NPASS Compound

Structure

CID328119 OpenBabel06191716202D 26 28 0 0 0 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 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 1.7321 -0.0000 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 -2.5981 -1.5000 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 -1.7321 0.0000 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 10 2 0 0 0 0 5 12 1 0 0 0 0 6 10 1 0 0 0 0 6 18 2 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 13 1 0 0 0 0 8 15 2 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 15 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 21 2 0 0 0 0 14 23 1 0 0 0 0 15 26 1 0 0 0 0 16 17 2 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.11
Volume:	351.951
LogP:	3.344
LogD:	2.849
LogS:	-4.304
# Rotatable Bonds:	5
TPSA:	87.36
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	2.292
Fsp3:	0.211
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:	-4.753
MDCK Permeability:	3.748391100089066e-05
Pgp-inhibitor:	0.953
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.188

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.037
Plasma Protein Binding (PPB):	77.32061767578125%
Volume Distribution (VD):	0.801
Pgp-substrate:	20.48537826538086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.818
CYP1A2-substrate:	0.978
CYP2C19-inhibitor:	0.599
CYP2C19-substrate:	0.763
CYP2C9-inhibitor:	0.612
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.192
CYP2D6-substrate:	0.938
CYP3A4-inhibitor:	0.733
CYP3A4-substrate:	0.467

ADMET: Excretion

Clearance (CL):	7.377
Half-life (T1/2):	0.46

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.889
AMES Toxicity:	0.297
Rat Oral Acute Toxicity:	0.101
Maximum Recommended Daily Dose:	0.294
Skin Sensitization:	0.292
Carcinogencity:	0.02
Eye Corrosion:	0.004
Eye Irritation:	0.212
Respiratory Toxicity:	0.503

Download Data

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

Natural Product: NPC328119

Natural Product ID:	NPC328119
*Common Name:**	5-Hydroxy-7,2',4',5'-Tetramethoxyflavone
IUPAC Name:	5-hydroxy-7-methoxy-2-(2,4,5-trimethoxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	JZIWGWPCBNNLJD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O7/c1-22-10-5-12(20)19-13(21)8-15(26-18(19)6-10)11-7-16(24-3)17(25-4)9-14(11)23-2/h5-9,20H,1-4H3
SMILES:	COC1=CC(=C2C(=C1)OC(=CC2=O)C3=CC(=C(C=C3OC)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458141
PubChem CID:	10428459
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-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
NPO19	Calliandra californica	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[7798967]
NPO19	Calliandra californica	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	8.0	mm	PMID[572707]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	11.0	mm	PMID[572707]

☑ 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 NPC328119 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	422
0.1-0.2	1874
0.2-0.3	4840
0.3-0.4	11325
0.4-0.5	6263
0.5-0.6	3744
0.6-0.7	4982
0.7-0.8	4777
0.8-0.85	2290
0.85-0.9	1356
0.9-0.95	640
0.95-1	184

