NPASS Compound

Structure

NPC43243 OpenBabel07101719142D 23 25 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 2.5981 -1.5000 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 3.4641 -0.0000 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 -0.5000 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 -1.7321 0.0000 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 -0.8660 -0.5000 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 -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 -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 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 -3.4641 -2.0000 0.0000 O 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 1.7321 -2.0000 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 21 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 9 2 0 0 0 0 7 9 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 13 2 0 0 0 0 11 21 1 0 0 0 0 12 14 2 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 20 2 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	314.08
Volume:	308.569
LogP:	2.911
LogD:	2.437
LogS:	-3.84
# Rotatable Bonds:	3
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.723
Synthetic Accessibility Score:	2.273
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.894
MDCK Permeability:	1.8732938769971952e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	92.99935150146484%
Volume Distribution (VD):	0.713
Pgp-substrate:	10.262638092041016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.864
CYP1A2-substrate:	0.943
CYP2C19-inhibitor:	0.403
CYP2C19-substrate:	0.143
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.744
CYP2D6-inhibitor:	0.418
CYP2D6-substrate:	0.281
CYP3A4-inhibitor:	0.396
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	2.634
Half-life (T1/2):	0.839

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.564
Rat Oral Acute Toxicity:	0.25
Maximum Recommended Daily Dose:	0.059
Skin Sensitization:	0.726
Carcinogencity:	0.15
Eye Corrosion:	0.004
Eye Irritation:	0.876
Respiratory Toxicity:	0.148

Download Data

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

Natural Product: NPC43243

Natural Product ID:	NPC43243
*Common Name:**	5,6-Dihydroxy-3,7-Dimethoxyflavone
IUPAC Name:	5,6-dihydroxy-3,7-dimethoxy-2-phenylchromen-4-one
Synonyms:
Standard InCHIKey:	ROUBTGBVCGLQRT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O6/c1-21-11-8-10-12(14(19)13(11)18)15(20)17(22-2)16(23-10)9-6-4-3-5-7-9/h3-8,18-19H,1-2H3
SMILES:	COc1c(oc2c(c1=O)c(O)c(c(c2)OC)O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269544
PubChem CID:	44259724
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
NPO30669	Gnaphalium affine	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10820110]
NPO30669	Gnaphalium affine	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1175	Organism	Spodoptera litura	Spodoptera litura	pED50	=	7.6	n.a.	PMID[570524]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	ED50	=	2.5	10'-7mol/cm2	PMID[570524]

☑ 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 NPC43243 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	480
0.1-0.2	2045
0.2-0.3	5283
0.3-0.4	11455
0.4-0.5	5595
0.5-0.6	4083
0.6-0.7	5142
0.7-0.8	4776
0.8-0.85	1856
0.85-0.9	1104
0.9-0.95	612
0.95-1	266

