NPASS Compound

Structure

CID287275 OpenBabel06191716092D 23 25 0 0 0 0 0 0 0 0999 V2000 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 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 2.5981 1.5000 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 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 -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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 -0.8660 0.5000 0.0000 C 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 10 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 13 15 2 0 0 0 0 14 16 2 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.1
Volume:	317.074
LogP:	2.957
LogD:	3.042
LogS:	-3.98
# Rotatable Bonds:	3
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.75
Synthetic Accessibility Score:	2.101
Fsp3:	0.167
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:	-4.749
MDCK Permeability:	3.140410262858495e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.91
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.749

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	95.39493560791016%
Volume Distribution (VD):	0.525
Pgp-substrate:	3.443037748336792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.907
CYP1A2-substrate:	0.961
CYP2C19-inhibitor:	0.867
CYP2C19-substrate:	0.265
CYP2C9-inhibitor:	0.685
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.517
CYP2D6-substrate:	0.939
CYP3A4-inhibitor:	0.8
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	5.345
Half-life (T1/2):	0.573

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.458
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.051
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.666
Skin Sensitization:	0.179
Carcinogencity:	0.078
Eye Corrosion:	0.007
Eye Irritation:	0.421
Respiratory Toxicity:	0.13

Download Data

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

Natural Product: NPC287275

Natural Product ID:	NPC287275
*Common Name:**	3-(3,4-Dimethoxyphenyl)-7-Hydroxy-4-Methylchromen-2-One
IUPAC Name:	3-(3,4-dimethoxyphenyl)-7-hydroxy-4-methylchromen-2-one
Synonyms:
Standard InCHIKey:	AQGVQGLSKSEDGI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O5/c1-10-13-6-5-12(19)9-15(13)23-18(20)17(10)11-4-7-14(21-2)16(8-11)22-3/h4-9,19H,1-3H3
SMILES:	COc1cc(ccc1OC)c1c(=O)oc2c(c1C)ccc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1528457
PubChem CID:	5393158
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0004154] Hydroxyisoflavonoids

*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
NPO22868	Pulsatilla dahurica	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22868	Pulsatilla dahurica	Species	Ranunculaceae	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
Potency	13

Activity Type	# Activity
Individual Protein	9
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	35481.3	nM	PMID[503754]
NPT61	Individual Protein	Beta-glucocerebrosidase	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[503754]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[503754]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[503754]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	23109.3	nM	PMID[503754]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[503754]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[503754]
NPT105	Individual Protein	Muscleblind-like protein 1	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[503754]
NPT2	Others	Unspecified		Potency	n.a.	14125.4	nM	PMID[503754]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	1778.3	nM	PMID[503754]
NPT2	Others	Unspecified		Potency	n.a.	8912.5	nM	PMID[503754]
NPT2	Others	Unspecified		Potency	n.a.	10000.0	nM	PMID[503754]
NPT2	Others	Unspecified		Potency	n.a.	14581.0	nM	PMID[503754]

