NPASS Compound

Structure

NPC38761 OpenBabel07101719512D 23 25 0 0 1 0 0 0 0 0999 V2000 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 0.0000 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 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 -1.7321 3.0000 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 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 18 2 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 19 1 0 0 0 0 16 13 1 1 0 0 0 16 23 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.13
Volume:	322.347
LogP:	3.764
LogD:	3.506
LogS:	-4.916
# Rotatable Bonds:	4
TPSA:	57.15
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.936
Synthetic Accessibility Score:	2.788
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.744
MDCK Permeability:	4.849911420024e-05
Pgp-inhibitor:	0.248
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	89.01451873779297%
Volume Distribution (VD):	0.908
Pgp-substrate:	8.471845626831055%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.899
CYP2C19-substrate:	0.916
CYP2C9-inhibitor:	0.609
CYP2C9-substrate:	0.954
CYP2D6-inhibitor:	0.5
CYP2D6-substrate:	0.953
CYP3A4-inhibitor:	0.725
CYP3A4-substrate:	0.717

ADMET: Excretion

Clearance (CL):	11.75
Half-life (T1/2):	0.299

ADMET: Toxicity

hERG Blockers:	0.194
Human Hepatotoxicity (H-HT):	0.229
Drug-inuced Liver Injury (DILI):	0.877
AMES Toxicity:	0.153
Rat Oral Acute Toxicity:	0.153
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.867
Carcinogencity:	0.156
Eye Corrosion:	0.004
Eye Irritation:	0.339
Respiratory Toxicity:	0.905

Download Data

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

Natural Product: NPC38761

Natural Product ID:	NPC38761
*Common Name:**	Erycebenin E
IUPAC Name:	2-[(2S)-5,7-dimethoxy-3,4-dihydro-2H-chromen-2-yl]-5-methoxyphenol
Synonyms:
Standard InCHIKey:	JCLYSCYJVYARSD-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C18H20O5/c1-20-11-4-5-13(15(19)8-11)16-7-6-14-17(22-3)9-12(21-2)10-18(14)23-16/h4-5,8-10,16,19H,6-7H2,1-3H3/t16-/m0/s1
SMILES:	COc1ccc(c(c1)O)[C@@H]1CCc2c(O1)cc(cc2OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL241569
PubChem CID:	16093658
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002592] 7-O-methylated flavonoids

*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
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	stem	n.a.	PMID[17077549]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	stems	n.a.	n.a.	PMID[17158054]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	37000.0	nM	PMID[569047]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	4300.0	nM	PMID[569047]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	2900.0	nM	PMID[569047]

☑ 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 NPC38761 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	347
0.1-0.2	1542
0.2-0.3	4722
0.3-0.4	13228
0.4-0.5	4771
0.5-0.6	4370
0.6-0.7	7278
0.7-0.8	5009
0.8-0.85	1000
0.85-0.9	287
0.9-0.95	106
0.95-1	37

