NPASS Compound

Structure

NPC94155 OpenBabel07101719522D 26 29 0 0 0 0 0 0 0 0999 V2000 -0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -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 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 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2646 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 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 6.9282 1.0000 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 2.5981 -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 -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 7.6713 1.6691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2701 2.4781 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 21 1 0 0 0 0 3 6 2 0 0 0 0 3 13 1 0 0 0 0 4 7 2 0 0 0 0 4 13 1 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 21 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 24 1 0 0 0 0 12 25 1 0 0 0 0 14 16 1 0 0 0 0 14 20 2 0 0 0 0 15 17 2 0 0 0 0 15 20 1 0 0 0 0 16 22 2 0 0 0 0 17 26 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 23 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.12
Volume:	357.769
LogP:	4.854
LogD:	3.91
LogS:	-4.86
# Rotatable Bonds:	3
TPSA:	64.99
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.664
Synthetic Accessibility Score:	2.74
Fsp3:	0.19
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:	-4.888
MDCK Permeability:	1.4459884368989151e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.06

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	102.77640533447266%
Volume Distribution (VD):	0.524
Pgp-substrate:	0.5960904955863953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.156
CYP2C19-inhibitor:	0.967
CYP2C19-substrate:	0.083
CYP2C9-inhibitor:	0.907
CYP2C9-substrate:	0.937
CYP2D6-inhibitor:	0.948
CYP2D6-substrate:	0.817
CYP3A4-inhibitor:	0.896
CYP3A4-substrate:	0.205

ADMET: Excretion

Clearance (CL):	11.969
Half-life (T1/2):	0.128

ADMET: Toxicity

hERG Blockers:	0.145
Human Hepatotoxicity (H-HT):	0.602
Drug-inuced Liver Injury (DILI):	0.615
AMES Toxicity:	0.202
Rat Oral Acute Toxicity:	0.358
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.585
Carcinogencity:	0.931
Eye Corrosion:	0.003
Eye Irritation:	0.278
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC94155

Natural Product ID:	NPC94155
*Common Name:**	Glabrachromene Ii
IUPAC Name:	(E)-3-(1,3-benzodioxol-5-yl)-1-(5-hydroxy-2,2-dimethylchromen-6-yl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	WKEIAFLNVZWDKU-ZZXKWVIFSA-N
Standard InCHI:	InChI=1S/C21H18O5/c1-21(2)10-9-15-17(26-21)8-5-14(20(15)23)16(22)6-3-13-4-7-18-19(11-13)25-12-24-18/h3-11,23H,12H2,1-2H3/b6-3+
SMILES:	O=C(c1ccc2c(c1O)C=CC(O2)(C)C)/C=C/c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581071
PubChem CID:	6442711
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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]

☑ 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	=	6560.0	nM	PMID[455153]

