NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.08
Volume:	264.902
LogP:	3.771
LogD:	3.136
LogS:	-4.949
# Rotatable Bonds:	2
TPSA:	39.44
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.701
Synthetic Accessibility Score:	1.857
Fsp3:	0.062
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:	-4.698
MDCK Permeability:	1.9336246623424813e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.11
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.109
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.072
Plasma Protein Binding (PPB):	94.43790435791016%
Volume Distribution (VD):	0.496
Pgp-substrate:	4.280845642089844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.915
CYP2C19-inhibitor:	0.92
CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.818
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.158
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.492
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	3.901
Half-life (T1/2):	0.342

ADMET: Toxicity

hERG Blockers:	0.172
Human Hepatotoxicity (H-HT):	0.074
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.816
Rat Oral Acute Toxicity:	0.137
Maximum Recommended Daily Dose:	0.069
Skin Sensitization:	0.444
Carcinogencity:	0.725
Eye Corrosion:	0.014
Eye Irritation:	0.956
Respiratory Toxicity:	0.529

Download Data

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

Natural Product: NPC41721

Natural Product ID:	NPC41721
*Common Name:**	5-Methoxy-2-Phenylchromen-4-One
IUPAC Name:	5-methoxy-2-phenylchromen-4-one
Synonyms:	5-Methoxyflavone
Standard InCHIKey:	XRQSPUXANRGDAV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O3/c1-18-13-8-5-9-14-16(13)12(17)10-15(19-14)11-6-3-2-4-7-11/h2-10H,1H3
SMILES:	COc1cccc2c1c(=O)cc(o2)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL16685
PubChem CID:	94525
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
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499335]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7714541]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760071]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7798964]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964801]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23628	Imperata cylindrica	Species	Poaceae	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
ED50	1
IC50	1
Others	7
Potency	21

Activity Type	# Activity
Individual Protein	24
Organism	2
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT581	Individual Protein	Cyclooxygenase-2	Mus musculus	Inhibition	=	28.0	%	PMID[458715]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	IC50	=	8700.0	nM	PMID[458717]
NPT249	Individual Protein	Glucocorticoid receptor	Homo sapiens	EC150	=	5.5	uM	PMID[458717]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	EC150	=	5.5	uM	PMID[458717]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	39810.7	nM	PMID[458718]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	28183.8	nM	PMID[458718]
NPT2628	Individual Protein	Luciferase	Photuris pennsylvanica	Potency	=	15848.9	nM	PMID[458718]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	44668.4	nM	PMID[458718]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	25118.9	nM	PMID[458718]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	14125.4	nM	PMID[458718]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	35481.3	nM	PMID[458718]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	7943.3	nM	PMID[458718]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	=	10000.0	nM	PMID[458718]
NPT531	Individual Protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	11220.2	nM	PMID[458719]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	31622.8	nM	PMID[458718]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	23778.1	nM	PMID[458719]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	15785.0	nM	PMID[458719]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	37.49	%	PMID[458721]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	29855.4	nM	PMID[458718]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	4448.8	nM	PMID[458719]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	444.9	nM	PMID[458719]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Protection	=	97.0	%	PMID[458716]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED50	=	2.6	mg.kg-1	PMID[458716]
NPT2	Others	Unspecified		Potency	=	3981.1	nM	PMID[458718]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	35481.3	nM	PMID[458718]
NPT2	Others	Unspecified		Potency	=	8912.5	nM	PMID[458718]
NPT2	Others	Unspecified		Inhibition	=	63.89	%	PMID[458720]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	18.33	%	PMID[458721]
NPT2	Others	Unspecified		Potency	n.a.	1995.3	nM	PMID[458719]

