NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.08
Volume:	238.321
LogP:	1.194
LogD:	1.467
LogS:	-2.074
# Rotatable Bonds:	5
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.574
Synthetic Accessibility Score:	1.983
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.544
MDCK Permeability:	3.654745523817837e-05
Pgp-inhibitor:	0.113
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.115

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.467
Plasma Protein Binding (PPB):	69.74150848388672%
Volume Distribution (VD):	0.688
Pgp-substrate:	19.153209686279297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.67
CYP1A2-substrate:	0.958
CYP2C19-inhibitor:	0.232
CYP2C19-substrate:	0.877
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.775
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.77
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.536

ADMET: Excretion

Clearance (CL):	8.249
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.076
Drug-inuced Liver Injury (DILI):	0.457
AMES Toxicity:	0.338
Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.236
Carcinogencity:	0.042
Eye Corrosion:	0.126
Eye Irritation:	0.807
Respiratory Toxicity:	0.77

Download Data

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

Natural Product: NPC143649

Natural Product ID:	NPC143649
*Common Name:**	1-(2,4,5-Trimethoxyphenyl)Propan-1,2-Dione
IUPAC Name:	1-(2,4,5-trimethoxyphenyl)propane-1,2-dione
Synonyms:
Standard InCHIKey:	UUZQHDNTPXKEID-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H14O5/c1-7(13)12(14)8-5-10(16-3)11(17-4)6-9(8)15-2/h5-6H,1-4H3
SMILES:	COc1cc(c(cc1OC)OC)C(=O)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450829
PubChem CID:	15172937
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0002811] Phenylpropanes

*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
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679319]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20476749]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[21936523]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21936523]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22951040]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23713285]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[26296476]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26305406]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[29116780]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29031	Rhizoma acori graminei	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8666	Acorus tatarinowii	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5681	Acorus gramineus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11169	Piper cubeba	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8666	Acorus tatarinowii	Species	Acoraceae	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
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	IC50	=	74000.0	nM	PMID[476978]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	IC50	>	100000.0	nM	PMID[476978]

