NPASS Compound

Structure

CID110443 OpenBabel06191715462D 25 27 0 0 1 0 0 0 0 0999 V2000 3.4633 -3.0479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5392 -1.8884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0298 1.3669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5914 -0.4586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6308 0.0673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8920 -1.2124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8666 -1.1355 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4355 0.3503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0262 0.9937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6666 -2.1576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3277 -0.9153 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3705 -1.2910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4381 0.5582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3672 -0.5603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4801 -0.7768 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5476 1.0723 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0516 0.9168 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9929 0.3011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5905 0.6966 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3023 -2.2016 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7604 -1.7413 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5082 1.7077 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9929 -0.6121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5476 0.5582 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 10 2 0 0 0 0 2 10 1 0 0 0 0 4 5 1 0 0 0 0 4 11 1 0 0 0 0 5 13 2 0 0 0 0 6 11 1 0 0 0 0 6 12 1 0 0 0 0 7 12 1 0 0 0 0 8 14 1 0 0 0 0 8 19 1 0 0 0 0 9 19 1 0 0 0 0 11 10 1 6 0 0 0 12 20 2 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 21 2 0 0 0 0 15 7 1 6 0 0 0 15 25 1 0 0 0 0 16 9 1 6 0 0 0 16 17 1 0 0 0 0 16 24 1 0 0 0 0 17 22 1 1 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 3 1 1 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.16
Volume:	351.07
LogP:	1.56
LogD:	0.228
LogS:	-1.813
# Rotatable Bonds:	1
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.571
Synthetic Accessibility Score:	6.483
Fsp3:	0.632
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.765
MDCK Permeability:	2.8251046387595125e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.176
Human Intestinal Absorption (HIA):	0.144
20% Bioavailability (F20%):	0.119
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.134
Plasma Protein Binding (PPB):	48.130226135253906%
Volume Distribution (VD):	0.574
Pgp-substrate:	64.79773712158203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.253
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.619
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.344
CYP3A4-substrate:	0.331

ADMET: Excretion

Clearance (CL):	7.73
Half-life (T1/2):	0.855

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.839
Drug-inuced Liver Injury (DILI):	0.891
AMES Toxicity:	0.148
Rat Oral Acute Toxicity:	0.269
Maximum Recommended Daily Dose:	0.447
Skin Sensitization:	0.168
Carcinogencity:	0.194
Eye Corrosion:	0.036
Eye Irritation:	0.063
Respiratory Toxicity:	0.287

Download Data

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

Natural Product: NPC110443

Natural Product ID:	NPC110443
*Common Name:**	Scabrolide E
IUPAC Name:	n.a.
Synonyms:	Scabrolide E
Standard InCHIKey:	OFFWLZVJUHOBDO-JORPYXKZSA-N
Standard InCHI:	InChI=1S/C19H24O6/c1-10(2)11-4-5-13-17(22)16(24-18(13)23)9-19(3)8-14(21)15(25-19)7-12(20)6-11/h5,11,15-17,22H,1,4,6-9H2,2-3H3/b13-5-/t11-,15-,16+,17-,19-/m0/s1
SMILES:	O=C1C[C@H](C/C=C/2C(=O)O[C@H](C[C@]3(O[C@@H](C1)C(=O)C3)C)[C@H]2O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519725
PubChem CID:	11187132
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO2303	Sinularia scabra	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502336]
NPO2303	Sinularia scabra	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15620256]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24459770]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12662	Torilis japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12662	Torilis japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13208	Discaria americana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12662	Torilis japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25180	Sargassum fluitans	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3101	Primula deorum	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15747	Ryania speciosa	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15633	Maasella edwardsi	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13208	Discaria americana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7354	Aralia bipinnata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14023	Cicer judaicum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2303	Sinularia scabra	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16505	Angelica komarovii	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12662	Torilis japonica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12403	Microdesmis keayana	Species	Pandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14537	Manfreda tigrina	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16342	Schizanthus hookeri	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16157	Chaetomium amygdalisporum	Species	Chaetomiaceae	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
ED50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.7	ug ml-1	PMID[523073]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.5	ug ml-1	PMID[523073]

