NPASS Compound

Structure

NPC469415 OpenBabel07101719402D 38 43 0 0 1 0 0 0 0 0999 V2000 -3.8861 2.2235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4370 -2.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1468 2.8634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2229 2.5431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0349 -5.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9658 -4.7598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2247 -6.2827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0865 -4.3319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3454 -5.8548 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0384 1.5828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9778 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9801 0.4883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7789 -1.2395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1382 -2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2764 -4.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0038 0.5445 0.0000 C 0 0 2 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 3.5644 1.4180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5881 1.4742 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0514 0.6569 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6029 -4.4516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4908 -0.2167 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9300 -1.2800 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6317 -1.8795 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9778 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9300 0.3022 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9778 -0.9778 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4195 -0.3852 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1011 2.2354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1487 2.3477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0751 0.7130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4131 -4.9991 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6720 -3.4762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1145 1.2624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4671 -0.2728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9541 -1.0340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3222 -2.0306 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5047 -0.4889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 24 1 0 0 0 0 3 4 1 0 0 0 0 4 10 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 15 2 0 0 0 0 9 15 1 0 0 0 0 10 34 1 0 0 0 0 11 17 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 24 1 0 0 0 0 13 26 1 0 0 0 0 14 25 1 0 0 0 0 14 33 1 0 0 0 0 15 21 1 0 0 0 0 16 12 1 1 0 0 0 16 18 1 0 0 0 0 16 35 1 0 0 0 0 17 25 1 1 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 18 29 1 6 0 0 0 19 20 1 0 0 0 0 19 30 1 1 0 0 0 20 22 1 0 0 0 0 20 31 1 6 0 0 0 21 32 2 0 0 0 0 21 33 1 0 0 0 0 22 35 1 0 0 0 0 22 36 1 1 0 0 0 23 25 1 0 0 0 0 23 37 1 0 0 0 0 23 38 1 0 0 0 0 24 27 1 1 0 0 0 24 37 1 0 0 0 0 25 27 1 6 0 0 0 26 34 1 6 0 0 0 26 38 1 0 0 0 0 27 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.23
Volume:	510.356
LogP:	2.02
LogD:	1.936
LogS:	-4.131
# Rotatable Bonds:	11
TPSA:	153.37
# H-Bond Aceptor:	11
# H-Bond Donor:	4
# Rings:	8
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.244
Synthetic Accessibility Score:	6.258
Fsp3:	0.741
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:	-5.983
MDCK Permeability:	2.491716804797761e-05
Pgp-inhibitor:	0.051
Pgp-substrate:	0.978
Human Intestinal Absorption (HIA):	0.45
20% Bioavailability (F20%):	0.273
30% Bioavailability (F30%):	0.637

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.117
Plasma Protein Binding (PPB):	69.30094146728516%
Volume Distribution (VD):	0.859
Pgp-substrate:	8.747713088989258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.99
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.64
CYP2C9-inhibitor:	0.02
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.575
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	6.377
Half-life (T1/2):	0.747

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.068
Drug-inuced Liver Injury (DILI):	0.13
AMES Toxicity:	0.962
Rat Oral Acute Toxicity:	0.098
Maximum Recommended Daily Dose:	0.072
Skin Sensitization:	0.916
Carcinogencity:	0.932
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.93

Download Data

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

Natural Product: NPC469415

Natural Product ID:	NPC469415
*Common Name:**	WZGDJBIFNLWZEF-POZPPLBNSA-N
IUPAC Name:	n.a.
Synonyms:	4-O-Butylpaeoniflorin
Standard InCHIKey:	WZGDJBIFNLWZEF-POZPPLBNSA-N
Standard InCHI:	InChI=1S/C27H36O11/c1-3-4-10-34-26-13-24(2)27(36-22-20(31)19(30)18(29)16(12-28)35-22)11-17(26)25(27,23(37-24)38-26)14-33-21(32)15-8-6-5-7-9-15/h5-9,16-20,22-23,28-31H,3-4,10-14H2,1-2H3/t16-,17+,18-,19+,20-,22+,23?,24+,25+,26-,27-/m1/s1
SMILES:	CCCCOC12CC3(C4(CC1C4(C(O3)O2)COC(=O)C5=CC=CC=C5)OC6C(C(C(C(O6)CO)O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1078184
PubChem CID:	44253994
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]
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]
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]
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	3

