NPASS Compound

Structure

CID243165 OpenBabel06191716042D 33 37 0 0 1 0 0 0 0 0999 V2000 0.1609 1.4959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3520 -0.6387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8603 -1.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7312 -0.9952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7297 -4.5273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1839 -0.0910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7150 -4.7367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8378 -0.8173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8796 1.5109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0073 -2.0146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1350 -0.5037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5446 -3.1158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3932 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0073 1.0073 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6244 -3.5255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2911 -0.4886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1350 -1.5110 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7519 1.0073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8796 -1.5109 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7519 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7520 -3.0218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4447 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3687 -0.6387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8796 -0.5036 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0073 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5983 1.4960 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8797 -3.5255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4447 0.9774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2186 -3.8643 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3492 -1.6637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7520 -2.0145 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5983 -0.4886 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 14 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 8 2 0 0 0 0 6 16 1 0 0 0 0 7 29 1 0 0 0 0 8 30 1 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 12 15 2 0 0 0 0 12 29 1 0 0 0 0 13 16 2 0 0 0 0 13 30 1 0 0 0 0 14 25 1 6 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 10 1 1 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 18 26 2 0 0 0 0 19 24 1 1 0 0 0 19 31 1 0 0 0 0 20 24 1 6 0 0 0 20 32 1 0 0 0 0 21 27 2 0 0 0 0 21 31 1 0 0 0 0 22 28 2 0 0 0 0 22 32 1 0 0 0 0 23 33 1 0 0 0 0 24 25 1 6 0 0 0 25 11 1 6 0 0 0 25 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.18
Volume:	450.04
LogP:	3.849
LogD:	2.783
LogS:	-4.582
# Rotatable Bonds:	6
TPSA:	105.18
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.631
Synthetic Accessibility Score:	5.971
Fsp3:	0.56
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:	-5.112
MDCK Permeability:	3.320339965284802e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.36
20% Bioavailability (F20%):	0.981
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.069
Plasma Protein Binding (PPB):	96.47049713134766%
Volume Distribution (VD):	1.33
Pgp-substrate:	9.170540809631348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.106
CYP1A2-substrate:	0.083
CYP2C19-inhibitor:	0.5
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.847
CYP2C9-substrate:	0.066
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.731
CYP3A4-substrate:	0.255

ADMET: Excretion

Clearance (CL):	13.385
Half-life (T1/2):	0.625

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.414
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.995
