NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.09
Volume:	267.538
LogP:	2.772
LogD:	2.871
LogS:	-4.401
# Rotatable Bonds:	2
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.824
Synthetic Accessibility Score:	2.439
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.645
MDCK Permeability:	1.855772097769659e-05
Pgp-inhibitor:	0.916
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.419
Plasma Protein Binding (PPB):	94.63250732421875%
Volume Distribution (VD):	0.559
Pgp-substrate:	3.170912265777588%

ADMET: Metabolism

CYP1A2-inhibitor:	0.902
CYP1A2-substrate:	0.89
CYP2C19-inhibitor:	0.969
CYP2C19-substrate:	0.565
CYP2C9-inhibitor:	0.903
CYP2C9-substrate:	0.873
CYP2D6-inhibitor:	0.468
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.738
CYP3A4-substrate:	0.403

ADMET: Excretion

Clearance (CL):	8.025
Half-life (T1/2):	0.156

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.91
AMES Toxicity:	0.745
Rat Oral Acute Toxicity:	0.323
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.167
Carcinogencity:	0.647
Eye Corrosion:	0.008
Eye Irritation:	0.919
Respiratory Toxicity:	0.787

Download Data

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

Natural Product: NPC228184

Natural Product ID:	NPC228184
*Common Name:**	5-Methoxy-2-Phenyl-2,3-Dihydrochromen-4-One
IUPAC Name:	5-methoxy-2-phenyl-2,3-dihydrochromen-4-one
Synonyms:	5-Methoxyflavanone
Standard InCHIKey:	YLLFUILNISGLHO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O3/c1-18-13-8-5-9-14-16(13)12(17)10-15(19-14)11-6-3-2-4-7-11/h2-9,15H,10H2,1H3
SMILES:	COc1cccc2c1C(=O)CC(O2)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL317869
PubChem CID:	147795
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002590] 5-O-methylated flavonoids

*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
NPO8300	Apis mellifera ligustica	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Others	4
Potency	7

Activity Type	# Activity
Cell Line	2
Individual Protein	6
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	35700.0	nM	PMID[454591]
NPT71	Cell Line	HEK293	Homo sapiens	FC	=	3.6	n.a.	PMID[454593]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	31622.8	nM	PMID[454594]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	31622.8	nM	PMID[454594]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	35481.3	nM	PMID[454594]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	26608.6	nM	PMID[454594]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	5011.9	nM	PMID[454594]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Protection	=	32.0	%	PMID[454592]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	25118.9	nM	PMID[454594]
NPT2	Others	Unspecified		Potency	=	14125.4	nM	PMID[454594]
NPT2	Others	Unspecified		Inhibition	=	108.3	%	PMID[454595]
NPT27	Others	Unspecified		Activity	<=	90.0	%	PMID[454596]

