NPASS Compound

Structure

NPC472703 OpenBabel07101718272D 26 27 0 0 1 0 0 0 0 0999 V2000 1.0418 -1.7000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3757 -1.0767 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 1.5388 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 0.5878 0.8090 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 -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 1 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 10 1 0 0 0 0 5 11 1 0 0 0 0 6 8 1 0 0 0 0 6 15 2 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 19 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 20 1 0 0 0 0 13 26 1 0 0 0 0 14 17 1 0 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 24 2 0 0 0 0 18 26 1 0 0 0 0 19 21 1 0 0 0 0 20 3 1 6 0 0 0 20 25 1 0 0 0 0 21 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	362.21
Volume:	385.428
LogP:	4.098
LogD:	3.728
LogS:	-4.583
# Rotatable Bonds:	8
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	3.426
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.097
MDCK Permeability:	2.265549665025901e-05
Pgp-inhibitor:	0.029
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.124
Plasma Protein Binding (PPB):	96.42434692382812%
Volume Distribution (VD):	0.206
Pgp-substrate:	3.129648447036743%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.685
CYP2C19-inhibitor:	0.085
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.274
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.127

ADMET: Excretion

Clearance (CL):	8.022
Half-life (T1/2):	0.563

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.074
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.014
Skin Sensitization:	0.132
Carcinogencity:	0.031
Eye Corrosion:	0.006
Eye Irritation:	0.277
Respiratory Toxicity:	0.04

Download Data

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

Natural Product: NPC472703

Natural Product ID:	NPC472703
*Common Name:**	PMMJBYVOCQEGKR-NHCUHLMSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PMMJBYVOCQEGKR-NHCUHLMSSA-N
Standard InCHI:	InChI=1S/C21H30O5/c1-19(2)10-5-11-21(19,4)16-8-6-15(7-9-16)18(24)26-13-12-20(3,25)14-17(22)23/h6-9,25H,5,10-14H2,1-4H3,(H,22,23)/t20-,21-/m1/s1
SMILES:	CC1(CCCC1(C)C2=CC=C(C=C2)C(=O)OCCC(C)(CC(=O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581619
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	3

Activity Type	# Activity
Cell Line	1
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1460	Cell Line	L929	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[508298]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	MIC	=	67.0	ug.mL-1	PMID[508298]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	67.0	ug.mL-1	PMID[508298]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	67.0	ug.mL-1	PMID[508298]