Maximum Recommended Daily Dose:	0.946
Skin Sensitization:	0.04
Carcinogencity:	0.852
Eye Corrosion:	0.004
Eye Irritation:	0.201
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC243165

Natural Product ID:	NPC243165
*Common Name:**	BFQFVXPTFYVLFJ-OUBULAPXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BFQFVXPTFYVLFJ-OUBULAPXSA-N
Standard InCHI:	InChI=1S/C25H28O8/c1-14-9-18(26)20(32-22(28)16-6-8-30-13-16)24(4)19(31-21(27)15-5-7-29-12-15)10-17-11-25(14,24)33-23(17,2)3/h5-8,12-14,17,19-20H,9-11H2,1-4H3/t14-,17-,19+,20+,24-,25+/m1/s1
SMILES:	C[C@@H]1CC(=O)[C@@H]([C@@]2(C)[C@H](C[C@@H]3C[C@]12OC3(C)C)OC(=O)c1ccoc1)OC(=O)c1ccoc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1165570
PubChem CID:	46850687
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

*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
NPO8412	Monanchora arbuscula	Species	Crambeidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[19743809]
NPO631	Osyris lanceolata	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20499922]
NPO4016	Ligularia fischeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24892518]
NPO8412	Monanchora arbuscula	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[25924111]
NPO4016	Ligularia fischeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4016	Ligularia fischeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO631	Osyris lanceolata	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4016	Ligularia fischeri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8117	Aureolaria virginica	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2871	Canistrocarpus cervicornis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8412	Monanchora arbuscula	Species	Crambeidae	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
MIC	7

Activity Type	# Activity
Organism	5
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	10.0	ug	PMID[509014]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	50.0	ug	PMID[509014]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	10.0	ug	PMID[509014]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	10.0	ug	PMID[509014]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.5	ug	PMID[509014]
NPT1	Others	Radical scavenging activity		MIC	=	10.0	ug	PMID[509014]

☑ 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 NPC243165 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	376
0.1-0.2	1703
0.2-0.3	3789
0.3-0.4	7006
0.4-0.5	12596
0.5-0.6	10014
0.6-0.7	6461
0.7-0.8	641
0.8-0.85	89
0.85-0.9	18
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9653	High Similarity	NPC240214
0.9429	High Similarity	NPC156077
0.8926	High Similarity	NPC294803
0.8926	High Similarity	NPC6815
0.8867	High Similarity	NPC147340
0.8867	High Similarity	NPC271460
0.871	High Similarity	NPC191828
0.8477	Intermediate Similarity	NPC221809
0.8366	Intermediate Similarity	NPC195325
0.8322	Intermediate Similarity	NPC20500
0.8313	Intermediate Similarity	NPC276735
0.8267	Intermediate Similarity	NPC473152
0.8258	Intermediate Similarity	NPC18135
0.825	Intermediate Similarity	NPC469846
0.8239	Intermediate Similarity	NPC305016
0.8228	Intermediate Similarity	NPC286722
0.8228	Intermediate Similarity	NPC249021
0.8212	Intermediate Similarity	NPC223415
0.8212	Intermediate Similarity	NPC470741
0.8194	Intermediate Similarity	NPC476122
0.8194	Intermediate Similarity	NPC156189
0.8188	Intermediate Similarity	NPC474722
0.8187	Intermediate Similarity	NPC470939
0.8176	Intermediate Similarity	NPC473473
0.8176	Intermediate Similarity	NPC475967
0.8176	Intermediate Similarity	NPC475295
0.817	Intermediate Similarity	NPC262198
0.8165	Intermediate Similarity	NPC126723
0.8165	Intermediate Similarity	NPC107646
0.8165	Intermediate Similarity	NPC209364
