NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.1
Volume:	279.016
LogP:	3.196
LogD:	3.059
LogS:	-3.193
# Rotatable Bonds:	3
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.75
Synthetic Accessibility Score:	2.366
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.998
MDCK Permeability:	1.367017648590263e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.107
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.861
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	98.95144653320312%
Volume Distribution (VD):	0.467
Pgp-substrate:	1.874334692955017%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.384
CYP2C19-substrate:	0.123
CYP2C9-inhibitor:	0.454
CYP2C9-substrate:	0.755
CYP2D6-inhibitor:	0.56
CYP2D6-substrate:	0.876
CYP3A4-inhibitor:	0.192
CYP3A4-substrate:	0.394

ADMET: Excretion

Clearance (CL):	12.855
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.205
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.812
Maximum Recommended Daily Dose:	0.895
Skin Sensitization:	0.965
Carcinogencity:	0.218
Eye Corrosion:	0.247
Eye Irritation:	0.951
Respiratory Toxicity:	0.673

Download Data

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

Natural Product: NPC45824

Natural Product ID:	NPC45824
*Common Name:**	5-Methoxy-3,5'-Dimethyl-2,3'-Oxybiphenyl-1,1',2'-Triol
IUPAC Name:	3-(2-hydroxy-4-methoxy-6-methylphenoxy)-5-methylbenzene-1,2-diol
Synonyms:
Standard InCHIKey:	JGXPRDVSWGDODG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O5/c1-8-4-11(16)14(18)13(5-8)20-15-9(2)6-10(19-3)7-12(15)17/h4-7,16-18H,1-3H3
SMILES:	Cc1cc(c(c(c1)Oc1c(C)cc(cc1O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2152644
PubChem CID:	24148517
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004155] Diphenylethers

*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
NPO32810	preussia typharum	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23046341]
NPO32810	preussia typharum	Species	Sporormiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24893224]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	11600.0	nM	PMID[568957]

