NPASS Compound

Structure

NPC20360 OpenBabel07101718272D 35 39 0 0 1 0 0 0 0 0999 V2000 -1.7885 3.6338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3513 -3.1020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0998 0.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4915 3.0727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9363 -2.2366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0880 -2.6143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0334 -1.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3368 -2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2821 -0.7673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0151 0.0971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7139 -0.8483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5609 -0.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2597 -1.5995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4915 1.2155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6873 -0.1773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4289 1.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8802 3.8269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4338 -1.1450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0916 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1832 -1.5025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4915 0.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4289 1.0382 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6873 1.6798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8831 0.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5458 2.2537 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8831 1.2155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.5025 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5458 0.7512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5932 4.7100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5458 2.2537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7290 -2.2537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2956 -0.1773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6873 2.6084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2589 3.1368 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 31 1 0 0 0 0 3 32 1 0 0 0 0 4 33 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 18 2 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 19 2 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 21 1 0 0 0 0 15 24 2 0 0 0 0 16 22 1 0 0 0 0 16 25 1 0 0 0 0 17 29 2 0 0 0 0 17 34 1 0 0 0 0 18 22 1 0 0 0 0 20 31 1 0 0 0 0 21 32 1 0 0 0 0 22 28 1 6 0 0 0 23 26 2 0 0 0 0 23 33 1 0 0 0 0 24 26 1 0 0 0 0 24 35 1 0 0 0 0 25 27 1 1 0 0 0 25 34 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 6 0 0 0 27 30 1 0 0 0 0 28 19 1 6 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	476.18
Volume:	485.229
LogP:	4.204
LogD:	3.649
LogS:	-5.572
# Rotatable Bonds:	7
TPSA:	83.45
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	3.809
Fsp3:	0.321
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.195
MDCK Permeability:	5.701586997020058e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.884

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.691
Plasma Protein Binding (PPB):	92.2186279296875%
Volume Distribution (VD):	0.997
Pgp-substrate:	7.090763092041016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.153
CYP1A2-substrate:	0.51
CYP2C19-inhibitor:	0.848
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.896
CYP2C9-substrate:	0.731
CYP2D6-inhibitor:	0.356
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.869

ADMET: Excretion

Clearance (CL):	8.53
Half-life (T1/2):	0.203

ADMET: Toxicity

hERG Blockers:	0.499
Human Hepatotoxicity (H-HT):	0.853
Drug-inuced Liver Injury (DILI):	0.917
AMES Toxicity:	0.7
Rat Oral Acute Toxicity:	0.565
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.051
Carcinogencity:	0.562
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.743

Download Data

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

Natural Product: NPC20360

Natural Product ID:	NPC20360
*Common Name:**	1-O-Acetylrocaglaol
IUPAC Name:	[(1R,3S,3aR,8bS)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1-yl] acetate
Synonyms:	1-O-Acetylrocaglaol
Standard InCHIKey:	CGFKKPRGWNMNFP-CEYYOHNYSA-N
Standard InCHI:	InChI=1S/C28H28O7/c1-17(29)34-25-16-22(18-8-6-5-7-9-18)28(19-10-12-20(31-2)13-11-19)27(25,30)26-23(33-4)14-21(32-3)15-24(26)35-28/h5-15,22,25,30H,16H2,1-4H3/t22-,25+,27+,28-/m0/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H](c2ccccc2)[C@@]2(c3ccc(cc3)OC)[C@@]1(c1c(cc(cc1O2)OC)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476922
PubChem CID:	11363545
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0003109] Flavaglines

*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
NPO3427	Aglaia rubiginosa	Species	Meliaceae	Eukaryota	twigs and leaves	n.a.	n.a.	PMID[15043407]
NPO3427	Aglaia rubiginosa	Species	Meliaceae	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
ED50	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	189.0	nM	PMID[537113]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	=	231.0	nM	PMID[537113]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	147.0	nM	PMID[537113]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	273.0	nM	PMID[537113]
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	210.0	nM	PMID[537113]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	210.0	nM	PMID[537113]

