NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.11
Volume:	270.175
LogP:	3.658
LogD:	3.352
LogS:	-4.186
# Rotatable Bonds:	2
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.894
Synthetic Accessibility Score:	2.487
Fsp3:	0.25
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:	-4.673
MDCK Permeability:	1.925859396578744e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.086

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.149
Plasma Protein Binding (PPB):	96.54364776611328%
Volume Distribution (VD):	1.476
Pgp-substrate:	2.099777936935425%

ADMET: Metabolism

CYP1A2-inhibitor:	0.954
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.967
CYP2C19-substrate:	0.405
CYP2C9-inhibitor:	0.862
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.824
CYP2D6-substrate:	0.941
CYP3A4-inhibitor:	0.798
CYP3A4-substrate:	0.622

ADMET: Excretion

Clearance (CL):	13.885
Half-life (T1/2):	0.314

ADMET: Toxicity

hERG Blockers:	0.294
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.463
AMES Toxicity:	0.515
Rat Oral Acute Toxicity:	0.125
Maximum Recommended Daily Dose:	0.8
Skin Sensitization:	0.692
Carcinogencity:	0.629
Eye Corrosion:	0.14
Eye Irritation:	0.892
Respiratory Toxicity:	0.735

Download Data

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

Natural Product: NPC36016

Natural Product ID:	NPC36016
*Common Name:**	(-)-7-Hydroxy-4'-Methoxyflavan
IUPAC Name:	(2S)-2-(4-methoxyphenyl)-3,4-dihydro-2H-chromen-7-ol
Synonyms:
Standard InCHIKey:	JTPMXGZHRQYFTB-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C16H16O3/c1-18-14-7-3-11(4-8-14)15-9-5-12-2-6-13(17)10-16(12)19-15/h2-4,6-8,10,15,17H,5,9H2,1H3/t15-/m0/s1
SMILES:	COc1ccc(cc1)[C@@H]1CCc2c(O1)cc(cc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253563
PubChem CID:	442277
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002596] 4'-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
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[11395279]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	n.a.	n.a.	PMID[11678652]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	whole plants	Shawnee National Forest, Harrisburg, IL, US	n.a.	PMID[11678652]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12016928]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12419367]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	stems	Ningming County, Guangxi autonomous region, China	2006-Jan	PMID[17883259]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	leaves	Kaohsiung, Taiwan	2006-SEP	PMID[18986201]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	Fruits	n.a.	n.a.	PMID[19296617]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19653666]
NPO12711	Ligularia altaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20073490]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21661731]
NPO4576	Corynandra viscosa	Species	Cleomaceae	Eukaryota	n.a.	leaf	n.a.	PMID[28135851]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	Thai	n.a.	PMID[3430167]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	formosan	n.a.	PMID[8864236]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358644]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4576	Corynandra viscosa	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4576	Corynandra viscosa	Species	Cleomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5495	Broussonetia papyrifera	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25680	Ramalina siliquosa	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12711	Ligularia altaica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10319	Calycodendron milnei	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO13784	Dalbergia candenatensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9612	Dryopteris dilatata	Species	Dryopteridaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	250000.0	nM	PMID[556183]

