NPASS Compound

Structure

NPC469399 OpenBabel07101718242D 42 47 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 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 2 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 0 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 28 1 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 12 30 1 0 0 0 0 13 19 1 0 0 0 0 13 28 1 0 0 0 0 14 38 1 0 0 0 0 15 29 1 0 0 0 0 15 39 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 19 1 0 0 0 0 18 29 1 1 0 0 0 19 31 1 6 0 0 0 20 14 1 6 0 0 0 20 21 1 0 0 0 0 20 40 1 0 0 0 0 21 22 1 0 0 0 0 21 32 1 1 0 0 0 22 23 1 0 0 0 0 22 33 1 6 0 0 0 23 26 1 0 0 0 0 23 34 1 1 0 0 0 24 35 2 0 0 0 0 24 38 1 0 0 0 0 25 36 2 0 0 0 0 25 39 1 0 0 0 0 26 40 1 0 0 0 0 26 41 1 6 0 0 0 27 29 1 0 0 0 0 27 37 2 0 0 0 0 27 42 1 0 0 0 0 28 30 1 1 0 0 0 28 42 1 0 0 0 0 29 30 1 1 0 0 0 30 41 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	266.13
Volume:	293.34
LogP:	4.83
LogD:	3.613
LogS:	-4.756
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.815
Synthetic Accessibility Score:	2.932
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.989
MDCK Permeability:	2.2442407498601824e-05
Pgp-inhibitor:	0.682
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.896
30% Bioavailability (F30%):	0.923

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.682
Plasma Protein Binding (PPB):	98.33728790283203%
Volume Distribution (VD):	0.627
Pgp-substrate:	1.4800833463668823%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.906
CYP2C19-inhibitor:	0.257
CYP2C19-substrate:	0.111
CYP2C9-inhibitor:	0.256
CYP2C9-substrate:	0.901
CYP2D6-inhibitor:	0.749
CYP2D6-substrate:	0.927
CYP3A4-inhibitor:	0.293
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	8.42
Half-life (T1/2):	0.434

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.406
AMES Toxicity:	0.747
Rat Oral Acute Toxicity:	0.227
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.815
Carcinogencity:	0.335
Eye Corrosion:	0.032
Eye Irritation:	0.969
Respiratory Toxicity:	0.453

Download Data

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

Natural Product: NPC469399

Natural Product ID:	NPC469399
*Common Name:**	Paeonivayin
IUPAC Name:	n.a.
Synonyms:	Paeonivayin
Standard InCHIKey:	ZHQGREQIJCCKHT-AJJQULSGSA-N
Standard InCHI:	InChI=1S/C30H32O12/c1-28-13-19(31)18-12-30(28,29(18,27(37)42-28)15-39-25(36)17-10-6-3-7-11-17)41-26-23(34)22(33)21(32)20(40-26)14-38-24(35)16-8-4-2-5-9-16/h2-11,18-23,26,31-34H,12-15H2,1H3/t18-,19-,20-,21-,22+,23-,26+,28+,29+,30-/m1/s1
SMILES:	CC12CC(C3CC1(C3(C(=O)O2)COC(=O)C4=CC=CC=C4)OC5C(C(C(C(O5)COC(=O)C6=CC=CC=C6)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077667
PubChem CID:	46882920
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
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	=	86.7	%	PMID[448315]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	88.3	%	PMID[448315]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	82.0	%	PMID[448315]
NPT848	Cell Line	N9	Homo sapiens	Inhibition	=	82.6	%	PMID[448315]
NPT848	Cell Line	N9	Homo sapiens	IC50	>	100000.0	nM	PMID[448315]