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC308451
0.9861	High Similarity	NPC226973
0.9861	High Similarity	NPC208043
0.9859	High Similarity	NPC62536
0.9859	High Similarity	NPC33265
0.9792	High Similarity	NPC306821
0.979	High Similarity	NPC195202
0.9726	High Similarity	NPC160951
0.9726	High Similarity	NPC280937
0.9726	High Similarity	NPC145379
0.9726	High Similarity	NPC274327
0.9726	High Similarity	NPC176775
0.9726	High Similarity	NPC231018
0.9726	High Similarity	NPC255350
0.9726	High Similarity	NPC47781
0.9726	High Similarity	NPC276409
0.9726	High Similarity	NPC246204
0.9726	High Similarity	NPC86485
0.9726	High Similarity	NPC250822
0.9726	High Similarity	NPC69394
0.9726	High Similarity	NPC183878
0.9726	High Similarity	NPC75279
0.9726	High Similarity	NPC22519
0.9722	High Similarity	NPC48479
0.9722	High Similarity	NPC177298
0.972	High Similarity	NPC12200
0.966	High Similarity	NPC167815
0.966	High Similarity	NPC32557
0.966	High Similarity	NPC227325
0.966	High Similarity	NPC4455
0.966	High Similarity	NPC20830
0.966	High Similarity	NPC189960
0.966	High Similarity	NPC280339
0.966	High Similarity	NPC146165
0.966	High Similarity	NPC208197
0.966	High Similarity	NPC92659
0.966	High Similarity	NPC128863
0.966	High Similarity	NPC201136
0.966	High Similarity	NPC213622
0.966	High Similarity	NPC50715
0.966	High Similarity	NPC2476
0.966	High Similarity	NPC256612
0.966	High Similarity	NPC196439
0.966	High Similarity	NPC183597
0.966	High Similarity	NPC138360
0.966	High Similarity	NPC163780
0.9658	High Similarity	NPC188203
0.9658	High Similarity	NPC162313
0.9658	High Similarity	NPC71334
0.9658	High Similarity	NPC241498
0.9658	High Similarity	NPC275836
0.9658	High Similarity	NPC131624
0.9658	High Similarity	NPC198826
0.9658	High Similarity	NPC57030
0.9658	High Similarity	NPC275722
0.9658	High Similarity	NPC83508
0.9658	High Similarity	NPC212678
0.9658	High Similarity	NPC120163
0.9658	High Similarity	NPC301323
0.9658	High Similarity	NPC301123
0.9658	High Similarity	NPC25270
0.9658	High Similarity	NPC156222
0.9658	High Similarity	NPC100887
0.9658	High Similarity	NPC256283
0.9658	High Similarity	NPC293183
0.9658	High Similarity	NPC239128
0.9658	High Similarity	NPC222830
0.9658	High Similarity	NPC187498
0.9655	High Similarity	NPC219330
0.9655	High Similarity	NPC50728
0.9655	High Similarity	NPC166753
0.9653	High Similarity	NPC120464
0.9595	High Similarity	NPC178854
0.9595	High Similarity	NPC100916
0.9595	High Similarity	NPC55619
0.9595	High Similarity	NPC474520
0.9595	High Similarity	NPC200388
0.9595	High Similarity	NPC49824
0.9592	High Similarity	NPC472915
0.9589	High Similarity	NPC117579
0.9589	High Similarity	NPC76376
0.9589	High Similarity	NPC236769
0.9586	High Similarity	NPC287101
0.9586	High Similarity	NPC183950
0.9586	High Similarity	NPC52005
0.9586	High Similarity	NPC223579
0.9586	High Similarity	NPC137062
0.9586	High Similarity	NPC159103
0.953	High Similarity	NPC110070
0.953	High Similarity	NPC224137
0.953	High Similarity	NPC78302
0.953	High Similarity	NPC101830
0.953	High Similarity	NPC189179
0.953	High Similarity	NPC93376
0.953	High Similarity	NPC235215
0.953	High Similarity	NPC75215
0.953	High Similarity	NPC476981
0.953	High Similarity	NPC7973
0.953	High Similarity	NPC203891
0.953	High Similarity	NPC227192
