NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.06
Volume:	241.737
LogP:	2.831
LogD:	2.705
LogS:	-3.435
# Rotatable Bonds:	1
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.666
Synthetic Accessibility Score:	2.065
Fsp3:	0.071
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:	-4.757
MDCK Permeability:	1.942173912539147e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.984
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.835

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	90.43097686767578%
Volume Distribution (VD):	0.721
Pgp-substrate:	13.481633186340332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.933
CYP2C19-inhibitor:	0.834
CYP2C19-substrate:	0.158
CYP2C9-inhibitor:	0.597
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.782
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.734
CYP3A4-substrate:	0.223

ADMET: Excretion

Clearance (CL):	4.457
Half-life (T1/2):	0.728

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.124
Drug-inuced Liver Injury (DILI):	0.901
AMES Toxicity:	0.774
Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.506
Skin Sensitization:	0.847
Carcinogencity:	0.843
Eye Corrosion:	0.231
Eye Irritation:	0.986
Respiratory Toxicity:	0.29

Download Data

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

Natural Product: NPC145673

Natural Product ID:	NPC145673
*Common Name:**	7-Hydroxy-1-Methoxyxanthone
IUPAC Name:	7-hydroxy-1-methoxyxanthen-9-one
Synonyms:
Standard InCHIKey:	FWBCCNVJDMEVSM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10O4/c1-17-11-3-2-4-12-13(11)14(16)9-7-8(15)5-6-10(9)18-12/h2-7,15H,1H3
SMILES:	COc1cccc2c1c(=O)c1cc(ccc1o2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2029867
PubChem CID:	10490332
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
NPO32798	polygala karensium	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22552195]

☑ 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
Others	1

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT493	Individual Protein	Neuraminidase	Influenza A virus	IC50	>	100.0	ug.mL-1	PMID[540515]
NPT2	Others	Unspecified		Ratio IC50	=	243.0	n.a.	PMID[540515]

