NPASS Compound

Structure

NPC469513 OpenBabel07101718182D 24 27 0 0 1 0 0 0 0 0999 V2000 2.0396 0.2424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5075 -2.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1904 -3.9701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2479 -3.6357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9512 -3.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0664 -2.6523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7696 -2.3378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1270 0.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9424 -1.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8272 -2.0034 0.0000 C 0 0 0 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 0.5329 0.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6457 -1.0200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5645 -1.4448 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3349 -0.4671 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4210 1.3286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4065 -0.3711 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3981 -1.9174 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4212 -2.4345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7033 -0.6855 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2319 -1.1783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 8 18 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 10 23 1 0 0 0 0 11 14 1 0 0 0 0 12 13 1 0 0 0 0 12 17 1 1 0 0 0 13 19 2 0 0 0 0 14 20 2 0 0 0 0 14 23 1 0 0 0 0 15 17 1 6 0 0 0 15 22 1 0 0 0 0 15 24 1 0 0 0 0 16 18 1 1 0 0 0 16 24 1 0 0 0 0 17 18 1 1 0 0 0 18 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.13
Volume:	325.217
LogP:	1.802
LogD:	1.422
LogS:	-3.968
# Rotatable Bonds:	5
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.838
Synthetic Accessibility Score:	5.352
Fsp3:	0.556
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:	-5.299
MDCK Permeability:	2.994126953126397e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.077
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.132
30% Bioavailability (F30%):	0.469

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.843
Plasma Protein Binding (PPB):	65.63927459716797%
Volume Distribution (VD):	0.463
Pgp-substrate:	39.22251892089844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.982
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.719
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.556
CYP3A4-substrate:	0.525

ADMET: Excretion

Clearance (CL):	6.951
Half-life (T1/2):	0.33

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.169
Drug-inuced Liver Injury (DILI):	0.559
AMES Toxicity:	0.976
Rat Oral Acute Toxicity:	0.757
Maximum Recommended Daily Dose:	0.491
Skin Sensitization:	0.308
Carcinogencity:	0.966
Eye Corrosion:	0.006
Eye Irritation:	0.093
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC469513

Natural Product ID:	NPC469513
*Common Name:**	Paeonidangenin
IUPAC Name:	n.a.
Synonyms:	Paeonidangenin
Standard InCHIKey:	GHLQXVJMYVGPCU-CAXGVCPASA-N
Standard InCHI:	InChI=1S/C18H20O6/c1-16-9-13(19)12-8-18(16,21)17(12,15(22-2)24-16)10-23-14(20)11-6-4-3-5-7-11/h3-7,12,15,21H,8-10H2,1-2H3/t12-,15+,16+,17+,18-/m1/s1
SMILES:	CC12CC(=O)C3CC1(C3(C(O2)OC)COC(=O)C4=CC=CC=C4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081704
PubChem CID:	46883511
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	roots	n.a.	n.a.	PMID[19691309]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
Others	4

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	89.9	%	PMID[553280]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	91.5	%	PMID[553280]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	85.0	%	PMID[553280]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	66.2	%	PMID[553280]
NPT848	Cell Line	N9	Homo sapiens	IC50	>	100000.0	nM	PMID[553280]

