NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.13
Volume:	217.223
LogP:	3.942
LogD:	3.777
LogS:	-3.341
# Rotatable Bonds:	5
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	1.801
Fsp3:	0.5
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:	-4.578
MDCK Permeability:	1.9706783859874122e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.619
Plasma Protein Binding (PPB):	94.98731231689453%
Volume Distribution (VD):	3.567
Pgp-substrate:	4.435711860656738%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.919
CYP2C19-inhibitor:	0.951
CYP2C19-substrate:	0.539
CYP2C9-inhibitor:	0.577
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.928
CYP2D6-substrate:	0.892
CYP3A4-inhibitor:	0.557
CYP3A4-substrate:	0.185

ADMET: Excretion

Clearance (CL):	11.298
Half-life (T1/2):	0.747

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.073
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.494
Skin Sensitization:	0.943
Carcinogencity:	0.039
Eye Corrosion:	0.951
Eye Irritation:	0.986
Respiratory Toxicity:	0.474

Download Data

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

Natural Product: NPC168657

Natural Product ID:	NPC168657
*Common Name:**	3-Methoxy-5-Pentylphenol
IUPAC Name:	3-methoxy-5-pentylphenol
Synonyms:
Standard InCHIKey:	MWWIDYNYLZQEQP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H18O2/c1-3-4-5-6-10-7-11(13)9-12(8-10)14-2/h7-9,13H,3-6H2,1-2H3
SMILES:	CCCCCc1cc(O)cc(c1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503824
PubChem CID:	14757449
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17124632]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125236]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	roots	n.a.	n.a.	PMID[17125236]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15741	Embelia ribes	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	6
Others	2

Activity Type	# Activity
Cell Line	5
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[535974]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[535974]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[535974]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[535974]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[535974]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	=	15920.0	nM	PMID[535975]
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	Inhibition	<	50.0	%	PMID[535975]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	Inhibition	<	50.0	%	PMID[535975]

