NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.05
Volume:	250.527
LogP:	2.698
LogD:	2.571
LogS:	-3.718
# Rotatable Bonds:	1
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.655
Synthetic Accessibility Score:	2.228
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:	-4.784
MDCK Permeability:	1.3906720596423838e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.594
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.536

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	91.63396453857422%
Volume Distribution (VD):	0.804
Pgp-substrate:	12.51502513885498%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.93
CYP2C19-inhibitor:	0.372
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.623
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.712
CYP2D6-substrate:	0.855
CYP3A4-inhibitor:	0.492
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	7.541
Half-life (T1/2):	0.811

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.76
Rat Oral Acute Toxicity:	0.151
Maximum Recommended Daily Dose:	0.612
Skin Sensitization:	0.882
Carcinogencity:	0.811
Eye Corrosion:	0.064
Eye Irritation:	0.916
Respiratory Toxicity:	0.337

Download Data

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

Natural Product: NPC149614

Natural Product ID:	NPC149614
*Common Name:**	Cratoxyarborenone F
IUPAC Name:	1,6-dihydroxy-4-methoxyxanthen-9-one
Synonyms:	cratoxyarborenone F
Standard InCHIKey:	ANQQUCRTGKYCDZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10O5/c1-18-10-5-4-9(16)12-13(17)8-3-2-7(15)6-11(8)19-14(10)12/h2-6,15-16H,1H3
SMILES:	COc1ccc(c2c1oc1cc(O)ccc1c2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444717
PubChem CID:	10061042
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
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	twig	n.a.	PMID[11908969]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	stem	n.a.	PMID[11908969]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11908969]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21650157]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	roots	Daba desert reserve (50 km South of Amman), Jordan	2009-APR	PMID[21650157]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO18005	Artemisia leucodes	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19359	Parmotrema delicatulum	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13263	Verbena brasiliensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16038	Ribes rubrum	Species	Grossulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19501	Pseudosuberites hyalinus	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11770	Amphicome emodi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9520	Cratoxylum sumatranum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14950	Ardisia polycephala	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6106	Hymeniacidon perlevis	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18995	Gaultheria itoana	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19227	Hippoglossus hippoglossus	Species	Pleuronectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17438	Polygala virgata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19560	Populus italica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18657	Galanthus gracilis	Species	Amaryllidaceae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	4.1	ug.mL-1	PMID[515595]

☑ 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 NPC149614 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	526
0.1-0.2	2160
0.2-0.3	5486
0.3-0.4	11531
0.4-0.5	5271
0.5-0.6	4138
0.6-0.7	5260
0.7-0.8	4618
0.8-0.85	1994
0.85-0.9	1015
0.9-0.95	481
0.95-1	217

