NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.13
Volume:	255.332
LogP:	4.089
LogD:	3.72
LogS:	-4.163
# Rotatable Bonds:	5
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.643
Synthetic Accessibility Score:	2.106
Fsp3:	0.357
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.521
MDCK Permeability:	2.9520537282223813e-05
Pgp-inhibitor:	0.058
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.49
30% Bioavailability (F30%):	0.103

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103
Plasma Protein Binding (PPB):	96.88239288330078%
Volume Distribution (VD):	2.924
Pgp-substrate:	4.025660991668701%

ADMET: Metabolism

CYP1A2-inhibitor:	0.977
CYP1A2-substrate:	0.38
CYP2C19-inhibitor:	0.918
CYP2C19-substrate:	0.141
CYP2C9-inhibitor:	0.685
CYP2C9-substrate:	0.871
CYP2D6-inhibitor:	0.79
CYP2D6-substrate:	0.555
CYP3A4-inhibitor:	0.277
CYP3A4-substrate:	0.169

ADMET: Excretion

Clearance (CL):	16.099
Half-life (T1/2):	0.81

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.09
Drug-inuced Liver Injury (DILI):	0.389
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.036
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.361
Carcinogencity:	0.148
Eye Corrosion:	0.022
Eye Irritation:	0.963
Respiratory Toxicity:	0.092

Download Data

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

Natural Product: NPC184219

Natural Product ID:	NPC184219
*Common Name:**	Ethyl 4-Hydroxy-3-(3-Methylbut-2-Enyl)Benzoate
IUPAC Name:	ethyl 4-hydroxy-3-(3-methylbut-2-enyl)benzoate
Synonyms:
Standard InCHIKey:	QOIOQZMIXLSVAI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H18O3/c1-4-17-14(16)12-7-8-13(15)11(9-12)6-5-10(2)3/h5,7-9,15H,4,6H2,1-3H3
SMILES:	CCOC(=O)c1ccc(c(c1)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506347
PubChem CID:	14485964
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters [CHEMONTID:0004701] p-Hydroxybenzoic acid esters [CHEMONTID:0004702] p-Hydroxybenzoic acid alkyl esters

*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
NPO32527	piper guanacastensis	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9090871]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3544	Organism	Ochlerotatus atropalpus	Ochlerotatus atropalpus	LC50	=	25.7	ug.mL-1	PMID[507377]

