NPASS Compound

Structure

NPC474520 OpenBabel07101718242D 30 32 0 0 0 0 0 0 0 0999 V2000 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 0.0000 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 -4.3301 1.5000 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 -4.3301 0.5000 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 -6.0622 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 -2.5981 -1.5000 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 -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 -6.0622 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 -0.0000 -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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 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 -0.8660 -2.5000 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 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 8 1 0 0 0 0 7 10 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 9 21 1 0 0 0 0 10 16 1 0 0 0 0 10 25 1 0 0 0 0 11 12 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 22 2 0 0 0 0 13 18 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 14 24 1 0 0 0 0 15 30 1 0 0 0 0 16 26 1 0 0 0 0 17 19 2 0 0 0 0 17 30 1 0 0 0 0 18 20 2 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.11
Volume:	395.617
LogP:	2.595
LogD:	2.213
LogS:	-3.873
# Rotatable Bonds:	6
TPSA:	137.05
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.546
Synthetic Accessibility Score:	2.819
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.04
MDCK Permeability:	2.2164178517414257e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.068
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	81.09696960449219%
Volume Distribution (VD):	0.928
Pgp-substrate:	31.648176193237305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.225
CYP1A2-substrate:	0.984
CYP2C19-inhibitor:	0.032
CYP2C19-substrate:	0.223
CYP2C9-inhibitor:	0.508
CYP2C9-substrate:	0.677
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.244
CYP3A4-inhibitor:	0.26
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	3.123
Half-life (T1/2):	0.797

ADMET: Toxicity

hERG Blockers:	0.395
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.207
Rat Oral Acute Toxicity:	0.267
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.66
Carcinogencity:	0.026
Eye Corrosion:	0.003
Eye Irritation:	0.695
Respiratory Toxicity:	0.073

Download Data

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

Natural Product: NPC474520

Natural Product ID:	NPC474520
*Common Name:**	3-O-Demethyldigicitrin
IUPAC Name:	3,5-dihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-6,7,8-trimethoxychromen-4-one
Synonyms:	3-O-Demethyldigicitrin
Standard InCHIKey:	SBECGZQEVBSJHM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O10/c1-25-10-7-8(6-9(21)16(10)26-2)15-14(24)12(22)11-13(23)18(27-3)20(29-5)19(28-4)17(11)30-15/h6-7,21,23-24H,1-5H3
SMILES:	COC1=CC(=CC(=C1OC)O)C2=C(C(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470678
PubChem CID:	44260075
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO32678	acronychia porteri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964782]
NPO33371	zieridium pseudobtusifolium	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[7964782]

☑ 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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2.0	ug.mL-1	PMID[454999]

☑ 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 NPC474520 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	446
0.1-0.2	1989
0.2-0.3	5134
0.3-0.4	11242
0.4-0.5	6100
0.5-0.6	3997
0.6-0.7	5099
0.7-0.8	4807
0.8-0.85	1914
0.85-0.9	1098
0.9-0.95	653
0.95-1	218