0.8137	Intermediate Similarity	NPC419
0.8125	Intermediate Similarity	NPC475381
0.8121	Intermediate Similarity	NPC236532
0.8121	Intermediate Similarity	NPC469848
0.8113	Intermediate Similarity	NPC246841
0.8113	Intermediate Similarity	NPC36655
0.8113	Intermediate Similarity	NPC472283
0.8113	Intermediate Similarity	NPC1408
0.8113	Intermediate Similarity	NPC261597
0.811	Intermediate Similarity	NPC88593
0.8108	Intermediate Similarity	NPC146872
0.8101	Intermediate Similarity	NPC44675
0.8101	Intermediate Similarity	NPC214541
0.8098	Intermediate Similarity	NPC476861
0.8098	Intermediate Similarity	NPC476850
0.8089	Intermediate Similarity	NPC476201
0.8089	Intermediate Similarity	NPC75906
0.8086	Intermediate Similarity	NPC123088
0.8077	Intermediate Similarity	NPC196864
0.8077	Intermediate Similarity	NPC476936
0.8077	Intermediate Similarity	NPC469335
0.8077	Intermediate Similarity	NPC159927
0.8077	Intermediate Similarity	NPC477404
0.8075	Intermediate Similarity	NPC6326
0.8075	Intermediate Similarity	NPC82851
0.8075	Intermediate Similarity	NPC197596
0.8063	Intermediate Similarity	NPC237155
0.8061	Intermediate Similarity	NPC294512
0.8054	Intermediate Similarity	NPC470742
0.8052	Intermediate Similarity	NPC62799
0.805	Intermediate Similarity	NPC263265
0.805	Intermediate Similarity	NPC60973
0.8049	Intermediate Similarity	NPC271235
0.8039	Intermediate Similarity	NPC251865
0.8038	Intermediate Similarity	NPC282445
0.8037	Intermediate Similarity	NPC478178
0.8037	Intermediate Similarity	NPC472141
0.8025	Intermediate Similarity	NPC39986
0.8025	Intermediate Similarity	NPC663
0.8025	Intermediate Similarity	NPC302369
0.8025	Intermediate Similarity	NPC14499
0.8025	Intermediate Similarity	NPC476035
0.8025	Intermediate Similarity	NPC224394
0.8025	Intermediate Similarity	NPC134254
0.8025	Intermediate Similarity	NPC475039
0.8013	Intermediate Similarity	NPC470790
0.8013	Intermediate Similarity	NPC470791
0.8012	Intermediate Similarity	NPC472653
0.8012	Intermediate Similarity	NPC25255
0.8	Intermediate Similarity	NPC469847
0.8	Intermediate Similarity	NPC167142
0.8	Intermediate Similarity	NPC299038
0.8	Intermediate Similarity	NPC470941
0.8	Intermediate Similarity	NPC187149
0.8	Intermediate Similarity	NPC472772
0.7988	Intermediate Similarity	NPC472651
0.7988	Intermediate Similarity	NPC478179
0.7987	Intermediate Similarity	NPC469850
0.7987	Intermediate Similarity	NPC476262
0.7975	Intermediate Similarity	NPC476857
0.7975	Intermediate Similarity	NPC476860
0.7975	Intermediate Similarity	NPC308205
0.7975	Intermediate Similarity	NPC476856
0.7975	Intermediate Similarity	NPC469503
0.7975	Intermediate Similarity	NPC476858
0.7975	Intermediate Similarity	NPC322546
0.7974	Intermediate Similarity	NPC267632
0.7974	Intermediate Similarity	NPC243577
0.7963	Intermediate Similarity	NPC193798
0.7963	Intermediate Similarity	NPC5079
0.7963	Intermediate Similarity	NPC329938
0.7963	Intermediate Similarity	NPC117986
0.795	Intermediate Similarity	NPC475226
0.795	Intermediate Similarity	NPC477403
0.7949	Intermediate Similarity	NPC19747
0.7939	Intermediate Similarity	NPC472652
0.7939	Intermediate Similarity	NPC327922
0.7937	Intermediate Similarity	NPC104736
0.7937	Intermediate Similarity	NPC204663
0.7927	Intermediate Similarity	NPC23387
0.7927	Intermediate Similarity	NPC86800
0.7927	Intermediate Similarity	NPC214600
0.7925	Intermediate Similarity	NPC57998
0.7922	Intermediate Similarity	NPC84479
0.7919	Intermediate Similarity	NPC92941
0.7917	Intermediate Similarity	NPC176413
0.7917	Intermediate Similarity	NPC56953
0.7914	Intermediate Similarity	NPC51568
0.7914	Intermediate Similarity	NPC165218
0.7914	Intermediate Similarity	NPC477405
0.7914	Intermediate Similarity	NPC234660
0.7914	Intermediate Similarity	NPC292389
