NPASS Compound

Structure

CID224342 OpenBabel06191716022D 28 30 0 0 0 0 0 0 0 0999 V2000 -0.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 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 0.8660 -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 2.5981 -1.5000 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 0.0000 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 3.4641 -0.0000 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 -4.5000 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 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 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 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 -0.8660 -1.5000 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 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 14 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 10 1 0 0 0 0 7 15 1 0 0 0 0 8 17 1 0 0 0 0 9 18 1 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 20 1 0 0 0 0 12 19 2 0 0 0 0 12 21 1 0 0 0 0 15 19 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 24 2 0 0 0 0 23 27 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.2
Volume:	412.06
LogP:	6.86
LogD:	3.566
LogS:	-3.198
# Rotatable Bonds:	4
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.429
Synthetic Accessibility Score:	3.149
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.21
MDCK Permeability:	1.286371480091475e-05
Pgp-inhibitor:	0.462
Pgp-substrate:	0.083
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	97.8990707397461%
Volume Distribution (VD):	4.431
Pgp-substrate:	2.8143911361694336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.655
CYP1A2-substrate:	0.198
CYP2C19-inhibitor:	0.431
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.541
CYP2C9-substrate:	0.769
CYP2D6-inhibitor:	0.285
CYP2D6-substrate:	0.463
CYP3A4-inhibitor:	0.097
CYP3A4-substrate:	0.092

ADMET: Excretion

Clearance (CL):	14.655
Half-life (T1/2):	0.503

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.86
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.103
Rat Oral Acute Toxicity:	0.235
Maximum Recommended Daily Dose:	0.45
Skin Sensitization:	0.943
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.292
Respiratory Toxicity:	0.414

Download Data

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

Natural Product: NPC224342

Natural Product ID:	NPC224342
*Common Name:**	6,8-Bis(3-Methylbut-2-Enyl)-9,10-Dihydrophenanthrene-2,3,5,7-Tetrol
IUPAC Name:	6,8-bis(3-methylbut-2-enyl)-9,10-dihydrophenanthrene-2,3,5,7-tetrol
Synonyms:
Standard InCHIKey:	YJJXCOSDPIJFJR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H28O4/c1-13(2)5-8-17-16-10-7-15-11-20(25)21(26)12-19(15)22(16)24(28)18(23(17)27)9-6-14(3)4/h5-6,11-12,25-28H,7-10H2,1-4H3
SMILES:	CC(=CCc1c(O)c(CC=C(C)C)c2c(c1O)c1cc(O)c(cc1CC2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1535695
PubChem CID:	480818
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	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
EC50	4
IC50	4

Activity Type	# Activity
Cell Line	3
Individual Protein	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1160	Cell Line	BJ	Homo sapiens	EC50	>	75000.0	nM	PMID[557276]
NPT1160	Cell Line	BJ	Homo sapiens	EC50	=	8578.0	nM	PMID[557276]
NPT1160	Cell Line	BJ	Homo sapiens	EC50	>	150000.0	nM	PMID[557276]
NPT2	Others	Unspecified		EC50	=	14702.0	nM	PMID[557276]
NPT799	Individual Protein	Intestinal alkaline phosphatase	Mus musculus	IC50	=	5450.0	nM	PMID[557276]
NPT798	Individual Protein	Alkaline phosphatase placental-like	Homo sapiens	IC50	>	100000.0	nM	PMID[557276]
NPT802	Individual Protein	Alkaline phosphatase, tissue-nonspecific isozyme	Homo sapiens	IC50	>	100000.0	nM	PMID[557276]
NPT801	Individual Protein	Intestinal alkaline phosphatase	Homo sapiens	IC50	>	100000.0	nM	PMID[557276]

