NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.09
Volume:	276.329
LogP:	3.752
LogD:	3.631
LogS:	-3.855
# Rotatable Bonds:	2
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.743
Synthetic Accessibility Score:	2.142
Fsp3:	0.125
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:	-4.808
MDCK Permeability:	1.5106834325706586e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.972
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.107

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	98.36360931396484%
Volume Distribution (VD):	0.572
Pgp-substrate:	2.1918063163757324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.828
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.653
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.774
CYP2D6-substrate:	0.913
CYP3A4-inhibitor:	0.804
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	10.991
Half-life (T1/2):	0.824

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.432
Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.833
Skin Sensitization:	0.663
Carcinogencity:	0.484
Eye Corrosion:	0.015
Eye Irritation:	0.934
Respiratory Toxicity:	0.324

Download Data

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

Natural Product: NPC188486

Natural Product ID:	NPC188486
*Common Name:**	Pterolinus B
IUPAC Name:	2-(4-hydroxyphenyl)-6-methoxy-3-methyl-1-benzofuran-5-ol
Synonyms:	Pterolinus B
Standard InCHIKey:	CQFHUONRLJIEPG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O4/c1-9-12-7-13(18)15(19-2)8-14(12)20-16(9)10-3-5-11(17)6-4-10/h3-8,17-18H,1-2H3
SMILES:	COc1cc2oc(c(c2cc1O)C)c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801599
PubChem CID:	53262811
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	Heartwood	India	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[21784631]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	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	5

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2.34	ug.mL-1	PMID[506183]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1.74	ug.mL-1	PMID[506183]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.19	ug.mL-1	PMID[506183]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	47.83	ug.mL-1	PMID[506183]
NPT2	Others	Unspecified		IC50	=	0.19	ug.mL-1	PMID[506183]

☑ 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 NPC188486 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	458
0.1-0.2	1991
0.2-0.3	4714
0.3-0.4	11648
0.4-0.5	5937
0.5-0.6	3749
0.6-0.7	5222
0.7-0.8	5354
0.8-0.85	2025
0.85-0.9	1047
0.9-0.95	513
0.95-1	39

