NPASS Compound

Structure

NPC155939 OpenBabel07101719252D 34 39 0 0 1 0 0 0 0 0999 V2000 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5120 -1.8685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1142 -2.1594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8943 -2.5438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1965 1.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5860 -2.1163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0625 0.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8601 -0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4533 0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1288 -2.2695 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 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 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4165 -2.9713 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -0.3478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 10 2 0 0 0 0 8 20 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 25 1 0 0 0 0 11 32 1 0 0 0 0 12 19 1 0 0 0 0 12 21 1 0 0 0 0 13 16 2 0 0 0 0 13 32 1 0 0 0 0 14 25 1 0 0 0 0 14 33 1 0 0 0 0 15 29 2 0 0 0 0 15 34 1 0 0 0 0 16 17 1 0 0 0 0 17 26 1 1 0 0 0 18 26 1 0 0 0 0 18 27 1 0 0 0 0 19 27 1 6 0 0 0 19 28 1 0 0 0 0 20 28 1 0 0 0 0 20 30 2 0 0 0 0 21 26 1 1 0 0 0 21 34 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 33 1 1 0 0 0 23 25 1 6 0 0 0 23 28 1 0 0 0 0 24 27 1 1 0 0 0 24 31 1 0 0 0 0 25 2 1 6 0 0 0 26 3 1 1 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	466.24
Volume:	478.428
LogP:	2.545
LogD:	2.283
LogS:	-4.607
# Rotatable Bonds:	3
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.519
Synthetic Accessibility Score:	5.54
Fsp3:	0.643
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:	-4.926
MDCK Permeability:	2.7730480724130757e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.548
Human Intestinal Absorption (HIA):	0.087
20% Bioavailability (F20%):	0.943
30% Bioavailability (F30%):	0.497

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.964
Plasma Protein Binding (PPB):	92.63324737548828%
Volume Distribution (VD):	2.769
Pgp-substrate:	11.10350227355957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.367
CYP2C9-inhibitor:	0.088
CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.847
CYP3A4-substrate:	0.433

ADMET: Excretion

Clearance (CL):	7.223
Half-life (T1/2):	0.459

ADMET: Toxicity

hERG Blockers:	0.797
Human Hepatotoxicity (H-HT):	0.395
Drug-inuced Liver Injury (DILI):	0.249
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.987
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.599
Carcinogencity:	0.802
Eye Corrosion:	0.007
Eye Irritation:	0.028
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC155939

Natural Product ID:	NPC155939
*Common Name:**	Ceramicine I
IUPAC Name:	n.a.
Synonyms:	Ceramicine I
Standard InCHIKey:	PCOIBLURWHFKMR-XWQWWSFPSA-N
Standard InCHI:	InChI=1S/C28H34O6/c1-15(29)34-21-12-19-27(4,18-7-6-17(26(18,21)3)16-9-11-32-13-16)24(31)22-23-25(2,14-33-22)10-8-20(30)28(19,23)5/h7-11,13,17,19,21-24,31H,6,12,14H2,1-5H3/t17-,19-,21-,22+,23-,24+,25-,26-,27-,28-/m0/s1
SMILES:	CC(=O)O[C@H]1C[C@H]2[C@@](C3=CC[C@H]([C@]13C)c1cocc1)(C)[C@H](O)[C@H]1[C@@H]3[C@]2(C)C(=O)C=C[C@@]3(C)CO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2335027
PubChem CID:	51041218
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
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19081726]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21428417]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[21428417]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23395661]
NPO5587	Chisocheton ceramicus	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
IC50	1
Others	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Ratio CC50/IC50	>	1.2	n.a.	PMID[511212]
NPT27	Others	Unspecified		CC50	>	50000.0	nM	PMID[511212]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	41000.0	nM	PMID[511212]

