NPASS Compound

Structure

NPC472755 OpenBabel07101719252D 34 35 0 0 1 0 0 0 0 0999 V2000 -4.3439 -6.0393 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5201 -3.8305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0401 2.4011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0401 -2.4011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6592 2.5969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0803 2.0072 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2430 -2.5071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0372 -5.3959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5881 0.4611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5881 -0.4611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9229 -4.1950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0401 -0.9221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5982 2.0720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8268 -4.4738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4504 1.6616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4504 -1.6616 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2505 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6524 2.0720 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2105 0.9221 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7125 -3.2729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0401 0.9221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6524 -2.0720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5982 -2.0720 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8002 -1.6616 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8002 1.6616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2105 -0.9221 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1964 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4419 2.9941 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0992 -1.9862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8922 1.3325 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4419 -2.9941 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2105 -2.4011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8087 -2.9941 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 8 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 8 14 1 0 0 0 0 9 10 1 0 0 0 0 10 26 1 0 0 0 0 11 14 2 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 15 21 1 0 0 0 0 16 4 1 6 0 0 0 16 23 1 0 0 0 0 17 21 1 0 0 0 0 17 27 1 0 0 0 0 18 25 1 0 0 0 0 18 28 1 6 0 0 0 19 9 1 6 0 0 0 19 25 1 0 0 0 0 19 34 1 0 0 0 0 20 29 2 0 0 0 0 20 33 1 0 0 0 0 21 30 2 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 31 2 0 0 0 0 23 33 1 6 0 0 0 24 26 1 6 0 0 0 24 32 1 0 0 0 0 26 7 1 1 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.27
Volume:	498.279
LogP:	2.74
LogD:	0.723
LogS:	-2.099
# Rotatable Bonds:	4
TPSA:	127.2
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	6.256
Fsp3:	0.769
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.725
MDCK Permeability:	1.587171936989762e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.959
Human Intestinal Absorption (HIA):	0.302
20% Bioavailability (F20%):	0.64
30% Bioavailability (F30%):	0.063

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.12
Plasma Protein Binding (PPB):	67.5418472290039%
Volume Distribution (VD):	0.909
Pgp-substrate:	21.614988327026367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.602
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.087
CYP3A4-substrate:	0.446

ADMET: Excretion