☑ 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 NPC184219 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	247
0.1-0.2	1293
0.2-0.3	3219
0.3-0.4	8049
0.4-0.5	10746
0.5-0.6	4212
0.6-0.7	8991
0.7-0.8	5324
0.8-0.85	550
0.85-0.9	47
0.9-0.95	17
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9829	High Similarity	NPC67300
0.9508	High Similarity	NPC473744
0.9402	High Similarity	NPC94298
0.9402	High Similarity	NPC27633
0.936	High Similarity	NPC302844
0.928	High Similarity	NPC473777
0.9237	High Similarity	NPC474890
0.9237	High Similarity	NPC161943
0.9237	High Similarity	NPC273282
0.9231	High Similarity	NPC131192
0.9187	High Similarity	NPC110211
0.9187	High Similarity	NPC204579
0.9113	High Similarity	NPC121104
0.9106	High Similarity	NPC49938
0.9068	High Similarity	NPC83718
0.8968	High Similarity	NPC194979
0.8898	High Similarity	NPC109778
0.8898	High Similarity	NPC327457
0.8898	High Similarity	NPC86774
0.8889	High Similarity	NPC2596
0.8889	High Similarity	NPC2401
0.8871	High Similarity	NPC221798
0.8862	High Similarity	NPC291189
0.8862	High Similarity	NPC69403
0.8862	High Similarity	NPC475192
0.8843	High Similarity	NPC61779
0.8837	High Similarity	NPC239855
0.8814	High Similarity	NPC242136
0.8797	High Similarity	NPC469911
0.879	High Similarity	NPC174991
0.8779	High Similarity	NPC475111
0.8779	High Similarity	NPC291454
0.873	High Similarity	NPC95309
0.8692	High Similarity	NPC66158
0.8689	High Similarity	NPC328459
0.8689	High Similarity	NPC90522
0.8689	High Similarity	NPC473767
0.8661	High Similarity	NPC37512
0.8651	High Similarity	NPC165556
0.8647	High Similarity	NPC221104
0.8632	High Similarity	NPC471954
0.8632	High Similarity	NPC75272
0.8618	High Similarity	NPC72977
0.8607	High Similarity	NPC94637
0.8593	High Similarity	NPC470842
0.8593	High Similarity	NPC184053
0.8583	High Similarity	NPC475236
0.8583	High Similarity	NPC473751
0.8582	High Similarity	NPC19622
0.8582	High Similarity	NPC112789
0.8561	High Similarity	NPC164136
0.8527	High Similarity	NPC226855
0.8525	High Similarity	NPC174087
0.8519	High Similarity	NPC275903
0.8512	High Similarity	NPC220540
0.8485	Intermediate Similarity	NPC27643
0.8478	Intermediate Similarity	NPC97188
0.8475	Intermediate Similarity	NPC95172
0.8462	Intermediate Similarity	NPC307732
0.8462	Intermediate Similarity	NPC29883
0.8462	Intermediate Similarity	NPC42292
0.8462	Intermediate Similarity	NPC245395
0.8456	Intermediate Similarity	NPC307990
0.8456	Intermediate Similarity	NPC16455
0.845	Intermediate Similarity	NPC229894
0.845	Intermediate Similarity	NPC193203
0.8444	Intermediate Similarity	NPC473988
0.8443	Intermediate Similarity	NPC128825
0.8433	Intermediate Similarity	NPC70380
0.8433	Intermediate Similarity	NPC170718
0.8433	Intermediate Similarity	NPC194579
0.8421	Intermediate Similarity	NPC142027
0.8421	Intermediate Similarity	NPC27407
0.8417	Intermediate Similarity	NPC469498
0.8413	Intermediate Similarity	NPC309765
0.8409	Intermediate Similarity	NPC114116
0.8409	Intermediate Similarity	NPC153783
0.8406	Intermediate Similarity	NPC151607
0.8406	Intermediate Similarity	NPC42540
0.8397	Intermediate Similarity	NPC214702
0.8397	Intermediate Similarity	NPC470831
0.8385	Intermediate Similarity	NPC170546
0.8385	Intermediate Similarity	NPC117899
0.8385	Intermediate Similarity	NPC939
0.8385	Intermediate Similarity	NPC66246
0.8382	Intermediate Similarity	NPC472601
0.8382	Intermediate Similarity	NPC64664
0.8382	Intermediate Similarity	NPC472600
0.8376	Intermediate Similarity	NPC184658
0.8372	Intermediate Similarity	NPC158654
0.837	Intermediate Similarity	NPC33144
0.837	Intermediate Similarity	NPC478200
0.837	Intermediate Similarity	NPC94248
0.837	Intermediate Similarity	NPC112135
0.837	Intermediate Similarity	NPC191835
0.837	Intermediate Similarity	NPC212693
0.8358	Intermediate Similarity	NPC158481
0.8347	Intermediate Similarity	NPC11824
0.8333	Intermediate Similarity	NPC128348
0.8333	Intermediate Similarity	NPC271451
0.8333	Intermediate Similarity	NPC112192
0.8333	Intermediate Similarity	NPC164236
