NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	212.05
Volume:	215.65
LogP:	2.965
LogD:	2.71
LogS:	-3.49
# Rotatable Bonds:	0
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.583
Synthetic Accessibility Score:	1.854
Fsp3:	0.0
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:	-4.752
MDCK Permeability:	1.634333784750197e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.718
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.714
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	93.24700164794922%
Volume Distribution (VD):	0.492
Pgp-substrate:	8.829041481018066%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.495
CYP2C19-inhibitor:	0.754
CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.376
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.794
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.467
CYP3A4-substrate:	0.205

ADMET: Excretion

Clearance (CL):	3.78
Half-life (T1/2):	0.635

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.156
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.791
Rat Oral Acute Toxicity:	0.247
Maximum Recommended Daily Dose:	0.518
Skin Sensitization:	0.927
Carcinogencity:	0.876
Eye Corrosion:	0.166
Eye Irritation:	0.989
Respiratory Toxicity:	0.317

Download Data

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

Natural Product: NPC278787

Natural Product ID:	NPC278787
*Common Name:**	2-Hydroxyxanthen-9-One
IUPAC Name:	2-hydroxyxanthen-9-one
Synonyms:
Standard InCHIKey:	WSACHQJPCNOREV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C13H8O3/c14-8-5-6-12-10(7-8)13(15)9-3-1-2-4-11(9)16-12/h1-7,14H
SMILES:	Oc1ccc2c(c1)c(=O)c1c(o2)cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL185960
PubChem CID:	74708
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
NPO18656	Iphigenia indica	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18656	Iphigenia indica	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18656	Iphigenia indica	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27687	Peliosanthes sinica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18656	Iphigenia indica	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19688	Mangifera odorata	Species	Anacardiaceae	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
EC50	1
IC50	2
Others	6

Activity Type	# Activity
Cell Line	2
Individual Protein	3
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	=	3800.0	nM	PMID[528795]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	0.0	%	PMID[528796]
NPT617	Organism	Danio rerio	Danio rerio	EC50	=	760.0	nM	PMID[528796]
NPT617	Organism	Danio rerio	Danio rerio	Activity	=	0.0	%	PMID[528796]
NPT2	Others	Unspecified		Inhibition	=	36.68	%	PMID[528797]
NPT2	Others	Unspecified		Inhibition	=	24.18	%	PMID[528797]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	IC50	=	5600.0	nM	PMID[528797]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	89.32	%	PMID[528797]