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC84515
0.9935	High Similarity	NPC312056
0.9868	High Similarity	NPC16935
0.9868	High Similarity	NPC196879
0.9742	High Similarity	NPC133065
0.9742	High Similarity	NPC39305
0.9742	High Similarity	NPC1755
0.9742	High Similarity	NPC1706
0.9742	High Similarity	NPC59295
0.9742	High Similarity	NPC263092
0.9737	High Similarity	NPC45131
0.9682	High Similarity	NPC247973
0.9679	High Similarity	NPC39306
0.9679	High Similarity	NPC45449
0.9679	High Similarity	NPC36320
0.9677	High Similarity	NPC238995
0.9551	High Similarity	NPC272722
0.9539	High Similarity	NPC125300
0.95	High Similarity	NPC230619
0.95	High Similarity	NPC54098
0.95	High Similarity	NPC174700
0.9494	High Similarity	NPC277480
0.9481	High Similarity	NPC472461
0.9441	High Similarity	NPC473834
0.9441	High Similarity	NPC216842
0.9441	High Similarity	NPC82217
0.9441	High Similarity	NPC476640
0.9441	High Similarity	NPC310794
0.9434	High Similarity	NPC50394
0.9434	High Similarity	NPC470704
0.943	High Similarity	NPC291110
0.943	High Similarity	NPC37183
0.9383	High Similarity	NPC287243
0.9375	High Similarity	NPC247136
0.9359	High Similarity	NPC195832
0.9351	High Similarity	NPC88645
0.9351	High Similarity	NPC206238
0.9351	High Similarity	NPC292214
0.9351	High Similarity	NPC167091
0.9351	High Similarity	NPC271779
0.9325	High Similarity	NPC8127
0.9325	High Similarity	NPC49667
0.9317	High Similarity	NPC476641
0.9317	High Similarity	NPC131866
0.9313	High Similarity	NPC86477
0.9308	High Similarity	NPC29411
0.9295	High Similarity	NPC99597
0.9295	High Similarity	NPC210084
0.929	High Similarity	NPC20830
0.929	High Similarity	NPC256612
0.929	High Similarity	NPC2928
0.9286	High Similarity	NPC293183
0.9286	High Similarity	NPC57030
0.9286	High Similarity	NPC187498
0.9286	High Similarity	NPC241498
0.9286	High Similarity	NPC131624
0.9286	High Similarity	NPC198826
0.9286	High Similarity	NPC161277
0.9286	High Similarity	NPC275722
0.9286	High Similarity	NPC39007
0.9286	High Similarity	NPC212678
0.9286	High Similarity	NPC83508
0.9286	High Similarity	NPC301323
0.9286	High Similarity	NPC25270
0.9286	High Similarity	NPC120163
0.9286	High Similarity	NPC199100
0.9286	High Similarity	NPC275836
0.9286	High Similarity	NPC100887
0.9286	High Similarity	NPC120537
0.9286	High Similarity	NPC256283
0.9286	High Similarity	NPC71334
0.9286	High Similarity	NPC156222
0.9286	High Similarity	NPC180234
0.9286	High Similarity	NPC239128
0.9286	High Similarity	NPC222830
0.9286	High Similarity	NPC188203
0.9286	High Similarity	NPC101996
0.9286	High Similarity	NPC162313
0.9276	High Similarity	NPC287395
0.9276	High Similarity	NPC183655
0.9245	High Similarity	NPC110257
0.9231	High Similarity	NPC472916
0.9231	High Similarity	NPC235165
0.9231	High Similarity	NPC255106
0.9226	High Similarity	NPC183878
0.9226	High Similarity	NPC160951
0.9226	High Similarity	NPC255350
0.9226	High Similarity	NPC69394
0.9226	High Similarity	NPC176775
0.9226	High Similarity	NPC47781
0.9226	High Similarity	NPC145379
0.9226	High Similarity	NPC22519
0.9226	High Similarity	NPC274327
0.9226	High Similarity	NPC231018
0.9221	High Similarity	NPC171010
0.9221	High Similarity	NPC251110
0.9221	High Similarity	NPC115324
0.9221	High Similarity	NPC117579
0.9221	High Similarity	NPC149614
0.9216	High Similarity	NPC102003