☑ 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 NPC469513 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	305
0.1-0.2	1185
0.2-0.3	2422
0.3-0.4	5118
0.4-0.5	9890
0.5-0.6	10761
0.6-0.7	11070
0.7-0.8	1701
0.8-0.85	227
0.85-0.9	15
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9444	High Similarity	NPC133430
0.9444	High Similarity	NPC469477
0.9384	High Similarity	NPC469417
0.9353	High Similarity	NPC77493
0.9189	High Similarity	NPC469399
0.9116	High Similarity	NPC5115
0.9013	High Similarity	NPC477627
0.8973	High Similarity	NPC469448
0.8859	High Similarity	NPC469456
0.8844	High Similarity	NPC222102
0.8844	High Similarity	NPC303429
0.8839	High Similarity	NPC469420
0.8828	High Similarity	NPC127857
0.8784	High Similarity	NPC51602
0.8784	High Similarity	NPC469415
0.8784	High Similarity	NPC471103
0.8782	High Similarity	NPC469419
0.8767	High Similarity	NPC477737
0.8733	High Similarity	NPC469422
0.8733	High Similarity	NPC34066
0.8716	High Similarity	NPC91730
0.8658	High Similarity	NPC197037
0.8649	High Similarity	NPC60509
0.8649	High Similarity	NPC250046
0.8649	High Similarity	NPC81698
0.8645	High Similarity	NPC471493
0.8616	High Similarity	NPC469421
0.8611	High Similarity	NPC97667
0.8611	High Similarity	NPC275592
0.8611	High Similarity	NPC171207
0.8611	High Similarity	NPC100913
0.8609	High Similarity	NPC473670
0.8609	High Similarity	NPC21410
0.8609	High Similarity	NPC469398
0.8609	High Similarity	NPC282239
0.86	High Similarity	NPC472548
0.86	High Similarity	NPC477905
0.8599	High Similarity	NPC102465
0.8591	High Similarity	NPC112216
0.8591	High Similarity	NPC198455
0.8591	High Similarity	NPC161239
0.8591	High Similarity	NPC7095
0.8591	High Similarity	NPC165260
0.8581	High Similarity	NPC150893
0.8581	High Similarity	NPC329960
0.8581	High Similarity	NPC295408
0.8581	High Similarity	NPC217918
0.8571	High Similarity	NPC471107
0.8571	High Similarity	NPC471100
0.8553	High Similarity	NPC106895
0.8553	High Similarity	NPC217091
0.8552	High Similarity	NPC27377
0.8552	High Similarity	NPC41481
0.8552	High Similarity	NPC291599
0.8552	High Similarity	NPC472576
0.8552	High Similarity	NPC118080
0.8552	High Similarity	NPC87448
0.8552	High Similarity	NPC16912
0.8552	High Similarity	NPC97947
0.8543	High Similarity	NPC248265
0.8543	High Similarity	NPC229545
0.8543	High Similarity	NPC219419
0.8543	High Similarity	NPC11588
0.8543	High Similarity	NPC134685
0.8533	High Similarity	NPC101043
0.8533	High Similarity	NPC306799
0.8531	High Similarity	NPC472551
0.8531	High Similarity	NPC472545
0.8506	High Similarity	NPC477623
0.8497	Intermediate Similarity	NPC472393
0.8497	Intermediate Similarity	NPC477735
0.8487	Intermediate Similarity	NPC114357
0.8487	Intermediate Similarity	NPC155329
0.8487	Intermediate Similarity	NPC259144
0.8487	Intermediate Similarity	NPC472549
0.8483	Intermediate Similarity	NPC477904
0.8483	Intermediate Similarity	NPC183270
0.8483	Intermediate Similarity	NPC90614
0.8483	Intermediate Similarity	NPC472547
0.8472	Intermediate Similarity	NPC39549
0.8462	Intermediate Similarity	NPC473216
0.8462	Intermediate Similarity	NPC473399
0.8462	Intermediate Similarity	NPC477893
0.8462	Intermediate Similarity	NPC477896
0.8456	Intermediate Similarity	NPC132652
0.8442	Intermediate Similarity	NPC477736
0.8442	Intermediate Similarity	NPC471102
0.8435	Intermediate Similarity	NPC477894
0.8435	Intermediate Similarity	NPC91703
0.8428	Intermediate Similarity	NPC477471
0.8428	Intermediate Similarity	NPC477473
0.8428	Intermediate Similarity	NPC477466
0.8428	Intermediate Similarity	NPC477469
0.8421	Intermediate Similarity	NPC242262
0.8421	Intermediate Similarity	NPC472658
0.8421	Intermediate Similarity	NPC304876
0.8421	Intermediate Similarity	NPC158333
0.8421	Intermediate Similarity	NPC1173
0.8421	Intermediate Similarity	NPC472030
0.8421	Intermediate Similarity	NPC472005
0.8421	Intermediate Similarity	NPC265395
0.8421	Intermediate Similarity	NPC257213
0.8421	Intermediate Similarity	NPC77719