☑ 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 NPC228184 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	395
0.1-0.2	1603
0.2-0.3	4460
0.3-0.4	11966
0.4-0.5	6166
0.5-0.6	4370
0.6-0.7	6644
0.7-0.8	5362
0.8-0.85	1228
0.85-0.9	405
0.9-0.95	93
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9597	High Similarity	NPC41721
0.9535	High Similarity	NPC99854
0.9389	High Similarity	NPC259685
0.9308	High Similarity	NPC125269
0.9248	High Similarity	NPC329203
0.9248	High Similarity	NPC310135
0.9248	High Similarity	NPC150648
0.9248	High Similarity	NPC265871
0.9248	High Similarity	NPC225153
0.9248	High Similarity	NPC274784
0.9248	High Similarity	NPC222342
0.9248	High Similarity	NPC20709
0.9248	High Similarity	NPC11566
0.9231	High Similarity	NPC292998
0.9225	High Similarity	NPC278556
0.9225	High Similarity	NPC284424
0.9179	High Similarity	NPC188243
0.9179	High Similarity	NPC472409
0.9179	High Similarity	NPC6407
0.9179	High Similarity	NPC110228
0.9167	High Similarity	NPC254741
0.9154	High Similarity	NPC473655
0.9154	High Similarity	NPC101294
0.9113	High Similarity	NPC314329
0.9111	High Similarity	NPC22467
0.9111	High Similarity	NPC4743
0.9111	High Similarity	NPC324386
0.9111	High Similarity	NPC213322
0.9111	High Similarity	NPC312391
0.9104	High Similarity	NPC140890
0.9098	High Similarity	NPC287246
0.9098	High Similarity	NPC476480
0.9098	High Similarity	NPC13768
0.9098	High Similarity	NPC296490
0.9098	High Similarity	NPC79943
0.9098	High Similarity	NPC32441
0.9098	High Similarity	NPC107586
0.9098	High Similarity	NPC84585
0.9098	High Similarity	NPC295261
0.9098	High Similarity	NPC12296
0.9098	High Similarity	NPC243083
0.907	High Similarity	NPC39753
0.907	High Similarity	NPC115998
0.9062	High Similarity	NPC475017
0.9044	High Similarity	NPC147145
0.9044	High Similarity	NPC324436
0.9044	High Similarity	NPC194432
0.9044	High Similarity	NPC223500
0.9044	High Similarity	NPC324134
0.9044	High Similarity	NPC265040
0.9044	High Similarity	NPC66515
0.9044	High Similarity	NPC37496
0.9044	High Similarity	NPC182852
0.9044	High Similarity	NPC306829
0.9044	High Similarity	NPC228504
0.9044	High Similarity	NPC1089
0.9044	High Similarity	NPC125855
0.9044	High Similarity	NPC227579
0.9044	High Similarity	NPC296917
0.9044	High Similarity	NPC40833
0.9044	High Similarity	NPC64915
0.9044	High Similarity	NPC166934
0.9044	High Similarity	NPC76372
0.9044	High Similarity	NPC161506
0.9044	High Similarity	NPC148757
0.9044	High Similarity	NPC167624
0.9044	High Similarity	NPC107572
0.9044	High Similarity	NPC220998
0.9044	High Similarity	NPC76338
0.9044	High Similarity	NPC78
0.9044	High Similarity	NPC328164
0.9044	High Similarity	NPC166482
0.9044	High Similarity	NPC32739
0.9044	High Similarity	NPC10937
0.9044	High Similarity	NPC177354
0.9037	High Similarity	NPC76445
0.9037	High Similarity	NPC284550
0.9037	High Similarity	NPC129853
0.903	High Similarity	NPC118813
0.903	High Similarity	NPC329225
0.903	High Similarity	NPC99333
0.903	High Similarity	NPC147686
0.903	High Similarity	NPC280284
0.903	High Similarity	NPC188947
0.903	High Similarity	NPC472460
0.9023	High Similarity	NPC161196
0.9008	High Similarity	NPC182428
0.9	High Similarity	NPC137264
0.8992	High Similarity	NPC197425
0.8984	High Similarity	NPC264428
0.8978	High Similarity	NPC150408
0.8978	High Similarity	NPC149026
0.8978	High Similarity	NPC125894
0.8978	High Similarity	NPC257097
0.8978	High Similarity	NPC169591
0.8978	High Similarity	NPC68104
