NPASS Compound

Structure

NPC470997 OpenBabel07101719252D 32 36 0 0 1 0 0 0 0 0999 V2000 4.3301 -2.5000 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 0.0000 -2.0000 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 2.5981 -2.5000 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 1.7321 -3.0000 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 -3.8601 -0.4523 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 -4.8546 -0.3478 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 4.3301 -1.5000 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 2.5981 -1.5000 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 0.5000 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 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 -5.0625 0.6303 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 5 7 1 0 0 0 0 5 16 1 0 0 0 0 6 8 2 0 0 0 0 6 17 1 0 0 0 0 7 18 2 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 15 1 0 0 0 0 11 24 1 0 0 0 0 12 31 1 0 0 0 0 13 15 2 0 0 0 0 13 31 1 0 0 0 0 14 27 2 0 0 0 0 14 32 1 0 0 0 0 15 16 1 0 0 0 0 16 24 1 6 0 0 0 17 21 1 0 0 0 0 17 32 1 1 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 19 25 1 1 0 0 0 19 26 1 0 0 0 0 20 26 1 0 0 0 0 20 28 2 0 0 0 0 21 22 1 0 0 0 0 21 26 1 1 0 0 0 22 23 1 0 0 0 0 22 29 1 6 0 0 0 23 25 1 6 0 0 0 23 30 1 0 0 0 0 24 2 1 6 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.22
Volume:	452.392
LogP:	2.249
LogD:	2.533
LogS:	-4.106
# 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:	-4.816
MDCK Permeability:	3.328983802930452e-05
Pgp-inhibitor:	0.891
Pgp-substrate:	0.34
Human Intestinal Absorption (HIA):	0.85
20% Bioavailability (F20%):	0.307
30% Bioavailability (F30%):	0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978
Plasma Protein Binding (PPB):	85.38018798828125%
Volume Distribution (VD):	0.767
Pgp-substrate:	21.41149139404297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.217
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.787
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.157
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.198
CYP3A4-inhibitor:	0.411
CYP3A4-substrate:	0.45

ADMET: Excretion

Clearance (CL):	9.657
Half-life (T1/2):	0.104

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.046
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.981
Maximum Recommended Daily Dose:	0.867
Skin Sensitization:	0.013
Carcinogencity:	0.871
Eye Corrosion:	0.003
Eye Irritation:	0.045
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC470997

Natural Product ID:	NPC470997
*Common Name:**	Ceramicine K
IUPAC Name:	[(4S,5S,6R,7S,8R,9S,10R,13S,17R)-17-(furan-3-yl)-6,7-dihydroxy-8,10,13-trimethyl-1-oxo-5,6,7,9,11,12,16,17-octahydro-4H-cyclopenta[a]phenanthren-4-yl] acetate
Synonyms:	Ceramicine K
Standard InCHIKey:	XLHWCQAKDXPQEB-ZFOFYTLHSA-N
Standard InCHI:	InChI=1S/C26H32O6/c1-14(27)32-17-6-8-20(28)26(4)19-9-11-24(2)16(15-10-12-31-13-15)5-7-18(24)25(19,3)23(30)22(29)21(17)26/h6-8,10,12-13,16-17,19,21-23,29-30H,5,9,11H2,1-4H3/t16-,17-,19-,21+,22+,23+,24-,25-,26-/m0/s1
SMILES:	CC(=O)OC1C=CC(=O)C2(C1C(C(C3(C2CCC4(C3=CCC4C5=COC=C5)C)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2335029
PubChem CID:	71720689
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002381] 17-furanylsteroids and derivatives

*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.	bark	n.a.	PMID[21428417]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	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[501708]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[501708]

