NPASS Compound

Structure

CID233776 OpenBabel06191716032D 24 27 0 0 0 0 0 0 0 0999 V2000 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9400 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 6 2 0 0 0 0 4 12 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 23 1 0 0 0 0 9 11 2 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 18 2 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 19 2 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 20 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.08
Volume:	323.177
LogP:	4.159
LogD:	3.03
LogS:	-6.503
# Rotatable Bonds:	3
TPSA:	61.81
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.565
Synthetic Accessibility Score:	2.359
Fsp3:	0.105
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.674
MDCK Permeability:	4.466689642868005e-05
Pgp-inhibitor:	0.985
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	84.93695068359375%
Volume Distribution (VD):	0.555
Pgp-substrate:	11.480426788330078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.969
CYP1A2-substrate:	0.953
CYP2C19-inhibitor:	0.855
CYP2C19-substrate:	0.129
CYP2C9-inhibitor:	0.749
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.667
CYP2D6-substrate:	0.947
CYP3A4-inhibitor:	0.847
CYP3A4-substrate:	0.289

ADMET: Excretion

Clearance (CL):	6.464
Half-life (T1/2):	0.149

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.361
Drug-inuced Liver Injury (DILI):	0.959
AMES Toxicity:	0.504
Rat Oral Acute Toxicity:	0.489
Maximum Recommended Daily Dose:	0.608
Skin Sensitization:	0.062
Carcinogencity:	0.749
Eye Corrosion:	0.003
Eye Irritation:	0.467
Respiratory Toxicity:	0.783

Download Data

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

Natural Product: NPC233776

Natural Product ID:	NPC233776
*Common Name:**	2-(2,5-Dimethoxyphenyl)Furo[2,3-H]Chromen-4-One
IUPAC Name:	2-(2,5-dimethoxyphenyl)furo[2,3-h]chromen-4-one
Synonyms:
Standard InCHIKey:	DLYWGMBSOSDGOR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H14O5/c1-21-11-3-5-16(22-2)14(9-11)18-10-15(20)12-4-6-17-13(7-8-23-17)19(12)24-18/h3-10H,1-2H3
SMILES:	COc1ccc(c(c1)c1cc(=O)c2ccc3c(cco3)c2o1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581064
PubChem CID:	11045499
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001759] Furanoflavones

*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
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	stem bark	Indonesia	1999-SEP	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	dry stem	n.a.	n.a.	PMID[25466192]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2398	Millettia erythrocalyx	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2398	Millettia erythrocalyx	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	87670.0	nM	PMID[449666]