☑ 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 NPC469399 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	346
0.1-0.2	1316
0.2-0.3	2653
0.3-0.4	5362
0.4-0.5	10202
0.5-0.6	11464
0.6-0.7	9009
0.7-0.8	1940
0.8-0.85	207
0.85-0.9	175
0.9-0.95	17
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9797	High Similarity	NPC469417
0.9728	High Similarity	NPC133430
0.9728	High Similarity	NPC469477
0.953	High Similarity	NPC5115
0.953	High Similarity	NPC34066
0.9524	High Similarity	NPC469448
0.94	High Similarity	NPC469422
0.9267	High Similarity	NPC477905
0.9267	High Similarity	NPC472548
0.9245	High Similarity	NPC469421
0.9236	High Similarity	NPC469420
0.92	High Similarity	NPC469415
0.9189	High Similarity	NPC469513
0.9177	High Similarity	NPC469419
0.9156	High Similarity	NPC477623
0.9145	High Similarity	NPC472549
0.9145	High Similarity	NPC469398
0.9133	High Similarity	NPC222102
0.9133	High Similarity	NPC303429
0.9085	High Similarity	NPC106895
0.9073	High Similarity	NPC471103
0.9057	High Similarity	NPC477473
0.9057	High Similarity	NPC477466
0.9057	High Similarity	NPC469396
0.9057	High Similarity	NPC477471
0.9057	High Similarity	NPC469458
0.9057	High Similarity	NPC88176
0.9057	High Similarity	NPC149002
0.9057	High Similarity	NPC477469
0.9054	High Similarity	NPC241951
0.9054	High Similarity	NPC470152
0.9054	High Similarity	NPC475759
0.9045	High Similarity	NPC471493
0.902	High Similarity	NPC282239
0.8994	High Similarity	NPC102465
0.8993	High Similarity	NPC469349
0.8993	High Similarity	NPC473088
0.8993	High Similarity	NPC471104
0.8993	High Similarity	NPC470157
0.8993	High Similarity	NPC171525
0.8993	High Similarity	NPC472575
0.8993	High Similarity	NPC29704
0.8993	High Similarity	NPC472572
0.8993	High Similarity	NPC200471
0.8993	High Similarity	NPC70403
0.8993	High Similarity	NPC470159
0.8993	High Similarity	NPC472568
0.8993	High Similarity	NPC184817
0.8993	High Similarity	NPC96903
0.8993	High Similarity	NPC158663
0.8993	High Similarity	NPC174982
0.8993	High Similarity	NPC476973
0.8993	High Similarity	NPC472571
0.8993	High Similarity	NPC177940
0.8986	High Similarity	NPC163087
0.8981	High Similarity	NPC329960
0.8981	High Similarity	NPC150893
0.8981	High Similarity	NPC295408
0.8981	High Similarity	NPC66193
0.898	High Similarity	NPC41481
0.898	High Similarity	NPC472576
0.898	High Similarity	NPC97947
0.898	High Similarity	NPC118080
0.898	High Similarity	NPC87448
0.898	High Similarity	NPC27377
0.898	High Similarity	NPC291599
0.8947	High Similarity	NPC51602
0.8947	High Similarity	NPC470153
0.894	High Similarity	NPC60509
0.894	High Similarity	NPC250046
0.894	High Similarity	NPC81698
0.8938	High Similarity	NPC469459
0.8926	High Similarity	NPC11685
0.8926	High Similarity	NPC163719
0.8926	High Similarity	NPC472569
0.8926	High Similarity	NPC70716
0.8926	High Similarity	NPC125106
0.8926	High Similarity	NPC25768
0.8926	High Similarity	NPC57628
0.8926	High Similarity	NPC188865
0.8926	High Similarity	NPC472570
0.8926	High Similarity	NPC95810
0.8926	High Similarity	NPC476974
0.8926	High Similarity	NPC472573
0.8926	High Similarity	NPC475122
0.8926	High Similarity	NPC95265
0.8924	High Similarity	NPC477627
0.8924	High Similarity	NPC471134
0.8912	High Similarity	NPC275592
0.8912	High Similarity	NPC97667
0.8912	High Similarity	NPC90614
0.8912	High Similarity	NPC100913
0.8912	High Similarity	NPC171207
0.8903	High Similarity	NPC472393
0.8896	High Similarity	NPC26033
0.8896	High Similarity	NPC473632