0.953	High Similarity	NPC470402
0.953	High Similarity	NPC472438
0.953	High Similarity	NPC29841
0.9527	High Similarity	NPC201451
0.9527	High Similarity	NPC26227
0.9527	High Similarity	NPC37392
0.9527	High Similarity	NPC472909
0.9527	High Similarity	NPC44079
0.9524	High Similarity	NPC142540
0.9524	High Similarity	NPC60972
0.9524	High Similarity	NPC134677
0.9524	High Similarity	NPC471982
0.9524	High Similarity	NPC39732
0.9521	High Similarity	NPC338131
0.9521	High Similarity	NPC239363
0.9521	High Similarity	NPC184136
0.9521	High Similarity	NPC179183
0.9517	High Similarity	NPC261548
0.9514	High Similarity	NPC110639
0.9514	High Similarity	NPC283002
0.9514	High Similarity	NPC215932
0.9514	High Similarity	NPC302408
0.9514	High Similarity	NPC40818
0.9514	High Similarity	NPC106461
0.9514	High Similarity	NPC14958
0.9507	High Similarity	NPC29536
0.9467	High Similarity	NPC7846
0.9467	High Similarity	NPC300943
0.9467	High Similarity	NPC191459
0.9467	High Similarity	NPC4481
0.9467	High Similarity	NPC176300
0.9467	High Similarity	NPC253634
0.9467	High Similarity	NPC261004
0.9467	High Similarity	NPC25495
0.9467	High Similarity	NPC288669
0.9467	High Similarity	NPC9609
0.9467	High Similarity	NPC19687
0.9467	High Similarity	NPC143828
0.9467	High Similarity	NPC152166
0.9467	High Similarity	NPC204854
0.9467	High Similarity	NPC18772
0.9467	High Similarity	NPC115798
0.9467	High Similarity	NPC18607
0.9467	High Similarity	NPC22472
0.9467	High Similarity	NPC105242
0.9467	High Similarity	NPC130894
0.9463	High Similarity	NPC98661
0.9463	High Similarity	NPC266960
0.9463	High Similarity	NPC292107
0.9463	High Similarity	NPC247017
0.9463	High Similarity	NPC245546
0.9463	High Similarity	NPC43243
0.9463	High Similarity	NPC472916
0.9463	High Similarity	NPC268161
0.9459	High Similarity	NPC236223
0.9459	High Similarity	NPC58382
0.9459	High Similarity	NPC78326
0.9459	High Similarity	NPC179126
0.9459	High Similarity	NPC270620
0.9459	High Similarity	NPC162351
0.9456	High Similarity	NPC262623
0.9456	High Similarity	NPC54394
0.9456	High Similarity	NPC28274
0.9456	High Similarity	NPC50403
0.9456	High Similarity	NPC149614
0.9456	High Similarity	NPC200740
0.9456	High Similarity	NPC133953
0.9456	High Similarity	NPC125062
0.9456	High Similarity	NPC252933
0.9452	High Similarity	NPC17286
0.9452	High Similarity	NPC296197
0.9452	High Similarity	NPC216318
0.9452	High Similarity	NPC259713
0.9448	High Similarity	NPC30647
0.9448	High Similarity	NPC55557
0.9448	High Similarity	NPC119660
0.9448	High Similarity	NPC205522
0.9448	High Similarity	NPC61871
0.9448	High Similarity	NPC93034
0.9448	High Similarity	NPC108406
0.9448	High Similarity	NPC85233
0.9444	High Similarity	NPC165512
0.9441	High Similarity	NPC70853
0.9441	High Similarity	NPC9966
0.9404	High Similarity	NPC476980
0.9404	High Similarity	NPC246478
0.94	High Similarity	NPC472911
0.94	High Similarity	NPC48208
0.94	High Similarity	NPC245758
0.94	High Similarity	NPC223787
0.94	High Similarity	NPC181960
0.94	High Similarity	NPC262286
0.94	High Similarity	NPC156057
0.94	High Similarity	NPC165977
0.94	High Similarity	NPC163524
0.94	High Similarity	NPC217677
0.94	High Similarity	NPC36852
0.94	High Similarity	NPC305663
0.94	High Similarity	NPC300727
0.94	High Similarity	NPC287979

