NPASS Compound

Structure

NPC178854 OpenBabel07101719242D 28 30 0 0 0 0 0 0 0 0999 V2000 -4.3301 2.5000 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 4.3301 -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 -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 -3.4641 -0.0000 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 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 1.7321 -2.0000 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 -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 0.8660 -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 -0.8660 -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 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 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 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 0.0000 -0.0000 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 7 2 0 0 0 0 6 10 1 0 0 0 0 7 12 1 0 0 0 0 8 10 2 0 0 0 0 8 13 1 0 0 0 0 9 11 2 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 18 2 0 0 0 0 14 25 1 0 0 0 0 15 16 1 0 0 0 0 15 19 2 0 0 0 0 16 20 1 0 0 0 0 16 22 2 0 0 0 0 17 20 2 0 0 0 0 17 28 1 0 0 0 0 18 19 1 0 0 0 0 18 26 1 0 0 0 0 19 28 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.12
Volume:	378.037
LogP:	2.876
LogD:	2.794
LogS:	-4.353
# Rotatable Bonds:	6
TPSA:	96.59
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.688
Synthetic Accessibility Score:	2.39
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:	-4.641
MDCK Permeability:	3.644003299996257e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	73.9904556274414%
Volume Distribution (VD):	0.922
Pgp-substrate:	28.569034576416016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.374
CYP1A2-substrate:	0.984
CYP2C19-inhibitor:	0.378
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.606
CYP2C9-substrate:	0.905
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.9
CYP3A4-inhibitor:	0.508
CYP3A4-substrate:	0.661

ADMET: Excretion

Clearance (CL):	7.078
Half-life (T1/2):	0.707

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.431
Rat Oral Acute Toxicity:	0.272
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.123
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.079
Respiratory Toxicity:	0.221

Download Data

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

Natural Product: NPC178854

Natural Product ID:	NPC178854
*Common Name:**	8-O-Methylretusin
IUPAC Name:	2-(3,4-dimethoxyphenyl)-5-hydroxy-3,7,8-trimethoxychromen-4-one
Synonyms:	8-O-Methylretusin
Standard InCHIKey:	NPMMYTVKEWLZKD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O8/c1-23-12-7-6-10(8-13(12)24-2)17-20(27-5)16(22)15-11(21)9-14(25-3)18(26-4)19(15)28-17/h6-9,21H,1-5H3
SMILES:	COc1ccc(cc1OC)c1c(c(=O)c2c(cc(c(c2o1)OC)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479326
PubChem CID:	10200272
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002593] 8-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
NPO11253	Knema glomerata	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8201311]
NPO11253	Knema glomerata	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	3
Others	2

Activity Type	# Activity
Cell Line	3
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	27.15	ug ml-1	PMID[458927]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	21.3	ug ml-1	PMID[458927]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	26.34	ug ml-1	PMID[458927]
NPT140	Organism	Artemia	Artemia	LC50	=	56.53	ug.mL-1	PMID[458927]
NPT141	Organism	Agrobacterium tumefaciens	Agrobacterium tumefaciens	T/C	=	52.0	%	PMID[458927]

☑ 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 NPC178854 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	438
0.1-0.2	1925
0.2-0.3	4965
0.3-0.4	11250
0.4-0.5	6158
0.5-0.6	3841
0.6-0.7	5226
0.7-0.8	4696
0.8-0.85	2108
0.85-0.9	1260
0.9-0.95	613
0.95-1	217

