NPASS Compound

Structure

NPC203747 OpenBabel07101719512D 23 25 0 0 0 0 0 0 0 0999 V2000 1.7321 2.0000 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 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 4.3301 -2.5000 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 -1.0000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 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 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 4 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 9 1 0 0 0 0 6 15 2 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 12 2 0 0 0 0 8 23 1 0 0 0 0 9 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 2 0 0 0 0 11 16 1 0 0 0 0 12 16 1 0 0 0 0 13 23 1 0 0 0 0 14 17 2 0 0 0 0 14 21 1 0 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 17 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	308.569
LogP:	2.62
LogD:	2.507
LogS:	-3.94
# Rotatable Bonds:	3
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.772
Synthetic Accessibility Score:	2.27
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.741
MDCK Permeability:	1.7937671145773493e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.951
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.023
Plasma Protein Binding (PPB):	91.4048843383789%
Volume Distribution (VD):	0.601
Pgp-substrate:	8.807875633239746%

ADMET: Metabolism

CYP1A2-inhibitor:	0.908
CYP1A2-substrate:	0.934
CYP2C19-inhibitor:	0.644
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.625
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.71
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.76
CYP3A4-substrate:	0.218

ADMET: Excretion

Clearance (CL):	6.778
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.152
Drug-inuced Liver Injury (DILI):	0.466
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.211
Maximum Recommended Daily Dose:	0.636
Skin Sensitization:	0.91
Carcinogencity:	0.12
Eye Corrosion:	0.008
Eye Irritation:	0.822
Respiratory Toxicity:	0.22

Download Data

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

Natural Product: NPC203747

Natural Product ID:	NPC203747
*Common Name:**	7,4'-Dihydroxy-3',5'-Dimethoxyisoflavone
IUPAC Name:	7-hydroxy-3-(4-hydroxy-3,5-dimethoxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	KAAIDCFNSXASKK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-21-14-5-9(6-15(22-2)17(14)20)12-8-23-13-7-10(18)3-4-11(13)16(12)19/h3-8,18,20H,1-2H3
SMILES:	COc1cc(cc(c1O)OC)c1coc2cc(ccc2c1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457942
PubChem CID:	5323742
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002605] 3'-O-methylated isoflavonoids [CHEMONTID:0002690] 3'-O-methylisoflavones

*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
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10814365]
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]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26476665]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9322358]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21911	Tephrosia purpurea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21911	Tephrosia purpurea	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	2
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	=	17.2	uM	PMID[568949]
NPT34	Cell Line	BV-2	Mus musculus	IC50	>	50000.0	nM	PMID[568950]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	63700.0	nM	PMID[568949]
NPT2	Others	Unspecified		Ratio	>	3.7	n.a.	PMID[568949]

☑ 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 NPC203747 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	441
0.1-0.2	1901
0.2-0.3	4684
0.3-0.4	11461
0.4-0.5	6158
0.5-0.6	3660
0.6-0.7	5062
0.7-0.8	5093
0.8-0.85	2297
0.85-0.9	1248
0.9-0.95	610
0.95-1	82