☑ 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 NPC41721 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	570
0.1-0.2	2163
0.2-0.3	5774
0.3-0.4	12333
0.4-0.5	4623
0.5-0.6	5320
0.6-0.7	5806
0.7-0.8	3992
0.8-0.85	1519
0.85-0.9	503
0.9-0.95	86
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.96	High Similarity	NPC284424
0.96	High Similarity	NPC278556
0.9597	High Similarity	NPC228184
0.9524	High Similarity	NPC101294
0.9524	High Similarity	NPC473655
0.9449	High Similarity	NPC292998
0.944	High Similarity	NPC39753
0.944	High Similarity	NPC115998
0.9365	High Similarity	NPC137264
0.936	High Similarity	NPC197425
0.935	High Similarity	NPC2771
0.9231	High Similarity	NPC194281
0.9231	High Similarity	NPC47815
0.9231	High Similarity	NPC231772
0.9231	High Similarity	NPC254741
0.9231	High Similarity	NPC473887
0.9231	High Similarity	NPC127447
0.9231	High Similarity	NPC234133
0.9231	High Similarity	NPC61546
0.9231	High Similarity	NPC29353
0.9231	High Similarity	NPC124784
0.9231	High Similarity	NPC72452
0.9231	High Similarity	NPC161196
0.9225	High Similarity	NPC125269
0.9225	High Similarity	NPC66705
0.9206	High Similarity	NPC187907
0.92	High Similarity	NPC475496
0.92	High Similarity	NPC49852
0.916	High Similarity	NPC266597
0.916	High Similarity	NPC250266
0.9154	High Similarity	NPC99854
0.9141	High Similarity	NPC113006
0.9127	High Similarity	NPC473907
0.9127	High Similarity	NPC125887
0.9127	High Similarity	NPC475017
0.9091	High Similarity	NPC17848
0.9091	High Similarity	NPC276905
0.9091	High Similarity	NPC54243
0.9084	High Similarity	NPC13408
0.907	High Similarity	NPC182428
0.907	High Similarity	NPC128216
0.9055	High Similarity	NPC211120
0.9055	High Similarity	NPC473894
0.9048	High Similarity	NPC264428
0.9023	High Similarity	NPC136095
0.9023	High Similarity	NPC78913
0.9023	High Similarity	NPC241838
0.9023	High Similarity	NPC143799
0.9023	High Similarity	NPC18260
0.9023	High Similarity	NPC152042
0.9015	High Similarity	NPC228661
0.9015	High Similarity	NPC103001
0.9015	High Similarity	NPC259685
0.9015	High Similarity	NPC157855
0.9008	High Similarity	NPC46869
0.9008	High Similarity	NPC32298
0.9	High Similarity	NPC274121
0.9	High Similarity	NPC57601
0.9	High Similarity	NPC50898
0.9	High Similarity	NPC213216
0.9	High Similarity	NPC223354
0.9	High Similarity	NPC78540
0.8955	High Similarity	NPC184536
0.8955	High Similarity	NPC159275
0.8955	High Similarity	NPC472409
0.8955	High Similarity	NPC103342
0.8955	High Similarity	NPC230285
0.8955	High Similarity	NPC269652
0.8955	High Similarity	NPC146679
0.8955	High Similarity	NPC59951
0.8955	High Similarity	NPC103904
0.8955	High Similarity	NPC281207
0.8955	High Similarity	NPC150522
0.8955	High Similarity	NPC241100
0.8947	High Similarity	NPC99333
0.8947	High Similarity	NPC201395
0.8947	High Similarity	NPC280284
0.8947	High Similarity	NPC188947
0.8939	High Similarity	NPC240593
0.8931	High Similarity	NPC172262
0.8931	High Similarity	NPC248872
0.8923	High Similarity	NPC229646
0.8915	High Similarity	NPC301717
0.8889	High Similarity	NPC90582
0.8889	High Similarity	NPC214919
0.8889	High Similarity	NPC124467
0.8889	High Similarity	NPC282300
0.8889	High Similarity	NPC262094
0.8889	High Similarity	NPC103362
0.8889	High Similarity	NPC136840
0.8889	High Similarity	NPC110969
0.8881	High Similarity	NPC274784
0.8881	High Similarity	NPC11566
0.8881	High Similarity	NPC329203
0.8881	High Similarity	NPC217186
