NPASS Compound

Structure

NPC470996 OpenBabel07101719252D 31 36 0 0 1 0 0 0 0 0999 V2000 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 0.1142 2.1594 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 -0.8660 1.5000 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 -1.7321 1.0000 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 -2.0685 -1.5827 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 -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 -1.0739 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1288 2.2695 0.0000 C 0 0 0 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 -0.8660 -0.5000 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 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4048 -2.2213 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 5 9 1 0 0 0 0 5 17 1 0 0 0 0 6 8 2 0 0 0 0 6 18 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 23 1 0 0 0 0 9 24 1 0 0 0 0 10 30 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 30 1 0 0 0 0 13 23 1 0 0 0 0 13 31 1 0 0 0 0 14 15 1 0 0 0 0 15 24 1 1 0 0 0 16 20 1 0 0 0 0 16 27 2 0 0 0 0 17 25 1 6 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 18 28 2 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 19 31 1 1 0 0 0 20 24 1 6 0 0 0 20 26 1 0 0 0 0 21 23 1 6 0 0 0 21 25 1 0 0 0 0 22 26 1 1 0 0 0 22 29 1 0 0 0 0 23 1 1 6 0 0 0 24 2 1 1 0 0 0 25 3 1 6 0 0 0 26 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.22
Volume:	452.392
LogP:	2.267
LogD:	1.832
LogS:	-4.153
# Rotatable Bonds:	3
TPSA:	96.97
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.535
Synthetic Accessibility Score:	5.239
Fsp3:	0.615
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:	-4.774
MDCK Permeability:	2.8586910048034042e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.907
Human Intestinal Absorption (HIA):	0.706
20% Bioavailability (F20%):	0.742
30% Bioavailability (F30%):	0.931

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.947
Plasma Protein Binding (PPB):	81.13016510009766%
Volume Distribution (VD):	0.617
Pgp-substrate:	20.086484909057617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.526
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.535
CYP3A4-substrate:	0.308

ADMET: Excretion

Clearance (CL):	7.753
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.992
Maximum Recommended Daily Dose:	0.982
Skin Sensitization:	0.422
Carcinogencity:	0.892
Eye Corrosion:	0.028
Eye Irritation:	0.037
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC470996

Natural Product ID:	NPC470996
*Common Name:**	Ceramicine J
IUPAC Name:	n.a.
Synonyms:	Ceramicine J
Standard InCHIKey:	WETZKRVINBGRBT-CESHVPDDSA-N
Standard InCHI:	InChI=1S/C26H32O5/c1-23-8-6-18(28)25(3)17-5-9-24(2)15(14-7-10-30-12-14)11-16(27)20(24)26(17,4)22(29)19(21(23)25)31-13-23/h6-8,10,12,15,17,19-22,29H,5,9,11,13H2,1-4H3/t15-,17+,19+,20+,21-,22+,23-,24-,25-,26+/m0/s1
SMILES:	CC12CCC3C4(C5C(C(C3(C1C(=O)CC2C6=COC=C6)C)O)OCC5(C=CC4=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2335028
PubChem CID:	71717014
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	1

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		CC50	>	50000.0	nM	PMID[560076]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[560076]