Activity Type	# Activity
Cell Line	1
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[553486]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	36200.0	nM	PMID[553485]
NPT35	Others	n.a.		IC50	=	10800.0	nM	PMID[553485]

☑ 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 NPC469415 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	359
0.1-0.2	1250
0.2-0.3	2639
0.3-0.4	5532
0.4-0.5	10263
0.5-0.6	14071
0.6-0.7	7143
0.7-0.8	1069
0.8-0.85	206
0.85-0.9	135
0.9-0.95	18
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9929	High Similarity	NPC222102
0.9929	High Similarity	NPC303429
0.9792	High Similarity	NPC469398
0.9792	High Similarity	NPC469422
0.9655	High Similarity	NPC34066
0.9527	High Similarity	NPC477623
0.9379	High Similarity	NPC469448
0.932	High Similarity	NPC133430
0.932	High Similarity	NPC469477
0.9257	High Similarity	NPC5115
0.92	High Similarity	NPC469399
0.915	High Similarity	NPC293568
0.915	High Similarity	NPC117943
0.9091	High Similarity	NPC472576
0.9091	High Similarity	NPC87448
0.9091	High Similarity	NPC291599
0.9091	High Similarity	NPC118080
0.9091	High Similarity	NPC27377
0.9091	High Similarity	NPC97947
0.9091	High Similarity	NPC41481
0.9038	High Similarity	NPC469459
0.9032	High Similarity	NPC120012
0.9021	High Similarity	NPC97667
0.9021	High Similarity	NPC90614
0.9021	High Similarity	NPC100913
0.9021	High Similarity	NPC275592
0.9021	High Similarity	NPC171207
0.9007	High Similarity	NPC469417
0.8974	High Similarity	NPC265600
0.8958	High Similarity	NPC16912
0.8917	High Similarity	NPC149002
0.8917	High Similarity	NPC469458
0.8917	High Similarity	NPC469396
0.8917	High Similarity	NPC88176
0.8904	High Similarity	NPC241951
0.8904	High Similarity	NPC470152
0.8904	High Similarity	NPC475759
0.8889	High Similarity	NPC472547
0.8868	High Similarity	NPC469421
0.8859	High Similarity	NPC476173
0.8854	High Similarity	NPC469420
0.8844	High Similarity	NPC470159
0.8844	High Similarity	NPC70403
0.8844	High Similarity	NPC472568
0.8844	High Similarity	NPC96903
0.8844	High Similarity	NPC471104
0.8844	High Similarity	NPC469349
0.8844	High Similarity	NPC29704
0.8844	High Similarity	NPC174982
0.8844	High Similarity	NPC177940
0.8844	High Similarity	NPC472572
0.8844	High Similarity	NPC473088
0.8844	High Similarity	NPC158663
0.8844	High Similarity	NPC171525
0.8844	High Similarity	NPC476973
0.8844	High Similarity	NPC184817
0.8844	High Similarity	NPC472571
0.8844	High Similarity	NPC200471
0.8844	High Similarity	NPC472575
0.8844	High Similarity	NPC470157
0.8836	High Similarity	NPC163087
0.8812	High Similarity	NPC477617
0.8808	High Similarity	NPC471135
0.8808	High Similarity	NPC472657
0.8808	High Similarity	NPC472658
0.8784	High Similarity	NPC469513
0.8784	High Similarity	NPC478263
0.8776	High Similarity	NPC57628
0.8776	High Similarity	NPC11685
0.8776	High Similarity	NPC70716
0.8776	High Similarity	NPC95265
0.8776	High Similarity	NPC125106
0.8776	High Similarity	NPC95810
0.8776	High Similarity	NPC472573
0.8776	High Similarity	NPC188865
0.8776	High Similarity	NPC38696
0.8776	High Similarity	NPC476974
0.8776	High Similarity	NPC472570
0.8776	High Similarity	NPC472569
0.8776	High Similarity	NPC25768
0.8776	High Similarity	NPC163719
0.8776	High Similarity	NPC475122
0.8767	High Similarity	NPC34012
0.875	High Similarity	NPC469456
0.875	High Similarity	NPC39549
0.8741	High Similarity	NPC472577
0.8741	High Similarity	NPC291638
0.8741	High Similarity	NPC17877
0.8741	High Similarity	NPC195647
0.8741	High Similarity	NPC66761
0.8716	High Similarity	NPC478264
0.8707	High Similarity	NPC91703
0.8701	High Similarity	NPC476784
0.8696	High Similarity	NPC148185
0.8693	High Similarity	NPC475548
0.8693	High Similarity	NPC290683