0.9216	High Similarity	NPC92722
0.9211	High Similarity	NPC17816
0.9202	High Similarity	NPC65885
0.9202	High Similarity	NPC261471
0.9182	High Similarity	NPC81679
0.9177	High Similarity	NPC476980
0.9172	High Similarity	NPC241904
0.9172	High Similarity	NPC472914
0.9172	High Similarity	NPC129684
0.9172	High Similarity	NPC472911
0.9172	High Similarity	NPC48208
0.9172	High Similarity	NPC222814
0.9172	High Similarity	NPC162869
0.9172	High Similarity	NPC245758
0.9172	High Similarity	NPC475267
0.9172	High Similarity	NPC262286
0.9172	High Similarity	NPC36852
0.9172	High Similarity	NPC472910
0.9172	High Similarity	NPC78225
0.9172	High Similarity	NPC474208
0.9172	High Similarity	NPC156057
0.9172	High Similarity	NPC469584
0.9172	High Similarity	NPC299520
0.9172	High Similarity	NPC181960
0.9172	High Similarity	NPC472913
0.9172	High Similarity	NPC96167
0.9172	High Similarity	NPC300727
0.9172	High Similarity	NPC474836
0.9167	High Similarity	NPC208197
0.9167	High Similarity	NPC163780
0.9167	High Similarity	NPC183597
0.9167	High Similarity	NPC44079
0.9167	High Similarity	NPC50715
0.9167	High Similarity	NPC227325
0.9167	High Similarity	NPC92659
0.9167	High Similarity	NPC128863
0.9167	High Similarity	NPC201136
0.9167	High Similarity	NPC146165
0.9167	High Similarity	NPC4455
0.9167	High Similarity	NPC2476
0.9167	High Similarity	NPC167815
0.9167	High Similarity	NPC201451
0.9167	High Similarity	NPC196439
0.9167	High Similarity	NPC26227
0.9167	High Similarity	NPC138360
0.9167	High Similarity	NPC213622
0.9167	High Similarity	NPC280339
0.9161	High Similarity	NPC35763
0.9161	High Similarity	NPC269451
0.9161	High Similarity	NPC181209
0.9161	High Similarity	NPC39732
0.9161	High Similarity	NPC207624
0.9161	High Similarity	NPC209487
0.9161	High Similarity	NPC216769
0.9161	High Similarity	NPC142540
0.9161	High Similarity	NPC60972
0.9161	High Similarity	NPC131266
0.9161	High Similarity	NPC245382
0.9161	High Similarity	NPC291802
0.9161	High Similarity	NPC121522
0.9161	High Similarity	NPC100263
0.9161	High Similarity	NPC304954
0.9161	High Similarity	NPC100971
0.9156	High Similarity	NPC62042
0.9156	High Similarity	NPC61620
0.9156	High Similarity	NPC29231
0.9156	High Similarity	NPC45873
0.9156	High Similarity	NPC184136
0.9156	High Similarity	NPC306821
0.9156	High Similarity	NPC248102
0.9156	High Similarity	NPC179183
0.9152	High Similarity	NPC297807
0.9152	High Similarity	NPC98546
0.915	High Similarity	NPC131451
0.915	High Similarity	NPC15329
0.9146	High Similarity	NPC290304
0.9146	High Similarity	NPC236327
0.9146	High Similarity	NPC227906
0.9141	High Similarity	NPC28589
0.9141	High Similarity	NPC248593
0.9136	High Similarity	NPC211309
0.9136	High Similarity	NPC202470
0.9125	High Similarity	NPC475985
0.9119	High Similarity	NPC162668
0.9119	High Similarity	NPC308992
0.9119	High Similarity	NPC258331
0.9114	High Similarity	NPC476242
0.9114	High Similarity	NPC55738
0.9108	High Similarity	NPC274730
0.9108	High Similarity	NPC247017
0.9108	High Similarity	NPC68093
0.9108	High Similarity	NPC43243
0.9108	High Similarity	NPC245546
0.9108	High Similarity	NPC49824
0.9108	High Similarity	NPC191146
0.9108	High Similarity	NPC98661
0.9108	High Similarity	NPC266960
0.9108	High Similarity	NPC138243
0.9103	High Similarity	NPC124714
0.9103	High Similarity	NPC250822