☑ 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 NPC278787 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	484
0.1-0.2	2182
0.2-0.3	5411
0.3-0.4	12365
0.4-0.5	4639
0.5-0.6	5318
0.6-0.7	6682
0.7-0.8	4874
0.8-0.85	674
0.85-0.9	57
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC141549
0.968	High Similarity	NPC7569
0.9318	High Similarity	NPC18457
0.9225	High Similarity	NPC118253
0.9179	High Similarity	NPC145673
0.9134	High Similarity	NPC298884
0.9127	High Similarity	NPC224657
0.9048	High Similarity	NPC193805
0.9044	High Similarity	NPC159855
0.9044	High Similarity	NPC169479
0.9024	High Similarity	NPC35744
0.8968	High Similarity	NPC93730
0.8837	High Similarity	NPC22783
0.881	High Similarity	NPC314329
0.8806	High Similarity	NPC472881
0.879	High Similarity	NPC32298
0.8786	High Similarity	NPC46941
0.8777	High Similarity	NPC473951
0.875	High Similarity	NPC4012
0.8723	High Similarity	NPC37135
0.8723	High Similarity	NPC186397
0.872	High Similarity	NPC54243
0.8662	High Similarity	NPC294502
0.8662	High Similarity	NPC200221
0.8662	High Similarity	NPC223988
0.8662	High Similarity	NPC266499
0.8623	High Similarity	NPC124365
0.8601	High Similarity	NPC101957
0.8601	High Similarity	NPC120105
0.8593	High Similarity	NPC22222
0.8593	High Similarity	NPC281513
0.8592	High Similarity	NPC194856
0.8592	High Similarity	NPC276930
0.8582	High Similarity	NPC301949
0.8582	High Similarity	NPC287533
0.8571	High Similarity	NPC201284
0.8571	High Similarity	NPC59551
0.8561	High Similarity	NPC197425
0.855	High Similarity	NPC71525
0.855	High Similarity	NPC470841
0.8548	High Similarity	NPC240163
0.8542	High Similarity	NPC149614
0.8542	High Similarity	NPC251110
0.854	High Similarity	NPC98395
0.8529	High Similarity	NPC141934
0.8529	High Similarity	NPC239495
0.8529	High Similarity	NPC9985
0.8521	High Similarity	NPC207729
0.8511	High Similarity	NPC47152
0.8511	High Similarity	NPC469764
0.8507	High Similarity	NPC474340
0.8496	Intermediate Similarity	NPC39753
0.8496	Intermediate Similarity	NPC115998
0.8489	Intermediate Similarity	NPC182421
0.8483	Intermediate Similarity	NPC75069
0.8473	Intermediate Similarity	NPC96915
0.8472	Intermediate Similarity	NPC227122
0.8472	Intermediate Similarity	NPC248102
0.8472	Intermediate Similarity	NPC61620
0.8472	Intermediate Similarity	NPC62042
0.8472	Intermediate Similarity	NPC179183
0.8462	Intermediate Similarity	NPC12367
0.8462	Intermediate Similarity	NPC118726
0.8451	Intermediate Similarity	NPC209278
0.8451	Intermediate Similarity	NPC211565
0.8451	Intermediate Similarity	NPC469758
0.8444	Intermediate Similarity	NPC128216
0.844	Intermediate Similarity	NPC306816
0.8433	Intermediate Similarity	NPC301717
0.8433	Intermediate Similarity	NPC137264
0.8433	Intermediate Similarity	NPC324488
0.8429	Intermediate Similarity	NPC329493
0.8425	Intermediate Similarity	NPC88645
0.8425	Intermediate Similarity	NPC167091
0.8425	Intermediate Similarity	NPC206238
0.8425	Intermediate Similarity	NPC292214
0.8425	Intermediate Similarity	NPC271779
0.8421	Intermediate Similarity	NPC473019
0.8414	Intermediate Similarity	NPC204515
0.8414	Intermediate Similarity	NPC117579
0.8413	Intermediate Similarity	NPC269414
0.8406	Intermediate Similarity	NPC228661
0.8406	Intermediate Similarity	NPC84585
0.8406	Intermediate Similarity	NPC476480
0.8403	Intermediate Similarity	NPC70764
0.8394	Intermediate Similarity	NPC324929
0.8392	Intermediate Similarity	NPC275772
0.8392	Intermediate Similarity	NPC71055
0.8392	Intermediate Similarity	NPC239312
0.8392	Intermediate Similarity	NPC130230
0.8382	Intermediate Similarity	NPC57601
0.8382	Intermediate Similarity	NPC265793
0.838	Intermediate Similarity	NPC303185
0.838	Intermediate Similarity	NPC155144
0.838	Intermediate Similarity	NPC98926
0.838	Intermediate Similarity	NPC184649
0.837	Intermediate Similarity	NPC472882
0.837	Intermediate Similarity	NPC113006
0.8369	Intermediate Similarity	NPC73028
0.8369	Intermediate Similarity	NPC1534
0.8357	Intermediate Similarity	NPC275734
0.8356	Intermediate Similarity	NPC281272