0.8693	High Similarity	NPC475638
0.8681	High Similarity	NPC472551
0.8681	High Similarity	NPC472545
0.8671	High Similarity	NPC474608
0.8667	High Similarity	NPC301556
0.8667	High Similarity	NPC476975
0.8667	High Similarity	NPC270590
0.8667	High Similarity	NPC92293
0.8667	High Similarity	NPC471101
0.8667	High Similarity	NPC266265
0.8658	High Similarity	NPC474935
0.8658	High Similarity	NPC240115
0.865	High Similarity	NPC469397
0.8636	High Similarity	NPC318447
0.8636	High Similarity	NPC322048
0.8611	High Similarity	NPC473216
0.8611	High Similarity	NPC473399
0.8609	High Similarity	NPC470245
0.8609	High Similarity	NPC473214
0.8608	High Similarity	NPC473557
0.8608	High Similarity	NPC473468
0.8608	High Similarity	NPC475567
0.8608	High Similarity	NPC477491
0.86	High Similarity	NPC281717
0.86	High Similarity	NPC217918
0.8598	High Similarity	NPC80360
0.8591	High Similarity	NPC92867
0.8591	High Similarity	NPC472556
0.8591	High Similarity	NPC311825
0.8571	High Similarity	NPC323001
0.8571	High Similarity	NPC326235
0.8553	High Similarity	NPC471103
0.8553	High Similarity	NPC475198
0.8553	High Similarity	NPC470153
0.8553	High Similarity	NPC475531
0.8553	High Similarity	NPC475175
0.8545	High Similarity	NPC195114
0.8544	High Similarity	NPC477627
0.8544	High Similarity	NPC471493
0.8543	High Similarity	NPC473215
0.8533	High Similarity	NPC20255
0.8526	High Similarity	NPC326328
0.8526	High Similarity	NPC323356
0.8526	High Similarity	NPC309991
0.8526	High Similarity	NPC471138
0.8523	High Similarity	NPC34943
0.8514	High Similarity	NPC472546
0.8506	High Similarity	NPC469730
0.8506	High Similarity	NPC473632
0.8506	High Similarity	NPC132599
0.8503	High Similarity	NPC4341
0.8503	High Similarity	NPC473085
0.8503	High Similarity	NPC48017
0.8503	High Similarity	NPC184747
0.8503	High Similarity	NPC476094
0.8503	High Similarity	NPC473081
0.8503	High Similarity	NPC477904
0.8503	High Similarity	NPC43241
0.8503	High Similarity	NPC473613
0.8503	High Similarity	NPC473758
0.8503	High Similarity	NPC211137
0.8503	High Similarity	NPC473060
0.8503	High Similarity	NPC473112
0.8503	High Similarity	NPC200592
0.8503	High Similarity	NPC147880
0.8503	High Similarity	NPC183270
0.8503	High Similarity	NPC473109
0.85	High Similarity	NPC102465
0.8497	Intermediate Similarity	NPC472548
0.8497	Intermediate Similarity	NPC477905
0.8494	Intermediate Similarity	NPC188217
0.8493	Intermediate Similarity	NPC183122
0.8493	Intermediate Similarity	NPC283375
0.8487	Intermediate Similarity	NPC91730
0.8485	Intermediate Similarity	NPC260300
0.8481	Intermediate Similarity	NPC329960
0.8481	Intermediate Similarity	NPC295408
0.8481	Intermediate Similarity	NPC150893
0.8477	Intermediate Similarity	NPC473760
0.8476	Intermediate Similarity	NPC469438
0.8467	Intermediate Similarity	NPC125882
0.8462	Intermediate Similarity	NPC319404
0.8456	Intermediate Similarity	NPC477894
0.8447	Intermediate Similarity	NPC477488
0.8447	Intermediate Similarity	NPC477471
0.8447	Intermediate Similarity	NPC477469
0.8447	Intermediate Similarity	NPC469419
0.8447	Intermediate Similarity	NPC477473
0.8447	Intermediate Similarity	NPC477466
0.8446	Intermediate Similarity	NPC77493
0.8446	Intermediate Similarity	NPC224491
0.8435	Intermediate Similarity	NPC214550
0.8435	Intermediate Similarity	NPC210591
0.8435	Intermediate Similarity	NPC475652
0.8431	Intermediate Similarity	NPC197037
0.8431	Intermediate Similarity	NPC51602
0.8418	Intermediate Similarity	NPC43304
0.8418	Intermediate Similarity	NPC477190
0.8418	Intermediate Similarity	NPC477188
0.8418	Intermediate Similarity	NPC478124
0.8411	Intermediate Similarity	NPC477737
0.8411	Intermediate Similarity	NPC48599
0.8411	Intermediate Similarity	NPC209592
0.8411	Intermediate Similarity	NPC473602