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 NPC328119 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	989
0.2-0.3	1818
0.3-0.4	2674
0.4-0.5	1750
0.5-0.6	977
0.6-0.7	374
0.7-0.8	119
0.8-0.85	37
0.85-0.9	11
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9726	High Similarity	NPD2801	Approved
0.9262	High Similarity	NPD1934	Approved
0.9241	High Similarity	NPD1511	Approved
0.9116	High Similarity	NPD1512	Approved
0.9073	High Similarity	NPD2393	Clinical (unspecified phase)
0.9013	High Similarity	NPD3817	Phase 2
0.8954	High Similarity	NPD3882	Suspended
0.8919	High Similarity	NPD4378	Clinical (unspecified phase)
0.8797	High Similarity	NPD6166	Phase 2
0.8797	High Similarity	NPD6167	Clinical (unspecified phase)
0.8797	High Similarity	NPD6168	Clinical (unspecified phase)
0.875	High Similarity	NPD7054	Approved
0.8696	High Similarity	NPD7472	Approved
0.8688	High Similarity	NPD3818	Discontinued
0.8662	High Similarity	NPD5494	Approved
0.865	High Similarity	NPD4338	Clinical (unspecified phase)
0.858	High Similarity	NPD7074	Phase 3
0.8571	High Similarity	NPD1552	Clinical (unspecified phase)
0.8571	High Similarity	NPD1550	Clinical (unspecified phase)
0.8562	High Similarity	NPD1510	Phase 2
0.8537	High Similarity	NPD7808	Phase 3
0.8528	High Similarity	NPD6797	Phase 2
0.8514	High Similarity	NPD1549	Phase 2
0.8506	High Similarity	NPD4380	Phase 2
0.8503	High Similarity	NPD2796	Approved
0.8476	Intermediate Similarity	NPD7251	Discontinued
0.8471	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD6232	Discontinued
0.8421	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8414	Intermediate Similarity	NPD1240	Approved
0.8395	Intermediate Similarity	NPD7473	Discontinued
0.8389	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD6799	Approved
0.8302	Intermediate Similarity	NPD7075	Discontinued
0.8299	Intermediate Similarity	NPD1607	Approved
0.8293	Intermediate Similarity	NPD5844	Phase 1
0.8291	Intermediate Similarity	NPD5402	Approved
0.8261	Intermediate Similarity	NPD1247	Approved
0.8228	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD7819	Suspended
0.8176	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD6801	Discontinued
0.8148	Intermediate Similarity	NPD6959	Discontinued
0.8133	Intermediate Similarity	NPD2935	Discontinued
0.8113	Intermediate Similarity	NPD1465	Phase 2
0.8101	Intermediate Similarity	NPD7411	Suspended
0.8072	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD3926	Phase 2
0.8041	Intermediate Similarity	NPD943	Approved
0.8039	Intermediate Similarity	NPD3750	Approved
0.8038	Intermediate Similarity	NPD6599	Discontinued
0.8025	Intermediate Similarity	NPD919	Approved
0.7987	Intermediate Similarity	NPD447	Suspended
0.7976	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD2800	Approved
0.7962	Intermediate Similarity	NPD5403	Approved
0.7962	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1551	Phase 2
0.7891	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD230	Phase 1
0.7834	Intermediate Similarity	NPD2532	Approved
0.7834	Intermediate Similarity	NPD2534	Approved
0.7834	Intermediate Similarity	NPD5401	Approved
0.7834	Intermediate Similarity	NPD2533	Approved
0.7824	Intermediate Similarity	NPD6559	Discontinued
0.78	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1613	Approved
0.7791	Intermediate Similarity	NPD7768	Phase 2
0.7784	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6100	Approved
0.7778	Intermediate Similarity	NPD6099	Approved
0.7771	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1933	Approved
0.7744	Intermediate Similarity	NPD3749	Approved
0.7742	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1243	Approved
0.7718	Intermediate Similarity	NPD3027	Phase 3
0.7712	Intermediate Similarity	NPD3748	Approved
0.7697	Intermediate Similarity	NPD6651	Approved
0.7692	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1653	Approved
0.7625	Intermediate Similarity	NPD920	Approved
0.7613	Intermediate Similarity	NPD2344	Approved
0.7605	Intermediate Similarity	NPD7199	Phase 2
0.7597	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4628	Phase 3
0.7572	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1203	Approved
0.7551	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2313	Discontinued
0.7547	Intermediate Similarity	NPD7390	Discontinued
0.7531	Intermediate Similarity	NPD3226	Approved
