NPASS Compound

Structure

NPC246166 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 -2.4081 0.5638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5991 -0.0240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 -0.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9487 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 3.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7213 -0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9013 1.8841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 3.2024 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 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 10 2 0 0 0 0 8 11 2 0 0 0 0 9 12 1 0 0 0 0 9 13 1 0 0 0 0 10 11 1 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 17 1 6 0 0 0 13 23 1 0 0 0 0 14 21 1 0 0 0 0 15 18 2 0 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.13
Volume:	322.398
LogP:	2.482
LogD:	2.548
LogS:	-2.865
# Rotatable Bonds:	5
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	3.378
Fsp3:	0.412
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:	-4.427
MDCK Permeability:	6.566662341356277e-05
Pgp-inhibitor:	0.275
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.967

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.284
Plasma Protein Binding (PPB):	50.05396270751953%
Volume Distribution (VD):	0.812
Pgp-substrate:	11.818016052246094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.667
CYP1A2-substrate:	0.359
CYP2C19-inhibitor:	0.791
CYP2C19-substrate:	0.153
CYP2C9-inhibitor:	0.784
CYP2C9-substrate:	0.335
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.421
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	9.137
Half-life (T1/2):	0.484

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.936
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.188
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.13
Skin Sensitization:	0.187
Carcinogencity:	0.761
Eye Corrosion:	0.004
Eye Irritation:	0.232
Respiratory Toxicity:	0.061

Download Data

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

Natural Product: NPC246166

Natural Product ID:	NPC246166
*Common Name:**	Avicennone A
IUPAC Name:	methyl 2-[(E)-[(5S)-5-(2-hydroxypropan-2-yl)-2-oxooxolan-3-ylidene]-methoxymethyl]benzoate
Synonyms:
Standard InCHIKey:	FPBVSQDBWGKPLR-REQDGWNSSA-N
Standard InCHI:	InChI=1S/C17H20O6/c1-17(2,20)13-9-12(16(19)23-13)14(21-3)10-7-5-6-8-11(10)15(18)22-4/h5-8,13,20H,9H2,1-4H3/b14-12+/t13-/m0/s1
SMILES:	CC(C)([C@@H]1C/C(=C(/c2ccccc2C(=O)OC)OC)/C(=O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL427443
PubChem CID:	44423351
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*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
NPO3629	Avicennia marina	Species	Acanthaceae	Eukaryota	twigs	n.a.	n.a.	PMID[17500572]
NPO3629	Avicennia marina	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19377635]
NPO3629	Avicennia marina	Species	Acanthaceae	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
GI50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	GI50	>	10.0	ug.mL-1	PMID[469620]
NPT111	Cell Line	K562	Homo sapiens	GI50	>	10.0	ug.mL-1	PMID[469620]
NPT165	Cell Line	HeLa	Homo sapiens	CC50	>	10.0	ug.mL-1	PMID[469620]

