NPASS Compound

Structure

NPC475045 OpenBabel07101719512D 35 35 0 0 1 0 0 0 0 0999 V2000 -2.3660 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1340 -3.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6340 -4.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6340 -1.0981 0.0000 C 0 0 0 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 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1340 -0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 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 0.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6340 -2.8301 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1340 -3.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 -1.0981 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 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 -2.8301 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 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 3.1340 -1.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1340 -3.6962 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 2.1340 -1.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 29 1 0 0 0 0 7 34 1 0 0 0 0 8 29 1 0 0 0 0 9 11 1 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 21 1 0 0 0 0 12 21 2 0 0 0 0 13 22 2 0 0 0 0 14 15 1 0 0 0 0 14 24 2 0 0 0 0 15 26 2 0 0 0 0 16 29 1 0 0 0 0 17 20 2 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 19 27 1 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 24 30 1 0 0 0 0 25 28 1 0 0 0 0 25 31 1 6 0 0 0 26 35 1 0 0 0 0 27 32 2 0 0 0 0 27 34 1 0 0 0 0 28 33 2 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.28
Volume:	530.597
LogP:	4.351
LogD:	4.505
LogS:	-5.156
# Rotatable Bonds:	16
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.144
Synthetic Accessibility Score:	4.139
Fsp3:	0.483
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.689
MDCK Permeability:	2.2530077330884524e-05
Pgp-inhibitor:	0.98
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.903

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.048
Plasma Protein Binding (PPB):	99.7867660522461%
Volume Distribution (VD):	0.247
Pgp-substrate:	0.8610196113586426%

ADMET: Metabolism

CYP1A2-inhibitor:	0.135
CYP1A2-substrate:	0.479
CYP2C19-inhibitor:	0.779
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.897
CYP2C9-substrate:	0.94
CYP2D6-inhibitor:	0.696
CYP2D6-substrate:	0.715
CYP3A4-inhibitor:	0.962
CYP3A4-substrate:	0.515

ADMET: Excretion

Clearance (CL):	8.974
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.292
Drug-inuced Liver Injury (DILI):	0.197
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.175
Maximum Recommended Daily Dose:	0.835
Skin Sensitization:	0.887
Carcinogencity:	0.677
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.4

Download Data

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

Natural Product: NPC475045

Natural Product ID:	NPC475045
*Common Name:**	Methyl 2-[5-Hydroxy-2-[(6E,10E,13S)-13-Hydroxy-3,7,11,15-Tetramethyl-12-Oxohexadeca-1,6,10,14-Tetraen-3-Yl]Oxyphenyl]Acetate
IUPAC Name:	methyl 2-[5-hydroxy-2-[(6E,10E,13S)-13-hydroxy-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,10,14-tetraen-3-yl]oxyphenyl]acetate
Synonyms:
Standard InCHIKey:	ZMYIWCZPWCZTCD-XNUXHYDJSA-N
Standard InCHI:	InChI=1S/C29H40O6/c1-8-29(6,35-26-15-14-24(30)18-23(26)19-27(32)34-7)16-10-12-21(4)11-9-13-22(5)28(33)25(31)17-20(2)3/h8,12-15,17-18,25,30-31H,1,9-11,16,19H2,2-7H3/b21-12+,22-13+/t25-,29?/m0/s1
SMILES:	CC(=CC(C(=O)C(=CCCC(=CCCC(C)(C=C)OC1=C(C=C(C=C1)O)CC(=O)OC)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494286
PubChem CID:	25136072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921416]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	subtidal zone (0-2 m) off the southwestern shore of Jeju Island, Korea	2003-Apr	PMID[18817444]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19006667]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377877]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28720331]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	50.0	ug.mL-1	PMID[506627]
NPT2	Others	Unspecified		IC50	>	200.0	ug.mL-1	PMID[506627]
NPT1	Others	Radical scavenging activity		RC50	=	12.55	ug ml-1	PMID[506627]

