NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	274.05
Volume:	259.317
LogP:	2.326
LogD:	2.035
LogS:	-3.433
# Rotatable Bonds:	0
TPSA:	111.13
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.369
Synthetic Accessibility Score:	2.72
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.105
MDCK Permeability:	5.910271283937618e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.068
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	94.33440399169922%
Volume Distribution (VD):	0.696
Pgp-substrate:	11.118804931640625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.765
CYP2C19-inhibitor:	0.048
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.579
CYP2C9-substrate:	0.766
CYP2D6-inhibitor:	0.283
CYP2D6-substrate:	0.203
CYP3A4-inhibitor:	0.129
CYP3A4-substrate:	0.061

ADMET: Excretion

Clearance (CL):	7.238
Half-life (T1/2):	0.915

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.077
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.55
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.92
Carcinogencity:	0.042
Eye Corrosion:	0.121
Eye Irritation:	0.937
Respiratory Toxicity:	0.171

Download Data

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

Natural Product: NPC151473

Natural Product ID:	NPC151473
*Common Name:**	1,3,5,6-Tetrahydroxy-8-Methylxanthone
IUPAC Name:	3,4,6,8-tetrahydroxy-1-methylxanthen-9-one
Synonyms:
Standard InCHIKey:	REMPMEBGVJJOHV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10O6/c1-5-2-8(17)12(18)14-10(5)13(19)11-7(16)3-6(15)4-9(11)20-14/h2-4,15-18H,1H3
SMILES:	Cc1cc(c(c2c1c(=O)c1c(cc(cc1o2)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465184
PubChem CID:	10401107
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
NPO1865	Penicillium raistrickii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748377]
NPO4553	Oxycorynia fascicularis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO5580	Alstonia glaucescens	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4265	Trichocereus pachanoi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6825	Clethra barbinervis	Species	Clethraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1865	Penicillium raistrickii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO556	Hypericum attenuatum	Species	Hypericaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	11.0	mm	PMID[456279]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	12.0	mm	PMID[456279]

☑ 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 NPC151473 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	540
0.1-0.2	2239
0.2-0.3	5254
0.3-0.4	11848
0.4-0.5	5193
0.5-0.6	4205
0.6-0.7	4960
0.7-0.8	5112
0.8-0.85	1910
0.85-0.9	913
0.9-0.95	492
0.95-1	31