☑ 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 NPC224342 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	396
0.1-0.2	1758
0.2-0.3	4938
0.3-0.4	13219
0.4-0.5	5706
0.5-0.6	5277
0.6-0.7	8194
0.7-0.8	2740
0.8-0.85	365
0.85-0.9	88
0.9-0.95	12
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9576	High Similarity	NPC39029
0.9487	High Similarity	NPC191866
0.9412	High Similarity	NPC237667
0.9328	High Similarity	NPC24125
0.9316	High Similarity	NPC277588
0.9256	High Similarity	NPC53567
0.9237	High Similarity	NPC144343
0.916	High Similarity	NPC176893
0.916	High Similarity	NPC217174
0.9145	High Similarity	NPC472893
0.9	High Similarity	NPC56329
0.9	High Similarity	NPC242715
0.9	High Similarity	NPC22902
0.8931	High Similarity	NPC132804
0.8931	High Similarity	NPC220344
0.8931	High Similarity	NPC243996
0.8931	High Similarity	NPC275061
0.8923	High Similarity	NPC30632
0.8915	High Similarity	NPC125649
0.8908	High Similarity	NPC115808
0.8898	High Similarity	NPC107240
0.8864	High Similarity	NPC12668
0.8864	High Similarity	NPC308768
0.8855	High Similarity	NPC200935
0.8855	High Similarity	NPC266453
0.8855	High Similarity	NPC230919
0.8846	High Similarity	NPC10314
0.8846	High Similarity	NPC294884
0.8846	High Similarity	NPC200557
0.8846	High Similarity	NPC241241
0.8846	High Similarity	NPC158142
0.8846	High Similarity	NPC69029
0.8846	High Similarity	NPC108198
0.8833	High Similarity	NPC470760
0.8824	High Similarity	NPC84999
0.8824	High Similarity	NPC246760
0.8814	High Similarity	NPC317869
0.8814	High Similarity	NPC263753
0.8814	High Similarity	NPC117846
0.8788	High Similarity	NPC105847
0.8788	High Similarity	NPC218131
0.8788	High Similarity	NPC243759
0.8779	High Similarity	NPC202846
0.8779	High Similarity	NPC143139
0.877	High Similarity	NPC472071
0.8739	High Similarity	NPC249270
0.8731	High Similarity	NPC183709
0.8731	High Similarity	NPC175838
0.8729	High Similarity	NPC43525
0.8729	High Similarity	NPC471179
0.8729	High Similarity	NPC46940
0.8718	High Similarity	NPC224870
0.8712	High Similarity	NPC151656
0.8712	High Similarity	NPC266006
0.8702	High Similarity	NPC313081
0.8682	High Similarity	NPC15543
0.8678	High Similarity	NPC16030
0.8647	High Similarity	NPC79622
0.8647	High Similarity	NPC29868
0.8647	High Similarity	NPC212942
0.8644	High Similarity	NPC225679
0.8644	High Similarity	NPC151537
0.8644	High Similarity	NPC95716
0.8644	High Similarity	NPC165770
0.8644	High Similarity	NPC4493
0.8644	High Similarity	NPC476632
0.8644	High Similarity	NPC268032
0.8626	High Similarity	NPC160697
0.8626	High Similarity	NPC209199
0.8618	High Similarity	NPC475245
0.8615	High Similarity	NPC228843
0.8615	High Similarity	NPC161958
0.8615	High Similarity	NPC14224
0.8607	High Similarity	NPC206
0.8582	High Similarity	NPC295719
0.8582	High Similarity	NPC73505
0.8582	High Similarity	NPC165026
0.8582	High Similarity	NPC34431
0.8571	High Similarity	NPC166995
0.8571	High Similarity	NPC35550
0.856	High Similarity	NPC471794
0.855	High Similarity	NPC474453
0.8519	High Similarity	NPC71046
0.8519	High Similarity	NPC265075
0.8516	High Similarity	NPC252131
0.8507	High Similarity	NPC114171
0.8507	High Similarity	NPC6300
0.8507	High Similarity	NPC184613
0.8507	High Similarity	NPC230124
0.85	High Similarity	NPC23804
0.85	High Similarity	NPC715
0.8496	Intermediate Similarity	NPC114155
0.8496	Intermediate Similarity	NPC205442
0.8496	Intermediate Similarity	NPC476639
0.8496	Intermediate Similarity	NPC300846
0.8487	Intermediate Similarity	NPC224527
0.8475	Intermediate Similarity	NPC19808
0.8475	Intermediate Similarity	NPC202647
0.8475	Intermediate Similarity	NPC33728
0.8468	Intermediate Similarity	NPC223451
0.8468	Intermediate Similarity	NPC69006
0.8462	Intermediate Similarity	NPC126836
0.8456	Intermediate Similarity	NPC470917
0.845	Intermediate Similarity	NPC28765
0.845	Intermediate Similarity	NPC215300