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC245546
1.0	High Similarity	NPC266960
0.9933	High Similarity	NPC101830
0.9933	High Similarity	NPC176665
0.9933	High Similarity	NPC110070
0.9933	High Similarity	NPC287979
0.9933	High Similarity	NPC163524
0.9933	High Similarity	NPC305663
0.9933	High Similarity	NPC203891
0.9932	High Similarity	NPC44079
0.9932	High Similarity	NPC26227
0.9932	High Similarity	NPC201451
0.9867	High Similarity	NPC261004
0.9867	High Similarity	NPC152166
0.9867	High Similarity	NPC115798
0.9867	High Similarity	NPC22472
0.9867	High Similarity	NPC288669
0.9867	High Similarity	NPC4481
0.9867	High Similarity	NPC18772
0.9867	High Similarity	NPC130894
0.9867	High Similarity	NPC300943
0.9867	High Similarity	NPC9609
0.9867	High Similarity	NPC191459
0.9867	High Similarity	NPC176300
0.9867	High Similarity	NPC253634
0.9867	High Similarity	NPC143828
0.9867	High Similarity	NPC7846
0.9867	High Similarity	NPC25495
0.9867	High Similarity	NPC204854
0.9867	High Similarity	NPC19687
0.9867	High Similarity	NPC105242
0.9867	High Similarity	NPC18607
0.9866	High Similarity	NPC247017
0.9866	High Similarity	NPC49824
0.9866	High Similarity	NPC292107
0.9866	High Similarity	NPC98661
0.98	High Similarity	NPC78302
0.98	High Similarity	NPC224137
0.98	High Similarity	NPC472438
0.98	High Similarity	NPC235215
0.98	High Similarity	NPC7973
0.98	High Similarity	NPC75215
0.98	High Similarity	NPC29841
0.98	High Similarity	NPC227192
0.98	High Similarity	NPC189179
0.98	High Similarity	NPC93376
0.9799	High Similarity	NPC214138
0.9799	High Similarity	NPC189960
0.9799	High Similarity	NPC32557
0.9797	High Similarity	NPC82325
0.9797	High Similarity	NPC275836
0.9797	High Similarity	NPC275722
0.9797	High Similarity	NPC131624
0.9797	High Similarity	NPC241498
0.9797	High Similarity	NPC256283
0.9797	High Similarity	NPC162313
0.9797	High Similarity	NPC212678
0.9797	High Similarity	NPC120163
0.9797	High Similarity	NPC25270
0.9797	High Similarity	NPC279989
0.9797	High Similarity	NPC198826
0.9797	High Similarity	NPC57030
0.9797	High Similarity	NPC239128
0.9797	High Similarity	NPC222830
0.9797	High Similarity	NPC187498
0.9797	High Similarity	NPC71334
0.9797	High Similarity	NPC156222
0.9797	High Similarity	NPC293183
0.9797	High Similarity	NPC83508
0.9797	High Similarity	NPC188203
0.9797	High Similarity	NPC301323
0.9797	High Similarity	NPC100887
0.9797	High Similarity	NPC301123
0.9735	High Similarity	NPC193842
0.9733	High Similarity	NPC265511
0.9733	High Similarity	NPC268161
0.9733	High Similarity	NPC474520
0.9733	High Similarity	NPC55619
0.9733	High Similarity	NPC100916
0.9733	High Similarity	NPC178854
0.9733	High Similarity	NPC200388
0.9732	High Similarity	NPC179126
0.9732	High Similarity	NPC78326
0.9732	High Similarity	NPC86485
0.9732	High Similarity	NPC69394
0.9732	High Similarity	NPC270620
0.9732	High Similarity	NPC183878
0.9732	High Similarity	NPC160951
0.9732	High Similarity	NPC231018
0.9732	High Similarity	NPC22519
0.9732	High Similarity	NPC274327
0.9732	High Similarity	NPC145379
0.9732	High Similarity	NPC236223
0.9732	High Similarity	NPC176775
0.9732	High Similarity	NPC255350
0.9732	High Similarity	NPC47781
0.973	High Similarity	NPC252933
0.973	High Similarity	NPC125062
0.973	High Similarity	NPC200740
0.973	High Similarity	NPC54394
