NPASS Compound

Structure

NPC471549 OpenBabel07101719242D 24 25 0 0 1 0 0 0 0 0999 V2000 1.2321 4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7321 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3776 -3.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0468 -2.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -2.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.7976 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 6 1 0 0 0 0 3 7 1 0 0 0 0 4 5 1 0 0 0 0 4 11 1 0 0 0 0 5 16 2 0 0 0 0 6 17 2 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 23 1 0 0 0 0 13 18 2 0 0 0 0 13 23 1 0 0 0 0 14 17 1 0 0 0 0 14 24 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 19 20 1 1 0 0 0 19 24 1 0 0 0 0 20 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	361.978
LogP:	4.072
LogD:	3.379
LogS:	-4.369
# Rotatable Bonds:	8
TPSA:	62.83
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.71
Synthetic Accessibility Score:	4.335
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.56
MDCK Permeability:	3.071675018873066e-05
Pgp-inhibitor:	0.716
Pgp-substrate:	0.229
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.384
30% Bioavailability (F30%):	0.107

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.371
Plasma Protein Binding (PPB):	95.5772933959961%
Volume Distribution (VD):	1.307
Pgp-substrate:	4.412272930145264%

ADMET: Metabolism

CYP1A2-inhibitor:	0.14
CYP1A2-substrate:	0.087
CYP2C19-inhibitor:	0.19
CYP2C19-substrate:	0.126
CYP2C9-inhibitor:	0.305
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.128
CYP2D6-substrate:	0.108
CYP3A4-inhibitor:	0.549
CYP3A4-substrate:	0.242

ADMET: Excretion

Clearance (CL):	11.204
Half-life (T1/2):	0.597

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.03
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.41
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.321
Carcinogencity:	0.727
Eye Corrosion:	0.004
Eye Irritation:	0.243
Respiratory Toxicity:	0.794

Download Data

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

Natural Product: NPC471549

Natural Product ID:	NPC471549
*Common Name:**	(2S)-2-[(2R,5E)-5-[3-(Furan-3-Yl)Propylidene]Oxan-2-Yl]-6-Methylhept-5-Ene-1,2-Diol
IUPAC Name:	(2S)-2-[(2R,5E)-5-[3-(furan-3-yl)propylidene]oxan-2-yl]-6-methylhept-5-ene-1,2-diol
Synonyms:
Standard InCHIKey:	JRRKNNHWQABOMA-ZKCRXDLMSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-16(2)5-4-11-20(22,15-21)19-9-8-17(14-24-19)6-3-7-18-10-12-23-13-18/h5-6,10,12-13,19,21-22H,3-4,7-9,11,14-15H2,1-2H3/b17-6+/t19-,20+/m1/s1
SMILES:	CC(=CCCC(CO)(C1CCC(=CCCC2=COC=C2)CO1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL256320
PubChem CID:	24801762
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	=	16.2	day	PMID[534479]
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Inhibition	=	14.4	%	PMID[534479]

