NPASS Compound

Structure

NPC38914 OpenBabel07101718292D 22 25 0 0 0 0 0 0 0 0999 V2000 -2.5981 -0.5000 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 -3.4641 0.0000 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 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 -1.7321 1.0000 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 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 -3.4641 1.0000 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 -2.5981 1.5000 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 -4.3301 1.5000 0.0000 O 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 -2.5981 2.5000 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 3 2 0 0 0 0 1 9 1 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 12 1 0 0 0 0 4 15 1 0 0 0 0 5 6 2 0 0 0 0 5 11 1 0 0 0 0 6 21 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 19 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	294.05
Volume:	288.585
LogP:	3.668
LogD:	2.707
LogS:	-4.12
# Rotatable Bonds:	1
TPSA:	83.81
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.524
Synthetic Accessibility Score:	2.494
Fsp3:	0.0
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:	-4.842
MDCK Permeability:	1.4020602066011634e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.895
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.95
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	95.33732604980469%
Volume Distribution (VD):	0.537
Pgp-substrate:	7.275201320648193%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.16
CYP2C19-inhibitor:	0.502
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.489
CYP2C9-substrate:	0.842
CYP2D6-inhibitor:	0.759
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.632
CYP3A4-substrate:	0.143

ADMET: Excretion

Clearance (CL):	6.826
Half-life (T1/2):	0.707

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.968
AMES Toxicity:	0.26
Rat Oral Acute Toxicity:	0.509
Maximum Recommended Daily Dose:	0.558
Skin Sensitization:	0.882
Carcinogencity:	0.802
Eye Corrosion:	0.003
Eye Irritation:	0.914
Respiratory Toxicity:	0.443

Download Data

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

Natural Product: NPC38914

Natural Product ID:	NPC38914
*Common Name:**	3',4'-Dihydroxy-4H-Furo[2,3-H]Chromen-4-One
IUPAC Name:	2-(3,4-dihydroxyphenyl)furo[2,3-h]chromen-4-one
Synonyms:
Standard InCHIKey:	HQXNJTYEMIKUKO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H10O5/c18-12-3-1-9(7-14(12)20)16-8-13(19)10-2-4-15-11(5-6-21-15)17(10)22-16/h1-8,18,20H
SMILES:	Oc1cc(ccc1O)c1cc(=O)c2c(o1)c1ccoc1cc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL573853
PubChem CID:	44537938
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
NPO3037	Derris indica	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[19515570]

☑ 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
Others	3

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity	SC50	=	55.1	%	PMID[514834]
NPT2	Others	Unspecified	Activity	=	335.0	uM	PMID[514834]
NPT2	Others	Unspecified	IC50	=	25.6	%	PMID[514834]
NPT1	Others	Radical scavenging activity	Activity	=	84.6	uM	PMID[514834]