☑ 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 NPC246166 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	230
0.1-0.2	942
0.2-0.3	2306
0.3-0.4	6084
0.4-0.5	10827
0.5-0.6	10093
0.6-0.7	10395
0.7-0.8	1702
0.8-0.85	116
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8814	High Similarity	NPC307651
0.85	High Similarity	NPC153053
0.8487	Intermediate Similarity	NPC321852
0.8475	Intermediate Similarity	NPC174099
0.8403	Intermediate Similarity	NPC260818
0.839	Intermediate Similarity	NPC10251
0.839	Intermediate Similarity	NPC474364
0.839	Intermediate Similarity	NPC265407
0.839	Intermediate Similarity	NPC17417
0.839	Intermediate Similarity	NPC83628
0.8376	Intermediate Similarity	NPC30594
0.8376	Intermediate Similarity	NPC37622
0.8361	Intermediate Similarity	NPC149691
0.8359	Intermediate Similarity	NPC476033
0.8347	Intermediate Similarity	NPC474363
0.8346	Intermediate Similarity	NPC477896
0.8333	Intermediate Similarity	NPC474314
0.8319	Intermediate Similarity	NPC214067
0.8319	Intermediate Similarity	NPC93084
0.8319	Intermediate Similarity	NPC196246
0.8319	Intermediate Similarity	NPC251854
0.8305	Intermediate Similarity	NPC56493
0.8264	Intermediate Similarity	NPC272524
0.8258	Intermediate Similarity	NPC239358
0.8258	Intermediate Similarity	NPC233692
0.8258	Intermediate Similarity	NPC233860
0.825	Intermediate Similarity	NPC305912
0.825	Intermediate Similarity	NPC474157
0.825	Intermediate Similarity	NPC1082
0.8235	Intermediate Similarity	NPC85493
0.8222	Intermediate Similarity	NPC27721
0.822	Intermediate Similarity	NPC119271
0.8217	Intermediate Similarity	NPC121272
0.8217	Intermediate Similarity	NPC79608
0.8209	Intermediate Similarity	NPC200154
0.8209	Intermediate Similarity	NPC477893
0.8209	Intermediate Similarity	NPC311339
0.8197	Intermediate Similarity	NPC308744
0.8195	Intermediate Similarity	NPC472248
0.8182	Intermediate Similarity	NPC82899
0.8182	Intermediate Similarity	NPC270699
0.8148	Intermediate Similarity	NPC202729
0.8134	Intermediate Similarity	NPC136994
0.8134	Intermediate Similarity	NPC88255
0.8134	Intermediate Similarity	NPC38420
0.8134	Intermediate Similarity	NPC28836
0.8134	Intermediate Similarity	NPC136608
0.8134	Intermediate Similarity	NPC311492
0.813	Intermediate Similarity	NPC474685
0.813	Intermediate Similarity	NPC210092
0.8125	Intermediate Similarity	NPC472703
0.8125	Intermediate Similarity	NPC223351
0.812	Intermediate Similarity	NPC89886
0.8106	Intermediate Similarity	NPC27712
0.8102	Intermediate Similarity	NPC97667
0.8102	Intermediate Similarity	NPC100913
0.8102	Intermediate Similarity	NPC171207
0.8102	Intermediate Similarity	NPC275592
0.8092	Intermediate Similarity	NPC472707
0.8074	Intermediate Similarity	NPC472247
0.8062	Intermediate Similarity	NPC472704
0.8062	Intermediate Similarity	NPC471466
0.806	Intermediate Similarity	NPC302844
0.8058	Intermediate Similarity	NPC95449
0.8058	Intermediate Similarity	NPC45307
0.8051	Intermediate Similarity	NPC31786
0.8049	Intermediate Similarity	NPC477411
0.8049	Intermediate Similarity	NPC237366
0.8043	Intermediate Similarity	NPC27377
0.8043	Intermediate Similarity	NPC474303
0.8043	Intermediate Similarity	NPC473497
0.8043	Intermediate Similarity	NPC97947
0.8043	Intermediate Similarity	NPC475413
0.8043	Intermediate Similarity	NPC472576
0.8043	Intermediate Similarity	NPC118080
0.8043	Intermediate Similarity	NPC16912
0.8043	Intermediate Similarity	NPC87448
0.8043	Intermediate Similarity	NPC41481
0.8043	Intermediate Similarity	NPC291599
0.8043	Intermediate Similarity	NPC77493
0.8033	Intermediate Similarity	NPC158282
0.8029	Intermediate Similarity	NPC475195
0.8015	Intermediate Similarity	NPC472545
0.8015	Intermediate Similarity	NPC472551
0.8015	Intermediate Similarity	NPC472706
0.8014	Intermediate Similarity	NPC469513
0.8014	Intermediate Similarity	NPC170668
0.7986	Intermediate Similarity	NPC469911
0.7985	Intermediate Similarity	NPC473777
0.7983	Intermediate Similarity	NPC209632
0.7971	Intermediate Similarity	NPC197666
0.7971	Intermediate Similarity	NPC472547
0.7971	Intermediate Similarity	NPC90614
0.7971	Intermediate Similarity	NPC126739
0.797	Intermediate Similarity	NPC272946
0.797	Intermediate Similarity	NPC475508
0.7967	Intermediate Similarity	NPC474176
