NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	210.09
Volume:	214.871
LogP:	3.108
LogD:	2.985
LogS:	-2.858
# Rotatable Bonds:	4
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.774
Synthetic Accessibility Score:	1.886
Fsp3:	0.364
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:	-4.546
MDCK Permeability:	2.2465632355306298e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.652

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.623
Plasma Protein Binding (PPB):	92.7127914428711%
Volume Distribution (VD):	0.827
Pgp-substrate:	5.577859878540039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.927
CYP2C19-inhibitor:	0.78
CYP2C19-substrate:	0.496
CYP2C9-inhibitor:	0.397
CYP2C9-substrate:	0.889
CYP2D6-inhibitor:	0.787
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.658
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	12.359
Half-life (T1/2):	0.615

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.029
Drug-inuced Liver Injury (DILI):	0.291
AMES Toxicity:	0.115
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.077
Skin Sensitization:	0.335
Carcinogencity:	0.047
Eye Corrosion:	0.249
Eye Irritation:	0.988
Respiratory Toxicity:	0.355

Download Data

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

Natural Product: NPC135837

Natural Product ID:	NPC135837
*Common Name:**	Ethyl Everninate
IUPAC Name:	ethyl 2-hydroxy-4-methoxy-6-methylbenzoate
Synonyms:
Standard InCHIKey:	PJOOIAZRUIIQMU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14O4/c1-4-15-11(13)10-7(2)5-8(14-3)6-9(10)12/h5-6,12H,4H2,1-3H3
SMILES:	CCOC(=O)c1c(C)cc(cc1O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1318588
PubChem CID:	80201
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0002344] Methoxybenzoic acids and derivatives [CHEMONTID:0002346] P-methoxybenzoic acids and 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
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2602	Usnea longissima	Species	Parmeliaceae	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
Others	2
Potency	3

Activity Type	# Activity
Individual Protein	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	14125.4	nM	PMID[575568]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	31622.8	nM	PMID[575568]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	111.06	%	PMID[575569]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	102.59	%	PMID[575569]

