NPASS Compound

Structure

NPC227192 OpenBabel07101719512D 26 28 0 0 0 0 0 0 0 0999 V2000 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 -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 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 -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 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 -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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 1.7321 2.0000 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 -3.4641 -0.0000 0.0000 O 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 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 5 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 8 2 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 19 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 26 1 0 0 0 0 12 18 2 0 0 0 0 12 24 1 0 0 0 0 13 14 1 0 0 0 0 13 15 2 0 0 0 0 14 16 1 0 0 0 0 14 20 2 0 0 0 0 15 18 1 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.08
Volume:	343.445
LogP:	2.693
LogD:	2.248
LogS:	-3.801
# Rotatable Bonds:	4
TPSA:	118.59
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	2.482
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.982
MDCK Permeability:	1.6281421267194673e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.036
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	89.61932373046875%
Volume Distribution (VD):	0.778
Pgp-substrate:	17.51498794555664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.674
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.109
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.709
CYP2C9-substrate:	0.74
CYP2D6-inhibitor:	0.183
CYP2D6-substrate:	0.433
CYP3A4-inhibitor:	0.398
CYP3A4-substrate:	0.193

ADMET: Excretion

Clearance (CL):	3.473
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.087
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.464
Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.095
Skin Sensitization:	0.43
Carcinogencity:	0.041
Eye Corrosion:	0.004
Eye Irritation:	0.807
Respiratory Toxicity:	0.109

Download Data

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

Natural Product: NPC227192

Natural Product ID:	NPC227192
*Common Name:**	3,5,4'-Trihydroxy-6,7,3'-Trimethoxyflavone
IUPAC Name:	3,5-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7-dimethoxychromen-4-one
Synonyms:
Standard InCHIKey:	RQJFJWHHIIPKGW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O8/c1-23-10-6-8(4-5-9(10)19)17-16(22)14(20)13-11(26-17)7-12(24-2)18(25-3)15(13)21/h4-7,19,21-22H,1-3H3
SMILES:	COc1cc(ccc1O)c1c(c(=O)c2c(cc(c(c2O)OC)OC)o1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3325484
PubChem CID:	6453535
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
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[25127164]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25176187]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26696523]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12728	Artemisia rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12728	Artemisia rupestris	Species	Asteraceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	4750.0	nM	PMID[485201]

☑ 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 NPC227192 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	474
0.1-0.2	2018
0.2-0.3	5215
0.3-0.4	11473
0.4-0.5	5640
0.5-0.6	3975
0.6-0.7	5130
0.7-0.8	4761
0.8-0.85	1948
0.85-0.9	1138
0.9-0.95	630
0.95-1	295