Clearance (CL):	7.821
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.049
Rat Oral Acute Toxicity:	0.917
Maximum Recommended Daily Dose:	0.873
Skin Sensitization:	0.721
Carcinogencity:	0.112
Eye Corrosion:	0.915
Eye Irritation:	0.082
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC472755

Natural Product ID:	NPC472755
*Common Name:**	GEOUBLSPQSYFCZ-CEGSKBCRSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GEOUBLSPQSYFCZ-CEGSKBCRSA-N
Standard InCHI:	InChI=1S/C26H40O8/c1-8-14(2)11-20(29)33-23-16(4)12-17(27)21(30)15(3)13-18(28)25(5,6)19-9-10-26(7,34-19)24(32)22(23)31/h11,13,16-19,23-24,27-28,32H,8-10,12H2,1-7H3/b14-11+,15-13+/t16-,17?,18+,19+,23-,24-,26-/m1/s1
SMILES:	CC/C(=C/C(=O)O[C@@H]1[C@H](C)CC(O)C(=O)/C(=C/[C@@H](C([C@H]2O[C@]([C@@H](C1=O)O)(C)CC2)(C)C)O)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3582002
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO33329	stillingia lineata	Species	Euphorbiaceae	Eukaryota	Leaves	Langevin, La Reunion, France	2009-Nov	PMID[25946116]

☑ 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
EC50	1
Others	3

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	Inhibition	<	40.0	%	PMID[554360]
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	<	40.0	%	PMID[554360]
NPT306	Cell Line	PC-3	Homo sapiens	Inhibition	<	40.0	%	PMID[554360]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	>	208000.0	nM	PMID[554360]

☑ 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 NPC472755 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	232
0.1-0.2	1302
0.2-0.3	4488
0.3-0.4	7682
0.4-0.5	14048
0.5-0.6	7947
0.6-0.7	4975
0.7-0.8	1781
0.8-0.85	184
0.85-0.9	52
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC472754
0.9583	High Similarity	NPC472753
0.9293	High Similarity	NPC472756
0.92	High Similarity	NPC472751
0.92	High Similarity	NPC472749
0.91	High Similarity	NPC472748
0.9	High Similarity	NPC472747
0.9	High Similarity	NPC472750
0.899	High Similarity	NPC46998
0.899	High Similarity	NPC185141
0.899	High Similarity	NPC110443
0.899	High Similarity	NPC133907
0.899	High Similarity	NPC128733
0.89	High Similarity	NPC149371
0.8866	High Similarity	NPC36954
0.8812	High Similarity	NPC475945
0.8812	High Similarity	NPC475871
0.88	High Similarity	NPC47880
0.8788	High Similarity	NPC471144
0.8763	High Similarity	NPC121825
0.8738	High Similarity	NPC477513
0.8713	High Similarity	NPC474747
0.8713	High Similarity	NPC320019
0.8713	High Similarity	NPC324017
0.866	High Similarity	NPC476300
0.866	High Similarity	NPC469645
0.866	High Similarity	NPC475912
0.866	High Similarity	NPC469692
0.8646	High Similarity	NPC474761
0.8646	High Similarity	NPC476004
0.8614	High Similarity	NPC201718
0.8614	High Similarity	NPC15993
0.8614	High Similarity	NPC474339
0.8614	High Similarity	NPC474742
0.8614	High Similarity	NPC476270
0.8614	High Similarity	NPC164598
0.8586	High Similarity	NPC39859
0.8586	High Similarity	NPC76862
0.8586	High Similarity	NPC470883
0.8586	High Similarity	NPC476315
0.8586	High Similarity	NPC158416
0.8571	High Similarity	NPC469632
0.8571	High Similarity	NPC38154
0.8557	High Similarity	NPC30515
0.8557	High Similarity	NPC184463
0.8545	High Similarity	NPC477092
0.8544	High Similarity	NPC474741
0.8544	High Similarity	NPC100487
0.8544	High Similarity	NPC203659
0.8544	High Similarity	NPC475676
0.8544	High Similarity	NPC220964
0.8515	High Similarity	NPC288876
0.8515	High Similarity	NPC475949
0.85	High Similarity	NPC40812
0.8485	Intermediate Similarity	NPC471142
0.8485	Intermediate Similarity	NPC270013
