NPASS Compound

Structure

CID305355 OpenBabel06191716112D 23 25 0 0 0 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 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 7.7942 1.5000 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 6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 4.3301 1.5000 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 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 6.0622 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 1.7321 -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 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 14 2 0 0 0 0 7 14 1 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 11 2 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 20 1 0 0 0 0 15 17 1 0 0 0 0 15 19 2 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 21 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.13
Volume:	331.449
LogP:	4.925
LogD:	4.044
LogS:	-4.767
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.672
Synthetic Accessibility Score:	2.522
Fsp3:	0.15
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:	-4.798
MDCK Permeability:	1.3995778317621443e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	101.74544525146484%
Volume Distribution (VD):	0.598
Pgp-substrate:	0.45735636353492737%

ADMET: Metabolism

CYP1A2-inhibitor:	0.979
CYP1A2-substrate:	0.144
CYP2C19-inhibitor:	0.944
CYP2C19-substrate:	0.104
CYP2C9-inhibitor:	0.907
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.908
CYP2D6-substrate:	0.692
CYP3A4-inhibitor:	0.801
CYP3A4-substrate:	0.205

ADMET: Excretion

Clearance (CL):	2.665
Half-life (T1/2):	0.205

ADMET: Toxicity

hERG Blockers:	0.162
Human Hepatotoxicity (H-HT):	0.615
Drug-inuced Liver Injury (DILI):	0.504
AMES Toxicity:	0.279
Rat Oral Acute Toxicity:	0.407
Maximum Recommended Daily Dose:	0.66
Skin Sensitization:	0.656
Carcinogencity:	0.823
Eye Corrosion:	0.004
Eye Irritation:	0.801
Respiratory Toxicity:	0.899

Download Data

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

Natural Product: NPC305355

Natural Product ID:	NPC305355
*Common Name:**	Lonchocarpin
IUPAC Name:	(E)-1-(5-hydroxy-2,2-dimethylchromen-6-yl)-3-phenylprop-2-en-1-one
Synonyms:	Lonchocarpin
Standard InCHIKey:	UEXPKLJRGIWQBF-CSKARUKUSA-N
Standard InCHI:	InChI=1S/C20H18O3/c1-20(2)13-12-16-18(23-20)11-9-15(19(16)22)17(21)10-8-14-6-4-3-5-7-14/h3-13,22H,1-2H3/b10-8+
SMILES:	O=C(c1ccc2c(c1O)C=CC(O2)(C)C)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457644
PubChem CID:	6283743
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]
NPO19856	Millettia pulchra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25630222]
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]
NPO4735	Lactuca floridana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27634	Scorzoneroides autumnalis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19856	Millettia pulchra	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	3
MIC	4
Others	10
Potency	4

Activity Type	# Activity
Cell Line	2
Individual Protein	4
NON-MOLECULAR	2
Organism	10
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	1122.0	nM	PMID[551845]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	62.9	%	PMID[551846]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[551845]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	7943.3	nM	PMID[551845]
NPT365	Individual Protein	NAD(P)H dehydrogenase [quinone] 1	Mus musculus	Ratio	=	1.7	n.a.	PMID[551847]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	3540.0	nM	PMID[551848]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	2000.0	ug.mL-1	PMID[551844]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MBC	=	2000.0	ug ml-1	PMID[551844]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	1000.0	ug.mL-1	PMID[551844]
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	=	1000.0	ug ml-1	PMID[551844]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	2000.0	ug.mL-1	PMID[551844]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MBC	=	2000.0	ug ml-1	PMID[551844]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2000.0	ug.mL-1	PMID[551844]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	2000.0	ug ml-1	PMID[551844]
NPT2	Others	Unspecified		Potency	n.a.	12589.3	nM	PMID[551845]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	84.0	%	PMID[551847]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	CC50	=	66040.0	nM	PMID[551849]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	21750.0	nM	PMID[551849]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	44530.0	nM	PMID[551849]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	3.03	n.a.	PMID[551849]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	1.48	n.a.	PMID[551849]

☑ 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 NPC305355 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	387
0.1-0.2	1615
0.2-0.3	4288
0.3-0.4	11327
0.4-0.5	6746
0.5-0.6	3799
0.6-0.7	5887
0.7-0.8	4953
0.8-0.85	1944
0.85-0.9	1074
0.9-0.95	571
0.95-1	106

