NPASS Compound

Structure

CID34421 OpenBabel06191715362D 37 42 0 0 1 0 0 0 0 0999 V2000 4.1834 1.1463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5655 4.0337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2253 0.7760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3688 1.7923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1096 2.0714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9841 -1.5182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0302 -1.4179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8307 1.4388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0254 -1.0843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6614 0.9592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8561 -0.6047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.4401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7027 0.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1375 0.4796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1404 2.1046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6408 3.7785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3126 -0.4424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3743 -0.6419 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8307 -0.4796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9592 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4806 2.0301 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0828 2.1770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6614 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6614 0.9592 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8307 -0.4796 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6614 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5737 1.2557 0.0000 C 0 0 1 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 0.8307 1.4388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9487 2.6210 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0425 4.4517 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8307 -1.4388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6567 0.3336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5737 -0.2964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2890 2.5465 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3995 2.8502 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 2 0 0 0 0 9 11 1 0 0 0 0 9 21 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 27 1 0 0 0 0 12 34 1 0 0 0 0 13 22 1 0 0 0 0 13 23 1 0 0 0 0 14 18 2 0 0 0 0 14 34 1 0 0 0 0 15 28 1 0 0 0 0 15 35 1 0 0 0 0 16 31 2 0 0 0 0 16 36 1 0 0 0 0 17 32 2 0 0 0 0 17 37 1 0 0 0 0 18 19 1 0 0 0 0 19 27 1 1 0 0 0 20 27 1 0 0 0 0 20 29 1 0 0 0 0 21 29 1 6 0 0 0 21 30 1 0 0 0 0 22 28 1 1 0 0 0 22 36 1 0 0 0 0 23 30 1 1 0 0 0 23 37 1 0 0 0 0 24 25 1 0 0 0 0 24 26 1 0 0 0 0 24 35 1 1 0 0 0 25 28 1 6 0 0 0 25 30 1 0 0 0 0 26 29 1 1 0 0 0 26 33 1 0 0 0 0 27 3 1 1 0 0 0 28 4 1 6 0 0 0 29 5 1 6 0 0 0 30 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.28
Volume:	524.447
LogP:	3.467
LogD:	3.031
LogS:	-4.658
# Rotatable Bonds:	5
TPSA:	95.2
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.46
Synthetic Accessibility Score:	5.395
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
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:	-5.089
MDCK Permeability:	4.042480941279791e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.03
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.871

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.321
Plasma Protein Binding (PPB):	90.3023910522461%
Volume Distribution (VD):	2.095
Pgp-substrate:	11.007467269897461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.415
CYP2C9-inhibitor:	0.145
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.662
CYP3A4-substrate:	0.377

ADMET: Excretion

Clearance (CL):	2.948
Half-life (T1/2):	0.522

ADMET: Toxicity

hERG Blockers:	0.387
Human Hepatotoxicity (H-HT):	0.785
Drug-inuced Liver Injury (DILI):	0.352
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.943
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.094
Carcinogencity:	0.024
Eye Corrosion:	0.004
Eye Irritation:	0.017
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC34421

Natural Product ID:	NPC34421
*Common Name:**	Diacetylvilasinin
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WGBLBVXSYGYVPN-VQDQNZKNSA-N
Standard InCHI:	InChI=1S/C30H40O7/c1-16(31)36-22-13-23(37-17(2)32)30(6)21-9-11-27(3)19(18-10-12-34-14-18)7-8-20(27)29(21,5)26(33)24-25(30)28(22,4)15-35-24/h8,10,12,14,19,21-26,33H,7,9,11,13,15H2,1-6H3/t19-,21-,22+,23-,24+,25-,26+,27-,28+,29-,30-/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@@H](OC(=O)C)[C@@]2([C@H]3[C@@]1(C)[C@H]1CC[C@@]4(C(=CC[C@H]4c4ccoc4)[C@]1(C)[C@@H]([C@@H]3OC2)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2229171
PubChem CID:	52952013
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193038]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1593280]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18816111]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[20669933]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[21381696]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381696]
NPO33254	munronia unifoliolata oliv	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22500574]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607354]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2614419]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26339153]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[28493718]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[9134742]
NPO4406	Azadirachta indica	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	14.6	%	PMID[537920]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	17.2	%	PMID[537920]