0.8356	Intermediate Similarity	NPC474843
0.8356	Intermediate Similarity	NPC120537
0.8356	Intermediate Similarity	NPC199100
0.8356	Intermediate Similarity	NPC180234
0.8356	Intermediate Similarity	NPC39007
0.8356	Intermediate Similarity	NPC161277
0.8356	Intermediate Similarity	NPC101996
0.8346	Intermediate Similarity	NPC171023
0.8346	Intermediate Similarity	NPC201419
0.8345	Intermediate Similarity	NPC329225
0.8345	Intermediate Similarity	NPC45873
0.8345	Intermediate Similarity	NPC472460
0.8345	Intermediate Similarity	NPC470107
0.8345	Intermediate Similarity	NPC112757
0.8345	Intermediate Similarity	NPC147686
0.8345	Intermediate Similarity	NPC1268
0.8333	Intermediate Similarity	NPC474264
0.8333	Intermediate Similarity	NPC130976
0.8333	Intermediate Similarity	NPC272721
0.8333	Intermediate Similarity	NPC196277
0.8333	Intermediate Similarity	NPC43669
0.8333	Intermediate Similarity	NPC5537
0.8322	Intermediate Similarity	NPC300540
0.8322	Intermediate Similarity	NPC196114
0.8322	Intermediate Similarity	NPC60389
0.8322	Intermediate Similarity	NPC299011
0.8322	Intermediate Similarity	NPC308799
0.8321	Intermediate Similarity	NPC248872
0.8321	Intermediate Similarity	NPC56332
0.8321	Intermediate Similarity	NPC172262
0.8311	Intermediate Similarity	NPC472453
0.831	Intermediate Similarity	NPC113770
0.8308	Intermediate Similarity	NPC300274
0.8299	Intermediate Similarity	NPC135522
0.8299	Intermediate Similarity	NPC472915
0.8299	Intermediate Similarity	NPC178964
0.8299	Intermediate Similarity	NPC95842
0.8299	Intermediate Similarity	NPC280530
0.8288	Intermediate Similarity	NPC202157
0.8288	Intermediate Similarity	NPC171010
0.8288	Intermediate Similarity	NPC39819
0.8288	Intermediate Similarity	NPC475076
0.8286	Intermediate Similarity	NPC261234
0.8286	Intermediate Similarity	NPC316480
0.8276	Intermediate Similarity	NPC17286
0.8276	Intermediate Similarity	NPC195351
0.8276	Intermediate Similarity	NPC183959
0.8276	Intermediate Similarity	NPC216318
0.8276	Intermediate Similarity	NPC259713
0.8276	Intermediate Similarity	NPC1612
0.8276	Intermediate Similarity	NPC296197
0.8273	Intermediate Similarity	NPC79943
0.8273	Intermediate Similarity	NPC32441
0.8273	Intermediate Similarity	NPC295261
0.8273	Intermediate Similarity	NPC107586
0.8273	Intermediate Similarity	NPC275055
0.8273	Intermediate Similarity	NPC287246
0.8273	Intermediate Similarity	NPC212767
0.8273	Intermediate Similarity	NPC12296
0.8273	Intermediate Similarity	NPC290291
0.8273	Intermediate Similarity	NPC296490
0.8273	Intermediate Similarity	NPC299379
0.8273	Intermediate Similarity	NPC243083
0.8273	Intermediate Similarity	NPC13768
0.8271	Intermediate Similarity	NPC45537
0.8264	Intermediate Similarity	NPC61284
0.8264	Intermediate Similarity	NPC113428
0.8264	Intermediate Similarity	NPC77378
0.8264	Intermediate Similarity	NPC252208
0.8261	Intermediate Similarity	NPC64157
0.8261	Intermediate Similarity	NPC278832
0.8258	Intermediate Similarity	NPC2771
0.8258	Intermediate Similarity	NPC4164
0.8255	Intermediate Similarity	NPC181960
0.8255	Intermediate Similarity	NPC99597
0.8255	Intermediate Similarity	NPC210084
0.8254	Intermediate Similarity	NPC161304
0.8252	Intermediate Similarity	NPC311144
0.8252	Intermediate Similarity	NPC70136
0.8248	Intermediate Similarity	NPC274121
0.8248	Intermediate Similarity	NPC50898
0.8248	Intermediate Similarity	NPC78540
0.8248	Intermediate Similarity	NPC213216
0.8244	Intermediate Similarity	NPC375356
0.8243	Intermediate Similarity	NPC2928
0.8243	Intermediate Similarity	NPC472909
0.8243	Intermediate Similarity	NPC37392
0.8243	Intermediate Similarity	NPC113906
0.8239	Intermediate Similarity	NPC144499
0.8239	Intermediate Similarity	NPC202981
0.8239	Intermediate Similarity	NPC310340
0.8227	Intermediate Similarity	NPC69769
0.8222	Intermediate Similarity	NPC196621
0.8219	Intermediate Similarity	NPC77858
0.8219	Intermediate Similarity	NPC184136
0.8219	Intermediate Similarity	NPC306821
0.8219	Intermediate Similarity	NPC29231
0.8219	Intermediate Similarity	NPC37348