0.8881	High Similarity	NPC301217
0.8881	High Similarity	NPC55018
0.8881	High Similarity	NPC310135
0.8881	High Similarity	NPC150648
0.8881	High Similarity	NPC20709
0.8881	High Similarity	NPC96565
0.8881	High Similarity	NPC225153
0.8881	High Similarity	NPC220062
0.8881	High Similarity	NPC265871
0.8881	High Similarity	NPC303633
0.8881	High Similarity	NPC53181
0.8881	High Similarity	NPC216978
0.8881	High Similarity	NPC222342
0.8872	High Similarity	NPC275055
0.8872	High Similarity	NPC290291
0.8872	High Similarity	NPC188879
0.8846	High Similarity	NPC64359
0.8846	High Similarity	NPC475589
0.8846	High Similarity	NPC31872
0.8846	High Similarity	NPC473584
0.8846	High Similarity	NPC475008
0.8846	High Similarity	NPC308037
0.8846	High Similarity	NPC186097
0.8846	High Similarity	NPC475009
0.8824	High Similarity	NPC226636
0.8824	High Similarity	NPC70853
0.8824	High Similarity	NPC9966
0.8824	High Similarity	NPC11561
0.8815	High Similarity	NPC474037
0.8815	High Similarity	NPC172986
0.8815	High Similarity	NPC110228
0.8815	High Similarity	NPC261227
0.8815	High Similarity	NPC171094
0.8815	High Similarity	NPC129853
0.8815	High Similarity	NPC188243
0.8815	High Similarity	NPC284550
0.8815	High Similarity	NPC475680
0.8815	High Similarity	NPC270883
0.8815	High Similarity	NPC6407
0.8815	High Similarity	NPC76445
0.8815	High Similarity	NPC305355
0.881	High Similarity	NPC193805
0.8806	High Similarity	NPC118813
0.8806	High Similarity	NPC124269
0.8797	High Similarity	NPC187432
0.8797	High Similarity	NPC256042
0.8797	High Similarity	NPC116775
0.8797	High Similarity	NPC216361
0.8797	High Similarity	NPC281917
0.878	High Similarity	NPC35744
0.8779	High Similarity	NPC10971
0.8779	High Similarity	NPC212631
0.8779	High Similarity	NPC205468
0.8779	High Similarity	NPC25937
0.8779	High Similarity	NPC87231
0.8779	High Similarity	NPC257756
0.8779	High Similarity	NPC129132
0.8769	High Similarity	NPC270369
0.8769	High Similarity	NPC5515
0.8759	High Similarity	NPC113089
0.8759	High Similarity	NPC23955
0.8759	High Similarity	NPC59522
0.8759	High Similarity	NPC470216
0.8759	High Similarity	NPC17262
0.875	High Similarity	NPC298884
0.875	High Similarity	NPC312391
0.875	High Similarity	NPC4743
0.875	High Similarity	NPC156590
0.875	High Similarity	NPC147688
0.875	High Similarity	NPC29536
0.875	High Similarity	NPC22783
0.875	High Similarity	NPC118840
0.875	High Similarity	NPC22467
0.875	High Similarity	NPC213322
0.875	High Similarity	NPC205006
0.875	High Similarity	NPC3188
0.875	High Similarity	NPC324386
0.875	High Similarity	NPC24075
0.875	High Similarity	NPC64908
0.875	High Similarity	NPC52576
0.8741	High Similarity	NPC473209
0.8741	High Similarity	NPC140890
0.8741	High Similarity	NPC261234
0.874	High Similarity	NPC65041
0.8731	High Similarity	NPC299379
0.8731	High Similarity	NPC32441
0.8731	High Similarity	NPC253616
0.8731	High Similarity	NPC79943
0.8731	High Similarity	NPC295261
0.8731	High Similarity	NPC303644
0.8731	High Similarity	NPC243083
0.8731	High Similarity	NPC162680
0.8731	High Similarity	NPC296490
0.8731	High Similarity	NPC476480
0.8731	High Similarity	NPC13768
0.8731	High Similarity	NPC209560
0.8731	High Similarity	NPC294409
0.8731	High Similarity	NPC12296
0.8731	High Similarity	NPC181124
0.8731	High Similarity	NPC7013
0.8731	High Similarity	NPC116632
0.8731	High Similarity	NPC107586
0.8731	High Similarity	NPC84585
0.8731	High Similarity	NPC287246
0.8722	High Similarity	NPC239495