0.8896	High Similarity	NPC469730
0.8896	High Similarity	NPC228204
0.8896	High Similarity	NPC469456
0.8896	High Similarity	NPC132599
0.8882	High Similarity	NPC91730
0.8882	High Similarity	NPC198455
0.8882	High Similarity	NPC161239
0.8882	High Similarity	NPC7095
0.8882	High Similarity	NPC165260
0.8868	High Similarity	NPC61891
0.8868	High Similarity	NPC477491
0.8867	High Similarity	NPC127857
0.8851	High Similarity	NPC77493
0.8851	High Similarity	NPC16912
0.8848	High Similarity	NPC469418
0.8846	High Similarity	NPC471102
0.8839	High Similarity	NPC217091
0.8834	High Similarity	NPC148185
0.8834	High Similarity	NPC477617
0.8831	High Similarity	NPC249471
0.8831	High Similarity	NPC472030
0.8831	High Similarity	NPC304876
0.8831	High Similarity	NPC158333
0.8831	High Similarity	NPC472022
0.8831	High Similarity	NPC257213
0.8831	High Similarity	NPC473414
0.8831	High Similarity	NPC256142
0.8831	High Similarity	NPC472005
0.8831	High Similarity	NPC265395
0.8831	High Similarity	NPC237549
0.8831	High Similarity	NPC242262
0.8831	High Similarity	NPC1173
0.8824	High Similarity	NPC197037
0.8816	High Similarity	NPC270590
0.8816	High Similarity	NPC92293
0.8816	High Similarity	NPC301556
0.8816	High Similarity	NPC266265
0.8816	High Similarity	NPC471101
0.8816	High Similarity	NPC476975
0.8808	High Similarity	NPC474935
0.8808	High Similarity	NPC477737
0.8784	High Similarity	NPC477904
0.8784	High Similarity	NPC183270
0.8782	High Similarity	NPC477735
0.8774	High Similarity	NPC114410
0.8774	High Similarity	NPC112523
0.8774	High Similarity	NPC473611
0.8774	High Similarity	NPC473670
0.8774	High Similarity	NPC21410
0.8758	High Similarity	NPC40138
0.8758	High Similarity	NPC473214
0.8758	High Similarity	NPC254558
0.8758	High Similarity	NPC470245
0.8758	High Similarity	NPC112216
0.875	High Similarity	NPC281717
0.875	High Similarity	NPC217918
0.8742	High Similarity	NPC471100
0.8742	High Similarity	NPC471107
0.8742	High Similarity	NPC472556
0.8735	High Similarity	NPC260300
0.8733	High Similarity	NPC91703
0.8733	High Similarity	NPC477894
0.8726	High Similarity	NPC477736
0.871	High Similarity	NPC134685
0.871	High Similarity	NPC472657
0.871	High Similarity	NPC472658
0.871	High Similarity	NPC248265
0.871	High Similarity	NPC77719
0.871	High Similarity	NPC219419
0.871	High Similarity	NPC11588
0.871	High Similarity	NPC229545
0.8704	High Similarity	NPC477488
0.8701	High Similarity	NPC306799
0.8701	High Similarity	NPC101043
0.8693	High Similarity	NPC473215
0.8688	High Similarity	NPC293568
0.8688	High Similarity	NPC117943
0.8679	High Similarity	NPC477190
0.8679	High Similarity	NPC275477
0.8679	High Similarity	NPC43304
0.8679	High Similarity	NPC477188
0.8662	High Similarity	NPC469771
0.8662	High Similarity	NPC322048
0.8662	High Similarity	NPC318447
0.8658	High Similarity	NPC473109
0.8658	High Similarity	NPC200592
0.8658	High Similarity	NPC473112
0.8658	High Similarity	NPC473060
0.8658	High Similarity	NPC473613
0.8658	High Similarity	NPC476094
0.8658	High Similarity	NPC211137
0.8658	High Similarity	NPC48017
0.8658	High Similarity	NPC4341
0.8658	High Similarity	NPC184747
0.8658	High Similarity	NPC43241
0.8658	High Similarity	NPC473758
0.8658	High Similarity	NPC147880
0.8658	High Similarity	NPC472547
0.8658	High Similarity	NPC473085
0.8658	High Similarity	NPC473081
0.8654	High Similarity	NPC259144
0.8654	High Similarity	NPC114357
0.8654	High Similarity	NPC155329
0.8649	High Similarity	NPC183122