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475680
0.9926	High Similarity	NPC147688
0.9926	High Similarity	NPC156590
0.9926	High Similarity	NPC64908
0.9926	High Similarity	NPC118840
0.9926	High Similarity	NPC205006
0.9853	High Similarity	NPC11561
0.9853	High Similarity	NPC226636
0.9852	High Similarity	NPC172986
0.9852	High Similarity	NPC261227
0.9852	High Similarity	NPC235239
0.9852	High Similarity	NPC270883
0.9781	High Similarity	NPC38219
0.9779	High Similarity	NPC110969
0.9779	High Similarity	NPC103362
0.9778	High Similarity	NPC220062
0.9778	High Similarity	NPC96565
0.9778	High Similarity	NPC55018
0.9778	High Similarity	NPC301217
0.9778	High Similarity	NPC303633
0.9778	High Similarity	NPC216978
0.971	High Similarity	NPC234629
0.971	High Similarity	NPC311741
0.9708	High Similarity	NPC62840
0.9708	High Similarity	NPC214236
0.9708	High Similarity	NPC299080
0.9708	High Similarity	NPC59739
0.9708	High Similarity	NPC144499
0.9708	High Similarity	NPC217083
0.9708	High Similarity	NPC78803
0.9708	High Similarity	NPC293852
0.9706	High Similarity	NPC159275
0.9706	High Similarity	NPC241100
0.9706	High Similarity	NPC69769
0.9706	High Similarity	NPC150522
0.9704	High Similarity	NPC201395
0.9638	High Similarity	NPC106985
0.9638	High Similarity	NPC18585
0.9638	High Similarity	NPC166138
0.9638	High Similarity	NPC219915
0.9635	High Similarity	NPC282300
0.9632	High Similarity	NPC78913
0.9632	High Similarity	NPC217186
0.9632	High Similarity	NPC18260
0.9632	High Similarity	NPC53181
0.963	High Similarity	NPC228661
0.9627	High Similarity	NPC151113
0.9571	High Similarity	NPC104406
0.9571	High Similarity	NPC79469
0.9571	High Similarity	NPC237635
0.9571	High Similarity	NPC23728
0.9571	High Similarity	NPC24673
0.9571	High Similarity	NPC201731
0.9571	High Similarity	NPC110303
0.9571	High Similarity	NPC97716
0.9568	High Similarity	NPC278175
0.9568	High Similarity	NPC469953
0.9568	High Similarity	NPC209040
0.9568	High Similarity	NPC257236
0.9565	High Similarity	NPC200694
0.9559	High Similarity	NPC470668
0.9559	High Similarity	NPC470669
0.9556	High Similarity	NPC13408
0.9504	High Similarity	NPC132592
0.9504	High Similarity	NPC272194
0.9504	High Similarity	NPC160821
0.9504	High Similarity	NPC266572
0.9504	High Similarity	NPC6511
0.95	High Similarity	NPC475052
0.95	High Similarity	NPC124729
0.95	High Similarity	NPC83357
0.95	High Similarity	NPC176229
0.95	High Similarity	NPC267375
0.95	High Similarity	NPC301276
0.95	High Similarity	NPC214774
0.95	High Similarity	NPC470647
0.95	High Similarity	NPC54577
0.95	High Similarity	NPC312973
0.95	High Similarity	NPC111786
0.95	High Similarity	NPC195621
0.95	High Similarity	NPC20488
0.95	High Similarity	NPC88964
0.95	High Similarity	NPC246948
0.95	High Similarity	NPC67805
0.95	High Similarity	NPC477955
0.95	High Similarity	NPC142405
0.9496	High Similarity	NPC257097
0.9496	High Similarity	NPC212932
0.9496	High Similarity	NPC9117
0.9496	High Similarity	NPC175504
0.9496	High Similarity	NPC91560
0.9496	High Similarity	NPC221432
0.9496	High Similarity	NPC190637
0.9496	High Similarity	NPC169591
0.9496	High Similarity	NPC68104
0.9496	High Similarity	NPC150408
0.9496	High Similarity	NPC164980
0.9496	High Similarity	NPC149026
0.9496	High Similarity	NPC75049
0.9496	High Similarity	NPC293053