☑ 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 NPC233776 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	559
0.1-0.2	2152
0.2-0.3	5142
0.3-0.4	12304
0.4-0.5	5487
0.5-0.6	4827
0.6-0.7	5779
0.7-0.8	4385
0.8-0.85	1702
0.85-0.9	335
0.9-0.95	18
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9864	High Similarity	NPC130015
0.9864	High Similarity	NPC38361
0.9728	High Similarity	NPC135303
0.9728	High Similarity	NPC148423
0.9592	High Similarity	NPC306788
0.9545	High Similarity	NPC65846
0.9533	High Similarity	NPC41719
0.953	High Similarity	NPC472407
0.9524	High Similarity	NPC198427
0.9456	High Similarity	NPC190572
0.9355	High Similarity	NPC193998
0.9338	High Similarity	NPC263676
0.9333	High Similarity	NPC472406
0.9211	High Similarity	NPC253872
0.9167	High Similarity	NPC264293
0.9145	High Similarity	NPC116604
0.9139	High Similarity	NPC88445
0.9125	High Similarity	NPC190351
0.9114	High Similarity	NPC38914
0.9079	High Similarity	NPC191104
0.9062	High Similarity	NPC41853
0.906	High Similarity	NPC17262
0.9045	High Similarity	NPC304387
0.9026	High Similarity	NPC472462
0.902	High Similarity	NPC170169
0.9007	High Similarity	NPC304443
0.9007	High Similarity	NPC74539
0.9	High Similarity	NPC241820
0.9	High Similarity	NPC167479
0.8968	High Similarity	NPC198490
0.8957	High Similarity	NPC66804
0.8954	High Similarity	NPC230713
0.8954	High Similarity	NPC78335
0.891	High Similarity	NPC247677
0.891	High Similarity	NPC160015
0.8903	High Similarity	NPC1477
0.8903	High Similarity	NPC213608
0.8903	High Similarity	NPC122365
0.8903	High Similarity	NPC183874
0.8896	High Similarity	NPC72455
0.8896	High Similarity	NPC62640
0.8889	High Similarity	NPC226644
0.8889	High Similarity	NPC37226
0.8889	High Similarity	NPC178202
0.8882	High Similarity	NPC17816
0.8874	High Similarity	NPC246903
0.8868	High Similarity	NPC219861
0.8854	High Similarity	NPC268360
0.8854	High Similarity	NPC296957
0.8854	High Similarity	NPC65504
0.8854	High Similarity	NPC260902
0.8854	High Similarity	NPC19097
0.8846	High Similarity	NPC148938
0.8844	High Similarity	NPC29638
0.8839	High Similarity	NPC5871
0.8839	High Similarity	NPC67654
0.8824	High Similarity	NPC266743
0.882	High Similarity	NPC193881
0.882	High Similarity	NPC67450
0.882	High Similarity	NPC277480
0.882	High Similarity	NPC155264
0.882	High Similarity	NPC210460
0.8812	High Similarity	NPC179464
0.88	High Similarity	NPC22467
0.8797	High Similarity	NPC472877
0.8797	High Similarity	NPC476349
0.8797	High Similarity	NPC476350
0.8797	High Similarity	NPC250076
0.8782	High Similarity	NPC235333
0.8782	High Similarity	NPC72370
0.8774	High Similarity	NPC115324
0.8774	High Similarity	NPC156244
0.8766	High Similarity	NPC37208
0.8766	High Similarity	NPC317492
0.8766	High Similarity	NPC221868
0.8766	High Similarity	NPC266499
0.8766	High Similarity	NPC296030
0.8766	High Similarity	NPC39929
0.8758	High Similarity	NPC130581
0.8758	High Similarity	NPC12148
0.8758	High Similarity	NPC37183
0.875	High Similarity	NPC155144
0.875	High Similarity	NPC98926
0.875	High Similarity	NPC208584
0.875	High Similarity	NPC234536
0.875	High Similarity	NPC78612
0.8742	High Similarity	NPC51146
0.8742	High Similarity	NPC166858
0.8742	High Similarity	NPC313036
0.8734	High Similarity	NPC96342
0.8734	High Similarity	NPC212967
0.8734	High Similarity	NPC246647
0.8734	High Similarity	NPC164110
0.8734	High Similarity	NPC269495
0.8726	High Similarity	NPC213936
0.8726	High Similarity	NPC278010