☑ 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 NPC94155 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	403
0.1-0.2	1716
0.2-0.3	4126
0.3-0.4	10136
0.4-0.5	8050
0.5-0.6	3306
0.6-0.7	5087
0.7-0.8	5689
0.8-0.85	3169
0.85-0.9	943
0.9-0.95	69
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC310206
0.9484	High Similarity	NPC113055
0.9427	High Similarity	NPC125991
0.9423	High Similarity	NPC269906
0.9416	High Similarity	NPC234255
0.9412	High Similarity	NPC68882
0.9412	High Similarity	NPC104728
0.9412	High Similarity	NPC35544
0.9408	High Similarity	NPC234152
0.9379	High Similarity	NPC223375
0.9379	High Similarity	NPC475825
0.9363	High Similarity	NPC34376
0.9355	High Similarity	NPC472455
0.9308	High Similarity	NPC470773
0.9304	High Similarity	NPC302741
0.9299	High Similarity	NPC328102
0.9295	High Similarity	NPC476981
0.929	High Similarity	NPC472280
0.9286	High Similarity	NPC237994
0.9259	High Similarity	NPC235575
0.9236	High Similarity	NPC184755
0.9236	High Similarity	NPC204879
0.9236	High Similarity	NPC215375
0.9236	High Similarity	NPC74178
0.9236	High Similarity	NPC62518
0.9231	High Similarity	NPC155063
0.9221	High Similarity	NPC154345
0.9198	High Similarity	NPC212748
0.9182	High Similarity	NPC18284
0.9182	High Similarity	NPC273021
0.9177	High Similarity	NPC476980
0.9177	High Similarity	NPC472624
0.9172	High Similarity	NPC167595
0.9172	High Similarity	NPC52889
0.9172	High Similarity	NPC218313
0.9172	High Similarity	NPC474681
0.9172	High Similarity	NPC284820
0.9172	High Similarity	NPC473272
0.9167	High Similarity	NPC168247
0.9167	High Similarity	NPC117992
0.9167	High Similarity	NPC284353
0.9167	High Similarity	NPC230149
0.9167	High Similarity	NPC152951
0.9167	High Similarity	NPC57674
0.9167	High Similarity	NPC256925
0.9161	High Similarity	NPC471982
0.915	High Similarity	NPC195202
0.9145	High Similarity	NPC88345
0.9136	High Similarity	NPC211309
0.9136	High Similarity	NPC471287
0.9125	High Similarity	NPC470772
0.9125	High Similarity	NPC124038
0.9119	High Similarity	NPC162668
0.9119	High Similarity	NPC295009
0.9119	High Similarity	NPC260640
0.9119	High Similarity	NPC470756
0.9108	High Similarity	NPC133970
0.9108	High Similarity	NPC6633
0.9108	High Similarity	NPC5322
0.9108	High Similarity	NPC282307
0.9108	High Similarity	NPC170026
0.9108	High Similarity	NPC471985
0.9103	High Similarity	NPC475895
0.9103	High Similarity	NPC279930
0.9103	High Similarity	NPC273462
0.9103	High Similarity	NPC227337
0.9103	High Similarity	NPC33051
0.9103	High Similarity	NPC49402
0.9103	High Similarity	NPC70433
0.9097	High Similarity	NPC308451
0.9097	High Similarity	NPC256406
0.9097	High Similarity	NPC318424
0.9091	High Similarity	NPC156635
0.9085	High Similarity	NPC12200
0.9085	High Similarity	NPC33265
0.9085	High Similarity	NPC62536
0.9079	High Similarity	NPC296575
0.9074	High Similarity	NPC76482
0.9074	High Similarity	NPC229729
0.9068	High Similarity	NPC300053
0.9068	High Similarity	NPC108433
0.9062	High Similarity	NPC472448
0.9062	High Similarity	NPC81679
0.9062	High Similarity	NPC469575
0.9062	High Similarity	NPC472635
0.9062	High Similarity	NPC83922
0.9057	High Similarity	NPC118256
0.9057	High Similarity	NPC475784
0.9057	High Similarity	NPC225624
0.9057	High Similarity	NPC119209
0.9057	High Similarity	NPC285973
0.9057	High Similarity	NPC192686
0.9051	High Similarity	NPC27337
0.9051	High Similarity	NPC78071
0.9051	High Similarity	NPC291508
