NPASS Compound

Structure

NPC163169 OpenBabel07101718322D 35 35 0 0 1 0 0 0 0 0999 V2000 -4.3301 -11.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 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 -2.5981 -8.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -8.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -10.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -10.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -10.0000 0.0000 C 0 0 0 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -11.5000 0.0000 O 0 0 0 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 -0.8660 -10.5000 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 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 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 35 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 20 2 0 0 0 0 10 21 1 0 0 0 0 11 20 1 0 0 0 0 12 22 2 0 0 0 0 13 14 1 0 0 0 0 13 21 2 0 0 0 0 14 23 1 0 0 0 0 15 19 2 0 0 0 0 15 26 1 0 0 0 0 16 23 1 0 0 0 0 16 25 2 0 0 0 0 17 24 2 0 0 0 0 17 25 1 0 0 0 0 18 24 1 0 0 0 0 18 27 1 0 0 0 0 22 28 1 0 0 0 0 23 29 2 0 0 0 0 24 29 1 0 0 0 0 25 30 1 0 0 0 0 26 28 1 0 0 0 0 26 31 1 1 0 0 0 27 32 2 0 0 0 0 27 35 1 0 0 0 0 28 33 2 0 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	484.28
Volume:	530.597
LogP:	4.365
LogD:	4.352
LogS:	-5.157
# Rotatable Bonds:	15
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.114
Synthetic Accessibility Score:	3.834
Fsp3:	0.483
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.77
MDCK Permeability:	2.7483627491164953e-05
Pgp-inhibitor:	0.59
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.063
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	98.65699005126953%
Volume Distribution (VD):	0.208
Pgp-substrate:	0.6126886010169983%

ADMET: Metabolism

CYP1A2-inhibitor:	0.219
CYP1A2-substrate:	0.332
CYP2C19-inhibitor:	0.754
CYP2C19-substrate:	0.315
CYP2C9-inhibitor:	0.93
CYP2C9-substrate:	0.984
CYP2D6-inhibitor:	0.746
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.899
CYP3A4-substrate:	0.266

ADMET: Excretion

Clearance (CL):	9.367
Half-life (T1/2):	0.934

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.304
Drug-inuced Liver Injury (DILI):	0.14
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.124
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.946
Carcinogencity:	0.102
Eye Corrosion:	0.003
Eye Irritation:	0.043
Respiratory Toxicity:	0.445

Download Data

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

Natural Product: NPC163169

Natural Product ID:	NPC163169
*Common Name:**	Methyl 2-(2,5-Dihydroxy-3-((S,2E,6E,10E)-13-Hydroxy-3,7,11,15-Tetramethyl-12-Oxohexadeca-2,6,10,14-Tetraenyl)Phenyl)Acetate
IUPAC Name:	methyl 2-[2,5-dihydroxy-3-[(2E,6E,10E,13S)-13-hydroxy-3,7,11,15-tetramethyl-12-oxohexadeca-2,6,10,14-tetraenyl]phenyl]acetate
Synonyms:
Standard InCHIKey:	FNUGYZQRFXZSJL-GZRHGYSKSA-N
Standard InCHI:	InChI=1S/C29H40O6/c1-19(2)15-26(31)28(33)22(5)12-8-11-20(3)9-7-10-21(4)13-14-23-16-25(30)17-24(29(23)34)18-27(32)35-6/h9,12-13,15-17,26,30-31,34H,7-8,10-11,14,18H2,1-6H3/b20-9+,21-13+,22-12+/t26-/m0/s1
SMILES:	COC(=O)Cc1cc(O)cc(c1O)C/C=C(/CC/C=C(/CC/C=C(/C(=O)[C@H](C=C(C)C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491822
PubChem CID:	25136077
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	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	23.0	ug.mL-1	PMID[496157]
NPT1	Others	Radical scavenging activity		RC50	=	0.31	ug ml-1	PMID[496157]