☑ 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 NPC34421 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	322
0.1-0.2	1179
0.2-0.3	2872
0.3-0.4	4922
0.4-0.5	9438
0.5-0.6	11238
0.6-0.7	10852
0.7-0.8	1375
0.8-0.85	343
0.85-0.9	132
0.9-0.95	16
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC98206
1.0	High Similarity	NPC237259
0.9728	High Similarity	NPC253201
0.9728	High Similarity	NPC302054
0.966	High Similarity	NPC472672
0.9655	High Similarity	NPC471007
0.9603	High Similarity	NPC470792
0.94	High Similarity	NPC296807
0.94	High Similarity	NPC155939
0.94	High Similarity	NPC141538
0.9355	High Similarity	NPC310572
0.9342	High Similarity	NPC472671
0.9276	High Similarity	NPC470119
0.9276	High Similarity	NPC214495
0.9276	High Similarity	NPC475066
0.9216	High Similarity	NPC475226
0.9195	High Similarity	NPC69647
0.9195	High Similarity	NPC125182
0.9189	High Similarity	NPC216755
0.915	High Similarity	NPC469847
0.9145	High Similarity	NPC92979
0.9139	High Similarity	NPC33938
0.9133	High Similarity	NPC470997
0.9133	High Similarity	NPC196846
0.9067	High Similarity	NPC472654
0.9067	High Similarity	NPC234494
0.9067	High Similarity	NPC471001
0.906	High Similarity	NPC471174
0.906	High Similarity	NPC255414
0.9045	High Similarity	NPC472670
0.9045	High Similarity	NPC307781
0.9026	High Similarity	NPC197137
0.9026	High Similarity	NPC194499
0.9013	High Similarity	NPC268905
0.9013	High Similarity	NPC308205
0.9013	High Similarity	NPC29695
0.9013	High Similarity	NPC322546
0.9013	High Similarity	NPC182427
0.8994	High Similarity	NPC470995
0.8994	High Similarity	NPC118086
0.8968	High Similarity	NPC475967
0.8938	High Similarity	NPC475641
0.8938	High Similarity	NPC475237
0.8931	High Similarity	NPC472673
0.8926	High Similarity	NPC5676
0.8917	High Similarity	NPC283209
0.891	High Similarity	NPC470789
0.8903	High Similarity	NPC88007
0.8903	High Similarity	NPC472777
0.8903	High Similarity	NPC472778
0.8903	High Similarity	NPC470118
0.8903	High Similarity	NPC299038
0.8903	High Similarity	NPC472776
0.8889	High Similarity	NPC470996
0.8889	High Similarity	NPC294511
0.8889	High Similarity	NPC121615
0.8867	High Similarity	NPC470999
0.8816	High Similarity	NPC470998
0.8816	High Similarity	NPC195325
0.8812	High Similarity	NPC271235
0.8805	High Similarity	NPC472141
0.8797	High Similarity	NPC285567
0.8782	High Similarity	NPC195954
0.878	High Similarity	NPC11062
0.8766	High Similarity	NPC471002
0.8742	High Similarity	NPC62692
0.8742	High Similarity	NPC27541
0.8742	High Similarity	NPC126984
0.8742	High Similarity	NPC61967
0.8734	High Similarity	NPC79571
0.8734	High Similarity	NPC68848
0.8734	High Similarity	NPC200782
0.8733	High Similarity	NPC251865
0.8726	High Similarity	NPC84349
0.8725	High Similarity	NPC121158
0.8704	High Similarity	NPC285227
0.8701	High Similarity	NPC471000
0.8701	High Similarity	NPC116717
0.8684	High Similarity	NPC302987
0.8679	High Similarity	NPC472139
0.8679	High Similarity	NPC472773
0.8671	High Similarity	NPC8389
0.8662	High Similarity	NPC261597
0.8662	High Similarity	NPC304692
0.8654	High Similarity	NPC44675
0.8654	High Similarity	NPC214541
0.8649	High Similarity	NPC90953
0.8645	High Similarity	NPC469503
0.8645	High Similarity	NPC246164
0.8636	High Similarity	NPC212257
0.8636	High Similarity	NPC228842
0.8634	High Similarity	NPC472651
0.863	High Similarity	NPC476947
0.8616	High Similarity	NPC472771
0.8616	High Similarity	NPC188649
0.8616	High Similarity	NPC18986
0.8616	High Similarity	NPC471003
0.8614	High Similarity	NPC470938
0.8599	High Similarity	NPC104736
0.8591	High Similarity	NPC56197
0.8591	High Similarity	NPC67003
0.8589	High Similarity	NPC294512
0.8581	High Similarity	NPC18135
0.8581	High Similarity	NPC291150
