NPASS Compound

Structure

NPC472706 OpenBabel07101719522D 27 28 0 0 1 0 0 0 0 0999 V2000 -0.1554 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7957 -1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -5.8660 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 -2.5981 -0.5000 0.0000 C 0 0 0 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 -1.7321 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 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -5.0000 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 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -6.0000 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 -2.9641 -5.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 5 7 1 0 0 0 0 5 14 2 0 0 0 0 6 8 2 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 20 1 0 0 0 0 12 27 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 21 1 6 0 0 0 16 22 1 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 25 2 0 0 0 0 18 27 1 0 0 0 0 19 21 1 0 0 0 0 20 3 1 6 0 0 0 20 26 1 0 0 0 0 21 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.2
Volume:	394.218
LogP:	3.139
LogD:	2.581
LogS:	-4.223
# Rotatable Bonds:	8
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.63
Synthetic Accessibility Score:	3.756
Fsp3:	0.619
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:	-5.269
MDCK Permeability:	2.5932597054634243e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.109
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.139
Plasma Protein Binding (PPB):	89.52393341064453%
Volume Distribution (VD):	0.209
Pgp-substrate:	9.468244552612305%

ADMET: Metabolism

CYP1A2-inhibitor:	0.034
CYP1A2-substrate:	0.342
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.723
CYP2C9-inhibitor:	0.079
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.239
CYP3A4-inhibitor:	0.035
CYP3A4-substrate:	0.122

ADMET: Excretion

Clearance (CL):	11.02
Half-life (T1/2):	0.554

ADMET: Toxicity

hERG Blockers:	0.051
Human Hepatotoxicity (H-HT):	0.043
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.073
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.044
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC472706

Natural Product ID:	NPC472706
*Common Name:**	UYLYUHNDNNVOPJ-HBGVWJBISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UYLYUHNDNNVOPJ-HBGVWJBISA-N
Standard InCHI:	InChI=1S/C21H30O6/c1-19(2)10-9-16(22)21(19,4)15-7-5-14(6-8-15)18(25)27-12-11-20(3,26)13-17(23)24/h5-8,16,22,26H,9-13H2,1-4H3,(H,23,24)/t16-,20-,21+/m1/s1
SMILES:	CC1(CCC(C1(C)C2=CC=C(C=C2)C(=O)OCCC(C)(CC(=O)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581622
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32768	basidiomycete deconica sp. 471	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25871540]

☑ 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	1
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	=	2.8	ug.mL-1	PMID[526630]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	67.0	ug.mL-1	PMID[526630]

