NPASS Compound

Structure

CID329091 OpenBabel06191716202D 25 27 0 0 1 0 0 0 0 0999 V2000 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 3 11 1 0 0 0 0 4 8 1 0 0 0 0 4 13 2 0 0 0 0 5 9 1 0 0 0 0 5 10 1 0 0 0 0 6 12 1 0 0 0 0 6 14 2 0 0 0 0 7 10 1 0 0 0 0 8 19 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 20 1 0 0 0 0 11 16 2 0 0 0 0 11 21 1 0 0 0 0 12 17 2 0 0 0 0 12 22 1 0 0 0 0 13 16 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 18 1 0 0 0 0 16 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.09
Volume:	334.655
LogP:	2.449
LogD:	1.772
LogS:	-3.451
# Rotatable Bonds:	3
TPSA:	131.36
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.28
Synthetic Accessibility Score:	3.519
Fsp3:	0.167
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:	-5.234
MDCK Permeability:	4.936883215123089e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.113
Human Intestinal Absorption (HIA):	0.362
20% Bioavailability (F20%):	0.853
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	91.18272399902344%
Volume Distribution (VD):	0.731
Pgp-substrate:	11.383410453796387%

ADMET: Metabolism

CYP1A2-inhibitor:	0.867
CYP1A2-substrate:	0.575
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.326
CYP2C9-substrate:	0.739
CYP2D6-inhibitor:	0.216
CYP2D6-substrate:	0.22
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	6.569
Half-life (T1/2):	0.89

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.081
Drug-inuced Liver Injury (DILI):	0.827
AMES Toxicity:	0.45
Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.933
Carcinogencity:	0.025
Eye Corrosion:	0.008
Eye Irritation:	0.916
Respiratory Toxicity:	0.151

Download Data

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

Natural Product: NPC329091

Natural Product ID:	NPC329091
*Common Name:**	Hyperxanthone C
IUPAC Name:	2,3,6,8-tetrahydroxy-1-(2-hydroxy-3-methylbut-3-enyl)xanthen-9-one
Synonyms:	Hyperxanthone C
Standard InCHIKey:	GONMHOQVFDWXLV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O7/c1-7(2)10(20)5-9-15-14(6-12(22)17(9)23)25-13-4-8(19)3-11(21)16(13)18(15)24/h3-4,6,10,19-23H,1,5H2,2H3
SMILES:	Oc1cc(O)c2c(c1)oc1c(c2=O)c(CC(C(=C)C)O)c(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484835
PubChem CID:	11302345
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 [CHEMONTID:0003519] 8-prenylated 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
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568778]
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	Uzbekistan	n.a.	PMID[15568778]
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27280968]
NPO11713	Hypericum scabrum	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	9300.0	ug.mL-1	PMID[531484]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	11200.0	ug.mL-1	PMID[531484]

