NPASS Compound

Structure

CID78284 OpenBabel06191715412D 27 30 0 0 0 0 0 0 0 0999 V2000 0.0098 -0.9320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8902 2.7318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6532 0.3840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 4.1647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8910 2.4429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7961 1.3931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8001 0.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0208 2.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2557 1.8343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2213 -0.0402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0139 1.8608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4354 1.3806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4182 0.4433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0587 1.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0415 0.4136 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8250 3.2491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8140 1.3934 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6305 1.8508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8137 0.4527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6186 -0.0176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6251 2.7816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6158 -0.9491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8731 1.8013 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8389 -0.0665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8348 4.1745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4275 3.2452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 22 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 17 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 15 2 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 21 2 0 0 0 0 16 26 1 0 0 0 0 17 18 2 0 0 0 0 17 19 1 0 0 0 0 18 21 1 0 0 0 0 19 20 2 0 0 0 0 19 22 1 0 0 0 0 20 23 1 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	369.16
Volume:	374.039
LogP:	4.206
LogD:	3.254
LogS:	-5.293
# Rotatable Bonds:	4
TPSA:	60.39
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.707
Synthetic Accessibility Score:	2.693
Fsp3:	0.333
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:	-4.858
MDCK Permeability:	2.4819064492476173e-05
Pgp-inhibitor:	0.823
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.089

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	78.2774887084961%
Volume Distribution (VD):	0.792
Pgp-substrate:	17.619287490844727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.5
CYP1A2-substrate:	0.983
CYP2C19-inhibitor:	0.256
CYP2C19-substrate:	0.927
CYP2C9-inhibitor:	0.13
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.211
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.175
CYP3A4-substrate:	0.646

ADMET: Excretion

Clearance (CL):	8.801
Half-life (T1/2):	0.508

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.85
AMES Toxicity:	0.408
Rat Oral Acute Toxicity:	0.283
Maximum Recommended Daily Dose:	0.249
Skin Sensitization:	0.911
Carcinogencity:	0.037
Eye Corrosion:	0.004
Eye Irritation:	0.101
Respiratory Toxicity:	0.849

Download Data

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

Natural Product: NPC78284

Natural Product ID:	NPC78284
*Common Name:**	XTYGTYHSWAJTPX-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	7-Hydroxy-Dehydroglaucine
Standard InCHIKey:	XTYGTYHSWAJTPX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H23NO5/c1-22-7-6-11-8-16(26-4)21(27-5)18-12-9-14(24-2)15(25-3)10-13(12)20(23)19(22)17(11)18/h8-10,23H,6-7H2,1-5H3
SMILES:	COc1cc2c(cc1OC)c(O)c1c3c2c(OC)c(OC)cc3CCN1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517328
PubChem CID:	10317002
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines

*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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[9599253]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868142]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11053	Annona purpurea	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2884	Annona squamosa	Species	Annonaceae	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
Others	8

Activity Type	# Activity
CELL-LINE	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	78.8	%	PMID[508022]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	21.8	%	PMID[508022]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	12.7	%	PMID[508022]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	0.0	%	PMID[508022]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	25.2	%	PMID[508022]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	64.9	%	PMID[508022]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	77.9	%	PMID[508022]