☑ 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 NPC472706 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	244
0.1-0.2	914
0.2-0.3	2158
0.3-0.4	5389
0.4-0.5	10955
0.5-0.6	13521
0.6-0.7	8363
0.7-0.8	1025
0.8-0.85	77
0.85-0.9	47
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9664	High Similarity	NPC472703
0.9583	High Similarity	NPC472704
0.9274	High Similarity	NPC472707
0.8837	High Similarity	NPC233692
0.8837	High Similarity	NPC239358
0.8828	High Similarity	NPC82712
0.8769	High Similarity	NPC472248
0.8731	High Similarity	NPC242355
0.8702	High Similarity	NPC28836
0.8702	High Similarity	NPC311492
0.8699	High Similarity	NPC472708
0.8692	High Similarity	NPC233860
0.8636	High Similarity	NPC200154
0.8615	High Similarity	NPC72915
0.8593	High Similarity	NPC475413
0.8593	High Similarity	NPC474303
0.8593	High Similarity	NPC473497
0.8571	High Similarity	NPC202729
0.8561	High Similarity	NPC477368
0.8538	High Similarity	NPC272946
0.8507	High Similarity	NPC27721
0.8496	Intermediate Similarity	NPC232888
0.8496	Intermediate Similarity	NPC477367
0.8485	Intermediate Similarity	NPC477364
0.8467	Intermediate Similarity	NPC45307
0.8444	Intermediate Similarity	NPC473301
0.8421	Intermediate Similarity	NPC153617
0.8421	Intermediate Similarity	NPC477359
0.8397	Intermediate Similarity	NPC475508
0.837	Intermediate Similarity	NPC86772
0.8358	Intermediate Similarity	NPC79699
0.8357	Intermediate Similarity	NPC205389
0.8309	Intermediate Similarity	NPC272523
0.8309	Intermediate Similarity	NPC170718
0.8309	Intermediate Similarity	NPC325805
0.8296	Intermediate Similarity	NPC217673
0.8296	Intermediate Similarity	NPC52523
0.8286	Intermediate Similarity	NPC170668
0.8284	Intermediate Similarity	NPC472250
0.8258	Intermediate Similarity	NPC42234
0.825	Intermediate Similarity	NPC469636
0.8239	Intermediate Similarity	NPC232583
0.8239	Intermediate Similarity	NPC25484
0.8239	Intermediate Similarity	NPC477097
0.8239	Intermediate Similarity	NPC477101
0.8239	Intermediate Similarity	NPC477099
0.8222	Intermediate Similarity	NPC475262
0.8222	Intermediate Similarity	NPC265459
0.8222	Intermediate Similarity	NPC270364
0.8222	Intermediate Similarity	NPC290833
0.8201	Intermediate Similarity	NPC153214
0.8188	Intermediate Similarity	NPC187566
0.8175	Intermediate Similarity	NPC9905
0.8167	Intermediate Similarity	NPC249811
0.8162	Intermediate Similarity	NPC285221
0.8162	Intermediate Similarity	NPC194769
0.8156	Intermediate Similarity	NPC478263
0.8148	Intermediate Similarity	NPC134937
0.8148	Intermediate Similarity	NPC48929
0.8148	Intermediate Similarity	NPC298547
0.8148	Intermediate Similarity	NPC324898
0.814	Intermediate Similarity	NPC223351
0.8134	Intermediate Similarity	NPC477360
0.8129	Intermediate Similarity	NPC51181
0.8116	Intermediate Similarity	NPC87934
0.8116	Intermediate Similarity	NPC162613
0.8102	Intermediate Similarity	NPC39549
0.8092	Intermediate Similarity	NPC477366
0.8088	Intermediate Similarity	NPC472247
0.8088	Intermediate Similarity	NPC279637
0.8088	Intermediate Similarity	NPC149401
0.8085	Intermediate Similarity	NPC478264
0.8085	Intermediate Similarity	NPC25043
0.8085	Intermediate Similarity	NPC134131
0.808	Intermediate Similarity	NPC149691
0.8071	Intermediate Similarity	NPC477096
0.8071	Intermediate Similarity	NPC82467
0.8071	Intermediate Similarity	NPC477094
0.8069	Intermediate Similarity	NPC477098
0.8069	Intermediate Similarity	NPC477100
0.8065	Intermediate Similarity	NPC307651
0.8065	Intermediate Similarity	NPC474363
0.8043	Intermediate Similarity	NPC276652
0.803	Intermediate Similarity	NPC477365
0.803	Intermediate Similarity	NPC110211
0.8029	Intermediate Similarity	NPC472551
0.8029	Intermediate Similarity	NPC472545
0.8015	Intermediate Similarity	NPC203486
0.8015	Intermediate Similarity	NPC126516
0.8015	Intermediate Similarity	NPC246166
0.8	Intermediate Similarity	NPC192658
0.7986	Intermediate Similarity	NPC90614
0.7986	Intermediate Similarity	NPC125033
0.7986	Intermediate Similarity	NPC251294
0.7986	Intermediate Similarity	NPC100913
0.7986	Intermediate Similarity	NPC476173
0.7986	Intermediate Similarity	NPC275592
0.7986	Intermediate Similarity	NPC472547