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC76465
0.9914	High Similarity	NPC100099
0.9914	High Similarity	NPC36016
0.9831	High Similarity	NPC17809
0.9831	High Similarity	NPC285040
0.9831	High Similarity	NPC103420
0.9831	High Similarity	NPC188022
0.9831	High Similarity	NPC102540
0.9748	High Similarity	NPC276212
0.9746	High Similarity	NPC197351
0.9746	High Similarity	NPC246648
0.9746	High Similarity	NPC106914
0.9746	High Similarity	NPC86502
0.9746	High Similarity	NPC134195
0.9658	High Similarity	NPC54972
0.9655	High Similarity	NPC8283
0.9655	High Similarity	NPC93398
0.9655	High Similarity	NPC258979
0.9587	High Similarity	NPC222572
0.9587	High Similarity	NPC274717
0.9587	High Similarity	NPC87224
0.9583	High Similarity	NPC230479
0.9583	High Similarity	NPC283049
0.9583	High Similarity	NPC50315
0.9583	High Similarity	NPC26879
0.9569	High Similarity	NPC59561
0.9569	High Similarity	NPC172253
0.9504	High Similarity	NPC149796
0.9426	High Similarity	NPC38664
0.9426	High Similarity	NPC53986
0.9426	High Similarity	NPC39064
0.9426	High Similarity	NPC47283
0.9402	High Similarity	NPC295259
0.9355	High Similarity	NPC196765
0.9355	High Similarity	NPC300875
0.9355	High Similarity	NPC206224
0.9355	High Similarity	NPC228369
0.9355	High Similarity	NPC162801
0.9355	High Similarity	NPC236014
0.9355	High Similarity	NPC12875
0.9355	High Similarity	NPC476166
0.9355	High Similarity	NPC129784
0.9355	High Similarity	NPC17343
0.9355	High Similarity	NPC280653
0.9355	High Similarity	NPC207892
0.9355	High Similarity	NPC150011
0.9355	High Similarity	NPC268917
0.9355	High Similarity	NPC164574
0.9355	High Similarity	NPC129106
0.9355	High Similarity	NPC103799
0.9355	High Similarity	NPC118114
0.935	High Similarity	NPC93962
0.9339	High Similarity	NPC207179
0.9339	High Similarity	NPC167571
0.9339	High Similarity	NPC278552
0.9328	High Similarity	NPC193364
0.9316	High Similarity	NPC74821
0.931	High Similarity	NPC54507
0.931	High Similarity	NPC85292
0.931	High Similarity	NPC229147
0.928	High Similarity	NPC13005
0.9274	High Similarity	NPC470225
0.9274	High Similarity	NPC27187
0.9262	High Similarity	NPC262573
0.9262	High Similarity	NPC471215
0.9224	High Similarity	NPC464
0.9224	High Similarity	NPC185541
0.9206	High Similarity	NPC11060
0.9206	High Similarity	NPC215037
0.9206	High Similarity	NPC85435
0.92	High Similarity	NPC293203
0.92	High Similarity	NPC68205
0.92	High Similarity	NPC271945
0.92	High Similarity	NPC181497
0.92	High Similarity	NPC244888
0.92	High Similarity	NPC118683
0.92	High Similarity	NPC211413
0.92	High Similarity	NPC164804
0.9194	High Similarity	NPC134360
0.9167	High Similarity	NPC97432
0.9167	High Similarity	NPC190454
0.9153	High Similarity	NPC131118
0.9134	High Similarity	NPC225696
0.9134	High Similarity	NPC223008
0.9134	High Similarity	NPC473107
0.9134	High Similarity	NPC476617
0.9134	High Similarity	NPC117048
0.9134	High Similarity	NPC476616
0.9134	High Similarity	NPC198154
0.9134	High Similarity	NPC97834
0.9134	High Similarity	NPC124085
0.9134	High Similarity	NPC115335
0.9134	High Similarity	NPC296915
0.9134	High Similarity	NPC476615
0.9098	High Similarity	NPC159132
0.9098	High Similarity	NPC256015
0.9098	High Similarity	NPC294156
0.9062	High Similarity	NPC470356
0.9062	High Similarity	NPC473413
0.9062	High Similarity	NPC94750