0.8485	Intermediate Similarity	NPC14961
0.8476	Intermediate Similarity	NPC233379
0.8476	Intermediate Similarity	NPC14862
0.8476	Intermediate Similarity	NPC474664
0.8469	Intermediate Similarity	NPC162205
0.8469	Intermediate Similarity	NPC288240
0.8469	Intermediate Similarity	NPC273579
0.8469	Intermediate Similarity	NPC295204
0.8455	Intermediate Similarity	NPC475401
0.8454	Intermediate Similarity	NPC51004
0.8447	Intermediate Similarity	NPC4620
0.8447	Intermediate Similarity	NPC110989
0.84	Intermediate Similarity	NPC476009
0.8396	Intermediate Similarity	NPC15218
0.8384	Intermediate Similarity	NPC474035
0.8384	Intermediate Similarity	NPC190294
0.8384	Intermediate Similarity	NPC81386
0.8381	Intermediate Similarity	NPC324327
0.8381	Intermediate Similarity	NPC72813
0.8381	Intermediate Similarity	NPC326994
0.8381	Intermediate Similarity	NPC194620
0.8381	Intermediate Similarity	NPC474421
0.8364	Intermediate Similarity	NPC471145
0.8364	Intermediate Similarity	NPC471146
0.8364	Intermediate Similarity	NPC475305
0.8351	Intermediate Similarity	NPC307411
0.835	Intermediate Similarity	NPC471148
0.835	Intermediate Similarity	NPC225353
0.8333	Intermediate Similarity	NPC317687
0.8333	Intermediate Similarity	NPC470922
0.8333	Intermediate Similarity	NPC179659
0.8318	Intermediate Similarity	NPC161816
0.8318	Intermediate Similarity	NPC115257
0.8318	Intermediate Similarity	NPC5103
0.8317	Intermediate Similarity	NPC323421
0.8317	Intermediate Similarity	NPC328562
0.8302	Intermediate Similarity	NPC169888
0.8302	Intermediate Similarity	NPC327286
0.8302	Intermediate Similarity	NPC55972
0.83	Intermediate Similarity	NPC475900
0.8286	Intermediate Similarity	NPC475802
0.8286	Intermediate Similarity	NPC16313
0.8286	Intermediate Similarity	NPC9303
0.8283	Intermediate Similarity	NPC81419
0.8283	Intermediate Similarity	NPC212486
0.8283	Intermediate Similarity	NPC179746
0.8269	Intermediate Similarity	NPC475873
0.8265	Intermediate Similarity	NPC473448
0.8257	Intermediate Similarity	NPC469463
0.8257	Intermediate Similarity	NPC469454
0.8257	Intermediate Similarity	NPC469496
0.8252	Intermediate Similarity	NPC477511
0.8252	Intermediate Similarity	NPC264477
0.8247	Intermediate Similarity	NPC202672
0.8241	Intermediate Similarity	NPC317107
0.8235	Intermediate Similarity	NPC187761
0.8235	Intermediate Similarity	NPC261377
0.8235	Intermediate Similarity	NPC83895
0.8235	Intermediate Similarity	NPC308567
0.8235	Intermediate Similarity	NPC141191
0.8235	Intermediate Similarity	NPC255592
0.8235	Intermediate Similarity	NPC161855
0.8224	Intermediate Similarity	NPC475922
0.8218	Intermediate Similarity	NPC477921
0.8218	Intermediate Similarity	NPC473859
0.8218	Intermediate Similarity	NPC230800
0.8218	Intermediate Similarity	NPC279621
0.8218	Intermediate Similarity	NPC17585
0.8218	Intermediate Similarity	NPC31645
0.8208	Intermediate Similarity	NPC26617
0.8182	Intermediate Similarity	NPC208886
0.8182	Intermediate Similarity	NPC476705
0.8182	Intermediate Similarity	NPC20713
0.8182	Intermediate Similarity	NPC473321
0.8182	Intermediate Similarity	NPC12172
0.8173	Intermediate Similarity	NPC473596
0.8148	Intermediate Similarity	NPC477103
0.8148	Intermediate Similarity	NPC257240
0.8144	Intermediate Similarity	NPC471738
0.8137	Intermediate Similarity	NPC169205
0.8125	Intermediate Similarity	NPC21469
0.8125	Intermediate Similarity	NPC137033
0.8125	Intermediate Similarity	NPC11804
0.8119	Intermediate Similarity	NPC477922
0.8119	Intermediate Similarity	NPC475659
0.81	Intermediate Similarity	NPC475302
0.8095	Intermediate Similarity	NPC69171
