NPASS Compound

Structure

NPC471544 OpenBabel07101718322D 25 27 0 0 1 0 0 0 0 0999 V2000 3.5981 -0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0981 -1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0981 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0116 0.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2026 2.3605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5981 -0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 1.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0981 2.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9641 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 2.5685 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.3660 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 15 1 0 0 0 0 2 15 1 0 0 0 0 3 4 1 0 0 0 0 3 9 1 0 0 0 0 4 15 2 0 0 0 0 5 6 1 0 0 0 0 5 16 1 0 0 0 0 6 18 1 0 0 0 0 7 10 1 0 0 0 0 7 17 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 19 1 0 0 0 0 11 23 1 0 0 0 0 12 16 2 0 0 0 0 12 23 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 20 1 0 0 0 0 14 24 1 0 0 0 0 17 19 1 1 0 0 0 17 24 1 0 0 0 0 18 20 1 6 0 0 0 18 25 1 0 0 0 0 19 22 1 6 0 0 0 20 10 1 1 0 0 0 20 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.21
Volume:	364.849
LogP:	4.037
LogD:	2.932
LogS:	-4.21
# Rotatable Bonds:	8
TPSA:	75.36
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.557
Synthetic Accessibility Score:	5.222
Fsp3:	0.7
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:	-4.655
MDCK Permeability:	1.2704669643426314e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.937
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.09
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153
Plasma Protein Binding (PPB):	97.04085540771484%
Volume Distribution (VD):	1.194
Pgp-substrate:	6.800584316253662%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.109
CYP2C19-inhibitor:	0.106
CYP2C19-substrate:	0.49
CYP2C9-inhibitor:	0.124
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.092
CYP3A4-inhibitor:	0.675
CYP3A4-substrate:	0.239

ADMET: Excretion

Clearance (CL):	14.764
Half-life (T1/2):	0.367

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.797
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.882
Maximum Recommended Daily Dose:	0.342
Skin Sensitization:	0.291
Carcinogencity:	0.734
Eye Corrosion:	0.004
Eye Irritation:	0.19
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC471544

Natural Product ID:	NPC471544
*Common Name:**	(S)-2-((2S,3S,6R)-2-(2-(Furan-3-Yl)Ethyl)-1,5-Dioxaspiro[2.5]Octan-6-Yl)-6-Methylhept-5-Ene-1,2-Diol
IUPAC Name:	(2S)-2-[(2R,3S,6R)-2-[2-(furan-3-yl)ethyl]-1,7-dioxaspiro[2.5]octan-6-yl]-6-methylhept-5-ene-1,2-diol
Synonyms:
Standard InCHIKey:	UPCWMJMYJYZEHI-ZRNYENFQSA-N
Standard InCHI:	InChI=1S/C20H30O5/c1-15(2)4-3-9-19(22,13-21)17-7-10-20(14-24-17)18(25-20)6-5-16-8-11-23-12-16/h4,8,11-12,17-18,21-22H,3,5-7,9-10,13-14H2,1-2H3/t17-,18-,19+,20+/m1/s1
SMILES:	OC[C@]([C@H]1CC[C@@]2(CO1)O[C@@H]2CCc1cocc1)(CCC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256106
PubChem CID:	44448224
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols

*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
NPO12372	Baccharis thymifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18232640]
NPO12372	Baccharis thymifolia	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Activity	=	9.9	day	PMID[506692]
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Inhibition	=	30.8	%	PMID[506692]