☑ 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 NPC155939 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	1233
0.2-0.3	2797
0.3-0.4	4855
0.4-0.5	9771
0.5-0.6	11265
0.6-0.7	10469
0.7-0.8	1474
0.8-0.85	318
0.85-0.9	143
0.9-0.95	44
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC141538
1.0	High Similarity	NPC296807
0.9726	High Similarity	NPC196846
0.9658	High Similarity	NPC471001
0.9658	High Similarity	NPC234494
0.9597	High Similarity	NPC92979
0.9521	High Similarity	NPC471174
0.947	High Similarity	NPC197137
0.9463	High Similarity	NPC33938
0.9463	High Similarity	NPC470996
0.9459	High Similarity	NPC470997
0.9452	High Similarity	NPC470999
0.9412	High Similarity	NPC470792
0.94	High Similarity	NPC34421
0.94	High Similarity	NPC98206
0.94	High Similarity	NPC237259
0.9388	High Similarity	NPC216755
0.9333	High Similarity	NPC471002
0.9324	High Similarity	NPC471007
0.9267	High Similarity	NPC471000
0.9257	High Similarity	NPC302987
0.9216	High Similarity	NPC470118
0.9205	High Similarity	NPC246164
0.9156	High Similarity	NPC475226
0.9156	High Similarity	NPC84349
0.9156	High Similarity	NPC472671
0.9145	High Similarity	NPC302054
0.9145	High Similarity	NPC253201
0.9139	High Similarity	NPC272590
0.9139	High Similarity	NPC116717
0.9139	High Similarity	NPC291150
0.9133	High Similarity	NPC472654
0.9133	High Similarity	NPC470998
0.9091	High Similarity	NPC475066
0.9091	High Similarity	NPC214495
0.9091	High Similarity	NPC470119
0.9079	High Similarity	NPC294511
0.9079	High Similarity	NPC472672
0.9079	High Similarity	NPC121615
0.9073	High Similarity	NPC5180
0.9041	High Similarity	NPC56197
0.9038	High Similarity	NPC471003
0.9007	High Similarity	NPC125182
0.9007	High Similarity	NPC69647
0.8993	High Similarity	NPC185456
0.8968	High Similarity	NPC472778
0.8968	High Similarity	NPC469847
0.8968	High Similarity	NPC472776
0.8968	High Similarity	NPC472777
0.8954	High Similarity	NPC268905
0.8938	High Similarity	NPC470995
0.8926	High Similarity	NPC238843
0.8926	High Similarity	NPC199044
0.8926	High Similarity	NPC251865
0.891	High Similarity	NPC475967
0.8882	High Similarity	NPC195325
0.8882	High Similarity	NPC285227
0.8874	High Similarity	NPC255414
0.8868	High Similarity	NPC307781
0.8868	High Similarity	NPC472670
0.8867	High Similarity	NPC34056
0.8861	High Similarity	NPC283209
0.8854	High Similarity	NPC470789
0.8846	High Similarity	NPC194499
0.8846	High Similarity	NPC299038
0.8839	High Similarity	NPC214541
0.8839	High Similarity	NPC44675
0.8831	High Similarity	NPC182427
0.8831	High Similarity	NPC308205
0.8831	High Similarity	NPC29695
0.8831	High Similarity	NPC322546
0.8824	High Similarity	NPC228842
0.8812	High Similarity	NPC310572
0.8808	High Similarity	NPC471292
0.8805	High Similarity	NPC276551
0.8797	High Similarity	NPC69028
0.8792	High Similarity	NPC121158
0.879	High Similarity	NPC307383
0.8774	High Similarity	NPC178932
0.8765	High Similarity	NPC475641
0.8765	High Similarity	NPC475237
0.8758	High Similarity	NPC472673
0.875	High Similarity	NPC71821
0.875	High Similarity	NPC472141
0.875	High Similarity	NPC470875
0.8742	High Similarity	NPC224394
0.8742	High Similarity	NPC285567
0.8742	High Similarity	NPC469338
0.8742	High Similarity	NPC663
0.8742	High Similarity	NPC5676
0.8742	High Similarity	NPC472773
0.8742	High Similarity	NPC292389
0.8726	High Similarity	NPC261597
0.8726	High Similarity	NPC88007
0.8726	High Similarity	NPC7059
0.8718	High Similarity	NPC469336
0.8718	High Similarity	NPC264943
0.8718	High Similarity	NPC35000
