 NPC9822 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	213
0.1-0.2	1146
0.2-0.3	3316
0.3-0.4	12343
0.4-0.5	14502
0.5-0.6	9529
0.6-0.7	1339
0.7-0.8	267
0.8-0.85	30
0.85-0.9	7
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC294134
0.9048	High Similarity	NPC288903
0.9011	High Similarity	NPC270654
0.8929	High Similarity	NPC323103
0.8824	High Similarity	NPC270507
0.8706	High Similarity	NPC103387
0.869	High Similarity	NPC121800
0.8621	High Similarity	NPC475710
0.8605	High Similarity	NPC285773
0.8571	High Similarity	NPC170484
0.8556	High Similarity	NPC213156
0.8556	High Similarity	NPC240108
0.8526	High Similarity	NPC42211
0.8444	Intermediate Similarity	NPC231591
0.8421	Intermediate Similarity	NPC118343
0.8391	Intermediate Similarity	NPC44830
0.8367	Intermediate Similarity	NPC269457
0.8256	Intermediate Similarity	NPC127343
0.8222	Intermediate Similarity	NPC322387
0.8191	Intermediate Similarity	NPC172925
0.8152	Intermediate Similarity	NPC274455
0.8152	Intermediate Similarity	NPC84288
0.8152	Intermediate Similarity	NPC86670
0.8152	Intermediate Similarity	NPC70940
0.8132	Intermediate Similarity	NPC329064
0.8125	Intermediate Similarity	NPC35448
0.8125	Intermediate Similarity	NPC78701
0.8085	Intermediate Similarity	NPC261181
0.8081	Intermediate Similarity	NPC269644
0.8065	Intermediate Similarity	NPC119631
0.8065	Intermediate Similarity	NPC141607
0.8065	Intermediate Similarity	NPC187725
0.8065	Intermediate Similarity	NPC317645
0.8043	Intermediate Similarity	NPC220893
0.8041	Intermediate Similarity	NPC146351
0.8041	Intermediate Similarity	NPC476042
0.8022	Intermediate Similarity	NPC89377
0.8021	Intermediate Similarity	NPC249912
0.8021	Intermediate Similarity	NPC226041
0.8021	Intermediate Similarity	NPC92754
0.8021	Intermediate Similarity	NPC289201
0.8021	Intermediate Similarity	NPC103048
0.8021	Intermediate Similarity	NPC276775
0.8	Intermediate Similarity	NPC95965
0.798	Intermediate Similarity	NPC474365
0.798	Intermediate Similarity	NPC301943
0.7979	Intermediate Similarity	NPC77273
0.7959	Intermediate Similarity	NPC473325
0.7941	Intermediate Similarity	NPC281604
0.7938	Intermediate Similarity	NPC225060
0.7931	Intermediate Similarity	NPC272260
0.7917	Intermediate Similarity	NPC12695
0.7907	Intermediate Similarity	NPC9796
0.7857	Intermediate Similarity	NPC221825
0.7857	Intermediate Similarity	NPC325497
0.7857	Intermediate Similarity	NPC7435
0.7843	Intermediate Similarity	NPC156648
0.7812	Intermediate Similarity	NPC130398
0.7812	Intermediate Similarity	NPC206764
0.781	Intermediate Similarity	NPC128368
0.7802	Intermediate Similarity	NPC58616
0.78	Intermediate Similarity	NPC329556
0.78	Intermediate Similarity	NPC160382
0.7778	Intermediate Similarity	NPC70624
0.7778	Intermediate Similarity	NPC208183
0.7778	Intermediate Similarity	NPC243289
0.7767	Intermediate Similarity	NPC469636
0.7767	Intermediate Similarity	NPC17417
0.7767	Intermediate Similarity	NPC10251
0.7765	Intermediate Similarity	NPC208075
0.7755	Intermediate Similarity	NPC271475
0.7755	Intermediate Similarity	NPC175852
0.7755	Intermediate Similarity	NPC210529
0.7755	Intermediate Similarity	NPC160548
0.7745	Intermediate Similarity	NPC94751
0.7745	Intermediate Similarity	NPC142326
0.7742	Intermediate Similarity	NPC304760
0.7727	Intermediate Similarity	NPC139901
0.7727	Intermediate Similarity	NPC151405
0.7717	Intermediate Similarity	NPC318107
0.7714	Intermediate Similarity	NPC79496
0.7714	Intermediate Similarity	NPC158282
0.7708	Intermediate Similarity	NPC34243
