NPASS Compound

Structure

NPC268081 OpenBabel07101719142D 24 25 0 0 0 0 0 0 0 0999 V2000 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 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 0.0000 3.0000 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 2.5981 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 0.0000 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 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 6 1 0 0 0 0 2 7 1 0 0 0 0 3 11 1 0 0 0 0 4 22 1 0 0 0 0 5 23 1 0 0 0 0 6 8 1 0 0 0 0 7 11 2 0 0 0 0 8 12 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 23 1 0 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 19 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 21 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.15
Volume:	345.563
LogP:	3.291
LogD:	3.311
LogS:	-5.354
# Rotatable Bonds:	6
TPSA:	65.74
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.456
Synthetic Accessibility Score:	2.78
Fsp3:	0.368
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.761
MDCK Permeability:	1.8154312783735804e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.908

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	86.11766052246094%
Volume Distribution (VD):	0.956
Pgp-substrate:	8.29045581817627%

ADMET: Metabolism

CYP1A2-inhibitor:	0.878
CYP1A2-substrate:	0.972
CYP2C19-inhibitor:	0.844
CYP2C19-substrate:	0.651
CYP2C9-inhibitor:	0.808
CYP2C9-substrate:	0.869
CYP2D6-inhibitor:	0.682
CYP2D6-substrate:	0.715
CYP3A4-inhibitor:	0.649
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	10.459
Half-life (T1/2):	0.539

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.62
Drug-inuced Liver Injury (DILI):	0.784
AMES Toxicity:	0.233
Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.399
Skin Sensitization:	0.409
Carcinogencity:	0.198
Eye Corrosion:	0.005
Eye Irritation:	0.358
Respiratory Toxicity:	0.921

Download Data

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

Natural Product: NPC268081

Natural Product ID:	NPC268081
*Common Name:**	5,7-Dimethoxy-8-[(E)-2-Methylbut-2-Enoyl]-4-Propylchromen-2-One
IUPAC Name:	5,7-dimethoxy-8-[(E)-2-methylbut-2-enoyl]-4-propylchromen-2-one
Synonyms:
Standard InCHIKey:	HJTTYQGWKFPWJE-YRNVUSSQSA-N
Standard InCHI:	InChI=1S/C19H22O5/c1-6-8-12-9-15(20)24-19-16(12)13(22-4)10-14(23-5)17(19)18(21)11(3)7-2/h7,9-10H,6,8H2,1-5H3/b11-7+
SMILES:	CCCc1cc(=O)oc2c1c(cc(c2C(=O)/C(=C/C)/C)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462675
PubChem CID:	6474785
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives

*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
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	Sarawak, Malaysia	n.a.	PMID[11430019]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1379639]
NPO19800	Calophyllum teysmannii	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792623]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792623]
NPO19800	Calophyllum teysmannii	Species	Calophyllaceae	Eukaryota	n.a.	latex	n.a.	PMID[8864237]
NPO19800	Calophyllum teysmannii	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19800	Calophyllum teysmannii	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19800	Calophyllum teysmannii	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	1000.0	nM	PMID[507332]