☑ 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 NPC143649 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	469
0.1-0.2	2112
0.2-0.3	6387
0.3-0.4	11786
0.4-0.5	4509
0.5-0.6	4662
0.6-0.7	5624
0.7-0.8	5806
0.8-0.85	1128
0.85-0.9	188
0.9-0.95	23
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC474274
0.9545	High Similarity	NPC157944
0.9407	High Similarity	NPC58229
0.9343	High Similarity	NPC182842
0.9333	High Similarity	NPC207418
0.9231	High Similarity	NPC150809
0.9209	High Similarity	NPC226987
0.9209	High Similarity	NPC120924
0.9209	High Similarity	NPC216314
0.9209	High Similarity	NPC231013
0.9209	High Similarity	NPC195919
0.9209	High Similarity	NPC143903
0.9191	High Similarity	NPC50823
0.9185	High Similarity	NPC46947
0.9185	High Similarity	NPC44573
0.9143	High Similarity	NPC93034
0.9143	High Similarity	NPC119660
0.9143	High Similarity	NPC205522
0.9137	High Similarity	NPC165512
0.9137	High Similarity	NPC472917
0.9078	High Similarity	NPC63256
0.9078	High Similarity	NPC10304
0.9078	High Similarity	NPC287395
0.9078	High Similarity	NPC183655
0.9071	High Similarity	NPC14958
0.9071	High Similarity	NPC110639
0.9071	High Similarity	NPC302408
0.9071	High Similarity	NPC283002
0.9071	High Similarity	NPC40818
0.9071	High Similarity	NPC106461
0.9071	High Similarity	NPC215932
0.9015	High Similarity	NPC299010
0.9014	High Similarity	NPC92722
0.9014	High Similarity	NPC102003
0.9007	High Similarity	NPC85233
0.9007	High Similarity	NPC30647
0.9007	High Similarity	NPC61871
0.9007	High Similarity	NPC55557
0.9	High Similarity	NPC136278
0.8951	High Similarity	NPC179183
0.8951	High Similarity	NPC156953
0.8951	High Similarity	NPC239363
0.8951	High Similarity	NPC472884
0.8944	High Similarity	NPC15329
0.8944	High Similarity	NPC131451
0.8944	High Similarity	NPC476058
0.8929	High Similarity	NPC113089
0.8929	High Similarity	NPC23955
0.8921	High Similarity	NPC185607
0.8921	High Similarity	NPC29536
0.8889	High Similarity	NPC171010
0.8889	High Similarity	NPC279061
0.8889	High Similarity	NPC149614
0.8889	High Similarity	NPC262623
0.8889	High Similarity	NPC19980
0.8889	High Similarity	NPC45291
0.8881	High Similarity	NPC181250
0.8881	High Similarity	NPC238366
0.8881	High Similarity	NPC69752
0.8865	High Similarity	NPC224687
0.8864	High Similarity	NPC304747
0.8857	High Similarity	NPC476054
0.8857	High Similarity	NPC119663
0.8857	High Similarity	NPC9966
0.8857	High Similarity	NPC70853
0.8841	High Similarity	NPC4796
0.8828	High Similarity	NPC131266
0.8828	High Similarity	NPC161277
0.8828	High Similarity	NPC35763
0.8828	High Similarity	NPC100263
0.8828	High Similarity	NPC216769
0.8828	High Similarity	NPC153008
0.8828	High Similarity	NPC269451
0.8828	High Similarity	NPC181209
0.8828	High Similarity	NPC52623
0.8828	High Similarity	NPC100971
0.8828	High Similarity	NPC245382
0.8828	High Similarity	NPC121522
0.8828	High Similarity	NPC291802
0.8828	High Similarity	NPC166201
0.8828	High Similarity	NPC148497
0.8828	High Similarity	NPC101996
0.8828	High Similarity	NPC39007
0.8828	High Similarity	NPC209487
0.8824	High Similarity	NPC208760
0.8819	High Similarity	NPC216917
0.8819	High Similarity	NPC103509
0.8819	High Similarity	NPC29056
0.8819	High Similarity	NPC259058
0.8819	High Similarity	NPC201547
0.8819	High Similarity	NPC306821
0.8815	High Similarity	NPC288743
0.8803	High Similarity	NPC165389
0.8797	High Similarity	NPC153547
0.8794	High Similarity	NPC27106
0.8794	High Similarity	NPC293201