Similarity Score	Similarity Level	Natural Product ID
0.9662	High Similarity	NPC274730
0.9658	High Similarity	NPC202157
0.9597	High Similarity	NPC136674
0.9597	High Similarity	NPC241904
0.9597	High Similarity	NPC300727
0.9589	High Similarity	NPC29231
0.9586	High Similarity	NPC43669
0.9586	High Similarity	NPC196277
0.9586	High Similarity	NPC272721
0.9533	High Similarity	NPC235448
0.9533	High Similarity	NPC476242
0.9533	High Similarity	NPC100123
0.953	High Similarity	NPC472907
0.9527	High Similarity	NPC472905
0.9527	High Similarity	NPC89474
0.9517	High Similarity	NPC77378
0.947	High Similarity	NPC56085
0.947	High Similarity	NPC471973
0.947	High Similarity	NPC320359
0.947	High Similarity	NPC139036
0.947	High Similarity	NPC228785
0.947	High Similarity	NPC200746
0.947	High Similarity	NPC14353
0.9467	High Similarity	NPC111969
0.9467	High Similarity	NPC472963
0.9463	High Similarity	NPC20541
0.9459	High Similarity	NPC180234
0.9459	High Similarity	NPC101996
0.9459	High Similarity	NPC120537
0.9459	High Similarity	NPC260979
0.9459	High Similarity	NPC199100
0.9456	High Similarity	NPC61620
0.9408	High Similarity	NPC40491
0.9408	High Similarity	NPC61010
0.9408	High Similarity	NPC278052
0.94	High Similarity	NPC142339
0.9396	High Similarity	NPC469550
0.9396	High Similarity	NPC49402
0.9396	High Similarity	NPC70433
0.9396	High Similarity	NPC227337
0.9396	High Similarity	NPC88645
0.9396	High Similarity	NPC273462
0.9396	High Similarity	NPC292214
0.9396	High Similarity	NPC206238
0.9396	High Similarity	NPC33051
0.9396	High Similarity	NPC167091
0.9396	High Similarity	NPC271779
0.9392	High Similarity	NPC31363
0.9392	High Similarity	NPC171010
0.9392	High Similarity	NPC251110
0.9384	High Similarity	NPC168803
0.9371	High Similarity	NPC275734
0.9346	High Similarity	NPC25152
0.9342	High Similarity	NPC474960
0.9342	High Similarity	NPC36217
0.9338	High Similarity	NPC217677
0.9338	High Similarity	NPC129684
0.9338	High Similarity	NPC299520
0.9338	High Similarity	NPC236796
0.9338	High Similarity	NPC165977
0.9338	High Similarity	NPC469584
0.9338	High Similarity	NPC187745
0.9338	High Similarity	NPC161960
0.9338	High Similarity	NPC304008
0.9333	High Similarity	NPC168247
0.9333	High Similarity	NPC117992
0.9333	High Similarity	NPC67396
0.9333	High Similarity	NPC230149
0.9333	High Similarity	NPC57674
0.9333	High Similarity	NPC152951
0.9329	High Similarity	NPC477231
0.9329	High Similarity	NPC302950
0.9329	High Similarity	NPC219582
0.9329	High Similarity	NPC236637
0.9329	High Similarity	NPC257648
0.9329	High Similarity	NPC161277
0.9329	High Similarity	NPC472912
0.9329	High Similarity	NPC39007
0.9324	High Similarity	NPC179183
0.9324	High Similarity	NPC62042
0.9324	High Similarity	NPC248102
0.932	High Similarity	NPC194856
0.932	High Similarity	NPC120464
0.932	High Similarity	NPC276930
0.9315	High Similarity	NPC209278
0.931	High Similarity	NPC59551
0.9286	High Similarity	NPC189473
0.9286	High Similarity	NPC23298
0.9286	High Similarity	NPC248638
0.9286	High Similarity	NPC236521
0.9286	High Similarity	NPC152659
0.9286	High Similarity	NPC475985
0.9286	High Similarity	NPC236132
0.9286	High Similarity	NPC220313
0.9286	High Similarity	NPC7483
0.9276	High Similarity	NPC55738
0.9276	High Similarity	NPC329091
0.9276	High Similarity	NPC474290
0.9272	High Similarity	NPC6633
