NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	336.1
Volume:	340.473
LogP:	4.418
LogD:	3.603
LogS:	-4.613
# Rotatable Bonds:	3
TPSA:	72.06
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	2.386
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.022
MDCK Permeability:	3.1308667530538514e-05
Pgp-inhibitor:	0.12
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	94.33690643310547%
Volume Distribution (VD):	0.536
Pgp-substrate:	6.497628211975098%

ADMET: Metabolism

CYP1A2-inhibitor:	0.958
CYP1A2-substrate:	0.923
CYP2C19-inhibitor:	0.835
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.791
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.434
CYP2D6-substrate:	0.889
CYP3A4-inhibitor:	0.294
CYP3A4-substrate:	0.236

ADMET: Excretion

Clearance (CL):	10.631
Half-life (T1/2):	0.747

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.17
Drug-inuced Liver Injury (DILI):	0.967
AMES Toxicity:	0.758
Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.795
Skin Sensitization:	0.899
Carcinogencity:	0.503
Eye Corrosion:	0.003
Eye Irritation:	0.894
Respiratory Toxicity:	0.564

Download Data

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

Natural Product: NPC476640

Natural Product ID:	NPC476640
*Common Name:**	4'-Deoxycandidusin A
IUPAC Name:	6,9-dimethoxy-7-phenyldibenzofuran-2,3-diol
Synonyms:	4'-Deoxycandidusin A
Standard InCHIKey:	LNKQUTQFZVRDLZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H16O5/c1-23-17-9-12(11-6-4-3-5-7-11)19(24-2)20-18(17)13-8-14(21)15(22)10-16(13)25-20/h3-10,21-22H,1-2H3
SMILES:	COC1=C2C3=CC(=C(C=C3OC2=C(C(=C1)C4=CC=CC=C4)OC)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	57333565
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0002584] Phenylbenzofurans

*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
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	rhizosphere	Sonoran desert	n.a.	PMID[15620238]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17542490]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17564467]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053517]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21366228]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718031]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21854017]
NPO33649	Aspergillus sp. YXf3	Species	Aspergillaceae	Eukaryota	isolated from a healthy leaf of Ginkgo biloba	the campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	healthy leaf of Ginkgo biloba	campus of Nanjing University, Nanjing, China	2008-OCT	PMID[22196792]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	isolated from the sponge Xestospongia testudinaria	n.a.	n.a.	PMID[22225637]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	Isolated from a sandy-loam soil sample	50 m inland from Waikiki Beach, Honolulu, Hawaii	2010-JUL	PMID[22400916]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22703109]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23527875]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24050204]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25001296]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25581396]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26273902]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31012585]
NPO31572	Aspergillus sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33305943]

☑ 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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	9050	nM	PMID[22196792]

☑ 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 NPC476640 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	491
0.1-0.2	2100
0.2-0.3	4842
0.3-0.4	11331
0.4-0.5	6190
0.5-0.6	3922
0.6-0.7	5281
0.7-0.8	5370
0.8-0.85	1781
0.85-0.9	1039
0.9-0.95	321
0.95-1	29