☑ 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 NPC475045 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	299
0.1-0.2	1304
0.2-0.3	3415
0.3-0.4	7774
0.4-0.5	10500
0.5-0.6	4453
0.6-0.7	7522
0.7-0.8	7239
0.8-0.85	167
0.85-0.9	13
0.9-0.95	4
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC474943
0.9924	High Similarity	NPC475005
0.9776	High Similarity	NPC475063
0.9776	High Similarity	NPC475044
0.9627	High Similarity	NPC476025
0.9627	High Similarity	NPC475028
0.9403	High Similarity	NPC476018
0.9403	High Similarity	NPC475029
0.9403	High Similarity	NPC475011
0.927	High Similarity	NPC475012
0.8889	High Similarity	NPC163169
0.8889	High Similarity	NPC123
0.8603	High Similarity	NPC476024
0.8551	High Similarity	NPC474143
0.8551	High Similarity	NPC474246
0.854	High Similarity	NPC59654
0.854	High Similarity	NPC271832
0.8529	High Similarity	NPC477211
0.8529	High Similarity	NPC477212
0.8529	High Similarity	NPC319422
0.8529	High Similarity	NPC477214
0.85	High Similarity	NPC477210
0.8489	Intermediate Similarity	NPC329427
0.8489	Intermediate Similarity	NPC317601
0.8478	Intermediate Similarity	NPC475880
0.8472	Intermediate Similarity	NPC164599
0.8472	Intermediate Similarity	NPC184053
0.8456	Intermediate Similarity	NPC474944
0.8429	Intermediate Similarity	NPC470871
0.8425	Intermediate Similarity	NPC89664
0.8425	Intermediate Similarity	NPC274085
0.8394	Intermediate Similarity	NPC95034
0.8394	Intermediate Similarity	NPC142087
0.8392	Intermediate Similarity	NPC98395
0.8382	Intermediate Similarity	NPC477213
0.8367	Intermediate Similarity	NPC98356
0.8356	Intermediate Similarity	NPC473090
0.8333	Intermediate Similarity	NPC201419
0.8322	Intermediate Similarity	NPC73411
0.8322	Intermediate Similarity	NPC215711
0.8321	Intermediate Similarity	NPC474945
0.8321	Intermediate Similarity	NPC476022
0.8321	Intermediate Similarity	NPC475236
0.8309	Intermediate Similarity	NPC221798
0.8299	Intermediate Similarity	NPC477409
0.8299	Intermediate Similarity	NPC469683
0.8289	Intermediate Similarity	NPC301233
0.8288	Intermediate Similarity	NPC474154
0.8288	Intermediate Similarity	NPC229916
0.8255	Intermediate Similarity	NPC472036
0.8255	Intermediate Similarity	NPC472969
0.8255	Intermediate Similarity	NPC210320
0.8235	Intermediate Similarity	NPC99381
0.8231	Intermediate Similarity	NPC469615
0.8224	Intermediate Similarity	NPC34965
0.8224	Intermediate Similarity	NPC183536
0.8212	Intermediate Similarity	NPC475890
0.8201	Intermediate Similarity	NPC2596
0.8201	Intermediate Similarity	NPC473744
0.82	Intermediate Similarity	NPC98809
0.82	Intermediate Similarity	NPC476394
0.8194	Intermediate Similarity	NPC57072
0.8194	Intermediate Similarity	NPC121243
0.8194	Intermediate Similarity	NPC240147
0.8194	Intermediate Similarity	NPC231475