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC189179
0.9933	High Similarity	NPC227192
0.9933	High Similarity	NPC78302
0.9933	High Similarity	NPC7973
0.9933	High Similarity	NPC93376
0.9933	High Similarity	NPC472438
0.9933	High Similarity	NPC235215
0.9933	High Similarity	NPC224137
0.9933	High Similarity	NPC75215
0.9933	High Similarity	NPC29841
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	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	NPC288669
0.9867	High Similarity	NPC105242
0.9867	High Similarity	NPC18607
0.9866	High Similarity	NPC268161
0.9866	High Similarity	NPC55619
0.9866	High Similarity	NPC100916
0.9866	High Similarity	NPC247017
0.9866	High Similarity	NPC49824
0.9866	High Similarity	NPC98661
0.9866	High Similarity	NPC200388
0.9865	High Similarity	NPC250822
0.9865	High Similarity	NPC276409
0.9865	High Similarity	NPC75279
0.98	High Similarity	NPC110070
0.98	High Similarity	NPC176665
0.98	High Similarity	NPC305663
0.98	High Similarity	NPC287979
0.98	High Similarity	NPC203891
0.98	High Similarity	NPC163524
0.98	High Similarity	NPC101830
0.9799	High Similarity	NPC138360
0.9799	High Similarity	NPC280339
0.9799	High Similarity	NPC128863
0.9799	High Similarity	NPC92659
0.9799	High Similarity	NPC208197
0.9799	High Similarity	NPC201451
0.9799	High Similarity	NPC183597
0.9799	High Similarity	NPC26227
0.9799	High Similarity	NPC227325
0.9799	High Similarity	NPC167815
0.9799	High Similarity	NPC201136
0.9799	High Similarity	NPC44079
0.9799	High Similarity	NPC196439
0.9799	High Similarity	NPC50715
0.9799	High Similarity	NPC4455
0.9799	High Similarity	NPC146165
0.9799	High Similarity	NPC163780
0.9799	High Similarity	NPC2476
0.9735	High Similarity	NPC193842
0.9733	High Similarity	NPC266960
0.9733	High Similarity	NPC43243
0.9733	High Similarity	NPC292107
0.9733	High Similarity	NPC178854
0.9733	High Similarity	NPC245546
0.9732	High Similarity	NPC69394
0.9732	High Similarity	NPC162351
0.9732	High Similarity	NPC86485
0.9732	High Similarity	NPC183878
0.9732	High Similarity	NPC160951
0.9732	High Similarity	NPC246204
0.9732	High Similarity	NPC22519
0.9732	High Similarity	NPC274327
0.9732	High Similarity	NPC145379
0.9732	High Similarity	NPC58382
0.9732	High Similarity	NPC231018
0.9732	High Similarity	NPC176775
0.9732	High Similarity	NPC255350
0.9732	High Similarity	NPC47781
0.973	High Similarity	NPC133953
0.973	High Similarity	NPC50403
0.973	High Similarity	NPC28274
0.9671	High Similarity	NPC246478
0.9667	High Similarity	NPC256612
0.9667	High Similarity	NPC20830
0.9667	High Similarity	NPC214138
0.9667	High Similarity	NPC32557
0.9667	High Similarity	NPC213622
0.9667	High Similarity	NPC189960
0.9664	High Similarity	NPC301123
0.9664	High Similarity	NPC83508
0.9664	High Similarity	NPC120163
0.9664	High Similarity	NPC301323
0.9664	High Similarity	NPC275722
0.9664	High Similarity	NPC25270
0.9664	High Similarity	NPC131624
0.9664	High Similarity	NPC156222
0.9664	High Similarity	NPC27208
0.9664	High Similarity	NPC241498
0.9664	High Similarity	NPC100887
0.9664	High Similarity	NPC256283
