NPASS Compound

Structure

NPC56204 OpenBabel07101718182D 26 28 0 0 1 0 0 0 0 0999 V2000 -0.9749 1.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9499 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1656 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -3.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9478 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -4.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9478 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2157 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1656 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -1.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9499 -4.0489 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -4.0489 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2157 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 -3.4254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7818 -3.4254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8138 -3.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1405 -2.7470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -0.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3837 -4.9499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5135 -4.0489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5637 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9309 -4.4143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 1 0 0 0 0 2 4 2 0 0 0 0 3 8 1 0 0 0 0 4 11 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 12 2 0 0 0 0 7 13 1 0 0 0 0 8 1 1 6 0 0 0 8 25 1 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 11 16 1 0 0 0 0 11 20 2 0 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 6 0 0 0 14 7 1 6 0 0 0 14 17 1 0 0 0 0 14 26 1 0 0 0 0 15 18 1 0 0 0 0 16 23 1 6 0 0 0 17 10 1 1 0 0 0 17 26 1 0 0 0 0 18 24 2 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.12
Volume:	348.718
LogP:	1.42
LogD:	1.258
LogS:	-3.977
# Rotatable Bonds:	0
TPSA:	133.66
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.355
Synthetic Accessibility Score:	4.588
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.535
MDCK Permeability:	3.095826104981825e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.081
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.172
Plasma Protein Binding (PPB):	72.35334777832031%
Volume Distribution (VD):	0.368
Pgp-substrate:	19.901546478271484%

ADMET: Metabolism

CYP1A2-inhibitor:	0.155
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.085
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.124
CYP2C9-substrate:	0.852
CYP2D6-inhibitor:	0.269
CYP2D6-substrate:	0.149
CYP3A4-inhibitor:	0.283
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	10.878
Half-life (T1/2):	0.692

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.734
AMES Toxicity:	0.15
Rat Oral Acute Toxicity:	0.089
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.447
Carcinogencity:	0.101
Eye Corrosion:	0.003
Eye Irritation:	0.153
Respiratory Toxicity:	0.116

Download Data

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

Natural Product: NPC56204

Natural Product ID:	NPC56204
*Common Name:**	TVTWZJGIBKNRLB-WRPUWGFISA-N
IUPAC Name:	n.a.
Synonyms:	4-O-Demethylhypothemycin
Standard InCHIKey:	TVTWZJGIBKNRLB-WRPUWGFISA-N
Standard InCHI:	InChI=1S/C18H20O8/c1-8-3-2-4-11(20)16(23)13(22)7-14-17(26-14)10-5-9(19)6-12(21)15(10)18(24)25-8/h2,4-6,8,13-14,16-17,19,21-23H,3,7H2,1H3/b4-2-/t8-,13-,14+,16+,17+/m0/s1
SMILES:	C[C@H]1C/C=CC(=O)[C@H]([C@H](C[C@@H]2[C@@H](c3cc(cc(c3C(=O)O1)O)O)O2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518087
PubChem CID:	16091602
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues [CHEMONTID:0001788] Zearalenones

*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
NPO14176	Hypomyces subiculosus	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17067161]
NPO14176	Hypomyces subiculosus	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20118535]
NPO14176	Hypomyces subiculosus	Species	Hypocreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	38.0	nM	PMID[523785]
NPT1915	Cell Line	COLO-829	Homo sapiens	IC50	=	100.0	nM	PMID[523785]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	1800.0	nM	PMID[523785]