☑ 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 NPC268081 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	428
0.1-0.2	1746
0.2-0.3	4607
0.3-0.4	10413
0.4-0.5	7829
0.5-0.6	4457
0.6-0.7	5926
0.7-0.8	4883
0.8-0.85	1647
0.85-0.9	530
0.9-0.95	214
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC253616
0.9699	High Similarity	NPC36414
0.9627	High Similarity	NPC472515
0.9478	High Similarity	NPC38153
0.9403	High Similarity	NPC472516
0.9394	High Similarity	NPC229646
0.9338	High Similarity	NPC136095
0.9338	High Similarity	NPC473209
0.9333	High Similarity	NPC103001
0.9328	High Similarity	NPC46869
0.9308	High Similarity	NPC473907
0.9281	High Similarity	NPC171656
0.927	High Similarity	NPC470856
0.9259	High Similarity	NPC174999
0.9259	High Similarity	NPC161196
0.9237	High Similarity	NPC473894
0.9231	High Similarity	NPC49852
0.9231	High Similarity	NPC475496
0.9197	High Similarity	NPC262635
0.9191	High Similarity	NPC474624
0.9191	High Similarity	NPC131782
0.9191	High Similarity	NPC138047
0.9191	High Similarity	NPC332594
0.9143	High Similarity	NPC294365
0.9143	High Similarity	NPC469953
0.9137	High Similarity	NPC36181
0.913	High Similarity	NPC16455
0.913	High Similarity	NPC307990
0.9124	High Similarity	NPC219584
0.9124	High Similarity	NPC199458
0.9124	High Similarity	NPC470083
0.9124	High Similarity	NPC17848
0.9124	High Similarity	NPC131130
0.9124	High Similarity	NPC183639
0.9118	High Similarity	NPC254741
0.9111	High Similarity	NPC66705
0.9111	High Similarity	NPC125920
0.9104	High Similarity	NPC54503
0.9104	High Similarity	NPC473655
0.9104	High Similarity	NPC101294
0.9104	High Similarity	NPC55147
0.9091	High Similarity	NPC191104
0.9078	High Similarity	NPC154217
0.9078	High Similarity	NPC470322
0.9078	High Similarity	NPC473927
0.9071	High Similarity	NPC87609
0.9071	High Similarity	NPC470296
0.9071	High Similarity	NPC196459
0.9071	High Similarity	NPC112791
0.9071	High Similarity	NPC94794
0.9071	High Similarity	NPC188632
0.9065	High Similarity	NPC103362
0.9065	High Similarity	NPC110969
0.9065	High Similarity	NPC254010
0.9065	High Similarity	NPC201820
0.9058	High Similarity	NPC139554
0.9058	High Similarity	NPC19476
0.9058	High Similarity	NPC11566
0.9058	High Similarity	NPC241975
0.9058	High Similarity	NPC23257
0.9051	High Similarity	NPC259685
0.9051	High Similarity	NPC157855
0.9044	High Similarity	NPC60667
0.9037	High Similarity	NPC108113
0.9037	High Similarity	NPC93756
0.9037	High Similarity	NPC292998
0.9037	High Similarity	NPC247743
0.903	High Similarity	NPC284424
0.903	High Similarity	NPC278556
0.9021	High Similarity	NPC88445
0.9014	High Similarity	NPC218300
0.9014	High Similarity	NPC180477
0.9014	High Similarity	NPC282335
0.9007	High Similarity	NPC469935
0.9007	High Similarity	NPC1886
0.9007	High Similarity	NPC178627
0.9007	High Similarity	NPC196137
0.9	High Similarity	NPC470556
0.9	High Similarity	NPC112829
0.9	High Similarity	NPC294432
0.9	High Similarity	NPC226636
0.9	High Similarity	NPC11561
0.9	High Similarity	NPC313036
0.8993	High Similarity	NPC221173
0.8993	High Similarity	NPC241100
0.8993	High Similarity	NPC172986
0.8993	High Similarity	NPC261227
0.8993	High Similarity	NPC472409
0.8993	High Similarity	NPC471587
0.8993	High Similarity	NPC474037
0.8993	High Similarity	NPC150522
0.8993	High Similarity	NPC159275
0.8993	High Similarity	NPC270883
0.8986	High Similarity	NPC470669
0.8986	High Similarity	NPC470668
0.8978	High Similarity	NPC156910