☑ 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 NPC110443 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	234
0.1-0.2	1269
0.2-0.3	4909
0.3-0.4	8928
0.4-0.5	14793
0.5-0.6	7482
0.6-0.7	3773
0.7-0.8	1174
0.8-0.85	115
0.85-0.9	12
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC133907
1.0	High Similarity	NPC128733
1.0	High Similarity	NPC185141
1.0	High Similarity	NPC46998
0.9355	High Similarity	NPC121825
0.9247	High Similarity	NPC469645
0.9247	High Similarity	NPC469692
0.9149	High Similarity	NPC469632
0.899	High Similarity	NPC472755
0.88	High Similarity	NPC475871
0.88	High Similarity	NPC475945
0.8788	High Similarity	NPC472753
0.8738	High Similarity	NPC38154
0.8713	High Similarity	NPC100487
0.87	High Similarity	NPC472754
0.87	High Similarity	NPC474747
0.87	High Similarity	NPC149371
0.8646	High Similarity	NPC81419
0.8646	High Similarity	NPC475912
0.8646	High Similarity	NPC179746
0.8617	High Similarity	NPC471047
0.8617	High Similarity	NPC469653
0.8617	High Similarity	NPC469628
0.8617	High Similarity	NPC469631
0.8617	High Similarity	NPC475906
0.86	High Similarity	NPC47880
0.86	High Similarity	NPC474339
0.86	High Similarity	NPC164598
0.86	High Similarity	NPC476270
0.86	High Similarity	NPC474742
0.86	High Similarity	NPC201718
0.8586	High Similarity	NPC471144
0.8544	High Similarity	NPC477513
0.8542	High Similarity	NPC261607
0.8542	High Similarity	NPC12172
0.8542	High Similarity	NPC300312
0.8542	High Similarity	NPC208886
0.8542	High Similarity	NPC111114
0.8529	High Similarity	NPC472756
0.8529	High Similarity	NPC474741
0.8519	High Similarity	NPC471145
0.8519	High Similarity	NPC471146
0.85	High Similarity	NPC288876
0.8469	Intermediate Similarity	NPC14961
0.8469	Intermediate Similarity	NPC270013
0.8469	Intermediate Similarity	NPC36954
0.8454	Intermediate Similarity	NPC273579
0.8454	Intermediate Similarity	NPC295204
0.8454	Intermediate Similarity	NPC162205
0.8454	Intermediate Similarity	NPC288240
0.8454	Intermediate Similarity	NPC475302
0.8431	Intermediate Similarity	NPC475873
0.8404	Intermediate Similarity	NPC261721
0.84	Intermediate Similarity	NPC187268
0.84	Intermediate Similarity	NPC141191
0.8367	Intermediate Similarity	NPC81386
0.8367	Intermediate Similarity	NPC474035
0.8351	Intermediate Similarity	NPC30515
0.8351	Intermediate Similarity	NPC184463
0.835	Intermediate Similarity	NPC203659
0.8333	Intermediate Similarity	NPC320019
0.8333	Intermediate Similarity	NPC471148
0.8333	Intermediate Similarity	NPC324017
0.8317	Intermediate Similarity	NPC475949
0.83	Intermediate Similarity	NPC169205
0.8283	Intermediate Similarity	NPC471142
0.8269	Intermediate Similarity	NPC472749
0.8269	Intermediate Similarity	NPC472751