0.973	High Similarity	NPC225731
0.9671	High Similarity	NPC246478
0.9667	High Similarity	NPC92659
0.9667	High Similarity	NPC256612
0.9667	High Similarity	NPC196439
0.9667	High Similarity	NPC227325
0.9667	High Similarity	NPC167815
0.9667	High Similarity	NPC50715
0.9667	High Similarity	NPC20830
0.9667	High Similarity	NPC183597
0.9667	High Similarity	NPC4455
0.9667	High Similarity	NPC128863
0.9667	High Similarity	NPC163780
0.9667	High Similarity	NPC201136
0.9667	High Similarity	NPC146165
0.9667	High Similarity	NPC2476
0.9667	High Similarity	NPC138360
0.9667	High Similarity	NPC280339
0.9667	High Similarity	NPC213622
0.9664	High Similarity	NPC123886
0.9664	High Similarity	NPC27208
0.9664	High Similarity	NPC55205
0.9664	High Similarity	NPC142540
0.9662	High Similarity	NPC184136
0.9662	High Similarity	NPC286342
0.9662	High Similarity	NPC188871
0.9662	High Similarity	NPC306821
0.9662	High Similarity	NPC149127
0.9605	High Similarity	NPC195832
0.96	High Similarity	NPC75279
0.96	High Similarity	NPC246204
0.96	High Similarity	NPC276409
0.96	High Similarity	NPC162351
0.96	High Similarity	NPC250822
0.96	High Similarity	NPC58382
0.9597	High Similarity	NPC28274
0.9597	High Similarity	NPC50403
0.9597	High Similarity	NPC226973
0.9597	High Similarity	NPC133953
0.9597	High Similarity	NPC208043
0.9597	High Similarity	NPC260895
0.9597	High Similarity	NPC236769
0.9595	High Similarity	NPC137062
0.9595	High Similarity	NPC159103
0.9595	High Similarity	NPC296197
0.9595	High Similarity	NPC87125
0.9595	High Similarity	NPC287101
0.9595	High Similarity	NPC195351
0.9595	High Similarity	NPC17286
0.9595	High Similarity	NPC270465
0.9595	High Similarity	NPC259713
0.9595	High Similarity	NPC223579
0.9595	High Similarity	NPC216318
0.9595	High Similarity	NPC183950
0.9595	High Similarity	NPC52005
0.9542	High Similarity	NPC263449
0.9539	High Similarity	NPC470402
0.9536	High Similarity	NPC2928
0.9536	High Similarity	NPC208197
0.9533	High Similarity	NPC134677
0.9533	High Similarity	NPC180234
0.9533	High Similarity	NPC39732
0.9533	High Similarity	NPC120537
0.9533	High Similarity	NPC199100
0.9533	High Similarity	NPC60972
0.953	High Similarity	NPC45873
0.953	High Similarity	NPC50728
0.953	High Similarity	NPC77858
0.953	High Similarity	NPC166753
0.9527	High Similarity	NPC120464
0.9484	High Similarity	NPC470459
0.9481	High Similarity	NPC308992
0.9477	High Similarity	NPC152904
0.9474	High Similarity	NPC235165
0.9474	High Similarity	NPC472916
0.9474	High Similarity	NPC255106
0.947	High Similarity	NPC88645
0.947	High Similarity	NPC292214
0.947	High Similarity	NPC206238
0.947	High Similarity	NPC167091
0.947	High Similarity	NPC271779
0.9467	High Similarity	NPC117579
0.9467	High Similarity	NPC308451
0.9467	High Similarity	NPC76376
0.9463	High Similarity	NPC69752
0.9463	High Similarity	NPC328119
0.9463	High Similarity	NPC48479
0.9463	High Similarity	NPC177298
0.9459	High Similarity	NPC275772
0.9459	High Similarity	NPC239312
0.9459	High Similarity	NPC12200
0.9459	High Similarity	NPC55557
0.9459	High Similarity	NPC108406
0.9459	High Similarity	NPC30647
0.9459	High Similarity	NPC130230
0.9459	High Similarity	NPC61871
0.9427	High Similarity	NPC76482
0.9423	High Similarity	NPC470457
0.9416	High Similarity	NPC476980
0.9412	High Similarity	NPC471479

