NPASS Compound

Structure

CID178932 OpenBabel06191715552D 34 38 0 0 1 0 0 0 0 0999 V2000 6.4244 3.7073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6212 2.3168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0007 1.8544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4098 3.2447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2287 3.6782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6068 2.7814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6495 1.0141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8036 2.3180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2696 1.7032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2123 0.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6061 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0156 4.1710 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8992 2.3130 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8025 1.3910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4095 1.3903 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0153 1.3902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4097 2.3176 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6063 0.9269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0154 3.2442 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3555 4.8216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8029 -0.4638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8180 1.8534 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0154 2.3171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9273 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8184 2.7805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8034 1.3907 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2127 2.7810 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5888 5.7185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8027 -1.3909 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6208 1.3896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6214 3.2437 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4620 4.5752 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8059 2.5060 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 5 32 1 0 0 0 0 6 8 1 0 0 0 0 6 17 1 0 0 0 0 7 9 2 0 0 0 0 7 14 1 0 0 0 0 8 26 1 0 0 0 0 9 33 1 0 0 0 0 10 15 1 0 0 0 0 11 18 1 0 0 0 0 11 21 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 14 2 0 0 0 0 13 33 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 18 2 0 0 0 0 16 10 1 6 0 0 0 16 22 1 0 0 0 0 16 23 1 0 0 0 0 17 27 1 6 0 0 0 18 26 1 0 0 0 0 19 25 1 0 0 0 0 19 27 1 1 0 0 0 20 28 2 0 0 0 0 20 32 1 0 0 0 0 21 29 2 0 0 0 0 21 34 1 0 0 0 0 22 25 1 0 0 0 0 22 30 1 6 0 0 0 23 27 1 0 0 0 0 23 31 2 0 0 0 0 24 26 1 1 0 0 0 24 34 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.23
Volume:	478.479
LogP:	3.259
LogD:	2.266
LogS:	-4.657
# Rotatable Bonds:	4
TPSA:	103.04
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.523
Synthetic Accessibility Score:	5.711
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.0
MDCK Permeability:	4.907936090603471e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.484
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.722
Plasma Protein Binding (PPB):	81.56912231445312%
Volume Distribution (VD):	1.478
Pgp-substrate:	14.415221214294434%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.105
CYP2C19-inhibitor:	0.352
CYP2C19-substrate:	0.296
CYP2C9-inhibitor:	0.809
CYP2C9-substrate:	0.084
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.57

ADMET: Excretion

Clearance (CL):	10.041
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.167
Drug-inuced Liver Injury (DILI):	0.732
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.171
Carcinogencity:	0.562
Eye Corrosion:	0.055
Eye Irritation:	0.066
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC178932

Natural Product ID:	NPC178932
*Common Name:**	Proceranolide
IUPAC Name:	n.a.
Synonyms:	3Beta-Deacetylfissinolide; Proceranolide
Standard InCHIKey:	WAIKPAHSFOBDTD-OLJNMEOCSA-N