☑ 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 NPC329091 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	418
0.1-0.2	1745
0.2-0.3	4191
0.3-0.4	10216
0.4-0.5	8034
0.5-0.6	3594
0.6-0.7	4968
0.7-0.8	5101
0.8-0.85	2474
0.85-0.9	1433
0.9-0.95	501
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC89474
0.9671	High Similarity	NPC241904
0.9671	High Similarity	NPC300727
0.9669	High Similarity	NPC67396
0.9613	High Similarity	NPC7483
0.9613	High Similarity	NPC475985
0.9608	High Similarity	NPC476242
0.9605	High Similarity	NPC274730
0.9605	High Similarity	NPC142339
0.9605	High Similarity	NPC24640
0.96	High Similarity	NPC202157
0.9554	High Similarity	NPC6588
0.9554	High Similarity	NPC477154
0.9554	High Similarity	NPC117854
0.9551	High Similarity	NPC326520
0.9551	High Similarity	NPC473286
0.9545	High Similarity	NPC14353
0.9545	High Similarity	NPC56085
0.9545	High Similarity	NPC228785
0.9545	High Similarity	NPC321399
0.9542	High Similarity	NPC48208
0.9542	High Similarity	NPC236796
0.9542	High Similarity	NPC156057
0.9542	High Similarity	NPC475267
0.9542	High Similarity	NPC474836
0.9542	High Similarity	NPC469584
0.9542	High Similarity	NPC474208
0.9542	High Similarity	NPC162869
0.9536	High Similarity	NPC474843
0.949	High Similarity	NPC170245
0.9484	High Similarity	NPC61010
0.9484	High Similarity	NPC32694
0.9484	High Similarity	NPC40491
0.9484	High Similarity	NPC474186
0.9484	High Similarity	NPC278052
0.9481	High Similarity	NPC100123
0.9481	High Similarity	NPC85121
0.9481	High Similarity	NPC210459
0.9477	High Similarity	NPC235165
0.9477	High Similarity	NPC255106
0.947	High Similarity	NPC204515
0.9423	High Similarity	NPC211107
0.9423	High Similarity	NPC472964
0.9419	High Similarity	NPC45146
0.9419	High Similarity	NPC474287
0.9419	High Similarity	NPC263449
0.9419	High Similarity	NPC36217
0.9419	High Similarity	NPC119224
0.9419	High Similarity	NPC472902
0.9419	High Similarity	NPC475886
0.9419	High Similarity	NPC235018
0.9419	High Similarity	NPC200746
0.9419	High Similarity	NPC320359
0.9416	High Similarity	NPC217677
0.9416	High Similarity	NPC472910
0.9416	High Similarity	NPC222814
0.9416	High Similarity	NPC472913
0.9416	High Similarity	NPC472914
0.9416	High Similarity	NPC99597
0.9416	High Similarity	NPC96167
0.9416	High Similarity	NPC223787
0.9416	High Similarity	NPC472911
0.9416	High Similarity	NPC245758
0.9416	High Similarity	NPC210084
0.9416	High Similarity	NPC470402
0.9416	High Similarity	NPC165977
0.9412	High Similarity	NPC37392
0.9412	High Similarity	NPC321779
0.9412	High Similarity	NPC113906
0.9408	High Similarity	NPC106976
0.9404	High Similarity	NPC62042
0.9363	High Similarity	NPC473313
0.9363	High Similarity	NPC220313
0.9363	High Similarity	NPC236132
0.9363	High Similarity	NPC197168
0.9363	High Similarity	NPC236521
0.9363	High Similarity	NPC152659
0.9363	High Similarity	NPC472278
0.9363	High Similarity	NPC329669
0.9363	High Similarity	NPC248638
0.9359	High Similarity	NPC474187
0.9359	High Similarity	NPC474351
0.9359	High Similarity	NPC308992
0.9359	High Similarity	NPC475883
0.9355	High Similarity	NPC250214
0.9355	High Similarity	NPC95936
0.9351	High Similarity	NPC472916
0.9351	High Similarity	NPC201837
0.9346	High Similarity	NPC298692
0.9346	High Similarity	NPC74924
0.9346	High Similarity	NPC213896
0.9346	High Similarity	NPC18727
0.9346	High Similarity	NPC192083
0.9304	High Similarity	NPC239752
0.9304	High Similarity	NPC475888
0.9304	High Similarity	NPC472450