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC254702
1.0	High Similarity	NPC139364
1.0	High Similarity	NPC80710
1.0	High Similarity	NPC194653
0.993	High Similarity	NPC69430
0.993	High Similarity	NPC333691
0.993	High Similarity	NPC142876
0.993	High Similarity	NPC264289
0.993	High Similarity	NPC264550
0.993	High Similarity	NPC40290
0.993	High Similarity	NPC139293
0.993	High Similarity	NPC200060
0.993	High Similarity	NPC195763
0.9858	High Similarity	NPC12377
0.9792	High Similarity	NPC256406
0.9789	High Similarity	NPC125449
0.9789	High Similarity	NPC188074
0.9724	High Similarity	NPC131266
0.9724	High Similarity	NPC291802
0.9724	High Similarity	NPC35763
0.9724	High Similarity	NPC100263
0.9724	High Similarity	NPC181209
0.9724	High Similarity	NPC209487
0.9724	High Similarity	NPC216769
0.9724	High Similarity	NPC269451
0.9724	High Similarity	NPC245382
0.9724	High Similarity	NPC121522
0.9724	High Similarity	NPC100971
0.9716	High Similarity	NPC242893
0.9716	High Similarity	NPC38065
0.9658	High Similarity	NPC124714
0.9655	High Similarity	NPC45291
0.9655	High Similarity	NPC19980
0.9653	High Similarity	NPC171916
0.9653	High Similarity	NPC38545
0.9645	High Similarity	NPC254659
0.9592	High Similarity	NPC39184
0.9586	High Similarity	NPC10467
0.9586	High Similarity	NPC85131
0.9586	High Similarity	NPC156953
0.9583	High Similarity	NPC238279
0.9583	High Similarity	NPC166036
0.9583	High Similarity	NPC203077
0.9577	High Similarity	NPC142165
0.9574	High Similarity	NPC284556
0.9574	High Similarity	NPC301178
0.9524	High Similarity	NPC469550
0.9524	High Similarity	NPC250557
0.9521	High Similarity	NPC31363
0.9521	High Similarity	NPC262623
0.9517	High Similarity	NPC137062
0.9517	High Similarity	NPC223579
0.9517	High Similarity	NPC52005
0.9517	High Similarity	NPC287101
0.9517	High Similarity	NPC183950
0.9507	High Similarity	NPC287722
0.9507	High Similarity	NPC471417
0.9507	High Similarity	NPC119663
0.9504	High Similarity	NPC110419
0.9459	High Similarity	NPC234255
0.9459	High Similarity	NPC134287
0.9459	High Similarity	NPC130589
0.9456	High Similarity	NPC477231
0.9456	High Similarity	NPC257648
0.9456	High Similarity	NPC260979
0.9456	High Similarity	NPC474993
0.9456	High Similarity	NPC323626
0.9456	High Similarity	NPC55205
0.9456	High Similarity	NPC39732
0.9456	High Similarity	NPC219582
0.9456	High Similarity	NPC302950
0.9456	High Similarity	NPC236637
0.9456	High Similarity	NPC472912
0.9456	High Similarity	NPC60972
0.9456	High Similarity	NPC324233
0.9452	High Similarity	NPC239363
0.9452	High Similarity	NPC29231
0.9452	High Similarity	NPC472279
0.9448	High Similarity	NPC287395
0.9448	High Similarity	NPC183655
0.9448	High Similarity	NPC218490
0.9448	High Similarity	NPC120464
0.9441	High Similarity	NPC207732
0.9437	High Similarity	NPC185607
0.9437	High Similarity	NPC312256
0.94	High Similarity	NPC184755
0.94	High Similarity	NPC74178
0.9396	High Similarity	NPC472455
0.9392	High Similarity	NPC18727
0.9388	High Similarity	NPC252933
0.9388	High Similarity	NPC54394
0.9388	High Similarity	NPC200740
0.9388	High Similarity	NPC125062
0.9384	High Similarity	NPC92722
0.9384	High Similarity	NPC177298
0.9384	High Similarity	NPC105512
0.9384	High Similarity	NPC48479
0.9384	High Similarity	NPC102003
0.9379	High Similarity	NPC168803
0.9379	High Similarity	NPC95864