0.9045	High Similarity	NPC200246
0.9045	High Similarity	NPC226025
0.9045	High Similarity	NPC478238
0.9038	High Similarity	NPC31627
0.9038	High Similarity	NPC60972
0.9038	High Similarity	NPC476238
0.9038	High Similarity	NPC327269
0.9038	High Similarity	NPC285623
0.9038	High Similarity	NPC39732
0.9038	High Similarity	NPC292460
0.9036	High Similarity	NPC67302
0.9032	High Similarity	NPC189270
0.9032	High Similarity	NPC88804
0.9032	High Similarity	NPC5840
0.9032	High Similarity	NPC50728
0.9032	High Similarity	NPC166753
0.9032	High Similarity	NPC3825
0.903	High Similarity	NPC472607
0.9024	High Similarity	NPC256760
0.9024	High Similarity	NPC261254
0.902	High Similarity	NPC12377
0.9018	High Similarity	NPC288813
0.9012	High Similarity	NPC119589
0.9012	High Similarity	NPC235610
0.9012	High Similarity	NPC113093
0.9012	High Similarity	NPC254306
0.9006	High Similarity	NPC309025
0.9006	High Similarity	NPC470178
0.9006	High Similarity	NPC243930
0.9006	High Similarity	NPC88023
0.9	High Similarity	NPC259456
0.9	High Similarity	NPC57715
0.9	High Similarity	NPC471290
0.9	High Similarity	NPC234644
0.9	High Similarity	NPC258331
0.9	High Similarity	NPC29876
0.9	High Similarity	NPC474038
0.9	High Similarity	NPC167678
0.8994	High Similarity	NPC187792
0.8987	High Similarity	NPC291878
0.8987	High Similarity	NPC195796
0.8987	High Similarity	NPC470600
0.8987	High Similarity	NPC35038
0.8987	High Similarity	NPC278778
0.8981	High Similarity	NPC168805
0.8981	High Similarity	NPC244371
0.8981	High Similarity	NPC121910
0.8981	High Similarity	NPC478213
0.8981	High Similarity	NPC170492
0.8981	High Similarity	NPC280937
0.8981	High Similarity	NPC189130
0.8974	High Similarity	NPC471675
0.8974	High Similarity	NPC236769
0.8974	High Similarity	NPC226973
0.8974	High Similarity	NPC208043
0.8974	High Similarity	NPC472580
0.897	High Similarity	NPC208668
0.8968	High Similarity	NPC223579
0.8968	High Similarity	NPC287101
0.8968	High Similarity	NPC328119
0.8968	High Similarity	NPC38545
0.8968	High Similarity	NPC171916
0.8968	High Similarity	NPC48479
0.8968	High Similarity	NPC177298
0.8968	High Similarity	NPC52005
0.8968	High Similarity	NPC137062
0.8968	High Similarity	NPC183950
0.8968	High Similarity	NPC159103
0.8963	High Similarity	NPC231194
0.8963	High Similarity	NPC150767
0.8963	High Similarity	NPC78734
0.8963	High Similarity	NPC105511
0.8963	High Similarity	NPC51326
0.8957	High Similarity	NPC477502
0.8957	High Similarity	NPC471288
0.8954	High Similarity	NPC234629
0.8954	High Similarity	NPC224687
0.8954	High Similarity	NPC311741
0.8954	High Similarity	NPC471590
0.8951	High Similarity	NPC311830
0.8951	High Similarity	NPC22832
0.8951	High Similarity	NPC303174
0.8951	High Similarity	NPC165720
0.8951	High Similarity	NPC472277
0.8947	High Similarity	NPC226636
0.8947	High Similarity	NPC11561
0.8947	High Similarity	NPC119663
0.8944	High Similarity	NPC300537
0.8944	High Similarity	NPC474033
0.8944	High Similarity	NPC127782
0.8944	High Similarity	NPC474034
0.8944	High Similarity	NPC93215
0.8944	High Similarity	NPC474162
0.8944	High Similarity	NPC474150
0.8944	High Similarity	NPC229632
0.8944	High Similarity	NPC261470
0.8938	High Similarity	NPC188433
0.8938	High Similarity	NPC28241
0.8938	High Similarity	NPC204290
0.8938	High Similarity	NPC474960
0.8938	High Similarity	NPC476283
0.8938	High Similarity	NPC471973
0.8931	High Similarity	NPC180011
0.8931	High Similarity	NPC219867
0.8931	High Similarity	NPC210048