☑ 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 NPC472703 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	225
0.1-0.2	952
0.2-0.3	2140
0.3-0.4	5668
0.4-0.5	11086
0.5-0.6	12672
0.6-0.7	8761
0.7-0.8	1081
0.8-0.85	95
0.85-0.9	13
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9914	High Similarity	NPC472704
0.9664	High Similarity	NPC472706
0.9106	High Similarity	NPC472707
0.8527	High Similarity	NPC233692
0.8527	High Similarity	NPC239358
0.8527	High Similarity	NPC233860
0.8516	High Similarity	NPC82712
0.8462	Intermediate Similarity	NPC472248
0.8448	Intermediate Similarity	NPC249811
0.8433	Intermediate Similarity	NPC242355
0.8433	Intermediate Similarity	NPC473497
0.8433	Intermediate Similarity	NPC475413
0.8433	Intermediate Similarity	NPC474303
0.8397	Intermediate Similarity	NPC28836
0.8397	Intermediate Similarity	NPC311492
0.8376	Intermediate Similarity	NPC469636
0.8374	Intermediate Similarity	NPC472708
0.8372	Intermediate Similarity	NPC272946
0.8333	Intermediate Similarity	NPC200154
0.8309	Intermediate Similarity	NPC45307
0.8308	Intermediate Similarity	NPC72915
0.8271	Intermediate Similarity	NPC202729
0.8258	Intermediate Similarity	NPC477359
0.8258	Intermediate Similarity	NPC153617
0.8258	Intermediate Similarity	NPC477368
0.8231	Intermediate Similarity	NPC475508
0.8209	Intermediate Similarity	NPC86772
0.8209	Intermediate Similarity	NPC27721
0.8197	Intermediate Similarity	NPC149691
0.8195	Intermediate Similarity	NPC79699
0.8195	Intermediate Similarity	NPC232888
0.8195	Intermediate Similarity	NPC477367
0.8182	Intermediate Similarity	NPC477364
0.8182	Intermediate Similarity	NPC307651
0.8148	Intermediate Similarity	NPC325805
0.8148	Intermediate Similarity	NPC272523
0.8148	Intermediate Similarity	NPC170718
0.8148	Intermediate Similarity	NPC473301
0.8134	Intermediate Similarity	NPC472551
0.8134	Intermediate Similarity	NPC472545
0.8129	Intermediate Similarity	NPC170668
0.8125	Intermediate Similarity	NPC295664
0.8125	Intermediate Similarity	NPC246166
0.812	Intermediate Similarity	NPC472250
0.812	Intermediate Similarity	NPC48929
0.811	Intermediate Similarity	NPC223351
0.8103	Intermediate Similarity	NPC474365
0.8103	Intermediate Similarity	NPC301943
0.8099	Intermediate Similarity	NPC128368
0.8095	Intermediate Similarity	NPC50872
0.8092	Intermediate Similarity	NPC147561
0.8092	Intermediate Similarity	NPC42234
0.8087	Intermediate Similarity	NPC70624
0.808	Intermediate Similarity	NPC204784
0.8074	Intermediate Similarity	NPC39549
0.8071	Intermediate Similarity	NPC205389
0.8062	Intermediate Similarity	NPC470765
0.806	Intermediate Similarity	NPC290833
0.806	Intermediate Similarity	NPC265459
0.806	Intermediate Similarity	NPC475262
0.806	Intermediate Similarity	NPC270364
0.8043	Intermediate Similarity	NPC153214
0.8033	Intermediate Similarity	NPC153053
0.8033	Intermediate Similarity	NPC474363
0.8029	Intermediate Similarity	NPC187566
0.8029	Intermediate Similarity	NPC77493
0.8017	Intermediate Similarity	NPC321852
0.8015	Intermediate Similarity	NPC9905
0.8	Intermediate Similarity	NPC52523
0.8	Intermediate Similarity	NPC194769
0.8	Intermediate Similarity	NPC285221
0.8	Intermediate Similarity	NPC469513
0.8	Intermediate Similarity	NPC473220
0.8	Intermediate Similarity	NPC203925
0.8	Intermediate Similarity	NPC470753
0.8	Intermediate Similarity	NPC217673
0.8	Intermediate Similarity	NPC110211
0.8	Intermediate Similarity	NPC325497
0.8	Intermediate Similarity	NPC204579
0.7985	Intermediate Similarity	NPC298547
0.7985	Intermediate Similarity	NPC203486
0.7985	Intermediate Similarity	NPC329913
0.7985	Intermediate Similarity	NPC134937
0.7985	Intermediate Similarity	NPC324898
0.7985	Intermediate Similarity	NPC126516
0.7971	Intermediate Similarity	NPC51181
0.7971	Intermediate Similarity	NPC183540
0.797	Intermediate Similarity	NPC477360
0.7967	Intermediate Similarity	NPC306740
0.7958	Intermediate Similarity	NPC477099
0.7958	Intermediate Similarity	NPC477097
0.7958	Intermediate Similarity	NPC477101
0.7958	Intermediate Similarity	NPC25484
0.7958	Intermediate Similarity	NPC232583
0.7956	Intermediate Similarity	NPC472547
0.7956	Intermediate Similarity	NPC162613
0.7956	Intermediate Similarity	NPC97667