☑ 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 NPC168657 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	282
0.1-0.2	1727
0.2-0.3	5462
0.3-0.4	13632
0.4-0.5	4235
0.5-0.6	5896
0.6-0.7	8053
0.7-0.8	2799
0.8-0.85	438
0.85-0.9	141
0.9-0.95	26
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9623	High Similarity	NPC276737
0.9623	High Similarity	NPC22610
0.9608	High Similarity	NPC164576
0.9533	High Similarity	NPC53906
0.9444	High Similarity	NPC150624
0.9444	High Similarity	NPC141090
0.9444	High Similarity	NPC114064
0.9358	High Similarity	NPC15860
0.9358	High Similarity	NPC127894
0.9358	High Similarity	NPC33270
0.9358	High Similarity	NPC69261
0.9358	High Similarity	NPC474933
0.9358	High Similarity	NPC219070
0.9358	High Similarity	NPC470759
0.9352	High Similarity	NPC808
0.9352	High Similarity	NPC167934
0.9245	High Similarity	NPC94045
0.9189	High Similarity	NPC184302
0.9182	High Similarity	NPC221549
0.9182	High Similarity	NPC195466
0.9182	High Similarity	NPC244816
0.9182	High Similarity	NPC50521
0.9099	High Similarity	NPC190514
0.9083	High Similarity	NPC228287
0.9083	High Similarity	NPC180508
0.9074	High Similarity	NPC280606
0.9065	High Similarity	NPC2682
0.8981	High Similarity	NPC296920
0.8981	High Similarity	NPC255068
0.8981	High Similarity	NPC90520
0.8947	High Similarity	NPC476633
0.8919	High Similarity	NPC203113
0.8919	High Similarity	NPC54507
0.8919	High Similarity	NPC229147
0.8919	High Similarity	NPC85292
0.8889	High Similarity	NPC303521
0.887	High Similarity	NPC77789
0.887	High Similarity	NPC18128
0.886	High Similarity	NPC102639
0.886	High Similarity	NPC218753
0.885	High Similarity	NPC20674
0.8846	High Similarity	NPC166313
0.8846	High Similarity	NPC192032
0.8846	High Similarity	NPC24407
0.8846	High Similarity	NPC137415
0.8846	High Similarity	NPC11280
0.8846	High Similarity	NPC294186
0.8846	High Similarity	NPC147310
0.8829	High Similarity	NPC464
0.8829	High Similarity	NPC185541
0.8793	High Similarity	NPC282496
0.8793	High Similarity	NPC233526
0.8793	High Similarity	NPC136319
0.8785	High Similarity	NPC35543
0.8783	High Similarity	NPC49341
0.8762	High Similarity	NPC249828
0.8762	High Similarity	NPC242342
0.8762	High Similarity	NPC168303
0.8762	High Similarity	NPC85479
0.8762	High Similarity	NPC302219
0.8762	High Similarity	NPC106396
0.8762	High Similarity	NPC94351
0.8762	High Similarity	NPC53051
0.8762	High Similarity	NPC71002
0.8762	High Similarity	NPC222522
0.8762	High Similarity	NPC146798
0.8762	High Similarity	NPC24404
0.8762	High Similarity	NPC313030
0.8761	High Similarity	NPC63083
0.8761	High Similarity	NPC131118
0.875	High Similarity	NPC193067
0.875	High Similarity	NPC166761
0.875	High Similarity	NPC10588
0.8707	High Similarity	NPC474864
0.8707	High Similarity	NPC57199
0.8707	High Similarity	NPC41562
0.8707	High Similarity	NPC135414
0.8704	High Similarity	NPC75440
0.8704	High Similarity	NPC245115
0.8684	High Similarity	NPC85895
0.8684	High Similarity	NPC137294
0.8679	High Similarity	NPC244513
0.8679	High Similarity	NPC227458
0.8679	High Similarity	NPC218879
0.8673	High Similarity	NPC259638
0.8667	High Similarity	NPC72947
0.8667	High Similarity	NPC284011
0.8649	High Similarity	NPC204120
0.8644	High Similarity	NPC475169
0.8644	High Similarity	NPC105031
0.8644	High Similarity	NPC193544
0.8644	High Similarity	NPC105925
0.8644	High Similarity	NPC472093
0.8644	High Similarity	NPC17943
0.8644	High Similarity	NPC251855
0.8644	High Similarity	NPC476254
0.8644	High Similarity	NPC116907
0.8644	High Similarity	NPC233410
0.8644	High Similarity	NPC298757
0.8644	High Similarity	NPC221077