☑ 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 NPC36016 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	350
0.1-0.2	1619
0.2-0.3	4791
0.3-0.4	13473
0.4-0.5	4480
0.5-0.6	4535
0.6-0.7	7439
0.7-0.8	4720
0.8-0.85	918
0.85-0.9	252
0.9-0.95	95
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC100099
0.9914	High Similarity	NPC38761
0.9914	High Similarity	NPC76465
0.9829	High Similarity	NPC134195
0.9829	High Similarity	NPC246648
0.9829	High Similarity	NPC106914
0.9829	High Similarity	NPC86502
0.9829	High Similarity	NPC197351
0.9746	High Similarity	NPC285040
0.9746	High Similarity	NPC17809
0.9746	High Similarity	NPC103420
0.9746	High Similarity	NPC188022
0.9746	High Similarity	NPC102540
0.9741	High Similarity	NPC54972
0.9739	High Similarity	NPC93398
0.9739	High Similarity	NPC258979
0.9739	High Similarity	NPC8283
0.9664	High Similarity	NPC276212
0.9583	High Similarity	NPC149796
0.9504	High Similarity	NPC87224
0.9504	High Similarity	NPC222572
0.9504	High Similarity	NPC274717
0.95	High Similarity	NPC26879
0.95	High Similarity	NPC230479
0.95	High Similarity	NPC50315
0.95	High Similarity	NPC283049
0.9483	High Similarity	NPC295259
0.9483	High Similarity	NPC59561
0.9483	High Similarity	NPC172253
0.9407	High Similarity	NPC193364
0.9397	High Similarity	NPC74821
0.9391	High Similarity	NPC85292
0.9391	High Similarity	NPC229147
0.9391	High Similarity	NPC54507
0.9344	High Similarity	NPC38664
0.9344	High Similarity	NPC39064
0.9344	High Similarity	NPC53986
0.9344	High Similarity	NPC47283
0.9304	High Similarity	NPC185541
0.9304	High Similarity	NPC464
0.9274	High Similarity	NPC476166
0.9274	High Similarity	NPC196765
0.9274	High Similarity	NPC236014
0.9274	High Similarity	NPC300875
0.9274	High Similarity	NPC12875
0.9274	High Similarity	NPC162801
0.9274	High Similarity	NPC280653
0.9274	High Similarity	NPC207892
0.9274	High Similarity	NPC150011
0.9274	High Similarity	NPC164574
0.9274	High Similarity	NPC129106
0.9274	High Similarity	NPC129784
0.9274	High Similarity	NPC118114
0.9274	High Similarity	NPC206224
0.9274	High Similarity	NPC228369
0.9274	High Similarity	NPC103799
0.9274	High Similarity	NPC17343
0.9274	High Similarity	NPC268917
0.9268	High Similarity	NPC93962
0.9256	High Similarity	NPC278552
0.9256	High Similarity	NPC207179
0.9256	High Similarity	NPC167571
0.9231	High Similarity	NPC131118
0.92	High Similarity	NPC13005
0.9194	High Similarity	NPC470225
0.9194	High Similarity	NPC27187
0.918	High Similarity	NPC471215
0.918	High Similarity	NPC262573
0.9127	High Similarity	NPC85435
0.9127	High Similarity	NPC11060
0.9127	High Similarity	NPC215037
0.912	High Similarity	NPC244888
0.912	High Similarity	NPC181497
0.912	High Similarity	NPC271945
0.912	High Similarity	NPC211413
0.912	High Similarity	NPC68205
0.912	High Similarity	NPC293203
0.912	High Similarity	NPC118683
0.912	High Similarity	NPC164804
0.9113	High Similarity	NPC134360
0.9083	High Similarity	NPC190454
0.9083	High Similarity	NPC97432
0.9055	High Similarity	NPC296915
0.9055	High Similarity	NPC223008
0.9055	High Similarity	NPC225696
0.9055	High Similarity	NPC198154
0.9055	High Similarity	NPC476617
0.9055	High Similarity	NPC115335
0.9055	High Similarity	NPC124085
0.9055	High Similarity	NPC117048
0.9055	High Similarity	NPC476616
0.9055	High Similarity	NPC97834
0.9055	High Similarity	NPC476615
0.9055	High Similarity	NPC473107
0.9016	High Similarity	NPC159132
0.9016	High Similarity	NPC270030
