NPASS Compound

Structure

NPC266006 OpenBabel07101718182D 22 24 0 0 0 0 0 0 0 0999 V2000 -2.5981 3.5000 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 0.8660 -1.5000 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 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 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 -2.5981 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 1.5000 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 0.0000 3.0000 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 0.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 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 -0.8660 3.5000 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 6 1 0 0 0 0 5 10 1 0 0 0 0 6 12 2 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 9 1 0 0 0 0 8 13 2 0 0 0 0 9 18 1 0 0 0 0 10 14 2 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 16 17 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.1
Volume:	302.415
LogP:	3.477
LogD:	3.223
LogS:	-3.914
# Rotatable Bonds:	3
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.725
Synthetic Accessibility Score:	2.437
Fsp3:	0.176
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:	-4.889
MDCK Permeability:	2.4208366085076705e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	90.37635040283203%
Volume Distribution (VD):	0.636
Pgp-substrate:	12.74748706817627%

ADMET: Metabolism

CYP1A2-inhibitor:	0.957
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.442
CYP2C19-substrate:	0.487
CYP2C9-inhibitor:	0.46
CYP2C9-substrate:	0.933
CYP2D6-inhibitor:	0.722
CYP2D6-substrate:	0.899
CYP3A4-inhibitor:	0.446
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	11.381
Half-life (T1/2):	0.714

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.034
Drug-inuced Liver Injury (DILI):	0.601
AMES Toxicity:	0.607
Rat Oral Acute Toxicity:	0.36
Maximum Recommended Daily Dose:	0.615
Skin Sensitization:	0.921
Carcinogencity:	0.07
Eye Corrosion:	0.13
Eye Irritation:	0.969
Respiratory Toxicity:	0.58

Download Data

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

Natural Product: NPC266006

Natural Product ID:	NPC266006
*Common Name:**	Plicatol A
IUPAC Name:	4,9,10-trimethoxyphenanthrene-2,5-diol
Synonyms:
Standard InCHIKey:	DRZYTLJQXLHYME-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O5/c1-20-13-8-9(18)7-11-15(13)14-10(5-4-6-12(14)19)16(21-2)17(11)22-3/h4-8,18-19H,1-3H3
SMILES:	COc1c(OC)c2cc(O)cc(c2c2c1cccc2O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL438339
PubChem CID:	44445445
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0003007] Phenanthrols

*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
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575955]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	stems	Yunnan Province, China	2004	PMID[17253844]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	purchased from Kyoungdong Oriental Herbal Market, Seoul, Korea	2006-APR	PMID[18052323]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	Stems	n.a.	n.a.	PMID[27310249]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3894	Dendrobium nobile	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3894	Dendrobium nobile	Species	Orchidaceae	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
IC50	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[542548]

