NPASS Compound

Structure

NPC471148 OpenBabel07101719132D 27 30 0 0 1 0 0 0 0 0999 V2000 -3.5682 -2.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7880 -4.3896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3715 -1.7735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8102 -2.7110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4410 -1.1941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7443 -0.5667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2546 -2.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3813 -1.7939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1561 -2.4137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6359 -2.1111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1290 -4.1947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4340 -1.7735 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.4427 -3.4363 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1864 -2.7110 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8119 -0.4687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5103 -3.3383 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8257 -4.8220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6221 -3.1797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6221 -2.2422 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -0.9375 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0843 -2.2821 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7277 -5.7544 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4340 -3.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6376 -4.3533 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8102 -3.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6221 -1.3047 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 1 0 0 0 0 2 11 2 0 0 0 0 3 12 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 10 1 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 8 14 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 12 26 1 0 0 0 0 13 7 1 6 0 0 0 13 16 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 1 0 0 0 15 20 1 1 0 0 0 15 27 1 0 0 0 0 16 11 1 1 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 26 1 0 0 0 0 20 9 1 1 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.17
Volume:	371.236
LogP:	1.404
LogD:	1.892
LogS:	-3.374
# Rotatable Bonds:	4
TPSA:	97.89
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.343
Synthetic Accessibility Score:	5.442
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.282
MDCK Permeability:	4.5893259084550664e-05
Pgp-inhibitor:	0.397
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.499
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167
Plasma Protein Binding (PPB):	84.8023452758789%
Volume Distribution (VD):	1.414
Pgp-substrate:	7.392848968505859%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.181
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.754
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.471
CYP3A4-substrate:	0.336

ADMET: Excretion

Clearance (CL):	9.078
Half-life (T1/2):	0.409

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.392
Drug-inuced Liver Injury (DILI):	0.632
AMES Toxicity:	0.811
Rat Oral Acute Toxicity:	0.656
Maximum Recommended Daily Dose:	0.372
Skin Sensitization:	0.398
Carcinogencity:	0.1
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.843

Download Data

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

Natural Product: NPC471148

Natural Product ID:	NPC471148
*Common Name:**	SRCUUILUHHZYDO-HEMHXPGDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SRCUUILUHHZYDO-HEMHXPGDSA-N
Standard InCHI:	InChI=1S/C20H26O7/c1-10-5-6-15-20(9-21,27-15)8-14(25-18(23)19(4)12(3)26-19)16-11(2)17(22)24-13(16)7-10/h7,12-16,21H,2,5-6,8-9H2,1,3-4H3/b10-7+/t12?,13-,14-,15-,16+,19?,20+/m1/s1
SMILES:	CC1C(O1)(C)C(=O)OC2CC3(C(O3)CCC(=CC4C2C(=C)C(=O)O4)C)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2380797
PubChem CID:	73345842
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO27591	Viguiera hypargyrea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO27591	Viguiera hypargyrea	Species	Asteraceae	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	3

Activity Type	# Activity
Individual Protein	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	33651.16	nM	PMID[536318]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[536318]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	33640.0	nM	PMID[536318]