0.9062	High Similarity	NPC474206
0.9062	High Similarity	NPC112246
0.9062	High Similarity	NPC121812
0.9062	High Similarity	NPC112939
0.9062	High Similarity	NPC61946
0.9062	High Similarity	NPC151224
0.9055	High Similarity	NPC77196
0.9055	High Similarity	NPC92805
0.9016	High Similarity	NPC474160
0.9008	High Similarity	NPC476633
0.8992	High Similarity	NPC227503
0.8992	High Similarity	NPC3049
0.8992	High Similarity	NPC471522
0.8992	High Similarity	NPC474639
0.8992	High Similarity	NPC16435
0.8992	High Similarity	NPC262585
0.8992	High Similarity	NPC230734
0.8992	High Similarity	NPC306441
0.8992	High Similarity	NPC20829
0.8992	High Similarity	NPC18189
0.8992	High Similarity	NPC234952
0.8984	High Similarity	NPC317380
0.8943	High Similarity	NPC270030
0.8923	High Similarity	NPC470308
0.8923	High Similarity	NPC474687
0.8923	High Similarity	NPC262328
0.8923	High Similarity	NPC87777
0.8923	High Similarity	NPC474282
0.8923	High Similarity	NPC470307
0.8923	High Similarity	NPC107551
0.8923	High Similarity	NPC326797
0.8923	High Similarity	NPC211549
0.8923	High Similarity	NPC103976
0.8923	High Similarity	NPC102904
0.8923	High Similarity	NPC176051
0.8915	High Similarity	NPC234333
0.8915	High Similarity	NPC260898
0.8915	High Similarity	NPC164787
0.8915	High Similarity	NPC47398
0.8915	High Similarity	NPC195022
0.8908	High Similarity	NPC33270
0.8908	High Similarity	NPC474933
0.8908	High Similarity	NPC69261
0.8906	High Similarity	NPC263064
0.8906	High Similarity	NPC475840
0.888	High Similarity	NPC46978
0.8871	High Similarity	NPC113495
0.8855	High Similarity	NPC471388
0.8855	High Similarity	NPC475836
0.8855	High Similarity	NPC32630
0.8846	High Similarity	NPC269091
0.8846	High Similarity	NPC270456
0.8846	High Similarity	NPC162659
0.8846	High Similarity	NPC470802
0.8846	High Similarity	NPC248727
0.8846	High Similarity	NPC302701
0.8846	High Similarity	NPC173660
0.8846	High Similarity	NPC265433
0.8828	High Similarity	NPC261619
0.8828	High Similarity	NPC127624
0.8828	High Similarity	NPC61477
0.8828	High Similarity	NPC202762
0.8828	High Similarity	NPC219876
0.8828	High Similarity	NPC126029
0.8828	High Similarity	NPC15658
0.8828	High Similarity	NPC86655
0.8828	High Similarity	NPC78770
0.8828	High Similarity	NPC185604
0.8824	High Similarity	NPC150624
0.8824	High Similarity	NPC141090
0.8824	High Similarity	NPC203113
0.8819	High Similarity	NPC32463
0.881	High Similarity	NPC219923
0.881	High Similarity	NPC31707
0.8803	High Similarity	NPC153795
0.8803	High Similarity	NPC42911
0.8803	High Similarity	NPC290353
0.8788	High Similarity	NPC184797
0.8788	High Similarity	NPC27495
0.8788	High Similarity	NPC309124
0.878	High Similarity	NPC150026
0.878	High Similarity	NPC18128
0.878	High Similarity	NPC77789
0.8779	High Similarity	NPC276490
0.877	High Similarity	NPC102639
0.8769	High Similarity	NPC125579
0.8769	High Similarity	NPC15109
0.8769	High Similarity	NPC11727
0.876	High Similarity	NPC184302
0.876	High Similarity	NPC168059
0.876	High Similarity	NPC229442
0.876	High Similarity	NPC469610
0.875	High Similarity	NPC127894
0.875	High Similarity	NPC15860
0.875	High Similarity	NPC470759
0.875	High Similarity	NPC219070
0.875	High Similarity	NPC268342
0.875	High Similarity	NPC250727
0.875	High Similarity	NPC220825
0.875	High Similarity	NPC8899

