NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.05
Volume:	238.872
LogP:	1.857
LogD:	1.459
LogS:	-2.616
# Rotatable Bonds:	5
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.759
Synthetic Accessibility Score:	2.148
Fsp3:	0.364
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.477
MDCK Permeability:	2.3186124963103794e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.88
Plasma Protein Binding (PPB):	43.43665313720703%
Volume Distribution (VD):	0.718
Pgp-substrate:	25.68897247314453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.692
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.374
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.752
CYP3A4-inhibitor:	0.151
CYP3A4-substrate:	0.687

ADMET: Excretion

Clearance (CL):	5.653
Half-life (T1/2):	0.743

ADMET: Toxicity

hERG Blockers:	0.309
Human Hepatotoxicity (H-HT):	0.117
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.542
Rat Oral Acute Toxicity:	0.341
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.657
Carcinogencity:	0.108
Eye Corrosion:	0.942
Eye Irritation:	0.937
Respiratory Toxicity:	0.811

Download Data

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

Natural Product: NPC207418

Natural Product ID:	NPC207418
*Common Name:**	2,3,4,5-Tetramethoxybenzoylchloride
IUPAC Name:	2,3,4,5-tetramethoxybenzoyl chloride
Synonyms:	2,3,4,5-Tetramethoxybenzoylchloride
Standard InCHIKey:	IVMDBXGELGZZFZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H13ClO5/c1-14-7-5-6(11(12)13)8(15-2)10(17-4)9(7)16-3/h5H,1-4H3
SMILES:	COc1c(OC)cc(c(c1OC)OC)C(=O)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL376803
PubChem CID:	44424387
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives

*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
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14738384]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[16643055]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24387703]
NPO30573	Antrodia camphorata	Species	Fomitopsidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[459649]