☑ 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 NPC145673 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	477
0.1-0.2	2016
0.2-0.3	5068
0.3-0.4	11893
0.4-0.5	5642
0.5-0.6	4299
0.6-0.7	5513
0.7-0.8	4482
0.8-0.85	2005
0.85-0.9	1093
0.9-0.95	202
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9851	High Similarity	NPC18457
0.9571	High Similarity	NPC46941
0.9565	High Similarity	NPC169479
0.9565	High Similarity	NPC159855
0.9437	High Similarity	NPC294502
0.9437	High Similarity	NPC200221
0.9437	High Similarity	NPC266499
0.9366	High Similarity	NPC186397
0.9366	High Similarity	NPC37135
0.9306	High Similarity	NPC149614
0.9301	High Similarity	NPC223988
0.9291	High Similarity	NPC469764
0.9254	High Similarity	NPC141549
0.9236	High Similarity	NPC120105
0.9236	High Similarity	NPC62042
0.9236	High Similarity	NPC179183
0.9236	High Similarity	NPC101957
0.9225	High Similarity	NPC209278
0.9225	High Similarity	NPC469758
0.9179	High Similarity	NPC278787
0.9178	High Similarity	NPC167091
0.9178	High Similarity	NPC271779
0.9178	High Similarity	NPC88645
0.9178	High Similarity	NPC206238
0.9178	High Similarity	NPC292214
0.9172	High Similarity	NPC117579
0.9161	High Similarity	NPC71055
0.9155	High Similarity	NPC303185
0.9155	High Similarity	NPC184649
0.9155	High Similarity	NPC98926
0.9149	High Similarity	NPC73028
0.9143	High Similarity	NPC182421
0.911	High Similarity	NPC199100
0.911	High Similarity	NPC75069
0.911	High Similarity	NPC39007
0.911	High Similarity	NPC120537
0.911	High Similarity	NPC474843
0.911	High Similarity	NPC281272
0.911	High Similarity	NPC161277
0.911	High Similarity	NPC180234
0.911	High Similarity	NPC101996
0.9103	High Similarity	NPC470107
0.9103	High Similarity	NPC227122
0.9097	High Similarity	NPC194856
0.9097	High Similarity	NPC5537
0.9097	High Similarity	NPC276930
0.9091	High Similarity	NPC196114
0.9091	High Similarity	NPC299011
0.9085	High Similarity	NPC59551
0.9085	High Similarity	NPC113770
0.9058	High Similarity	NPC9985
0.9058	High Similarity	NPC239495
0.9048	High Similarity	NPC135522
0.9048	High Similarity	NPC472915
0.9041	High Similarity	NPC39819
0.9041	High Similarity	NPC204515
0.9041	High Similarity	NPC475076
0.9041	High Similarity	NPC171010
0.9041	High Similarity	NPC251110
0.9034	High Similarity	NPC70764
0.9028	High Similarity	NPC207729
0.9021	High Similarity	NPC311144
0.9014	High Similarity	NPC310340
0.9014	High Similarity	NPC1534
0.9014	High Similarity	NPC202981
0.9007	High Similarity	NPC275734
0.9	High Similarity	NPC472460
0.9	High Similarity	NPC329225
0.9	High Similarity	NPC99333
0.9	High Similarity	NPC147686
0.9	High Similarity	NPC280284
0.9	High Similarity	NPC188947
0.8993	High Similarity	NPC181960
0.8993	High Similarity	NPC99597
0.8993	High Similarity	NPC210084
0.8986	High Similarity	NPC37392
0.8986	High Similarity	NPC2928
0.8986	High Similarity	NPC113906
0.8986	High Similarity	NPC472909
0.8978	High Similarity	NPC128216
0.8973	High Similarity	NPC184136
0.8973	High Similarity	NPC37348
0.8973	High Similarity	NPC248102
0.8973	High Similarity	NPC306821
0.8973	High Similarity	NPC61620
0.8973	High Similarity	NPC29231
0.8971	High Similarity	NPC137264
0.8966	High Similarity	NPC12367
0.8966	High Similarity	NPC39195
0.8966	High Similarity	NPC118726
0.8963	High Similarity	NPC197425
0.8958	High Similarity	NPC290133
0.8958	High Similarity	NPC187282
0.8958	High Similarity	NPC231013
0.8958	High Similarity	NPC24136
0.8951	High Similarity	NPC166138