☑ 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 NPC471544 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	262
0.1-0.2	1117
0.2-0.3	2987
0.3-0.4	7306
0.4-0.5	11965
0.5-0.6	7843
0.6-0.7	9791
0.7-0.8	1371
0.8-0.85	44
0.85-0.9	8
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473344
0.9683	High Similarity	NPC471545
0.9194	High Similarity	NPC471549
0.9194	High Similarity	NPC473379
0.8984	High Similarity	NPC471573
0.8984	High Similarity	NPC471554
0.8984	High Similarity	NPC471501
0.8984	High Similarity	NPC473355
0.8976	High Similarity	NPC471559
0.8855	High Similarity	NPC17681
0.8788	High Similarity	NPC97740
0.8788	High Similarity	NPC45358
0.8571	High Similarity	NPC137295
0.855	High Similarity	NPC137570
0.855	High Similarity	NPC476016
0.8511	High Similarity	NPC5676
0.8467	Intermediate Similarity	NPC473268
0.8417	Intermediate Similarity	NPC67003
0.8409	Intermediate Similarity	NPC474830
0.8403	Intermediate Similarity	NPC69647
0.8403	Intermediate Similarity	NPC125182
0.8397	Intermediate Similarity	NPC474829
0.8382	Intermediate Similarity	NPC106247
0.8356	Intermediate Similarity	NPC268905
0.8346	Intermediate Similarity	NPC474279
0.8346	Intermediate Similarity	NPC474438
0.8333	Intermediate Similarity	NPC329694
0.8333	Intermediate Similarity	NPC81912
0.8333	Intermediate Similarity	NPC474260
0.8333	Intermediate Similarity	NPC329922
0.831	Intermediate Similarity	NPC86935
0.8309	Intermediate Similarity	NPC474425
0.8309	Intermediate Similarity	NPC474426
0.8309	Intermediate Similarity	NPC474407
0.8286	Intermediate Similarity	NPC90296
0.8264	Intermediate Similarity	NPC255414
0.8255	Intermediate Similarity	NPC187149
0.8255	Intermediate Similarity	NPC299038
0.8239	Intermediate Similarity	NPC243577
0.8231	Intermediate Similarity	NPC474378
0.8231	Intermediate Similarity	NPC44577
0.8231	Intermediate Similarity	NPC474219
0.8207	Intermediate Similarity	NPC7388
0.8201	Intermediate Similarity	NPC186626
0.8188	Intermediate Similarity	NPC158525
0.8176	Intermediate Similarity	NPC57998
0.8169	Intermediate Similarity	NPC121158
0.8146	Intermediate Similarity	NPC335761
0.8138	Intermediate Similarity	NPC250228
0.8133	Intermediate Similarity	NPC45101
0.8129	Intermediate Similarity	NPC46896
0.8129	Intermediate Similarity	NPC303217
0.8121	Intermediate Similarity	NPC214541
0.8121	Intermediate Similarity	NPC44675
0.812	Intermediate Similarity	NPC71274
0.812	Intermediate Similarity	NPC75557
0.8108	Intermediate Similarity	NPC75906
0.8106	Intermediate Similarity	NPC475818
0.8105	Intermediate Similarity	NPC271657
0.8092	Intermediate Similarity	NPC18347
0.8092	Intermediate Similarity	NPC149896
0.8092	Intermediate Similarity	NPC5079
0.8092	Intermediate Similarity	NPC79557
0.8085	Intermediate Similarity	NPC107571
0.8085	Intermediate Similarity	NPC90953
0.8079	Intermediate Similarity	NPC475967
0.8062	Intermediate Similarity	NPC208906
0.8062	Intermediate Similarity	NPC144745
0.8058	Intermediate Similarity	NPC14650
0.8058	Intermediate Similarity	NPC476947
0.8056	Intermediate Similarity	NPC251865
0.8045	Intermediate Similarity	NPC118853
0.8043	Intermediate Similarity	NPC218838
0.8042	Intermediate Similarity	NPC184053
0.8039	Intermediate Similarity	NPC134254
0.8039	Intermediate Similarity	NPC234660
0.8039	Intermediate Similarity	NPC302369
0.8039	Intermediate Similarity	NPC39986
0.8039	Intermediate Similarity	NPC51568
0.803	Intermediate Similarity	NPC263870
0.803	Intermediate Similarity	NPC477967
0.8029	Intermediate Similarity	NPC89133
0.8029	Intermediate Similarity	NPC61788
0.8028	Intermediate Similarity	NPC282973
0.8026	Intermediate Similarity	NPC472653
0.8026	Intermediate Similarity	NPC477402
0.8026	Intermediate Similarity	NPC25255
0.8015	Intermediate Similarity	NPC474817
0.8013	Intermediate Similarity	NPC261597
0.8013	Intermediate Similarity	NPC194499
0.8013	Intermediate Similarity	NPC36655
0.8	Intermediate Similarity	NPC472282
0.8	Intermediate Similarity	NPC264943
0.8	Intermediate Similarity	NPC195920
0.8	Intermediate Similarity	NPC472651
0.8	Intermediate Similarity	NPC177331
0.7987	Intermediate Similarity	NPC476858
0.7987	Intermediate Similarity	NPC476856
0.7987	Intermediate Similarity	NPC476857