0.8421	Intermediate Similarity	NPC249471
0.8421	Intermediate Similarity	NPC256142
0.8421	Intermediate Similarity	NPC472657
0.8421	Intermediate Similarity	NPC473414
0.8421	Intermediate Similarity	NPC472022
0.8421	Intermediate Similarity	NPC237549
0.8408	Intermediate Similarity	NPC117943
0.8408	Intermediate Similarity	NPC293568
0.8397	Intermediate Similarity	NPC55744
0.8397	Intermediate Similarity	NPC43304
0.8397	Intermediate Similarity	NPC477188
0.8397	Intermediate Similarity	NPC477190
0.8392	Intermediate Similarity	NPC474608
0.8389	Intermediate Similarity	NPC478263
0.8378	Intermediate Similarity	NPC188865
0.8378	Intermediate Similarity	NPC475122
0.8378	Intermediate Similarity	NPC470152
0.8378	Intermediate Similarity	NPC57628
0.8378	Intermediate Similarity	NPC11685
0.8378	Intermediate Similarity	NPC125106
0.8378	Intermediate Similarity	NPC472573
0.8378	Intermediate Similarity	NPC95265
0.8378	Intermediate Similarity	NPC472569
0.8378	Intermediate Similarity	NPC475759
0.8378	Intermediate Similarity	NPC70716
0.8378	Intermediate Similarity	NPC241951
0.8378	Intermediate Similarity	NPC163719
0.8378	Intermediate Similarity	NPC476974
0.8378	Intermediate Similarity	NPC472570
0.8378	Intermediate Similarity	NPC25768
0.8378	Intermediate Similarity	NPC95810
0.8367	Intermediate Similarity	NPC182869
0.8366	Intermediate Similarity	NPC114410
0.8366	Intermediate Similarity	NPC26033
0.8366	Intermediate Similarity	NPC112523
0.8366	Intermediate Similarity	NPC228204
0.8354	Intermediate Similarity	NPC469418
0.8354	Intermediate Similarity	NPC477491
0.8344	Intermediate Similarity	NPC476173
0.8344	Intermediate Similarity	NPC478073
0.8344	Intermediate Similarity	NPC254558
0.8344	Intermediate Similarity	NPC66193
0.8333	Intermediate Similarity	NPC291638
0.8333	Intermediate Similarity	NPC17877
0.8333	Intermediate Similarity	NPC472577
0.8333	Intermediate Similarity	NPC195647
0.8333	Intermediate Similarity	NPC66761
0.8322	Intermediate Similarity	NPC29704
0.8322	Intermediate Similarity	NPC476973
0.8322	Intermediate Similarity	NPC70403
0.8322	Intermediate Similarity	NPC472572
0.8322	Intermediate Similarity	NPC472575
0.8322	Intermediate Similarity	NPC184817
0.8322	Intermediate Similarity	NPC478264
0.8322	Intermediate Similarity	NPC177940
0.8322	Intermediate Similarity	NPC470159
0.8322	Intermediate Similarity	NPC470157
0.8322	Intermediate Similarity	NPC200471
0.8322	Intermediate Similarity	NPC473088
0.8322	Intermediate Similarity	NPC472571
0.8322	Intermediate Similarity	NPC174982
0.8322	Intermediate Similarity	NPC472568
0.8322	Intermediate Similarity	NPC469349
0.8322	Intermediate Similarity	NPC158663
0.8322	Intermediate Similarity	NPC471104
0.8322	Intermediate Similarity	NPC96903
0.8322	Intermediate Similarity	NPC171525
0.8313	Intermediate Similarity	NPC469458
0.8313	Intermediate Similarity	NPC88176
0.8313	Intermediate Similarity	NPC469459
0.8313	Intermediate Similarity	NPC469396
0.8313	Intermediate Similarity	NPC149002
0.8312	Intermediate Similarity	NPC11410
0.8311	Intermediate Similarity	NPC163087
0.8311	Intermediate Similarity	NPC95449
0.8302	Intermediate Similarity	NPC120012
0.8299	Intermediate Similarity	NPC213567
0.8299	Intermediate Similarity	NPC224491
0.8291	Intermediate Similarity	NPC471134
0.8289	Intermediate Similarity	NPC470153
0.8278	Intermediate Similarity	NPC473215
0.8267	Intermediate Similarity	NPC474935
0.8258	Intermediate Similarity	NPC469771
0.8258	Intermediate Similarity	NPC181924
0.8255	Intermediate Similarity	NPC38696
0.8255	Intermediate Similarity	NPC80895
0.8255	Intermediate Similarity	NPC471912
0.825	Intermediate Similarity	NPC265600
0.8247	Intermediate Similarity	NPC473632
0.8247	Intermediate Similarity	NPC473611
0.8247	Intermediate Similarity	NPC251139
0.8247	Intermediate Similarity	NPC132599
0.8247	Intermediate Similarity	NPC469730
0.8243	Intermediate Similarity	NPC34012
0.8243	Intermediate Similarity	NPC472546
0.8243	Intermediate Similarity	NPC183540
0.8239	Intermediate Similarity	NPC147561