0.8951	High Similarity	NPC106985
0.8951	High Similarity	NPC18585
0.8944	High Similarity	NPC3188
0.8936	High Similarity	NPC310135
0.8936	High Similarity	NPC261234
0.8936	High Similarity	NPC316480
0.8936	High Similarity	NPC20709
0.8936	High Similarity	NPC222342
0.8936	High Similarity	NPC329203
0.8936	High Similarity	NPC265871
0.8936	High Similarity	NPC150648
0.8936	High Similarity	NPC274784
0.8936	High Similarity	NPC225153
0.8929	High Similarity	NPC243083
0.8929	High Similarity	NPC287246
0.8929	High Similarity	NPC275055
0.8929	High Similarity	NPC212767
0.8929	High Similarity	NPC12296
0.8929	High Similarity	NPC266597
0.8929	High Similarity	NPC296490
0.8929	High Similarity	NPC79943
0.8929	High Similarity	NPC476480
0.8929	High Similarity	NPC107586
0.8929	High Similarity	NPC228661
0.8929	High Similarity	NPC32441
0.8929	High Similarity	NPC13768
0.8929	High Similarity	NPC84585
0.8929	High Similarity	NPC250266
0.8929	High Similarity	NPC295261
0.8929	High Similarity	NPC290291
0.8926	High Similarity	NPC472916
0.8926	High Similarity	NPC255106
0.8926	High Similarity	NPC235165
0.8919	High Similarity	NPC95842
0.8919	High Similarity	NPC178964
0.8919	High Similarity	NPC280937
0.8919	High Similarity	NPC280530
0.8912	High Similarity	NPC226973
0.8912	High Similarity	NPC208043
0.8912	High Similarity	NPC202157
0.8912	High Similarity	NPC308451
0.8905	High Similarity	NPC113006
0.8904	High Similarity	NPC183959
0.8904	High Similarity	NPC1612
0.8897	High Similarity	NPC115998
0.8897	High Similarity	NPC308200
0.8897	High Similarity	NPC17816
0.8897	High Similarity	NPC39753
0.8897	High Similarity	NPC130230
0.8897	High Similarity	NPC7569
0.8897	High Similarity	NPC275772
0.8897	High Similarity	NPC239312
0.8889	High Similarity	NPC311741
0.8889	High Similarity	NPC234629
0.8889	High Similarity	NPC155144
0.8881	High Similarity	NPC144499
0.8874	High Similarity	NPC471976
0.8873	High Similarity	NPC281207
0.8873	High Similarity	NPC6407
0.8873	High Similarity	NPC110228
0.8873	High Similarity	NPC129853
0.8873	High Similarity	NPC69769
0.8873	High Similarity	NPC188243
0.8873	High Similarity	NPC284550
0.8873	High Similarity	NPC76445
0.8873	High Similarity	NPC269652
0.8867	High Similarity	NPC472913
0.8867	High Similarity	NPC96167
0.8867	High Similarity	NPC474836
0.8867	High Similarity	NPC245758
0.8867	High Similarity	NPC262286
0.8867	High Similarity	NPC162869
0.8867	High Similarity	NPC48208
0.8867	High Similarity	NPC472911
0.8867	High Similarity	NPC475267
0.8867	High Similarity	NPC156057
0.8867	High Similarity	NPC472910
0.8867	High Similarity	NPC196448
0.8867	High Similarity	NPC78225
0.8867	High Similarity	NPC36852
0.8867	High Similarity	NPC222814
0.8867	High Similarity	NPC472914
0.8867	High Similarity	NPC476981
0.8867	High Similarity	NPC474208
0.8865	High Similarity	NPC278323
0.8865	High Similarity	NPC268691
0.8865	High Similarity	NPC55162
0.8865	High Similarity	NPC309154
0.8865	High Similarity	NPC124269
0.8865	High Similarity	NPC90665
0.8865	High Similarity	NPC12175
0.8865	High Similarity	NPC118813
0.8865	High Similarity	NPC279668
0.8859	High Similarity	NPC256612
0.8859	High Similarity	NPC20830
0.8859	High Similarity	NPC255807
0.8859	High Similarity	NPC31018
0.8857	High Similarity	NPC47815
0.8857	High Similarity	NPC473391
0.8857	High Similarity	NPC124784
0.8857	High Similarity	NPC235428
0.8857	High Similarity	NPC127447
0.8857	High Similarity	NPC87545
0.8857	High Similarity	NPC194281