☑ 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 NPC20360 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	317
0.1-0.2	1341
0.2-0.3	3235
0.3-0.4	8092
0.4-0.5	10835
0.5-0.6	5034
0.6-0.7	9467
0.7-0.8	4161
0.8-0.85	193
0.85-0.9	14
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9571	High Similarity	NPC184607
0.95	High Similarity	NPC470937
0.9267	High Similarity	NPC329743
0.9205	High Similarity	NPC73422
0.9205	High Similarity	NPC310399
0.9145	High Similarity	NPC90336
0.9139	High Similarity	NPC209473
0.8993	High Similarity	NPC51543
0.8933	High Similarity	NPC87363
0.891	High Similarity	NPC475621
0.8882	High Similarity	NPC189730
0.8816	High Similarity	NPC164152
0.8688	High Similarity	NPC271755
0.8688	High Similarity	NPC254071
0.8688	High Similarity	NPC222665
0.8688	High Similarity	NPC149502
0.8681	High Similarity	NPC474687
0.8652	High Similarity	NPC162801
0.8611	High Similarity	NPC3049
0.8601	High Similarity	NPC117048
0.8601	High Similarity	NPC124085
0.8531	High Similarity	NPC85435
0.8528	High Similarity	NPC263955
0.8528	High Similarity	NPC23593
0.8493	Intermediate Similarity	NPC475836
0.8483	Intermediate Similarity	NPC18189
0.8483	Intermediate Similarity	NPC20829
0.8483	Intermediate Similarity	NPC262585
0.8476	Intermediate Similarity	NPC29587
0.8467	Intermediate Similarity	NPC211758
0.8467	Intermediate Similarity	NPC87794
0.8466	Intermediate Similarity	NPC107739
0.8462	Intermediate Similarity	NPC13005
0.844	Intermediate Similarity	NPC87224
0.844	Intermediate Similarity	NPC39064
0.844	Intermediate Similarity	NPC222572
0.844	Intermediate Similarity	NPC47283
0.8424	Intermediate Similarity	NPC236089
0.8403	Intermediate Similarity	NPC215037
0.8392	Intermediate Similarity	NPC228369
0.8392	Intermediate Similarity	NPC196765
0.8392	Intermediate Similarity	NPC476166
0.8392	Intermediate Similarity	NPC12875
0.8392	Intermediate Similarity	NPC129106
0.8392	Intermediate Similarity	NPC268917
0.8392	Intermediate Similarity	NPC236014
0.8392	Intermediate Similarity	NPC150011
0.8392	Intermediate Similarity	NPC280653
0.8392	Intermediate Similarity	NPC164574
0.8392	Intermediate Similarity	NPC207892
0.8392	Intermediate Similarity	NPC300875
0.8392	Intermediate Similarity	NPC206224
0.8392	Intermediate Similarity	NPC17343
0.8392	Intermediate Similarity	NPC129784
0.8392	Intermediate Similarity	NPC118114
0.8389	Intermediate Similarity	NPC274721
0.8389	Intermediate Similarity	NPC155392
0.8389	Intermediate Similarity	NPC135767
0.8345	Intermediate Similarity	NPC223008
0.8345	Intermediate Similarity	NPC115335
0.8345	Intermediate Similarity	NPC225696
0.8345	Intermediate Similarity	NPC97834
0.8345	Intermediate Similarity	NPC296915
0.8345	Intermediate Similarity	NPC198154
0.8344	Intermediate Similarity	NPC324492