0.8716	High Similarity	NPC90953
0.871	High Similarity	NPC469503
0.8704	High Similarity	NPC118086
0.8701	High Similarity	NPC156189
0.8696	High Similarity	NPC472651
0.8688	High Similarity	NPC470940
0.8688	High Similarity	NPC469849
0.8679	High Similarity	NPC472771
0.8679	High Similarity	NPC79571
0.8679	High Similarity	NPC5079
0.8679	High Similarity	NPC18986
0.8679	High Similarity	NPC68848
0.8679	High Similarity	NPC200782
0.8659	High Similarity	NPC94763
0.8659	High Similarity	NPC236004
0.8658	High Similarity	NPC67003
0.8654	High Similarity	NPC57998
0.8654	High Similarity	NPC30222
0.8645	High Similarity	NPC18135
0.8642	High Similarity	NPC271235
0.8642	High Similarity	NPC471397
0.8642	High Similarity	NPC472652
0.8631	High Similarity	NPC242068
0.8631	High Similarity	NPC247563
0.8627	High Similarity	NPC250228
0.8625	High Similarity	NPC165218
0.8625	High Similarity	NPC234660
0.8625	High Similarity	NPC51568
0.8625	High Similarity	NPC472139
0.8625	High Similarity	NPC477405
0.8616	High Similarity	NPC287559
0.8616	High Similarity	NPC477402
0.8616	High Similarity	NPC8389
0.8609	High Similarity	NPC243577
0.8608	High Similarity	NPC304692
0.8608	High Similarity	NPC195954
0.8608	High Similarity	NPC187149
0.8608	High Similarity	NPC36655
0.859	High Similarity	NPC75906
0.8589	High Similarity	NPC82602
0.8581	High Similarity	NPC212257
0.858	High Similarity	NPC476850
0.858	High Similarity	NPC173516
0.858	High Similarity	NPC476861
0.858	High Similarity	NPC472775
0.858	High Similarity	NPC100333
0.858	High Similarity	NPC478179
0.858	High Similarity	NPC472774
0.8571	High Similarity	NPC470182
0.8571	High Similarity	NPC93666
0.8571	High Similarity	NPC123088
0.8571	High Similarity	NPC476947
0.8563	High Similarity	NPC470938
0.8562	High Similarity	NPC218838
0.8562	High Similarity	NPC5741
0.8562	High Similarity	NPC188649
0.8562	High Similarity	NPC207978
0.8562	High Similarity	NPC329938
0.8562	High Similarity	NPC82851
0.8562	High Similarity	NPC211777
0.8554	High Similarity	NPC478177
0.8545	High Similarity	NPC471437
0.8545	High Similarity	NPC469576
0.8544	High Similarity	NPC104736
0.8528	High Similarity	NPC472765
0.8528	High Similarity	NPC472766
0.8521	High Similarity	NPC105395
0.8519	High Similarity	NPC478178
0.8519	High Similarity	NPC97574
0.8519	High Similarity	NPC93172
0.8519	High Similarity	NPC121995
0.8519	High Similarity	NPC475779
0.8516	High Similarity	NPC470791
0.8516	High Similarity	NPC470790
0.8509	High Similarity	NPC288602
0.8509	High Similarity	NPC88841
0.8509	High Similarity	NPC198047
0.8509	High Similarity	NPC471168
0.8503	High Similarity	NPC11062
0.85	High Similarity	NPC335761
0.85	High Similarity	NPC472653
0.8494	Intermediate Similarity	NPC469633
0.8491	Intermediate Similarity	NPC472772
0.8491	Intermediate Similarity	NPC45101
0.8487	Intermediate Similarity	NPC223415
0.8487	Intermediate Similarity	NPC80635
0.8471	Intermediate Similarity	NPC476201
0.8466	Intermediate Similarity	NPC472764
0.8466	Intermediate Similarity	NPC472282
0.8462	Intermediate Similarity	NPC469335
0.8462	Intermediate Similarity	NPC159927
0.8457	Intermediate Similarity	NPC126984
0.8457	Intermediate Similarity	NPC27541
0.8457	Intermediate Similarity	NPC62692
0.8457	Intermediate Similarity	NPC61967
0.8457	Intermediate Similarity	NPC476856
0.8457	Intermediate Similarity	NPC476858
0.8457	Intermediate Similarity	NPC476857
0.8447	Intermediate Similarity	NPC149896
0.8447	Intermediate Similarity	NPC472668
0.8447	Intermediate Similarity	NPC263432
0.8442	Intermediate Similarity	NPC346