☑ 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 NPC266006 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	559
0.1-0.2	2001
0.2-0.3	5468
0.3-0.4	12809
0.4-0.5	4470
0.5-0.6	3948
0.6-0.7	7106
0.7-0.8	5218
0.8-0.85	707
0.85-0.9	290
0.9-0.95	100
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9848	High Similarity	NPC308768
0.9848	High Similarity	NPC12668
0.9773	High Similarity	NPC220344
0.9773	High Similarity	NPC275061
0.9773	High Similarity	NPC218131
0.9773	High Similarity	NPC105847
0.9773	High Similarity	NPC132804
0.9773	High Similarity	NPC243996
0.9773	High Similarity	NPC243759
0.9701	High Similarity	NPC175838
0.9697	High Similarity	NPC151656
0.9697	High Similarity	NPC56329
0.9697	High Similarity	NPC230919
0.9697	High Similarity	NPC200935
0.9697	High Similarity	NPC242715
0.9697	High Similarity	NPC266453
0.9697	High Similarity	NPC22902
0.9621	High Similarity	NPC202846
0.9621	High Similarity	NPC30632
0.9621	High Similarity	NPC143139
0.9621	High Similarity	NPC205442
0.9556	High Similarity	NPC183709
0.9552	High Similarity	NPC73505
0.9552	High Similarity	NPC295719
0.9552	High Similarity	NPC34431
0.9552	High Similarity	NPC165026
0.9545	High Similarity	NPC294884
0.9545	High Similarity	NPC200557
0.9545	High Similarity	NPC69029
0.9545	High Similarity	NPC241241
0.9545	High Similarity	NPC158142
0.9545	High Similarity	NPC111655
0.9545	High Similarity	NPC108198
0.9545	High Similarity	NPC10314
0.9538	High Similarity	NPC149337
0.9538	High Similarity	NPC471983
0.9478	High Similarity	NPC212942
0.9478	High Similarity	NPC79622
0.9478	High Similarity	NPC29868
0.947	High Similarity	NPC160697
0.947	High Similarity	NPC125649
0.9403	High Similarity	NPC272157
0.9403	High Similarity	NPC90615
0.9403	High Similarity	NPC73535
0.9403	High Similarity	NPC25111
0.9403	High Similarity	NPC6262
0.9403	High Similarity	NPC201145
0.9398	High Similarity	NPC313081
0.9333	High Similarity	NPC184613
0.9328	High Similarity	NPC300846
0.9328	High Similarity	NPC114155
0.9328	High Similarity	NPC476639
0.9318	High Similarity	NPC228843
0.9308	High Similarity	NPC215300
0.9308	High Similarity	NPC38017
0.9281	High Similarity	NPC126291
0.9254	High Similarity	NPC283009
0.9254	High Similarity	NPC261873
0.9242	High Similarity	NPC282508
0.9231	High Similarity	NPC471986
0.9231	High Similarity	NPC53781
0.9214	High Similarity	NPC262297
0.9197	High Similarity	NPC472089
0.9191	High Similarity	NPC230124
0.9191	High Similarity	NPC6300
0.9191	High Similarity	NPC114171
0.9185	High Similarity	NPC170328
0.9185	High Similarity	NPC472648
0.9185	High Similarity	NPC133463
0.9185	High Similarity	NPC191462
0.9185	High Similarity	NPC472649
0.9185	High Similarity	NPC472647
0.9185	High Similarity	NPC206525
0.9179	High Similarity	NPC209199
0.9179	High Similarity	NPC103967
0.9173	High Similarity	NPC161958
0.9173	High Similarity	NPC14224
0.9167	High Similarity	NPC126836
0.9154	High Similarity	NPC223953
0.9154	High Similarity	NPC170485
0.913	High Similarity	NPC472088
0.913	High Similarity	NPC470917
0.913	High Similarity	NPC472087
0.9118	High Similarity	NPC472646
0.9118	High Similarity	NPC71465
0.9111	High Similarity	NPC256262
0.9111	High Similarity	NPC37410
0.9111	High Similarity	NPC258780
0.9104	High Similarity	NPC32778
0.9098	High Similarity	NPC15543
0.9084	High Similarity	NPC473221
0.9077	High Similarity	NPC105031
0.9077	High Similarity	NPC105718
0.9077	High Similarity	NPC278955
0.9077	High Similarity	NPC113495