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 NPC145673 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	467
0.1-0.2	993
0.2-0.3	1629
0.3-0.4	2730
0.4-0.5	1822
0.5-0.6	1048
0.6-0.7	298
0.7-0.8	108
0.8-0.85	40
0.85-0.9	12
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD1549	Phase 2
0.8929	High Similarity	NPD1552	Clinical (unspecified phase)
0.8929	High Similarity	NPD1550	Clinical (unspecified phase)
0.8792	High Similarity	NPD2801	Approved
0.8786	High Similarity	NPD1510	Phase 2
0.8768	High Similarity	NPD1240	Approved
0.8759	High Similarity	NPD4378	Clinical (unspecified phase)
0.8725	High Similarity	NPD1934	Approved
0.869	High Similarity	NPD1511	Approved
0.8667	High Similarity	NPD2393	Clinical (unspecified phase)
0.8643	High Similarity	NPD1607	Approved
0.8592	High Similarity	NPD1551	Phase 2
0.8571	High Similarity	NPD1512	Approved
0.8487	Intermediate Similarity	NPD5402	Approved
0.8462	Intermediate Similarity	NPD2796	Approved
0.8462	Intermediate Similarity	NPD2935	Discontinued
0.8421	Intermediate Similarity	NPD7819	Suspended
0.8378	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD3750	Approved
0.8344	Intermediate Similarity	NPD4380	Phase 2
0.8312	Intermediate Similarity	NPD3882	Suspended
0.8289	Intermediate Similarity	NPD7411	Suspended
0.8276	Intermediate Similarity	NPD2346	Discontinued
0.8269	Intermediate Similarity	NPD5494	Approved
0.8261	Intermediate Similarity	NPD1203	Approved
0.8258	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD7075	Discontinued
0.8247	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD2313	Discontinued
0.8219	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD6166	Phase 2
0.8158	Intermediate Similarity	NPD3226	Approved
0.8141	Intermediate Similarity	NPD3749	Approved
0.8101	Intermediate Similarity	NPD6959	Discontinued
0.8077	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD7768	Phase 2
0.8075	Intermediate Similarity	NPD3818	Discontinued
0.8067	Intermediate Similarity	NPD6799	Approved
0.8056	Intermediate Similarity	NPD447	Suspended
0.8043	Intermediate Similarity	NPD9717	Approved
0.8041	Intermediate Similarity	NPD2800	Approved
0.8026	Intermediate Similarity	NPD5403	Approved
0.8014	Intermediate Similarity	NPD3748	Approved
0.8013	Intermediate Similarity	NPD5401	Approved
0.8013	Intermediate Similarity	NPD3817	Phase 2
0.7988	Intermediate Similarity	NPD6559	Discontinued
0.7987	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD943	Approved
0.7975	Intermediate Similarity	NPD7074	Phase 3
0.7959	Intermediate Similarity	NPD6099	Approved
0.7959	Intermediate Similarity	NPD6100	Approved
0.795	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7054	Approved
0.7908	Intermediate Similarity	NPD920	Approved
0.7905	Intermediate Similarity	NPD2344	Approved
0.7891	Intermediate Similarity	NPD2799	Discontinued
0.7891	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6844	Discontinued
0.7885	Intermediate Similarity	NPD6801	Discontinued
0.7875	Intermediate Similarity	NPD1247	Approved
0.7872	Intermediate Similarity	NPD1470	Approved
0.7871	Intermediate Similarity	NPD6599	Discontinued
0.7866	Intermediate Similarity	NPD7472	Approved
0.7847	Intermediate Similarity	NPD411	Approved
0.7842	Intermediate Similarity	NPD1610	Phase 2
0.7834	Intermediate Similarity	NPD1465	Phase 2
0.7832	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD6832	Phase 2
0.7826	Intermediate Similarity	NPD6232	Discontinued
0.7818	Intermediate Similarity	NPD6797	Phase 2
0.7817	Intermediate Similarity	NPD2798	Approved
0.7805	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD5844	Phase 1
0.78	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1243	Approved
0.7791	Intermediate Similarity	NPD7473	Discontinued
0.7778	Intermediate Similarity	NPD2533	Approved
0.7778	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2534	Approved
0.7778	Intermediate Similarity	NPD2532	Approved
0.7771	Intermediate Similarity	NPD7251	Discontinued
0.777	Intermediate Similarity	NPD4308	Phase 3
0.7762	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1613	Approved
0.7725	Intermediate Similarity	NPD7808	Phase 3
0.7724	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1201	Approved
0.7708	Intermediate Similarity	NPD4908	Phase 1
0.7697	Intermediate Similarity	NPD2309	Approved
0.7687	Intermediate Similarity	NPD1933	Approved