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 NPC155939 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	867
0.2-0.3	2005
0.3-0.4	2599
0.4-0.5	2020
0.5-0.6	1025
0.6-0.7	329
0.7-0.8	23
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8481	Intermediate Similarity	NPD5761	Phase 2
0.8481	Intermediate Similarity	NPD5760	Phase 2
0.814	Intermediate Similarity	NPD8434	Phase 2
0.8059	Intermediate Similarity	NPD6765	Approved
0.8059	Intermediate Similarity	NPD6764	Approved
0.7874	Intermediate Similarity	NPD6785	Approved
0.7874	Intermediate Similarity	NPD6784	Approved
0.7834	Intermediate Similarity	NPD4628	Phase 3
0.7619	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD8127	Discontinued
0.7378	Intermediate Similarity	NPD6273	Approved
0.7312	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6599	Discontinued
0.7176	Intermediate Similarity	NPD7819	Suspended
0.7151	Intermediate Similarity	NPD7075	Discontinued
0.7151	Intermediate Similarity	NPD6559	Discontinued
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7126	Intermediate Similarity	NPD7199	Phase 2
0.7108	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD5762	Approved
0.7099	Intermediate Similarity	NPD5763	Approved
0.7091	Intermediate Similarity	NPD7236	Approved
0.7079	Intermediate Similarity	NPD5844	Phase 1
0.7071	Intermediate Similarity	NPD8404	Phase 2
0.7018	Intermediate Similarity	NPD6801	Discontinued
0.7	Intermediate Similarity	NPD6355	Discontinued
0.6994	Remote Similarity	NPD4966	Approved
0.6994	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4965	Approved
0.6994	Remote Similarity	NPD4967	Phase 2
0.6975	Remote Similarity	NPD2799	Discontinued
0.6971	Remote Similarity	NPD5494	Approved
0.697	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6799	Approved
0.6946	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3226	Approved
0.6927	Remote Similarity	NPD3818	Discontinued
0.6927	Remote Similarity	NPD7799	Discontinued
0.6923	Remote Similarity	NPD920	Approved
0.6914	Remote Similarity	NPD919	Approved
0.6914	Remote Similarity	NPD6234	Discontinued
0.6901	Remote Similarity	NPD7028	Phase 2
0.6897	Remote Similarity	NPD3882	Suspended
0.689	Remote Similarity	NPD2346	Discontinued
0.689	Remote Similarity	NPD1471	Phase 3
0.6885	Remote Similarity	NPD8312	Approved
0.6885	Remote Similarity	NPD8313	Approved
0.6882	Remote Similarity	NPD7239	Suspended
0.6879	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8032	Phase 2
0.6872	Remote Similarity	NPD7473	Discontinued
0.6868	Remote Similarity	NPD7685	Pre-registration
0.6867	Remote Similarity	NPD8166	Discontinued
0.6867	Remote Similarity	NPD4110	Phase 3
0.6867	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3750	Approved
0.6857	Remote Similarity	NPD3749	Approved
0.6842	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3817	Phase 2
0.6839	Remote Similarity	NPD1608	Approved
0.6833	Remote Similarity	NPD7228	Approved
0.6833	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4140	Approved
0.6821	Remote Similarity	NPD1934	Approved
0.6821	Remote Similarity	NPD37	Approved
0.6805	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD7497	Discontinued
0.6802	Remote Similarity	NPD4380	Phase 2
0.6791	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.679	Remote Similarity	NPD5735	Approved
0.6788	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2344	Approved
0.6788	Remote Similarity	NPD6002	Phase 3
0.6788	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6005	Phase 3
0.6788	Remote Similarity	NPD6004	Phase 3
0.6786	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3748	Approved
0.6766	Remote Similarity	NPD7003	Approved
0.6763	Remote Similarity	NPD7411	Suspended
0.6761	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD3057	Approved
0.6743	Remote Similarity	NPD5402	Approved
0.6743	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4107	Approved
0.6727	Remote Similarity	NPD2796	Approved
0.6727	Remote Similarity	NPD6100	Approved
0.6727	Remote Similarity	NPD6099	Approved
0.6725	Remote Similarity	NPD5403	Approved
0.6725	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD2313	Discontinued
