NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.03
Volume:	236.847
LogP:	1.07
LogD:	0.598
LogS:	-3.042
# Rotatable Bonds:	2
TPSA:	73.5
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.825
Synthetic Accessibility Score:	3.879
Fsp3:	0.083
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:	-4.685
MDCK Permeability:	2.2573682144866325e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.771
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	84.89787292480469%
Volume Distribution (VD):	0.631
Pgp-substrate:	27.791339874267578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.937
CYP1A2-substrate:	0.622
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.062
CYP2D6-substrate:	0.839
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	4.542
Half-life (T1/2):	0.878

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.267
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.841
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.656
Carcinogencity:	0.941
Eye Corrosion:	0.008
Eye Irritation:	0.919
Respiratory Toxicity:	0.625

Download Data

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

Natural Product: NPC472881

Natural Product ID:	NPC472881
*Common Name:**	CZQRJKNTXXRWAS-SNAWJCMRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CZQRJKNTXXRWAS-SNAWJCMRSA-N
Standard InCHI:	InChI=1S/C12H10O4S/c1-17(15)5-4-9-7-11(14)10-6-8(13)2-3-12(10)16-9/h2-7,13H,1H3/b5-4+
SMILES:	CS(=O)/C=C/c1cc(=O)c2c(o1)ccc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593556
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579873]
NPO23424	Dirca palustris	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26225905]
NPO23424	Dirca palustris	Species	Thymelaeaceae	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	3
Others	1

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[540337]
NPT27	Others	Unspecified		IC50	>	10000.0	nM	PMID[540337]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[540337]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC90	=	7.8	ug.mL-1	PMID[540337]

