NPASS Compound

Structure

CID312056 OpenBabel06191716122D 22 24 0 0 0 0 0 0 0 0999 V2000 -1.7213 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4344 1.4898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1399 2.5602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 1.0739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9781 0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9487 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1180 2.7681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7872 2.0250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 4.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4271 3.7192 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 3.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7653 2.2329 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 9 1 0 0 0 0 2 20 1 0 0 0 0 3 21 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 14 1 0 0 0 0 6 10 2 0 0 0 0 6 12 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 17 2 0 0 0 0 9 22 1 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 17 1 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 22 1 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	300.1
Volume:	302.415
LogP:	3.267
LogD:	3.328
LogS:	-4.408
# Rotatable Bonds:	3
TPSA:	72.06
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.769
Synthetic Accessibility Score:	2.273
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.838
MDCK Permeability:	2.622062311274931e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.753
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	95.94078826904297%
Volume Distribution (VD):	0.602
Pgp-substrate:	6.921742916107178%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.736
CYP2C19-substrate:	0.141
CYP2C9-inhibitor:	0.565
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.632
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.697
CYP3A4-substrate:	0.613

ADMET: Excretion

Clearance (CL):	10.629
Half-life (T1/2):	0.725

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.307
Drug-inuced Liver Injury (DILI):	0.932
AMES Toxicity:	0.561
Rat Oral Acute Toxicity:	0.081
Maximum Recommended Daily Dose:	0.73
Skin Sensitization:	0.491
Carcinogencity:	0.074
Eye Corrosion:	0.005
Eye Irritation:	0.76
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: NPC312056

Natural Product ID:	NPC312056
*Common Name:**	Pterolinus A
IUPAC Name:	3-(3-hydroxy-4-methoxyphenyl)-6-methoxy-2-methyl-1-benzofuran-5-ol
Synonyms:	Pterolinus A
Standard InCHIKey:	ZQLLSZOQHBGUJG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H16O5/c1-9-17(10-4-5-14(20-2)12(18)6-10)11-7-13(19)16(21-3)8-15(11)22-9/h4-8,18-19H,1-3H3
SMILES:	COc1ccc(cc1O)c1c(C)oc2c1cc(O)c(c2)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1801598
PubChem CID:	53262810
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
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	Heartwood	India	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	heartwood	n.a.	PMID[21488654]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	heartwood	n.a.	n.a.	PMID[21784631]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1087	Pterocarpus santalinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1087	Pterocarpus santalinus	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

Activity Type	# Activity
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	0.33	ug.mL-1	PMID[505103]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2.54	ug.mL-1	PMID[505103]
NPT2	Others	Unspecified		IC50	=	0.33	ug.mL-1	PMID[505103]

☑ 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 NPC312056 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	456
0.1-0.2	1955
0.2-0.3	4684
0.3-0.4	11241
0.4-0.5	6331
0.5-0.6	3677
0.6-0.7	5137
0.7-0.8	5275
0.8-0.85	2183
0.85-0.9	1129
0.9-0.95	578
0.95-1	51

