NPASS Compound

Structure

NPC474766 OpenBabel07101719132D 23 25 0 0 0 0 0 0 0 0999 V2000 -1.7321 -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 -0.8660 -2.5000 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 3.4641 -3.0000 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 4.3301 -2.5000 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 -0.8660 -1.5000 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 0.0000 -1.0000 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 0.8660 -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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 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 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 23 1 0 0 0 0 3 13 1 0 0 0 0 4 6 1 0 0 0 0 4 9 1 0 0 0 0 5 7 1 0 0 0 0 5 10 2 0 0 0 0 6 12 1 0 0 0 0 7 11 2 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 19 1 0 0 0 0 11 14 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 20 2 0 0 0 0 14 17 1 0 0 0 0 15 17 1 0 0 0 0 15 18 2 0 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 17 22 2 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.1
Volume:	317.074
LogP:	4.187
LogD:	3.037
LogS:	-4.167
# Rotatable Bonds:	3
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.39
Synthetic Accessibility Score:	2.598
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.96
MDCK Permeability:	1.2951140888617374e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.071
20% Bioavailability (F20%):	0.035
30% Bioavailability (F30%):	0.469

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	98.02574157714844%
Volume Distribution (VD):	0.495
Pgp-substrate:	3.9521329402923584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.84
CYP2C19-inhibitor:	0.285
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.729
CYP2C9-substrate:	0.81
CYP2D6-inhibitor:	0.667
CYP2D6-substrate:	0.31
CYP3A4-inhibitor:	0.365
CYP3A4-substrate:	0.126

ADMET: Excretion

Clearance (CL):	7.315
Half-life (T1/2):	0.633

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.693
Rat Oral Acute Toxicity:	0.203
Maximum Recommended Daily Dose:	0.406
Skin Sensitization:	0.922
Carcinogencity:	0.577
Eye Corrosion:	0.003
Eye Irritation:	0.912
Respiratory Toxicity:	0.33

Download Data

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

Natural Product: NPC474766

Natural Product ID:	NPC474766
*Common Name:**	Ephemeranthone
IUPAC Name:	7-hydroxy-2-methoxy-3-propanoyl-9,10-dihydrophenanthrene-1,4-dione
Synonyms:	Ephemeranthone
Standard InCHIKey:	MBJQRQOKXCSGJB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O5/c1-3-13(20)15-17(22)14-11-7-5-10(19)8-9(11)4-6-12(14)16(21)18(15)23-2/h5,7-8,19H,3-4,6H2,1-2H3
SMILES:	CCC(=O)C1=C(OC)C(=O)C2=C(C1=O)c1ccc(cc1CC2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481835
PubChem CID:	44575342
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
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10514302]
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9461658]
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	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
Others	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.	Activity	=	5.3	%	PMID[501078]