☑ 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 NPC472881 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	380
0.1-0.2	2359
0.2-0.3	6097
0.3-0.4	12563
0.4-0.5	4485
0.5-0.6	6451
0.6-0.7	7042
0.7-0.8	3270
0.8-0.85	42
0.85-0.9	4
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9538	High Similarity	NPC472882
0.8992	High Similarity	NPC472888
0.8947	High Similarity	NPC7569
0.8881	High Similarity	NPC141549
0.8806	High Similarity	NPC278787
0.8676	High Similarity	NPC118253
0.86	High Similarity	NPC472886
0.8582	High Similarity	NPC298884
0.8571	High Similarity	NPC224657
0.8496	Intermediate Similarity	NPC4012
0.8444	Intermediate Similarity	NPC71525
0.84	Intermediate Similarity	NPC472887
0.8392	Intermediate Similarity	NPC145673
0.838	Intermediate Similarity	NPC18457
0.8378	Intermediate Similarity	NPC472884
0.8358	Intermediate Similarity	NPC193805
0.8357	Intermediate Similarity	NPC22222
0.8357	Intermediate Similarity	NPC281513
0.831	Intermediate Similarity	NPC98395
0.8295	Intermediate Similarity	NPC240163
0.8284	Intermediate Similarity	NPC93730
0.8239	Intermediate Similarity	NPC472883
0.8176	Intermediate Similarity	NPC472885
0.8175	Intermediate Similarity	NPC45537
0.8175	Intermediate Similarity	NPC22783
0.8175	Intermediate Similarity	NPC470841
0.8168	Intermediate Similarity	NPC269414
0.8151	Intermediate Similarity	NPC169479
0.8151	Intermediate Similarity	NPC159855
0.8116	Intermediate Similarity	NPC201419
0.8106	Intermediate Similarity	NPC32298
0.8082	Intermediate Similarity	NPC329493
0.8074	Intermediate Similarity	NPC46634
0.8074	Intermediate Similarity	NPC311219
0.8071	Intermediate Similarity	NPC324488
0.8071	Intermediate Similarity	NPC205360
0.8058	Intermediate Similarity	NPC187907
0.8058	Intermediate Similarity	NPC473019
0.8054	Intermediate Similarity	NPC46941
0.8045	Intermediate Similarity	NPC54243
0.8041	Intermediate Similarity	NPC473951
0.8014	Intermediate Similarity	NPC474340
0.8014	Intermediate Similarity	NPC124365
0.8013	Intermediate Similarity	NPC101957
0.8013	Intermediate Similarity	NPC120105
0.8	Intermediate Similarity	NPC186397
0.8	Intermediate Similarity	NPC12367
0.8	Intermediate Similarity	NPC118726
0.8	Intermediate Similarity	NPC268691
0.8	Intermediate Similarity	NPC37135
0.7987	Intermediate Similarity	NPC308799
0.7986	Intermediate Similarity	NPC477534
0.7986	Intermediate Similarity	NPC130976
0.7985	Intermediate Similarity	NPC470092
0.7973	Intermediate Similarity	NPC89664
0.7973	Intermediate Similarity	NPC274085
0.7972	Intermediate Similarity	NPC298900
0.797	Intermediate Similarity	NPC171023
0.7958	Intermediate Similarity	NPC128216
0.7956	Intermediate Similarity	NPC265910
0.7956	Intermediate Similarity	NPC91475
0.7947	Intermediate Similarity	NPC266499
0.7947	Intermediate Similarity	NPC223988
0.7947	Intermediate Similarity	NPC200221
0.7947	Intermediate Similarity	NPC294502
0.7943	Intermediate Similarity	NPC270369
0.7943	Intermediate Similarity	NPC137264
0.7943	Intermediate Similarity	NPC5515
0.7933	Intermediate Similarity	NPC113428
0.7933	Intermediate Similarity	NPC30647
0.7933	Intermediate Similarity	NPC239312
0.7933	Intermediate Similarity	NPC61284
0.7933	Intermediate Similarity	NPC61871
0.7933	Intermediate Similarity	NPC130230
0.7933	Intermediate Similarity	NPC275772
0.7933	Intermediate Similarity	NPC55557
0.7929	Intermediate Similarity	NPC197425
0.7919	Intermediate Similarity	NPC98926
0.7917	Intermediate Similarity	NPC64157
0.7917	Intermediate Similarity	NPC278832
0.7917	Intermediate Similarity	NPC242712
0.7917	Intermediate Similarity	NPC141934
0.7914	Intermediate Similarity	NPC95034
0.7914	Intermediate Similarity	NPC142087
0.791	Intermediate Similarity	NPC35744
0.791	Intermediate Similarity	NPC232178
0.7905	Intermediate Similarity	NPC1534
0.7902	Intermediate Similarity	NPC477210
0.7902	Intermediate Similarity	NPC265793
0.7899	Intermediate Similarity	NPC4164
0.7895	Intermediate Similarity	NPC306821
0.7895	Intermediate Similarity	NPC45873
0.7895	Intermediate Similarity	NPC184136
0.7895	Intermediate Similarity	NPC240664
0.7887	Intermediate Similarity	NPC473584
0.7887	Intermediate Similarity	NPC477406
0.7887	Intermediate Similarity	NPC113006