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC189179
1.0	High Similarity	NPC75215
1.0	High Similarity	NPC93376
1.0	High Similarity	NPC224137
0.9933	High Similarity	NPC7846
0.9933	High Similarity	NPC25495
0.9933	High Similarity	NPC204854
0.9933	High Similarity	NPC19687
0.9933	High Similarity	NPC49824
0.9933	High Similarity	NPC22472
0.9933	High Similarity	NPC9609
0.9933	High Similarity	NPC261004
0.9933	High Similarity	NPC288669
0.9933	High Similarity	NPC152166
0.9933	High Similarity	NPC191459
0.9933	High Similarity	NPC98661
0.9933	High Similarity	NPC143828
0.9933	High Similarity	NPC474520
0.9933	High Similarity	NPC115798
0.9933	High Similarity	NPC247017
0.9933	High Similarity	NPC18607
0.9933	High Similarity	NPC18772
0.9933	High Similarity	NPC130894
0.9933	High Similarity	NPC4481
0.9933	High Similarity	NPC300943
0.9933	High Similarity	NPC105242
0.9933	High Similarity	NPC176300
0.9933	High Similarity	NPC253634
0.9867	High Similarity	NPC110070
0.9867	High Similarity	NPC472438
0.9867	High Similarity	NPC29841
0.9867	High Similarity	NPC287979
0.9867	High Similarity	NPC7973
0.9867	High Similarity	NPC203891
0.9867	High Similarity	NPC235215
0.9867	High Similarity	NPC78302
0.9867	High Similarity	NPC101830
0.9867	High Similarity	NPC305663
0.9867	High Similarity	NPC176665
0.9867	High Similarity	NPC163524
0.9866	High Similarity	NPC183597
0.9866	High Similarity	NPC146165
0.9866	High Similarity	NPC2476
0.9866	High Similarity	NPC163780
0.9866	High Similarity	NPC201136
0.9866	High Similarity	NPC167815
0.9866	High Similarity	NPC44079
0.9866	High Similarity	NPC227325
0.9866	High Similarity	NPC128863
0.9866	High Similarity	NPC280339
0.9866	High Similarity	NPC201451
0.9866	High Similarity	NPC4455
0.9866	High Similarity	NPC92659
0.9866	High Similarity	NPC26227
0.9866	High Similarity	NPC196439
0.9866	High Similarity	NPC138360
0.9866	High Similarity	NPC50715
0.9801	High Similarity	NPC193842
0.98	High Similarity	NPC266960
0.98	High Similarity	NPC292107
0.98	High Similarity	NPC245546
0.98	High Similarity	NPC55619
0.98	High Similarity	NPC268161
0.98	High Similarity	NPC200388
0.98	High Similarity	NPC43243
0.98	High Similarity	NPC100916
0.98	High Similarity	NPC178854
0.9799	High Similarity	NPC250822
0.9799	High Similarity	NPC86485
0.9799	High Similarity	NPC255350
0.9799	High Similarity	NPC47781
0.9799	High Similarity	NPC75279
0.9799	High Similarity	NPC22519
0.9799	High Similarity	NPC160951
0.9799	High Similarity	NPC274327
0.9799	High Similarity	NPC69394
0.9799	High Similarity	NPC183878
0.9799	High Similarity	NPC145379
0.9799	High Similarity	NPC231018
0.9799	High Similarity	NPC176775
0.9799	High Similarity	NPC276409
0.9733	High Similarity	NPC208197
0.9733	High Similarity	NPC189960
0.9733	High Similarity	NPC256612
0.9733	High Similarity	NPC213622
0.9733	High Similarity	NPC32557
0.9733	High Similarity	NPC20830
0.9733	High Similarity	NPC214138
0.9732	High Similarity	NPC156222
0.9732	High Similarity	NPC27208
0.9732	High Similarity	NPC100887
0.9732	High Similarity	NPC256283
0.9732	High Similarity	NPC120163
0.9732	High Similarity	NPC212678
0.9732	High Similarity	NPC275836
0.9732	High Similarity	NPC275722
0.9732	High Similarity	NPC142540
0.9732	High Similarity	NPC25270
0.9732	High Similarity	NPC241498
0.9732	High Similarity	NPC162313