0.8333	Intermediate Similarity	NPC66384
0.8333	Intermediate Similarity	NPC309717
0.8333	Intermediate Similarity	NPC189106
0.8333	Intermediate Similarity	NPC303737
0.8333	Intermediate Similarity	NPC159721
0.8321	Intermediate Similarity	NPC183348
0.8321	Intermediate Similarity	NPC37530
0.8321	Intermediate Similarity	NPC84772
0.8321	Intermediate Similarity	NPC472604
0.8321	Intermediate Similarity	NPC472035
0.8321	Intermediate Similarity	NPC472603
0.8321	Intermediate Similarity	NPC470987
0.8321	Intermediate Similarity	NPC472605
0.8321	Intermediate Similarity	NPC478201
0.8321	Intermediate Similarity	NPC313123
0.8321	Intermediate Similarity	NPC282230
0.8321	Intermediate Similarity	NPC21378
0.8321	Intermediate Similarity	NPC478217
0.832	Intermediate Similarity	NPC233282
0.8309	Intermediate Similarity	NPC105456
0.8309	Intermediate Similarity	NPC275356
0.8309	Intermediate Similarity	NPC139634
0.8309	Intermediate Similarity	NPC52358
0.8309	Intermediate Similarity	NPC88269
0.8308	Intermediate Similarity	NPC186098
0.8308	Intermediate Similarity	NPC293453
0.8308	Intermediate Similarity	NPC80694
0.8305	Intermediate Similarity	NPC226699
0.8298	Intermediate Similarity	NPC17600
0.8296	Intermediate Similarity	NPC261292
0.8296	Intermediate Similarity	NPC71256
0.8296	Intermediate Similarity	NPC41461
0.8296	Intermediate Similarity	NPC12165
0.8296	Intermediate Similarity	NPC25287
0.8296	Intermediate Similarity	NPC156910
0.8296	Intermediate Similarity	NPC274109
0.8296	Intermediate Similarity	NPC24394
0.8296	Intermediate Similarity	NPC249606
0.8296	Intermediate Similarity	NPC1486
0.8296	Intermediate Similarity	NPC477244
0.8296	Intermediate Similarity	NPC66349
0.8296	Intermediate Similarity	NPC477242
0.8296	Intermediate Similarity	NPC168105
0.8296	Intermediate Similarity	NPC301915
0.8296	Intermediate Similarity	NPC150399
0.8296	Intermediate Similarity	NPC98115
0.8296	Intermediate Similarity	NPC186838
0.8296	Intermediate Similarity	NPC222633
0.8296	Intermediate Similarity	NPC477243
0.8291	Intermediate Similarity	NPC303141
0.8279	Intermediate Similarity	NPC81808
0.8264	Intermediate Similarity	NPC17693
0.8264	Intermediate Similarity	NPC199462
0.8258	Intermediate Similarity	NPC15083
0.8258	Intermediate Similarity	NPC470976
0.8258	Intermediate Similarity	NPC219892
0.8258	Intermediate Similarity	NPC189823
0.8258	Intermediate Similarity	NPC470977
0.8258	Intermediate Similarity	NPC18798
0.8258	Intermediate Similarity	NPC196979
0.8258	Intermediate Similarity	NPC324482
0.8258	Intermediate Similarity	NPC198249
0.8254	Intermediate Similarity	NPC216216
0.8248	Intermediate Similarity	NPC137009
0.8248	Intermediate Similarity	NPC327187
0.8248	Intermediate Similarity	NPC158472
0.8248	Intermediate Similarity	NPC23257
0.8248	Intermediate Similarity	NPC99441
0.8248	Intermediate Similarity	NPC470211
0.8248	Intermediate Similarity	NPC168471
0.8244	Intermediate Similarity	NPC230818
0.8244	Intermediate Similarity	NPC78662
0.8244	Intermediate Similarity	NPC8005
0.8239	Intermediate Similarity	NPC247219
0.8239	Intermediate Similarity	NPC52931
0.8235	Intermediate Similarity	NPC153979
0.8235	Intermediate Similarity	NPC332594
0.8235	Intermediate Similarity	NPC472419
0.8235	Intermediate Similarity	NPC62735
0.8235	Intermediate Similarity	NPC472602
0.8235	Intermediate Similarity	NPC31274
0.8235	Intermediate Similarity	NPC317119
0.8235	Intermediate Similarity	NPC23870
0.8231	Intermediate Similarity	NPC293387
0.8227	Intermediate Similarity	NPC66991
0.8226	Intermediate Similarity	NPC122117
0.8222	Intermediate Similarity	NPC151113
0.8222	Intermediate Similarity	NPC131039
0.8222	Intermediate Similarity	NPC163029
0.8222	Intermediate Similarity	NPC156092
0.8222	Intermediate Similarity	NPC60667
0.8222	Intermediate Similarity	NPC235115
0.8222	Intermediate Similarity	NPC156892
0.8222	Intermediate Similarity	NPC50455
0.8222	Intermediate Similarity	NPC84699
0.8222	Intermediate Similarity	NPC326847
0.8222	Intermediate Similarity	NPC13575
0.822	Intermediate Similarity	NPC6984