0.8265	Intermediate Similarity	NPC212486
0.8265	Intermediate Similarity	NPC476300
0.8252	Intermediate Similarity	NPC110989
0.8252	Intermediate Similarity	NPC472747
0.8252	Intermediate Similarity	NPC472750
0.8247	Intermediate Similarity	NPC476004
0.8247	Intermediate Similarity	NPC474761
0.8247	Intermediate Similarity	NPC129419
0.8247	Intermediate Similarity	NPC51004
0.8235	Intermediate Similarity	NPC15993
0.8229	Intermediate Similarity	NPC475902
0.8229	Intermediate Similarity	NPC202672
0.8229	Intermediate Similarity	NPC476803
0.8218	Intermediate Similarity	NPC473326
0.8211	Intermediate Similarity	NPC279859
0.8211	Intermediate Similarity	NPC475461
0.8211	Intermediate Similarity	NPC469910
0.8211	Intermediate Similarity	NPC305475
0.8211	Intermediate Similarity	NPC38576
0.82	Intermediate Similarity	NPC76862
0.82	Intermediate Similarity	NPC473859
0.82	Intermediate Similarity	NPC158416
0.82	Intermediate Similarity	NPC39859
0.82	Intermediate Similarity	NPC476009
0.82	Intermediate Similarity	NPC477921
0.82	Intermediate Similarity	NPC470883
0.82	Intermediate Similarity	NPC476315
0.82	Intermediate Similarity	NPC185553
0.8182	Intermediate Similarity	NPC190294
0.8173	Intermediate Similarity	NPC472748
0.8163	Intermediate Similarity	NPC469627
0.8163	Intermediate Similarity	NPC473321
0.8163	Intermediate Similarity	NPC20713
0.8155	Intermediate Similarity	NPC140591
0.8155	Intermediate Similarity	NPC225353
0.8155	Intermediate Similarity	NPC86077
0.8155	Intermediate Similarity	NPC303653
0.8155	Intermediate Similarity	NPC291500
0.8155	Intermediate Similarity	NPC189609
0.8155	Intermediate Similarity	NPC197835
0.8144	Intermediate Similarity	NPC295312
0.8144	Intermediate Similarity	NPC268298
0.8144	Intermediate Similarity	NPC307411
0.8125	Intermediate Similarity	NPC186148
0.8125	Intermediate Similarity	NPC471738
0.8125	Intermediate Similarity	NPC179659
0.8119	Intermediate Similarity	NPC40812
0.8105	Intermediate Similarity	NPC470755
0.8105	Intermediate Similarity	NPC21469
0.8105	Intermediate Similarity	NPC165162
0.8105	Intermediate Similarity	NPC255307
0.81	Intermediate Similarity	NPC193645
0.81	Intermediate Similarity	NPC275960
0.81	Intermediate Similarity	NPC90121
0.81	Intermediate Similarity	NPC475900
0.81	Intermediate Similarity	NPC475659
0.81	Intermediate Similarity	NPC48803
0.81	Intermediate Similarity	NPC477922
0.8095	Intermediate Similarity	NPC469852
0.8095	Intermediate Similarity	NPC243998
0.8081	Intermediate Similarity	NPC165383
0.8061	Intermediate Similarity	NPC473619
0.8061	Intermediate Similarity	NPC474232
0.8061	Intermediate Similarity	NPC71533
0.8061	Intermediate Similarity	NPC106510
0.8058	Intermediate Similarity	NPC264477