☑ 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 NPC287275 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	398
0.1-0.2	1888
0.2-0.3	4621
0.3-0.4	10620
0.4-0.5	6978
0.5-0.6	3772
0.6-0.7	5229
0.7-0.8	4865
0.8-0.85	2604
0.85-0.9	1505
0.9-0.95	211
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9306	High Similarity	NPC139839
0.9241	High Similarity	NPC195202
0.9172	High Similarity	NPC62536
0.9172	High Similarity	NPC33265
0.9172	High Similarity	NPC12200
0.9133	High Similarity	NPC108456
0.9116	High Similarity	NPC50728
0.9116	High Similarity	NPC166753
0.911	High Similarity	NPC107636
0.906	High Similarity	NPC475895
0.9054	High Similarity	NPC236769
0.9054	High Similarity	NPC208043
0.9054	High Similarity	NPC226973
0.9054	High Similarity	NPC308451
0.9048	High Similarity	NPC177298
0.9048	High Similarity	NPC159103
0.9048	High Similarity	NPC183950
0.9048	High Similarity	NPC48479
0.9048	High Similarity	NPC328119
0.9048	High Similarity	NPC137062
0.9048	High Similarity	NPC287101
0.9048	High Similarity	NPC223579
0.9048	High Similarity	NPC52005
0.9007	High Similarity	NPC474886
0.8993	High Similarity	NPC39732
0.8993	High Similarity	NPC60972
0.8993	High Similarity	NPC289968
0.8986	High Similarity	NPC219330
0.8986	High Similarity	NPC306821
0.898	High Similarity	NPC261548
0.898	High Similarity	NPC120464
0.8961	High Similarity	NPC234004
0.8958	High Similarity	NPC34245
0.8958	High Similarity	NPC7439
0.8958	High Similarity	NPC110067
0.8958	High Similarity	NPC256555
0.8958	High Similarity	NPC91492
0.894	High Similarity	NPC54928
0.8933	High Similarity	NPC145379
0.8933	High Similarity	NPC179126
0.8933	High Similarity	NPC255350
0.8933	High Similarity	NPC22519
0.8933	High Similarity	NPC47781
0.8933	High Similarity	NPC86485
0.8933	High Similarity	NPC78326
0.8933	High Similarity	NPC176775
0.8933	High Similarity	NPC236223
0.8933	High Similarity	NPC231018
0.8933	High Similarity	NPC274327
0.8933	High Similarity	NPC160951
0.8933	High Similarity	NPC183878
0.8933	High Similarity	NPC69394
0.8933	High Similarity	NPC270620
0.8926	High Similarity	NPC252933
0.8926	High Similarity	NPC472535
0.8926	High Similarity	NPC474170
0.8926	High Similarity	NPC474388
0.8926	High Similarity	NPC54394
0.8926	High Similarity	NPC76376
0.8926	High Similarity	NPC125062
0.8926	High Similarity	NPC75695
0.8926	High Similarity	NPC200740
0.8921	High Similarity	NPC245120
0.8919	High Similarity	NPC473091
0.8912	High Similarity	NPC108406
0.8912	High Similarity	NPC142863
0.8904	High Similarity	NPC262282
0.8903	High Similarity	NPC142614
0.8897	High Similarity	NPC119663
0.8897	High Similarity	NPC9966
0.8897	High Similarity	NPC70853
0.8896	High Similarity	NPC8300
0.8889	High Similarity	NPC53889
0.8889	High Similarity	NPC110419
0.8874	High Similarity	NPC20830
0.8874	High Similarity	NPC256612
0.8874	High Similarity	NPC201136
0.8874	High Similarity	NPC20541
0.8874	High Similarity	NPC32557
0.8874	High Similarity	NPC50715
0.8874	High Similarity	NPC196439
0.8874	High Similarity	NPC189960
0.8874	High Similarity	NPC227325
0.8874	High Similarity	NPC128863
0.8874	High Similarity	NPC471800
0.8874	High Similarity	NPC92659
0.8874	High Similarity	NPC280339
0.8874	High Similarity	NPC213622
0.8874	High Similarity	NPC2476
0.8874	High Similarity	NPC234255
0.8874	High Similarity	NPC4455
0.8874	High Similarity	NPC146165
0.8874	High Similarity	NPC138360
0.8874	High Similarity	NPC167815
0.8874	High Similarity	NPC183597