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 NPC184219 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	901
0.2-0.3	1445
0.3-0.4	2466
0.4-0.5	2068
0.5-0.6	1306
0.6-0.7	562
0.7-0.8	159
0.8-0.85	7
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9402	High Similarity	NPD9545	Approved
0.8657	High Similarity	NPD7421	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD9493	Approved
0.8195	Intermediate Similarity	NPD1240	Approved
0.8134	Intermediate Similarity	NPD230	Phase 1
0.8095	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD1607	Approved
0.8058	Intermediate Similarity	NPD4628	Phase 3
0.8045	Intermediate Similarity	NPD3764	Approved
0.8029	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD7411	Suspended
0.7956	Intermediate Similarity	NPD1510	Phase 2
0.7914	Intermediate Similarity	NPD1549	Phase 2
0.7914	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD7075	Discontinued
0.7846	Intermediate Similarity	NPD9717	Approved
0.7842	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD2532	Approved
0.7832	Intermediate Similarity	NPD2534	Approved
0.7832	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD2533	Approved
0.7826	Intermediate Similarity	NPD2799	Discontinued
0.7803	Intermediate Similarity	NPD1164	Approved
0.7787	Intermediate Similarity	NPD74	Approved
0.7787	Intermediate Similarity	NPD9266	Approved
0.777	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD7819	Suspended
0.7762	Intermediate Similarity	NPD6799	Approved
0.771	Intermediate Similarity	NPD1608	Approved
0.7708	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD9267	Approved
0.7705	Intermediate Similarity	NPD9264	Approved
0.7705	Intermediate Similarity	NPD9263	Approved
0.7703	Intermediate Similarity	NPD6801	Discontinued
0.7687	Intermediate Similarity	NPD4380	Phase 2
0.7676	Intermediate Similarity	NPD3750	Approved
0.7676	Intermediate Similarity	NPD7003	Approved
0.7669	Intermediate Similarity	NPD1203	Approved
0.7667	Intermediate Similarity	NPD7768	Phase 2
0.7643	Intermediate Similarity	NPD2796	Approved
0.7643	Intermediate Similarity	NPD1551	Phase 2
0.7634	Intermediate Similarity	NPD422	Phase 1
0.7619	Intermediate Similarity	NPD7458	Discontinued
0.7619	Intermediate Similarity	NPD1241	Discontinued
0.7615	Intermediate Similarity	NPD4626	Approved
0.7615	Intermediate Similarity	NPD1778	Approved
0.7606	Intermediate Similarity	NPD1243	Approved
0.7576	Intermediate Similarity	NPD3972	Approved
0.7569	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6599	Discontinued
0.7556	Intermediate Similarity	NPD9494	Approved
0.7552	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD5691	Approved
0.7537	Intermediate Similarity	NPD2797	Approved
0.7533	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7483	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD920	Approved
0.7481	Intermediate Similarity	NPD17	Approved
0.748	Intermediate Similarity	NPD3134	Approved
0.7466	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD2344	Approved
0.7465	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD1283	Approved
0.7447	Intermediate Similarity	NPD7033	Discontinued
0.7434	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6651	Approved
0.7419	Intermediate Similarity	NPD1358	Approved
0.7417	Intermediate Similarity	NPD1238	Approved
0.7397	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5405	Approved
0.7394	Intermediate Similarity	NPD4477	Approved
0.7394	Intermediate Similarity	NPD5408	Approved
0.7394	Intermediate Similarity	NPD4476	Approved
0.7394	Intermediate Similarity	NPD5406	Approved
0.7394	Intermediate Similarity	NPD5404	Approved
0.7391	Intermediate Similarity	NPD6798	Discontinued
0.7391	Intermediate Similarity	NPD3268	Approved
0.7383	Intermediate Similarity	NPD3226	Approved
0.7377	Intermediate Similarity	NPD9261	Approved
0.7368	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1201	Approved
0.736	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2182	Approved
0.7353	Intermediate Similarity	NPD2798	Approved
0.7353	Intermediate Similarity	NPD1019	Discontinued
0.7353	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6004	Phase 3
0.7343	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD6005	Phase 3
0.7343	Intermediate Similarity	NPD6002	Phase 3
0.7328	Intermediate Similarity	NPD1894	Discontinued
0.7324	Intermediate Similarity	NPD3748	Approved