0.8794	High Similarity	NPC142165
0.8786	High Similarity	NPC214919
0.8786	High Similarity	NPC124467
0.8786	High Similarity	NPC299154
0.8779	High Similarity	NPC65041
0.8767	High Similarity	NPC478213
0.8767	High Similarity	NPC244371
0.8767	High Similarity	NPC250557
0.8767	High Similarity	NPC472408
0.8767	High Similarity	NPC292214
0.8767	High Similarity	NPC88645
0.8767	High Similarity	NPC206238
0.8767	High Similarity	NPC186507
0.8767	High Similarity	NPC271779
0.8767	High Similarity	NPC128961
0.8767	High Similarity	NPC124714
0.8767	High Similarity	NPC280937
0.8767	High Similarity	NPC57211
0.8767	High Similarity	NPC167091
0.8767	High Similarity	NPC472915
0.8759	High Similarity	NPC226973
0.8759	High Similarity	NPC198615
0.8759	High Similarity	NPC474663
0.8759	High Similarity	NPC117579
0.8759	High Similarity	NPC308451
0.8759	High Similarity	NPC208043
0.875	High Similarity	NPC328119
0.875	High Similarity	NPC155098
0.8741	High Similarity	NPC117463
0.8741	High Similarity	NPC472885
0.8741	High Similarity	NPC299923
0.8732	High Similarity	NPC471590
0.8732	High Similarity	NPC296575
0.8723	High Similarity	NPC254659
0.8723	High Similarity	NPC287722
0.8707	High Similarity	NPC134287
0.8707	High Similarity	NPC130589
0.8707	High Similarity	NPC256612
0.8707	High Similarity	NPC39184
0.8707	High Similarity	NPC2928
0.8707	High Similarity	NPC208197
0.8707	High Similarity	NPC478238
0.8707	High Similarity	NPC20830
0.8699	High Similarity	NPC71334
0.8699	High Similarity	NPC156222
0.8699	High Similarity	NPC301123
0.8699	High Similarity	NPC180234
0.8699	High Similarity	NPC293183
0.8699	High Similarity	NPC120163
0.8699	High Similarity	NPC188203
0.8699	High Similarity	NPC275836
0.8699	High Similarity	NPC256283
0.8699	High Similarity	NPC162313
0.8699	High Similarity	NPC57030
0.8699	High Similarity	NPC142540
0.8699	High Similarity	NPC239128
0.8699	High Similarity	NPC134677
0.8699	High Similarity	NPC187498
0.8699	High Similarity	NPC212678
0.8699	High Similarity	NPC120537
0.8699	High Similarity	NPC25270
0.8699	High Similarity	NPC199100
0.8699	High Similarity	NPC292460
0.8699	High Similarity	NPC83508
0.8699	High Similarity	NPC222830
0.8699	High Similarity	NPC131624
0.8699	High Similarity	NPC241498
0.8699	High Similarity	NPC301323
0.8699	High Similarity	NPC100887
0.8699	High Similarity	NPC275722
0.8699	High Similarity	NPC198826
0.869	High Similarity	NPC248102
0.869	High Similarity	NPC45873
0.869	High Similarity	NPC10467
0.8681	High Similarity	NPC218490
0.8671	High Similarity	NPC12377
0.8671	High Similarity	NPC310259
0.8652	High Similarity	NPC301178
0.8652	High Similarity	NPC284556
0.8652	High Similarity	NPC312256
0.8649	High Similarity	NPC180340
0.8649	High Similarity	NPC472916
0.8649	High Similarity	NPC45131
0.8639	High Similarity	NPC231018
0.8639	High Similarity	NPC75279
0.8639	High Similarity	NPC160951
0.8639	High Similarity	NPC69394
0.8639	High Similarity	NPC183878
0.8639	High Similarity	NPC255350
0.8639	High Similarity	NPC22519
0.8639	High Similarity	NPC86485
0.8639	High Similarity	NPC176775
0.8639	High Similarity	NPC274327
0.8639	High Similarity	NPC145379
0.8639	High Similarity	NPC276409
0.8639	High Similarity	NPC47781
0.8639	High Similarity	NPC250822
0.8639	High Similarity	NPC476289
0.8633	High Similarity	NPC470962
0.863	High Similarity	NPC288316
0.863	High Similarity	NPC251110
0.8623	High Similarity	NPC160425
0.8621	High Similarity	NPC216318
0.8621	High Similarity	NPC264289