0.9664	High Similarity	NPC222830
0.9664	High Similarity	NPC293183
0.9664	High Similarity	NPC239128
0.9664	High Similarity	NPC187498
0.9664	High Similarity	NPC134677
0.9664	High Similarity	NPC188203
0.9664	High Similarity	NPC123886
0.9664	High Similarity	NPC142540
0.9664	High Similarity	NPC162313
0.9664	High Similarity	NPC275836
0.9664	High Similarity	NPC198826
0.9664	High Similarity	NPC57030
0.9664	High Similarity	NPC212678
0.9664	High Similarity	NPC71334
0.9662	High Similarity	NPC219330
0.961	High Similarity	NPC470459
0.9603	High Similarity	NPC265511
0.96	High Similarity	NPC236223
0.96	High Similarity	NPC78326
0.96	High Similarity	NPC270620
0.96	High Similarity	NPC179126
0.9597	High Similarity	NPC226973
0.9597	High Similarity	NPC225731
0.9597	High Similarity	NPC200740
0.9597	High Similarity	NPC208043
0.9597	High Similarity	NPC76376
0.9597	High Similarity	NPC125062
0.9597	High Similarity	NPC252933
0.9597	High Similarity	NPC54394
0.9595	High Similarity	NPC48479
0.9595	High Similarity	NPC177298
0.9595	High Similarity	NPC328119
0.9548	High Similarity	NPC470457
0.9539	High Similarity	NPC470402
0.9533	High Similarity	NPC82325
0.9533	High Similarity	NPC55205
0.9533	High Similarity	NPC39732
0.9533	High Similarity	NPC279989
0.9533	High Similarity	NPC60972
0.953	High Similarity	NPC50728
0.953	High Similarity	NPC184136
0.953	High Similarity	NPC77858
0.953	High Similarity	NPC166753
0.953	High Similarity	NPC306821
0.9527	High Similarity	NPC120464
0.9487	High Similarity	NPC470462
0.9484	High Similarity	NPC41301
0.9477	High Similarity	NPC195832
0.9477	High Similarity	NPC152904
0.9474	High Similarity	NPC472916
0.947	High Similarity	NPC280937
0.947	High Similarity	NPC250557
0.9467	High Similarity	NPC236769
0.9467	High Similarity	NPC308451
0.9463	High Similarity	NPC223579
0.9463	High Similarity	NPC183950
0.9463	High Similarity	NPC52005
0.9463	High Similarity	NPC181250
0.9463	High Similarity	NPC259713
0.9463	High Similarity	NPC216318
0.9463	High Similarity	NPC17286
0.9463	High Similarity	NPC195351
0.9463	High Similarity	NPC87125
0.9463	High Similarity	NPC296197
0.9463	High Similarity	NPC270465
0.9463	High Similarity	NPC137062
0.9463	High Similarity	NPC159103
0.9463	High Similarity	NPC287101
0.9459	High Similarity	NPC61871
0.9459	High Similarity	NPC55557
0.9459	High Similarity	NPC33265
0.9459	High Similarity	NPC30647
0.9459	High Similarity	NPC62536
0.9427	High Similarity	NPC76482
0.9427	High Similarity	NPC158761
0.9427	High Similarity	NPC295082
0.9427	High Similarity	NPC470456
0.9416	High Similarity	NPC263449
0.9416	High Similarity	NPC476980
0.9412	High Similarity	NPC78225
0.9412	High Similarity	NPC474836
0.9412	High Similarity	NPC472910
0.9412	High Similarity	NPC469584
0.9412	High Similarity	NPC222814
0.9412	High Similarity	NPC262286
0.9412	High Similarity	NPC472913
0.9412	High Similarity	NPC472914
0.9412	High Similarity	NPC48208
0.9412	High Similarity	NPC241904
0.9412	High Similarity	NPC96167
0.9412	High Similarity	NPC156057
0.9412	High Similarity	NPC475267
0.9412	High Similarity	NPC162869