0.8644	High Similarity	NPC57490
0.8644	High Similarity	NPC293801
0.8644	High Similarity	NPC208950
0.8644	High Similarity	NPC203133
0.8644	High Similarity	NPC131397
0.8644	High Similarity	NPC117214
0.8644	High Similarity	NPC113495
0.8632	High Similarity	NPC121115
0.8632	High Similarity	NPC96940
0.8632	High Similarity	NPC220598
0.8632	High Similarity	NPC197757
0.8632	High Similarity	NPC228922
0.8632	High Similarity	NPC165375
0.8632	High Similarity	NPC84086
0.8624	High Similarity	NPC82016
0.8621	High Similarity	NPC285289
0.8621	High Similarity	NPC75713
0.8621	High Similarity	NPC212965
0.8611	High Similarity	NPC233320
0.8611	High Similarity	NPC61033
0.8611	High Similarity	NPC305603
0.8598	High Similarity	NPC37802
0.8571	High Similarity	NPC170485
0.8571	High Similarity	NPC245060
0.8571	High Similarity	NPC82299
0.8571	High Similarity	NPC76451
0.8571	High Similarity	NPC112596
0.8571	High Similarity	NPC223953
0.8559	High Similarity	NPC140521
0.8559	High Similarity	NPC206487
0.8559	High Similarity	NPC138248
0.8559	High Similarity	NPC228503
0.8559	High Similarity	NPC5796
0.8559	High Similarity	NPC78446
0.8547	High Similarity	NPC74137
0.8547	High Similarity	NPC120638
0.8547	High Similarity	NPC246967
0.8534	High Similarity	NPC166759
0.8529	High Similarity	NPC295295
0.8522	High Similarity	NPC226629
0.8519	High Similarity	NPC473653
0.8519	High Similarity	NPC12640
0.8519	High Similarity	NPC201662
0.8519	High Similarity	NPC99836
0.8505	High Similarity	NPC241891
0.85	High Similarity	NPC159968
0.85	High Similarity	NPC74817
0.85	High Similarity	NPC169474
0.85	High Similarity	NPC246620
0.85	High Similarity	NPC236760
0.85	High Similarity	NPC124452
0.85	High Similarity	NPC236791
0.85	High Similarity	NPC82679
0.85	High Similarity	NPC293054
0.85	High Similarity	NPC473221
0.85	High Similarity	NPC127587
0.85	High Similarity	NPC324112
0.85	High Similarity	NPC282000
0.8491	Intermediate Similarity	NPC100340
0.8491	Intermediate Similarity	NPC143659
0.8487	Intermediate Similarity	NPC278955
0.8487	Intermediate Similarity	NPC60885
0.8487	Intermediate Similarity	NPC234400
0.8487	Intermediate Similarity	NPC105718
0.8487	Intermediate Similarity	NPC249836
0.8475	Intermediate Similarity	NPC474160
0.8475	Intermediate Similarity	NPC95168
0.8468	Intermediate Similarity	NPC203924
0.8468	Intermediate Similarity	NPC275627
0.8455	Intermediate Similarity	NPC165386
0.8448	Intermediate Similarity	NPC229401
0.8448	Intermediate Similarity	NPC474565
0.8447	Intermediate Similarity	NPC16649
0.844	Intermediate Similarity	NPC232523
0.844	Intermediate Similarity	NPC204901
0.844	Intermediate Similarity	NPC158253
0.843	Intermediate Similarity	NPC186843
0.843	Intermediate Similarity	NPC28765
0.843	Intermediate Similarity	NPC154866
0.843	Intermediate Similarity	NPC211179
0.843	Intermediate Similarity	NPC470213
0.843	Intermediate Similarity	NPC206615
0.843	Intermediate Similarity	NPC38604
0.843	Intermediate Similarity	NPC266691
0.843	Intermediate Similarity	NPC98631
0.8426	Intermediate Similarity	NPC246056
0.8426	Intermediate Similarity	NPC134829
0.8421	Intermediate Similarity	NPC123559
0.8417	Intermediate Similarity	NPC28730
0.8417	Intermediate Similarity	NPC78974
0.8417	Intermediate Similarity	NPC214406
0.8417	Intermediate Similarity	NPC223136
0.8417	Intermediate Similarity	NPC103823
0.8417	Intermediate Similarity	NPC44748
0.8417	Intermediate Similarity	NPC18924
0.8411	Intermediate Similarity	NPC305205
0.8403	Intermediate Similarity	NPC270030
0.8403	Intermediate Similarity	NPC183446
0.8393	Intermediate Similarity	NPC98372
0.839	Intermediate Similarity	NPC36016