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC179183
0.9863	High Similarity	NPC271779
0.9863	High Similarity	NPC88645
0.9863	High Similarity	NPC292214
0.9863	High Similarity	NPC206238
0.9863	High Similarity	NPC167091
0.9862	High Similarity	NPC117579
0.9795	High Similarity	NPC161277
0.9795	High Similarity	NPC199100
0.9795	High Similarity	NPC101996
0.9795	High Similarity	NPC180234
0.9795	High Similarity	NPC39007
0.9795	High Similarity	NPC120537
0.9728	High Similarity	NPC472915
0.9726	High Similarity	NPC251110
0.9726	High Similarity	NPC171010
0.9722	High Similarity	NPC46941
0.9664	High Similarity	NPC181960
0.9664	High Similarity	NPC99597
0.9664	High Similarity	NPC210084
0.9662	High Similarity	NPC2928
0.9662	High Similarity	NPC37392
0.9662	High Similarity	NPC472909
0.9658	High Similarity	NPC306821
0.9658	High Similarity	NPC61620
0.9658	High Similarity	NPC29231
0.9658	High Similarity	NPC248102
0.9658	High Similarity	NPC62042
0.9653	High Similarity	NPC231013
0.9597	High Similarity	NPC472916
0.9597	High Similarity	NPC235165
0.9597	High Similarity	NPC255106
0.9595	High Similarity	NPC280937
0.9592	High Similarity	NPC226973
0.9592	High Similarity	NPC308451
0.9592	High Similarity	NPC208043
0.9589	High Similarity	NPC294502
0.9589	High Similarity	NPC200221
0.9533	High Similarity	NPC222814
0.9533	High Similarity	NPC78225
0.9533	High Similarity	NPC96167
0.9533	High Similarity	NPC474836
0.9533	High Similarity	NPC36852
0.9533	High Similarity	NPC162869
0.9533	High Similarity	NPC476981
0.9533	High Similarity	NPC262286
0.9533	High Similarity	NPC48208
0.9533	High Similarity	NPC472913
0.9533	High Similarity	NPC245758
0.9533	High Similarity	NPC472914
0.9533	High Similarity	NPC475267
0.9533	High Similarity	NPC474208
0.9533	High Similarity	NPC156057
0.9533	High Similarity	NPC472910
0.9533	High Similarity	NPC472911
0.953	High Similarity	NPC256612
0.953	High Similarity	NPC31018
0.953	High Similarity	NPC255807
0.953	High Similarity	NPC20830
0.9527	High Similarity	NPC239128
0.9527	High Similarity	NPC256283
0.9527	High Similarity	NPC71334
0.9527	High Similarity	NPC301123
0.9527	High Similarity	NPC120163
0.9527	High Similarity	NPC241498
0.9527	High Similarity	NPC188203
0.9527	High Similarity	NPC275836
0.9527	High Similarity	NPC275722
0.9527	High Similarity	NPC100887
0.9527	High Similarity	NPC222830
0.9527	High Similarity	NPC131624
0.9527	High Similarity	NPC198826
0.9527	High Similarity	NPC293183
0.9527	High Similarity	NPC187498
0.9527	High Similarity	NPC83508
0.9527	High Similarity	NPC212678
0.9527	High Similarity	NPC57030
0.9527	High Similarity	NPC301323
0.9527	High Similarity	NPC162313
0.9527	High Similarity	NPC25270
0.9527	High Similarity	NPC156222
0.9524	High Similarity	NPC45873
0.9524	High Similarity	NPC156953
0.9521	High Similarity	NPC196277
0.9521	High Similarity	NPC194856
0.9521	High Similarity	NPC43669
0.9521	High Similarity	NPC183655
0.9521	High Similarity	NPC63256
0.9521	High Similarity	NPC287395
0.9521	High Similarity	NPC276930
0.9521	High Similarity	NPC10304
0.9521	High Similarity	NPC272721
0.9474	High Similarity	NPC308992
0.947	High Similarity	NPC152904
0.9467	High Similarity	NPC138243
0.9467	High Similarity	NPC191146
0.9467	High Similarity	NPC68093
0.9463	High Similarity	NPC47781
0.9463	High Similarity	NPC22519