Standard InCHI:	InChI=1S/C27H34O7/c1-25(2)19(12-20(28)32-5)27(4)17-6-8-26(3)18(15(17)10-16(22(25)30)23(27)31)11-21(29)34-24(26)14-7-9-33-13-14/h7,9,13,16-17,19,22,24,30H,6,8,10-12H2,1-5H3/t16-,17-,19-,22+,24-,26+,27+/m0/s1
SMILES:	CC1(C)[C@H](CC(=O)OC)[C@@]2(C)[C@H]3CC[C@]4(C)C(=C3C[C@@H]([C@H]1O)C2=O)CC(=O)O[C@H]4c1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1081393
PubChem CID:	23258999
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
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	rind	n.a.	DOI[10.1002/hlca.200800177]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[17323995]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	bark	n.a.	PMID[17450509]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19081726]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	seed kernels	n.a.	n.a.	PMID[19908853]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20112995]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[20146503]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20411928]
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]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	Thai	n.a.	PMID[21733687]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22724531]
NPO5587	Chisocheton ceramicus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23395661]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	seeds	n.a.	n.a.	PMID[26114936]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31895570]
NPO28813	Xylocarpus granatum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6445	Xylocarpus moluccensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	50740.0	nM	PMID[447870]
NPT2	Others	Unspecified		IC50	>	27000.0	nM	PMID[447870]

☑ 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 NPC178932 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	336
0.1-0.2	1337
0.2-0.3	2951
0.3-0.4	5221
0.4-0.5	9816
0.5-0.6	10519
0.6-0.7	8992
0.7-0.8	2994
0.8-0.85	264
0.85-0.9	195
0.9-0.95	66
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC469336
0.966	High Similarity	NPC469503
0.9658	High Similarity	NPC469335
0.9658	High Similarity	NPC159927
0.9603	High Similarity	NPC69028
0.9533	High Similarity	NPC472772
0.953	High Similarity	NPC35000
0.9524	High Similarity	NPC477404
0.9524	High Similarity	NPC196864
0.9477	High Similarity	NPC276551
0.9463	High Similarity	NPC30222
0.9416	High Similarity	NPC470875
0.9412	High Similarity	NPC477405
0.9412	High Similarity	NPC469338
0.9412	High Similarity	NPC292389
0.94	High Similarity	NPC469850
0.94	High Similarity	NPC264943
0.9351	High Similarity	NPC470940
0.9351	High Similarity	NPC469849
0.9346	High Similarity	NPC5079
0.9346	High Similarity	NPC472771
0.9333	High Similarity	NPC282445
0.9295	High Similarity	NPC471397
0.9286	High Similarity	NPC234660
0.9286	High Similarity	NPC472773
0.9286	High Similarity	NPC51568
0.9281	High Similarity	NPC477402
0.9276	High Similarity	NPC249021
0.9276	High Similarity	NPC472283
0.9267	High Similarity	NPC75906
0.9247	High Similarity	NPC142113
0.9247	High Similarity	NPC476944
0.9231	High Similarity	NPC472282
0.9231	High Similarity	NPC173516
0.9226	High Similarity	NPC476857
0.9226	High Similarity	NPC476856
0.9226	High Similarity	NPC476858
0.9221	High Similarity	NPC263432
0.9216	High Similarity	NPC474611
0.9216	High Similarity	NPC477403
0.9216	High Similarity	NPC307383
0.9205	High Similarity	NPC57998
0.9195	High Similarity	NPC472654
0.9195	High Similarity	NPC195325
0.9189	High Similarity	NPC250228
0.9184	High Similarity	NPC41182
0.9161	High Similarity	NPC419
0.9161	High Similarity	NPC663
0.9161	High Similarity	NPC224394
0.9156	High Similarity	NPC335761
0.9156	High Similarity	NPC25255
0.9145	High Similarity	NPC92979
0.9145	High Similarity	NPC281258
0.9133	High Similarity	NPC476122
0.9108	High Similarity	NPC476861
0.9108	High Similarity	NPC472775
0.9108	High Similarity	NPC476853
0.9108	High Similarity	NPC472774
0.9108	High Similarity	NPC476850
0.9103	High Similarity	NPC123088
0.9097	High Similarity	NPC329938
0.9097	High Similarity	NPC211777
0.9097	High Similarity	NPC82851
0.9097	High Similarity	NPC200782
0.9097	High Similarity	NPC193798
0.9097	High Similarity	NPC207978
0.9085	High Similarity	NPC60973
0.9085	High Similarity	NPC209364
0.906	High Similarity	NPC471174