0.8874	High Similarity	NPC163780
0.8867	High Similarity	NPC275836
0.8867	High Similarity	NPC279989
0.8867	High Similarity	NPC187498
0.8867	High Similarity	NPC55205
0.8867	High Similarity	NPC301123
0.8867	High Similarity	NPC241498
0.8867	High Similarity	NPC82325
0.8867	High Similarity	NPC57030
0.8867	High Similarity	NPC199773
0.8867	High Similarity	NPC162313
0.8867	High Similarity	NPC71334
0.8867	High Similarity	NPC222830
0.8867	High Similarity	NPC188203
0.8867	High Similarity	NPC257648
0.8867	High Similarity	NPC120163
0.8867	High Similarity	NPC156222
0.8867	High Similarity	NPC83508
0.8867	High Similarity	NPC100887
0.8867	High Similarity	NPC301323
0.8867	High Similarity	NPC275722
0.8867	High Similarity	NPC472912
0.8867	High Similarity	NPC212678
0.8867	High Similarity	NPC471982
0.8867	High Similarity	NPC131624
0.8867	High Similarity	NPC293183
0.8867	High Similarity	NPC256283
0.8867	High Similarity	NPC239128
0.8867	High Similarity	NPC25270
0.8867	High Similarity	NPC477231
0.8867	High Similarity	NPC144162
0.8867	High Similarity	NPC198826
0.8859	High Similarity	NPC177839
0.8859	High Similarity	NPC338131
0.8844	High Similarity	NPC12377
0.8844	High Similarity	NPC476347
0.8836	High Similarity	NPC113089
0.8836	High Similarity	NPC95123
0.8836	High Similarity	NPC66404
0.8836	High Similarity	NPC207732
0.8828	High Similarity	NPC29536
0.8828	High Similarity	NPC312256
0.8824	High Similarity	NPC168616
0.8824	High Similarity	NPC238381
0.8824	High Similarity	NPC87317
0.8824	High Similarity	NPC83763
0.8819	High Similarity	NPC183642
0.8819	High Similarity	NPC170812
0.8819	High Similarity	NPC310370
0.8816	High Similarity	NPC49824
0.8816	High Similarity	NPC265511
0.8816	High Similarity	NPC472455
0.8816	High Similarity	NPC178854
0.8808	High Similarity	NPC58382
0.8808	High Similarity	NPC18727
0.8808	High Similarity	NPC186507
0.8808	High Similarity	NPC276409
0.8808	High Similarity	NPC162351
0.8808	High Similarity	NPC472915
0.8808	High Similarity	NPC246204
0.8808	High Similarity	NPC280937
0.8808	High Similarity	NPC250822
0.8808	High Similarity	NPC75279
0.8803	High Similarity	NPC286843
0.88	High Similarity	NPC50403
0.88	High Similarity	NPC117579
0.88	High Similarity	NPC28274
0.88	High Similarity	NPC31363
0.88	High Similarity	NPC133953
0.8794	High Similarity	NPC111635
0.8794	High Similarity	NPC92830
0.8792	High Similarity	NPC474648
0.8792	High Similarity	NPC87125
0.8792	High Similarity	NPC270465
0.8786	High Similarity	NPC307289
0.8784	High Similarity	NPC476348
0.8784	High Similarity	NPC168803
0.8784	High Similarity	NPC187398
0.8782	High Similarity	NPC85057
0.8782	High Similarity	NPC130920
0.8776	High Similarity	NPC134621
0.8776	High Similarity	NPC136278
0.8776	High Similarity	NPC471590
0.8776	High Similarity	NPC157133
0.8774	High Similarity	NPC471745
0.8774	High Similarity	NPC476372
0.8774	High Similarity	NPC476371
0.8767	High Similarity	NPC134975
0.8766	High Similarity	NPC292415
0.8766	High Similarity	NPC24164
0.8759	High Similarity	NPC472335
0.8759	High Similarity	NPC472332
0.8758	High Similarity	NPC224137
0.8758	High Similarity	NPC160512
0.8758	High Similarity	NPC470402
0.8758	High Similarity	NPC183851
0.8758	High Similarity	NPC63454
0.8758	High Similarity	NPC75215
0.8758	High Similarity	NPC203891
0.8758	High Similarity	NPC68324
0.8758	High Similarity	NPC156818
0.8758	High Similarity	NPC38779
0.8758	High Similarity	NPC183
0.8758	High Similarity	NPC284820
0.8758	High Similarity	NPC93376