0.9304	High Similarity	NPC275780
0.9304	High Similarity	NPC224280
0.9304	High Similarity	NPC25361
0.9299	High Similarity	NPC201800
0.9299	High Similarity	NPC329760
0.9299	High Similarity	NPC25152
0.9299	High Similarity	NPC470694
0.9299	High Similarity	NPC220912
0.9295	High Similarity	NPC139036
0.9295	High Similarity	NPC80375
0.9295	High Similarity	NPC470183
0.929	High Similarity	NPC36852
0.929	High Similarity	NPC472598
0.929	High Similarity	NPC474055
0.929	High Similarity	NPC299520
0.929	High Similarity	NPC129684
0.929	High Similarity	NPC78225
0.929	High Similarity	NPC262286
0.929	High Similarity	NPC181960
0.9286	High Similarity	NPC472909
0.9286	High Similarity	NPC477503
0.9286	High Similarity	NPC213622
0.9286	High Similarity	NPC2928
0.9286	High Similarity	NPC45849
0.9286	High Similarity	NPC200761
0.9286	High Similarity	NPC470327
0.9281	High Similarity	NPC302950
0.9281	High Similarity	NPC236637
0.9281	High Similarity	NPC199100
0.9281	High Similarity	NPC180234
0.9281	High Similarity	NPC219582
0.9281	High Similarity	NPC120537
0.9281	High Similarity	NPC101996
0.9276	High Similarity	NPC151473
0.9276	High Similarity	NPC338131
0.9276	High Similarity	NPC184136
0.9272	High Similarity	NPC188679
0.9272	High Similarity	NPC194856
0.9272	High Similarity	NPC276930
0.9272	High Similarity	NPC294852
0.9272	High Similarity	NPC321011
0.9245	High Similarity	NPC39091
0.9245	High Similarity	NPC477517
0.9241	High Similarity	NPC189473
0.9241	High Similarity	NPC270837
0.9241	High Similarity	NPC23298
0.9241	High Similarity	NPC186686
0.9241	High Similarity	NPC207690
0.9241	High Similarity	NPC41301
0.9241	High Similarity	NPC474240
0.9236	High Similarity	NPC266314
0.9236	High Similarity	NPC472275
0.9236	High Similarity	NPC228383
0.9231	High Similarity	NPC152904
0.9231	High Similarity	NPC172770
0.9231	High Similarity	NPC474290
0.9231	High Similarity	NPC469658
0.9231	High Similarity	NPC22192
0.9231	High Similarity	NPC185258
0.9226	High Similarity	NPC291878
0.9226	High Similarity	NPC472626
0.9226	High Similarity	NPC195796
0.9226	High Similarity	NPC138243
0.9226	High Similarity	NPC164427
0.9226	High Similarity	NPC13858
0.9226	High Similarity	NPC470328
0.9226	High Similarity	NPC471500
0.9226	High Similarity	NPC209614
0.9226	High Similarity	NPC320825
0.9226	High Similarity	NPC278778
0.9226	High Similarity	NPC326037
0.9226	High Similarity	NPC191146
0.9226	High Similarity	NPC68093
0.9226	High Similarity	NPC35038
0.9226	High Similarity	NPC250922
0.9221	High Similarity	NPC183878
0.9221	High Similarity	NPC75279
0.9221	High Similarity	NPC160951
0.9221	High Similarity	NPC206238
0.9221	High Similarity	NPC255350
0.9221	High Similarity	NPC271779
0.9221	High Similarity	NPC176775
0.9221	High Similarity	NPC167091
0.9221	High Similarity	NPC69394
0.9221	High Similarity	NPC47781
0.9221	High Similarity	NPC292214
0.9221	High Similarity	NPC145379
0.9221	High Similarity	NPC22519
0.9221	High Similarity	NPC280937
0.9221	High Similarity	NPC276409
0.9221	High Similarity	NPC231018
0.9221	High Similarity	NPC472915
0.9221	High Similarity	NPC274327
0.9221	High Similarity	NPC88645
0.9221	High Similarity	NPC250822
0.9216	High Similarity	NPC117579
0.9216	High Similarity	NPC171010
0.9211	High Similarity	NPC1612
0.9211	High Similarity	NPC183959
0.9205	High Similarity	NPC207729
0.9187	High Similarity	NPC243877
0.9187	High Similarity	NPC14662
0.9187	High Similarity	NPC474024
0.9182	High Similarity	NPC37183

