NPASS Compound

Structure

NPC469417 OpenBabel07101719402D 43 48 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 3.5791 3.9344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3489 -0.7055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5726 3.8204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9837 3.1310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4065 -0.3711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5305 -1.6889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9706 2.9031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3817 2.2136 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 -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 4.5759 -0.5385 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 4.3752 2.0997 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 3.9805 -1.3419 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3785 -2.2592 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7831 -3.0626 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7896 -2.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7733 1.1823 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 2.3915 -2.0313 0.0000 C 0 0 1 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 5.3720 -2.3732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1811 -3.9800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1942 -3.7521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7668 1.0683 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2479 -3.6357 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 4.1778 0.3789 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1240 -2.3178 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9870 -1.2279 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 1.2319 -1.1783 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 38 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 13 31 1 0 0 0 0 14 20 1 0 0 0 0 14 29 1 0 0 0 0 15 39 1 0 0 0 0 16 30 1 0 0 0 0 16 40 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 30 1 1 0 0 0 20 32 2 0 0 0 0 21 15 1 6 0 0 0 21 22 1 0 0 0 0 21 41 1 0 0 0 0 22 23 1 0 0 0 0 22 33 1 1 0 0 0 23 24 1 0 0 0 0 23 34 1 6 0 0 0 24 27 1 0 0 0 0 24 35 1 1 0 0 0 25 36 2 0 0 0 0 25 39 1 0 0 0 0 26 37 2 0 0 0 0 26 40 1 0 0 0 0 27 41 1 0 0 0 0 27 42 1 6 0 0 0 28 30 1 6 0 0 0 28 38 1 0 0 0 0 28 43 1 0 0 0 0 29 31 1 1 0 0 0 29 43 1 0 0 0 0 30 31 1 1 0 0 0 31 42 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	598.21
Volume:	575.148
LogP:	2.317
LogD:	1.605
LogS:	-4.18
# Rotatable Bonds:	11
TPSA:	167.28
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.351
Synthetic Accessibility Score:	5.868
Fsp3:	0.516
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.85
MDCK Permeability:	3.5363238566787913e-05
Pgp-inhibitor:	0.622
Pgp-substrate:	0.969
Human Intestinal Absorption (HIA):	0.123
20% Bioavailability (F20%):	0.71
30% Bioavailability (F30%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.22
Plasma Protein Binding (PPB):	91.71196746826172%
Volume Distribution (VD):	0.696
Pgp-substrate:	7.682213306427002%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.974
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.266
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.239
CYP3A4-substrate:	0.355

ADMET: Excretion

Clearance (CL):	7.183
Half-life (T1/2):	0.64

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.818
AMES Toxicity:	0.929
Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.634
Carcinogencity:	0.369
Eye Corrosion:	0.003
Eye Irritation:	0.226
Respiratory Toxicity:	0.817

Download Data

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

Natural Product: NPC469417

Natural Product ID:	NPC469417
*Common Name:**	Paeonidanin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FHQISCVSTDQXSV-WNKDLFHOSA-N
Standard InCHI:	InChI=1S/C31H34O12/c1-29-14-20(32)19-13-31(29,30(19,28(38-2)43-29)16-40-26(37)18-11-7-4-8-12-18)42-27-24(35)23(34)22(33)21(41-27)15-39-25(36)17-9-5-3-6-10-17/h3-12,19,21-24,27-28,33-35H,13-16H2,1-2H3/t19-,21-,22-,23+,24-,27+,28+,29+,30+,31-/m1/s1
SMILES:	CC12CC(=O)C3CC1(C3(C(O2)OC)COC(=O)C4=CC=CC=C4)OC5C(C(C(C(O5)COC(=O)C6=CC=CC=C6)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078412
PubChem CID:	44253993
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11339628]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17260795]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	Daejeon, Korea	2007-Jan	PMID[19670875]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	roots	n.a.	n.a.	PMID[19691309]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[20822014]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[22547314]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	root bark	Bozhou, Anhui Province, China	2010-AUG	PMID[24377852]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	flower	n.a.	PMID[24504864]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	Flowers	LuoYang, HeNan, China	n.a.	PMID[24621197]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30226	Paeonia albiflora	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22550	Paeonia suffruticosa	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2
Others	4