☑ 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 NPC207418 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	498
0.1-0.2	2460
0.2-0.3	7767
0.3-0.4	11610
0.4-0.5	3672
0.5-0.6	5637
0.6-0.7	6628
0.7-0.8	4197
0.8-0.85	205
0.85-0.9	19
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC143649
0.9197	High Similarity	NPC474274
0.9197	High Similarity	NPC157944
0.8803	High Similarity	NPC58229
0.875	High Similarity	NPC182842
0.8686	High Similarity	NPC299010
0.863	High Similarity	NPC143903
0.863	High Similarity	NPC231013
0.863	High Similarity	NPC120924
0.863	High Similarity	NPC226987
0.863	High Similarity	NPC216314
0.863	High Similarity	NPC195919
0.8613	High Similarity	NPC150809
0.8601	High Similarity	NPC50823
0.8592	High Similarity	NPC44573
0.8592	High Similarity	NPC46947
0.8571	High Similarity	NPC93034
0.8571	High Similarity	NPC205522
0.8571	High Similarity	NPC119660
0.8562	High Similarity	NPC472917
0.8562	High Similarity	NPC165512
0.854	High Similarity	NPC304747
0.8514	High Similarity	NPC63256
0.8514	High Similarity	NPC10304
0.8514	High Similarity	NPC183655
0.8514	High Similarity	NPC287395
0.8503	High Similarity	NPC302408
0.8503	High Similarity	NPC283002
0.8503	High Similarity	NPC106461
0.8503	High Similarity	NPC40818
0.8503	High Similarity	NPC14958
0.8503	High Similarity	NPC215932
0.8503	High Similarity	NPC110639
0.85	High Similarity	NPC288743
0.8483	Intermediate Similarity	NPC299154
0.8456	Intermediate Similarity	NPC102003
0.8456	Intermediate Similarity	NPC92722
0.8446	Intermediate Similarity	NPC85233
0.8446	Intermediate Similarity	NPC61871
0.8446	Intermediate Similarity	NPC30647
0.8446	Intermediate Similarity	NPC55557
0.844	Intermediate Similarity	NPC155098
0.8435	Intermediate Similarity	NPC136278
0.84	Intermediate Similarity	NPC156953
0.84	Intermediate Similarity	NPC239363
0.84	Intermediate Similarity	NPC179183
0.84	Intermediate Similarity	NPC472884
0.8389	Intermediate Similarity	NPC131451
0.8389	Intermediate Similarity	NPC476058
0.8389	Intermediate Similarity	NPC15329
0.8367	Intermediate Similarity	NPC27106
0.8367	Intermediate Similarity	NPC113089
0.8367	Intermediate Similarity	NPC23955
0.8356	Intermediate Similarity	NPC185607
0.8356	Intermediate Similarity	NPC29536
0.8345	Intermediate Similarity	NPC153547
0.8344	Intermediate Similarity	NPC279061
0.8344	Intermediate Similarity	NPC149614
0.8344	Intermediate Similarity	NPC262623
0.8344	Intermediate Similarity	NPC45291
0.8344	Intermediate Similarity	NPC19980
0.8344	Intermediate Similarity	NPC171010
0.8333	Intermediate Similarity	NPC181250
0.8333	Intermediate Similarity	NPC238366
0.8333	Intermediate Similarity	NPC69752
0.8311	Intermediate Similarity	NPC224687
0.8299	Intermediate Similarity	NPC119663
0.8299	Intermediate Similarity	NPC70853
0.8299	Intermediate Similarity	NPC9966
0.8299	Intermediate Similarity	NPC476054
0.8289	Intermediate Similarity	NPC269451
0.8289	Intermediate Similarity	NPC100971
0.8289	Intermediate Similarity	NPC291802
0.8289	Intermediate Similarity	NPC166201
0.8289	Intermediate Similarity	NPC245382
0.8289	Intermediate Similarity	NPC161277
0.8289	Intermediate Similarity	NPC209487
0.8289	Intermediate Similarity	NPC153008
0.8289	Intermediate Similarity	NPC131266
0.8289	Intermediate Similarity	NPC121522
0.8289	Intermediate Similarity	NPC101996
0.8289	Intermediate Similarity	NPC148497
0.8289	Intermediate Similarity	NPC216769
0.8289	Intermediate Similarity	NPC35763
0.8289	Intermediate Similarity	NPC100263
0.8289	Intermediate Similarity	NPC39007
0.8289	Intermediate Similarity	NPC52623
0.8289	Intermediate Similarity	NPC181209
0.8278	Intermediate Similarity	NPC306821
0.8278	Intermediate Similarity	NPC216917
0.8278	Intermediate Similarity	NPC201547
0.8278	Intermediate Similarity	NPC29056
0.8278	Intermediate Similarity	NPC103509
0.8278	Intermediate Similarity	NPC259058
0.8276	Intermediate Similarity	NPC4796
0.8264	Intermediate Similarity	NPC112068
0.8264	Intermediate Similarity	NPC95679
0.8264	Intermediate Similarity	NPC25305
0.8264	Intermediate Similarity	NPC125417
0.8264	Intermediate Similarity	NPC110899