0.8978	High Similarity	NPC59522
0.8978	High Similarity	NPC221432
0.8978	High Similarity	NPC39329
0.8978	High Similarity	NPC164980
0.8978	High Similarity	NPC310130
0.8978	High Similarity	NPC175504
0.8978	High Similarity	NPC77794
0.8978	High Similarity	NPC278249
0.8978	High Similarity	NPC478086
0.8978	High Similarity	NPC107177
0.8978	High Similarity	NPC85162
0.8978	High Similarity	NPC223812
0.8978	High Similarity	NPC185276
0.8978	High Similarity	NPC143896
0.8978	High Similarity	NPC75049
0.8978	High Similarity	NPC91560
0.8978	High Similarity	NPC214166
0.8978	High Similarity	NPC316816
0.8978	High Similarity	NPC81697
0.8976	High Similarity	NPC2771
0.8971	High Similarity	NPC52576
0.8971	High Similarity	NPC279650
0.8971	High Similarity	NPC96408
0.8971	High Similarity	NPC248372
0.8971	High Similarity	NPC166689
0.8971	High Similarity	NPC17170
0.8971	High Similarity	NPC110038
0.8971	High Similarity	NPC156190
0.8971	High Similarity	NPC3188
0.8971	High Similarity	NPC258630
0.8963	High Similarity	NPC261234
0.8963	High Similarity	NPC136095
0.8955	High Similarity	NPC290291
0.8955	High Similarity	NPC275055
0.8939	High Similarity	NPC223354
0.8915	High Similarity	NPC125887
0.8913	High Similarity	NPC235217
0.8913	High Similarity	NPC197252
0.8913	High Similarity	NPC469764
0.8913	High Similarity	NPC473015
0.8913	High Similarity	NPC131568
0.8913	High Similarity	NPC209040
0.8913	High Similarity	NPC473014
0.8913	High Similarity	NPC131579
0.8913	High Similarity	NPC473013
0.8913	High Similarity	NPC87486
0.8913	High Similarity	NPC124780
0.8913	High Similarity	NPC236766
0.8905	High Similarity	NPC73028
0.8905	High Similarity	NPC202981
0.8897	High Similarity	NPC171094
0.8889	High Similarity	NPC17848
0.8889	High Similarity	NPC124269
0.8881	High Similarity	NPC61546
0.8881	High Similarity	NPC72452
0.8881	High Similarity	NPC231772
0.8881	High Similarity	NPC234133
0.8881	High Similarity	NPC473887
0.8881	High Similarity	NPC29353
0.8881	High Similarity	NPC47815
0.8881	High Similarity	NPC127447
0.8881	High Similarity	NPC194281
0.8881	High Similarity	NPC124784
0.8881	High Similarity	NPC240593
0.8872	High Similarity	NPC66705
0.8871	High Similarity	NPC35744
0.8849	High Similarity	NPC109183
0.8849	High Similarity	NPC470131
0.8849	High Similarity	NPC195621
0.8849	High Similarity	NPC472629
0.8849	High Similarity	NPC470647
0.8849	High Similarity	NPC475052
0.8849	High Similarity	NPC473078
0.8849	High Similarity	NPC470132
0.8849	High Similarity	NPC301276
0.8849	High Similarity	NPC127059
0.8849	High Similarity	NPC20488
0.8849	High Similarity	NPC67805
0.8849	High Similarity	NPC214774
0.8849	High Similarity	NPC267375
0.8849	High Similarity	NPC246948
0.8849	High Similarity	NPC469758
0.8849	High Similarity	NPC142405
0.8849	High Similarity	NPC176229
0.8849	High Similarity	NPC312973
0.8849	High Similarity	NPC111786
0.8849	High Similarity	NPC285630
0.8849	High Similarity	NPC54577
0.8849	High Similarity	NPC470134
0.8849	High Similarity	NPC470133
0.8849	High Similarity	NPC83357
0.8849	High Similarity	NPC88964
0.8846	High Similarity	NPC187907
0.8846	High Similarity	NPC211120
0.8841	High Similarity	NPC113770
0.8837	High Similarity	NPC475496
0.8837	High Similarity	NPC49852
0.8824	High Similarity	NPC316480
0.8824	High Similarity	NPC18260
0.8824	High Similarity	NPC78913
0.8815	High Similarity	NPC228661
0.8815	High Similarity	NPC250266
0.8815	High Similarity	NPC157855
0.8815	High Similarity	NPC103001