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC189960
0.9932	High Similarity	NPC32557
0.9867	High Similarity	NPC152166
0.9867	High Similarity	NPC261004
0.9867	High Similarity	NPC115798
0.9867	High Similarity	NPC22472
0.9867	High Similarity	NPC4481
0.9867	High Similarity	NPC130894
0.9867	High Similarity	NPC300943
0.9867	High Similarity	NPC9609
0.9867	High Similarity	NPC191459
0.9867	High Similarity	NPC18772
0.9867	High Similarity	NPC288669
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
0.9865	High Similarity	NPC246204
0.9865	High Similarity	NPC86485
0.98	High Similarity	NPC78302
0.98	High Similarity	NPC224137
0.98	High Similarity	NPC176665
0.98	High Similarity	NPC472438
0.98	High Similarity	NPC7973
0.98	High Similarity	NPC305663
0.98	High Similarity	NPC75215
0.98	High Similarity	NPC287979
0.98	High Similarity	NPC29841
0.98	High Similarity	NPC203891
0.98	High Similarity	NPC163524
0.98	High Similarity	NPC93376
0.98	High Similarity	NPC110070
0.98	High Similarity	NPC227192
0.98	High Similarity	NPC235215
0.98	High Similarity	NPC189179
0.98	High Similarity	NPC101830
0.9797	High Similarity	NPC134677
0.9797	High Similarity	NPC301123
0.9735	High Similarity	NPC193842
0.9733	High Similarity	NPC49824
0.9733	High Similarity	NPC266960
0.9733	High Similarity	NPC268161
0.9733	High Similarity	NPC98661
0.9733	High Similarity	NPC43243
0.9733	High Similarity	NPC100916
0.9733	High Similarity	NPC292107
0.9733	High Similarity	NPC474520
0.9733	High Similarity	NPC55619
0.9733	High Similarity	NPC247017
0.9733	High Similarity	NPC200388
0.9733	High Similarity	NPC245546
0.973	High Similarity	NPC208043
0.973	High Similarity	NPC236769
0.973	High Similarity	NPC226973
0.973	High Similarity	NPC76376
0.9667	High Similarity	NPC146165
0.9667	High Similarity	NPC26227
0.9667	High Similarity	NPC201451
0.9667	High Similarity	NPC196439
0.9667	High Similarity	NPC50715
0.9667	High Similarity	NPC183597
0.9667	High Similarity	NPC4455
0.9667	High Similarity	NPC128863
0.9667	High Similarity	NPC44079
0.9667	High Similarity	NPC214138
0.9667	High Similarity	NPC163780
0.9667	High Similarity	NPC201136
0.9667	High Similarity	NPC227325
0.9667	High Similarity	NPC167815
0.9667	High Similarity	NPC2476
0.9667	High Similarity	NPC92659
0.9667	High Similarity	NPC138360
0.9667	High Similarity	NPC280339
0.9662	High Similarity	NPC259058
0.9662	High Similarity	NPC50728
0.9662	High Similarity	NPC201547
0.9662	High Similarity	NPC166753
0.9662	High Similarity	NPC306821
0.9662	High Similarity	NPC219330
0.9603	High Similarity	NPC265511
0.96	High Similarity	NPC236223
0.96	High Similarity	NPC255350
0.96	High Similarity	NPC75279
0.96	High Similarity	NPC160951
0.96	High Similarity	NPC231018
0.96	High Similarity	NPC274327
0.96	High Similarity	NPC183878
0.96	High Similarity	NPC145379
0.96	High Similarity	NPC276409
0.96	High Similarity	NPC176775
0.96	High Similarity	NPC162351
0.96	High Similarity	NPC69394
0.96	High Similarity	NPC78326
0.96	High Similarity	NPC250822
0.96	High Similarity	NPC58382
0.96	High Similarity	NPC270620
0.96	High Similarity	NPC179126
0.96	High Similarity	NPC47781
0.96	High Similarity	NPC22519