0.8188	Intermediate Similarity	NPC308799
0.8188	Intermediate Similarity	NPC472033
0.8182	Intermediate Similarity	NPC233350
0.8182	Intermediate Similarity	NPC182217
0.8182	Intermediate Similarity	NPC70680
0.8176	Intermediate Similarity	NPC213900
0.8176	Intermediate Similarity	NPC469642
0.8176	Intermediate Similarity	NPC105381
0.8176	Intermediate Similarity	NPC10302
0.817	Intermediate Similarity	NPC84721
0.8169	Intermediate Similarity	NPC129889
0.8169	Intermediate Similarity	NPC307006
0.8163	Intermediate Similarity	NPC474385
0.8162	Intermediate Similarity	NPC132518
0.8162	Intermediate Similarity	NPC477151
0.8162	Intermediate Similarity	NPC291189
0.8162	Intermediate Similarity	NPC69403
0.8156	Intermediate Similarity	NPC473777
0.8151	Intermediate Similarity	NPC477537
0.8151	Intermediate Similarity	NPC477535
0.8138	Intermediate Similarity	NPC221046
0.8133	Intermediate Similarity	NPC4958
0.8133	Intermediate Similarity	NPC83975
0.8133	Intermediate Similarity	NPC98009
0.8133	Intermediate Similarity	NPC92054
0.8133	Intermediate Similarity	NPC66991
0.8133	Intermediate Similarity	NPC140722
0.8133	Intermediate Similarity	NPC113428
0.8133	Intermediate Similarity	NPC61284
0.8129	Intermediate Similarity	NPC474401
0.8129	Intermediate Similarity	NPC474398
0.8129	Intermediate Similarity	NPC121104
0.8129	Intermediate Similarity	NPC71525
0.8129	Intermediate Similarity	NPC476026
0.8129	Intermediate Similarity	NPC474441
0.8125	Intermediate Similarity	NPC278832
0.8125	Intermediate Similarity	NPC64230
0.8125	Intermediate Similarity	NPC71638
0.8125	Intermediate Similarity	NPC64157
0.8121	Intermediate Similarity	NPC472034
0.8117	Intermediate Similarity	NPC237560
0.8113	Intermediate Similarity	NPC471823
0.8112	Intermediate Similarity	NPC68517
0.8108	Intermediate Similarity	NPC472006
0.8108	Intermediate Similarity	NPC476164
0.8108	Intermediate Similarity	NPC476310
0.8108	Intermediate Similarity	NPC51106
0.8106	Intermediate Similarity	NPC322358
0.8105	Intermediate Similarity	NPC19380
0.8105	Intermediate Similarity	NPC474843
0.8105	Intermediate Similarity	NPC146277
0.8099	Intermediate Similarity	NPC302844
0.8099	Intermediate Similarity	NPC118253
0.8095	Intermediate Similarity	NPC471444
0.8095	Intermediate Similarity	NPC257003
0.8092	Intermediate Similarity	NPC37348
0.8092	Intermediate Similarity	NPC61258
0.8089	Intermediate Similarity	NPC3629
0.8088	Intermediate Similarity	NPC476165
0.8085	Intermediate Similarity	NPC109778
0.8085	Intermediate Similarity	NPC327457
0.8085	Intermediate Similarity	NPC86774
0.8082	Intermediate Similarity	NPC303683
0.8082	Intermediate Similarity	NPC26241
0.8082	Intermediate Similarity	NPC216312
0.8082	Intermediate Similarity	NPC474875
0.8082	Intermediate Similarity	NPC29771
0.8082	Intermediate Similarity	NPC295492
