NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.1
Volume:	255.566
LogP:	2.98
LogD:	2.807
LogS:	-3.523
# Rotatable Bonds:	3
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.66
Synthetic Accessibility Score:	3.638
Fsp3:	0.357
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:	-4.592
MDCK Permeability:	1.425899699825095e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.79
Plasma Protein Binding (PPB):	79.90677642822266%
Volume Distribution (VD):	1.296
Pgp-substrate:	19.803552627563477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.547
CYP1A2-substrate:	0.693
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.58
CYP2C9-inhibitor:	0.112
CYP2C9-substrate:	0.551
CYP2D6-inhibitor:	0.083
CYP2D6-substrate:	0.425
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.259

ADMET: Excretion

Clearance (CL):	7.245
Half-life (T1/2):	0.292

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.576
Drug-inuced Liver Injury (DILI):	0.611
AMES Toxicity:	0.629
Rat Oral Acute Toxicity:	0.138
Maximum Recommended Daily Dose:	0.337
Skin Sensitization:	0.137
Carcinogencity:	0.56
Eye Corrosion:	0.012
Eye Irritation:	0.782
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC171870

Natural Product ID:	NPC171870
*Common Name:**	6-Hydroxy-3-Methoxytremetone
IUPAC Name:	1-[(2S,3R)-6-hydroxy-3-methoxy-2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl]ethanone
Synonyms:
Standard InCHIKey:	PHYSEYYYFQMJGP-UONOGXRCSA-N
Standard InCHI:	InChI=1S/C14H16O4/c1-7(2)13-14(17-4)10-5-9(8(3)15)11(16)6-12(10)18-13/h5-6,13-14,16H,1H2,2-4H3/t13-,14+/m0/s1
SMILES:	C=C(C)[C@H]1[C@@H](c2cc(C(=O)C)c(cc2O1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459268
PubChem CID:	15281118
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000119] Acetophenones

*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
NPO13981	Helianthella quinquenervis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882437]
NPO13981	Helianthella quinquenervis	Species	Asteraceae	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
ED50	3
IC50	2
Others	1

Activity Type	# Activity
Cell Line	3
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	34.0	ug ml-1	PMID[560075]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	16.0	ug ml-1	PMID[560075]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	31.0	ug ml-1	PMID[560075]
NPT140	Organism	Artemia	Artemia	LC50	=	68.0	ug.mL-1	PMID[560075]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	323.0	ug.mL-1	PMID[560075]
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	61.0	ug.mL-1	PMID[560075]

☑ 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 NPC171870 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	347
0.1-0.2	1430
0.2-0.3	3923
0.3-0.4	9387
0.4-0.5	9140
0.5-0.6	3595
0.6-0.7	5742
0.7-0.8	5535
0.8-0.85	2236
0.85-0.9	1066
0.9-0.95	293
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC37206
0.9562	High Similarity	NPC137009
0.9504	High Similarity	NPC202494
0.95	High Similarity	NPC297788
0.95	High Similarity	NPC470857
0.9496	High Similarity	NPC130206
0.9441	High Similarity	NPC472421
0.9424	High Similarity	NPC74397
0.9407	High Similarity	NPC247743
0.9375	High Similarity	NPC472423
0.9375	High Similarity	NPC474772
0.9375	High Similarity	NPC472580
0.9375	High Similarity	NPC474744
0.9343	High Similarity	NPC156910
0.931	High Similarity	NPC31627
0.931	High Similarity	NPC477957
0.931	High Similarity	NPC476238
0.931	High Similarity	NPC285623
0.931	High Similarity	NPC327269
0.931	High Similarity	NPC473996
0.9301	High Similarity	NPC168085
0.9281	High Similarity	NPC471697
