NPASS Compound

Structure

NPC93034 OpenBabel07101718322D 27 28 0 0 0 0 0 0 0 0999 V2000 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 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 -1.0000 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 3.4641 3.0000 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 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 3.4641 2.0000 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 1.5000 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 5.1962 2.0000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 17 1 0 0 0 0 13 18 1 0 0 0 0 13 21 2 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 19 2 0 0 0 0 17 25 1 0 0 0 0 18 20 2 0 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.14
Volume:	377.803
LogP:	2.854
LogD:	2.85
LogS:	-4.581
# Rotatable Bonds:	8
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.56
Synthetic Accessibility Score:	2.261
Fsp3:	0.25
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:	-4.661
MDCK Permeability:	1.8421160348225385e-05
Pgp-inhibitor:	0.833
Pgp-substrate:	0.969
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.062
Plasma Protein Binding (PPB):	83.26924133300781%
Volume Distribution (VD):	0.456
Pgp-substrate:	16.308305740356445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.569
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.436
CYP2C19-substrate:	0.828
CYP2C9-inhibitor:	0.25
CYP2C9-substrate:	0.924
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.786
CYP3A4-substrate:	0.7

ADMET: Excretion

Clearance (CL):	8.91
Half-life (T1/2):	0.66

ADMET: Toxicity

hERG Blockers:	0.364
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.666
AMES Toxicity:	0.121
Rat Oral Acute Toxicity:	0.307
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.765
Carcinogencity:	0.117
Eye Corrosion:	0.004
Eye Irritation:	0.641
Respiratory Toxicity:	0.822

Download Data

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

Natural Product: NPC93034

Natural Product ID:	NPC93034
*Common Name:**	2'-Hydroxy-3,4,4',6'-Tetramethoxychalcone
IUPAC Name:	(E)-3-(3,4-dimethoxyphenyl)-1-(6-hydroxy-2,3,4-trimethoxyphenyl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	YYGVWBCOVUSNQT-SOFGYWHQSA-N
Standard InCHI:	InChI=1S/C20H22O7/c1-23-15-9-7-12(10-16(15)24-2)6-8-13(21)18-14(22)11-17(25-3)19(26-4)20(18)27-5/h6-11,22H,1-5H3/b8-6+
SMILES:	COc1ccc(cc1OC)/C=C/C(=O)c1c(O)cc(c(c1OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458376
PubChem CID:	13802644
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO22658	Piper obliquum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18276144]
NPO22658	Piper obliquum	Species	Piperaceae	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
MIC	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	10.0	ug.mL-1	PMID[488702]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	10.0	ug.mL-1	PMID[488702]

☑ 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 NPC93034 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	1666
0.2-0.3	4628
0.3-0.4	11116
0.4-0.5	6560
0.5-0.6	3485
0.6-0.7	5025
0.7-0.8	6032
0.8-0.85	2366
0.85-0.9	1226
0.9-0.95	180
0.95-1	15