0.9732	High Similarity	NPC134677
0.9732	High Similarity	NPC239128
0.9732	High Similarity	NPC187498
0.9732	High Similarity	NPC222830
0.9732	High Similarity	NPC71334
0.9732	High Similarity	NPC57030
0.9732	High Similarity	NPC301123
0.9732	High Similarity	NPC83508
0.9732	High Similarity	NPC301323
0.9732	High Similarity	NPC188203
0.9732	High Similarity	NPC198826
0.9732	High Similarity	NPC293183
0.9732	High Similarity	NPC131624
0.9669	High Similarity	NPC265511
0.9667	High Similarity	NPC162351
0.9667	High Similarity	NPC58382
0.9667	High Similarity	NPC236223
0.9667	High Similarity	NPC179126
0.9667	High Similarity	NPC78326
0.9667	High Similarity	NPC270620
0.9667	High Similarity	NPC246204
0.9664	High Similarity	NPC54394
0.9664	High Similarity	NPC28274
0.9664	High Similarity	NPC226973
0.9664	High Similarity	NPC125062
0.9664	High Similarity	NPC133953
0.9664	High Similarity	NPC225731
0.9664	High Similarity	NPC208043
0.9664	High Similarity	NPC252933
0.9664	High Similarity	NPC200740
0.9664	High Similarity	NPC50403
0.9608	High Similarity	NPC246478
0.9605	High Similarity	NPC470402
0.96	High Similarity	NPC82325
0.96	High Similarity	NPC55205
0.96	High Similarity	NPC60972
0.96	High Similarity	NPC123886
0.96	High Similarity	NPC39732
0.96	High Similarity	NPC279989
0.9597	High Similarity	NPC50728
0.9597	High Similarity	NPC219330
0.9597	High Similarity	NPC166753
0.9597	High Similarity	NPC77858
0.9597	High Similarity	NPC184136
0.9597	High Similarity	NPC306821
0.9548	High Similarity	NPC470459
0.9542	High Similarity	NPC195832
0.9542	High Similarity	NPC152904
0.9539	High Similarity	NPC472916
0.9533	High Similarity	NPC76376
0.9533	High Similarity	NPC308451
0.9533	High Similarity	NPC236769
0.953	High Similarity	NPC296197
0.953	High Similarity	NPC137062
0.953	High Similarity	NPC183950
0.953	High Similarity	NPC177298
0.953	High Similarity	NPC17286
0.953	High Similarity	NPC87125
0.953	High Similarity	NPC195351
0.953	High Similarity	NPC328119
0.953	High Similarity	NPC52005
0.953	High Similarity	NPC270465
0.953	High Similarity	NPC259713
0.953	High Similarity	NPC223579
0.953	High Similarity	NPC159103
0.953	High Similarity	NPC287101
0.953	High Similarity	NPC48479
0.953	High Similarity	NPC216318
0.949	High Similarity	NPC76482
0.949	High Similarity	NPC295082
0.9487	High Similarity	NPC470457
0.9481	High Similarity	NPC476980
0.9481	High Similarity	NPC263449
0.9477	High Similarity	NPC472910
0.9477	High Similarity	NPC474836
0.9477	High Similarity	NPC78225
0.9477	High Similarity	NPC48208
0.9477	High Similarity	NPC472913
0.9477	High Similarity	NPC222814
0.9477	High Similarity	NPC96167
0.9477	High Similarity	NPC472914
0.9477	High Similarity	NPC162869
0.9477	High Similarity	NPC156057
0.9477	High Similarity	NPC245758
0.9477	High Similarity	NPC174908
0.9477	High Similarity	NPC474208
0.9477	High Similarity	NPC472911
0.9477	High Similarity	NPC475267
0.9474	High Similarity	NPC2928
0.947	High Similarity	NPC180234
0.947	High Similarity	NPC199100
0.947	High Similarity	NPC120537
0.9467	High Similarity	NPC149127
0.9467	High Similarity	NPC188871
0.9467	High Similarity	NPC259058
0.9467	High Similarity	NPC286342
0.9467	High Similarity	NPC45873
0.9467	High Similarity	NPC201547
0.9463	High Similarity	NPC195202
0.9463	High Similarity	NPC120464

