NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.1
Volume:	270.225
LogP:	2.941
LogD:	2.922
LogS:	-4.665
# Rotatable Bonds:	4
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	2.197
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.631
MDCK Permeability:	2.327521906408947e-05
Pgp-inhibitor:	0.037
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.24
Plasma Protein Binding (PPB):	85.4896240234375%
Volume Distribution (VD):	0.902
Pgp-substrate:	13.043899536132812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.901
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.828
CYP2C19-substrate:	0.3
CYP2C9-inhibitor:	0.62
CYP2C9-substrate:	0.805
CYP2D6-inhibitor:	0.095
CYP2D6-substrate:	0.677
CYP3A4-inhibitor:	0.09
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	11.39
Half-life (T1/2):	0.463

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.325
Drug-inuced Liver Injury (DILI):	0.884
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.282
Skin Sensitization:	0.082
Carcinogencity:	0.842
Eye Corrosion:	0.012
Eye Irritation:	0.839
Respiratory Toxicity:	0.231

Download Data

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

Natural Product: NPC36414

Natural Product ID:	NPC36414
*Common Name:**	7-Methoxy-6-(3-Methylbutanoyl)Chromen-2-One
IUPAC Name:	7-methoxy-6-(3-methylbutanoyl)chromen-2-one
Synonyms:
Standard InCHIKey:	ZXVIZFSHTAUXCC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O4/c1-9(2)6-12(16)11-7-10-4-5-15(17)19-13(10)8-14(11)18-3/h4-5,7-9H,6H2,1-3H3
SMILES:	COc1cc2oc(=O)ccc2cc1C(=O)CC(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2003701
PubChem CID:	235195
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
NPO13526	Medicago hybrida	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
GI50	58

Activity Type	# Activity
Cell Line	58

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	39174.19	nM	PMID[502975]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	57809.6	nM	PMID[502975]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	66374.31	nM	PMID[502975]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	56104.8	nM	PMID[502975]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	62373.48	nM	PMID[502975]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	23550.49	nM	PMID[502975]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	71121.35	nM	PMID[502975]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	71449.63	nM	PMID[502975]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	78704.58	nM	PMID[502975]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	99311.6	nM	PMID[502975]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	94841.85	nM	PMID[502975]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	73790.42	nM	PMID[502975]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	62517.27	nM	PMID[502975]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	22908.68	nM	PMID[502975]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	38547.84	nM	PMID[502975]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	28641.78	nM	PMID[502975]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[502975]

☑ 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 NPC36414 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	433
0.1-0.2	1788
0.2-0.3	4899
0.3-0.4	10884
0.4-0.5	7046
0.5-0.6	4564
0.6-0.7	6114
0.7-0.8	4777
0.8-0.85	1494
0.85-0.9	486
0.9-0.95	179
0.95-1	33

