NPASS Compound

Structure

NPC475957 OpenBabel07101719242D 24 26 0 0 1 0 0 0 0 0999 V2000 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 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 -1.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 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 -0.0000 -0.0000 0.0000 C 0 0 2 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 19 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 14 2 0 0 0 0 10 11 1 0 0 0 0 11 14 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 15 22 2 0 0 0 0 16 17 1 0 0 0 0 16 23 2 0 0 0 0 17 18 1 0 0 0 0 17 24 1 6 0 0 0 18 19 1 0 0 0 0 18 20 1 6 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	350.785
LogP:	2.927
LogD:	1.356
LogS:	-3.334
# Rotatable Bonds:	1
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.827
Synthetic Accessibility Score:	4.272
Fsp3:	0.6
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:	-4.705
MDCK Permeability:	1.8282851669937372e-05
Pgp-inhibitor:	0.284
Pgp-substrate:	0.958
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.707
30% Bioavailability (F30%):	0.03

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.51
Plasma Protein Binding (PPB):	85.2041244506836%
Volume Distribution (VD):	1.911
Pgp-substrate:	21.042116165161133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.704
CYP2C19-inhibitor:	0.094
CYP2C19-substrate:	0.892
CYP2C9-inhibitor:	0.303
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.277
CYP3A4-inhibitor:	0.101
CYP3A4-substrate:	0.741

ADMET: Excretion

Clearance (CL):	7.883
Half-life (T1/2):	0.307

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.66
AMES Toxicity:	0.035
Rat Oral Acute Toxicity:	0.374
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.305
Carcinogencity:	0.024
Eye Corrosion:	0.006
Eye Irritation:	0.826
Respiratory Toxicity:	0.954

Download Data

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

Natural Product: NPC475957

Natural Product ID:	NPC475957
*Common Name:**	Hypargenin A
IUPAC Name:	(4aS,10S,10aS)-6,10-dihydroxy-1,1,4a-trimethyl-7-propan-2-yl-2,3,10,10a-tetrahydrophenanthrene-4,9-dione
Synonyms:
Standard InCHIKey:	MJQYLJQAKPFSAI-HBFSDRIKSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-10(2)11-8-12-13(9-14(11)21)20(5)15(22)6-7-19(3,4)18(20)17(24)16(12)23/h8-10,17-18,21,24H,6-7H2,1-5H3/t17-,18+,20+/m1/s1
SMILES:	CC(C)C1=C(C=C2C(=C1)C(=O)C(C3C2(C(=O)CCC3(C)C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519712
PubChem CID:	14239563
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO26904	Salvia hypargeia	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[3236010]
NPO26904	Salvia hypargeia	Species	Lamiaceae	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
MIC	2
Others	5

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	15.6	ug.mL-1	PMID[450040]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	15.6	ug.mL-1	PMID[450040]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	>	7.0	mm	PMID[450040]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	IZ	>	7.0	mm	PMID[450040]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	IZ	>	7.0	mm	PMID[450040]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	>	7.0	mm	PMID[450040]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	>	7.0	mm	PMID[450040]