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 NPC474520 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	415
0.1-0.2	1001
0.2-0.3	1970
0.3-0.4	2676
0.4-0.5	1676
0.5-0.6	947
0.6-0.7	309
0.7-0.8	107
0.8-0.85	26
0.85-0.9	15
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9732	High Similarity	NPD2801	Approved
0.9262	High Similarity	NPD1512	Approved
0.9221	High Similarity	NPD3882	Suspended
0.9156	High Similarity	NPD3817	Phase 2
0.915	High Similarity	NPD1934	Approved
0.9128	High Similarity	NPD1511	Approved
0.9057	High Similarity	NPD6166	Phase 2
0.9057	High Similarity	NPD6167	Clinical (unspecified phase)
0.9057	High Similarity	NPD6168	Clinical (unspecified phase)
0.9018	High Similarity	NPD4338	Clinical (unspecified phase)
0.8968	High Similarity	NPD2393	Clinical (unspecified phase)
0.8827	High Similarity	NPD3818	Discontinued
0.8816	High Similarity	NPD4378	Clinical (unspecified phase)
0.878	High Similarity	NPD6797	Phase 2
0.8773	High Similarity	NPD7054	Approved
0.8727	High Similarity	NPD7251	Discontinued
0.872	High Similarity	NPD7472	Approved
0.8675	High Similarity	NPD7808	Phase 3
0.8616	High Similarity	NPD4868	Clinical (unspecified phase)
0.8606	High Similarity	NPD7074	Phase 3
0.8553	High Similarity	NPD5402	Approved
0.8457	Intermediate Similarity	NPD5494	Approved
0.8447	Intermediate Similarity	NPD7075	Discontinued
0.8418	Intermediate Similarity	NPD4380	Phase 2
0.8387	Intermediate Similarity	NPD6799	Approved
0.8354	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8293	Intermediate Similarity	NPD1247	Approved
0.8261	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD1465	Phase 2
0.8235	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1510	Phase 2
0.8217	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD3926	Phase 2
0.8182	Intermediate Similarity	NPD1549	Phase 2
0.817	Intermediate Similarity	NPD2796	Approved
0.8113	Intermediate Similarity	NPD5403	Approved
0.8079	Intermediate Similarity	NPD943	Approved
0.8079	Intermediate Similarity	NPD1240	Approved
0.8075	Intermediate Similarity	NPD6599	Discontinued
0.8065	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD5844	Phase 1
0.7988	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD5401	Approved
0.7974	Intermediate Similarity	NPD1607	Approved
0.7964	Intermediate Similarity	NPD6959	Discontinued
0.7952	Intermediate Similarity	NPD919	Approved
0.7914	Intermediate Similarity	NPD7411	Suspended
0.7908	Intermediate Similarity	NPD230	Phase 1
0.7871	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2935	Discontinued
0.7815	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6190	Approved
0.7792	Intermediate Similarity	NPD447	Suspended
0.7785	Intermediate Similarity	NPD2800	Approved
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6559	Discontinued
0.7736	Intermediate Similarity	NPD3750	Approved
0.773	Intermediate Similarity	NPD1653	Approved
0.7727	Intermediate Similarity	NPD1613	Approved
0.7727	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2534	Approved
0.7654	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2532	Approved
0.7654	Intermediate Similarity	NPD2533	Approved
0.7647	Intermediate Similarity	NPD3027	Phase 3
0.7633	Intermediate Similarity	NPD6234	Discontinued
0.763	Intermediate Similarity	NPD3751	Discontinued
0.7616	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD3787	Discontinued
0.7597	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1551	Phase 2
0.7584	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3749	Approved
0.7569	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7199	Phase 2
0.7516	Intermediate Similarity	NPD6651	Approved
0.7516	Intermediate Similarity	NPD9494	Approved
0.7516	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD6099	Approved
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD3226	Approved
0.7455	Intermediate Similarity	NPD920	Approved
0.7453	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1243	Approved
0.7452	Intermediate Similarity	NPD1933	Approved
0.744	Intermediate Similarity	NPD37	Approved
0.7438	Intermediate Similarity	NPD2344	Approved
0.7421	Intermediate Similarity	NPD3748	Approved
0.7421	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
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