Similarity Score	Similarity Level	Natural Product ID
0.9776	High Similarity	NPC472515
0.9774	High Similarity	NPC253616
0.9699	High Similarity	NPC472516
0.9699	High Similarity	NPC268081
0.9485	High Similarity	NPC473209
0.9416	High Similarity	NPC470856
0.9398	High Similarity	NPC229646
0.9398	High Similarity	NPC55147
0.9348	High Similarity	NPC254010
0.9343	High Similarity	NPC136095
0.9338	High Similarity	NPC38153
0.9338	High Similarity	NPC103001
0.9254	High Similarity	NPC54503
0.9242	High Similarity	NPC473894
0.922	High Similarity	NPC470322
0.922	High Similarity	NPC154217
0.9203	High Similarity	NPC262635
0.9197	High Similarity	NPC332594
0.9191	High Similarity	NPC46869
0.9167	High Similarity	NPC473907
0.9149	High Similarity	NPC1886
0.9149	High Similarity	NPC171656
0.9149	High Similarity	NPC294365
0.9149	High Similarity	NPC196137
0.9143	High Similarity	NPC313036
0.913	High Similarity	NPC183639
0.913	High Similarity	NPC199458
0.9124	High Similarity	NPC254741
0.9124	High Similarity	NPC161196
0.9097	High Similarity	NPC191104
0.9091	High Similarity	NPC49852
0.9091	High Similarity	NPC475496
0.9085	High Similarity	NPC181388
0.9078	High Similarity	NPC188632
0.9078	High Similarity	NPC87609
0.9078	High Similarity	NPC470296
0.9078	High Similarity	NPC94794
0.9078	High Similarity	NPC112791
0.9078	High Similarity	NPC196459
0.9071	High Similarity	NPC201820
0.9071	High Similarity	NPC24075
0.9065	High Similarity	NPC19476
0.9065	High Similarity	NPC241975
0.9058	High Similarity	NPC474624
0.9058	High Similarity	NPC138047
0.9058	High Similarity	NPC131782
0.9044	High Similarity	NPC292998
0.9044	High Similarity	NPC247743
0.9034	High Similarity	NPC98028
0.9028	High Similarity	NPC88445
0.9021	High Similarity	NPC74539
0.9021	High Similarity	NPC304443
0.9021	High Similarity	NPC282335
0.9021	High Similarity	NPC218300
0.9014	High Similarity	NPC469953
0.9014	High Similarity	NPC469935
0.9014	High Similarity	NPC178627
0.9007	High Similarity	NPC470556
0.9007	High Similarity	NPC36181
0.9007	High Similarity	NPC51146
0.9007	High Similarity	NPC166858
0.8993	High Similarity	NPC470668
0.8993	High Similarity	NPC470083
0.8993	High Similarity	NPC219584
0.8993	High Similarity	NPC17848
0.8993	High Similarity	NPC131130
0.8993	High Similarity	NPC470669
0.8986	High Similarity	NPC174999
0.8978	High Similarity	NPC125920
0.8978	High Similarity	NPC66705
0.8971	High Similarity	NPC101294
0.8971	High Similarity	NPC473655
0.8966	High Similarity	NPC474735
0.8958	High Similarity	NPC161864
0.8958	High Similarity	NPC208303
0.8958	High Similarity	NPC266743
0.8951	High Similarity	NPC473927
0.8944	High Similarity	NPC470553
0.8944	High Similarity	NPC96216
0.8944	High Similarity	NPC470909
0.8944	High Similarity	NPC307895
0.8944	High Similarity	NPC474939
0.8939	High Similarity	NPC65041
0.8936	High Similarity	NPC103362
0.8936	High Similarity	NPC110969
0.8936	High Similarity	NPC282300
0.8936	High Similarity	NPC470555
0.8929	High Similarity	NPC11566
0.8929	High Similarity	NPC23257
0.8921	High Similarity	NPC259685
0.8921	High Similarity	NPC157855
0.8913	High Similarity	NPC60667
0.8913	High Similarity	NPC151113
0.8905	High Similarity	NPC108113
0.8905	High Similarity	NPC223354
0.8905	High Similarity	NPC93756
0.8904	High Similarity	NPC290671
0.8897	High Similarity	NPC284424
0.8897	High Similarity	NPC278556
