NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	232.11
Volume:	246.776
LogP:	3.106
LogD:	2.686
LogS:	-3.761
# Rotatable Bonds:	3
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	2.902
Fsp3:	0.357
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.565
MDCK Permeability:	1.5001348401710857e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.872
Plasma Protein Binding (PPB):	84.43697357177734%
Volume Distribution (VD):	1.232
Pgp-substrate:	9.441497802734375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.91
CYP1A2-substrate:	0.93
CYP2C19-inhibitor:	0.856
CYP2C19-substrate:	0.781
CYP2C9-inhibitor:	0.346
CYP2C9-substrate:	0.848
CYP2D6-inhibitor:	0.111
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.073
CYP3A4-substrate:	0.442

ADMET: Excretion

Clearance (CL):	7.874
Half-life (T1/2):	0.31

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.834
Drug-inuced Liver Injury (DILI):	0.826
AMES Toxicity:	0.476
Rat Oral Acute Toxicity:	0.092
Maximum Recommended Daily Dose:	0.788
Skin Sensitization:	0.062
Carcinogencity:	0.897
Eye Corrosion:	0.071
Eye Irritation:	0.777
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC247743

Natural Product ID:	NPC247743
*Common Name:**	6-Methoxy-Tremetone
IUPAC Name:	1-[(2R)-6-methoxy-2-prop-1-en-2-yl-2,3-dihydro-1-benzofuran-5-yl]ethanone
Synonyms:	6-Methoxy-Tremetone
Standard InCHIKey:	IYMJMWNDRCWQPW-GFCCVEGCSA-N
Standard InCHI:	InChI=1S/C14H16O3/c1-8(2)12-6-10-5-11(9(3)15)14(16-4)7-13(10)17-12/h5,7,12H,1,6H2,2-4H3/t12-/m1/s1
SMILES:	C=C(C)[C@H]1Cc2cc(C(=O)C)c(cc2O1)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL459267
PubChem CID:	10585660
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
NPO17812	Jatropha neopauciflora	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17125233]
NPO24286	Micromonospora lupini	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17475486]
NPO21731	Acanthella cavernosa	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	PMID[2045823]
NPO24286	Micromonospora lupini	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21226490]
NPO13981	Helianthella quinquenervis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882437]
NPO20119	Aconitum sungpanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24200	Piper angustifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24200	Piper angustifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20119	Aconitum sungpanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20119	Aconitum sungpanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO6174	Croton malambo	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24200	Piper angustifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23806	Polygala triphylla	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21430	Myctophum asperum	Species	Myctophidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21440	Trixis wrightii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17273	Empedobacter haloabium	Species	Flavobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20119	Aconitum sungpanense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14151	Macaca fascicularis	Species	Cercopithecidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24420	Aria japonica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21731	Acanthella cavernosa	Species	Axinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24286	Micromonospora lupini	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7123	Aria intermedia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23983	Siphonoglossa buchii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23661	Spiraea koreana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23937	0tholaena pallens	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17812	Jatropha neopauciflora	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13981	Helianthella quinquenervis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4721	Amphiachyris dracunculoides	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	=	33.0	ug ml-1	PMID[480173]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	16.0	ug ml-1	PMID[480173]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	1.0	ug ml-1	PMID[480173]
