NPASS Compound

Structure

CID63256 OpenBabel06191715402D 23 25 0 0 0 0 0 0 0 0999 V2000 6.0622 -0.5000 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 -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 3.4641 -2.0000 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 -0.0000 -2.0000 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 -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 0.8660 -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 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 -0.0000 -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 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -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 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 11 1 0 0 0 0 7 9 2 0 0 0 0 7 10 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 19 1 0 0 0 0 10 11 2 0 0 0 0 10 15 1 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 16 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 17 2 0 0 0 0 15 18 2 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.09
Volume:	311.205
LogP:	2.816
LogD:	2.696
LogS:	-3.834
# Rotatable Bonds:	4
TPSA:	67.13
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.689
Synthetic Accessibility Score:	2.171
Fsp3:	0.235
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:	-4.618
MDCK Permeability:	5.360656723496504e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.259
Plasma Protein Binding (PPB):	75.1812973022461%
Volume Distribution (VD):	0.879
Pgp-substrate:	23.873287200927734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.67
CYP1A2-substrate:	0.983
CYP2C19-inhibitor:	0.754
CYP2C19-substrate:	0.896
CYP2C9-inhibitor:	0.51
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.124
CYP2D6-substrate:	0.922
CYP3A4-inhibitor:	0.592
CYP3A4-substrate:	0.667

ADMET: Excretion

Clearance (CL):	3.863
Half-life (T1/2):	0.346

ADMET: Toxicity

hERG Blockers:	0.186
Human Hepatotoxicity (H-HT):	0.117
Drug-inuced Liver Injury (DILI):	0.893
AMES Toxicity:	0.561
Rat Oral Acute Toxicity:	0.262
Maximum Recommended Daily Dose:	0.067
Skin Sensitization:	0.584
Carcinogencity:	0.046
Eye Corrosion:	0.021
Eye Irritation:	0.732
Respiratory Toxicity:	0.293

Download Data

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

Natural Product: NPC63256

Natural Product ID:	NPC63256
*Common Name:**	1,2,3,7-Tetramethoxyxanthen-9-One
IUPAC Name:	1,2,3,7-tetramethoxyxanthen-9-one
Synonyms:
Standard InCHIKey:	FYLQNKRJVPRLKX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O6/c1-19-9-5-6-11-10(7-9)15(18)14-12(23-11)8-13(20-2)16(21-3)17(14)22-4/h5-8H,1-4H3
SMILES:	COc1ccc2c(c1)c(=O)c1c(cc(c(c1OC)OC)OC)o2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3704821
PubChem CID:	14528828
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1484	Bupleurum scorzonerifolium	Species	Apiaceae	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	2

Activity Type	# Activity
Protein Complex	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	>	100000.0	nM	PMID[548557]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	>	100000	nM	Patent: US9114126 B2

☑ 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 NPC63256 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	509
0.1-0.2	2023
0.2-0.3	5279
0.3-0.4	11894
0.4-0.5	5266
0.5-0.6	4047
0.6-0.7	5449
0.7-0.8	4719
0.8-0.85	2090
0.85-0.9	945
0.9-0.95	437
0.95-1	39