☑ 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 NPC78284 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	446
0.1-0.2	2314
0.2-0.3	10921
0.3-0.4	6969
0.4-0.5	8041
0.5-0.6	11443
0.6-0.7	1958
0.7-0.8	520
0.8-0.85	74
0.85-0.9	7
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9314	High Similarity	NPC320088
0.9191	High Similarity	NPC190461
0.9091	High Similarity	NPC276674
0.9091	High Similarity	NPC33902
0.8939	High Similarity	NPC474904
0.8908	High Similarity	NPC285941
0.8833	High Similarity	NPC312531
0.8571	High Similarity	NPC81218
0.8571	High Similarity	NPC117188
0.8571	High Similarity	NPC205421
0.8571	High Similarity	NPC158376
0.8571	High Similarity	NPC474931
0.8571	High Similarity	NPC12053
0.8571	High Similarity	NPC306555
0.8571	High Similarity	NPC145832
0.8563	High Similarity	NPC13504
0.8563	High Similarity	NPC477563
0.8563	High Similarity	NPC196447
0.8563	High Similarity	NPC306843
0.8563	High Similarity	NPC96603
0.8563	High Similarity	NPC78222
0.8563	High Similarity	NPC136508
0.8563	High Similarity	NPC253043
0.8563	High Similarity	NPC212794
0.8556	High Similarity	NPC179704
0.8508	High Similarity	NPC249405
0.8506	High Similarity	NPC324144
0.8503	High Similarity	NPC17677
0.8495	Intermediate Similarity	NPC162653
0.8492	Intermediate Similarity	NPC287588
0.84	Intermediate Similarity	NPC1229
0.8382	Intermediate Similarity	NPC476572
0.8372	Intermediate Similarity	NPC99659
0.8372	Intermediate Similarity	NPC325871
0.8343	Intermediate Similarity	NPC60186
0.8324	Intermediate Similarity	NPC239775
0.8306	Intermediate Similarity	NPC248642
0.8289	Intermediate Similarity	NPC302001
0.8286	Intermediate Similarity	NPC166014
0.8286	Intermediate Similarity	NPC27410
0.8278	Intermediate Similarity	NPC66341
0.8278	Intermediate Similarity	NPC477020
0.8278	Intermediate Similarity	NPC192135
0.8272	Intermediate Similarity	NPC471489
0.8268	Intermediate Similarity	NPC69712
0.8268	Intermediate Similarity	NPC26240
0.8268	Intermediate Similarity	NPC477562
0.8261	Intermediate Similarity	NPC156576
0.8242	Intermediate Similarity	NPC114364
0.8242	Intermediate Similarity	NPC320223
0.8235	Intermediate Similarity	NPC294244
0.8232	Intermediate Similarity	NPC128560
0.8232	Intermediate Similarity	NPC199465
0.8232	Intermediate Similarity	NPC229166
0.8197	Intermediate Similarity	NPC126284
0.8197	Intermediate Similarity	NPC192939
0.8197	Intermediate Similarity	NPC215747
0.8167	Intermediate Similarity	NPC118274
0.8167	Intermediate Similarity	NPC168753
0.8156	Intermediate Similarity	NPC150879
0.8144	Intermediate Similarity	NPC156728
0.8144	Intermediate Similarity	NPC244606
0.8142	Intermediate Similarity	NPC260118
0.8108	Intermediate Similarity	NPC28425
0.8092	Intermediate Similarity	NPC81733
0.8092	Intermediate Similarity	NPC326316
0.8087	Intermediate Similarity	NPC265383
0.8073	Intermediate Similarity	NPC212163
0.8056	Intermediate Similarity	NPC247389
0.8056	Intermediate Similarity	NPC298979
0.8054	Intermediate Similarity	NPC119579
0.8045	Intermediate Similarity	NPC169743
0.8045	Intermediate Similarity	NPC302527
0.8045	Intermediate Similarity	NPC16805
0.8045	Intermediate Similarity	NPC134858
0.8045	Intermediate Similarity	NPC167546
0.8021	Intermediate Similarity	NPC193906
0.8021	Intermediate Similarity	NPC23080
0.8021	Intermediate Similarity	NPC180253
0.8021	Intermediate Similarity	NPC219170
0.8011	Intermediate Similarity	NPC116284
0.8	Intermediate Similarity	NPC474507
0.8	Intermediate Similarity	NPC476432
0.8	Intermediate Similarity	NPC476573
0.8	Intermediate Similarity	NPC24264
0.8	Intermediate Similarity	NPC311936
0.8	Intermediate Similarity	NPC35627
0.8	Intermediate Similarity	NPC81247
0.8	Intermediate Similarity	NPC219341
0.799	Intermediate Similarity	NPC295676
0.7989	Intermediate Similarity	NPC233650
0.7979	Intermediate Similarity	NPC477186
0.7979	Intermediate Similarity	NPC214116
0.7968	Intermediate Similarity	NPC135772
0.7957	Intermediate Similarity	NPC476574
0.7957	Intermediate Similarity	NPC477561
0.7957	Intermediate Similarity	NPC155442
0.7957	Intermediate Similarity	NPC312918
0.7956	Intermediate Similarity	NPC210140