☑ 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 NPC470996 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	372
0.1-0.2	1311
0.2-0.3	3032
0.3-0.4	5429
0.4-0.5	11440
0.5-0.6	10765
0.6-0.7	9173
0.7-0.8	901
0.8-0.85	211
0.85-0.9	56
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9724	High Similarity	NPC196846
0.9517	High Similarity	NPC302987
0.9463	High Similarity	NPC296807
0.9463	High Similarity	NPC141538
0.9463	High Similarity	NPC155939
0.9333	High Similarity	NPC92979
0.9315	High Similarity	NPC470999
0.9257	High Similarity	NPC234494
0.9247	High Similarity	NPC185456
0.9211	High Similarity	NPC197137
0.9189	High Similarity	NPC471007
0.9128	High Similarity	NPC470998
0.9128	High Similarity	NPC471001
0.9073	High Similarity	NPC33938
0.9067	High Similarity	NPC470997
0.9026	High Similarity	NPC84349
0.9007	High Similarity	NPC471000
0.8993	High Similarity	NPC471174
0.891	High Similarity	NPC470792
0.8889	High Similarity	NPC237259
0.8889	High Similarity	NPC34421
0.8889	High Similarity	NPC98206
0.8882	High Similarity	NPC291150
0.8882	High Similarity	NPC272590
0.8882	High Similarity	NPC116717
0.8867	High Similarity	NPC216755
0.8824	High Similarity	NPC471002
0.8816	High Similarity	NPC5180
0.8792	High Similarity	NPC199044
0.8792	High Similarity	NPC238843
0.8758	High Similarity	NPC285227
0.8733	High Similarity	NPC5676
0.8718	High Similarity	NPC470118
0.8718	High Similarity	NPC469847
0.8701	High Similarity	NPC246164
0.8701	High Similarity	NPC121615
0.8701	High Similarity	NPC294511
0.869	High Similarity	NPC476947
0.8681	High Similarity	NPC218838
0.8679	High Similarity	NPC276551
0.8675	High Similarity	NPC471292
0.8671	High Similarity	NPC69028
0.8662	High Similarity	NPC472671
0.8662	High Similarity	NPC475226
0.8649	High Similarity	NPC67003
0.8649	High Similarity	NPC56197
0.8645	High Similarity	NPC253201
0.8645	High Similarity	NPC178932
0.8645	High Similarity	NPC302054
0.8627	High Similarity	NPC69647
0.8627	High Similarity	NPC472654
0.8627	High Similarity	NPC125182
0.8625	High Similarity	NPC470875
0.8623	High Similarity	NPC242068
0.8623	High Similarity	NPC247563
0.8616	High Similarity	NPC292389
0.8616	High Similarity	NPC283209
0.8616	High Similarity	NPC469338
0.8616	High Similarity	NPC472773
0.8609	High Similarity	NPC34056
0.86	High Similarity	NPC243577
0.8599	High Similarity	NPC214495
0.8599	High Similarity	NPC472776
0.8599	High Similarity	NPC475066
0.8599	High Similarity	NPC470119
0.8599	High Similarity	NPC472777
0.8599	High Similarity	NPC472778
0.859	High Similarity	NPC264943
0.859	High Similarity	NPC469336
0.8581	High Similarity	NPC472672
0.8581	High Similarity	NPC268905
0.8562	High Similarity	NPC470940
0.8562	High Similarity	NPC469849
0.8553	High Similarity	NPC18986
0.8553	High Similarity	NPC471003
0.8553	High Similarity	NPC472771
0.8553	High Similarity	NPC5741
0.8545	High Similarity	NPC478177
0.8544	High Similarity	NPC475967
0.8544	High Similarity	NPC472823
0.8543	High Similarity	NPC251865
0.8537	High Similarity	NPC471437
0.8533	High Similarity	NPC52412
0.8519	High Similarity	NPC472765
0.8519	High Similarity	NPC471397
0.8519	High Similarity	NPC472766
0.8519	High Similarity	NPC472673
0.8512	High Similarity	NPC105395
0.8506	High Similarity	NPC195325
0.85	High Similarity	NPC477405
0.85	High Similarity	NPC471168
0.85	High Similarity	NPC285567
0.85	High Similarity	NPC663
0.85	High Similarity	NPC224394
0.8497	Intermediate Similarity	NPC255414
0.8491	Intermediate Similarity	NPC287559
0.8491	Intermediate Similarity	NPC477402
0.8481	Intermediate Similarity	NPC299038
0.8481	Intermediate Similarity	NPC194499
0.8477	Intermediate Similarity	NPC476946
0.8471	Intermediate Similarity	NPC214541
0.8471	Intermediate Similarity	NPC44675
0.8467	Intermediate Similarity	NPC205765
0.8466	Intermediate Similarity	NPC470995
0.8462	Intermediate Similarity	NPC75906
0.8457	Intermediate Similarity	NPC173516