☑ 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 NPC471148 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	248
0.1-0.2	1526
0.2-0.3	5351
0.3-0.4	10816
0.4-0.5	13643
0.5-0.6	7174
0.6-0.7	2955
0.7-0.8	804
0.8-0.85	103
0.85-0.9	63
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9592	High Similarity	NPC477513
0.9479	High Similarity	NPC164598
0.9479	High Similarity	NPC474339
0.9368	High Similarity	NPC471140
0.9175	High Similarity	NPC475949
0.9082	High Similarity	NPC477511
0.9082	High Similarity	NPC264477
0.9062	High Similarity	NPC473859
0.898	High Similarity	NPC288876
0.8958	High Similarity	NPC475659
0.8889	High Similarity	NPC201718
0.8878	High Similarity	NPC471144
0.8866	High Similarity	NPC230800
0.8866	High Similarity	NPC279621
0.8854	High Similarity	NPC471147
0.8824	High Similarity	NPC194620
0.8824	High Similarity	NPC72813
0.8824	High Similarity	NPC324327
0.8824	High Similarity	NPC326994
0.8824	High Similarity	NPC474421
0.8812	High Similarity	NPC477510
0.8812	High Similarity	NPC471143
0.88	High Similarity	NPC149371
0.8788	High Similarity	NPC477512
0.8763	High Similarity	NPC14961
0.8763	High Similarity	NPC270013
0.875	High Similarity	NPC125674
0.875	High Similarity	NPC228451
0.875	High Similarity	NPC212486
0.875	High Similarity	NPC475838
0.8738	High Similarity	NPC169888
0.8738	High Similarity	NPC233379
0.8738	High Similarity	NPC474664
0.8738	High Similarity	NPC327286
0.8738	High Similarity	NPC14862
0.8738	High Similarity	NPC55972
0.8725	High Similarity	NPC9303
0.8725	High Similarity	NPC16313
0.87	High Similarity	NPC47880
0.87	High Similarity	NPC476270
0.8687	High Similarity	NPC473326
0.8687	High Similarity	NPC474213
0.8673	High Similarity	NPC17585
0.866	High Similarity	NPC57405
0.866	High Similarity	NPC474035
0.866	High Similarity	NPC303942
0.866	High Similarity	NPC474247
0.866	High Similarity	NPC81386
0.8654	High Similarity	NPC15218
0.8654	High Similarity	NPC475922
0.8627	High Similarity	NPC474741
0.8617	High Similarity	NPC266957
0.8571	High Similarity	NPC471141
0.8571	High Similarity	NPC161816
0.8571	High Similarity	NPC115257
0.8557	High Similarity	NPC475912
0.8544	High Similarity	NPC475802
0.8529	High Similarity	NPC4620
0.8529	High Similarity	NPC475945
0.8529	High Similarity	NPC475871
0.8519	High Similarity	NPC474333
0.8515	High Similarity	NPC473332
0.8511	High Similarity	NPC50637
0.85	High Similarity	NPC208233
0.8485	Intermediate Similarity	NPC35498
0.8485	Intermediate Similarity	NPC476315
0.8469	Intermediate Similarity	NPC121825
0.8454	Intermediate Similarity	NPC30515
0.8454	Intermediate Similarity	NPC475881
0.8454	Intermediate Similarity	NPC184463
0.8454	Intermediate Similarity	NPC20713
0.8454	Intermediate Similarity	NPC70251
0.8447	Intermediate Similarity	NPC220964
0.8447	Intermediate Similarity	NPC475676
0.844	Intermediate Similarity	NPC296822
0.8438	Intermediate Similarity	NPC151770
0.8431	Intermediate Similarity	NPC474747
0.8411	Intermediate Similarity	NPC473877
0.8384	Intermediate Similarity	NPC471142
0.8384	Intermediate Similarity	NPC36954
0.8367	Intermediate Similarity	NPC475302
0.8367	Intermediate Similarity	NPC469692
0.8367	Intermediate Similarity	NPC179746
0.8367	Intermediate Similarity	NPC81419
0.8367	Intermediate Similarity	NPC476300
0.8367	Intermediate Similarity	NPC469645
0.8365	Intermediate Similarity	NPC44004
0.8351	Intermediate Similarity	NPC474232
0.8351	Intermediate Similarity	NPC475855
0.8351	Intermediate Similarity	NPC51004
0.8351	Intermediate Similarity	NPC473619
0.835	Intermediate Similarity	NPC472755
0.8333	Intermediate Similarity	NPC472753
0.8333	Intermediate Similarity	NPC474742
0.8333	Intermediate Similarity	NPC202672
0.8333	Intermediate Similarity	NPC287089
0.8333	Intermediate Similarity	NPC46998
0.8333	Intermediate Similarity	NPC476803
0.8333	Intermediate Similarity	NPC133907
0.8333	Intermediate Similarity	NPC185141
0.8333	Intermediate Similarity	NPC110443
0.8333	Intermediate Similarity	NPC128733
0.8316	Intermediate Similarity	NPC469910