0.7887	Intermediate Similarity	NPC475589
0.7887	Intermediate Similarity	NPC31872
0.7883	Intermediate Similarity	NPC477153
0.7883	Intermediate Similarity	NPC182646
0.7881	Intermediate Similarity	NPC5537
0.7879	Intermediate Similarity	NPC161304
0.7877	Intermediate Similarity	NPC57380
0.7872	Intermediate Similarity	NPC115998
0.7872	Intermediate Similarity	NPC39753
0.7868	Intermediate Similarity	NPC476165
0.7867	Intermediate Similarity	NPC301949
0.7867	Intermediate Similarity	NPC60389
0.7863	Intermediate Similarity	NPC279916
0.7852	Intermediate Similarity	NPC14177
0.7847	Intermediate Similarity	NPC172262
0.7847	Intermediate Similarity	NPC248872
0.7843	Intermediate Similarity	NPC308451
0.7843	Intermediate Similarity	NPC475076
0.7843	Intermediate Similarity	NPC208043
0.7843	Intermediate Similarity	NPC149614
0.7843	Intermediate Similarity	NPC226973
0.7842	Intermediate Similarity	NPC51037
0.7842	Intermediate Similarity	NPC306765
0.7832	Intermediate Similarity	NPC25937
0.7832	Intermediate Similarity	NPC10971
0.7832	Intermediate Similarity	NPC477536
0.7829	Intermediate Similarity	NPC216318
0.7829	Intermediate Similarity	NPC296197
0.7829	Intermediate Similarity	NPC17286
0.7829	Intermediate Similarity	NPC259713
0.7829	Intermediate Similarity	NPC195351
0.7826	Intermediate Similarity	NPC56332
0.7823	Intermediate Similarity	NPC477537
0.782	Intermediate Similarity	NPC163398
0.7817	Intermediate Similarity	NPC301717
0.7815	Intermediate Similarity	NPC252208
0.781	Intermediate Similarity	NPC49441
0.7808	Intermediate Similarity	NPC250266
0.7808	Intermediate Similarity	NPC299379
0.7808	Intermediate Similarity	NPC266597
0.7808	Intermediate Similarity	NPC332594
0.7808	Intermediate Similarity	NPC228661
0.7806	Intermediate Similarity	NPC256612
0.7806	Intermediate Similarity	NPC20830
0.7801	Intermediate Similarity	NPC261759
0.78	Intermediate Similarity	NPC47152
0.78	Intermediate Similarity	NPC472917
0.78	Intermediate Similarity	NPC70136
0.78	Intermediate Similarity	NPC155144
0.78	Intermediate Similarity	NPC469764
0.7793	Intermediate Similarity	NPC77955
0.7793	Intermediate Similarity	NPC151113
0.7793	Intermediate Similarity	NPC324929
0.7792	Intermediate Similarity	NPC239128
0.7792	Intermediate Similarity	NPC83508
0.7792	Intermediate Similarity	NPC71334
0.7792	Intermediate Similarity	NPC75069
0.7792	Intermediate Similarity	NPC301323
0.7792	Intermediate Similarity	NPC57030
0.7792	Intermediate Similarity	NPC212678
0.7792	Intermediate Similarity	NPC256283
0.7792	Intermediate Similarity	NPC222830
0.7792	Intermediate Similarity	NPC25270
0.7792	Intermediate Similarity	NPC162313
0.7792	Intermediate Similarity	NPC187498
0.7792	Intermediate Similarity	NPC275836
0.7792	Intermediate Similarity	NPC120163
0.7792	Intermediate Similarity	NPC131624
0.7792	Intermediate Similarity	NPC301123
0.7792	Intermediate Similarity	NPC100887
0.7792	Intermediate Similarity	NPC198826
0.7792	Intermediate Similarity	NPC156222
0.7792	Intermediate Similarity	NPC293183
0.7792	Intermediate Similarity	NPC275722
0.7792	Intermediate Similarity	NPC188203
0.7792	Intermediate Similarity	NPC241498
0.7786	Intermediate Similarity	NPC181715
0.7778	Intermediate Similarity	NPC201284
0.7778	Intermediate Similarity	NPC37348
0.7778	Intermediate Similarity	NPC108113
0.7778	Intermediate Similarity	NPC62042
0.7778	Intermediate Similarity	NPC50898
0.7778	Intermediate Similarity	NPC227122
0.7778	Intermediate Similarity	NPC93756
0.7778	Intermediate Similarity	NPC274121
0.7778	Intermediate Similarity	NPC223457
0.7778	Intermediate Similarity	NPC78540
0.7778	Intermediate Similarity	NPC295036
0.7778	Intermediate Similarity	NPC57601
0.7778	Intermediate Similarity	NPC213216
0.7778	Intermediate Similarity	NPC77858
0.7778	Intermediate Similarity	NPC179183
0.777	Intermediate Similarity	NPC281207
0.777	Intermediate Similarity	NPC2771
0.777	Intermediate Similarity	NPC269652
0.7763	Intermediate Similarity	NPC194856
0.7763	Intermediate Similarity	NPC228012
0.7763	Intermediate Similarity	NPC276930
0.7755	Intermediate Similarity	NPC112757
0.7755	Intermediate Similarity	NPC1268
0.7755	Intermediate Similarity	NPC477408
0.7755	Intermediate Similarity	NPC475045
0.7755	Intermediate Similarity	NPC475012