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 NPC228184 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	989
0.2-0.3	1412
0.3-0.4	2643
0.4-0.5	1889
0.5-0.6	1235
0.6-0.7	447
0.7-0.8	144
0.8-0.85	23
0.85-0.9	5
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9313	High Similarity	NPD2796	Approved
0.9113	High Similarity	NPD1547	Clinical (unspecified phase)
0.9098	High Similarity	NPD1550	Clinical (unspecified phase)
0.9098	High Similarity	NPD1552	Clinical (unspecified phase)
0.903	High Similarity	NPD1549	Phase 2
0.8647	High Similarity	NPD1240	Approved
0.8529	High Similarity	NPD1510	Phase 2
0.8519	High Similarity	NPD1607	Approved
0.8511	High Similarity	NPD4378	Clinical (unspecified phase)
0.8511	High Similarity	NPD5401	Approved
0.8485	Intermediate Similarity	NPD6832	Phase 2
0.8483	Intermediate Similarity	NPD1934	Approved
0.844	Intermediate Similarity	NPD6799	Approved
0.8425	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD7411	Suspended
0.8394	Intermediate Similarity	NPD3748	Approved
0.8392	Intermediate Similarity	NPD5403	Approved
0.8367	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1551	Phase 2
0.8299	Intermediate Similarity	NPD7819	Suspended
0.8255	Intermediate Similarity	NPD7075	Discontinued
0.8252	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD6801	Discontinued
0.8219	Intermediate Similarity	NPD6599	Discontinued
0.8219	Intermediate Similarity	NPD4380	Phase 2
0.8175	Intermediate Similarity	NPD1933	Approved
0.8156	Intermediate Similarity	NPD1243	Approved
0.8146	Intermediate Similarity	NPD5494	Approved
0.8133	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD3750	Approved
0.8088	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD2798	Approved
0.8056	Intermediate Similarity	NPD1511	Approved
0.8043	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD920	Approved
0.8	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5402	Approved
0.8	Intermediate Similarity	NPD3817	Phase 2
0.7985	Intermediate Similarity	NPD3267	Approved
0.7985	Intermediate Similarity	NPD1203	Approved
0.7985	Intermediate Similarity	NPD3266	Approved
0.7972	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD2313	Discontinued
0.7953	Intermediate Similarity	NPD1241	Discontinued
0.7947	Intermediate Similarity	NPD7768	Phase 2
0.7945	Intermediate Similarity	NPD1512	Approved
0.7935	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD6166	Phase 2
0.7935	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD2801	Approved
0.7926	Intermediate Similarity	NPD1019	Discontinued
0.7902	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD9717	Approved
0.7857	Intermediate Similarity	NPD6959	Discontinued
0.7852	Intermediate Similarity	NPD2797	Approved
0.7842	Intermediate Similarity	NPD4307	Phase 2
0.7829	Intermediate Similarity	NPD3882	Suspended
0.7821	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD1610	Phase 2
0.7786	Intermediate Similarity	NPD1548	Phase 1
0.7785	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3749	Approved
0.7762	Intermediate Similarity	NPD2346	Discontinued
0.7746	Intermediate Similarity	NPD2799	Discontinued
0.7746	Intermediate Similarity	NPD7033	Discontinued
0.7736	Intermediate Similarity	NPD7074	Phase 3
0.7708	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD3268	Approved
0.7698	Intermediate Similarity	NPD1296	Phase 2
0.7692	Intermediate Similarity	NPD6099	Approved
0.7692	Intermediate Similarity	NPD6100	Approved
0.7681	Intermediate Similarity	NPD4908	Phase 1
0.7673	Intermediate Similarity	NPD7054	Approved
0.7669	Intermediate Similarity	NPD17	Approved
0.7655	Intermediate Similarity	NPD2654	Approved
0.7655	Intermediate Similarity	NPD2800	Approved
0.764	Intermediate Similarity	NPD6559	Discontinued
0.7639	Intermediate Similarity	NPD2344	Approved
0.7635	Intermediate Similarity	NPD4661	Approved
0.7635	Intermediate Similarity	NPD4662	Approved
0.763	Intermediate Similarity	NPD3972	Approved
0.7625	Intermediate Similarity	NPD7472	Approved
0.7622	Intermediate Similarity	NPD4308	Phase 3
0.7613	Intermediate Similarity	NPD919	Approved
0.761	Intermediate Similarity	NPD3818	Discontinued
0.7597	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6797	Phase 2
0.7571	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD2935	Discontinued
0.7566	Intermediate Similarity	NPD5889	Approved
0.7566	Intermediate Similarity	NPD5890	Approved
0.7556	Intermediate Similarity	NPD422	Phase 1