☑ 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 NPC56204 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	352
0.1-0.2	1383
0.2-0.3	3503
0.3-0.4	7636
0.4-0.5	10249
0.5-0.6	4941
0.6-0.7	6327
0.7-0.8	7409
0.8-0.85	730
0.85-0.9	149
0.9-0.95	15
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC99381
0.965	High Similarity	NPC83272
0.9456	High Similarity	NPC469619
0.9456	High Similarity	NPC469670
0.9379	High Similarity	NPC257558
0.932	High Similarity	NPC215711
0.932	High Similarity	NPC73411
0.931	High Similarity	NPC210966
0.931	High Similarity	NPC478203
0.931	High Similarity	NPC126882
0.9301	High Similarity	NPC158472
0.9252	High Similarity	NPC210320
0.9236	High Similarity	NPC244923
0.9184	High Similarity	NPC107625
0.9161	High Similarity	NPC212693
0.9161	High Similarity	NPC478200
0.9161	High Similarity	NPC33144
0.9161	High Similarity	NPC94248
0.9161	High Similarity	NPC191835
0.9133	High Similarity	NPC240768
0.9133	High Similarity	NPC200773
0.9133	High Similarity	NPC215921
0.9133	High Similarity	NPC70016
0.911	High Similarity	NPC354984
0.9103	High Similarity	NPC478217
0.9103	High Similarity	NPC313123
0.9103	High Similarity	NPC472035
0.9103	High Similarity	NPC478201
0.9097	High Similarity	NPC52358
0.9091	High Similarity	NPC70380
0.9085	High Similarity	NPC472889
0.9079	High Similarity	NPC478230
0.9079	High Similarity	NPC69043
0.9079	High Similarity	NPC472890
0.9073	High Similarity	NPC478224
0.9048	High Similarity	NPC280404
0.9048	High Similarity	NPC210425
0.9048	High Similarity	NPC277426
0.9048	High Similarity	NPC86373
0.9013	High Similarity	NPC478231
0.9013	High Similarity	NPC137301
0.8993	High Similarity	NPC472036
0.898	High Similarity	NPC51106
0.898	High Similarity	NPC472006
0.898	High Similarity	NPC478202
0.8973	High Similarity	NPC158634
0.8966	High Similarity	NPC105456
0.8966	High Similarity	NPC139634
0.8961	High Similarity	NPC478225
0.8958	High Similarity	NPC71256
0.8954	High Similarity	NPC478221
0.8954	High Similarity	NPC208173
0.8954	High Similarity	NPC317585
0.8954	High Similarity	NPC170189
0.8947	High Similarity	NPC76041
0.8947	High Similarity	NPC115249
0.8947	High Similarity	NPC184284
0.894	High Similarity	NPC472891
0.8926	High Similarity	NPC473023
0.8926	High Similarity	NPC472033
0.8912	High Similarity	NPC474385
0.8897	High Similarity	NPC475974
0.8897	High Similarity	NPC472602
0.8897	High Similarity	NPC177307
0.8897	High Similarity	NPC9121
0.8882	High Similarity	NPC91809
0.8867	High Similarity	NPC166583
0.8867	High Similarity	NPC53362
0.8867	High Similarity	NPC81835
0.8859	High Similarity	NPC472034
0.8844	High Similarity	NPC472604
0.8844	High Similarity	NPC67650
0.8844	High Similarity	NPC53649
0.8844	High Similarity	NPC1704
0.8844	High Similarity	NPC472603
0.8844	High Similarity	NPC472605
0.8836	High Similarity	NPC32360
0.8836	High Similarity	NPC268052
0.8828	High Similarity	NPC474771
0.8828	High Similarity	NPC474849
0.8828	High Similarity	NPC178467
0.8828	High Similarity	NPC149372
0.8828	High Similarity	NPC65837
0.8816	High Similarity	NPC164762
0.8811	High Similarity	NPC153783
0.88	High Similarity	NPC51513
0.88	High Similarity	NPC202112
0.8792	High Similarity	NPC151607
0.8792	High Similarity	NPC42540
0.879	High Similarity	NPC317544
0.8776	High Similarity	NPC472601
0.8776	High Similarity	NPC472600
0.8767	High Similarity	NPC126739
0.8767	High Similarity	NPC197666
0.8767	High Similarity	NPC472403
0.8766	High Similarity	NPC281703
0.8766	High Similarity	NPC125487