0.8971	High Similarity	NPC61499
0.8971	High Similarity	NPC125269
0.8971	High Similarity	NPC229128
0.8963	High Similarity	NPC10971
0.8958	High Similarity	NPC474660
0.8958	High Similarity	NPC180351
0.8951	High Similarity	NPC266743
0.8947	High Similarity	NPC211120
0.8944	High Similarity	NPC57470
0.8944	High Similarity	NPC181388
0.8939	High Similarity	NPC37512
0.8936	High Similarity	NPC184738
0.8936	High Similarity	NPC307895
0.8936	High Similarity	NPC474939
0.8936	High Similarity	NPC33653
0.8936	High Similarity	NPC96216
0.8936	High Similarity	NPC59522
0.8936	High Similarity	NPC470909
0.8936	High Similarity	NPC470553
0.8931	High Similarity	NPC65041
0.8929	High Similarity	NPC147688
0.8929	High Similarity	NPC205006
0.8929	High Similarity	NPC471640
0.8929	High Similarity	NPC470555
0.8929	High Similarity	NPC282300
0.8929	High Similarity	NPC64908
0.8929	High Similarity	NPC24075
0.8929	High Similarity	NPC156590
0.8929	High Similarity	NPC471644
0.8929	High Similarity	NPC118840
0.8921	High Similarity	NPC78913
0.8921	High Similarity	NPC96565
0.8921	High Similarity	NPC220062
0.8921	High Similarity	NPC216978
0.8921	High Similarity	NPC55018
0.8921	High Similarity	NPC301217
0.8921	High Similarity	NPC217186
0.8921	High Similarity	NPC18260
0.8921	High Similarity	NPC53181
0.8921	High Similarity	NPC303633
0.8905	High Similarity	NPC99854
0.8905	High Similarity	NPC101752
0.8905	High Similarity	NPC151113
0.8897	High Similarity	NPC223354
0.8889	High Similarity	NPC475589
0.8889	High Similarity	NPC19238
0.8889	High Similarity	NPC175159
0.8889	High Similarity	NPC473584
0.8889	High Similarity	NPC31872
0.8889	High Similarity	NPC164299
0.8881	High Similarity	NPC74539
0.8881	High Similarity	NPC304443
0.8881	High Similarity	NPC297886
0.8881	High Similarity	NPC140120
0.8881	High Similarity	NPC249942
0.8881	High Similarity	NPC129650
0.8873	High Similarity	NPC288910
0.8873	High Similarity	NPC470554
0.8873	High Similarity	NPC118059
0.8873	High Similarity	NPC311741
0.8873	High Similarity	NPC179970
0.8873	High Similarity	NPC234629
0.8873	High Similarity	NPC133060
0.8865	High Similarity	NPC51146
0.8865	High Similarity	NPC471643
0.8865	High Similarity	NPC471639
0.8865	High Similarity	NPC147145
0.8865	High Similarity	NPC166858
0.8857	High Similarity	NPC305355
0.8857	High Similarity	NPC235239
0.8857	High Similarity	NPC69769
0.8857	High Similarity	NPC475680
0.8855	High Similarity	NPC73413
0.8855	High Similarity	NPC201667
0.8849	High Similarity	NPC470671
0.8849	High Similarity	NPC474504
0.8849	High Similarity	NPC470672
0.8849	High Similarity	NPC474487
0.8849	High Similarity	NPC201395
0.8849	High Similarity	NPC124269
0.8841	High Similarity	NPC274109
0.8841	High Similarity	NPC1486
0.8841	High Similarity	NPC477243
0.8841	High Similarity	NPC61546
0.8841	High Similarity	NPC41461
0.8841	High Similarity	NPC72452
0.8841	High Similarity	NPC477244
0.8841	High Similarity	NPC98115
0.8841	High Similarity	NPC12165
0.8841	High Similarity	NPC25287
0.8841	High Similarity	NPC150399
0.8841	High Similarity	NPC66349
0.8841	High Similarity	NPC168105
0.8841	High Similarity	NPC186838
0.8841	High Similarity	NPC477242
0.8841	High Similarity	NPC249606
0.8836	High Similarity	NPC256141
0.8832	High Similarity	NPC144027
0.8832	High Similarity	NPC236974
0.8828	High Similarity	NPC473466
0.8828	High Similarity	NPC151973
0.8828	High Similarity	NPC474735
0.8824	High Similarity	NPC203817
0.8824	High Similarity	NPC182428