0.9077	High Similarity	NPC105925
0.9065	High Similarity	NPC469630
0.9058	High Similarity	NPC265075
0.9037	High Similarity	NPC276026
0.9037	High Similarity	NPC56764
0.9037	High Similarity	NPC555
0.9037	High Similarity	NPC206737
0.9037	High Similarity	NPC289258
0.9037	High Similarity	NPC469659
0.9037	High Similarity	NPC188378
0.9037	High Similarity	NPC7515
0.903	High Similarity	NPC218884
0.9023	High Similarity	NPC254000
0.9023	High Similarity	NPC224157
0.9023	High Similarity	NPC192687
0.9015	High Similarity	NPC28765
0.9015	High Similarity	NPC154866
0.9015	High Similarity	NPC23012
0.9008	High Similarity	NPC82299
0.9007	High Similarity	NPC233980
0.9	High Similarity	NPC228503
0.9	High Similarity	NPC138248
0.9	High Similarity	NPC469795
0.8986	High Similarity	NPC472092
0.8986	High Similarity	NPC472091
0.8986	High Similarity	NPC273623
0.8986	High Similarity	NPC472090
0.8971	High Similarity	NPC214853
0.8971	High Similarity	NPC180602
0.8971	High Similarity	NPC240279
0.8971	High Similarity	NPC55239
0.8947	High Similarity	NPC190144
0.8944	High Similarity	NPC474397
0.8939	High Similarity	NPC169474
0.8939	High Similarity	NPC293054
0.8939	High Similarity	NPC252131
0.8939	High Similarity	NPC82679
0.8939	High Similarity	NPC266555
0.8939	High Similarity	NPC246620
0.8939	High Similarity	NPC21563
0.8939	High Similarity	NPC324112
0.8939	High Similarity	NPC124452
0.8939	High Similarity	NPC236760
0.8939	High Similarity	NPC282000
0.8939	High Similarity	NPC74817
0.8939	High Similarity	NPC236791
0.8939	High Similarity	NPC159968
0.8923	High Similarity	NPC282496
0.8923	High Similarity	NPC233526
0.8913	High Similarity	NPC55947
0.8913	High Similarity	NPC260741
0.8913	High Similarity	NPC32630
0.8913	High Similarity	NPC70682
0.8905	High Similarity	NPC133025
0.8897	High Similarity	NPC311256
0.8889	High Similarity	NPC303144
0.8889	High Similarity	NPC6451
0.8889	High Similarity	NPC102256
0.8881	High Similarity	NPC311680
0.8881	High Similarity	NPC51840
0.8881	High Similarity	NPC234488
0.8881	High Similarity	NPC299221
0.8873	High Similarity	NPC33832
0.8865	High Similarity	NPC50250
0.8865	High Similarity	NPC473845
0.8865	High Similarity	NPC473108
0.8864	High Similarity	NPC78974
0.8864	High Similarity	NPC223136
0.8864	High Similarity	NPC103823
0.8864	High Similarity	NPC214406
0.8864	High Similarity	NPC18924
0.8864	High Similarity	NPC44748
0.8864	High Similarity	NPC28730
0.8857	High Similarity	NPC191231
0.8849	High Similarity	NPC266650
0.8841	High Similarity	NPC35550
0.8841	High Similarity	NPC86605
0.8841	High Similarity	NPC301765
0.8841	High Similarity	NPC46277
0.8841	High Similarity	NPC156948
0.8841	High Similarity	NPC3072
0.8824	High Similarity	NPC469610
0.8815	High Similarity	NPC45715
0.8815	High Similarity	NPC160623
0.8815	High Similarity	NPC232275
0.8815	High Similarity	NPC8899
0.8815	High Similarity	NPC474356
0.8815	High Similarity	NPC12275
0.8806	High Similarity	NPC58164
0.8806	High Similarity	NPC469963
0.8806	High Similarity	NPC471518
0.8806	High Similarity	NPC469951
0.8806	High Similarity	NPC471519
0.8806	High Similarity	NPC10225
0.8803	High Similarity	NPC221318
0.8803	High Similarity	NPC469557
0.8803	High Similarity	NPC125617
0.8797	High Similarity	NPC127587
0.8797	High Similarity	NPC242032
0.8794	High Similarity	NPC258083
0.8788	High Similarity	NPC299584
0.8788	High Similarity	NPC221077
0.8788	High Similarity	NPC251855
0.8788	High Similarity	NPC298757
0.8788	High Similarity	NPC265483

