NPASS Compound

Structure

NPC17809 OpenBabel07101718222D 21 23 0 0 1 0 0 0 0 0999 V2000 1.7321 1.0000 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 -0.5000 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 -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 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 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 -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 0.8660 -1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 1 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 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 1.7321 -3.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 20 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 16 2 0 0 0 0 10 17 1 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 14 19 1 0 0 0 0 15 11 1 1 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 17 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.12
Volume:	296.261
LogP:	3.824
LogD:	3.411
LogS:	-3.329
# Rotatable Bonds:	2
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.887
Synthetic Accessibility Score:	2.899
Fsp3:	0.294
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:	-4.671
MDCK Permeability:	1.5121404430828989e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.039
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	97.02922821044922%
Volume Distribution (VD):	1.16
Pgp-substrate:	2.4243130683898926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.791
CYP1A2-substrate:	0.954
CYP2C19-inhibitor:	0.845
CYP2C19-substrate:	0.537
CYP2C9-inhibitor:	0.727
CYP2C9-substrate:	0.953
CYP2D6-inhibitor:	0.601
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.347
CYP3A4-substrate:	0.587

ADMET: Excretion

Clearance (CL):	14.103
Half-life (T1/2):	0.542

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.168
Drug-inuced Liver Injury (DILI):	0.098
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.408
Maximum Recommended Daily Dose:	0.692
Skin Sensitization:	0.934
Carcinogencity:	0.292
Eye Corrosion:	0.004
Eye Irritation:	0.884
Respiratory Toxicity:	0.728

Download Data

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

Natural Product: NPC17809

Natural Product ID:	NPC17809
*Common Name:**	(2S)-4',5-Dihydroxy-7-Methoxy-8-Methylflavan
IUPAC Name:	(2S)-2-(4-hydroxyphenyl)-7-methoxy-8-methyl-3,4-dihydro-2H-chromen-5-ol
Synonyms:
Standard InCHIKey:	FAZHAXUNXPANOK-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C17H18O4/c1-10-16(20-2)9-14(19)13-7-8-15(21-17(10)13)11-3-5-12(18)6-4-11/h3-6,9,15,18-19H,7-8H2,1-2H3/t15-/m0/s1
SMILES:	Cc1c(cc(c2CC[C@@H](c3ccc(cc3)O)Oc12)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL253562
PubChem CID:	44257197
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
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12016928]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	stems	Ningming County, Guangxi autonomous region, China	2006-Jan	PMID[17883259]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21661731]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
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]
NPO12714	Dracaena cochinchinensis	Species	Asparagaceae	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	=	55900.0	nM	PMID[549922]