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	86.6	%	PMID[544717]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	74.9	%	PMID[544717]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	59.1	%	PMID[544717]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	57.2	%	PMID[544717]
NPT848	Cell Line	N9	Homo sapiens	IC50	=	36200.0	nM	PMID[544717]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[544718]

☑ 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 NPC469417 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	333
0.1-0.2	1201
0.2-0.3	2523
0.3-0.4	4877
0.4-0.5	9725
0.5-0.6	11269
0.6-0.7	10067
0.7-0.8	2308
0.8-0.85	205
0.85-0.9	173
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9797	High Similarity	NPC469399
0.9589	High Similarity	NPC469448
0.9527	High Similarity	NPC133430
0.9527	High Similarity	NPC469477
0.9419	High Similarity	NPC469420
0.9384	High Similarity	NPC469513
0.9359	High Similarity	NPC469419
0.9333	High Similarity	NPC34066
0.9333	High Similarity	NPC5115
0.9205	High Similarity	NPC469422
0.92	High Similarity	NPC472548
0.92	High Similarity	NPC477905
0.9182	High Similarity	NPC469421
0.9103	High Similarity	NPC477627
0.9079	High Similarity	NPC469456
0.9079	High Similarity	NPC472549
0.9051	High Similarity	NPC102465
0.9041	High Similarity	NPC77493
0.9038	High Similarity	NPC150893
0.9038	High Similarity	NPC295408
0.9038	High Similarity	NPC329960
0.902	High Similarity	NPC106895
0.9007	High Similarity	NPC471103
0.9007	High Similarity	NPC469415
0.9	High Similarity	NPC60509
0.9	High Similarity	NPC250046
0.9	High Similarity	NPC81698
0.8994	High Similarity	NPC477471
0.8994	High Similarity	NPC477473
0.8994	High Similarity	NPC477466
0.8994	High Similarity	NPC477469
0.8981	High Similarity	NPC471493
0.8968	High Similarity	NPC477623
0.8954	High Similarity	NPC469398
0.8954	High Similarity	NPC282239
0.894	High Similarity	NPC165260
0.894	High Similarity	NPC198455
0.894	High Similarity	NPC161239
0.894	High Similarity	NPC303429
0.894	High Similarity	NPC222102
0.894	High Similarity	NPC7095
0.8926	High Similarity	NPC127857
0.8917	High Similarity	NPC66193
0.8902	High Similarity	NPC469418
0.8896	High Similarity	NPC217091
0.8889	High Similarity	NPC473414
0.8889	High Similarity	NPC1173
0.8889	High Similarity	NPC472030
0.8889	High Similarity	NPC242262
0.8889	High Similarity	NPC158333
0.8889	High Similarity	NPC265395
0.8889	High Similarity	NPC472005
0.8889	High Similarity	NPC249471
0.8889	High Similarity	NPC237549
0.8889	High Similarity	NPC256142
0.8889	High Similarity	NPC472022
0.8889	High Similarity	NPC304876
0.8889	High Similarity	NPC257213
0.8882	High Similarity	NPC51602
0.8875	High Similarity	NPC469396
0.8875	High Similarity	NPC149002
0.8875	High Similarity	NPC88176
0.8875	High Similarity	NPC469458
0.8867	High Similarity	NPC477737
0.8861	High Similarity	NPC471134
0.8859	High Similarity	NPC470152
0.8859	High Similarity	NPC241951
0.8859	High Similarity	NPC475759
0.8839	High Similarity	NPC472393
0.8839	High Similarity	NPC477735
0.8831	High Similarity	NPC473670
0.8831	High Similarity	NPC21410
0.8831	High Similarity	NPC228204
0.8831	High Similarity	NPC26033
0.8831	High Similarity	NPC112523
0.8831	High Similarity	NPC114410
0.8816	High Similarity	NPC112216
0.8816	High Similarity	NPC91730
0.8805	High Similarity	NPC61891
0.8805	High Similarity	NPC477491
0.88	High Similarity	NPC472568
0.88	High Similarity	NPC469349
0.88	High Similarity	NPC171525
0.88	High Similarity	NPC472572
0.88	High Similarity	NPC174982
0.88	High Similarity	NPC70403
0.88	High Similarity	NPC184817
0.88	High Similarity	NPC29704
0.88	High Similarity	NPC472575
0.88	High Similarity	NPC158663
0.88	High Similarity	NPC200471