0.9597	High Similarity	NPC308451
0.9595	High Similarity	NPC69752
0.9595	High Similarity	NPC159103
0.9595	High Similarity	NPC181250
0.9595	High Similarity	NPC328119
0.9542	High Similarity	NPC246478
0.9536	High Similarity	NPC20830
0.9536	High Similarity	NPC256612
0.9536	High Similarity	NPC213622
0.9536	High Similarity	NPC208197
0.9533	High Similarity	NPC100887
0.9533	High Similarity	NPC222830
0.9533	High Similarity	NPC131624
0.9533	High Similarity	NPC239128
0.9533	High Similarity	NPC198826
0.9533	High Similarity	NPC293183
0.9533	High Similarity	NPC187498
0.9533	High Similarity	NPC212678
0.9533	High Similarity	NPC57030
0.9533	High Similarity	NPC162313
0.9533	High Similarity	NPC25270
0.9533	High Similarity	NPC279989
0.9533	High Similarity	NPC123886
0.9533	High Similarity	NPC275722
0.9533	High Similarity	NPC156222
0.9533	High Similarity	NPC83508
0.9533	High Similarity	NPC27208
0.9533	High Similarity	NPC256283
0.9533	High Similarity	NPC82325
0.9533	High Similarity	NPC71334
0.9533	High Similarity	NPC120163
0.9533	High Similarity	NPC188203
0.9533	High Similarity	NPC301323
0.9533	High Similarity	NPC241498
0.9533	High Similarity	NPC275836
0.9533	High Similarity	NPC142540
0.9527	High Similarity	NPC195202
0.9527	High Similarity	NPC261548
0.9484	High Similarity	NPC470459
0.9477	High Similarity	NPC195832
0.9477	High Similarity	NPC152904
0.947	High Similarity	NPC280937
0.947	High Similarity	NPC472915
0.9467	High Similarity	NPC125062
0.9467	High Similarity	NPC252933
0.9467	High Similarity	NPC117579
0.9467	High Similarity	NPC225731
0.9467	High Similarity	NPC54394
0.9467	High Similarity	NPC28274
0.9467	High Similarity	NPC50403
0.9467	High Similarity	NPC200740
0.9467	High Similarity	NPC133953
0.9459	High Similarity	NPC12200
0.9459	High Similarity	NPC33265
0.9459	High Similarity	NPC62536
0.9459	High Similarity	NPC85233
0.9427	High Similarity	NPC76482
0.9423	High Similarity	NPC470457
0.9412	High Similarity	NPC470402
0.9412	High Similarity	NPC476981
0.9408	High Similarity	NPC37392
0.9408	High Similarity	NPC241774
0.9408	High Similarity	NPC276059
0.9408	High Similarity	NPC34725
0.9408	High Similarity	NPC122623
0.9408	High Similarity	NPC472909
0.9404	High Similarity	NPC60972
0.9404	High Similarity	NPC39732
0.9404	High Similarity	NPC55205
0.94	High Similarity	NPC286342
0.94	High Similarity	NPC184136
0.94	High Similarity	NPC188871
0.94	High Similarity	NPC77858
0.94	High Similarity	NPC149127
0.9392	High Similarity	NPC215932
0.9392	High Similarity	NPC40818
0.9392	High Similarity	NPC14958
0.9392	High Similarity	NPC110639
0.9392	High Similarity	NPC302408
0.9392	High Similarity	NPC283002
0.9392	High Similarity	NPC106461
0.9392	High Similarity	NPC310259
0.9367	High Similarity	NPC280493
0.9363	High Similarity	NPC470462
0.9351	High Similarity	NPC154304
0.9351	High Similarity	NPC190487
0.9346	High Similarity	NPC257277
0.9346	High Similarity	NPC303255
0.9346	High Similarity	NPC472916
0.9342	High Similarity	NPC476289
0.9338	High Similarity	NPC149614
0.9338	High Similarity	NPC262623
0.9338	High Similarity	NPC260895
0.9333	High Similarity	NPC48479
0.9333	High Similarity	NPC17286
0.9333	High Similarity	NPC259713