0.9016	High Similarity	NPC294156
0.9016	High Similarity	NPC256015
0.8984	High Similarity	NPC94750
0.8984	High Similarity	NPC474206
0.8984	High Similarity	NPC61946
0.8984	High Similarity	NPC470356
0.8984	High Similarity	NPC151224
0.8984	High Similarity	NPC121812
0.8984	High Similarity	NPC112246
0.8984	High Similarity	NPC112939
0.8984	High Similarity	NPC473413
0.8983	High Similarity	NPC33270
0.8983	High Similarity	NPC474933
0.8983	High Similarity	NPC69261
0.8976	High Similarity	NPC77196
0.8976	High Similarity	NPC92805
0.8952	High Similarity	NPC46978
0.8934	High Similarity	NPC474160
0.8926	High Similarity	NPC476633
0.8915	High Similarity	NPC3049
0.8915	High Similarity	NPC227503
0.8915	High Similarity	NPC471522
0.8915	High Similarity	NPC262585
0.8915	High Similarity	NPC474639
0.8915	High Similarity	NPC306441
0.8915	High Similarity	NPC234952
0.8915	High Similarity	NPC20829
0.8915	High Similarity	NPC16435
0.8915	High Similarity	NPC18189
0.8915	High Similarity	NPC230734
0.8906	High Similarity	NPC317380
0.8898	High Similarity	NPC141090
0.8898	High Similarity	NPC150624
0.8852	High Similarity	NPC150026
0.8846	High Similarity	NPC103976
0.8846	High Similarity	NPC470307
0.8846	High Similarity	NPC470308
0.8846	High Similarity	NPC87777
0.8846	High Similarity	NPC211549
0.8846	High Similarity	NPC326797
0.8846	High Similarity	NPC102904
0.8846	High Similarity	NPC262328
0.8846	High Similarity	NPC107551
0.8846	High Similarity	NPC474687
0.8846	High Similarity	NPC474282
0.8846	High Similarity	NPC176051
0.8843	High Similarity	NPC102639
0.8837	High Similarity	NPC234333
0.8837	High Similarity	NPC47398
0.8837	High Similarity	NPC195022
0.8837	High Similarity	NPC164787
0.8837	High Similarity	NPC260898
0.8833	High Similarity	NPC184302
0.8828	High Similarity	NPC263064
0.8828	High Similarity	NPC475840
0.8814	High Similarity	NPC808
0.8814	High Similarity	NPC53906
0.881	High Similarity	NPC472797
0.879	High Similarity	NPC81641
0.879	High Similarity	NPC131397
0.879	High Similarity	NPC476254
0.879	High Similarity	NPC113495
0.8779	High Similarity	NPC32630
0.8779	High Similarity	NPC471388
0.8779	High Similarity	NPC475836
0.8769	High Similarity	NPC248727
0.8769	High Similarity	NPC162659
0.8769	High Similarity	NPC470802
0.8769	High Similarity	NPC270456
0.8769	High Similarity	NPC302701
0.8769	High Similarity	NPC173660
0.8769	High Similarity	NPC269091
0.8769	High Similarity	NPC265433
0.875	High Similarity	NPC190514
0.875	High Similarity	NPC219876
0.875	High Similarity	NPC78770
0.875	High Similarity	NPC15658
0.875	High Similarity	NPC185604
0.875	High Similarity	NPC261619
0.875	High Similarity	NPC127624
0.875	High Similarity	NPC86655
0.875	High Similarity	NPC61477
0.875	High Similarity	NPC472798
0.875	High Similarity	NPC202762
0.875	High Similarity	NPC126029
0.874	High Similarity	NPC32463
0.8739	High Similarity	NPC203113
0.873	High Similarity	NPC219923
0.873	High Similarity	NPC31707
0.873	High Similarity	NPC38604
0.873	High Similarity	NPC211179
0.8729	High Similarity	NPC228287
0.8729	High Similarity	NPC180508
0.8729	High Similarity	NPC276737
0.8729	High Similarity	NPC22610
0.872	High Similarity	NPC170485
0.8718	High Similarity	NPC153795
0.8718	High Similarity	NPC42911
0.8718	High Similarity	NPC290353
0.8712	High Similarity	NPC27495
0.8712	High Similarity	NPC309124
0.8712	High Similarity	NPC184797
0.8702	High Similarity	NPC276490
0.8699	High Similarity	NPC77789