☑ 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 NPC475957 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	321
0.1-0.2	1383
0.2-0.3	2828
0.3-0.4	7108
0.4-0.5	11153
0.5-0.6	7089
0.6-0.7	9499
0.7-0.8	2967
0.8-0.85	269
0.85-0.9	61
0.9-0.95	15
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9692	High Similarity	NPC78307
0.947	High Similarity	NPC202225
0.9394	High Similarity	NPC477139
0.9389	High Similarity	NPC471851
0.9237	High Similarity	NPC171460
0.9231	High Similarity	NPC78364
0.9231	High Similarity	NPC176130
0.9231	High Similarity	NPC69424
0.9231	High Similarity	NPC84672
0.9203	High Similarity	NPC248068
0.9167	High Similarity	NPC108129
0.9149	High Similarity	NPC5568
0.9084	High Similarity	NPC72667
0.9015	High Similarity	NPC3009
0.9008	High Similarity	NPC254492
0.9	High Similarity	NPC181334
0.8947	High Similarity	NPC276238
0.8947	High Similarity	NPC303910
0.8944	High Similarity	NPC143685
0.8921	High Similarity	NPC471853
0.8873	High Similarity	NPC478160
0.8855	High Similarity	NPC199273
0.8824	High Similarity	NPC111845
0.8815	High Similarity	NPC93015
0.8803	High Similarity	NPC79627
0.8794	High Similarity	NPC308572
0.8788	High Similarity	NPC123506
0.8788	High Similarity	NPC137750
0.8779	High Similarity	NPC471187
0.8777	High Similarity	NPC230811
0.8768	High Similarity	NPC474311
0.8732	High Similarity	NPC478164
0.8731	High Similarity	NPC96024
0.8702	High Similarity	NPC282577
0.8686	High Similarity	NPC138472
0.8686	High Similarity	NPC52407
0.8676	High Similarity	NPC476847
0.8671	High Similarity	NPC471906
0.8662	High Similarity	NPC135524
0.8647	High Similarity	NPC87985
0.8633	High Similarity	NPC86524
0.8633	High Similarity	NPC471670
0.8633	High Similarity	NPC472308
0.863	High Similarity	NPC474310
0.8626	High Similarity	NPC154696
0.8601	High Similarity	NPC100242
0.8592	High Similarity	NPC305845
0.8592	High Similarity	NPC204045
0.8582	High Similarity	NPC15837
0.8582	High Similarity	NPC71610
0.8561	High Similarity	NPC153088
0.8561	High Similarity	NPC11250
0.8561	High Similarity	NPC80035
0.8552	High Similarity	NPC314437
0.8551	High Similarity	NPC314048
0.8551	High Similarity	NPC115458
0.8531	High Similarity	NPC469855
0.8531	High Similarity	NPC477209
0.8531	High Similarity	NPC193555
0.8531	High Similarity	NPC471972
0.8531	High Similarity	NPC471971
0.8531	High Similarity	NPC30846
0.8531	High Similarity	NPC474961
0.8521	High Similarity	NPC476534
0.8519	High Similarity	NPC262936
0.8519	High Similarity	NPC30491
0.8511	High Similarity	NPC13715
0.8511	High Similarity	NPC4214
0.8496	Intermediate Similarity	NPC198014
0.8496	Intermediate Similarity	NPC273683
0.8493	Intermediate Similarity	NPC52692
0.8489	Intermediate Similarity	NPC23894
0.8489	Intermediate Similarity	NPC474659
0.8467	Intermediate Similarity	NPC199253
0.8467	Intermediate Similarity	NPC136588
0.8456	Intermediate Similarity	NPC48248
0.844	Intermediate Similarity	NPC277559
0.844	Intermediate Similarity	NPC477592
0.844	Intermediate Similarity	NPC49911
0.844	Intermediate Similarity	NPC36868
0.8433	Intermediate Similarity	NPC68756
0.8433	Intermediate Similarity	NPC152525
0.8421	Intermediate Similarity	NPC91478
0.8421	Intermediate Similarity	NPC176208
0.8417	Intermediate Similarity	NPC4170
0.8417	Intermediate Similarity	NPC53896
0.8417	Intermediate Similarity	NPC59459
0.8414	Intermediate Similarity	NPC469856
0.8414	Intermediate Similarity	NPC244691
0.8414	Intermediate Similarity	NPC469854
0.8409	Intermediate Similarity	NPC32322
0.8409	Intermediate Similarity	NPC259703
0.8406	Intermediate Similarity	NPC291001
0.8406	Intermediate Similarity	NPC164295
0.8406	Intermediate Similarity	NPC17083
0.8394	Intermediate Similarity	NPC25736
0.8392	Intermediate Similarity	NPC315578
0.8392	Intermediate Similarity	NPC181560
0.8392	Intermediate Similarity	NPC169452
0.838	Intermediate Similarity	NPC469680
0.838	Intermediate Similarity	NPC471974
0.838	Intermediate Similarity	NPC469681
0.8369	Intermediate Similarity	NPC272268