☑ 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 NPC163169 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	265
0.1-0.2	1120
0.2-0.3	2946
0.3-0.4	7083
0.4-0.5	11737
0.5-0.6	5723
0.6-0.7	10770
0.7-0.8	2929
0.8-0.85	98
0.85-0.9	20
0.9-0.95	2
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC123
0.9677	High Similarity	NPC476024
0.9516	High Similarity	NPC474944
0.936	High Similarity	NPC476022
0.936	High Similarity	NPC474945
0.8889	High Similarity	NPC475045
0.8871	High Similarity	NPC476020
0.8824	High Similarity	NPC475063
0.8824	High Similarity	NPC475044
0.8815	High Similarity	NPC475005
0.8815	High Similarity	NPC474943
0.874	High Similarity	NPC475192
0.8676	High Similarity	NPC476025
0.8676	High Similarity	NPC475028
0.8657	High Similarity	NPC204582
0.8626	High Similarity	NPC473744
0.8618	High Similarity	NPC473931
0.8618	High Similarity	NPC474050
0.8618	High Similarity	NPC474114
0.8618	High Similarity	NPC114918
0.855	High Similarity	NPC319422
0.855	High Similarity	NPC477214
0.855	High Similarity	NPC477211
0.855	High Similarity	NPC477212
0.8537	High Similarity	NPC296144
0.8537	High Similarity	NPC28784
0.8529	High Similarity	NPC475111
0.8468	Intermediate Similarity	NPC197513
0.8462	Intermediate Similarity	NPC474803
0.8456	Intermediate Similarity	NPC475011
0.8433	Intermediate Similarity	NPC473777
0.8397	Intermediate Similarity	NPC477213
0.8357	Intermediate Similarity	NPC471444
0.8345	Intermediate Similarity	NPC306835
0.8345	Intermediate Similarity	NPC476477
0.8345	Intermediate Similarity	NPC216312
0.8345	Intermediate Similarity	NPC256463
0.8345	Intermediate Similarity	NPC299405
0.8345	Intermediate Similarity	NPC111422
0.8345	Intermediate Similarity	NPC471602
0.8345	Intermediate Similarity	NPC29771
0.8321	Intermediate Similarity	NPC475029
0.8321	Intermediate Similarity	NPC476018
0.8309	Intermediate Similarity	NPC239855
0.8293	Intermediate Similarity	NPC208229
0.8286	Intermediate Similarity	NPC147542
0.8286	Intermediate Similarity	NPC37992
0.8286	Intermediate Similarity	NPC241349
0.8286	Intermediate Similarity	NPC327916
0.8286	Intermediate Similarity	NPC32749
0.8286	Intermediate Similarity	NPC220496
0.8286	Intermediate Similarity	NPC42262
0.8281	Intermediate Similarity	NPC473767
0.8244	Intermediate Similarity	NPC477153
0.8235	Intermediate Similarity	NPC246693
0.8235	Intermediate Similarity	NPC110609
0.8235	Intermediate Similarity	NPC302844
0.8235	Intermediate Similarity	NPC242358
0.8227	Intermediate Similarity	NPC257003
0.8226	Intermediate Similarity	NPC228609
0.8214	Intermediate Similarity	NPC475012
0.8211	Intermediate Similarity	NPC26013
0.8211	Intermediate Similarity	NPC282855
0.8203	Intermediate Similarity	NPC474890
0.8203	Intermediate Similarity	NPC161943
0.8203	Intermediate Similarity	NPC273282
0.8189	Intermediate Similarity	NPC83718
0.8182	Intermediate Similarity	NPC184219
0.8169	Intermediate Similarity	NPC474300
0.8168	Intermediate Similarity	NPC67300
0.8138	Intermediate Similarity	NPC5568
0.813	Intermediate Similarity	NPC68260
0.813	Intermediate Similarity	NPC279887
0.812	Intermediate Similarity	NPC472592
0.812	Intermediate Similarity	NPC287473
0.8112	Intermediate Similarity	NPC476473
0.8092	Intermediate Similarity	NPC472892
0.8092	Intermediate Similarity	NPC31936
0.8082	Intermediate Similarity	NPC94781
0.806	Intermediate Similarity	NPC473751
0.806	Intermediate Similarity	NPC204579
0.806	Intermediate Similarity	NPC110211
0.8058	Intermediate Similarity	NPC233350
0.8058	Intermediate Similarity	NPC70859
0.8058	Intermediate Similarity	NPC61153
0.8058	Intermediate Similarity	NPC130899
0.8058	Intermediate Similarity	NPC182217
0.8058	Intermediate Similarity	NPC283590
0.8058	Intermediate Similarity	NPC70680
0.8056	Intermediate Similarity	NPC274085
0.8056	Intermediate Similarity	NPC89664
0.8056	Intermediate Similarity	NPC477409
0.8054	Intermediate Similarity	NPC470408
0.8054	Intermediate Similarity	NPC182921
0.8054	Intermediate Similarity	NPC218870
0.8054	Intermediate Similarity	NPC474824
0.8045	Intermediate Similarity	NPC117794
0.8043	Intermediate Similarity	NPC477280
0.8043	Intermediate Similarity	NPC19719
