NPASS Compound

Structure

NPC52530 OpenBabel07101718282D 22 24 0 0 1 0 0 0 0 0999 V2000 -4.3301 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 -3.4641 -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 -3.4641 0.0000 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 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 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 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 5 2 0 0 0 0 2 8 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 9 2 0 0 0 0 7 12 1 0 0 0 0 9 17 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 22 1 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 14 19 2 0 0 0 0 15 16 1 0 0 0 0 15 20 1 1 0 0 0 16 8 1 6 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	293.909
LogP:	1.518
LogD:	1.869
LogS:	-3.649
# Rotatable Bonds:	2
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.782
Synthetic Accessibility Score:	3.117
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.974
MDCK Permeability:	6.3714223870192654e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.178

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.118
Plasma Protein Binding (PPB):	94.3634033203125%
Volume Distribution (VD):	0.636
Pgp-substrate:	6.286901473999023%

ADMET: Metabolism

CYP1A2-inhibitor:	0.163
CYP1A2-substrate:	0.386
CYP2C19-inhibitor:	0.189
CYP2C19-substrate:	0.101
CYP2C9-inhibitor:	0.349
CYP2C9-substrate:	0.887
CYP2D6-inhibitor:	0.474
CYP2D6-substrate:	0.722
CYP3A4-inhibitor:	0.652
CYP3A4-substrate:	0.267

ADMET: Excretion

Clearance (CL):	9.151
Half-life (T1/2):	0.714

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.647
AMES Toxicity:	0.36
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.028
Skin Sensitization:	0.21
Carcinogencity:	0.504
Eye Corrosion:	0.003
Eye Irritation:	0.169
Respiratory Toxicity:	0.048

Download Data

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

Natural Product: NPC52530

Natural Product ID:	NPC52530
*Common Name:**	Erycibenin D
IUPAC Name:	(2R,3R)-3,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:
Standard InCHIKey:	OILXOIAGIWQYOO-JKSUJKDBSA-N
Standard InCHI:	InChI=1S/C16H14O6/c1-21-13-6-8(2-5-11(13)18)16-15(20)14(19)10-4-3-9(17)7-12(10)22-16/h2-7,15-18,20H,1H3/t15-,16+/m0/s1
SMILES:	COc1cc(ccc1O)[C@@H]1[C@H](C(=O)c2ccc(cc2O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL241571
PubChem CID:	16093656
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002595] 3'-O-methylated flavonoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	stem	n.a.	PMID[17077549]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	stems	n.a.	n.a.	PMID[17158054]
NPO14114	Dalbergia parviflora	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[19928832]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14114	Dalbergia parviflora	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
IC50	3
Others	8

Activity Type	# Activity
Cell Line	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	100000.0	nM	PMID[528812]
NPT396	Cell Line	T47D	Homo sapiens	Activity	>	100.0	uM	PMID[528813]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	0.3	uM	PMID[528813]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	>	100.0	uM	PMID[528813]
NPT396	Cell Line	T47D	Homo sapiens	Activity	=	5.7	uM	PMID[528813]

☑ 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 NPC52530 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	403
0.1-0.2	1630
0.2-0.3	4270
0.3-0.4	9947
0.4-0.5	7937
0.5-0.6	3434
0.6-0.7	4745
0.7-0.8	5316
0.8-0.85	2735
0.85-0.9	1555
0.9-0.95	643
0.95-1	82