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC10304
0.9858	High Similarity	NPC231013
0.979	High Similarity	NPC238366
0.9789	High Similarity	NPC205522
0.9718	High Similarity	NPC110639
0.9718	High Similarity	NPC14958
0.9718	High Similarity	NPC215932
0.9718	High Similarity	NPC106461
0.9718	High Similarity	NPC40818
0.965	High Similarity	NPC85233
0.9648	High Similarity	NPC136278
0.9589	High Similarity	NPC166201
0.958	High Similarity	NPC283002
0.958	High Similarity	NPC302408
0.958	High Similarity	NPC195919
0.958	High Similarity	NPC216314
0.958	High Similarity	NPC120924
0.9577	High Similarity	NPC23955
0.9577	High Similarity	NPC293201
0.9577	High Similarity	NPC113089
0.9524	High Similarity	NPC472408
0.9524	High Similarity	NPC186507
0.9524	High Similarity	NPC472915
0.9521	High Similarity	NPC198615
0.9521	High Similarity	NPC149614
0.9521	High Similarity	NPC117579
0.9521	High Similarity	NPC474663
0.9517	High Similarity	NPC69752
0.9514	High Similarity	NPC470511
0.951	High Similarity	NPC471590
0.951	High Similarity	NPC165512
0.9507	High Similarity	NPC70853
0.9507	High Similarity	NPC9966
0.9504	High Similarity	NPC58229
0.9463	High Similarity	NPC181960
0.9459	High Similarity	NPC472909
0.9459	High Similarity	NPC37392
0.9452	High Similarity	NPC179183
0.9452	High Similarity	NPC29056
0.9452	High Similarity	NPC259058
0.9452	High Similarity	NPC201547
0.9448	High Similarity	NPC476342
0.9441	High Similarity	NPC182842
0.9437	High Similarity	NPC29536
0.9437	High Similarity	NPC124467
0.9437	High Similarity	NPC214919
0.9396	High Similarity	NPC303255
0.9396	High Similarity	NPC472916
0.9392	High Similarity	NPC280937
0.9392	High Similarity	NPC128961
0.9392	High Similarity	NPC88645
0.9392	High Similarity	NPC292214
0.9392	High Similarity	NPC206238
0.9392	High Similarity	NPC244371
0.9392	High Similarity	NPC167091
0.9392	High Similarity	NPC271779
0.9388	High Similarity	NPC226973
0.9388	High Similarity	NPC308451
0.9388	High Similarity	NPC208043
0.9384	High Similarity	NPC181250
0.9384	High Similarity	NPC474648
0.9379	High Similarity	NPC299923
0.9338	High Similarity	NPC298093
0.9333	High Similarity	NPC78225
0.9333	High Similarity	NPC472910
0.9333	High Similarity	NPC48208
0.9333	High Similarity	NPC474208
0.9333	High Similarity	NPC258644
0.9333	High Similarity	NPC474836
0.9333	High Similarity	NPC262286
0.9333	High Similarity	NPC476981
0.9333	High Similarity	NPC96167
0.9333	High Similarity	NPC19097
0.9333	High Similarity	NPC245758
0.9333	High Similarity	NPC472914
0.9333	High Similarity	NPC156057
0.9333	High Similarity	NPC99597
0.9333	High Similarity	NPC162869
0.9333	High Similarity	NPC472911
0.9333	High Similarity	NPC475267
0.9333	High Similarity	NPC222814
0.9333	High Similarity	NPC36852
0.9333	High Similarity	NPC472913
0.9333	High Similarity	NPC210084
0.9329	High Similarity	NPC2928
0.9329	High Similarity	NPC31018
0.9329	High Similarity	NPC20830
0.9329	High Similarity	NPC256612
0.9329	High Similarity	NPC255807
0.9324	High Similarity	NPC134677
0.9324	High Similarity	NPC120537
0.9324	High Similarity	NPC161277
0.9324	High Similarity	NPC199100
0.9324	High Similarity	NPC40033
0.9324	High Similarity	NPC101996
0.9324	High Similarity	NPC180234
0.9324	High Similarity	NPC39007
0.932	High Similarity	NPC306821
0.9315	High Similarity	NPC183236