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 NPC227192 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	444
0.1-0.2	995
0.2-0.3	1896
0.3-0.4	2684
0.4-0.5	1675
0.5-0.6	961
0.6-0.7	338
0.7-0.8	101
0.8-0.85	36
0.85-0.9	11
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9799	High Similarity	NPD2801	Approved
0.9329	High Similarity	NPD1512	Approved
0.9286	High Similarity	NPD3882	Suspended
0.9221	High Similarity	NPD3817	Phase 2
0.9216	High Similarity	NPD1934	Approved
0.9195	High Similarity	NPD1511	Approved
0.9119	High Similarity	NPD6168	Clinical (unspecified phase)
0.9119	High Similarity	NPD6167	Clinical (unspecified phase)
0.9119	High Similarity	NPD6166	Phase 2
0.908	High Similarity	NPD4338	Clinical (unspecified phase)
0.9032	High Similarity	NPD2393	Clinical (unspecified phase)
0.8889	High Similarity	NPD3818	Discontinued
0.8882	High Similarity	NPD4378	Clinical (unspecified phase)
0.8841	High Similarity	NPD6797	Phase 2
0.8834	High Similarity	NPD7054	Approved
0.8788	High Similarity	NPD7251	Discontinued
0.878	High Similarity	NPD7472	Approved
0.8735	High Similarity	NPD7808	Phase 3
0.8667	High Similarity	NPD7074	Phase 3
0.8616	High Similarity	NPD5402	Approved
0.8562	High Similarity	NPD4868	Clinical (unspecified phase)
0.8519	High Similarity	NPD5494	Approved
0.8509	High Similarity	NPD7075	Discontinued
0.8481	Intermediate Similarity	NPD4380	Phase 2
0.8452	Intermediate Similarity	NPD6799	Approved
0.8415	Intermediate Similarity	NPD6232	Discontinued
0.8395	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD6801	Discontinued
0.8373	Intermediate Similarity	NPD7473	Discontinued
0.8354	Intermediate Similarity	NPD1247	Approved
0.8323	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1510	Phase 2
0.8284	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD3926	Phase 2
0.8247	Intermediate Similarity	NPD1549	Phase 2
0.8235	Intermediate Similarity	NPD2796	Approved
0.821	Intermediate Similarity	NPD1465	Phase 2
0.8176	Intermediate Similarity	NPD5403	Approved
0.8146	Intermediate Similarity	NPD1240	Approved
0.8146	Intermediate Similarity	NPD943	Approved
0.8137	Intermediate Similarity	NPD6599	Discontinued
0.8098	Intermediate Similarity	NPD7819	Suspended
0.8059	Intermediate Similarity	NPD5844	Phase 1
0.805	Intermediate Similarity	NPD5401	Approved
0.8049	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1607	Approved
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD919	Approved
0.7975	Intermediate Similarity	NPD7411	Suspended
0.7935	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6959	Discontinued
0.7885	Intermediate Similarity	NPD2935	Discontinued
0.7881	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6190	Approved
0.7857	Intermediate Similarity	NPD447	Suspended
0.7857	Intermediate Similarity	NPD230	Phase 1
0.784	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6559	Discontinued
0.7815	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD3750	Approved
0.7792	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1613	Approved
0.7791	Intermediate Similarity	NPD1653	Approved
0.7736	Intermediate Similarity	NPD2800	Approved
0.7719	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3027	Phase 3
0.7709	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3751	Discontinued
0.7674	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3787	Discontinued
0.7658	Intermediate Similarity	NPD1551	Phase 2
0.764	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3749	Approved
0.7624	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD2532	Approved
0.7607	Intermediate Similarity	NPD2534	Approved
0.7607	Intermediate Similarity	NPD2533	Approved
0.7602	Intermediate Similarity	NPD7199	Phase 2
0.7588	Intermediate Similarity	NPD6234	Discontinued
0.7582	Intermediate Similarity	NPD9494	Approved
0.7578	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7768	Phase 2
0.755	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD3226	Approved
0.7527	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1933	Approved
0.7516	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD2344	Approved
0.7484	Intermediate Similarity	NPD3748	Approved
0.7469	Intermediate Similarity	NPD4628	Phase 3
0.7468	Intermediate Similarity	NPD6651	Approved
0.7458	Intermediate Similarity	NPD5953	Discontinued
0.7438	Intermediate Similarity	NPD6100	Approved