0.7986	Intermediate Similarity	NPC475660
0.7985	Intermediate Similarity	NPC147561
0.7984	Intermediate Similarity	NPC128368
0.7984	Intermediate Similarity	NPC50872
0.7971	Intermediate Similarity	NPC205305
0.7971	Intermediate Similarity	NPC327511
0.797	Intermediate Similarity	NPC477370
0.7967	Intermediate Similarity	NPC476003
0.7955	Intermediate Similarity	NPC477363
0.7955	Intermediate Similarity	NPC275576
0.7955	Intermediate Similarity	NPC476033
0.7943	Intermediate Similarity	NPC95449
0.7939	Intermediate Similarity	NPC228739
0.7939	Intermediate Similarity	NPC477362
0.7931	Intermediate Similarity	NPC161955
0.7929	Intermediate Similarity	NPC87448
0.7929	Intermediate Similarity	NPC291599
0.7929	Intermediate Similarity	NPC97947
0.7929	Intermediate Similarity	NPC118080
0.7929	Intermediate Similarity	NPC473654
0.7929	Intermediate Similarity	NPC41481
0.7929	Intermediate Similarity	NPC472576
0.7929	Intermediate Similarity	NPC27377
0.7929	Intermediate Similarity	NPC266374
0.7914	Intermediate Similarity	NPC53361
0.7914	Intermediate Similarity	NPC121268
0.791	Intermediate Similarity	NPC37968
0.7907	Intermediate Similarity	NPC133302
0.7902	Intermediate Similarity	NPC312393
0.7902	Intermediate Similarity	NPC477095
0.7899	Intermediate Similarity	NPC477358
0.7895	Intermediate Similarity	NPC473220
0.7895	Intermediate Similarity	NPC470753
0.7895	Intermediate Similarity	NPC204579
0.7895	Intermediate Similarity	NPC169913
0.7895	Intermediate Similarity	NPC477357
0.7891	Intermediate Similarity	NPC469456
0.7887	Intermediate Similarity	NPC34943
0.7883	Intermediate Similarity	NPC329913
0.7879	Intermediate Similarity	NPC295664
0.7872	Intermediate Similarity	NPC183540
0.7857	Intermediate Similarity	NPC97667
0.7857	Intermediate Similarity	NPC171207
0.7857	Intermediate Similarity	NPC306740
0.7847	Intermediate Similarity	NPC327031
0.7847	Intermediate Similarity	NPC132652
0.7833	Intermediate Similarity	NPC301943
0.7833	Intermediate Similarity	NPC474365
0.7832	Intermediate Similarity	NPC92867
0.7832	Intermediate Similarity	NPC125882
0.7832	Intermediate Similarity	NPC127857
0.7832	Intermediate Similarity	NPC311825
0.7829	Intermediate Similarity	NPC204784
0.7826	Intermediate Similarity	NPC477893
0.782	Intermediate Similarity	NPC470765
0.782	Intermediate Similarity	NPC79608
0.7817	Intermediate Similarity	NPC191387
0.7817	Intermediate Similarity	NPC477894
0.7817	Intermediate Similarity	NPC163087
0.7817	Intermediate Similarity	NPC131966
0.7817	Intermediate Similarity	NPC91703
0.7815	Intermediate Similarity	NPC70624
0.7808	Intermediate Similarity	NPC471103
0.7805	Intermediate Similarity	NPC83628
0.7805	Intermediate Similarity	NPC265407
0.7801	Intermediate Similarity	NPC224491
0.7801	Intermediate Similarity	NPC77493
0.7801	Intermediate Similarity	NPC16912
0.7793	Intermediate Similarity	NPC60509
0.7793	Intermediate Similarity	NPC81698
0.7793	Intermediate Similarity	NPC250046
0.7778	Intermediate Similarity	NPC20255
0.7778	Intermediate Similarity	NPC469513
0.7778	Intermediate Similarity	NPC240115
0.7778	Intermediate Similarity	NPC473602
0.7778	Intermediate Similarity	NPC153053
0.7778	Intermediate Similarity	NPC87069
0.777	Intermediate Similarity	NPC472374
0.777	Intermediate Similarity	NPC472372
0.7769	Intermediate Similarity	NPC473243
0.7762	Intermediate Similarity	NPC470152
0.7762	Intermediate Similarity	NPC241951
0.7762	Intermediate Similarity	NPC475122
0.7762	Intermediate Similarity	NPC475759
0.7761	Intermediate Similarity	NPC253681
0.776	Intermediate Similarity	NPC321852
0.7755	Intermediate Similarity	NPC477905
0.7755	Intermediate Similarity	NPC472548
0.7754	Intermediate Similarity	NPC474608
0.7746	Intermediate Similarity	NPC475135
0.7746	Intermediate Similarity	NPC34012
0.7746	Intermediate Similarity	NPC472546
0.774	Intermediate Similarity	NPC91730
0.774	Intermediate Similarity	NPC165260
0.774	Intermediate Similarity	NPC198455
0.774	Intermediate Similarity	NPC161239
0.774	Intermediate Similarity	NPC7095
0.7737	Intermediate Similarity	NPC238370
0.7731	Intermediate Similarity	NPC325497
0.7731	Intermediate Similarity	NPC203925
0.773	Intermediate Similarity	NPC477904
0.773	Intermediate Similarity	NPC183270