☑ 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 NPC38914 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	562
0.1-0.2	2230
0.2-0.3	5253
0.3-0.4	12024
0.4-0.5	5243
0.5-0.6	4329
0.6-0.7	5709
0.7-0.8	4504
0.8-0.85	1860
0.85-0.9	896
0.9-0.95	85
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC241820
0.9383	High Similarity	NPC131866
0.9371	High Similarity	NPC193998
0.9355	High Similarity	NPC253872
0.9325	High Similarity	NPC248593
0.9325	High Similarity	NPC28589
0.9317	High Similarity	NPC277480
0.929	High Similarity	NPC116604
0.9255	High Similarity	NPC37183
0.9231	High Similarity	NPC38361
0.9231	High Similarity	NPC263676
0.9231	High Similarity	NPC130015
0.9193	High Similarity	NPC65846
0.9187	High Similarity	NPC304387
0.9152	High Similarity	NPC310794
0.9152	High Similarity	NPC277510
0.9141	High Similarity	NPC247973
0.9141	High Similarity	NPC50394
0.9136	High Similarity	NPC291110
0.913	High Similarity	NPC219861
0.9125	High Similarity	NPC328102
0.9114	High Similarity	NPC233776
0.9108	High Similarity	NPC125300
0.9103	High Similarity	NPC148423
0.9103	High Similarity	NPC135303
0.9097	High Similarity	NPC306788
0.9091	High Similarity	NPC157522
0.9068	High Similarity	NPC258331
0.9068	High Similarity	NPC188486
0.9062	High Similarity	NPC196879
0.9062	High Similarity	NPC16935
0.9057	High Similarity	NPC472461
0.9051	High Similarity	NPC472462
0.9045	High Similarity	NPC472407
0.9045	High Similarity	NPC170169
0.9036	High Similarity	NPC233956
0.9024	High Similarity	NPC167479
0.9018	High Similarity	NPC29411
0.9012	High Similarity	NPC84515
0.9012	High Similarity	NPC81679
0.9012	High Similarity	NPC312056
0.9012	High Similarity	NPC272722
0.9006	High Similarity	NPC476283
0.8994	High Similarity	NPC198490
0.8981	High Similarity	NPC88804
0.8981	High Similarity	NPC230713
0.8981	High Similarity	NPC3825
0.8981	High Similarity	NPC78335
0.8974	High Similarity	NPC119059
0.897	High Similarity	NPC41853
0.897	High Similarity	NPC202470
0.896	High Similarity	NPC60848
0.8957	High Similarity	NPC124038
0.8957	High Similarity	NPC472581
0.8957	High Similarity	NPC15819
0.8951	High Similarity	NPC74854
0.8951	High Similarity	NPC30655
0.8951	High Similarity	NPC45124
0.8944	High Similarity	NPC472877
0.8938	High Similarity	NPC160015
0.8938	High Similarity	NPC282307
0.8938	High Similarity	NPC45131
0.8938	High Similarity	NPC170026
0.8938	High Similarity	NPC247677
0.8938	High Similarity	NPC472455
0.8935	High Similarity	NPC104682
0.8931	High Similarity	NPC41719
0.8931	High Similarity	NPC122365
0.8931	High Similarity	NPC213896
0.8931	High Similarity	NPC192083
0.8931	High Similarity	NPC213608
0.8931	High Similarity	NPC1477
0.8931	High Similarity	NPC183874
0.8924	High Similarity	NPC154345
0.8922	High Similarity	NPC261471
0.8917	High Similarity	NPC1612
0.8917	High Similarity	NPC226644
0.8917	High Similarity	NPC37226
0.8917	High Similarity	NPC183959
0.8917	High Similarity	NPC178202
0.8917	High Similarity	NPC38545
0.8917	High Similarity	NPC171916
0.8917	High Similarity	NPC105512
0.8916	High Similarity	NPC281835
0.891	High Similarity	NPC17816
0.891	High Similarity	NPC95864
0.891	High Similarity	NPC198427
0.891	High Similarity	NPC108406
0.8903	High Similarity	NPC155144
0.8903	High Similarity	NPC70136
0.8902	High Similarity	NPC300053
0.8902	High Similarity	NPC108433
0.8902	High Similarity	NPC36320
0.8902	High Similarity	NPC472277
0.8889	High Similarity	NPC476980
0.8889	High Similarity	NPC220582