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC216842
1.0	High Similarity	NPC82217
0.9938	High Similarity	NPC230619
0.9938	High Similarity	NPC287243
0.9938	High Similarity	NPC54098
0.9877	High Similarity	NPC49667
0.9877	High Similarity	NPC8127
0.9876	High Similarity	NPC476641
0.9755	High Similarity	NPC65885
0.9752	High Similarity	NPC470704
0.9627	High Similarity	NPC36320
0.9627	High Similarity	NPC45449
0.9578	High Similarity	NPC98546
0.9578	High Similarity	NPC297807
0.9565	High Similarity	NPC1706
0.9565	High Similarity	NPC1755
0.9565	High Similarity	NPC263092
0.9565	High Similarity	NPC39305
0.9565	High Similarity	NPC59295
0.9503	High Similarity	NPC272722
0.9503	High Similarity	NPC238995
0.9503	High Similarity	NPC84515
0.9503	High Similarity	NPC312056
0.9464	High Similarity	NPC47883
0.9455	High Similarity	NPC174700
0.9441	High Similarity	NPC188486
0.9398	High Similarity	NPC473834
0.939	High Similarity	NPC50394
0.9333	High Similarity	NPC247136
0.9325	High Similarity	NPC133065
0.9317	High Similarity	NPC16935
0.9317	High Similarity	NPC195832
0.9317	High Similarity	NPC196879
0.9298	High Similarity	NPC226725
0.9281	High Similarity	NPC149846
0.9273	High Similarity	NPC247973
0.9268	High Similarity	NPC39306
0.9244	High Similarity	NPC248315
0.924	High Similarity	NPC154527
0.9217	High Similarity	NPC202470
0.9212	High Similarity	NPC277480
0.9193	High Similarity	NPC45131
0.9193	High Similarity	NPC472461
0.9172	High Similarity	NPC471841
0.9167	High Similarity	NPC310794
0.9152	High Similarity	NPC37183
0.9136	High Similarity	NPC203891
0.9136	High Similarity	NPC101830
0.9136	High Similarity	NPC110070
0.9128	High Similarity	NPC71260
0.9118	High Similarity	NPC77179
0.9118	High Similarity	NPC23553
0.9112	High Similarity	NPC227906
0.9086	High Similarity	NPC60848
0.908	High Similarity	NPC7846
0.908	High Similarity	NPC19687
0.908	High Similarity	NPC130894
0.908	High Similarity	NPC9609
0.908	High Similarity	NPC18772
0.908	High Similarity	NPC288669
0.908	High Similarity	NPC25495
0.908	High Similarity	NPC22472
0.908	High Similarity	NPC261004
0.908	High Similarity	NPC176300
0.908	High Similarity	NPC105242
0.908	High Similarity	NPC18607
0.908	High Similarity	NPC193842
0.908	High Similarity	NPC143828
0.908	High Similarity	NPC300943
0.908	High Similarity	NPC115798
0.908	High Similarity	NPC152166
0.908	High Similarity	NPC204854
0.908	High Similarity	NPC253634
0.908	High Similarity	NPC191459
0.908	High Similarity	NPC4481
0.9074	High Similarity	NPC245546
0.9074	High Similarity	NPC49824
0.9074	High Similarity	NPC292107
0.9074	High Similarity	NPC266960
0.9074	High Similarity	NPC43243
0.9074	High Similarity	NPC265511
0.907	High Similarity	NPC228209
0.907	High Similarity	NPC471842
0.907	High Similarity	NPC240508
0.9053	High Similarity	NPC117450
0.9048	High Similarity	NPC131866
0.9048	High Similarity	NPC28042
0.9036	High Similarity	NPC291110
0.9029	High Similarity	NPC295436
0.9024	High Similarity	NPC246478
0.9018	High Similarity	NPC75215
0.9018	High Similarity	NPC93376
0.9018	High Similarity	NPC78302
0.9018	High Similarity	NPC227192
0.9018	High Similarity	NPC287979
0.9018	High Similarity	NPC29841
0.9018	High Similarity	NPC224137
0.9018	High Similarity	NPC163524
0.9018	High Similarity	NPC472438
0.9018	High Similarity	NPC305663