0.7692	Intermediate Similarity	NPC196246
0.7692	Intermediate Similarity	NPC93084
0.7692	Intermediate Similarity	NPC158854
0.7692	Intermediate Similarity	NPC251854
0.7692	Intermediate Similarity	NPC214067
0.7684	Intermediate Similarity	NPC110704
0.767	Intermediate Similarity	NPC56493
0.766	Intermediate Similarity	NPC173443
0.7647	Intermediate Similarity	NPC271437
0.7624	Intermediate Similarity	NPC89886
0.7624	Intermediate Similarity	NPC60679
0.7624	Intermediate Similarity	NPC255676
0.7619	Intermediate Similarity	NPC1082
0.7619	Intermediate Similarity	NPC474157
0.7619	Intermediate Similarity	NPC305912
0.7596	Intermediate Similarity	NPC31274
0.7596	Intermediate Similarity	NPC40178
0.7579	Intermediate Similarity	NPC185501
0.7573	Intermediate Similarity	NPC329705
0.7573	Intermediate Similarity	NPC474111
0.7573	Intermediate Similarity	NPC119271
0.7556	Intermediate Similarity	NPC165212
0.7553	Intermediate Similarity	NPC477693
0.7553	Intermediate Similarity	NPC477704
0.7551	Intermediate Similarity	NPC261947
0.7549	Intermediate Similarity	NPC114594
0.7549	Intermediate Similarity	NPC19136
0.7547	Intermediate Similarity	NPC270699
0.7547	Intermediate Similarity	NPC82899
0.7526	Intermediate Similarity	NPC23453
0.7525	Intermediate Similarity	NPC188895
0.7524	Intermediate Similarity	NPC174099
0.7523	Intermediate Similarity	NPC128249
0.75	Intermediate Similarity	NPC86987
0.75	Intermediate Similarity	NPC476484
0.75	Intermediate Similarity	NPC203925
0.75	Intermediate Similarity	NPC20485
0.75	Intermediate Similarity	NPC47536
0.75	Intermediate Similarity	NPC210092
0.7476	Intermediate Similarity	NPC105899
0.7476	Intermediate Similarity	NPC209632
0.7475	Intermediate Similarity	NPC477767
0.7473	Intermediate Similarity	NPC73637
0.7473	Intermediate Similarity	NPC121478
0.7455	Intermediate Similarity	NPC325295
0.7455	Intermediate Similarity	NPC76308
0.7455	Intermediate Similarity	NPC469574
0.7453	Intermediate Similarity	NPC210089
0.7453	Intermediate Similarity	NPC476003
0.7453	Intermediate Similarity	NPC167504
0.7447	Intermediate Similarity	NPC96625
0.7447	Intermediate Similarity	NPC69057
0.7444	Intermediate Similarity	NPC184030
0.7444	Intermediate Similarity	NPC164449
0.7444	Intermediate Similarity	NPC95868
0.7444	Intermediate Similarity	NPC477703
0.7444	Intermediate Similarity	NPC71664
0.7442	Intermediate Similarity	NPC285679
0.7429	Intermediate Similarity	NPC83628
0.7429	Intermediate Similarity	NPC474364
0.7429	Intermediate Similarity	NPC265407
0.7426	Intermediate Similarity	NPC133809
0.7426	Intermediate Similarity	NPC158623
0.7426	Intermediate Similarity	NPC136810
0.7426	Intermediate Similarity	NPC225079
0.7426	Intermediate Similarity	NPC128248
0.7419	Intermediate Similarity	NPC123476
0.7416	Intermediate Similarity	NPC137847
0.7416	Intermediate Similarity	NPC76455
0.7407	Intermediate Similarity	NPC307651
0.7407	Intermediate Similarity	NPC153053
0.74	Intermediate Similarity	NPC229242
0.74	Intermediate Similarity	NPC145052
0.7396	Intermediate Similarity	NPC62765
0.7391	Intermediate Similarity	NPC273758
0.7386	Intermediate Similarity	NPC175393
0.7383	Intermediate Similarity	NPC321852
0.7379	Intermediate Similarity	NPC31786
0.7379	Intermediate Similarity	NPC249067
0.7363	Intermediate Similarity	NPC12936
0.7363	Intermediate Similarity	NPC273033
0.7356	Intermediate Similarity	NPC108218
0.7353	Intermediate Similarity	NPC45613
0.7353	Intermediate Similarity	NPC474112
0.7333	Intermediate Similarity	NPC470007