0.8889	High Similarity	NPC472624
0.8889	High Similarity	NPC304839
0.8882	High Similarity	NPC65504
0.8882	High Similarity	NPC268360
0.8882	High Similarity	NPC291508
0.8882	High Similarity	NPC260902
0.8882	High Similarity	NPC296957
0.8875	High Similarity	NPC152951
0.8875	High Similarity	NPC321779
0.8875	High Similarity	NPC168247
0.8875	High Similarity	NPC230149
0.8875	High Similarity	NPC57674
0.8875	High Similarity	NPC117992
0.8875	High Similarity	NPC148938
0.8875	High Similarity	NPC113906
0.8875	High Similarity	NPC234255
0.8875	High Similarity	NPC39184
0.8875	High Similarity	NPC472280
0.8875	High Similarity	NPC133392
0.8868	High Similarity	NPC323626
0.8868	High Similarity	NPC63187
0.8868	High Similarity	NPC5871
0.8868	High Similarity	NPC67654
0.8868	High Similarity	NPC324233
0.8868	High Similarity	NPC157784
0.8868	High Similarity	NPC37684
0.8868	High Similarity	NPC106976
0.8868	High Similarity	NPC39732
0.8868	High Similarity	NPC60972
0.8868	High Similarity	NPC471982
0.8862	High Similarity	NPC307286
0.8862	High Similarity	NPC174700
0.8861	High Similarity	NPC184136
0.8861	High Similarity	NPC10467
0.8855	High Similarity	NPC288813
0.8854	High Similarity	NPC321011
0.8854	High Similarity	NPC12367
0.8854	High Similarity	NPC188679
0.8854	High Similarity	NPC3036
0.8854	High Similarity	NPC203077
0.8854	High Similarity	NPC166036
0.8854	High Similarity	NPC218490
0.8854	High Similarity	NPC118726
0.8854	High Similarity	NPC294852
0.8854	High Similarity	NPC238279
0.8848	High Similarity	NPC235610
0.8846	High Similarity	NPC190572
0.8841	High Similarity	NPC329669
0.8841	High Similarity	NPC472281
0.8841	High Similarity	NPC472278
0.8841	High Similarity	NPC205265
0.8841	High Similarity	NPC1755
0.8841	High Similarity	NPC1706
0.8841	High Similarity	NPC473313
0.8841	High Similarity	NPC18100
0.8841	High Similarity	NPC59295
0.8841	High Similarity	NPC133065
0.8841	High Similarity	NPC39305
0.8841	High Similarity	NPC263092
0.8839	High Similarity	NPC38065
0.8839	High Similarity	NPC242893
0.8839	High Similarity	NPC279121
0.8834	High Similarity	NPC187354
0.8834	High Similarity	NPC264293
0.8827	High Similarity	NPC476350
0.8827	High Similarity	NPC53545
0.8827	High Similarity	NPC74178
0.8827	High Similarity	NPC184755
0.8827	High Similarity	NPC476349
0.8827	High Similarity	NPC204879
0.8827	High Similarity	NPC117418
0.882	High Similarity	NPC6633
0.882	High Similarity	NPC291878
0.882	High Similarity	NPC133970
0.882	High Similarity	NPC195796
0.882	High Similarity	NPC474638
0.882	High Similarity	NPC35038
0.882	High Similarity	NPC5322
0.882	High Similarity	NPC278778
0.8817	High Similarity	NPC8127
0.8817	High Similarity	NPC164384
0.8817	High Similarity	NPC49667
0.8812	High Similarity	NPC189130
0.8812	High Similarity	NPC49402
0.8812	High Similarity	NPC235333
0.8812	High Similarity	NPC74924
0.8812	High Similarity	NPC72370
0.8812	High Similarity	NPC170492
0.8812	High Similarity	NPC70433
0.8812	High Similarity	NPC273462
0.8812	High Similarity	NPC298692
0.8812	High Similarity	NPC141212
0.8812	High Similarity	NPC33051
0.8812	High Similarity	NPC227337
0.881	High Similarity	NPC62640
0.8805	High Similarity	NPC260895
0.8805	High Similarity	NPC115324
0.8805	High Similarity	NPC31363
0.8805	High Similarity	NPC156244
0.8805	High Similarity	NPC59162
0.8805	High Similarity	NPC205046
0.8805	High Similarity	NPC304295
0.8805	High Similarity	NPC204515
0.8805	High Similarity	NPC256406