0.8058	Intermediate Similarity	NPC477511
0.8041	Intermediate Similarity	NPC177629
0.8041	Intermediate Similarity	NPC58219
0.8041	Intermediate Similarity	NPC476805
0.8041	Intermediate Similarity	NPC472008
0.8039	Intermediate Similarity	NPC187761
0.8039	Intermediate Similarity	NPC54843
0.8039	Intermediate Similarity	NPC83895
0.8039	Intermediate Similarity	NPC474213
0.8021	Intermediate Similarity	NPC469483
0.802	Intermediate Similarity	NPC230800
0.802	Intermediate Similarity	NPC279621
0.802	Intermediate Similarity	NPC17585
0.8019	Intermediate Similarity	NPC469853
0.8019	Intermediate Similarity	NPC26617
0.8	Intermediate Similarity	NPC303942
0.8	Intermediate Similarity	NPC158756
0.8	Intermediate Similarity	NPC474338
0.8	Intermediate Similarity	NPC191476
0.8	Intermediate Similarity	NPC96259
0.8	Intermediate Similarity	NPC167219
0.8	Intermediate Similarity	NPC70424
0.8	Intermediate Similarity	NPC243618
0.8	Intermediate Similarity	NPC57405
0.8	Intermediate Similarity	NPC141193
0.8	Intermediate Similarity	NPC114979
0.7981	Intermediate Similarity	NPC39996
0.798	Intermediate Similarity	NPC476705
0.7963	Intermediate Similarity	NPC5103
0.7959	Intermediate Similarity	NPC92974
0.7959	Intermediate Similarity	NPC173926
0.7959	Intermediate Similarity	NPC474032
0.7944	Intermediate Similarity	NPC475960
0.7941	Intermediate Similarity	NPC328562
0.7941	Intermediate Similarity	NPC474313
0.7941	Intermediate Similarity	NPC323421
0.7938	Intermediate Similarity	NPC472007
0.7938	Intermediate Similarity	NPC72513
0.7938	Intermediate Similarity	NPC266957
0.7925	Intermediate Similarity	NPC223450
0.7921	Intermediate Similarity	NPC304886
0.7917	Intermediate Similarity	NPC125290
0.7917	Intermediate Similarity	NPC261380
0.79	Intermediate Similarity	NPC228451
0.79	Intermediate Similarity	NPC475838
0.79	Intermediate Similarity	NPC125674
0.7895	Intermediate Similarity	NPC473390
0.7895	Intermediate Similarity	NPC169575
0.7895	Intermediate Similarity	NPC40746
0.7895	Intermediate Similarity	NPC131669
0.7895	Intermediate Similarity	NPC475947
0.7885	Intermediate Similarity	NPC150923
0.7879	Intermediate Similarity	NPC166554
0.7879	Intermediate Similarity	NPC179394
0.7879	Intermediate Similarity	NPC316228
0.7879	Intermediate Similarity	NPC475855
0.7879	Intermediate Similarity	NPC473448
0.7879	Intermediate Similarity	NPC144133
0.7879	Intermediate Similarity	NPC65359
0.7876	Intermediate Similarity	NPC477092
0.7864	Intermediate Similarity	NPC261377
0.7864	Intermediate Similarity	NPC255592
0.7864	Intermediate Similarity	NPC470541
0.7864	Intermediate Similarity	NPC300584
0.7864	Intermediate Similarity	NPC308567
0.7857	Intermediate Similarity	NPC53158