☑ 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 NPC45824 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	509
0.1-0.2	2135
0.2-0.3	7493
0.3-0.4	12297
0.4-0.5	3328
0.5-0.6	4344
0.6-0.7	6773
0.7-0.8	4453
0.8-0.85	803
0.85-0.9	374
0.9-0.95	180
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC214860
0.9836	High Similarity	NPC216836
0.9531	High Similarity	NPC472337
0.952	High Similarity	NPC10225
0.952	High Similarity	NPC58164
0.9457	High Similarity	NPC472336
0.9457	High Similarity	NPC472334
0.9449	High Similarity	NPC127624
0.9444	High Similarity	NPC311680
0.9444	High Similarity	NPC299221
0.9444	High Similarity	NPC51840
0.9444	High Similarity	NPC234488
0.9431	High Similarity	NPC183446
0.9385	High Similarity	NPC103976
0.9385	High Similarity	NPC326797
0.9385	High Similarity	NPC474282
0.9385	High Similarity	NPC276490
0.9385	High Similarity	NPC107551
0.9385	High Similarity	NPC102904
0.9385	High Similarity	NPC176051
0.9375	High Similarity	NPC37196
0.9375	High Similarity	NPC94236
0.9375	High Similarity	NPC229442
0.9375	High Similarity	NPC168059
0.936	High Similarity	NPC210355
0.9355	High Similarity	NPC82483
0.9355	High Similarity	NPC265483
0.9355	High Similarity	NPC299584
0.9344	High Similarity	NPC145780
0.9313	High Similarity	NPC245207
0.9313	High Similarity	NPC319647
0.9313	High Similarity	NPC127218
0.9313	High Similarity	NPC25966
0.9302	High Similarity	NPC106215
0.9302	High Similarity	NPC310854
0.9297	High Similarity	NPC6451
0.9297	High Similarity	NPC161203
0.9297	High Similarity	NPC86655
0.9297	High Similarity	NPC202762
0.9286	High Similarity	NPC266691
0.928	High Similarity	NPC223136
0.928	High Similarity	NPC28730
0.928	High Similarity	NPC44748
0.928	High Similarity	NPC78974
0.928	High Similarity	NPC18924
0.928	High Similarity	NPC214406
0.928	High Similarity	NPC103823
0.9242	High Similarity	NPC160283
0.9242	High Similarity	NPC254759
0.9242	High Similarity	NPC259519
0.9231	High Similarity	NPC234333
0.9231	High Similarity	NPC474206
0.9231	High Similarity	NPC121812
0.9231	High Similarity	NPC195022
0.9231	High Similarity	NPC47398
0.9231	High Similarity	NPC134968
0.9231	High Similarity	NPC201357
0.9231	High Similarity	NPC94750
0.9231	High Similarity	NPC112246
0.9231	High Similarity	NPC260898
0.9231	High Similarity	NPC281521
0.9231	High Similarity	NPC255147
0.9231	High Similarity	NPC112939
0.9231	High Similarity	NPC470356
0.9225	High Similarity	NPC475840
0.9225	High Similarity	NPC36661
0.9219	High Similarity	NPC474356
0.9219	High Similarity	NPC45715
0.9219	High Similarity	NPC232275
0.9219	High Similarity	NPC472597
0.9219	High Similarity	NPC12275
0.9206	High Similarity	NPC293054
0.9206	High Similarity	NPC236791
0.9206	High Similarity	NPC324112
0.9206	High Similarity	NPC169474
0.9206	High Similarity	NPC5447
0.9206	High Similarity	NPC159968
0.9206	High Similarity	NPC82679
0.9206	High Similarity	NPC74817
0.9206	High Similarity	NPC250432
0.9206	High Similarity	NPC124452
0.9206	High Similarity	NPC282000
0.9206	High Similarity	NPC246620
0.92	High Similarity	NPC60885
0.92	High Similarity	NPC234400
0.9194	High Similarity	NPC95168
0.9173	High Similarity	NPC471389
0.9173	High Similarity	NPC247291
0.9173	High Similarity	NPC311530
0.9167	High Similarity	NPC292882
0.916	High Similarity	NPC474639
0.916	High Similarity	NPC270456
0.916	High Similarity	NPC162659
0.916	High Similarity	NPC248727
0.916	High Similarity	NPC16435