0.8302	Intermediate Similarity	NPC38154
0.83	Intermediate Similarity	NPC76862
0.83	Intermediate Similarity	NPC158416
0.83	Intermediate Similarity	NPC39859
0.83	Intermediate Similarity	NPC477921
0.83	Intermediate Similarity	NPC470883
0.8283	Intermediate Similarity	NPC473316
0.8283	Intermediate Similarity	NPC190294
0.8283	Intermediate Similarity	NPC473330
0.8283	Intermediate Similarity	NPC140543
0.8269	Intermediate Similarity	NPC472756
0.8265	Intermediate Similarity	NPC473321
0.8265	Intermediate Similarity	NPC12172
0.8265	Intermediate Similarity	NPC208886
0.8252	Intermediate Similarity	NPC324017
0.8252	Intermediate Similarity	NPC320019
0.8252	Intermediate Similarity	NPC472754
0.8247	Intermediate Similarity	NPC307411
0.8247	Intermediate Similarity	NPC166919
0.8247	Intermediate Similarity	NPC474032
0.8247	Intermediate Similarity	NPC475971
0.8229	Intermediate Similarity	NPC231889
0.8211	Intermediate Similarity	NPC255307
0.82	Intermediate Similarity	NPC477922
0.8182	Intermediate Similarity	NPC273579
0.8182	Intermediate Similarity	NPC165383
0.8182	Intermediate Similarity	NPC162205
0.8182	Intermediate Similarity	NPC295204
0.8182	Intermediate Similarity	NPC288240
0.8173	Intermediate Similarity	NPC69171
0.8173	Intermediate Similarity	NPC19239
0.8173	Intermediate Similarity	NPC474165
0.8173	Intermediate Similarity	NPC474166
0.8163	Intermediate Similarity	NPC179394
0.8163	Intermediate Similarity	NPC475748
0.8163	Intermediate Similarity	NPC144133
0.8163	Intermediate Similarity	NPC476004
0.8163	Intermediate Similarity	NPC474761
0.8155	Intermediate Similarity	NPC15993
0.8144	Intermediate Similarity	NPC473715
0.8137	Intermediate Similarity	NPC187268
0.8137	Intermediate Similarity	NPC161855
0.8131	Intermediate Similarity	NPC42662
0.8125	Intermediate Similarity	NPC305475
0.8125	Intermediate Similarity	NPC475461
0.8119	Intermediate Similarity	NPC473291
0.8119	Intermediate Similarity	NPC476009
0.8113	Intermediate Similarity	NPC26617
0.8105	Intermediate Similarity	NPC114979
0.8105	Intermediate Similarity	NPC158756
0.8105	Intermediate Similarity	NPC191476
0.81	Intermediate Similarity	NPC476267
0.8095	Intermediate Similarity	NPC100487
0.8081	Intermediate Similarity	NPC158061
0.8081	Intermediate Similarity	NPC476705
0.8077	Intermediate Similarity	NPC39996
0.8077	Intermediate Similarity	NPC183571
0.8056	Intermediate Similarity	NPC473594
0.8056	Intermediate Similarity	NPC474586
0.8056	Intermediate Similarity	NPC473975
0.8056	Intermediate Similarity	NPC473843
0.8039	Intermediate Similarity	NPC474313
0.8039	Intermediate Similarity	NPC323421
0.8039	Intermediate Similarity	NPC328562
0.8037	Intermediate Similarity	NPC94377
0.8036	Intermediate Similarity	NPC475401
0.8021	Intermediate Similarity	NPC38468
0.8021	Intermediate Similarity	NPC470755
0.8021	Intermediate Similarity	NPC50362
0.8021	Intermediate Similarity	NPC319795
0.802	Intermediate Similarity	NPC474947
0.802	Intermediate Similarity	NPC475900
0.802	Intermediate Similarity	NPC107476
0.8019	Intermediate Similarity	NPC243998
0.8	Intermediate Similarity	NPC231601
0.8	Intermediate Similarity	NPC473390
0.8	Intermediate Similarity	NPC131669
0.8	Intermediate Similarity	NPC475873
0.7982	Intermediate Similarity	NPC194619
0.7982	Intermediate Similarity	NPC317107
0.798	Intermediate Similarity	NPC469368
0.798	Intermediate Similarity	NPC469718
0.798	Intermediate Similarity	NPC329857
0.798	Intermediate Similarity	NPC65359
0.7979	Intermediate Similarity	NPC141810
0.7965	Intermediate Similarity	NPC477092
0.7961	Intermediate Similarity	NPC279561
0.7959	Intermediate Similarity	NPC476707
0.7959	Intermediate Similarity	NPC476706
0.7959	Intermediate Similarity	NPC475819
0.7959	Intermediate Similarity	NPC476805
0.7959	Intermediate Similarity	NPC281516
0.7946	Intermediate Similarity	NPC475305
0.7946	Intermediate Similarity	NPC471146
0.7944	Intermediate Similarity	NPC475510
0.7944	Intermediate Similarity	NPC475587
0.7944	Intermediate Similarity	NPC266514