0.8457	Intermediate Similarity	NPC476850
0.8457	Intermediate Similarity	NPC472774
0.8457	Intermediate Similarity	NPC476861
0.8457	Intermediate Similarity	NPC472775
0.8457	Intermediate Similarity	NPC472764
0.8452	Intermediate Similarity	NPC228842
0.8447	Intermediate Similarity	NPC123088
0.8442	Intermediate Similarity	NPC93666
0.8438	Intermediate Similarity	NPC329938
0.8438	Intermediate Similarity	NPC68848
0.8438	Intermediate Similarity	NPC263432
0.8428	Intermediate Similarity	NPC307383
0.8425	Intermediate Similarity	NPC471006
0.8424	Intermediate Similarity	NPC236004
0.8424	Intermediate Similarity	NPC94763
0.8414	Intermediate Similarity	NPC61788
0.8411	Intermediate Similarity	NPC121158
0.84	Intermediate Similarity	NPC90296
0.8395	Intermediate Similarity	NPC472670
0.8395	Intermediate Similarity	NPC475779
0.8395	Intermediate Similarity	NPC472141
0.8395	Intermediate Similarity	NPC121995
0.8395	Intermediate Similarity	NPC307781
0.8385	Intermediate Similarity	NPC165218
0.8378	Intermediate Similarity	NPC46896
0.8377	Intermediate Similarity	NPC71821
0.8375	Intermediate Similarity	NPC470789
0.8365	Intermediate Similarity	NPC261597
0.8365	Intermediate Similarity	NPC304692
0.8365	Intermediate Similarity	NPC88007
0.8365	Intermediate Similarity	NPC472772
0.8365	Intermediate Similarity	NPC7059
0.8364	Intermediate Similarity	NPC469848
0.8354	Intermediate Similarity	NPC281258
0.8354	Intermediate Similarity	NPC35000
0.8344	Intermediate Similarity	NPC310572
0.8344	Intermediate Similarity	NPC472282
0.8344	Intermediate Similarity	NPC472651
0.8344	Intermediate Similarity	NPC308205
0.8344	Intermediate Similarity	NPC322546
0.8344	Intermediate Similarity	NPC182427
0.8344	Intermediate Similarity	NPC29695
0.8344	Intermediate Similarity	NPC469503
0.8333	Intermediate Similarity	NPC476856
0.8333	Intermediate Similarity	NPC476857
0.8333	Intermediate Similarity	NPC159927
0.8333	Intermediate Similarity	NPC476858
0.8333	Intermediate Similarity	NPC90953
0.8333	Intermediate Similarity	NPC469335
0.8333	Intermediate Similarity	NPC470938
0.8323	Intermediate Similarity	NPC471166
0.8323	Intermediate Similarity	NPC79571
0.8323	Intermediate Similarity	NPC197596
0.8323	Intermediate Similarity	NPC5079
0.8323	Intermediate Similarity	NPC200782
0.8323	Intermediate Similarity	NPC471167
0.8323	Intermediate Similarity	NPC472767
0.8322	Intermediate Similarity	NPC4764
0.8313	Intermediate Similarity	NPC471632
0.8313	Intermediate Similarity	NPC477403
0.8313	Intermediate Similarity	NPC469576
0.8311	Intermediate Similarity	NPC158525
0.8303	Intermediate Similarity	NPC475237
0.8303	Intermediate Similarity	NPC475641
0.8302	Intermediate Similarity	NPC104736
0.8302	Intermediate Similarity	NPC469485
0.8293	Intermediate Similarity	NPC472652
0.8293	Intermediate Similarity	NPC271235
0.8293	Intermediate Similarity	NPC160651
0.8291	Intermediate Similarity	NPC57998
0.8291	Intermediate Similarity	NPC30222
0.8289	Intermediate Similarity	NPC263337
0.8282	Intermediate Similarity	NPC478178
0.828	Intermediate Similarity	NPC18135
0.8272	Intermediate Similarity	NPC234660
0.8272	Intermediate Similarity	NPC51568
0.8272	Intermediate Similarity	NPC472139
0.8272	Intermediate Similarity	NPC419
0.8267	Intermediate Similarity	NPC471996
0.8263	Intermediate Similarity	NPC469633
0.8261	Intermediate Similarity	NPC25255
0.8261	Intermediate Similarity	NPC191828
0.8261	Intermediate Similarity	NPC8389
0.8258	Intermediate Similarity	NPC250228
0.825	Intermediate Similarity	NPC195954
0.825	Intermediate Similarity	NPC36655
0.825	Intermediate Similarity	NPC167142
0.825	Intermediate Similarity	NPC187149
0.825	Intermediate Similarity	NPC173544
0.825	Intermediate Similarity	NPC472283
0.8247	Intermediate Similarity	NPC56731
0.8242	Intermediate Similarity	NPC118086
0.8242	Intermediate Similarity	NPC82602
0.8242	Intermediate Similarity	NPC44602