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC326037
0.9933	High Similarity	NPC320825
0.9933	High Similarity	NPC13858
0.9803	High Similarity	NPC308992
0.98	High Similarity	NPC250922
0.9799	High Similarity	NPC246328
0.9799	High Similarity	NPC27532
0.9799	High Similarity	NPC256346
0.9799	High Similarity	NPC325028
0.9737	High Similarity	NPC263449
0.9737	High Similarity	NPC282009
0.9737	High Similarity	NPC287328
0.9735	High Similarity	NPC471515
0.9735	High Similarity	NPC67876
0.9735	High Similarity	NPC471479
0.9732	High Similarity	NPC240476
0.9732	High Similarity	NPC36835
0.9732	High Similarity	NPC260491
0.9732	High Similarity	NPC236637
0.9732	High Similarity	NPC9743
0.9732	High Similarity	NPC246162
0.9732	High Similarity	NPC219582
0.9732	High Similarity	NPC61506
0.9732	High Similarity	NPC302950
0.9673	High Similarity	NPC471499
0.9671	High Similarity	NPC22192
0.9671	High Similarity	NPC55738
0.9669	High Similarity	NPC471500
0.9669	High Similarity	NPC474638
0.9667	High Similarity	NPC18727
0.9667	High Similarity	NPC141212
0.9608	High Similarity	NPC470183
0.9608	High Similarity	NPC470326
0.9605	High Similarity	NPC210084
0.9605	High Similarity	NPC291508
0.9605	High Similarity	NPC472598
0.9605	High Similarity	NPC99597
0.9605	High Similarity	NPC474055
0.96	High Similarity	NPC55205
0.96	High Similarity	NPC19721
0.9548	High Similarity	NPC472625
0.9545	High Similarity	NPC173137
0.9539	High Similarity	NPC201837
0.9539	High Similarity	NPC235165
0.9539	High Similarity	NPC278778
0.9539	High Similarity	NPC255106
0.9539	High Similarity	NPC291878
0.9539	High Similarity	NPC35038
0.9539	High Similarity	NPC195796
0.9536	High Similarity	NPC469550
0.9533	High Similarity	NPC200740
0.9533	High Similarity	NPC125062
0.9533	High Similarity	NPC31363
0.9533	High Similarity	NPC54394
0.9533	High Similarity	NPC252933
0.953	High Similarity	NPC1612
0.953	High Similarity	NPC183959
0.9487	High Similarity	NPC36916
0.9487	High Similarity	NPC72787
0.9487	High Similarity	NPC7688
0.9487	High Similarity	NPC7154
0.9487	High Similarity	NPC125039
0.9487	High Similarity	NPC36
0.9487	High Similarity	NPC58223
0.9484	High Similarity	NPC474033
0.9484	High Similarity	NPC476247
0.9484	High Similarity	NPC474034
0.9484	High Similarity	NPC472964
0.9481	High Similarity	NPC471744
0.9481	High Similarity	NPC472902
0.9477	High Similarity	NPC474836
0.9477	High Similarity	NPC129684
0.9477	High Similarity	NPC48208
0.9477	High Similarity	NPC299520
0.9477	High Similarity	NPC162869
0.9477	High Similarity	NPC156057
0.9477	High Similarity	NPC474208
0.9477	High Similarity	NPC27337
0.9477	High Similarity	NPC475267
0.9474	High Similarity	NPC2928
0.9474	High Similarity	NPC321779
0.9474	High Similarity	NPC45849
0.9474	High Similarity	NPC200761
0.9474	High Similarity	NPC470327
0.9474	High Similarity	NPC477503
0.947	High Similarity	NPC279989
0.947	High Similarity	NPC260979
0.947	High Similarity	NPC472912
0.947	High Similarity	NPC477231
0.947	High Similarity	NPC82325
0.947	High Similarity	NPC257648
0.9467	High Similarity	NPC29231
0.9467	High Similarity	NPC338131
0.9463	High Similarity	NPC321011
0.9463	High Similarity	NPC218569
0.9463	High Similarity	NPC294852
0.9463	High Similarity	NPC188679
0.9427	High Similarity	NPC477517
0.9427	High Similarity	NPC471213
0.9423	High Similarity	NPC124038
