NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	524.31
Volume:	573.928
LogP:	2.619
LogD:	2.665
LogS:	-4.237
# Rotatable Bonds:	13
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.276
Synthetic Accessibility Score:	5.143
Fsp3:	0.469
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.995
MDCK Permeability:	2.9392624128377065e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.885
Human Intestinal Absorption (HIA):	0.171
20% Bioavailability (F20%):	0.071
30% Bioavailability (F30%):	0.053

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.253
Plasma Protein Binding (PPB):	98.12493133544922%
Volume Distribution (VD):	0.895
Pgp-substrate:	2.187324047088623%

ADMET: Metabolism

CYP1A2-inhibitor:	0.098
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.106
CYP2C19-substrate:	0.899
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.891
CYP2D6-inhibitor:	0.376
CYP2D6-substrate:	0.499
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.834

ADMET: Excretion

Clearance (CL):	8.854
Half-life (T1/2):	0.715

ADMET: Toxicity

hERG Blockers:	0.206
Human Hepatotoxicity (H-HT):	0.809
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.866
Maximum Recommended Daily Dose:	0.972
Skin Sensitization:	0.159
Carcinogencity:	0.585
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.837

Download Data

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

Natural Product: NPC477245

Natural Product ID:	NPC477245
*Common Name:**	Hyafurone A1
IUPAC Name:	2-hydroxy-2,4-dimethyl-5-[(5Z,7E,9E,11E)-2,4,14-trihydroxy-9,13,15-trimethyl-17-phenylheptadeca-5,7,9,11-tetraenyl]furan-3-one
Synonyms:
Standard InCHIKey:	NMMBWYBMSULADK-DTRVTNFDSA-N
Standard InCHI:	InChI=1S/C32H44O6/c1-22(13-11-14-23(2)30(35)24(3)18-19-26-15-7-6-8-16-26)12-9-10-17-27(33)20-28(34)21-29-25(4)31(36)32(5,37)38-29/h6-17,23-24,27-28,30,33-35,37H,18-21H2,1-5H3/b12-9+,14-11+,17-10-,22-13+
SMILES:	CC1=C(OC(C1=O)(C)O)CC(CC(/C=C\C=C\C(=C\C=C\C(C)C(C(C)CCC2=CC=CC=C2)O)\C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90681737
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002951] Long-chain fatty alcohols

*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
NPO33535	Hyalangium minutum	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22497473]
NPO33535	Hyalangium minutum	Species	Archangiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24848583]

☑ 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
MIC	12

Activity Type	# Activity
Cell Line	1
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	=	2670	nM	PMID[24848583]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	<=	67	ug/ml	PMID[24848583]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	<=	67	ug/ml	PMID[24848583]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	<=	67	ug/ml	PMID[24848583]
NPT5748	Organism	Nocardia canis	Nocardia canis	MIC	<=	67	ug/ml	PMID[24848583]
NPT2631	Organism	Chromobacterium violaceum	Chromobacterium violaceum	MIC	<=	67	ug/ml	PMID[24848583]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	<=	67	ug/ml	PMID[24848583]
NPT1177	Organism	Mycobacterium phlei	Mycobacterium phlei	MIC	<=	67	ug/ml	PMID[24848583]
NPT3481	Organism	Mucor hiemalis	Mucor hiemalis	MIC	<=	67	ug/ml	PMID[24848583]
NPT765	Organism	Schizosaccharomyces pombe	Schizosaccharomyces pombe	MIC	<=	67	ug/ml	PMID[24848583]
NPT3628	Organism	Rhodotorula glutinis	Rhodotorula glutinis	MIC	<=	67	ug/ml	PMID[24848583]
NPT772	Organism	Pichia anomala	Wickerhamomyces anomalus	MIC	<=	67	ug/ml	PMID[24848583]
NPT20	Organism	Candida albicans	Candida albicans	MIC	<=	67	ug/ml	PMID[24848583]