☑ 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 NPC135837 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	327
0.1-0.2	1562
0.2-0.3	4067
0.3-0.4	9047
0.4-0.5	9232
0.5-0.6	3433
0.6-0.7	5920
0.7-0.8	6626
0.8-0.85	1906
0.85-0.9	447
0.9-0.95	111
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
0.9846	High Similarity	NPC180905
0.9846	High Similarity	NPC182496
0.9701	High Similarity	NPC67650
0.9701	High Similarity	NPC90411
0.9701	High Similarity	NPC1704
0.9692	High Similarity	NPC153783
0.963	High Similarity	NPC474385
0.9559	High Similarity	NPC472006
0.9559	High Similarity	NPC469542
0.9559	High Similarity	NPC51106
0.9556	High Similarity	NPC475730
0.9538	High Similarity	NPC219892
0.9538	High Similarity	NPC189823
0.9489	High Similarity	NPC210425
0.9489	High Similarity	NPC277426
0.9489	High Similarity	NPC86373
0.9489	High Similarity	NPC280404
0.9481	High Similarity	NPC165172
0.9474	High Similarity	NPC235115
0.947	High Similarity	NPC175943
0.942	High Similarity	NPC472034
0.9412	High Similarity	NPC220106
0.9407	High Similarity	NPC268052
0.9407	High Similarity	NPC32360
0.9403	High Similarity	NPC70380
0.9353	High Similarity	NPC107625
0.9353	High Similarity	NPC472033
0.9348	High Similarity	NPC95123
0.9348	High Similarity	NPC66404
0.9343	High Similarity	NPC105648
0.9343	High Similarity	NPC250755
0.9343	High Similarity	NPC469579
0.9333	High Similarity	NPC33144
0.9333	High Similarity	NPC212693
0.9333	High Similarity	NPC478200
0.9333	High Similarity	NPC94248
0.9333	High Similarity	NPC191835
0.9308	High Similarity	NPC293453
0.9286	High Similarity	NPC210320
0.9286	High Similarity	NPC472036
0.9281	High Similarity	NPC312789
0.9281	High Similarity	NPC134621
0.9281	High Similarity	NPC473692
0.927	High Similarity	NPC158634
0.9265	High Similarity	NPC247409
0.9265	High Similarity	NPC92655
0.9265	High Similarity	NPC52358
0.9265	High Similarity	NPC105456
0.9265	High Similarity	NPC139634
0.922	High Similarity	NPC215711
0.922	High Similarity	NPC73411
0.922	High Similarity	NPC240253
0.922	High Similarity	NPC471642
0.922	High Similarity	NPC240622
0.922	High Similarity	NPC471641
0.9214	High Similarity	NPC237208
0.9214	High Similarity	NPC267509
0.9197	High Similarity	NPC158472
0.9191	High Similarity	NPC472602
0.9185	High Similarity	NPC50455
0.9185	High Similarity	NPC158481
0.9185	High Similarity	NPC242712
0.9167	High Similarity	NPC42292
0.9167	High Similarity	NPC307732
0.9155	High Similarity	NPC77325
0.9155	High Similarity	NPC4423
0.9155	High Similarity	NPC476684
0.9155	High Similarity	NPC270160
0.9155	High Similarity	NPC237440
0.9149	High Similarity	NPC14098
0.9143	High Similarity	NPC32470
0.9143	High Similarity	NPC29577
0.913	High Similarity	NPC53649
0.913	High Similarity	NPC472035
0.913	High Similarity	NPC478217
0.913	High Similarity	NPC37530
0.913	High Similarity	NPC313123
0.913	High Similarity	NPC244923
0.913	High Similarity	NPC478201
0.9124	High Similarity	NPC88269
0.9124	High Similarity	NPC57380
0.9124	High Similarity	NPC275356
0.9118	High Similarity	NPC194579
0.9118	High Similarity	NPC71256
0.9091	High Similarity	NPC96501
0.9091	High Similarity	NPC119929
0.9091	High Similarity	NPC469670
0.9091	High Similarity	NPC469619
0.9085	High Similarity	NPC153417
0.9084	High Similarity	NPC128428
0.9084	High Similarity	NPC305518
0.9078	High Similarity	NPC225173
0.9078	High Similarity	NPC163846
0.9078	High Similarity	NPC138978
0.9078	High Similarity	NPC260946