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 NPC472881 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	378
0.1-0.2	1026
0.2-0.3	1551
0.3-0.4	2775
0.4-0.5	1916
0.5-0.6	1119
0.6-0.7	313
0.7-0.8	69
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8129	Intermediate Similarity	NPD2313	Discontinued
0.8085	Intermediate Similarity	NPD447	Suspended
0.8074	Intermediate Similarity	NPD9717	Approved
0.8029	Intermediate Similarity	NPD1203	Approved
0.7986	Intermediate Similarity	NPD2935	Discontinued
0.7931	Intermediate Similarity	NPD2346	Discontinued
0.7872	Intermediate Similarity	NPD411	Approved
0.7808	Intermediate Similarity	NPD2344	Approved
0.7793	Intermediate Similarity	NPD2799	Discontinued
0.7742	Intermediate Similarity	NPD2801	Approved
0.7737	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1511	Approved
0.7714	Intermediate Similarity	NPD2798	Approved
0.7687	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6844	Discontinued
0.7632	Intermediate Similarity	NPD1512	Approved
0.76	Intermediate Similarity	NPD2309	Approved
0.7597	Intermediate Similarity	NPD3226	Approved
0.7586	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD9493	Approved
0.7551	Intermediate Similarity	NPD1510	Phase 2
0.7533	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1240	Approved
0.7517	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1549	Phase 2
0.75	Intermediate Similarity	NPD1551	Phase 2
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7481	Intermediate Similarity	NPD6671	Approved
0.7468	Intermediate Similarity	NPD5402	Approved
0.7465	Intermediate Similarity	NPD1019	Discontinued
0.7463	Intermediate Similarity	NPD1241	Discontinued
0.745	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4308	Phase 3
0.7429	Intermediate Similarity	NPD1481	Phase 2
0.7415	Intermediate Similarity	NPD1607	Approved
0.741	Intermediate Similarity	NPD3496	Discontinued
0.741	Intermediate Similarity	NPD5953	Discontinued
0.7394	Intermediate Similarity	NPD1470	Approved
0.7357	Intermediate Similarity	NPD1535	Discovery
0.7342	Intermediate Similarity	NPD1934	Approved
0.7338	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7440	Discontinued
0.7312	Intermediate Similarity	NPD3882	Suspended
0.7303	Intermediate Similarity	NPD3750	Approved
0.7296	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2797	Approved
0.7267	Intermediate Similarity	NPD2796	Approved
0.726	Intermediate Similarity	NPD3268	Approved
0.7237	Intermediate Similarity	NPD2800	Approved
0.7234	Intermediate Similarity	NPD1201	Approved
0.7219	Intermediate Similarity	NPD1471	Phase 3
0.7219	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7286	Phase 2
0.7183	Intermediate Similarity	NPD1608	Approved
0.7179	Intermediate Similarity	NPD5049	Phase 3
0.7172	Intermediate Similarity	NPD9494	Approved
0.7162	Intermediate Similarity	NPD4307	Phase 2
0.7124	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1933	Approved
0.7107	Intermediate Similarity	NPD4380	Phase 2
0.709	Intermediate Similarity	NPD9266	Approved
0.709	Intermediate Similarity	NPD74	Approved
0.7081	Intermediate Similarity	NPD7819	Suspended
0.7068	Intermediate Similarity	NPD968	Approved
0.7055	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD6799	Approved
0.7047	Intermediate Similarity	NPD943	Approved
0.7037	Intermediate Similarity	NPD3817	Phase 2
0.7037	Intermediate Similarity	NPD2296	Approved
0.7034	Intermediate Similarity	NPD3266	Approved
0.7034	Intermediate Similarity	NPD3267	Approved
0.703	Intermediate Similarity	NPD1247	Approved
0.7025	Intermediate Similarity	NPD920	Approved
0.7025	Intermediate Similarity	NPD5403	Approved
0.7024	Intermediate Similarity	NPD3818	Discontinued
0.7015	Intermediate Similarity	NPD9263	Approved
0.7015	Intermediate Similarity	NPD9267	Approved
0.7015	Intermediate Similarity	NPD9264	Approved
0.7013	Intermediate Similarity	NPD1243	Approved
0.7006	Intermediate Similarity	NPD5401	Approved
0.6993	Remote Similarity	NPD422	Phase 1
0.6992	Remote Similarity	NPD9697	Approved
0.698	Remote Similarity	NPD4062	Phase 3
0.6974	Remote Similarity	NPD3748	Approved
0.6972	Remote Similarity	NPD17	Approved
