NPASS Compound

Structure

NPC179732 OpenBabel07101718222D 22 23 0 0 1 0 0 0 0 0999 V2000 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 22 1 0 0 0 0 3 6 1 0 0 0 0 4 9 2 0 0 0 0 4 10 1 0 0 0 0 5 16 1 0 0 0 0 6 17 2 0 0 0 0 7 3 1 6 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 5 1 6 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 18 1 0 0 0 0 10 15 2 0 0 0 0 10 22 1 0 0 0 0 11 12 2 0 0 0 0 11 14 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 19 1 6 0 0 0 14 20 2 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.11
Volume:	299.233
LogP:	-0.248
LogD:	-0.117
LogS:	-1.772
# Rotatable Bonds:	4
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.592
Synthetic Accessibility Score:	4.021
Fsp3:	0.467
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:	-5.647
MDCK Permeability:	3.45174908034096e-06
Pgp-inhibitor:	0.016
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.477
20% Bioavailability (F20%):	0.494
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	43.1308479309082%
Volume Distribution (VD):	0.964
Pgp-substrate:	49.72709274291992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.09
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.375
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.468
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.187
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.24

ADMET: Excretion

Clearance (CL):	4.326
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.105
Human Hepatotoxicity (H-HT):	0.14
Drug-inuced Liver Injury (DILI):	0.827
AMES Toxicity:	0.425
Rat Oral Acute Toxicity:	0.066
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.58
Carcinogencity:	0.024
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.079

Download Data

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

Natural Product: NPC179732

Natural Product ID:	NPC179732
*Common Name:**	Fusarnaphthoquinone A
IUPAC Name:	(2S,3S,4S)-4,5,8-trihydroxy-2-(hydroxymethyl)-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2H-naphthalen-1-one
Synonyms:
Standard InCHIKey:	WUEWJCUSVRCGFI-DAROEXNTSA-N
Standard InCHI:	InChI=1S/C15H18O7/c1-6(17)3-7-8(5-16)14(20)11-9(18)4-10(22-2)15(21)12(11)13(7)19/h4,7-8,13,16,18-19,21H,3,5H2,1-2H3/t7-,8+,13-/m0/s1
SMILES:	CC(=O)C[C@H]1[C@@H](CO)C(=O)c2c(cc(c(c2[C@H]1O)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1224799
PubChem CID:	46938752
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO32910	fusarium spp. psu-f135	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815366]

☑ 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
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	130000.0	nM	PMID[453444]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	22000.0	nM	PMID[453444]