0.7914	Intermediate Similarity	NPC469338
0.7914	Intermediate Similarity	NPC471168
0.7901	Intermediate Similarity	NPC335761
0.7898	Intermediate Similarity	NPC472654
0.7898	Intermediate Similarity	NPC211625
0.7888	Intermediate Similarity	NPC195131
0.7888	Intermediate Similarity	NPC81405
0.7888	Intermediate Similarity	NPC470118
0.7888	Intermediate Similarity	NPC304692
0.7885	Intermediate Similarity	NPC10088
0.7881	Intermediate Similarity	NPC476943
0.7879	Intermediate Similarity	NPC473753
0.7879	Intermediate Similarity	NPC476853
0.7879	Intermediate Similarity	NPC473766
0.7879	Intermediate Similarity	NPC173516
0.7879	Intermediate Similarity	NPC476224
0.7879	Intermediate Similarity	NPC472774
0.7879	Intermediate Similarity	NPC472775
0.7875	Intermediate Similarity	NPC469336
0.7875	Intermediate Similarity	NPC75310
0.7866	Intermediate Similarity	NPC469849
0.7866	Intermediate Similarity	NPC470940
0.7866	Intermediate Similarity	NPC159520
0.7866	Intermediate Similarity	NPC276551
0.7862	Intermediate Similarity	NPC182427
0.7862	Intermediate Similarity	NPC29695
0.7862	Intermediate Similarity	NPC476939
0.7862	Intermediate Similarity	NPC476940
0.7862	Intermediate Similarity	NPC268905
0.7857	Intermediate Similarity	NPC236004
0.7857	Intermediate Similarity	NPC205071
0.7853	Intermediate Similarity	NPC472668
0.7853	Intermediate Similarity	NPC263432
0.7853	Intermediate Similarity	NPC69028
0.7853	Intermediate Similarity	NPC472771
0.7848	Intermediate Similarity	NPC46551
0.7844	Intermediate Similarity	NPC160818
0.7844	Intermediate Similarity	NPC169299
0.7844	Intermediate Similarity	NPC159232
0.7844	Intermediate Similarity	NPC285227
0.784	Intermediate Similarity	NPC140952
0.784	Intermediate Similarity	NPC474932
0.7831	Intermediate Similarity	NPC471397
0.7831	Intermediate Similarity	NPC160651
0.7826	Intermediate Similarity	NPC41880
0.7821	Intermediate Similarity	NPC346
0.7821	Intermediate Similarity	NPC276676
0.7818	Intermediate Similarity	NPC149945
0.7818	Intermediate Similarity	NPC470875
0.7812	Intermediate Similarity	NPC30222
0.7812	Intermediate Similarity	NPC178932
0.7806	Intermediate Similarity	NPC86935
0.7805	Intermediate Similarity	NPC472669
0.7805	Intermediate Similarity	NPC472139
0.7805	Intermediate Similarity	NPC285567
0.7805	Intermediate Similarity	NPC476197
0.7805	Intermediate Similarity	NPC472773
0.7799	Intermediate Similarity	NPC116717
0.7792	Intermediate Similarity	NPC52412
0.7792	Intermediate Similarity	NPC475519
0.7792	Intermediate Similarity	NPC121158
0.7791	Intermediate Similarity	NPC477402
0.7791	Intermediate Similarity	NPC470789
0.7785	Intermediate Similarity	NPC471001
0.7784	Intermediate Similarity	NPC470995
0.7784	Intermediate Similarity	NPC302392
0.7784	Intermediate Similarity	NPC82602
0.7778	Intermediate Similarity	NPC214495
0.7778	Intermediate Similarity	NPC470119
0.7778	Intermediate Similarity	NPC472777
0.7778	Intermediate Similarity	NPC45101
0.7778	Intermediate Similarity	NPC472778
0.7778	Intermediate Similarity	NPC472776
0.7771	Intermediate Similarity	NPC270312
0.7771	Intermediate Similarity	NPC255414
0.7771	Intermediate Similarity	NPC250228
0.7771	Intermediate Similarity	NPC472282
0.7765	Intermediate Similarity	NPC478177

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 NPC243165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	1271
0.2-0.3	2669
0.3-0.4	2652
0.4-0.5	1559
0.5-0.6	555
0.6-0.7	118
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7683	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD5761	Phase 2
0.7546	Intermediate Similarity	NPD5760	Phase 2
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD1471	Phase 3
0.7073	Intermediate Similarity	NPD920	Approved
0.7048	Intermediate Similarity	NPD6599	Discontinued