0.8759	High Similarity	NPC235115
0.8758	High Similarity	NPC205918
0.875	High Similarity	NPC270160
0.875	High Similarity	NPC77325
0.875	High Similarity	NPC4423
0.875	High Similarity	NPC237440
0.875	High Similarity	NPC84142
0.8742	High Similarity	NPC472049
0.8726	High Similarity	NPC472055
0.8725	High Similarity	NPC469542
0.8725	High Similarity	NPC159721
0.8725	High Similarity	NPC471731
0.8718	High Similarity	NPC478226
0.8718	High Similarity	NPC473395
0.8718	High Similarity	NPC246466
0.8716	High Similarity	NPC475730
0.871	High Similarity	NPC79998
0.871	High Similarity	NPC16082
0.871	High Similarity	NPC82592
0.8707	High Similarity	NPC275356
0.8707	High Similarity	NPC474655
0.8707	High Similarity	NPC471819
0.8707	High Similarity	NPC247409
0.8701	High Similarity	NPC213224
0.8699	High Similarity	NPC194579
0.8693	High Similarity	NPC179178
0.869	High Similarity	NPC27407
0.869	High Similarity	NPC142027
0.8684	High Similarity	NPC221352
0.8684	High Similarity	NPC153417
0.8671	High Similarity	NPC117985
0.8671	High Similarity	NPC189823
0.8671	High Similarity	NPC219892
0.8662	High Similarity	NPC470339
0.8658	High Similarity	NPC82913
0.8658	High Similarity	NPC471733
0.8658	High Similarity	NPC469579
0.8654	High Similarity	NPC472050
0.8649	High Similarity	NPC64664
0.8649	High Similarity	NPC155205
0.8645	High Similarity	NPC471695
0.8645	High Similarity	NPC281477
0.8645	High Similarity	NPC155686
0.8645	High Similarity	NPC55092
0.8634	High Similarity	NPC283041
0.8627	High Similarity	NPC120171
0.8627	High Similarity	NPC280753
0.8627	High Similarity	NPC476684
0.8627	High Similarity	NPC44378
0.8625	High Similarity	NPC191930
0.8621	High Similarity	NPC474097
0.8618	High Similarity	NPC52106
0.8618	High Similarity	NPC476463
0.8618	High Similarity	NPC14098
0.8616	High Similarity	NPC48860
0.86	High Similarity	NPC472610
0.8599	High Similarity	NPC84935
0.8599	High Similarity	NPC190020
0.8599	High Similarity	NPC77679
0.8591	High Similarity	NPC130485
0.8591	High Similarity	NPC90411
0.8581	High Similarity	NPC88269
0.8581	High Similarity	NPC92655
0.8581	High Similarity	NPC167903
0.8581	High Similarity	NPC470340
0.8571	High Similarity	NPC135837
0.8571	High Similarity	NPC20237
0.8562	High Similarity	NPC94781
0.8562	High Similarity	NPC249181
0.8562	High Similarity	NPC172329
0.8562	High Similarity	NPC240253
0.8562	High Similarity	NPC471641
0.8562	High Similarity	NPC471642
0.8562	High Similarity	NPC240622
0.8562	High Similarity	NPC2569
0.8553	High Similarity	NPC201560
0.8553	High Similarity	NPC268366
0.8552	High Similarity	NPC43627
0.8543	High Similarity	NPC103910
0.8543	High Similarity	NPC184702
0.8542	High Similarity	NPC198249
0.8535	High Similarity	NPC150227
0.8533	High Similarity	NPC322112
0.8533	High Similarity	NPC49108
0.8533	High Similarity	NPC250755
0.8516	High Similarity	NPC132990
0.8516	High Similarity	NPC46882
0.8516	High Similarity	NPC227485
0.8514	High Similarity	NPC221104
0.8503	High Similarity	NPC158481
0.8503	High Similarity	NPC156892
0.8503	High Similarity	NPC208069
0.8503	High Similarity	NPC291454
0.8497	Intermediate Similarity	NPC471734
0.8497	Intermediate Similarity	NPC137296
0.8497	Intermediate Similarity	NPC8817
0.8493	Intermediate Similarity	NPC175943
0.8483	Intermediate Similarity	NPC476389
0.8483	Intermediate Similarity	NPC478190
0.8481	Intermediate Similarity	NPC257309
0.8472	Intermediate Similarity	NPC247477
0.8472	Intermediate Similarity	NPC17840
0.8471	Intermediate Similarity	NPC473241