0.8443	Intermediate Similarity	NPC261973
0.8438	Intermediate Similarity	NPC170485
0.8433	Intermediate Similarity	NPC25111
0.8433	Intermediate Similarity	NPC272157
0.8433	Intermediate Similarity	NPC73535
0.8433	Intermediate Similarity	NPC6262
0.8433	Intermediate Similarity	NPC201145
0.8433	Intermediate Similarity	NPC90615
0.843	Intermediate Similarity	NPC195922
0.8409	Intermediate Similarity	NPC32778
0.8397	Intermediate Similarity	NPC471983
0.8397	Intermediate Similarity	NPC282508
0.8397	Intermediate Similarity	NPC149337
0.839	Intermediate Similarity	NPC105727
0.839	Intermediate Similarity	NPC63698
0.839	Intermediate Similarity	NPC174981
0.839	Intermediate Similarity	NPC61885
0.839	Intermediate Similarity	NPC58427
0.839	Intermediate Similarity	NPC114392
0.839	Intermediate Similarity	NPC233835
0.839	Intermediate Similarity	NPC34864
0.8382	Intermediate Similarity	NPC472089
0.8374	Intermediate Similarity	NPC304510
0.8374	Intermediate Similarity	NPC172219
0.8374	Intermediate Similarity	NPC299180
0.8372	Intermediate Similarity	NPC471986
0.8372	Intermediate Similarity	NPC476536
0.8372	Intermediate Similarity	NPC53781
0.837	Intermediate Similarity	NPC32630
0.8359	Intermediate Similarity	NPC105031
0.8346	Intermediate Similarity	NPC276026
0.8346	Intermediate Similarity	NPC206737
0.8346	Intermediate Similarity	NPC555
0.8346	Intermediate Similarity	NPC7515
0.8346	Intermediate Similarity	NPC188378
0.8346	Intermediate Similarity	NPC289258
0.8346	Intermediate Similarity	NPC56764
0.8346	Intermediate Similarity	NPC469659
0.8345	Intermediate Similarity	NPC126291
0.8333	Intermediate Similarity	NPC176279
0.8333	Intermediate Similarity	NPC260323
0.8333	Intermediate Similarity	NPC469795
0.8333	Intermediate Similarity	NPC218884
0.8333	Intermediate Similarity	NPC473845
0.8321	Intermediate Similarity	NPC472087
0.8321	Intermediate Similarity	NPC472088
0.8321	Intermediate Similarity	NPC191231
0.8319	Intermediate Similarity	NPC254833
0.8319	Intermediate Similarity	NPC314187
0.8319	Intermediate Similarity	NPC186385
0.8319	Intermediate Similarity	NPC299568
0.8319	Intermediate Similarity	NPC228343
0.8319	Intermediate Similarity	NPC58865
0.8309	Intermediate Similarity	NPC198038
0.8309	Intermediate Similarity	NPC234568
0.8308	Intermediate Similarity	NPC23012
0.8308	Intermediate Similarity	NPC154866
0.8308	Intermediate Similarity	NPC38017
0.8306	Intermediate Similarity	NPC471671
0.8305	Intermediate Similarity	NPC176527
0.8305	Intermediate Similarity	NPC151477
0.8295	Intermediate Similarity	NPC82299
0.8295	Intermediate Similarity	NPC9292
0.8295	Intermediate Similarity	NPC145659
0.8291	Intermediate Similarity	NPC37802
0.8286	Intermediate Similarity	NPC262297
0.8284	Intermediate Similarity	NPC37410
0.8284	Intermediate Similarity	NPC256262
0.8284	Intermediate Similarity	NPC240279
0.8284	Intermediate Similarity	NPC55239
0.8284	Intermediate Similarity	NPC261873
0.8284	Intermediate Similarity	NPC111655
0.8284	Intermediate Similarity	NPC214853
0.8284	Intermediate Similarity	NPC180602
0.8284	Intermediate Similarity	NPC283009
0.8281	Intermediate Similarity	NPC138248
0.8281	Intermediate Similarity	NPC228503
0.8268	Intermediate Similarity	NPC120172
0.8258	Intermediate Similarity	NPC312341
0.8258	Intermediate Similarity	NPC160623
0.824	Intermediate Similarity	NPC469644
0.824	Intermediate Similarity	NPC151197
0.8235	Intermediate Similarity	NPC11554
0.8231	Intermediate Similarity	NPC282000
0.8231	Intermediate Similarity	NPC236760
0.8231	Intermediate Similarity	NPC246620
0.8231	Intermediate Similarity	NPC473221
0.8231	Intermediate Similarity	NPC82679
0.8231	Intermediate Similarity	NPC324112
0.8231	Intermediate Similarity	NPC169474
0.8231	Intermediate Similarity	NPC266555
0.8231	Intermediate Similarity	NPC74817
0.8231	Intermediate Similarity	NPC159968
0.8231	Intermediate Similarity	NPC236791
0.8231	Intermediate Similarity	NPC293054