0.7401	Intermediate Similarity	NPD5953	Discontinued
0.7378	Intermediate Similarity	NPD7390	Discontinued
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.736	Intermediate Similarity	NPD7685	Pre-registration
0.7348	Intermediate Similarity	NPD8434	Phase 2
0.7333	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7228	Approved
0.7325	Intermediate Similarity	NPD6233	Phase 2
0.7318	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD2403	Approved
0.7312	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2799	Discontinued
0.7303	Intermediate Similarity	NPD9269	Phase 2
0.7288	Intermediate Similarity	NPD7286	Phase 2
0.7287	Intermediate Similarity	NPD6779	Approved
0.7287	Intermediate Similarity	NPD6777	Approved
0.7287	Intermediate Similarity	NPD6780	Approved
0.7287	Intermediate Similarity	NPD6778	Approved
0.7287	Intermediate Similarity	NPD6781	Approved
0.7287	Intermediate Similarity	NPD6782	Approved
0.7287	Intermediate Similarity	NPD6776	Approved
0.7273	Intermediate Similarity	NPD1203	Approved
0.7256	Intermediate Similarity	NPD2309	Approved
0.7244	Intermediate Similarity	NPD6832	Phase 2
0.7235	Intermediate Similarity	NPD6844	Discontinued
0.7229	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2346	Discontinued
0.7212	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1548	Phase 1
0.7195	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3018	Phase 2
0.7173	Intermediate Similarity	NPD7435	Discontinued
0.7159	Intermediate Similarity	NPD5242	Approved
0.7158	Intermediate Similarity	NPD8150	Discontinued
0.7152	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7151	Intermediate Similarity	NPD5353	Approved
0.7134	Intermediate Similarity	NPD4908	Phase 1
0.7134	Intermediate Similarity	NPD2654	Approved
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD422	Phase 1
0.7119	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2798	Approved
0.7102	Intermediate Similarity	NPD5710	Approved
0.7102	Intermediate Similarity	NPD5711	Approved
0.7099	Intermediate Similarity	NPD7033	Discontinued
0.7088	Intermediate Similarity	NPD8312	Approved
0.7088	Intermediate Similarity	NPD8313	Approved
0.7083	Intermediate Similarity	NPD7697	Approved
0.7083	Intermediate Similarity	NPD7696	Phase 3
0.7083	Intermediate Similarity	NPD7698	Approved
0.7078	Intermediate Similarity	NPD9717	Approved
0.7076	Intermediate Similarity	NPD6386	Approved
0.7076	Intermediate Similarity	NPD6385	Approved
0.7066	Intermediate Similarity	NPD4357	Discontinued
0.7051	Intermediate Similarity	NPD2797	Approved
0.7047	Intermediate Similarity	NPD7871	Phase 2
0.7047	Intermediate Similarity	NPD7870	Phase 2
0.7044	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD9268	Approved
0.7032	Intermediate Similarity	NPD2983	Phase 2
0.7032	Intermediate Similarity	NPD2982	Phase 2
0.7026	Intermediate Similarity	NPD7701	Phase 2
0.7021	Intermediate Similarity	NPD6534	Approved
0.7021	Intermediate Similarity	NPD4363	Phase 3
0.7021	Intermediate Similarity	NPD6535	Approved
0.7021	Intermediate Similarity	NPD4360	Phase 2
0.702	Intermediate Similarity	NPD5536	Phase 2
0.7019	Intermediate Similarity	NPD6355	Discontinued
0.7013	Intermediate Similarity	NPD1610	Phase 2
0.7013	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4308	Phase 3
0.699	Remote Similarity	NPD8151	Discontinued
0.6987	Remote Similarity	NPD3225	Approved
0.6974	Remote Similarity	NPD7584	Approved
0.6968	Remote Similarity	NPD1608	Approved
0.6968	Remote Similarity	NPD2981	Phase 2
0.6962	Remote Similarity	NPD2861	Phase 2
0.6957	Remote Similarity	NPD4060	Phase 1
0.6954	Remote Similarity	NPD7874	Approved
0.6954	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2354	Approved
0.6944	Remote Similarity	NPD2163	Approved
0.694	Remote Similarity	NPD7549	Discontinued
0.6937	Remote Similarity	NPD411	Approved
0.6931	Remote Similarity	NPD2899	Discontinued
0.6928	Remote Similarity	NPD1652	Phase 2
0.6923	Remote Similarity	NPD4749	Approved
0.6923	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7783	Phase 2
0.6919	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7801	Approved
0.6911	Remote Similarity	NPD7700	Phase 2
0.6911	Remote Similarity	NPD7699	Phase 2

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