0.6972	Remote Similarity	NPD1778	Approved
0.697	Remote Similarity	NPD5494	Approved
0.6968	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3225	Approved
0.6957	Remote Similarity	NPD7411	Suspended
0.6951	Remote Similarity	NPD7075	Discontinued
0.6951	Remote Similarity	NPD3749	Approved
0.695	Remote Similarity	NPD9545	Approved
0.6933	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2531	Phase 2
0.6919	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6166	Phase 2
0.6905	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2532	Approved
0.6899	Remote Similarity	NPD2534	Approved
0.6899	Remote Similarity	NPD4661	Approved
0.6899	Remote Similarity	NPD2533	Approved
0.6899	Remote Similarity	NPD4662	Approved
0.6899	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7768	Phase 2
0.6882	Remote Similarity	NPD7054	Approved
0.6875	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1611	Approved
0.6871	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4628	Phase 3
0.6853	Remote Similarity	NPD2107	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1876	Approved
0.6842	Remote Similarity	NPD7472	Approved
0.6832	Remote Similarity	NPD2649	Approved
0.6832	Remote Similarity	NPD2651	Approved
0.6832	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3972	Approved
0.6826	Remote Similarity	NPD6959	Discontinued
0.6818	Remote Similarity	NPD5712	Approved
0.6818	Remote Similarity	NPD6099	Approved
0.6818	Remote Similarity	NPD6100	Approved
0.681	Remote Similarity	NPD6801	Discontinued
0.6803	Remote Similarity	NPD1164	Approved
0.6802	Remote Similarity	NPD6797	Phase 2
0.6802	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3764	Approved
0.6795	Remote Similarity	NPD1652	Phase 2
0.679	Remote Similarity	NPD6599	Discontinued
0.6788	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7229	Phase 3
0.6786	Remote Similarity	NPD9281	Approved
0.6776	Remote Similarity	NPD230	Phase 1
0.6772	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7251	Discontinued
0.6763	Remote Similarity	NPD6559	Discontinued
0.6757	Remote Similarity	NPD5647	Approved
0.6755	Remote Similarity	NPD6233	Phase 2
0.6753	Remote Similarity	NPD7033	Discontinued
0.6747	Remote Similarity	NPD6971	Discontinued
0.6744	Remote Similarity	NPD7074	Phase 3
0.6735	Remote Similarity	NPD1283	Approved
0.6724	Remote Similarity	NPD7808	Phase 3
0.6721	Remote Similarity	NPD2339	Phase 3
0.6716	Remote Similarity	NPD9261	Approved
0.6714	Remote Similarity	NPD1398	Phase 1
0.6713	Remote Similarity	NPD1894	Discontinued
0.6711	Remote Similarity	NPD3142	Approved
0.6711	Remote Similarity	NPD3140	Approved
0.6711	Remote Similarity	NPD2861	Phase 2
0.6709	Remote Similarity	NPD2354	Approved
0.6708	Remote Similarity	NPD8012	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD919	Approved
0.6706	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1296	Phase 2
0.6689	Remote Similarity	NPD6798	Discontinued
0.6686	Remote Similarity	NPD8312	Approved
0.6686	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8313	Approved
0.6686	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD1559	Discontinued
0.6667	Remote Similarity	NPD5585	Approved
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD1184	Approved
0.6667	Remote Similarity	NPD4340	Discontinued
0.6667	Remote Similarity	NPD1465	Phase 2
0.6646	Remote Similarity	NPD6273	Approved
0.6646	Remote Similarity	NPD7003	Approved
0.6645	Remote Similarity	NPD520	Approved
0.6643	Remote Similarity	NPD5536	Phase 2
0.6642	Remote Similarity	NPD290	Approved
0.6624	Remote Similarity	NPD2424	Discontinued
0.6623	Remote Similarity	NPD6651	Approved
0.6622	Remote Similarity	NPD6696	Suspended
0.6621	Remote Similarity	NPD4626	Approved
0.6606	Remote Similarity	NPD6279	Approved
0.6606	Remote Similarity	NPD6280	Approved
0.6603	Remote Similarity	NPD1519	Approved
0.6603	Remote Similarity	NPD6032	Approved
0.6603	Remote Similarity	NPD1538	Phase 1
0.6603	Remote Similarity	NPD1537	Approved
0.6603	Remote Similarity	NPD2862	Discontinued
0.6601	Remote Similarity	NPD4060	Phase 1
0.6599	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD1548	Phase 1

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