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 NPC268081 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	1002
0.2-0.3	1733
0.3-0.4	2684
0.4-0.5	1841
0.5-0.6	1037
0.6-0.7	339
0.7-0.8	105
0.8-0.85	33
0.85-0.9	11
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9197	High Similarity	NPD1243	Approved
0.8978	High Similarity	NPD2796	Approved
0.8881	High Similarity	NPD920	Approved
0.8865	High Similarity	NPD643	Clinical (unspecified phase)
0.8803	High Similarity	NPD6799	Approved
0.8767	High Similarity	NPD7411	Suspended
0.8741	High Similarity	NPD642	Clinical (unspecified phase)
0.8741	High Similarity	NPD4378	Clinical (unspecified phase)
0.8707	High Similarity	NPD6801	Discontinued
0.8649	High Similarity	NPD7096	Clinical (unspecified phase)
0.8649	High Similarity	NPD7819	Suspended
0.8611	High Similarity	NPD7410	Clinical (unspecified phase)
0.8571	High Similarity	NPD6599	Discontinued
0.85	High Similarity	NPD3748	Approved
0.8478	Intermediate Similarity	NPD1240	Approved
0.8477	Intermediate Similarity	NPD7075	Discontinued
0.8456	Intermediate Similarity	NPD6832	Phase 2
0.8451	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD1549	Phase 2
0.8421	Intermediate Similarity	NPD919	Approved
0.8392	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8369	Intermediate Similarity	NPD1510	Phase 2
0.8357	Intermediate Similarity	NPD1607	Approved
0.8333	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD2799	Discontinued
0.8224	Intermediate Similarity	NPD3817	Phase 2
0.8207	Intermediate Similarity	NPD3750	Approved
0.8201	Intermediate Similarity	NPD1296	Phase 2
0.82	Intermediate Similarity	NPD4380	Phase 2
0.817	Intermediate Similarity	NPD7768	Phase 2
0.8158	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD9717	Approved
0.8138	Intermediate Similarity	NPD2800	Approved
0.8121	Intermediate Similarity	NPD5403	Approved
0.8108	Intermediate Similarity	NPD2534	Approved
0.8108	Intermediate Similarity	NPD2533	Approved
0.8108	Intermediate Similarity	NPD2532	Approved
0.8108	Intermediate Similarity	NPD5401	Approved
0.8105	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD6651	Approved
0.8082	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8071	Intermediate Similarity	NPD2313	Discontinued
0.8056	Intermediate Similarity	NPD2935	Discontinued
0.8056	Intermediate Similarity	NPD1551	Phase 2
0.8043	Intermediate Similarity	NPD1019	Discontinued
0.8014	Intermediate Similarity	NPD2654	Approved
0.8013	Intermediate Similarity	NPD5494	Approved
0.8	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3749	Approved
0.7971	Intermediate Similarity	NPD3267	Approved
0.7971	Intermediate Similarity	NPD3266	Approved
0.7971	Intermediate Similarity	NPD1203	Approved
0.7941	Intermediate Similarity	NPD422	Phase 1
0.7922	Intermediate Similarity	NPD2801	Approved
0.7919	Intermediate Similarity	NPD1511	Approved
0.7902	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD5953	Discontinued
0.7888	Intermediate Similarity	NPD7286	Phase 2
0.7857	Intermediate Similarity	NPD1934	Approved
0.7848	Intermediate Similarity	NPD1247	Approved
0.7832	Intermediate Similarity	NPD4307	Phase 2
0.7821	Intermediate Similarity	NPD3882	Suspended
0.7817	Intermediate Similarity	NPD3268	Approved
0.7815	Intermediate Similarity	NPD1512	Approved
0.781	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3226	Approved
0.7778	Intermediate Similarity	NPD5124	Phase 1
0.7778	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1933	Approved
0.7763	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD5402	Approved
0.7736	Intermediate Similarity	NPD6959	Discontinued
0.7718	Intermediate Similarity	NPD4628	Phase 3
0.7718	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2797	Approved
0.7707	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6232	Discontinued
0.7677	Intermediate Similarity	NPD5890	Approved
0.7677	Intermediate Similarity	NPD5889	Approved
0.7669	Intermediate Similarity	NPD1241	Discontinued
0.7669	Intermediate Similarity	NPD5844	Phase 1
0.766	Intermediate Similarity	NPD2798	Approved
0.7654	Intermediate Similarity	NPD7473	Discontinued
0.764	Intermediate Similarity	NPD3926	Phase 2
0.7635	Intermediate Similarity	NPD2346	Discontinued
0.7626	Intermediate Similarity	NPD3972	Approved
0.7619	Intermediate Similarity	NPD4308	Phase 3
0.7619	Intermediate Similarity	NPD7033	Discontinued
0.7613	Intermediate Similarity	NPD6585	Discontinued