☑ 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 NPC470997 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	305
0.1-0.2	1193
0.2-0.3	2788
0.3-0.4	5103
0.4-0.5	9975
0.5-0.6	10982
0.6-0.7	10271
0.7-0.8	1643
0.8-0.85	259
0.85-0.9	140
0.9-0.95	31
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC33938
0.979	High Similarity	NPC234494
0.9653	High Similarity	NPC470998
0.9592	High Similarity	NPC92979
0.9514	High Similarity	NPC302987
0.9459	High Similarity	NPC141538
0.9459	High Similarity	NPC155939
0.9459	High Similarity	NPC296807
0.9379	High Similarity	NPC471174
0.932	High Similarity	NPC196846
0.9296	High Similarity	NPC56197
0.9252	High Similarity	NPC472654
0.9247	High Similarity	NPC216755
0.9241	High Similarity	NPC185456
0.9178	High Similarity	NPC471292
0.9172	High Similarity	NPC238843
0.9172	High Similarity	NPC199044
0.915	High Similarity	NPC470792
0.9133	High Similarity	NPC253201
0.9133	High Similarity	NPC34421
0.9133	High Similarity	NPC98206
0.9133	High Similarity	NPC237259
0.9133	High Similarity	NPC302054
0.9128	High Similarity	NPC272590
0.9122	High Similarity	NPC471001
0.9079	High Similarity	NPC197137
0.9067	High Similarity	NPC246164
0.9067	High Similarity	NPC472672
0.9067	High Similarity	NPC470996
0.8993	High Similarity	NPC125182
0.8993	High Similarity	NPC69647
0.8954	High Similarity	NPC470118
0.8926	High Similarity	NPC471007
0.8924	High Similarity	NPC470995
0.8919	High Similarity	NPC470999
0.8912	High Similarity	NPC476944
0.8896	High Similarity	NPC472671
0.8896	High Similarity	NPC475226
0.8882	High Similarity	NPC178932
0.8859	High Similarity	NPC255414
0.8851	High Similarity	NPC5676
0.8846	High Similarity	NPC224394
0.8846	High Similarity	NPC663
0.8844	High Similarity	NPC476946
0.8839	High Similarity	NPC470789
0.8831	High Similarity	NPC472778
0.8831	High Similarity	NPC472776
0.8831	High Similarity	NPC475066
0.8831	High Similarity	NPC214495
0.8831	High Similarity	NPC470119
0.8831	High Similarity	NPC194499
0.8831	High Similarity	NPC472777
0.8824	High Similarity	NPC264943
0.8824	High Similarity	NPC35000
0.8824	High Similarity	NPC469336
0.8816	High Similarity	NPC121615
0.8816	High Similarity	NPC268905
0.8816	High Similarity	NPC294511
0.8816	High Similarity	NPC471002
0.8816	High Similarity	NPC469503
0.8811	High Similarity	NPC476947
0.8808	High Similarity	NPC156189
0.8803	High Similarity	NPC218838
0.8792	High Similarity	NPC346
0.879	High Similarity	NPC276551
0.8784	High Similarity	NPC251865
0.8782	High Similarity	NPC69028
0.8776	High Similarity	NPC121158
0.8774	High Similarity	NPC84349
0.8774	High Similarity	NPC307383
0.8774	High Similarity	NPC475967
0.8758	High Similarity	NPC30222
0.875	High Similarity	NPC471000
0.875	High Similarity	NPC116717
0.8742	High Similarity	NPC195325
0.8734	High Similarity	NPC470875
0.8726	High Similarity	NPC283209
0.8726	High Similarity	NPC469338
0.8726	High Similarity	NPC472773
0.8726	High Similarity	NPC292389
0.871	High Similarity	NPC469847
0.871	High Similarity	NPC299038
0.871	High Similarity	NPC88007
0.8707	High Similarity	NPC205765
0.8701	High Similarity	NPC44675
0.8701	High Similarity	NPC281258
0.8701	High Similarity	NPC214541
0.8671	High Similarity	NPC469849
0.8671	High Similarity	NPC470940
0.8662	High Similarity	NPC200782
0.8662	High Similarity	NPC61788
0.8662	High Similarity	NPC472771
0.8662	High Similarity	NPC5079
0.8662	High Similarity	NPC68848
0.8649	High Similarity	NPC52412
0.8639	High Similarity	NPC67003
0.8636	High Similarity	NPC57998
0.8634	High Similarity	NPC285227
0.863	High Similarity	NPC476943
