NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.08
Volume:	270.459
LogP:	3.11
LogD:	3.167
LogS:	-3.919
# Rotatable Bonds:	3
TPSA:	61.06
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.793
Synthetic Accessibility Score:	2.397
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.844
MDCK Permeability:	3.848161213682033e-05
Pgp-inhibitor:	0.526
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	85.45360565185547%
Volume Distribution (VD):	0.814
Pgp-substrate:	19.30992317199707%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.702
CYP2C19-substrate:	0.808
CYP2C9-inhibitor:	0.595
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.459
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.557
CYP3A4-substrate:	0.567

ADMET: Excretion

Clearance (CL):	11.251
Half-life (T1/2):	0.685

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.953
AMES Toxicity:	0.707
Rat Oral Acute Toxicity:	0.633
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.529
Carcinogencity:	0.454
Eye Corrosion:	0.018
Eye Irritation:	0.802
Respiratory Toxicity:	0.657

Download Data

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

Natural Product: NPC39305

Natural Product ID:	NPC39305
*Common Name:**	3,4,9-Trimethoxydibenzofuran-2-Ol
IUPAC Name:	3,4,9-trimethoxydibenzofuran-2-ol
Synonyms:
Standard InCHIKey:	SUNJBUBFVVXZHX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O5/c1-17-10-5-4-6-11-12(10)8-7-9(16)14(18-2)15(19-3)13(8)20-11/h4-7,16H,1-3H3
SMILES:	COc1c(OC)c(O)cc2c1oc1c2c(OC)ccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1269080
PubChem CID:	49831344
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0000015] Dibenzofurans

*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
NPO5061.1	Rhaphiolepis indica var. tashiroi	Varieties	Rosaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1021/np100200s]
NPO5061.1	Rhaphiolepis indica var. tashiroi	Varieties	Rosaceae	Eukaryota	Roots	Wutai, Pingtung County, Taiwan	2007-SEP	PMID[20839880]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	27420.0	nM	PMID[565113]

☑ 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 NPC39305 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	477
0.1-0.2	2012
0.2-0.3	4817
0.3-0.4	11237
0.4-0.5	6245
0.5-0.6	3906
0.6-0.7	5225
0.7-0.8	5321
0.8-0.85	1818
0.85-0.9	1072
0.9-0.95	478
0.95-1	89