0.7327	Intermediate Similarity	NPC217621
0.7326	Intermediate Similarity	NPC155429
0.7326	Intermediate Similarity	NPC74458
0.7315	Intermediate Similarity	NPC272524
0.7315	Intermediate Similarity	NPC469547
0.7312	Intermediate Similarity	NPC95429
0.7308	Intermediate Similarity	NPC471186
0.7308	Intermediate Similarity	NPC321670
0.7303	Intermediate Similarity	NPC298023
0.7303	Intermediate Similarity	NPC179726
0.7303	Intermediate Similarity	NPC329318
0.73	Intermediate Similarity	NPC253423
0.7297	Intermediate Similarity	NPC45794
0.729	Intermediate Similarity	NPC260818
0.7283	Intermediate Similarity	NPC475199
0.7283	Intermediate Similarity	NPC283012
0.7273	Intermediate Similarity	NPC51345
0.7264	Intermediate Similarity	NPC318327
0.7264	Intermediate Similarity	NPC269023
0.7264	Intermediate Similarity	NPC99846
0.7257	Intermediate Similarity	NPC473243
0.7257	Intermediate Similarity	NPC280827
0.7257	Intermediate Similarity	NPC243059
0.7255	Intermediate Similarity	NPC112552
0.7255	Intermediate Similarity	NPC264728
0.7255	Intermediate Similarity	NPC52472
0.7253	Intermediate Similarity	NPC157055
0.7248	Intermediate Similarity	NPC308744
0.7245	Intermediate Similarity	NPC323164
0.7238	Intermediate Similarity	NPC1065
0.7238	Intermediate Similarity	NPC37622
0.7238	Intermediate Similarity	NPC30594

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 NPC9822 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	893
0.2-0.3	1167
0.3-0.4	3176
0.4-0.5	2262
0.5-0.6	1081
0.6-0.7	309
0.7-0.8	55
0.8-0.85	15
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9326	High Similarity	NPD1989	Approved
0.8795	High Similarity	NPD9490	Approved
0.8605	High Similarity	NPD9491	Approved
0.8556	High Similarity	NPD3673	Approved
0.8556	High Similarity	NPD3672	Approved
0.8462	Intermediate Similarity	NPD1239	Approved
0.8452	Intermediate Similarity	NPD225	Approved
0.8452	Intermediate Similarity	NPD227	Approved
0.8427	Intermediate Similarity	NPD1087	Approved
0.8421	Intermediate Similarity	NPD7798	Approved
0.8421	Intermediate Similarity	NPD1238	Approved
0.828	Intermediate Similarity	NPD1563	Approved
0.8242	Intermediate Similarity	NPD800	Approved
0.8191	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD226	Approved
0.8152	Intermediate Similarity	NPD1089	Approved
0.8152	Intermediate Similarity	NPD1090	Approved
0.8152	Intermediate Similarity	NPD1086	Approved
0.8085	Intermediate Similarity	NPD1202	Approved
0.8041	Intermediate Similarity	NPD2066	Phase 3
0.8039	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD4793	Discontinued
0.8021	Intermediate Similarity	NPD1566	Phase 3
0.8021	Intermediate Similarity	NPD1564	Approved
0.8021	Intermediate Similarity	NPD1565	Approved
0.7979	Intermediate Similarity	NPD1088	Approved
0.7917	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD5347	Phase 2
0.7849	Intermediate Similarity	NPD5346	Phase 2
0.7812	Intermediate Similarity	NPD1693	Approved
0.78	Intermediate Similarity	NPD1929	Approved
0.78	Intermediate Similarity	NPD1930	Approved
0.78	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD2182	Approved
0.7755	Intermediate Similarity	NPD9495	Approved
0.7723	Intermediate Similarity	NPD5909	Discontinued
0.7717	Intermediate Similarity	NPD9257	Approved
0.7717	Intermediate Similarity	NPD9259	Approved
0.7708	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4234	Approved
0.7692	Intermediate Similarity	NPD1756	Approved
0.7692	Intermediate Similarity	NPD1752	Approved
0.7692	Intermediate Similarity	NPD4233	Approved