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 NPC278787 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	466
0.1-0.2	1010
0.2-0.3	1426
0.3-0.4	2699
0.4-0.5	1876
0.5-0.6	1162
0.6-0.7	377
0.7-0.8	114
0.8-0.85	15
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.881	High Similarity	NPD1547	Clinical (unspecified phase)
0.8779	High Similarity	NPD2313	Discontinued
0.8676	High Similarity	NPD2346	Discontinued
0.8538	High Similarity	NPD1203	Approved
0.8467	Intermediate Similarity	NPD2935	Discontinued
0.8406	Intermediate Similarity	NPD2344	Approved
0.8345	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD2798	Approved
0.8273	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD2799	Discontinued
0.8182	Intermediate Similarity	NPD1511	Approved
0.8175	Intermediate Similarity	NPD447	Suspended
0.8169	Intermediate Similarity	NPD2309	Approved
0.8168	Intermediate Similarity	NPD9717	Approved
0.8151	Intermediate Similarity	NPD3226	Approved
0.8129	Intermediate Similarity	NPD1510	Phase 2
0.812	Intermediate Similarity	NPD1470	Approved
0.8108	Intermediate Similarity	NPD6844	Discontinued
0.8102	Intermediate Similarity	NPD1240	Approved
0.8092	Intermediate Similarity	NPD1201	Approved
0.8069	Intermediate Similarity	NPD1512	Approved
0.8054	Intermediate Similarity	NPD2801	Approved
0.8047	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1934	Approved
0.7986	Intermediate Similarity	NPD1607	Approved
0.7969	Intermediate Similarity	NPD6671	Approved
0.7956	Intermediate Similarity	NPD411	Approved
0.7943	Intermediate Similarity	NPD1551	Phase 2
0.7933	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1481	Phase 2
0.7881	Intermediate Similarity	NPD5402	Approved
0.7872	Intermediate Similarity	NPD4308	Phase 3
0.7852	Intermediate Similarity	NPD2797	Approved
0.7847	Intermediate Similarity	NPD3750	Approved
0.782	Intermediate Similarity	NPD1535	Discovery
0.7817	Intermediate Similarity	NPD2796	Approved
0.781	Intermediate Similarity	NPD6832	Phase 2
0.7769	Intermediate Similarity	NPD9493	Approved
0.7762	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD1608	Approved
0.7755	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD4380	Phase 2
0.7698	Intermediate Similarity	NPD3268	Approved
0.7697	Intermediate Similarity	NPD7819	Suspended
0.768	Intermediate Similarity	NPD968	Approved
0.7674	Intermediate Similarity	NPD1241	Discontinued
0.7662	Intermediate Similarity	NPD3749	Approved
0.7662	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD1933	Approved
0.7655	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD1471	Phase 3
0.7609	Intermediate Similarity	NPD2861	Phase 2
0.7597	Intermediate Similarity	NPD3882	Suspended
0.7589	Intermediate Similarity	NPD943	Approved
0.7589	Intermediate Similarity	NPD4307	Phase 2
0.7566	Intermediate Similarity	NPD7411	Suspended
0.7564	Intermediate Similarity	NPD5494	Approved
0.755	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD7075	Discontinued
0.7537	Intermediate Similarity	NPD17	Approved
0.7536	Intermediate Similarity	NPD1019	Discontinued
0.7532	Intermediate Similarity	NPD2296	Approved
0.7532	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD3748	Approved
0.7484	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6166	Phase 2
0.7484	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD3496	Discontinued
0.7468	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1164	Approved
0.7464	Intermediate Similarity	NPD3267	Approved
0.7464	Intermediate Similarity	NPD3266	Approved
0.7448	Intermediate Similarity	NPD6099	Approved
0.7448	Intermediate Similarity	NPD6100	Approved
0.7447	Intermediate Similarity	NPD3764	Approved
0.7422	Intermediate Similarity	NPD74	Approved
0.7422	Intermediate Similarity	NPD9266	Approved
0.7417	Intermediate Similarity	NPD5403	Approved
0.7415	Intermediate Similarity	NPD2800	Approved
0.7405	Intermediate Similarity	NPD6959	Discontinued
0.74	Intermediate Similarity	NPD4662	Approved
0.74	Intermediate Similarity	NPD5401	Approved
0.74	Intermediate Similarity	NPD4661	Approved
0.7391	Intermediate Similarity	NPD1876	Approved
0.7391	Intermediate Similarity	NPD3225	Approved
0.7379	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD3972	Approved
0.7372	Intermediate Similarity	NPD7768	Phase 2
0.7365	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD9494	Approved
0.7355	Intermediate Similarity	NPD1465	Phase 2
0.7344	Intermediate Similarity	NPD9267	Approved