0.8261	Intermediate Similarity	NPC154275
0.8255	Intermediate Similarity	NPC165389
0.8252	Intermediate Similarity	NPC208760
0.8243	Intermediate Similarity	NPC142165
0.8243	Intermediate Similarity	NPC293201
0.8235	Intermediate Similarity	NPC472915
0.8235	Intermediate Similarity	NPC472408
0.8235	Intermediate Similarity	NPC57211
0.8235	Intermediate Similarity	NPC88645
0.8235	Intermediate Similarity	NPC167091
0.8235	Intermediate Similarity	NPC244371
0.8235	Intermediate Similarity	NPC206238
0.8235	Intermediate Similarity	NPC128961
0.8235	Intermediate Similarity	NPC292214
0.8235	Intermediate Similarity	NPC250557
0.8235	Intermediate Similarity	NPC124714
0.8235	Intermediate Similarity	NPC271779
0.8235	Intermediate Similarity	NPC478213
0.8235	Intermediate Similarity	NPC280937
0.8235	Intermediate Similarity	NPC186507
0.8231	Intermediate Similarity	NPC214919
0.8231	Intermediate Similarity	NPC124467
0.8224	Intermediate Similarity	NPC198615
0.8224	Intermediate Similarity	NPC226973
0.8224	Intermediate Similarity	NPC474663
0.8224	Intermediate Similarity	NPC208043
0.8224	Intermediate Similarity	NPC117579
0.8224	Intermediate Similarity	NPC308451
0.8212	Intermediate Similarity	NPC328119
0.82	Intermediate Similarity	NPC117463
0.82	Intermediate Similarity	NPC299923
0.82	Intermediate Similarity	NPC472885
0.8194	Intermediate Similarity	NPC160425
0.8188	Intermediate Similarity	NPC65041
0.8188	Intermediate Similarity	NPC296575
0.8188	Intermediate Similarity	NPC471590
0.8182	Intermediate Similarity	NPC130589
0.8182	Intermediate Similarity	NPC478238
0.8182	Intermediate Similarity	NPC39184
0.8182	Intermediate Similarity	NPC20830
0.8182	Intermediate Similarity	NPC2928
0.8182	Intermediate Similarity	NPC208197
0.8182	Intermediate Similarity	NPC134287
0.8182	Intermediate Similarity	NPC256612
0.8176	Intermediate Similarity	NPC254659
0.8176	Intermediate Similarity	NPC287722
0.817	Intermediate Similarity	NPC187498
0.817	Intermediate Similarity	NPC83508
0.817	Intermediate Similarity	NPC241498
0.817	Intermediate Similarity	NPC25270
0.817	Intermediate Similarity	NPC275722
0.817	Intermediate Similarity	NPC57030
0.817	Intermediate Similarity	NPC100887
0.817	Intermediate Similarity	NPC198826
0.817	Intermediate Similarity	NPC222830
0.817	Intermediate Similarity	NPC301123
0.817	Intermediate Similarity	NPC293183
0.817	Intermediate Similarity	NPC292460
0.817	Intermediate Similarity	NPC71334
0.817	Intermediate Similarity	NPC142540
0.817	Intermediate Similarity	NPC199100
0.817	Intermediate Similarity	NPC134677
0.817	Intermediate Similarity	NPC212678
0.817	Intermediate Similarity	NPC275836
0.817	Intermediate Similarity	NPC180234
0.817	Intermediate Similarity	NPC188203
0.817	Intermediate Similarity	NPC131624
0.817	Intermediate Similarity	NPC156222
0.817	Intermediate Similarity	NPC301323
0.817	Intermediate Similarity	NPC120537
0.817	Intermediate Similarity	NPC162313
0.817	Intermediate Similarity	NPC239128
0.817	Intermediate Similarity	NPC256283
0.817	Intermediate Similarity	NPC120163
0.8158	Intermediate Similarity	NPC45873
0.8158	Intermediate Similarity	NPC10467
0.8158	Intermediate Similarity	NPC248102
0.8146	Intermediate Similarity	NPC218490
0.8133	Intermediate Similarity	NPC310259
0.8133	Intermediate Similarity	NPC12377
0.8129	Intermediate Similarity	NPC45131
0.8129	Intermediate Similarity	NPC180340
0.8129	Intermediate Similarity	NPC472916
0.8125	Intermediate Similarity	NPC274613
0.8125	Intermediate Similarity	NPC38101
0.8117	Intermediate Similarity	NPC75279
0.8117	Intermediate Similarity	NPC86485
0.8117	Intermediate Similarity	NPC160951
0.8117	Intermediate Similarity	NPC250822
0.8117	Intermediate Similarity	NPC69394
0.8117	Intermediate Similarity	NPC183878
0.8117	Intermediate Similarity	NPC231018
0.8117	Intermediate Similarity	NPC476289
0.8117	Intermediate Similarity	NPC176775
0.8117	Intermediate Similarity	NPC276409
0.8117	Intermediate Similarity	NPC255350
0.8117	Intermediate Similarity	NPC47781
0.8117	Intermediate Similarity	NPC145379
0.8117	Intermediate Similarity	NPC22519
0.8117	Intermediate Similarity	NPC274327