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC119660
0.9859	High Similarity	NPC102003
0.9859	High Similarity	NPC92722
0.9789	High Similarity	NPC15329
0.9789	High Similarity	NPC131451
0.9722	High Similarity	NPC262623
0.9714	High Similarity	NPC119663
0.9653	High Similarity	NPC239363
0.9653	High Similarity	NPC156953
0.965	High Similarity	NPC287395
0.965	High Similarity	NPC183655
0.9648	High Similarity	NPC165389
0.9589	High Similarity	NPC124714
0.9589	High Similarity	NPC472915
0.9586	High Similarity	NPC226973
0.9586	High Similarity	NPC308451
0.9586	High Similarity	NPC208043
0.9571	High Similarity	NPC58229
0.9524	High Similarity	NPC20830
0.9524	High Similarity	NPC256612
0.9521	High Similarity	NPC35763
0.9521	High Similarity	NPC100971
0.9521	High Similarity	NPC100263
0.9521	High Similarity	NPC269451
0.9521	High Similarity	NPC291802
0.9521	High Similarity	NPC181209
0.9521	High Similarity	NPC131266
0.9521	High Similarity	NPC209487
0.9521	High Similarity	NPC245382
0.9521	High Similarity	NPC216769
0.9521	High Similarity	NPC121522
0.9517	High Similarity	NPC306821
0.9507	High Similarity	NPC142165
0.9459	High Similarity	NPC472916
0.9456	High Similarity	NPC145379
0.9456	High Similarity	NPC69394
0.9456	High Similarity	NPC255350
0.9456	High Similarity	NPC183878
0.9456	High Similarity	NPC86485
0.9456	High Similarity	NPC274327
0.9456	High Similarity	NPC250557
0.9456	High Similarity	NPC280937
0.9456	High Similarity	NPC231018
0.9456	High Similarity	NPC22519
0.9456	High Similarity	NPC47781
0.9456	High Similarity	NPC176775
0.9456	High Similarity	NPC160951
0.9452	High Similarity	NPC149614
0.9452	High Similarity	NPC45291
0.9452	High Similarity	NPC19980
0.9452	High Similarity	NPC117579
0.9448	High Similarity	NPC328119
0.9437	High Similarity	NPC471417
0.9437	High Similarity	NPC254659
0.9396	High Similarity	NPC476981
0.9396	High Similarity	NPC181960
0.9392	High Similarity	NPC134287
0.9392	High Similarity	NPC213622
0.9392	High Similarity	NPC32557
0.9392	High Similarity	NPC138360
0.9392	High Similarity	NPC37392
0.9392	High Similarity	NPC167815
0.9392	High Similarity	NPC227325
0.9392	High Similarity	NPC183597
0.9392	High Similarity	NPC472909
0.9392	High Similarity	NPC208197
0.9392	High Similarity	NPC163780
0.9392	High Similarity	NPC2476
0.9392	High Similarity	NPC196439
0.9392	High Similarity	NPC128863
0.9392	High Similarity	NPC4455
0.9392	High Similarity	NPC50715
0.9392	High Similarity	NPC280339
0.9392	High Similarity	NPC201136
0.9392	High Similarity	NPC39184
0.9392	High Similarity	NPC146165
0.9392	High Similarity	NPC130589
0.9392	High Similarity	NPC92659
0.9392	High Similarity	NPC2928
0.9392	High Similarity	NPC189960
0.9388	High Similarity	NPC39732
0.9388	High Similarity	NPC188203
0.9388	High Similarity	NPC241498
0.9388	High Similarity	NPC162313
0.9388	High Similarity	NPC120163
0.9388	High Similarity	NPC293183
0.9388	High Similarity	NPC275836
0.9388	High Similarity	NPC222830
0.9388	High Similarity	NPC275722
0.9388	High Similarity	NPC198826
0.9388	High Similarity	NPC187498
0.9388	High Similarity	NPC57030
0.9388	High Similarity	NPC60972
0.9388	High Similarity	NPC83508
0.9388	High Similarity	NPC212678
0.9388	High Similarity	NPC301323
0.9388	High Similarity	NPC239128
0.9388	High Similarity	NPC131624
0.9388	High Similarity	NPC25270
0.9388	High Similarity	NPC71334