☑ 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 NPC471549 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	207
0.1-0.2	1007
0.2-0.3	3034
0.3-0.4	7941
0.4-0.5	12728
0.5-0.6	8209
0.6-0.7	8863
0.7-0.8	630
0.8-0.85	51
0.85-0.9	24
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473379
0.925	High Similarity	NPC471559
0.9194	High Similarity	NPC471544
0.9194	High Similarity	NPC473344
0.8943	High Similarity	NPC474830
0.8943	High Similarity	NPC476016
0.8934	High Similarity	NPC474829
0.8889	High Similarity	NPC471545
0.8862	High Similarity	NPC81912
0.8862	High Similarity	NPC474260
0.8862	High Similarity	NPC329922
0.8862	High Similarity	NPC329694
0.881	High Similarity	NPC17681
0.879	High Similarity	NPC471573
0.879	High Similarity	NPC471501
0.879	High Similarity	NPC473355
0.879	High Similarity	NPC471554
0.877	High Similarity	NPC475818
0.874	High Similarity	NPC97740
0.872	High Similarity	NPC474279
0.872	High Similarity	NPC474438
0.8696	High Similarity	NPC177331
0.8678	High Similarity	NPC474817
0.8629	High Similarity	NPC71274
0.8629	High Similarity	NPC75557
0.8594	High Similarity	NPC45358
0.8583	High Similarity	NPC208906
0.8583	High Similarity	NPC144745
0.8537	High Similarity	NPC477967
0.8537	High Similarity	NPC289911
0.8537	High Similarity	NPC263870
0.8537	High Similarity	NPC283284
0.8527	High Similarity	NPC474426
0.8527	High Similarity	NPC474407
0.8527	High Similarity	NPC474425
0.8475	Intermediate Similarity	NPC26157
0.8475	Intermediate Similarity	NPC1811
0.8468	Intermediate Similarity	NPC476351
0.8455	Intermediate Similarity	NPC474136
0.8455	Intermediate Similarity	NPC79557
0.8417	Intermediate Similarity	NPC28054
0.8409	Intermediate Similarity	NPC473268
0.84	Intermediate Similarity	NPC118853
0.8397	Intermediate Similarity	NPC476947
0.8385	Intermediate Similarity	NPC218838
0.8361	Intermediate Similarity	NPC243704
0.8346	Intermediate Similarity	NPC137570
0.8291	Intermediate Similarity	NPC471521
0.8291	Intermediate Similarity	NPC473356
0.8268	Intermediate Similarity	NPC23086
0.8235	Intermediate Similarity	NPC105249
0.8231	Intermediate Similarity	NPC61788
0.8175	Intermediate Similarity	NPC476946
0.8168	Intermediate Similarity	NPC473982
0.816	Intermediate Similarity	NPC1848
0.8145	Intermediate Similarity	NPC473969
0.813	Intermediate Similarity	NPC217180
0.813	Intermediate Similarity	NPC312525
0.813	Intermediate Similarity	NPC131801
0.8125	Intermediate Similarity	NPC138139
0.8125	Intermediate Similarity	NPC46536
0.8116	Intermediate Similarity	NPC137295
0.8115	Intermediate Similarity	NPC205523
0.8115	Intermediate Similarity	NPC150895
0.811	Intermediate Similarity	NPC243269
0.811	Intermediate Similarity	NPC477038
0.811	Intermediate Similarity	NPC477965
0.8102	Intermediate Similarity	NPC52412
0.8095	Intermediate Similarity	NPC317217
0.8092	Intermediate Similarity	NPC89133
0.8065	Intermediate Similarity	NPC21831
0.8065	Intermediate Similarity	NPC187547
0.8062	Intermediate Similarity	NPC83178
0.8058	Intermediate Similarity	NPC5676
0.8049	Intermediate Similarity	NPC45536
0.8045	Intermediate Similarity	NPC106247
0.8014	Intermediate Similarity	NPC7388
0.8	Intermediate Similarity	NPC186626
0.8	Intermediate Similarity	NPC112706
0.8	Intermediate Similarity	NPC207294
0.8	Intermediate Similarity	NPC215109
0.8	Intermediate Similarity	NPC170604
0.7969	Intermediate Similarity	NPC188377
0.7969	Intermediate Similarity	NPC65735
0.7958	Intermediate Similarity	NPC69647
0.7958	Intermediate Similarity	NPC125182
0.7956	Intermediate Similarity	NPC90296
0.7956	Intermediate Similarity	NPC67003
0.7926	Intermediate Similarity	NPC303217
0.7923	Intermediate Similarity	NPC95567
0.7923	Intermediate Similarity	NPC319140
0.7914	Intermediate Similarity	NPC243577
0.7907	Intermediate Similarity	NPC179354
0.7891	Intermediate Similarity	NPC16922
0.7883	Intermediate Similarity	NPC90953
0.7883	Intermediate Similarity	NPC107571
0.7863	Intermediate Similarity	NPC329707
0.7863	Intermediate Similarity	NPC477040
0.7863	Intermediate Similarity	NPC477039
0.7863	Intermediate Similarity	NPC477966
0.7863	Intermediate Similarity	NPC477123