0.9272	High Similarity	NPC5322
0.9272	High Similarity	NPC24640
0.9272	High Similarity	NPC191146
0.9272	High Similarity	NPC235165
0.9272	High Similarity	NPC255106
0.9272	High Similarity	NPC68093
0.9272	High Similarity	NPC115853
0.9272	High Similarity	NPC133970
0.9272	High Similarity	NPC138243
0.9267	High Similarity	NPC18727
0.9262	High Similarity	NPC117579
0.9262	High Similarity	NPC149614
0.9257	High Similarity	NPC177298
0.9257	High Similarity	NPC259713
0.9257	High Similarity	NPC137062
0.9257	High Similarity	NPC223579
0.9257	High Similarity	NPC287101
0.9257	High Similarity	NPC216318
0.9257	High Similarity	NPC52005
0.9257	High Similarity	NPC296197
0.9257	High Similarity	NPC17286
0.9257	High Similarity	NPC48479
0.9257	High Similarity	NPC183950
0.9252	High Similarity	NPC207729
0.9241	High Similarity	NPC310340
0.9241	High Similarity	NPC175013
0.9226	High Similarity	NPC326520
0.9226	High Similarity	NPC275780
0.9226	High Similarity	NPC472450
0.9226	High Similarity	NPC239752
0.9221	High Similarity	NPC294965
0.9221	High Similarity	NPC201800
0.9221	High Similarity	NPC472964
0.9216	High Similarity	NPC474287
0.9216	High Similarity	NPC472902
0.9216	High Similarity	NPC119224
0.9216	High Similarity	NPC475886
0.9216	High Similarity	NPC235018
0.9216	High Similarity	NPC45146
0.9211	High Similarity	NPC222814
0.9211	High Similarity	NPC475267
0.9211	High Similarity	NPC36852
0.9211	High Similarity	NPC474836
0.9211	High Similarity	NPC472910
0.9211	High Similarity	NPC219867
0.9211	High Similarity	NPC245758
0.9211	High Similarity	NPC474208
0.9211	High Similarity	NPC48208
0.9211	High Similarity	NPC156057
0.9211	High Similarity	NPC472911
0.9211	High Similarity	NPC162869
0.9211	High Similarity	NPC96167
0.9211	High Similarity	NPC180011
0.9211	High Similarity	NPC472914
0.9211	High Similarity	NPC472913
0.9211	High Similarity	NPC78225
0.9211	High Similarity	NPC210084
0.9211	High Similarity	NPC99597
0.9211	High Similarity	NPC218313
0.9211	High Similarity	NPC262286
0.9211	High Similarity	NPC474681
0.9205	High Similarity	NPC255807
0.9205	High Similarity	NPC470327
0.9205	High Similarity	NPC477503
0.9205	High Similarity	NPC472280
0.9205	High Similarity	NPC2928
0.9205	High Similarity	NPC45849
0.9205	High Similarity	NPC200761
0.9205	High Similarity	NPC256925
0.9205	High Similarity	NPC200246
0.9205	High Similarity	NPC31018
0.92	High Similarity	NPC301323
0.92	High Similarity	NPC275836
0.92	High Similarity	NPC241498
0.92	High Similarity	NPC149889
0.92	High Similarity	NPC100887
0.92	High Similarity	NPC471982
0.92	High Similarity	NPC120163
0.92	High Similarity	NPC239128
0.92	High Similarity	NPC187498
0.92	High Similarity	NPC293183
0.92	High Similarity	NPC60972
0.92	High Similarity	NPC71334
0.92	High Similarity	NPC275722
0.92	High Similarity	NPC156222
0.92	High Similarity	NPC198826
0.92	High Similarity	NPC131624
0.92	High Similarity	NPC83508
0.92	High Similarity	NPC312338
0.92	High Similarity	NPC212678
0.92	High Similarity	NPC222830
0.92	High Similarity	NPC25270
0.92	High Similarity	NPC188203
0.92	High Similarity	NPC57030
0.92	High Similarity	NPC39732
0.92	High Similarity	NPC162313
0.92	High Similarity	NPC256283
0.9195	High Similarity	NPC338131
0.9195	High Similarity	NPC45873
0.9189	High Similarity	NPC3036
0.9189	High Similarity	NPC321011