0.9388	High Similarity	NPC301123
0.9388	High Similarity	NPC100887
0.9388	High Similarity	NPC256283
0.9388	High Similarity	NPC156222
0.9384	High Similarity	NPC472279
0.9384	High Similarity	NPC179183
0.9384	High Similarity	NPC10467
0.9379	High Similarity	NPC195202
0.9375	High Similarity	NPC195919
0.9375	High Similarity	NPC143903
0.9375	High Similarity	NPC216314
0.9375	High Similarity	NPC12377
0.9375	High Similarity	NPC226987
0.9375	High Similarity	NPC120924
0.9371	High Similarity	NPC207732
0.9366	High Similarity	NPC284556
0.9366	High Similarity	NPC312256
0.9366	High Similarity	NPC301178
0.9357	High Similarity	NPC44573
0.9333	High Similarity	NPC195832
0.9333	High Similarity	NPC190487
0.9333	High Similarity	NPC154304
0.9329	High Similarity	NPC49824
0.9329	High Similarity	NPC178854
0.9324	High Similarity	NPC206238
0.9324	High Similarity	NPC292214
0.9324	High Similarity	NPC75279
0.9324	High Similarity	NPC167091
0.9324	High Similarity	NPC271779
0.9324	High Similarity	NPC88645
0.9324	High Similarity	NPC250822
0.9324	High Similarity	NPC276409
0.9315	High Similarity	NPC195763
0.9315	High Similarity	NPC264550
0.9315	High Similarity	NPC139293
0.9315	High Similarity	NPC69430
0.9315	High Similarity	NPC333691
0.9315	High Similarity	NPC142876
0.9315	High Similarity	NPC264289
0.9315	High Similarity	NPC200060
0.9315	High Similarity	NPC40290
0.931	High Similarity	NPC205522
0.931	High Similarity	NPC33265
0.931	High Similarity	NPC12200
0.931	High Similarity	NPC62536
0.9301	High Similarity	NPC287722
0.9296	High Similarity	NPC110419
0.9286	High Similarity	NPC472364
0.9286	High Similarity	NPC473391
0.9272	High Similarity	NPC188967
0.9272	High Similarity	NPC476980
0.9267	High Similarity	NPC162869
0.9267	High Similarity	NPC472911
0.9267	High Similarity	NPC156057
0.9267	High Similarity	NPC474208
0.9267	High Similarity	NPC475267
0.9267	High Similarity	NPC472914
0.9267	High Similarity	NPC96167
0.9267	High Similarity	NPC472913
0.9267	High Similarity	NPC99597
0.9267	High Similarity	NPC78225
0.9267	High Similarity	NPC78103
0.9267	High Similarity	NPC93376
0.9267	High Similarity	NPC224137
0.9267	High Similarity	NPC222814
0.9267	High Similarity	NPC110070
0.9267	High Similarity	NPC262286
0.9267	High Similarity	NPC210084
0.9267	High Similarity	NPC75215
0.9267	High Similarity	NPC227192
0.9267	High Similarity	NPC203891
0.9267	High Similarity	NPC470402
0.9267	High Similarity	NPC474836
0.9267	High Similarity	NPC472910
0.9267	High Similarity	NPC48208
0.9267	High Similarity	NPC36852
0.9267	High Similarity	NPC101830
0.9267	High Similarity	NPC189179
0.9267	High Similarity	NPC245758
0.9262	High Similarity	NPC255807
0.9262	High Similarity	NPC201451
0.9262	High Similarity	NPC44079
0.9262	High Similarity	NPC26227
0.9262	High Similarity	NPC31018
0.9257	High Similarity	NPC180234
0.9257	High Similarity	NPC161277
0.9257	High Similarity	NPC477231
0.9257	High Similarity	NPC134677
0.9257	High Similarity	NPC120537
0.9257	High Similarity	NPC39007
0.9257	High Similarity	NPC257648
0.9257	High Similarity	NPC101996
0.9257	High Similarity	NPC142540
0.9257	High Similarity	NPC199100
0.9252	High Similarity	NPC45873
0.9252	High Similarity	NPC50728
0.9252	High Similarity	NPC184136
0.9252	High Similarity	NPC166753
0.9247	High Similarity	NPC80710
0.9247	High Similarity	NPC10304