0.9419	High Similarity	NPC474038
0.9419	High Similarity	NPC472632
0.9419	High Similarity	NPC112418
0.9419	High Similarity	NPC472634
0.9419	High Similarity	NPC26326
0.9419	High Similarity	NPC158188
0.9419	High Similarity	NPC289771
0.9416	High Similarity	NPC152904
0.9412	High Similarity	NPC209614
0.9412	High Similarity	NPC265511
0.9412	High Similarity	NPC472916
0.9412	High Similarity	NPC472626
0.9412	High Similarity	NPC470328
0.9408	High Similarity	NPC206238
0.9408	High Similarity	NPC270620
0.9408	High Similarity	NPC88645
0.9408	High Similarity	NPC192083
0.9408	High Similarity	NPC292214
0.9408	High Similarity	NPC213896
0.9408	High Similarity	NPC236223
0.9408	High Similarity	NPC271779
0.9408	High Similarity	NPC167091
0.9408	High Similarity	NPC78326
0.9408	High Similarity	NPC179126
0.9404	High Similarity	NPC50403
0.9404	High Similarity	NPC260895
0.9404	High Similarity	NPC28274
0.9404	High Similarity	NPC133953
0.94	High Similarity	NPC137062
0.94	High Similarity	NPC183950
0.94	High Similarity	NPC270465
0.94	High Similarity	NPC159103
0.94	High Similarity	NPC52005
0.94	High Similarity	NPC223579
0.94	High Similarity	NPC87125
0.94	High Similarity	NPC105512
0.94	High Similarity	NPC287101
0.9396	High Similarity	NPC21835
0.9396	High Similarity	NPC211466
0.9396	High Similarity	NPC44721
0.9396	High Similarity	NPC40086
0.9396	High Similarity	NPC176869
0.9396	High Similarity	NPC122828
0.9396	High Similarity	NPC95864
0.9396	High Similarity	NPC3779
0.9396	High Similarity	NPC476182
0.9363	High Similarity	NPC475888
0.9363	High Similarity	NPC234052
0.9363	High Similarity	NPC224280
0.9363	High Similarity	NPC62261
0.9359	High Similarity	NPC472635
0.9359	High Similarity	NPC471745
0.9359	High Similarity	NPC211107
0.9355	High Similarity	NPC472631
0.9355	High Similarity	NPC475784
0.9355	High Similarity	NPC119209
0.9355	High Similarity	NPC36217
0.9355	High Similarity	NPC472630
0.9355	High Similarity	NPC118256
0.9355	High Similarity	NPC472624
0.9355	High Similarity	NPC174953
0.9355	High Similarity	NPC192686
0.9351	High Similarity	NPC472910
0.9351	High Similarity	NPC470402
0.9351	High Similarity	NPC96167
0.9351	High Similarity	NPC223787
0.9351	High Similarity	NPC472914
0.9351	High Similarity	NPC245758
0.9351	High Similarity	NPC472911
0.9351	High Similarity	NPC472913
0.9351	High Similarity	NPC222814
0.9346	High Similarity	NPC117992
0.9346	High Similarity	NPC255807
0.9346	High Similarity	NPC201451
0.9346	High Similarity	NPC67396
0.9346	High Similarity	NPC57674
0.9346	High Similarity	NPC230149
0.9346	High Similarity	NPC31018
0.9346	High Similarity	NPC37392
0.9346	High Similarity	NPC44079
0.9346	High Similarity	NPC226025
0.9346	High Similarity	NPC168247
0.9346	High Similarity	NPC26227
0.9346	High Similarity	NPC152951
0.9342	High Similarity	NPC304954
0.9342	High Similarity	NPC39732
0.9342	High Similarity	NPC243171
0.9342	High Similarity	NPC161277
0.9342	High Similarity	NPC101996
0.9342	High Similarity	NPC123886
0.9342	High Similarity	NPC60972
0.9342	High Similarity	NPC199100
0.9342	High Similarity	NPC35567
0.9342	High Similarity	NPC39007
0.9342	High Similarity	NPC180234
0.9342	High Similarity	NPC171651
0.9342	High Similarity	NPC120537
0.9342	High Similarity	NPC106976
0.9338	High Similarity	NPC149127
0.9338	High Similarity	NPC286342