0.7956	Intermediate Similarity	NPC87934
0.7956	Intermediate Similarity	NPC100913
0.7956	Intermediate Similarity	NPC90614
0.7956	Intermediate Similarity	NPC171207
0.7956	Intermediate Similarity	NPC275592
0.7955	Intermediate Similarity	NPC471832
0.7955	Intermediate Similarity	NPC194979
0.7939	Intermediate Similarity	NPC115797
0.7939	Intermediate Similarity	NPC51448
0.7934	Intermediate Similarity	NPC476003
0.7934	Intermediate Similarity	NPC260818
0.7929	Intermediate Similarity	NPC127857
0.7926	Intermediate Similarity	NPC472247
0.7926	Intermediate Similarity	NPC149401
0.7926	Intermediate Similarity	NPC279637
0.7923	Intermediate Similarity	NPC121272
0.7923	Intermediate Similarity	NPC275576
0.7923	Intermediate Similarity	NPC100402
0.7923	Intermediate Similarity	NPC9180
0.7923	Intermediate Similarity	NPC476033
0.792	Intermediate Similarity	NPC45794
0.7917	Intermediate Similarity	NPC83628
0.7917	Intermediate Similarity	NPC265407
0.7917	Intermediate Similarity	NPC17417
0.7917	Intermediate Similarity	NPC10251
0.7914	Intermediate Similarity	NPC95449
0.7914	Intermediate Similarity	NPC477094
0.7914	Intermediate Similarity	NPC82467
0.7914	Intermediate Similarity	NPC477096
0.7913	Intermediate Similarity	NPC35448
0.7913	Intermediate Similarity	NPC78701
0.7907	Intermediate Similarity	NPC85511
0.7907	Intermediate Similarity	NPC228739
0.7899	Intermediate Similarity	NPC266374
0.7899	Intermediate Similarity	NPC27377
0.7899	Intermediate Similarity	NPC472576
0.7899	Intermediate Similarity	NPC16912
0.7899	Intermediate Similarity	NPC97947
0.7899	Intermediate Similarity	NPC291599
0.7899	Intermediate Similarity	NPC118080
0.7899	Intermediate Similarity	NPC41481
0.7899	Intermediate Similarity	NPC224491
0.7899	Intermediate Similarity	NPC87448
0.7883	Intermediate Similarity	NPC276652
0.7874	Intermediate Similarity	NPC473243
0.7872	Intermediate Similarity	NPC478263
0.7869	Intermediate Similarity	NPC270699
0.7869	Intermediate Similarity	NPC82899
0.7863	Intermediate Similarity	NPC25458
0.7863	Intermediate Similarity	NPC169913
0.7863	Intermediate Similarity	NPC188895
0.7863	Intermediate Similarity	NPC304873
0.7852	Intermediate Similarity	NPC474608
0.7851	Intermediate Similarity	NPC196246
0.7851	Intermediate Similarity	NPC93084
0.7851	Intermediate Similarity	NPC214067
0.7851	Intermediate Similarity	NPC251854
0.7845	Intermediate Similarity	NPC146351
0.7845	Intermediate Similarity	NPC217621
0.7842	Intermediate Similarity	NPC472546
0.7842	Intermediate Similarity	NPC192658
0.7836	Intermediate Similarity	NPC238370
0.7836	Intermediate Similarity	NPC125153
0.7833	Intermediate Similarity	NPC56493
0.7832	Intermediate Similarity	NPC125033
0.7826	Intermediate Similarity	NPC251294
0.7826	Intermediate Similarity	NPC183270
0.7826	Intermediate Similarity	NPC276775
0.7826	Intermediate Similarity	NPC249912
0.7826	Intermediate Similarity	NPC475660
0.7826	Intermediate Similarity	NPC92754
0.7826	Intermediate Similarity	NPC477904
0.7823	Intermediate Similarity	NPC221275
0.7817	Intermediate Similarity	NPC132652
0.781	Intermediate Similarity	NPC205305
0.781	Intermediate Similarity	NPC327511
0.7805	Intermediate Similarity	NPC474176
0.7801	Intermediate Similarity	NPC25043
0.7801	Intermediate Similarity	NPC134131
0.7801	Intermediate Similarity	NPC478264
0.7794	Intermediate Similarity	NPC291638
0.7794	Intermediate Similarity	NPC477893
0.7794	Intermediate Similarity	NPC17877
0.7794	Intermediate Similarity	NPC195647
0.7794	Intermediate Similarity	NPC472577
0.7794	Intermediate Similarity	NPC66761
0.7793	Intermediate Similarity	NPC477100
0.7793	Intermediate Similarity	NPC477098
0.7787	Intermediate Similarity	NPC210089
0.7787	Intermediate Similarity	NPC474157
0.7787	Intermediate Similarity	NPC305912
0.7787	Intermediate Similarity	NPC1082
0.7786	Intermediate Similarity	NPC91703
0.7786	Intermediate Similarity	NPC79608
0.7786	Intermediate Similarity	NPC163087
0.7786	Intermediate Similarity	NPC477894
0.7786	Intermediate Similarity	NPC476599
0.7786	Intermediate Similarity	NPC477366
0.7778	Intermediate Similarity	NPC471103
0.7778	Intermediate Similarity	NPC51602
0.777	Intermediate Similarity	NPC473654
0.7769	Intermediate Similarity	NPC477362
0.7769	Intermediate Similarity	NPC85493