0.8581	High Similarity	NPC272590
0.858	High Similarity	NPC472652
0.8571	High Similarity	NPC93172
0.8571	High Similarity	NPC105395
0.8571	High Similarity	NPC97574
0.8571	High Similarity	NPC121995
0.8571	High Similarity	NPC470790
0.8571	High Similarity	NPC470791
0.8562	High Similarity	NPC302369
0.8562	High Similarity	NPC288602
0.8562	High Similarity	NPC134254
0.8562	High Similarity	NPC39986
0.8562	High Similarity	NPC88841
0.8562	High Similarity	NPC471168
0.8562	High Similarity	NPC71821
0.8553	High Similarity	NPC335761
0.8544	High Similarity	NPC187149
0.8544	High Similarity	NPC7059
0.8544	High Similarity	NPC36655
0.8543	High Similarity	NPC476946
0.8528	High Similarity	NPC82602
0.8526	High Similarity	NPC476201
0.8519	High Similarity	NPC472774
0.8519	High Similarity	NPC472775
0.8516	High Similarity	NPC5180
0.8516	High Similarity	NPC156189
0.8509	High Similarity	NPC470182
0.8509	High Similarity	NPC276551
0.85	High Similarity	NPC69028
0.85	High Similarity	NPC5741
0.85	High Similarity	NPC82851
0.8493	Intermediate Similarity	NPC218838
0.8491	Intermediate Similarity	NPC307383
0.8491	Intermediate Similarity	NPC474611
0.8485	Intermediate Similarity	NPC471437
0.8485	Intermediate Similarity	NPC236004
0.8485	Intermediate Similarity	NPC94763
0.8483	Intermediate Similarity	NPC89133
0.8481	Intermediate Similarity	NPC41880
0.8471	Intermediate Similarity	NPC57998
0.8471	Intermediate Similarity	NPC282445
0.8471	Intermediate Similarity	NPC178932
0.8466	Intermediate Similarity	NPC160651
0.8466	Intermediate Similarity	NPC296558
0.8466	Intermediate Similarity	NPC472765
0.8466	Intermediate Similarity	NPC471397
0.8466	Intermediate Similarity	NPC472766
0.8462	Intermediate Similarity	NPC242068
0.8462	Intermediate Similarity	NPC247563
0.8457	Intermediate Similarity	NPC470875
0.8457	Intermediate Similarity	NPC86800
0.8457	Intermediate Similarity	NPC277618
0.8447	Intermediate Similarity	NPC477405
0.8447	Intermediate Similarity	NPC663
0.8447	Intermediate Similarity	NPC292389
0.8447	Intermediate Similarity	NPC475039
0.8447	Intermediate Similarity	NPC469846
0.8447	Intermediate Similarity	NPC469338
0.8447	Intermediate Similarity	NPC476035
0.8447	Intermediate Similarity	NPC165218
0.8447	Intermediate Similarity	NPC224394
0.8447	Intermediate Similarity	NPC14499
0.8442	Intermediate Similarity	NPC250228
0.8438	Intermediate Similarity	NPC472653
0.8438	Intermediate Similarity	NPC287559
0.8434	Intermediate Similarity	NPC56953
0.8434	Intermediate Similarity	NPC176413
0.8431	Intermediate Similarity	NPC34056
0.8431	Intermediate Similarity	NPC41182
0.8431	Intermediate Similarity	NPC185456
0.8428	Intermediate Similarity	NPC45101
0.8428	Intermediate Similarity	NPC472772
0.8424	Intermediate Similarity	NPC469848
0.8421	Intermediate Similarity	NPC243577
0.8418	Intermediate Similarity	NPC476262
0.8418	Intermediate Similarity	NPC35000
0.8418	Intermediate Similarity	NPC469336
0.8418	Intermediate Similarity	NPC264943
0.8408	Intermediate Similarity	NPC75906
0.8408	Intermediate Similarity	NPC476939
0.8408	Intermediate Similarity	NPC476940
0.8405	Intermediate Similarity	NPC476850
0.8405	Intermediate Similarity	NPC472282
0.8405	Intermediate Similarity	NPC100333
0.8405	Intermediate Similarity	NPC173516
0.8405	Intermediate Similarity	NPC472764
0.8405	Intermediate Similarity	NPC476861
0.8395	Intermediate Similarity	NPC276735
0.8395	Intermediate Similarity	NPC469849
0.8395	Intermediate Similarity	NPC123088
0.8395	Intermediate Similarity	NPC271657
0.8395	Intermediate Similarity	NPC470940
0.8387	Intermediate Similarity	NPC93666
0.8385	Intermediate Similarity	NPC263432
0.8385	Intermediate Similarity	NPC329938
0.8385	Intermediate Similarity	NPC471166

