NPASS Compound

Structure

CID105847 OpenBabel06191715452D 21 23 0 0 0 0 0 0 0 0999 V2000 3.4641 -3.0000 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 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 1.7321 -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 -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 -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 0.8660 -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 -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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 3.4641 -2.0000 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 4 2 0 0 0 0 3 5 1 0 0 0 0 4 9 1 0 0 0 0 5 10 2 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 12 2 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 14 2 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.08
Volume:	285.119
LogP:	3.298
LogD:	2.919
LogS:	-3.957
# Rotatable Bonds:	2
TPSA:	79.15
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.498
Synthetic Accessibility Score:	2.523
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	3
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.07
MDCK Permeability:	1.2747342225338798e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	93.22199249267578%
Volume Distribution (VD):	0.54
Pgp-substrate:	11.133479118347168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.144
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.539
CYP2C9-substrate:	0.864
CYP2D6-inhibitor:	0.523
CYP2D6-substrate:	0.751
CYP3A4-inhibitor:	0.218
CYP3A4-substrate:	0.166

ADMET: Excretion

Clearance (CL):	11.969
Half-life (T1/2):	0.865

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.027
Drug-inuced Liver Injury (DILI):	0.901
AMES Toxicity:	0.7
Rat Oral Acute Toxicity:	0.326
Maximum Recommended Daily Dose:	0.818
Skin Sensitization:	0.95
Carcinogencity:	0.256
Eye Corrosion:	0.206
Eye Irritation:	0.964
Respiratory Toxicity:	0.606

Download Data

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

Natural Product: NPC105847

Natural Product ID:	NPC105847
*Common Name:**	4,9-Dimethoxyphenanthrene-2,3,5-Triol
IUPAC Name:	4,9-dimethoxyphenanthrene-2,3,5-triol
Synonyms:
Standard InCHIKey:	GSABLXRGQAKZDS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H14O5/c1-20-12-7-8-6-11(18)15(19)16(21-2)13(8)14-9(12)4-3-5-10(14)17/h3-7,17-19H,1-2H3
SMILES:	COc1cc2cc(c(c(c2c2c1cccc2O)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL254807
PubChem CID:	24762428
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	=	9000.0	nM	PMID[542981]