0.8082	Intermediate Similarity	NPC473988
0.8082	Intermediate Similarity	NPC471602
0.8082	Intermediate Similarity	NPC111422
0.8082	Intermediate Similarity	NPC476820
0.8082	Intermediate Similarity	NPC299405
0.8082	Intermediate Similarity	NPC205751
0.8082	Intermediate Similarity	NPC274891
0.8082	Intermediate Similarity	NPC256463
0.8082	Intermediate Similarity	NPC476819
0.8082	Intermediate Similarity	NPC306835
0.8082	Intermediate Similarity	NPC476477
0.8079	Intermediate Similarity	NPC471641
0.8079	Intermediate Similarity	NPC471642
0.8079	Intermediate Similarity	NPC240622
0.8079	Intermediate Similarity	NPC240253
0.8079	Intermediate Similarity	NPC228012
0.8067	Intermediate Similarity	NPC286038
0.8067	Intermediate Similarity	NPC474422
0.8067	Intermediate Similarity	NPC107625
0.8065	Intermediate Similarity	NPC473275
0.8065	Intermediate Similarity	NPC470896
0.8058	Intermediate Similarity	NPC110211
0.8058	Intermediate Similarity	NPC204579
0.8056	Intermediate Similarity	NPC298900
0.8056	Intermediate Similarity	NPC139519
0.8056	Intermediate Similarity	NPC51087
0.8056	Intermediate Similarity	NPC161856
0.8056	Intermediate Similarity	NPC291119
0.8056	Intermediate Similarity	NPC281169
0.8054	Intermediate Similarity	NPC277426
0.8054	Intermediate Similarity	NPC210425
0.8054	Intermediate Similarity	NPC280404
0.8054	Intermediate Similarity	NPC113397
0.8054	Intermediate Similarity	NPC86373
0.8052	Intermediate Similarity	NPC193200
0.805	Intermediate Similarity	NPC280923
0.8043	Intermediate Similarity	NPC474237
0.8041	Intermediate Similarity	NPC242756
0.8039	Intermediate Similarity	NPC93498
0.8039	Intermediate Similarity	NPC75695
0.8039	Intermediate Similarity	NPC48671
0.8039	Intermediate Similarity	NPC163883
0.803	Intermediate Similarity	NPC197513
0.8029	Intermediate Similarity	NPC49441
0.8028	Intermediate Similarity	NPC15083
0.8027	Intermediate Similarity	NPC147542
0.8027	Intermediate Similarity	NPC32749
0.8027	Intermediate Similarity	NPC327916
0.8027	Intermediate Similarity	NPC42262
0.8027	Intermediate Similarity	NPC37992
0.8027	Intermediate Similarity	NPC326065
0.8027	Intermediate Similarity	NPC241349
0.8027	Intermediate Similarity	NPC220496
0.8026	Intermediate Similarity	NPC266499
0.8026	Intermediate Similarity	NPC4423
0.8026	Intermediate Similarity	NPC223988
0.8026	Intermediate Similarity	NPC473091
0.8026	Intermediate Similarity	NPC77325
0.8025	Intermediate Similarity	NPC471976
0.8014	Intermediate Similarity	NPC142703
0.8014	Intermediate Similarity	NPC152942
0.8014	Intermediate Similarity	NPC278068
0.8014	Intermediate Similarity	NPC37250
0.8014	Intermediate Similarity	NPC325625
0.8014	Intermediate Similarity	NPC302857
0.8014	Intermediate Similarity	NPC284409
0.8014	Intermediate Similarity	NPC219428