0.88	High Similarity	NPC472571
0.88	High Similarity	NPC470159
0.88	High Similarity	NPC470157
0.88	High Similarity	NPC177940
0.88	High Similarity	NPC96903
0.88	High Similarity	NPC471104
0.88	High Similarity	NPC473088
0.88	High Similarity	NPC476973
0.8792	High Similarity	NPC163087
0.8784	High Similarity	NPC27377
0.8784	High Similarity	NPC41481
0.8784	High Similarity	NPC472576
0.8784	High Similarity	NPC97947
0.8784	High Similarity	NPC118080
0.8784	High Similarity	NPC291599
0.8784	High Similarity	NPC87448
0.8782	High Similarity	NPC477736
0.8782	High Similarity	NPC471102
0.8766	High Similarity	NPC472657
0.8766	High Similarity	NPC77719
0.8766	High Similarity	NPC472658
0.8758	High Similarity	NPC470153
0.8758	High Similarity	NPC469459
0.8758	High Similarity	NPC101043
0.8758	High Similarity	NPC306799
0.8758	High Similarity	NPC197037
0.8733	High Similarity	NPC70716
0.8733	High Similarity	NPC95265
0.8733	High Similarity	NPC125106
0.8733	High Similarity	NPC476974
0.8733	High Similarity	NPC95810
0.8733	High Similarity	NPC472573
0.8733	High Similarity	NPC188865
0.8733	High Similarity	NPC472569
0.8733	High Similarity	NPC472570
0.8733	High Similarity	NPC475122
0.8733	High Similarity	NPC25768
0.8733	High Similarity	NPC57628
0.8733	High Similarity	NPC11685
0.8733	High Similarity	NPC163719
0.8718	High Similarity	NPC469771
0.8716	High Similarity	NPC90614
0.8716	High Similarity	NPC100913
0.8716	High Similarity	NPC275592
0.8716	High Similarity	NPC477904
0.8716	High Similarity	NPC171207
0.8716	High Similarity	NPC183270
0.8716	High Similarity	NPC97667
0.871	High Similarity	NPC473632
0.871	High Similarity	NPC469730
0.871	High Similarity	NPC132599
0.8696	High Similarity	NPC40138
0.8693	High Similarity	NPC473214
0.8693	High Similarity	NPC254558
0.8693	High Similarity	NPC470245
0.8684	High Similarity	NPC217918
0.8675	High Similarity	NPC472556
0.8675	High Similarity	NPC471107
0.8675	High Similarity	NPC471100
0.8667	High Similarity	NPC477894
0.8667	High Similarity	NPC91703
0.8659	High Similarity	NPC477617
0.8659	High Similarity	NPC148185
0.8658	High Similarity	NPC16912
0.8645	High Similarity	NPC134685
0.8645	High Similarity	NPC11588
0.8645	High Similarity	NPC248265
0.8645	High Similarity	NPC219419
0.8645	High Similarity	NPC229545
0.8642	High Similarity	NPC477488
0.8627	High Similarity	NPC301556
0.8627	High Similarity	NPC270590
0.8627	High Similarity	NPC473215
0.8627	High Similarity	NPC92293
0.8627	High Similarity	NPC476975
0.8627	High Similarity	NPC471101
0.8627	High Similarity	NPC266265
0.8618	High Similarity	NPC474935
0.8616	High Similarity	NPC477190
0.8616	High Similarity	NPC275477
0.8616	High Similarity	NPC43304
0.8616	High Similarity	NPC55744
0.8616	High Similarity	NPC477188
0.86	High Similarity	NPC182869
0.8591	High Similarity	NPC472547
0.859	High Similarity	NPC259144
0.859	High Similarity	NPC155329
0.859	High Similarity	NPC114357
0.859	High Similarity	NPC473611
0.8571	High Similarity	NPC477896
0.8571	High Similarity	NPC477893
0.8563	High Similarity	NPC260300
0.8562	High Similarity	NPC281717
0.8562	High Similarity	NPC478073
0.8544	High Similarity	NPC476784
0.8533	High Similarity	NPC224491
0.8526	High Similarity	NPC69425
0.8509	High Similarity	NPC117943
0.8509	High Similarity	NPC293568
0.8481	Intermediate Similarity	NPC318447
0.8481	Intermediate Similarity	NPC322048
0.8481	Intermediate Similarity	NPC181924
0.8467	Intermediate Similarity	NPC473109
0.8467	Intermediate Similarity	NPC476094
0.8467	Intermediate Similarity	NPC475400
0.8467	Intermediate Similarity	NPC473081
0.8467	Intermediate Similarity	NPC211137
0.8467	Intermediate Similarity	NPC473758
0.8467	Intermediate Similarity	NPC4341