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 NPC151473 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	479
0.1-0.2	1068
0.2-0.3	1910
0.3-0.4	2704
0.4-0.5	1606
0.5-0.6	923
0.6-0.7	315
0.7-0.8	100
0.8-0.85	30
0.85-0.9	8
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9329	High Similarity	NPD1934	Approved
0.9178	High Similarity	NPD1511	Approved
0.9139	High Similarity	NPD2801	Approved
0.9054	High Similarity	NPD1512	Approved
0.9013	High Similarity	NPD2393	Clinical (unspecified phase)
0.8896	High Similarity	NPD3882	Suspended
0.8889	High Similarity	NPD1465	Phase 2
0.8742	High Similarity	NPD6167	Clinical (unspecified phase)
0.8742	High Similarity	NPD6166	Phase 2
0.8742	High Similarity	NPD6168	Clinical (unspecified phase)
0.8639	High Similarity	NPD1552	Clinical (unspecified phase)
0.8639	High Similarity	NPD1550	Clinical (unspecified phase)
0.8581	High Similarity	NPD1549	Phase 2
0.8535	High Similarity	NPD4868	Clinical (unspecified phase)
0.8528	High Similarity	NPD7074	Phase 3
0.8519	High Similarity	NPD3818	Discontinued
0.85	High Similarity	NPD6232	Discontinued
0.8483	Intermediate Similarity	NPD943	Approved
0.8471	Intermediate Similarity	NPD3817	Phase 2
0.8466	Intermediate Similarity	NPD7054	Approved
0.8457	Intermediate Similarity	NPD7473	Discontinued
0.8456	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7472	Approved
0.8408	Intermediate Similarity	NPD7819	Suspended
0.8378	Intermediate Similarity	NPD1510	Phase 2
0.8375	Intermediate Similarity	NPD5494	Approved
0.8366	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD1240	Approved
0.8264	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD6797	Phase 2
0.825	Intermediate Similarity	NPD7075	Discontinued
0.825	Intermediate Similarity	NPD3749	Approved
0.8243	Intermediate Similarity	NPD1607	Approved
0.8224	Intermediate Similarity	NPD3750	Approved
0.8217	Intermediate Similarity	NPD4380	Phase 2
0.821	Intermediate Similarity	NPD6959	Discontinued
0.8207	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7251	Discontinued
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7808	Phase 3
0.8137	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5844	Phase 1
0.8129	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD2796	Approved
0.8065	Intermediate Similarity	NPD6799	Approved
0.8039	Intermediate Similarity	NPD2800	Approved
0.8036	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3926	Phase 2
0.7987	Intermediate Similarity	NPD1613	Approved
0.7987	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6100	Approved
0.7961	Intermediate Similarity	NPD6099	Approved
0.7937	Intermediate Similarity	NPD7411	Suspended
0.7933	Intermediate Similarity	NPD230	Phase 1
0.7933	Intermediate Similarity	NPD447	Suspended
0.7898	Intermediate Similarity	NPD2534	Approved
0.7898	Intermediate Similarity	NPD2532	Approved
0.7898	Intermediate Similarity	NPD2533	Approved
0.7895	Intermediate Similarity	NPD3748	Approved
0.7888	Intermediate Similarity	NPD6801	Discontinued
0.7879	Intermediate Similarity	NPD1247	Approved
0.7866	Intermediate Similarity	NPD919	Approved
0.7812	Intermediate Similarity	NPD3226	Approved
0.7811	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2344	Approved
0.7792	Intermediate Similarity	NPD2346	Discontinued
0.7778	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7199	Phase 2
0.7758	Intermediate Similarity	NPD6234	Discontinued
0.7738	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1551	Phase 2
0.7692	Intermediate Similarity	NPD1243	Approved
0.7688	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD5402	Approved
0.7679	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6559	Discontinued
0.7651	Intermediate Similarity	NPD9494	Approved
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7636	Intermediate Similarity	NPD7768	Phase 2
0.761	Intermediate Similarity	NPD7390	Discontinued
0.7595	Intermediate Similarity	NPD2309	Approved
0.7582	Intermediate Similarity	NPD1933	Approved
0.7578	Intermediate Similarity	NPD5403	Approved
0.7571	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD5401	Approved
0.7561	Intermediate Similarity	NPD37	Approved
0.755	Intermediate Similarity	NPD3027	Phase 3
0.7548	Intermediate Similarity	NPD2799	Discontinued
0.7544	Intermediate Similarity	NPD7228	Approved