0.7685	Intermediate Similarity	NPD4576	Approved
0.7685	Intermediate Similarity	NPD4574	Approved
0.7664	Intermediate Similarity	NPD2629	Approved
0.7642	Intermediate Similarity	NPD2607	Approved
0.7619	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5926	Approved
0.7525	Intermediate Similarity	NPD1932	Approved
0.7524	Intermediate Similarity	NPD2067	Discontinued
0.7476	Intermediate Similarity	NPD5048	Discontinued
0.7455	Intermediate Similarity	NPD2347	Approved
0.7444	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2652	Approved
0.7407	Intermediate Similarity	NPD2650	Approved
0.7404	Intermediate Similarity	NPD5706	Approved
0.7404	Intermediate Similarity	NPD5704	Approved
0.7404	Intermediate Similarity	NPD5705	Approved
0.7396	Intermediate Similarity	NPD9256	Approved
0.7396	Intermediate Similarity	NPD9258	Approved
0.7379	Intermediate Similarity	NPD164	Approved
0.7379	Intermediate Similarity	NPD1237	Approved
0.7363	Intermediate Similarity	NPD942	Approved
0.7345	Intermediate Similarity	NPD4136	Approved
0.7345	Intermediate Similarity	NPD4106	Approved
0.7345	Intermediate Similarity	NPD4135	Approved
0.7339	Intermediate Similarity	NPD4766	Approved
0.7315	Intermediate Similarity	NPD7094	Approved
0.7315	Intermediate Similarity	NPD6858	Approved
0.7282	Intermediate Similarity	NPD6647	Phase 2
0.7281	Intermediate Similarity	NPD7437	Approved
0.7281	Intermediate Similarity	NPD7436	Approved
0.7264	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5306	Approved
0.7257	Intermediate Similarity	NPD5305	Approved
0.7232	Intermediate Similarity	NPD1894	Discontinued
0.7182	Intermediate Similarity	NPD5951	Approved
0.7172	Intermediate Similarity	NPD1066	Discontinued
0.7168	Intermediate Similarity	NPD4105	Approved
0.7168	Intermediate Similarity	NPD4102	Approved
0.7157	Intermediate Similarity	NPD3097	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6065	Approved
0.713	Intermediate Similarity	NPD4807	Approved
0.713	Intermediate Similarity	NPD4806	Approved
0.713	Intermediate Similarity	NPD6287	Discontinued
0.7115	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2329	Discontinued
0.71	Intermediate Similarity	NPD9260	Approved
0.7094	Intermediate Similarity	NPD5667	Approved
0.7091	Intermediate Similarity	NPD1374	Approved
0.7091	Intermediate Similarity	NPD1370	Approved
0.7091	Intermediate Similarity	NPD1371	Approved
0.7091	Intermediate Similarity	NPD1373	Approved
0.7083	Intermediate Similarity	NPD1282	Approved
0.7075	Intermediate Similarity	NPD6685	Approved
0.7037	Intermediate Similarity	NPD5235	Approved
0.7037	Intermediate Similarity	NPD5239	Approved
0.7037	Intermediate Similarity	NPD5237	Approved
0.7037	Intermediate Similarity	NPD5240	Approved
0.7037	Intermediate Similarity	NPD5236	Approved
0.7021	Intermediate Similarity	NPD3971	Phase 1
0.7018	Intermediate Similarity	NPD5981	Approved
0.7	Intermediate Similarity	NPD1279	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD2611	Approved
0.6983	Remote Similarity	NPD3131	Approved
0.6983	Remote Similarity	NPD2612	Approved
0.6983	Remote Similarity	NPD4215	Approved
0.6983	Remote Similarity	NPD4218	Approved
0.6983	Remote Similarity	NPD2610	Approved
0.6983	Remote Similarity	NPD3132	Approved
0.6983	Remote Similarity	NPD4216	Approved
0.6983	Remote Similarity	NPD4217	Approved
0.6983	Remote Similarity	NPD2609	Approved
0.6983	Remote Similarity	NPD2608	Approved
0.6961	Remote Similarity	NPD9566	Approved
0.6952	Remote Similarity	NPD5765	Approved