0.7607	Intermediate Similarity	NPD3818	Discontinued
0.7569	Intermediate Similarity	NPD411	Approved
0.7536	Intermediate Similarity	NPD17	Approved
0.7534	Intermediate Similarity	NPD447	Suspended
0.753	Intermediate Similarity	NPD6559	Discontinued
0.7518	Intermediate Similarity	NPD3225	Approved
0.7518	Intermediate Similarity	NPD9545	Approved
0.7517	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9493	Approved
0.7485	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7469	Intermediate Similarity	NPD5711	Approved
0.7469	Intermediate Similarity	NPD5710	Approved
0.7455	Intermediate Similarity	NPD7054	Approved
0.7434	Intermediate Similarity	NPD3887	Approved
0.7421	Intermediate Similarity	NPD4288	Approved
0.7415	Intermediate Similarity	NPD230	Phase 1
0.741	Intermediate Similarity	NPD7472	Approved
0.741	Intermediate Similarity	NPD7074	Phase 3
0.74	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2353	Approved
0.7383	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2403	Approved
0.7376	Intermediate Similarity	NPD1608	Approved
0.7371	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD6797	Phase 2
0.7358	Intermediate Similarity	NPD1465	Phase 2
0.7347	Intermediate Similarity	NPD3140	Approved
0.7347	Intermediate Similarity	NPD3142	Approved
0.7342	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6099	Approved
0.7333	Intermediate Similarity	NPD5535	Approved
0.7333	Intermediate Similarity	NPD6100	Approved
0.7328	Intermediate Similarity	NPD9697	Approved
0.7321	Intermediate Similarity	NPD7251	Discontinued
0.732	Intermediate Similarity	NPD2309	Approved
0.7303	Intermediate Similarity	NPD1652	Phase 2
0.7285	Intermediate Similarity	NPD1471	Phase 3
0.7285	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7808	Phase 3
0.7262	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6808	Phase 2
0.7244	Intermediate Similarity	NPD2186	Approved
0.7244	Intermediate Similarity	NPD5049	Phase 3
0.723	Intermediate Similarity	NPD943	Approved
0.7219	Intermediate Similarity	NPD6104	Discontinued
0.7215	Intermediate Similarity	NPD7458	Discontinued
0.7214	Intermediate Similarity	NPD5691	Approved
0.7211	Intermediate Similarity	NPD6798	Discontinued
0.7211	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2354	Approved
0.7205	Intermediate Similarity	NPD5353	Approved
0.7202	Intermediate Similarity	NPD1729	Discontinued
0.7176	Intermediate Similarity	NPD9261	Approved
0.7153	Intermediate Similarity	NPD1876	Approved
0.7152	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD3134	Approved
0.7143	Intermediate Similarity	NPD7003	Approved
0.7143	Intermediate Similarity	NPD1548	Phase 1
0.7115	Intermediate Similarity	NPD7390	Discontinued
0.7108	Intermediate Similarity	NPD5242	Approved
0.7107	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4477	Approved
0.7105	Intermediate Similarity	NPD4476	Approved
0.7103	Intermediate Similarity	NPD1164	Approved
0.7095	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1358	Approved
0.7081	Intermediate Similarity	NPD6280	Approved
0.7081	Intermediate Similarity	NPD6279	Approved
0.7075	Intermediate Similarity	NPD4908	Phase 1
0.707	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6355	Discontinued
0.7063	Intermediate Similarity	NPD1281	Approved
0.7062	Intermediate Similarity	NPD4363	Phase 3
0.7062	Intermediate Similarity	NPD4360	Phase 2
0.7059	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6004	Phase 3
0.7059	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6002	Phase 3
0.7059	Intermediate Similarity	NPD6005	Phase 3
0.7051	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD8032	Phase 2
0.7042	Intermediate Similarity	NPD1778	Approved
0.7042	Intermediate Similarity	NPD4626	Approved
0.7029	Intermediate Similarity	NPD4287	Approved
0.7025	Intermediate Similarity	NPD6273	Approved
0.7022	Intermediate Similarity	NPD4361	Phase 2
0.7022	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1894	Discontinued
0.7012	Intermediate Similarity	NPD6971	Discontinued
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2979	Phase 3
0.7	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5404	Approved
0.6993	Remote Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD5408	Approved
0.6993	Remote Similarity	NPD5405	Approved
0.6988	Remote Similarity	NPD7199	Phase 2
0.6987	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3764	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