0.9281	High Similarity	NPC139554
0.927	High Similarity	NPC60667
0.927	High Similarity	NPC84699
0.9241	High Similarity	NPC471675
0.9241	High Similarity	NPC472636
0.9236	High Similarity	NPC317492
0.9231	High Similarity	NPC47388
0.9231	High Similarity	NPC473133
0.9231	High Similarity	NPC470670
0.9231	High Similarity	NPC85773
0.9231	High Similarity	NPC91902
0.9231	High Similarity	NPC14875
0.9225	High Similarity	NPC316535
0.9209	High Similarity	NPC131130
0.9203	High Similarity	NPC470398
0.9203	High Similarity	NPC470397
0.9203	High Similarity	NPC174999
0.9197	High Similarity	NPC164136
0.9197	High Similarity	NPC144027
0.9197	High Similarity	NPC125920
0.9197	High Similarity	NPC236974
0.9191	High Similarity	NPC203817
0.9172	High Similarity	NPC180351
0.9167	High Similarity	NPC10097
0.9155	High Similarity	NPC175504
0.9155	High Similarity	NPC143896
0.9155	High Similarity	NPC39329
0.9155	High Similarity	NPC221432
0.9155	High Similarity	NPC150408
0.9155	High Similarity	NPC91560
0.9155	High Similarity	NPC75049
0.9155	High Similarity	NPC68104
0.9155	High Similarity	NPC310130
0.9155	High Similarity	NPC169591
0.9155	High Similarity	NPC257097
0.9155	High Similarity	NPC164980
0.9155	High Similarity	NPC149026
0.9149	High Similarity	NPC156190
0.9149	High Similarity	NPC258630
0.9149	High Similarity	NPC166689
0.9149	High Similarity	NPC279650
0.9149	High Similarity	NPC17170
0.9149	High Similarity	NPC96408
0.9143	High Similarity	NPC23257
0.9124	High Similarity	NPC93756
0.9124	High Similarity	NPC108113
0.9118	High Similarity	NPC27490
0.9111	High Similarity	NPC84772
0.911	High Similarity	NPC472420
0.911	High Similarity	NPC263384
0.911	High Similarity	NPC244577
0.911	High Similarity	NPC472422
0.911	High Similarity	NPC471676
0.9103	High Similarity	NPC139966
0.9103	High Similarity	NPC296030
0.9103	High Similarity	NPC307052
0.9103	High Similarity	NPC39929
0.9097	High Similarity	NPC130581
0.9097	High Similarity	NPC12148
0.9091	High Similarity	NPC470890
0.9091	High Similarity	NPC473013
0.9091	High Similarity	NPC236766
0.9091	High Similarity	NPC197252
0.9091	High Similarity	NPC473015
0.9091	High Similarity	NPC209040
0.9091	High Similarity	NPC224714
0.9085	High Similarity	NPC265040
0.9085	High Similarity	NPC177354
0.9085	High Similarity	NPC64915
0.9085	High Similarity	NPC10937
0.9085	High Similarity	NPC228504
0.9085	High Similarity	NPC324436
0.9085	High Similarity	NPC220998
0.9085	High Similarity	NPC328164
0.9085	High Similarity	NPC66515
0.9085	High Similarity	NPC40833
0.9085	High Similarity	NPC182852
0.9085	High Similarity	NPC296917
0.9085	High Similarity	NPC148757
0.9085	High Similarity	NPC306829
0.9085	High Similarity	NPC276565
0.9085	High Similarity	NPC166934
0.9085	High Similarity	NPC1089
0.9085	High Similarity	NPC194432
0.9085	High Similarity	NPC125855
0.9085	High Similarity	NPC167624
0.9085	High Similarity	NPC107572
0.9085	High Similarity	NPC324134
0.9085	High Similarity	NPC76338
0.9085	High Similarity	NPC32739
0.9085	High Similarity	NPC76372
0.9085	High Similarity	NPC227579
0.9085	High Similarity	NPC161506
0.9085	High Similarity	NPC37496
0.9085	High Similarity	NPC78
0.9085	High Similarity	NPC166482
0.9085	High Similarity	NPC223500
0.9078	High Similarity	NPC307990
0.9078	High Similarity	NPC28337
0.9078	High Similarity	NPC16455
0.9078	High Similarity	NPC470856
0.9078	High Similarity	NPC471587
0.9071	High Similarity	NPC470672
0.9071	High Similarity	NPC124269
0.9071	High Similarity	NPC470671
0.9071	High Similarity	NPC474487
0.9071	High Similarity	NPC474504
0.9071	High Similarity	NPC470399