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 NPC43243 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	450
0.1-0.2	1006
0.2-0.3	1906
0.3-0.4	2679
0.4-0.5	1673
0.5-0.6	954
0.6-0.7	332
0.7-0.8	96
0.8-0.85	34
0.85-0.9	11
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9732	High Similarity	NPD2801	Approved
0.9392	High Similarity	NPD1512	Approved
0.9346	High Similarity	NPD3882	Suspended
0.9276	High Similarity	NPD1934	Approved
0.9257	High Similarity	NPD1511	Approved
0.9156	High Similarity	NPD3817	Phase 2
0.9018	High Similarity	NPD4338	Clinical (unspecified phase)
0.8968	High Similarity	NPD2393	Clinical (unspecified phase)
0.8938	High Similarity	NPD6167	Clinical (unspecified phase)
0.8938	High Similarity	NPD6166	Phase 2
0.8938	High Similarity	NPD6168	Clinical (unspecified phase)
0.8816	High Similarity	NPD4378	Clinical (unspecified phase)
0.878	High Similarity	NPD6797	Phase 2
0.8727	High Similarity	NPD7251	Discontinued
0.8712	High Similarity	NPD3818	Discontinued
0.8675	High Similarity	NPD7808	Phase 3
0.8659	High Similarity	NPD7054	Approved
0.8606	High Similarity	NPD7472	Approved
0.8553	High Similarity	NPD5402	Approved
0.8519	High Similarity	NPD1247	Approved
0.8506	High Similarity	NPD6799	Approved
0.8494	Intermediate Similarity	NPD7074	Phase 3
0.8457	Intermediate Similarity	NPD5494	Approved
0.8447	Intermediate Similarity	NPD7075	Discontinued
0.8385	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8355	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1510	Phase 2
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8302	Intermediate Similarity	NPD4380	Phase 2
0.8301	Intermediate Similarity	NPD1549	Phase 2
0.8242	Intermediate Similarity	NPD6232	Discontinued
0.8221	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7473	Discontinued
0.82	Intermediate Similarity	NPD1240	Approved
0.82	Intermediate Similarity	NPD943	Approved
0.8187	Intermediate Similarity	NPD6599	Discontinued
0.8171	Intermediate Similarity	NPD919	Approved
0.817	Intermediate Similarity	NPD2796	Approved
0.8148	Intermediate Similarity	NPD1465	Phase 2
0.8118	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD5403	Approved
0.8101	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD5401	Approved
0.8092	Intermediate Similarity	NPD1607	Approved
0.8084	Intermediate Similarity	NPD3926	Phase 2
0.8065	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7819	Suspended
0.7908	Intermediate Similarity	NPD230	Phase 1
0.7908	Intermediate Similarity	NPD447	Suspended
0.7879	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3750	Approved
0.7843	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1613	Approved
0.7836	Intermediate Similarity	NPD3751	Discontinued
0.7821	Intermediate Similarity	NPD2935	Discontinued
0.7805	Intermediate Similarity	NPD7411	Suspended
0.7799	Intermediate Similarity	NPD6190	Approved
0.7785	Intermediate Similarity	NPD2800	Approved
0.7751	Intermediate Similarity	NPD6959	Discontinued
0.7707	Intermediate Similarity	NPD1551	Phase 2
0.7706	Intermediate Similarity	NPD3787	Discontinued
0.7679	Intermediate Similarity	NPD3749	Approved
0.7669	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6559	Discontinued
0.7647	Intermediate Similarity	NPD3027	Phase 3
0.7632	Intermediate Similarity	NPD9494	Approved
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1653	Approved
0.7597	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1933	Approved
0.7561	Intermediate Similarity	NPD920	Approved
0.7556	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2344	Approved
0.7546	Intermediate Similarity	NPD2534	Approved
0.7546	Intermediate Similarity	NPD2532	Approved
0.7546	Intermediate Similarity	NPD2533	Approved
0.7532	Intermediate Similarity	NPD3748	Approved
0.7515	Intermediate Similarity	NPD7768	Phase 2
0.7514	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3226	Approved
0.7453	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1243	Approved
0.7442	Intermediate Similarity	NPD7199	Phase 2
0.7439	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6233	Phase 2
0.7427	Intermediate Similarity	NPD6234	Discontinued
0.7421	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4628	Phase 3
0.7386	Intermediate Similarity	NPD1203	Approved
0.738	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6100	Approved