0.693	Remote Similarity	NPD4479	Discontinued
0.6923	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD5204	Approved
0.6893	Remote Similarity	NPD253	Approved
0.687	Remote Similarity	NPD6993	Approved
0.687	Remote Similarity	NPD6994	Approved
0.687	Remote Similarity	NPD5585	Approved
0.686	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4617	Approved
0.686	Remote Similarity	NPD5203	Approved
0.686	Remote Similarity	NPD5201	Approved
0.686	Remote Similarity	NPD6832	Phase 2
0.686	Remote Similarity	NPD4620	Approved
0.6837	Remote Similarity	NPD531	Approved
0.6833	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3644	Approved
0.6818	Remote Similarity	NPD3642	Approved
0.6818	Remote Similarity	NPD3643	Approved
0.6814	Remote Similarity	NPD4198	Discontinued
0.681	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.681	Remote Similarity	NPD17	Approved
0.6807	Remote Similarity	NPD2199	Approved
0.6807	Remote Similarity	NPD2198	Approved
0.6803	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7609	Phase 3
0.6786	Remote Similarity	NPD6010	Discontinued
0.6786	Remote Similarity	NPD1241	Discontinued
0.6765	Remote Similarity	NPD4094	Approved
0.6762	Remote Similarity	NPD2550	Approved
0.6762	Remote Similarity	NPD2558	Approved
0.6762	Remote Similarity	NPD2552	Approved
0.6762	Remote Similarity	NPD2555	Approved
0.6762	Remote Similarity	NPD2549	Approved
0.6762	Remote Similarity	NPD2553	Approved
0.6759	Remote Similarity	NPD467	Phase 1
0.6757	Remote Similarity	NPD6912	Phase 3
0.6754	Remote Similarity	NPD3797	Approved
0.675	Remote Similarity	NPD2159	Approved
0.675	Remote Similarity	NPD2160	Approved
0.675	Remote Similarity	NPD2626	Approved
0.675	Remote Similarity	NPD2625	Approved
0.675	Remote Similarity	NPD2628	Approved
0.675	Remote Similarity	NPD2627	Approved
0.6748	Remote Similarity	NPD4619	Approved
0.6748	Remote Similarity	NPD4621	Approved
0.6739	Remote Similarity	NPD9294	Approved
0.6735	Remote Similarity	NPD650	Approved
0.6733	Remote Similarity	NPD1508	Approved
0.6733	Remote Similarity	NPD7631	Approved
0.6727	Remote Similarity	NPD5278	Discontinued
0.6726	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1855	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD9716	Approved
0.6698	Remote Similarity	NPD4189	Approved
0.6698	Remote Similarity	NPD4188	Approved
0.6696	Remote Similarity	NPD5535	Approved
0.6696	Remote Similarity	NPD5277	Phase 2
0.6695	Remote Similarity	NPD5618	Discontinued
0.6695	Remote Similarity	NPD1281	Approved
0.6667	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7008	Discontinued
0.6667	Remote Similarity	NPD2201	Approved
0.6667	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2345	Approved
0.664	Remote Similarity	NPD5119	Approved
0.664	Remote Similarity	NPD6310	Approved
0.664	Remote Similarity	NPD6309	Approved
0.664	Remote Similarity	NPD5120	Approved
0.664	Remote Similarity	NPD2979	Phase 3
0.664	Remote Similarity	NPD5184	Approved
0.664	Remote Similarity	NPD5121	Approved
0.664	Remote Similarity	NPD3373	Approved
0.664	Remote Similarity	NPD5182	Approved
0.664	Remote Similarity	NPD5185	Approved
0.664	Remote Similarity	NPD6311	Approved
0.6639	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD1608	Approved
0.6639	Remote Similarity	NPD1481	Phase 2
0.6638	Remote Similarity	NPD9545	Approved
0.6638	Remote Similarity	NPD3798	Phase 3
0.6638	Remote Similarity	NPD2617	Discontinued
0.6637	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD3598	Phase 3

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