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 NPC41721 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	506
0.1-0.2	993
0.2-0.3	1502
0.3-0.4	2782
0.4-0.5	1902
0.5-0.6	1017
0.6-0.7	304
0.7-0.8	91
0.8-0.85	36
0.85-0.9	16
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD2796	Approved
0.8731	High Similarity	NPD1552	Clinical (unspecified phase)
0.8731	High Similarity	NPD1550	Clinical (unspecified phase)
0.872	High Similarity	NPD1547	Clinical (unspecified phase)
0.8702	High Similarity	NPD1240	Approved
0.8696	High Similarity	NPD4378	Clinical (unspecified phase)
0.8667	High Similarity	NPD1549	Phase 2
0.8582	High Similarity	NPD1510	Phase 2
0.8582	High Similarity	NPD3748	Approved
0.8571	High Similarity	NPD1607	Approved
0.8561	High Similarity	NPD5401	Approved
0.8538	High Similarity	NPD6832	Phase 2
0.8489	Intermediate Similarity	NPD6799	Approved
0.844	Intermediate Similarity	NPD5403	Approved
0.8429	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD1551	Phase 2
0.8357	Intermediate Similarity	NPD1511	Approved
0.8333	Intermediate Similarity	NPD1243	Approved
0.8273	Intermediate Similarity	NPD3750	Approved
0.8244	Intermediate Similarity	NPD2798	Approved
0.8239	Intermediate Similarity	NPD1512	Approved
0.8222	Intermediate Similarity	NPD1933	Approved
0.8219	Intermediate Similarity	NPD2801	Approved
0.8207	Intermediate Similarity	NPD7411	Suspended
0.8168	Intermediate Similarity	NPD3267	Approved
0.8168	Intermediate Similarity	NPD3266	Approved
0.8168	Intermediate Similarity	NPD1203	Approved
0.8163	Intermediate Similarity	NPD3817	Phase 2
0.8156	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD6801	Discontinued
0.8151	Intermediate Similarity	NPD1934	Approved
0.8143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD6599	Discontinued
0.8134	Intermediate Similarity	NPD2313	Discontinued
0.8134	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD7819	Suspended
0.8088	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD9717	Approved
0.8056	Intermediate Similarity	NPD920	Approved
0.8042	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD5402	Approved
0.8041	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.803	Intermediate Similarity	NPD2797	Approved
0.8015	Intermediate Similarity	NPD4307	Phase 2
0.8014	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1241	Discontinued
0.797	Intermediate Similarity	NPD1019	Discontinued
0.7969	Intermediate Similarity	NPD1548	Phase 1
0.7933	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD7075	Discontinued
0.7868	Intermediate Similarity	NPD1296	Phase 2
0.7868	Intermediate Similarity	NPD3268	Approved
0.7867	Intermediate Similarity	NPD7768	Phase 2
0.7867	Intermediate Similarity	NPD3882	Suspended
0.7863	Intermediate Similarity	NPD422	Phase 1
0.7829	Intermediate Similarity	NPD5494	Approved
0.782	Intermediate Similarity	NPD3225	Approved
0.7817	Intermediate Similarity	NPD2654	Approved
0.7817	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD2799	Discontinued
0.7786	Intermediate Similarity	NPD4308	Phase 3
0.7742	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.771	Intermediate Similarity	NPD17	Approved
0.7697	Intermediate Similarity	NPD3749	Approved
0.7692	Intermediate Similarity	NPD2800	Approved
0.7676	Intermediate Similarity	NPD2344	Approved
0.7676	Intermediate Similarity	NPD2346	Discontinued
0.7674	Intermediate Similarity	NPD9493	Approved
0.7669	Intermediate Similarity	NPD3972	Approved
0.766	Intermediate Similarity	NPD7033	Discontinued
0.7647	Intermediate Similarity	NPD919	Approved
0.7628	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6166	Phase 2
0.7628	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD6099	Approved
0.7606	Intermediate Similarity	NPD6100	Approved
0.7606	Intermediate Similarity	NPD2935	Discontinued
0.7595	Intermediate Similarity	NPD7054	Approved
0.7595	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD1610	Phase 2
0.7591	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3226	Approved
0.7564	Intermediate Similarity	NPD3926	Phase 2
0.7556	Intermediate Similarity	NPD1876	Approved
0.7548	Intermediate Similarity	NPD1247	Approved
0.7548	Intermediate Similarity	NPD6959	Discontinued
0.7547	Intermediate Similarity	NPD7472	Approved
0.7537	Intermediate Similarity	NPD1608	Approved
0.7532	Intermediate Similarity	NPD3818	Discontinued
0.7518	Intermediate Similarity	NPD6651	Approved