☑ 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 NPC105847 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	563
0.1-0.2	1987
0.2-0.3	5636
0.3-0.4	12676
0.4-0.5	4507
0.5-0.6	3981
0.6-0.7	7123
0.7-0.8	5047
0.8-0.85	669
0.85-0.9	376
0.9-0.95	98
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC218131
1.0	High Similarity	NPC243759
0.9924	High Similarity	NPC151656
0.9924	High Similarity	NPC230919
0.9924	High Similarity	NPC266453
0.9924	High Similarity	NPC308768
0.9924	High Similarity	NPC12668
0.9924	High Similarity	NPC200935
0.9848	High Similarity	NPC275061
0.9848	High Similarity	NPC220344
0.9848	High Similarity	NPC243996
0.9848	High Similarity	NPC132804
0.9776	High Similarity	NPC175838
0.9773	High Similarity	NPC56329
0.9773	High Similarity	NPC242715
0.9773	High Similarity	NPC266006
0.9773	High Similarity	NPC22902
0.9697	High Similarity	NPC30632
0.9697	High Similarity	NPC202846
0.9697	High Similarity	NPC143139
0.9695	High Similarity	NPC160697
0.963	High Similarity	NPC183709
0.9627	High Similarity	NPC165026
0.9627	High Similarity	NPC295719
0.9627	High Similarity	NPC73505
0.9627	High Similarity	NPC34431
0.9621	High Similarity	NPC69029
0.9621	High Similarity	NPC158142
0.9621	High Similarity	NPC108198
0.9621	High Similarity	NPC10314
0.9621	High Similarity	NPC241241
0.9621	High Similarity	NPC200557
0.9621	High Similarity	NPC294884
0.9552	High Similarity	NPC212942
0.9552	High Similarity	NPC79622
0.9552	High Similarity	NPC29868
0.9545	High Similarity	NPC125649
0.9478	High Similarity	NPC25111
0.9478	High Similarity	NPC6262
0.9478	High Similarity	NPC272157
0.9478	High Similarity	NPC201145
0.9478	High Similarity	NPC90615
0.9478	High Similarity	NPC73535
0.9474	High Similarity	NPC313081
0.9407	High Similarity	NPC184613
0.9403	High Similarity	NPC476639
0.9403	High Similarity	NPC300846
0.9403	High Similarity	NPC114155
0.9403	High Similarity	NPC205442
0.9394	High Similarity	NPC228843
0.9353	High Similarity	NPC126291
0.9328	High Similarity	NPC111655
0.9328	High Similarity	NPC261873
0.9328	High Similarity	NPC283009
0.9318	High Similarity	NPC149337
0.9318	High Similarity	NPC471983
0.9286	High Similarity	NPC262297
0.927	High Similarity	NPC472089
0.9265	High Similarity	NPC6300
0.9265	High Similarity	NPC114171
0.9265	High Similarity	NPC230124
0.9254	High Similarity	NPC103967
0.9254	High Similarity	NPC209199
0.9248	High Similarity	NPC161958
0.9248	High Similarity	NPC14224
0.9242	High Similarity	NPC126836
0.9237	High Similarity	NPC38017
0.9237	High Similarity	NPC23012
0.9237	High Similarity	NPC215300
0.9203	High Similarity	NPC472087
0.9203	High Similarity	NPC472088
0.9203	High Similarity	NPC470917
0.9185	High Similarity	NPC256262
0.9179	High Similarity	NPC32778
0.9173	High Similarity	NPC15543
0.916	High Similarity	NPC53781
0.916	High Similarity	NPC266555
0.9137	High Similarity	NPC469630
0.913	High Similarity	NPC265075
0.9111	High Similarity	NPC206737
0.9111	High Similarity	NPC56764
0.9111	High Similarity	NPC469659
0.9111	High Similarity	NPC188378
0.9111	High Similarity	NPC555
0.9111	High Similarity	NPC276026
0.9111	High Similarity	NPC289258
0.9111	High Similarity	NPC7515
0.9104	High Similarity	NPC218884
0.9091	High Similarity	NPC28765
0.9091	High Similarity	NPC154866
0.9078	High Similarity	NPC233980
0.9071	High Similarity	NPC469795
0.9058	High Similarity	NPC472091
0.9058	High Similarity	NPC472092
0.9058	High Similarity	NPC472090
0.9044	High Similarity	NPC180602