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC263092
1.0	High Similarity	NPC59295
1.0	High Similarity	NPC1706
1.0	High Similarity	NPC1755
0.9935	High Similarity	NPC238995
0.9808	High Similarity	NPC45449
0.9808	High Similarity	NPC36320
0.9742	High Similarity	NPC188486
0.974	High Similarity	NPC16935
0.9679	High Similarity	NPC84515
0.9679	High Similarity	NPC272722
0.9679	High Similarity	NPC312056
0.9625	High Similarity	NPC54098
0.9625	High Similarity	NPC230619
0.9613	High Similarity	NPC196879
0.961	High Similarity	NPC472461
0.9565	High Similarity	NPC82217
0.9565	High Similarity	NPC216842
0.9565	High Similarity	NPC476640
0.9506	High Similarity	NPC287243
0.95	High Similarity	NPC247136
0.9494	High Similarity	NPC133065
0.9487	High Similarity	NPC195832
0.9484	High Similarity	NPC45131
0.9448	High Similarity	NPC49667
0.9448	High Similarity	NPC8127
0.9441	High Similarity	NPC476641
0.9437	High Similarity	NPC470704
0.9437	High Similarity	NPC247973
0.9434	High Similarity	NPC39306
0.9416	High Similarity	NPC125300
0.9325	High Similarity	NPC65885
0.9321	High Similarity	NPC28042
0.929	High Similarity	NPC304954
0.9286	High Similarity	NPC260582
0.9273	High Similarity	NPC98546
0.9264	High Similarity	NPC174700
0.9259	High Similarity	NPC202470
0.9255	High Similarity	NPC277480
0.9236	High Similarity	NPC245546
0.9236	High Similarity	NPC43243
0.9236	High Similarity	NPC266960
0.9231	High Similarity	NPC88645
0.9231	High Similarity	NPC167091
0.9231	High Similarity	NPC292214
0.9231	High Similarity	NPC206238
0.9231	High Similarity	NPC271779
0.9207	High Similarity	NPC473834
0.9207	High Similarity	NPC310794
0.9198	High Similarity	NPC50394
0.9193	High Similarity	NPC291110
0.9193	High Similarity	NPC37183
0.9177	High Similarity	NPC203891
0.9177	High Similarity	NPC101830
0.9177	High Similarity	NPC176665
0.9177	High Similarity	NPC110070
0.9177	High Similarity	NPC305663
0.9177	High Similarity	NPC163524
0.9177	High Similarity	NPC287979
0.9172	High Similarity	NPC201451
0.9172	High Similarity	NPC26227
0.9172	High Similarity	NPC44079
0.9167	High Similarity	NPC161277
0.9167	High Similarity	NPC101996
0.9167	High Similarity	NPC199100
0.9167	High Similarity	NPC120537
0.9167	High Similarity	NPC39007
0.9167	High Similarity	NPC180234
0.9157	High Similarity	NPC297807
0.9156	High Similarity	NPC19545
0.9156	High Similarity	NPC287395
0.9156	High Similarity	NPC183655
0.913	High Similarity	NPC110257
0.9125	High Similarity	NPC308992
0.9119	High Similarity	NPC191459
0.9119	High Similarity	NPC288669
0.9119	High Similarity	NPC130894
0.9119	High Similarity	NPC9609
0.9119	High Similarity	NPC300943
0.9119	High Similarity	NPC18772
0.9119	High Similarity	NPC176300
0.9119	High Similarity	NPC22472
0.9119	High Similarity	NPC143828
0.9119	High Similarity	NPC105242
0.9119	High Similarity	NPC115798
0.9119	High Similarity	NPC7846
0.9119	High Similarity	NPC261004
0.9119	High Similarity	NPC253634
0.9119	High Similarity	NPC55738
0.9119	High Similarity	NPC204854
0.9119	High Similarity	NPC4481
0.9119	High Similarity	NPC152166
0.9119	High Similarity	NPC25495
0.9119	High Similarity	NPC19687
0.9119	High Similarity	NPC193842
0.9119	High Similarity	NPC18607
0.9114	High Similarity	NPC265511
0.9114	High Similarity	NPC247017
0.9114	High Similarity	NPC98661
0.9114	High Similarity	NPC292107