0.8897	High Similarity	NPC164299
0.8897	High Similarity	NPC19238
0.8897	High Similarity	NPC175159
0.8897	High Similarity	NPC469932
0.8889	High Similarity	NPC180477
0.8889	High Similarity	NPC297886
0.8889	High Similarity	NPC249942
0.8889	High Similarity	NPC140120
0.8881	High Similarity	NPC234629
0.8881	High Similarity	NPC133060
0.8881	High Similarity	NPC311741
0.8881	High Similarity	NPC470554
0.8881	High Similarity	NPC179970
0.8881	High Similarity	NPC118059
0.8881	High Similarity	NPC246903
0.8881	High Similarity	NPC288910
0.8873	High Similarity	NPC294432
0.8873	High Similarity	NPC11561
0.8873	High Similarity	NPC112829
0.8873	High Similarity	NPC226636
0.8865	High Similarity	NPC16455
0.8865	High Similarity	NPC472409
0.8865	High Similarity	NPC150522
0.8865	High Similarity	NPC307990
0.8865	High Similarity	NPC474037
0.8865	High Similarity	NPC159275
0.8865	High Similarity	NPC172986
0.8865	High Similarity	NPC261227
0.8865	High Similarity	NPC221173
0.8865	High Similarity	NPC270883
0.8865	High Similarity	NPC241100
0.8865	High Similarity	NPC471587
0.8857	High Similarity	NPC470671
0.8857	High Similarity	NPC474504
0.8857	High Similarity	NPC470672
0.8857	High Similarity	NPC474487
0.8849	High Similarity	NPC156910
0.8841	High Similarity	NPC61499
0.8841	High Similarity	NPC229128
0.8841	High Similarity	NPC125269
0.8836	High Similarity	NPC474660
0.8836	High Similarity	NPC158866
0.8836	High Similarity	NPC180351
0.8832	High Similarity	NPC182428
0.8832	High Similarity	NPC25937
0.8828	High Similarity	NPC469933
0.8824	High Similarity	NPC472517
0.8819	High Similarity	NPC25844
0.8819	High Similarity	NPC477955
0.8819	High Similarity	NPC470910
0.8819	High Similarity	NPC57470
0.8815	High Similarity	NPC211120
0.8811	High Similarity	NPC166138
0.8811	High Similarity	NPC18585
0.8811	High Similarity	NPC184738
0.8811	High Similarity	NPC59522
0.8811	High Similarity	NPC33653
0.8811	High Similarity	NPC17262
0.8811	High Similarity	NPC106985
0.8806	High Similarity	NPC37512
0.8806	High Similarity	NPC293387
0.8803	High Similarity	NPC156590
0.8803	High Similarity	NPC118840
0.8803	High Similarity	NPC147688
0.8803	High Similarity	NPC64908
0.8803	High Similarity	NPC471640
0.8803	High Similarity	NPC471644
0.8803	High Similarity	NPC229916
0.8803	High Similarity	NPC205006
0.8797	High Similarity	NPC471827
0.8797	High Similarity	NPC165556
0.8797	High Similarity	NPC471828
0.8794	High Similarity	NPC55018
0.8794	High Similarity	NPC18260
0.8794	High Similarity	NPC217186
0.8794	High Similarity	NPC96565
0.8794	High Similarity	NPC472343
0.8794	High Similarity	NPC301217
0.8794	High Similarity	NPC139554
0.8794	High Similarity	NPC473076
0.8794	High Similarity	NPC220062
0.8794	High Similarity	NPC216978
0.8794	High Similarity	NPC78913
0.8794	High Similarity	NPC303633
0.8794	High Similarity	NPC477956
0.8794	High Similarity	NPC53181
0.8788	High Similarity	NPC472518
0.8786	High Similarity	NPC153979
0.8784	High Similarity	NPC131725
0.8777	High Similarity	NPC101752
0.8777	High Similarity	NPC99854
0.8777	High Similarity	NPC104796
0.8776	High Similarity	NPC312549
0.8776	High Similarity	NPC209142
0.8767	High Similarity	NPC104236
0.8767	High Similarity	NPC164205
0.8759	High Similarity	NPC31872
0.8759	High Similarity	NPC24673
0.8759	High Similarity	NPC201731
0.8759	High Similarity	NPC97716
0.8759	High Similarity	NPC285748