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 NPC56204 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	916
0.2-0.3	1911
0.3-0.4	2599
0.4-0.5	1910
0.5-0.6	1000
0.6-0.7	374
0.7-0.8	135
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8366	Intermediate Similarity	NPD2533	Approved
0.8366	Intermediate Similarity	NPD2532	Approved
0.8366	Intermediate Similarity	NPD2534	Approved
0.8365	Intermediate Similarity	NPD7075	Discontinued
0.8333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD230	Phase 1
0.8291	Intermediate Similarity	NPD7819	Suspended
0.8255	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6801	Discontinued
0.8217	Intermediate Similarity	NPD4380	Phase 2
0.8182	Intermediate Similarity	NPD6799	Approved
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD3817	Phase 2
0.8125	Intermediate Similarity	NPD5402	Approved
0.8101	Intermediate Similarity	NPD6599	Discontinued
0.8075	Intermediate Similarity	NPD3882	Suspended
0.8063	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6166	Phase 2
0.8049	Intermediate Similarity	NPD6232	Discontinued
0.8025	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD1934	Approved
0.7964	Intermediate Similarity	NPD3818	Discontinued
0.7963	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD5403	Approved
0.7895	Intermediate Similarity	NPD1510	Phase 2
0.7886	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1240	Approved
0.7867	Intermediate Similarity	NPD943	Approved
0.7861	Intermediate Similarity	NPD8150	Discontinued
0.7857	Intermediate Similarity	NPD1549	Phase 2
0.7848	Intermediate Similarity	NPD1512	Approved
0.784	Intermediate Similarity	NPD2801	Approved
0.7826	Intermediate Similarity	NPD7411	Suspended
0.7824	Intermediate Similarity	NPD6797	Phase 2
0.7824	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD6190	Approved
0.7811	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD5401	Approved
0.7778	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6959	Discontinued
0.7765	Intermediate Similarity	NPD7074	Phase 3
0.7763	Intermediate Similarity	NPD1607	Approved
0.7756	Intermediate Similarity	NPD3750	Approved
0.7733	Intermediate Similarity	NPD7808	Phase 3
0.7727	Intermediate Similarity	NPD2935	Discontinued
0.7727	Intermediate Similarity	NPD2796	Approved
0.7722	Intermediate Similarity	NPD1511	Approved
0.7706	Intermediate Similarity	NPD7054	Approved
0.7706	Intermediate Similarity	NPD5844	Phase 1
0.7697	Intermediate Similarity	NPD3749	Approved
0.7692	Intermediate Similarity	NPD9545	Approved
0.7683	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD6559	Discontinued
0.7661	Intermediate Similarity	NPD7472	Approved
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7643	Intermediate Similarity	NPD4628	Phase 3
0.7633	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1465	Phase 2
0.7619	Intermediate Similarity	NPD5710	Approved
0.7619	Intermediate Similarity	NPD5711	Approved
0.761	Intermediate Similarity	NPD7390	Discontinued
0.7593	Intermediate Similarity	NPD3226	Approved
0.7562	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD9493	Approved
0.7551	Intermediate Similarity	NPD9269	Phase 2
0.753	Intermediate Similarity	NPD7768	Phase 2
0.7515	Intermediate Similarity	NPD3787	Discontinued
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD3764	Approved
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.75	Intermediate Similarity	NPD5494	Approved
0.7469	Intermediate Similarity	NPD920	Approved
0.7468	Intermediate Similarity	NPD2800	Approved
0.7459	Intermediate Similarity	NPD7435	Discontinued
0.744	Intermediate Similarity	NPD919	Approved
0.7436	Intermediate Similarity	NPD3748	Approved
0.7419	Intermediate Similarity	NPD8320	Phase 1
0.7419	Intermediate Similarity	NPD8319	Approved
0.7414	Intermediate Similarity	NPD5953	Discontinued
0.7397	Intermediate Similarity	NPD9268	Approved
0.7391	Intermediate Similarity	NPD6776	Approved
0.7391	Intermediate Similarity	NPD6779	Approved
0.7391	Intermediate Similarity	NPD6777	Approved
0.7391	Intermediate Similarity	NPD6780	Approved
0.7391	Intermediate Similarity	NPD6781	Approved
0.7391	Intermediate Similarity	NPD6778	Approved