0.9018	High Similarity	NPC235215
0.9018	High Similarity	NPC189179
0.9018	High Similarity	NPC7973
0.9018	High Similarity	NPC176665
0.9012	High Similarity	NPC475996
0.9012	High Similarity	NPC26227
0.9012	High Similarity	NPC189960
0.9012	High Similarity	NPC44079
0.9012	High Similarity	NPC201451
0.9012	High Similarity	NPC32557
0.9012	High Similarity	NPC256612
0.9012	High Similarity	NPC20830
0.9006	High Similarity	NPC246877
0.9006	High Similarity	NPC304954
0.9006	High Similarity	NPC221820
0.9006	High Similarity	NPC125300
0.9	High Similarity	NPC289244
0.8994	High Similarity	NPC248593
0.8994	High Similarity	NPC28589
0.8988	High Similarity	NPC280493
0.8976	High Similarity	NPC270837
0.897	High Similarity	NPC308992
0.8963	High Similarity	NPC154304
0.8963	High Similarity	NPC152904
0.8963	High Similarity	NPC190487
0.8963	High Similarity	NPC55738
0.896	High Similarity	NPC246153
0.896	High Similarity	NPC8927
0.8957	High Similarity	NPC178854
0.8957	High Similarity	NPC137100
0.8957	High Similarity	NPC247017
0.8957	High Similarity	NPC474520
0.8957	High Similarity	NPC55619
0.8957	High Similarity	NPC200388
0.8957	High Similarity	NPC472916
0.8957	High Similarity	NPC100916
0.8957	High Similarity	NPC98661
0.8957	High Similarity	NPC268161
0.8953	High Similarity	NPC476273
0.8951	High Similarity	NPC179126
0.8951	High Similarity	NPC292214
0.8951	High Similarity	NPC145379
0.8951	High Similarity	NPC47781
0.8951	High Similarity	NPC78326
0.8951	High Similarity	NPC88645
0.8951	High Similarity	NPC255350
0.8951	High Similarity	NPC86485
0.8951	High Similarity	NPC160951
0.8951	High Similarity	NPC274327
0.8951	High Similarity	NPC271779
0.8951	High Similarity	NPC176775
0.8951	High Similarity	NPC231018
0.8951	High Similarity	NPC206238
0.8951	High Similarity	NPC183878
0.8951	High Similarity	NPC22519
0.8951	High Similarity	NPC270620
0.8951	High Similarity	NPC69394
0.8951	High Similarity	NPC236223
0.8951	High Similarity	NPC167091
0.8947	High Similarity	NPC24258
0.8941	High Similarity	NPC30550
0.8941	High Similarity	NPC261471
0.8929	High Similarity	NPC86477
0.8929	High Similarity	NPC76482
0.8922	High Similarity	NPC224280
0.8922	High Similarity	NPC234052
0.8922	High Similarity	NPC29411
0.8916	High Similarity	NPC81679
0.8916	High Similarity	NPC294965
0.8914	High Similarity	NPC240808
0.8909	High Similarity	NPC263449
0.8909	High Similarity	NPC476980
0.8909	High Similarity	NPC188967
0.8908	High Similarity	NPC476170
0.8902	High Similarity	NPC99597
0.8902	High Similarity	NPC472911
0.8902	High Similarity	NPC471479
0.8902	High Similarity	NPC475267
0.8902	High Similarity	NPC474208
0.8902	High Similarity	NPC472914
0.8902	High Similarity	NPC96167
0.8902	High Similarity	NPC210084
0.8902	High Similarity	NPC299520
0.8902	High Similarity	NPC156057
0.8902	High Similarity	NPC245758
0.8902	High Similarity	NPC300727
0.8902	High Similarity	NPC262286
0.8902	High Similarity	NPC78225
0.8902	High Similarity	NPC67876
0.8902	High Similarity	NPC469584
0.8902	High Similarity	NPC472910
0.8902	High Similarity	NPC471515
0.8902	High Similarity	NPC36852
0.8902	High Similarity	NPC185526
0.8902	High Similarity	NPC472913
0.8902	High Similarity	NPC48208
0.8902	High Similarity	NPC241904
0.8902	High Similarity	NPC181960
0.8902	High Similarity	NPC162869
0.8902	High Similarity	NPC222814