0.8344	Intermediate Similarity	NPC317053
0.8333	Intermediate Similarity	NPC317237
0.8333	Intermediate Similarity	NPC471824
0.8333	Intermediate Similarity	NPC44530
0.8333	Intermediate Similarity	NPC277951
0.8322	Intermediate Similarity	NPC27187
0.8322	Intermediate Similarity	NPC470225
0.8311	Intermediate Similarity	NPC184797
0.8311	Intermediate Similarity	NPC309124
0.8302	Intermediate Similarity	NPC470936
0.8298	Intermediate Similarity	NPC471215
0.8298	Intermediate Similarity	NPC50315
0.8298	Intermediate Similarity	NPC230479
0.8298	Intermediate Similarity	NPC283049
0.8298	Intermediate Similarity	NPC26879
0.8298	Intermediate Similarity	NPC262573
0.8289	Intermediate Similarity	NPC320671
0.8289	Intermediate Similarity	NPC327412
0.8289	Intermediate Similarity	NPC328567
0.8289	Intermediate Similarity	NPC320970
0.8288	Intermediate Similarity	NPC33986
0.8286	Intermediate Similarity	NPC256015
0.8286	Intermediate Similarity	NPC294156
0.8278	Intermediate Similarity	NPC181615
0.8278	Intermediate Similarity	NPC469701
0.8276	Intermediate Similarity	NPC92805
0.8264	Intermediate Similarity	NPC181497
0.8264	Intermediate Similarity	NPC271945
0.8264	Intermediate Similarity	NPC103799
0.8255	Intermediate Similarity	NPC476334
0.8255	Intermediate Similarity	NPC287286
0.8255	Intermediate Similarity	NPC152771
0.8255	Intermediate Similarity	NPC108674
0.8255	Intermediate Similarity	NPC195357
0.8243	Intermediate Similarity	NPC236306
0.8243	Intermediate Similarity	NPC151946
0.8243	Intermediate Similarity	NPC232164
0.8243	Intermediate Similarity	NPC473739
0.8243	Intermediate Similarity	NPC279573
0.8235	Intermediate Similarity	NPC252402
0.8235	Intermediate Similarity	NPC102934
0.8231	Intermediate Similarity	NPC126101
0.8231	Intermediate Similarity	NPC38099
0.8231	Intermediate Similarity	NPC26954
0.8231	Intermediate Similarity	NPC141717
0.8228	Intermediate Similarity	NPC125495
0.8224	Intermediate Similarity	NPC260397
0.8224	Intermediate Similarity	NPC40222
0.8224	Intermediate Similarity	NPC268515
0.8219	Intermediate Similarity	NPC98179
0.8219	Intermediate Similarity	NPC253574
0.8212	Intermediate Similarity	NPC470097
0.8212	Intermediate Similarity	NPC114119
0.8212	Intermediate Similarity	NPC471415
0.8212	Intermediate Similarity	NPC475492
0.82	Intermediate Similarity	NPC107161
0.82	Intermediate Similarity	NPC131971
0.82	Intermediate Similarity	NPC472353
0.8188	Intermediate Similarity	NPC312881
0.8188	Intermediate Similarity	NPC160283
0.8188	Intermediate Similarity	NPC27495
0.8188	Intermediate Similarity	NPC254759
0.8187	Intermediate Similarity	NPC92589
0.8182	Intermediate Similarity	NPC53986
0.8182	Intermediate Similarity	NPC38664
0.8182	Intermediate Similarity	NPC219923
0.8176	Intermediate Similarity	NPC232246
0.8176	Intermediate Similarity	NPC212124