0.8627	High Similarity	NPC291150
0.8625	High Similarity	NPC471397
0.8618	High Similarity	NPC470791
0.8618	High Similarity	NPC470790
0.8616	High Similarity	NPC307781
0.8616	High Similarity	NPC472670
0.8609	High Similarity	NPC250228
0.8608	High Similarity	NPC477405
0.8608	High Similarity	NPC285567
0.8608	High Similarity	NPC165218
0.8608	High Similarity	NPC234660
0.8608	High Similarity	NPC51568
0.86	High Similarity	NPC34056
0.8599	High Similarity	NPC477402
0.8591	High Similarity	NPC267632
0.8591	High Similarity	NPC243577
0.859	High Similarity	NPC304692
0.859	High Similarity	NPC472772
0.859	High Similarity	NPC195954
0.859	High Similarity	NPC261597
0.8581	High Similarity	NPC25351
0.8571	High Similarity	NPC29695
0.8571	High Similarity	NPC308205
0.8571	High Similarity	NPC75906
0.8571	High Similarity	NPC90953
0.8571	High Similarity	NPC182427
0.8571	High Similarity	NPC322546
0.8562	High Similarity	NPC173516
0.8562	High Similarity	NPC228842
0.8562	High Similarity	NPC472651
0.8562	High Similarity	NPC5180
0.8562	High Similarity	NPC472774
0.8562	High Similarity	NPC310830
0.8562	High Similarity	NPC472775
0.8562	High Similarity	NPC310572
0.8562	High Similarity	NPC212257
0.8562	High Similarity	NPC469335
0.8562	High Similarity	NPC478179
0.8562	High Similarity	NPC159927
0.8553	High Similarity	NPC93666
0.8553	High Similarity	NPC470182
0.8544	High Similarity	NPC5741
0.8544	High Similarity	NPC188649
0.8544	High Similarity	NPC329938
0.8544	High Similarity	NPC471003
0.8544	High Similarity	NPC18986
0.8544	High Similarity	NPC82851
0.8544	High Similarity	NPC211777
0.8544	High Similarity	NPC263432
0.8544	High Similarity	NPC79571
0.8544	High Similarity	NPC207978
0.8535	High Similarity	NPC474611
0.8533	High Similarity	NPC142113
0.8528	High Similarity	NPC94763
0.8528	High Similarity	NPC236004
0.8526	High Similarity	NPC104736
0.8526	High Similarity	NPC41880
0.8519	High Similarity	NPC475641
0.8519	High Similarity	NPC475237
0.8516	High Similarity	NPC282445
0.8509	High Similarity	NPC472766
0.8509	High Similarity	NPC472673
0.8509	High Similarity	NPC271235
0.8509	High Similarity	NPC472652
0.8509	High Similarity	NPC472765
0.8506	High Similarity	NPC18135
0.8503	High Similarity	NPC220094
0.85	High Similarity	NPC472141
0.85	High Similarity	NPC93172
0.85	High Similarity	NPC478178
0.85	High Similarity	NPC121995
0.85	High Similarity	NPC97574
0.8491	Intermediate Similarity	NPC88841
0.8491	Intermediate Similarity	NPC288602
0.8491	Intermediate Similarity	NPC198047
0.8487	Intermediate Similarity	NPC71821
0.8481	Intermediate Similarity	NPC472653
0.8481	Intermediate Similarity	NPC8389
0.8481	Intermediate Similarity	NPC287559
0.8481	Intermediate Similarity	NPC335761
0.8477	Intermediate Similarity	NPC41182
0.8471	Intermediate Similarity	NPC249021
0.8471	Intermediate Similarity	NPC187149
0.8471	Intermediate Similarity	NPC36655
0.8471	Intermediate Similarity	NPC45101
0.8471	Intermediate Similarity	NPC7059
0.8457	Intermediate Similarity	NPC82602
0.8457	Intermediate Similarity	NPC118086
0.8452	Intermediate Similarity	NPC476201
0.8447	Intermediate Similarity	NPC476850
0.8447	Intermediate Similarity	NPC476861
0.8447	Intermediate Similarity	NPC100333
0.8447	Intermediate Similarity	NPC472764
0.8447	Intermediate Similarity	NPC472282
0.8446	Intermediate Similarity	NPC202260
0.8442	Intermediate Similarity	NPC196864
0.8442	Intermediate Similarity	NPC477404
0.8438	Intermediate Similarity	NPC476857
0.8438	Intermediate Similarity	NPC476858
0.8438	Intermediate Similarity	NPC476856
0.8438	Intermediate Similarity	NPC123088