0.7681	Intermediate Similarity	NPD1548	Phase 1
0.7664	Intermediate Similarity	NPD9493	Approved
0.766	Intermediate Similarity	NPD1608	Approved
0.7655	Intermediate Similarity	NPD4625	Phase 3
0.7647	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD2797	Approved
0.7606	Intermediate Similarity	NPD4749	Approved
0.7605	Intermediate Similarity	NPD5953	Discontinued
0.7605	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD3268	Approved
0.759	Intermediate Similarity	NPD7286	Phase 2
0.7589	Intermediate Similarity	NPD422	Phase 1
0.7569	Intermediate Similarity	NPD1019	Discontinued
0.7568	Intermediate Similarity	NPD230	Phase 1
0.7561	Intermediate Similarity	NPD3926	Phase 2
0.7531	Intermediate Similarity	NPD919	Approved
0.753	Intermediate Similarity	NPD3751	Discontinued
0.7517	Intermediate Similarity	NPD6651	Approved
0.7517	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD4307	Phase 2
0.7471	Intermediate Similarity	NPD8312	Approved
0.7471	Intermediate Similarity	NPD8313	Approved
0.7471	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD6671	Approved
0.7447	Intermediate Similarity	NPD17	Approved
0.7436	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD3225	Approved
0.7417	Intermediate Similarity	NPD7033	Discontinued
0.7417	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1481	Phase 2
0.7412	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4628	Phase 3
0.7379	Intermediate Similarity	NPD3267	Approved
0.7379	Intermediate Similarity	NPD3266	Approved
0.7375	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7390	Discontinued
0.7365	Intermediate Similarity	NPD3764	Approved
0.7365	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4288	Approved
0.7343	Intermediate Similarity	NPD1535	Discovery
0.7342	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1471	Phase 3
0.7319	Intermediate Similarity	NPD1241	Discontinued
0.7296	Intermediate Similarity	NPD1653	Approved
0.7289	Intermediate Similarity	NPD3787	Discontinued
0.7289	Intermediate Similarity	NPD5710	Approved
0.7289	Intermediate Similarity	NPD5711	Approved
0.7273	Intermediate Similarity	NPD3496	Discontinued
0.7248	Intermediate Similarity	NPD1296	Phase 2
0.7191	Intermediate Similarity	NPD4363	Phase 3
0.7191	Intermediate Similarity	NPD4360	Phase 2
0.7185	Intermediate Similarity	NPD968	Approved
0.7183	Intermediate Similarity	NPD9545	Approved
0.7182	Intermediate Similarity	NPD6777	Approved
0.7182	Intermediate Similarity	NPD6781	Approved
0.7182	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6778	Approved
0.7182	Intermediate Similarity	NPD6776	Approved
0.7182	Intermediate Similarity	NPD6780	Approved
0.7182	Intermediate Similarity	NPD6779	Approved
0.7182	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD3027	Phase 3
0.7159	Intermediate Similarity	NPD4287	Approved
0.7159	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6971	Discontinued
0.7143	Intermediate Similarity	NPD5406	Approved
0.7143	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD1164	Approved
0.7143	Intermediate Similarity	NPD5405	Approved
0.7143	Intermediate Similarity	NPD5404	Approved
0.7134	Intermediate Similarity	NPD2296	Approved
0.7133	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2654	Approved
0.7107	Intermediate Similarity	NPD4661	Approved
0.7107	Intermediate Similarity	NPD4662	Approved
0.7105	Intermediate Similarity	NPD5124	Phase 1
0.7105	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6823	Phase 2
0.7101	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6233	Phase 2
0.7083	Intermediate Similarity	NPD1778	Approved
0.7083	Intermediate Similarity	NPD7229	Phase 3
0.708	Intermediate Similarity	NPD9266	Approved
0.708	Intermediate Similarity	NPD74	Approved
0.7075	Intermediate Similarity	NPD1876	Approved
0.7065	Intermediate Similarity	NPD7697	Approved
0.7065	Intermediate Similarity	NPD7435	Discontinued
0.7065	Intermediate Similarity	NPD7696	Phase 3
0.7065	Intermediate Similarity	NPD7698	Approved
0.7055	Intermediate Similarity	NPD5890	Approved
0.7055	Intermediate Similarity	NPD3972	Approved
0.7055	Intermediate Similarity	NPD5889	Approved
0.7052	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD9494	Approved
0.7045	Intermediate Similarity	NPD8150	Discontinued
0.7045	Intermediate Similarity	NPD8434	Phase 2
0.7044	Intermediate Similarity	NPD6143	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