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 NPC93034 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	955
0.2-0.3	1756
0.3-0.4	2669
0.4-0.5	1760
0.5-0.6	1043
0.6-0.7	426
0.7-0.8	139
0.8-0.85	23
0.85-0.9	13
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9456	High Similarity	NPD2801	Approved
0.9073	High Similarity	NPD3882	Suspended
0.9	High Similarity	NPD1934	Approved
0.8844	High Similarity	NPD1511	Approved
0.8816	High Similarity	NPD2393	Clinical (unspecified phase)
0.8794	High Similarity	NPD1240	Approved
0.8725	High Similarity	NPD1512	Approved
0.8681	High Similarity	NPD1510	Phase 2
0.8671	High Similarity	NPD1607	Approved
0.8662	High Similarity	NPD6232	Discontinued
0.8654	High Similarity	NPD5494	Approved
0.8636	High Similarity	NPD3817	Phase 2
0.8616	High Similarity	NPD7473	Discontinued
0.8562	High Similarity	NPD3818	Discontinued
0.8553	High Similarity	NPD6168	Clinical (unspecified phase)
0.8553	High Similarity	NPD6167	Clinical (unspecified phase)
0.8553	High Similarity	NPD6166	Phase 2
0.8533	High Similarity	NPD4378	Clinical (unspecified phase)
0.8531	High Similarity	NPD943	Approved
0.8497	Intermediate Similarity	NPD4380	Phase 2
0.8493	Intermediate Similarity	NPD2935	Discontinued
0.8415	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD7054	Approved
0.8378	Intermediate Similarity	NPD1549	Phase 2
0.8344	Intermediate Similarity	NPD6799	Approved
0.8344	Intermediate Similarity	NPD7472	Approved
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7074	Phase 3
0.8311	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD1247	Approved
0.8243	Intermediate Similarity	NPD2796	Approved
0.8193	Intermediate Similarity	NPD7808	Phase 3
0.8182	Intermediate Similarity	NPD6797	Phase 2
0.8182	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7075	Discontinued
0.8171	Intermediate Similarity	NPD5844	Phase 1
0.817	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD5402	Approved
0.8148	Intermediate Similarity	NPD3926	Phase 2
0.8133	Intermediate Similarity	NPD7251	Discontinued
0.8101	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7819	Suspended
0.8095	Intermediate Similarity	NPD230	Phase 1
0.8095	Intermediate Similarity	NPD447	Suspended
0.8054	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD1465	Phase 2
0.7975	Intermediate Similarity	NPD7411	Suspended
0.7945	Intermediate Similarity	NPD3027	Phase 3
0.7937	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD2532	Approved
0.7935	Intermediate Similarity	NPD2533	Approved
0.7935	Intermediate Similarity	NPD2534	Approved
0.7931	Intermediate Similarity	NPD9494	Approved
0.7925	Intermediate Similarity	NPD6801	Discontinued
0.7902	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD919	Approved
0.7881	Intermediate Similarity	NPD1551	Phase 2
0.7857	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD2800	Approved
0.7815	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6959	Discontinued
0.78	Intermediate Similarity	NPD6651	Approved
0.7792	Intermediate Similarity	NPD3750	Approved
0.777	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD3749	Approved
0.7722	Intermediate Similarity	NPD5403	Approved
0.7712	Intermediate Similarity	NPD2344	Approved
0.7706	Intermediate Similarity	NPD6559	Discontinued
0.7701	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7768	Phase 2
0.7665	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD5536	Phase 2
0.7643	Intermediate Similarity	NPD4357	Discontinued
0.7635	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD6190	Approved
0.7616	Intermediate Similarity	NPD1933	Approved
0.7613	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD920	Approved
0.7605	Intermediate Similarity	NPD5242	Approved
0.7595	Intermediate Similarity	NPD5401	Approved
0.7593	Intermediate Similarity	NPD37	Approved
0.7586	Intermediate Similarity	NPD9269	Phase 2
0.7582	Intermediate Similarity	NPD2799	Discontinued
0.7568	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3018	Phase 2
0.7564	Intermediate Similarity	NPD4628	Phase 3
0.7552	Intermediate Similarity	NPD9268	Approved
0.7551	Intermediate Similarity	NPD1203	Approved
0.755	Intermediate Similarity	NPD1613	Approved
0.755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD5953	Discontinued
0.7532	Intermediate Similarity	NPD7390	Discontinued
0.7531	Intermediate Similarity	NPD6385	Approved
0.7531	Intermediate Similarity	NPD6386	Approved