0.8369	Intermediate Similarity	NPC315275
0.8367	Intermediate Similarity	NPC478018
0.8358	Intermediate Similarity	NPC275145
0.8357	Intermediate Similarity	NPC50924
0.8356	Intermediate Similarity	NPC34482
0.8346	Intermediate Similarity	NPC120545
0.8346	Intermediate Similarity	NPC162935
0.8346	Intermediate Similarity	NPC253627
0.8346	Intermediate Similarity	NPC249340
0.8345	Intermediate Similarity	NPC165612
0.8345	Intermediate Similarity	NPC66593
0.8345	Intermediate Similarity	NPC70622
0.8333	Intermediate Similarity	NPC272907
0.8333	Intermediate Similarity	NPC2681
0.8333	Intermediate Similarity	NPC27659
0.8333	Intermediate Similarity	NPC31799
0.8333	Intermediate Similarity	NPC253488
0.8322	Intermediate Similarity	NPC242994
0.8322	Intermediate Similarity	NPC26924
0.8322	Intermediate Similarity	NPC190457
0.8322	Intermediate Similarity	NPC162939
0.8322	Intermediate Similarity	NPC138099
0.8321	Intermediate Similarity	NPC229894
0.831	Intermediate Similarity	NPC53001
0.831	Intermediate Similarity	NPC471452
0.831	Intermediate Similarity	NPC119542
0.831	Intermediate Similarity	NPC471905
0.8308	Intermediate Similarity	NPC477137
0.8308	Intermediate Similarity	NPC308311
0.8308	Intermediate Similarity	NPC38893
0.8299	Intermediate Similarity	NPC470570
0.8299	Intermediate Similarity	NPC136878
0.8299	Intermediate Similarity	NPC471970
0.8298	Intermediate Similarity	NPC477596
0.8298	Intermediate Similarity	NPC22644
0.8298	Intermediate Similarity	NPC103082
0.8298	Intermediate Similarity	NPC283088
0.8296	Intermediate Similarity	NPC74507
0.8296	Intermediate Similarity	NPC234890
0.8288	Intermediate Similarity	NPC196941
0.8288	Intermediate Similarity	NPC29932
0.8288	Intermediate Similarity	NPC309169
0.8288	Intermediate Similarity	NPC48762
0.8286	Intermediate Similarity	NPC225051
0.8286	Intermediate Similarity	NPC49742
0.8278	Intermediate Similarity	NPC472211
0.8276	Intermediate Similarity	NPC85310
0.8276	Intermediate Similarity	NPC201297
0.8276	Intermediate Similarity	NPC184935
0.8276	Intermediate Similarity	NPC469520
0.8276	Intermediate Similarity	NPC73061
0.8273	Intermediate Similarity	NPC41847
0.8273	Intermediate Similarity	NPC239134
0.8273	Intermediate Similarity	NPC18798
0.8271	Intermediate Similarity	NPC472981
0.8261	Intermediate Similarity	NPC117899
0.8261	Intermediate Similarity	NPC99731
0.8258	Intermediate Similarity	NPC473767
0.8258	Intermediate Similarity	NPC476645
0.8252	Intermediate Similarity	NPC87723
0.8252	Intermediate Similarity	NPC91887
0.8252	Intermediate Similarity	NPC50615
0.8252	Intermediate Similarity	NPC51531
0.8252	Intermediate Similarity	NPC477849
0.8252	Intermediate Similarity	NPC114333
0.8252	Intermediate Similarity	NPC5014
0.8252	Intermediate Similarity	NPC165191
0.8252	Intermediate Similarity	NPC157284
0.8252	Intermediate Similarity	NPC46242
0.8252	Intermediate Similarity	NPC297797
0.8252	Intermediate Similarity	NPC289358
0.8252	Intermediate Similarity	NPC42384
0.8252	Intermediate Similarity	NPC473479
0.8252	Intermediate Similarity	NPC28592
0.8252	Intermediate Similarity	NPC23667
0.8252	Intermediate Similarity	NPC245760
0.8252	Intermediate Similarity	NPC473779
0.8252	Intermediate Similarity	NPC149773
0.8252	Intermediate Similarity	NPC477593
0.8252	Intermediate Similarity	NPC469857
0.8243	Intermediate Similarity	NPC478163
0.8239	Intermediate Similarity	NPC191976
0.8239	Intermediate Similarity	NPC38158
0.8239	Intermediate Similarity	NPC254847
0.8239	Intermediate Similarity	NPC193358
0.8231	Intermediate Similarity	NPC192948
0.8231	Intermediate Similarity	NPC478019
0.8231	Intermediate Similarity	NPC12402
0.8231	Intermediate Similarity	NPC35797
0.8227	Intermediate Similarity	NPC12070
0.8227	Intermediate Similarity	NPC477594
0.8201	Intermediate Similarity	NPC198305
0.8194	Intermediate Similarity	NPC294330
0.8188	Intermediate Similarity	NPC473719
0.8188	Intermediate Similarity	NPC282923
0.8188	Intermediate Similarity	NPC193203
0.8182	Intermediate Similarity	NPC53414