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 NPC188486 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	431
0.1-0.2	996
0.2-0.3	1771
0.3-0.4	2741
0.4-0.5	1701
0.5-0.6	982
0.6-0.7	364
0.7-0.8	120
0.8-0.85	27
0.85-0.9	11
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9226	High Similarity	NPD2801	Approved
0.9108	High Similarity	NPD3882	Suspended
0.9038	High Similarity	NPD1934	Approved
0.8766	High Similarity	NPD1511	Approved
0.8742	High Similarity	NPD2393	Clinical (unspecified phase)
0.8727	High Similarity	NPD3818	Discontinued
0.8704	High Similarity	NPD5494	Approved
0.8659	High Similarity	NPD3926	Phase 2
0.8654	High Similarity	NPD1512	Approved
0.865	High Similarity	NPD1247	Approved
0.8606	High Similarity	NPD6168	Clinical (unspecified phase)
0.8606	High Similarity	NPD6167	Clinical (unspecified phase)
0.8606	High Similarity	NPD6166	Phase 2
0.8405	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD2344	Approved
0.8373	Intermediate Similarity	NPD6232	Discontinued
0.8354	Intermediate Similarity	NPD3749	Approved
0.8344	Intermediate Similarity	NPD3817	Phase 2
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.8303	Intermediate Similarity	NPD919	Approved
0.8294	Intermediate Similarity	NPD7074	Phase 3
0.8282	Intermediate Similarity	NPD1465	Phase 2
0.8256	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD5844	Phase 1
0.8235	Intermediate Similarity	NPD7054	Approved
0.8224	Intermediate Similarity	NPD1240	Approved
0.8224	Intermediate Similarity	NPD943	Approved
0.8205	Intermediate Similarity	NPD1549	Phase 2
0.8198	Intermediate Similarity	NPD6559	Discontinued
0.8187	Intermediate Similarity	NPD7472	Approved
0.8165	Intermediate Similarity	NPD2309	Approved
0.8141	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1510	Phase 2
0.8117	Intermediate Similarity	NPD1607	Approved
0.8098	Intermediate Similarity	NPD4380	Phase 2
0.8063	Intermediate Similarity	NPD6799	Approved
0.8038	Intermediate Similarity	NPD2800	Approved
0.8035	Intermediate Similarity	NPD6797	Phase 2
0.8025	Intermediate Similarity	NPD920	Approved
0.8024	Intermediate Similarity	NPD7075	Discontinued
0.8024	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7251	Discontinued
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7962	Intermediate Similarity	NPD2796	Approved
0.7952	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7819	Suspended
0.7943	Intermediate Similarity	NPD7808	Phase 3
0.7931	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1243	Approved
0.7914	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD5402	Approved
0.7901	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6959	Discontinued
0.7862	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD2935	Discontinued
0.7831	Intermediate Similarity	NPD7411	Suspended
0.7821	Intermediate Similarity	NPD230	Phase 1
0.7821	Intermediate Similarity	NPD447	Suspended
0.7791	Intermediate Similarity	NPD2533	Approved
0.7791	Intermediate Similarity	NPD2534	Approved
0.7791	Intermediate Similarity	NPD2532	Approved
0.7785	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6801	Discontinued
0.7778	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3750	Approved
0.7751	Intermediate Similarity	NPD7768	Phase 2
0.7746	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7199	Phase 2
0.7662	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD1613	Approved
0.7643	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1551	Phase 2
0.7622	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD2296	Approved
0.7586	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD3027	Phase 3
0.7558	Intermediate Similarity	NPD6234	Discontinued
0.7557	Intermediate Similarity	NPD3751	Discontinued
0.7548	Intermediate Similarity	NPD9494	Approved
0.7546	Intermediate Similarity	NPD4628	Phase 3
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.7485	Intermediate Similarity	NPD5403	Approved
0.7485	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD8434	Phase 2
0.747	Intermediate Similarity	NPD5401	Approved
0.7469	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2799	Discontinued
0.7453	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3748	Approved
0.7439	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4287	Approved