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 NPC287275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	387
0.1-0.2	995
0.2-0.3	1750
0.3-0.4	2591
0.4-0.5	1809
0.5-0.6	1036
0.6-0.7	397
0.7-0.8	105
0.8-0.85	53
0.85-0.9	25
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8933	High Similarity	NPD2801	Approved
0.8874	High Similarity	NPD3817	Phase 2
0.8742	High Similarity	NPD1934	Approved
0.8707	High Similarity	NPD1511	Approved
0.8693	High Similarity	NPD4868	Clinical (unspecified phase)
0.8643	High Similarity	NPD6859	Clinical (unspecified phase)
0.8591	High Similarity	NPD1512	Approved
0.8571	High Similarity	NPD3882	Suspended
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.85	High Similarity	NPD5844	Phase 1
0.8456	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD1465	Phase 2
0.8418	Intermediate Similarity	NPD6232	Discontinued
0.84	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD7054	Approved
0.8378	Intermediate Similarity	NPD3750	Approved
0.8367	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7472	Approved
0.8333	Intermediate Similarity	NPD6799	Approved
0.8323	Intermediate Similarity	NPD3818	Discontinued
0.8313	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6166	Phase 2
0.8293	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD7075	Discontinued
0.8261	Intermediate Similarity	NPD422	Phase 1
0.8261	Intermediate Similarity	NPD7473	Discontinued
0.8239	Intermediate Similarity	NPD7199	Phase 2
0.8221	Intermediate Similarity	NPD7074	Phase 3
0.8205	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD7819	Suspended
0.8182	Intermediate Similarity	NPD7808	Phase 3
0.8176	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6797	Phase 2
0.8163	Intermediate Similarity	NPD1510	Phase 2
0.8156	Intermediate Similarity	NPD2797	Approved
0.8141	Intermediate Similarity	NPD6801	Discontinued
0.8137	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3268	Approved
0.8121	Intermediate Similarity	NPD1549	Phase 2
0.8121	Intermediate Similarity	NPD7251	Discontinued
0.8117	Intermediate Similarity	NPD1653	Approved
0.8113	Intermediate Similarity	NPD919	Approved
0.8112	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD2796	Approved
0.8085	Intermediate Similarity	NPD3225	Approved
0.8082	Intermediate Similarity	NPD447	Suspended
0.8082	Intermediate Similarity	NPD230	Phase 1
0.8077	Intermediate Similarity	NPD7411	Suspended
0.8067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8042	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD3748	Approved
0.8039	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1240	Approved
0.8014	Intermediate Similarity	NPD1613	Approved
0.8013	Intermediate Similarity	NPD4380	Phase 2
0.8013	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8013	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD1551	Phase 2
0.795	Intermediate Similarity	NPD5494	Approved
0.7943	Intermediate Similarity	NPD1608	Approved
0.7935	Intermediate Similarity	NPD5403	Approved
0.7931	Intermediate Similarity	NPD3027	Phase 3
0.7925	Intermediate Similarity	NPD5402	Approved
0.7911	Intermediate Similarity	NPD37	Approved
0.7905	Intermediate Similarity	NPD1607	Approved
0.7888	Intermediate Similarity	NPD6234	Discontinued
0.7875	Intermediate Similarity	NPD4966	Approved
0.7875	Intermediate Similarity	NPD4967	Phase 2
0.7875	Intermediate Similarity	NPD4965	Approved
0.7875	Intermediate Similarity	NPD7768	Phase 2
0.7867	Intermediate Similarity	NPD6099	Approved
0.7867	Intermediate Similarity	NPD2935	Discontinued
0.7867	Intermediate Similarity	NPD6100	Approved
0.7843	Intermediate Similarity	NPD6190	Approved
0.7842	Intermediate Similarity	NPD1548	Phase 1
0.7838	Intermediate Similarity	NPD1933	Approved
0.7826	Intermediate Similarity	NPD3749	Approved
0.7812	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD5401	Approved
0.78	Intermediate Similarity	NPD4308	Phase 3
0.78	Intermediate Similarity	NPD7033	Discontinued
0.7778	Intermediate Similarity	NPD3267	Approved
0.7778	Intermediate Similarity	NPD1203	Approved
0.7778	Intermediate Similarity	NPD3266	Approved
0.7762	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1296	Phase 2
0.7755	Intermediate Similarity	NPD6798	Discontinued
0.774	Intermediate Similarity	NPD4908	Phase 1
0.773	Intermediate Similarity	NPD17	Approved
0.7725	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD5124	Phase 1
0.7718	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1652	Phase 2