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7483	Intermediate Similarity	NPD5890	Approved
0.7483	Intermediate Similarity	NPD5889	Approved
0.7482	Intermediate Similarity	NPD411	Approved
0.7466	Intermediate Similarity	NPD2309	Approved
0.7464	Intermediate Similarity	NPD4908	Phase 1
0.7453	Intermediate Similarity	NPD7251	Discontinued
0.7451	Intermediate Similarity	NPD4288	Approved
0.745	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD447	Suspended
0.7438	Intermediate Similarity	NPD7074	Phase 3
0.7432	Intermediate Similarity	NPD4661	Approved
0.7432	Intermediate Similarity	NPD4662	Approved
0.7417	Intermediate Similarity	NPD6585	Discontinued
0.7407	Intermediate Similarity	NPD7808	Phase 3
0.7407	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD9697	Approved
0.7357	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6559	Discontinued
0.7339	Intermediate Similarity	NPD9261	Approved
0.7333	Intermediate Similarity	NPD1201	Approved
0.732	Intermediate Similarity	NPD6844	Discontinued
0.731	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1471	Phase 3
0.7301	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1894	Discontinued
0.729	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD4625	Phase 3
0.7284	Intermediate Similarity	NPD5953	Discontinued
0.7279	Intermediate Similarity	NPD4628	Phase 3
0.7278	Intermediate Similarity	NPD6232	Discontinued
0.7267	Intermediate Similarity	NPD7286	Phase 2
0.7254	Intermediate Similarity	NPD943	Approved
0.7254	Intermediate Similarity	NPD3140	Approved
0.7254	Intermediate Similarity	NPD3142	Approved
0.725	Intermediate Similarity	NPD7473	Discontinued
0.7234	Intermediate Similarity	NPD6798	Discontinued
0.7231	Intermediate Similarity	NPD5535	Approved
0.7226	Intermediate Similarity	NPD4749	Approved
0.7203	Intermediate Similarity	NPD5124	Phase 1
0.7203	Intermediate Similarity	NPD4618	Approved
0.7203	Intermediate Similarity	NPD4622	Approved
0.7203	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2534	Approved
0.72	Intermediate Similarity	NPD2532	Approved
0.72	Intermediate Similarity	NPD2533	Approved
0.7179	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9545	Approved
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD1470	Approved
0.7111	Intermediate Similarity	NPD1651	Approved
0.7111	Intermediate Similarity	NPD5585	Approved
0.7109	Intermediate Similarity	NPD9264	Approved
0.7109	Intermediate Similarity	NPD9263	Approved
0.7109	Intermediate Similarity	NPD9267	Approved
0.7103	Intermediate Similarity	NPD5689	Approved
0.7103	Intermediate Similarity	NPD5688	Approved
0.7099	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6280	Approved
0.7097	Intermediate Similarity	NPD6279	Approved
0.7095	Intermediate Similarity	NPD1652	Phase 2
0.7092	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2403	Approved
0.7075	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2353	Approved
0.7063	Intermediate Similarity	NPD6233	Phase 2
0.7059	Intermediate Similarity	NPD1778	Approved
0.7055	Intermediate Similarity	NPD5844	Phase 1
0.7054	Intermediate Similarity	NPD74	Approved
0.7054	Intermediate Similarity	NPD9266	Approved
0.7032	Intermediate Similarity	NPD2366	Approved
0.7029	Intermediate Similarity	NPD1481	Phase 2
0.7025	Intermediate Similarity	NPD6971	Discontinued
0.7023	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1613	Approved
0.7013	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3887	Approved
0.6993	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD3764	Approved
0.6977	Remote Similarity	NPD4363	Phase 3
0.6977	Remote Similarity	NPD290	Approved
0.6977	Remote Similarity	NPD4360	Phase 2
0.6966	Remote Similarity	NPD6355	Discontinued
0.6963	Remote Similarity	NPD5536	Phase 2
0.696	Remote Similarity	NPD1238	Approved
0.6957	Remote Similarity	NPD1281	Approved
0.6957	Remote Similarity	NPD1535	Discovery
0.6943	Remote Similarity	NPD1465	Phase 2
0.694	Remote Similarity	NPD2557	Approved
0.6936	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD4361	Phase 2
0.6933	Remote Similarity	NPD7003	Approved
0.6928	Remote Similarity	NPD6104	Discontinued
0.6913	Remote Similarity	NPD2897	Discontinued
0.6909	Remote Similarity	NPD1729	Discontinued
0.6908	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7390	Discontinued
0.6903	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3018	Phase 2
0.6899	Remote Similarity	NPD3134	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