0.9114	High Similarity	NPC49824
0.9103	High Similarity	NPC251110
0.9103	High Similarity	NPC149614
0.9103	High Similarity	NPC171010
0.9103	High Similarity	NPC225731
0.9096	High Similarity	NPC24258
0.9091	High Similarity	NPC149846
0.9091	High Similarity	NPC86847
0.9091	High Similarity	NPC140840
0.9091	High Similarity	NPC233956
0.9085	High Similarity	NPC281835
0.9085	High Similarity	NPC131866
0.908	High Similarity	NPC86477
0.9074	High Similarity	NPC29411
0.9074	High Similarity	NPC187923
0.9062	High Similarity	NPC246478
0.9062	High Similarity	NPC263449
0.9057	High Similarity	NPC210084
0.9057	High Similarity	NPC93376
0.9057	High Similarity	NPC227192
0.9057	High Similarity	NPC75215
0.9057	High Similarity	NPC78302
0.9057	High Similarity	NPC472438
0.9057	High Similarity	NPC29841
0.9057	High Similarity	NPC224137
0.9057	High Similarity	NPC235215
0.9057	High Similarity	NPC99597
0.9057	High Similarity	NPC7973
0.9057	High Similarity	NPC189179
0.9051	High Similarity	NPC189960
0.9051	High Similarity	NPC268008
0.9051	High Similarity	NPC256612
0.9051	High Similarity	NPC32557
0.9051	High Similarity	NPC20830
0.9051	High Similarity	NPC214138
0.9051	High Similarity	NPC2928
0.9048	High Similarity	NPC47883
0.9045	High Similarity	NPC275722
0.9045	High Similarity	NPC25270
0.9045	High Similarity	NPC275836
0.9045	High Similarity	NPC256283
0.9045	High Similarity	NPC71334
0.9045	High Similarity	NPC162313
0.9045	High Similarity	NPC156222
0.9045	High Similarity	NPC57030
0.9045	High Similarity	NPC301123
0.9045	High Similarity	NPC120163
0.9045	High Similarity	NPC293183
0.9045	High Similarity	NPC131624
0.9045	High Similarity	NPC27208
0.9045	High Similarity	NPC187498
0.9045	High Similarity	NPC222830
0.9045	High Similarity	NPC55205
0.9045	High Similarity	NPC239128
0.9045	High Similarity	NPC198826
0.9045	High Similarity	NPC83508
0.9045	High Similarity	NPC188203
0.9045	High Similarity	NPC82325
0.9045	High Similarity	NPC100887
0.9045	High Similarity	NPC301323
0.9045	High Similarity	NPC212678
0.9045	High Similarity	NPC279989
0.9045	High Similarity	NPC241498
0.9038	High Similarity	NPC62042
0.9038	High Similarity	NPC248102
0.9038	High Similarity	NPC29231
0.9038	High Similarity	NPC179183
0.9038	High Similarity	NPC61620
0.9038	High Similarity	NPC45873
0.9036	High Similarity	NPC289244
0.9006	High Similarity	NPC162668
0.9	High Similarity	NPC152904
0.8994	High Similarity	NPC255106
0.8994	High Similarity	NPC55619
0.8994	High Similarity	NPC178854
0.8994	High Similarity	NPC472916
0.8994	High Similarity	NPC474520
0.8994	High Similarity	NPC100916
0.8994	High Similarity	NPC201837
0.8994	High Similarity	NPC474638
0.8994	High Similarity	NPC268161
0.8994	High Similarity	NPC200388
0.8994	High Similarity	NPC235165
0.8988	High Similarity	NPC476273
0.8987	High Similarity	NPC236223
0.8987	High Similarity	NPC69394
0.8987	High Similarity	NPC179126
0.8987	High Similarity	NPC183878
0.8987	High Similarity	NPC274327
0.8987	High Similarity	NPC145379
0.8987	High Similarity	NPC270620
0.8987	High Similarity	NPC160951
0.8987	High Similarity	NPC78326
0.8987	High Similarity	NPC86485
0.8987	High Similarity	NPC255350
0.8987	High Similarity	NPC176775
0.8987	High Similarity	NPC22519
0.8987	High Similarity	NPC231018
0.8987	High Similarity	NPC189130
0.8987	High Similarity	NPC47781