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 NPC470997 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	880
0.2-0.3	1915
0.3-0.4	2575
0.4-0.5	2047
0.5-0.6	1096
0.6-0.7	355
0.7-0.8	23
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
0.8581	High Similarity	NPD5761	Phase 2
0.8581	High Similarity	NPD5760	Phase 2
0.8118	Intermediate Similarity	NPD8434	Phase 2
0.8036	Intermediate Similarity	NPD6764	Approved
0.8036	Intermediate Similarity	NPD6765	Approved
0.7849	Intermediate Similarity	NPD6784	Approved
0.7849	Intermediate Similarity	NPD6785	Approved
0.7613	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD4628	Phase 3
0.7562	Intermediate Similarity	NPD6273	Approved
0.7484	Intermediate Similarity	NPD7236	Approved
0.7396	Intermediate Similarity	NPD8127	Discontinued
0.7256	Intermediate Similarity	NPD7239	Suspended
0.7247	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD7458	Discontinued
0.717	Intermediate Similarity	NPD2346	Discontinued
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD6559	Discontinued
0.7108	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6355	Discontinued
0.7066	Intermediate Similarity	NPD6599	Discontinued
0.7063	Intermediate Similarity	NPD1471	Phase 3
0.7051	Intermediate Similarity	NPD8032	Phase 2
0.7045	Intermediate Similarity	NPD5844	Phase 1
0.7041	Intermediate Similarity	NPD8404	Phase 2
0.7037	Intermediate Similarity	NPD8166	Discontinued
0.7018	Intermediate Similarity	NPD7075	Discontinued
0.7006	Intermediate Similarity	NPD4140	Approved
0.6994	Remote Similarity	NPD7199	Phase 2
0.6988	Remote Similarity	NPD920	Approved
0.6987	Remote Similarity	NPD2313	Discontinued
0.6964	Remote Similarity	NPD7028	Phase 2
0.6959	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5763	Approved
0.6957	Remote Similarity	NPD5762	Approved
0.6957	Remote Similarity	NPD2344	Approved
0.6941	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5494	Approved
0.6933	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7003	Approved
0.6933	Remote Similarity	NPD4110	Phase 3
0.6905	Remote Similarity	NPD3226	Approved
0.6893	Remote Similarity	NPD3818	Discontinued
0.6893	Remote Similarity	NPD7799	Discontinued
0.6882	Remote Similarity	NPD6801	Discontinued
0.6879	Remote Similarity	NPD3268	Approved
0.6867	Remote Similarity	NPD642	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7057	Phase 3
0.686	Remote Similarity	NPD4965	Approved
0.686	Remote Similarity	NPD4967	Phase 2
0.686	Remote Similarity	NPD4966	Approved
0.686	Remote Similarity	NPD7058	Phase 2
0.6855	Remote Similarity	NPD5735	Approved
0.6852	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6005	Phase 3
0.6852	Remote Similarity	NPD6004	Phase 3
0.6852	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6002	Phase 3
0.6851	Remote Similarity	NPD8312	Approved
0.6851	Remote Similarity	NPD8313	Approved
0.6836	Remote Similarity	NPD7473	Discontinued
0.6833	Remote Similarity	NPD7685	Pre-registration
0.6829	Remote Similarity	NPD3750	Approved
0.6821	Remote Similarity	NPD3749	Approved
0.6818	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6653	Approved
0.6807	Remote Similarity	NPD6799	Approved
0.6802	Remote Similarity	NPD3817	Phase 2
0.6797	Remote Similarity	NPD3972	Approved
0.679	Remote Similarity	NPD2935	Discontinued
0.6788	Remote Similarity	NPD2309	Approved
0.6784	Remote Similarity	NPD37	Approved
0.6784	Remote Similarity	NPD1934	Approved
0.6782	Remote Similarity	NPD919	Approved
0.6782	Remote Similarity	NPD6234	Discontinued
0.6774	Remote Similarity	NPD2797	Approved
0.6772	Remote Similarity	NPD6798	Discontinued
0.6771	Remote Similarity	NPD7497	Discontinued
0.6766	Remote Similarity	NPD2532	Approved
0.6766	Remote Similarity	NPD2534	Approved
0.6766	Remote Similarity	NPD2533	Approved
0.6765	Remote Similarity	NPD4380	Phase 2
0.6763	Remote Similarity	NPD3882	Suspended
0.6752	Remote Similarity	NPD6832	Phase 2
0.6747	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5647	Approved
0.673	Remote Similarity	NPD6663	Approved
0.673	Remote Similarity	NPD6233	Phase 2