0.8176	Intermediate Similarity	NPC153818
0.8176	Intermediate Similarity	NPC184861
0.8176	Intermediate Similarity	NPC281014
0.8176	Intermediate Similarity	NPC477938
0.8176	Intermediate Similarity	NPC294456
0.8176	Intermediate Similarity	NPC155963
0.8176	Intermediate Similarity	NPC225106
0.8163	Intermediate Similarity	NPC11727
0.8163	Intermediate Similarity	NPC15109
0.8163	Intermediate Similarity	NPC151224
0.8163	Intermediate Similarity	NPC125579
0.8163	Intermediate Similarity	NPC472525
0.8158	Intermediate Similarity	NPC475719
0.8158	Intermediate Similarity	NPC106126
0.8158	Intermediate Similarity	NPC43716
0.8158	Intermediate Similarity	NPC101255
0.8158	Intermediate Similarity	NPC108994
0.8146	Intermediate Similarity	NPC173203
0.8146	Intermediate Similarity	NPC81638
0.8146	Intermediate Similarity	NPC163508
0.8144	Intermediate Similarity	NPC206061
0.8141	Intermediate Similarity	NPC302610
0.8138	Intermediate Similarity	NPC211413
0.8138	Intermediate Similarity	NPC164804
0.8138	Intermediate Similarity	NPC68205
0.8138	Intermediate Similarity	NPC293203
0.8138	Intermediate Similarity	NPC29734
0.8138	Intermediate Similarity	NPC472590
0.8138	Intermediate Similarity	NPC118683
0.8138	Intermediate Similarity	NPC244888
0.8133	Intermediate Similarity	NPC247291
0.8133	Intermediate Similarity	NPC178054
0.8133	Intermediate Similarity	NPC263261
0.8133	Intermediate Similarity	NPC87725
0.8133	Intermediate Similarity	NPC5155
0.8133	Intermediate Similarity	NPC100482
0.8133	Intermediate Similarity	NPC277331
0.8125	Intermediate Similarity	NPC93962
0.8121	Intermediate Similarity	NPC292882
0.8121	Intermediate Similarity	NPC211110
0.8117	Intermediate Similarity	NPC169510
0.8108	Intermediate Similarity	NPC230734
0.8108	Intermediate Similarity	NPC474639
0.8108	Intermediate Similarity	NPC78746
0.8108	Intermediate Similarity	NPC248727
0.8108	Intermediate Similarity	NPC471988
0.8108	Intermediate Similarity	NPC162659
0.8108	Intermediate Similarity	NPC224543
0.8108	Intermediate Similarity	NPC188380
0.8108	Intermediate Similarity	NPC270456
0.8108	Intermediate Similarity	NPC265433
0.8108	Intermediate Similarity	NPC327735
0.8108	Intermediate Similarity	NPC471719
0.8108	Intermediate Similarity	NPC227503
0.8105	Intermediate Similarity	NPC212697
0.8105	Intermediate Similarity	NPC162193
0.8099	Intermediate Similarity	NPC207179
0.8099	Intermediate Similarity	NPC167571
0.8099	Intermediate Similarity	NPC278552
0.8095	Intermediate Similarity	NPC67247
0.8095	Intermediate Similarity	NPC213173
0.8095	Intermediate Similarity	NPC204353
0.8095	Intermediate Similarity	NPC55149
0.8095	Intermediate Similarity	NPC307412
0.8095	Intermediate Similarity	NPC50896
0.8095	Intermediate Similarity	NPC476616
0.8095	Intermediate Similarity	NPC476617