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 NPC266006 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	477
0.1-0.2	979
0.2-0.3	1727
0.3-0.4	2798
0.4-0.5	1608
0.5-0.6	884
0.6-0.7	557
0.7-0.8	111
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8667	High Similarity	NPD3027	Phase 3
0.8667	High Similarity	NPD4625	Phase 3
0.8497	Intermediate Similarity	NPD6232	Discontinued
0.8467	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1613	Approved
0.8345	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7473	Discontinued
0.8321	Intermediate Similarity	NPD4908	Phase 1
0.8116	Intermediate Similarity	NPD3018	Phase 2
0.8113	Intermediate Similarity	NPD5844	Phase 1
0.8092	Intermediate Similarity	NPD37	Approved
0.7956	Intermediate Similarity	NPD4749	Approved
0.7956	Intermediate Similarity	NPD2982	Phase 2
0.7956	Intermediate Similarity	NPD2983	Phase 2
0.7956	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD6234	Discontinued
0.7941	Intermediate Similarity	NPD1610	Phase 2
0.7939	Intermediate Similarity	NPD5283	Phase 1
0.7935	Intermediate Similarity	NPD4965	Approved
0.7935	Intermediate Similarity	NPD4967	Phase 2
0.7935	Intermediate Similarity	NPD4966	Approved
0.7914	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6674	Discontinued
0.7891	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD2981	Phase 2
0.7832	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD3620	Phase 2
0.7817	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1548	Phase 1
0.7724	Intermediate Similarity	NPD4097	Suspended
0.7708	Intermediate Similarity	NPD4060	Phase 1
0.7692	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD4626	Approved
0.7652	Intermediate Similarity	NPD228	Approved
0.7628	Intermediate Similarity	NPD1934	Approved
0.7625	Intermediate Similarity	NPD7199	Phase 2
0.7625	Intermediate Similarity	NPD6959	Discontinued
0.7615	Intermediate Similarity	NPD2342	Discontinued
0.7607	Intermediate Similarity	NPD7228	Approved
0.7606	Intermediate Similarity	NPD2861	Phase 2
0.758	Intermediate Similarity	NPD2801	Approved
0.7554	Intermediate Similarity	NPD3705	Approved
0.7548	Intermediate Similarity	NPD4005	Discontinued
0.7531	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD6696	Suspended
0.7517	Intermediate Similarity	NPD3540	Phase 1
0.75	Intermediate Similarity	NPD4750	Phase 3
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1651	Approved
0.7463	Intermediate Similarity	NPD7635	Approved
0.745	Intermediate Similarity	NPD3539	Phase 1
0.745	Intermediate Similarity	NPD6100	Approved
0.745	Intermediate Similarity	NPD6099	Approved
0.7447	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4055	Discovery
0.7434	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1283	Approved
0.7368	Intermediate Similarity	NPD3022	Approved
0.7368	Intermediate Similarity	NPD3021	Approved
0.7362	Intermediate Similarity	NPD7229	Phase 3
0.7358	Intermediate Similarity	NPD1465	Phase 2
0.7338	Intermediate Similarity	NPD5691	Approved
0.7338	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7390	Discontinued
0.7338	Intermediate Similarity	NPD1511	Approved
0.7338	Intermediate Similarity	NPD7041	Phase 2
0.7338	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1611	Approved
0.7297	Intermediate Similarity	NPD3657	Discovery
0.7294	Intermediate Similarity	NPD8053	Approved
0.7294	Intermediate Similarity	NPD8054	Approved
0.7292	Intermediate Similarity	NPD4624	Approved
0.729	Intermediate Similarity	NPD2534	Approved
0.729	Intermediate Similarity	NPD2533	Approved
0.729	Intermediate Similarity	NPD2532	Approved
0.729	Intermediate Similarity	NPD7447	Phase 1
0.7285	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD4380	Phase 2
0.7273	Intermediate Similarity	NPD8651	Approved
0.7273	Intermediate Similarity	NPD7124	Phase 2
0.7267	Intermediate Similarity	NPD7768	Phase 2
0.7267	Intermediate Similarity	NPD3882	Suspended
0.7261	Intermediate Similarity	NPD1653	Approved
0.7255	Intermediate Similarity	NPD7003	Approved
0.7255	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3750	Approved
0.725	Intermediate Similarity	NPD7819	Suspended
0.7248	Intermediate Similarity	NPD1607	Approved
0.7244	Intermediate Similarity	NPD1512	Approved
0.7239	Intermediate Similarity	NPD5494	Approved
0.7231	Intermediate Similarity	NPD846	Approved