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 NPC94155 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	954
0.2-0.3	1720
0.3-0.4	2669
0.4-0.5	1849
0.5-0.6	993
0.6-0.7	421
0.7-0.8	142
0.8-0.85	45
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9193	High Similarity	NPD3818	Discontinued
0.8868	High Similarity	NPD3882	Suspended
0.8861	High Similarity	NPD2801	Approved
0.8861	High Similarity	NPD2393	Clinical (unspecified phase)
0.8797	High Similarity	NPD1934	Approved
0.8788	High Similarity	NPD7054	Approved
0.8735	High Similarity	NPD7074	Phase 3
0.8735	High Similarity	NPD7472	Approved
0.871	High Similarity	NPD4378	Clinical (unspecified phase)
0.8696	High Similarity	NPD4381	Clinical (unspecified phase)
0.8645	High Similarity	NPD1511	Approved
0.8599	High Similarity	NPD6980	Clinical (unspecified phase)
0.859	High Similarity	NPD7410	Clinical (unspecified phase)
0.8589	High Similarity	NPD5494	Approved
0.858	High Similarity	NPD7808	Phase 3
0.8571	High Similarity	NPD6797	Phase 2
0.8571	High Similarity	NPD3817	Phase 2
0.8535	High Similarity	NPD1512	Approved
0.8521	High Similarity	NPD7251	Discontinued
0.8521	High Similarity	NPD6559	Discontinued
0.8471	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7075	Discontinued
0.8452	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD4380	Phase 2
0.8415	Intermediate Similarity	NPD919	Approved
0.8395	Intermediate Similarity	NPD7819	Suspended
0.8395	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6166	Phase 2
0.8383	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD6232	Discontinued
0.8366	Intermediate Similarity	NPD1510	Phase 2
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.8333	Intermediate Similarity	NPD6801	Discontinued
0.8323	Intermediate Similarity	NPD1549	Phase 2
0.8312	Intermediate Similarity	NPD2796	Approved
0.8291	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD7411	Suspended
0.8258	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1240	Approved
0.8204	Intermediate Similarity	NPD1247	Approved
0.8182	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6799	Approved
0.8129	Intermediate Similarity	NPD5844	Phase 1
0.8121	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD1607	Approved
0.8107	Intermediate Similarity	NPD3926	Phase 2
0.8095	Intermediate Similarity	NPD7199	Phase 2
0.8038	Intermediate Similarity	NPD1243	Approved
0.8024	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD3750	Approved
0.7975	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7768	Phase 2
0.7962	Intermediate Similarity	NPD2935	Discontinued
0.7953	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD1933	Approved
0.7925	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD2800	Approved
0.7914	Intermediate Similarity	NPD920	Approved
0.7901	Intermediate Similarity	NPD2532	Approved
0.7901	Intermediate Similarity	NPD2534	Approved
0.7901	Intermediate Similarity	NPD2533	Approved
0.7892	Intermediate Similarity	NPD37	Approved
0.7888	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6959	Discontinued
0.7875	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD943	Approved
0.787	Intermediate Similarity	NPD6234	Discontinued
0.7857	Intermediate Similarity	NPD4966	Approved
0.7857	Intermediate Similarity	NPD4967	Phase 2
0.7857	Intermediate Similarity	NPD4965	Approved
0.7844	Intermediate Similarity	NPD1465	Phase 2
0.7805	Intermediate Similarity	NPD5403	Approved
0.7798	Intermediate Similarity	NPD5402	Approved
0.7791	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1551	Phase 2
0.7727	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD447	Suspended
0.7692	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2344	Approved
0.7683	Intermediate Similarity	NPD5401	Approved
0.768	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD3748	Approved
0.7673	Intermediate Similarity	NPD2799	Discontinued
0.7651	Intermediate Similarity	NPD1653	Approved
0.7628	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2313	Discontinued
0.7627	Intermediate Similarity	NPD5953	Discontinued
0.7605	Intermediate Similarity	NPD7458	Discontinued
0.7605	Intermediate Similarity	NPD3226	Approved
0.7597	Intermediate Similarity	NPD2798	Approved
0.7594	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7685	Pre-registration
0.7562	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD7228	Approved