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 NPC20360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	255
0.1-0.2	818
0.2-0.3	1688
0.3-0.4	2635
0.4-0.5	2005
0.5-0.6	1106
0.6-0.7	547
0.7-0.8	94
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.831	Intermediate Similarity	NPD4908	Phase 1
0.8194	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7199	Phase 2
0.8086	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6002	Phase 3
0.8	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6004	Phase 3
0.8	Intermediate Similarity	NPD6005	Phase 3
0.8	Intermediate Similarity	NPD5763	Approved
0.8	Intermediate Similarity	NPD5762	Approved
0.7943	Intermediate Similarity	NPD1610	Phase 2
0.7905	Intermediate Similarity	NPD6355	Discontinued
0.7862	Intermediate Similarity	NPD2861	Phase 2
0.7838	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1613	Approved
0.7823	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD6798	Discontinued
0.7785	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD5124	Phase 1
0.7733	Intermediate Similarity	NPD6653	Approved
0.773	Intermediate Similarity	NPD6234	Discontinued
0.7718	Intermediate Similarity	NPD4140	Approved
0.7718	Intermediate Similarity	NPD4060	Phase 1
0.7716	Intermediate Similarity	NPD4965	Approved
0.7716	Intermediate Similarity	NPD4966	Approved
0.7716	Intermediate Similarity	NPD4967	Phase 2
0.7687	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5735	Approved
0.7662	Intermediate Similarity	NPD1652	Phase 2
0.766	Intermediate Similarity	NPD1548	Phase 1
0.7651	Intermediate Similarity	NPD6233	Phase 2
0.7643	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD37	Approved
0.7635	Intermediate Similarity	NPD3027	Phase 3
0.7632	Intermediate Similarity	NPD7033	Discontinued
0.7619	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD422	Phase 1
0.7517	Intermediate Similarity	NPD7095	Approved
0.7485	Intermediate Similarity	NPD7229	Phase 3
0.7485	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4749	Approved
0.7455	Intermediate Similarity	NPD7075	Discontinued
0.7451	Intermediate Similarity	NPD7097	Phase 1
0.7412	Intermediate Similarity	NPD7228	Approved
0.74	Intermediate Similarity	NPD4625	Phase 3
0.7394	Intermediate Similarity	NPD7768	Phase 2
0.7389	Intermediate Similarity	NPD3750	Approved
0.7389	Intermediate Similarity	NPD7466	Approved
0.7389	Intermediate Similarity	NPD4628	Phase 3
0.7386	Intermediate Similarity	NPD6353	Approved
0.7378	Intermediate Similarity	NPD8455	Phase 2
0.7368	Intermediate Similarity	NPD5844	Phase 1
0.7365	Intermediate Similarity	NPD6362	Approved
0.7365	Intermediate Similarity	NPD2797	Approved
0.7362	Intermediate Similarity	NPD7411	Suspended
0.7358	Intermediate Similarity	NPD6799	Approved
0.7357	Intermediate Similarity	NPD5535	Approved
0.7351	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1091	Approved
0.7325	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD1934	Approved
0.7317	Intermediate Similarity	NPD6801	Discontinued
0.7315	Intermediate Similarity	NPD5647	Approved
0.7301	Intermediate Similarity	NPD6599	Discontinued
0.7299	Intermediate Similarity	NPD7549	Discontinued
0.7296	Intermediate Similarity	NPD5058	Phase 3
0.7284	Intermediate Similarity	NPD1653	Approved
0.7278	Intermediate Similarity	NPD3892	Phase 2
0.7278	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7213	Phase 3
0.725	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7212	Phase 2
0.7248	Intermediate Similarity	NPD3094	Phase 2
0.7246	Intermediate Similarity	NPD3749	Approved
0.7246	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6559	Discontinued
0.7237	Intermediate Similarity	NPD3268	Approved
0.723	Intermediate Similarity	NPD5327	Phase 3
0.7229	Intermediate Similarity	NPD3817	Phase 2
0.7222	Intermediate Similarity	NPD5403	Approved
0.7215	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4340	Discontinued
0.7205	Intermediate Similarity	NPD7447	Phase 1
0.7205	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4380	Phase 2
0.7193	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6166	Phase 2
0.7193	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8651	Approved
0.7179	Intermediate Similarity	NPD5588	Approved
0.7179	Intermediate Similarity	NPD3748	Approved