0.9496	High Similarity	NPC24821
0.9496	High Similarity	NPC11700
0.9496	High Similarity	NPC478086
0.9496	High Similarity	NPC39329
0.9496	High Similarity	NPC316816
0.9496	High Similarity	NPC143896
0.9496	High Similarity	NPC214166
0.9496	High Similarity	NPC310130
0.9493	High Similarity	NPC14871
0.9493	High Similarity	NPC3188
0.9489	High Similarity	NPC23257
0.9485	High Similarity	NPC157855
0.9485	High Similarity	NPC317119
0.9485	High Similarity	NPC266597
0.9485	High Similarity	NPC250266
0.9478	High Similarity	NPC57601
0.9437	High Similarity	NPC65775
0.9437	High Similarity	NPC221868
0.9437	High Similarity	NPC37208
0.9437	High Similarity	NPC10027
0.9433	High Similarity	NPC296998
0.9433	High Similarity	NPC473077
0.9433	High Similarity	NPC180477
0.9433	High Similarity	NPC166757
0.9433	High Similarity	NPC283234
0.9433	High Similarity	NPC14001
0.9429	High Similarity	NPC273538
0.9429	High Similarity	NPC319752
0.9429	High Similarity	NPC131568
0.9429	High Similarity	NPC197252
0.9429	High Similarity	NPC236766
0.9429	High Similarity	NPC326500
0.9429	High Similarity	NPC473013
0.9429	High Similarity	NPC216538
0.9429	High Similarity	NPC473015
0.9429	High Similarity	NPC131579
0.9424	High Similarity	NPC148757
0.9424	High Similarity	NPC76372
0.9424	High Similarity	NPC473042
0.9424	High Similarity	NPC32739
0.9424	High Similarity	NPC66515
0.9424	High Similarity	NPC107572
0.9424	High Similarity	NPC324134
0.9424	High Similarity	NPC161506
0.9424	High Similarity	NPC36181
0.9424	High Similarity	NPC147145
0.9424	High Similarity	NPC324436
0.9424	High Similarity	NPC194432
0.9424	High Similarity	NPC167624
0.9424	High Similarity	NPC37496
0.9424	High Similarity	NPC166934
0.9424	High Similarity	NPC220998
0.9424	High Similarity	NPC76338
0.9424	High Similarity	NPC227579
0.9424	High Similarity	NPC228504
0.9424	High Similarity	NPC78
0.9424	High Similarity	NPC166482
0.9424	High Similarity	NPC223500
0.9424	High Similarity	NPC328164
0.9424	High Similarity	NPC177354
0.9424	High Similarity	NPC64915
0.9424	High Similarity	NPC10937
0.9424	High Similarity	NPC265040
0.9424	High Similarity	NPC40833
0.9424	High Similarity	NPC125855
0.9424	High Similarity	NPC182852
0.9424	High Similarity	NPC296917
0.9424	High Similarity	NPC1089
0.9424	High Similarity	NPC306829
0.942	High Similarity	NPC219917
0.942	High Similarity	NPC172250
0.942	High Similarity	NPC80962
0.942	High Similarity	NPC471587
0.942	High Similarity	NPC326109
0.942	High Similarity	NPC213659
0.942	High Similarity	NPC259166
0.942	High Similarity	NPC48624
0.942	High Similarity	NPC204985
0.942	High Similarity	NPC215311
0.942	High Similarity	NPC144118
0.9416	High Similarity	NPC254168
0.9416	High Similarity	NPC21350
0.9416	High Similarity	NPC272844
0.9416	High Similarity	NPC248995
0.9416	High Similarity	NPC124269
0.9416	High Similarity	NPC131130
0.9412	High Similarity	NPC186838
0.9412	High Similarity	NPC29353
0.9412	High Similarity	NPC477244
0.9412	High Similarity	NPC477242
0.9412	High Similarity	NPC124784
0.9412	High Similarity	NPC240593
0.9412	High Similarity	NPC66349
0.9412	High Similarity	NPC1486
0.9412	High Similarity	NPC274109
0.9412	High Similarity	NPC161196
0.9412	High Similarity	NPC231772
0.9412	High Similarity	NPC473887
0.9412	High Similarity	NPC168105
0.9412	High Similarity	NPC127447