0.8726	High Similarity	NPC250769
0.8726	High Similarity	NPC297531
0.8726	High Similarity	NPC295608
0.8726	High Similarity	NPC99199
0.872	High Similarity	NPC248593
0.872	High Similarity	NPC157522
0.872	High Similarity	NPC28589
0.8718	High Similarity	NPC207624
0.8716	High Similarity	NPC254741
0.871	High Similarity	NPC167576
0.871	High Similarity	NPC37348
0.871	High Similarity	NPC101957
0.871	High Similarity	NPC120105
0.8701	High Similarity	NPC135325
0.8701	High Similarity	NPC37135
0.8701	High Similarity	NPC168085
0.8701	High Similarity	NPC186397
0.8701	High Similarity	NPC272194
0.8696	High Similarity	NPC109180
0.8696	High Similarity	NPC472581
0.8693	High Similarity	NPC300267
0.8693	High Similarity	NPC210826
0.8693	High Similarity	NPC51641
0.8688	High Similarity	NPC30655
0.8688	High Similarity	NPC45124
0.8688	High Similarity	NPC74854
0.8684	High Similarity	NPC225884
0.8684	High Similarity	NPC302181
0.8679	High Similarity	NPC40583
0.8671	High Similarity	NPC45131
0.8671	High Similarity	NPC180924
0.8667	High Similarity	NPC310794
0.8662	High Similarity	NPC131725
0.8662	High Similarity	NPC472408
0.8662	High Similarity	NPC128961
0.8659	High Similarity	NPC131866
0.8654	High Similarity	NPC58668
0.8654	High Similarity	NPC193976
0.8654	High Similarity	NPC23668
0.8654	High Similarity	NPC106372
0.865	High Similarity	NPC50394
0.865	High Similarity	NPC247973
0.8645	High Similarity	NPC223988
0.8642	High Similarity	NPC291110
0.8642	High Similarity	NPC136641
0.8639	High Similarity	NPC292998
0.8636	High Similarity	NPC205522
0.8627	High Similarity	NPC230943
0.8627	High Similarity	NPC179970
0.8625	High Similarity	NPC169
0.8625	High Similarity	NPC304839
0.8625	High Similarity	NPC220582
0.8625	High Similarity	NPC49009
0.8625	High Similarity	NPC243509
0.8625	High Similarity	NPC298093
0.8623	High Similarity	NPC472606
0.8618	High Similarity	NPC53192
0.8616	High Similarity	NPC270044
0.8616	High Similarity	NPC196448
0.8599	High Similarity	NPC142308
0.8599	High Similarity	NPC166201
0.8591	High Similarity	NPC161196
0.859	High Similarity	NPC155882
0.8581	High Similarity	NPC10304
0.8581	High Similarity	NPC63256
0.8571	High Similarity	NPC188486
0.8571	High Similarity	NPC14822
0.8571	High Similarity	NPC195919
0.8571	High Similarity	NPC215932
0.8571	High Similarity	NPC231013
0.8571	High Similarity	NPC216314
0.8571	High Similarity	NPC110639
0.8571	High Similarity	NPC182428
0.8571	High Similarity	NPC40818
0.8571	High Similarity	NPC24761
0.8571	High Similarity	NPC258331
0.8571	High Similarity	NPC106461
0.8571	High Similarity	NPC120924
0.8571	High Similarity	NPC216092
0.8571	High Similarity	NPC14958
0.8562	High Similarity	NPC189650
0.8562	High Similarity	NPC196879
0.8562	High Similarity	NPC16935
0.8562	High Similarity	NPC33320
0.8554	High Similarity	NPC233956
0.8553	High Similarity	NPC180340
0.8553	High Similarity	NPC254010
0.8545	High Similarity	NPC144288
0.8544	High Similarity	NPC186507
0.8543	High Similarity	NPC136095
0.8543	High Similarity	NPC262635
0.8543	High Similarity	NPC11566
0.8533	High Similarity	NPC259685
0.8526	High Similarity	NPC238366
0.8519	High Similarity	NPC84515
0.8519	High Similarity	NPC312056
0.8519	High Similarity	NPC273021
0.8519	High Similarity	NPC81679
0.8519	High Similarity	NPC18284
0.8516	High Similarity	NPC471285
0.8516	High Similarity	NPC85233
0.8514	High Similarity	NPC223354
0.8509	High Similarity	NPC239270
0.8509	High Similarity	NPC260296