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 NPC475045 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	266
0.1-0.2	871
0.2-0.3	1794
0.3-0.4	2414
0.4-0.5	1975
0.5-0.6	1146
0.6-0.7	529
0.7-0.8	154
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8148	Intermediate Similarity	NPD3496	Discontinued
0.8117	Intermediate Similarity	NPD5402	Approved
0.8027	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD4628	Phase 3
0.7958	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD1778	Approved
0.7899	Intermediate Similarity	NPD1608	Approved
0.7898	Intermediate Similarity	NPD7075	Discontinued
0.7877	Intermediate Similarity	NPD7033	Discontinued
0.7852	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD2935	Discontinued
0.7821	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD6799	Approved
0.78	Intermediate Similarity	NPD6190	Approved
0.7794	Intermediate Similarity	NPD9545	Approved
0.7763	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD3882	Suspended
0.7711	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD7819	Suspended
0.7707	Intermediate Similarity	NPD2801	Approved
0.7704	Intermediate Similarity	NPD6671	Approved
0.7681	Intermediate Similarity	NPD17	Approved
0.7677	Intermediate Similarity	NPD3226	Approved
0.7671	Intermediate Similarity	NPD6355	Discontinued
0.7671	Intermediate Similarity	NPD447	Suspended
0.7662	Intermediate Similarity	NPD5403	Approved
0.7658	Intermediate Similarity	NPD3817	Phase 2
0.7655	Intermediate Similarity	NPD6233	Phase 2
0.7651	Intermediate Similarity	NPD6002	Phase 3
0.7651	Intermediate Similarity	NPD6004	Phase 3
0.7651	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6005	Phase 3
0.7643	Intermediate Similarity	NPD6801	Discontinued
0.7643	Intermediate Similarity	NPD9717	Approved
0.76	Intermediate Similarity	NPD1549	Phase 2
0.76	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6798	Discontinued
0.7586	Intermediate Similarity	NPD3268	Approved
0.7586	Intermediate Similarity	NPD2313	Discontinued
0.7584	Intermediate Similarity	NPD1551	Phase 2
0.7584	Intermediate Similarity	NPD6100	Approved
0.7584	Intermediate Similarity	NPD6099	Approved
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7569	Intermediate Similarity	NPD6832	Phase 2
0.7558	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD230	Phase 1
0.7533	Intermediate Similarity	NPD2346	Discontinued
0.7533	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6844	Discontinued
0.7532	Intermediate Similarity	NPD2534	Approved
0.7532	Intermediate Similarity	NPD2533	Approved
0.7532	Intermediate Similarity	NPD1934	Approved
0.7532	Intermediate Similarity	NPD2532	Approved
0.7532	Intermediate Similarity	NPD5401	Approved
0.7518	Intermediate Similarity	NPD1481	Phase 2
0.7517	Intermediate Similarity	NPD2799	Discontinued
0.7516	Intermediate Similarity	NPD6599	Discontinued
0.7515	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD6653	Approved
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1512	Approved
0.7483	Intermediate Similarity	NPD1203	Approved
0.7483	Intermediate Similarity	NPD2797	Approved
0.7471	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7411	Suspended
0.7467	Intermediate Similarity	NPD2796	Approved
0.7466	Intermediate Similarity	NPD411	Approved
0.7466	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1535	Discovery
0.744	Intermediate Similarity	NPD7251	Discontinued
0.7432	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5647	Approved
0.7427	Intermediate Similarity	NPD8434	Phase 2
0.7426	Intermediate Similarity	NPD1241	Discontinued
0.7417	Intermediate Similarity	NPD5763	Approved
0.7417	Intermediate Similarity	NPD5762	Approved
0.7417	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD3225	Approved
0.741	Intermediate Similarity	NPD3818	Discontinued
0.7405	Intermediate Similarity	NPD4380	Phase 2
0.74	Intermediate Similarity	NPD4308	Phase 3
0.74	Intermediate Similarity	NPD1510	Phase 2
0.7396	Intermediate Similarity	NPD7808	Phase 3
0.7381	Intermediate Similarity	NPD6797	Phase 2
0.7379	Intermediate Similarity	NPD2861	Phase 2
0.7378	Intermediate Similarity	NPD3787	Discontinued
0.7365	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1240	Approved
0.7365	Intermediate Similarity	NPD7054	Approved