0.7324	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4308	Phase 3
0.7313	Intermediate Similarity	NPD1481	Phase 2
0.7313	Intermediate Similarity	NPD9269	Phase 2
0.7312	Intermediate Similarity	NPD5953	Discontinued
0.731	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6232	Discontinued
0.7297	Intermediate Similarity	NPD9509	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7286	Phase 2
0.7296	Intermediate Similarity	NPD5844	Phase 1
0.7295	Intermediate Similarity	NPD846	Approved
0.7295	Intermediate Similarity	NPD940	Approved
0.7287	Intermediate Similarity	NPD9281	Approved
0.7286	Intermediate Similarity	NPD943	Approved
0.7279	Intermediate Similarity	NPD1470	Approved
0.7273	Intermediate Similarity	NPD9268	Approved
0.7273	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD411	Approved
0.726	Intermediate Similarity	NPD2309	Approved
0.726	Intermediate Similarity	NPD6190	Approved
0.7241	Intermediate Similarity	NPD2800	Approved
0.7239	Intermediate Similarity	NPD1535	Discovery
0.7239	Intermediate Similarity	NPD1281	Approved
0.7237	Intermediate Similarity	NPD1934	Approved
0.7234	Intermediate Similarity	NPD447	Suspended
0.7234	Intermediate Similarity	NPD6355	Discontinued
0.7234	Intermediate Similarity	NPD5124	Phase 1
0.7234	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD255	Approved
0.7231	Intermediate Similarity	NPD256	Approved
0.7222	Intermediate Similarity	NPD2346	Discontinued
0.7214	Intermediate Similarity	NPD520	Approved
0.7208	Intermediate Similarity	NPD3882	Suspended
0.7206	Intermediate Similarity	NPD3225	Approved
0.7194	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD8166	Discontinued
0.7181	Intermediate Similarity	NPD5049	Phase 3
0.7181	Intermediate Similarity	NPD6273	Approved
0.7179	Intermediate Similarity	NPD9258	Approved
0.7179	Intermediate Similarity	NPD9256	Approved
0.7177	Intermediate Similarity	NPD164	Approved
0.7176	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7473	Discontinued
0.7167	Intermediate Similarity	NPD1809	Phase 2
0.7164	Intermediate Similarity	NPD3496	Discontinued
0.7164	Intermediate Similarity	NPD3847	Discontinued
0.7163	Intermediate Similarity	NPD3140	Approved
0.7163	Intermediate Similarity	NPD4060	Phase 1
0.7163	Intermediate Similarity	NPD3142	Approved
0.7162	Intermediate Similarity	NPD1511	Approved
0.7161	Intermediate Similarity	NPD3749	Approved
0.7154	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD845	Approved
0.7143	Intermediate Similarity	NPD2354	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7143	Intermediate Similarity	NPD3817	Phase 2
0.7143	Intermediate Similarity	NPD3887	Approved
0.7133	Intermediate Similarity	NPD5403	Approved
0.7125	Intermediate Similarity	NPD7177	Discontinued
0.7115	Intermediate Similarity	NPD919	Approved
0.7114	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7440	Discontinued
0.7092	Intermediate Similarity	NPD6663	Approved
0.7089	Intermediate Similarity	NPD5710	Approved
0.7089	Intermediate Similarity	NPD5711	Approved
0.7081	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD1876	Approved
0.7078	Intermediate Similarity	NPD2801	Approved
0.7071	Intermediate Similarity	NPD7008	Discontinued
0.7068	Intermediate Similarity	NPD1548	Phase 1
0.7067	Intermediate Similarity	NPD1512	Approved
0.7067	Intermediate Similarity	NPD2186	Approved
0.7059	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD454	Approved
0.705	Intermediate Similarity	NPD5736	Approved
0.7042	Intermediate Similarity	NPD4307	Phase 2
0.7042	Intermediate Similarity	NPD2979	Phase 3
0.704	Intermediate Similarity	NPD1237	Approved
0.7039	Intermediate Similarity	NPD3455	Phase 2
0.7029	Intermediate Similarity	NPD3267	Approved
0.7029	Intermediate Similarity	NPD3266	Approved
0.7025	Intermediate Similarity	NPD2859	Approved
0.7025	Intermediate Similarity	NPD2860	Approved
0.7025	Intermediate Similarity	NPD6959	Discontinued
0.7023	Intermediate Similarity	NPD5951	Approved
0.7021	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1651	Approved
0.7014	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5401	Approved
0.7	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2353	Approved
0.6985	Remote Similarity	NPD1610	Phase 2
0.6984	Remote Similarity	NPD9697	Approved
0.698	Remote Similarity	NPD6652	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6666	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