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC84515
0.9935	High Similarity	NPC188486
0.9806	High Similarity	NPC133065
0.9804	High Similarity	NPC16935
0.9804	High Similarity	NPC196879
0.9745	High Similarity	NPC247973
0.9744	High Similarity	NPC45449
0.9744	High Similarity	NPC36320
0.9744	High Similarity	NPC39306
0.9679	High Similarity	NPC263092
0.9679	High Similarity	NPC39305
0.9679	High Similarity	NPC59295
0.9679	High Similarity	NPC1706
0.9679	High Similarity	NPC1755
0.9673	High Similarity	NPC45131
0.9615	High Similarity	NPC272722
0.9615	High Similarity	NPC238995
0.9563	High Similarity	NPC174700
0.9557	High Similarity	NPC277480
0.9503	High Similarity	NPC476640
0.9503	High Similarity	NPC473834
0.9503	High Similarity	NPC82217
0.9503	High Similarity	NPC310794
0.9503	High Similarity	NPC216842
0.9497	High Similarity	NPC50394
0.9494	High Similarity	NPC291110
0.9494	High Similarity	NPC37183
0.9477	High Similarity	NPC125300
0.9444	High Similarity	NPC287243
0.9441	High Similarity	NPC230619
0.9441	High Similarity	NPC54098
0.9437	High Similarity	NPC247136
0.9423	High Similarity	NPC195832
0.9419	High Similarity	NPC472461
0.9387	High Similarity	NPC49667
0.9387	High Similarity	NPC8127
0.9379	High Similarity	NPC131866
0.9379	High Similarity	NPC476641
0.9375	High Similarity	NPC470704
0.9355	High Similarity	NPC20830
0.9355	High Similarity	NPC256612
0.9295	High Similarity	NPC472916
0.929	High Similarity	NPC274327
0.929	High Similarity	NPC183878
0.929	High Similarity	NPC231018
0.929	High Similarity	NPC160951
0.929	High Similarity	NPC206238
0.929	High Similarity	NPC292214
0.929	High Similarity	NPC22519
0.929	High Similarity	NPC255350
0.929	High Similarity	NPC88645
0.929	High Similarity	NPC145379
0.929	High Similarity	NPC47781
0.929	High Similarity	NPC167091
0.929	High Similarity	NPC271779
0.929	High Similarity	NPC69394
0.929	High Similarity	NPC176775
0.9281	High Similarity	NPC92722
0.9281	High Similarity	NPC102003
0.9264	High Similarity	NPC261471
0.9264	High Similarity	NPC65885
0.9255	High Similarity	NPC86477
0.925	High Similarity	NPC29411
0.9245	High Similarity	NPC81679
0.9241	High Similarity	NPC476980
0.9236	High Similarity	NPC210084
0.9236	High Similarity	NPC262286
0.9236	High Similarity	NPC222814
0.9236	High Similarity	NPC36852
0.9236	High Similarity	NPC472910
0.9236	High Similarity	NPC474836
0.9236	High Similarity	NPC245758
0.9236	High Similarity	NPC469584
0.9236	High Similarity	NPC299520
0.9236	High Similarity	NPC129684
0.9236	High Similarity	NPC181960
0.9236	High Similarity	NPC241904
0.9236	High Similarity	NPC474208
0.9236	High Similarity	NPC472911
0.9236	High Similarity	NPC156057
0.9236	High Similarity	NPC475267
0.9236	High Similarity	NPC96167
0.9236	High Similarity	NPC162869
0.9236	High Similarity	NPC472914
0.9236	High Similarity	NPC78225
0.9236	High Similarity	NPC99597
0.9236	High Similarity	NPC472913
0.9236	High Similarity	NPC48208
0.9236	High Similarity	NPC300727
0.9231	High Similarity	NPC92659
0.9231	High Similarity	NPC128863
0.9231	High Similarity	NPC183597
0.9231	High Similarity	NPC50715
0.9231	High Similarity	NPC163780
0.9231	High Similarity	NPC167815
0.9231	High Similarity	NPC196439
0.9231	High Similarity	NPC138360
0.9231	High Similarity	NPC2476
0.9231	High Similarity	NPC280339
0.9231	High Similarity	NPC146165