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 NPC38761 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	930
0.2-0.3	1607
0.3-0.4	2686
0.4-0.5	1724
0.5-0.6	1057
0.6-0.7	658
0.7-0.8	168
0.8-0.85	13
0.85-0.9	4
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9426	High Similarity	NPD4908	Phase 1
0.9328	High Similarity	NPD1610	Phase 2
0.9316	High Similarity	NPD1548	Phase 1
0.9274	High Similarity	NPD4907	Clinical (unspecified phase)
0.8828	High Similarity	NPD1613	Approved
0.8828	High Similarity	NPD1612	Clinical (unspecified phase)
0.8661	High Similarity	NPD1529	Clinical (unspecified phase)
0.8594	High Similarity	NPD4625	Phase 3
0.8583	High Similarity	NPD2861	Phase 2
0.8583	High Similarity	NPD1530	Clinical (unspecified phase)
0.856	High Similarity	NPD4749	Approved
0.8527	High Similarity	NPD6859	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD7213	Phase 3
0.8467	Intermediate Similarity	NPD7212	Phase 2
0.845	Intermediate Similarity	NPD3027	Phase 3
0.8433	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8433	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD422	Phase 1
0.8385	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD1549	Phase 2
0.8333	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5124	Phase 1
0.8273	Intermediate Similarity	NPD7447	Phase 1
0.811	Intermediate Similarity	NPD1091	Approved
0.8103	Intermediate Similarity	NPD940	Approved
0.8103	Intermediate Similarity	NPD846	Approved
0.8014	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2684	Approved
0.7984	Intermediate Similarity	NPD6583	Phase 3
0.7984	Intermediate Similarity	NPD6671	Approved
0.7984	Intermediate Similarity	NPD6582	Phase 2
0.7983	Intermediate Similarity	NPD968	Approved
0.7956	Intermediate Similarity	NPD2796	Approved
0.7945	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD290	Approved
0.7914	Intermediate Similarity	NPD1652	Phase 2
0.7914	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD7843	Approved
0.7886	Intermediate Similarity	NPD5535	Approved
0.7883	Intermediate Similarity	NPD1510	Phase 2
0.7883	Intermediate Similarity	NPD7033	Discontinued
0.7877	Intermediate Similarity	NPD1934	Approved
0.7857	Intermediate Similarity	NPD3750	Approved
0.7852	Intermediate Similarity	NPD1240	Approved
0.7836	Intermediate Similarity	NPD6798	Discontinued
0.7826	Intermediate Similarity	NPD6099	Approved
0.7826	Intermediate Similarity	NPD6100	Approved
0.781	Intermediate Similarity	NPD4536	Approved
0.781	Intermediate Similarity	NPD4538	Approved
0.781	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD7411	Suspended
0.7803	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD6584	Phase 3
0.7786	Intermediate Similarity	NPD8651	Approved
0.7785	Intermediate Similarity	NPD7075	Discontinued
0.7762	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD3018	Phase 2
0.774	Intermediate Similarity	NPD4380	Phase 2
0.7737	Intermediate Similarity	NPD1607	Approved
0.773	Intermediate Similarity	NPD7466	Approved
0.7727	Intermediate Similarity	NPD2797	Approved
0.7721	Intermediate Similarity	NPD4060	Phase 1
0.771	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD7157	Approved
0.7674	Intermediate Similarity	NPD6516	Phase 2
0.7674	Intermediate Similarity	NPD5846	Approved
0.7672	Intermediate Similarity	NPD2860	Approved
0.7672	Intermediate Similarity	NPD2859	Approved
0.7667	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD3225	Approved
0.7642	Intermediate Similarity	NPD5451	Approved
0.7626	Intermediate Similarity	NPD5588	Approved
0.7626	Intermediate Similarity	NPD5960	Phase 3
0.7606	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD3892	Phase 2
0.76	Intermediate Similarity	NPD821	Approved
0.76	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7768	Phase 2
0.7586	Intermediate Similarity	NPD2934	Approved
0.7586	Intermediate Similarity	NPD2933	Approved
0.7584	Intermediate Similarity	NPD7819	Suspended
0.7576	Intermediate Similarity	NPD2982	Phase 2
0.7576	Intermediate Similarity	NPD2983	Phase 2
0.7574	Intermediate Similarity	NPD3268	Approved
0.7571	Intermediate Similarity	NPD1551	Phase 2
0.7569	Intermediate Similarity	NPD6799	Approved
0.7563	Intermediate Similarity	NPD1242	Phase 1
0.7559	Intermediate Similarity	NPD2557	Approved
0.7554	Intermediate Similarity	NPD2200	Suspended
0.7551	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD6355	Discontinued
0.7519	Intermediate Similarity	NPD6581	Approved
0.7519	Intermediate Similarity	NPD6580	Approved
0.7518	Intermediate Similarity	NPD6233	Phase 2