0.8095	Intermediate Similarity	NPC474165
0.8087	Intermediate Similarity	NPC67251
0.8081	Intermediate Similarity	NPC475748
0.8081	Intermediate Similarity	NPC474232
0.8081	Intermediate Similarity	NPC473619
0.8073	Intermediate Similarity	NPC304180
0.8073	Intermediate Similarity	NPC179798
0.8073	Intermediate Similarity	NPC287311
0.8073	Intermediate Similarity	NPC475495
0.8061	Intermediate Similarity	NPC474471
0.8061	Intermediate Similarity	NPC475902
0.8061	Intermediate Similarity	NPC227379
0.8061	Intermediate Similarity	NPC471047
0.8061	Intermediate Similarity	NPC469628
0.8061	Intermediate Similarity	NPC475906
0.8061	Intermediate Similarity	NPC469631
0.8061	Intermediate Similarity	NPC469653
0.8061	Intermediate Similarity	NPC153805
0.8058	Intermediate Similarity	NPC187268
0.8058	Intermediate Similarity	NPC473326
0.8058	Intermediate Similarity	NPC474213
0.8056	Intermediate Similarity	NPC477102
0.8056	Intermediate Similarity	NPC42662
0.8041	Intermediate Similarity	NPC261721
0.8041	Intermediate Similarity	NPC469483
0.8039	Intermediate Similarity	NPC185553
0.8039	Intermediate Similarity	NPC473291
0.8036	Intermediate Similarity	NPC476712
0.8036	Intermediate Similarity	NPC476713
0.8021	Intermediate Similarity	NPC3464
0.8021	Intermediate Similarity	NPC474780
0.8021	Intermediate Similarity	NPC151176
0.8021	Intermediate Similarity	NPC475963
0.802	Intermediate Similarity	NPC57405
0.802	Intermediate Similarity	NPC303942
0.802	Intermediate Similarity	NPC474247
0.8019	Intermediate Similarity	NPC146731
0.8019	Intermediate Similarity	NPC258532
0.8019	Intermediate Similarity	NPC296950
0.8019	Intermediate Similarity	NPC477510
0.8019	Intermediate Similarity	NPC471143
0.8017	Intermediate Similarity	NPC476729
0.8017	Intermediate Similarity	NPC24651
0.8	Intermediate Similarity	NPC39996
0.8	Intermediate Similarity	NPC269530
0.8	Intermediate Similarity	NPC189609
0.8	Intermediate Similarity	NPC105725
0.8	Intermediate Similarity	NPC477093
0.8	Intermediate Similarity	NPC300312
0.8	Intermediate Similarity	NPC197835
0.8	Intermediate Similarity	NPC291500
0.8	Intermediate Similarity	NPC303653
0.8	Intermediate Similarity	NPC118405
0.8	Intermediate Similarity	NPC138757
0.8	Intermediate Similarity	NPC473877
0.8	Intermediate Similarity	NPC473522
0.8	Intermediate Similarity	NPC261607

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 NPC472755 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	1908
0.2-0.3	3566
0.3-0.4	2173
0.4-0.5	825
0.5-0.6	274
0.6-0.7	171
0.7-0.8	16
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
0.8208	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6371	Approved
0.8	Intermediate Similarity	NPD7983	Approved
0.7941	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD46	Approved
0.79	Intermediate Similarity	NPD6698	Approved
0.7549	Intermediate Similarity	NPD7838	Discovery
0.7549	Intermediate Similarity	NPD5785	Approved
0.7547	Intermediate Similarity	NPD4225	Approved
0.7477	Intermediate Similarity	NPD6686	Approved
0.7434	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD6319	Approved
0.7333	Intermediate Similarity	NPD5282	Discontinued
0.7265	Intermediate Similarity	NPD7115	Discovery
0.7238	Intermediate Similarity	NPD5778	Approved
0.7238	Intermediate Similarity	NPD5779	Approved
0.7228	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD8297	Approved
0.7131	Intermediate Similarity	NPD7492	Approved
0.7083	Intermediate Similarity	NPD6054	Approved
0.7073	Intermediate Similarity	NPD6616	Approved
0.7064	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5363	Approved