0.9077	High Similarity	NPC201728
0.9077	High Similarity	NPC262671
0.9065	High Similarity	NPC96692
0.9065	High Similarity	NPC82913
0.9058	High Similarity	NPC472601
0.9058	High Similarity	NPC155205
0.9058	High Similarity	NPC99441
0.9058	High Similarity	NPC472600
0.9028	High Similarity	NPC70016
0.9028	High Similarity	NPC204350
0.9028	High Similarity	NPC215921
0.9028	High Similarity	NPC240768
0.9028	High Similarity	NPC200773
0.9021	High Similarity	NPC233267
0.9021	High Similarity	NPC291049
0.9014	High Similarity	NPC125801
0.9014	High Similarity	NPC12305
0.9007	High Similarity	NPC75694
0.9	High Similarity	NPC310340
0.9	High Similarity	NPC159721
0.9	High Similarity	NPC478202
0.8993	High Similarity	NPC472603
0.8993	High Similarity	NPC472605
0.8993	High Similarity	NPC275734
0.8993	High Similarity	NPC472604
0.8986	High Similarity	NPC471819
0.8978	High Similarity	NPC178467
0.8978	High Similarity	NPC474771
0.8978	High Similarity	NPC474849
0.8978	High Similarity	NPC65837
0.8978	High Similarity	NPC149372
0.8966	High Similarity	NPC167903
0.8966	High Similarity	NPC273483
0.8966	High Similarity	NPC271681
0.8963	High Similarity	NPC203817
0.8958	High Similarity	NPC470107
0.8958	High Similarity	NPC295036
0.8958	High Similarity	NPC60413
0.8958	High Similarity	NPC179178
0.8955	High Similarity	NPC470831
0.8955	High Similarity	NPC214702
0.8951	High Similarity	NPC2569
0.8951	High Similarity	NPC37139
0.8951	High Similarity	NPC105415
0.8951	High Similarity	NPC172329
0.8947	High Similarity	NPC212379
0.8947	High Similarity	NPC69235
0.8936	High Similarity	NPC210966
0.8936	High Similarity	NPC151607
0.8936	High Similarity	NPC42540
0.8936	High Similarity	NPC475201
0.8936	High Similarity	NPC478203
0.8936	High Similarity	NPC126882
0.8929	High Similarity	NPC471640
0.8929	High Similarity	NPC94076
0.8929	High Similarity	NPC182255
0.8929	High Similarity	NPC49108
0.8929	High Similarity	NPC471644
0.8913	High Similarity	NPC177307
0.8913	High Similarity	NPC9121
0.8913	High Similarity	NPC472403
0.8913	High Similarity	NPC475974
0.8905	High Similarity	NPC291454
0.8904	High Similarity	NPC281477
0.8904	High Similarity	NPC472799
0.8897	High Similarity	NPC227166
0.8897	High Similarity	NPC133856
0.8897	High Similarity	NPC223457
0.8889	High Similarity	NPC6923
0.8889	High Similarity	NPC475589
0.8889	High Similarity	NPC198927
0.8889	High Similarity	NPC31872
0.8889	High Similarity	NPC473584
0.8881	High Similarity	NPC8817
0.8881	High Similarity	NPC12694
0.8881	High Similarity	NPC473271
0.8881	High Similarity	NPC137296
0.8873	High Similarity	NPC257558
0.8873	High Similarity	NPC83272
0.8872	High Similarity	NPC186098
0.8872	High Similarity	NPC80694
0.8872	High Similarity	NPC41263
0.8865	High Similarity	NPC472610
0.8865	High Similarity	NPC471731
0.8865	High Similarity	NPC471643
0.8865	High Similarity	NPC84266
0.8865	High Similarity	NPC471639
0.8864	High Similarity	NPC95309
0.8857	High Similarity	NPC16455
0.8857	High Similarity	NPC307990
0.8855	High Similarity	NPC6888
0.8849	High Similarity	NPC474655
0.8844	High Similarity	NPC89625
0.8844	High Similarity	NPC199926
0.8844	High Similarity	NPC149618
0.8844	High Similarity	NPC99381
0.8844	High Similarity	NPC16082
0.8844	High Similarity	NPC79998
0.8844	High Similarity	NPC82592
0.8841	High Similarity	NPC472364
0.8841	High Similarity	NPC476333
0.8841	High Similarity	NPC193792
0.8841	High Similarity	NPC472367
0.8841	High Similarity	NPC261292
0.8841	High Similarity	NPC301915