0.7966	Intermediate Similarity	NPC301943
0.7966	Intermediate Similarity	NPC474365
0.7956	Intermediate Similarity	NPC39549
0.7951	Intermediate Similarity	NPC476003
0.7943	Intermediate Similarity	NPC127857
0.7941	Intermediate Similarity	NPC290833
0.7941	Intermediate Similarity	NPC265459
0.7941	Intermediate Similarity	NPC475262
0.7934	Intermediate Similarity	NPC469636
0.7929	Intermediate Similarity	NPC477894
0.7929	Intermediate Similarity	NPC184053
0.7923	Intermediate Similarity	NPC228739
0.7923	Intermediate Similarity	NPC138798
0.792	Intermediate Similarity	NPC226093
0.792	Intermediate Similarity	NPC210531
0.7917	Intermediate Similarity	NPC471103
0.7917	Intermediate Similarity	NPC306799
0.7917	Intermediate Similarity	NPC101043
0.7917	Intermediate Similarity	NPC51602
0.791	Intermediate Similarity	NPC291419
0.791	Intermediate Similarity	NPC60825
0.7899	Intermediate Similarity	NPC9905
0.7899	Intermediate Similarity	NPC114594
0.7899	Intermediate Similarity	NPC473301
0.7891	Intermediate Similarity	NPC105709
0.7887	Intermediate Similarity	NPC213900
0.7887	Intermediate Similarity	NPC477737
0.7883	Intermediate Similarity	NPC194769
0.7883	Intermediate Similarity	NPC285221
0.7881	Intermediate Similarity	NPC45613
0.7879	Intermediate Similarity	NPC110211
0.7879	Intermediate Similarity	NPC204579
0.7879	Intermediate Similarity	NPC169913
0.7879	Intermediate Similarity	NPC51292
0.7877	Intermediate Similarity	NPC200773
0.7877	Intermediate Similarity	NPC240768
0.7872	Intermediate Similarity	NPC470152
0.7872	Intermediate Similarity	NPC476974
0.7872	Intermediate Similarity	NPC241951
0.7872	Intermediate Similarity	NPC188865
0.7872	Intermediate Similarity	NPC472569
0.7872	Intermediate Similarity	NPC472573
0.7872	Intermediate Similarity	NPC163719
0.7872	Intermediate Similarity	NPC475122
0.7872	Intermediate Similarity	NPC472570
0.7872	Intermediate Similarity	NPC25768
0.7872	Intermediate Similarity	NPC11685
0.7872	Intermediate Similarity	NPC95810
0.7872	Intermediate Similarity	NPC242756
0.7872	Intermediate Similarity	NPC475759
0.7872	Intermediate Similarity	NPC57628
0.7872	Intermediate Similarity	NPC70716
0.7872	Intermediate Similarity	NPC125106
0.7872	Intermediate Similarity	NPC95265
0.7868	Intermediate Similarity	NPC472250
0.7868	Intermediate Similarity	NPC477368
0.7868	Intermediate Similarity	NPC477359
0.7868	Intermediate Similarity	NPC474608
0.7868	Intermediate Similarity	NPC329913
0.7863	Intermediate Similarity	NPC325497
0.7863	Intermediate Similarity	NPC295664
0.7862	Intermediate Similarity	NPC477905
0.7862	Intermediate Similarity	NPC472548
0.7857	Intermediate Similarity	NPC182869
0.7857	Intermediate Similarity	NPC192658
0.7852	Intermediate Similarity	NPC7012
0.7847	Intermediate Similarity	NPC81835
0.7842	Intermediate Similarity	NPC87934
0.7842	Intermediate Similarity	NPC162613
0.784	Intermediate Similarity	NPC306740
0.7836	Intermediate Similarity	NPC226855
0.7836	Intermediate Similarity	NPC82712
0.7836	Intermediate Similarity	NPC147561
0.7833	Intermediate Similarity	NPC269457
0.7832	Intermediate Similarity	NPC205389
0.7826	Intermediate Similarity	NPC86772
0.7823	Intermediate Similarity	NPC128368
0.7823	Intermediate Similarity	NPC161611
0.782	Intermediate Similarity	NPC115797
0.782	Intermediate Similarity	NPC51448
0.7817	Intermediate Similarity	NPC476973
0.7817	Intermediate Similarity	NPC471104
0.7817	Intermediate Similarity	NPC158663
0.7817	Intermediate Similarity	NPC472568
0.7817	Intermediate Similarity	NPC29704
0.7817	Intermediate Similarity	NPC171525
0.7817	Intermediate Similarity	NPC473090
0.7817	Intermediate Similarity	NPC469349
0.7817	Intermediate Similarity	NPC184817
0.7817	Intermediate Similarity	NPC70403
0.7817	Intermediate Similarity	NPC470159
0.7817	Intermediate Similarity	NPC96903
0.7817	Intermediate Similarity	NPC472575
0.7817	Intermediate Similarity	NPC200471
0.7817	Intermediate Similarity	NPC177940
0.7817	Intermediate Similarity	NPC472572
0.7817	Intermediate Similarity	NPC470157
0.7817	Intermediate Similarity	NPC174982
0.7817	Intermediate Similarity	NPC472571
0.7817	Intermediate Similarity	NPC469615
0.7817	Intermediate Similarity	NPC473088
0.7815	Intermediate Similarity	NPC60679
0.7812	Intermediate Similarity	NPC204784