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 NPC143649 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	417
0.1-0.2	1109
0.2-0.3	2139
0.3-0.4	2739
0.4-0.5	1481
0.5-0.6	872
0.6-0.7	276
0.7-0.8	105
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8639	High Similarity	NPD2801	Approved
0.8477	Intermediate Similarity	NPD5494	Approved
0.8421	Intermediate Similarity	NPD1247	Approved
0.8322	Intermediate Similarity	NPD1934	Approved
0.8278	Intermediate Similarity	NPD3882	Suspended
0.8276	Intermediate Similarity	NPD1511	Approved
0.8212	Intermediate Similarity	NPD3817	Phase 2
0.8201	Intermediate Similarity	NPD1240	Approved
0.8163	Intermediate Similarity	NPD1512	Approved
0.8099	Intermediate Similarity	NPD1510	Phase 2
0.8085	Intermediate Similarity	NPD1607	Approved
0.8056	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD919	Approved
0.8042	Intermediate Similarity	NPD2796	Approved
0.8026	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD230	Phase 1
0.8014	Intermediate Similarity	NPD447	Suspended
0.7987	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD3926	Phase 2
0.7943	Intermediate Similarity	NPD943	Approved
0.7905	Intermediate Similarity	NPD6799	Approved
0.7898	Intermediate Similarity	NPD6232	Discontinued
0.7867	Intermediate Similarity	NPD920	Approved
0.7862	Intermediate Similarity	NPD7473	Discontinued
0.7847	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD3818	Discontinued
0.7808	Intermediate Similarity	NPD1549	Phase 2
0.7799	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD6166	Phase 2
0.7799	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD1243	Approved
0.7755	Intermediate Similarity	NPD2654	Approved
0.774	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD9494	Approved
0.7712	Intermediate Similarity	NPD4380	Phase 2
0.7692	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1465	Phase 2
0.7671	Intermediate Similarity	NPD2935	Discontinued
0.7654	Intermediate Similarity	NPD7054	Approved
0.7635	Intermediate Similarity	NPD2800	Approved
0.7628	Intermediate Similarity	NPD5402	Approved
0.7628	Intermediate Similarity	NPD5353	Approved
0.7616	Intermediate Similarity	NPD2534	Approved
0.7616	Intermediate Similarity	NPD2532	Approved
0.7616	Intermediate Similarity	NPD2533	Approved
0.7616	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7472	Approved
0.7607	Intermediate Similarity	NPD7074	Phase 3
0.7597	Intermediate Similarity	NPD6599	Discontinued
0.7584	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD9268	Approved
0.7564	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7819	Suspended
0.7546	Intermediate Similarity	NPD5844	Phase 1
0.7517	Intermediate Similarity	NPD1933	Approved
0.75	Intermediate Similarity	NPD6801	Discontinued
0.7483	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD9269	Phase 2
0.747	Intermediate Similarity	NPD7808	Phase 3
0.7466	Intermediate Similarity	NPD6651	Approved
0.7455	Intermediate Similarity	NPD6797	Phase 2
0.7426	Intermediate Similarity	NPD5536	Phase 2
0.7421	Intermediate Similarity	NPD7075	Discontinued
0.7421	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7251	Discontinued
0.7407	Intermediate Similarity	NPD5242	Approved
0.7386	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3748	Approved
0.7365	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD2403	Approved
0.7325	Intermediate Similarity	NPD6386	Approved
0.7325	Intermediate Similarity	NPD7411	Suspended
0.7325	Intermediate Similarity	NPD6385	Approved
0.7315	Intermediate Similarity	NPD1551	Phase 2
0.7284	Intermediate Similarity	NPD6959	Discontinued
0.7279	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1019	Discontinued
0.7273	Intermediate Similarity	NPD5401	Approved
0.7246	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD9717	Approved
0.7222	Intermediate Similarity	NPD3018	Phase 2
0.7192	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5403	Approved
0.7172	Intermediate Similarity	NPD6832	Phase 2
0.7163	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1241	Discontinued
0.7124	Intermediate Similarity	NPD3750	Approved
0.7123	Intermediate Similarity	NPD3027	Phase 3
0.7113	Intermediate Similarity	NPD3972	Approved
0.7113	Intermediate Similarity	NPD2981	Phase 2