0.9463	High Similarity	NPC176775
0.9463	High Similarity	NPC160951
0.9463	High Similarity	NPC255350
0.9463	High Similarity	NPC145379
0.9463	High Similarity	NPC69394
0.9463	High Similarity	NPC183878
0.9463	High Similarity	NPC86485
0.9463	High Similarity	NPC231018
0.9463	High Similarity	NPC274327
0.9459	High Similarity	NPC204515
0.9459	High Similarity	NPC262623
0.9459	High Similarity	NPC31363
0.9456	High Similarity	NPC17286
0.9456	High Similarity	NPC296197
0.9456	High Similarity	NPC216318
0.9456	High Similarity	NPC328119
0.9456	High Similarity	NPC259713
0.9452	High Similarity	NPC12200
0.9452	High Similarity	NPC77378
0.9452	High Similarity	NPC207729
0.9452	High Similarity	NPC93034
0.9452	High Similarity	NPC119660
0.9448	High Similarity	NPC472917
0.9444	High Similarity	NPC169479
0.9444	High Similarity	NPC159855
0.9412	High Similarity	NPC472448
0.9412	High Similarity	NPC83922
0.9408	High Similarity	NPC476980
0.9408	High Similarity	NPC263449
0.9404	High Similarity	NPC217677
0.9404	High Similarity	NPC299520
0.9404	High Similarity	NPC300727
0.9404	High Similarity	NPC165977
0.9404	High Similarity	NPC469584
0.9404	High Similarity	NPC129684
0.9404	High Similarity	NPC241904
0.94	High Similarity	NPC146165
0.94	High Similarity	NPC117992
0.94	High Similarity	NPC138360
0.94	High Similarity	NPC50715
0.94	High Similarity	NPC189960
0.94	High Similarity	NPC230149
0.94	High Similarity	NPC196439
0.94	High Similarity	NPC113906
0.94	High Similarity	NPC4455
0.94	High Similarity	NPC57674
0.94	High Similarity	NPC213622
0.94	High Similarity	NPC2476
0.94	High Similarity	NPC44079
0.94	High Similarity	NPC280339
0.94	High Similarity	NPC167815
0.94	High Similarity	NPC163780
0.94	High Similarity	NPC26227
0.94	High Similarity	NPC128863
0.94	High Similarity	NPC208197
0.94	High Similarity	NPC201136
0.94	High Similarity	NPC201451
0.94	High Similarity	NPC183597
0.94	High Similarity	NPC168247
0.94	High Similarity	NPC32557
0.94	High Similarity	NPC227325
0.94	High Similarity	NPC152951
0.94	High Similarity	NPC92659
0.9396	High Similarity	NPC121522
0.9396	High Similarity	NPC100263
0.9396	High Similarity	NPC245382
0.9396	High Similarity	NPC257648
0.9396	High Similarity	NPC131266
0.9396	High Similarity	NPC181209
0.9396	High Similarity	NPC100971
0.9396	High Similarity	NPC209487
0.9396	High Similarity	NPC291802
0.9396	High Similarity	NPC477231
0.9396	High Similarity	NPC302950
0.9396	High Similarity	NPC236637
0.9396	High Similarity	NPC216769
0.9396	High Similarity	NPC269451
0.9396	High Similarity	NPC219582
0.9396	High Similarity	NPC142540
0.9396	High Similarity	NPC60972
0.9396	High Similarity	NPC39732
0.9396	High Similarity	NPC35763
0.9392	High Similarity	NPC184136
0.9392	High Similarity	NPC239363
0.9392	High Similarity	NPC338131
0.9388	High Similarity	NPC12367
0.9388	High Similarity	NPC195202
0.9388	High Similarity	NPC118726
0.9384	High Similarity	NPC209278
0.9346	High Similarity	NPC162668
0.9346	High Similarity	NPC167678
0.9346	High Similarity	NPC266314
0.9346	High Similarity	NPC29876
0.9346	High Similarity	NPC258331
0.9346	High Similarity	NPC474187
0.9342	High Similarity	NPC476242
0.9342	High Similarity	NPC250214
0.9342	High Similarity	NPC190487
0.9342	High Similarity	NPC95936
0.9342	High Similarity	NPC154304
0.9342	High Similarity	NPC16935