0.755	Intermediate Similarity	NPD3226	Approved
0.7532	Intermediate Similarity	NPD3926	Phase 2
0.7531	Intermediate Similarity	NPD7251	Discontinued
0.7518	Intermediate Similarity	NPD3225	Approved
0.7518	Intermediate Similarity	NPD1876	Approved
0.7516	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD9493	Approved
0.7485	Intermediate Similarity	NPD7808	Phase 3
0.7483	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6651	Approved
0.7483	Intermediate Similarity	NPD4628	Phase 3
0.7451	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6798	Discontinued
0.7432	Intermediate Similarity	NPD2309	Approved
0.7432	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4618	Approved
0.7413	Intermediate Similarity	NPD5124	Phase 1
0.7413	Intermediate Similarity	NPD4622	Approved
0.7403	Intermediate Similarity	NPD6844	Discontinued
0.74	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6585	Discontinued
0.7378	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4625	Phase 3
0.7372	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5953	Discontinued
0.7346	Intermediate Similarity	NPD7286	Phase 2
0.7346	Intermediate Similarity	NPD5844	Phase 1
0.7343	Intermediate Similarity	NPD3140	Approved
0.7343	Intermediate Similarity	NPD1613	Approved
0.7343	Intermediate Similarity	NPD3142	Approved
0.7343	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD411	Approved
0.732	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD4749	Approved
0.731	Intermediate Similarity	NPD5688	Approved
0.731	Intermediate Similarity	NPD5689	Approved
0.7308	Intermediate Similarity	NPD4288	Approved
0.7305	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1201	Approved
0.7292	Intermediate Similarity	NPD447	Suspended
0.7285	Intermediate Similarity	NPD2534	Approved
0.7285	Intermediate Similarity	NPD2532	Approved
0.7285	Intermediate Similarity	NPD2533	Approved
0.7279	Intermediate Similarity	NPD1471	Phase 3
0.7259	Intermediate Similarity	NPD1894	Discontinued
0.725	Intermediate Similarity	NPD6232	Discontinued
0.723	Intermediate Similarity	NPD2897	Discontinued
0.7222	Intermediate Similarity	NPD943	Approved
0.7222	Intermediate Similarity	NPD7473	Discontinued
0.7203	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3887	Approved
0.7197	Intermediate Similarity	NPD5535	Approved
0.7183	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1652	Phase 2
0.7179	Intermediate Similarity	NPD6279	Approved
0.7179	Intermediate Similarity	NPD6280	Approved
0.7172	Intermediate Similarity	NPD6355	Discontinued
0.7165	Intermediate Similarity	NPD9261	Approved
0.7153	Intermediate Similarity	NPD6233	Phase 2
0.7152	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4360	Phase 2
0.7151	Intermediate Similarity	NPD4363	Phase 3
0.7143	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD9545	Approved
0.7113	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2861	Phase 2
0.7108	Intermediate Similarity	NPD6104	Discontinued
0.7097	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD1470	Approved
0.708	Intermediate Similarity	NPD5585	Approved
0.708	Intermediate Similarity	NPD1651	Approved
0.7077	Intermediate Similarity	NPD290	Approved
0.7075	Intermediate Similarity	NPD2200	Suspended
0.7073	Intermediate Similarity	NPD3751	Discontinued
0.7073	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2403	Approved
0.7054	Intermediate Similarity	NPD9697	Approved
0.7047	Intermediate Similarity	NPD2353	Approved
0.7047	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6808	Phase 2
0.7037	Intermediate Similarity	NPD2557	Approved
0.7037	Intermediate Similarity	NPD3787	Discontinued
0.7029	Intermediate Similarity	NPD1778	Approved
0.7025	Intermediate Similarity	NPD1465	Phase 2
0.7024	Intermediate Similarity	NPD8313	Approved
0.7024	Intermediate Similarity	NPD8312	Approved
0.702	Intermediate Similarity	NPD7466	Approved
0.7013	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD2424	Discontinued
0.6993	Remote Similarity	NPD7213	Phase 3
0.6993	Remote Similarity	NPD7212	Phase 2
0.6988	Remote Similarity	NPD1729	Discontinued
0.698	Remote Similarity	NPD4477	Approved
0.698	Remote Similarity	NPD4476	Approved
0.6971	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3764	Approved
0.6947	Remote Similarity	NPD9263	Approved
0.6947	Remote Similarity	NPD9264	Approved
0.6947	Remote Similarity	NPD9267	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