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 NPC329091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	391
0.1-0.2	952
0.2-0.3	1856
0.3-0.4	2632
0.4-0.5	1791
0.5-0.6	956
0.6-0.7	401
0.7-0.8	120
0.8-0.85	33
0.85-0.9	14
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9346	High Similarity	NPD2393	Clinical (unspecified phase)
0.9281	High Similarity	NPD1934	Approved
0.9221	High Similarity	NPD2801	Approved
0.8944	High Similarity	NPD6166	Phase 2
0.8944	High Similarity	NPD6168	Clinical (unspecified phase)
0.8944	High Similarity	NPD6167	Clinical (unspecified phase)
0.8882	High Similarity	NPD1511	Approved
0.8766	High Similarity	NPD1512	Approved
0.8742	High Similarity	NPD4868	Clinical (unspecified phase)
0.8742	High Similarity	NPD3882	Suspended
0.8727	High Similarity	NPD7074	Phase 3
0.872	High Similarity	NPD3818	Discontinued
0.8696	High Similarity	NPD5494	Approved
0.8683	High Similarity	NPD4338	Clinical (unspecified phase)
0.8667	High Similarity	NPD7054	Approved
0.8614	High Similarity	NPD7472	Approved
0.8609	High Similarity	NPD1550	Clinical (unspecified phase)
0.8609	High Similarity	NPD1552	Clinical (unspecified phase)
0.8563	High Similarity	NPD6797	Phase 2
0.8554	High Similarity	NPD5844	Phase 1
0.8553	High Similarity	NPD1549	Phase 2
0.8544	High Similarity	NPD4380	Phase 2
0.8528	High Similarity	NPD6959	Discontinued
0.8512	High Similarity	NPD7251	Discontinued
0.85	High Similarity	NPD7819	Suspended
0.8462	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD3817	Phase 2
0.8385	Intermediate Similarity	NPD1465	Phase 2
0.8364	Intermediate Similarity	NPD6232	Discontinued
0.8353	Intermediate Similarity	NPD7808	Phase 3
0.8344	Intermediate Similarity	NPD7075	Discontinued
0.8343	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7473	Discontinued
0.8301	Intermediate Similarity	NPD2796	Approved
0.8272	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD1510	Phase 2
0.8221	Intermediate Similarity	NPD5402	Approved
0.8194	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD2532	Approved
0.8113	Intermediate Similarity	NPD2534	Approved
0.8113	Intermediate Similarity	NPD2533	Approved
0.8098	Intermediate Similarity	NPD6801	Discontinued
0.8092	Intermediate Similarity	NPD943	Approved
0.8092	Intermediate Similarity	NPD1240	Approved
0.8092	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD1613	Approved
0.805	Intermediate Similarity	NPD6799	Approved
0.8037	Intermediate Similarity	NPD7411	Suspended
0.8012	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1607	Approved
0.7977	Intermediate Similarity	NPD6559	Discontinued
0.7975	Intermediate Similarity	NPD3750	Approved
0.7975	Intermediate Similarity	NPD6599	Discontinued
0.7953	Intermediate Similarity	NPD3751	Discontinued
0.7929	Intermediate Similarity	NPD3787	Discontinued
0.7922	Intermediate Similarity	NPD230	Phase 1
0.7911	Intermediate Similarity	NPD2800	Approved
0.7885	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD1247	Approved
0.7865	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6234	Discontinued
0.7836	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD2935	Discontinued
0.7834	Intermediate Similarity	NPD6100	Approved
0.7834	Intermediate Similarity	NPD6099	Approved
0.7829	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD5403	Approved
0.7778	Intermediate Similarity	NPD3027	Phase 3
0.7778	Intermediate Similarity	NPD3926	Phase 2
0.7771	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD37	Approved
0.7765	Intermediate Similarity	NPD7199	Phase 2
0.775	Intermediate Similarity	NPD4628	Phase 3
0.7746	Intermediate Similarity	NPD7228	Approved
0.7738	Intermediate Similarity	NPD4966	Approved
0.7738	Intermediate Similarity	NPD4967	Phase 2
0.7738	Intermediate Similarity	NPD7768	Phase 2
0.7738	Intermediate Similarity	NPD4965	Approved
0.7697	Intermediate Similarity	NPD3226	Approved
0.7676	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD2346	Discontinued
0.7669	Intermediate Similarity	NPD5401	Approved
0.7658	Intermediate Similarity	NPD3748	Approved
0.7636	Intermediate Similarity	NPD1653	Approved
0.7616	Intermediate Similarity	NPD5710	Approved
0.7616	Intermediate Similarity	NPD5711	Approved
0.7613	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD1551	Phase 2
0.7607	Intermediate Similarity	NPD7390	Discontinued