NPT140	Organism	Artemia	Artemia	LC50	=	8.0	ug.mL-1	PMID[480173]
NPT117	Organism	Echinochloa crus-galli	Echinochloa crus-galli	IC50	=	68.0	ug.mL-1	PMID[480173]
NPT965	Organism	Amaranthus hypochondriacus	Amaranthus hypochondriacus	IC50	=	11.0	ug.mL-1	PMID[480173]

☑ 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 NPC247743 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	401
0.1-0.2	1671
0.2-0.3	4369
0.3-0.4	11005
0.4-0.5	7395
0.5-0.6	4265
0.6-0.7	6414
0.7-0.8	5031
0.8-0.85	1491
0.85-0.9	625
0.9-0.95	29
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9478	High Similarity	NPC470856
0.9407	High Similarity	NPC171870
0.9403	High Similarity	NPC137009
0.9403	High Similarity	NPC37206
0.9323	High Similarity	NPC29638
0.9313	High Similarity	NPC229646
0.9118	High Similarity	NPC11566
0.9111	High Similarity	NPC259685
0.9077	High Similarity	NPC473907
0.9051	High Similarity	NPC472409
0.9044	High Similarity	NPC36414
0.9037	High Similarity	NPC268081
0.9037	High Similarity	NPC254741
0.9037	High Similarity	NPC156910
0.9008	High Similarity	NPC473894
0.9007	High Similarity	NPC168085
0.9	High Similarity	NPC49852
0.9	High Similarity	NPC475496
0.8993	High Similarity	NPC17262
0.8992	High Similarity	NPC470858
0.8992	High Similarity	NPC65041
0.8984	High Similarity	NPC141252
0.8984	High Similarity	NPC11799
0.8978	High Similarity	NPC139554
0.8978	High Similarity	NPC262635
0.8971	High Similarity	NPC253616
0.8963	High Similarity	NPC60667
0.8963	High Similarity	NPC99854
0.8963	High Similarity	NPC84699
0.8963	High Similarity	NPC46869
0.8955	High Similarity	NPC292998
0.8947	High Similarity	NPC470859
0.8944	High Similarity	NPC317492
0.8936	High Similarity	NPC202494
0.8936	High Similarity	NPC471285
0.8929	High Similarity	NPC171656
0.8929	High Similarity	NPC297788
0.8929	High Similarity	NPC470857
0.8921	High Similarity	NPC147145
0.8921	High Similarity	NPC130206
0.8913	High Similarity	NPC28337
0.8905	High Similarity	NPC131130
0.8897	High Similarity	NPC470398
0.8897	High Similarity	NPC161196
0.8897	High Similarity	NPC174999
0.8897	High Similarity	NPC470397
0.8889	High Similarity	NPC164136
0.8889	High Similarity	NPC144027
0.8889	High Similarity	NPC125920
0.8889	High Similarity	NPC236974
0.8889	High Similarity	NPC125269
0.8881	High Similarity	NPC203817
0.8881	High Similarity	NPC472421
0.8865	High Similarity	NPC300267
0.8865	High Similarity	NPC51641
0.8865	High Similarity	NPC190572
0.8864	High Similarity	NPC170546
0.8864	High Similarity	NPC66246
0.8857	High Similarity	NPC310130
0.8857	High Similarity	NPC169591
0.8857	High Similarity	NPC150408
0.8857	High Similarity	NPC257097
0.8857	High Similarity	NPC164980
0.8857	High Similarity	NPC59522
0.8857	High Similarity	NPC68104
0.8857	High Similarity	NPC221432
0.8857	High Similarity	NPC175504
0.8857	High Similarity	NPC143896
0.8857	High Similarity	NPC91560
0.8857	High Similarity	NPC75049
0.8857	High Similarity	NPC149026
0.8857	High Similarity	NPC39329
0.8849	High Similarity	NPC166689
0.8849	High Similarity	NPC96408
0.8849	High Similarity	NPC156190
0.8849	High Similarity	NPC22467
0.8849	High Similarity	NPC279650
0.8849	High Similarity	NPC258630
0.8849	High Similarity	NPC74397
0.8849	High Similarity	NPC254010
0.8849	High Similarity	NPC17170
0.8841	High Similarity	NPC23257
0.8841	High Similarity	NPC472515
0.8832	High Similarity	NPC157855
0.8824	High Similarity	NPC151113
0.8819	High Similarity	NPC472423
0.8819	High Similarity	NPC474744
0.8819	High Similarity	NPC472580
0.8819	High Similarity	NPC474772
0.8815	High Similarity	NPC108113
0.8815	High Similarity	NPC93756
0.8815	High Similarity	NPC223354
0.8811	High Similarity	NPC296030
0.8811	High Similarity	NPC39929
0.8806	High Similarity	NPC27490
0.8806	High Similarity	NPC284424
0.8803	High Similarity	NPC12148
0.8803	High Similarity	NPC198427