0.931	High Similarity	NPC310259
0.9301	High Similarity	NPC185607
0.9291	High Similarity	NPC44573
0.9276	High Similarity	NPC165549
0.9272	High Similarity	NPC152904
0.9267	High Similarity	NPC68093
0.9267	High Similarity	NPC255106
0.9267	High Similarity	NPC180340
0.9267	High Similarity	NPC138243
0.9267	High Similarity	NPC191146
0.9267	High Similarity	NPC235165
0.9262	High Similarity	NPC86485
0.9262	High Similarity	NPC69394
0.9262	High Similarity	NPC160951
0.9262	High Similarity	NPC176775
0.9262	High Similarity	NPC231018
0.9262	High Similarity	NPC47781
0.9262	High Similarity	NPC22519
0.9262	High Similarity	NPC145379
0.9262	High Similarity	NPC274327
0.9262	High Similarity	NPC255350
0.9262	High Similarity	NPC183878
0.9257	High Similarity	NPC262623
0.9257	High Similarity	NPC251110
0.9257	High Similarity	NPC171010
0.9252	High Similarity	NPC328119
0.9247	High Similarity	NPC117463
0.9247	High Similarity	NPC119660
0.9247	High Similarity	NPC46941
0.9247	High Similarity	NPC93034
0.9216	High Similarity	NPC83922
0.9216	High Similarity	NPC472448
0.9211	High Similarity	NPC476980
0.9205	High Similarity	NPC241904
0.9205	High Similarity	NPC165977
0.9205	High Similarity	NPC217677
0.9205	High Similarity	NPC300727
0.9205	High Similarity	NPC469584
0.9205	High Similarity	NPC129684
0.9205	High Similarity	NPC299520
0.92	High Similarity	NPC117992
0.92	High Similarity	NPC138360
0.92	High Similarity	NPC189960
0.92	High Similarity	NPC196439
0.92	High Similarity	NPC128863
0.92	High Similarity	NPC230149
0.92	High Similarity	NPC34725
0.92	High Similarity	NPC92659
0.92	High Similarity	NPC50715
0.92	High Similarity	NPC113906
0.92	High Similarity	NPC4455
0.92	High Similarity	NPC57674
0.92	High Similarity	NPC213622
0.92	High Similarity	NPC2476
0.92	High Similarity	NPC241774
0.92	High Similarity	NPC276059
0.92	High Similarity	NPC280339
0.92	High Similarity	NPC167815
0.92	High Similarity	NPC227325
0.92	High Similarity	NPC201136
0.92	High Similarity	NPC163780
0.92	High Similarity	NPC208197
0.92	High Similarity	NPC183597
0.92	High Similarity	NPC168247
0.92	High Similarity	NPC122623
0.92	High Similarity	NPC32557
0.92	High Similarity	NPC146165
0.92	High Similarity	NPC152951
0.9195	High Similarity	NPC301123
0.9195	High Similarity	NPC60972
0.9195	High Similarity	NPC477231
0.9195	High Similarity	NPC162313
0.9195	High Similarity	NPC257648
0.9195	High Similarity	NPC275722
0.9195	High Similarity	NPC188203
0.9195	High Similarity	NPC83508
0.9195	High Similarity	NPC241498
0.9195	High Similarity	NPC301323
0.9195	High Similarity	NPC100887
0.9195	High Similarity	NPC120163
0.9195	High Similarity	NPC292460
0.9195	High Similarity	NPC222830
0.9195	High Similarity	NPC275836
0.9195	High Similarity	NPC39732
0.9195	High Similarity	NPC156222
0.9195	High Similarity	NPC198826
0.9195	High Similarity	NPC57030
0.9195	High Similarity	NPC256283
0.9195	High Similarity	NPC212678
0.9195	High Similarity	NPC187498
0.9195	High Similarity	NPC239128
0.9195	High Similarity	NPC131624
0.9195	High Similarity	NPC293183
0.9195	High Similarity	NPC25270
0.9195	High Similarity	NPC71334
0.9189	High Similarity	NPC239363
0.9189	High Similarity	NPC29231
0.9189	High Similarity	NPC156953
0.9189	High Similarity	NPC5840
0.9189	High Similarity	NPC62042
0.9189	High Similarity	NPC338131