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 NPC469417 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	738
0.2-0.3	1569
0.3-0.4	2930
0.4-0.5	2364
0.5-0.6	989
0.6-0.7	228
0.7-0.8	53
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
0.8476	Intermediate Similarity	NPD7799	Discontinued
0.8129	Intermediate Similarity	NPD8407	Phase 2
0.8059	Intermediate Similarity	NPD8368	Discontinued
0.7988	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7236	Approved
0.7943	Intermediate Similarity	NPD8361	Approved
0.7943	Intermediate Similarity	NPD8435	Approved
0.7943	Intermediate Similarity	NPD8360	Approved
0.7867	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD8434	Phase 2
0.7826	Intermediate Similarity	NPD7239	Suspended
0.7753	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD8313	Approved
0.7657	Intermediate Similarity	NPD8312	Approved
0.765	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD8150	Discontinued
0.7486	Intermediate Similarity	NPD8485	Approved
0.7456	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7458	Discontinued
0.7443	Intermediate Similarity	NPD7685	Pre-registration
0.7414	Intermediate Similarity	NPD7228	Approved
0.7414	Intermediate Similarity	NPD3818	Discontinued
0.7396	Intermediate Similarity	NPD7058	Phase 2
0.7396	Intermediate Similarity	NPD7057	Phase 3
0.7394	Intermediate Similarity	NPD8319	Approved
0.7394	Intermediate Similarity	NPD8320	Phase 1
0.7377	Intermediate Similarity	NPD6534	Approved
0.7377	Intermediate Similarity	NPD6535	Approved
0.7351	Intermediate Similarity	NPD7700	Phase 2
0.7351	Intermediate Similarity	NPD7699	Phase 2
0.7345	Intermediate Similarity	NPD6559	Discontinued
0.734	Intermediate Similarity	NPD7435	Discontinued
0.733	Intermediate Similarity	NPD7074	Phase 3
0.7321	Intermediate Similarity	NPD37	Approved
0.7317	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5126	Approved
0.7315	Intermediate Similarity	NPD5125	Phase 3
0.7294	Intermediate Similarity	NPD4967	Phase 2
0.7294	Intermediate Similarity	NPD4965	Approved
0.7294	Intermediate Similarity	NPD4966	Approved
0.7284	Intermediate Similarity	NPD4628	Phase 3
0.7273	Intermediate Similarity	NPD7054	Approved
0.7273	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7240	Approved
0.7232	Intermediate Similarity	NPD7472	Approved
0.7209	Intermediate Similarity	NPD6234	Discontinued
0.7207	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7266	Discontinued
0.7202	Intermediate Similarity	NPD4380	Phase 2
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6777	Approved
0.7181	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8455	Phase 2
0.7176	Intermediate Similarity	NPD7819	Suspended
0.7159	Intermediate Similarity	NPD7473	Discontinued
0.7151	Intermediate Similarity	NPD7251	Discontinued
0.7151	Intermediate Similarity	NPD7075	Discontinued
0.7135	Intermediate Similarity	NPD6213	Phase 3
0.7135	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6212	Phase 3
0.7128	Intermediate Similarity	NPD8462	Phase 1
0.7126	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD7874	Approved
0.7111	Intermediate Similarity	NPD7808	Phase 3
0.7095	Intermediate Similarity	NPD6797	Phase 2
0.7093	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5844	Phase 1
0.7076	Intermediate Similarity	NPD5761	Phase 2
0.7076	Intermediate Similarity	NPD5760	Phase 2
0.707	Intermediate Similarity	NPD7008	Discontinued
0.7069	Intermediate Similarity	NPD5494	Approved
0.7068	Intermediate Similarity	NPD7696	Phase 3
0.7068	Intermediate Similarity	NPD7697	Approved
0.7068	Intermediate Similarity	NPD7698	Approved
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7048	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7870	Phase 2
0.7031	Intermediate Similarity	NPD7871	Phase 2
0.703	Intermediate Similarity	NPD6190	Approved
0.7029	Intermediate Similarity	NPD7199	Phase 2
0.7029	Intermediate Similarity	NPD8127	Discontinued
0.7025	Intermediate Similarity	NPD3764	Approved
0.7022	Intermediate Similarity	NPD3751	Discontinued
0.7016	Intermediate Similarity	NPD6823	Phase 2