0.8803	High Similarity	NPC130581
0.8797	High Similarity	NPC84772
0.8797	High Similarity	NPC183348
0.8797	High Similarity	NPC282230
0.8794	High Similarity	NPC473015
0.8794	High Similarity	NPC179970
0.8794	High Similarity	NPC87486
0.8794	High Similarity	NPC209040
0.8794	High Similarity	NPC294365
0.8794	High Similarity	NPC224714
0.8794	High Similarity	NPC470890
0.8794	High Similarity	NPC473013
0.8794	High Similarity	NPC197252
0.8794	High Similarity	NPC236766
0.8794	High Similarity	NPC124780
0.8786	High Similarity	NPC227579
0.8786	High Similarity	NPC10937
0.8786	High Similarity	NPC148757
0.8786	High Similarity	NPC125855
0.8786	High Similarity	NPC223500
0.8786	High Similarity	NPC167624
0.8786	High Similarity	NPC107572
0.8786	High Similarity	NPC265040
0.8786	High Similarity	NPC194432
0.8786	High Similarity	NPC40833
0.8786	High Similarity	NPC1089
0.8786	High Similarity	NPC76372
0.8786	High Similarity	NPC161506
0.8786	High Similarity	NPC66515
0.8786	High Similarity	NPC51146
0.8786	High Similarity	NPC313036
0.8786	High Similarity	NPC324436
0.8786	High Similarity	NPC32739
0.8786	High Similarity	NPC166858
0.8786	High Similarity	NPC328164
0.8786	High Similarity	NPC324134
0.8786	High Similarity	NPC228504
0.8786	High Similarity	NPC78
0.8786	High Similarity	NPC166482
0.8786	High Similarity	NPC220998
0.8786	High Similarity	NPC182852
0.8786	High Similarity	NPC296917
0.8786	High Similarity	NPC37496
0.8786	High Similarity	NPC166934
0.8786	High Similarity	NPC177354
0.8786	High Similarity	NPC64915
0.8786	High Similarity	NPC306829
0.8786	High Similarity	NPC76338
0.8777	High Similarity	NPC471587
0.8777	High Similarity	NPC307990
0.8777	High Similarity	NPC16455
0.8769	High Similarity	NPC255073
0.8768	High Similarity	NPC470672
0.8768	High Similarity	NPC17848
0.8768	High Similarity	NPC470399
0.8768	High Similarity	NPC124269
0.8768	High Similarity	NPC470671
0.8768	High Similarity	NPC474504
0.8768	High Similarity	NPC474487
0.8759	High Similarity	NPC476238
0.8759	High Similarity	NPC285623
0.8759	High Similarity	NPC327269
0.8759	High Similarity	NPC472516
0.8759	High Similarity	NPC240593
0.8759	High Similarity	NPC477957
0.8759	High Similarity	NPC31627
0.8759	High Similarity	NPC187826
0.8759	High Similarity	NPC473996
0.875	High Similarity	NPC472406
0.875	High Similarity	NPC321896
0.875	High Similarity	NPC191104
0.875	High Similarity	NPC476185
0.8741	High Similarity	NPC101294
0.8741	High Similarity	NPC266743
0.8741	High Similarity	NPC182428
0.8741	High Similarity	NPC135325
0.8741	High Similarity	NPC473655
0.8732	High Similarity	NPC210826
0.8732	High Similarity	NPC187282
0.8732	High Similarity	NPC290133
0.8732	High Similarity	NPC472629
0.8732	High Similarity	NPC474302
0.8732	High Similarity	NPC24136
0.8731	High Similarity	NPC15083
0.8731	High Similarity	NPC470976
0.8731	High Similarity	NPC470977
0.8731	High Similarity	NPC324482
0.8731	High Similarity	NPC196979
0.8723	High Similarity	NPC85162
0.8723	High Similarity	NPC106985
0.8723	High Similarity	NPC107177
0.8723	High Similarity	NPC166138
0.8723	High Similarity	NPC278249
0.8723	High Similarity	NPC223812
0.8723	High Similarity	NPC478086
0.8723	High Similarity	NPC225884
0.8723	High Similarity	NPC214166
0.8723	High Similarity	NPC77794
0.8723	High Similarity	NPC316816
0.8723	High Similarity	NPC185276
0.8723	High Similarity	NPC125894
0.8723	High Similarity	NPC18585

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 NPC247743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	1018
0.2-0.3	1734
0.3-0.4	2711
0.4-0.5	1715
0.5-0.6	1090
0.6-0.7	368
0.7-0.8	120
0.8-0.85	29
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9179	High Similarity	NPD2796	Approved
0.8978	High Similarity	NPD1243	Approved
0.8786	High Similarity	NPD643	Clinical (unspecified phase)
0.8671	High Similarity	NPD920	Approved
0.8662	High Similarity	NPD642	Clinical (unspecified phase)
0.8633	High Similarity	NPD1549	Phase 2
0.8561	High Similarity	NPD1550	Clinical (unspecified phase)