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 NPC476640 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	444
0.1-0.2	1012
0.2-0.3	1851
0.3-0.4	2713
0.4-0.5	1725
0.5-0.6	935
0.6-0.7	316
0.7-0.8	113
0.8-0.85	25
0.85-0.9	12
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9074	High Similarity	NPD3882	Suspended
0.8951	High Similarity	NPD2801	Approved
0.8698	High Similarity	NPD6166	Phase 2
0.8698	High Similarity	NPD6168	Clinical (unspecified phase)
0.8698	High Similarity	NPD6167	Clinical (unspecified phase)
0.8659	High Similarity	NPD1934	Approved
0.8529	High Similarity	NPD3926	Phase 2
0.8521	High Similarity	NPD1247	Approved
0.8519	High Similarity	NPD1512	Approved
0.8494	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8488	Intermediate Similarity	NPD3818	Discontinued
0.8471	Intermediate Similarity	NPD6232	Discontinued
0.8462	Intermediate Similarity	NPD5494	Approved
0.8443	Intermediate Similarity	NPD3817	Phase 2
0.843	Intermediate Similarity	NPD7473	Discontinued
0.8395	Intermediate Similarity	NPD1511	Approved
0.8352	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5844	Phase 1
0.8284	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD3749	Approved
0.8232	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD6599	Discontinued
0.8192	Intermediate Similarity	NPD6559	Discontinued
0.8187	Intermediate Similarity	NPD919	Approved
0.8136	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD6797	Phase 2
0.8129	Intermediate Similarity	NPD7075	Discontinued
0.8092	Intermediate Similarity	NPD6959	Discontinued
0.809	Intermediate Similarity	NPD7251	Discontinued
0.8079	Intermediate Similarity	NPD7074	Phase 3
0.8061	Intermediate Similarity	NPD6799	Approved
0.8059	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD7808	Phase 3
0.8023	Intermediate Similarity	NPD7054	Approved
0.8012	Intermediate Similarity	NPD5402	Approved
0.7978	Intermediate Similarity	NPD7472	Approved
0.7978	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD1465	Phase 2
0.7914	Intermediate Similarity	NPD2344	Approved
0.7904	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6801	Discontinued
0.7888	Intermediate Similarity	NPD1607	Approved
0.7882	Intermediate Similarity	NPD4380	Phase 2
0.7866	Intermediate Similarity	NPD1549	Phase 2
0.7816	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1510	Phase 2
0.7764	Intermediate Similarity	NPD1240	Approved
0.7764	Intermediate Similarity	NPD943	Approved
0.7759	Intermediate Similarity	NPD7768	Phase 2
0.7753	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7819	Suspended
0.7744	Intermediate Similarity	NPD2796	Approved
0.7733	Intermediate Similarity	NPD7411	Suspended
0.7725	Intermediate Similarity	NPD2309	Approved
0.7722	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD2533	Approved
0.7692	Intermediate Similarity	NPD2534	Approved
0.7667	Intermediate Similarity	NPD3751	Discontinued
0.7605	Intermediate Similarity	NPD2800	Approved
0.7602	Intermediate Similarity	NPD5403	Approved
0.7602	Intermediate Similarity	NPD920	Approved
0.7584	Intermediate Similarity	NPD7199	Phase 2
0.7581	Intermediate Similarity	NPD8434	Phase 2
0.7576	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6234	Discontinued
0.7542	Intermediate Similarity	NPD3787	Discontinued
0.753	Intermediate Similarity	NPD2935	Discontinued
0.7529	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7390	Discontinued
0.7515	Intermediate Similarity	NPD6190	Approved
0.7514	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD1243	Approved
0.7485	Intermediate Similarity	NPD5401	Approved
0.7485	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD4628	Phase 3
0.7456	Intermediate Similarity	NPD3750	Approved
0.744	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1551	Phase 2
0.7407	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD230	Phase 1
0.7394	Intermediate Similarity	NPD447	Suspended
0.7386	Intermediate Similarity	NPD37	Approved
0.7384	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD1471	Phase 3
0.7368	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4965	Approved
0.736	Intermediate Similarity	NPD4967	Phase 2
0.736	Intermediate Similarity	NPD4966	Approved
0.7346	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6776	Approved
0.7333	Intermediate Similarity	NPD6782	Approved