☑ 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 NPC17809 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	360
0.1-0.2	1573
0.2-0.3	4705
0.3-0.4	13226
0.4-0.5	4751
0.5-0.6	4387
0.6-0.7	7247
0.7-0.8	4997
0.8-0.85	1057
0.85-0.9	251
0.9-0.95	122
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC103420
1.0	High Similarity	NPC188022
1.0	High Similarity	NPC102540
1.0	High Similarity	NPC285040
0.9916	High Similarity	NPC276212
0.9915	High Similarity	NPC106914
0.9915	High Similarity	NPC246648
0.9915	High Similarity	NPC197351
0.9915	High Similarity	NPC134195
0.9915	High Similarity	NPC86502
0.9831	High Similarity	NPC38761
0.9831	High Similarity	NPC76465
0.9752	High Similarity	NPC274717
0.9746	High Similarity	NPC100099
0.9746	High Similarity	NPC36016
0.9669	High Similarity	NPC149796
0.959	High Similarity	NPC38664
0.959	High Similarity	NPC53986
0.9516	High Similarity	NPC206224
0.9516	High Similarity	NPC300875
0.9516	High Similarity	NPC12875
0.9516	High Similarity	NPC280653
0.9516	High Similarity	NPC236014
0.9516	High Similarity	NPC103799
0.9516	High Similarity	NPC129106
0.9516	High Similarity	NPC164574
0.9516	High Similarity	NPC118114
0.9516	High Similarity	NPC228369
0.9516	High Similarity	NPC268917
0.9516	High Similarity	NPC129784
0.9516	High Similarity	NPC196765
0.9516	High Similarity	NPC476166
0.9516	High Similarity	NPC207892
0.9516	High Similarity	NPC17343
0.9516	High Similarity	NPC150011
0.9512	High Similarity	NPC93962
0.9496	High Similarity	NPC54972
0.9492	High Similarity	NPC93398
0.9492	High Similarity	NPC258979
0.9492	High Similarity	NPC8283
0.944	High Similarity	NPC13005
0.9435	High Similarity	NPC27187
0.9435	High Similarity	NPC470225
0.9431	High Similarity	NPC222572
0.9431	High Similarity	NPC87224
0.9426	High Similarity	NPC283049
0.9426	High Similarity	NPC26879
0.9426	High Similarity	NPC230479
0.9426	High Similarity	NPC50315
0.9407	High Similarity	NPC59561
0.9407	High Similarity	NPC172253
0.9365	High Similarity	NPC85435
0.936	High Similarity	NPC181497
0.936	High Similarity	NPC211413
0.936	High Similarity	NPC271945
0.936	High Similarity	NPC68205
0.936	High Similarity	NPC244888
0.936	High Similarity	NPC293203
0.936	High Similarity	NPC118683
0.936	High Similarity	NPC164804
0.9355	High Similarity	NPC134360
0.9322	High Similarity	NPC131118
0.9291	High Similarity	NPC97834
0.9291	High Similarity	NPC296915
0.9291	High Similarity	NPC124085
0.9291	High Similarity	NPC223008
0.9291	High Similarity	NPC473107
0.9291	High Similarity	NPC117048
0.9291	High Similarity	NPC225696
0.9291	High Similarity	NPC115335
0.9291	High Similarity	NPC198154
0.9274	High Similarity	NPC47283
0.9274	High Similarity	NPC39064
0.9262	High Similarity	NPC159132
0.9244	High Similarity	NPC295259
0.9219	High Similarity	NPC473413
0.9213	High Similarity	NPC92805
0.9213	High Similarity	NPC77196
0.9206	High Similarity	NPC162801
0.9187	High Similarity	NPC207179
0.9187	High Similarity	NPC278552
0.9187	High Similarity	NPC167571
0.9174	High Similarity	NPC193364
0.9174	High Similarity	NPC476633
0.916	High Similarity	NPC74821
0.9153	High Similarity	NPC54507
0.9153	High Similarity	NPC229147
0.9153	High Similarity	NPC85292
0.9147	High Similarity	NPC20829
0.9147	High Similarity	NPC3049
0.9147	High Similarity	NPC471522
0.9147	High Similarity	NPC18189
0.9147	High Similarity	NPC262585
0.9113	High Similarity	NPC262573
0.9113	High Similarity	NPC471215
0.9077	High Similarity	NPC470308