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 NPC469415 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	770
0.2-0.3	1750
0.3-0.4	3090
0.4-0.5	2260
0.5-0.6	804
0.6-0.7	163
0.7-0.8	23
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
0.8232	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7799	Discontinued
0.7836	Intermediate Similarity	NPD8407	Phase 2
0.777	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD8368	Discontinued
0.7532	Intermediate Similarity	NPD7236	Approved
0.7529	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD8434	Phase 2
0.741	Intermediate Similarity	NPD4967	Phase 2
0.741	Intermediate Similarity	NPD4965	Approved
0.741	Intermediate Similarity	NPD4966	Approved
0.7407	Intermediate Similarity	NPD7239	Suspended
0.7386	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD8361	Approved
0.736	Intermediate Similarity	NPD8435	Approved
0.736	Intermediate Similarity	NPD8360	Approved
0.7356	Intermediate Similarity	NPD7240	Approved
0.7329	Intermediate Similarity	NPD5126	Approved
0.7329	Intermediate Similarity	NPD5125	Phase 3
0.7321	Intermediate Similarity	NPD6234	Discontinued
0.7247	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD37	Approved
0.7222	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7266	Discontinued
0.7182	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8313	Approved
0.7175	Intermediate Similarity	NPD8312	Approved
0.7159	Intermediate Similarity	NPD6559	Discontinued
0.7097	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8455	Phase 2
0.7081	Intermediate Similarity	NPD4628	Phase 3
0.7062	Intermediate Similarity	NPD7685	Pre-registration
0.7034	Intermediate Similarity	NPD2629	Approved
0.7	Intermediate Similarity	NPD7057	Phase 3
0.7	Intermediate Similarity	NPD7058	Phase 2
0.6993	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7074	Phase 3
0.6946	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7458	Discontinued
0.6936	Remote Similarity	NPD8127	Discontinued
0.6936	Remote Similarity	NPD7199	Phase 2
0.6935	Remote Similarity	NPD8485	Approved
0.6932	Remote Similarity	NPD3818	Discontinued
0.6898	Remote Similarity	NPD7699	Phase 2
0.6898	Remote Similarity	NPD7700	Phase 2
0.6893	Remote Similarity	NPD5844	Phase 1
0.6893	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7054	Approved
0.6872	Remote Similarity	NPD8462	Phase 1
0.6871	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4198	Discontinued
0.6868	Remote Similarity	NPD8150	Discontinued
0.6859	Remote Similarity	NPD8320	Phase 1
0.6859	Remote Similarity	NPD8319	Approved
0.6859	Remote Similarity	NPD7008	Discontinued
0.6854	Remote Similarity	NPD7472	Approved
0.6848	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD7741	Discontinued
0.6829	Remote Similarity	NPD6190	Approved
0.6828	Remote Similarity	NPD6534	Approved
0.6828	Remote Similarity	NPD6535	Approved
0.6828	Remote Similarity	NPD969	Suspended
0.6826	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD3764	Approved
0.6806	Remote Similarity	NPD7435	Discontinued
0.6784	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7819	Suspended
0.6783	Remote Similarity	NPD6686	Approved
0.6778	Remote Similarity	NPD7251	Discontinued
0.6772	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD8166	Discontinued
0.6766	Remote Similarity	NPD6273	Approved
0.6763	Remote Similarity	NPD7075	Discontinued
0.6761	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.674	Remote Similarity	NPD7808	Phase 3
0.674	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2182	Approved
0.6727	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD6797	Phase 2
0.6719	Remote Similarity	NPD7497	Discontinued
0.6719	Remote Similarity	NPD7680	Approved
0.6711	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7028	Phase 2
0.6706	Remote Similarity	NPD4380	Phase 2
0.6705	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5951	Approved
0.6686	Remote Similarity	NPD5761	Phase 2
0.6686	Remote Similarity	NPD1653	Approved
0.6686	Remote Similarity	NPD5760	Phase 2
0.6686	Remote Similarity	NPD5494	Approved
0.6685	Remote Similarity	NPD6764	Approved