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 NPC39305 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	434
0.1-0.2	996
0.2-0.3	1861
0.3-0.4	2696
0.4-0.5	1704
0.5-0.6	959
0.6-0.7	346
0.7-0.8	107
0.8-0.85	28
0.85-0.9	14
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9236	High Similarity	NPD3882	Suspended
0.8987	High Similarity	NPD2801	Approved
0.8889	High Similarity	NPD1247	Approved
0.8805	High Similarity	NPD1934	Approved
0.8782	High Similarity	NPD1512	Approved
0.8667	High Similarity	NPD3926	Phase 2
0.8654	High Similarity	NPD1511	Approved
0.8614	High Similarity	NPD6166	Phase 2
0.8614	High Similarity	NPD6168	Clinical (unspecified phase)
0.8614	High Similarity	NPD6167	Clinical (unspecified phase)
0.8537	High Similarity	NPD919	Approved
0.8519	High Similarity	NPD2393	Clinical (unspecified phase)
0.8512	High Similarity	NPD3818	Discontinued
0.8485	Intermediate Similarity	NPD5494	Approved
0.8466	Intermediate Similarity	NPD3817	Phase 2
0.8372	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6799	Approved
0.8182	Intermediate Similarity	NPD1465	Phase 2
0.8166	Intermediate Similarity	NPD6232	Discontinued
0.8153	Intermediate Similarity	NPD2344	Approved
0.815	Intermediate Similarity	NPD6797	Phase 2
0.8144	Intermediate Similarity	NPD3749	Approved
0.8144	Intermediate Similarity	NPD7075	Discontinued
0.8129	Intermediate Similarity	NPD7473	Discontinued
0.8117	Intermediate Similarity	NPD943	Approved
0.8117	Intermediate Similarity	NPD1240	Approved
0.811	Intermediate Similarity	NPD6599	Discontinued
0.8103	Intermediate Similarity	NPD7251	Discontinued
0.8101	Intermediate Similarity	NPD1549	Phase 2
0.8092	Intermediate Similarity	NPD7074	Phase 3
0.8072	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8057	Intermediate Similarity	NPD7808	Phase 3
0.8038	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD7054	Approved
0.8035	Intermediate Similarity	NPD5844	Phase 1
0.8025	Intermediate Similarity	NPD1510	Phase 2
0.8024	Intermediate Similarity	NPD5402	Approved
0.8013	Intermediate Similarity	NPD1607	Approved
0.8	Intermediate Similarity	NPD6559	Discontinued
0.7989	Intermediate Similarity	NPD7472	Approved
0.795	Intermediate Similarity	NPD2309	Approved
0.7943	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD920	Approved
0.7911	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6801	Discontinued
0.7892	Intermediate Similarity	NPD4380	Phase 2
0.7826	Intermediate Similarity	NPD2800	Approved
0.7826	Intermediate Similarity	NPD1243	Approved
0.7824	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7819	Suspended
0.775	Intermediate Similarity	NPD2796	Approved
0.7727	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD230	Phase 1
0.7722	Intermediate Similarity	NPD447	Suspended
0.7711	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6959	Discontinued
0.7683	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD3751	Discontinued
0.764	Intermediate Similarity	NPD2935	Discontinued
0.7633	Intermediate Similarity	NPD7411	Suspended
0.7628	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD5403	Approved
0.7596	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1471	Phase 3
0.759	Intermediate Similarity	NPD2532	Approved
0.759	Intermediate Similarity	NPD2533	Approved
0.759	Intermediate Similarity	NPD5401	Approved
0.759	Intermediate Similarity	NPD2534	Approved
0.7564	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3750	Approved
0.7558	Intermediate Similarity	NPD7768	Phase 2
0.7557	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1613	Approved
0.7547	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1551	Phase 2
0.7527	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7199	Phase 2
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7452	Intermediate Similarity	NPD9494	Approved
0.7443	Intermediate Similarity	NPD3787	Discontinued
0.7425	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6190	Approved
0.7399	Intermediate Similarity	NPD2296	Approved
0.7371	Intermediate Similarity	NPD6234	Discontinued
0.7362	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2403	Approved
0.7358	Intermediate Similarity	NPD3027	Phase 3
0.7349	Intermediate Similarity	NPD4628	Phase 3
0.731	Intermediate Similarity	NPD3226	Approved