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 NPC52530 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	366
0.1-0.2	937
0.2-0.3	1789
0.3-0.4	2606
0.4-0.5	1779
0.5-0.6	987
0.6-0.7	480
0.7-0.8	145
0.8-0.85	37
0.85-0.9	13
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9732	High Similarity	NPD1934	Approved
0.9487	High Similarity	NPD6167	Clinical (unspecified phase)
0.9487	High Similarity	NPD6166	Phase 2
0.9487	High Similarity	NPD6168	Clinical (unspecified phase)
0.9408	High Similarity	NPD2393	Clinical (unspecified phase)
0.9286	High Similarity	NPD3882	Suspended
0.92	High Similarity	NPD1512	Approved
0.9156	High Similarity	NPD2801	Approved
0.9067	High Similarity	NPD1511	Approved
0.9012	High Similarity	NPD7074	Phase 3
0.9006	High Similarity	NPD3818	Discontinued
0.8974	High Similarity	NPD3817	Phase 2
0.8957	High Similarity	NPD6797	Phase 2
0.8951	High Similarity	NPD7054	Approved
0.8902	High Similarity	NPD7251	Discontinued
0.8896	High Similarity	NPD7472	Approved
0.8861	High Similarity	NPD7075	Discontinued
0.8859	High Similarity	NPD1549	Phase 2
0.8848	High Similarity	NPD7808	Phase 3
0.8848	High Similarity	NPD4338	Clinical (unspecified phase)
0.8839	High Similarity	NPD4380	Phase 2
0.8797	High Similarity	NPD4868	Clinical (unspecified phase)
0.8792	High Similarity	NPD1552	Clinical (unspecified phase)
0.8792	High Similarity	NPD1550	Clinical (unspecified phase)
0.879	High Similarity	NPD7096	Clinical (unspecified phase)
0.8758	High Similarity	NPD4378	Clinical (unspecified phase)
0.8742	High Similarity	NPD4381	Clinical (unspecified phase)
0.8634	High Similarity	NPD5494	Approved
0.8614	High Similarity	NPD7993	Clinical (unspecified phase)
0.8608	High Similarity	NPD6801	Discontinued
0.8571	High Similarity	NPD6799	Approved
0.8533	High Similarity	NPD1510	Phase 2
0.8494	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD2796	Approved
0.8389	Intermediate Similarity	NPD1240	Approved
0.8389	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1613	Approved
0.8385	Intermediate Similarity	NPD5402	Approved
0.8383	Intermediate Similarity	NPD5844	Phase 1
0.8365	Intermediate Similarity	NPD6599	Discontinued
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8323	Intermediate Similarity	NPD1465	Phase 2
0.8291	Intermediate Similarity	NPD5403	Approved
0.828	Intermediate Similarity	NPD5401	Approved
0.8278	Intermediate Similarity	NPD1607	Approved
0.8272	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD943	Approved
0.8242	Intermediate Similarity	NPD1247	Approved
0.8235	Intermediate Similarity	NPD6559	Discontinued
0.8232	Intermediate Similarity	NPD919	Approved
0.8199	Intermediate Similarity	NPD7411	Suspended
0.8193	Intermediate Similarity	NPD6232	Discontinued
0.8165	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7473	Discontinued
0.8144	Intermediate Similarity	NPD3926	Phase 2
0.8133	Intermediate Similarity	NPD6959	Discontinued
0.8121	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3027	Phase 3
0.8054	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3751	Discontinued
0.7974	Intermediate Similarity	NPD230	Phase 1
0.7935	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD4628	Phase 3
0.7911	Intermediate Similarity	NPD3750	Approved
0.7898	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1551	Phase 2
0.7882	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6190	Approved
0.7857	Intermediate Similarity	NPD447	Suspended
0.7844	Intermediate Similarity	NPD3749	Approved
0.784	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1653	Approved
0.7784	Intermediate Similarity	NPD7768	Phase 2
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7765	Intermediate Similarity	NPD3787	Discontinued
0.7742	Intermediate Similarity	NPD1933	Approved
0.774	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2800	Approved
0.7736	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7199	Phase 2
0.7697	Intermediate Similarity	NPD9494	Approved
0.7688	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD920	Approved
0.7622	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD2344	Approved
0.7607	Intermediate Similarity	NPD2532	Approved
0.7607	Intermediate Similarity	NPD2534	Approved
0.7607	Intermediate Similarity	NPD2533	Approved
0.7595	Intermediate Similarity	NPD3748	Approved
0.7588	Intermediate Similarity	NPD6234	Discontinued