0.7231	Intermediate Similarity	NPD940	Approved
0.7226	Intermediate Similarity	NPD7213	Phase 3
0.7226	Intermediate Similarity	NPD7212	Phase 2
0.7226	Intermediate Similarity	NPD4357	Discontinued
0.7225	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3094	Phase 2
0.7222	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6559	Discontinued
0.7219	Intermediate Similarity	NPD7240	Approved
0.7219	Intermediate Similarity	NPD2935	Discontinued
0.7211	Intermediate Similarity	NPD5109	Approved
0.7211	Intermediate Similarity	NPD5110	Phase 2
0.7211	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD5111	Phase 2
0.7205	Intermediate Similarity	NPD3817	Phase 2
0.7205	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1669	Approved
0.7194	Intermediate Similarity	NPD5536	Phase 2
0.719	Intermediate Similarity	NPD5177	Phase 3
0.7183	Intermediate Similarity	NPD1281	Approved
0.7183	Intermediate Similarity	NPD422	Phase 1
0.7181	Intermediate Similarity	NPD5735	Approved
0.7179	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7549	Discontinued
0.7174	Intermediate Similarity	NPD6671	Approved
0.7172	Intermediate Similarity	NPD6584	Phase 3
0.717	Intermediate Similarity	NPD4678	Approved
0.717	Intermediate Similarity	NPD4675	Approved
0.7163	Intermediate Similarity	NPD2286	Discontinued
0.7154	Intermediate Similarity	NPD1242	Phase 1
0.7153	Intermediate Similarity	NPD1398	Phase 1
0.7152	Intermediate Similarity	NPD1510	Phase 2
0.7152	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5929	Approved
0.7143	Intermediate Similarity	NPD3892	Phase 2
0.7134	Intermediate Similarity	NPD6746	Phase 2
0.7125	Intermediate Similarity	NPD5090	Approved
0.7125	Intermediate Similarity	NPD5089	Approved
0.7124	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7340	Approved
0.7114	Intermediate Similarity	NPD1240	Approved
0.7114	Intermediate Similarity	NPD1558	Phase 1
0.7114	Intermediate Similarity	NPD2238	Phase 2
0.7114	Intermediate Similarity	NPD2979	Phase 3
0.7111	Intermediate Similarity	NPD5451	Approved
0.7107	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5408	Approved
0.7105	Intermediate Similarity	NPD5405	Approved
0.7105	Intermediate Similarity	NPD2438	Suspended
0.7105	Intermediate Similarity	NPD5404	Approved
0.7105	Intermediate Similarity	NPD5406	Approved
0.7101	Intermediate Similarity	NPD7074	Phase 3
0.7097	Intermediate Similarity	NPD5241	Discontinued
0.7097	Intermediate Similarity	NPD2219	Phase 1
0.7095	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4536	Approved
0.7086	Intermediate Similarity	NPD4538	Approved
0.7086	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6111	Discontinued
0.7083	Intermediate Similarity	NPD3818	Discontinued
0.7083	Intermediate Similarity	NPD8251	Approved
0.7083	Intermediate Similarity	NPD8099	Discontinued
0.7083	Intermediate Similarity	NPD8252	Approved
0.7083	Intermediate Similarity	NPD5327	Phase 3
0.7078	Intermediate Similarity	NPD3060	Approved
0.707	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD5124	Phase 1
0.7067	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3092	Approved
0.7059	Intermediate Similarity	NPD5763	Approved
0.7059	Intermediate Similarity	NPD5762	Approved
0.7055	Intermediate Similarity	NPD6788	Approved
0.7055	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD709	Approved
0.7042	Intermediate Similarity	NPD5125	Phase 3
0.7042	Intermediate Similarity	NPD5126	Approved
0.7041	Intermediate Similarity	NPD8156	Discontinued
0.7041	Intermediate Similarity	NPD7054	Approved
0.7039	Intermediate Similarity	NPD4108	Discontinued
0.7032	Intermediate Similarity	NPD6331	Phase 2
0.7029	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7095	Approved
0.7021	Intermediate Similarity	NPD3091	Approved
0.7019	Intermediate Similarity	NPD7411	Suspended
0.7014	Intermediate Similarity	NPD2233	Approved
0.7014	Intermediate Similarity	NPD2232	Approved
0.7014	Intermediate Similarity	NPD2230	Approved
0.7013	Intermediate Similarity	NPD7037	Approved
0.7012	Intermediate Similarity	NPD7075	Discontinued
0.7	Intermediate Similarity	NPD3226	Approved
0.7	Intermediate Similarity	NPD7472	Approved
0.7	Intermediate Similarity	NPD4140	Approved
0.6987	Remote Similarity	NPD2677	Approved
0.6987	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6798	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