0.916	High Similarity	NPC306441
0.916	High Similarity	NPC230734
0.916	High Similarity	NPC173660
0.916	High Similarity	NPC227503
0.916	High Similarity	NPC265433
0.9154	High Similarity	NPC317380
0.9147	High Similarity	NPC7903
0.9147	High Similarity	NPC35932
0.9147	High Similarity	NPC160991
0.9147	High Similarity	NPC16208
0.9147	High Similarity	NPC184447
0.9141	High Similarity	NPC224157
0.9141	High Similarity	NPC192687
0.9141	High Similarity	NPC229231
0.9141	High Similarity	NPC472338
0.9141	High Similarity	NPC91291
0.9141	High Similarity	NPC220935
0.9134	High Similarity	NPC46274
0.9134	High Similarity	NPC63179
0.9134	High Similarity	NPC154866
0.9134	High Similarity	NPC28765
0.9134	High Similarity	NPC226331
0.9127	High Similarity	NPC181361
0.912	High Similarity	NPC122792
0.912	High Similarity	NPC228972
0.9113	High Similarity	NPC262253
0.9113	High Similarity	NPC473411
0.9113	High Similarity	NPC71579
0.9104	High Similarity	NPC107161
0.9104	High Similarity	NPC472335
0.9104	High Similarity	NPC472332
0.9091	High Similarity	NPC211549
0.9084	High Similarity	NPC151224
0.9084	High Similarity	NPC61946
0.9077	High Similarity	NPC11060
0.9077	High Similarity	NPC269528
0.907	High Similarity	NPC82503
0.907	High Similarity	NPC268342
0.907	High Similarity	NPC42760
0.907	High Similarity	NPC309787
0.907	High Similarity	NPC220825
0.907	High Similarity	NPC268266
0.9062	High Similarity	NPC210623
0.9062	High Similarity	NPC218856
0.9062	High Similarity	NPC222004
0.9062	High Similarity	NPC190629
0.9062	High Similarity	NPC273295
0.9062	High Similarity	NPC3439
0.9062	High Similarity	NPC226788
0.9062	High Similarity	NPC285339
0.9062	High Similarity	NPC470258
0.9062	High Similarity	NPC202582
0.9062	High Similarity	NPC190144
0.9055	High Similarity	NPC50368
0.9055	High Similarity	NPC252131
0.9055	High Similarity	NPC470699
0.9055	High Similarity	NPC266555
0.9048	High Similarity	NPC57490
0.9048	High Similarity	NPC208950
0.9048	High Similarity	NPC475169
0.9048	High Similarity	NPC221077
0.9048	High Similarity	NPC105925
0.9048	High Similarity	NPC116907
0.9048	High Similarity	NPC251855
0.9048	High Similarity	NPC298757
0.9048	High Similarity	NPC117214
0.9048	High Similarity	NPC472093
0.9048	High Similarity	NPC203133
0.9048	High Similarity	NPC233410
0.9048	High Similarity	NPC193544
0.9048	High Similarity	NPC17943
0.904	High Similarity	NPC228922
0.904	High Similarity	NPC121115
0.904	High Similarity	NPC197757
0.9037	High Similarity	NPC102044
0.9037	High Similarity	NPC47633
0.9037	High Similarity	NPC477616
0.9037	High Similarity	NPC85264
0.9032	High Similarity	NPC285289
0.9032	High Similarity	NPC75713
0.9024	High Similarity	NPC232084
0.9024	High Similarity	NPC247364
0.9024	High Similarity	NPC10932
0.9024	High Similarity	NPC61516
0.9023	High Similarity	NPC70682
0.9023	High Similarity	NPC260741
0.9023	High Similarity	NPC471388
0.9015	High Similarity	NPC302701
0.9015	High Similarity	NPC470802
0.9015	High Similarity	NPC269091
0.9008	High Similarity	NPC170694
0.9	High Similarity	NPC261619
0.9	High Similarity	NPC470752
0.9	High Similarity	NPC185604
0.9	High Similarity	NPC219876
0.9	High Similarity	NPC126029
0.9	High Similarity	NPC15658
0.9	High Similarity	NPC61477
0.9	High Similarity	NPC78770
0.8992	High Similarity	NPC469612
0.8992	High Similarity	NPC126836
0.8992	High Similarity	NPC474481
0.8992	High Similarity	NPC469614
0.8984	High Similarity	NPC19694
0.8976	High Similarity	NPC112596