0.9044	High Similarity	NPC214853
0.9044	High Similarity	NPC240279
0.9044	High Similarity	NPC55239
0.903	High Similarity	NPC282508
0.9015	High Similarity	NPC21563
0.9015	High Similarity	NPC74817
0.9015	High Similarity	NPC324112
0.9015	High Similarity	NPC236791
0.9015	High Similarity	NPC159968
0.9015	High Similarity	NPC82679
0.9015	High Similarity	NPC236760
0.9015	High Similarity	NPC124452
0.9015	High Similarity	NPC169474
0.9015	High Similarity	NPC293054
0.9015	High Similarity	NPC252131
0.9015	High Similarity	NPC246620
0.9015	High Similarity	NPC282000
0.9015	High Similarity	NPC471986
0.9014	High Similarity	NPC474397
0.9008	High Similarity	NPC278955
0.9008	High Similarity	NPC105718
0.8986	High Similarity	NPC260741
0.8986	High Similarity	NPC32630
0.8986	High Similarity	NPC55947
0.8986	High Similarity	NPC70682
0.8978	High Similarity	NPC206525
0.8978	High Similarity	NPC472648
0.8978	High Similarity	NPC472649
0.8978	High Similarity	NPC133025
0.8978	High Similarity	NPC472647
0.8978	High Similarity	NPC133463
0.8978	High Similarity	NPC170328
0.8978	High Similarity	NPC191462
0.8971	High Similarity	NPC311256
0.8963	High Similarity	NPC86655
0.8963	High Similarity	NPC303144
0.8963	High Similarity	NPC202762
0.8963	High Similarity	NPC6451
0.8955	High Similarity	NPC299221
0.8955	High Similarity	NPC234488
0.8955	High Similarity	NPC311680
0.8955	High Similarity	NPC51840
0.8939	High Similarity	NPC18924
0.8939	High Similarity	NPC44748
0.8939	High Similarity	NPC78974
0.8939	High Similarity	NPC223953
0.8939	High Similarity	NPC28730
0.8939	High Similarity	NPC223136
0.8939	High Similarity	NPC170485
0.8939	High Similarity	NPC214406
0.8939	High Similarity	NPC103823
0.8936	High Similarity	NPC473845
0.8936	High Similarity	NPC50250
0.8936	High Similarity	NPC473108
0.8931	High Similarity	NPC5796
0.8931	High Similarity	NPC138248
0.8931	High Similarity	NPC228503
0.8931	High Similarity	NPC206487
0.8929	High Similarity	NPC191231
0.8921	High Similarity	NPC266650
0.8913	High Similarity	NPC3072
0.8913	High Similarity	NPC46277
0.8913	High Similarity	NPC301765
0.8913	High Similarity	NPC156948
0.8913	High Similarity	NPC86605
0.8913	High Similarity	NPC35550
0.8913	High Similarity	NPC71465
0.8913	High Similarity	NPC472646
0.8905	High Similarity	NPC258780
0.8905	High Similarity	NPC37410
0.8889	High Similarity	NPC232275
0.8889	High Similarity	NPC45715
0.8889	High Similarity	NPC12275
0.8889	High Similarity	NPC474356
0.8881	High Similarity	NPC58164
0.8881	High Similarity	NPC10225
0.8872	High Similarity	NPC127587
0.8872	High Similarity	NPC473221
0.8864	High Similarity	NPC475169
0.8864	High Similarity	NPC233410
0.8864	High Similarity	NPC105925
0.8864	High Similarity	NPC221077
0.8864	High Similarity	NPC116907
0.8864	High Similarity	NPC472093
0.8864	High Similarity	NPC299584
0.8864	High Similarity	NPC298757
0.8864	High Similarity	NPC117214
0.8864	High Similarity	NPC113495
0.8864	High Similarity	NPC203133
0.8864	High Similarity	NPC82483
0.8864	High Similarity	NPC251855
0.8864	High Similarity	NPC234400
0.8864	High Similarity	NPC17943
0.8864	High Similarity	NPC105031
0.8864	High Similarity	NPC265483
0.8864	High Similarity	NPC60885
0.8864	High Similarity	NPC208950
0.8864	High Similarity	NPC193544
0.8864	High Similarity	NPC57490
0.8857	High Similarity	NPC71046
0.8857	High Similarity	NPC35216
0.8857	High Similarity	NPC19158
0.8855	High Similarity	NPC84086
0.8849	High Similarity	NPC22517