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 NPC178854 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	994
0.2-0.3	1793
0.3-0.4	2648
0.4-0.5	1788
0.5-0.6	981
0.6-0.7	375
0.7-0.8	111
0.8-0.85	34
0.85-0.9	14
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.96	High Similarity	NPD2801	Approved
0.9281	High Similarity	NPD3817	Phase 2
0.9221	High Similarity	NPD3882	Suspended
0.9133	High Similarity	NPD1512	Approved
0.9026	High Similarity	NPD1934	Approved
0.9018	High Similarity	NPD4338	Clinical (unspecified phase)
0.9	High Similarity	NPD1511	Approved
0.894	High Similarity	NPD4378	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)
0.8846	High Similarity	NPD2393	Clinical (unspecified phase)
0.8788	High Similarity	NPD7808	Phase 3
0.878	High Similarity	NPD6797	Phase 2
0.8727	High Similarity	NPD7251	Discontinued
0.8712	High Similarity	NPD3818	Discontinued
0.8671	High Similarity	NPD5402	Approved
0.8659	High Similarity	NPD7054	Approved
0.8606	High Similarity	NPD7472	Approved
0.8571	High Similarity	NPD5494	Approved
0.8562	High Similarity	NPD7075	Discontinued
0.8519	High Similarity	NPD1247	Approved
0.8506	High Similarity	NPD6799	Approved
0.8494	Intermediate Similarity	NPD7074	Phase 3
0.8466	Intermediate Similarity	NPD6232	Discontinued
0.8428	Intermediate Similarity	NPD6801	Discontinued
0.8424	Intermediate Similarity	NPD7473	Discontinued
0.8418	Intermediate Similarity	NPD4380	Phase 2
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
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD3926	Phase 2
0.8301	Intermediate Similarity	NPD1549	Phase 2
0.8289	Intermediate Similarity	NPD2796	Approved
0.8228	Intermediate Similarity	NPD5403	Approved
0.82	Intermediate Similarity	NPD1240	Approved
0.8187	Intermediate Similarity	NPD6599	Discontinued
0.8171	Intermediate Similarity	NPD919	Approved
0.8148	Intermediate Similarity	NPD7819	Suspended
0.8118	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD5844	Phase 1
0.8101	Intermediate Similarity	NPD5401	Approved
0.8098	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1607	Approved
0.8065	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD1465	Phase 2
0.8025	Intermediate Similarity	NPD7411	Suspended
0.7964	Intermediate Similarity	NPD6959	Discontinued
0.7961	Intermediate Similarity	NPD943	Approved
0.7935	Intermediate Similarity	NPD2935	Discontinued
0.7908	Intermediate Similarity	NPD447	Suspended
0.7888	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD3750	Approved
0.7799	Intermediate Similarity	NPD6190	Approved
0.7785	Intermediate Similarity	NPD2800	Approved
0.7765	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6559	Discontinued
0.7756	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3751	Discontinued
0.7719	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1551	Phase 2
0.7706	Intermediate Similarity	NPD3787	Discontinued
0.7697	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD3749	Approved
0.7677	Intermediate Similarity	NPD230	Phase 1
0.7667	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2534	Approved
0.7654	Intermediate Similarity	NPD2532	Approved
0.7654	Intermediate Similarity	NPD2533	Approved
0.7632	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1653	Approved
0.7619	Intermediate Similarity	NPD7768	Phase 2
0.7613	Intermediate Similarity	NPD1613	Approved
0.7613	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3226	Approved
0.7568	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD1933	Approved
0.7562	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD920	Approved
0.7556	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2344	Approved
0.7544	Intermediate Similarity	NPD7199	Phase 2
0.7532	Intermediate Similarity	NPD3748	Approved
0.7532	Intermediate Similarity	NPD3027	Phase 3
0.7516	Intermediate Similarity	NPD6651	Approved
0.75	Intermediate Similarity	NPD5953	Discontinued
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7484	Intermediate Similarity	NPD6099	Approved
0.7453	Intermediate Similarity	NPD1243	Approved
0.744	Intermediate Similarity	NPD37	Approved
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	NPD2799	Discontinued