☑ 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 NPC474766 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	250
0.1-0.2	1397
0.2-0.3	3258
0.3-0.4	8968
0.4-0.5	9970
0.5-0.6	5921
0.6-0.7	10391
0.7-0.8	2432
0.8-0.85	97
0.85-0.9	7
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9661	High Similarity	NPC164947
0.9256	High Similarity	NPC135062
0.8908	High Similarity	NPC325646
0.8908	High Similarity	NPC28951
0.8898	High Similarity	NPC27659
0.8636	High Similarity	NPC475549
0.8605	High Similarity	NPC253488
0.8583	High Similarity	NPC15837
0.8561	High Similarity	NPC22644
0.8492	Intermediate Similarity	NPC273683
0.848	Intermediate Similarity	NPC154696
0.845	Intermediate Similarity	NPC237225
0.8433	Intermediate Similarity	NPC264022
0.8425	Intermediate Similarity	NPC199273
0.8425	Intermediate Similarity	NPC474803
0.8403	Intermediate Similarity	NPC21162
0.84	Intermediate Similarity	NPC259703
0.84	Intermediate Similarity	NPC32322
0.8385	Intermediate Similarity	NPC171460
0.837	Intermediate Similarity	NPC475104
0.8359	Intermediate Similarity	NPC123506
0.8358	Intermediate Similarity	NPC38158
0.8333	Intermediate Similarity	NPC312560
0.8321	Intermediate Similarity	NPC198305
0.832	Intermediate Similarity	NPC318552
0.832	Intermediate Similarity	NPC190501
0.8308	Intermediate Similarity	NPC96024
0.8308	Intermediate Similarity	NPC24869
0.8295	Intermediate Similarity	NPC51037
0.8295	Intermediate Similarity	NPC254492
0.8295	Intermediate Similarity	NPC71610
0.8281	Intermediate Similarity	NPC164014
0.8271	Intermediate Similarity	NPC171968
0.8268	Intermediate Similarity	NPC282577
0.8268	Intermediate Similarity	NPC91478
0.8268	Intermediate Similarity	NPC176208
0.8261	Intermediate Similarity	NPC201297
0.8258	Intermediate Similarity	NPC244699
0.824	Intermediate Similarity	NPC42657
0.8231	Intermediate Similarity	NPC262936
0.8231	Intermediate Similarity	NPC72667
0.8231	Intermediate Similarity	NPC30491
0.8201	Intermediate Similarity	NPC478164
0.8195	Intermediate Similarity	NPC309430
0.8195	Intermediate Similarity	NPC239302
0.8189	Intermediate Similarity	NPC120545
0.8182	Intermediate Similarity	NPC172673
0.8175	Intermediate Similarity	NPC478121
0.8169	Intermediate Similarity	NPC474556
0.8168	Intermediate Similarity	NPC165257
0.8167	Intermediate Similarity	NPC88141
0.8154	Intermediate Similarity	NPC231774
0.8154	Intermediate Similarity	NPC306765
0.8145	Intermediate Similarity	NPC477453
0.814	Intermediate Similarity	NPC310540
0.8134	Intermediate Similarity	NPC59459
0.8134	Intermediate Similarity	NPC78307
0.8134	Intermediate Similarity	NPC53896
0.8134	Intermediate Similarity	NPC4170
0.8125	Intermediate Similarity	NPC121168
0.8125	Intermediate Similarity	NPC139171
0.8115	Intermediate Similarity	NPC231717
0.811	Intermediate Similarity	NPC236520
0.811	Intermediate Similarity	NPC294361
0.8106	Intermediate Similarity	NPC146647
0.8106	Intermediate Similarity	NPC276238
0.8106	Intermediate Similarity	NPC25736
0.8106	Intermediate Similarity	NPC34414
0.8102	Intermediate Similarity	NPC173980
0.8099	Intermediate Similarity	NPC222905
0.8095	Intermediate Similarity	NPC258366
0.8095	Intermediate Similarity	NPC31296
0.8095	Intermediate Similarity	NPC79933
0.8095	Intermediate Similarity	NPC473974
0.8092	Intermediate Similarity	NPC78364
0.8092	Intermediate Similarity	NPC69424
0.8092	Intermediate Similarity	NPC176130
0.8092	Intermediate Similarity	NPC84672
0.8092	Intermediate Similarity	NPC471530
0.8088	Intermediate Similarity	NPC471670
0.8085	Intermediate Similarity	NPC478160
0.8074	Intermediate Similarity	NPC50924
0.8067	Intermediate Similarity	NPC70843
0.8067	Intermediate Similarity	NPC188677
0.8065	Intermediate Similarity	NPC23402
0.8062	Intermediate Similarity	NPC198014
0.8062	Intermediate Similarity	NPC471187
0.806	Intermediate Similarity	NPC165612
0.806	Intermediate Similarity	NPC477407
0.8058	Intermediate Similarity	NPC110810
0.8056	Intermediate Similarity	NPC475718
0.8049	Intermediate Similarity	NPC11824
0.8047	Intermediate Similarity	NPC253627
0.8045	Intermediate Similarity	NPC470725
0.8043	Intermediate Similarity	NPC477408
0.8033	Intermediate Similarity	NPC470355
0.8031	Intermediate Similarity	NPC473136