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 NPC36016 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	962
0.2-0.3	1560
0.3-0.4	2705
0.4-0.5	1725
0.5-0.6	1036
0.6-0.7	665
0.7-0.8	161
0.8-0.85	15
0.85-0.9	3
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9407	High Similarity	NPD1610	Phase 2
0.9397	High Similarity	NPD1548	Phase 1
0.9344	High Similarity	NPD4908	Phase 1
0.9194	High Similarity	NPD4907	Clinical (unspecified phase)
0.875	High Similarity	NPD1612	Clinical (unspecified phase)
0.875	High Similarity	NPD1613	Approved
0.8661	High Similarity	NPD4625	Phase 3
0.8651	High Similarity	NPD2861	Phase 2
0.8629	High Similarity	NPD4749	Approved
0.8583	High Similarity	NPD1529	Clinical (unspecified phase)
0.8504	High Similarity	NPD1530	Clinical (unspecified phase)
0.8468	Intermediate Similarity	NPD422	Phase 1
0.845	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.845	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD7212	Phase 2
0.8394	Intermediate Similarity	NPD7213	Phase 3
0.8372	Intermediate Similarity	NPD3027	Phase 3
0.8358	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD1549	Phase 2
0.8258	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD5124	Phase 1
0.8201	Intermediate Similarity	NPD7447	Phase 1
0.8174	Intermediate Similarity	NPD846	Approved
0.8174	Intermediate Similarity	NPD940	Approved
0.8067	Intermediate Similarity	NPD2684	Approved
0.8051	Intermediate Similarity	NPD968	Approved
0.8049	Intermediate Similarity	NPD6671	Approved
0.8047	Intermediate Similarity	NPD6582	Phase 2
0.8047	Intermediate Similarity	NPD6583	Phase 3
0.8031	Intermediate Similarity	NPD1091	Approved
0.8015	Intermediate Similarity	NPD2796	Approved
0.7983	Intermediate Similarity	NPD290	Approved
0.7943	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD1240	Approved
0.7883	Intermediate Similarity	NPD6099	Approved
0.7883	Intermediate Similarity	NPD6100	Approved
0.7877	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7863	Intermediate Similarity	NPD6584	Phase 3
0.7863	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7842	Intermediate Similarity	NPD1652	Phase 2
0.7842	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7823	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.781	Intermediate Similarity	NPD7033	Discontinued
0.781	Intermediate Similarity	NPD1510	Phase 2
0.7808	Intermediate Similarity	NPD1934	Approved
0.7805	Intermediate Similarity	NPD5535	Approved
0.7805	Intermediate Similarity	NPD7843	Approved
0.7794	Intermediate Similarity	NPD1607	Approved
0.7786	Intermediate Similarity	NPD7466	Approved
0.7786	Intermediate Similarity	NPD3750	Approved
0.7786	Intermediate Similarity	NPD2797	Approved
0.7761	Intermediate Similarity	NPD6798	Discontinued
0.774	Intermediate Similarity	NPD7411	Suspended
0.7739	Intermediate Similarity	NPD2860	Approved
0.7739	Intermediate Similarity	NPD2859	Approved
0.7737	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD4538	Approved
0.7737	Intermediate Similarity	NPD4536	Approved
0.7734	Intermediate Similarity	NPD6516	Phase 2
0.7734	Intermediate Similarity	NPD5846	Approved
0.7718	Intermediate Similarity	NPD7075	Discontinued
0.771	Intermediate Similarity	NPD8651	Approved
0.7705	Intermediate Similarity	NPD5451	Approved
0.7692	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4380	Phase 2
0.7669	Intermediate Similarity	NPD3018	Phase 2
0.7661	Intermediate Similarity	NPD821	Approved
0.7652	Intermediate Similarity	NPD2933	Approved
0.7652	Intermediate Similarity	NPD2934	Approved
0.7647	Intermediate Similarity	NPD4060	Phase 1
0.7635	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD1242	Phase 1
0.7619	Intermediate Similarity	NPD2557	Approved
0.7619	Intermediate Similarity	NPD7157	Approved
0.7609	Intermediate Similarity	NPD2200	Suspended
0.76	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD6581	Approved
0.7578	Intermediate Similarity	NPD6580	Approved
0.7576	Intermediate Similarity	NPD3225	Approved
0.7561	Intermediate Similarity	NPD4750	Phase 3
0.7559	Intermediate Similarity	NPD3596	Phase 2
0.7554	Intermediate Similarity	NPD5588	Approved
0.7554	Intermediate Similarity	NPD5960	Phase 3
0.7542	Intermediate Similarity	NPD3020	Approved
0.7536	Intermediate Similarity	NPD3054	Approved
0.7536	Intermediate Similarity	NPD3052	Approved
0.7535	Intermediate Similarity	NPD3892	Phase 2
0.7535	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD7768	Phase 2
0.7533	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD3268	Approved