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 NPC168657 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	300
0.1-0.2	1049
0.2-0.3	1739
0.3-0.4	2703
0.4-0.5	1719
0.5-0.6	1012
0.6-0.7	528
0.7-0.8	88
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8632	High Similarity	NPD4749	Approved
0.8417	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8361	Intermediate Similarity	NPD3027	Phase 3
0.8318	Intermediate Similarity	NPD940	Approved
0.8318	Intermediate Similarity	NPD846	Approved
0.8305	Intermediate Similarity	NPD1610	Phase 2
0.8293	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD4750	Phase 3
0.8276	Intermediate Similarity	NPD1548	Phase 1
0.8211	Intermediate Similarity	NPD4625	Phase 3
0.8142	Intermediate Similarity	NPD228	Approved
0.813	Intermediate Similarity	NPD4908	Phase 1
0.8056	Intermediate Similarity	NPD1242	Phase 1
0.8049	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD6671	Approved
0.8	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD422	Phase 1
0.7984	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD1613	Approved
0.785	Intermediate Similarity	NPD844	Approved
0.7724	Intermediate Similarity	NPD2983	Phase 2
0.7724	Intermediate Similarity	NPD2982	Phase 2
0.7719	Intermediate Similarity	NPD2684	Approved
0.771	Intermediate Similarity	NPD6099	Approved
0.771	Intermediate Similarity	NPD6100	Approved
0.7699	Intermediate Similarity	NPD968	Approved
0.7661	Intermediate Similarity	NPD6696	Suspended
0.7642	Intermediate Similarity	NPD2981	Phase 2
0.7632	Intermediate Similarity	NPD290	Approved
0.7619	Intermediate Similarity	NPD3018	Phase 2
0.7619	Intermediate Similarity	NPD2861	Phase 2
0.7615	Intermediate Similarity	NPD288	Approved
0.7597	Intermediate Similarity	NPD1240	Approved
0.7593	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD5283	Phase 1
0.7541	Intermediate Similarity	NPD4626	Approved
0.7541	Intermediate Similarity	NPD1778	Approved
0.7523	Intermediate Similarity	NPD2860	Approved
0.7523	Intermediate Similarity	NPD2859	Approved
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD2230	Approved
0.75	Intermediate Similarity	NPD2232	Approved
0.75	Intermediate Similarity	NPD2233	Approved
0.7481	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD1607	Approved
0.7477	Intermediate Similarity	NPD3020	Approved
0.7463	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD2238	Phase 2
0.7458	Intermediate Similarity	NPD821	Approved
0.7458	Intermediate Similarity	NPD7843	Approved
0.7453	Intermediate Similarity	NPD9295	Approved
0.7442	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD2933	Approved
0.7431	Intermediate Similarity	NPD2934	Approved
0.7419	Intermediate Similarity	NPD1091	Approved
0.7417	Intermediate Similarity	NPD7157	Approved
0.7402	Intermediate Similarity	NPD6584	Phase 3
0.7368	Intermediate Similarity	NPD1510	Phase 2
0.7353	Intermediate Similarity	NPD9093	Approved
0.735	Intermediate Similarity	NPD5451	Approved
0.7339	Intermediate Similarity	NPD3496	Discontinued
0.7339	Intermediate Similarity	NPD845	Approved
0.7317	Intermediate Similarity	NPD1357	Approved
0.7293	Intermediate Similarity	NPD6111	Discontinued
0.7287	Intermediate Similarity	NPD596	Approved
0.7287	Intermediate Similarity	NPD600	Approved
0.7282	Intermediate Similarity	NPD9089	Approved
0.728	Intermediate Similarity	NPD3705	Approved
0.7273	Intermediate Similarity	NPD709	Approved
0.7258	Intermediate Similarity	NPD2667	Approved
0.7258	Intermediate Similarity	NPD2668	Approved
0.7258	Intermediate Similarity	NPD17	Approved
0.725	Intermediate Similarity	NPD1398	Phase 1
0.7241	Intermediate Similarity	NPD1445	Approved
0.7241	Intermediate Similarity	NPD1444	Approved
0.7238	Intermediate Similarity	NPD111	Approved
0.7226	Intermediate Similarity	NPD3892	Phase 2
0.7222	Intermediate Similarity	NPD2231	Phase 2
0.7222	Intermediate Similarity	NPD2235	Phase 2
0.7207	Intermediate Similarity	NPD1809	Phase 2
0.7203	Intermediate Similarity	NPD3022	Approved
0.7203	Intermediate Similarity	NPD3021	Approved
0.7177	Intermediate Similarity	NPD1651	Approved
0.7177	Intermediate Similarity	NPD5691	Approved
0.7174	Intermediate Similarity	NPD2219	Phase 1
0.7167	Intermediate Similarity	NPD1138	Approved
0.7165	Intermediate Similarity	NPD6582	Phase 2
0.7165	Intermediate Similarity	NPD6583	Phase 3
0.7165	Intermediate Similarity	NPD1669	Approved
0.7165	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7447	Phase 1
0.7143	Intermediate Similarity	NPD3157	Approved