0.6685	Remote Similarity	NPD6765	Approved
0.6667	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD7961	Discontinued
0.665	Remote Similarity	NPD8404	Phase 2
0.6649	Remote Similarity	NPD6782	Approved
0.6649	Remote Similarity	NPD6778	Approved
0.6649	Remote Similarity	NPD6777	Approved
0.6649	Remote Similarity	NPD6781	Approved
0.6649	Remote Similarity	NPD6780	Approved
0.6649	Remote Similarity	NPD6779	Approved
0.6649	Remote Similarity	NPD6776	Approved
0.6649	Remote Similarity	NPD7999	Approved
0.6645	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7698	Approved
0.6632	Remote Similarity	NPD7697	Approved
0.6632	Remote Similarity	NPD7696	Phase 3
0.6629	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7507	Approved
0.6608	Remote Similarity	NPD6599	Discontinued
0.6607	Remote Similarity	NPD2532	Approved
0.6607	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2533	Approved
0.6607	Remote Similarity	NPD2534	Approved
0.6606	Remote Similarity	NPD6674	Discontinued
0.6603	Remote Similarity	NPD7319	Approved
0.66	Remote Similarity	NPD7328	Approved
0.66	Remote Similarity	NPD7327	Approved
0.6599	Remote Similarity	NPD7874	Approved
0.6599	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD7473	Discontinued
0.6585	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6004	Phase 3
0.6585	Remote Similarity	NPD6002	Phase 3
0.6585	Remote Similarity	NPD6005	Phase 3
0.6585	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD230	Phase 1
0.6582	Remote Similarity	NPD7701	Phase 2
0.6577	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6663	Approved
0.6552	Remote Similarity	NPD5402	Approved
0.655	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD8151	Discontinued
0.6541	Remote Similarity	NPD6785	Approved
0.6541	Remote Similarity	NPD6784	Approved
0.6532	Remote Similarity	NPD6801	Discontinued
0.6517	Remote Similarity	NPD6232	Discontinued
0.6513	Remote Similarity	NPD7871	Phase 2
0.6513	Remote Similarity	NPD7870	Phase 2
0.6508	Remote Similarity	NPD6213	Phase 3
0.6508	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6212	Phase 3
0.6503	Remote Similarity	NPD7097	Phase 1
0.6494	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD2346	Discontinued
0.6482	Remote Similarity	NPD7783	Phase 2
0.6482	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6482	Remote Similarity	NPD7801	Approved
0.6481	Remote Similarity	NPD6355	Discontinued
0.6471	Remote Similarity	NPD8513	Phase 3
0.6471	Remote Similarity	NPD8516	Approved
0.6471	Remote Similarity	NPD8378	Approved
0.6471	Remote Similarity	NPD8296	Approved
0.6471	Remote Similarity	NPD8379	Approved
0.6471	Remote Similarity	NPD8517	Approved
0.6471	Remote Similarity	NPD7503	Approved
0.6471	Remote Similarity	NPD8380	Approved
0.6471	Remote Similarity	NPD8033	Approved
0.6471	Remote Similarity	NPD8335	Approved
0.6471	Remote Similarity	NPD8515	Approved
0.6468	Remote Similarity	NPD7930	Approved
0.6467	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7003	Approved
0.6464	Remote Similarity	NPD3751	Discontinued
0.6458	Remote Similarity	NPD164	Approved
0.6457	Remote Similarity	NPD3817	Phase 2
0.6452	Remote Similarity	NPD6287	Discontinued
0.6448	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD6166	Phase 2
0.6444	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD1934	Approved
0.6433	Remote Similarity	NPD5403	Approved
0.6429	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD3787	Discontinued
0.6424	Remote Similarity	NPD2935	Discontinued
0.6415	Remote Similarity	NPD5736	Approved
0.6412	Remote Similarity	NPD5401	Approved
0.6407	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD9545	Approved
0.6405	Remote Similarity	NPD8294	Approved
0.6405	Remote Similarity	NPD8377	Approved
0.64	Remote Similarity	NPD1465	Phase 2
0.64	Remote Similarity	NPD6010	Discontinued
0.6389	Remote Similarity	NPD6647	Phase 2
0.6386	Remote Similarity	NPD5763	Approved
0.6386	Remote Similarity	NPD5762	Approved
0.6386	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7411	Suspended
0.6374	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6685	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