0.7344	Intermediate Similarity	NPD9264	Approved
0.7344	Intermediate Similarity	NPD9263	Approved
0.7333	Intermediate Similarity	NPD8313	Approved
0.7333	Intermediate Similarity	NPD8312	Approved
0.7333	Intermediate Similarity	NPD6799	Approved
0.7317	Intermediate Similarity	NPD6559	Discontinued
0.7308	Intermediate Similarity	NPD3817	Phase 2
0.7305	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7074	Phase 3
0.7299	Intermediate Similarity	NPD1611	Approved
0.7299	Intermediate Similarity	NPD1610	Phase 2
0.7297	Intermediate Similarity	NPD1243	Approved
0.7285	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1283	Approved
0.7259	Intermediate Similarity	NPD1894	Discontinued
0.7255	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7003	Approved
0.7248	Intermediate Similarity	NPD4628	Phase 3
0.7239	Intermediate Similarity	NPD7054	Approved
0.7237	Intermediate Similarity	NPD6273	Approved
0.7234	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD1651	Approved
0.7203	Intermediate Similarity	NPD6798	Discontinued
0.72	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7472	Approved
0.7194	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD920	Approved
0.7188	Intermediate Similarity	NPD9697	Approved
0.7188	Intermediate Similarity	NPD1247	Approved
0.7179	Intermediate Similarity	NPD6801	Discontinued
0.7172	Intermediate Similarity	NPD4618	Approved
0.7172	Intermediate Similarity	NPD1184	Approved
0.7172	Intermediate Similarity	NPD4622	Approved
0.7171	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6599	Discontinued
0.7153	Intermediate Similarity	NPD6233	Phase 2
0.7153	Intermediate Similarity	NPD1778	Approved
0.7152	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7440	Discontinued
0.7152	Intermediate Similarity	NPD6797	Phase 2
0.7143	Intermediate Similarity	NPD6232	Discontinued
0.7143	Intermediate Similarity	NPD1398	Phase 1
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7134	Intermediate Similarity	NPD5844	Phase 1
0.7134	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD4625	Phase 3
0.7132	Intermediate Similarity	NPD9545	Approved
0.7132	Intermediate Similarity	NPD1548	Phase 1
0.7117	Intermediate Similarity	NPD7473	Discontinued
0.7108	Intermediate Similarity	NPD7251	Discontinued
0.7103	Intermediate Similarity	NPD1613	Approved
0.7103	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2651	Approved
0.7097	Intermediate Similarity	NPD2649	Approved
0.7095	Intermediate Similarity	NPD5405	Approved
0.7095	Intermediate Similarity	NPD5404	Approved
0.7095	Intermediate Similarity	NPD5406	Approved
0.7095	Intermediate Similarity	NPD5408	Approved
0.7086	Intermediate Similarity	NPD2354	Approved
0.708	Intermediate Similarity	NPD5585	Approved
0.7075	Intermediate Similarity	NPD5689	Approved
0.7075	Intermediate Similarity	NPD5688	Approved
0.7073	Intermediate Similarity	NPD3751	Discontinued
0.7071	Intermediate Similarity	NPD4749	Approved
0.707	Intermediate Similarity	NPD6279	Approved
0.707	Intermediate Similarity	NPD6280	Approved
0.7066	Intermediate Similarity	NPD7808	Phase 3
0.7059	Intermediate Similarity	NPD2532	Approved
0.7059	Intermediate Similarity	NPD2534	Approved
0.7059	Intermediate Similarity	NPD2533	Approved
0.7055	Intermediate Similarity	NPD6355	Discontinued
0.7051	Intermediate Similarity	NPD6585	Discontinued
0.705	Intermediate Similarity	NPD422	Phase 1
0.705	Intermediate Similarity	NPD1281	Approved
0.7048	Intermediate Similarity	NPD1252	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD3300	Phase 2
0.7035	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD9261	Approved
0.7027	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD7095	Approved
0.7013	Intermediate Similarity	NPD5049	Phase 3
0.7012	Intermediate Similarity	NPD3446	Phase 1
0.7008	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5890	Approved
0.7006	Intermediate Similarity	NPD5889	Approved
0.6992	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7458	Discontinued
0.6986	Remote Similarity	NPD3140	Approved
0.6986	Remote Similarity	NPD4060	Phase 1
0.6986	Remote Similarity	NPD3142	Approved
0.6985	Remote Similarity	NPD7340	Approved
0.698	Remote Similarity	NPD1537	Approved
0.698	Remote Similarity	NPD6032	Approved
0.698	Remote Similarity	NPD4477	Approved
0.698	Remote Similarity	NPD1519	Approved
0.698	Remote Similarity	NPD4476	Approved
0.698	Remote Similarity	NPD1538	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