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 NPC472706 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	207
0.1-0.2	694
0.2-0.3	1477
0.3-0.4	2699
0.4-0.5	2385
0.5-0.6	1265
0.6-0.7	378
0.7-0.8	44
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8085	Intermediate Similarity	NPD7236	Approved
0.803	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7239	Suspended
0.7852	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4628	Phase 3
0.7661	Intermediate Similarity	NPD2182	Approved
0.763	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6085	Phase 2
0.7591	Intermediate Similarity	NPD7008	Discontinued
0.758	Intermediate Similarity	NPD7799	Discontinued
0.7519	Intermediate Similarity	NPD6287	Discontinued
0.75	Intermediate Similarity	NPD6685	Approved
0.7451	Intermediate Similarity	NPD7057	Phase 3
0.7451	Intermediate Similarity	NPD7058	Phase 2
0.7444	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5951	Approved
0.7432	Intermediate Similarity	NPD6273	Approved
0.7385	Intermediate Similarity	NPD4198	Discontinued
0.7381	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD9545	Approved
0.7339	Intermediate Similarity	NPD164	Approved
0.7308	Intermediate Similarity	NPD2629	Approved
0.7308	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD1238	Approved
0.728	Intermediate Similarity	NPD5048	Discontinued
0.7258	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6647	Phase 2
0.7258	Intermediate Similarity	NPD5765	Approved
0.7241	Intermediate Similarity	NPD6005	Phase 3
0.7241	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6004	Phase 3
0.7241	Intermediate Similarity	NPD6002	Phase 3
0.7241	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6010	Discontinued
0.7218	Intermediate Similarity	NPD7741	Discontinued
0.7197	Intermediate Similarity	NPD9493	Approved
0.7163	Intermediate Similarity	NPD3764	Approved
0.7154	Intermediate Similarity	NPD6858	Approved
0.7154	Intermediate Similarity	NPD2066	Phase 3
0.7154	Intermediate Similarity	NPD7094	Approved
0.7133	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6599	Discontinued
0.7122	Intermediate Similarity	NPD5647	Approved
0.7111	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1693	Approved
0.7103	Intermediate Similarity	NPD7033	Discontinued
0.7099	Intermediate Similarity	NPD2650	Approved
0.7099	Intermediate Similarity	NPD2652	Approved
0.7083	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1088	Approved
0.7077	Intermediate Similarity	NPD6912	Phase 3
0.7077	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1237	Approved
0.7059	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD2067	Discontinued
0.702	Intermediate Similarity	NPD2534	Approved
0.702	Intermediate Similarity	NPD2532	Approved
0.702	Intermediate Similarity	NPD2533	Approved
0.6993	Remote Similarity	NPD7961	Discontinued
0.6993	Remote Similarity	NPD6663	Approved
0.6987	Remote Similarity	NPD5761	Phase 2
0.6987	Remote Similarity	NPD5760	Phase 2
0.6985	Remote Similarity	NPD1778	Approved
0.6984	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1929	Approved
0.6984	Remote Similarity	NPD1930	Approved
0.6963	Remote Similarity	NPD7009	Phase 2
0.6957	Remote Similarity	NPD3972	Approved
0.6957	Remote Similarity	NPD9717	Approved
0.695	Remote Similarity	NPD5736	Approved
0.6939	Remote Similarity	NPD1551	Phase 2
0.6935	Remote Similarity	NPD9495	Approved
0.6929	Remote Similarity	NPD6362	Approved
0.6918	Remote Similarity	NPD2567	Approved
0.6918	Remote Similarity	NPD2569	Approved
0.6917	Remote Similarity	NPD1086	Approved
0.6917	Remote Similarity	NPD1089	Approved
0.6917	Remote Similarity	NPD9256	Approved
0.6917	Remote Similarity	NPD9258	Approved
0.6917	Remote Similarity	NPD1090	Approved
0.6911	Remote Similarity	NPD1989	Approved
0.6905	Remote Similarity	NPD1932	Approved
0.6901	Remote Similarity	NPD6832	Phase 2
0.6892	Remote Similarity	NPD2346	Discontinued
0.6871	Remote Similarity	NPD2799	Discontinued
0.6871	Remote Similarity	NPD7305	Phase 1
0.6871	Remote Similarity	NPD4308	Phase 3
0.6867	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD5125	Phase 3
0.6861	Remote Similarity	NPD5126	Approved
0.6849	Remote Similarity	NPD6653	Approved