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 NPC36414 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	394
0.1-0.2	974
0.2-0.3	1715
0.3-0.4	2690
0.4-0.5	1820
0.5-0.6	1064
0.6-0.7	336
0.7-0.8	105
0.8-0.85	33
0.85-0.9	12
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9203	High Similarity	NPD1243	Approved
0.9021	High Similarity	NPD920	Approved
0.9007	High Similarity	NPD643	Clinical (unspecified phase)
0.8986	High Similarity	NPD2796	Approved
0.8881	High Similarity	NPD642	Clinical (unspecified phase)
0.875	High Similarity	NPD4378	Clinical (unspecified phase)
0.8681	High Similarity	NPD6799	Approved
0.8658	High Similarity	NPD7096	Clinical (unspecified phase)
0.8658	High Similarity	NPD7819	Suspended
0.8649	High Similarity	NPD7411	Suspended
0.8592	High Similarity	NPD970	Clinical (unspecified phase)
0.8591	High Similarity	NPD6801	Discontinued
0.8553	High Similarity	NPD919	Approved
0.8511	High Similarity	NPD3748	Approved
0.8511	High Similarity	NPD1510	Phase 2
0.8493	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8489	Intermediate Similarity	NPD1240	Approved
0.8487	Intermediate Similarity	NPD7075	Discontinued
0.8462	Intermediate Similarity	NPD1549	Phase 2
0.8456	Intermediate Similarity	NPD6599	Discontinued
0.8392	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8392	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.838	Intermediate Similarity	NPD2799	Discontinued
0.8369	Intermediate Similarity	NPD1607	Approved
0.8333	Intermediate Similarity	NPD6832	Phase 2
0.8276	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD3817	Phase 2
0.8235	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD3750	Approved
0.8214	Intermediate Similarity	NPD1296	Phase 2
0.8214	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD4380	Phase 2
0.8194	Intermediate Similarity	NPD1551	Phase 2
0.8182	Intermediate Similarity	NPD7768	Phase 2
0.817	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD9717	Approved
0.8141	Intermediate Similarity	NPD5494	Approved
0.8095	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD2313	Discontinued
0.8069	Intermediate Similarity	NPD2935	Discontinued
0.8058	Intermediate Similarity	NPD1019	Discontinued
0.8054	Intermediate Similarity	NPD1511	Approved
0.8027	Intermediate Similarity	NPD2800	Approved
0.8013	Intermediate Similarity	NPD5403	Approved
0.8013	Intermediate Similarity	NPD3749	Approved
0.8013	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD5401	Approved
0.8	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD2532	Approved
0.7986	Intermediate Similarity	NPD1203	Approved
0.7986	Intermediate Similarity	NPD3267	Approved
0.7986	Intermediate Similarity	NPD3266	Approved
0.7986	Intermediate Similarity	NPD6651	Approved
0.7975	Intermediate Similarity	NPD1247	Approved
0.7956	Intermediate Similarity	NPD422	Phase 1
0.7947	Intermediate Similarity	NPD1512	Approved
0.7935	Intermediate Similarity	NPD2801	Approved
0.7917	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD5953	Discontinued
0.7871	Intermediate Similarity	NPD1934	Approved
0.7847	Intermediate Similarity	NPD4307	Phase 2
0.7834	Intermediate Similarity	NPD3882	Suspended
0.7832	Intermediate Similarity	NPD3268	Approved
0.7826	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD17	Approved
0.7801	Intermediate Similarity	NPD2798	Approved
0.7793	Intermediate Similarity	NPD5124	Phase 1
0.7793	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD3226	Approved
0.7791	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7286	Phase 2
0.7785	Intermediate Similarity	NPD2654	Approved
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7473	Discontinued
0.7771	Intermediate Similarity	NPD5402	Approved
0.7733	Intermediate Similarity	NPD4628	Phase 3
0.7733	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD2797	Approved
0.7708	Intermediate Similarity	NPD411	Approved
0.7702	Intermediate Similarity	NPD6232	Discontinued
0.7687	Intermediate Similarity	NPD1241	Discontinued
0.7683	Intermediate Similarity	NPD5844	Phase 1
0.7671	Intermediate Similarity	NPD447	Suspended
0.7671	Intermediate Similarity	NPD1933	Approved
0.7654	Intermediate Similarity	NPD3926	Phase 2
0.7651	Intermediate Similarity	NPD2346	Discontinued
0.7643	Intermediate Similarity	NPD1608	Approved
0.764	Intermediate Similarity	NPD6959	Discontinued
0.7635	Intermediate Similarity	NPD4308	Phase 3
0.7622	Intermediate Similarity	NPD3818	Discontinued
0.761	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD5889	Approved