0.8561	High Similarity	NPD1552	Clinical (unspecified phase)
0.8531	High Similarity	NPD4378	Clinical (unspecified phase)
0.8529	High Similarity	NPD1240	Approved
0.8446	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD1510	Phase 2
0.8411	Intermediate Similarity	NPD5494	Approved
0.8406	Intermediate Similarity	NPD1607	Approved
0.8333	Intermediate Similarity	NPD6799	Approved
0.8322	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD7819	Suspended
0.8311	Intermediate Similarity	NPD7411	Suspended
0.831	Intermediate Similarity	NPD2800	Approved
0.8278	Intermediate Similarity	NPD7075	Discontinued
0.8276	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD6801	Discontinued
0.8243	Intermediate Similarity	NPD4380	Phase 2
0.8224	Intermediate Similarity	NPD919	Approved
0.8182	Intermediate Similarity	NPD2654	Approved
0.8151	Intermediate Similarity	NPD2532	Approved
0.8151	Intermediate Similarity	NPD2533	Approved
0.8151	Intermediate Similarity	NPD2534	Approved
0.8121	Intermediate Similarity	NPD6599	Discontinued
0.812	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD1247	Approved
0.8092	Intermediate Similarity	NPD3882	Suspended
0.8013	Intermediate Similarity	NPD1934	Approved
0.7986	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD3748	Approved
0.7887	Intermediate Similarity	NPD6651	Approved
0.7885	Intermediate Similarity	NPD6959	Discontinued
0.7857	Intermediate Similarity	NPD7768	Phase 2
0.7857	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD1551	Phase 2
0.7846	Intermediate Similarity	NPD1241	Discontinued
0.7842	Intermediate Similarity	NPD6832	Phase 2
0.7838	Intermediate Similarity	NPD1511	Approved
0.7793	Intermediate Similarity	NPD2344	Approved
0.7792	Intermediate Similarity	NPD3817	Phase 2
0.7785	Intermediate Similarity	NPD3926	Phase 2
0.7778	Intermediate Similarity	NPD2799	Discontinued
0.775	Intermediate Similarity	NPD3818	Discontinued
0.7733	Intermediate Similarity	NPD1512	Approved
0.7727	Intermediate Similarity	NPD2801	Approved
0.7702	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD1019	Discontinued
0.7692	Intermediate Similarity	NPD3749	Approved
0.7682	Intermediate Similarity	NPD5403	Approved
0.7669	Intermediate Similarity	NPD6559	Discontinued
0.7667	Intermediate Similarity	NPD5401	Approved
0.7664	Intermediate Similarity	NPD9717	Approved
0.7654	Intermediate Similarity	NPD1729	Discontinued
0.7635	Intermediate Similarity	NPD3750	Approved
0.7635	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6166	Phase 2
0.7625	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD5953	Discontinued
0.7603	Intermediate Similarity	NPD2935	Discontinued
0.7584	Intermediate Similarity	NPD2309	Approved
0.7566	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1471	Phase 3
0.7536	Intermediate Similarity	NPD3972	Approved
0.7531	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD4628	Phase 3
0.7516	Intermediate Similarity	NPD2403	Approved
0.7516	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7286	Phase 2
0.7483	Intermediate Similarity	NPD1296	Phase 2
0.7483	Intermediate Similarity	NPD2313	Discontinued
0.7452	Intermediate Similarity	NPD5402	Approved
0.7448	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD2798	Approved
0.7439	Intermediate Similarity	NPD7074	Phase 3
0.7436	Intermediate Similarity	NPD6280	Approved
0.7436	Intermediate Similarity	NPD6279	Approved
0.7426	Intermediate Similarity	NPD9545	Approved
0.7415	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5711	Approved
0.7391	Intermediate Similarity	NPD5710	Approved
0.7379	Intermediate Similarity	NPD3140	Approved
0.7379	Intermediate Similarity	NPD3142	Approved
0.7378	Intermediate Similarity	NPD7054	Approved
0.7378	Intermediate Similarity	NPD5844	Phase 1
0.7376	Intermediate Similarity	NPD1203	Approved
0.7365	Intermediate Similarity	NPD6099	Approved
0.7365	Intermediate Similarity	NPD6100	Approved
0.7338	Intermediate Similarity	NPD422	Phase 1
0.7333	Intermediate Similarity	NPD7472	Approved
0.7329	Intermediate Similarity	NPD230	Phase 1