0.7987	Intermediate Similarity	NPC123088
0.7987	Intermediate Similarity	NPC147168
0.7986	Intermediate Similarity	NPC254198
0.7986	Intermediate Similarity	NPC288209
0.7986	Intermediate Similarity	NPC476946
0.7986	Intermediate Similarity	NPC80635
0.7974	Intermediate Similarity	NPC193798
0.7974	Intermediate Similarity	NPC200782
0.797	Intermediate Similarity	NPC476351
0.7961	Intermediate Similarity	NPC262872
0.7961	Intermediate Similarity	NPC472779
0.7959	Intermediate Similarity	NPC471007
0.7949	Intermediate Similarity	NPC471397
0.7949	Intermediate Similarity	NPC271235
0.7949	Intermediate Similarity	NPC472652
0.7947	Intermediate Similarity	NPC469485
0.7945	Intermediate Similarity	NPC475864
0.7945	Intermediate Similarity	NPC104924
0.7935	Intermediate Similarity	NPC23387
0.7931	Intermediate Similarity	NPC476944
0.7926	Intermediate Similarity	NPC23086
0.7922	Intermediate Similarity	NPC477405
0.7922	Intermediate Similarity	NPC472773
0.7919	Intermediate Similarity	NPC18135
0.7914	Intermediate Similarity	NPC470859
0.7914	Intermediate Similarity	NPC214097
0.7908	Intermediate Similarity	NPC470789
0.7907	Intermediate Similarity	NPC28054
0.7905	Intermediate Similarity	NPC470998
0.7905	Intermediate Similarity	NPC195325
0.7905	Intermediate Similarity	NPC472654
0.7895	Intermediate Similarity	NPC173544
0.7895	Intermediate Similarity	NPC472777
0.7895	Intermediate Similarity	NPC472776
0.7895	Intermediate Similarity	NPC289911
0.7895	Intermediate Similarity	NPC283284
0.7895	Intermediate Similarity	NPC88007
0.7895	Intermediate Similarity	NPC472778
0.7891	Intermediate Similarity	NPC221809
0.7885	Intermediate Similarity	NPC476850
0.7885	Intermediate Similarity	NPC476853
0.7885	Intermediate Similarity	NPC476861
0.7885	Intermediate Similarity	NPC173516
0.7877	Intermediate Similarity	NPC469642
0.7872	Intermediate Similarity	NPC212729
0.7871	Intermediate Similarity	NPC476860
0.7871	Intermediate Similarity	NPC146991
0.7871	Intermediate Similarity	NPC276551
0.7867	Intermediate Similarity	NPC121615
0.7867	Intermediate Similarity	NPC469503
0.7867	Intermediate Similarity	NPC294511
0.7863	Intermediate Similarity	NPC243704
0.7862	Intermediate Similarity	NPC242756
0.7862	Intermediate Similarity	NPC110305
0.7857	Intermediate Similarity	NPC117986
0.7857	Intermediate Similarity	NPC207978
0.7857	Intermediate Similarity	NPC211777
0.7857	Intermediate Similarity	NPC69028
0.7857	Intermediate Similarity	NPC472771
0.7857	Intermediate Similarity	NPC263432
0.7852	Intermediate Similarity	NPC104172
0.7852	Intermediate Similarity	NPC196846
0.7852	Intermediate Similarity	NPC227980
0.7852	Intermediate Similarity	NPC228842
0.7852	Intermediate Similarity	NPC88886
0.7847	Intermediate Similarity	NPC205765
0.7843	Intermediate Similarity	NPC477403
0.7843	Intermediate Similarity	NPC472671
0.7842	Intermediate Similarity	NPC473982
0.7838	Intermediate Similarity	NPC14875
0.7838	Intermediate Similarity	NPC474220
0.7838	Intermediate Similarity	NPC471618
0.7838	Intermediate Similarity	NPC474255
0.7834	Intermediate Similarity	NPC160651
0.7829	Intermediate Similarity	NPC209364
0.7829	Intermediate Similarity	NPC107646
0.7829	Intermediate Similarity	NPC263265
0.7829	Intermediate Similarity	NPC60973
0.7829	Intermediate Similarity	NPC126723
0.7826	Intermediate Similarity	NPC21460
0.7823	Intermediate Similarity	NPC346
0.7823	Intermediate Similarity	NPC474044
0.7823	Intermediate Similarity	NPC287495
0.7823	Intermediate Similarity	NPC9370
0.7821	Intermediate Similarity	NPC470875
0.782	Intermediate Similarity	NPC474136
0.7817	Intermediate Similarity	NPC294470
0.7817	Intermediate Similarity	NPC286130
0.7817	Intermediate Similarity	NPC310830
0.7815	Intermediate Similarity	NPC253201
0.7815	Intermediate Similarity	NPC34421
0.7815	Intermediate Similarity	NPC237259
0.7815	Intermediate Similarity	NPC178932
0.7815	Intermediate Similarity	NPC302054
0.7815	Intermediate Similarity	NPC98206
0.7815	Intermediate Similarity	NPC282445
0.7812	Intermediate Similarity	NPC1811
0.7812	Intermediate Similarity	NPC26157
0.7808	Intermediate Similarity	NPC307346
0.7808	Intermediate Similarity	NPC261733
0.7808	Intermediate Similarity	NPC267004