0.7598	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6190	Approved
0.7584	Intermediate Similarity	NPD8312	Approved
0.7584	Intermediate Similarity	NPD8313	Approved
0.7581	Intermediate Similarity	NPD6781	Approved
0.7581	Intermediate Similarity	NPD6778	Approved
0.7581	Intermediate Similarity	NPD6782	Approved
0.7581	Intermediate Similarity	NPD6777	Approved
0.7581	Intermediate Similarity	NPD6779	Approved
0.7581	Intermediate Similarity	NPD6780	Approved
0.7581	Intermediate Similarity	NPD6776	Approved
0.7578	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD2344	Approved
0.7561	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD919	Approved
0.7531	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4908	Phase 1
0.747	Intermediate Similarity	NPD920	Approved
0.747	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD447	Suspended
0.746	Intermediate Similarity	NPD7435	Discontinued
0.7459	Intermediate Similarity	NPD8434	Phase 2
0.7459	Intermediate Similarity	NPD8150	Discontinued
0.7456	Intermediate Similarity	NPD6844	Discontinued
0.7455	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD8151	Discontinued
0.7438	Intermediate Similarity	NPD2799	Discontinued
0.7423	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6651	Approved
0.7419	Intermediate Similarity	NPD2861	Phase 2
0.7416	Intermediate Similarity	NPD5953	Discontinued
0.7405	Intermediate Similarity	NPD4363	Phase 3
0.7405	Intermediate Similarity	NPD4360	Phase 2
0.7401	Intermediate Similarity	NPD7286	Phase 2
0.7389	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2309	Approved
0.7374	Intermediate Similarity	NPD7685	Pre-registration
0.7371	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7783	Phase 2
0.7368	Intermediate Similarity	NPD7698	Approved
0.7368	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7696	Phase 3
0.7368	Intermediate Similarity	NPD7697	Approved
0.7368	Intermediate Similarity	NPD1610	Phase 2
0.7362	Intermediate Similarity	NPD1243	Approved
0.7349	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7870	Phase 2
0.733	Intermediate Similarity	NPD7871	Phase 2
0.7329	Intermediate Similarity	NPD7033	Discontinued
0.7325	Intermediate Similarity	NPD4625	Phase 3
0.7316	Intermediate Similarity	NPD6823	Phase 2
0.7314	Intermediate Similarity	NPD7229	Phase 3
0.7312	Intermediate Similarity	NPD6535	Approved
0.7312	Intermediate Similarity	NPD6534	Approved
0.7308	Intermediate Similarity	NPD9494	Approved
0.7306	Intermediate Similarity	NPD7701	Phase 2
0.7289	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2313	Discontinued
0.7278	Intermediate Similarity	NPD7240	Approved
0.7256	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1933	Approved
0.7231	Intermediate Similarity	NPD7874	Approved
0.7231	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD9269	Phase 2
0.7196	Intermediate Similarity	NPD7700	Phase 2
0.7196	Intermediate Similarity	NPD7699	Phase 2
0.7194	Intermediate Similarity	NPD7801	Approved
0.7193	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1203	Approved
0.7179	Intermediate Similarity	NPD1470	Approved
0.7175	Intermediate Similarity	NPD5242	Approved
0.717	Intermediate Similarity	NPD3268	Approved
0.717	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD5353	Approved
0.7161	Intermediate Similarity	NPD4749	Approved
0.7161	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1201	Approved
0.7135	Intermediate Similarity	NPD2403	Approved
0.7134	Intermediate Similarity	NPD2798	Approved
0.7125	Intermediate Similarity	NPD6233	Phase 2
0.711	Intermediate Similarity	NPD5761	Phase 2
0.711	Intermediate Similarity	NPD5760	Phase 2
0.7105	Intermediate Similarity	NPD1548	Phase 1
0.7101	Intermediate Similarity	NPD6273	Approved
0.7097	Intermediate Similarity	NPD1608	Approved
0.7097	Intermediate Similarity	NPD4287	Approved
0.7091	Intermediate Similarity	NPD2424	Discontinued
0.709	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD4361	Phase 2
0.7088	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4060	Phase 1
0.7077	Intermediate Similarity	NPD7584	Approved
0.7074	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6212	Phase 3
0.7074	Intermediate Similarity	NPD6213	Phase 3
0.707	Intermediate Similarity	NPD2797	Approved
0.7069	Intermediate Similarity	NPD4288	Approved
0.7063	Intermediate Similarity	NPD1699	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data