0.7956	Intermediate Similarity	NPC210918
0.7955	Intermediate Similarity	NPC244112
0.7944	Intermediate Similarity	NPC225774
0.7933	Intermediate Similarity	NPC80759
0.7933	Intermediate Similarity	NPC79402
0.7923	Intermediate Similarity	NPC200888
0.7914	Intermediate Similarity	NPC276060
0.791	Intermediate Similarity	NPC186063
0.7903	Intermediate Similarity	NPC220961
0.7892	Intermediate Similarity	NPC476577
0.7892	Intermediate Similarity	NPC173416
0.7892	Intermediate Similarity	NPC148709
0.7884	Intermediate Similarity	NPC57036
0.7884	Intermediate Similarity	NPC22928
0.7877	Intermediate Similarity	NPC271388
0.7877	Intermediate Similarity	NPC119649
0.7877	Intermediate Similarity	NPC235143
0.7877	Intermediate Similarity	NPC230956
0.7877	Intermediate Similarity	NPC205255
0.7857	Intermediate Similarity	NPC204947
0.7842	Intermediate Similarity	NPC112676
0.7842	Intermediate Similarity	NPC296742
0.7841	Intermediate Similarity	NPC26601
0.7838	Intermediate Similarity	NPC477558
0.7826	Intermediate Similarity	NPC19520
0.7826	Intermediate Similarity	NPC149090
0.7821	Intermediate Similarity	NPC221864
0.7819	Intermediate Similarity	NPC476575
0.7812	Intermediate Similarity	NPC478093
0.7809	Intermediate Similarity	NPC170503
0.7809	Intermediate Similarity	NPC203784
0.7809	Intermediate Similarity	NPC126519
0.7801	Intermediate Similarity	NPC82763
0.7789	Intermediate Similarity	NPC224293
0.7778	Intermediate Similarity	NPC306902
0.7778	Intermediate Similarity	NPC160298
0.7778	Intermediate Similarity	NPC266753
0.7778	Intermediate Similarity	NPC232924
0.7778	Intermediate Similarity	NPC477559
0.7772	Intermediate Similarity	NPC30182
0.7772	Intermediate Similarity	NPC473589
0.7772	Intermediate Similarity	NPC478092
0.7772	Intermediate Similarity	NPC478091
0.7772	Intermediate Similarity	NPC6152
0.7759	Intermediate Similarity	NPC476151
0.7753	Intermediate Similarity	NPC207757
0.7753	Intermediate Similarity	NPC278799
0.7753	Intermediate Similarity	NPC110416
0.7753	Intermediate Similarity	NPC5238
0.7753	Intermediate Similarity	NPC469817
0.7753	Intermediate Similarity	NPC249797
0.7753	Intermediate Similarity	NPC2413
0.7753	Intermediate Similarity	NPC204828
0.7753	Intermediate Similarity	NPC127674
0.7753	Intermediate Similarity	NPC276588
0.7753	Intermediate Similarity	NPC184026
0.7753	Intermediate Similarity	NPC54379
0.7753	Intermediate Similarity	NPC39701
0.7753	Intermediate Similarity	NPC193949
0.7753	Intermediate Similarity	NPC295691
0.7753	Intermediate Similarity	NPC172765
0.7753	Intermediate Similarity	NPC189266
0.7751	Intermediate Similarity	NPC285254
0.775	Intermediate Similarity	NPC207873
0.775	Intermediate Similarity	NPC100573
0.7749	Intermediate Similarity	NPC186546
0.7749	Intermediate Similarity	NPC476576
0.7747	Intermediate Similarity	NPC24465
0.7746	Intermediate Similarity	NPC185838
0.7737	Intermediate Similarity	NPC302245
0.7737	Intermediate Similarity	NPC95426
0.7737	Intermediate Similarity	NPC16357
0.7737	Intermediate Similarity	NPC69213
0.7735	Intermediate Similarity	NPC24954
0.7727	Intermediate Similarity	NPC88249
0.7727	Intermediate Similarity	NPC151895
0.7727	Intermediate Similarity	NPC220858
0.7727	Intermediate Similarity	NPC192768
0.7727	Intermediate Similarity	NPC97221
0.772	Intermediate Similarity	NPC117717
0.7714	Intermediate Similarity	NPC428
0.7714	Intermediate Similarity	NPC135538
0.7714	Intermediate Similarity	NPC476571
0.7714	Intermediate Similarity	NPC24233
0.7714	Intermediate Similarity	NPC246587
0.7714	Intermediate Similarity	NPC147390
0.7714	Intermediate Similarity	NPC130941
0.7713	Intermediate Similarity	NPC267408
0.7705	Intermediate Similarity	NPC264850
0.7705	Intermediate Similarity	NPC13916
0.7701	Intermediate Similarity	NPC241704
0.77	Intermediate Similarity	NPC308943
0.7696	Intermediate Similarity	NPC65312
0.7696	Intermediate Similarity	NPC139783
0.7688	Intermediate Similarity	NPC2314
0.768	Intermediate Similarity	NPC29472
0.7676	Intermediate Similarity	NPC152212
0.767	Intermediate Similarity	NPC477565
0.767	Intermediate Similarity	NPC103379
0.767	Intermediate Similarity	NPC92541
0.767	Intermediate Similarity	NPC219162