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 NPC305355 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	969
0.2-0.3	1467
0.3-0.4	2638
0.4-0.5	1879
0.5-0.6	1189
0.6-0.7	438
0.7-0.8	142
0.8-0.85	40
0.85-0.9	16
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9568	High Similarity	NPD7410	Clinical (unspecified phase)
0.9429	High Similarity	NPD4378	Clinical (unspecified phase)
0.9185	High Similarity	NPD1240	Approved
0.9137	High Similarity	NPD1549	Phase 2
0.913	High Similarity	NPD2796	Approved
0.9065	High Similarity	NPD1550	Clinical (unspecified phase)
0.9065	High Similarity	NPD1552	Clinical (unspecified phase)
0.9058	High Similarity	NPD1510	Phase 2
0.9051	High Similarity	NPD1607	Approved
0.8912	High Similarity	NPD7411	Suspended
0.8844	High Similarity	NPD4380	Phase 2
0.8792	High Similarity	NPD2393	Clinical (unspecified phase)
0.8742	High Similarity	NPD7075	Discontinued
0.8733	High Similarity	NPD8443	Clinical (unspecified phase)
0.8725	High Similarity	NPD6801	Discontinued
0.869	High Similarity	NPD1511	Approved
0.8667	High Similarity	NPD7096	Clinical (unspecified phase)
0.8667	High Similarity	NPD7819	Suspended
0.8611	High Similarity	NPD3750	Approved
0.8571	High Similarity	NPD1512	Approved
0.8562	High Similarity	NPD6799	Approved
0.8543	High Similarity	NPD2801	Approved
0.8542	High Similarity	NPD1243	Approved
0.8542	High Similarity	NPD7421	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1934	Approved
0.8431	Intermediate Similarity	NPD7768	Phase 2
0.8414	Intermediate Similarity	NPD2800	Approved
0.8408	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD3749	Approved
0.8344	Intermediate Similarity	NPD6599	Discontinued
0.8312	Intermediate Similarity	NPD3882	Suspended
0.8276	Intermediate Similarity	NPD2344	Approved
0.8264	Intermediate Similarity	NPD3748	Approved
0.8264	Intermediate Similarity	NPD2799	Discontinued
0.8252	Intermediate Similarity	NPD6651	Approved
0.825	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD2313	Discontinued
0.8219	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6959	Discontinued
0.8207	Intermediate Similarity	NPD1551	Phase 2
0.8207	Intermediate Similarity	NPD2935	Discontinued
0.8146	Intermediate Similarity	NPD920	Approved
0.8146	Intermediate Similarity	NPD5403	Approved
0.8133	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD3817	Phase 2
0.8129	Intermediate Similarity	NPD1203	Approved
0.8082	Intermediate Similarity	NPD6100	Approved
0.8082	Intermediate Similarity	NPD6099	Approved
0.8075	Intermediate Similarity	NPD3818	Discontinued
0.8071	Intermediate Similarity	NPD2798	Approved
0.8063	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6166	Phase 2
0.8063	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD2309	Approved
0.8049	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD5494	Approved
0.8037	Intermediate Similarity	NPD5953	Discontinued
0.8025	Intermediate Similarity	NPD7286	Phase 2
0.8014	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD2797	Approved
0.7987	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD3268	Approved
0.7971	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD422	Phase 1
0.7941	Intermediate Similarity	NPD1548	Phase 1
0.7937	Intermediate Similarity	NPD6232	Discontinued
0.7922	Intermediate Similarity	NPD3226	Approved
0.7914	Intermediate Similarity	NPD7054	Approved
0.7914	Intermediate Similarity	NPD9717	Approved
0.7901	Intermediate Similarity	NPD7473	Discontinued
0.7895	Intermediate Similarity	NPD2532	Approved
0.7895	Intermediate Similarity	NPD2533	Approved
0.7895	Intermediate Similarity	NPD2534	Approved
0.7891	Intermediate Similarity	NPD4308	Phase 3
0.7891	Intermediate Similarity	NPD7033	Discontinued
0.7879	Intermediate Similarity	NPD6559	Discontinued
0.7867	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7074	Phase 3
0.7866	Intermediate Similarity	NPD7472	Approved
0.7862	Intermediate Similarity	NPD943	Approved
0.7848	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD6832	Phase 2
0.7818	Intermediate Similarity	NPD6797	Phase 2
0.7785	Intermediate Similarity	NPD2346	Discontinued
0.7785	Intermediate Similarity	NPD5402	Approved
0.7778	Intermediate Similarity	NPD4625	Phase 3
0.7771	Intermediate Similarity	NPD7251	Discontinued
0.775	Intermediate Similarity	NPD919	Approved
0.7748	Intermediate Similarity	NPD4628	Phase 3
0.7725	Intermediate Similarity	NPD7808	Phase 3