0.8031	Intermediate Similarity	NPC206778
0.8031	Intermediate Similarity	NPC285829
0.803	Intermediate Similarity	NPC48248
0.8029	Intermediate Similarity	NPC119542
0.8029	Intermediate Similarity	NPC475957
0.8016	Intermediate Similarity	NPC328694
0.8015	Intermediate Similarity	NPC22222
0.8015	Intermediate Similarity	NPC283088
0.8015	Intermediate Similarity	NPC471929
0.8015	Intermediate Similarity	NPC471930
0.8015	Intermediate Similarity	NPC3224
0.8015	Intermediate Similarity	NPC471935
0.8015	Intermediate Similarity	NPC281513
0.8	Intermediate Similarity	NPC181334
0.8	Intermediate Similarity	NPC254603
0.7985	Intermediate Similarity	NPC471851
0.7985	Intermediate Similarity	NPC85342
0.7984	Intermediate Similarity	NPC307174
0.7984	Intermediate Similarity	NPC11250
0.797	Intermediate Similarity	NPC99731
0.7969	Intermediate Similarity	NPC190971
0.7969	Intermediate Similarity	NPC241001
0.7956	Intermediate Similarity	NPC7464
0.7955	Intermediate Similarity	NPC324209
0.7943	Intermediate Similarity	NPC224884
0.7943	Intermediate Similarity	NPC209085
0.7941	Intermediate Similarity	NPC202225
0.7939	Intermediate Similarity	NPC87985
0.7939	Intermediate Similarity	NPC137416
0.7939	Intermediate Similarity	NPC137750
0.7934	Intermediate Similarity	NPC11554
0.7931	Intermediate Similarity	NPC58310
0.7931	Intermediate Similarity	NPC295977
0.7926	Intermediate Similarity	NPC58685
0.7926	Intermediate Similarity	NPC110609
0.7926	Intermediate Similarity	NPC246693
0.7926	Intermediate Similarity	NPC242358
0.7923	Intermediate Similarity	NPC375356
0.792	Intermediate Similarity	NPC322197
0.7917	Intermediate Similarity	NPC29989
0.7917	Intermediate Similarity	NPC69332
0.7917	Intermediate Similarity	NPC95178
0.7914	Intermediate Similarity	NPC470407
0.791	Intermediate Similarity	NPC108129
0.791	Intermediate Similarity	NPC475741
0.791	Intermediate Similarity	NPC55949
0.7907	Intermediate Similarity	NPC162935
0.7907	Intermediate Similarity	NPC249340
0.7899	Intermediate Similarity	NPC261573
0.7899	Intermediate Similarity	NPC290601
0.7899	Intermediate Similarity	NPC8931
0.7899	Intermediate Similarity	NPC118366
0.7899	Intermediate Similarity	NPC186647
0.7899	Intermediate Similarity	NPC120693
0.7899	Intermediate Similarity	NPC471152
0.7899	Intermediate Similarity	NPC36868
0.7895	Intermediate Similarity	NPC201419
0.7895	Intermediate Similarity	NPC469930
0.7895	Intermediate Similarity	NPC3009
0.7895	Intermediate Similarity	NPC234175
0.7887	Intermediate Similarity	NPC477409
0.7887	Intermediate Similarity	NPC29932
0.7879	Intermediate Similarity	NPC1991
0.7877	Intermediate Similarity	NPC306011
0.7877	Intermediate Similarity	NPC472838
0.7872	Intermediate Similarity	NPC229218
0.7872	Intermediate Similarity	NPC141817
0.7872	Intermediate Similarity	NPC308572
0.7872	Intermediate Similarity	NPC176030
0.7872	Intermediate Similarity	NPC192597
0.7872	Intermediate Similarity	NPC169214
0.7869	Intermediate Similarity	NPC95172
0.7868	Intermediate Similarity	NPC475627
0.7868	Intermediate Similarity	NPC475346
0.7868	Intermediate Similarity	NPC263817
0.7868	Intermediate Similarity	NPC18982
0.7868	Intermediate Similarity	NPC477139
0.7868	Intermediate Similarity	NPC475457
0.7863	Intermediate Similarity	NPC75432
0.7863	Intermediate Similarity	NPC173978
0.7863	Intermediate Similarity	NPC234890
0.7863	Intermediate Similarity	NPC280869
0.7863	Intermediate Similarity	NPC74507
0.7863	Intermediate Similarity	NPC15127
0.7862	Intermediate Similarity	NPC80370
0.7862	Intermediate Similarity	NPC84142
0.7857	Intermediate Similarity	NPC19290
0.7857	Intermediate Similarity	NPC61062
0.7857	Intermediate Similarity	NPC299252
0.7857	Intermediate Similarity	NPC82336
0.7857	Intermediate Similarity	NPC277394
0.7857	Intermediate Similarity	NPC78987
0.7852	Intermediate Similarity	NPC93015
0.7852	Intermediate Similarity	NPC72669
0.7852	Intermediate Similarity	NPC474517
0.7852	Intermediate Similarity	NPC205360
0.7851	Intermediate Similarity	NPC34715
0.7851	Intermediate Similarity	NPC228737
0.7847	Intermediate Similarity	NPC58373
0.7846	Intermediate Similarity	NPC300274
0.7842	Intermediate Similarity	NPC114333
0.7842	Intermediate Similarity	NPC289358
0.7842	Intermediate Similarity	NPC42384