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 NPC149614 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	1034
0.2-0.3	1917
0.3-0.4	2645
0.4-0.5	1657
0.5-0.6	950
0.6-0.7	313
0.7-0.8	102
0.8-0.85	34
0.85-0.9	12
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9463	High Similarity	NPD2801	Approved
0.9396	High Similarity	NPD1934	Approved
0.9116	High Similarity	NPD1511	Approved
0.9079	High Similarity	NPD2393	Clinical (unspecified phase)
0.8993	High Similarity	NPD1512	Approved
0.8961	High Similarity	NPD3882	Suspended
0.891	High Similarity	NPD5494	Approved
0.8904	High Similarity	NPD1549	Phase 2
0.8836	High Similarity	NPD1552	Clinical (unspecified phase)
0.8836	High Similarity	NPD1550	Clinical (unspecified phase)
0.8805	High Similarity	NPD6168	Clinical (unspecified phase)
0.8805	High Similarity	NPD6167	Clinical (unspecified phase)
0.8805	High Similarity	NPD6166	Phase 2
0.8699	High Similarity	NPD1510	Phase 2
0.8696	High Similarity	NPD3818	Discontinued
0.8681	High Similarity	NPD1240	Approved
0.8675	High Similarity	NPD4378	Clinical (unspecified phase)
0.8654	High Similarity	NPD3817	Phase 2
0.8599	High Similarity	NPD4868	Clinical (unspecified phase)
0.8589	High Similarity	NPD7074	Phase 3
0.8562	High Similarity	NPD1607	Approved
0.8545	High Similarity	NPD4338	Clinical (unspecified phase)
0.8528	High Similarity	NPD7054	Approved
0.8516	High Similarity	NPD4380	Phase 2
0.85	High Similarity	NPD1247	Approved
0.8476	Intermediate Similarity	NPD7472	Approved
0.8471	Intermediate Similarity	NPD1465	Phase 2
0.8447	Intermediate Similarity	NPD6232	Discontinued
0.8428	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD7075	Discontinued
0.8425	Intermediate Similarity	NPD943	Approved
0.8415	Intermediate Similarity	NPD5844	Phase 1
0.8405	Intermediate Similarity	NPD7473	Discontinued
0.8389	Intermediate Similarity	NPD2796	Approved
0.8354	Intermediate Similarity	NPD7819	Suspended
0.8354	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7808	Phase 3
0.8313	Intermediate Similarity	NPD6797	Phase 2
0.8312	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD7251	Discontinued
0.8247	Intermediate Similarity	NPD6799	Approved
0.8243	Intermediate Similarity	NPD447	Suspended
0.8228	Intermediate Similarity	NPD7411	Suspended
0.8187	Intermediate Similarity	NPD5402	Approved
0.8187	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3926	Phase 2
0.8158	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD919	Approved
0.8146	Intermediate Similarity	NPD2935	Discontinued
0.8095	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD3749	Approved
0.8082	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6801	Discontinued
0.8054	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD1613	Approved
0.8052	Intermediate Similarity	NPD3750	Approved
0.805	Intermediate Similarity	NPD6599	Discontinued
0.8049	Intermediate Similarity	NPD6959	Discontinued
0.8026	Intermediate Similarity	NPD1551	Phase 2
0.8	Intermediate Similarity	NPD230	Phase 1
0.7987	Intermediate Similarity	NPD2800	Approved
0.7976	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6559	Discontinued
0.7904	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1933	Approved
0.7862	Intermediate Similarity	NPD920	Approved
0.7857	Intermediate Similarity	NPD2344	Approved
0.7843	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7768	Phase 2
0.7764	Intermediate Similarity	NPD3226	Approved
0.7756	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1243	Approved
0.775	Intermediate Similarity	NPD5403	Approved
0.7742	Intermediate Similarity	NPD2346	Discontinued
0.7736	Intermediate Similarity	NPD2533	Approved
0.7736	Intermediate Similarity	NPD5401	Approved
0.7736	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2532	Approved
0.7736	Intermediate Similarity	NPD2534	Approved
0.7735	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD3748	Approved
0.7718	Intermediate Similarity	NPD9494	Approved
0.7707	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3751	Discontinued
0.7703	Intermediate Similarity	NPD1203	Approved
0.7702	Intermediate Similarity	NPD1653	Approved
0.7682	Intermediate Similarity	NPD2313	Discontinued
0.7682	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6100	Approved
0.7677	Intermediate Similarity	NPD6099	Approved
0.7673	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2309	Approved
0.7627	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3027	Phase 3