0.7375	Intermediate Similarity	NPD1933	Approved
0.7368	Intermediate Similarity	NPD37	Approved
0.7362	Intermediate Similarity	NPD2346	Discontinued
0.7362	Intermediate Similarity	NPD1471	Phase 3
0.7348	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD4965	Approved
0.7341	Intermediate Similarity	NPD4967	Phase 2
0.7341	Intermediate Similarity	NPD4966	Approved
0.7337	Intermediate Similarity	NPD1653	Approved
0.7333	Intermediate Similarity	NPD5953	Discontinued
0.733	Intermediate Similarity	NPD3787	Discontinued
0.7318	Intermediate Similarity	NPD7286	Phase 2
0.7312	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1203	Approved
0.7305	Intermediate Similarity	NPD7390	Discontinued
0.7301	Intermediate Similarity	NPD6100	Approved
0.7301	Intermediate Similarity	NPD6099	Approved
0.7296	Intermediate Similarity	NPD2313	Discontinued
0.7289	Intermediate Similarity	NPD6190	Approved
0.7288	Intermediate Similarity	NPD5242	Approved
0.7267	Intermediate Similarity	NPD6280	Approved
0.7267	Intermediate Similarity	NPD6279	Approved
0.7263	Intermediate Similarity	NPD7228	Approved
0.7247	Intermediate Similarity	NPD2403	Approved
0.7232	Intermediate Similarity	NPD5710	Approved
0.7232	Intermediate Similarity	NPD7229	Phase 3
0.7232	Intermediate Similarity	NPD5711	Approved
0.7226	Intermediate Similarity	NPD9269	Phase 2
0.7222	Intermediate Similarity	NPD6651	Approved
0.7198	Intermediate Similarity	NPD7685	Pre-registration
0.7188	Intermediate Similarity	NPD3764	Approved
0.717	Intermediate Similarity	NPD4908	Phase 1
0.7167	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD2163	Approved
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6808	Phase 2
0.7126	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8313	Approved
0.712	Intermediate Similarity	NPD8312	Approved
0.7115	Intermediate Similarity	NPD1608	Approved
0.7115	Intermediate Similarity	NPD9717	Approved
0.7101	Intermediate Similarity	NPD4357	Discontinued
0.7081	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2654	Approved
0.7063	Intermediate Similarity	NPD6832	Phase 2
0.7051	Intermediate Similarity	NPD1610	Phase 2
0.7051	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6777	Approved
0.7047	Intermediate Similarity	NPD6779	Approved
0.7047	Intermediate Similarity	NPD6780	Approved
0.7047	Intermediate Similarity	NPD6778	Approved
0.7047	Intermediate Similarity	NPD6776	Approved
0.7047	Intermediate Similarity	NPD6781	Approved
0.7047	Intermediate Similarity	NPD6782	Approved
0.7044	Intermediate Similarity	NPD2798	Approved
0.7029	Intermediate Similarity	NPD5760	Phase 2
0.7029	Intermediate Similarity	NPD5761	Phase 2
0.702	Intermediate Similarity	NPD8151	Discontinued
0.7018	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6385	Approved
0.7011	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6386	Approved
0.7	Intermediate Similarity	NPD2861	Phase 2
0.6995	Remote Similarity	NPD1729	Discontinued
0.6989	Remote Similarity	NPD5353	Approved
0.6981	Remote Similarity	NPD1470	Approved
0.6979	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD7907	Approved
0.6975	Remote Similarity	NPD411	Approved
0.6975	Remote Similarity	NPD3268	Approved
0.6973	Remote Similarity	NPD7549	Discontinued
0.6971	Remote Similarity	NPD6844	Discontinued
0.6968	Remote Similarity	NPD9268	Approved
0.6961	Remote Similarity	NPD4111	Phase 1
0.6961	Remote Similarity	NPD4665	Approved
0.6957	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6355	Discontinued
0.695	Remote Similarity	NPD7783	Phase 2
0.695	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5536	Phase 2
0.6943	Remote Similarity	NPD422	Phase 1
0.6939	Remote Similarity	NPD7435	Discontinued
0.6933	Remote Similarity	NPD6233	Phase 2
0.6928	Remote Similarity	NPD4308	Phase 3
0.6928	Remote Similarity	NPD7033	Discontinued
0.6927	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4361	Phase 2
0.6923	Remote Similarity	NPD17	Approved
0.6915	Remote Similarity	NPD8150	Discontinued
0.6914	Remote Similarity	NPD4625	Phase 3
0.6904	Remote Similarity	NPD7870	Phase 2
0.6904	Remote Similarity	NPD7871	Phase 2
0.6903	Remote Similarity	NPD1548	Phase 1
0.6899	Remote Similarity	NPD3972	Approved
0.6897	Remote Similarity	NPD5808	Clinical (unspecified phase)

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