0.9379	High Similarity	NPC12200
0.9379	High Similarity	NPC108406
0.9375	High Similarity	NPC157133
0.9338	High Similarity	NPC474960
0.9333	High Similarity	NPC78103
0.9333	High Similarity	NPC291508
0.9333	High Similarity	NPC299520
0.9333	High Similarity	NPC52530
0.9333	High Similarity	NPC52889
0.9333	High Similarity	NPC129684
0.9333	High Similarity	NPC99597
0.9333	High Similarity	NPC67876
0.9333	High Similarity	NPC210084
0.9329	High Similarity	NPC472280
0.9329	High Similarity	NPC152951
0.9329	High Similarity	NPC230149
0.9329	High Similarity	NPC57674
0.9329	High Similarity	NPC213622
0.9329	High Similarity	NPC2928
0.9329	High Similarity	NPC168247
0.9329	High Similarity	NPC20830
0.9329	High Similarity	NPC256612
0.9329	High Similarity	NPC117992
0.9324	High Similarity	NPC241498
0.9324	High Similarity	NPC162313
0.9324	High Similarity	NPC120163
0.9324	High Similarity	NPC104728
0.9324	High Similarity	NPC222830
0.9324	High Similarity	NPC293183
0.9324	High Similarity	NPC35544
0.9324	High Similarity	NPC275836
0.9324	High Similarity	NPC131624
0.9324	High Similarity	NPC239128
0.9324	High Similarity	NPC57030
0.9324	High Similarity	NPC279989
0.9324	High Similarity	NPC198826
0.9324	High Similarity	NPC188203
0.9324	High Similarity	NPC100887
0.9324	High Similarity	NPC471982
0.9324	High Similarity	NPC301323
0.9324	High Similarity	NPC212678
0.9324	High Similarity	NPC83508
0.9324	High Similarity	NPC187498
0.9324	High Similarity	NPC237994
0.9324	High Similarity	NPC82325
0.9324	High Similarity	NPC71334
0.9324	High Similarity	NPC156222
0.9324	High Similarity	NPC275722
0.9324	High Similarity	NPC25270
0.9324	High Similarity	NPC256283
0.9315	High Similarity	NPC119059
0.9315	High Similarity	NPC15329
0.9315	High Similarity	NPC196277
0.9315	High Similarity	NPC195202
0.9315	High Similarity	NPC43669
0.9315	High Similarity	NPC3036
0.9315	High Similarity	NPC272721
0.9315	High Similarity	NPC474903
0.9315	High Similarity	NPC131451
0.931	High Similarity	NPC143903
0.931	High Similarity	NPC226987
0.9296	High Similarity	NPC50823
0.9291	High Similarity	NPC162680
0.9291	High Similarity	NPC7013
0.9291	High Similarity	NPC303644
0.9291	High Similarity	NPC116632
0.9291	High Similarity	NPC181124
0.9291	High Similarity	NPC209560
0.9291	High Similarity	NPC212767
0.9291	High Similarity	NPC294409
0.9276	High Similarity	NPC295009
0.9276	High Similarity	NPC260640
0.9272	High Similarity	NPC55738
0.9272	High Similarity	NPC204879
0.9267	High Similarity	NPC326037
0.9267	High Similarity	NPC265511
0.9267	High Similarity	NPC35038
0.9267	High Similarity	NPC255106
0.9267	High Similarity	NPC170026
0.9267	High Similarity	NPC195796
0.9267	High Similarity	NPC6633
0.9267	High Similarity	NPC133970
0.9267	High Similarity	NPC13858
0.9267	High Similarity	NPC5322
0.9267	High Similarity	NPC474638
0.9267	High Similarity	NPC472916
0.9267	High Similarity	NPC282307
0.9267	High Similarity	NPC278778
0.9267	High Similarity	NPC320825
0.9267	High Similarity	NPC235165
0.9267	High Similarity	NPC291878
0.9262	High Similarity	NPC292214
0.9262	High Similarity	NPC273462
0.9262	High Similarity	NPC160951
0.9262	High Similarity	NPC176775
0.9262	High Similarity	NPC206238
0.9262	High Similarity	NPC271779
0.9262	High Similarity	NPC167091
0.9262	High Similarity	NPC78326
0.9262	High Similarity	NPC69394