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 NPC472703 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	727
0.2-0.3	1393
0.3-0.4	2599
0.4-0.5	2482
0.5-0.6	1280
0.6-0.7	420
0.7-0.8	47
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
0.8092	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8083	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD2182	Approved
0.7801	Intermediate Similarity	NPD7236	Approved
0.7752	Intermediate Similarity	NPD6287	Discontinued
0.7727	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD7008	Discontinued
0.768	Intermediate Similarity	NPD5951	Approved
0.766	Intermediate Similarity	NPD4628	Phase 3
0.7655	Intermediate Similarity	NPD7239	Suspended
0.7623	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4198	Discontinued
0.7597	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD164	Approved
0.7578	Intermediate Similarity	NPD9545	Approved
0.7542	Intermediate Similarity	NPD1238	Approved
0.754	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD9493	Approved
0.7405	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD2066	Phase 3
0.7372	Intermediate Similarity	NPD3764	Approved
0.735	Intermediate Similarity	NPD1693	Approved
0.7333	Intermediate Similarity	NPD6085	Phase 2
0.7333	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD1088	Approved
0.7325	Intermediate Similarity	NPD7799	Discontinued
0.7324	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD2650	Approved
0.7323	Intermediate Similarity	NPD2652	Approved
0.7315	Intermediate Similarity	NPD6599	Discontinued
0.7302	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD2629	Approved
0.7266	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD5048	Discontinued
0.7213	Intermediate Similarity	NPD1930	Approved
0.7213	Intermediate Similarity	NPD1929	Approved
0.7213	Intermediate Similarity	NPD6647	Phase 2
0.7213	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2533	Approved
0.7211	Intermediate Similarity	NPD2532	Approved
0.7211	Intermediate Similarity	NPD2534	Approved
0.7197	Intermediate Similarity	NPD1778	Approved
0.7194	Intermediate Similarity	NPD7961	Discontinued
0.719	Intermediate Similarity	NPD7058	Phase 2
0.719	Intermediate Similarity	NPD7057	Phase 3
0.7188	Intermediate Similarity	NPD6010	Discontinued
0.7177	Intermediate Similarity	NPD6685	Approved
0.7176	Intermediate Similarity	NPD7741	Discontinued
0.7164	Intermediate Similarity	NPD3972	Approved
0.7164	Intermediate Similarity	NPD9717	Approved
0.7162	Intermediate Similarity	NPD6273	Approved
0.7155	Intermediate Similarity	NPD1090	Approved
0.7155	Intermediate Similarity	NPD9256	Approved
0.7155	Intermediate Similarity	NPD1086	Approved
0.7155	Intermediate Similarity	NPD1089	Approved
0.7155	Intermediate Similarity	NPD9258	Approved
0.7143	Intermediate Similarity	NPD2067	Discontinued
0.7143	Intermediate Similarity	NPD1989	Approved
0.7133	Intermediate Similarity	NPD1551	Phase 2
0.7131	Intermediate Similarity	NPD1932	Approved
0.7101	Intermediate Similarity	NPD6832	Phase 2
0.7095	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2346	Discontinued
0.7069	Intermediate Similarity	NPD800	Approved
0.7063	Intermediate Similarity	NPD4308	Phase 3
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7063	Intermediate Similarity	NPD2799	Discontinued
0.7055	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD1237	Approved
0.7016	Intermediate Similarity	NPD5909	Discontinued
0.7014	Intermediate Similarity	NPD2935	Discontinued
0.7	Intermediate Similarity	NPD2313	Discontinued
0.7	Intermediate Similarity	NPD411	Approved
0.6993	Remote Similarity	NPD2569	Approved
0.6993	Remote Similarity	NPD2567	Approved
0.6986	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6858	Approved
0.6977	Remote Similarity	NPD7094	Approved
0.6975	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1202	Approved
0.6972	Remote Similarity	NPD230	Phase 1
0.697	Remote Similarity	NPD7610	Discontinued
0.6966	Remote Similarity	NPD6002	Phase 3
0.6966	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6004	Phase 3
0.6966	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6005	Phase 3
0.6957	Remote Similarity	NPD9257	Approved
0.6957	Remote Similarity	NPD2798	Approved
0.6957	Remote Similarity	NPD9259	Approved