0.7103	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD9493	Approved
0.7099	Intermediate Similarity	NPD3749	Approved
0.7097	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD411	Approved
0.7063	Intermediate Similarity	NPD37	Approved
0.7063	Intermediate Similarity	NPD2983	Phase 2
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2982	Phase 2
0.7055	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2344	Approved
0.7034	Intermediate Similarity	NPD2798	Approved
0.7025	Intermediate Similarity	NPD1653	Approved
0.7024	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2799	Discontinued
0.7011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6559	Discontinued
0.7	Intermediate Similarity	NPD9545	Approved
0.6987	Remote Similarity	NPD4357	Discontinued
0.6981	Remote Similarity	NPD3226	Approved
0.698	Remote Similarity	NPD1613	Approved
0.698	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD1203	Approved
0.6964	Remote Similarity	NPD3751	Discontinued
0.6959	Remote Similarity	NPD2313	Discontinued
0.6959	Remote Similarity	NPD1296	Phase 2
0.6948	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4967	Phase 2
0.6933	Remote Similarity	NPD7768	Phase 2
0.6933	Remote Similarity	NPD4966	Approved
0.6933	Remote Similarity	NPD4965	Approved
0.6928	Remote Similarity	NPD5711	Approved
0.6928	Remote Similarity	NPD2346	Discontinued
0.6928	Remote Similarity	NPD1471	Phase 3
0.6928	Remote Similarity	NPD5710	Approved
0.6923	Remote Similarity	NPD3705	Approved
0.6923	Remote Similarity	NPD7286	Phase 2
0.6903	Remote Similarity	NPD4628	Phase 3
0.6901	Remote Similarity	NPD17	Approved
0.6899	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1876	Approved
0.6894	Remote Similarity	NPD5089	Approved
0.6894	Remote Similarity	NPD5090	Approved
0.6884	Remote Similarity	NPD5283	Phase 1
0.6879	Remote Similarity	NPD7390	Discontinued
0.6867	Remote Similarity	NPD7199	Phase 2
0.6863	Remote Similarity	NPD6099	Approved
0.6863	Remote Similarity	NPD6100	Approved
0.6861	Remote Similarity	NPD228	Approved
0.6859	Remote Similarity	NPD2309	Approved
0.6859	Remote Similarity	NPD6190	Approved
0.6851	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6234	Discontinued
0.6842	Remote Similarity	NPD5953	Discontinued
0.6836	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3146	Approved
0.6826	Remote Similarity	NPD3787	Discontinued
0.681	Remote Similarity	NPD4585	Approved
0.6806	Remote Similarity	NPD422	Phase 1
0.6795	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5978	Approved
0.6768	Remote Similarity	NPD5977	Approved
0.6767	Remote Similarity	NPD9261	Approved
0.6759	Remote Similarity	NPD1608	Approved
0.6753	Remote Similarity	NPD3539	Phase 1
0.6748	Remote Similarity	NPD6844	Discontinued
0.6743	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD1470	Approved
0.6713	Remote Similarity	NPD1651	Approved
0.6711	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.671	Remote Similarity	NPD3540	Phase 1
0.6691	Remote Similarity	NPD1358	Approved
0.6667	Remote Similarity	NPD824	Approved
0.6667	Remote Similarity	NPD5297	Approved
0.6667	Remote Similarity	NPD2163	Approved
0.6647	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2219	Phase 1
0.6645	Remote Similarity	NPD4307	Phase 2
0.6645	Remote Similarity	NPD3142	Approved
0.6645	Remote Similarity	NPD3140	Approved
0.6627	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD6111	Discontinued
0.6622	Remote Similarity	NPD3267	Approved
0.6622	Remote Similarity	NPD3266	Approved
0.6621	Remote Similarity	NPD3496	Discontinued
0.6609	Remote Similarity	NPD7685	Pre-registration
0.6609	Remote Similarity	NPD6104	Discontinued
0.6603	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD2353	Approved
0.6598	Remote Similarity	NPD2899	Discontinued
0.6595	Remote Similarity	NPD5006	Approved
0.6595	Remote Similarity	NPD5005	Approved
0.659	Remote Similarity	NPD1729	Discontinued
0.6585	Remote Similarity	NPD6873	Phase 2
0.6576	Remote Similarity	NPD6780	Approved
0.6576	Remote Similarity	NPD6779	Approved
0.6576	Remote Similarity	NPD6782	Approved
0.6576	Remote Similarity	NPD6776	Approved
0.6576	Remote Similarity	NPD6778	Approved
0.6576	Remote Similarity	NPD6777	Approved
0.6576	Remote Similarity	NPD6781	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