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 NPC135837 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	990
0.2-0.3	1817
0.3-0.4	2535
0.4-0.5	1765
0.5-0.6	1128
0.6-0.7	439
0.7-0.8	153
0.8-0.85	33
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9699	High Similarity	NPD970	Clinical (unspecified phase)
0.9007	High Similarity	NPD2532	Approved
0.9007	High Similarity	NPD2534	Approved
0.9007	High Similarity	NPD2533	Approved
0.8649	High Similarity	NPD7819	Suspended
0.8633	High Similarity	NPD1510	Phase 2
0.8613	High Similarity	NPD1240	Approved
0.8511	High Similarity	NPD1550	Clinical (unspecified phase)
0.8511	High Similarity	NPD1552	Clinical (unspecified phase)
0.8489	Intermediate Similarity	NPD1607	Approved
0.8451	Intermediate Similarity	NPD1549	Phase 2
0.844	Intermediate Similarity	NPD1551	Phase 2
0.8417	Intermediate Similarity	NPD230	Phase 1
0.8333	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD3750	Approved
0.8288	Intermediate Similarity	NPD6799	Approved
0.8288	Intermediate Similarity	NPD1511	Approved
0.8258	Intermediate Similarity	NPD6232	Discontinued
0.8231	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1934	Approved
0.8201	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD2935	Discontinued
0.8182	Intermediate Similarity	NPD9545	Approved
0.8176	Intermediate Similarity	NPD1512	Approved
0.8158	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD9717	Approved
0.8146	Intermediate Similarity	NPD7411	Suspended
0.8141	Intermediate Similarity	NPD5710	Approved
0.8141	Intermediate Similarity	NPD5711	Approved
0.8117	Intermediate Similarity	NPD3749	Approved
0.8117	Intermediate Similarity	NPD7075	Discontinued
0.8105	Intermediate Similarity	NPD3817	Phase 2
0.8101	Intermediate Similarity	NPD7473	Discontinued
0.8079	Intermediate Similarity	NPD6599	Discontinued
0.8077	Intermediate Similarity	NPD6959	Discontinued
0.8056	Intermediate Similarity	NPD2796	Approved
0.8052	Intermediate Similarity	NPD3882	Suspended
0.8052	Intermediate Similarity	NPD7768	Phase 2
0.8039	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD2801	Approved
0.803	Intermediate Similarity	NPD9493	Approved
0.8014	Intermediate Similarity	NPD2800	Approved
0.8014	Intermediate Similarity	NPD1243	Approved
0.7987	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD3748	Approved
0.7971	Intermediate Similarity	NPD1203	Approved
0.7961	Intermediate Similarity	NPD4380	Phase 2
0.7943	Intermediate Similarity	NPD411	Approved
0.7941	Intermediate Similarity	NPD422	Phase 1
0.7935	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD1465	Phase 2
0.7902	Intermediate Similarity	NPD447	Suspended
0.7881	Intermediate Similarity	NPD920	Approved
0.7867	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6801	Discontinued
0.7852	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD6651	Approved
0.7838	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5844	Phase 1
0.7778	Intermediate Similarity	NPD3226	Approved
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD1608	Approved
0.7748	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD919	Approved
0.7718	Intermediate Similarity	NPD4628	Phase 3
0.7708	Intermediate Similarity	NPD943	Approved
0.7702	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6166	Phase 2
0.7702	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6100	Approved
0.7687	Intermediate Similarity	NPD6099	Approved
0.7676	Intermediate Similarity	NPD6832	Phase 2
0.7669	Intermediate Similarity	NPD7054	Approved
0.766	Intermediate Similarity	NPD1019	Discontinued
0.7655	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2654	Approved
0.7647	Intermediate Similarity	NPD5403	Approved
0.7643	Intermediate Similarity	NPD5402	Approved
0.7635	Intermediate Similarity	NPD2346	Discontinued
0.7632	Intermediate Similarity	NPD5401	Approved
0.7626	Intermediate Similarity	NPD9269	Phase 2
0.7622	Intermediate Similarity	NPD7074	Phase 3
0.7622	Intermediate Similarity	NPD7472	Approved
0.7619	Intermediate Similarity	NPD2799	Discontinued
0.7607	Intermediate Similarity	NPD3818	Discontinued
0.7591	Intermediate Similarity	NPD9268	Approved
0.759	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5953	Discontinued
0.7576	Intermediate Similarity	NPD6797	Phase 2
0.7569	Intermediate Similarity	NPD3764	Approved
0.7566	Intermediate Similarity	NPD7390	Discontinued
0.7536	Intermediate Similarity	NPD17	Approved