☑ 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 NPC179732 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	413
0.1-0.2	1604
0.2-0.3	4029
0.3-0.4	9709
0.4-0.5	8809
0.5-0.6	3688
0.6-0.7	5243
0.7-0.8	6863
0.8-0.85	1817
0.85-0.9	496
0.9-0.95	22
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC472048
0.9608	High Similarity	NPC161947
0.9608	High Similarity	NPC155302
0.9545	High Similarity	NPC87431
0.9484	High Similarity	NPC215612
0.9097	High Similarity	NPC234485
0.9097	High Similarity	NPC68727
0.9091	High Similarity	NPC470337
0.9091	High Similarity	NPC470338
0.9091	High Similarity	NPC51824
0.9091	High Similarity	NPC113608
0.9091	High Similarity	NPC268992
0.9057	High Similarity	NPC7483
0.9045	High Similarity	NPC477410
0.9045	High Similarity	NPC329091
0.9045	High Similarity	NPC45846
0.9038	High Similarity	NPC470762
0.9038	High Similarity	NPC474167
0.9032	High Similarity	NPC281477
0.9032	High Similarity	NPC127172
0.9006	High Similarity	NPC117854
0.9006	High Similarity	NPC477154
0.9006	High Similarity	NPC6588
0.9	High Similarity	NPC25361
0.9	High Similarity	NPC326520
0.8987	High Similarity	NPC228785
0.8987	High Similarity	NPC56085
0.8987	High Similarity	NPC14353
0.8987	High Similarity	NPC84571
0.8981	High Similarity	NPC300727
0.8981	High Similarity	NPC469584
0.8981	High Similarity	NPC78103
0.8981	High Similarity	NPC241904
0.8974	High Similarity	NPC82592
0.8974	High Similarity	NPC134287
0.8974	High Similarity	NPC16082
0.8974	High Similarity	NPC130589
0.8968	High Similarity	NPC180944
0.8968	High Similarity	NPC470340
0.8961	High Similarity	NPC103509
0.8954	High Similarity	NPC287395
0.8954	High Similarity	NPC183655
0.8947	High Similarity	NPC143903
0.8947	High Similarity	NPC226987
0.8944	High Similarity	NPC170245
0.8938	High Similarity	NPC236132
0.8938	High Similarity	NPC197168
0.8938	High Similarity	NPC475985
0.8938	High Similarity	NPC270837
0.8931	High Similarity	NPC40491
0.8931	High Similarity	NPC474186
0.8931	High Similarity	NPC278052
0.8931	High Similarity	NPC311740
0.8931	High Similarity	NPC61010
0.8924	High Similarity	NPC470339
0.8924	High Similarity	NPC476242
0.8924	High Similarity	NPC100123
0.8917	High Similarity	NPC317383
0.8917	High Similarity	NPC274730
0.8917	High Similarity	NPC164427
0.891	High Similarity	NPC250557
0.891	High Similarity	NPC124714
0.891	High Similarity	NPC273248
0.8903	High Similarity	NPC19980
0.8903	High Similarity	NPC45291
0.8902	High Similarity	NPC471969
0.8896	High Similarity	NPC102003
0.8896	High Similarity	NPC92722
0.8896	High Similarity	NPC134293
0.8875	High Similarity	NPC294965
0.8875	High Similarity	NPC48860
0.8868	High Similarity	NPC472055
0.8868	High Similarity	NPC475886
0.8868	High Similarity	NPC474287
0.8868	High Similarity	NPC320359
0.8868	High Similarity	NPC36217
0.8861	High Similarity	NPC472913
0.8861	High Similarity	NPC77679
0.8861	High Similarity	NPC96167
0.8861	High Similarity	NPC474836
0.8861	High Similarity	NPC245758
0.8861	High Similarity	NPC84935
0.8861	High Similarity	NPC162869
0.8861	High Similarity	NPC48208
0.8861	High Similarity	NPC37543
0.8861	High Similarity	NPC199463
0.8861	High Similarity	NPC472911
0.8861	High Similarity	NPC190020
0.8861	High Similarity	NPC475267
0.8861	High Similarity	NPC156057
0.8861	High Similarity	NPC472910
0.8861	High Similarity	NPC217677
0.8861	High Similarity	NPC470402
0.8861	High Similarity	NPC165977
0.8861	High Similarity	NPC472914
0.8861	High Similarity	NPC223787