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 NPC203747 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	429
0.1-0.2	985
0.2-0.3	1763
0.3-0.4	2652
0.4-0.5	1777
0.5-0.6	986
0.6-0.7	397
0.7-0.8	96
0.8-0.85	44
0.85-0.9	13
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9456	High Similarity	NPD1934	Approved
0.9262	High Similarity	NPD2801	Approved
0.9172	High Similarity	NPD1511	Approved
0.9149	High Similarity	NPD1510	Phase 2
0.9139	High Similarity	NPD3882	Suspended
0.9133	High Similarity	NPD2393	Clinical (unspecified phase)
0.9048	High Similarity	NPD1512	Approved
0.8865	High Similarity	NPD1240	Approved
0.8861	High Similarity	NPD3818	Discontinued
0.8854	High Similarity	NPD6167	Clinical (unspecified phase)
0.8854	High Similarity	NPD6166	Phase 2
0.8854	High Similarity	NPD6168	Clinical (unspecified phase)
0.8824	High Similarity	NPD3817	Phase 2
0.8808	High Similarity	NPD4380	Phase 2
0.8741	High Similarity	NPD1607	Approved
0.8732	High Similarity	NPD943	Approved
0.8699	High Similarity	NPD1549	Phase 2
0.8688	High Similarity	NPD7054	Approved
0.8634	High Similarity	NPD7074	Phase 3
0.8634	High Similarity	NPD7472	Approved
0.863	High Similarity	NPD1552	Clinical (unspecified phase)
0.863	High Similarity	NPD1550	Clinical (unspecified phase)
0.86	High Similarity	NPD4378	Clinical (unspecified phase)
0.8562	High Similarity	NPD2796	Approved
0.8526	High Similarity	NPD4868	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD6232	Discontinued
0.8471	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7075	Discontinued
0.8466	Intermediate Similarity	NPD6797	Phase 2
0.8447	Intermediate Similarity	NPD7473	Discontinued
0.8415	Intermediate Similarity	NPD7251	Discontinued
0.8411	Intermediate Similarity	NPD6799	Approved
0.8397	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD5494	Approved
0.8364	Intermediate Similarity	NPD7808	Phase 3
0.8364	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8322	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD7819	Suspended
0.8247	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD6599	Discontinued
0.8187	Intermediate Similarity	NPD919	Approved
0.8165	Intermediate Similarity	NPD1465	Phase 2
0.8163	Intermediate Similarity	NPD230	Phase 1
0.8153	Intermediate Similarity	NPD7411	Suspended
0.8138	Intermediate Similarity	NPD3027	Phase 3
0.8125	Intermediate Similarity	NPD9494	Approved
0.8113	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD3750	Approved
0.8092	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD1247	Approved
0.8067	Intermediate Similarity	NPD2935	Discontinued
0.8024	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD5403	Approved
0.8012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD5402	Approved
0.7988	Intermediate Similarity	NPD3926	Phase 2
0.7973	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1613	Approved
0.7972	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1551	Phase 2
0.7945	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6559	Discontinued
0.7866	Intermediate Similarity	NPD6959	Discontinued
0.784	Intermediate Similarity	NPD7768	Phase 2
0.7831	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD447	Suspended
0.7792	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3749	Approved
0.7771	Intermediate Similarity	NPD2533	Approved
0.7771	Intermediate Similarity	NPD2534	Approved
0.7771	Intermediate Similarity	NPD2532	Approved
0.7763	Intermediate Similarity	NPD3748	Approved
0.7748	Intermediate Similarity	NPD6651	Approved
0.7742	Intermediate Similarity	NPD4628	Phase 3
0.7718	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD2798	Approved
0.7682	Intermediate Similarity	NPD1933	Approved
0.7677	Intermediate Similarity	NPD1243	Approved
0.7677	Intermediate Similarity	NPD2800	Approved
0.7673	Intermediate Similarity	NPD920	Approved
0.7662	Intermediate Similarity	NPD2344	Approved
0.7657	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD7199	Phase 2
0.7643	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6234	Discontinued
0.758	Intermediate Similarity	NPD6190	Approved
0.7569	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD37	Approved
0.7534	Intermediate Similarity	NPD9269	Phase 2
0.7516	Intermediate Similarity	NPD1653	Approved
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD5953	Discontinued