0.8043	Intermediate Similarity	NPC477281
0.803	Intermediate Similarity	NPC49441
0.803	Intermediate Similarity	NPC132518
0.803	Intermediate Similarity	NPC477151
0.803	Intermediate Similarity	NPC297193
0.8029	Intermediate Similarity	NPC474246
0.8029	Intermediate Similarity	NPC474143
0.8028	Intermediate Similarity	NPC315578
0.8028	Intermediate Similarity	NPC469911
0.8028	Intermediate Similarity	NPC3218
0.8027	Intermediate Similarity	NPC44378
0.8027	Intermediate Similarity	NPC120171
0.8027	Intermediate Similarity	NPC280753
0.8015	Intermediate Similarity	NPC278928
0.8015	Intermediate Similarity	NPC59654
0.8015	Intermediate Similarity	NPC271832
0.8014	Intermediate Similarity	NPC475974
0.8014	Intermediate Similarity	NPC112135
0.8	Intermediate Similarity	NPC209959
0.7986	Intermediate Similarity	NPC68517
0.7986	Intermediate Similarity	NPC354984
0.7985	Intermediate Similarity	NPC240744
0.7985	Intermediate Similarity	NPC167055
0.7984	Intermediate Similarity	NPC269414
0.7984	Intermediate Similarity	NPC160199
0.7973	Intermediate Similarity	NPC56204
0.7972	Intermediate Similarity	NPC244923
0.7972	Intermediate Similarity	NPC477277
0.7972	Intermediate Similarity	NPC477278
0.7971	Intermediate Similarity	NPC309430
0.7971	Intermediate Similarity	NPC327204
0.7971	Intermediate Similarity	NPC88864
0.7971	Intermediate Similarity	NPC323379
0.797	Intermediate Similarity	NPC275145
0.797	Intermediate Similarity	NPC174991
0.7959	Intermediate Similarity	NPC473719
0.7958	Intermediate Similarity	NPC114620
0.7958	Intermediate Similarity	NPC26241
0.7958	Intermediate Similarity	NPC476820
0.7958	Intermediate Similarity	NPC205751
0.7958	Intermediate Similarity	NPC26924
0.7958	Intermediate Similarity	NPC274891
0.7958	Intermediate Similarity	NPC295492
0.7958	Intermediate Similarity	NPC295339
0.7958	Intermediate Similarity	NPC476819
0.7958	Intermediate Similarity	NPC103337
0.7958	Intermediate Similarity	NPC303683
0.7958	Intermediate Similarity	NPC474875
0.7947	Intermediate Similarity	NPC474861
0.7943	Intermediate Similarity	NPC475957
0.7943	Intermediate Similarity	NPC149372
0.7943	Intermediate Similarity	NPC178467
0.7943	Intermediate Similarity	NPC194579
0.7943	Intermediate Similarity	NPC65837
0.7943	Intermediate Similarity	NPC474771
0.7943	Intermediate Similarity	NPC474849
0.7941	Intermediate Similarity	NPC24869
0.7931	Intermediate Similarity	NPC103910
0.7931	Intermediate Similarity	NPC29932
0.7929	Intermediate Similarity	NPC27407
0.7929	Intermediate Similarity	NPC142027
0.7926	Intermediate Similarity	NPC15837
0.7919	Intermediate Similarity	NPC205918
0.7914	Intermediate Similarity	NPC213485
0.7914	Intermediate Similarity	NPC78307
0.7914	Intermediate Similarity	NPC40524
0.7914	Intermediate Similarity	NPC471749
0.7914	Intermediate Similarity	NPC139074
0.7902	Intermediate Similarity	NPC477279
0.7899	Intermediate Similarity	NPC198249
0.7887	Intermediate Similarity	NPC61590
0.7887	Intermediate Similarity	NPC302857
0.7887	Intermediate Similarity	NPC9121
0.7887	Intermediate Similarity	NPC152942
0.7887	Intermediate Similarity	NPC142703
0.7887	Intermediate Similarity	NPC219428
0.7887	Intermediate Similarity	NPC278068
0.7887	Intermediate Similarity	NPC212693
0.7887	Intermediate Similarity	NPC94248
0.7887	Intermediate Similarity	NPC177307
0.7887	Intermediate Similarity	NPC472403
0.7887	Intermediate Similarity	NPC37250
0.7887	Intermediate Similarity	NPC191835
0.7879	Intermediate Similarity	NPC165197
0.7877	Intermediate Similarity	NPC75295
0.7877	Intermediate Similarity	NPC258856
0.7877	Intermediate Similarity	NPC474630
0.7868	Intermediate Similarity	NPC121104
0.7862	Intermediate Similarity	NPC143898
0.7857	Intermediate Similarity	NPC474097
0.7857	Intermediate Similarity	NPC202225
0.7857	Intermediate Similarity	NPC477210
0.7852	Intermediate Similarity	NPC315520
0.7852	Intermediate Similarity	NPC127975
0.7852	Intermediate Similarity	NPC131799
0.7852	Intermediate Similarity	NPC475407
0.7847	Intermediate Similarity	NPC472603
0.7847	Intermediate Similarity	NPC472604
0.7847	Intermediate Similarity	NPC472605
0.7847	Intermediate Similarity	NPC272907
0.7847	Intermediate Similarity	NPC184053