0.8861	High Similarity	NPC222814
0.8861	High Similarity	NPC474208
0.8854	High Similarity	NPC79998
0.8854	High Similarity	NPC199926
0.8854	High Similarity	NPC175192
0.8854	High Similarity	NPC38898
0.8854	High Similarity	NPC39184
0.8846	High Similarity	NPC312338
0.8846	High Similarity	NPC181209
0.8846	High Similarity	NPC35763
0.8846	High Similarity	NPC100971
0.8846	High Similarity	NPC149889
0.8846	High Similarity	NPC121522
0.8846	High Similarity	NPC245382
0.8846	High Similarity	NPC209487
0.8846	High Similarity	NPC100263
0.8846	High Similarity	NPC269451
0.8846	High Similarity	NPC216769
0.8846	High Similarity	NPC161778
0.8846	High Similarity	NPC291802
0.8846	High Similarity	NPC131266
0.8839	High Similarity	NPC472279
0.8839	High Similarity	NPC239363
0.8839	High Similarity	NPC225854
0.8839	High Similarity	NPC216917
0.8831	High Similarity	NPC476058
0.8831	High Similarity	NPC474903
0.8831	High Similarity	NPC15329
0.8831	High Similarity	NPC131451
0.8827	High Similarity	NPC472452
0.882	High Similarity	NPC248638
0.882	High Similarity	NPC476822
0.882	High Similarity	NPC152659
0.882	High Similarity	NPC220313
0.882	High Similarity	NPC236521
0.882	High Similarity	NPC101769
0.8812	High Similarity	NPC474187
0.8812	High Similarity	NPC475883
0.8812	High Similarity	NPC258331
0.8812	High Similarity	NPC474351
0.8812	High Similarity	NPC266314
0.8812	High Similarity	NPC201560
0.8812	High Similarity	NPC66288
0.881	High Similarity	NPC182693
0.8805	High Similarity	NPC85121
0.8805	High Similarity	NPC250214
0.8805	High Similarity	NPC95936
0.8797	High Similarity	NPC255106
0.8797	High Similarity	NPC150227
0.8797	High Similarity	NPC5379
0.8797	High Similarity	NPC14561
0.8797	High Similarity	NPC469474
0.8797	High Similarity	NPC142339
0.8797	High Similarity	NPC235165
0.8797	High Similarity	NPC276815
0.8797	High Similarity	NPC25850
0.8797	High Similarity	NPC77807
0.879	High Similarity	NPC477047
0.879	High Similarity	NPC287504
0.879	High Similarity	NPC25127
0.879	High Similarity	NPC93552
0.879	High Similarity	NPC89474
0.879	High Similarity	NPC477048
0.8782	High Similarity	NPC202157
0.8782	High Similarity	NPC262623
0.8782	High Similarity	NPC171010
0.8782	High Similarity	NPC272566
0.8773	High Similarity	NPC474024
0.8773	High Similarity	NPC470456
0.8766	High Similarity	NPC93034
0.8766	High Similarity	NPC119660
0.8766	High Similarity	NPC61871
0.8766	High Similarity	NPC55557
0.8766	High Similarity	NPC30647
0.8765	High Similarity	NPC8070
0.8765	High Similarity	NPC472450
0.8765	High Similarity	NPC470457
0.8765	High Similarity	NPC473286
0.8765	High Similarity	NPC275780
0.8765	High Similarity	NPC239752
0.8765	High Similarity	NPC475888
0.8758	High Similarity	NPC220912
0.8758	High Similarity	NPC472917
0.8758	High Similarity	NPC211107
0.8758	High Similarity	NPC191360
0.8758	High Similarity	NPC472964
0.8758	High Similarity	NPC201800
0.8758	High Similarity	NPC25152
0.8758	High Similarity	NPC81679
0.875	High Similarity	NPC200746
0.875	High Similarity	NPC321399
0.875	High Similarity	NPC263449
0.875	High Similarity	NPC119224
0.875	High Similarity	NPC472902
0.8742	High Similarity	NPC474055
0.8742	High Similarity	NPC178976
0.8742	High Similarity	NPC236796
0.8742	High Similarity	NPC181960
0.8742	High Similarity	NPC262286
0.8742	High Similarity	NPC283301
0.8742	High Similarity	NPC299520
0.8742	High Similarity	NPC99597
0.8742	High Similarity	NPC36852
0.8742	High Similarity	NPC129684