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD6099	Approved
0.7484	Intermediate Similarity	NPD7390	Discontinued
0.7483	Intermediate Similarity	NPD5536	Phase 2
0.7483	Intermediate Similarity	NPD2313	Discontinued
0.7469	Intermediate Similarity	NPD3226	Approved
0.7468	Intermediate Similarity	NPD2309	Approved
0.7466	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7685	Pre-registration
0.7456	Intermediate Similarity	NPD5242	Approved
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7427	Intermediate Similarity	NPD3751	Discontinued
0.7419	Intermediate Similarity	NPD2799	Discontinued
0.741	Intermediate Similarity	NPD4966	Approved
0.741	Intermediate Similarity	NPD4967	Phase 2
0.741	Intermediate Similarity	NPD4965	Approved
0.74	Intermediate Similarity	NPD3018	Phase 2
0.7384	Intermediate Similarity	NPD7286	Phase 2
0.7383	Intermediate Similarity	NPD1470	Approved
0.7375	Intermediate Similarity	NPD4357	Discontinued
0.7374	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7458	Discontinued
0.7351	Intermediate Similarity	NPD6832	Phase 2
0.7351	Intermediate Similarity	NPD4908	Phase 1
0.7347	Intermediate Similarity	NPD1610	Phase 2
0.7347	Intermediate Similarity	NPD1201	Approved
0.7342	Intermediate Similarity	NPD2654	Approved
0.7338	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7228	Approved
0.7325	Intermediate Similarity	NPD2346	Discontinued
0.731	Intermediate Similarity	NPD9545	Approved
0.7308	Intermediate Similarity	NPD7033	Discontinued
0.7308	Intermediate Similarity	NPD4308	Phase 3
0.7308	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD228	Approved
0.7297	Intermediate Similarity	NPD9717	Approved
0.7297	Intermediate Similarity	NPD3972	Approved
0.7296	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD9493	Approved
0.7273	Intermediate Similarity	NPD6385	Approved
0.7273	Intermediate Similarity	NPD6386	Approved
0.726	Intermediate Similarity	NPD9268	Approved
0.7255	Intermediate Similarity	NPD3268	Approved
0.7255	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2982	Phase 2
0.7248	Intermediate Similarity	NPD2983	Phase 2
0.7246	Intermediate Similarity	NPD5353	Approved
0.723	Intermediate Similarity	NPD422	Phase 1
0.7193	Intermediate Similarity	NPD5710	Approved
0.7193	Intermediate Similarity	NPD5711	Approved
0.7193	Intermediate Similarity	NPD3787	Discontinued
0.7181	Intermediate Similarity	NPD2981	Phase 2
0.7181	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD5406	Approved
0.7152	Intermediate Similarity	NPD5405	Approved
0.7152	Intermediate Similarity	NPD5408	Approved
0.7152	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD411	Approved
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7117	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7266	Discontinued
0.7104	Intermediate Similarity	NPD4363	Phase 3
0.7104	Intermediate Similarity	NPD4360	Phase 2
0.7097	Intermediate Similarity	NPD6779	Approved
0.7097	Intermediate Similarity	NPD6782	Approved
0.7097	Intermediate Similarity	NPD6776	Approved
0.7097	Intermediate Similarity	NPD6781	Approved
0.7097	Intermediate Similarity	NPD6780	Approved
0.7097	Intermediate Similarity	NPD6777	Approved
0.7097	Intermediate Similarity	NPD6778	Approved
0.7086	Intermediate Similarity	NPD1876	Approved
0.7086	Intermediate Similarity	NPD3225	Approved
0.7083	Intermediate Similarity	NPD5283	Phase 1
0.7081	Intermediate Similarity	NPD8166	Discontinued
0.7079	Intermediate Similarity	NPD8312	Approved
0.7079	Intermediate Similarity	NPD8313	Approved
0.7068	Intermediate Similarity	NPD8151	Discontinued
0.7065	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4361	Phase 2
0.7056	Intermediate Similarity	NPD8434	Phase 2
0.7056	Intermediate Similarity	NPD8150	Discontinued
0.7053	Intermediate Similarity	NPD7584	Approved
0.7051	Intermediate Similarity	NPD4307	Phase 2
0.7048	Intermediate Similarity	NPD3455	Phase 2
0.7039	Intermediate Similarity	NPD3267	Approved
0.7039	Intermediate Similarity	NPD1164	Approved
0.7039	Intermediate Similarity	NPD3266	Approved
0.7037	Intermediate Similarity	NPD2354	Approved
0.7024	Intermediate Similarity	NPD6844	Discontinued
0.7012	Intermediate Similarity	NPD4662	Approved
0.7012	Intermediate Similarity	NPD4661	Approved
0.7011	Intermediate Similarity	NPD7784	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