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 NPC471148 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	233
0.1-0.2	2160
0.2-0.3	3731
0.3-0.4	2077
0.4-0.5	626
0.5-0.6	269
0.6-0.7	46
0.7-0.8	8
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
0.8113	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.8021	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.798	Intermediate Similarity	NPD6698	Approved
0.798	Intermediate Similarity	NPD46	Approved
0.7727	Intermediate Similarity	NPD6371	Approved
0.7624	Intermediate Similarity	NPD7838	Discovery
0.7379	Intermediate Similarity	NPD7983	Approved
0.7353	Intermediate Similarity	NPD1695	Approved
0.7345	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5344	Discontinued
0.717	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4225	Approved
0.7075	Intermediate Similarity	NPD5282	Discontinued
0.7018	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6686	Approved
0.6909	Remote Similarity	NPD6648	Approved
0.6891	Remote Similarity	NPD7115	Discovery
0.6818	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5785	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6635	Remote Similarity	NPD5363	Approved
0.6602	Remote Similarity	NPD7154	Phase 3
0.6591	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6319	Approved
0.6571	Remote Similarity	NPD4249	Approved
0.6569	Remote Similarity	NPD5369	Approved
0.656	Remote Similarity	NPD7642	Approved
0.6552	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4250	Approved
0.6509	Remote Similarity	NPD4251	Approved
0.6505	Remote Similarity	NPD4269	Approved
0.6505	Remote Similarity	NPD4270	Approved
0.6496	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD8273	Phase 1
0.6429	Remote Similarity	NPD7829	Approved
0.6429	Remote Similarity	NPD7830	Approved
0.6417	Remote Similarity	NPD6053	Discontinued
0.6415	Remote Similarity	NPD5786	Approved
0.6406	Remote Similarity	NPD8074	Phase 3
0.6378	Remote Similarity	NPD7492	Approved
0.6339	Remote Similarity	NPD7839	Suspended
0.6333	Remote Similarity	NPD2204	Approved
0.6328	Remote Similarity	NPD6616	Approved
0.6321	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6054	Approved
0.6311	Remote Similarity	NPD4820	Approved
0.6311	Remote Similarity	NPD4822	Approved
0.6311	Remote Similarity	NPD4821	Approved
0.6311	Remote Similarity	NPD4819	Approved
0.6311	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD4252	Approved
0.6286	Remote Similarity	NPD6110	Phase 1
0.6286	Remote Similarity	NPD5362	Discontinued
0.6279	Remote Similarity	NPD7078	Approved
0.627	Remote Similarity	NPD6016	Approved
0.627	Remote Similarity	NPD6015	Approved
0.6239	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6101	Approved
0.6231	Remote Similarity	NPD7736	Approved
0.623	Remote Similarity	NPD4632	Approved
0.6228	Remote Similarity	NPD7638	Approved
0.622	Remote Similarity	NPD5988	Approved
0.622	Remote Similarity	NPD6370	Approved
0.6211	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD8451	Approved
0.619	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6435	Approved
0.619	Remote Similarity	NPD6059	Approved
0.619	Remote Similarity	NPD5209	Approved
0.6183	Remote Similarity	NPD7319	Approved
0.6174	Remote Similarity	NPD7640	Approved
0.6174	Remote Similarity	NPD7639	Approved
0.6172	Remote Similarity	NPD8328	Phase 3
0.6168	Remote Similarity	NPD1694	Approved
0.6154	Remote Similarity	NPD8448	Approved
0.6154	Remote Similarity	NPD8293	Discontinued
0.6148	Remote Similarity	NPD8297	Approved
0.614	Remote Similarity	NPD6083	Phase 2
0.614	Remote Similarity	NPD6084	Phase 2
0.6134	Remote Similarity	NPD5697	Approved
0.6126	Remote Similarity	NPD6411	Approved
0.6126	Remote Similarity	NPD7637	Suspended
0.6117	Remote Similarity	NPD4268	Approved
0.6117	Remote Similarity	NPD4271	Approved
0.6106	Remote Similarity	NPD5695	Phase 3
0.6094	Remote Similarity	NPD8080	Discontinued
0.6087	Remote Similarity	NPD5696	Approved
0.6083	Remote Similarity	NPD6881	Approved
0.6083	Remote Similarity	NPD6899	Approved
0.608	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.608	Remote Similarity	NPD6009	Approved
0.6077	Remote Similarity	NPD7507	Approved