0.6728	Remote Similarity	NPD4308	Phase 3
0.6728	Remote Similarity	NPD3748	Approved
0.6725	Remote Similarity	NPD7411	Suspended
0.6724	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.671	Remote Similarity	NPD1876	Approved
0.6709	Remote Similarity	NPD7095	Approved
0.6709	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2424	Discontinued
0.6705	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5402	Approved
0.6705	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD7228	Approved
0.6704	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1608	Approved
0.6687	Remote Similarity	NPD6099	Approved
0.6687	Remote Similarity	NPD6100	Approved
0.6687	Remote Similarity	NPD2796	Approved
0.6685	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6232	Discontinued
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD2800	Approved
0.6667	Remote Similarity	NPD3267	Approved
0.6667	Remote Similarity	NPD6808	Phase 2
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7229	Phase 3
0.6649	Remote Similarity	NPD8150	Discontinued
0.6647	Remote Similarity	NPD2801	Approved
0.6646	Remote Similarity	NPD447	Suspended
0.663	Remote Similarity	NPD7074	Phase 3
0.663	Remote Similarity	NPD8407	Phase 2
0.6626	Remote Similarity	NPD7033	Discontinued
0.6624	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD2798	Approved
0.661	Remote Similarity	NPD1247	Approved
0.6606	Remote Similarity	NPD1549	Phase 2
0.6605	Remote Similarity	NPD6353	Approved
0.6603	Remote Similarity	NPD1283	Approved
0.6592	Remote Similarity	NPD6166	Phase 2
0.6592	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5403	Approved
0.6588	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2354	Approved
0.6587	Remote Similarity	NPD3887	Approved
0.6585	Remote Similarity	NPD2438	Suspended
0.6585	Remote Similarity	NPD1551	Phase 2
0.6584	Remote Similarity	NPD4060	Phase 1
0.6584	Remote Similarity	NPD2979	Phase 3
0.6584	Remote Similarity	NPD4307	Phase 2
0.6582	Remote Similarity	NPD9494	Approved
0.6582	Remote Similarity	NPD5736	Approved
0.6575	Remote Similarity	NPD7054	Approved
0.6575	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7768	Phase 2
0.6568	Remote Similarity	NPD5401	Approved
0.6566	Remote Similarity	NPD1243	Approved
0.6562	Remote Similarity	NPD3764	Approved
0.6561	Remote Similarity	NPD6362	Approved
0.6557	Remote Similarity	NPD8368	Discontinued
0.6557	Remote Similarity	NPD7240	Approved
0.6552	Remote Similarity	NPD1465	Phase 2
0.6552	Remote Similarity	NPD8455	Phase 2
0.6546	Remote Similarity	NPD3057	Approved
0.6545	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5327	Phase 3
0.6538	Remote Similarity	NPD7472	Approved
0.6536	Remote Similarity	NPD5585	Approved
0.6532	Remote Similarity	NPD6677	Suspended
0.6528	Remote Similarity	NPD4107	Approved
0.6522	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD3751	Discontinued
0.6517	Remote Similarity	NPD6959	Discontinued
0.6516	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD2649	Approved
0.6512	Remote Similarity	NPD2651	Approved
0.6509	Remote Similarity	NPD1511	Approved
0.6506	Remote Similarity	NPD4534	Discontinued
0.6506	Remote Similarity	NPD970	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD6844	Discontinued
0.6494	Remote Similarity	NPD1778	Approved
0.6494	Remote Similarity	NPD17	Approved
0.6485	Remote Similarity	NPD4476	Approved
0.6485	Remote Similarity	NPD4477	Approved
0.648	Remote Similarity	NPD7315	Approved
0.6474	Remote Similarity	NPD9717	Approved
0.6467	Remote Similarity	NPD1241	Discontinued
0.6467	Remote Similarity	NPD7251	Discontinued
0.6462	Remote Similarity	NPD3533	Approved
0.6462	Remote Similarity	NPD2972	Approved
0.6462	Remote Similarity	NPD2491	Approved
0.6456	Remote Similarity	NPD1203	Approved
0.6452	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.645	Remote Similarity	NPD7440	Discontinued
0.6444	Remote Similarity	NPD3926	Phase 2
0.6442	Remote Similarity	NPD230	Phase 1
0.6442	Remote Similarity	NPD1933	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