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 NPC163169 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	831
0.2-0.3	1696
0.3-0.4	2674
0.4-0.5	2084
0.5-0.6	1108
0.6-0.7	477
0.7-0.8	41
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
0.7692	Intermediate Similarity	NPD2935	Discontinued
0.7671	Intermediate Similarity	NPD6190	Approved
0.7652	Intermediate Similarity	NPD9545	Approved
0.7535	Intermediate Similarity	NPD230	Phase 1
0.7534	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7075	Discontinued
0.74	Intermediate Similarity	NPD2532	Approved
0.74	Intermediate Similarity	NPD2534	Approved
0.74	Intermediate Similarity	NPD2533	Approved
0.7355	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD1470	Approved
0.7308	Intermediate Similarity	NPD5402	Approved
0.7305	Intermediate Similarity	NPD8150	Discontinued
0.7285	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD4628	Phase 3
0.7248	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD9269	Phase 2
0.7244	Intermediate Similarity	NPD7819	Suspended
0.7239	Intermediate Similarity	NPD9493	Approved
0.7235	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD3496	Discontinued
0.7218	Intermediate Similarity	NPD2629	Approved
0.7208	Intermediate Similarity	NPD3226	Approved
0.7206	Intermediate Similarity	NPD9268	Approved
0.7179	Intermediate Similarity	NPD6801	Discontinued
0.7174	Intermediate Similarity	NPD1201	Approved
0.7163	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6004	Phase 3
0.7162	Intermediate Similarity	NPD6002	Phase 3
0.7162	Intermediate Similarity	NPD6005	Phase 3
0.7162	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4380	Phase 2
0.7152	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5844	Phase 1
0.7122	Intermediate Similarity	NPD1608	Approved
0.7114	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD943	Approved
0.7095	Intermediate Similarity	NPD5405	Approved
0.7095	Intermediate Similarity	NPD5404	Approved
0.7095	Intermediate Similarity	NPD5408	Approved
0.7095	Intermediate Similarity	NPD5406	Approved
0.7083	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3764	Approved
0.7083	Intermediate Similarity	NPD2313	Discontinued
0.7059	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2346	Discontinued
0.7041	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6663	Approved
0.7029	Intermediate Similarity	NPD1778	Approved
0.7029	Intermediate Similarity	NPD4626	Approved
0.7027	Intermediate Similarity	NPD7033	Discontinued
0.7027	Intermediate Similarity	NPD1510	Phase 2
0.7027	Intermediate Similarity	NPD2799	Discontinued
0.7023	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD9266	Approved
0.7023	Intermediate Similarity	NPD74	Approved
0.702	Intermediate Similarity	NPD8166	Discontinued
0.7012	Intermediate Similarity	NPD7473	Discontinued
0.7008	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7411	Suspended
0.6993	Remote Similarity	NPD7390	Discontinued
0.6993	Remote Similarity	NPD6799	Approved
0.6993	Remote Similarity	NPD5736	Approved
0.6987	Remote Similarity	NPD7458	Discontinued
0.6986	Remote Similarity	NPD1240	Approved
0.6984	Remote Similarity	NPD9495	Approved
0.6977	Remote Similarity	NPD1237	Approved
0.6972	Remote Similarity	NPD1164	Approved
0.6964	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD9263	Approved
0.6947	Remote Similarity	NPD9264	Approved
0.6947	Remote Similarity	NPD9267	Approved
0.694	Remote Similarity	NPD7635	Approved
0.6939	Remote Similarity	NPD6355	Discontinued
0.6937	Remote Similarity	NPD3882	Suspended
0.6933	Remote Similarity	NPD7266	Discontinued
0.6933	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6232	Discontinued
0.6928	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3300	Phase 2
0.6923	Remote Similarity	NPD5048	Discontinued
0.6919	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2801	Approved
0.6908	Remote Similarity	NPD3400	Discontinued
0.6906	Remote Similarity	NPD17	Approved
0.6899	Remote Similarity	NPD6647	Phase 2
0.6892	Remote Similarity	NPD1607	Approved
0.6887	Remote Similarity	NPD1549	Phase 2