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 NPC233776 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	469
0.1-0.2	1046
0.2-0.3	1753
0.3-0.4	2818
0.4-0.5	1800
0.5-0.6	876
0.6-0.7	263
0.7-0.8	101
0.8-0.85	17
0.85-0.9	4
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9167	High Similarity	NPD1247	Approved
0.9007	High Similarity	NPD920	Approved
0.8874	High Similarity	NPD642	Clinical (unspecified phase)
0.8742	High Similarity	NPD643	Clinical (unspecified phase)
0.8625	High Similarity	NPD5494	Approved
0.8591	High Similarity	NPD2796	Approved
0.8562	High Similarity	NPD919	Approved
0.8543	High Similarity	NPD1243	Approved
0.8387	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD7411	Suspended
0.8225	Intermediate Similarity	NPD6559	Discontinued
0.8199	Intermediate Similarity	NPD2801	Approved
0.8199	Intermediate Similarity	NPD7819	Suspended
0.8199	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD1510	Phase 2
0.8153	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD3926	Phase 2
0.8117	Intermediate Similarity	NPD1549	Phase 2
0.8052	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3749	Approved
0.8025	Intermediate Similarity	NPD1934	Approved
0.8012	Intermediate Similarity	NPD4380	Phase 2
0.7988	Intermediate Similarity	NPD3882	Suspended
0.7976	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1511	Approved
0.7975	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD2344	Approved
0.7927	Intermediate Similarity	NPD3817	Phase 2
0.7914	Intermediate Similarity	NPD6801	Discontinued
0.7904	Intermediate Similarity	NPD6959	Discontinued
0.7895	Intermediate Similarity	NPD1240	Approved
0.7882	Intermediate Similarity	NPD3818	Discontinued
0.7875	Intermediate Similarity	NPD1512	Approved
0.7862	Intermediate Similarity	NPD6799	Approved
0.7834	Intermediate Similarity	NPD2800	Approved
0.7831	Intermediate Similarity	NPD7075	Discontinued
0.7821	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1471	Phase 3
0.7818	Intermediate Similarity	NPD5402	Approved
0.7806	Intermediate Similarity	NPD3748	Approved
0.7792	Intermediate Similarity	NPD1607	Approved
0.7778	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7768	Phase 2
0.7756	Intermediate Similarity	NPD2935	Discontinued
0.7736	Intermediate Similarity	NPD2309	Approved
0.7733	Intermediate Similarity	NPD5844	Phase 1
0.773	Intermediate Similarity	NPD3226	Approved
0.7725	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2533	Approved
0.7702	Intermediate Similarity	NPD2534	Approved
0.7702	Intermediate Similarity	NPD2532	Approved
0.7683	Intermediate Similarity	NPD6599	Discontinued
0.7661	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6166	Phase 2
0.7661	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2313	Discontinued
0.7647	Intermediate Similarity	NPD6232	Discontinued
0.7643	Intermediate Similarity	NPD1551	Phase 2
0.7616	Intermediate Similarity	NPD7473	Discontinued
0.7607	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD3750	Approved
0.756	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6808	Phase 2
0.7529	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6280	Approved
0.7485	Intermediate Similarity	NPD5401	Approved
0.7485	Intermediate Similarity	NPD6279	Approved
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7468	Intermediate Similarity	NPD2799	Discontinued
0.7458	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7229	Phase 3
0.7429	Intermediate Similarity	NPD7054	Approved
0.7419	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6832	Phase 2
0.7394	Intermediate Similarity	NPD5403	Approved
0.7389	Intermediate Similarity	NPD8434	Phase 2
0.7386	Intermediate Similarity	NPD7472	Approved
0.7386	Intermediate Similarity	NPD7074	Phase 3
0.7358	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5953	Discontinued
0.7345	Intermediate Similarity	NPD6797	Phase 2
0.733	Intermediate Similarity	NPD7286	Phase 2
0.732	Intermediate Similarity	NPD3267	Approved
0.732	Intermediate Similarity	NPD3266	Approved
0.7303	Intermediate Similarity	NPD7251	Discontinued
0.7284	Intermediate Similarity	NPD2654	Approved
0.7267	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7808	Phase 3
0.7257	Intermediate Similarity	NPD2403	Approved