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 NPC474766 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	955
0.2-0.3	1233
0.3-0.4	2485
0.4-0.5	2271
0.5-0.6	1316
0.6-0.7	572
0.7-0.8	62
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8468	Intermediate Similarity	NPD2932	Approved
0.832	Intermediate Similarity	NPD3019	Approved
0.7956	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD1201	Approved
0.7829	Intermediate Similarity	NPD3026	Approved
0.7829	Intermediate Similarity	NPD3023	Approved
0.7812	Intermediate Similarity	NPD1651	Approved
0.7812	Intermediate Similarity	NPD3025	Approved
0.7812	Intermediate Similarity	NPD3024	Approved
0.7803	Intermediate Similarity	NPD1470	Approved
0.7727	Intermediate Similarity	NPD1283	Approved
0.7721	Intermediate Similarity	NPD6663	Approved
0.7717	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD5736	Approved
0.7676	Intermediate Similarity	NPD8166	Discontinued
0.7615	Intermediate Similarity	NPD4626	Approved
0.7569	Intermediate Similarity	NPD3300	Phase 2
0.75	Intermediate Similarity	NPD1281	Approved
0.7463	Intermediate Similarity	NPD1876	Approved
0.7462	Intermediate Similarity	NPD3091	Approved
0.7447	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3972	Approved
0.7417	Intermediate Similarity	NPD3020	Approved
0.741	Intermediate Similarity	NPD4060	Phase 1
0.7405	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD5405	Approved
0.7394	Intermediate Similarity	NPD5408	Approved
0.7394	Intermediate Similarity	NPD2935	Discontinued
0.7394	Intermediate Similarity	NPD5406	Approved
0.7394	Intermediate Similarity	NPD5404	Approved
0.7391	Intermediate Similarity	NPD3764	Approved
0.7388	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD1241	Discontinued
0.7311	Intermediate Similarity	NPD2860	Approved
0.7311	Intermediate Similarity	NPD2859	Approved
0.731	Intermediate Similarity	NPD7003	Approved
0.7302	Intermediate Similarity	NPD3021	Approved
0.7302	Intermediate Similarity	NPD3022	Approved
0.7286	Intermediate Similarity	NPD2979	Phase 3
0.7279	Intermediate Similarity	NPD7390	Discontinued
0.7273	Intermediate Similarity	NPD5691	Approved
0.7259	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3092	Approved
0.723	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD2933	Approved
0.7227	Intermediate Similarity	NPD2934	Approved
0.7227	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2346	Discontinued
0.7219	Intermediate Similarity	NPD7028	Phase 2
0.7218	Intermediate Similarity	NPD3095	Discontinued
0.7218	Intermediate Similarity	NPD4059	Approved
0.7214	Intermediate Similarity	NPD8032	Phase 2
0.7194	Intermediate Similarity	NPD7095	Approved
0.7192	Intermediate Similarity	NPD3750	Approved
0.7181	Intermediate Similarity	NPD6273	Approved
0.7167	Intermediate Similarity	NPD844	Approved
0.7154	Intermediate Similarity	NPD5951	Approved
0.7153	Intermediate Similarity	NPD3094	Phase 2
0.7143	Intermediate Similarity	NPD2342	Discontinued
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7132	Intermediate Similarity	NPD7635	Approved
0.7132	Intermediate Similarity	NPD1755	Approved
0.7121	Intermediate Similarity	NPD5536	Phase 2
0.7114	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6355	Discontinued
0.7107	Intermediate Similarity	NPD288	Approved
0.7103	Intermediate Similarity	NPD1471	Phase 3
0.7101	Intermediate Similarity	NPD2798	Approved
0.709	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2799	Discontinued
0.7083	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9545	Approved
0.7055	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD1237	Approved
0.7034	Intermediate Similarity	NPD2531	Phase 2
0.7034	Intermediate Similarity	NPD2438	Suspended
0.7031	Intermediate Similarity	NPD4750	Phase 3
0.7029	Intermediate Similarity	NPD1164	Approved
0.7029	Intermediate Similarity	NPD2797	Approved
0.7027	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD2629	Approved
0.7021	Intermediate Similarity	NPD3268	Approved
0.7015	Intermediate Similarity	NPD4093	Discontinued
0.7008	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2344	Approved
0.6978	Remote Similarity	NPD4624	Approved
0.6977	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD6233	Phase 2
0.6968	Remote Similarity	NPD7819	Suspended