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 NPC179732 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	371
0.1-0.2	1009
0.2-0.3	2070
0.3-0.4	2642
0.4-0.5	1682
0.5-0.6	868
0.6-0.7	376
0.7-0.8	115
0.8-0.85	14
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8671	High Similarity	NPD2801	Approved
0.8608	High Similarity	NPD1934	Approved
0.8553	High Similarity	NPD2393	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD7473	Discontinued
0.8415	Intermediate Similarity	NPD6232	Discontinued
0.8333	Intermediate Similarity	NPD3882	Suspended
0.8313	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6166	Phase 2
0.8293	Intermediate Similarity	NPD5494	Approved
0.8217	Intermediate Similarity	NPD1511	Approved
0.8214	Intermediate Similarity	NPD3818	Discontinued
0.8166	Intermediate Similarity	NPD5844	Phase 1
0.8137	Intermediate Similarity	NPD4380	Phase 2
0.8129	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7074	Phase 3
0.8113	Intermediate Similarity	NPD1512	Approved
0.8081	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7054	Approved
0.805	Intermediate Similarity	NPD2534	Approved
0.805	Intermediate Similarity	NPD2533	Approved
0.805	Intermediate Similarity	NPD2532	Approved
0.8024	Intermediate Similarity	NPD6959	Discontinued
0.8012	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD1465	Phase 2
0.7939	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3817	Phase 2
0.7935	Intermediate Similarity	NPD1510	Phase 2
0.7927	Intermediate Similarity	NPD37	Approved
0.7922	Intermediate Similarity	NPD1607	Approved
0.7917	Intermediate Similarity	NPD1247	Approved
0.7908	Intermediate Similarity	NPD943	Approved
0.7908	Intermediate Similarity	NPD1240	Approved
0.7904	Intermediate Similarity	NPD6234	Discontinued
0.7861	Intermediate Similarity	NPD6797	Phase 2
0.7834	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7251	Discontinued
0.7809	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1549	Phase 2
0.7784	Intermediate Similarity	NPD4965	Approved
0.7784	Intermediate Similarity	NPD4967	Phase 2
0.7784	Intermediate Similarity	NPD4966	Approved
0.7771	Intermediate Similarity	NPD7819	Suspended
0.7771	Intermediate Similarity	NPD7808	Phase 3
0.7742	Intermediate Similarity	NPD230	Phase 1
0.7738	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7075	Discontinued
0.7712	Intermediate Similarity	NPD3027	Phase 3
0.7711	Intermediate Similarity	NPD6801	Discontinued
0.7707	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7228	Approved
0.7665	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2935	Discontinued
0.7657	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2800	Approved
0.7624	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5402	Approved
0.759	Intermediate Similarity	NPD6599	Discontinued
0.758	Intermediate Similarity	NPD6651	Approved
0.7547	Intermediate Similarity	NPD2796	Approved
0.7546	Intermediate Similarity	NPD6799	Approved
0.7545	Intermediate Similarity	NPD7411	Suspended
0.7543	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD9494	Approved
0.7457	Intermediate Similarity	NPD5711	Approved
0.7457	Intermediate Similarity	NPD5710	Approved
0.7452	Intermediate Similarity	NPD1613	Approved
0.7452	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7390	Discontinued
0.7433	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD3226	Approved
0.7414	Intermediate Similarity	NPD3926	Phase 2
0.7399	Intermediate Similarity	NPD7199	Phase 2
0.7394	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD919	Approved
0.7371	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4628	Phase 3
0.734	Intermediate Similarity	NPD6779	Approved
0.734	Intermediate Similarity	NPD6776	Approved
0.734	Intermediate Similarity	NPD6780	Approved
0.734	Intermediate Similarity	NPD6781	Approved
0.734	Intermediate Similarity	NPD6778	Approved
0.734	Intermediate Similarity	NPD6782	Approved
0.734	Intermediate Similarity	NPD6777	Approved
0.7329	Intermediate Similarity	NPD6099	Approved
0.7329	Intermediate Similarity	NPD6100	Approved
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7308	Intermediate Similarity	NPD8434	Phase 2
0.7305	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD447	Suspended