0.9231	High Similarity	NPC4455
0.9231	High Similarity	NPC208197
0.9231	High Similarity	NPC213622
0.9231	High Similarity	NPC201136
0.9231	High Similarity	NPC227325
0.9231	High Similarity	NPC2928
0.9226	High Similarity	NPC187498
0.9226	High Similarity	NPC161277
0.9226	High Similarity	NPC60972
0.9226	High Similarity	NPC222830
0.9226	High Similarity	NPC241498
0.9226	High Similarity	NPC198826
0.9226	High Similarity	NPC120163
0.9226	High Similarity	NPC212678
0.9226	High Similarity	NPC199100
0.9226	High Similarity	NPC83508
0.9226	High Similarity	NPC100887
0.9226	High Similarity	NPC301323
0.9226	High Similarity	NPC25270
0.9226	High Similarity	NPC101996
0.9226	High Similarity	NPC71334
0.9226	High Similarity	NPC156222
0.9226	High Similarity	NPC39007
0.9226	High Similarity	NPC180234
0.9226	High Similarity	NPC207624
0.9226	High Similarity	NPC275836
0.9226	High Similarity	NPC239128
0.9226	High Similarity	NPC120537
0.9226	High Similarity	NPC188203
0.9226	High Similarity	NPC256283
0.9226	High Similarity	NPC57030
0.9226	High Similarity	NPC162313
0.9226	High Similarity	NPC131624
0.9226	High Similarity	NPC293183
0.9226	High Similarity	NPC39732
0.9226	High Similarity	NPC275722
0.9216	High Similarity	NPC131451
0.9216	High Similarity	NPC287395
0.9216	High Similarity	NPC183655
0.9216	High Similarity	NPC15329
0.9212	High Similarity	NPC297807
0.9207	High Similarity	NPC227906
0.9198	High Similarity	NPC211309
0.9187	High Similarity	NPC110257
0.9187	High Similarity	NPC475985
0.9182	High Similarity	NPC258331
0.9177	High Similarity	NPC476242
0.9172	High Similarity	NPC235165
0.9172	High Similarity	NPC255106
0.9172	High Similarity	NPC191146
0.9172	High Similarity	NPC138243
0.9172	High Similarity	NPC274730
0.9172	High Similarity	NPC68093
0.9172	High Similarity	NPC49824
0.9167	High Similarity	NPC250822
0.9167	High Similarity	NPC276409
0.9167	High Similarity	NPC75279
0.9167	High Similarity	NPC472915
0.9167	High Similarity	NPC280937
0.9167	High Similarity	NPC124714
0.9161	High Similarity	NPC226973
0.9161	High Similarity	NPC149614
0.9161	High Similarity	NPC106372
0.9161	High Similarity	NPC170169
0.9161	High Similarity	NPC193976
0.9161	High Similarity	NPC251110
0.9161	High Similarity	NPC117579
0.9161	High Similarity	NPC115324
0.9161	High Similarity	NPC171010
0.9161	High Similarity	NPC58668
0.9161	High Similarity	NPC23668
0.9161	High Similarity	NPC208043
0.9161	High Similarity	NPC308451
0.915	High Similarity	NPC119660
0.915	High Similarity	NPC93034
0.915	High Similarity	NPC17816
0.9141	High Similarity	NPC78830
0.9141	High Similarity	NPC218533
0.913	High Similarity	NPC326520
0.913	High Similarity	NPC472277
0.9125	High Similarity	NPC472448
0.9125	High Similarity	NPC83922
0.9119	High Similarity	NPC14353
0.9119	High Similarity	NPC228785
0.9119	High Similarity	NPC56085
0.9114	High Similarity	NPC476981
0.9114	High Similarity	NPC75215
0.9114	High Similarity	NPC227192
0.9114	High Similarity	NPC203891
0.9114	High Similarity	NPC101830
0.9114	High Similarity	NPC93376
0.9114	High Similarity	NPC110070
0.9114	High Similarity	NPC224137
0.9114	High Similarity	NPC189179
0.9114	High Similarity	NPC470402
0.9108	High Similarity	NPC26227
0.9108	High Similarity	NPC44079
0.9108	High Similarity	NPC37392
0.9108	High Similarity	NPC168247
0.9108	High Similarity	NPC255807