0.6959	Remote Similarity	NPD919	Approved
0.6951	Remote Similarity	NPD642	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6765	Approved
0.691	Remote Similarity	NPD6764	Approved
0.6832	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7819	Suspended
0.6816	Remote Similarity	NPD6559	Discontinued
0.6802	Remote Similarity	NPD7075	Discontinued
0.68	Remote Similarity	NPD3926	Phase 2
0.6788	Remote Similarity	NPD6799	Approved
0.6784	Remote Similarity	NPD5402	Approved
0.6782	Remote Similarity	NPD1247	Approved
0.6765	Remote Similarity	NPD6801	Discontinued
0.6758	Remote Similarity	NPD6785	Approved
0.6758	Remote Similarity	NPD6784	Approved
0.6724	Remote Similarity	NPD5494	Approved
0.6686	Remote Similarity	NPD3226	Approved
0.6686	Remote Similarity	NPD3817	Phase 2
0.6685	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD2796	Approved
0.6647	Remote Similarity	NPD5401	Approved
0.6646	Remote Similarity	NPD1243	Approved
0.6624	Remote Similarity	NPD6832	Phase 2
0.6609	Remote Similarity	NPD3749	Approved
0.6605	Remote Similarity	NPD2799	Discontinued
0.6578	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD1551	Phase 2
0.6552	Remote Similarity	NPD3882	Suspended
0.6548	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2346	Discontinued
0.6517	Remote Similarity	NPD8404	Phase 2
0.6512	Remote Similarity	NPD7411	Suspended
0.6506	Remote Similarity	NPD4628	Phase 3
0.6503	Remote Similarity	NPD3748	Approved
0.6461	Remote Similarity	NPD6808	Phase 2
0.645	Remote Similarity	NPD2534	Approved
0.645	Remote Similarity	NPD2533	Approved
0.645	Remote Similarity	NPD2532	Approved
0.6444	Remote Similarity	NPD7473	Discontinued
0.6424	Remote Similarity	NPD2344	Approved
0.642	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD6273	Approved
0.64	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6232	Discontinued
0.6364	Remote Similarity	NPD4966	Approved
0.6364	Remote Similarity	NPD4967	Phase 2
0.6364	Remote Similarity	NPD7768	Phase 2
0.6364	Remote Similarity	NPD4965	Approved
0.6364	Remote Similarity	NPD2935	Discontinued
0.6347	Remote Similarity	NPD2800	Approved
0.6343	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD2313	Discontinued
0.6319	Remote Similarity	NPD3818	Discontinued
0.6313	Remote Similarity	NPD6959	Discontinued
0.631	Remote Similarity	NPD3750	Approved
0.631	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD6234	Discontinued
0.629	Remote Similarity	NPD8312	Approved
0.629	Remote Similarity	NPD8313	Approved
0.6287	Remote Similarity	NPD1549	Phase 2
0.6284	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD2309	Approved
0.6264	Remote Similarity	NPD4380	Phase 2
0.6257	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6244	Remote Similarity	NPD7435	Discontinued
0.6237	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6355	Discontinued
0.6216	Remote Similarity	NPD5953	Discontinued
0.6213	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD6166	Phase 2
0.6209	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5844	Phase 1
0.6193	Remote Similarity	NPD6280	Approved
0.6193	Remote Similarity	NPD1934	Approved
0.6193	Remote Similarity	NPD37	Approved
0.6193	Remote Similarity	NPD6279	Approved
0.619	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.618	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD3887	Approved
0.6164	Remote Similarity	NPD1876	Approved
0.6159	Remote Similarity	NPD4307	Phase 2
0.6154	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD7799	Discontinued
0.6141	Remote Similarity	NPD3751	Discontinued
0.614	Remote Similarity	NPD7236	Approved
0.6139	Remote Similarity	NPD3972	Approved
0.6133	Remote Similarity	NPD8127	Discontinued
0.6129	Remote Similarity	NPD6797	Phase 2
0.6124	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.612	Remote Similarity	NPD2403	Approved