0.7714	Intermediate Similarity	NPD1610	Phase 2
0.7712	Intermediate Similarity	NPD7390	Discontinued
0.7708	Intermediate Similarity	NPD4908	Phase 1
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7687	Intermediate Similarity	NPD5124	Phase 1
0.7687	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD3225	Approved
0.766	Intermediate Similarity	NPD3972	Approved
0.7654	Intermediate Similarity	NPD1247	Approved
0.7651	Intermediate Similarity	NPD1729	Discontinued
0.7622	Intermediate Similarity	NPD3266	Approved
0.7622	Intermediate Similarity	NPD3267	Approved
0.7619	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4307	Phase 2
0.76	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4360	Phase 2
0.7586	Intermediate Similarity	NPD4363	Phase 3
0.7566	Intermediate Similarity	NPD2654	Approved
0.7562	Intermediate Similarity	NPD4288	Approved
0.7561	Intermediate Similarity	NPD3926	Phase 2
0.7554	Intermediate Similarity	NPD9545	Approved
0.7543	Intermediate Similarity	NPD4361	Phase 2
0.7543	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD9493	Approved
0.7535	Intermediate Similarity	NPD1608	Approved
0.7532	Intermediate Similarity	NPD6585	Discontinued
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD1164	Approved
0.7484	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1296	Phase 2
0.7483	Intermediate Similarity	NPD4749	Approved
0.7483	Intermediate Similarity	NPD3764	Approved
0.7465	Intermediate Similarity	NPD1201	Approved
0.7453	Intermediate Similarity	NPD2296	Approved
0.7452	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1933	Approved
0.7445	Intermediate Similarity	NPD1241	Discontinued
0.7425	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7003	Approved
0.7396	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5049	Phase 3
0.7379	Intermediate Similarity	NPD1470	Approved
0.7376	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5889	Approved
0.7375	Intermediate Similarity	NPD5890	Approved
0.7368	Intermediate Similarity	NPD5408	Approved
0.7368	Intermediate Similarity	NPD5404	Approved
0.7368	Intermediate Similarity	NPD5405	Approved
0.7368	Intermediate Similarity	NPD5406	Approved
0.7365	Intermediate Similarity	NPD411	Approved
0.7358	Intermediate Similarity	NPD7458	Discontinued
0.7356	Intermediate Similarity	NPD4287	Approved
0.7355	Intermediate Similarity	NPD2354	Approved
0.7347	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD447	Suspended
0.7333	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD17	Approved
0.7322	Intermediate Similarity	NPD7584	Approved
0.732	Intermediate Similarity	NPD1471	Phase 3
0.732	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD5710	Approved
0.7289	Intermediate Similarity	NPD5711	Approved
0.7279	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD6104	Discontinued
0.725	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6798	Discontinued
0.7222	Intermediate Similarity	NPD7577	Discontinued
0.7219	Intermediate Similarity	NPD230	Phase 1
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4662	Approved
0.7215	Intermediate Similarity	NPD4661	Approved
0.7211	Intermediate Similarity	NPD1019	Discontinued
0.7208	Intermediate Similarity	NPD2353	Approved
0.7208	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1876	Approved
0.719	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7229	Phase 3
0.7172	Intermediate Similarity	NPD1481	Phase 2
0.7152	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3140	Approved
0.7152	Intermediate Similarity	NPD1613	Approved
0.7152	Intermediate Similarity	NPD3142	Approved
0.7143	Intermediate Similarity	NPD4476	Approved
0.7143	Intermediate Similarity	NPD4477	Approved
0.7134	Intermediate Similarity	NPD3887	Approved
0.7134	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD3751	Discontinued
0.7117	Intermediate Similarity	NPD6844	Discontinued
0.7117	Intermediate Similarity	NPD6280	Approved
0.7117	Intermediate Similarity	NPD6279	Approved
0.7114	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1535	Discovery
0.7101	Intermediate Similarity	NPD2403	Approved
0.708	Intermediate Similarity	NPD74	Approved
0.708	Intermediate Similarity	NPD9266	Approved
0.7073	Intermediate Similarity	NPD5761	Phase 2
0.7073	Intermediate Similarity	NPD5760	Phase 2
0.7069	Intermediate Similarity	NPD8312	Approved
0.7069	Intermediate Similarity	NPD8313	Approved

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