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 NPC471544 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	860
0.2-0.3	2094
0.3-0.4	2672
0.4-0.5	2038
0.5-0.6	968
0.6-0.7	273
0.7-0.8	7
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
0.7763	Intermediate Similarity	NPD5761	Phase 2
0.7763	Intermediate Similarity	NPD5760	Phase 2
0.7671	Intermediate Similarity	NPD4628	Phase 3
0.7226	Intermediate Similarity	NPD4380	Phase 2
0.7197	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6559	Discontinued
0.716	Intermediate Similarity	NPD8434	Phase 2
0.7134	Intermediate Similarity	NPD1934	Approved
0.7132	Intermediate Similarity	NPD9092	Discovery
0.7114	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD1549	Phase 2
0.7063	Intermediate Similarity	NPD7075	Discontinued
0.7059	Intermediate Similarity	NPD6799	Approved
0.7047	Intermediate Similarity	NPD2796	Approved
0.7032	Intermediate Similarity	NPD920	Approved
0.702	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3882	Suspended
0.7	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7033	Discontinued
0.6964	Remote Similarity	NPD6764	Approved
0.6964	Remote Similarity	NPD6765	Approved
0.6954	Remote Similarity	NPD2424	Discontinued
0.6944	Remote Similarity	NPD9494	Approved
0.6928	Remote Similarity	NPD3818	Discontinued
0.6923	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6801	Discontinued
0.6909	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6166	Phase 2
0.6909	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6599	Discontinued
0.6887	Remote Similarity	NPD6005	Phase 3
0.6887	Remote Similarity	NPD6002	Phase 3
0.6887	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6004	Phase 3
0.6887	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2344	Approved
0.6883	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5494	Approved
0.6835	Remote Similarity	NPD9545	Approved
0.6831	Remote Similarity	NPD1608	Approved
0.6829	Remote Similarity	NPD1247	Approved
0.6826	Remote Similarity	NPD2163	Approved
0.6821	Remote Similarity	NPD1551	Phase 2
0.6815	Remote Similarity	NPD5403	Approved
0.681	Remote Similarity	NPD919	Approved
0.681	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD6785	Approved
0.6802	Remote Similarity	NPD6784	Approved
0.6795	Remote Similarity	NPD5401	Approved
0.6795	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5844	Phase 1
0.6779	Remote Similarity	NPD6355	Discontinued
0.677	Remote Similarity	NPD2801	Approved
0.677	Remote Similarity	NPD7819	Suspended
0.6765	Remote Similarity	NPD7685	Pre-registration
0.6761	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6233	Phase 2
0.6755	Remote Similarity	NPD1510	Phase 2
0.675	Remote Similarity	NPD7411	Suspended
0.6748	Remote Similarity	NPD3749	Approved
0.6746	Remote Similarity	NPD7074	Phase 3
0.6733	Remote Similarity	NPD6653	Approved
0.6731	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5402	Approved
0.6728	Remote Similarity	NPD3817	Phase 2
0.6728	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD2684	Approved
0.6715	Remote Similarity	NPD1241	Discontinued
0.6713	Remote Similarity	NPD9717	Approved
0.6711	Remote Similarity	NPD1240	Approved
0.671	Remote Similarity	NPD3887	Approved
0.671	Remote Similarity	NPD2309	Approved
0.671	Remote Similarity	NPD2354	Approved
0.6689	Remote Similarity	NPD6798	Discontinued
0.6688	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1243	Approved
0.6686	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD6832	Phase 2
0.6667	Remote Similarity	NPD230	Phase 1
0.6667	Remote Similarity	NPD447	Suspended
0.6647	Remote Similarity	NPD7472	Approved
0.6645	Remote Similarity	NPD4308	Phase 3
0.6644	Remote Similarity	NPD5647	Approved
0.6643	Remote Similarity	NPD1091	Approved
0.6642	Remote Similarity	NPD7843	Approved
0.6642	Remote Similarity	NPD290	Approved
0.6627	Remote Similarity	NPD3751	Discontinued
0.6624	Remote Similarity	NPD1511	Approved
0.6623	Remote Similarity	NPD1607	Approved
0.662	Remote Similarity	NPD17	Approved
0.6619	Remote Similarity	NPD7157	Approved