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 NPC110443 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	1915
0.2-0.3	3703
0.3-0.4	2150
0.4-0.5	764
0.5-0.6	277
0.6-0.7	115
0.7-0.8	8
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
0.81	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.8019	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6371	Approved
0.7524	Intermediate Similarity	NPD4225	Approved
0.7451	Intermediate Similarity	NPD7983	Approved
0.7353	Intermediate Similarity	NPD5785	Approved
0.7353	Intermediate Similarity	NPD6698	Approved
0.7353	Intermediate Similarity	NPD46	Approved
0.73	Intermediate Similarity	NPD5786	Approved
0.72	Intermediate Similarity	NPD5363	Approved
0.72	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5282	Discontinued
0.7105	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7115	Discovery
0.7019	Intermediate Similarity	NPD7838	Discovery
0.69	Remote Similarity	NPD4269	Approved
0.69	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.69	Remote Similarity	NPD4270	Approved
0.6887	Remote Similarity	NPD5778	Approved
0.6887	Remote Similarity	NPD5779	Approved
0.6881	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7154	Phase 3
0.681	Remote Similarity	NPD6650	Approved
0.681	Remote Similarity	NPD6649	Approved
0.68	Remote Similarity	NPD5369	Approved
0.6783	Remote Similarity	NPD6373	Approved
0.6783	Remote Similarity	NPD6372	Approved
0.6777	Remote Similarity	NPD6319	Approved
0.6769	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD1695	Approved
0.6754	Remote Similarity	NPD5697	Approved
0.6752	Remote Similarity	NPD8297	Approved
0.6733	Remote Similarity	NPD6435	Approved
0.6721	Remote Similarity	NPD8513	Phase 3
0.6721	Remote Similarity	NPD8516	Approved
0.6721	Remote Similarity	NPD8517	Approved
0.6721	Remote Similarity	NPD8515	Approved
0.67	Remote Similarity	NPD4252	Approved
0.6696	Remote Similarity	NPD7320	Approved
0.6696	Remote Similarity	NPD6686	Approved
0.6696	Remote Similarity	NPD6899	Approved
0.6696	Remote Similarity	NPD6881	Approved
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.664	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6638	Remote Similarity	NPD6012	Approved
0.6638	Remote Similarity	NPD6014	Approved
0.6638	Remote Similarity	NPD6013	Approved
0.661	Remote Similarity	NPD6053	Discontinued
0.6609	Remote Similarity	NPD5701	Approved
0.6607	Remote Similarity	NPD5344	Discontinued
0.6604	Remote Similarity	NPD6101	Approved
0.6604	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7078	Approved
0.6585	Remote Similarity	NPD6015	Approved
0.6585	Remote Similarity	NPD6016	Approved
0.6581	Remote Similarity	NPD6883	Approved
0.6581	Remote Similarity	NPD7290	Approved
0.6581	Remote Similarity	NPD7102	Approved
0.6566	Remote Similarity	NPD4756	Discovery
0.6552	Remote Similarity	NPD6011	Approved
0.6552	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7839	Suspended
0.6538	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1694	Approved
0.6535	Remote Similarity	NPD4822	Approved
0.6535	Remote Similarity	NPD5368	Approved
0.6535	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7736	Approved
0.6535	Remote Similarity	NPD4821	Approved
0.6535	Remote Similarity	NPD4819	Approved
0.6535	Remote Similarity	NPD4820	Approved
0.6532	Remote Similarity	NPD6370	Approved
0.6532	Remote Similarity	NPD5988	Approved
0.6525	Remote Similarity	NPD6869	Approved
0.6525	Remote Similarity	NPD6617	Approved
0.6525	Remote Similarity	NPD8130	Phase 1
0.6525	Remote Similarity	NPD6847	Approved
0.6505	Remote Similarity	NPD6110	Phase 1
0.6504	Remote Similarity	NPD6059	Approved
0.6486	Remote Similarity	NPD6084	Phase 2
0.6486	Remote Similarity	NPD6083	Phase 2
0.6481	Remote Similarity	NPD6411	Approved
0.648	Remote Similarity	NPD7642	Approved
0.6476	Remote Similarity	NPD4249	Approved
0.6471	Remote Similarity	NPD6882	Approved
0.6457	Remote Similarity	NPD8074	Phase 3
0.6457	Remote Similarity	NPD8293	Discontinued
0.6455	Remote Similarity	NPD5695	Phase 3
0.6429	Remote Similarity	NPD5696	Approved
0.6417	Remote Similarity	NPD4632	Approved
0.6415	Remote Similarity	NPD4250	Approved
0.6415	Remote Similarity	NPD4251	Approved