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 NPC224342 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	999
0.2-0.3	1606
0.3-0.4	3106
0.4-0.5	1625
0.5-0.6	968
0.6-0.7	412
0.7-0.8	68
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8319	Intermediate Similarity	NPD4750	Phase 3
0.8319	Intermediate Similarity	NPD3022	Approved
0.8319	Intermediate Similarity	NPD3021	Approved
0.8151	Intermediate Similarity	NPD2342	Discontinued
0.8106	Intermediate Similarity	NPD4625	Phase 3
0.7967	Intermediate Similarity	NPD7635	Approved
0.7955	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD940	Approved
0.7881	Intermediate Similarity	NPD846	Approved
0.7836	Intermediate Similarity	NPD3027	Phase 3
0.7826	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD1242	Phase 1
0.7762	Intermediate Similarity	NPD7390	Discontinued
0.7708	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3094	Phase 2
0.7664	Intermediate Similarity	NPD1613	Approved
0.7664	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD3092	Approved
0.7615	Intermediate Similarity	NPD2286	Discontinued
0.7563	Intermediate Similarity	NPD3020	Approved
0.7536	Intermediate Similarity	NPD943	Approved
0.7519	Intermediate Similarity	NPD4749	Approved
0.7518	Intermediate Similarity	NPD5406	Approved
0.7518	Intermediate Similarity	NPD5404	Approved
0.7518	Intermediate Similarity	NPD5408	Approved
0.7518	Intermediate Similarity	NPD5405	Approved
0.75	Intermediate Similarity	NPD4908	Phase 1
0.748	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD3091	Approved
0.7458	Intermediate Similarity	NPD2860	Approved
0.7458	Intermediate Similarity	NPD844	Approved
0.7458	Intermediate Similarity	NPD2859	Approved
0.7419	Intermediate Similarity	NPD6232	Discontinued
0.741	Intermediate Similarity	NPD3620	Phase 2
0.741	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2420	Approved
0.7397	Intermediate Similarity	NPD2421	Approved
0.7395	Intermediate Similarity	NPD288	Approved
0.7388	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD2933	Approved
0.7373	Intermediate Similarity	NPD2934	Approved
0.7353	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD3019	Approved
0.7348	Intermediate Similarity	NPD4059	Approved
0.7338	Intermediate Similarity	NPD6234	Discontinued
0.7311	Intermediate Similarity	NPD1809	Phase 2
0.7287	Intermediate Similarity	NPD497	Approved
0.7279	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7473	Discontinued
0.7273	Intermediate Similarity	NPD4093	Discontinued
0.7266	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1201	Approved
0.7239	Intermediate Similarity	NPD1610	Phase 2
0.7237	Intermediate Similarity	NPD37	Approved
0.7222	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3095	Discontinued
0.7218	Intermediate Similarity	NPD2932	Approved
0.7209	Intermediate Similarity	NPD496	Approved
0.7209	Intermediate Similarity	NPD495	Approved
0.7209	Intermediate Similarity	NPD498	Approved
0.7203	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4097	Suspended
0.7176	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3018	Phase 2
0.7163	Intermediate Similarity	NPD4060	Phase 1
0.7153	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD845	Approved
0.7123	Intermediate Similarity	NPD6674	Discontinued
0.7097	Intermediate Similarity	NPD4965	Approved
0.7097	Intermediate Similarity	NPD4966	Approved
0.7097	Intermediate Similarity	NPD4967	Phase 2
0.709	Intermediate Similarity	NPD4626	Approved
0.7083	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5844	Phase 1
0.7077	Intermediate Similarity	NPD5283	Phase 1
0.7073	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD1548	Phase 1
0.7054	Intermediate Similarity	NPD228	Approved
0.7034	Intermediate Similarity	NPD6099	Approved
0.7034	Intermediate Similarity	NPD6100	Approved
0.7021	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7228	Approved
0.7007	Intermediate Similarity	NPD2982	Phase 2
0.7007	Intermediate Similarity	NPD2983	Phase 2
0.7	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3845	Phase 1
0.6977	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD8166	Discontinued
0.6957	Remote Similarity	NPD6696	Suspended
0.6934	Remote Similarity	NPD2981	Phase 2
0.6934	Remote Similarity	NPD9269	Phase 2