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 NPC78284 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	245
0.1-0.2	796
0.2-0.3	1077
0.3-0.4	1836
0.4-0.5	2636
0.5-0.6	1970
0.6-0.7	530
0.7-0.8	60
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
0.772	Intermediate Similarity	NPD7262	Phase 1
0.7717	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7696	Intermediate Similarity	NPD7906	Approved
0.7647	Intermediate Similarity	NPD7479	Phase 2
0.7611	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD2420	Approved
0.76	Intermediate Similarity	NPD2421	Approved
0.7596	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD5938	Phase 3
0.7579	Intermediate Similarity	NPD4577	Approved
0.7579	Intermediate Similarity	NPD4578	Approved
0.7557	Intermediate Similarity	NPD4584	Approved
0.7552	Intermediate Similarity	NPD4663	Approved
0.7514	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD3051	Approved
0.7473	Intermediate Similarity	NPD2969	Approved
0.7473	Intermediate Similarity	NPD2970	Approved
0.7448	Intermediate Similarity	NPD8054	Approved
0.7448	Intermediate Similarity	NPD8053	Approved
0.7436	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD2489	Approved
0.7433	Intermediate Similarity	NPD27	Approved
0.7423	Intermediate Similarity	NPD3398	Discontinued
0.7396	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5241	Discontinued
0.738	Intermediate Similarity	NPD4083	Discontinued
0.7373	Intermediate Similarity	NPD7922	Phase 1
0.7312	Intermediate Similarity	NPD6037	Discontinued
0.7306	Intermediate Similarity	NPD7310	Approved
0.7306	Intermediate Similarity	NPD7312	Approved
0.7306	Intermediate Similarity	NPD7311	Approved
0.7306	Intermediate Similarity	NPD7313	Approved
0.7286	Intermediate Similarity	NPD5582	Discontinued
0.7268	Intermediate Similarity	NPD7309	Approved
0.7263	Intermediate Similarity	NPD8251	Approved
0.7263	Intermediate Similarity	NPD8252	Approved
0.7263	Intermediate Similarity	NPD8099	Discontinued
0.7254	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8156	Discontinued
0.7217	Intermediate Similarity	NPD2899	Discontinued
0.7217	Intermediate Similarity	NPD3763	Approved
0.7212	Intermediate Similarity	NPD4502	Phase 2
0.7204	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7831	Phase 2
0.7204	Intermediate Similarity	NPD7833	Phase 2
0.7192	Intermediate Similarity	NPD3452	Approved
0.7192	Intermediate Similarity	NPD3450	Approved
0.7192	Intermediate Similarity	NPD2493	Approved
0.7192	Intermediate Similarity	NPD2494	Approved
0.7183	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2973	Approved
0.7164	Intermediate Similarity	NPD2975	Approved
0.7164	Intermediate Similarity	NPD2974	Approved
0.7164	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4481	Phase 3
0.7158	Intermediate Similarity	NPD2898	Approved
0.7156	Intermediate Similarity	NPD8149	Discontinued
0.7151	Intermediate Similarity	NPD6788	Approved
0.715	Intermediate Similarity	NPD6496	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4859	Phase 1
0.7143	Intermediate Similarity	NPD4010	Discontinued
0.7143	Intermediate Similarity	NPD6612	Phase 2
0.7128	Intermediate Similarity	NPD5895	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD6090	Discontinued
0.7114	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3301	Approved
0.7088	Intermediate Similarity	NPD6030	Approved
0.7088	Intermediate Similarity	NPD6031	Approved
0.7087	Intermediate Similarity	NPD4583	Approved
0.7087	Intermediate Similarity	NPD4582	Approved
0.7083	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7298	Approved
0.7079	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4580	Approved
0.7059	Intermediate Similarity	NPD6494	Phase 2
0.7056	Intermediate Similarity	NPD3845	Phase 1
0.7053	Intermediate Similarity	NPD5530	Phase 1
0.7053	Intermediate Similarity	NPD6071	Discontinued
0.7043	Intermediate Similarity	NPD6283	Phase 2
0.7039	Intermediate Similarity	NPD4004	Approved
0.7039	Intermediate Similarity	NPD4002	Approved
0.7027	Intermediate Similarity	NPD4772	Phase 2
0.7027	Intermediate Similarity	NPD4773	Phase 2
0.7011	Intermediate Similarity	NPD4017	Approved
0.701	Intermediate Similarity	NPD3920	Phase 2
0.701	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3560	Approved