0.7554	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD6099	Approved
0.7547	Intermediate Similarity	NPD6100	Approved
0.7546	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD3226	Approved
0.7516	Intermediate Similarity	NPD1243	Approved
0.7514	Intermediate Similarity	NPD7685	Pre-registration
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD8434	Phase 2
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7228	Approved
0.7485	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD4966	Approved
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7458	Intermediate Similarity	NPD5953	Discontinued
0.7451	Intermediate Similarity	NPD1203	Approved
0.7443	Intermediate Similarity	NPD7286	Phase 2
0.7436	Intermediate Similarity	NPD2313	Discontinued
0.7436	Intermediate Similarity	NPD6798	Discontinued
0.7433	Intermediate Similarity	NPD6779	Approved
0.7433	Intermediate Similarity	NPD6776	Approved
0.7433	Intermediate Similarity	NPD6780	Approved
0.7433	Intermediate Similarity	NPD6781	Approved
0.7433	Intermediate Similarity	NPD6782	Approved
0.7433	Intermediate Similarity	NPD6777	Approved
0.7433	Intermediate Similarity	NPD6778	Approved
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7423	Intermediate Similarity	NPD2309	Approved
0.7419	Intermediate Similarity	NPD4908	Phase 1
0.7417	Intermediate Similarity	NPD1610	Phase 2
0.7405	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8150	Discontinued
0.7394	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2799	Discontinued
0.7375	Intermediate Similarity	NPD7033	Discontinued
0.7362	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6651	Approved
0.7351	Intermediate Similarity	NPD4360	Phase 2
0.7351	Intermediate Similarity	NPD4363	Phase 3
0.7325	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7314	Intermediate Similarity	NPD5242	Approved
0.731	Intermediate Similarity	NPD5353	Approved
0.7308	Intermediate Similarity	NPD6832	Phase 2
0.7296	Intermediate Similarity	NPD6355	Discontinued
0.7294	Intermediate Similarity	NPD6844	Discontinued
0.7292	Intermediate Similarity	NPD7584	Approved
0.7288	Intermediate Similarity	NPD2163	Approved
0.7284	Intermediate Similarity	NPD7266	Discontinued
0.7278	Intermediate Similarity	NPD6233	Phase 2
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7255	Intermediate Similarity	NPD9269	Phase 2
0.7255	Intermediate Similarity	NPD9717	Approved
0.7229	Intermediate Similarity	NPD7390	Discontinued
0.7225	Intermediate Similarity	NPD7698	Approved
0.7225	Intermediate Similarity	NPD7697	Approved
0.7225	Intermediate Similarity	NPD7696	Phase 3
0.7219	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8151	Discontinued
0.7212	Intermediate Similarity	NPD2354	Approved
0.7195	Intermediate Similarity	NPD1652	Phase 2
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7186	Intermediate Similarity	NPD4661	Approved
0.7186	Intermediate Similarity	NPD4662	Approved
0.7179	Intermediate Similarity	NPD2798	Approved
0.7175	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD2403	Approved
0.7166	Intermediate Similarity	NPD6534	Approved
0.7166	Intermediate Similarity	NPD6535	Approved
0.7165	Intermediate Similarity	NPD7701	Phase 2
0.716	Intermediate Similarity	NPD4308	Phase 3
0.7159	Intermediate Similarity	NPD5710	Approved
0.7159	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7135	Intermediate Similarity	NPD6386	Approved
0.7135	Intermediate Similarity	NPD6385	Approved
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7134	Intermediate Similarity	NPD2861	Phase 2
0.7127	Intermediate Similarity	NPD7038	Approved
0.7127	Intermediate Similarity	NPD7039	Approved
0.7125	Intermediate Similarity	NPD4060	Phase 1
0.7108	Intermediate Similarity	NPD3887	Approved
0.7107	Intermediate Similarity	NPD411	Approved
0.7107	Intermediate Similarity	NPD3268	Approved
0.7102	Intermediate Similarity	NPD8127	Discontinued
0.7092	Intermediate Similarity	NPD7874	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5536	Phase 2
0.7083	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5124	Phase 1
0.7079	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD422	Phase 1
0.7073	Intermediate Similarity	NPD1471	Phase 3
0.7072	Intermediate Similarity	NPD3823	Discontinued
0.7069	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4111	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