0.7857	Intermediate Similarity	NPC4898
0.7857	Intermediate Similarity	NPC476944
0.7852	Intermediate Similarity	NPC158525
0.7846	Intermediate Similarity	NPC74612
0.7832	Intermediate Similarity	NPC470998
0.7817	Intermediate Similarity	NPC255414
0.781	Intermediate Similarity	NPC472376
0.7794	Intermediate Similarity	NPC46896
0.7793	Intermediate Similarity	NPC44577
0.7793	Intermediate Similarity	NPC147168
0.7786	Intermediate Similarity	NPC290955
0.7778	Intermediate Similarity	NPC288209
0.777	Intermediate Similarity	NPC205765
0.7769	Intermediate Similarity	NPC300098
0.7769	Intermediate Similarity	NPC290193
0.7762	Intermediate Similarity	NPC471007
0.7761	Intermediate Similarity	NPC471817
0.776	Intermediate Similarity	NPC474987
0.7752	Intermediate Similarity	NPC272899
0.7746	Intermediate Similarity	NPC346
0.7744	Intermediate Similarity	NPC476925
0.7744	Intermediate Similarity	NPC21460
0.7737	Intermediate Similarity	NPC310830
0.7727	Intermediate Similarity	NPC327527
0.7727	Intermediate Similarity	NPC26532
0.7727	Intermediate Similarity	NPC279877
0.7727	Intermediate Similarity	NPC476917
0.7721	Intermediate Similarity	NPC92941
0.7721	Intermediate Similarity	NPC14650
0.7717	Intermediate Similarity	NPC137710
0.7714	Intermediate Similarity	NPC121158
0.7708	Intermediate Similarity	NPC234494
0.7703	Intermediate Similarity	NPC45101
0.7698	Intermediate Similarity	NPC201370
0.7698	Intermediate Similarity	NPC473983
0.7692	Intermediate Similarity	NPC250228
0.7692	Intermediate Similarity	NPC476938
0.7692	Intermediate Similarity	NPC302987
0.7692	Intermediate Similarity	NPC476937
0.7687	Intermediate Similarity	NPC214541
0.7687	Intermediate Similarity	NPC477645
0.7687	Intermediate Similarity	NPC298190
0.7687	Intermediate Similarity	NPC281258
0.7687	Intermediate Similarity	NPC44675
0.7681	Intermediate Similarity	NPC476943
0.7681	Intermediate Similarity	NPC220094
0.7676	Intermediate Similarity	NPC469642
0.7671	Intermediate Similarity	NPC33938
0.7671	Intermediate Similarity	NPC268905
0.7664	Intermediate Similarity	NPC204592
0.766	Intermediate Similarity	NPC242756
0.766	Intermediate Similarity	NPC267632
0.7655	Intermediate Similarity	NPC196846
0.7655	Intermediate Similarity	NPC470997
0.7652	Intermediate Similarity	NPC246392
0.7651	Intermediate Similarity	NPC475967
0.7639	Intermediate Similarity	NPC476942
0.7639	Intermediate Similarity	NPC476941
0.7634	Intermediate Similarity	NPC471074
0.7634	Intermediate Similarity	NPC303010
0.7634	Intermediate Similarity	NPC473885
0.7619	Intermediate Similarity	NPC302054
0.7619	Intermediate Similarity	NPC98206
0.7619	Intermediate Similarity	NPC237259
0.7619	Intermediate Similarity	NPC34421
0.7619	Intermediate Similarity	NPC253201
0.7612	Intermediate Similarity	NPC939
0.7609	Intermediate Similarity	NPC278832
0.7609	Intermediate Similarity	NPC64157
0.7609	Intermediate Similarity	NPC470742
0.7606	Intermediate Similarity	NPC86935
0.7606	Intermediate Similarity	NPC251865
0.76	Intermediate Similarity	NPC477402
0.7591	Intermediate Similarity	NPC265793
0.7591	Intermediate Similarity	NPC159786
0.7589	Intermediate Similarity	NPC184053
0.7584	Intermediate Similarity	NPC194499
0.7584	Intermediate Similarity	NPC299038
0.7584	Intermediate Similarity	NPC36655
0.7584	Intermediate Similarity	NPC187149
0.7584	Intermediate Similarity	NPC261597
0.7581	Intermediate Similarity	NPC22678
0.7574	Intermediate Similarity	NPC470740
0.7568	Intermediate Similarity	NPC264943
0.7559	Intermediate Similarity	NPC227660
0.7557	Intermediate Similarity	NPC130275
0.7554	Intermediate Similarity	NPC130976
0.7552	Intermediate Similarity	NPC185456
0.7551	Intermediate Similarity	NPC121615
0.7551	Intermediate Similarity	NPC474219
0.7551	Intermediate Similarity	NPC472672
0.7551	Intermediate Similarity	NPC294511
0.7551	Intermediate Similarity	NPC474378
0.7551	Intermediate Similarity	NPC470996
0.755	Intermediate Similarity	NPC263432
0.755	Intermediate Similarity	NPC200782
0.7537	Intermediate Similarity	NPC120836
0.7537	Intermediate Similarity	NPC223063
0.7536	Intermediate Similarity	NPC146872