0.9051	High Similarity	NPC160651
0.9045	High Similarity	NPC475779
0.9045	High Similarity	NPC23387
0.9038	High Similarity	NPC134254
0.9038	High Similarity	NPC198047
0.9038	High Similarity	NPC39986
0.9038	High Similarity	NPC302369
0.9026	High Similarity	NPC286722
0.9026	High Similarity	NPC167142
0.902	High Similarity	NPC214541
0.902	High Similarity	NPC44675
0.9013	High Similarity	NPC476201
0.8993	High Similarity	NPC346
0.8993	High Similarity	NPC262198
0.8981	High Similarity	NPC476860
0.8981	High Similarity	NPC470182
0.898	High Similarity	NPC121158
0.8974	High Similarity	NPC472767
0.8974	High Similarity	NPC470939
0.8974	High Similarity	NPC96443
0.8974	High Similarity	NPC290400
0.8968	High Similarity	NPC262872
0.8968	High Similarity	NPC475967
0.8968	High Similarity	NPC475295
0.8968	High Similarity	NPC473473
0.8966	High Similarity	NPC476943
0.8961	High Similarity	NPC469485
0.8961	High Similarity	NPC107646
0.8947	High Similarity	NPC272590
0.8933	High Similarity	NPC216755
0.8933	High Similarity	NPC470941
0.8924	High Similarity	NPC97574
0.8924	High Similarity	NPC93172
0.8919	High Similarity	NPC267632
0.8917	High Similarity	NPC476197
0.8917	High Similarity	NPC165218
0.891	High Similarity	NPC472653
0.8903	High Similarity	NPC261597
0.8903	High Similarity	NPC472776
0.8903	High Similarity	NPC472777
0.8903	High Similarity	NPC45101
0.8903	High Similarity	NPC173544
0.8903	High Similarity	NPC472778
0.8903	High Similarity	NPC299038
0.8897	High Similarity	NPC310830
0.8896	High Similarity	NPC75310
0.8896	High Similarity	NPC476262
0.8889	High Similarity	NPC476939
0.8889	High Similarity	NPC476940
0.8882	High Similarity	NPC46551
0.8882	High Similarity	NPC470997
0.8868	High Similarity	NPC473766
0.8868	High Similarity	NPC473753
0.8868	High Similarity	NPC100333
0.8861	High Similarity	NPC472664
0.8859	High Similarity	NPC251865
0.8854	High Similarity	NPC117986
0.8854	High Similarity	NPC18986
0.8854	High Similarity	NPC149896
0.8851	High Similarity	NPC62103
0.8851	High Similarity	NPC20578
0.8846	High Similarity	NPC140952
0.8846	High Similarity	NPC237155
0.8844	High Similarity	NPC67003
0.8839	High Similarity	NPC263265
0.8839	High Similarity	NPC41880
0.8836	High Similarity	NPC220094
0.8816	High Similarity	NPC211625
0.8816	High Similarity	NPC125182
0.8816	High Similarity	NPC69647
0.8812	High Similarity	NPC271235
0.8808	High Similarity	NPC255414
0.8808	High Similarity	NPC221809
0.8805	High Similarity	NPC478178
0.8805	High Similarity	NPC121995
0.88	High Similarity	NPC185456
0.8792	High Similarity	NPC223415
0.8792	High Similarity	NPC243577
0.879	High Similarity	NPC287559
0.879	High Similarity	NPC475381
0.879	High Similarity	NPC305016
0.8782	High Similarity	NPC36655
0.8782	High Similarity	NPC197137
0.8782	High Similarity	NPC304692
0.8782	High Similarity	NPC81405
0.8782	High Similarity	NPC187149
0.8774	High Similarity	NPC155939
0.8774	High Similarity	NPC296807
0.8774	High Similarity	NPC141538
0.8766	High Similarity	NPC33938
0.8766	High Similarity	NPC44577
0.8766	High Similarity	NPC475777
0.8766	High Similarity	NPC246164
0.8758	High Similarity	NPC156189
0.8758	High Similarity	NPC212257
0.8758	High Similarity	NPC82602
0.875	High Similarity	NPC472764
0.875	High Similarity	NPC476941
0.875	High Similarity	NPC476942
0.875	High Similarity	NPC472651
0.8742	High Similarity	NPC471292
0.8742	High Similarity	NPC271657
0.8734	High Similarity	NPC188649
0.8734	High Similarity	NPC197596
0.8734	High Similarity	NPC18347
0.8733	High Similarity	NPC238843
0.8733	High Similarity	NPC199044
0.8726	High Similarity	NPC475226
0.8718	High Similarity	NPC104736
0.8718	High Similarity	NPC204663
0.8718	High Similarity	NPC126723
0.871	High Similarity	NPC114880
0.8704	High Similarity	NPC169299
0.8704	High Similarity	NPC160818
0.8701	High Similarity	NPC18135
0.8699	High Similarity	NPC46896
0.8696	High Similarity	NPC472766
0.8696	High Similarity	NPC472652
0.8696	High Similarity	NPC472765
0.8696	High Similarity	NPC296558
0.8693	High Similarity	NPC234494
0.8688	High Similarity	NPC149945
0.8684	High Similarity	NPC476938
0.8684	High Similarity	NPC302987
0.8684	High Similarity	NPC476937
0.8679	High Similarity	NPC288602