0.7175	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7819	Suspended
0.716	Intermediate Similarity	NPD6273	Approved
0.716	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5958	Discontinued
0.7152	Intermediate Similarity	NPD1549	Phase 2
0.7152	Intermediate Similarity	NPD2424	Discontinued
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD7240	Approved
0.7143	Intermediate Similarity	NPD3620	Phase 2
0.7143	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6099	Approved
0.7134	Intermediate Similarity	NPD6100	Approved
0.7134	Intermediate Similarity	NPD2796	Approved
0.7126	Intermediate Similarity	NPD5402	Approved
0.7118	Intermediate Similarity	NPD8127	Discontinued
0.7115	Intermediate Similarity	NPD4538	Approved
0.7115	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4536	Approved
0.711	Intermediate Similarity	NPD3818	Discontinued
0.7099	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5401	Approved
0.7093	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4624	Approved
0.7083	Intermediate Similarity	NPD7157	Approved
0.7083	Intermediate Similarity	NPD3882	Suspended
0.7081	Intermediate Similarity	NPD6666	Approved
0.7081	Intermediate Similarity	NPD6667	Approved
0.7078	Intermediate Similarity	NPD4062	Phase 3
0.7076	Intermediate Similarity	NPD6232	Discontinued
0.7075	Intermediate Similarity	NPD5846	Approved
0.7075	Intermediate Similarity	NPD6516	Phase 2
0.7071	Intermediate Similarity	NPD2684	Approved
0.7067	Intermediate Similarity	NPD3225	Approved
0.7066	Intermediate Similarity	NPD5760	Phase 2
0.7066	Intermediate Similarity	NPD5761	Phase 2
0.7066	Intermediate Similarity	NPD2801	Approved
0.7063	Intermediate Similarity	NPD4110	Phase 3
0.7063	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5494	Approved
0.7052	Intermediate Similarity	NPD7473	Discontinued
0.7047	Intermediate Similarity	NPD1608	Approved
0.7039	Intermediate Similarity	NPD5736	Approved
0.7032	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3496	Discontinued
0.7025	Intermediate Similarity	NPD6032	Approved
0.7025	Intermediate Similarity	NPD1551	Phase 2
0.7013	Intermediate Similarity	NPD3764	Approved
0.7012	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD290	Approved
0.7	Intermediate Similarity	NPD6674	Discontinued
0.6993	Remote Similarity	NPD7843	Approved
0.698	Remote Similarity	NPD3092	Approved
0.6977	Remote Similarity	NPD3787	Discontinued
0.6974	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6663	Approved
0.6962	Remote Similarity	NPD5960	Phase 3
0.6962	Remote Similarity	NPD1510	Phase 2
0.6959	Remote Similarity	NPD6746	Phase 2
0.6951	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7741	Discontinued
0.6937	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD4534	Discontinued
0.6933	Remote Similarity	NPD1511	Approved
0.6932	Remote Similarity	NPD7074	Phase 3
0.6928	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3018	Phase 2
0.6919	Remote Similarity	NPD6959	Discontinued
0.6908	Remote Similarity	NPD3266	Approved
0.6908	Remote Similarity	NPD987	Approved
0.6908	Remote Similarity	NPD3267	Approved
0.6905	Remote Similarity	NPD4433	Discontinued
0.6892	Remote Similarity	NPD5585	Approved
0.689	Remote Similarity	NPD2533	Approved
0.689	Remote Similarity	NPD2534	Approved
0.689	Remote Similarity	NPD2532	Approved
0.6887	Remote Similarity	NPD6583	Phase 3
0.6887	Remote Similarity	NPD6582	Phase 2
0.6883	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7054	Approved
0.6875	Remote Similarity	NPD7266	Discontinued
0.6875	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1465	Phase 2
0.6863	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6584	Phase 3
0.6859	Remote Similarity	NPD8032	Phase 2
0.6855	Remote Similarity	NPD2799	Discontinued
0.6855	Remote Similarity	NPD4308	Phase 3
0.6849	Remote Similarity	NPD6671	Approved
0.6848	Remote Similarity	NPD1512	Approved
0.6846	Remote Similarity	NPD1778	Approved
0.6846	Remote Similarity	NPD4626	Approved
0.6846	Remote Similarity	NPD17	Approved
0.6845	Remote Similarity	NPD6072	Discontinued
0.6842	Remote Similarity	NPD6971	Discontinued
0.6836	Remote Similarity	NPD7472	Approved
0.6835	Remote Similarity	NPD2157	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