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 NPC246166 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	667
0.2-0.3	1476
0.3-0.4	2672
0.4-0.5	2336
0.5-0.6	1300
0.6-0.7	481
0.7-0.8	22
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8559	High Similarity	NPD2181	Clinical (unspecified phase)
0.839	Intermediate Similarity	NPD2182	Approved
0.8051	Intermediate Similarity	NPD164	Approved
0.7984	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD2067	Discontinued
0.7801	Intermediate Similarity	NPD4628	Phase 3
0.7778	Intermediate Similarity	NPD3764	Approved
0.7744	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD9545	Approved
0.7664	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD230	Phase 1
0.7481	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1238	Approved
0.7347	Intermediate Similarity	NPD2534	Approved
0.7347	Intermediate Similarity	NPD2532	Approved
0.7347	Intermediate Similarity	NPD2533	Approved
0.7329	Intermediate Similarity	NPD7236	Approved
0.7323	Intermediate Similarity	NPD969	Suspended
0.7319	Intermediate Similarity	NPD7008	Discontinued
0.7287	Intermediate Similarity	NPD2629	Approved
0.7244	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6647	Phase 2
0.7231	Intermediate Similarity	NPD4198	Discontinued
0.7222	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD5125	Phase 3
0.7218	Intermediate Similarity	NPD5126	Approved
0.719	Intermediate Similarity	NPD9495	Approved
0.7162	Intermediate Similarity	NPD6799	Approved
0.7154	Intermediate Similarity	NPD5951	Approved
0.7152	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6190	Approved
0.7123	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6355	Discontinued
0.7103	Intermediate Similarity	NPD2346	Discontinued
0.7101	Intermediate Similarity	NPD5647	Approved
0.7086	Intermediate Similarity	NPD7239	Suspended
0.7078	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1608	Approved
0.7055	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD9494	Approved
0.7047	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD9493	Approved
0.7045	Intermediate Similarity	NPD694	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD5909	Discontinued
0.7034	Intermediate Similarity	NPD9258	Approved
0.7034	Intermediate Similarity	NPD9256	Approved
0.7021	Intermediate Similarity	NPD2313	Discontinued
0.7008	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD447	Suspended
0.6993	Remote Similarity	NPD6599	Discontinued
0.6987	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6002	Phase 3
0.6986	Remote Similarity	NPD6004	Phase 3
0.6986	Remote Similarity	NPD6005	Phase 3
0.6985	Remote Similarity	NPD6287	Discontinued
0.6972	Remote Similarity	NPD6233	Phase 2
0.6968	Remote Similarity	NPD7819	Suspended
0.6966	Remote Similarity	NPD2799	Discontinued
0.6963	Remote Similarity	NPD5305	Approved
0.6963	Remote Similarity	NPD5306	Approved
0.696	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1930	Approved
0.696	Remote Similarity	NPD1929	Approved
0.6954	Remote Similarity	NPD6273	Approved
0.6946	Remote Similarity	NPD8434	Phase 2
0.6944	Remote Similarity	NPD6653	Approved
0.6943	Remote Similarity	NPD7075	Discontinued
0.6934	Remote Similarity	NPD9717	Approved
0.6929	Remote Similarity	NPD3662	Phase 3
0.6929	Remote Similarity	NPD5204	Approved
0.6929	Remote Similarity	NPD3664	Approved
0.6929	Remote Similarity	NPD3661	Approved
0.6929	Remote Similarity	NPD6685	Approved
0.6929	Remote Similarity	NPD3663	Approved
0.6928	Remote Similarity	NPD3226	Approved
0.6914	Remote Similarity	NPD7799	Discontinued
0.6913	Remote Similarity	NPD3887	Approved
0.6913	Remote Similarity	NPD2354	Approved
0.6912	Remote Similarity	NPD4106	Approved
0.6912	Remote Similarity	NPD4135	Approved
0.6912	Remote Similarity	NPD4136	Approved
0.6905	Remote Similarity	NPD1237	Approved
0.6901	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD6798	Discontinued
0.6883	Remote Similarity	NPD4380	Phase 2
0.6879	Remote Similarity	NPD6832	Phase 2
0.6879	Remote Similarity	NPD3882	Suspended
0.6875	Remote Similarity	NPD1358	Approved
0.6871	Remote Similarity	NPD5844	Phase 1
0.6861	Remote Similarity	NPD4807	Approved
0.6861	Remote Similarity	NPD4806	Approved