0.7289	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2163	Approved
0.7273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD3748	Approved
0.7256	Intermediate Similarity	NPD2799	Discontinued
0.7251	Intermediate Similarity	NPD1653	Approved
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4287	Approved
0.7215	Intermediate Similarity	NPD1203	Approved
0.7205	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD37	Approved
0.7178	Intermediate Similarity	NPD1933	Approved
0.7174	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2346	Discontinued
0.7167	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4965	Approved
0.7159	Intermediate Similarity	NPD4967	Phase 2
0.7159	Intermediate Similarity	NPD4966	Approved
0.7158	Intermediate Similarity	NPD5953	Discontinued
0.7143	Intermediate Similarity	NPD7286	Phase 2
0.7134	Intermediate Similarity	NPD9269	Phase 2
0.7118	Intermediate Similarity	NPD7390	Discontinued
0.7111	Intermediate Similarity	NPD5242	Approved
0.7108	Intermediate Similarity	NPD6100	Approved
0.7108	Intermediate Similarity	NPD6099	Approved
0.7099	Intermediate Similarity	NPD2313	Discontinued
0.7088	Intermediate Similarity	NPD7228	Approved
0.7086	Intermediate Similarity	NPD6280	Approved
0.7086	Intermediate Similarity	NPD6279	Approved
0.7083	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6355	Discontinued
0.7073	Intermediate Similarity	NPD7907	Approved
0.7062	Intermediate Similarity	NPD6780	Approved
0.7062	Intermediate Similarity	NPD6779	Approved
0.7062	Intermediate Similarity	NPD6782	Approved
0.7062	Intermediate Similarity	NPD6781	Approved
0.7062	Intermediate Similarity	NPD6777	Approved
0.7062	Intermediate Similarity	NPD6776	Approved
0.7062	Intermediate Similarity	NPD6778	Approved
0.7056	Intermediate Similarity	NPD5710	Approved
0.7056	Intermediate Similarity	NPD5711	Approved
0.7056	Intermediate Similarity	NPD7229	Phase 3
0.7055	Intermediate Similarity	NPD6233	Phase 2
0.7041	Intermediate Similarity	NPD7435	Discontinued
0.703	Intermediate Similarity	NPD6651	Approved
0.7027	Intermediate Similarity	NPD7685	Pre-registration
0.7025	Intermediate Similarity	NPD9717	Approved
0.7025	Intermediate Similarity	NPD1608	Approved
0.7	Intermediate Similarity	NPD2354	Approved
0.6995	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6798	Discontinued
0.6994	Remote Similarity	NPD3764	Approved
0.6977	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD4665	Approved
0.6976	Remote Similarity	NPD4111	Phase 1
0.6975	Remote Similarity	NPD4908	Phase 1
0.697	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1610	Phase 2
0.6962	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6808	Phase 2
0.6952	Remote Similarity	NPD8312	Approved
0.6952	Remote Similarity	NPD8313	Approved
0.6941	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD8150	Discontinued
0.6919	Remote Similarity	NPD4357	Discontinued
0.6919	Remote Similarity	NPD1729	Discontinued
0.6919	Remote Similarity	NPD7870	Phase 2
0.6919	Remote Similarity	NPD7871	Phase 2
0.6909	Remote Similarity	NPD4060	Phase 1
0.6894	Remote Similarity	NPD1470	Approved
0.689	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.689	Remote Similarity	NPD411	Approved
0.6882	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2654	Approved
0.6879	Remote Similarity	NPD9268	Approved
0.6871	Remote Similarity	NPD6832	Phase 2
0.6869	Remote Similarity	NPD7697	Approved
0.6869	Remote Similarity	NPD7696	Phase 3
0.6869	Remote Similarity	NPD7698	Approved
0.6866	Remote Similarity	NPD8151	Discontinued
0.6855	Remote Similarity	NPD422	Phase 1
0.6854	Remote Similarity	NPD5761	Phase 2
0.6854	Remote Similarity	NPD5760	Phase 2
0.6853	Remote Similarity	NPD2493	Approved
0.6853	Remote Similarity	NPD2494	Approved
0.6852	Remote Similarity	NPD2798	Approved
0.6845	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6385	Approved
0.6836	Remote Similarity	NPD6386	Approved
0.6835	Remote Similarity	NPD17	Approved
0.6832	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7874	Approved
0.6816	Remote Similarity	NPD5353	Approved
0.6816	Remote Similarity	NPD7701	Phase 2
0.6815	Remote Similarity	NPD1548	Phase 1
0.681	Remote Similarity	NPD2861	Phase 2
0.6809	Remote Similarity	NPD7549	Discontinued
0.6804	Remote Similarity	NPD6535	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