0.6933	Remote Similarity	NPD1511	Approved
0.6929	Remote Similarity	NPD5736	Approved
0.6923	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6959	Discontinued
0.6918	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD3026	Approved
0.6912	Remote Similarity	NPD3023	Approved
0.6906	Remote Similarity	NPD3053	Approved
0.6906	Remote Similarity	NPD3055	Approved
0.6903	Remote Similarity	NPD1934	Approved
0.6889	Remote Similarity	NPD1651	Approved
0.6889	Remote Similarity	NPD3024	Approved
0.6889	Remote Similarity	NPD3025	Approved
0.6884	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7266	Discontinued
0.687	Remote Similarity	NPD9379	Approved
0.687	Remote Similarity	NPD9377	Approved
0.6864	Remote Similarity	NPD9094	Approved
0.6859	Remote Similarity	NPD1465	Phase 2
0.6859	Remote Similarity	NPD2801	Approved
0.6849	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1512	Approved
0.6838	Remote Similarity	NPD1751	Approved
0.6838	Remote Similarity	NPD4589	Approved
0.6835	Remote Similarity	NPD1283	Approved
0.6835	Remote Similarity	NPD5311	Approved
0.6835	Remote Similarity	NPD5310	Approved
0.6831	Remote Similarity	NPD5156	Approved
0.6831	Remote Similarity	NPD5155	Approved
0.6825	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4005	Discontinued
0.6818	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5303	Approved
0.6815	Remote Similarity	NPD5304	Approved
0.6813	Remote Similarity	NPD7199	Phase 2
0.6809	Remote Similarity	NPD2861	Phase 2
0.6806	Remote Similarity	NPD3062	Approved
0.6806	Remote Similarity	NPD3059	Approved
0.6806	Remote Similarity	NPD3061	Approved
0.6776	Remote Similarity	NPD3645	Discontinued
0.6769	Remote Similarity	NPD1792	Phase 2
0.6765	Remote Similarity	NPD5691	Approved
0.6761	Remote Similarity	NPD2605	Approved
0.6761	Remote Similarity	NPD2606	Approved
0.6759	Remote Similarity	NPD230	Phase 1
0.6759	Remote Similarity	NPD5735	Approved
0.6755	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD1611	Approved
0.6738	Remote Similarity	NPD4624	Approved
0.6736	Remote Similarity	NPD6405	Approved
0.6736	Remote Similarity	NPD6407	Approved
0.6736	Remote Similarity	NPD6663	Approved
0.6733	Remote Similarity	NPD3750	Approved
0.6728	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD5126	Approved
0.6715	Remote Similarity	NPD5125	Phase 3
0.6715	Remote Similarity	NPD9384	Approved
0.6715	Remote Similarity	NPD9381	Approved
0.6712	Remote Similarity	NPD5314	Approved
0.6712	Remote Similarity	NPD2568	Approved
0.6711	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7041	Phase 2
0.6692	Remote Similarity	NPD1398	Phase 1
0.6692	Remote Similarity	NPD2234	Approved
0.6692	Remote Similarity	NPD2229	Approved
0.6692	Remote Similarity	NPD2228	Approved
0.6691	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3637	Approved
0.669	Remote Similarity	NPD3635	Approved
0.669	Remote Similarity	NPD1555	Discontinued
0.669	Remote Similarity	NPD3636	Approved
0.6689	Remote Similarity	NPD6190	Approved
0.6687	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6166	Phase 2
0.6687	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2532	Approved
0.6667	Remote Similarity	NPD2533	Approved
0.6667	Remote Similarity	NPD2534	Approved
0.6667	Remote Similarity	NPD7340	Approved
0.6667	Remote Similarity	NPD3028	Approved
0.6667	Remote Similarity	NPD1164	Approved
0.6646	Remote Similarity	NPD7819	Suspended
0.6644	Remote Similarity	NPD3657	Discovery
0.6644	Remote Similarity	NPD4721	Approved
0.6644	Remote Similarity	NPD4726	Approved
0.6644	Remote Similarity	NPD3540	Phase 1
0.6644	Remote Similarity	NPD4725	Approved
0.6643	Remote Similarity	NPD1669	Approved
0.6643	Remote Similarity	NPD9622	Approved
0.6643	Remote Similarity	NPD3595	Approved
0.6643	Remote Similarity	NPD3594	Approved
0.6642	Remote Similarity	NPD9268	Approved
0.6627	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD8053	Approved
0.6627	Remote Similarity	NPD8054	Approved
0.6625	Remote Similarity	NPD4055	Discovery
0.6623	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7003	Approved
0.662	Remote Similarity	NPD2195	Approved
0.662	Remote Similarity	NPD2194	Approved
0.6619	Remote Similarity	NPD1281	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