0.7613	Intermediate Similarity	NPD2799	Discontinued
0.761	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4628	Phase 3
0.7572	Intermediate Similarity	NPD5953	Discontinued
0.7558	Intermediate Similarity	NPD7286	Phase 2
0.7551	Intermediate Similarity	NPD1610	Phase 2
0.7542	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD9717	Approved
0.7484	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6651	Approved
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.7458	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6190	Approved
0.7434	Intermediate Similarity	NPD4908	Phase 1
0.7427	Intermediate Similarity	NPD5242	Approved
0.7427	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD37	Approved
0.741	Intermediate Similarity	NPD6844	Discontinued
0.7397	Intermediate Similarity	NPD1548	Phase 1
0.7396	Intermediate Similarity	NPD6234	Discontinued
0.7386	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1608	Approved
0.7383	Intermediate Similarity	NPD9269	Phase 2
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7381	Intermediate Similarity	NPD4965	Approved
0.7351	Intermediate Similarity	NPD1470	Approved
0.7347	Intermediate Similarity	NPD9268	Approved
0.7346	Intermediate Similarity	NPD7390	Discontinued
0.7338	Intermediate Similarity	NPD411	Approved
0.7338	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD5353	Approved
0.732	Intermediate Similarity	NPD6832	Phase 2
0.7315	Intermediate Similarity	NPD422	Phase 1
0.7303	Intermediate Similarity	NPD2798	Approved
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD5710	Approved
0.7267	Intermediate Similarity	NPD5711	Approved
0.7258	Intermediate Similarity	NPD6781	Approved
0.7258	Intermediate Similarity	NPD6779	Approved
0.7258	Intermediate Similarity	NPD6780	Approved
0.7258	Intermediate Similarity	NPD6776	Approved
0.7258	Intermediate Similarity	NPD6777	Approved
0.7258	Intermediate Similarity	NPD6782	Approved
0.7258	Intermediate Similarity	NPD6778	Approved
0.7255	Intermediate Similarity	NPD2861	Phase 2
0.7247	Intermediate Similarity	NPD8312	Approved
0.7247	Intermediate Similarity	NPD8313	Approved
0.7246	Intermediate Similarity	NPD6385	Approved
0.7246	Intermediate Similarity	NPD6386	Approved
0.7239	Intermediate Similarity	NPD4357	Discontinued
0.7232	Intermediate Similarity	NPD7685	Pre-registration
0.7226	Intermediate Similarity	NPD3268	Approved
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7211	Intermediate Similarity	NPD5536	Phase 2
0.72	Intermediate Similarity	NPD1201	Approved
0.72	Intermediate Similarity	NPD7228	Approved
0.7195	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7549	Discontinued
0.7188	Intermediate Similarity	NPD1471	Phase 3
0.7184	Intermediate Similarity	NPD2403	Approved
0.7181	Intermediate Similarity	NPD17	Approved
0.7174	Intermediate Similarity	NPD4363	Phase 3
0.7174	Intermediate Similarity	NPD4360	Phase 2
0.717	Intermediate Similarity	NPD7033	Discontinued
0.7162	Intermediate Similarity	NPD9545	Approved
0.7161	Intermediate Similarity	NPD4625	Phase 3
0.7152	Intermediate Similarity	NPD1481	Phase 2
0.7143	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD3018	Phase 2
0.7143	Intermediate Similarity	NPD7696	Phase 3
0.7143	Intermediate Similarity	NPD9493	Approved
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD7698	Approved
0.7143	Intermediate Similarity	NPD7697	Approved
0.7127	Intermediate Similarity	NPD8150	Discontinued
0.7124	Intermediate Similarity	NPD2797	Approved
0.7118	Intermediate Similarity	NPD2296	Approved
0.7118	Intermediate Similarity	NPD4288	Approved
0.7115	Intermediate Similarity	NPD3764	Approved
0.7105	Intermediate Similarity	NPD7870	Phase 2
0.7105	Intermediate Similarity	NPD7871	Phase 2
0.7105	Intermediate Similarity	NPD4749	Approved
0.7099	Intermediate Similarity	NPD2654	Approved
0.7097	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1535	Discovery
0.7078	Intermediate Similarity	NPD1019	Discontinued
0.7076	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD2899	Discontinued
0.707	Intermediate Similarity	NPD6233	Phase 2
0.7069	Intermediate Similarity	NPD7229	Phase 3
0.7059	Intermediate Similarity	NPD3225	Approved
0.7055	Intermediate Similarity	NPD1241	Discontinued
0.7048	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD8151	Discontinued
0.7039	Intermediate Similarity	NPD3972	Approved
0.7031	Intermediate Similarity	NPD7584	Approved
0.7025	Intermediate Similarity	NPD4307	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