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 NPC469399 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	773
0.2-0.3	1682
0.3-0.4	3045
0.4-0.5	2258
0.5-0.6	877
0.6-0.7	179
0.7-0.8	45
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
0.8313	Intermediate Similarity	NPD7799	Discontinued
0.8187	Intermediate Similarity	NPD8407	Phase 2
0.8155	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD8368	Discontinued
0.8	Intermediate Similarity	NPD8360	Approved
0.8	Intermediate Similarity	NPD8361	Approved
0.8	Intermediate Similarity	NPD8435	Approved
0.7886	Intermediate Similarity	NPD8434	Phase 2
0.7815	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7236	Approved
0.7778	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7239	Suspended
0.7541	Intermediate Similarity	NPD8485	Approved
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.7486	Intermediate Similarity	NPD8150	Discontinued
0.7471	Intermediate Similarity	NPD7228	Approved
0.7432	Intermediate Similarity	NPD6534	Approved
0.7432	Intermediate Similarity	NPD6535	Approved
0.7412	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7699	Phase 2
0.7405	Intermediate Similarity	NPD7700	Phase 2
0.7401	Intermediate Similarity	NPD7685	Pre-registration
0.7394	Intermediate Similarity	NPD7435	Discontinued
0.7381	Intermediate Similarity	NPD37	Approved
0.7371	Intermediate Similarity	NPD3818	Discontinued
0.7354	Intermediate Similarity	NPD8320	Phase 1
0.7354	Intermediate Similarity	NPD8319	Approved
0.7353	Intermediate Similarity	NPD4965	Approved
0.7353	Intermediate Similarity	NPD4966	Approved
0.7353	Intermediate Similarity	NPD4967	Phase 2
0.7305	Intermediate Similarity	NPD7458	Discontinued
0.7303	Intermediate Similarity	NPD6559	Discontinued
0.7303	Intermediate Similarity	NPD7240	Approved
0.7288	Intermediate Similarity	NPD7074	Phase 3
0.7273	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6234	Discontinued
0.7267	Intermediate Similarity	NPD5126	Approved
0.7267	Intermediate Similarity	NPD5125	Phase 3
0.7263	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7058	Phase 2
0.7251	Intermediate Similarity	NPD7057	Phase 3
0.7239	Intermediate Similarity	NPD4628	Phase 3
0.7234	Intermediate Similarity	NPD6782	Approved
0.7234	Intermediate Similarity	NPD6780	Approved
0.7234	Intermediate Similarity	NPD6777	Approved
0.7234	Intermediate Similarity	NPD6781	Approved
0.7234	Intermediate Similarity	NPD6776	Approved
0.7234	Intermediate Similarity	NPD6778	Approved
0.7234	Intermediate Similarity	NPD6779	Approved
0.7232	Intermediate Similarity	NPD5844	Phase 1
0.7232	Intermediate Similarity	NPD7054	Approved
0.7232	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6190	Approved
0.7191	Intermediate Similarity	NPD7472	Approved
0.7179	Intermediate Similarity	NPD8462	Phase 1
0.7165	Intermediate Similarity	NPD7874	Approved
0.7165	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7266	Discontinued
0.716	Intermediate Similarity	NPD4380	Phase 2
0.7151	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8455	Phase 2
0.7135	Intermediate Similarity	NPD7819	Suspended
0.7135	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5494	Approved
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.712	Intermediate Similarity	NPD7698	Approved
0.7119	Intermediate Similarity	NPD7473	Discontinued
0.7111	Intermediate Similarity	NPD7251	Discontinued
0.711	Intermediate Similarity	NPD7075	Discontinued
0.7097	Intermediate Similarity	NPD6213	Phase 3
0.7097	Intermediate Similarity	NPD6212	Phase 3
0.7097	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7199	Phase 2
0.7083	Intermediate Similarity	NPD7871	Phase 2
0.7083	Intermediate Similarity	NPD7870	Phase 2
0.7083	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3751	Discontinued
0.7072	Intermediate Similarity	NPD7808	Phase 3
0.7068	Intermediate Similarity	NPD6823	Phase 2
0.7062	Intermediate Similarity	NPD7701	Phase 2
0.7056	Intermediate Similarity	NPD6797	Phase 2
0.7045	Intermediate Similarity	NPD3787	Discontinued
0.7045	Intermediate Similarity	NPD6232	Discontinued
0.7041	Intermediate Similarity	NPD7801	Approved
0.7035	Intermediate Similarity	NPD8404	Phase 2