0.7365	Intermediate Similarity	NPD4060	Phase 1
0.7355	Intermediate Similarity	NPD1511	Approved
0.7355	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD3887	Approved
0.7329	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD422	Phase 1
0.7321	Intermediate Similarity	NPD7472	Approved
0.7321	Intermediate Similarity	NPD7074	Phase 3
0.731	Intermediate Similarity	NPD1019	Discontinued
0.7308	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2344	Approved
0.7297	Intermediate Similarity	NPD4062	Phase 3
0.7292	Intermediate Similarity	NPD6696	Suspended
0.7284	Intermediate Similarity	NPD7768	Phase 2
0.7279	Intermediate Similarity	NPD7095	Approved
0.7278	Intermediate Similarity	NPD1653	Approved
0.7267	Intermediate Similarity	NPD1607	Approved
0.7266	Intermediate Similarity	NPD9493	Approved
0.726	Intermediate Similarity	NPD9494	Approved
0.7256	Intermediate Similarity	NPD5494	Approved
0.7251	Intermediate Similarity	NPD8312	Approved
0.7251	Intermediate Similarity	NPD8313	Approved
0.7241	Intermediate Similarity	NPD3267	Approved
0.7241	Intermediate Similarity	NPD6362	Approved
0.7241	Intermediate Similarity	NPD3266	Approved
0.7239	Intermediate Similarity	NPD3749	Approved
0.7237	Intermediate Similarity	NPD6032	Approved
0.7234	Intermediate Similarity	NPD5585	Approved
0.723	Intermediate Similarity	NPD3764	Approved
0.7226	Intermediate Similarity	NPD2354	Approved
0.7225	Intermediate Similarity	NPD8150	Discontinued
0.7215	Intermediate Similarity	NPD920	Approved
0.7203	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5124	Phase 1
0.7197	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3146	Approved
0.7186	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4626	Approved
0.7171	Intermediate Similarity	NPD3748	Approved
0.717	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD1894	Discontinued
0.716	Intermediate Similarity	NPD7286	Phase 2
0.7152	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6386	Approved
0.7143	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7143	Intermediate Similarity	NPD6385	Approved
0.7143	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6559	Discontinued
0.7135	Intermediate Similarity	NPD7685	Pre-registration
0.7133	Intermediate Similarity	NPD4307	Phase 2
0.7125	Intermediate Similarity	NPD7458	Discontinued
0.7115	Intermediate Similarity	NPD2309	Approved
0.7114	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7985	Registered
0.7113	Intermediate Similarity	NPD5691	Approved
0.7108	Intermediate Similarity	NPD1247	Approved
0.7108	Intermediate Similarity	NPD8127	Discontinued
0.7108	Intermediate Similarity	NPD6959	Discontinued
0.7105	Intermediate Similarity	NPD7097	Phase 1
0.7101	Intermediate Similarity	NPD7177	Discontinued
0.7101	Intermediate Similarity	NPD2163	Approved
0.7097	Intermediate Similarity	NPD2800	Approved
0.7091	Intermediate Similarity	NPD919	Approved
0.7089	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1091	Approved
0.7078	Intermediate Similarity	NPD2353	Approved
0.7078	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD5953	Discontinued
0.7075	Intermediate Similarity	NPD2798	Approved
0.707	Intermediate Similarity	NPD7440	Discontinued
0.7066	Intermediate Similarity	NPD7229	Phase 3
0.7066	Intermediate Similarity	NPD6232	Discontinued
0.7055	Intermediate Similarity	NPD1465	Phase 2
0.7055	Intermediate Similarity	NPD8455	Phase 2
0.7044	Intermediate Similarity	NPD5049	Phase 3
0.7037	Intermediate Similarity	NPD3134	Approved
0.7037	Intermediate Similarity	NPD968	Approved
0.7019	Intermediate Similarity	NPD2651	Approved
0.7019	Intermediate Similarity	NPD2649	Approved
0.7013	Intermediate Similarity	NPD4476	Approved
0.7013	Intermediate Similarity	NPD4477	Approved
0.7013	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1652	Phase 2
0.6987	Remote Similarity	NPD1243	Approved
0.6986	Remote Similarity	NPD4359	Approved
0.6986	Remote Similarity	NPD4749	Approved
0.6986	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD290	Approved
0.6985	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1358	Approved
0.6982	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6778	Approved
0.6978	Remote Similarity	NPD6776	Approved
0.6978	Remote Similarity	NPD6779	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