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 NPC312056 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	424
0.1-0.2	973
0.2-0.3	1796
0.3-0.4	2697
0.4-0.5	1767
0.5-0.6	957
0.6-0.7	367
0.7-0.8	120
0.8-0.85	32
0.85-0.9	10
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.929	High Similarity	NPD2801	Approved
0.9172	High Similarity	NPD3882	Suspended
0.8981	High Similarity	NPD1934	Approved
0.8805	High Similarity	NPD2393	Clinical (unspecified phase)
0.8788	High Similarity	NPD3818	Discontinued
0.8765	High Similarity	NPD5494	Approved
0.872	High Similarity	NPD3926	Phase 2
0.871	High Similarity	NPD1511	Approved
0.8667	High Similarity	NPD6166	Phase 2
0.8667	High Similarity	NPD6167	Clinical (unspecified phase)
0.8667	High Similarity	NPD6168	Clinical (unspecified phase)
0.8599	High Similarity	NPD1512	Approved
0.8598	High Similarity	NPD1247	Approved
0.8466	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD6232	Discontinued
0.8405	Intermediate Similarity	NPD3817	Phase 2
0.8393	Intermediate Similarity	NPD7473	Discontinued
0.8353	Intermediate Similarity	NPD7074	Phase 3
0.8323	Intermediate Similarity	NPD2344	Approved
0.8314	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD3749	Approved
0.8302	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD5844	Phase 1
0.8294	Intermediate Similarity	NPD7054	Approved
0.8256	Intermediate Similarity	NPD6559	Discontinued
0.8253	Intermediate Similarity	NPD919	Approved
0.8246	Intermediate Similarity	NPD7472	Approved
0.8232	Intermediate Similarity	NPD1465	Phase 2
0.817	Intermediate Similarity	NPD1240	Approved
0.817	Intermediate Similarity	NPD943	Approved
0.816	Intermediate Similarity	NPD4380	Phase 2
0.8153	Intermediate Similarity	NPD1549	Phase 2
0.8125	Intermediate Similarity	NPD6799	Approved
0.8113	Intermediate Similarity	NPD2309	Approved
0.8092	Intermediate Similarity	NPD6797	Phase 2
0.8089	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7075	Discontinued
0.8077	Intermediate Similarity	NPD1510	Phase 2
0.8075	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1607	Approved
0.8049	Intermediate Similarity	NPD6599	Discontinued
0.8046	Intermediate Similarity	NPD7251	Discontinued
0.8025	Intermediate Similarity	NPD2796	Approved
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD7808	Phase 3
0.7989	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2800	Approved
0.7975	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD920	Approved
0.7964	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD5402	Approved
0.7941	Intermediate Similarity	NPD6959	Discontinued
0.7911	Intermediate Similarity	NPD2935	Discontinued
0.7892	Intermediate Similarity	NPD7411	Suspended
0.7875	Intermediate Similarity	NPD1243	Approved
0.7853	Intermediate Similarity	NPD2533	Approved
0.7853	Intermediate Similarity	NPD2534	Approved
0.7853	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD2532	Approved
0.7844	Intermediate Similarity	NPD6801	Discontinued
0.7833	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7768	Phase 2
0.7803	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD447	Suspended
0.7771	Intermediate Similarity	NPD230	Phase 1
0.7736	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD7199	Phase 2
0.773	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3750	Approved
0.7683	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3027	Phase 3
0.7616	Intermediate Similarity	NPD6234	Discontinued
0.7613	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD4628	Phase 3
0.7595	Intermediate Similarity	NPD1613	Approved
0.7595	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1551	Phase 2
0.7569	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD5403	Approved
0.7544	Intermediate Similarity	NPD2296	Approved
0.7527	Intermediate Similarity	NPD8434	Phase 2
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD9494	Approved
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3226	Approved
0.7427	Intermediate Similarity	NPD37	Approved
0.7425	Intermediate Similarity	NPD5401	Approved
0.7423	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3748	Approved
0.7403	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD4966	Approved
0.7399	Intermediate Similarity	NPD4965	Approved