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 NPC45824 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	437
0.1-0.2	976
0.2-0.3	2344
0.3-0.4	2556
0.4-0.5	1399
0.5-0.6	799
0.6-0.7	534
0.7-0.8	93
0.8-0.85	9
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9206	High Similarity	NPD1530	Clinical (unspecified phase)
0.9134	High Similarity	NPD1529	Clinical (unspecified phase)
0.9	High Similarity	NPD1612	Clinical (unspecified phase)
0.9	High Similarity	NPD1613	Approved
0.8915	High Similarity	NPD3027	Phase 3
0.8356	Intermediate Similarity	NPD2801	Approved
0.8333	Intermediate Similarity	NPD3018	Phase 2
0.8268	Intermediate Similarity	NPD1548	Phase 1
0.8264	Intermediate Similarity	NPD1653	Approved
0.8168	Intermediate Similarity	NPD2982	Phase 2
0.8168	Intermediate Similarity	NPD2983	Phase 2
0.8154	Intermediate Similarity	NPD1610	Phase 2
0.8145	Intermediate Similarity	NPD228	Approved
0.8134	Intermediate Similarity	NPD4908	Phase 1
0.8092	Intermediate Similarity	NPD2981	Phase 2
0.8041	Intermediate Similarity	NPD1934	Approved
0.8015	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD1511	Approved
0.7926	Intermediate Similarity	NPD2861	Phase 2
0.7899	Intermediate Similarity	NPD1558	Phase 1
0.7895	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD4749	Approved
0.7881	Intermediate Similarity	NPD3882	Suspended
0.7877	Intermediate Similarity	NPD1512	Approved
0.7867	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD4625	Phase 3
0.7763	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD6671	Approved
0.7744	Intermediate Similarity	NPD422	Phase 1
0.7744	Intermediate Similarity	NPD1091	Approved
0.7742	Intermediate Similarity	NPD968	Approved
0.7734	Intermediate Similarity	NPD5283	Phase 1
0.7692	Intermediate Similarity	NPD3540	Phase 1
0.7667	Intermediate Similarity	NPD4675	Approved
0.7667	Intermediate Similarity	NPD4678	Approved
0.7643	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6166	Phase 2
0.7635	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7626	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3539	Phase 1
0.7582	Intermediate Similarity	NPD3817	Phase 2
0.7548	Intermediate Similarity	NPD6234	Discontinued
0.754	Intermediate Similarity	NPD290	Approved
0.7518	Intermediate Similarity	NPD4060	Phase 1
0.7516	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD7054	Approved
0.7481	Intermediate Similarity	NPD3705	Approved
0.748	Intermediate Similarity	NPD1242	Phase 1
0.7465	Intermediate Similarity	NPD230	Phase 1
0.7453	Intermediate Similarity	NPD7472	Approved
0.7453	Intermediate Similarity	NPD7074	Phase 3
0.7438	Intermediate Similarity	NPD3818	Discontinued
0.7423	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD3022	Approved
0.7422	Intermediate Similarity	NPD3021	Approved
0.7391	Intermediate Similarity	NPD5844	Phase 1
0.7383	Intermediate Similarity	NPD4357	Discontinued
0.7368	Intermediate Similarity	NPD5536	Phase 2
0.7365	Intermediate Similarity	NPD2219	Phase 1
0.7365	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6674	Discontinued
0.7347	Intermediate Similarity	NPD1652	Phase 2
0.7347	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD2684	Approved
0.7342	Intermediate Similarity	NPD7199	Phase 2
0.7338	Intermediate Similarity	NPD37	Approved
0.7338	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4123	Phase 3
0.7333	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD6696	Suspended
0.7308	Intermediate Similarity	NPD4965	Approved
0.7308	Intermediate Similarity	NPD4967	Phase 2
0.7308	Intermediate Similarity	NPD4966	Approved
0.7301	Intermediate Similarity	NPD6797	Phase 2
0.728	Intermediate Similarity	NPD846	Approved
0.728	Intermediate Similarity	NPD940	Approved
0.7279	Intermediate Similarity	NPD3496	Discontinued
0.7278	Intermediate Similarity	NPD5494	Approved
0.7273	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3620	Phase 2
0.726	Intermediate Similarity	NPD6100	Approved
0.726	Intermediate Similarity	NPD6099	Approved
0.7259	Intermediate Similarity	NPD1357	Approved
0.7256	Intermediate Similarity	NPD7251	Discontinued
0.7255	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD7843	Approved
0.725	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7228	Approved
0.7222	Intermediate Similarity	NPD447	Suspended
0.7219	Intermediate Similarity	NPD7447	Phase 1
0.7218	Intermediate Similarity	NPD7157	Approved
0.7212	Intermediate Similarity	NPD7808	Phase 3