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 NPC471549 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	789
0.2-0.3	1902
0.3-0.4	2728
0.4-0.5	2091
0.5-0.6	1123
0.6-0.7	297
0.7-0.8	11
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
0.7343	Intermediate Similarity	NPD4628	Phase 3
0.7333	Intermediate Similarity	NPD5760	Phase 2
0.7333	Intermediate Similarity	NPD5761	Phase 2
0.7258	Intermediate Similarity	NPD2684	Approved
0.7254	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2424	Discontinued
0.7177	Intermediate Similarity	NPD290	Approved
0.7165	Intermediate Similarity	NPD7843	Approved
0.7154	Intermediate Similarity	NPD9092	Discovery
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1241	Discontinued
0.709	Intermediate Similarity	NPD9717	Approved
0.7059	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6798	Discontinued
0.7029	Intermediate Similarity	NPD6832	Phase 2
0.7021	Intermediate Similarity	NPD6355	Discontinued
0.7007	Intermediate Similarity	NPD5647	Approved
0.7	Intermediate Similarity	NPD7157	Approved
0.7	Intermediate Similarity	NPD6233	Phase 2
0.6975	Remote Similarity	NPD6559	Discontinued
0.6972	Remote Similarity	NPD6653	Approved
0.6957	Remote Similarity	NPD9494	Approved
0.6913	Remote Similarity	NPD4662	Approved
0.6913	Remote Similarity	NPD4661	Approved
0.6897	Remote Similarity	NPD2344	Approved
0.6883	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4062	Phase 3
0.6875	Remote Similarity	NPD7033	Discontinued
0.6875	Remote Similarity	NPD4308	Phase 3
0.6849	Remote Similarity	NPD1549	Phase 2
0.6846	Remote Similarity	NPD6799	Approved
0.6824	Remote Similarity	NPD3887	Approved
0.6824	Remote Similarity	NPD2354	Approved
0.6821	Remote Similarity	NPD5403	Approved
0.6812	Remote Similarity	NPD1203	Approved
0.6812	Remote Similarity	NPD2797	Approved
0.6812	Remote Similarity	NPD6362	Approved
0.6803	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5401	Approved
0.6797	Remote Similarity	NPD4380	Phase 2
0.6783	Remote Similarity	NPD447	Suspended
0.6783	Remote Similarity	NPD1933	Approved
0.6781	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD1358	Approved
0.6766	Remote Similarity	NPD8434	Phase 2
0.6763	Remote Similarity	NPD1019	Discontinued
0.6759	Remote Similarity	NPD2799	Discontinued
0.6755	Remote Similarity	NPD6273	Approved
0.6752	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD7075	Discontinued
0.6744	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3972	Approved
0.6713	Remote Similarity	NPD3142	Approved
0.6713	Remote Similarity	NPD3140	Approved
0.6713	Remote Similarity	NPD4307	Phase 2
0.6712	Remote Similarity	NPD1551	Phase 2
0.6712	Remote Similarity	NPD2796	Approved
0.6711	Remote Similarity	NPD2309	Approved
0.671	Remote Similarity	NPD1934	Approved
0.671	Remote Similarity	NPD6801	Discontinued
0.6708	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.669	Remote Similarity	NPD2313	Discontinued
0.669	Remote Similarity	NPD7097	Phase 1
0.669	Remote Similarity	NPD3268	Approved
0.6688	Remote Similarity	NPD3882	Suspended
0.6688	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD6004	Phase 3
0.6667	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD6765	Approved
0.6645	Remote Similarity	NPD5049	Phase 3
0.6643	Remote Similarity	NPD2798	Approved
0.6642	Remote Similarity	NPD1091	Approved
0.6623	Remote Similarity	NPD2651	Approved
0.6623	Remote Similarity	NPD2649	Approved
0.662	Remote Similarity	NPD7095	Approved
0.6619	Remote Similarity	NPD1876	Approved
0.6601	Remote Similarity	NPD920	Approved
0.6599	Remote Similarity	NPD2935	Discontinued
0.6599	Remote Similarity	NPD2239	Approved
0.6599	Remote Similarity	NPD2240	Approved
0.6593	Remote Similarity	NPD1894	Discontinued
0.6593	Remote Similarity	NPD9545	Approved
0.6582	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD411	Approved
0.6569	Remote Similarity	NPD3496	Discontinued
0.6567	Remote Similarity	NPD9493	Approved
0.6562	Remote Similarity	NPD3134	Approved