0.7399	Intermediate Similarity	NPD4967	Phase 2
0.7396	Intermediate Similarity	NPD1653	Approved
0.7394	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5953	Discontinued
0.7386	Intermediate Similarity	NPD3787	Discontinued
0.7374	Intermediate Similarity	NPD7286	Phase 2
0.7366	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7390	Discontinued
0.7362	Intermediate Similarity	NPD6099	Approved
0.7362	Intermediate Similarity	NPD6100	Approved
0.7351	Intermediate Similarity	NPD4287	Approved
0.7349	Intermediate Similarity	NPD6190	Approved
0.7345	Intermediate Similarity	NPD5242	Approved
0.7329	Intermediate Similarity	NPD1933	Approved
0.7326	Intermediate Similarity	NPD6280	Approved
0.7326	Intermediate Similarity	NPD6279	Approved
0.7318	Intermediate Similarity	NPD7228	Approved
0.7317	Intermediate Similarity	NPD2346	Discontinued
0.7317	Intermediate Similarity	NPD1471	Phase 3
0.7303	Intermediate Similarity	NPD2403	Approved
0.7288	Intermediate Similarity	NPD7229	Phase 3
0.7288	Intermediate Similarity	NPD5710	Approved
0.7288	Intermediate Similarity	NPD5711	Approved
0.7284	Intermediate Similarity	NPD6651	Approved
0.7261	Intermediate Similarity	NPD1203	Approved
0.7253	Intermediate Similarity	NPD7685	Pre-registration
0.725	Intermediate Similarity	NPD2313	Discontinued
0.7233	Intermediate Similarity	NPD4908	Phase 1
0.7222	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2163	Approved
0.7219	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6808	Phase 2
0.7186	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD9269	Phase 2
0.7174	Intermediate Similarity	NPD8312	Approved
0.7174	Intermediate Similarity	NPD8313	Approved
0.716	Intermediate Similarity	NPD4357	Discontinued
0.7143	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3764	Approved
0.7126	Intermediate Similarity	NPD2654	Approved
0.7125	Intermediate Similarity	NPD6832	Phase 2
0.7117	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2798	Approved
0.7098	Intermediate Similarity	NPD6779	Approved
0.7098	Intermediate Similarity	NPD6776	Approved
0.7098	Intermediate Similarity	NPD6777	Approved
0.7098	Intermediate Similarity	NPD6782	Approved
0.7098	Intermediate Similarity	NPD6781	Approved
0.7098	Intermediate Similarity	NPD6780	Approved
0.7098	Intermediate Similarity	NPD6778	Approved
0.7086	Intermediate Similarity	NPD5761	Phase 2
0.7086	Intermediate Similarity	NPD5760	Phase 2
0.7071	Intermediate Similarity	NPD8151	Discontinued
0.707	Intermediate Similarity	NPD1608	Approved
0.707	Intermediate Similarity	NPD9717	Approved
0.7069	Intermediate Similarity	NPD6386	Approved
0.7069	Intermediate Similarity	NPD6385	Approved
0.7065	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2861	Phase 2
0.7049	Intermediate Similarity	NPD1729	Discontinued
0.7045	Intermediate Similarity	NPD5353	Approved
0.7037	Intermediate Similarity	NPD3268	Approved
0.7031	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD6844	Discontinued
0.7027	Intermediate Similarity	NPD7549	Discontinued
0.7024	Intermediate Similarity	NPD7907	Approved
0.7013	Intermediate Similarity	NPD5536	Phase 2
0.7012	Intermediate Similarity	NPD6355	Discontinued
0.701	Intermediate Similarity	NPD4111	Phase 1
0.701	Intermediate Similarity	NPD4665	Approved
0.7006	Intermediate Similarity	NPD1610	Phase 2
0.7006	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7783	Phase 2
0.6994	Remote Similarity	NPD6233	Phase 2
0.699	Remote Similarity	NPD7435	Discontinued
0.6988	Remote Similarity	NPD7033	Discontinued
0.6979	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4361	Phase 2
0.6977	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4625	Phase 3
0.6968	Remote Similarity	NPD8150	Discontinued
0.6962	Remote Similarity	NPD3972	Approved
0.6957	Remote Similarity	NPD3018	Phase 2
0.6954	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7870	Phase 2
0.6954	Remote Similarity	NPD7871	Phase 2
0.6946	Remote Similarity	NPD5405	Approved
0.6946	Remote Similarity	NPD5406	Approved
0.6946	Remote Similarity	NPD5404	Approved
0.6946	Remote Similarity	NPD5408	Approved
0.6937	Remote Similarity	NPD1470	Approved
0.6937	Remote Similarity	NPD2797	Approved
0.6933	Remote Similarity	NPD411	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