0.6066	Remote Similarity	NPD6650	Approved
0.6066	Remote Similarity	NPD6649	Approved
0.605	Remote Similarity	NPD6008	Approved
0.605	Remote Similarity	NPD7128	Approved
0.605	Remote Similarity	NPD6675	Approved
0.605	Remote Similarity	NPD5739	Approved
0.605	Remote Similarity	NPD6402	Approved
0.6047	Remote Similarity	NPD7604	Phase 2
0.6038	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD6012	Approved
0.6033	Remote Similarity	NPD6014	Approved
0.6033	Remote Similarity	NPD6372	Approved
0.6033	Remote Similarity	NPD6013	Approved
0.6033	Remote Similarity	NPD6373	Approved
0.6019	Remote Similarity	NPD4756	Discovery
0.6016	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5983	Phase 2
0.6016	Remote Similarity	NPD8444	Approved
0.6015	Remote Similarity	NPD8392	Approved
0.6015	Remote Similarity	NPD8390	Approved
0.6015	Remote Similarity	NPD8391	Approved
0.6	Remote Similarity	NPD8341	Approved
0.6	Remote Similarity	NPD5368	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD8342	Approved
0.6	Remote Similarity	NPD8299	Approved
0.6	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD8340	Approved
0.5984	Remote Similarity	NPD7290	Approved
0.5984	Remote Similarity	NPD6883	Approved
0.5984	Remote Similarity	NPD4634	Approved
0.5984	Remote Similarity	NPD7102	Approved
0.597	Remote Similarity	NPD7260	Phase 2
0.5962	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6011	Approved
0.595	Remote Similarity	NPD7320	Approved
0.5946	Remote Similarity	NPD5370	Suspended
0.5938	Remote Similarity	NPD3197	Phase 1
0.5935	Remote Similarity	NPD8130	Phase 1
0.5935	Remote Similarity	NPD6847	Approved
0.5935	Remote Similarity	NPD6869	Approved
0.5935	Remote Similarity	NPD6617	Approved
0.5929	Remote Similarity	NPD6399	Phase 3
0.5913	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD7641	Discontinued
0.5896	Remote Similarity	NPD5956	Approved
0.5893	Remote Similarity	NPD3168	Discontinued
0.5891	Remote Similarity	NPD6921	Approved
0.5887	Remote Similarity	NPD6882	Approved
0.5854	Remote Similarity	NPD2067	Discontinued
0.5841	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5693	Phase 1
0.584	Remote Similarity	NPD8133	Approved
0.5839	Remote Similarity	NPD8415	Approved
0.5833	Remote Similarity	NPD5332	Approved
0.5833	Remote Similarity	NPD5331	Approved
0.5833	Remote Similarity	NPD6336	Discontinued
0.5827	Remote Similarity	NPD7500	Approved
0.5827	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5809	Remote Similarity	NPD6845	Suspended
0.5794	Remote Similarity	NPD4790	Discontinued
0.5781	Remote Similarity	NPD7328	Approved
0.5781	Remote Similarity	NPD7327	Approved
0.578	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7503	Approved
0.5769	Remote Similarity	NPD8033	Approved
0.5766	Remote Similarity	NPD7524	Approved
0.5748	Remote Similarity	NPD6274	Approved
0.5746	Remote Similarity	NPD6033	Approved
0.5736	Remote Similarity	NPD7516	Approved
0.5726	Remote Similarity	NPD6421	Discontinued
0.5714	Remote Similarity	NPD1700	Approved
0.5714	Remote Similarity	NPD6672	Approved
0.5714	Remote Similarity	NPD5737	Approved
0.5702	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD8377	Approved
0.5692	Remote Similarity	NPD8294	Approved
0.569	Remote Similarity	NPD5210	Approved
0.569	Remote Similarity	NPD4629	Approved
0.568	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD8039	Approved
0.5667	Remote Similarity	NPD5211	Phase 2
0.5667	Remote Similarity	NPD7632	Discontinued
0.5667	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5664	Remote Similarity	NPD4753	Phase 2
0.5649	Remote Similarity	NPD8379	Approved
0.5649	Remote Similarity	NPD8268	Approved
0.5649	Remote Similarity	NPD8269	Approved
0.5649	Remote Similarity	NPD8335	Approved
0.5649	Remote Similarity	NPD8378	Approved
0.5649	Remote Similarity	NPD8266	Approved
0.5649	Remote Similarity	NPD8267	Approved
0.5649	Remote Similarity	NPD8380	Approved
0.5649	Remote Similarity	NPD8296	Approved
0.5645	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.563	Remote Similarity	NPD4696	Approved
0.563	Remote Similarity	NPD5285	Approved
0.563	Remote Similarity	NPD5286	Approved
0.5616	Remote Similarity	NPD2575	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