0.6556	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD2353	Approved
0.6554	Remote Similarity	NPD2346	Discontinued
0.6554	Remote Similarity	NPD1471	Phase 3
0.6552	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7411	Suspended
0.6533	Remote Similarity	NPD4110	Phase 3
0.6533	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5588	Approved
0.6524	Remote Similarity	NPD2163	Approved
0.6524	Remote Similarity	NPD3818	Discontinued
0.6519	Remote Similarity	NPD5402	Approved
0.651	Remote Similarity	NPD5958	Discontinued
0.651	Remote Similarity	NPD4534	Discontinued
0.6509	Remote Similarity	NPD6785	Approved
0.6509	Remote Similarity	NPD6784	Approved
0.6508	Remote Similarity	NPD291	Approved
0.6503	Remote Similarity	NPD6166	Phase 2
0.6503	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.65	Remote Similarity	NPD919	Approved
0.6497	Remote Similarity	NPD6844	Discontinued
0.6496	Remote Similarity	NPD1778	Approved
0.6496	Remote Similarity	NPD6516	Phase 2
0.6496	Remote Similarity	NPD5846	Approved
0.6493	Remote Similarity	NPD6671	Approved
0.6486	Remote Similarity	NPD5712	Approved
0.6483	Remote Similarity	NPD1240	Approved
0.6475	Remote Similarity	NPD1608	Approved
0.6471	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1652	Phase 2
0.6463	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD4538	Approved
0.6463	Remote Similarity	NPD4536	Approved
0.646	Remote Similarity	NPD5494	Approved
0.6458	Remote Similarity	NPD3764	Approved
0.6456	Remote Similarity	NPD7819	Suspended
0.6454	Remote Similarity	NPD3267	Approved
0.6454	Remote Similarity	NPD3266	Approved
0.6449	Remote Similarity	NPD3847	Discontinued
0.6447	Remote Similarity	NPD5058	Phase 3
0.6447	Remote Similarity	NPD7440	Discontinued
0.6443	Remote Similarity	NPD5762	Approved
0.6443	Remote Similarity	NPD5763	Approved
0.6438	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD3749	Approved
0.6438	Remote Similarity	NPD5124	Phase 1
0.6429	Remote Similarity	NPD3685	Discontinued
0.6424	Remote Similarity	NPD3750	Approved
0.6424	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.642	Remote Similarity	NPD1247	Approved
0.6419	Remote Similarity	NPD1510	Phase 2
0.6415	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD2067	Discontinued
0.6408	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD3823	Discontinued
0.6405	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD5536	Phase 2
0.6395	Remote Similarity	NPD1607	Approved
0.6392	Remote Similarity	NPD7577	Discontinued
0.6391	Remote Similarity	NPD5535	Approved
0.6391	Remote Similarity	NPD821	Approved
0.6389	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD3869	Phase 3
0.6387	Remote Similarity	NPD3873	Phase 3
0.6386	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5844	Phase 1
0.6383	Remote Similarity	NPD8651	Approved
0.6383	Remote Similarity	NPD3225	Approved
0.6376	Remote Similarity	NPD6032	Approved
0.637	Remote Similarity	NPD4060	Phase 1
0.6358	Remote Similarity	NPD1243	Approved
0.6357	Remote Similarity	NPD1481	Phase 2
0.6352	Remote Similarity	NPD8455	Phase 2
0.6352	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD2801	Approved
0.6347	Remote Similarity	NPD7074	Phase 3
0.6338	Remote Similarity	NPD987	Approved
0.6336	Remote Similarity	NPD2182	Approved
0.6312	Remote Similarity	NPD2415	Discontinued
0.6312	Remote Similarity	NPD3817	Phase 2
0.6311	Remote Similarity	NPD9365	Approved
0.6309	Remote Similarity	NPD3748	Approved
0.6309	Remote Similarity	NPD5960	Phase 3
0.6308	Remote Similarity	NPD968	Approved
0.6306	Remote Similarity	NPD7458	Discontinued
0.6304	Remote Similarity	NPD5585	Approved
0.6301	Remote Similarity	NPD3163	Approved
0.6301	Remote Similarity	NPD3162	Approved
0.6294	Remote Similarity	NPD558	Phase 2
0.6291	Remote Similarity	NPD2897	Discontinued
0.6289	Remote Similarity	NPD6279	Approved
0.6289	Remote Similarity	NPD6280	Approved
0.6287	Remote Similarity	NPD7054	Approved
0.6286	Remote Similarity	NPD1535	Discovery

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