0.7212	Intermediate Similarity	NPD7549	Discontinued
0.7211	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD7266	Discontinued
0.7211	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6233	Phase 2
0.7195	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD8651	Approved
0.7188	Intermediate Similarity	NPD6232	Discontinued
0.7162	Intermediate Similarity	NPD1549	Phase 2
0.7162	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4750	Phase 3
0.7153	Intermediate Similarity	NPD1240	Approved
0.7152	Intermediate Similarity	NPD6799	Approved
0.7152	Intermediate Similarity	NPD7212	Phase 2
0.7152	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7213	Phase 3
0.7143	Intermediate Similarity	NPD2935	Discontinued
0.7143	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD4005	Discontinued
0.7143	Intermediate Similarity	NPD291	Approved
0.7134	Intermediate Similarity	NPD5402	Approved
0.7133	Intermediate Similarity	NPD2677	Approved
0.7133	Intermediate Similarity	NPD6190	Approved
0.7126	Intermediate Similarity	NPD8053	Approved
0.7126	Intermediate Similarity	NPD8054	Approved
0.7123	Intermediate Similarity	NPD4538	Approved
0.7123	Intermediate Similarity	NPD4536	Approved
0.7123	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3060	Approved
0.7113	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1535	Discovery
0.7097	Intermediate Similarity	NPD4380	Phase 2
0.7095	Intermediate Similarity	NPD1375	Discontinued
0.7095	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD6584	Phase 3
0.7086	Intermediate Similarity	NPD7124	Phase 2
0.7083	Intermediate Similarity	NPD2674	Phase 3
0.708	Intermediate Similarity	NPD1778	Approved
0.7075	Intermediate Similarity	NPD1510	Phase 2
0.7073	Intermediate Similarity	NPD9296	Approved
0.7071	Intermediate Similarity	NPD2922	Phase 1
0.7068	Intermediate Similarity	NPD1398	Phase 1
0.7067	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3892	Phase 2
0.7067	Intermediate Similarity	NPD3750	Approved
0.7063	Intermediate Similarity	NPD7095	Approved
0.7055	Intermediate Similarity	NPD1607	Approved
0.7055	Intermediate Similarity	NPD7473	Discontinued
0.705	Intermediate Similarity	NPD1481	Phase 2
0.7044	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7075	Discontinued
0.7042	Intermediate Similarity	NPD9494	Approved
0.7039	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1774	Approved
0.7034	Intermediate Similarity	NPD943	Approved
0.7019	Intermediate Similarity	NPD1247	Approved
0.7014	Intermediate Similarity	NPD6798	Discontinued
0.7014	Intermediate Similarity	NPD3144	Approved
0.7014	Intermediate Similarity	NPD3145	Approved
0.7007	Intermediate Similarity	NPD6111	Discontinued
0.7	Intermediate Similarity	NPD4162	Approved
0.7	Intermediate Similarity	NPD5177	Phase 3
0.7	Intermediate Similarity	NPD4236	Phase 3
0.7	Intermediate Similarity	NPD4237	Approved
0.6986	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6355	Discontinued
0.6986	Remote Similarity	NPD5124	Phase 1
0.6978	Remote Similarity	NPD1611	Approved
0.6966	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5588	Approved
0.6959	Remote Similarity	NPD5960	Phase 3
0.6959	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6516	Phase 2
0.6957	Remote Similarity	NPD5677	Discontinued
0.6957	Remote Similarity	NPD5846	Approved
0.695	Remote Similarity	NPD3225	Approved
0.6948	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4055	Discovery
0.6934	Remote Similarity	NPD1182	Approved
0.6929	Remote Similarity	NPD1608	Approved
0.6913	Remote Similarity	NPD2796	Approved
0.6912	Remote Similarity	NPD7340	Approved
0.6903	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1424	Approved
0.6879	Remote Similarity	NPD6582	Phase 2
0.6879	Remote Similarity	NPD6583	Phase 3
0.6879	Remote Similarity	NPD6599	Discontinued
0.6875	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4340	Discontinued
0.6871	Remote Similarity	NPD3787	Discontinued
0.6867	Remote Similarity	NPD5763	Approved
0.6867	Remote Similarity	NPD5762	Approved
0.6866	Remote Similarity	NPD821	Approved
0.6866	Remote Similarity	NPD5535	Approved
0.6863	Remote Similarity	NPD5058	Phase 3
0.6861	Remote Similarity	NPD1408	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3686	Approved
0.6859	Remote Similarity	NPD3687	Approved
0.6855	Remote Similarity	NPD2977	Approved
0.6855	Remote Similarity	NPD7819	Suspended

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