0.6833	Remote Similarity	NPD800	Approved
0.6828	Remote Similarity	NPD4140	Approved
0.6824	Remote Similarity	NPD2935	Discontinued
0.6824	Remote Similarity	NPD7137	Phase 2
0.6806	Remote Similarity	NPD411	Approved
0.6806	Remote Similarity	NPD2313	Discontinued
0.68	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5909	Discontinued
0.6781	Remote Similarity	NPD230	Phase 1
0.6772	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7819	Suspended
0.6766	Remote Similarity	NPD6764	Approved
0.6766	Remote Similarity	NPD8368	Discontinued
0.6766	Remote Similarity	NPD6765	Approved
0.6765	Remote Similarity	NPD7610	Discontinued
0.6761	Remote Similarity	NPD2798	Approved
0.6759	Remote Similarity	NPD7715	Approved
0.6759	Remote Similarity	NPD7713	Phase 3
0.6759	Remote Similarity	NPD7714	Approved
0.6755	Remote Similarity	NPD7003	Approved
0.6748	Remote Similarity	NPD1202	Approved
0.6748	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD8407	Phase 2
0.6735	Remote Similarity	NPD1607	Approved
0.6733	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6799	Approved
0.6731	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD3226	Approved
0.6731	Remote Similarity	NPD7458	Discontinued
0.6723	Remote Similarity	NPD9257	Approved
0.6723	Remote Similarity	NPD9259	Approved
0.6718	Remote Similarity	NPD2329	Discontinued
0.6714	Remote Similarity	NPD1608	Approved
0.6714	Remote Similarity	NPD6637	Approved
0.6712	Remote Similarity	NPD4307	Phase 2
0.6711	Remote Similarity	NPD2796	Approved
0.669	Remote Similarity	NPD1203	Approved
0.669	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD1087	Approved
0.6667	Remote Similarity	NPD1317	Discontinued
0.6667	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2613	Approved
0.6646	Remote Similarity	NPD7075	Discontinued
0.6646	Remote Similarity	NPD7411	Suspended
0.6645	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4110	Phase 3
0.6645	Remote Similarity	NPD2575	Approved
0.6644	Remote Similarity	NPD1510	Phase 2
0.6643	Remote Similarity	NPD3131	Approved
0.6643	Remote Similarity	NPD2610	Approved
0.6643	Remote Similarity	NPD2611	Approved
0.6643	Remote Similarity	NPD4217	Approved
0.6643	Remote Similarity	NPD4218	Approved
0.6643	Remote Similarity	NPD1019	Discontinued
0.6643	Remote Similarity	NPD4215	Approved
0.6643	Remote Similarity	NPD2612	Approved
0.6643	Remote Similarity	NPD2609	Approved
0.6643	Remote Similarity	NPD2608	Approved
0.6643	Remote Similarity	NPD4216	Approved
0.6643	Remote Similarity	NPD3132	Approved
0.6641	Remote Similarity	NPD9264	Approved
0.6641	Remote Similarity	NPD9267	Approved
0.6641	Remote Similarity	NPD9263	Approved
0.6623	Remote Similarity	NPD1549	Phase 2
0.662	Remote Similarity	NPD2199	Approved
0.662	Remote Similarity	NPD2198	Approved
0.662	Remote Similarity	NPD1876	Approved
0.6619	Remote Similarity	NPD5305	Approved
0.6619	Remote Similarity	NPD5306	Approved
0.6608	Remote Similarity	NPD6784	Approved
0.6608	Remote Similarity	NPD6785	Approved
0.6604	Remote Similarity	NPD6801	Discontinued
0.6603	Remote Similarity	NPD5403	Approved
0.66	Remote Similarity	NPD5408	Approved
0.66	Remote Similarity	NPD5405	Approved
0.66	Remote Similarity	NPD5406	Approved
0.66	Remote Similarity	NPD5404	Approved
0.6599	Remote Similarity	NPD1240	Approved
0.6597	Remote Similarity	NPD3661	Approved
0.6597	Remote Similarity	NPD3663	Approved
0.6597	Remote Similarity	NPD3662	Phase 3
0.6597	Remote Similarity	NPD3664	Approved
0.6591	Remote Similarity	NPD9266	Approved
0.6591	Remote Similarity	NPD74	Approved
0.6587	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD1239	Approved
0.6584	Remote Similarity	NPD7768	Phase 2
0.6582	Remote Similarity	NPD4380	Phase 2
0.6581	Remote Similarity	NPD5401	Approved
0.6575	Remote Similarity	NPD3268	Approved
0.6575	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD2797	Approved
0.6571	Remote Similarity	NPD4106	Approved
0.6571	Remote Similarity	NPD4135	Approved
0.6571	Remote Similarity	NPD4136	Approved
0.6569	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD7685	Pre-registration
0.6567	Remote Similarity	NPD9508	Approved
0.6567	Remote Similarity	NPD969	Suspended
0.6556	Remote Similarity	NPD5763	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