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 NPC207418 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	429
0.1-0.2	1165
0.2-0.3	2339
0.3-0.4	2687
0.4-0.5	1440
0.5-0.6	805
0.6-0.7	222
0.7-0.8	62
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
0.8117	Intermediate Similarity	NPD2801	Approved
0.7975	Intermediate Similarity	NPD5494	Approved
0.7925	Intermediate Similarity	NPD1247	Approved
0.7821	Intermediate Similarity	NPD1934	Approved
0.7785	Intermediate Similarity	NPD3882	Suspended
0.7763	Intermediate Similarity	NPD1511	Approved
0.774	Intermediate Similarity	NPD230	Phase 1
0.774	Intermediate Similarity	NPD447	Suspended
0.7722	Intermediate Similarity	NPD3817	Phase 2
0.7671	Intermediate Similarity	NPD1240	Approved
0.7667	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD1512	Approved
0.7584	Intermediate Similarity	NPD1510	Phase 2
0.7578	Intermediate Similarity	NPD919	Approved
0.7568	Intermediate Similarity	NPD1607	Approved
0.7547	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6232	Discontinued
0.7533	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD2403	Approved
0.7448	Intermediate Similarity	NPD9494	Approved
0.7432	Intermediate Similarity	NPD943	Approved
0.7419	Intermediate Similarity	NPD6799	Approved
0.741	Intermediate Similarity	NPD7473	Discontinued
0.7391	Intermediate Similarity	NPD5353	Approved
0.7389	Intermediate Similarity	NPD920	Approved
0.7365	Intermediate Similarity	NPD3818	Discontinued
0.7351	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6166	Phase 2
0.7349	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1465	Phase 2
0.732	Intermediate Similarity	NPD1549	Phase 2
0.7305	Intermediate Similarity	NPD9268	Approved
0.7303	Intermediate Similarity	NPD2935	Discontinued
0.7273	Intermediate Similarity	NPD2654	Approved
0.7273	Intermediate Similarity	NPD1243	Approved
0.7267	Intermediate Similarity	NPD1933	Approved
0.7261	Intermediate Similarity	NPD2534	Approved
0.7261	Intermediate Similarity	NPD2533	Approved
0.7261	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD2532	Approved
0.7255	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD9269	Phase 2
0.7219	Intermediate Similarity	NPD5844	Phase 1
0.7219	Intermediate Similarity	NPD7054	Approved
0.7178	Intermediate Similarity	NPD5402	Approved
0.7176	Intermediate Similarity	NPD7472	Approved
0.7176	Intermediate Similarity	NPD7074	Phase 3
0.7161	Intermediate Similarity	NPD2800	Approved
0.7152	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.7117	Intermediate Similarity	NPD7819	Suspended
0.7117	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5242	Approved
0.7078	Intermediate Similarity	NPD1551	Phase 2
0.7055	Intermediate Similarity	NPD6801	Discontinued
0.7052	Intermediate Similarity	NPD7808	Phase 3
0.7042	Intermediate Similarity	NPD5536	Phase 2
0.7039	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6797	Phase 2
0.7027	Intermediate Similarity	NPD1019	Discontinued
0.7025	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6386	Approved
0.6994	Remote Similarity	NPD7251	Discontinued
0.6994	Remote Similarity	NPD6385	Approved
0.6993	Remote Similarity	NPD6651	Approved
0.6988	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7075	Discontinued
0.6986	Remote Similarity	NPD9717	Approved
0.698	Remote Similarity	NPD3018	Phase 2
0.6937	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3748	Approved
0.6903	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7411	Suspended
0.6871	Remote Similarity	NPD2981	Phase 2
0.6864	Remote Similarity	NPD6959	Discontinued
0.6853	Remote Similarity	NPD9493	Approved
0.6842	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD411	Approved
0.6839	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5401	Approved
0.6824	Remote Similarity	NPD2982	Phase 2
0.6824	Remote Similarity	NPD2983	Phase 2
0.6821	Remote Similarity	NPD6832	Phase 2
0.681	Remote Similarity	NPD1653	Approved
0.6776	Remote Similarity	NPD3027	Phase 3
0.677	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.677	Remote Similarity	NPD4357	Discontinued