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 NPC470996 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	901
0.2-0.3	2092
0.3-0.4	2722
0.4-0.5	1973
0.5-0.6	915
0.6-0.7	211
0.7-0.8	11
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
0.859	High Similarity	NPD5760	Phase 2
0.859	High Similarity	NPD5761	Phase 2
0.7941	Intermediate Similarity	NPD6765	Approved
0.7941	Intermediate Similarity	NPD6764	Approved
0.7919	Intermediate Similarity	NPD8434	Phase 2
0.7759	Intermediate Similarity	NPD6785	Approved
0.7759	Intermediate Similarity	NPD6784	Approved
0.7605	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.731	Intermediate Similarity	NPD8127	Discontinued
0.7256	Intermediate Similarity	NPD6273	Approved
0.7188	Intermediate Similarity	NPD1471	Phase 3
0.7099	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7028	Phase 2
0.6981	Remote Similarity	NPD5735	Approved
0.6975	Remote Similarity	NPD5762	Approved
0.6975	Remote Similarity	NPD5763	Approved
0.697	Remote Similarity	NPD7236	Approved
0.6959	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5494	Approved
0.6944	Remote Similarity	NPD6559	Discontinued
0.6923	Remote Similarity	NPD7458	Discontinued
0.6919	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7199	Phase 2
0.6886	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6599	Discontinued
0.6879	Remote Similarity	NPD3882	Suspended
0.6875	Remote Similarity	NPD6355	Discontinued
0.6871	Remote Similarity	NPD2344	Approved
0.686	Remote Similarity	NPD7819	Suspended
0.686	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7075	Discontinued
0.6824	Remote Similarity	NPD3226	Approved
0.6818	Remote Similarity	NPD1247	Approved
0.6816	Remote Similarity	NPD3818	Discontinued
0.6802	Remote Similarity	NPD1934	Approved
0.68	Remote Similarity	NPD8404	Phase 2
0.6784	Remote Similarity	NPD4380	Phase 2
0.6778	Remote Similarity	NPD5844	Phase 1
0.6765	Remote Similarity	NPD7239	Suspended
0.675	Remote Similarity	NPD8032	Phase 2
0.6748	Remote Similarity	NPD2799	Discontinued
0.6747	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4110	Phase 3
0.6742	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD3057	Approved
0.6731	Remote Similarity	NPD1876	Approved
0.6722	Remote Similarity	NPD7799	Discontinued
0.6722	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.671	Remote Similarity	NPD3972	Approved
0.6708	Remote Similarity	NPD4140	Approved
0.6707	Remote Similarity	NPD2309	Approved
0.6707	Remote Similarity	NPD6100	Approved
0.6707	Remote Similarity	NPD6099	Approved
0.6707	Remote Similarity	NPD2796	Approved
0.6705	Remote Similarity	NPD6801	Discontinued
0.6704	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD4965	Approved
0.6686	Remote Similarity	NPD4966	Approved
0.6686	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD7685	Pre-registration
0.6649	Remote Similarity	NPD2972	Approved
0.6649	Remote Similarity	NPD2491	Approved
0.6649	Remote Similarity	NPD3533	Approved
0.6648	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD8166	Discontinued
0.6647	Remote Similarity	NPD7411	Suspended
0.663	Remote Similarity	NPD2163	Approved
0.6629	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1549	Phase 2
0.6627	Remote Similarity	NPD6799	Approved
0.6627	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD6353	Approved
0.6623	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7497	Discontinued
0.6611	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6166	Phase 2
0.6611	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6234	Discontinued
0.661	Remote Similarity	NPD919	Approved
0.6608	Remote Similarity	NPD920	Approved
0.6604	Remote Similarity	NPD9494	Approved
0.6595	Remote Similarity	NPD8312	Approved
0.6595	Remote Similarity	NPD8313	Approved
0.6588	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2800	Approved
0.6584	Remote Similarity	NPD3268	Approved
0.6575	Remote Similarity	NPD7473	Discontinued
0.6566	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6002	Phase 3
0.6566	Remote Similarity	NPD6005	Phase 3