0.7319	Intermediate Similarity	NPD17	Approved
0.7315	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1876	Approved
0.7297	Intermediate Similarity	NPD7033	Discontinued
0.7289	Intermediate Similarity	NPD6797	Phase 2
0.7285	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6808	Phase 2
0.7284	Intermediate Similarity	NPD6232	Discontinued
0.7279	Intermediate Similarity	NPD9493	Approved
0.726	Intermediate Similarity	NPD943	Approved
0.7256	Intermediate Similarity	NPD7473	Discontinued
0.7246	Intermediate Similarity	NPD7251	Discontinued
0.7244	Intermediate Similarity	NPD3226	Approved
0.7241	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD411	Approved
0.7214	Intermediate Similarity	NPD1610	Phase 2
0.7211	Intermediate Similarity	NPD447	Suspended
0.7211	Intermediate Similarity	NPD5124	Phase 1
0.7211	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1933	Approved
0.7202	Intermediate Similarity	NPD7808	Phase 3
0.72	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6005	Phase 3
0.72	Intermediate Similarity	NPD2346	Discontinued
0.72	Intermediate Similarity	NPD6002	Phase 3
0.72	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6004	Phase 3
0.7174	Intermediate Similarity	NPD1548	Phase 1
0.7163	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD5889	Approved
0.7152	Intermediate Similarity	NPD5890	Approved
0.7152	Intermediate Similarity	NPD2424	Discontinued
0.7143	Intermediate Similarity	NPD4307	Phase 2
0.7143	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6104	Discontinued
0.7143	Intermediate Similarity	NPD4361	Phase 2
0.7133	Intermediate Similarity	NPD3266	Approved
0.7133	Intermediate Similarity	NPD3267	Approved
0.7124	Intermediate Similarity	NPD3887	Approved
0.7122	Intermediate Similarity	NPD1651	Approved
0.7122	Intermediate Similarity	NPD5691	Approved
0.7103	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4908	Phase 1
0.7101	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4662	Approved
0.7097	Intermediate Similarity	NPD4661	Approved
0.7091	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4363	Phase 3
0.7086	Intermediate Similarity	NPD4360	Phase 2
0.7083	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7229	Phase 3
0.7071	Intermediate Similarity	NPD1778	Approved
0.7044	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7390	Discontinued
0.7019	Intermediate Similarity	NPD5353	Approved
0.7019	Intermediate Similarity	NPD2296	Approved
0.7014	Intermediate Similarity	NPD2797	Approved
0.7007	Intermediate Similarity	NPD3268	Approved
0.7006	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6585	Discontinued
0.698	Remote Similarity	NPD6355	Discontinued
0.6957	Remote Similarity	NPD1465	Phase 2
0.6957	Remote Similarity	NPD5760	Phase 2
0.6957	Remote Similarity	NPD5761	Phase 2
0.6954	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4308	Phase 3
0.6947	Remote Similarity	NPD9261	Approved
0.6943	Remote Similarity	NPD6273	Approved
0.6918	Remote Similarity	NPD9494	Approved
0.6918	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7458	Discontinued
0.6917	Remote Similarity	NPD3134	Approved
0.6914	Remote Similarity	NPD4288	Approved
0.6909	Remote Similarity	NPD7199	Phase 2
0.6908	Remote Similarity	NPD4476	Approved
0.6908	Remote Similarity	NPD4477	Approved
0.6903	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1164	Approved
0.6892	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6798	Discontinued
0.6883	Remote Similarity	NPD1652	Phase 2
0.6875	Remote Similarity	NPD4749	Approved
0.6871	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD1358	Approved
0.6863	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2353	Approved
0.6853	Remote Similarity	NPD1281	Approved
0.6839	Remote Similarity	NPD8434	Phase 2
0.6839	Remote Similarity	NPD7003	Approved
0.6838	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2186	Approved
0.6831	Remote Similarity	NPD4626	Approved
0.6826	Remote Similarity	NPD5242	Approved
0.6826	Remote Similarity	NPD7184	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