0.9065	High Similarity	NPC187826
0.9048	High Similarity	NPC243171
0.9048	High Similarity	NPC256141
0.9048	High Similarity	NPC171651
0.9048	High Similarity	NPC35567
0.9044	High Similarity	NPC324482
0.9041	High Similarity	NPC321896
0.9041	High Similarity	NPC476185
0.9037	High Similarity	NPC230818
0.9034	High Similarity	NPC135325
0.9028	High Similarity	NPC187282
0.9028	High Similarity	NPC300267
0.9028	High Similarity	NPC210826
0.9028	High Similarity	NPC474302
0.9028	High Similarity	NPC472629
0.9028	High Similarity	NPC316769
0.9028	High Similarity	NPC290133
0.9028	High Similarity	NPC24136
0.9028	High Similarity	NPC51641
0.9021	High Similarity	NPC316816
0.9021	High Similarity	NPC125894
0.9021	High Similarity	NPC278249
0.9021	High Similarity	NPC77794
0.9021	High Similarity	NPC107177
0.9021	High Similarity	NPC255133
0.9021	High Similarity	NPC18886
0.9021	High Similarity	NPC166138
0.9021	High Similarity	NPC18585
0.9021	High Similarity	NPC478086
0.9021	High Similarity	NPC106985
0.9021	High Similarity	NPC223812
0.9021	High Similarity	NPC242100
0.9021	High Similarity	NPC185276
0.9021	High Similarity	NPC81697
0.9021	High Similarity	NPC214166
0.9021	High Similarity	NPC85162
0.9014	High Similarity	NPC110038
0.9014	High Similarity	NPC3188
0.9014	High Similarity	NPC4743
0.9014	High Similarity	NPC470089
0.9014	High Similarity	NPC324386
0.9014	High Similarity	NPC312391
0.9014	High Similarity	NPC470087
0.9014	High Similarity	NPC213322
0.9014	High Similarity	NPC110969
0.9014	High Similarity	NPC248372
0.9014	High Similarity	NPC321980
0.9007	High Similarity	NPC470211
0.9007	High Similarity	NPC140890
0.9007	High Similarity	NPC473076
0.9	High Similarity	NPC188879
0.8993	High Similarity	NPC151113
0.8986	High Similarity	NPC223701
0.8986	High Similarity	NPC469405
0.8986	High Similarity	NPC223457
0.8986	High Similarity	NPC122365
0.8986	High Similarity	NPC293286
0.8986	High Similarity	NPC7989
0.8986	High Similarity	NPC472583
0.898	High Similarity	NPC262038
0.898	High Similarity	NPC319910
0.898	High Similarity	NPC262039
0.898	High Similarity	NPC318424
0.898	High Similarity	NPC474021
0.898	High Similarity	NPC278476
0.898	High Similarity	NPC471677
0.898	High Similarity	NPC254412
0.898	High Similarity	NPC474023
0.8978	High Similarity	NPC31872
0.8978	High Similarity	NPC475589

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 NPC171870 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	921
0.2-0.3	1806
0.3-0.4	2568
0.4-0.5	1827
0.5-0.6	1109
0.6-0.7	433
0.7-0.8	138
0.8-0.85	29
0.85-0.9	14
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8936	High Similarity	NPD1549	Phase 2
0.8865	High Similarity	NPD1552	Clinical (unspecified phase)
0.8865	High Similarity	NPD1550	Clinical (unspecified phase)
0.8828	High Similarity	NPD4378	Clinical (unspecified phase)
0.8808	High Similarity	NPD7075	Discontinued
0.8784	High Similarity	NPD4380	Phase 2
0.8733	High Similarity	NPD2393	Clinical (unspecified phase)
0.8733	High Similarity	NPD7096	Clinical (unspecified phase)
0.8723	High Similarity	NPD1510	Phase 2
0.8705	High Similarity	NPD1240	Approved
0.8662	High Similarity	NPD2796	Approved
0.8618	High Similarity	NPD3882	Suspended
0.8611	High Similarity	NPD2800	Approved
0.8582	High Similarity	NPD1607	Approved
0.8571	High Similarity	NPD7410	Clinical (unspecified phase)
0.8553	High Similarity	NPD8443	Clinical (unspecified phase)
0.8543	High Similarity	NPD6801	Discontinued
0.8543	High Similarity	NPD1934	Approved
0.8503	High Similarity	NPD6799	Approved
0.8483	Intermediate Similarity	NPD1243	Approved
0.8477	Intermediate Similarity	NPD7411	Suspended