0.6566	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6004	Phase 3
0.6564	Remote Similarity	NPD3448	Approved
0.6561	Remote Similarity	NPD5327	Phase 3
0.6557	Remote Similarity	NPD7074	Phase 3
0.6556	Remote Similarity	NPD3926	Phase 2
0.6554	Remote Similarity	NPD3749	Approved
0.6548	Remote Similarity	NPD7003	Approved
0.6548	Remote Similarity	NPD3750	Approved
0.6541	Remote Similarity	NPD5647	Approved
0.6538	Remote Similarity	NPD7228	Approved
0.6536	Remote Similarity	NPD9092	Discovery
0.6534	Remote Similarity	NPD3817	Phase 2
0.6532	Remote Similarity	NPD2651	Approved
0.6532	Remote Similarity	NPD2649	Approved
0.6519	Remote Similarity	NPD8651	Approved
0.6514	Remote Similarity	NPD37	Approved
0.6508	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7054	Approved
0.6503	Remote Similarity	NPD3620	Phase 2
0.6503	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD1608	Approved
0.6491	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6798	Discontinued
0.6481	Remote Similarity	NPD2313	Discontinued
0.6474	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD5676	Approved
0.6467	Remote Similarity	NPD7472	Approved
0.6462	Remote Similarity	NPD4107	Approved
0.6448	Remote Similarity	NPD3751	Discontinued
0.6446	Remote Similarity	NPD3748	Approved
0.6446	Remote Similarity	NPD1510	Phase 2
0.6446	Remote Similarity	NPD7033	Discontinued
0.6444	Remote Similarity	NPD6959	Discontinued
0.6442	Remote Similarity	NPD6663	Approved
0.6441	Remote Similarity	NPD5978	Approved
0.6441	Remote Similarity	NPD5977	Approved
0.6441	Remote Similarity	NPD5402	Approved
0.644	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD2798	Approved
0.6433	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD1511	Approved
0.6432	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2424	Discontinued
0.6424	Remote Similarity	NPD6653	Approved
0.642	Remote Similarity	NPD7095	Approved
0.642	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD5403	Approved
0.6416	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2932	Approved
0.6409	Remote Similarity	NPD6808	Phase 2
0.6409	Remote Similarity	NPD6232	Discontinued
0.6405	Remote Similarity	NPD7157	Approved
0.6404	Remote Similarity	NPD7058	Phase 2
0.6404	Remote Similarity	NPD7057	Phase 3
0.6402	Remote Similarity	NPD8150	Discontinued
0.6398	Remote Similarity	NPD7240	Approved
0.6398	Remote Similarity	NPD7251	Discontinued
0.6395	Remote Similarity	NPD2532	Approved
0.6395	Remote Similarity	NPD5401	Approved
0.6395	Remote Similarity	NPD2534	Approved
0.6395	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD2533	Approved
0.6383	Remote Similarity	NPD8407	Phase 2
0.6382	Remote Similarity	NPD1241	Discontinued
0.638	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.638	Remote Similarity	NPD3764	Approved
0.6375	Remote Similarity	NPD3266	Approved
0.6375	Remote Similarity	NPD3267	Approved
0.6364	Remote Similarity	NPD7808	Phase 3
0.6358	Remote Similarity	NPD1512	Approved
0.6345	Remote Similarity	NPD4482	Phase 3
0.6344	Remote Similarity	NPD6797	Phase 2
0.6335	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD4111	Phase 1
0.6329	Remote Similarity	NPD4665	Approved
0.6328	Remote Similarity	NPD6279	Approved
0.6328	Remote Similarity	NPD6280	Approved
0.6328	Remote Similarity	NPD6844	Discontinued
0.6325	Remote Similarity	NPD1607	Approved
0.6319	Remote Similarity	NPD7315	Approved
0.6319	Remote Similarity	NPD7229	Phase 3
0.6319	Remote Similarity	NPD3787	Discontinued
0.6316	Remote Similarity	NPD3887	Approved
0.6316	Remote Similarity	NPD2354	Approved
0.6313	Remote Similarity	NPD7768	Phase 2
0.631	Remote Similarity	NPD1551	Phase 2
0.631	Remote Similarity	NPD8368	Discontinued
0.6306	Remote Similarity	NPD3019	Approved
0.6306	Remote Similarity	NPD17	Approved
0.6303	Remote Similarity	NPD4060	Phase 1
0.6303	Remote Similarity	NPD1240	Approved
0.6302	Remote Similarity	NPD2488	Approved
0.6302	Remote Similarity	NPD2490	Approved
0.6301	Remote Similarity	NPD4661	Approved
0.6301	Remote Similarity	NPD4662	Approved
0.6296	Remote Similarity	NPD5736	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