0.7557	Intermediate Similarity	NPD3751	Discontinued
0.7547	Intermediate Similarity	NPD6651	Approved
0.7546	Intermediate Similarity	NPD4628	Phase 3
0.7546	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7539	Intermediate Similarity	NPD7584	Approved
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.7514	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD2309	Approved
0.75	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD8313	Approved
0.75	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD230	Phase 1
0.7469	Intermediate Similarity	NPD2346	Discontinued
0.7453	Intermediate Similarity	NPD7033	Discontinued
0.7436	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3787	Discontinued
0.7421	Intermediate Similarity	NPD1613	Approved
0.7421	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1203	Approved
0.7407	Intermediate Similarity	NPD6778	Approved
0.7407	Intermediate Similarity	NPD6776	Approved
0.7407	Intermediate Similarity	NPD6780	Approved
0.7407	Intermediate Similarity	NPD6782	Approved
0.7407	Intermediate Similarity	NPD6781	Approved
0.7407	Intermediate Similarity	NPD6779	Approved
0.7407	Intermediate Similarity	NPD6777	Approved
0.7353	Intermediate Similarity	NPD7028	Phase 2
0.7346	Intermediate Similarity	NPD4308	Phase 3
0.7342	Intermediate Similarity	NPD3027	Phase 3
0.734	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5710	Approved
0.733	Intermediate Similarity	NPD5711	Approved
0.7305	Intermediate Similarity	NPD7390	Discontinued
0.7296	Intermediate Similarity	NPD3268	Approved
0.7296	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7435	Discontinued
0.7292	Intermediate Similarity	NPD7696	Phase 3
0.7292	Intermediate Similarity	NPD7697	Approved
0.7292	Intermediate Similarity	NPD7698	Approved
0.729	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD4361	Phase 2
0.7287	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD8434	Phase 2
0.7282	Intermediate Similarity	NPD8151	Discontinued
0.7278	Intermediate Similarity	NPD6832	Phase 2
0.7254	Intermediate Similarity	NPD7870	Phase 2
0.7254	Intermediate Similarity	NPD7871	Phase 2
0.7239	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4625	Phase 3
0.7232	Intermediate Similarity	NPD7229	Phase 3
0.7226	Intermediate Similarity	NPD9717	Approved
0.7215	Intermediate Similarity	NPD9494	Approved
0.7198	Intermediate Similarity	NPD7240	Approved
0.7197	Intermediate Similarity	NPD2797	Approved
0.7191	Intermediate Similarity	NPD5242	Approved
0.7188	Intermediate Similarity	NPD3764	Approved
0.7186	Intermediate Similarity	NPD6190	Approved
0.7182	Intermediate Similarity	NPD1729	Discontinued
0.7174	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4908	Phase 1
0.7169	Intermediate Similarity	NPD2654	Approved
0.7161	Intermediate Similarity	NPD422	Phase 1
0.7161	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5124	Phase 1
0.716	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2403	Approved
0.715	Intermediate Similarity	NPD6823	Phase 2
0.7143	Intermediate Similarity	NPD4360	Phase 2
0.7143	Intermediate Similarity	NPD4363	Phase 3
0.7143	Intermediate Similarity	NPD6534	Approved
0.7143	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD6535	Approved
0.7143	Intermediate Similarity	NPD7585	Approved
0.7126	Intermediate Similarity	NPD8455	Phase 2
0.7124	Intermediate Similarity	NPD1548	Phase 1
0.7121	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7783	Phase 2
0.7115	Intermediate Similarity	NPD1608	Approved
0.7112	Intermediate Similarity	NPD4287	Approved
0.7101	Intermediate Similarity	NPD4357	Discontinued
0.7099	Intermediate Similarity	NPD4307	Phase 2
0.7093	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7583	Approved
0.7091	Intermediate Similarity	NPD5405	Approved
0.7091	Intermediate Similarity	NPD5404	Approved
0.7091	Intermediate Similarity	NPD5408	Approved
0.7091	Intermediate Similarity	NPD5406	Approved
0.7086	Intermediate Similarity	NPD4288	Approved
0.7081	Intermediate Similarity	NPD411	Approved
0.7071	Intermediate Similarity	NPD7874	Approved
0.7071	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5005	Approved
0.7062	Intermediate Similarity	NPD5006	Approved
0.7059	Intermediate Similarity	NPD5536	Phase 2
0.7051	Intermediate Similarity	NPD1610	Phase 2
0.7048	Intermediate Similarity	NPD1471	Phase 3
0.7048	Intermediate Similarity	NPD2343	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