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 NPC63256 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	447
0.1-0.2	1010
0.2-0.3	1769
0.3-0.4	2729
0.4-0.5	1746
0.5-0.6	928
0.6-0.7	365
0.7-0.8	110
0.8-0.85	32
0.85-0.9	11
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9338	High Similarity	NPD5494	Approved
0.9262	High Similarity	NPD2801	Approved
0.9067	High Similarity	NPD1934	Approved
0.8882	High Similarity	NPD2393	Clinical (unspecified phase)
0.8824	High Similarity	NPD3817	Phase 2
0.8819	High Similarity	NPD2796	Approved
0.8766	High Similarity	NPD3882	Suspended
0.8662	High Similarity	NPD1247	Approved
0.8658	High Similarity	NPD1511	Approved
0.8616	High Similarity	NPD6166	Phase 2
0.8616	High Similarity	NPD6168	Clinical (unspecified phase)
0.8616	High Similarity	NPD6167	Clinical (unspecified phase)
0.8553	High Similarity	NPD3926	Phase 2
0.8543	High Similarity	NPD1512	Approved
0.8509	High Similarity	NPD3818	Discontinued
0.8477	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1549	Phase 2
0.8411	Intermediate Similarity	NPD6799	Approved
0.8408	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD7074	Phase 3
0.8397	Intermediate Similarity	NPD7819	Suspended
0.8397	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7054	Approved
0.8344	Intermediate Similarity	NPD5844	Phase 1
0.8323	Intermediate Similarity	NPD4380	Phase 2
0.8302	Intermediate Similarity	NPD919	Approved
0.8293	Intermediate Similarity	NPD7472	Approved
0.8261	Intermediate Similarity	NPD6232	Discontinued
0.8243	Intermediate Similarity	NPD1510	Phase 2
0.8239	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD7075	Discontinued
0.8228	Intermediate Similarity	NPD5402	Approved
0.8221	Intermediate Similarity	NPD7473	Discontinued
0.8219	Intermediate Similarity	NPD1240	Approved
0.8205	Intermediate Similarity	NPD6599	Discontinued
0.8163	Intermediate Similarity	NPD1933	Approved
0.8153	Intermediate Similarity	NPD7411	Suspended
0.8144	Intermediate Similarity	NPD7808	Phase 3
0.8133	Intermediate Similarity	NPD6797	Phase 2
0.8117	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD1607	Approved
0.8101	Intermediate Similarity	NPD6801	Discontinued
0.8084	Intermediate Similarity	NPD7251	Discontinued
0.805	Intermediate Similarity	NPD1465	Phase 2
0.8013	Intermediate Similarity	NPD920	Approved
0.8	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3748	Approved
0.7973	Intermediate Similarity	NPD943	Approved
0.7947	Intermediate Similarity	NPD2935	Discontinued
0.7919	Intermediate Similarity	NPD447	Suspended
0.7917	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD1243	Approved
0.7885	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6959	Discontinued
0.7832	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3749	Approved
0.7785	Intermediate Similarity	NPD5403	Approved
0.7771	Intermediate Similarity	NPD5242	Approved
0.7771	Intermediate Similarity	NPD5401	Approved
0.7765	Intermediate Similarity	NPD6559	Discontinued
0.7756	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3750	Approved
0.7727	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6832	Phase 2
0.7703	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2800	Approved
0.7669	Intermediate Similarity	NPD5353	Approved
0.7662	Intermediate Similarity	NPD2346	Discontinued
0.7647	Intermediate Similarity	NPD2799	Discontinued
0.7635	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7768	Phase 2
0.7616	Intermediate Similarity	NPD1613	Approved
0.7616	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD5536	Phase 2
0.76	Intermediate Similarity	NPD2313	Discontinued
0.7597	Intermediate Similarity	NPD1551	Phase 2
0.7595	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6386	Approved
0.7593	Intermediate Similarity	NPD6385	Approved
0.7578	Intermediate Similarity	NPD3226	Approved
0.7569	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD230	Phase 1
0.7548	Intermediate Similarity	NPD2344	Approved
0.7547	Intermediate Similarity	NPD2534	Approved
0.7547	Intermediate Similarity	NPD2532	Approved
0.7547	Intermediate Similarity	NPD2533	Approved
0.7545	Intermediate Similarity	NPD7199	Phase 2
0.7529	Intermediate Similarity	NPD3751	Discontinued
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7515	Intermediate Similarity	NPD2403	Approved
0.75	Intermediate Similarity	NPD3787	Discontinued