0.701	Intermediate Similarity	NPD7701	Phase 2
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6599	Discontinued
0.699	Remote Similarity	NPD7801	Approved
0.6989	Remote Similarity	NPD6232	Discontinued
0.6989	Remote Similarity	NPD3787	Discontinued
0.6987	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD8404	Phase 2
0.6981	Remote Similarity	NPD7961	Discontinued
0.697	Remote Similarity	NPD8166	Discontinued
0.6964	Remote Similarity	NPD6273	Approved
0.6959	Remote Similarity	NPD7411	Suspended
0.6941	Remote Similarity	NPD3226	Approved
0.6936	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7319	Approved
0.6919	Remote Similarity	NPD6801	Discontinued
0.6914	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2629	Approved
0.691	Remote Similarity	NPD6166	Phase 2
0.691	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7783	Phase 2
0.6904	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.689	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2346	Discontinued
0.6879	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4198	Discontinued
0.6863	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD3749	Approved
0.6854	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5402	Approved
0.6839	Remote Similarity	NPD7507	Approved
0.6839	Remote Similarity	NPD3817	Phase 2
0.6821	Remote Similarity	NPD1934	Approved
0.6821	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2532	Approved
0.6805	Remote Similarity	NPD2534	Approved
0.6805	Remote Similarity	NPD2533	Approved
0.68	Remote Similarity	NPD5951	Approved
0.6797	Remote Similarity	NPD8517	Approved
0.6797	Remote Similarity	NPD8513	Phase 3
0.6797	Remote Similarity	NPD8516	Approved
0.6797	Remote Similarity	NPD8515	Approved
0.6776	Remote Similarity	NPD6765	Approved
0.6776	Remote Similarity	NPD6764	Approved
0.6765	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6799	Approved
0.6744	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6959	Discontinued
0.6735	Remote Similarity	NPD7999	Approved
0.6732	Remote Similarity	NPD7741	Discontinued
0.6725	Remote Similarity	NPD5403	Approved
0.6722	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7497	Discontinued
0.6716	Remote Similarity	NPD7930	Approved
0.671	Remote Similarity	NPD8328	Phase 3
0.671	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6674	Discontinued
0.6707	Remote Similarity	NPD7097	Phase 1
0.6706	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD5401	Approved
0.6705	Remote Similarity	NPD7028	Phase 2
0.6705	Remote Similarity	NPD3882	Suspended
0.6684	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7003	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD2799	Discontinued
0.6646	Remote Similarity	NPD7736	Approved
0.6645	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7680	Approved
0.6631	Remote Similarity	NPD6785	Approved
0.6631	Remote Similarity	NPD6784	Approved
0.6627	Remote Similarity	NPD5406	Approved
0.6627	Remote Similarity	NPD5408	Approved
0.6627	Remote Similarity	NPD5404	Approved
0.6627	Remote Similarity	NPD5405	Approved
0.6623	Remote Similarity	NPD6010	Discontinued
0.6622	Remote Similarity	NPD2182	Approved
0.6618	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7768	Phase 2
0.6605	Remote Similarity	NPD2313	Discontinued
0.6591	Remote Similarity	NPD2801	Approved
0.6591	Remote Similarity	NPD1465	Phase 2
0.6587	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD230	Phase 1
0.6568	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7305	Phase 1
0.6566	Remote Similarity	NPD7033	Discontinued
0.6562	Remote Similarity	NPD2798	Approved
0.6561	Remote Similarity	NPD6287	Discontinued
0.6558	Remote Similarity	NPD7610	Discontinued
0.6556	Remote Similarity	NPD6858	Approved
0.6556	Remote Similarity	NPD7094	Approved
0.6548	Remote Similarity	NPD1549	Phase 2
0.6533	Remote Similarity	NPD7584	Approved
0.6533	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5048	Discontinued
0.6529	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD2935	Discontinued
0.6527	Remote Similarity	NPD2796	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