0.8446	Intermediate Similarity	NPD2532	Approved
0.8446	Intermediate Similarity	NPD2534	Approved
0.8446	Intermediate Similarity	NPD2533	Approved
0.8442	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD5494	Approved
0.8333	Intermediate Similarity	NPD920	Approved
0.8311	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD6599	Discontinued
0.8288	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1511	Approved
0.825	Intermediate Similarity	NPD3818	Discontinued
0.8247	Intermediate Similarity	NPD2801	Approved
0.82	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD6651	Approved
0.8165	Intermediate Similarity	NPD6959	Discontinued
0.816	Intermediate Similarity	NPD6559	Discontinued
0.8153	Intermediate Similarity	NPD919	Approved
0.8151	Intermediate Similarity	NPD1551	Phase 2
0.8146	Intermediate Similarity	NPD1512	Approved
0.8141	Intermediate Similarity	NPD7768	Phase 2
0.8125	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD6166	Phase 2
0.8108	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1247	Approved
0.8025	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3749	Approved
0.7974	Intermediate Similarity	NPD5403	Approved
0.7973	Intermediate Similarity	NPD2344	Approved
0.7962	Intermediate Similarity	NPD3817	Phase 2
0.7933	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD4628	Phase 3
0.7933	Intermediate Similarity	NPD3750	Approved
0.7927	Intermediate Similarity	NPD7074	Phase 3
0.7917	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD2935	Discontinued
0.7892	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD5953	Discontinued
0.7867	Intermediate Similarity	NPD2654	Approved
0.7866	Intermediate Similarity	NPD7054	Approved
0.7857	Intermediate Similarity	NPD9717	Approved
0.7843	Intermediate Similarity	NPD5401	Approved
0.7838	Intermediate Similarity	NPD2799	Discontinued
0.7818	Intermediate Similarity	NPD7472	Approved
0.7818	Intermediate Similarity	NPD1729	Discontinued
0.7778	Intermediate Similarity	NPD6232	Discontinued
0.7771	Intermediate Similarity	NPD6797	Phase 2
0.7763	Intermediate Similarity	NPD2309	Approved
0.7758	Intermediate Similarity	NPD5844	Phase 1
0.7758	Intermediate Similarity	NPD7286	Phase 2
0.7755	Intermediate Similarity	NPD230	Phase 1
0.7744	Intermediate Similarity	NPD7473	Discontinued
0.7736	Intermediate Similarity	NPD5402	Approved
0.773	Intermediate Similarity	NPD3926	Phase 2
0.7725	Intermediate Similarity	NPD7251	Discontinued
0.7718	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1203	Approved
0.7687	Intermediate Similarity	NPD943	Approved
0.7679	Intermediate Similarity	NPD7808	Phase 3
0.7669	Intermediate Similarity	NPD5710	Approved
0.7669	Intermediate Similarity	NPD5711	Approved
0.766	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD447	Suspended
0.7626	Intermediate Similarity	NPD9545	Approved
0.76	Intermediate Similarity	NPD3748	Approved
0.7582	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD2313	Discontinued
0.7551	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6099	Approved
0.755	Intermediate Similarity	NPD6100	Approved
0.7535	Intermediate Similarity	NPD422	Phase 1
0.7534	Intermediate Similarity	NPD6832	Phase 2
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7033	Discontinued
0.7482	Intermediate Similarity	NPD9493	Approved
0.747	Intermediate Similarity	NPD2403	Approved
0.7458	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1465	Phase 2
0.7451	Intermediate Similarity	NPD2424	Discontinued
0.7432	Intermediate Similarity	NPD411	Approved
0.7421	Intermediate Similarity	NPD3226	Approved
0.7415	Intermediate Similarity	NPD4908	Phase 1