0.9077	High Similarity	NPC474687
0.9077	High Similarity	NPC470307
0.9068	High Similarity	NPC464
0.9068	High Similarity	NPC185541
0.9062	High Similarity	NPC11060
0.9062	High Similarity	NPC215037
0.9016	High Similarity	NPC190454
0.9016	High Similarity	NPC97432
0.9008	High Similarity	NPC32630
0.9008	High Similarity	NPC475836
0.9	High Similarity	NPC470802
0.8992	High Similarity	NPC476617
0.8992	High Similarity	NPC476615
0.8992	High Similarity	NPC476616
0.8976	High Similarity	NPC32463
0.8952	High Similarity	NPC294156
0.8952	High Similarity	NPC256015
0.8943	High Similarity	NPC150026
0.8923	High Similarity	NPC112246
0.8923	High Similarity	NPC94750
0.8923	High Similarity	NPC125579
0.8923	High Similarity	NPC470356
0.8923	High Similarity	NPC474206
0.8923	High Similarity	NPC112939
0.8923	High Similarity	NPC151224
0.8923	High Similarity	NPC121812
0.8923	High Similarity	NPC61946
0.888	High Similarity	NPC81641
0.8872	High Similarity	NPC5155
0.8872	High Similarity	NPC265075
0.8871	High Similarity	NPC474160
0.8864	High Similarity	NPC260741
0.8864	High Similarity	NPC70682
0.8855	High Similarity	NPC16435
0.8855	High Similarity	NPC227503
0.8855	High Similarity	NPC474639
0.8855	High Similarity	NPC230734
0.8855	High Similarity	NPC306441
0.8855	High Similarity	NPC234952
0.8846	High Similarity	NPC317380
0.8846	High Similarity	NPC131950
0.8806	High Similarity	NPC5253
0.8806	High Similarity	NPC49542
0.8806	High Similarity	NPC139976
0.8806	High Similarity	NPC230718
0.8806	High Similarity	NPC84207
0.8806	High Similarity	NPC128337
0.88	High Similarity	NPC270030
0.879	High Similarity	NPC57199
0.8788	High Similarity	NPC107551
0.8788	High Similarity	NPC102904
0.8788	High Similarity	NPC176051
0.8788	High Similarity	NPC326797
0.8788	High Similarity	NPC211549
0.8788	High Similarity	NPC103976
0.8788	High Similarity	NPC87777
0.8788	High Similarity	NPC262328
0.8788	High Similarity	NPC474282
0.8779	High Similarity	NPC164787
0.8779	High Similarity	NPC195022
0.8779	High Similarity	NPC260898
0.8779	High Similarity	NPC234333
0.8779	High Similarity	NPC47398
0.8769	High Similarity	NPC177712
0.8769	High Similarity	NPC24913
0.8769	High Similarity	NPC475840
0.8769	High Similarity	NPC263064
0.876	High Similarity	NPC33270
0.876	High Similarity	NPC160623
0.876	High Similarity	NPC474933
0.876	High Similarity	NPC69261
0.875	High Similarity	NPC16577
0.874	High Similarity	NPC473134
0.874	High Similarity	NPC46978
0.8731	High Similarity	NPC277331
0.8731	High Similarity	NPC35216
0.8731	High Similarity	NPC100482
0.873	High Similarity	NPC293801
0.873	High Similarity	NPC105031
0.873	High Similarity	NPC113495
0.8722	High Similarity	NPC144512
0.8722	High Similarity	NPC471388
0.8722	High Similarity	NPC137262
0.8722	High Similarity	NPC47040
0.8722	High Similarity	NPC35501
0.8722	High Similarity	NPC278600
0.8722	High Similarity	NPC37428
0.8712	High Similarity	NPC173660
0.8712	High Similarity	NPC265433
0.8712	High Similarity	NPC269091
0.8712	High Similarity	NPC248727
0.8712	High Similarity	NPC162659
0.8712	High Similarity	NPC302701
0.8712	High Similarity	NPC270456
0.8692	High Similarity	NPC202762
0.8692	High Similarity	NPC185604
0.8692	High Similarity	NPC78770
0.8692	High Similarity	NPC86655
0.8692	High Similarity	NPC261619
0.8692	High Similarity	NPC126029
0.8692	High Similarity	NPC61477
0.8692	High Similarity	NPC219876
0.8692	High Similarity	NPC472798
0.8692	High Similarity	NPC127624