0.8679	High Similarity	NPC88841
0.8675	High Similarity	NPC5676
0.8671	High Similarity	NPC191828
0.8667	High Similarity	NPC470741
0.8667	High Similarity	NPC103134

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 NPC178932 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	290
0.1-0.2	951
0.2-0.3	1999
0.3-0.4	2605
0.4-0.5	1989
0.5-0.6	964
0.6-0.7	303
0.7-0.8	46
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8774	High Similarity	NPD5761	Phase 2
0.8774	High Similarity	NPD5760	Phase 2
0.8294	Intermediate Similarity	NPD8434	Phase 2
0.8098	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6764	Approved
0.7791	Intermediate Similarity	NPD6765	Approved
0.7744	Intermediate Similarity	NPD7819	Suspended
0.7622	Intermediate Similarity	NPD7411	Suspended
0.7614	Intermediate Similarity	NPD6785	Approved
0.7614	Intermediate Similarity	NPD6784	Approved
0.759	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD4628	Phase 3
0.753	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD3749	Approved
0.7486	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD920	Approved
0.7484	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6273	Approved
0.7412	Intermediate Similarity	NPD5494	Approved
0.7396	Intermediate Similarity	NPD7075	Discontinued
0.7362	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2346	Discontinued
0.7358	Intermediate Similarity	NPD1471	Phase 3
0.7349	Intermediate Similarity	NPD6599	Discontinued
0.7341	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD5844	Phase 1
0.7289	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2533	Approved
0.7256	Intermediate Similarity	NPD2532	Approved
0.7256	Intermediate Similarity	NPD2534	Approved
0.7246	Intermediate Similarity	NPD4380	Phase 2
0.7239	Intermediate Similarity	NPD7236	Approved
0.7239	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2799	Discontinued
0.7222	Intermediate Similarity	NPD3750	Approved
0.7219	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD8313	Approved
0.7207	Intermediate Similarity	NPD8312	Approved
0.7205	Intermediate Similarity	NPD1549	Phase 2
0.7193	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2796	Approved
0.7168	Intermediate Similarity	NPD6959	Discontinued
0.7168	Intermediate Similarity	NPD8127	Discontinued
0.716	Intermediate Similarity	NPD2800	Approved
0.716	Intermediate Similarity	NPD6801	Discontinued
0.7152	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7768	Phase 2
0.7125	Intermediate Similarity	NPD3748	Approved
0.712	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8404	Phase 2
0.7102	Intermediate Similarity	NPD7473	Discontinued
0.7091	Intermediate Similarity	NPD6799	Approved
0.7083	Intermediate Similarity	NPD7458	Discontinued
0.7081	Intermediate Similarity	NPD1551	Phase 2
0.7081	Intermediate Similarity	NPD6100	Approved
0.7081	Intermediate Similarity	NPD6099	Approved
0.7076	Intermediate Similarity	NPD5402	Approved
0.707	Intermediate Similarity	NPD3268	Approved
0.707	Intermediate Similarity	NPD2313	Discontinued
0.7069	Intermediate Similarity	NPD1247	Approved
0.7062	Intermediate Similarity	NPD3818	Discontinued
0.7059	Intermediate Similarity	NPD1934	Approved
0.7055	Intermediate Similarity	NPD1243	Approved
0.7052	Intermediate Similarity	NPD919	Approved
0.7037	Intermediate Similarity	NPD2344	Approved
0.7033	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7239	Suspended
0.7022	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7033	Discontinued
0.6995	Remote Similarity	NPD8150	Discontinued
0.6994	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7074	Phase 3
0.6977	Remote Similarity	NPD3817	Phase 2
0.6975	Remote Similarity	NPD2935	Discontinued
0.6966	Remote Similarity	NPD7799	Discontinued
0.6964	Remote Similarity	NPD5403	Approved
0.6962	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD6166	Phase 2
0.6949	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5401	Approved
0.6946	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6832	Phase 2
0.6936	Remote Similarity	NPD3882	Suspended
0.6932	Remote Similarity	NPD6808	Phase 2
0.6932	Remote Similarity	NPD7229	Phase 3
0.6932	Remote Similarity	NPD6232	Discontinued