0.7413	Intermediate Similarity	NPD1610	Phase 2
0.7401	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD4361	Phase 2
0.74	Intermediate Similarity	NPD5124	Phase 1
0.74	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1019	Discontinued
0.7391	Intermediate Similarity	NPD1241	Discontinued
0.7386	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6002	Phase 3
0.7386	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6004	Phase 3
0.7386	Intermediate Similarity	NPD6005	Phase 3
0.7376	Intermediate Similarity	NPD1548	Phase 1
0.7368	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD9494	Approved
0.7345	Intermediate Similarity	NPD4360	Phase 2
0.7345	Intermediate Similarity	NPD4363	Phase 3
0.7333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1613	Approved
0.7325	Intermediate Similarity	NPD7390	Discontinued
0.7315	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7458	Discontinued
0.7285	Intermediate Similarity	NPD6355	Discontinued
0.7279	Intermediate Similarity	NPD2798	Approved
0.7278	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1471	Phase 3
0.7238	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6104	Discontinued
0.7209	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1296	Phase 2
0.72	Intermediate Similarity	NPD3268	Approved
0.72	Intermediate Similarity	NPD6798	Discontinued
0.72	Intermediate Similarity	NPD8434	Phase 2
0.7195	Intermediate Similarity	NPD2296	Approved
0.7189	Intermediate Similarity	NPD7584	Approved
0.7186	Intermediate Similarity	NPD7199	Phase 2
0.7181	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1652	Phase 2
0.7178	Intermediate Similarity	NPD37	Approved
0.7171	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1933	Approved
0.717	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4662	Approved
0.717	Intermediate Similarity	NPD4661	Approved
0.7169	Intermediate Similarity	NPD6234	Discontinued
0.7152	Intermediate Similarity	NPD4965	Approved
0.7152	Intermediate Similarity	NPD4967	Phase 2
0.7152	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7134	Intermediate Similarity	NPD5760	Phase 2
0.7134	Intermediate Similarity	NPD5761	Phase 2
0.7133	Intermediate Similarity	NPD3027	Phase 3
0.7126	Intermediate Similarity	NPD8313	Approved
0.7126	Intermediate Similarity	NPD8312	Approved
0.7123	Intermediate Similarity	NPD1608	Approved
0.7123	Intermediate Similarity	NPD3972	Approved
0.7101	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1164	Approved
0.7095	Intermediate Similarity	NPD2797	Approved
0.7089	Intermediate Similarity	NPD3887	Approved
0.7086	Intermediate Similarity	NPD3764	Approved
0.7086	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD3751	Discontinued
0.7075	Intermediate Similarity	NPD4749	Approved
0.7073	Intermediate Similarity	NPD6279	Approved
0.7073	Intermediate Similarity	NPD6280	Approved
0.7059	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5647	Approved
0.7041	Intermediate Similarity	NPD6808	Phase 2
0.7037	Intermediate Similarity	NPD1653	Approved
0.7034	Intermediate Similarity	NPD1778	Approved
0.7022	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD4287	Approved
0.702	Intermediate Similarity	NPD4625	Phase 3
0.7019	Intermediate Similarity	NPD5049	Phase 3
0.7007	Intermediate Similarity	NPD9269	Phase 2
0.6993	Remote Similarity	NPD4060	Phase 1
0.6993	Remote Similarity	NPD3142	Approved
0.6993	Remote Similarity	NPD3140	Approved
0.6988	Remote Similarity	NPD4288	Approved
0.6988	Remote Similarity	NPD5353	Approved
0.6981	Remote Similarity	NPD2354	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