0.75	Intermediate Similarity	NPD2982	Phase 2
0.75	Intermediate Similarity	NPD6799	Approved
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD2983	Phase 2
0.7483	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD6355	Discontinued
0.7463	Intermediate Similarity	NPD3691	Phase 2
0.7463	Intermediate Similarity	NPD3690	Phase 2
0.745	Intermediate Similarity	NPD6801	Discontinued
0.7448	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD6233	Phase 2
0.7442	Intermediate Similarity	NPD1894	Discontinued
0.7431	Intermediate Similarity	NPD5058	Phase 3
0.7429	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3748	Approved
0.7424	Intermediate Similarity	NPD2981	Phase 2
0.7419	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6166	Phase 2
0.7419	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1653	Approved
0.74	Intermediate Similarity	NPD2801	Approved
0.7391	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2238	Phase 2
0.7385	Intermediate Similarity	NPD3443	Approved
0.7385	Intermediate Similarity	NPD3049	Approved
0.7385	Intermediate Similarity	NPD3445	Approved
0.7385	Intermediate Similarity	NPD3444	Approved
0.7379	Intermediate Similarity	NPD1511	Approved
0.7368	Intermediate Similarity	NPD5327	Phase 3
0.7368	Intermediate Similarity	NPD3685	Discontinued
0.7357	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD7097	Phase 1
0.7353	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD5403	Approved
0.7338	Intermediate Similarity	NPD5735	Approved
0.7338	Intermediate Similarity	NPD6959	Discontinued
0.7338	Intermediate Similarity	NPD4340	Discontinued
0.7328	Intermediate Similarity	NPD2554	Approved
0.7328	Intermediate Similarity	NPD1778	Approved
0.7328	Intermediate Similarity	NPD2556	Approved
0.7328	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD5283	Phase 1
0.7319	Intermediate Similarity	NPD7477	Discontinued
0.7315	Intermediate Similarity	NPD6599	Discontinued
0.7313	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD6696	Suspended
0.731	Intermediate Similarity	NPD6666	Approved
0.731	Intermediate Similarity	NPD6667	Approved
0.7308	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3882	Suspended
0.7302	Intermediate Similarity	NPD228	Approved
0.7293	Intermediate Similarity	NPD1608	Approved
0.7293	Intermediate Similarity	NPD2231	Phase 2
0.7293	Intermediate Similarity	NPD2235	Phase 2
0.7292	Intermediate Similarity	NPD4628	Phase 3
0.7285	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1512	Approved
0.7278	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2424	Discontinued
0.7273	Intermediate Similarity	NPD3847	Discontinued
0.7273	Intermediate Similarity	NPD3496	Discontinued
0.7266	Intermediate Similarity	NPD4140	Approved
0.7246	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1296	Phase 2
0.7239	Intermediate Similarity	NPD6543	Approved
0.7239	Intermediate Similarity	NPD6540	Phase 3
0.7239	Intermediate Similarity	NPD6542	Approved
0.7239	Intermediate Similarity	NPD6539	Approved
0.7233	Intermediate Similarity	NPD7074	Phase 3
0.7218	Intermediate Similarity	NPD1535	Discovery
0.7211	Intermediate Similarity	NPD5401	Approved
0.7203	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD4626	Approved
0.7197	Intermediate Similarity	NPD2667	Approved
0.7197	Intermediate Similarity	NPD2668	Approved
0.7194	Intermediate Similarity	NPD4062	Phase 3
0.7192	Intermediate Similarity	NPD6815	Approved
0.7188	Intermediate Similarity	NPD1241	Discontinued
0.7185	Intermediate Similarity	NPD6541	Approved
0.7185	Intermediate Similarity	NPD6538	Approved
0.7177	Intermediate Similarity	NPD3134	Approved
0.7174	Intermediate Similarity	NPD7095	Approved
0.7174	Intermediate Similarity	NPD5163	Phase 2
0.7174	Intermediate Similarity	NPD6179	Discontinued
0.7172	Intermediate Similarity	NPD4535	Phase 3
0.717	Intermediate Similarity	NPD7054	Approved
0.717	Intermediate Similarity	NPD5844	Phase 1
0.7164	Intermediate Similarity	NPD1481	Phase 2
0.7163	Intermediate Similarity	NPD4097	Suspended
0.7163	Intermediate Similarity	NPD6353	Approved
0.7153	Intermediate Similarity	NPD4993	Discontinued
0.7153	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6072	Discontinued
0.7143	Intermediate Similarity	NPD6559	Discontinued
0.7143	Intermediate Similarity	NPD7041	Phase 2
0.7143	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1558	Phase 1
0.7133	Intermediate Similarity	NPD4476	Approved
0.7133	Intermediate Similarity	NPD4477	Approved
0.7133	Intermediate Similarity	NPD2935	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