0.7037	Intermediate Similarity	NPD7839	Suspended
0.7025	Intermediate Similarity	NPD8513	Phase 3
0.7025	Intermediate Similarity	NPD8515	Approved
0.7025	Intermediate Similarity	NPD8517	Approved
0.7025	Intermediate Similarity	NPD8516	Approved
0.7018	Intermediate Similarity	NPD6881	Approved
0.7018	Intermediate Similarity	NPD6899	Approved
0.7018	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7078	Approved
0.6991	Remote Similarity	NPD7128	Approved
0.6991	Remote Similarity	NPD6675	Approved
0.6991	Remote Similarity	NPD5739	Approved
0.6991	Remote Similarity	NPD6402	Approved
0.699	Remote Similarity	NPD5786	Approved
0.6983	Remote Similarity	NPD6649	Approved
0.6983	Remote Similarity	NPD6650	Approved
0.6967	Remote Similarity	NPD6370	Approved
0.696	Remote Similarity	NPD7736	Approved
0.6957	Remote Similarity	NPD6372	Approved
0.6957	Remote Similarity	NPD6373	Approved
0.6942	Remote Similarity	NPD6059	Approved
0.6937	Remote Similarity	NPD5344	Discontinued
0.693	Remote Similarity	NPD5697	Approved
0.6923	Remote Similarity	NPD6882	Approved
0.6923	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD8328	Phase 3
0.6905	Remote Similarity	NPD7319	Approved
0.6897	Remote Similarity	NPD7102	Approved
0.6897	Remote Similarity	NPD6883	Approved
0.6897	Remote Similarity	NPD7290	Approved
0.6885	Remote Similarity	NPD6016	Approved
0.6885	Remote Similarity	NPD6015	Approved
0.688	Remote Similarity	NPD8293	Discontinued
0.687	Remote Similarity	NPD7320	Approved
0.6864	Remote Similarity	NPD4632	Approved
0.6863	Remote Similarity	NPD7154	Phase 3
0.6838	Remote Similarity	NPD6847	Approved
0.6838	Remote Similarity	NPD8130	Phase 1
0.6838	Remote Similarity	NPD6617	Approved
0.6838	Remote Similarity	NPD6869	Approved
0.6829	Remote Similarity	NPD5988	Approved
0.6822	Remote Similarity	NPD6411	Approved
0.6818	Remote Similarity	NPD6084	Phase 2
0.6818	Remote Similarity	NPD6083	Phase 2
0.681	Remote Similarity	NPD6014	Approved
0.681	Remote Similarity	NPD6012	Approved
0.681	Remote Similarity	NPD6013	Approved
0.68	Remote Similarity	NPD7507	Approved
0.6783	Remote Similarity	NPD5701	Approved
0.678	Remote Similarity	NPD6053	Discontinued
0.6774	Remote Similarity	NPD7642	Approved
0.6765	Remote Similarity	NPD4270	Approved
0.6765	Remote Similarity	NPD4269	Approved
0.6765	Remote Similarity	NPD6435	Approved
0.6752	Remote Similarity	NPD4634	Approved
0.6746	Remote Similarity	NPD8074	Phase 3
0.6724	Remote Similarity	NPD6011	Approved
0.67	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6110	Phase 1
0.6696	Remote Similarity	NPD7640	Approved
0.6696	Remote Similarity	NPD7639	Approved
0.6694	Remote Similarity	NPD8080	Discontinued
0.6694	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.664	Remote Similarity	NPD7830	Approved
0.664	Remote Similarity	NPD7604	Phase 2
0.664	Remote Similarity	NPD7829	Approved
0.6636	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6101	Approved
0.6636	Remote Similarity	NPD5695	Phase 3
0.6636	Remote Similarity	NPD1695	Approved
0.6613	Remote Similarity	NPD5983	Phase 2
0.6607	Remote Similarity	NPD7638	Approved
0.6604	Remote Similarity	NPD4251	Approved
0.6604	Remote Similarity	NPD4250	Approved
0.6602	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5209	Approved
0.6579	Remote Similarity	NPD5211	Phase 2
0.6571	Remote Similarity	NPD1694	Approved
0.6569	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4821	Approved
0.6569	Remote Similarity	NPD4252	Approved
0.6569	Remote Similarity	NPD4820	Approved
0.6569	Remote Similarity	NPD4819	Approved