0.6883	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3817	Phase 2
0.6875	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4060	Phase 1
0.6867	Remote Similarity	NPD6099	Approved
0.6867	Remote Similarity	NPD6100	Approved
0.6859	Remote Similarity	NPD5403	Approved
0.6855	Remote Similarity	NPD1934	Approved
0.6849	Remote Similarity	NPD3268	Approved
0.6849	Remote Similarity	NPD6798	Discontinued
0.6848	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6166	Phase 2
0.6842	Remote Similarity	NPD2067	Discontinued
0.6839	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD5691	Approved
0.6835	Remote Similarity	NPD6599	Discontinued
0.6833	Remote Similarity	NPD7435	Discontinued
0.6832	Remote Similarity	NPD7768	Phase 2
0.6825	Remote Similarity	NPD844	Approved
0.6824	Remote Similarity	NPD447	Suspended
0.6824	Remote Similarity	NPD8312	Approved
0.6824	Remote Similarity	NPD8313	Approved
0.6821	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5763	Approved
0.6821	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5762	Approved
0.6818	Remote Similarity	NPD7236	Approved
0.681	Remote Similarity	NPD5494	Approved
0.6803	Remote Similarity	NPD6233	Phase 2
0.6802	Remote Similarity	NPD8434	Phase 2
0.68	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD3750	Approved
0.679	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6671	Approved
0.6786	Remote Similarity	NPD2932	Approved
0.6786	Remote Similarity	NPD3019	Approved
0.6783	Remote Similarity	NPD1283	Approved
0.6783	Remote Similarity	NPD6696	Suspended
0.6779	Remote Similarity	NPD6651	Approved
0.6768	Remote Similarity	NPD6959	Discontinued
0.6766	Remote Similarity	NPD3818	Discontinued
0.6761	Remote Similarity	NPD9717	Approved
0.6761	Remote Similarity	NPD6534	Approved
0.6761	Remote Similarity	NPD6535	Approved
0.6759	Remote Similarity	NPD9494	Approved
0.6757	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2796	Approved
0.6755	Remote Similarity	NPD1551	Phase 2
0.6752	Remote Similarity	NPD920	Approved
0.675	Remote Similarity	NPD6844	Discontinued
0.675	Remote Similarity	NPD37	Approved
0.6747	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD7699	Phase 2
0.6742	Remote Similarity	NPD7700	Phase 2
0.6736	Remote Similarity	NPD2797	Approved
0.6732	Remote Similarity	NPD2800	Approved
0.6731	Remote Similarity	NPD5401	Approved
0.6731	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5711	Approved
0.6727	Remote Similarity	NPD5710	Approved
0.6726	Remote Similarity	NPD7286	Phase 2
0.6716	Remote Similarity	NPD4750	Phase 3
0.6715	Remote Similarity	NPD9281	Approved
0.6715	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1755	Approved
0.6712	Remote Similarity	NPD6832	Phase 2
0.6706	Remote Similarity	NPD7251	Discontinued
0.6706	Remote Similarity	NPD6559	Discontinued
0.669	Remote Similarity	NPD2798	Approved
0.669	Remote Similarity	NPD6085	Phase 2
0.669	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD4248	Discontinued
0.6688	Remote Similarity	NPD1512	Approved
0.6688	Remote Similarity	NPD7003	Approved
0.6687	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD845	Approved
0.6667	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD6781	Approved
0.6667	Remote Similarity	NPD6780	Approved
0.6667	Remote Similarity	NPD6778	Approved
0.6667	Remote Similarity	NPD6776	Approved
0.6667	Remote Similarity	NPD6777	Approved
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD7177	Discontinued
0.6667	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD6782	Approved
0.6667	Remote Similarity	NPD7808	Phase 3
0.6667	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6653	Approved
0.6648	Remote Similarity	NPD7698	Approved
0.6648	Remote Similarity	NPD7696	Phase 3
0.6648	Remote Similarity	NPD7697	Approved
0.6647	Remote Similarity	NPD6797	Phase 2
0.6647	Remote Similarity	NPD5953	Discontinued
0.6646	Remote Similarity	NPD919	Approved
0.6644	Remote Similarity	NPD826	Approved
0.6644	Remote Similarity	NPD825	Approved
0.6644	Remote Similarity	NPD2861	Phase 2
0.6644	Remote Similarity	NPD2979	Phase 3

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