0.7421	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD2403	Approved
0.7412	Intermediate Similarity	NPD4967	Phase 2
0.7412	Intermediate Similarity	NPD4965	Approved
0.7412	Intermediate Similarity	NPD4966	Approved
0.7407	Intermediate Similarity	NPD4628	Phase 3
0.7405	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD9494	Approved
0.7386	Intermediate Similarity	NPD1203	Approved
0.7386	Intermediate Similarity	NPD7286	Phase 2
0.7378	Intermediate Similarity	NPD7390	Discontinued
0.7368	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2309	Approved
0.7355	Intermediate Similarity	NPD6832	Phase 2
0.7348	Intermediate Similarity	NPD8434	Phase 2
0.7337	Intermediate Similarity	NPD6844	Discontinued
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7317	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1548	Phase 1
0.7314	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3018	Phase 2
0.7287	Intermediate Similarity	NPD6779	Approved
0.7287	Intermediate Similarity	NPD6780	Approved
0.7287	Intermediate Similarity	NPD6778	Approved
0.7287	Intermediate Similarity	NPD6777	Approved
0.7287	Intermediate Similarity	NPD6776	Approved
0.7287	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD6782	Approved
0.7263	Intermediate Similarity	NPD7685	Pre-registration
0.7263	Intermediate Similarity	NPD7435	Discontinued
0.7261	Intermediate Similarity	NPD3268	Approved
0.7261	Intermediate Similarity	NPD6798	Discontinued
0.7257	Intermediate Similarity	NPD5242	Approved
0.7244	Intermediate Similarity	NPD4908	Phase 1
0.7237	Intermediate Similarity	NPD422	Phase 1
0.7233	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2798	Approved
0.7205	Intermediate Similarity	NPD7033	Discontinued
0.7195	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD9717	Approved
0.7176	Intermediate Similarity	NPD6386	Approved
0.7176	Intermediate Similarity	NPD6385	Approved
0.7173	Intermediate Similarity	NPD7697	Approved
0.7173	Intermediate Similarity	NPD7696	Phase 3
0.7173	Intermediate Similarity	NPD7698	Approved
0.7169	Intermediate Similarity	NPD4357	Discontinued
0.7161	Intermediate Similarity	NPD2797	Approved
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7152	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD2983	Phase 2
0.7143	Intermediate Similarity	NPD2982	Phase 2
0.7135	Intermediate Similarity	NPD7870	Phase 2
0.7135	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD7871	Phase 2
0.7134	Intermediate Similarity	NPD2654	Approved
0.7133	Intermediate Similarity	NPD5536	Phase 2
0.7125	Intermediate Similarity	NPD6355	Discontinued
0.7124	Intermediate Similarity	NPD1610	Phase 2
0.7124	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1471	Phase 3
0.7112	Intermediate Similarity	NPD4360	Phase 2
0.7112	Intermediate Similarity	NPD4363	Phase 3
0.7102	Intermediate Similarity	NPD5710	Approved
0.7102	Intermediate Similarity	NPD5711	Approved
0.7099	Intermediate Similarity	NPD4308	Phase 3
0.7097	Intermediate Similarity	NPD3225	Approved
0.7088	Intermediate Similarity	NPD8312	Approved
0.7088	Intermediate Similarity	NPD8313	Approved
0.7078	Intermediate Similarity	NPD1608	Approved
0.7078	Intermediate Similarity	NPD9269	Phase 2
0.7078	Intermediate Similarity	NPD2981	Phase 2
0.707	Intermediate Similarity	NPD2861	Phase 2
0.7063	Intermediate Similarity	NPD4060	Phase 1
0.7048	Intermediate Similarity	NPD2354	Approved
0.7044	Intermediate Similarity	NPD411	Approved
0.7041	Intermediate Similarity	NPD7874	Approved
0.7041	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2163	Approved
0.7039	Intermediate Similarity	NPD9268	Approved
0.7033	Intermediate Similarity	NPD7549	Discontinued
0.7026	Intermediate Similarity	NPD7701	Phase 2
0.7024	Intermediate Similarity	NPD3146	Approved
0.7024	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6534	Approved
0.7021	Intermediate Similarity	NPD6535	Approved
0.7006	Intermediate Similarity	NPD7229	Phase 3
0.6984	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4361	Phase 2
0.6982	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7095	Approved
0.6981	Remote Similarity	NPD4625	Phase 3
0.6977	Remote Similarity	NPD7615	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