0.7035	Intermediate Similarity	NPD5761	Phase 2
0.7035	Intermediate Similarity	NPD5760	Phase 2
0.7026	Intermediate Similarity	NPD8151	Discontinued
0.7025	Intermediate Similarity	NPD7008	Discontinued
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8127	Discontinued
0.6987	Remote Similarity	NPD7319	Approved
0.6981	Remote Similarity	NPD3764	Approved
0.6964	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6599	Discontinued
0.6954	Remote Similarity	NPD7783	Phase 2
0.6954	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6273	Approved
0.6919	Remote Similarity	NPD7411	Suspended
0.691	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5402	Approved
0.6897	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6801	Discontinued
0.6872	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6166	Phase 2
0.6872	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2629	Approved
0.6864	Remote Similarity	NPD2534	Approved
0.6864	Remote Similarity	NPD2533	Approved
0.6864	Remote Similarity	NPD2532	Approved
0.6856	Remote Similarity	NPD7497	Discontinued
0.6839	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7961	Discontinued
0.6826	Remote Similarity	NPD8166	Discontinued
0.6824	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD4198	Discontinued
0.6818	Remote Similarity	NPD3749	Approved
0.6814	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3226	Approved
0.68	Remote Similarity	NPD3817	Phase 2
0.6797	Remote Similarity	NPD7741	Discontinued
0.6795	Remote Similarity	NPD7507	Approved
0.6782	Remote Similarity	NPD1934	Approved
0.678	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5951	Approved
0.6753	Remote Similarity	NPD8516	Approved
0.6753	Remote Similarity	NPD8517	Approved
0.6753	Remote Similarity	NPD8515	Approved
0.6753	Remote Similarity	NPD8513	Phase 3
0.6747	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD2346	Discontinued
0.6736	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.671	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6799	Approved
0.6705	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6959	Discontinued
0.6701	Remote Similarity	NPD7999	Approved
0.6686	Remote Similarity	NPD5403	Approved
0.6685	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7680	Approved
0.6683	Remote Similarity	NPD7930	Approved
0.6667	Remote Similarity	NPD5401	Approved
0.6667	Remote Similarity	NPD6674	Discontinued
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD7768	Phase 2
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6765	Approved
0.6649	Remote Similarity	NPD6764	Approved
0.6648	Remote Similarity	NPD2801	Approved
0.6648	Remote Similarity	NPD1465	Phase 2
0.6646	Remote Similarity	NPD230	Phase 1
0.6627	Remote Similarity	NPD7003	Approved
0.6627	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7516	Approved
0.6622	Remote Similarity	NPD6686	Approved
0.6603	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD5408	Approved
0.6587	Remote Similarity	NPD5404	Approved
0.6587	Remote Similarity	NPD5406	Approved
0.6587	Remote Similarity	NPD5405	Approved
0.6587	Remote Similarity	NPD2935	Discontinued
0.6579	Remote Similarity	NPD6010	Discontinued
0.6577	Remote Similarity	NPD2182	Approved
0.6571	Remote Similarity	NPD7028	Phase 2
0.6571	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD8059	Phase 3
0.6561	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD8328	Phase 3
0.6558	Remote Similarity	NPD7328	Approved
0.6558	Remote Similarity	NPD7327	Approved
0.6529	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD7033	Discontinued
0.6527	Remote Similarity	NPD2799	Discontinued
0.6509	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD1549	Phase 2
0.6508	Remote Similarity	NPD6784	Approved
0.6508	Remote Similarity	NPD6785	Approved
0.6507	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7583	Approved
0.65	Remote Similarity	NPD7584	Approved
0.65	Remote Similarity	NPD7736	Approved
0.6488	Remote Similarity	NPD2796	Approved
0.6486	Remote Similarity	NPD5048	Discontinued
0.6484	Remote Similarity	NPD5710	Approved
0.6484	Remote Similarity	NPD5711	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