0.7527	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7484	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4965	Approved
0.747	Intermediate Similarity	NPD4966	Approved
0.747	Intermediate Similarity	NPD4967	Phase 2
0.7468	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD9494	Approved
0.7457	Intermediate Similarity	NPD5953	Discontinued
0.7456	Intermediate Similarity	NPD3787	Discontinued
0.7442	Intermediate Similarity	NPD7286	Phase 2
0.7434	Intermediate Similarity	NPD3268	Approved
0.7421	Intermediate Similarity	NPD2309	Approved
0.7421	Intermediate Similarity	NPD6190	Approved
0.7417	Intermediate Similarity	NPD6832	Phase 2
0.7417	Intermediate Similarity	NPD4908	Phase 1
0.7415	Intermediate Similarity	NPD422	Phase 1
0.7405	Intermediate Similarity	NPD2654	Approved
0.7403	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD2798	Approved
0.7394	Intermediate Similarity	NPD6844	Discontinued
0.7389	Intermediate Similarity	NPD2346	Discontinued
0.7372	Intermediate Similarity	NPD7033	Discontinued
0.7365	Intermediate Similarity	NPD9717	Approved
0.7351	Intermediate Similarity	NPD3018	Phase 2
0.7333	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2797	Approved
0.732	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD5242	Approved
0.731	Intermediate Similarity	NPD5536	Phase 2
0.7305	Intermediate Similarity	NPD5353	Approved
0.7297	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1610	Phase 2
0.7273	Intermediate Similarity	NPD6233	Phase 2
0.7267	Intermediate Similarity	NPD2403	Approved
0.7267	Intermediate Similarity	NPD3225	Approved
0.7261	Intermediate Similarity	NPD4308	Phase 3
0.7253	Intermediate Similarity	NPD4360	Phase 2
0.7253	Intermediate Similarity	NPD4363	Phase 3
0.7251	Intermediate Similarity	NPD5711	Approved
0.7251	Intermediate Similarity	NPD5710	Approved
0.7248	Intermediate Similarity	NPD1608	Approved
0.7248	Intermediate Similarity	NPD9269	Phase 2
0.7247	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2861	Phase 2
0.7229	Intermediate Similarity	NPD6385	Approved
0.7229	Intermediate Similarity	NPD6386	Approved
0.7222	Intermediate Similarity	NPD4357	Discontinued
0.7216	Intermediate Similarity	NPD7685	Pre-registration
0.7211	Intermediate Similarity	NPD9268	Approved
0.7208	Intermediate Similarity	NPD411	Approved
0.72	Intermediate Similarity	NPD4749	Approved
0.72	Intermediate Similarity	NPD2983	Phase 2
0.72	Intermediate Similarity	NPD2982	Phase 2
0.7184	Intermediate Similarity	NPD7228	Approved
0.7178	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7549	Discontinued
0.7174	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7134	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2981	Phase 2
0.7133	Intermediate Similarity	NPD1481	Phase 2
0.712	Intermediate Similarity	NPD4361	Phase 2
0.712	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8434	Phase 2
0.7105	Intermediate Similarity	NPD3267	Approved
0.7105	Intermediate Similarity	NPD3266	Approved
0.7101	Intermediate Similarity	NPD4288	Approved
0.7097	Intermediate Similarity	NPD6798	Discontinued
0.7081	Intermediate Similarity	NPD1652	Phase 2
0.7073	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1535	Discovery
0.7067	Intermediate Similarity	NPD1201	Approved
0.7059	Intermediate Similarity	NPD6778	Approved
0.7059	Intermediate Similarity	NPD6779	Approved
0.7059	Intermediate Similarity	NPD6781	Approved
0.7059	Intermediate Similarity	NPD6780	Approved
0.7059	Intermediate Similarity	NPD6782	Approved
0.7059	Intermediate Similarity	NPD6776	Approved
0.7059	Intermediate Similarity	NPD6777	Approved
0.7052	Intermediate Similarity	NPD7229	Phase 3
0.7047	Intermediate Similarity	NPD17	Approved
0.7039	Intermediate Similarity	NPD8312	Approved
0.7039	Intermediate Similarity	NPD8313	Approved
0.7027	Intermediate Similarity	NPD9545	Approved
0.7024	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7039	Approved
0.7022	Intermediate Similarity	NPD7038	Approved
0.702	Intermediate Similarity	NPD3972	Approved
0.7018	Intermediate Similarity	NPD6971	Discontinued
0.7016	Intermediate Similarity	NPD7584	Approved
0.7007	Intermediate Similarity	NPD9493	Approved
0.7006	Intermediate Similarity	NPD7458	Discontinued
0.7006	Intermediate Similarity	NPD4307	Phase 2
0.7	Intermediate Similarity	NPD3496	Discontinued
0.6993	Remote Similarity	NPD1470	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