0.7288	Intermediate Similarity	NPD3751	Discontinued
0.7262	Intermediate Similarity	NPD1653	Approved
0.7257	Intermediate Similarity	NPD3787	Discontinued
0.7256	Intermediate Similarity	NPD3750	Approved
0.7244	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD8313	Approved
0.7238	Intermediate Similarity	NPD8312	Approved
0.7225	Intermediate Similarity	NPD3749	Approved
0.7225	Intermediate Similarity	NPD7435	Discontinued
0.7222	Intermediate Similarity	NPD1551	Phase 2
0.7222	Intermediate Similarity	NPD7240	Approved
0.7216	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8151	Discontinued
0.7212	Intermediate Similarity	NPD6190	Approved
0.7202	Intermediate Similarity	NPD5403	Approved
0.7202	Intermediate Similarity	NPD920	Approved
0.7197	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD2403	Approved
0.7168	Intermediate Similarity	NPD7768	Phase 2
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7135	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD7698	Approved
0.7135	Intermediate Similarity	NPD7697	Approved
0.7127	Intermediate Similarity	NPD7685	Pre-registration
0.7125	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3620	Phase 2
0.7115	Intermediate Similarity	NPD1470	Approved
0.711	Intermediate Similarity	NPD5353	Approved
0.7098	Intermediate Similarity	NPD7870	Phase 2
0.7098	Intermediate Similarity	NPD7871	Phase 2
0.7097	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5401	Approved
0.7083	Intermediate Similarity	NPD6823	Phase 2
0.7078	Intermediate Similarity	NPD1201	Approved
0.7077	Intermediate Similarity	NPD7701	Phase 2
0.7074	Intermediate Similarity	NPD6534	Approved
0.7074	Intermediate Similarity	NPD6535	Approved
0.7073	Intermediate Similarity	NPD2346	Discontinued
0.7056	Intermediate Similarity	NPD7801	Approved
0.7056	Intermediate Similarity	NPD7286	Phase 2
0.7055	Intermediate Similarity	NPD2799	Discontinued
0.7048	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD5242	Approved
0.7011	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7874	Approved
0.7005	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD1243	Approved
0.6982	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5953	Discontinued
0.697	Remote Similarity	NPD7783	Phase 2
0.697	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1471	Phase 3
0.697	Remote Similarity	NPD2344	Approved
0.6964	Remote Similarity	NPD3300	Phase 2
0.6963	Remote Similarity	NPD7699	Phase 2
0.6963	Remote Similarity	NPD7700	Phase 2
0.6962	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3748	Approved
0.6927	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7458	Discontinued
0.6919	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.691	Remote Similarity	NPD8127	Discontinued
0.6897	Remote Similarity	NPD4665	Approved
0.6897	Remote Similarity	NPD4111	Phase 1
0.6895	Remote Similarity	NPD4363	Phase 3
0.6895	Remote Similarity	NPD4360	Phase 2
0.6886	Remote Similarity	NPD2654	Approved
0.6886	Remote Similarity	NPD6674	Discontinued
0.6883	Remote Similarity	NPD9268	Approved
0.6882	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7229	Phase 3
0.6864	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5761	Phase 2
0.6857	Remote Similarity	NPD5760	Phase 2
0.6855	Remote Similarity	NPD2798	Approved
0.6845	Remote Similarity	NPD8166	Discontinued
0.6842	Remote Similarity	NPD6213	Phase 3
0.6842	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6212	Phase 3
0.6835	Remote Similarity	NPD1283	Approved
0.681	Remote Similarity	NPD4060	Phase 1
0.6807	Remote Similarity	NPD5405	Approved
0.6807	Remote Similarity	NPD5404	Approved
0.6807	Remote Similarity	NPD5406	Approved
0.6807	Remote Similarity	NPD5408	Approved
0.6805	Remote Similarity	NPD2309	Approved
0.6798	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.679	Remote Similarity	NPD3268	Approved
0.679	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7680	Approved
0.6774	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1651	Approved
0.677	Remote Similarity	NPD4908	Phase 1
0.6769	Remote Similarity	NPD2493	Approved
0.6769	Remote Similarity	NPD2494	Approved
0.6752	Remote Similarity	NPD1610	Phase 2

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