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 NPC38914 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	481
0.1-0.2	1052
0.2-0.3	1943
0.3-0.4	2766
0.4-0.5	1627
0.5-0.6	885
0.6-0.7	271
0.7-0.8	86
0.8-0.85	25
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8931	High Similarity	NPD2393	Clinical (unspecified phase)
0.8839	High Similarity	NPD1511	Approved
0.8834	High Similarity	NPD1247	Approved
0.875	High Similarity	NPD1934	Approved
0.8726	High Similarity	NPD1512	Approved
0.8704	High Similarity	NPD3882	Suspended
0.8696	High Similarity	NPD2801	Approved
0.8683	High Similarity	NPD3818	Discontinued
0.8485	Intermediate Similarity	NPD919	Approved
0.848	Intermediate Similarity	NPD6559	Discontinued
0.8438	Intermediate Similarity	NPD920	Approved
0.8428	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD4380	Phase 2
0.8364	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8343	Intermediate Similarity	NPD6166	Phase 2
0.8323	Intermediate Similarity	NPD5494	Approved
0.8323	Intermediate Similarity	NPD1510	Phase 2
0.8302	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD1549	Phase 2
0.8232	Intermediate Similarity	NPD7411	Suspended
0.8217	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD3749	Approved
0.8199	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD3817	Phase 2
0.8118	Intermediate Similarity	NPD6232	Discontinued
0.8095	Intermediate Similarity	NPD7075	Discontinued
0.8095	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7054	Approved
0.8081	Intermediate Similarity	NPD7473	Discontinued
0.807	Intermediate Similarity	NPD3926	Phase 2
0.8065	Intermediate Similarity	NPD943	Approved
0.8046	Intermediate Similarity	NPD7472	Approved
0.8046	Intermediate Similarity	NPD7074	Phase 3
0.8038	Intermediate Similarity	NPD2796	Approved
0.8024	Intermediate Similarity	NPD7819	Suspended
0.8024	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1243	Approved
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7987	Intermediate Similarity	NPD2344	Approved
0.7964	Intermediate Similarity	NPD6801	Discontinued
0.7955	Intermediate Similarity	NPD7251	Discontinued
0.7953	Intermediate Similarity	NPD6959	Discontinued
0.7949	Intermediate Similarity	NPD1240	Approved
0.7917	Intermediate Similarity	NPD1465	Phase 2
0.7898	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD2800	Approved
0.7886	Intermediate Similarity	NPD5844	Phase 1
0.7848	Intermediate Similarity	NPD1607	Approved
0.7824	Intermediate Similarity	NPD7768	Phase 2
0.7812	Intermediate Similarity	NPD1551	Phase 2
0.7809	Intermediate Similarity	NPD7808	Phase 3
0.7805	Intermediate Similarity	NPD6799	Approved
0.7791	Intermediate Similarity	NPD2309	Approved
0.7784	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5402	Approved
0.7758	Intermediate Similarity	NPD2532	Approved
0.7758	Intermediate Similarity	NPD2534	Approved
0.7758	Intermediate Similarity	NPD2533	Approved
0.773	Intermediate Similarity	NPD3750	Approved
0.7679	Intermediate Similarity	NPD3226	Approved
0.7673	Intermediate Similarity	NPD230	Phase 1
0.7654	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6599	Discontinued
0.761	Intermediate Similarity	NPD1613	Approved
0.761	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2313	Discontinued
0.7593	Intermediate Similarity	NPD2935	Discontinued
0.758	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD5403	Approved
0.7545	Intermediate Similarity	NPD5401	Approved
0.7541	Intermediate Similarity	NPD8434	Phase 2
0.7531	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3748	Approved
0.7423	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD9494	Approved
0.7403	Intermediate Similarity	NPD5953	Discontinued
0.7389	Intermediate Similarity	NPD7286	Phase 2
0.7346	Intermediate Similarity	NPD447	Suspended
0.7345	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD1471	Phase 3
0.7333	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3751	Discontinued
0.7333	Intermediate Similarity	NPD2346	Discontinued
0.733	Intermediate Similarity	NPD6234	Discontinued
0.7317	Intermediate Similarity	NPD2799	Discontinued