0.758	Intermediate Similarity	NPD5890	Approved
0.7545	Intermediate Similarity	NPD6559	Discontinued
0.7536	Intermediate Similarity	NPD9545	Approved
0.7533	Intermediate Similarity	NPD2344	Approved
0.7518	Intermediate Similarity	NPD3972	Approved
0.7518	Intermediate Similarity	NPD9493	Approved
0.7517	Intermediate Similarity	NPD7033	Discontinued
0.7516	Intermediate Similarity	NPD6585	Discontinued
0.7515	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7054	Approved
0.7438	Intermediate Similarity	NPD4288	Approved
0.7432	Intermediate Similarity	NPD230	Phase 1
0.7425	Intermediate Similarity	NPD7074	Phase 3
0.7425	Intermediate Similarity	NPD7472	Approved
0.7417	Intermediate Similarity	NPD1471	Phase 3
0.7417	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3225	Approved
0.74	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2403	Approved
0.7394	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6797	Phase 2
0.7378	Intermediate Similarity	NPD5710	Approved
0.7378	Intermediate Similarity	NPD5711	Approved
0.7375	Intermediate Similarity	NPD1465	Phase 2
0.7365	Intermediate Similarity	NPD943	Approved
0.7358	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6100	Approved
0.7351	Intermediate Similarity	NPD6099	Approved
0.7348	Intermediate Similarity	NPD9697	Approved
0.7347	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7458	Discontinued
0.7338	Intermediate Similarity	NPD2309	Approved
0.7338	Intermediate Similarity	NPD3887	Approved
0.7337	Intermediate Similarity	NPD7251	Discontinued
0.7324	Intermediate Similarity	NPD1281	Approved
0.732	Intermediate Similarity	NPD1652	Phase 2
0.7303	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2353	Approved
0.7294	Intermediate Similarity	NPD7808	Phase 3
0.7292	Intermediate Similarity	NPD1876	Approved
0.7288	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7003	Approved
0.7273	Intermediate Similarity	NPD7229	Phase 3
0.7273	Intermediate Similarity	NPD6808	Phase 2
0.7248	Intermediate Similarity	NPD3140	Approved
0.7248	Intermediate Similarity	NPD3142	Approved
0.7241	Intermediate Similarity	NPD1164	Approved
0.7234	Intermediate Similarity	NPD5691	Approved
0.7233	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD5535	Approved
0.7222	Intermediate Similarity	NPD5353	Approved
0.7219	Intermediate Similarity	NPD1729	Discontinued
0.7211	Intermediate Similarity	NPD4908	Phase 1
0.7203	Intermediate Similarity	NPD1610	Phase 2
0.72	Intermediate Similarity	NPD6355	Discontinued
0.7197	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD9261	Approved
0.719	Intermediate Similarity	NPD6004	Phase 3
0.719	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6002	Phase 3
0.719	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6005	Phase 3
0.7183	Intermediate Similarity	NPD1778	Approved
0.7181	Intermediate Similarity	NPD8032	Phase 2
0.7176	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4363	Phase 3
0.7175	Intermediate Similarity	NPD4360	Phase 2
0.7172	Intermediate Similarity	NPD1283	Approved
0.7164	Intermediate Similarity	NPD3134	Approved
0.7163	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD6273	Approved
0.7152	Intermediate Similarity	NPD5049	Phase 3
0.7152	Intermediate Similarity	NPD2186	Approved
0.7135	Intermediate Similarity	NPD6104	Discontinued
0.7135	Intermediate Similarity	NPD4361	Phase 2
0.7135	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2979	Phase 3
0.7126	Intermediate Similarity	NPD5242	Approved
0.7124	Intermediate Similarity	NPD4476	Approved
0.7124	Intermediate Similarity	NPD4477	Approved
0.7115	Intermediate Similarity	NPD2354	Approved
0.7114	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6798	Discontinued
0.7113	Intermediate Similarity	NPD1651	Approved
0.7111	Intermediate Similarity	NPD1358	Approved
0.7108	Intermediate Similarity	NPD7199	Phase 2
0.7099	Intermediate Similarity	NPD6279	Approved
0.7099	Intermediate Similarity	NPD6280	Approved
0.707	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4626	Approved
0.7045	Intermediate Similarity	NPD4287	Approved
0.703	Intermediate Similarity	NPD6971	Discontinued
0.7025	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7390	Discontinued
0.7024	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2438	Suspended
0.7013	Intermediate Similarity	NPD5405	Approved
0.7013	Intermediate Similarity	NPD5404	Approved
0.7013	Intermediate Similarity	NPD5406	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