0.6408	Remote Similarity	NPD5209	Approved
0.6408	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD5211	Phase 2
0.6387	Remote Similarity	NPD2204	Approved
0.6357	Remote Similarity	NPD7319	Approved
0.6349	Remote Similarity	NPD8328	Phase 3
0.6337	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD4271	Approved
0.6337	Remote Similarity	NPD4268	Approved
0.6311	Remote Similarity	NPD6274	Approved
0.6303	Remote Similarity	NPD4634	Approved
0.6296	Remote Similarity	NPD5370	Suspended
0.6293	Remote Similarity	NPD5141	Approved
0.6273	Remote Similarity	NPD6399	Phase 3
0.627	Remote Similarity	NPD8080	Discontinued
0.626	Remote Similarity	NPD6009	Approved
0.625	Remote Similarity	NPD7507	Approved
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5286	Approved
0.6228	Remote Similarity	NPD5285	Approved
0.6228	Remote Similarity	NPD6648	Approved
0.6228	Remote Similarity	NPD4696	Approved
0.622	Remote Similarity	NPD7829	Approved
0.622	Remote Similarity	NPD7830	Approved
0.6218	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD4755	Approved
0.619	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5983	Phase 2
0.619	Remote Similarity	NPD5331	Approved
0.619	Remote Similarity	NPD5332	Approved
0.6182	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5693	Phase 1
0.6167	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7100	Approved
0.616	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD4790	Discontinued
0.6136	Remote Similarity	NPD7260	Phase 2
0.6132	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6317	Approved
0.6124	Remote Similarity	NPD8451	Approved
0.6121	Remote Similarity	NPD5224	Approved
0.6121	Remote Similarity	NPD4633	Approved
0.6121	Remote Similarity	NPD5226	Approved
0.6121	Remote Similarity	NPD5225	Approved
0.6106	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4697	Phase 3
0.6105	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6008	Approved
0.6094	Remote Similarity	NPD7604	Phase 2
0.609	Remote Similarity	NPD6845	Suspended
0.6087	Remote Similarity	NPD7640	Approved
0.6087	Remote Similarity	NPD4700	Approved
0.6087	Remote Similarity	NPD7639	Approved
0.608	Remote Similarity	NPD6314	Approved
0.608	Remote Similarity	NPD6313	Approved
0.608	Remote Similarity	NPD7641	Discontinued
0.608	Remote Similarity	NPD6335	Approved
0.6077	Remote Similarity	NPD8448	Approved
0.6074	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5174	Approved
0.6068	Remote Similarity	NPD5175	Approved
0.6063	Remote Similarity	NPD8444	Approved
0.6063	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6672	Approved
0.6055	Remote Similarity	NPD5737	Approved
0.6053	Remote Similarity	NPD7902	Approved
0.6047	Remote Similarity	NPD8341	Approved
0.6047	Remote Similarity	NPD8299	Approved
0.6047	Remote Similarity	NPD8340	Approved
0.6047	Remote Similarity	NPD8342	Approved
0.6042	Remote Similarity	NPD7331	Phase 2
0.6036	Remote Similarity	NPD7637	Suspended
0.6034	Remote Similarity	NPD5223	Approved
0.6033	Remote Similarity	NPD2067	Discontinued
0.6031	Remote Similarity	NPD6033	Approved
0.6018	Remote Similarity	NPD5210	Approved
0.6018	Remote Similarity	NPD4629	Approved
0.6	Remote Similarity	NPD7638	Approved
0.6	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD6336	Discontinued
0.6	Remote Similarity	NPD8273	Phase 1
0.6	Remote Similarity	NPD8415	Approved
0.6	Remote Similarity	NPD3197	Phase 1
0.5984	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD5221	Approved
0.5965	Remote Similarity	NPD5222	Approved
0.5965	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.594	Remote Similarity	NPD5956	Approved
0.594	Remote Similarity	NPD8390	Approved
0.594	Remote Similarity	NPD8392	Approved
0.594	Remote Similarity	NPD8391	Approved
0.5938	Remote Similarity	NPD7341	Phase 2
0.5938	Remote Similarity	NPD6909	Approved
0.5938	Remote Similarity	NPD8268	Approved
0.5938	Remote Similarity	NPD8267	Approved
0.5938	Remote Similarity	NPD8266	Approved
0.5938	Remote Similarity	NPD6908	Approved
0.5938	Remote Similarity	NPD6921	Approved
0.5938	Remote Similarity	NPD8269	Approved
0.5926	Remote Similarity	NPD1696	Phase 3
0.592	Remote Similarity	NPD6868	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