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 NPC475957 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	936
0.2-0.3	1401
0.3-0.4	2652
0.4-0.5	2181
0.5-0.6	1190
0.6-0.7	455
0.7-0.8	55
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8239	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD3019	Approved
0.7985	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD1470	Approved
0.7926	Intermediate Similarity	NPD2932	Approved
0.7862	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD1201	Approved
0.78	Intermediate Similarity	NPD7390	Discontinued
0.7748	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD7003	Approved
0.7687	Intermediate Similarity	NPD5408	Approved
0.7687	Intermediate Similarity	NPD5406	Approved
0.7687	Intermediate Similarity	NPD5404	Approved
0.7687	Intermediate Similarity	NPD5405	Approved
0.7662	Intermediate Similarity	NPD7458	Discontinued
0.7647	Intermediate Similarity	NPD3091	Approved
0.7639	Intermediate Similarity	NPD6663	Approved
0.7609	Intermediate Similarity	NPD3023	Approved
0.7609	Intermediate Similarity	NPD3026	Approved
0.7606	Intermediate Similarity	NPD5736	Approved
0.7591	Intermediate Similarity	NPD3024	Approved
0.7591	Intermediate Similarity	NPD3025	Approved
0.7533	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD8166	Discontinued
0.7481	Intermediate Similarity	NPD5951	Approved
0.7468	Intermediate Similarity	NPD6273	Approved
0.7436	Intermediate Similarity	NPD3226	Approved
0.7436	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3092	Approved
0.741	Intermediate Similarity	NPD3095	Discontinued
0.7386	Intermediate Similarity	NPD3300	Phase 2
0.7376	Intermediate Similarity	NPD3972	Approved
0.7368	Intermediate Similarity	NPD4628	Phase 3
0.7343	Intermediate Similarity	NPD3094	Phase 2
0.7312	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6959	Discontinued
0.7286	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD7236	Approved
0.7267	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD943	Approved
0.7229	Intermediate Similarity	NPD7473	Discontinued
0.7219	Intermediate Similarity	NPD2935	Discontinued
0.7211	Intermediate Similarity	NPD3764	Approved
0.7209	Intermediate Similarity	NPD8150	Discontinued
0.7208	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2534	Approved
0.7179	Intermediate Similarity	NPD2533	Approved
0.7179	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2532	Approved
0.7163	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1283	Approved
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7152	Intermediate Similarity	NPD6232	Discontinued
0.7152	Intermediate Similarity	NPD7239	Suspended
0.7143	Intermediate Similarity	NPD7008	Discontinued
0.7143	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1237	Approved
0.7105	Intermediate Similarity	NPD6100	Approved
0.7105	Intermediate Similarity	NPD6099	Approved
0.7103	Intermediate Similarity	NPD1164	Approved
0.7092	Intermediate Similarity	NPD1651	Approved
0.709	Intermediate Similarity	NPD2342	Discontinued
0.708	Intermediate Similarity	NPD7635	Approved
0.707	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4380	Phase 2
0.7059	Intermediate Similarity	NPD1471	Phase 3
0.7045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD4626	Approved
0.7042	Intermediate Similarity	NPD4059	Approved
0.7039	Intermediate Similarity	NPD1510	Phase 2
0.7037	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1607	Approved
0.7019	Intermediate Similarity	NPD7411	Suspended
0.7013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7075	Discontinued
0.7	Intermediate Similarity	NPD4060	Phase 1
0.7	Intermediate Similarity	NPD4956	Approved
0.6987	Remote Similarity	NPD6190	Approved
0.6978	Remote Similarity	NPD2629	Approved
0.6957	Remote Similarity	NPD6599	Discontinued
0.6948	Remote Similarity	NPD2344	Approved
0.6944	Remote Similarity	NPD1281	Approved
0.6939	Remote Similarity	NPD2798	Approved
0.6933	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD5039	Approved
0.6918	Remote Similarity	NPD1876	Approved
0.6912	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1549	Phase 2