0.7484	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD6099	Approved
0.7458	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2654	Approved
0.745	Intermediate Similarity	NPD2798	Approved
0.7439	Intermediate Similarity	NPD6844	Discontinued
0.7419	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3027	Phase 3
0.7415	Intermediate Similarity	NPD3972	Approved
0.741	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1653	Approved
0.7405	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD3018	Phase 2
0.7399	Intermediate Similarity	NPD5953	Discontinued
0.7384	Intermediate Similarity	NPD7286	Phase 2
0.7374	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2309	Approved
0.7333	Intermediate Similarity	NPD37	Approved
0.7329	Intermediate Similarity	NPD17	Approved
0.7325	Intermediate Similarity	NPD1471	Phase 3
0.7305	Intermediate Similarity	NPD4965	Approved
0.7305	Intermediate Similarity	NPD4966	Approved
0.7305	Intermediate Similarity	NPD4967	Phase 2
0.7297	Intermediate Similarity	NPD2981	Phase 2
0.7296	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6651	Approved
0.7288	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD9494	Approved
0.7284	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4307	Phase 2
0.7267	Intermediate Similarity	NPD1203	Approved
0.7267	Intermediate Similarity	NPD3267	Approved
0.7267	Intermediate Similarity	NPD3266	Approved
0.725	Intermediate Similarity	NPD6190	Approved
0.7248	Intermediate Similarity	NPD2982	Phase 2
0.7248	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2983	Phase 2
0.7246	Intermediate Similarity	NPD5977	Approved
0.7246	Intermediate Similarity	NPD5978	Approved
0.7237	Intermediate Similarity	NPD4908	Phase 1
0.7219	Intermediate Similarity	NPD1019	Discontinued
0.7219	Intermediate Similarity	NPD6234	Discontinued
0.7216	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD5283	Phase 1
0.7203	Intermediate Similarity	NPD1241	Discontinued
0.7181	Intermediate Similarity	NPD1608	Approved
0.7181	Intermediate Similarity	NPD9717	Approved
0.716	Intermediate Similarity	NPD7390	Discontinued
0.716	Intermediate Similarity	NPD4357	Discontinued
0.7151	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD3887	Approved
0.7143	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3268	Approved
0.7143	Intermediate Similarity	NPD1296	Phase 2
0.7126	Intermediate Similarity	NPD6280	Approved
0.7126	Intermediate Similarity	NPD6279	Approved
0.7119	Intermediate Similarity	NPD7549	Discontinued
0.7117	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1610	Phase 2
0.7112	Intermediate Similarity	NPD5005	Approved
0.7112	Intermediate Similarity	NPD5006	Approved
0.7107	Intermediate Similarity	NPD2353	Approved
0.7107	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6777	Approved
0.7097	Intermediate Similarity	NPD6780	Approved
0.7097	Intermediate Similarity	NPD6776	Approved
0.7097	Intermediate Similarity	NPD6779	Approved
0.7097	Intermediate Similarity	NPD6782	Approved
0.7097	Intermediate Similarity	NPD6781	Approved
0.7097	Intermediate Similarity	NPD6778	Approved
0.7097	Intermediate Similarity	NPD6233	Phase 2
0.7093	Intermediate Similarity	NPD5711	Approved
0.7093	Intermediate Similarity	NPD7229	Phase 3
0.7093	Intermediate Similarity	NPD5710	Approved
0.7089	Intermediate Similarity	NPD4308	Phase 3
0.7089	Intermediate Similarity	NPD7033	Discontinued
0.7086	Intermediate Similarity	NPD1876	Approved
0.7079	Intermediate Similarity	NPD8312	Approved
0.7079	Intermediate Similarity	NPD8313	Approved
0.7066	Intermediate Similarity	NPD5889	Approved
0.7066	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD5890	Approved
0.7062	Intermediate Similarity	NPD7685	Pre-registration
0.7059	Intermediate Similarity	NPD2861	Phase 2
0.7051	Intermediate Similarity	NPD3142	Approved
0.7051	Intermediate Similarity	NPD3140	Approved
0.7041	Intermediate Similarity	NPD4288	Approved
0.7039	Intermediate Similarity	NPD2797	Approved
0.7032	Intermediate Similarity	NPD6798	Discontinued
0.7032	Intermediate Similarity	NPD411	Approved
0.7029	Intermediate Similarity	NPD7228	Approved
0.7029	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD9268	Approved
0.7012	Intermediate Similarity	NPD4661	Approved
0.7012	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4662	Approved
0.7012	Intermediate Similarity	NPD3146	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data