0.6108	Remote Similarity	NPD1510	Phase 2
0.6105	Remote Similarity	NPD8150	Discontinued
0.6098	Remote Similarity	NPD8032	Phase 2
0.6096	Remote Similarity	NPD7251	Discontinued
0.6091	Remote Similarity	NPD6780	Approved
0.6091	Remote Similarity	NPD6779	Approved
0.6091	Remote Similarity	NPD6781	Approved
0.6091	Remote Similarity	NPD6778	Approved
0.6091	Remote Similarity	NPD6776	Approved
0.6091	Remote Similarity	NPD6782	Approved
0.6091	Remote Similarity	NPD6777	Approved
0.6087	Remote Similarity	NPD2798	Approved
0.6087	Remote Similarity	NPD1019	Discontinued
0.6084	Remote Similarity	NPD1607	Approved
0.6071	Remote Similarity	NPD2438	Suspended
0.6067	Remote Similarity	NPD2801	Approved
0.6064	Remote Similarity	NPD7808	Phase 3
0.6061	Remote Similarity	NPD1240	Approved
0.6061	Remote Similarity	NPD2979	Phase 3
0.6059	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6059	Remote Similarity	NPD7874	Approved
0.6057	Remote Similarity	NPD7239	Suspended
0.6054	Remote Similarity	NPD7228	Approved
0.6051	Remote Similarity	NPD17	Approved
0.6043	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6041	Remote Similarity	NPD8285	Discontinued
0.6037	Remote Similarity	NPD3764	Approved
0.6037	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD6005	Phase 3
0.6036	Remote Similarity	NPD6004	Phase 3
0.6036	Remote Similarity	NPD6002	Phase 3
0.6036	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD1512	Approved
0.6025	Remote Similarity	NPD1203	Approved
0.6025	Remote Similarity	NPD3266	Approved
0.6025	Remote Similarity	NPD3267	Approved
0.6024	Remote Similarity	NPD1933	Approved
0.6023	Remote Similarity	NPD7003	Approved
0.6022	Remote Similarity	NPD7286	Phase 2
0.6012	Remote Similarity	NPD7033	Discontinued
0.6012	Remote Similarity	NPD4308	Phase 3
0.6011	Remote Similarity	NPD3787	Discontinued
0.6011	Remote Similarity	NPD5711	Approved
0.6011	Remote Similarity	NPD7229	Phase 3
0.6011	Remote Similarity	NPD5710	Approved
0.601	Remote Similarity	NPD4107	Approved
0.6	Remote Similarity	NPD7698	Approved
0.6	Remote Similarity	NPD7696	Phase 3
0.6	Remote Similarity	NPD8407	Phase 2
0.6	Remote Similarity	NPD7697	Approved
0.5989	Remote Similarity	NPD7074	Phase 3
0.5987	Remote Similarity	NPD5585	Approved
0.5976	Remote Similarity	NPD6100	Approved
0.5976	Remote Similarity	NPD6099	Approved
0.597	Remote Similarity	NPD7870	Phase 2
0.597	Remote Similarity	NPD7871	Phase 2
0.597	Remote Similarity	NPD8319	Approved
0.597	Remote Similarity	NPD8320	Phase 1
0.5959	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD7199	Phase 2
0.5943	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD2353	Approved
0.5941	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.5941	Remote Similarity	NPD5762	Approved
0.5941	Remote Similarity	NPD5763	Approved
0.5939	Remote Similarity	NPD6798	Discontinued
0.5939	Remote Similarity	NPD3268	Approved
0.5939	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD9717	Approved
0.5938	Remote Similarity	NPD1608	Approved
0.5936	Remote Similarity	NPD7054	Approved
0.5932	Remote Similarity	NPD7458	Discontinued
0.5928	Remote Similarity	NPD447	Suspended
0.5926	Remote Similarity	NPD7240	Approved
0.5926	Remote Similarity	NPD8368	Discontinued
0.5926	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD2797	Approved
0.592	Remote Similarity	NPD1511	Approved
0.5904	Remote Similarity	NPD6233	Phase 2
0.5904	Remote Similarity	NPD7472	Approved
0.59	Remote Similarity	NPD4482	Phase 3
0.5895	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6651	Approved
0.5882	Remote Similarity	NPD7701	Phase 2
0.5879	Remote Similarity	NPD7095	Approved
0.5876	Remote Similarity	NPD4287	Approved
0.5875	Remote Similarity	NPD1281	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