0.6708	Remote Similarity	NPD6798	Discontinued
0.6708	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3764	Approved
0.6706	Remote Similarity	NPD2534	Approved
0.6706	Remote Similarity	NPD2532	Approved
0.6706	Remote Similarity	NPD5401	Approved
0.6706	Remote Similarity	NPD2533	Approved
0.6704	Remote Similarity	NPD6232	Discontinued
0.6686	Remote Similarity	NPD2801	Approved
0.6685	Remote Similarity	NPD7240	Approved
0.6684	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD3533	Approved
0.6667	Remote Similarity	NPD5647	Approved
0.6667	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD8407	Phase 2
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD2972	Approved
0.6648	Remote Similarity	NPD1247	Approved
0.6647	Remote Similarity	NPD1549	Phase 2
0.6646	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7095	Approved
0.6645	Remote Similarity	NPD17	Approved
0.663	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6166	Phase 2
0.6627	Remote Similarity	NPD2309	Approved
0.6627	Remote Similarity	NPD1551	Phase 2
0.6624	Remote Similarity	NPD3972	Approved
0.6615	Remote Similarity	NPD4482	Phase 3
0.6612	Remote Similarity	NPD7054	Approved
0.6612	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7229	Phase 3
0.661	Remote Similarity	NPD7768	Phase 2
0.6608	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD2800	Approved
0.6607	Remote Similarity	NPD1243	Approved
0.6605	Remote Similarity	NPD3268	Approved
0.6595	Remote Similarity	NPD8368	Discontinued
0.6591	Remote Similarity	NPD8455	Phase 2
0.6591	Remote Similarity	NPD1465	Phase 2
0.6587	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2491	Approved
0.6576	Remote Similarity	NPD7472	Approved
0.6575	Remote Similarity	NPD3926	Phase 2
0.6564	Remote Similarity	NPD6663	Approved
0.6562	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7177	Discontinued
0.6557	Remote Similarity	NPD3751	Discontinued
0.6554	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6653	Approved
0.6541	Remote Similarity	NPD1876	Approved
0.6541	Remote Similarity	NPD8651	Approved
0.6538	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1778	Approved
0.6538	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD3887	Approved
0.6529	Remote Similarity	NPD2354	Approved
0.6524	Remote Similarity	NPD4060	Phase 1
0.6522	Remote Similarity	NPD9494	Approved
0.6519	Remote Similarity	NPD7315	Approved
0.6517	Remote Similarity	NPD7058	Phase 2
0.6517	Remote Similarity	NPD7057	Phase 3
0.6506	Remote Similarity	NPD7097	Phase 1
0.6505	Remote Similarity	NPD7251	Discontinued
0.65	Remote Similarity	NPD2797	Approved
0.6497	Remote Similarity	NPD3448	Approved
0.6485	Remote Similarity	NPD5676	Approved
0.6481	Remote Similarity	NPD6832	Phase 2
0.6477	Remote Similarity	NPD6385	Approved
0.6477	Remote Similarity	NPD6386	Approved
0.6477	Remote Similarity	NPD6677	Suspended
0.6471	Remote Similarity	NPD7808	Phase 3
0.6467	Remote Similarity	NPD1510	Phase 2
0.6467	Remote Similarity	NPD2163	Approved
0.6467	Remote Similarity	NPD4308	Phase 3
0.6464	Remote Similarity	NPD6959	Discontinued
0.6463	Remote Similarity	NPD6233	Phase 2
0.646	Remote Similarity	NPD2798	Approved
0.6459	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD2651	Approved
0.6457	Remote Similarity	NPD2649	Approved
0.6453	Remote Similarity	NPD1511	Approved
0.6452	Remote Similarity	NPD6797	Phase 2
0.645	Remote Similarity	NPD2424	Discontinued
0.645	Remote Similarity	NPD4534	Discontinued
0.6446	Remote Similarity	NPD6353	Approved
0.6438	Remote Similarity	NPD1283	Approved
0.6433	Remote Similarity	NPD6190	Approved
0.6429	Remote Similarity	NPD3787	Discontinued
0.6429	Remote Similarity	NPD2935	Discontinued
0.6429	Remote Similarity	NPD2438	Suspended
0.6429	Remote Similarity	NPD6808	Phase 2
0.6421	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.642	Remote Similarity	NPD5736	Approved
0.6416	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.641	Remote Similarity	NPD9545	Approved
0.6398	Remote Similarity	NPD3266	Approved
0.6398	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD3267	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