☑ 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 NPC477245 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	176
0.1-0.2	869
0.2-0.3	2104
0.3-0.4	6778
0.4-0.5	12718
0.5-0.6	15818
0.6-0.7	4113
0.7-0.8	113
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477246
0.9434	High Similarity	NPC477247
0.8482	Intermediate Similarity	NPC477250
0.8364	Intermediate Similarity	NPC477251
0.7724	Intermediate Similarity	NPC475328
0.7632	Intermediate Similarity	NPC474307
0.7597	Intermediate Similarity	NPC17567
0.757	Intermediate Similarity	NPC108026
0.7563	Intermediate Similarity	NPC87069
0.75	Intermediate Similarity	NPC230331
0.75	Intermediate Similarity	NPC80115
0.746	Intermediate Similarity	NPC470815
0.7458	Intermediate Similarity	NPC323007
0.7456	Intermediate Similarity	NPC91820
0.7456	Intermediate Similarity	NPC82426
0.7436	Intermediate Similarity	NPC475282
0.7411	Intermediate Similarity	NPC145052
0.7411	Intermediate Similarity	NPC154517
0.7411	Intermediate Similarity	NPC135951
0.7387	Intermediate Similarity	NPC30361
0.7377	Intermediate Similarity	NPC470820
0.7364	Intermediate Similarity	NPC23453
0.7364	Intermediate Similarity	NPC477370
0.7328	Intermediate Similarity	NPC289415
0.7328	Intermediate Similarity	NPC319995
0.7317	Intermediate Similarity	NPC471553
0.7308	Intermediate Similarity	NPC226101
0.7308	Intermediate Similarity	NPC237182
0.7297	Intermediate Similarity	NPC473347
0.7295	Intermediate Similarity	NPC476476
0.7293	Intermediate Similarity	NPC136608
0.7293	Intermediate Similarity	NPC38420
0.7288	Intermediate Similarity	NPC469511
0.7288	Intermediate Similarity	NPC182549
0.7288	Intermediate Similarity	NPC114741
0.7287	Intermediate Similarity	NPC477365
0.7273	Intermediate Similarity	NPC475569
0.7273	Intermediate Similarity	NPC476976
0.7266	Intermediate Similarity	NPC477249
0.7266	Intermediate Similarity	NPC477248
0.7266	Intermediate Similarity	NPC474803
0.7265	Intermediate Similarity	NPC136962
0.7257	Intermediate Similarity	NPC317280
0.7257	Intermediate Similarity	NPC329387
0.7252	Intermediate Similarity	NPC49272
0.725	Intermediate Similarity	NPC185840
0.7244	Intermediate Similarity	NPC141970
0.7244	Intermediate Similarity	NPC108286
0.7244	Intermediate Similarity	NPC140561
0.7231	Intermediate Similarity	NPC58061
0.7231	Intermediate Similarity	NPC231627
0.7213	Intermediate Similarity	NPC469509
0.7209	Intermediate Similarity	NPC477366
0.7209	Intermediate Similarity	NPC45821
0.7209	Intermediate Similarity	NPC477363
0.7209	Intermediate Similarity	NPC470816
0.7206	Intermediate Similarity	NPC475195
0.72	Intermediate Similarity	NPC476020
0.7197	Intermediate Similarity	NPC476977
0.7188	Intermediate Similarity	NPC138798
0.7188	Intermediate Similarity	NPC472373