0.686	Remote Similarity	NPD1202	Approved
0.6857	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6085	Phase 2
0.6855	Remote Similarity	NPD2066	Phase 3
0.6853	Remote Similarity	NPD4062	Phase 3
0.685	Remote Similarity	NPD5048	Discontinued
0.6849	Remote Similarity	NPD7033	Discontinued
0.6848	Remote Similarity	NPD7685	Pre-registration
0.6846	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD3750	Approved
0.6839	Remote Similarity	NPD6385	Approved
0.6839	Remote Similarity	NPD6386	Approved
0.6838	Remote Similarity	NPD9259	Approved
0.6838	Remote Similarity	NPD17	Approved
0.6838	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD9257	Approved
0.6835	Remote Similarity	NPD1876	Approved
0.6835	Remote Similarity	NPD3749	Approved
0.6826	Remote Similarity	NPD8407	Phase 2
0.6818	Remote Similarity	NPD7458	Discontinued
0.6815	Remote Similarity	NPD5402	Approved
0.6815	Remote Similarity	NPD3817	Phase 2
0.6812	Remote Similarity	NPD3972	Approved
0.6812	Remote Similarity	NPD6637	Approved
0.6812	Remote Similarity	NPD9269	Phase 2
0.6803	Remote Similarity	NPD2935	Discontinued
0.6797	Remote Similarity	NPD5403	Approved
0.6797	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6801	Discontinued
0.6786	Remote Similarity	NPD2626	Approved
0.6786	Remote Similarity	NPD2627	Approved
0.6786	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2625	Approved
0.6786	Remote Similarity	NPD2160	Approved
0.6786	Remote Similarity	NPD2159	Approved
0.6786	Remote Similarity	NPD2628	Approved
0.6783	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD5401	Approved
0.6772	Remote Similarity	NPD7057	Phase 3
0.6772	Remote Similarity	NPD7058	Phase 2
0.677	Remote Similarity	NPD6232	Discontinued
0.6765	Remote Similarity	NPD4102	Approved
0.6765	Remote Similarity	NPD4105	Approved
0.6765	Remote Similarity	NPD9268	Approved
0.6757	Remote Similarity	NPD2344	Approved
0.6757	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5763	Approved
0.6757	Remote Similarity	NPD5762	Approved
0.6747	Remote Similarity	NPD8368	Discontinued
0.6746	Remote Similarity	NPD1932	Approved
0.6746	Remote Similarity	NPD8150	Discontinued
0.6739	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD2798	Approved
0.6738	Remote Similarity	NPD1019	Discontinued
0.6735	Remote Similarity	NPD3748	Approved
0.6735	Remote Similarity	NPD4308	Phase 3
0.6733	Remote Similarity	NPD7003	Approved
0.6733	Remote Similarity	NPD2575	Approved
0.673	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1778	Approved
0.6714	Remote Similarity	NPD2199	Approved
0.6714	Remote Similarity	NPD2198	Approved
0.6714	Remote Similarity	NPD1283	Approved
0.6714	Remote Similarity	NPD5667	Approved
0.6712	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.671	Remote Similarity	NPD3455	Phase 2
0.671	Remote Similarity	NPD2651	Approved
0.671	Remote Similarity	NPD2649	Approved
0.671	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3818	Discontinued
0.6693	Remote Similarity	NPD5765	Approved
0.6693	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1241	Discontinued
0.6691	Remote Similarity	NPD1894	Discontinued
0.669	Remote Similarity	NPD2979	Phase 3
0.6689	Remote Similarity	NPD2796	Approved
0.6689	Remote Similarity	NPD2438	Suspended
0.6689	Remote Similarity	NPD1551	Phase 2
0.6688	Remote Similarity	NPD1934	Approved
0.6688	Remote Similarity	NPD37	Approved
0.6688	Remote Similarity	NPD920	Approved
0.6687	Remote Similarity	NPD6234	Discontinued
0.6686	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6362	Approved
0.6667	Remote Similarity	NPD3134	Approved
0.6667	Remote Similarity	NPD1693	Approved
0.6667	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD4966	Approved
0.6667	Remote Similarity	NPD2569	Approved
0.6667	Remote Similarity	NPD4621	Approved
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD4965	Approved
0.6667	Remote Similarity	NPD2797	Approved
0.6667	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4619	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD2567	Approved
0.6667	Remote Similarity	NPD5711	Approved
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD5710	Approved
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6765	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