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 NPC17809 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	944
0.2-0.3	1614
0.3-0.4	2669
0.4-0.5	1746
0.5-0.6	1016
0.6-0.7	662
0.7-0.8	162
0.8-0.85	14
0.85-0.9	3
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9435	High Similarity	NPD4907	Clinical (unspecified phase)
0.9274	High Similarity	NPD4908	Phase 1
0.9174	High Similarity	NPD1610	Phase 2
0.916	High Similarity	NPD1548	Phase 1
0.875	High Similarity	NPD4625	Phase 3
0.8692	High Similarity	NPD1612	Clinical (unspecified phase)
0.8692	High Similarity	NPD1613	Approved
0.8527	High Similarity	NPD1529	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD5124	Phase 1
0.8485	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.845	Intermediate Similarity	NPD2861	Phase 2
0.845	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD4749	Approved
0.8397	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD7213	Phase 3
0.8345	Intermediate Similarity	NPD7212	Phase 2
0.8321	Intermediate Similarity	NPD3027	Phase 3
0.8309	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8268	Intermediate Similarity	NPD422	Phase 1
0.8248	Intermediate Similarity	NPD1549	Phase 2
0.8156	Intermediate Similarity	NPD7447	Phase 1
0.8156	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD1091	Approved
0.7966	Intermediate Similarity	NPD940	Approved
0.7966	Intermediate Similarity	NPD846	Approved
0.7956	Intermediate Similarity	NPD4538	Approved
0.7956	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD4536	Approved
0.7945	Intermediate Similarity	NPD7411	Suspended
0.7939	Intermediate Similarity	NPD8651	Approved
0.7919	Intermediate Similarity	NPD7075	Discontinued
0.7902	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD4380	Phase 2
0.7869	Intermediate Similarity	NPD2684	Approved
0.7868	Intermediate Similarity	NPD4060	Phase 1
0.7863	Intermediate Similarity	NPD6583	Phase 3
0.7863	Intermediate Similarity	NPD6582	Phase 2
0.7863	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6671	Approved
0.7851	Intermediate Similarity	NPD968	Approved
0.7842	Intermediate Similarity	NPD2796	Approved
0.7838	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.782	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1652	Phase 2
0.7787	Intermediate Similarity	NPD290	Approved
0.777	Intermediate Similarity	NPD1934	Approved
0.777	Intermediate Similarity	NPD7033	Discontinued
0.777	Intermediate Similarity	NPD5588	Approved
0.777	Intermediate Similarity	NPD1510	Phase 2
0.777	Intermediate Similarity	NPD5960	Phase 3
0.776	Intermediate Similarity	NPD5535	Approved
0.776	Intermediate Similarity	NPD7843	Approved
0.7746	Intermediate Similarity	NPD3750	Approved
0.7737	Intermediate Similarity	NPD1240	Approved
0.7733	Intermediate Similarity	NPD7768	Phase 2
0.7721	Intermediate Similarity	NPD6798	Discontinued
0.7718	Intermediate Similarity	NPD7819	Suspended
0.7714	Intermediate Similarity	NPD6099	Approved
0.7714	Intermediate Similarity	NPD6100	Approved
0.7687	Intermediate Similarity	NPD6584	Phase 3
0.7651	Intermediate Similarity	NPD6801	Discontinued
0.7639	Intermediate Similarity	NPD5058	Phase 3
0.763	Intermediate Similarity	NPD3018	Phase 2
0.7626	Intermediate Similarity	NPD1607	Approved
0.7622	Intermediate Similarity	NPD7466	Approved
0.7622	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD2797	Approved
0.7578	Intermediate Similarity	NPD7157	Approved
0.7566	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD5846	Approved
0.7557	Intermediate Similarity	NPD6516	Phase 2
0.7556	Intermediate Similarity	NPD3691	Phase 2
0.7556	Intermediate Similarity	NPD3690	Phase 2
0.7542	Intermediate Similarity	NPD2860	Approved
0.7542	Intermediate Similarity	NPD2859	Approved
0.7537	Intermediate Similarity	NPD3225	Approved
0.7532	Intermediate Similarity	NPD6959	Discontinued
0.752	Intermediate Similarity	NPD5451	Approved
0.7518	Intermediate Similarity	NPD3846	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3892	Phase 2
0.7483	Intermediate Similarity	NPD2424	Discontinued
0.748	Intermediate Similarity	NPD821	Approved
0.7468	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD6799	Approved
0.7465	Intermediate Similarity	NPD1551	Phase 2
0.7464	Intermediate Similarity	NPD3268	Approved
0.7463	Intermediate Similarity	NPD2982	Phase 2
0.7463	Intermediate Similarity	NPD2983	Phase 2
0.7458	Intermediate Similarity	NPD2934	Approved
0.7458	Intermediate Similarity	NPD2933	Approved
0.745	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7097	Phase 1