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 NPC469513 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	733
0.2-0.3	1600
0.3-0.4	2826
0.4-0.5	2331
0.5-0.6	1052
0.6-0.7	334
0.7-0.8	18
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8148	Intermediate Similarity	NPD7799	Discontinued
0.8024	Intermediate Similarity	NPD8407	Phase 2
0.7986	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD8368	Discontinued
0.7727	Intermediate Similarity	NPD7236	Approved
0.7703	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD8434	Phase 2
0.7529	Intermediate Similarity	NPD8361	Approved
0.7529	Intermediate Similarity	NPD8435	Approved
0.7529	Intermediate Similarity	NPD8360	Approved
0.7484	Intermediate Similarity	NPD7239	Suspended
0.7414	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4628	Phase 3
0.7329	Intermediate Similarity	NPD7458	Discontinued
0.7294	Intermediate Similarity	NPD3818	Discontinued
0.7284	Intermediate Similarity	NPD6599	Discontinued
0.7257	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2533	Approved
0.7188	Intermediate Similarity	NPD2534	Approved
0.7188	Intermediate Similarity	NPD2532	Approved
0.7181	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5126	Approved
0.7172	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5125	Phase 3
0.7169	Intermediate Similarity	NPD7057	Phase 3
0.7169	Intermediate Similarity	NPD7058	Phase 2
0.7143	Intermediate Similarity	NPD8313	Approved
0.7143	Intermediate Similarity	NPD8312	Approved
0.7126	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6559	Discontinued
0.7125	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD2629	Approved
0.7105	Intermediate Similarity	NPD3764	Approved
0.7099	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD37	Approved
0.7088	Intermediate Similarity	NPD8485	Approved
0.7083	Intermediate Similarity	NPD6234	Discontinued
0.7081	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4965	Approved
0.7066	Intermediate Similarity	NPD4966	Approved
0.7066	Intermediate Similarity	NPD4967	Phase 2
0.7063	Intermediate Similarity	NPD4198	Discontinued
0.705	Intermediate Similarity	NPD2182	Approved
0.7048	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7819	Suspended
0.7035	Intermediate Similarity	NPD7473	Discontinued
0.7029	Intermediate Similarity	NPD7685	Pre-registration
0.7022	Intermediate Similarity	NPD8150	Discontinued
0.7019	Intermediate Similarity	NPD6799	Approved
0.6978	Remote Similarity	NPD6535	Approved
0.6978	Remote Similarity	NPD6534	Approved
0.6968	Remote Similarity	NPD230	Phase 1
0.6964	Remote Similarity	NPD3882	Suspended
0.6962	Remote Similarity	NPD2346	Discontinued
0.6959	Remote Similarity	NPD6232	Discontinued
0.6948	Remote Similarity	NPD7961	Discontinued
0.6946	Remote Similarity	NPD5761	Phase 2
0.6946	Remote Similarity	NPD5760	Phase 2
0.6944	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD2799	Discontinued
0.6941	Remote Similarity	NPD5494	Approved
0.6937	Remote Similarity	NPD8166	Discontinued
0.6928	Remote Similarity	NPD7008	Discontinued
0.6927	Remote Similarity	NPD8462	Phase 1
0.6923	Remote Similarity	NPD7075	Discontinued
0.6915	Remote Similarity	NPD8320	Phase 1
0.6915	Remote Similarity	NPD8319	Approved
0.6914	Remote Similarity	NPD7074	Phase 3
0.6909	Remote Similarity	NPD3226	Approved
0.6905	Remote Similarity	NPD3817	Phase 2
0.6901	Remote Similarity	NPD7199	Phase 2
0.6897	Remote Similarity	NPD7228	Approved
0.6893	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5951	Approved
0.6875	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4380	Phase 2
0.6867	Remote Similarity	NPD7028	Phase 2
0.6865	Remote Similarity	NPD7699	Phase 2
0.6865	Remote Similarity	NPD7700	Phase 2
0.6862	Remote Similarity	NPD7435	Discontinued
0.6857	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7054	Approved
0.6855	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6287	Discontinued
0.6845	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD6764	Approved
0.6836	Remote Similarity	NPD6765	Approved
0.6832	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7472	Approved