0.7375	Intermediate Similarity	NPD6099	Approved
0.7362	Intermediate Similarity	NPD2309	Approved
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7318	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7314	Intermediate Similarity	NPD2403	Approved
0.7312	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2799	Discontinued
0.7303	Intermediate Similarity	NPD5953	Discontinued
0.7303	Intermediate Similarity	NPD9269	Phase 2
0.7296	Intermediate Similarity	NPD6651	Approved
0.7288	Intermediate Similarity	NPD7286	Phase 2
0.7263	Intermediate Similarity	NPD7685	Pre-registration
0.7261	Intermediate Similarity	NPD6798	Discontinued
0.7253	Intermediate Similarity	NPD8434	Phase 2
0.7237	Intermediate Similarity	NPD422	Phase 1
0.7235	Intermediate Similarity	NPD6844	Discontinued
0.7235	Intermediate Similarity	NPD37	Approved
0.7233	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4967	Phase 2
0.7209	Intermediate Similarity	NPD4966	Approved
0.7209	Intermediate Similarity	NPD4965	Approved
0.7196	Intermediate Similarity	NPD6778	Approved
0.7196	Intermediate Similarity	NPD6776	Approved
0.7196	Intermediate Similarity	NPD6779	Approved
0.7196	Intermediate Similarity	NPD6777	Approved
0.7196	Intermediate Similarity	NPD6782	Approved
0.7196	Intermediate Similarity	NPD6780	Approved
0.7196	Intermediate Similarity	NPD6781	Approved
0.719	Intermediate Similarity	NPD9717	Approved
0.7173	Intermediate Similarity	NPD7435	Discontinued
0.7169	Intermediate Similarity	NPD7390	Discontinued
0.7159	Intermediate Similarity	NPD5242	Approved
0.7152	Intermediate Similarity	NPD2354	Approved
0.7152	Intermediate Similarity	NPD3268	Approved
0.7135	Intermediate Similarity	NPD7228	Approved
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7134	Intermediate Similarity	NPD4908	Phase 1
0.7125	Intermediate Similarity	NPD6355	Discontinued
0.7124	Intermediate Similarity	NPD1610	Phase 2
0.7124	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1471	Phase 3
0.7115	Intermediate Similarity	NPD2798	Approved
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7099	Intermediate Similarity	NPD7033	Discontinued
0.7097	Intermediate Similarity	NPD3225	Approved
0.7091	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1608	Approved
0.7076	Intermediate Similarity	NPD6386	Approved
0.7076	Intermediate Similarity	NPD6385	Approved
0.707	Intermediate Similarity	NPD3018	Phase 2
0.7066	Intermediate Similarity	NPD4357	Discontinued
0.7065	Intermediate Similarity	NPD8150	Discontinued
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7052	Intermediate Similarity	NPD5353	Approved
0.7051	Intermediate Similarity	NPD2797	Approved
0.7044	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD411	Approved
0.7039	Intermediate Similarity	NPD2163	Approved
0.7039	Intermediate Similarity	NPD9268	Approved
0.703	Intermediate Similarity	NPD2654	Approved
0.7024	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4363	Phase 3
0.7021	Intermediate Similarity	NPD4360	Phase 2
0.702	Intermediate Similarity	NPD5536	Phase 2
0.7006	Intermediate Similarity	NPD5711	Approved
0.7006	Intermediate Similarity	NPD5710	Approved
0.6995	Remote Similarity	NPD7697	Approved
0.6995	Remote Similarity	NPD7698	Approved
0.6995	Remote Similarity	NPD8313	Approved
0.6995	Remote Similarity	NPD8312	Approved
0.6995	Remote Similarity	NPD7696	Phase 3
0.6982	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7095	Approved
0.6968	Remote Similarity	NPD1481	Phase 2
0.6962	Remote Similarity	NPD2861	Phase 2
0.6959	Remote Similarity	NPD7871	Phase 2
0.6959	Remote Similarity	NPD228	Approved
0.6959	Remote Similarity	NPD7870	Phase 2
0.6954	Remote Similarity	NPD4288	Approved
0.6954	Remote Similarity	NPD7874	Approved
0.6954	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD3267	Approved
0.6943	Remote Similarity	NPD3266	Approved
0.6943	Remote Similarity	NPD1470	Approved
0.694	Remote Similarity	NPD7549	Discontinued
0.6939	Remote Similarity	NPD7701	Phase 2
0.6931	Remote Similarity	NPD6535	Approved
0.6931	Remote Similarity	NPD6534	Approved
0.6931	Remote Similarity	NPD2899	Discontinued
0.6928	Remote Similarity	NPD1652	Phase 2
0.6923	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2983	Phase 2
0.6923	Remote Similarity	NPD3146	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