0.7536	Intermediate Similarity	NPD1778	Approved
0.7536	Intermediate Similarity	NPD4626	Approved
0.753	Intermediate Similarity	NPD7251	Discontinued
0.7518	Intermediate Similarity	NPD1283	Approved
0.7517	Intermediate Similarity	NPD2344	Approved
0.7485	Intermediate Similarity	NPD7808	Phase 3
0.7483	Intermediate Similarity	NPD9494	Approved
0.7464	Intermediate Similarity	NPD5691	Approved
0.7455	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7286	Phase 2
0.7453	Intermediate Similarity	NPD5494	Approved
0.745	Intermediate Similarity	NPD5405	Approved
0.745	Intermediate Similarity	NPD5404	Approved
0.745	Intermediate Similarity	NPD5406	Approved
0.745	Intermediate Similarity	NPD5408	Approved
0.7448	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1296	Phase 2
0.7429	Intermediate Similarity	NPD1201	Approved
0.7429	Intermediate Similarity	NPD1610	Phase 2
0.7425	Intermediate Similarity	NPD6559	Discontinued
0.7424	Intermediate Similarity	NPD74	Approved
0.7424	Intermediate Similarity	NPD9266	Approved
0.7421	Intermediate Similarity	NPD4288	Approved
0.7419	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7199	Phase 2
0.7405	Intermediate Similarity	NPD37	Approved
0.7403	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6234	Discontinued
0.7391	Intermediate Similarity	NPD1548	Phase 1
0.7383	Intermediate Similarity	NPD7033	Discontinued
0.7375	Intermediate Similarity	NPD4965	Approved
0.7375	Intermediate Similarity	NPD4966	Approved
0.7375	Intermediate Similarity	NPD4967	Phase 2
0.7372	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7229	Phase 3
0.7348	Intermediate Similarity	NPD9267	Approved
0.7348	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD9263	Approved
0.7348	Intermediate Similarity	NPD9264	Approved
0.7343	Intermediate Similarity	NPD2797	Approved
0.7343	Intermediate Similarity	NPD1164	Approved
0.7343	Intermediate Similarity	NPD1470	Approved
0.7341	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2313	Discontinued
0.7329	Intermediate Similarity	NPD3268	Approved
0.7325	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2309	Approved
0.7317	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4908	Phase 1
0.7305	Intermediate Similarity	NPD1281	Approved
0.7301	Intermediate Similarity	NPD1247	Approved
0.7292	Intermediate Similarity	NPD2798	Approved
0.7278	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3225	Approved
0.7267	Intermediate Similarity	NPD4308	Phase 3
0.7255	Intermediate Similarity	NPD7003	Approved
0.7234	Intermediate Similarity	NPD3496	Discontinued
0.723	Intermediate Similarity	NPD4060	Phase 1
0.7212	Intermediate Similarity	NPD3926	Phase 2
0.7211	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD5353	Approved
0.7203	Intermediate Similarity	NPD4749	Approved
0.7192	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD3751	Discontinued
0.7183	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1933	Approved
0.7181	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5124	Phase 1
0.7172	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1241	Discontinued
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7134	Intermediate Similarity	NPD6273	Approved
0.7133	Intermediate Similarity	NPD1481	Phase 2
0.7126	Intermediate Similarity	NPD4287	Approved
0.7126	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2979	Phase 3
0.7114	Intermediate Similarity	NPD1613	Approved
0.7108	Intermediate Similarity	NPD5242	Approved
0.7107	Intermediate Similarity	NPD7458	Discontinued
0.7105	Intermediate Similarity	NPD4477	Approved
0.7105	Intermediate Similarity	NPD4476	Approved
0.7103	Intermediate Similarity	NPD3266	Approved
0.7103	Intermediate Similarity	NPD3267	Approved
0.7101	Intermediate Similarity	NPD9281	Approved
0.7095	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7177	Discontinued
0.7083	Intermediate Similarity	NPD7228	Approved
0.7078	Intermediate Similarity	NPD1652	Phase 2
0.7075	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6355	Discontinued
0.7063	Intermediate Similarity	NPD1535	Discovery
0.7059	Intermediate Similarity	NPD6004	Phase 3
0.7059	Intermediate Similarity	NPD6005	Phase 3
0.7059	Intermediate Similarity	NPD6002	Phase 3
0.7059	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1471	Phase 3
0.7059	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3787	Discontinued
0.7047	Intermediate Similarity	NPD520	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