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 NPC105847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	483
0.1-0.2	977
0.2-0.3	1790
0.3-0.4	2791
0.4-0.5	1593
0.5-0.6	868
0.6-0.7	546
0.7-0.8	94
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8741	High Similarity	NPD3027	Phase 3
0.8667	High Similarity	NPD1529	Clinical (unspecified phase)
0.8593	High Similarity	NPD1530	Clinical (unspecified phase)
0.8551	High Similarity	NPD1613	Approved
0.8551	High Similarity	NPD1612	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD4625	Phase 3
0.8323	Intermediate Similarity	NPD6232	Discontinued
0.8273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD7473	Discontinued
0.8129	Intermediate Similarity	NPD4908	Phase 1
0.8013	Intermediate Similarity	NPD6234	Discontinued
0.795	Intermediate Similarity	NPD5844	Phase 1
0.7929	Intermediate Similarity	NPD3018	Phase 2
0.7922	Intermediate Similarity	NPD37	Approved
0.7902	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD3620	Phase 2
0.7883	Intermediate Similarity	NPD1610	Phase 2
0.7863	Intermediate Similarity	NPD228	Approved
0.7838	Intermediate Similarity	NPD6674	Discontinued
0.7838	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD1934	Approved
0.7771	Intermediate Similarity	NPD4967	Phase 2
0.7771	Intermediate Similarity	NPD4966	Approved
0.7771	Intermediate Similarity	NPD4965	Approved
0.777	Intermediate Similarity	NPD2982	Phase 2
0.777	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2983	Phase 2
0.777	Intermediate Similarity	NPD4749	Approved
0.7756	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD5283	Phase 1
0.773	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1548	Phase 1
0.7698	Intermediate Similarity	NPD2981	Phase 2
0.7669	Intermediate Similarity	NPD7228	Approved
0.7655	Intermediate Similarity	NPD4060	Phase 1
0.7643	Intermediate Similarity	NPD2801	Approved
0.7639	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7199	Phase 2
0.7557	Intermediate Similarity	NPD2342	Discontinued
0.7551	Intermediate Similarity	NPD4097	Suspended
0.7547	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD6166	Phase 2
0.7546	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD1465	Phase 2
0.7518	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1511	Approved
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD4626	Approved
0.7469	Intermediate Similarity	NPD6959	Discontinued
0.7444	Intermediate Similarity	NPD3021	Approved
0.7444	Intermediate Similarity	NPD3022	Approved
0.7431	Intermediate Similarity	NPD2861	Phase 2
0.7419	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1512	Approved
0.7389	Intermediate Similarity	NPD4005	Discontinued
0.7376	Intermediate Similarity	NPD3705	Approved
0.7353	Intermediate Similarity	NPD8054	Approved
0.7353	Intermediate Similarity	NPD8053	Approved
0.7351	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3540	Phase 1
0.7343	Intermediate Similarity	NPD6696	Suspended
0.7343	Intermediate Similarity	NPD1283	Approved
0.7329	Intermediate Similarity	NPD3882	Suspended
0.7325	Intermediate Similarity	NPD1653	Approved
0.7313	Intermediate Similarity	NPD4750	Phase 3
0.7308	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD1558	Phase 1
0.7286	Intermediate Similarity	NPD1651	Approved
0.7285	Intermediate Similarity	NPD3539	Phase 1
0.7285	Intermediate Similarity	NPD6099	Approved
0.7285	Intermediate Similarity	NPD6100	Approved
0.7284	Intermediate Similarity	NPD4055	Discovery
0.7283	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7635	Approved
0.7273	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1611	Approved
0.7244	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD4380	Phase 2
0.7222	Intermediate Similarity	NPD8651	Approved
0.7212	Intermediate Similarity	NPD7229	Phase 3
0.7208	Intermediate Similarity	NPD3750	Approved
0.72	Intermediate Similarity	NPD1607	Approved
0.7179	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7041	Phase 2
0.7179	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7390	Discontinued
0.7176	Intermediate Similarity	NPD7240	Approved
0.7176	Intermediate Similarity	NPD6559	Discontinued
0.7172	Intermediate Similarity	NPD3094	Phase 2
0.7163	Intermediate Similarity	NPD5691	Approved
0.716	Intermediate Similarity	NPD7074	Phase 3
0.716	Intermediate Similarity	NPD3817	Phase 2
0.7152	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3818	Discontinued