0.7391	Intermediate Similarity	NPD6782	Approved
0.7389	Intermediate Similarity	NPD5405	Approved
0.7389	Intermediate Similarity	NPD5404	Approved
0.7389	Intermediate Similarity	NPD5406	Approved
0.7389	Intermediate Similarity	NPD5408	Approved
0.7386	Intermediate Similarity	NPD8313	Approved
0.7386	Intermediate Similarity	NPD8312	Approved
0.7386	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7700	Phase 2
0.7377	Intermediate Similarity	NPD7699	Phase 2
0.7374	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3926	Phase 2
0.736	Intermediate Similarity	NPD8434	Phase 2
0.7358	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD447	Suspended
0.7349	Intermediate Similarity	NPD37	Approved
0.7346	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2346	Discontinued
0.7337	Intermediate Similarity	NPD6234	Discontinued
0.7325	Intermediate Similarity	NPD2799	Discontinued
0.7321	Intermediate Similarity	NPD4966	Approved
0.7321	Intermediate Similarity	NPD4965	Approved
0.7321	Intermediate Similarity	NPD4967	Phase 2
0.7308	Intermediate Similarity	NPD6651	Approved
0.7303	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7286	Phase 2
0.7285	Intermediate Similarity	NPD1470	Approved
0.7267	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8151	Discontinued
0.7256	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7199	Phase 2
0.7251	Intermediate Similarity	NPD1247	Approved
0.725	Intermediate Similarity	NPD1243	Approved
0.7228	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7874	Approved
0.7225	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9717	Approved
0.7192	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7697	Approved
0.7181	Intermediate Similarity	NPD7698	Approved
0.7181	Intermediate Similarity	NPD7696	Phase 3
0.7175	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7143	Intermediate Similarity	NPD7228	Approved
0.7134	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1201	Approved
0.7125	Intermediate Similarity	NPD2344	Approved
0.712	Intermediate Similarity	NPD7701	Phase 2
0.7105	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4060	Phase 1
0.7066	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6213	Phase 3
0.7065	Intermediate Similarity	NPD6212	Phase 3
0.7063	Intermediate Similarity	NPD6100	Approved
0.7063	Intermediate Similarity	NPD6099	Approved
0.7059	Intermediate Similarity	NPD1203	Approved
0.7059	Intermediate Similarity	NPD1164	Approved
0.7051	Intermediate Similarity	NPD2313	Discontinued
0.7051	Intermediate Similarity	NPD411	Approved
0.703	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6355	Discontinued
0.7019	Intermediate Similarity	NPD7266	Discontinued
0.7012	Intermediate Similarity	NPD3300	Phase 2
0.7011	Intermediate Similarity	NPD7229	Phase 3
0.701	Intermediate Similarity	NPD7801	Approved
0.7006	Intermediate Similarity	NPD1653	Approved
0.7	Intermediate Similarity	NPD7033	Discontinued
0.6994	Remote Similarity	NPD8166	Discontinued
0.6993	Remote Similarity	NPD9266	Approved
0.6993	Remote Similarity	NPD74	Approved
0.6987	Remote Similarity	NPD3027	Phase 3
0.6979	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5242	Approved
0.6968	Remote Similarity	NPD9494	Approved
0.6962	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5353	Approved
0.6951	Remote Similarity	NPD2309	Approved
0.6947	Remote Similarity	NPD6823	Phase 2
0.6944	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6798	Discontinued
0.6933	Remote Similarity	NPD2654	Approved
0.6931	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9263	Approved
0.6923	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9267	Approved
0.6923	Remote Similarity	NPD9264	Approved
0.6923	Remote Similarity	NPD7783	Phase 2
0.6909	Remote Similarity	NPD7236	Approved
0.6908	Remote Similarity	NPD422	Phase 1
0.6903	Remote Similarity	NPD1019	Discontinued
0.6903	Remote Similarity	NPD2798	Approved
0.6897	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD8368	Discontinued
0.6887	Remote Similarity	NPD4626	Approved
0.6886	Remote Similarity	NPD6273	Approved
0.6882	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2182	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