0.7185	Intermediate Similarity	NPC202729
0.7177	Intermediate Similarity	NPC122117
0.7176	Intermediate Similarity	NPC93632
0.7176	Intermediate Similarity	NPC37968
0.7168	Intermediate Similarity	NPC289201
0.7164	Intermediate Similarity	NPC470143
0.7164	Intermediate Similarity	NPC322503
0.7154	Intermediate Similarity	NPC276047
0.7154	Intermediate Similarity	NPC267733
0.7154	Intermediate Similarity	NPC81135
0.7143	Intermediate Similarity	NPC475827
0.7143	Intermediate Similarity	NPC474223
0.7143	Intermediate Similarity	NPC280827
0.7143	Intermediate Similarity	NPC475804
0.7143	Intermediate Similarity	NPC474222
0.7143	Intermediate Similarity	NPC243059
0.7143	Intermediate Similarity	NPC184633
0.7132	Intermediate Similarity	NPC57607
0.7132	Intermediate Similarity	NPC284022
0.7132	Intermediate Similarity	NPC145287
0.7132	Intermediate Similarity	NPC471758
0.7132	Intermediate Similarity	NPC477369
0.7132	Intermediate Similarity	NPC27721
0.7131	Intermediate Similarity	NPC474641
0.7121	Intermediate Similarity	NPC475452
0.7121	Intermediate Similarity	NPC472388
0.7121	Intermediate Similarity	NPC475671
0.7119	Intermediate Similarity	NPC472316
0.7119	Intermediate Similarity	NPC475203
0.7119	Intermediate Similarity	NPC472315
0.7119	Intermediate Similarity	NPC474376
0.7119	Intermediate Similarity	NPC37115
0.7109	Intermediate Similarity	NPC12016
0.7109	Intermediate Similarity	NPC474254
0.7109	Intermediate Similarity	NPC474159
0.7109	Intermediate Similarity	NPC65627
0.7107	Intermediate Similarity	NPC470825
0.7107	Intermediate Similarity	NPC234376
0.7105	Intermediate Similarity	NPC262826
0.7103	Intermediate Similarity	NPC99482
0.7099	Intermediate Similarity	NPC268607
0.7099	Intermediate Similarity	NPC103533
0.7097	Intermediate Similarity	NPC28951
0.7097	Intermediate Similarity	NPC325646
0.7097	Intermediate Similarity	NPC123559
0.7094	Intermediate Similarity	NPC242913
0.7094	Intermediate Similarity	NPC280616
0.7094	Intermediate Similarity	NPC19136
0.7094	Intermediate Similarity	NPC171831
0.7094	Intermediate Similarity	NPC47286
0.709	Intermediate Similarity	NPC15850
0.7077	Intermediate Similarity	NPC236405
0.7063	Intermediate Similarity	NPC470814
0.7059	Intermediate Similarity	NPC20485
0.7059	Intermediate Similarity	NPC277788
0.7054	Intermediate Similarity	NPC8990
0.7054	Intermediate Similarity	NPC477362
0.7054	Intermediate Similarity	NPC473881
0.7049	Intermediate Similarity	NPC265002
0.7045	Intermediate Similarity	NPC225103
0.704	Intermediate Similarity	NPC476266
0.7037	Intermediate Similarity	NPC477280
0.7037	Intermediate Similarity	NPC19719
0.7037	Intermediate Similarity	NPC28836
0.7037	Intermediate Similarity	NPC477281
0.7034	Intermediate Similarity	NPC321670