0.7235	Intermediate Similarity	NPD5761	Phase 2
0.7235	Intermediate Similarity	NPD5760	Phase 2
0.7219	Intermediate Similarity	NPD5889	Approved
0.7219	Intermediate Similarity	NPD5890	Approved
0.7215	Intermediate Similarity	NPD943	Approved
0.7212	Intermediate Similarity	NPD7390	Discontinued
0.7193	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD2296	Approved
0.7176	Intermediate Similarity	NPD6844	Discontinued
0.7161	Intermediate Similarity	NPD2798	Approved
0.7151	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD5710	Approved
0.7135	Intermediate Similarity	NPD1465	Phase 2
0.7125	Intermediate Similarity	NPD6651	Approved
0.712	Intermediate Similarity	NPD4287	Approved
0.7107	Intermediate Similarity	NPD4307	Phase 2
0.7089	Intermediate Similarity	NPD3268	Approved
0.7089	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3751	Discontinued
0.7066	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1933	Approved
0.7059	Intermediate Similarity	NPD6585	Discontinued
0.7053	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1019	Discontinued
0.7043	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD17	Approved
0.7037	Intermediate Similarity	NPD7033	Discontinued
0.703	Intermediate Similarity	NPD4628	Phase 3
0.7027	Intermediate Similarity	NPD1241	Discontinued
0.7027	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4361	Phase 2
0.7021	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD3972	Approved
0.7	Intermediate Similarity	NPD1729	Discontinued
0.7	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6100	Approved
0.6994	Remote Similarity	NPD6099	Approved
0.6989	Remote Similarity	NPD7199	Phase 2
0.6987	Remote Similarity	NPD1203	Approved
0.6981	Remote Similarity	NPD1296	Phase 2
0.6968	Remote Similarity	NPD4360	Phase 2
0.6968	Remote Similarity	NPD4363	Phase 3
0.6962	Remote Similarity	NPD4908	Phase 1
0.6957	Remote Similarity	NPD447	Suspended
0.6957	Remote Similarity	NPD230	Phase 1
0.6949	Remote Similarity	NPD3787	Discontinued
0.6933	Remote Similarity	NPD4308	Phase 3
0.6928	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1876	Approved
0.6919	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5242	Approved
0.6908	Remote Similarity	NPD1548	Phase 1
0.6905	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD9717	Approved
0.6903	Remote Similarity	NPD1608	Approved
0.6897	Remote Similarity	NPD4288	Approved
0.6895	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3764	Approved
0.6872	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1651	Approved
0.6848	Remote Similarity	NPD8313	Approved
0.6848	Remote Similarity	NPD8312	Approved
0.6839	Remote Similarity	NPD1610	Phase 2
0.6823	Remote Similarity	NPD8285	Discontinued
0.6818	Remote Similarity	NPD6971	Discontinued
0.6815	Remote Similarity	NPD3225	Approved
0.6813	Remote Similarity	NPD4625	Phase 3
0.6796	Remote Similarity	NPD7177	Discontinued
0.6796	Remote Similarity	NPD2163	Approved
0.6792	Remote Similarity	NPD2861	Phase 2
0.679	Remote Similarity	NPD2979	Phase 3
0.679	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1613	Approved
0.6788	Remote Similarity	NPD5406	Approved
0.6788	Remote Similarity	NPD5408	Approved
0.6788	Remote Similarity	NPD6780	Approved
0.6788	Remote Similarity	NPD6777	Approved
0.6788	Remote Similarity	NPD5404	Approved
0.6788	Remote Similarity	NPD6781	Approved
0.6788	Remote Similarity	NPD6782	Approved
0.6788	Remote Similarity	NPD5405	Approved
0.6788	Remote Similarity	NPD6776	Approved
0.6788	Remote Similarity	NPD6779	Approved
0.6788	Remote Similarity	NPD6778	Approved
0.6786	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD37	Approved
0.6776	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1470	Approved
0.6772	Remote Similarity	NPD2797	Approved
0.677	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.677	Remote Similarity	NPD411	Approved
0.6765	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4965	Approved
0.6761	Remote Similarity	NPD4966	Approved
0.6761	Remote Similarity	NPD4967	Phase 2
0.675	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5124	Phase 1
0.6739	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD7871	Phase 2
0.6735	Remote Similarity	NPD7870	Phase 2

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