0.7143	Intermediate Similarity	NPD5124	Phase 1
0.7143	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3158	Phase 1
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7132	Intermediate Similarity	NPD602	Approved
0.7132	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD858	Approved
0.7132	Intermediate Similarity	NPD859	Approved
0.7132	Intermediate Similarity	NPD4624	Approved
0.7132	Intermediate Similarity	NPD599	Approved
0.7121	Intermediate Similarity	NPD839	Approved
0.7121	Intermediate Similarity	NPD840	Approved
0.7117	Intermediate Similarity	NPD9296	Approved
0.7109	Intermediate Similarity	NPD1283	Approved
0.7101	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD3134	Approved
0.709	Intermediate Similarity	NPD4097	Suspended
0.709	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1137	Approved
0.7083	Intermediate Similarity	NPD1139	Approved
0.708	Intermediate Similarity	NPD1549	Phase 2
0.7077	Intermediate Similarity	NPD1712	Approved
0.7073	Intermediate Similarity	NPD7340	Approved
0.7071	Intermediate Similarity	NPD7213	Phase 3
0.7071	Intermediate Similarity	NPD7212	Phase 2
0.7068	Intermediate Similarity	NPD4060	Phase 1
0.7068	Intermediate Similarity	NPD3620	Phase 2
0.7068	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1558	Phase 1
0.7063	Intermediate Similarity	NPD3847	Discontinued
0.7059	Intermediate Similarity	NPD2935	Discontinued
0.7059	Intermediate Similarity	NPD1551	Phase 2
0.7059	Intermediate Similarity	NPD1792	Phase 2
0.7054	Intermediate Similarity	NPD2797	Approved
0.7034	Intermediate Similarity	NPD1358	Approved
0.7025	Intermediate Similarity	NPD5535	Approved
0.7021	Intermediate Similarity	NPD2532	Approved
0.7021	Intermediate Similarity	NPD2533	Approved
0.7021	Intermediate Similarity	NPD2534	Approved
0.7007	Intermediate Similarity	NPD3540	Phase 1
0.7	Intermediate Similarity	NPD3691	Phase 2
0.7	Intermediate Similarity	NPD558	Phase 2
0.7	Intermediate Similarity	NPD3690	Phase 2
0.6992	Remote Similarity	NPD2674	Phase 3
0.6986	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD9500	Approved
0.6978	Remote Similarity	NPD3750	Approved
0.6977	Remote Similarity	NPD8651	Approved
0.696	Remote Similarity	NPD9545	Approved
0.695	Remote Similarity	NPD1511	Approved
0.695	Remote Similarity	NPD4357	Discontinued
0.6944	Remote Similarity	NPD4005	Discontinued
0.6935	Remote Similarity	NPD9493	Approved
0.6934	Remote Similarity	NPD2796	Approved
0.6934	Remote Similarity	NPD3539	Phase 1
0.6929	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1934	Approved
0.6918	Remote Similarity	NPD37	Approved
0.6912	Remote Similarity	NPD2200	Suspended
0.6906	Remote Similarity	NPD1652	Phase 2
0.6906	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5585	Approved
0.6899	Remote Similarity	NPD5327	Phase 3
0.6899	Remote Similarity	NPD3685	Discontinued
0.6899	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5735	Approved
0.6885	Remote Similarity	NPD7635	Approved
0.6881	Remote Similarity	NPD9094	Approved
0.688	Remote Similarity	NPD5536	Phase 2
0.6879	Remote Similarity	NPD7124	Phase 2
0.6875	Remote Similarity	NPD776	Approved
0.6875	Remote Similarity	NPD1653	Approved
0.6875	Remote Similarity	NPD1281	Approved
0.6871	Remote Similarity	NPD2801	Approved
0.6861	Remote Similarity	NPD7033	Discontinued
0.6861	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2557	Approved
0.6853	Remote Similarity	NPD1512	Approved
0.685	Remote Similarity	NPD5846	Approved
0.685	Remote Similarity	NPD6516	Phase 2
0.6847	Remote Similarity	NPD9365	Approved
0.6846	Remote Similarity	NPD3225	Approved
0.6842	Remote Similarity	NPD7095	Approved
0.6838	Remote Similarity	NPD6653	Approved
0.6838	Remote Similarity	NPD6651	Approved
0.6829	Remote Similarity	NPD1241	Discontinued
0.6825	Remote Similarity	NPD1182	Approved
0.6825	Remote Similarity	NPD3091	Approved
0.6822	Remote Similarity	NPD9717	Approved
0.6818	Remote Similarity	NPD9494	Approved
0.6815	Remote Similarity	NPD4140	Approved
0.68	Remote Similarity	NPD3596	Phase 2
0.68	Remote Similarity	NPD6234	Discontinued
0.6791	Remote Similarity	NPD3268	Approved
0.6791	Remote Similarity	NPD1296	Phase 2
0.6791	Remote Similarity	NPD3145	Approved
0.6791	Remote Similarity	NPD3144	Approved
0.6791	Remote Similarity	NPD1039	Discontinued
0.6788	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4536	Approved
0.6788	Remote Similarity	NPD4538	Approved
0.6786	Remote Similarity	NPD3060	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