0.6948	Remote Similarity	NPD7819	Suspended
0.6939	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7003	Approved
0.6935	Remote Similarity	NPD5765	Approved
0.6935	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2329	Discontinued
0.6923	Remote Similarity	NPD1607	Approved
0.6918	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD7009	Phase 2
0.6913	Remote Similarity	NPD6799	Approved
0.6912	Remote Similarity	NPD6637	Approved
0.6912	Remote Similarity	NPD1608	Approved
0.6908	Remote Similarity	NPD3226	Approved
0.6908	Remote Similarity	NPD7458	Discontinued
0.6901	Remote Similarity	NPD4307	Phase 2
0.6897	Remote Similarity	NPD1087	Approved
0.6885	Remote Similarity	NPD9495	Approved
0.6884	Remote Similarity	NPD1203	Approved
0.6875	Remote Similarity	NPD1317	Discontinued
0.685	Remote Similarity	NPD9264	Approved
0.685	Remote Similarity	NPD9263	Approved
0.685	Remote Similarity	NPD9267	Approved
0.6849	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1019	Discontinued
0.6835	Remote Similarity	NPD5647	Approved
0.6831	Remote Similarity	NPD6663	Approved
0.6831	Remote Similarity	NPD7713	Phase 3
0.6828	Remote Similarity	NPD7305	Phase 1
0.6828	Remote Similarity	NPD1510	Phase 2
0.6818	Remote Similarity	NPD7411	Suspended
0.6815	Remote Similarity	NPD5306	Approved
0.6815	Remote Similarity	NPD5305	Approved
0.6815	Remote Similarity	NPD5125	Phase 3
0.6815	Remote Similarity	NPD5126	Approved
0.6812	Remote Similarity	NPD1876	Approved
0.6807	Remote Similarity	NPD1239	Approved
0.6797	Remote Similarity	NPD74	Approved
0.6797	Remote Similarity	NPD9266	Approved
0.6786	Remote Similarity	NPD5736	Approved
0.6783	Remote Similarity	NPD1240	Approved
0.6781	Remote Similarity	NPD5406	Approved
0.6781	Remote Similarity	NPD5408	Approved
0.6781	Remote Similarity	NPD5404	Approved
0.6781	Remote Similarity	NPD2796	Approved
0.6781	Remote Similarity	NPD5405	Approved
0.6769	Remote Similarity	NPD6912	Phase 3
0.6769	Remote Similarity	NPD9508	Approved
0.6765	Remote Similarity	NPD4135	Approved
0.6765	Remote Similarity	NPD4136	Approved
0.6765	Remote Similarity	NPD4106	Approved
0.6763	Remote Similarity	NPD2797	Approved
0.6761	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3268	Approved
0.6752	Remote Similarity	NPD7768	Phase 2
0.6744	Remote Similarity	NPD4233	Approved
0.6744	Remote Similarity	NPD4234	Approved
0.6742	Remote Similarity	NPD4766	Approved
0.6741	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD447	Suspended
0.6736	Remote Similarity	NPD6355	Discontinued
0.6736	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5761	Phase 2
0.6731	Remote Similarity	NPD5760	Phase 2
0.6727	Remote Similarity	NPD8368	Discontinued
0.6723	Remote Similarity	NPD3673	Approved
0.6723	Remote Similarity	NPD3672	Approved
0.6719	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD5277	Phase 2
0.6715	Remote Similarity	NPD4807	Approved
0.6715	Remote Similarity	NPD4806	Approved
0.6713	Remote Similarity	NPD7714	Approved
0.6713	Remote Similarity	NPD7715	Approved
0.6711	Remote Similarity	NPD8166	Discontinued
0.6711	Remote Similarity	NPD3750	Approved
0.6711	Remote Similarity	NPD4110	Phase 3
0.6711	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7075	Discontinued
0.6707	Remote Similarity	NPD8407	Phase 2
0.6696	Remote Similarity	NPD9491	Approved
0.6691	Remote Similarity	NPD2198	Approved
0.6691	Remote Similarity	NPD17	Approved
0.6691	Remote Similarity	NPD2199	Approved
0.6691	Remote Similarity	NPD1283	Approved
0.6689	Remote Similarity	NPD1549	Phase 2
0.6688	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9261	Approved
0.6667	Remote Similarity	NPD1564	Approved
0.6667	Remote Similarity	NPD3661	Approved
0.6667	Remote Similarity	NPD1565	Approved
0.6667	Remote Similarity	NPD3662	Phase 3
0.6667	Remote Similarity	NPD3664	Approved
0.6667	Remote Similarity	NPD3663	Approved
0.6667	Remote Similarity	NPD1566	Phase 3
0.6645	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2800	Approved
0.6643	Remote Similarity	NPD1164	Approved
0.6643	Remote Similarity	NPD6362	Approved
0.6641	Remote Similarity	NPD969	Suspended
0.6627	Remote Similarity	NPD8434	Phase 2
0.6622	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD1550	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data