0.7447	Intermediate Similarity	NPD2200	Suspended
0.7442	Intermediate Similarity	NPD2557	Approved
0.7438	Intermediate Similarity	NPD1242	Phase 1
0.7429	Intermediate Similarity	NPD6355	Discontinued
0.7415	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD6233	Phase 2
0.7407	Intermediate Similarity	NPD6696	Suspended
0.7405	Intermediate Similarity	NPD6581	Approved
0.7405	Intermediate Similarity	NPD6580	Approved
0.7397	Intermediate Similarity	NPD6667	Approved
0.7397	Intermediate Similarity	NPD6666	Approved
0.7394	Intermediate Similarity	NPD3748	Approved
0.7389	Intermediate Similarity	NPD6166	Phase 2
0.7389	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD2981	Phase 2
0.7385	Intermediate Similarity	NPD3596	Phase 2
0.7383	Intermediate Similarity	NPD1653	Approved
0.7381	Intermediate Similarity	NPD4750	Phase 3
0.7379	Intermediate Similarity	NPD4535	Phase 3
0.7376	Intermediate Similarity	NPD3052	Approved
0.7376	Intermediate Similarity	NPD3054	Approved
0.7368	Intermediate Similarity	NPD2801	Approved
0.7358	Intermediate Similarity	NPD5844	Phase 1
0.7355	Intermediate Similarity	NPD3020	Approved
0.7351	Intermediate Similarity	NPD6072	Discontinued
0.7348	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD1511	Approved
0.7347	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7041	Phase 2
0.7343	Intermediate Similarity	NPD2935	Discontinued
0.7333	Intermediate Similarity	NPD5327	Phase 3
0.7333	Intermediate Similarity	NPD3685	Discontinued
0.7329	Intermediate Similarity	NPD6559	Discontinued
0.7324	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5403	Approved
0.731	Intermediate Similarity	NPD6674	Discontinued
0.7305	Intermediate Similarity	NPD5735	Approved
0.7305	Intermediate Similarity	NPD4340	Discontinued
0.7293	Intermediate Similarity	NPD4626	Approved
0.7292	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6005	Phase 3
0.7292	Intermediate Similarity	NPD6004	Phase 3
0.7292	Intermediate Similarity	NPD6002	Phase 3
0.7287	Intermediate Similarity	NPD5283	Phase 1
0.7286	Intermediate Similarity	NPD6407	Approved
0.7286	Intermediate Similarity	NPD6405	Approved
0.7285	Intermediate Similarity	NPD6599	Discontinued
0.7273	Intermediate Similarity	NPD1894	Discontinued
0.7273	Intermediate Similarity	NPD3882	Suspended
0.7261	Intermediate Similarity	NPD7229	Phase 3
0.726	Intermediate Similarity	NPD4628	Phase 3
0.7255	Intermediate Similarity	NPD8455	Phase 2
0.7254	Intermediate Similarity	NPD4097	Suspended
0.7248	Intermediate Similarity	NPD1512	Approved
0.7244	Intermediate Similarity	NPD5494	Approved
0.7239	Intermediate Similarity	NPD3496	Discontinued
0.7239	Intermediate Similarity	NPD3847	Discontinued
0.7234	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD2238	Phase 2
0.7234	Intermediate Similarity	NPD4140	Approved
0.7222	Intermediate Similarity	NPD4477	Approved
0.7222	Intermediate Similarity	NPD4476	Approved
0.7218	Intermediate Similarity	NPD3443	Approved
0.7218	Intermediate Similarity	NPD3444	Approved
0.7218	Intermediate Similarity	NPD3049	Approved
0.7218	Intermediate Similarity	NPD3445	Approved
0.7218	Intermediate Similarity	NPD5691	Approved
0.7214	Intermediate Similarity	NPD1296	Phase 2
0.7205	Intermediate Similarity	NPD7074	Phase 3
0.7192	Intermediate Similarity	NPD2800	Approved
0.719	Intermediate Similarity	NPD37	Approved
0.7185	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD1535	Discovery
0.7181	Intermediate Similarity	NPD5401	Approved
0.7179	Intermediate Similarity	NPD6234	Discontinued
0.7176	Intermediate Similarity	NPD6387	Discontinued
0.7172	Intermediate Similarity	NPD5762	Approved
0.7172	Intermediate Similarity	NPD5763	Approved
0.7172	Intermediate Similarity	NPD7030	Discontinued
0.7164	Intermediate Similarity	NPD1778	Approved
0.7164	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2556	Approved
0.7164	Intermediate Similarity	NPD2554	Approved
0.7163	Intermediate Similarity	NPD4062	Phase 3
0.7163	Intermediate Similarity	NPD7477	Discontinued
0.7161	Intermediate Similarity	NPD4967	Phase 2
0.7161	Intermediate Similarity	NPD4965	Approved
0.7161	Intermediate Similarity	NPD4966	Approved
0.7154	Intermediate Similarity	NPD1398	Phase 1
0.7153	Intermediate Similarity	NPD2799	Discontinued
0.7153	Intermediate Similarity	NPD4108	Discontinued
0.7153	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7741	Discontinued
0.7143	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7095	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data