0.7303	Intermediate Similarity	NPD7229	Phase 3
0.7278	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7390	Discontinued
0.7273	Intermediate Similarity	NPD4287	Approved
0.7267	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD2296	Approved
0.7207	Intermediate Similarity	NPD5710	Approved
0.7207	Intermediate Similarity	NPD5711	Approved
0.7205	Intermediate Similarity	NPD3027	Phase 3
0.7204	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4628	Phase 3
0.72	Intermediate Similarity	NPD5760	Phase 2
0.72	Intermediate Similarity	NPD5761	Phase 2
0.7195	Intermediate Similarity	NPD6651	Approved
0.7189	Intermediate Similarity	NPD8313	Approved
0.7189	Intermediate Similarity	NPD8312	Approved
0.717	Intermediate Similarity	NPD1203	Approved
0.716	Intermediate Similarity	NPD6190	Approved
0.716	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD37	Approved
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4965	Approved
0.7119	Intermediate Similarity	NPD4966	Approved
0.7119	Intermediate Similarity	NPD4967	Phase 2
0.7111	Intermediate Similarity	NPD3787	Discontinued
0.7111	Intermediate Similarity	NPD6808	Phase 2
0.711	Intermediate Similarity	NPD1653	Approved
0.7105	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1548	Phase 1
0.7089	Intermediate Similarity	NPD9269	Phase 2
0.7083	Intermediate Similarity	NPD4361	Phase 2
0.7083	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6100	Approved
0.7066	Intermediate Similarity	NPD6099	Approved
0.7065	Intermediate Similarity	NPD1729	Discontinued
0.7055	Intermediate Similarity	NPD3268	Approved
0.7055	Intermediate Similarity	NPD3764	Approved
0.7049	Intermediate Similarity	NPD2163	Approved
0.7049	Intermediate Similarity	NPD7228	Approved
0.7045	Intermediate Similarity	NPD6279	Approved
0.7045	Intermediate Similarity	NPD6280	Approved
0.7037	Intermediate Similarity	NPD4908	Phase 1
0.7033	Intermediate Similarity	NPD2403	Approved
0.7031	Intermediate Similarity	NPD4360	Phase 2
0.7031	Intermediate Similarity	NPD4363	Phase 3
0.703	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD1933	Approved
0.7025	Intermediate Similarity	NPD1610	Phase 2
0.7006	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8151	Discontinued
0.6989	Remote Similarity	NPD7685	Pre-registration
0.6964	Remote Similarity	NPD5408	Approved
0.6964	Remote Similarity	NPD5404	Approved
0.6964	Remote Similarity	NPD5405	Approved
0.6964	Remote Similarity	NPD5406	Approved
0.6957	Remote Similarity	NPD1470	Approved
0.6944	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD4665	Approved
0.6942	Remote Similarity	NPD4111	Phase 1
0.6937	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6832	Phase 2
0.6914	Remote Similarity	NPD2798	Approved
0.6905	Remote Similarity	NPD4308	Phase 3
0.69	Remote Similarity	NPD7584	Approved
0.6894	Remote Similarity	NPD3225	Approved
0.6893	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4625	Phase 3
0.6885	Remote Similarity	NPD5242	Approved
0.6875	Remote Similarity	NPD9717	Approved
0.6875	Remote Similarity	NPD7907	Approved
0.6872	Remote Similarity	NPD4288	Approved
0.6854	Remote Similarity	NPD6844	Discontinued
0.6853	Remote Similarity	NPD6780	Approved
0.6853	Remote Similarity	NPD6776	Approved
0.6853	Remote Similarity	NPD6782	Approved
0.6853	Remote Similarity	NPD6777	Approved
0.6853	Remote Similarity	NPD6778	Approved
0.6853	Remote Similarity	NPD6779	Approved
0.6853	Remote Similarity	NPD6781	Approved
0.6852	Remote Similarity	NPD3267	Approved
0.6852	Remote Similarity	NPD3266	Approved
0.6848	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2654	Approved
0.6835	Remote Similarity	NPD9268	Approved
0.6816	Remote Similarity	NPD8455	Phase 2
0.6813	Remote Similarity	NPD422	Phase 1
0.6813	Remote Similarity	NPD1201	Approved
0.6809	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD8150	Discontinued
0.6798	Remote Similarity	NPD5890	Approved
0.6798	Remote Similarity	NPD5889	Approved
0.6784	Remote Similarity	NPD2424	Discontinued
0.678	Remote Similarity	NPD7458	Discontinued
0.6778	Remote Similarity	NPD5616	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