0.7712	Intermediate Similarity	NPD1243	Approved
0.7697	Intermediate Similarity	NPD3926	Phase 2
0.7692	Intermediate Similarity	NPD2533	Approved
0.7692	Intermediate Similarity	NPD2534	Approved
0.7692	Intermediate Similarity	NPD2532	Approved
0.7671	Intermediate Similarity	NPD3018	Phase 2
0.7662	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD943	Approved
0.7635	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1610	Phase 2
0.7619	Intermediate Similarity	NPD6832	Phase 2
0.7607	Intermediate Similarity	NPD6971	Discontinued
0.76	Intermediate Similarity	NPD6355	Discontinued
0.7595	Intermediate Similarity	NPD920	Approved
0.759	Intermediate Similarity	NPD5242	Approved
0.7588	Intermediate Similarity	NPD6559	Discontinued
0.7584	Intermediate Similarity	NPD6233	Phase 2
0.7576	Intermediate Similarity	NPD1247	Approved
0.7576	Intermediate Similarity	NPD6959	Discontinued
0.7569	Intermediate Similarity	NPD9717	Approved
0.7564	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7228	Approved
0.7551	Intermediate Similarity	NPD9494	Approved
0.7548	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4110	Phase 3
0.7544	Intermediate Similarity	NPD7549	Discontinued
0.7533	Intermediate Similarity	NPD4060	Phase 1
0.7533	Intermediate Similarity	NPD4307	Phase 2
0.7532	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7229	Phase 3
0.7518	Intermediate Similarity	NPD5536	Phase 2
0.7517	Intermediate Similarity	NPD2983	Phase 2
0.7517	Intermediate Similarity	NPD2982	Phase 2
0.7516	Intermediate Similarity	NPD4357	Discontinued
0.7516	Intermediate Similarity	NPD6386	Approved
0.7516	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6385	Approved
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4288	Approved
0.7485	Intermediate Similarity	NPD5353	Approved
0.7485	Intermediate Similarity	NPD7685	Pre-registration
0.7483	Intermediate Similarity	NPD1778	Approved
0.7483	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD8127	Discontinued
0.7468	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3146	Approved
0.7468	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD9545	Approved
0.7451	Intermediate Similarity	NPD2799	Discontinued
0.745	Intermediate Similarity	NPD7095	Approved
0.745	Intermediate Similarity	NPD4625	Phase 3
0.7448	Intermediate Similarity	NPD9269	Phase 2
0.7448	Intermediate Similarity	NPD2981	Phase 2
0.7448	Intermediate Similarity	NPD1481	Phase 2
0.7427	Intermediate Similarity	NPD5953	Discontinued
0.7413	Intermediate Similarity	NPD9268	Approved
0.74	Intermediate Similarity	NPD411	Approved
0.74	Intermediate Similarity	NPD2313	Discontinued
0.7397	Intermediate Similarity	NPD4749	Approved
0.7384	Intermediate Similarity	NPD7038	Approved
0.7384	Intermediate Similarity	NPD7039	Approved
0.7379	Intermediate Similarity	NPD1535	Discovery
0.7372	Intermediate Similarity	NPD2800	Approved
0.7368	Intermediate Similarity	NPD4340	Discontinued
0.7355	Intermediate Similarity	NPD7266	Discontinued
0.7353	Intermediate Similarity	NPD3751	Discontinued
0.7351	Intermediate Similarity	NPD4062	Phase 3
0.7343	Intermediate Similarity	NPD1894	Discontinued
0.7321	Intermediate Similarity	NPD3787	Discontinued
0.731	Intermediate Similarity	NPD3496	Discontinued
0.731	Intermediate Similarity	NPD7286	Phase 2
0.7288	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5535	Approved
0.7285	Intermediate Similarity	NPD3764	Approved
0.7284	Intermediate Similarity	NPD7458	Discontinued
0.7284	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2346	Discontinued
0.7244	Intermediate Similarity	NPD2344	Approved
0.7241	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5283	Phase 1
0.723	Intermediate Similarity	NPD1283	Approved
0.7214	Intermediate Similarity	NPD228	Approved
0.7213	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD8455	Phase 2
0.7208	Intermediate Similarity	NPD6651	Approved
0.7205	Intermediate Similarity	NPD6273	Approved
0.72	Intermediate Similarity	NPD2861	Phase 2
0.7184	Intermediate Similarity	NPD7240	Approved
0.7179	Intermediate Similarity	NPD4476	Approved
0.7179	Intermediate Similarity	NPD4477	Approved
0.7171	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD2354	Approved
0.7159	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2614	Approved
0.7143	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3540	Phase 1

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