0.6608	Remote Similarity	NPD6797	Phase 2
0.6608	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.66	Remote Similarity	NPD3142	Approved
0.66	Remote Similarity	NPD3140	Approved
0.6597	Remote Similarity	NPD3972	Approved
0.6587	Remote Similarity	NPD3787	Discontinued
0.6582	Remote Similarity	NPD2533	Approved
0.6582	Remote Similarity	NPD4661	Approved
0.6582	Remote Similarity	NPD2534	Approved
0.6582	Remote Similarity	NPD4662	Approved
0.6582	Remote Similarity	NPD2532	Approved
0.6581	Remote Similarity	NPD2800	Approved
0.6577	Remote Similarity	NPD2313	Discontinued
0.6577	Remote Similarity	NPD3764	Approved
0.657	Remote Similarity	NPD7251	Discontinued
0.6564	Remote Similarity	NPD8455	Phase 2
0.6561	Remote Similarity	NPD5058	Phase 3
0.6558	Remote Similarity	NPD1471	Phase 3
0.6548	Remote Similarity	NPD3926	Phase 2
0.6541	Remote Similarity	NPD6273	Approved
0.6541	Remote Similarity	NPD1512	Approved
0.6538	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD3750	Approved
0.6536	Remote Similarity	NPD2799	Discontinued
0.6536	Remote Similarity	NPD5588	Approved
0.6533	Remote Similarity	NPD4062	Phase 3
0.6532	Remote Similarity	NPD7808	Phase 3
0.6531	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1019	Discontinued
0.6522	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD3823	Discontinued
0.6503	Remote Similarity	NPD1778	Approved
0.6497	Remote Similarity	NPD6190	Approved
0.6494	Remote Similarity	NPD6100	Approved
0.6494	Remote Similarity	NPD6099	Approved
0.6494	Remote Similarity	NPD2935	Discontinued
0.649	Remote Similarity	NPD4307	Phase 2
0.649	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1652	Phase 2
0.6471	Remote Similarity	NPD4538	Approved
0.6471	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4536	Approved
0.6467	Remote Similarity	NPD3268	Approved
0.6463	Remote Similarity	NPD6362	Approved
0.6463	Remote Similarity	NPD1203	Approved
0.6463	Remote Similarity	NPD2797	Approved
0.6461	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2346	Discontinued
0.6452	Remote Similarity	NPD2353	Approved
0.6452	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD1933	Approved
0.6447	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7199	Phase 2
0.6429	Remote Similarity	NPD5960	Phase 3
0.6429	Remote Similarity	NPD6959	Discontinued
0.6429	Remote Similarity	NPD3748	Approved
0.642	Remote Similarity	NPD2651	Approved
0.642	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3226	Approved
0.642	Remote Similarity	NPD2649	Approved
0.6419	Remote Similarity	NPD2798	Approved
0.6412	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.641	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6844	Discontinued
0.64	Remote Similarity	NPD8313	Approved
0.64	Remote Similarity	NPD8312	Approved
0.64	Remote Similarity	NPD3027	Phase 3
0.6395	Remote Similarity	NPD8651	Approved
0.6395	Remote Similarity	NPD1876	Approved
0.6386	Remote Similarity	NPD7768	Phase 2
0.6382	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD1613	Approved
0.6377	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7097	Phase 1
0.6364	Remote Similarity	NPD1465	Phase 2
0.6358	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD411	Approved
0.6346	Remote Similarity	NPD5762	Approved
0.6346	Remote Similarity	NPD5763	Approved
0.6345	Remote Similarity	NPD3496	Discontinued
0.6341	Remote Similarity	NPD6385	Approved
0.6341	Remote Similarity	NPD6386	Approved
0.634	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.634	Remote Similarity	NPD5124	Phase 1
0.6337	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD5049	Phase 3
0.6333	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD8127	Discontinued
0.6329	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD4110	Phase 3
0.6325	Remote Similarity	NPD5353	Approved
0.6319	Remote Similarity	NPD7458	Discontinued
0.6312	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD5958	Discontinued
0.6306	Remote Similarity	NPD4534	Discontinued
0.6303	Remote Similarity	NPD7577	Discontinued

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