0.7529	Intermediate Similarity	NPD7286	Phase 2
0.7516	Intermediate Similarity	NPD3226	Approved
0.7516	Intermediate Similarity	NPD2309	Approved
0.7514	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD2654	Approved
0.75	Intermediate Similarity	NPD5353	Approved
0.75	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.747	Intermediate Similarity	NPD6234	Discontinued
0.7468	Intermediate Similarity	NPD3748	Approved
0.7455	Intermediate Similarity	NPD4967	Phase 2
0.7455	Intermediate Similarity	NPD4966	Approved
0.7455	Intermediate Similarity	NPD4965	Approved
0.7453	Intermediate Similarity	NPD1653	Approved
0.7429	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6100	Approved
0.7419	Intermediate Similarity	NPD6099	Approved
0.7417	Intermediate Similarity	NPD2313	Discontinued
0.7415	Intermediate Similarity	NPD2983	Phase 2
0.7415	Intermediate Similarity	NPD2982	Phase 2
0.74	Intermediate Similarity	NPD6832	Phase 2
0.7386	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7199	Phase 2
0.7372	Intermediate Similarity	NPD2346	Discontinued
0.7358	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3972	Approved
0.7347	Intermediate Similarity	NPD2981	Phase 2
0.7347	Intermediate Similarity	NPD9717	Approved
0.7343	Intermediate Similarity	NPD9493	Approved
0.7337	Intermediate Similarity	NPD5710	Approved
0.7337	Intermediate Similarity	NPD5711	Approved
0.7337	Intermediate Similarity	NPD3787	Discontinued
0.7315	Intermediate Similarity	NPD1470	Approved
0.7299	Intermediate Similarity	NPD7685	Pre-registration
0.7294	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6844	Discontinued
0.7257	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD9545	Approved
0.7233	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6781	Approved
0.7228	Intermediate Similarity	NPD6780	Approved
0.7228	Intermediate Similarity	NPD6776	Approved
0.7228	Intermediate Similarity	NPD6779	Approved
0.7228	Intermediate Similarity	NPD6778	Approved
0.7228	Intermediate Similarity	NPD6782	Approved
0.7228	Intermediate Similarity	NPD6777	Approved
0.7195	Intermediate Similarity	NPD7458	Discontinued
0.719	Intermediate Similarity	NPD411	Approved
0.7171	Intermediate Similarity	NPD4908	Phase 1
0.7168	Intermediate Similarity	NPD7228	Approved
0.7162	Intermediate Similarity	NPD422	Phase 1
0.7162	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1201	Approved
0.716	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2403	Approved
0.7133	Intermediate Similarity	NPD5283	Phase 1
0.7128	Intermediate Similarity	NPD2899	Discontinued
0.7123	Intermediate Similarity	NPD1548	Phase 1
0.7114	Intermediate Similarity	NPD1608	Approved
0.7113	Intermediate Similarity	NPD228	Approved
0.7112	Intermediate Similarity	NPD7697	Approved
0.7112	Intermediate Similarity	NPD7698	Approved
0.7112	Intermediate Similarity	NPD7435	Discontinued
0.7112	Intermediate Similarity	NPD7696	Phase 3
0.7103	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8150	Discontinued
0.7095	Intermediate Similarity	NPD8434	Phase 2
0.7089	Intermediate Similarity	NPD5405	Approved
0.7089	Intermediate Similarity	NPD5404	Approved
0.7089	Intermediate Similarity	NPD5408	Approved
0.7089	Intermediate Similarity	NPD5406	Approved
0.7078	Intermediate Similarity	NPD3268	Approved
0.7078	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3764	Approved
0.7074	Intermediate Similarity	NPD7871	Phase 2
0.7074	Intermediate Similarity	NPD7870	Phase 2
0.7047	Intermediate Similarity	NPD1610	Phase 2
0.7044	Intermediate Similarity	NPD3540	Phase 1
0.7032	Intermediate Similarity	NPD6233	Phase 2
0.7025	Intermediate Similarity	NPD4308	Phase 3
0.7025	Intermediate Similarity	NPD7033	Discontinued
0.7022	Intermediate Similarity	NPD8313	Approved
0.7022	Intermediate Similarity	NPD8312	Approved
0.702	Intermediate Similarity	NPD1876	Approved
0.7016	Intermediate Similarity	NPD8151	Discontinued
0.7012	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1481	Phase 2
0.6993	Remote Similarity	NPD2861	Phase 2
0.6988	Remote Similarity	NPD824	Approved
0.6982	Remote Similarity	NPD5977	Approved
0.6982	Remote Similarity	NPD5978	Approved
0.6982	Remote Similarity	NPD2296	Approved
0.6981	Remote Similarity	NPD3539	Phase 1
0.6974	Remote Similarity	NPD2797	Approved
0.6974	Remote Similarity	NPD1164	Approved
0.6973	Remote Similarity	NPD8090	Clinical (unspecified phase)

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