0.7438	Intermediate Similarity	NPD6099	Approved
0.7436	Intermediate Similarity	NPD2313	Discontinued
0.7416	Intermediate Similarity	NPD7685	Pre-registration
0.7407	Intermediate Similarity	NPD1243	Approved
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7396	Intermediate Similarity	NPD37	Approved
0.7394	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6233	Phase 2
0.7375	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2799	Discontinued
0.7374	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4967	Phase 2
0.7368	Intermediate Similarity	NPD4966	Approved
0.7368	Intermediate Similarity	NPD4965	Approved
0.7366	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7286	Phase 2
0.734	Intermediate Similarity	NPD6776	Approved
0.734	Intermediate Similarity	NPD6779	Approved
0.734	Intermediate Similarity	NPD6780	Approved
0.734	Intermediate Similarity	NPD6781	Approved
0.734	Intermediate Similarity	NPD6782	Approved
0.734	Intermediate Similarity	NPD6778	Approved
0.734	Intermediate Similarity	NPD6777	Approved
0.7338	Intermediate Similarity	NPD1203	Approved
0.7333	Intermediate Similarity	NPD7390	Discontinued
0.7317	Intermediate Similarity	NPD2309	Approved
0.7308	Intermediate Similarity	NPD6832	Phase 2
0.7294	Intermediate Similarity	NPD6844	Discontinued
0.7288	Intermediate Similarity	NPD7228	Approved
0.7284	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2403	Approved
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7255	Intermediate Similarity	NPD9269	Phase 2
0.7244	Intermediate Similarity	NPD3018	Phase 2
0.7225	Intermediate Similarity	NPD7435	Discontinued
0.7216	Intermediate Similarity	NPD5242	Approved
0.7215	Intermediate Similarity	NPD3268	Approved
0.7215	Intermediate Similarity	NPD6798	Discontinued
0.7213	Intermediate Similarity	NPD8150	Discontinued
0.7197	Intermediate Similarity	NPD4908	Phase 1
0.719	Intermediate Similarity	NPD422	Phase 1
0.7188	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2798	Approved
0.7175	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7033	Discontinued
0.7152	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD8313	Approved
0.7135	Intermediate Similarity	NPD6386	Approved
0.7135	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD7698	Approved
0.7135	Intermediate Similarity	NPD6385	Approved
0.7135	Intermediate Similarity	NPD7697	Approved
0.7126	Intermediate Similarity	NPD4357	Discontinued
0.7115	Intermediate Similarity	NPD2797	Approved
0.711	Intermediate Similarity	NPD5353	Approved
0.7107	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7870	Phase 2
0.7098	Intermediate Similarity	NPD7871	Phase 2
0.7097	Intermediate Similarity	NPD2983	Phase 2
0.7097	Intermediate Similarity	NPD2982	Phase 2
0.7091	Intermediate Similarity	NPD2654	Approved
0.7086	Intermediate Similarity	NPD5536	Phase 2
0.7081	Intermediate Similarity	NPD6355	Discontinued
0.7078	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1610	Phase 2
0.7077	Intermediate Similarity	NPD7701	Phase 2
0.7074	Intermediate Similarity	NPD6534	Approved
0.7074	Intermediate Similarity	NPD4360	Phase 2
0.7074	Intermediate Similarity	NPD6535	Approved
0.7074	Intermediate Similarity	NPD4363	Phase 3
0.7062	Intermediate Similarity	NPD5710	Approved
0.7062	Intermediate Similarity	NPD5711	Approved
0.7055	Intermediate Similarity	NPD4308	Phase 3
0.7051	Intermediate Similarity	NPD3225	Approved
0.7032	Intermediate Similarity	NPD2981	Phase 2
0.7032	Intermediate Similarity	NPD1608	Approved
0.7026	Intermediate Similarity	NPD7584	Approved
0.7025	Intermediate Similarity	NPD2861	Phase 2
0.7019	Intermediate Similarity	NPD4060	Phase 1
0.7006	Intermediate Similarity	NPD2354	Approved
0.7005	Intermediate Similarity	NPD7874	Approved
0.7005	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2163	Approved
0.7	Intermediate Similarity	NPD411	Approved
0.6995	Remote Similarity	NPD7549	Discontinued
0.6993	Remote Similarity	NPD9268	Approved
0.6988	Remote Similarity	NPD1652	Phase 2
0.6982	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2899	Discontinued
0.697	Remote Similarity	NPD7783	Phase 2
0.697	Remote Similarity	NPD7801	Approved
0.697	Remote Similarity	NPD7266	Discontinued
0.697	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1471	Phase 3
0.6966	Remote Similarity	NPD7229	Phase 3
0.6963	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