0.7027	Intermediate Similarity	NPC476484
0.7025	Intermediate Similarity	NPC63345
0.7025	Intermediate Similarity	NPC43584
0.7023	Intermediate Similarity	NPC198918
0.7023	Intermediate Similarity	NPC92283
0.7023	Intermediate Similarity	NPC204214
0.7023	Intermediate Similarity	NPC477357
0.7023	Intermediate Similarity	NPC124878
0.7023	Intermediate Similarity	NPC35338
0.7023	Intermediate Similarity	NPC231888
0.7023	Intermediate Similarity	NPC63404
0.7023	Intermediate Similarity	NPC290276
0.7023	Intermediate Similarity	NPC10121
0.7023	Intermediate Similarity	NPC10883
0.7023	Intermediate Similarity	NPC61181
0.7019	Intermediate Similarity	NPC469894
0.7018	Intermediate Similarity	NPC103048
0.7016	Intermediate Similarity	NPC471616
0.7015	Intermediate Similarity	NPC233692
0.7009	Intermediate Similarity	NPC304538
0.7009	Intermediate Similarity	NPC160382
0.7008	Intermediate Similarity	NPC282409
0.7008	Intermediate Similarity	NPC469702
0.7	Intermediate Similarity	NPC244454
0.7	Intermediate Similarity	NPC162925
0.7	Intermediate Similarity	NPC281604
0.7	Intermediate Similarity	NPC87153
0.7	Intermediate Similarity	NPC284957
0.7	Intermediate Similarity	NPC317163
0.6992	Remote Similarity	NPC11025
0.6992	Remote Similarity	NPC473443
0.6992	Remote Similarity	NPC253595
0.6991	Remote Similarity	NPC206764
0.6985	Remote Similarity	NPC477367
0.6985	Remote Similarity	NPC472247
0.6985	Remote Similarity	NPC232888
0.6985	Remote Similarity	NPC23894
0.6985	Remote Similarity	NPC474659
0.6983	Remote Similarity	NPC469481
0.6978	Remote Similarity	NPC475413
0.6978	Remote Similarity	NPC473497
0.6978	Remote Similarity	NPC474303
0.6977	Remote Similarity	NPC273336
0.6977	Remote Similarity	NPC182333
0.6975	Remote Similarity	NPC51174
0.6972	Remote Similarity	NPC170668
0.697	Remote Similarity	NPC175333
0.697	Remote Similarity	NPC478165
0.697	Remote Similarity	NPC478162
0.6963	Remote Similarity	NPC472248
0.6963	Remote Similarity	NPC323379
0.6963	Remote Similarity	NPC327204
0.696	Remote Similarity	NPC148055
0.6957	Remote Similarity	NPC476120
0.6957	Remote Similarity	NPC179411
0.6953	Remote Similarity	NPC469548
0.6953	Remote Similarity	NPC476448
0.6953	Remote Similarity	NPC476445
0.6953	Remote Similarity	NPC229600
0.695	Remote Similarity	NPC186296
0.6949	Remote Similarity	NPC249067
0.6949	Remote Similarity	NPC148060
0.6947	Remote Similarity	NPC79608
0.6947	Remote Similarity	NPC476599
0.6947	Remote Similarity	NPC28069
0.6947	Remote Similarity	NPC77651
0.6947	Remote Similarity	NPC470158
0.6947	Remote Similarity	NPC475933
0.694	Remote Similarity	NPC163169
0.694	Remote Similarity	NPC123
0.6935	Remote Similarity	NPC474114
0.6935	Remote Similarity	NPC474050
0.6935	Remote Similarity	NPC473931