0.6813	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD9545	Approved
0.6792	Remote Similarity	NPD2935	Discontinued
0.6791	Remote Similarity	NPD6778	Approved
0.6791	Remote Similarity	NPD6782	Approved
0.6791	Remote Similarity	NPD6779	Approved
0.6791	Remote Similarity	NPD6776	Approved
0.6791	Remote Similarity	NPD6781	Approved
0.6791	Remote Similarity	NPD6777	Approved
0.6791	Remote Similarity	NPD6780	Approved
0.679	Remote Similarity	NPD6190	Approved
0.6786	Remote Similarity	NPD8404	Phase 2
0.6786	Remote Similarity	NPD6801	Discontinued
0.6786	Remote Similarity	NPD1934	Approved
0.6783	Remote Similarity	NPD969	Suspended
0.6783	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6797	Phase 2
0.6779	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2313	Discontinued
0.677	Remote Similarity	NPD2800	Approved
0.6765	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD164	Approved
0.6761	Remote Similarity	NPD5844	Phase 1
0.675	Remote Similarity	NPD7266	Discontinued
0.6746	Remote Similarity	NPD2801	Approved
0.6742	Remote Similarity	NPD7240	Approved
0.6742	Remote Similarity	NPD7251	Discontinued
0.6739	Remote Similarity	NPD6212	Phase 3
0.6739	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6213	Phase 3
0.6732	Remote Similarity	NPD2798	Approved
0.6727	Remote Similarity	NPD6273	Approved
0.6726	Remote Similarity	NPD7411	Suspended
0.6725	Remote Similarity	NPD3749	Approved
0.6713	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8127	Discontinued
0.6705	Remote Similarity	NPD3751	Discontinued
0.6704	Remote Similarity	NPD7808	Phase 3
0.6691	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD1930	Approved
0.6691	Remote Similarity	NPD1929	Approved
0.6687	Remote Similarity	NPD920	Approved
0.6685	Remote Similarity	NPD6784	Approved
0.6685	Remote Similarity	NPD6785	Approved
0.6667	Remote Similarity	NPD3787	Discontinued
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5711	Approved
0.6667	Remote Similarity	NPD5710	Approved
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7874	Approved
0.6647	Remote Similarity	NPD8455	Phase 2
0.6646	Remote Similarity	NPD1471	Phase 3
0.6626	Remote Similarity	NPD7003	Approved
0.6626	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7305	Phase 1
0.6625	Remote Similarity	NPD1510	Phase 2
0.6608	Remote Similarity	NPD5402	Approved
0.6604	Remote Similarity	NPD1607	Approved
0.66	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8151	Discontinued
0.6597	Remote Similarity	NPD7696	Phase 3
0.6597	Remote Similarity	NPD7697	Approved
0.6597	Remote Similarity	NPD7698	Approved
0.6596	Remote Similarity	NPD5048	Discontinued
0.6594	Remote Similarity	NPD1238	Approved
0.6594	Remote Similarity	NPD2066	Phase 3
0.659	Remote Similarity	NPD919	Approved
0.6585	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD5408	Approved
0.6584	Remote Similarity	NPD5406	Approved
0.6584	Remote Similarity	NPD5405	Approved
0.6584	Remote Similarity	NPD5404	Approved
0.6584	Remote Similarity	NPD2796	Approved
0.6582	Remote Similarity	NPD943	Approved
0.6582	Remote Similarity	NPD1240	Approved
0.6579	Remote Similarity	NPD3972	Approved
0.6579	Remote Similarity	NPD1608	Approved
0.6577	Remote Similarity	NPD7741	Discontinued
0.6575	Remote Similarity	NPD6010	Discontinued
0.6566	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7870	Phase 2
0.6562	Remote Similarity	NPD7871	Phase 2
0.6558	Remote Similarity	NPD1470	Approved
0.6546	Remote Similarity	NPD7701	Phase 2
0.6545	Remote Similarity	NPD6823	Phase 2
0.6543	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2344	Approved
0.6541	Remote Similarity	NPD447	Suspended
0.6541	Remote Similarity	NPD6355	Discontinued
0.6541	Remote Similarity	NPD1933	Approved
0.6531	Remote Similarity	NPD7801	Approved
0.6528	Remote Similarity	NPD2067	Discontinued
0.6528	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3750	Approved
0.6524	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4110	Phase 3
0.6522	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7033	Discontinued
0.6516	Remote Similarity	NPD6085	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data