0.6766	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD9545	Approved
0.6755	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5403	Approved
0.6747	Remote Similarity	NPD37	Approved
0.6733	Remote Similarity	NPD1203	Approved
0.6711	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2353	Approved
0.6709	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3750	Approved
0.6686	Remote Similarity	NPD3749	Approved
0.6646	Remote Similarity	NPD6190	Approved
0.6646	Remote Similarity	NPD3887	Approved
0.6645	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1613	Approved
0.6644	Remote Similarity	NPD3972	Approved
0.6643	Remote Similarity	NPD1241	Discontinued
0.663	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5710	Approved
0.6628	Remote Similarity	NPD5711	Approved
0.6627	Remote Similarity	NPD4966	Approved
0.6627	Remote Similarity	NPD4967	Phase 2
0.6627	Remote Similarity	NPD4965	Approved
0.6627	Remote Similarity	NPD7768	Phase 2
0.6623	Remote Similarity	NPD1296	Phase 2
0.661	Remote Similarity	NPD6559	Discontinued
0.6604	Remote Similarity	NPD2344	Approved
0.6584	Remote Similarity	NPD4628	Phase 3
0.6582	Remote Similarity	NPD2799	Discontinued
0.6579	Remote Similarity	NPD2798	Approved
0.6577	Remote Similarity	NPD3705	Approved
0.6571	Remote Similarity	NPD3751	Discontinued
0.657	Remote Similarity	NPD7199	Phase 2
0.6566	Remote Similarity	NPD3226	Approved
0.6554	Remote Similarity	NPD17	Approved
0.6552	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.655	Remote Similarity	NPD6234	Discontinued
0.6543	Remote Similarity	NPD2354	Approved
0.6541	Remote Similarity	NPD3539	Phase 1
0.6534	Remote Similarity	NPD7286	Phase 2
0.6528	Remote Similarity	NPD5283	Phase 1
0.6524	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3146	Approved
0.6522	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD9261	Approved
0.6516	Remote Similarity	NPD2313	Discontinued
0.6503	Remote Similarity	NPD228	Approved
0.65	Remote Similarity	NPD2346	Discontinued
0.65	Remote Similarity	NPD3540	Phase 1
0.65	Remote Similarity	NPD1471	Phase 3
0.6494	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5089	Approved
0.6488	Remote Similarity	NPD5090	Approved
0.6481	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD422	Phase 1
0.6467	Remote Similarity	NPD824	Approved
0.6463	Remote Similarity	NPD5297	Approved
0.6463	Remote Similarity	NPD7390	Discontinued
0.6461	Remote Similarity	NPD5953	Discontinued
0.6454	Remote Similarity	NPD1358	Approved
0.6447	Remote Similarity	NPD1876	Approved
0.6442	Remote Similarity	NPD2309	Approved
0.6442	Remote Similarity	NPD2219	Phase 1
0.6438	Remote Similarity	NPD6099	Approved
0.6438	Remote Similarity	NPD6100	Approved
0.6437	Remote Similarity	NPD3787	Discontinued
0.6425	Remote Similarity	NPD7685	Pre-registration
0.6424	Remote Similarity	NPD1608	Approved
0.6412	Remote Similarity	NPD4585	Approved
0.6407	Remote Similarity	NPD957	Approved
0.6398	Remote Similarity	NPD4360	Phase 2
0.6398	Remote Similarity	NPD4363	Phase 3
0.6387	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5978	Approved
0.6374	Remote Similarity	NPD5977	Approved
0.6353	Remote Similarity	NPD6844	Discontinued
0.6338	Remote Similarity	NPD9267	Approved
0.6338	Remote Similarity	NPD9263	Approved
0.6338	Remote Similarity	NPD9264	Approved
0.6335	Remote Similarity	NPD5005	Approved
0.6335	Remote Similarity	NPD5006	Approved
0.6333	Remote Similarity	NPD1778	Approved
0.6331	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD4307	Phase 2
0.6312	Remote Similarity	NPD6111	Discontinued
0.6306	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD1470	Approved
0.6294	Remote Similarity	NPD6873	Phase 2
0.6294	Remote Similarity	NPD74	Approved
0.6294	Remote Similarity	NPD958	Approved
0.6294	Remote Similarity	NPD9266	Approved
0.6292	Remote Similarity	NPD7228	Approved
0.6292	Remote Similarity	NPD2822	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD2163	Approved
0.6291	Remote Similarity	NPD3496	Discontinued
0.6284	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD4361	Phase 2
0.6277	Remote Similarity	NPD4362	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