0.6966	Remote Similarity	NPD1510	Phase 2
0.6963	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2286	Discontinued
0.6959	Remote Similarity	NPD4628	Phase 3
0.6944	Remote Similarity	NPD1607	Approved
0.6935	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1608	Approved
0.6933	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD9494	Approved
0.6928	Remote Similarity	NPD7458	Discontinued
0.6928	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3226	Approved
0.6923	Remote Similarity	NPD943	Approved
0.6923	Remote Similarity	NPD4140	Approved
0.6923	Remote Similarity	NPD1240	Approved
0.6918	Remote Similarity	NPD6100	Approved
0.6918	Remote Similarity	NPD4476	Approved
0.6918	Remote Similarity	NPD4477	Approved
0.6918	Remote Similarity	NPD6099	Approved
0.6917	Remote Similarity	NPD9493	Approved
0.6913	Remote Similarity	NPD6190	Approved
0.6912	Remote Similarity	NPD3847	Discontinued
0.6887	Remote Similarity	NPD2532	Approved
0.6887	Remote Similarity	NPD2534	Approved
0.6887	Remote Similarity	NPD2533	Approved
0.6885	Remote Similarity	NPD1809	Phase 2
0.6875	Remote Similarity	NPD6232	Discontinued
0.6867	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.686	Remote Similarity	NPD845	Approved
0.6859	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD2066	Phase 3
0.6853	Remote Similarity	NPD4062	Phase 3
0.6852	Remote Similarity	NPD7473	Discontinued
0.6849	Remote Similarity	NPD3748	Approved
0.6842	Remote Similarity	NPD255	Approved
0.6842	Remote Similarity	NPD256	Approved
0.6838	Remote Similarity	NPD1751	Approved
0.6835	Remote Similarity	NPD7075	Discontinued
0.6831	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5283	Phase 1
0.6813	Remote Similarity	NPD6959	Discontinued
0.6812	Remote Similarity	NPD1481	Phase 2
0.6812	Remote Similarity	NPD4878	Approved
0.6806	Remote Similarity	NPD3620	Phase 2
0.6806	Remote Similarity	NPD826	Approved
0.6806	Remote Similarity	NPD825	Approved
0.6806	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.68	Remote Similarity	NPD2309	Approved
0.6794	Remote Similarity	NPD228	Approved
0.6786	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2313	Discontinued
0.6772	Remote Similarity	NPD5909	Discontinued
0.6772	Remote Similarity	NPD3882	Suspended
0.6769	Remote Similarity	NPD1792	Phase 2
0.6763	Remote Similarity	NPD5327	Phase 3
0.6757	Remote Similarity	NPD5763	Approved
0.6757	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5762	Approved
0.6755	Remote Similarity	NPD7236	Approved
0.6752	Remote Similarity	NPD111	Approved
0.6752	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD5033	Approved
0.6746	Remote Similarity	NPD846	Approved
0.6746	Remote Similarity	NPD940	Approved
0.6739	Remote Similarity	NPD1535	Discovery
0.6738	Remote Similarity	NPD258	Approved
0.6738	Remote Similarity	NPD257	Approved
0.6735	Remote Similarity	NPD4308	Phase 3
0.6733	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4110	Phase 3
0.6732	Remote Similarity	NPD1512	Approved
0.6727	Remote Similarity	NPD4956	Approved
0.6716	Remote Similarity	NPD4198	Discontinued
0.6716	Remote Similarity	NPD6671	Approved
0.6715	Remote Similarity	NPD17	Approved
0.6713	Remote Similarity	NPD7008	Discontinued
0.6713	Remote Similarity	NPD4625	Phase 3
0.6712	Remote Similarity	NPD4097	Suspended
0.6712	Remote Similarity	NPD6651	Approved
0.6712	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1549	Phase 2
0.6711	Remote Similarity	NPD4534	Discontinued
0.6709	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD1930	Approved
0.6693	Remote Similarity	NPD1929	Approved
0.6692	Remote Similarity	NPD2234	Approved
0.6692	Remote Similarity	NPD2228	Approved
0.6692	Remote Similarity	NPD74	Approved
0.6692	Remote Similarity	NPD2229	Approved
0.6692	Remote Similarity	NPD9266	Approved
0.6691	Remote Similarity	NPD1894	Discontinued
0.669	Remote Similarity	NPD3635	Approved
0.669	Remote Similarity	NPD3636	Approved
0.669	Remote Similarity	NPD3637	Approved
0.6689	Remote Similarity	NPD2354	Approved
0.6688	Remote Similarity	NPD37	Approved
0.6688	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD1444	Approved
0.6667	Remote Similarity	NPD1242	Phase 1
0.6667	Remote Similarity	NPD3266	Approved
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)

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