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 NPC477245 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	704
0.2-0.3	1505
0.3-0.4	3053
0.4-0.5	2340
0.5-0.6	1246
0.6-0.7	134
0.7-0.8	10
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
0.7928	Intermediate Similarity	NPD6647	Phase 2
0.7565	Intermediate Similarity	NPD6685	Approved
0.7521	Intermediate Similarity	NPD2067	Discontinued
0.7481	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5048	Discontinued
0.7304	Intermediate Similarity	NPD5765	Approved
0.7304	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7741	Discontinued
0.7107	Intermediate Similarity	NPD969	Suspended
0.7107	Intermediate Similarity	NPD6912	Phase 3
0.7073	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2629	Approved
0.7	Intermediate Similarity	NPD689	Discontinued
0.696	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1237	Approved
0.6949	Remote Similarity	NPD5909	Discontinued
0.6903	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5126	Approved
0.6875	Remote Similarity	NPD5125	Phase 3
0.6818	Remote Similarity	NPD1282	Approved
0.681	Remote Similarity	NPD9495	Approved
0.6746	Remote Similarity	NPD4198	Discontinued
0.6639	Remote Similarity	NPD6406	Approved
0.6613	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.661	Remote Similarity	NPD7798	Approved
0.661	Remote Similarity	NPD2066	Phase 3
0.6607	Remote Similarity	NPD531	Approved
0.6552	Remote Similarity	NPD1693	Approved
0.6549	Remote Similarity	NPD5347	Phase 2
0.6549	Remote Similarity	NPD6004	Phase 3
0.6549	Remote Similarity	NPD6002	Phase 3
0.6549	Remote Similarity	NPD5346	Phase 2
0.6549	Remote Similarity	NPD6005	Phase 3
0.6549	Remote Similarity	NPD5762	Approved
0.6549	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD7266	Discontinued
0.6549	Remote Similarity	NPD5763	Approved
0.6549	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD6355	Discontinued
0.6525	Remote Similarity	NPD5926	Approved
0.6519	Remote Similarity	NPD6085	Phase 2
0.6519	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD6858	Approved
0.6508	Remote Similarity	NPD7094	Approved
0.6491	Remote Similarity	NPD3673	Approved
0.6491	Remote Similarity	NPD3672	Approved
0.6486	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.648	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD1929	Approved
0.6446	Remote Similarity	NPD1930	Approved
0.6438	Remote Similarity	NPD7236	Approved
0.6429	Remote Similarity	NPD5124	Phase 1
0.6429	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7033	Discontinued
0.6404	Remote Similarity	NPD800	Approved
0.6403	Remote Similarity	NPD7961	Discontinued
0.6391	Remote Similarity	NPD4807	Approved
0.6391	Remote Similarity	NPD1091	Approved
0.6391	Remote Similarity	NPD4806	Approved
0.6383	Remote Similarity	NPD6653	Approved
0.6378	Remote Similarity	NPD7843	Approved
0.6377	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD4793	Discontinued
0.6364	Remote Similarity	NPD5305	Approved
0.6364	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5306	Approved
0.6355	Remote Similarity	NPD9294	Approved
0.635	Remote Similarity	NPD5736	Approved
0.6348	Remote Similarity	NPD1086	Approved
0.6348	Remote Similarity	NPD1090	Approved
0.6348	Remote Similarity	NPD1089	Approved
0.6338	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD9545	Approved
0.6333	Remote Similarity	NPD3020	Approved
0.6328	Remote Similarity	NPD2652	Approved
0.6328	Remote Similarity	NPD2650	Approved
0.6328	Remote Similarity	NPD6010	Discontinued
0.6325	Remote Similarity	NPD3719	Approved
0.6325	Remote Similarity	NPD3718	Approved
0.6324	Remote Similarity	NPD6362	Approved
0.6316	Remote Similarity	NPD3496	Discontinued
0.6306	Remote Similarity	NPD3971	Phase 1
0.6304	Remote Similarity	NPD2613	Approved
0.6301	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD4628	Phase 3
0.6296	Remote Similarity	NPD3685	Discontinued
0.629	Remote Similarity	NPD3134	Approved
0.6284	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD226	Approved
0.6259	Remote Similarity	NPD6190	Approved
0.625	Remote Similarity	NPD7137	Phase 2
0.6242	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD4060	Phase 1
0.6239	Remote Similarity	NPD1088	Approved