0.6927	Remote Similarity	NPD7054	Approved
0.6914	Remote Similarity	NPD1510	Phase 2
0.6909	Remote Similarity	NPD7003	Approved
0.6889	Remote Similarity	NPD7472	Approved
0.6883	Remote Similarity	NPD1608	Approved
0.6872	Remote Similarity	NPD3751	Discontinued
0.6868	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD2309	Approved
0.686	Remote Similarity	NPD37	Approved
0.6859	Remote Similarity	NPD3267	Approved
0.6859	Remote Similarity	NPD3266	Approved
0.6851	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4965	Approved
0.6839	Remote Similarity	NPD4967	Phase 2
0.6839	Remote Similarity	NPD4966	Approved
0.6836	Remote Similarity	NPD5710	Approved
0.6836	Remote Similarity	NPD5711	Approved
0.6829	Remote Similarity	NPD6005	Phase 3
0.6829	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6004	Phase 3
0.6829	Remote Similarity	NPD6002	Phase 3
0.6829	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2801	Approved
0.6813	Remote Similarity	NPD7251	Discontinued
0.6813	Remote Similarity	NPD8032	Phase 2
0.6807	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.679	Remote Similarity	NPD1607	Approved
0.6778	Remote Similarity	NPD7228	Approved
0.6776	Remote Similarity	NPD7808	Phase 3
0.677	Remote Similarity	NPD1240	Approved
0.677	Remote Similarity	NPD4140	Approved
0.6763	Remote Similarity	NPD6844	Discontinued
0.6758	Remote Similarity	NPD6797	Phase 2
0.6753	Remote Similarity	NPD7435	Discontinued
0.6752	Remote Similarity	NPD2797	Approved
0.675	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3764	Approved
0.6742	Remote Similarity	NPD3787	Discontinued
0.674	Remote Similarity	NPD7286	Phase 2
0.6728	Remote Similarity	NPD6355	Discontinued
0.6728	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD1465	Phase 2
0.6724	Remote Similarity	NPD8455	Phase 2
0.6721	Remote Similarity	NPD7685	Pre-registration
0.6719	Remote Similarity	NPD8285	Discontinued
0.671	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2798	Approved
0.6707	Remote Similarity	NPD8166	Discontinued
0.6707	Remote Similarity	NPD4308	Phase 3
0.6705	Remote Similarity	NPD5889	Approved
0.6705	Remote Similarity	NPD5890	Approved
0.6705	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD3926	Phase 2
0.6703	Remote Similarity	NPD8407	Phase 2
0.6688	Remote Similarity	NPD17	Approved
0.6687	Remote Similarity	NPD6651	Approved
0.6686	Remote Similarity	NPD1511	Approved
0.6685	Remote Similarity	NPD7199	Phase 2
0.6685	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7177	Discontinued
0.6684	Remote Similarity	NPD4107	Approved
0.6667	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD6234	Discontinued
0.6667	Remote Similarity	NPD5953	Discontinued
0.6667	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD4287	Approved
0.6648	Remote Similarity	NPD7057	Phase 3
0.6648	Remote Similarity	NPD7058	Phase 2
0.6646	Remote Similarity	NPD7097	Phase 1
0.6646	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1203	Approved
0.663	Remote Similarity	NPD7240	Approved
0.663	Remote Similarity	NPD8368	Discontinued
0.6627	Remote Similarity	NPD5763	Approved
0.6627	Remote Similarity	NPD5762	Approved
0.6626	Remote Similarity	NPD5124	Phase 1
0.6626	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD447	Suspended
0.6618	Remote Similarity	NPD4111	Phase 1
0.6618	Remote Similarity	NPD4665	Approved
0.6615	Remote Similarity	NPD3057	Approved
0.6608	Remote Similarity	NPD1512	Approved
0.6607	Remote Similarity	NPD4110	Phase 3
0.6607	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6780	Approved
0.6598	Remote Similarity	NPD6779	Approved
0.6598	Remote Similarity	NPD6781	Approved
0.6598	Remote Similarity	NPD6776	Approved
0.6598	Remote Similarity	NPD6778	Approved
0.6598	Remote Similarity	NPD6782	Approved
0.6598	Remote Similarity	NPD6777	Approved
0.6591	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD7497	Discontinued
0.6582	Remote Similarity	NPD7696	Phase 3
0.6582	Remote Similarity	NPD7698	Approved
0.6582	Remote Similarity	NPD7697	Approved
0.6582	Remote Similarity	NPD3225	Approved
0.6581	Remote Similarity	NPD1778	Approved
0.6581	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD4307	Phase 2

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