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 NPC34421 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	831
0.2-0.3	2014
0.3-0.4	2629
0.4-0.5	2012
0.5-0.6	1048
0.6-0.7	316
0.7-0.8	19
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8535	High Similarity	NPD5761	Phase 2
0.8535	High Similarity	NPD5760	Phase 2
0.7977	Intermediate Similarity	NPD8434	Phase 2
0.7791	Intermediate Similarity	NPD6764	Approved
0.7791	Intermediate Similarity	NPD6765	Approved
0.7679	Intermediate Similarity	NPD8127	Discontinued
0.7658	Intermediate Similarity	NPD4628	Phase 3
0.7614	Intermediate Similarity	NPD6785	Approved
0.7614	Intermediate Similarity	NPD6784	Approved
0.7531	Intermediate Similarity	NPD6273	Approved
0.7386	Intermediate Similarity	NPD6559	Discontinued
0.7353	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD4965	Approved
0.7337	Intermediate Similarity	NPD4966	Approved
0.7337	Intermediate Similarity	NPD4967	Phase 2
0.7318	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD5844	Phase 1
0.7267	Intermediate Similarity	NPD7199	Phase 2
0.7251	Intermediate Similarity	NPD6234	Discontinued
0.725	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD37	Approved
0.7159	Intermediate Similarity	NPD7228	Approved
0.7152	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5762	Approved
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.7143	Intermediate Similarity	NPD5763	Approved
0.7135	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7819	Suspended
0.7117	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7075	Discontinued
0.7086	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6355	Discontinued
0.7037	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6002	Phase 3
0.7037	Intermediate Similarity	NPD6004	Phase 3
0.7037	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6005	Phase 3
0.703	Intermediate Similarity	NPD7236	Approved
0.7017	Intermediate Similarity	NPD8313	Approved
0.7017	Intermediate Similarity	NPD8312	Approved
0.7016	Intermediate Similarity	NPD7497	Discontinued
0.7	Intermediate Similarity	NPD7240	Approved
0.6982	Remote Similarity	NPD7458	Discontinued
0.6981	Remote Similarity	NPD4140	Approved
0.6959	Remote Similarity	NPD6801	Discontinued
0.6937	Remote Similarity	NPD5735	Approved
0.6936	Remote Similarity	NPD7768	Phase 2
0.6935	Remote Similarity	NPD8404	Phase 2
0.6919	Remote Similarity	NPD8455	Phase 2
0.6919	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD8032	Phase 2
0.6914	Remote Similarity	NPD5494	Approved
0.691	Remote Similarity	NPD7473	Discontinued
0.6909	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7003	Approved
0.6909	Remote Similarity	NPD3750	Approved
0.6909	Remote Similarity	NPD4110	Phase 3
0.6886	Remote Similarity	NPD6799	Approved
0.6886	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3226	Approved
0.6879	Remote Similarity	NPD3817	Phase 2
0.6879	Remote Similarity	NPD5402	Approved
0.6872	Remote Similarity	NPD7799	Discontinued
0.6872	Remote Similarity	NPD3818	Discontinued
0.6871	Remote Similarity	NPD1551	Phase 2
0.6864	Remote Similarity	NPD920	Approved
0.6864	Remote Similarity	NPD5403	Approved
0.686	Remote Similarity	NPD1934	Approved
0.6857	Remote Similarity	NPD919	Approved
0.6855	Remote Similarity	NPD6798	Discontinued
0.6845	Remote Similarity	NPD5401	Approved
0.6842	Remote Similarity	NPD4380	Phase 2
0.6836	Remote Similarity	NPD6232	Discontinued
0.6829	Remote Similarity	NPD2346	Discontinued
0.6824	Remote Similarity	NPD7239	Suspended
0.6815	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6233	Phase 2
0.6813	Remote Similarity	NPD7685	Pre-registration
0.681	Remote Similarity	NPD2799	Discontinued
0.681	Remote Similarity	NPD3748	Approved
0.6807	Remote Similarity	NPD8166	Discontinued
0.6802	Remote Similarity	NPD7411	Suspended
0.68	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.68	Remote Similarity	NPD3749	Approved
0.6792	Remote Similarity	NPD7095	Approved
0.6792	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.679	Remote Similarity	NPD6653	Approved