0.7333	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6781	Approved
0.7333	Intermediate Similarity	NPD6778	Approved
0.7333	Intermediate Similarity	NPD6777	Approved
0.7333	Intermediate Similarity	NPD6780	Approved
0.7333	Intermediate Similarity	NPD1613	Approved
0.7333	Intermediate Similarity	NPD6779	Approved
0.7326	Intermediate Similarity	NPD8312	Approved
0.7326	Intermediate Similarity	NPD8313	Approved
0.7321	Intermediate Similarity	NPD6099	Approved
0.7321	Intermediate Similarity	NPD6100	Approved
0.7316	Intermediate Similarity	NPD4287	Approved
0.731	Intermediate Similarity	NPD7435	Discontinued
0.7283	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7228	Approved
0.7278	Intermediate Similarity	NPD2346	Discontinued
0.7268	Intermediate Similarity	NPD2403	Approved
0.7256	Intermediate Similarity	NPD3027	Phase 3
0.7245	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD8150	Discontinued
0.7207	Intermediate Similarity	NPD2296	Approved
0.7189	Intermediate Similarity	NPD2163	Approved
0.7186	Intermediate Similarity	NPD7871	Phase 2
0.7186	Intermediate Similarity	NPD7870	Phase 2
0.7181	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6233	Phase 2
0.7163	Intermediate Similarity	NPD7907	Approved
0.716	Intermediate Similarity	NPD2799	Discontinued
0.716	Intermediate Similarity	NPD3748	Approved
0.7159	Intermediate Similarity	NPD1653	Approved
0.7158	Intermediate Similarity	NPD7229	Phase 3
0.7158	Intermediate Similarity	NPD5710	Approved
0.7158	Intermediate Similarity	NPD5711	Approved
0.7151	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7696	Phase 3
0.7136	Intermediate Similarity	NPD7698	Approved
0.7136	Intermediate Similarity	NPD7697	Approved
0.7134	Intermediate Similarity	NPD9494	Approved
0.7129	Intermediate Similarity	NPD8151	Discontinued
0.7118	Intermediate Similarity	NPD5404	Approved
0.7118	Intermediate Similarity	NPD5406	Approved
0.7118	Intermediate Similarity	NPD5405	Approved
0.7118	Intermediate Similarity	NPD5408	Approved
0.7108	Intermediate Similarity	NPD6798	Discontinued
0.7108	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7874	Approved
0.7094	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4908	Phase 1
0.7083	Intermediate Similarity	NPD1933	Approved
0.7081	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7701	Phase 2
0.7077	Intermediate Similarity	NPD6534	Approved
0.7077	Intermediate Similarity	NPD6535	Approved
0.7076	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD5953	Discontinued
0.7067	Intermediate Similarity	NPD4111	Phase 1
0.7067	Intermediate Similarity	NPD4665	Approved
0.7059	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7783	Phase 2
0.7059	Intermediate Similarity	NPD7286	Phase 2
0.7056	Intermediate Similarity	NPD5761	Phase 2
0.7056	Intermediate Similarity	NPD5760	Phase 2
0.7052	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7685	Pre-registration
0.7035	Intermediate Similarity	NPD2493	Approved
0.7035	Intermediate Similarity	NPD2494	Approved
0.7027	Intermediate Similarity	NPD5242	Approved
0.7022	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3764	Approved
0.7006	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2313	Discontinued
0.7	Intermediate Similarity	NPD6280	Approved
0.7	Intermediate Similarity	NPD6279	Approved
0.6982	Remote Similarity	NPD6355	Discontinued
0.6976	Remote Similarity	NPD7801	Approved
0.697	Remote Similarity	NPD7699	Phase 2
0.697	Remote Similarity	NPD7700	Phase 2
0.695	Remote Similarity	NPD3450	Approved
0.695	Remote Similarity	NPD3452	Approved
0.6946	Remote Similarity	NPD4625	Phase 3
0.6941	Remote Similarity	NPD6651	Approved
0.6931	Remote Similarity	NPD4583	Approved
0.6931	Remote Similarity	NPD4582	Approved
0.6927	Remote Similarity	NPD7458	Discontinued
0.6915	Remote Similarity	NPD7177	Discontinued
0.6915	Remote Similarity	NPD6823	Phase 2
0.6911	Remote Similarity	NPD7549	Discontinued
0.6909	Remote Similarity	NPD1203	Approved
0.6909	Remote Similarity	NPD1470	Approved
0.6902	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6808	Phase 2
0.6881	Remote Similarity	NPD4002	Approved
0.6881	Remote Similarity	NPD4004	Approved
0.6867	Remote Similarity	NPD2798	Approved
0.686	Remote Similarity	NPD4308	Phase 3
0.6859	Remote Similarity	NPD7039	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