0.6901	Remote Similarity	NPD9545	Approved
0.6897	Remote Similarity	NPD4878	Approved
0.6892	Remote Similarity	NPD4208	Discontinued
0.6887	Remote Similarity	NPD2979	Phase 3
0.6887	Remote Similarity	NPD4140	Approved
0.6887	Remote Similarity	NPD1240	Approved
0.6887	Remote Similarity	NPD3620	Phase 2
0.6887	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5034	Approved
0.6879	Remote Similarity	NPD4954	Approved
0.6879	Remote Similarity	NPD36	Approved
0.6879	Remote Similarity	NPD5026	Approved
0.6879	Remote Similarity	NPD5028	Approved
0.6879	Remote Similarity	NPD4955	Approved
0.6872	Remote Similarity	NPD6535	Approved
0.6872	Remote Similarity	NPD6534	Approved
0.6871	Remote Similarity	NPD6801	Discontinued
0.6867	Remote Similarity	NPD3268	Approved
0.6864	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6166	Phase 2
0.6864	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5691	Approved
0.6849	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1755	Approved
0.6848	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3882	Suspended
0.6846	Remote Similarity	NPD1809	Phase 2
0.6839	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD8312	Approved
0.6839	Remote Similarity	NPD8313	Approved
0.6839	Remote Similarity	NPD5035	Approved
0.6839	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7610	Discontinued
0.6821	Remote Similarity	NPD8032	Phase 2
0.6821	Remote Similarity	NPD5030	Phase 2
0.6821	Remote Similarity	NPD7961	Discontinued
0.6818	Remote Similarity	NPD8434	Phase 2
0.6818	Remote Similarity	NPD3020	Approved
0.6815	Remote Similarity	NPD3750	Approved
0.6797	Remote Similarity	NPD4097	Suspended
0.6797	Remote Similarity	NPD6651	Approved
0.6794	Remote Similarity	NPD288	Approved
0.6788	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7177	Discontinued
0.6779	Remote Similarity	NPD9494	Approved
0.6776	Remote Similarity	NPD6782	Approved
0.6776	Remote Similarity	NPD6777	Approved
0.6776	Remote Similarity	NPD6776	Approved
0.6776	Remote Similarity	NPD6779	Approved
0.6776	Remote Similarity	NPD6778	Approved
0.6776	Remote Similarity	NPD6781	Approved
0.6776	Remote Similarity	NPD6780	Approved
0.6774	Remote Similarity	NPD2438	Suspended
0.6774	Remote Similarity	NPD2796	Approved
0.6772	Remote Similarity	NPD2309	Approved
0.6768	Remote Similarity	NPD37	Approved
0.6768	Remote Similarity	NPD1934	Approved
0.6763	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7700	Phase 2
0.6758	Remote Similarity	NPD7699	Phase 2
0.6755	Remote Similarity	NPD2313	Discontinued
0.6755	Remote Similarity	NPD6798	Discontinued
0.6752	Remote Similarity	NPD2800	Approved
0.6747	Remote Similarity	NPD7058	Phase 2
0.6747	Remote Similarity	NPD7057	Phase 3
0.6743	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3021	Approved
0.6739	Remote Similarity	NPD3022	Approved
0.6739	Remote Similarity	NPD4750	Phase 3
0.6732	Remote Similarity	NPD6355	Discontinued
0.6732	Remote Similarity	NPD230	Phase 1
0.6731	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5760	Phase 2
0.6727	Remote Similarity	NPD5761	Phase 2
0.6726	Remote Similarity	NPD5494	Approved
0.6725	Remote Similarity	NPD5033	Approved
0.6723	Remote Similarity	NPD5038	Approved
0.6723	Remote Similarity	NPD5037	Approved
0.672	Remote Similarity	NPD8320	Phase 1
0.672	Remote Similarity	NPD8319	Approved
0.6718	Remote Similarity	NPD844	Approved
0.671	Remote Similarity	NPD7743	Approved
0.671	Remote Similarity	NPD7742	Approved
0.669	Remote Similarity	NPD2286	Discontinued
0.669	Remote Similarity	NPD3317	Approved
0.6686	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD1930	Approved
0.6667	Remote Similarity	NPD7696	Phase 3
0.6667	Remote Similarity	NPD7697	Approved
0.6667	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1929	Approved
0.6667	Remote Similarity	NPD7698	Approved
0.6667	Remote Similarity	NPD9269	Phase 2
0.6667	Remote Similarity	NPD3495	Discontinued
0.6667	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5036	Approved
0.6667	Remote Similarity	NPD2531	Phase 2
0.6647	Remote Similarity	NPD5711	Approved

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