0.6782	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6166	Phase 2
0.676	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3764	Approved
0.6746	Remote Similarity	NPD2532	Approved
0.6746	Remote Similarity	NPD2534	Approved
0.6746	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2533	Approved
0.6744	Remote Similarity	NPD7028	Phase 2
0.6743	Remote Similarity	NPD3882	Suspended
0.6742	Remote Similarity	NPD7229	Phase 3
0.6726	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6663	Approved
0.6706	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD6100	Approved
0.6649	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7054	Approved
0.6647	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2797	Approved
0.6646	Remote Similarity	NPD7097	Phase 1
0.6646	Remote Similarity	NPD2313	Discontinued
0.6634	Remote Similarity	NPD7047	Phase 3
0.6629	Remote Similarity	NPD2801	Approved
0.6629	Remote Similarity	NPD1465	Phase 2
0.6625	Remote Similarity	NPD6832	Phase 2
0.6612	Remote Similarity	NPD7472	Approved
0.6609	Remote Similarity	NPD6677	Suspended
0.6606	Remote Similarity	NPD7033	Discontinued
0.6606	Remote Similarity	NPD4308	Phase 3
0.6592	Remote Similarity	NPD6959	Discontinued
0.6592	Remote Similarity	NPD1247	Approved
0.6591	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1549	Phase 2
0.6587	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6353	Approved
0.6582	Remote Similarity	NPD7680	Approved
0.6575	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6190	Approved
0.6566	Remote Similarity	NPD2438	Suspended
0.6564	Remote Similarity	NPD4060	Phase 1
0.6562	Remote Similarity	NPD5736	Approved
0.6557	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7315	Approved
0.6548	Remote Similarity	NPD1243	Approved
0.6548	Remote Similarity	NPD6674	Discontinued
0.6543	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD3268	Approved
0.6543	Remote Similarity	NPD8150	Discontinued
0.6541	Remote Similarity	NPD7038	Approved
0.6541	Remote Similarity	NPD7039	Approved
0.6541	Remote Similarity	NPD7251	Discontinued
0.6527	Remote Similarity	NPD1471	Phase 3
0.6527	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD8407	Phase 2
0.6524	Remote Similarity	NPD447	Suspended
0.6519	Remote Similarity	NPD5327	Phase 3
0.6514	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7808	Phase 3
0.6503	Remote Similarity	NPD3751	Discontinued
0.6503	Remote Similarity	NPD7177	Discontinued
0.6503	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5647	Approved
0.6491	Remote Similarity	NPD1511	Approved
0.6488	Remote Similarity	NPD2424	Discontinued
0.6488	Remote Similarity	NPD4534	Discontinued
0.6486	Remote Similarity	NPD6797	Phase 2
0.6478	Remote Similarity	NPD8651	Approved
0.6478	Remote Similarity	NPD1876	Approved
0.6478	Remote Similarity	NPD1283	Approved
0.6474	Remote Similarity	NPD1778	Approved
0.6474	Remote Similarity	NPD17	Approved
0.6464	Remote Similarity	NPD3787	Discontinued
0.6463	Remote Similarity	NPD3620	Phase 2
0.6463	Remote Similarity	NPD4307	Phase 2
0.6463	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD2979	Phase 3
0.6462	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD7057	Phase 3
0.6461	Remote Similarity	NPD7058	Phase 2
0.6453	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD8368	Discontinued
0.645	Remote Similarity	NPD1652	Phase 2
0.645	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.645	Remote Similarity	NPD2800	Approved
0.6447	Remote Similarity	NPD3057	Approved
0.6442	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6362	Approved
0.6433	Remote Similarity	NPD7440	Discontinued
0.6429	Remote Similarity	NPD4107	Approved
0.6429	Remote Similarity	NPD3926	Phase 2
0.6429	Remote Similarity	NPD2344	Approved
0.6424	Remote Similarity	NPD230	Phase 1
0.6424	Remote Similarity	NPD5124	Phase 1
0.6424	Remote Similarity	NPD1933	Approved
0.6424	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD1899	Clinical (unspecified phase)

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