0.7532	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.753	Intermediate Similarity	NPD4967	Phase 2
0.753	Intermediate Similarity	NPD4966	Approved
0.753	Intermediate Similarity	NPD4965	Approved
0.7517	Intermediate Similarity	NPD1470	Approved
0.7517	Intermediate Similarity	NPD1203	Approved
0.7515	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7483	Intermediate Similarity	NPD1610	Phase 2
0.7483	Intermediate Similarity	NPD1201	Approved
0.7469	Intermediate Similarity	NPD920	Approved
0.7468	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4625	Phase 3
0.7432	Intermediate Similarity	NPD1608	Approved
0.7432	Intermediate Similarity	NPD9269	Phase 2
0.7421	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6651	Approved
0.7412	Intermediate Similarity	NPD5711	Approved
0.7412	Intermediate Similarity	NPD5710	Approved
0.7401	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2313	Discontinued
0.7383	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4908	Phase 1
0.7365	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1471	Phase 3
0.733	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1653	Approved
0.7315	Intermediate Similarity	NPD9717	Approved
0.7314	Intermediate Similarity	NPD5953	Discontinued
0.7288	Intermediate Similarity	NPD8312	Approved
0.7288	Intermediate Similarity	NPD8313	Approved
0.7278	Intermediate Similarity	NPD4287	Approved
0.7273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3764	Approved
0.7273	Intermediate Similarity	NPD3268	Approved
0.7267	Intermediate Similarity	NPD4749	Approved
0.7262	Intermediate Similarity	NPD4288	Approved
0.7248	Intermediate Similarity	NPD422	Phase 1
0.7237	Intermediate Similarity	NPD2798	Approved
0.723	Intermediate Similarity	NPD17	Approved
0.7211	Intermediate Similarity	NPD1548	Phase 1
0.72	Intermediate Similarity	NPD7286	Phase 2
0.7175	Intermediate Similarity	NPD7685	Pre-registration
0.7173	Intermediate Similarity	NPD8151	Discontinued
0.7171	Intermediate Similarity	NPD2797	Approved
0.7168	Intermediate Similarity	NPD5242	Approved
0.7162	Intermediate Similarity	NPD9268	Approved
0.7161	Intermediate Similarity	NPD411	Approved
0.716	Intermediate Similarity	NPD6190	Approved
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD2403	Approved
0.7112	Intermediate Similarity	NPD6777	Approved
0.7112	Intermediate Similarity	NPD6778	Approved
0.7112	Intermediate Similarity	NPD6782	Approved
0.7112	Intermediate Similarity	NPD6780	Approved
0.7112	Intermediate Similarity	NPD6781	Approved
0.7112	Intermediate Similarity	NPD6776	Approved
0.7112	Intermediate Similarity	NPD6779	Approved
0.711	Intermediate Similarity	NPD7229	Phase 3
0.7107	Intermediate Similarity	NPD4308	Phase 3
0.7079	Intermediate Similarity	NPD7240	Approved
0.7075	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8150	Discontinued
0.7072	Intermediate Similarity	NPD8434	Phase 2
0.707	Intermediate Similarity	NPD4060	Phase 1
0.7066	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5406	Approved
0.7063	Intermediate Similarity	NPD5408	Approved
0.7063	Intermediate Similarity	NPD5404	Approved
0.7063	Intermediate Similarity	NPD5405	Approved
0.7059	Intermediate Similarity	NPD3267	Approved
0.7059	Intermediate Similarity	NPD3266	Approved
0.7059	Intermediate Similarity	NPD2296	Approved
0.7059	Intermediate Similarity	NPD5353	Approved
0.7056	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2654	Approved
0.7032	Intermediate Similarity	NPD6832	Phase 2
0.7027	Intermediate Similarity	NPD4360	Phase 2
0.7027	Intermediate Similarity	NPD4363	Phase 3
0.7025	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD7033	Discontinued
0.6993	Remote Similarity	NPD3225	Approved
0.6983	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4357	Discontinued
0.6968	Remote Similarity	NPD3018	Phase 2
0.6966	Remote Similarity	NPD228	Approved
0.6962	Remote Similarity	NPD1558	Phase 1
0.6959	Remote Similarity	NPD5977	Approved
0.6959	Remote Similarity	NPD5978	Approved
0.6952	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2354	Approved
0.6943	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6798	Discontinued
0.6943	Remote Similarity	NPD1296	Phase 2
0.6923	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7783	Phase 2
0.6918	Remote Similarity	NPD6355	Discontinued
0.6913	Remote Similarity	NPD5536	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data