0.7134	Intermediate Similarity	NPD2533	Approved
0.7134	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2532	Approved
0.7134	Intermediate Similarity	NPD2534	Approved
0.7134	Intermediate Similarity	NPD7447	Phase 1
0.7133	Intermediate Similarity	NPD5735	Approved
0.7133	Intermediate Similarity	NPD3657	Discovery
0.7133	Intermediate Similarity	NPD1281	Approved
0.7133	Intermediate Similarity	NPD422	Phase 1
0.7123	Intermediate Similarity	NPD4624	Approved
0.7117	Intermediate Similarity	NPD7768	Phase 2
0.7115	Intermediate Similarity	NPD7124	Phase 2
0.7113	Intermediate Similarity	NPD2286	Discontinued
0.7105	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1510	Phase 2
0.7101	Intermediate Similarity	NPD7054	Approved
0.7099	Intermediate Similarity	NPD7819	Suspended
0.7099	Intermediate Similarity	NPD1242	Phase 1
0.7097	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7003	Approved
0.7091	Intermediate Similarity	NPD5494	Approved
0.7078	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4357	Discontinued
0.707	Intermediate Similarity	NPD7212	Phase 2
0.707	Intermediate Similarity	NPD7213	Phase 3
0.7067	Intermediate Similarity	NPD1240	Approved
0.7059	Intermediate Similarity	NPD2935	Discontinued
0.7059	Intermediate Similarity	NPD7472	Approved
0.7055	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5110	Phase 2
0.7047	Intermediate Similarity	NPD5109	Approved
0.7047	Intermediate Similarity	NPD5111	Phase 2
0.7047	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD846	Approved
0.7045	Intermediate Similarity	NPD940	Approved
0.7039	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4536	Approved
0.7039	Intermediate Similarity	NPD4538	Approved
0.7035	Intermediate Similarity	NPD7549	Discontinued
0.7035	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1669	Approved
0.7032	Intermediate Similarity	NPD5177	Phase 3
0.7029	Intermediate Similarity	NPD7906	Approved
0.7025	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5536	Phase 2
0.7019	Intermediate Similarity	NPD4678	Approved
0.7019	Intermediate Similarity	NPD4675	Approved
0.7018	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD3092	Approved
0.7013	Intermediate Similarity	NPD5762	Approved
0.7013	Intermediate Similarity	NPD7266	Discontinued
0.7013	Intermediate Similarity	NPD5763	Approved
0.7012	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6584	Phase 3
0.7	Intermediate Similarity	NPD6671	Approved
0.7	Intermediate Similarity	NPD709	Approved
0.6994	Remote Similarity	NPD4578	Approved
0.6994	Remote Similarity	NPD4577	Approved
0.6994	Remote Similarity	NPD5929	Approved
0.6993	Remote Similarity	NPD5126	Approved
0.6993	Remote Similarity	NPD5125	Phase 3
0.6988	Remote Similarity	NPD6746	Phase 2
0.6987	Remote Similarity	NPD3892	Phase 2
0.698	Remote Similarity	NPD7095	Approved
0.6978	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1398	Phase 1
0.6975	Remote Similarity	NPD5089	Approved
0.6975	Remote Similarity	NPD5090	Approved
0.6971	Remote Similarity	NPD4663	Approved
0.697	Remote Similarity	NPD7075	Discontinued
0.6957	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3226	Approved
0.6954	Remote Similarity	NPD2238	Phase 2
0.6954	Remote Similarity	NPD2979	Phase 3
0.6954	Remote Similarity	NPD943	Approved
0.695	Remote Similarity	NPD7340	Approved
0.6948	Remote Similarity	NPD5404	Approved
0.6948	Remote Similarity	NPD5405	Approved
0.6948	Remote Similarity	NPD5406	Approved
0.6948	Remote Similarity	NPD5408	Approved
0.6948	Remote Similarity	NPD2438	Suspended
0.6943	Remote Similarity	NPD2677	Approved
0.6943	Remote Similarity	NPD2219	Phase 1
0.6943	Remote Similarity	NPD5241	Discontinued
0.6941	Remote Similarity	NPD8252	Approved
0.6941	Remote Similarity	NPD8251	Approved
0.6941	Remote Similarity	NPD8099	Discontinued
0.6934	Remote Similarity	NPD5451	Approved
0.6933	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6798	Discontinued
0.6928	Remote Similarity	NPD6111	Discontinued
0.6923	Remote Similarity	NPD3060	Approved
0.6923	Remote Similarity	NPD2489	Approved
0.6923	Remote Similarity	NPD27	Approved
0.6919	Remote Similarity	NPD6797	Phase 2
0.6918	Remote Similarity	NPD5327	Phase 3
0.6909	Remote Similarity	NPD6788	Approved
0.6908	Remote Similarity	NPD230	Phase 1
0.6908	Remote Similarity	NPD5124	Phase 1

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