0.7005	Intermediate Similarity	NPD3559	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD3557	Approved
0.7005	Intermediate Similarity	NPD3556	Approved
0.7005	Intermediate Similarity	NPD3558	Approved
0.7005	Intermediate Similarity	NPD2560	Approved
0.7005	Intermediate Similarity	NPD2563	Approved
0.7	Intermediate Similarity	NPD2490	Approved
0.7	Intermediate Similarity	NPD2488	Approved
0.6978	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD3924	Approved
0.6965	Remote Similarity	NPD3923	Approved
0.6965	Remote Similarity	NPD3921	Approved
0.6965	Remote Similarity	NPD3922	Approved
0.6963	Remote Similarity	NPD5164	Discontinued
0.6961	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.695	Remote Similarity	NPD2843	Phase 2
0.695	Remote Similarity	NPD2845	Phase 2
0.6949	Remote Similarity	NPD1753	Discontinued
0.6943	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD7263	Phase 2
0.6927	Remote Similarity	NPD3975	Discontinued
0.6916	Remote Similarity	NPD7047	Phase 3
0.6915	Remote Similarity	NPD6063	Approved
0.6915	Remote Similarity	NPD5641	Discontinued
0.6912	Remote Similarity	NPD4604	Approved
0.6912	Remote Similarity	NPD4605	Approved
0.6908	Remote Similarity	NPD3516	Approved
0.6908	Remote Similarity	NPD3515	Approved
0.6906	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD3641	Approved
0.6902	Remote Similarity	NPD3639	Approved
0.6902	Remote Similarity	NPD3640	Phase 3
0.6898	Remote Similarity	NPD1769	Discontinued
0.6889	Remote Similarity	NPD3060	Approved
0.6887	Remote Similarity	NPD5936	Approved
0.6887	Remote Similarity	NPD5939	Approved
0.6884	Remote Similarity	NPD6339	Approved
0.6884	Remote Similarity	NPD6340	Approved
0.6881	Remote Similarity	NPD6997	Phase 2
0.6875	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5847	Phase 1
0.6872	Remote Similarity	NPD4726	Approved
0.6872	Remote Similarity	NPD42	Phase 2
0.6872	Remote Similarity	NPD6042	Phase 2
0.6872	Remote Similarity	NPD4725	Approved
0.6872	Remote Similarity	NPD4721	Approved
0.6872	Remote Similarity	NPD5810	Discontinued
0.6869	Remote Similarity	NPD2971	Approved
0.6869	Remote Similarity	NPD2968	Approved
0.6857	Remote Similarity	NPD7222	Phase 2
0.6854	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7278	Phase 2
0.6849	Remote Similarity	NPD7279	Phase 2
0.6847	Remote Similarity	NPD7125	Discontinued
0.6845	Remote Similarity	NPD3778	Approved
0.6845	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.683	Remote Similarity	NPD6723	Discontinued
0.6829	Remote Similarity	NPD7034	Discontinued
0.6829	Remote Similarity	NPD6527	Approved
0.6829	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD6357	Discontinued
0.6828	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD7802	Discontinued
0.6818	Remote Similarity	NPD3110	Approved
0.6818	Remote Similarity	NPD3109	Approved
0.6802	Remote Similarity	NPD6297	Approved
0.6796	Remote Similarity	NPD5177	Phase 3
0.6793	Remote Similarity	NPD4123	Phase 3
0.6792	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7169	Suspended
0.6776	Remote Similarity	NPD3816	Phase 1
0.6776	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD3815	Phase 1
0.6766	Remote Similarity	NPD4951	Discontinued
0.6761	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD5819	Phase 2
0.6756	Remote Similarity	NPD6625	Approved
0.6754	Remote Similarity	NPD4055	Discovery
0.6748	Remote Similarity	NPD5872	Discontinued
0.6745	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5709	Phase 3
0.6717	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD5071	Phase 2
0.6705	Remote Similarity	NPD5718	Phase 2
0.6703	Remote Similarity	NPD4237	Approved
0.6703	Remote Similarity	NPD4236	Phase 3
0.6703	Remote Similarity	NPD7447	Phase 1
0.6702	Remote Similarity	NPD5617	Suspended
0.67	Remote Similarity	NPD7630	Phase 3
0.67	Remote Similarity	NPD7628	Phase 3
0.67	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7225	Discontinued
0.6698	Remote Similarity	NPD6290	Phase 2
0.6697	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2978	Approved
0.6684	Remote Similarity	NPD2977	Approved
0.6684	Remote Similarity	NPD4666	Phase 3
0.6684	Remote Similarity	NPD2162	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD2176	Approved
0.6683	Remote Similarity	NPD2175	Phase 3

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