0.7517	Intermediate Similarity	NPD6801	Discontinued
0.7517	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4750	Phase 3
0.75	Intermediate Similarity	NPD3596	Phase 2
0.75	Intermediate Similarity	NPD2981	Phase 2
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD5058	Phase 3
0.7484	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6166	Phase 2
0.7483	Intermediate Similarity	NPD1653	Approved
0.7482	Intermediate Similarity	NPD3054	Approved
0.7482	Intermediate Similarity	NPD3052	Approved
0.7479	Intermediate Similarity	NPD3020	Approved
0.7467	Intermediate Similarity	NPD2801	Approved
0.7462	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1511	Approved
0.7444	Intermediate Similarity	NPD3685	Discontinued
0.7429	Intermediate Similarity	NPD7097	Phase 1
0.7429	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD5403	Approved
0.741	Intermediate Similarity	NPD4340	Discontinued
0.7407	Intermediate Similarity	NPD3690	Phase 2
0.7407	Intermediate Similarity	NPD3691	Phase 2
0.7403	Intermediate Similarity	NPD6959	Discontinued
0.7402	Intermediate Similarity	NPD5283	Phase 1
0.7385	Intermediate Similarity	NPD1894	Discontinued
0.7383	Intermediate Similarity	NPD6599	Discontinued
0.7376	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3882	Suspended
0.7361	Intermediate Similarity	NPD4628	Phase 3
0.7348	Intermediate Similarity	NPD3496	Discontinued
0.7348	Intermediate Similarity	NPD3847	Discontinued
0.7347	Intermediate Similarity	NPD1512	Approved
0.7343	Intermediate Similarity	NPD2424	Discontinued
0.7342	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2238	Phase 2
0.7338	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD3049	Approved
0.7328	Intermediate Similarity	NPD3444	Approved
0.7328	Intermediate Similarity	NPD3445	Approved
0.7328	Intermediate Similarity	NPD3443	Approved
0.7319	Intermediate Similarity	NPD1296	Phase 2
0.7313	Intermediate Similarity	NPD5327	Phase 3
0.7296	Intermediate Similarity	NPD7074	Phase 3
0.7293	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD1535	Discovery
0.7286	Intermediate Similarity	NPD5735	Approved
0.7279	Intermediate Similarity	NPD5401	Approved
0.7273	Intermediate Similarity	NPD2554	Approved
0.7273	Intermediate Similarity	NPD1778	Approved
0.7273	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2556	Approved
0.7266	Intermediate Similarity	NPD4062	Phase 3
0.7266	Intermediate Similarity	NPD7477	Discontinued
0.726	Intermediate Similarity	NPD6666	Approved
0.726	Intermediate Similarity	NPD6667	Approved
0.7259	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD6696	Suspended
0.7246	Intermediate Similarity	NPD7095	Approved
0.7244	Intermediate Similarity	NPD228	Approved
0.7241	Intermediate Similarity	NPD4535	Phase 3
0.7239	Intermediate Similarity	NPD2235	Phase 2
0.7239	Intermediate Similarity	NPD1481	Phase 2
0.7239	Intermediate Similarity	NPD1608	Approved
0.7239	Intermediate Similarity	NPD2231	Phase 2
0.7237	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD5844	Phase 1
0.7233	Intermediate Similarity	NPD7054	Approved
0.7222	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6072	Discontinued
0.7214	Intermediate Similarity	NPD4140	Approved
0.7211	Intermediate Similarity	NPD7041	Phase 2
0.7211	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3749	Approved
0.7206	Intermediate Similarity	NPD3267	Approved
0.7206	Intermediate Similarity	NPD3266	Approved
0.7206	Intermediate Similarity	NPD1203	Approved
0.7205	Intermediate Similarity	NPD6559	Discontinued
0.7203	Intermediate Similarity	NPD2935	Discontinued
0.7194	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3817	Phase 2
0.7188	Intermediate Similarity	NPD7472	Approved
0.7185	Intermediate Similarity	NPD6540	Phase 3
0.7185	Intermediate Similarity	NPD6542	Approved
0.7185	Intermediate Similarity	NPD6543	Approved
0.7185	Intermediate Similarity	NPD6539	Approved
0.7179	Intermediate Similarity	NPD7199	Phase 2
0.7174	Intermediate Similarity	NPD6832	Phase 2
0.7172	Intermediate Similarity	NPD6674	Discontinued
0.7171	Intermediate Similarity	NPD37	Approved
0.717	Intermediate Similarity	NPD3818	Discontinued
0.7161	Intermediate Similarity	NPD6234	Discontinued
0.7153	Intermediate Similarity	NPD5762	Approved
0.7153	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD3540	Phase 1
0.7153	Intermediate Similarity	NPD6005	Phase 3
0.7153	Intermediate Similarity	NPD5763	Approved
0.7153	Intermediate Similarity	NPD6006	Clinical (unspecified phase)

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