0.6234	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6232	Remote Similarity	NPD3662	Phase 3
0.6232	Remote Similarity	NPD3664	Approved
0.6232	Remote Similarity	NPD3663	Approved
0.6232	Remote Similarity	NPD3661	Approved
0.6231	Remote Similarity	NPD7157	Approved
0.623	Remote Similarity	NPD846	Approved
0.623	Remote Similarity	NPD940	Approved
0.6225	Remote Similarity	NPD7239	Suspended
0.6222	Remote Similarity	NPD6637	Approved
0.6218	Remote Similarity	NPD2860	Approved
0.6218	Remote Similarity	NPD2859	Approved
0.6218	Remote Similarity	NPD7075	Discontinued
0.6218	Remote Similarity	NPD1989	Approved
0.6214	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6798	Discontinued
0.6214	Remote Similarity	NPD3268	Approved
0.6212	Remote Similarity	NPD4479	Discontinued
0.6211	Remote Similarity	NPD7799	Discontinued
0.6207	Remote Similarity	NPD7838	Discovery
0.6204	Remote Similarity	NPD2160	Approved
0.6204	Remote Similarity	NPD2626	Approved
0.6204	Remote Similarity	NPD2627	Approved
0.6204	Remote Similarity	NPD2628	Approved
0.6204	Remote Similarity	NPD2625	Approved
0.6204	Remote Similarity	NPD2159	Approved
0.6204	Remote Similarity	NPD2797	Approved
0.6197	Remote Similarity	NPD4340	Discontinued
0.6194	Remote Similarity	NPD4136	Approved
0.6194	Remote Similarity	NPD4135	Approved
0.6194	Remote Similarity	NPD4106	Approved
0.619	Remote Similarity	NPD2182	Approved
0.619	Remote Similarity	NPD2575	Approved
0.619	Remote Similarity	NPD2684	Approved
0.6187	Remote Similarity	NPD4908	Phase 1
0.6186	Remote Similarity	NPD845	Approved
0.6181	Remote Similarity	NPD7305	Phase 1
0.617	Remote Similarity	NPD3615	Approved
0.617	Remote Similarity	NPD4746	Phase 3
0.617	Remote Similarity	NPD2566	Approved
0.617	Remote Similarity	NPD3090	Approved
0.617	Remote Similarity	NPD2571	Approved
0.617	Remote Similarity	NPD3616	Approved
0.617	Remote Similarity	NPD3088	Approved
0.617	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.617	Remote Similarity	NPD3089	Approved
0.617	Remote Similarity	NPD3087	Approved
0.617	Remote Similarity	NPD2573	Approved
0.617	Remote Similarity	NPD2574	Discontinued
0.617	Remote Similarity	NPD3614	Approved
0.617	Remote Similarity	NPD2570	Approved
0.617	Remote Similarity	NPD6233	Phase 2
0.617	Remote Similarity	NPD4745	Approved
0.617	Remote Similarity	NPD6663	Approved
0.6168	Remote Similarity	NPD9716	Approved
0.6164	Remote Similarity	NPD2424	Discontinued
0.6161	Remote Similarity	NPD9491	Approved
0.6159	Remote Similarity	NPD5403	Approved
0.6159	Remote Similarity	NPD2798	Approved
0.6159	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD2788	Approved
0.6159	Remote Similarity	NPD5647	Approved
0.6148	Remote Similarity	NPD4216	Approved
0.6148	Remote Similarity	NPD2611	Approved
0.6148	Remote Similarity	NPD2612	Approved
0.6148	Remote Similarity	NPD2609	Approved
0.6148	Remote Similarity	NPD2608	Approved
0.6148	Remote Similarity	NPD4215	Approved
0.6148	Remote Similarity	NPD3132	Approved
0.6148	Remote Similarity	NPD4217	Approved
0.6148	Remote Similarity	NPD2610	Approved
0.6148	Remote Similarity	NPD422	Phase 1
0.6148	Remote Similarity	NPD3131	Approved
0.6148	Remote Similarity	NPD4218	Approved
0.6143	Remote Similarity	NPD3027	Phase 3
0.6143	Remote Similarity	NPD7095	Approved
0.6142	Remote Similarity	NPD1317	Discontinued
0.6142	Remote Similarity	NPD4750	Phase 3
0.6134	Remote Similarity	NPD6049	Phase 2
0.6134	Remote Similarity	NPD2933	Approved
0.6134	Remote Similarity	NPD2934	Approved
0.6134	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD4814	Discontinued
0.6133	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD4626	Approved
0.6119	Remote Similarity	NPD1778	Approved
0.6116	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6115	Remote Similarity	NPD2861	Phase 2
0.6115	Remote Similarity	NPD5204	Approved
0.6111	Remote Similarity	NPD7097	Phase 1
0.6111	Remote Similarity	NPD9532	Phase 3
0.6111	Remote Similarity	NPD290	Approved
0.6111	Remote Similarity	NPD1358	Approved
0.6103	Remote Similarity	NPD1608	Approved
0.6099	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD3764	Approved
0.6099	Remote Similarity	NPD6410	Clinical (unspecified phase)

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