0.6569	Remote Similarity	NPD4822	Approved
0.6569	Remote Similarity	NPD5368	Approved
0.6557	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6648	Approved
0.6538	Remote Similarity	NPD5362	Discontinued
0.6535	Remote Similarity	NPD6336	Discontinued
0.6509	Remote Similarity	NPD4249	Approved
0.6496	Remote Similarity	NPD6412	Phase 2
0.6489	Remote Similarity	NPD6845	Suspended
0.648	Remote Similarity	NPD8444	Approved
0.648	Remote Similarity	NPD6921	Approved
0.648	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD6274	Approved
0.6471	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5141	Approved
0.646	Remote Similarity	NPD5696	Approved
0.6452	Remote Similarity	NPD7101	Approved
0.6452	Remote Similarity	NPD7100	Approved
0.6436	Remote Similarity	NPD4756	Discovery
0.6434	Remote Similarity	NPD6033	Approved
0.6406	Remote Similarity	NPD8273	Phase 1
0.6406	Remote Similarity	NPD8451	Approved
0.6404	Remote Similarity	NPD4696	Approved
0.6404	Remote Similarity	NPD5286	Approved
0.6404	Remote Similarity	NPD5285	Approved
0.6391	Remote Similarity	NPD8415	Approved
0.6389	Remote Similarity	NPD5737	Approved
0.6389	Remote Similarity	NPD6672	Approved
0.6373	Remote Similarity	NPD4271	Approved
0.6373	Remote Similarity	NPD4268	Approved
0.6372	Remote Similarity	NPD4755	Approved
0.6371	Remote Similarity	NPD6335	Approved
0.6371	Remote Similarity	NPD7641	Discontinued
0.6364	Remote Similarity	NPD5693	Phase 1
0.6357	Remote Similarity	NPD8448	Approved
0.6328	Remote Similarity	NPD8341	Approved
0.6328	Remote Similarity	NPD8299	Approved
0.6328	Remote Similarity	NPD8342	Approved
0.6328	Remote Similarity	NPD8340	Approved
0.6306	Remote Similarity	NPD6399	Phase 3
0.6296	Remote Similarity	NPD7524	Approved
0.6293	Remote Similarity	NPD5224	Approved
0.6293	Remote Similarity	NPD5225	Approved
0.6293	Remote Similarity	NPD5226	Approved
0.6293	Remote Similarity	NPD4633	Approved
0.629	Remote Similarity	NPD6317	Approved
0.629	Remote Similarity	NPD7500	Approved
0.6271	Remote Similarity	NPD6008	Approved
0.6262	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD4700	Approved
0.624	Remote Similarity	NPD6313	Approved
0.624	Remote Similarity	NPD7328	Approved
0.624	Remote Similarity	NPD7327	Approved
0.624	Remote Similarity	NPD6314	Approved
0.6239	Remote Similarity	NPD5175	Approved
0.6239	Remote Similarity	NPD5174	Approved
0.622	Remote Similarity	NPD6909	Approved
0.622	Remote Similarity	NPD6908	Approved
0.622	Remote Similarity	NPD8033	Approved
0.622	Remote Similarity	NPD7503	Approved
0.6218	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD5956	Approved
0.6212	Remote Similarity	NPD8392	Approved
0.6212	Remote Similarity	NPD8391	Approved
0.6212	Remote Similarity	NPD8390	Approved
0.621	Remote Similarity	NPD6868	Approved
0.6207	Remote Similarity	NPD5223	Approved
0.619	Remote Similarity	NPD7516	Approved
0.6182	Remote Similarity	NPD5370	Suspended
0.6182	Remote Similarity	NPD6904	Approved
0.6182	Remote Similarity	NPD6673	Approved
0.6182	Remote Similarity	NPD4753	Phase 2
0.6182	Remote Similarity	NPD6080	Approved
0.6179	Remote Similarity	NPD8133	Approved
0.6168	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4729	Approved
0.6167	Remote Similarity	NPD4730	Approved
0.616	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7632	Discontinued
0.6148	Remote Similarity	NPD2204	Approved
0.6148	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD8377	Approved
0.6142	Remote Similarity	NPD8294	Approved
0.614	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5221	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