NPASS Compound

Structure

NPC247964 OpenBabel07101718312D 33 36 0 0 1 0 0 0 0 0999 V2000 5.1808 -4.3005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1808 -0.8364 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 3.5116 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 -2.5685 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6808 -3.4345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 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 4.1808 -0.8364 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 1 0 0 0 0 0 0 0 0 0 5.1808 -2.5685 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 5.6808 -1.7024 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 3.6808 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6808 -3.4345 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6808 -1.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7026 -1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 30 1 0 0 0 0 4 5 2 0 0 0 0 4 15 1 0 0 0 0 5 20 1 0 0 0 0 6 17 1 0 0 0 0 6 18 1 0 0 0 0 7 16 1 0 0 0 0 7 21 2 0 0 0 0 8 15 2 0 0 0 0 8 24 1 0 0 0 0 9 16 1 0 0 0 0 9 22 2 0 0 0 0 10 19 2 0 0 0 0 10 23 1 0 0 0 0 11 17 2 0 0 0 0 11 32 1 0 0 0 0 12 31 1 0 0 0 0 13 19 1 0 0 0 0 13 26 2 0 0 0 0 14 27 2 0 0 0 0 14 31 1 0 0 0 0 16 23 2 0 0 0 0 17 22 1 0 0 0 0 18 12 1 6 0 0 0 18 25 1 0 0 0 0 19 21 1 0 0 0 0 20 24 2 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 33 1 0 0 0 0 23 33 1 0 0 0 0 24 30 1 0 0 0 0 25 15 1 1 0 0 0 25 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.15
Volume:	450.687
LogP:	4.245
LogD:	2.994
LogS:	-3.947
# Rotatable Bonds:	7
TPSA:	115.43
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.407
Synthetic Accessibility Score:	3.847
Fsp3:	0.28
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:	-4.788
MDCK Permeability:	1.3039017176197376e-05
Pgp-inhibitor:	0.237
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.543

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	88.05316925048828%
Volume Distribution (VD):	1.154
Pgp-substrate:	14.347553253173828%

ADMET: Metabolism

CYP1A2-inhibitor:	0.815
CYP1A2-substrate:	0.66
CYP2C19-inhibitor:	0.869
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.908
CYP2C9-substrate:	0.791
CYP2D6-inhibitor:	0.908
CYP2D6-substrate:	0.371
CYP3A4-inhibitor:	0.86
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	2.113
Half-life (T1/2):	0.861

ADMET: Toxicity

hERG Blockers:	0.131
Human Hepatotoxicity (H-HT):	0.345
Drug-inuced Liver Injury (DILI):	0.651
AMES Toxicity:	0.391
Rat Oral Acute Toxicity:	0.195
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.084
Carcinogencity:	0.918
Eye Corrosion:	0.003
Eye Irritation:	0.062
Respiratory Toxicity:	0.28

Download Data

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

Natural Product: NPC247964

Natural Product ID:	NPC247964
*Common Name:**	Propolis-Benzofuran A
IUPAC Name:	[(2R,3S)-5-(6-acetyl-5-hydroxy-1-benzofuran-2-yl)-2-(4-hydroxy-3-methoxyphenyl)-3,4-dihydro-2H-pyran-3-yl]methyl acetate
Synonyms:
Standard InCHIKey:	LRCVZTUZPOPXCV-BVZFJXPGSA-N
Standard InCHI:	InChI=1S/C25H24O8/c1-13(26)19-10-23-16(7-21(19)29)9-22(33-23)17-6-18(12-31-14(2)27)25(32-11-17)15-4-5-20(28)24(8-15)30-3/h4-5,7-11,18,25,28-29H,6,12H2,1-3H3/t18-,25-/m0/s1
SMILES:	CC(=O)c1cc2c(cc1O)cc(C1=CO[C@@H](c3ccc(c(c3)OC)O)[C@@H](C1)COC(=O)C)o2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486786
PubChem CID:	10003994
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

*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
NPO30782	Brazilian propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	DOI[10.1248/cpb.47.1521]
NPO30782	Brazilian propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[11000036]
NPO30782	Brazilian propolis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[8951168]
NPO30782	Brazilian propolis	n.a.	n.a.	n.a.	n.a.	Brazilian propolis	n.a.	PMID[9677271]

☑ 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
ED50	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT453	Cell Line	HT-1080	Homo sapiens	ED50	=	13.9	ug ml-1	PMID[551664]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	12.4	ug ml-1	PMID[551664]

☑ 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 NPC247964 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	373
0.1-0.2	1553
0.2-0.3	3585
0.3-0.4	8374
0.4-0.5	10007
0.5-0.6	3991
0.6-0.7	5433
0.7-0.8	6763
0.8-0.85	2055
0.85-0.9	561
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.929	High Similarity	NPC475996
0.9264	High Similarity	NPC89131
0.908	High Similarity	NPC300680
0.9059	High Similarity	NPC297807
0.8976	High Similarity	NPC29411
0.897	High Similarity	NPC312056
0.897	High Similarity	NPC84515
0.8953	High Similarity	NPC47883
0.8947	High Similarity	NPC98546
0.8941	High Similarity	NPC287243
0.8909	High Similarity	NPC188486
0.8902	High Similarity	NPC16935
0.8902	High Similarity	NPC196879
0.8882	High Similarity	NPC261471
0.8882	High Similarity	NPC216842
0.8882	High Similarity	NPC476640
0.8882	High Similarity	NPC82217
0.8882	High Similarity	NPC310794
0.8869	High Similarity	NPC86477
0.8869	High Similarity	NPC247973
0.8862	High Similarity	NPC36320
0.8855	High Similarity	NPC81679
0.8824	High Similarity	NPC54098
0.8824	High Similarity	NPC230619
0.8824	High Similarity	NPC174700
0.882	High Similarity	NPC243891
0.881	High Similarity	NPC277480
0.8802	High Similarity	NPC223006
0.8802	High Similarity	NPC272750
0.8802	High Similarity	NPC134047
0.8802	High Similarity	NPC173729
0.8802	High Similarity	NPC477689
0.8802	High Similarity	NPC133065
0.8795	High Similarity	NPC469889
0.878	High Similarity	NPC45131
0.8779	High Similarity	NPC164384
0.8779	High Similarity	NPC8127
0.8779	High Similarity	NPC49667
0.8772	High Similarity	NPC37606
0.8772	High Similarity	NPC473834
0.8772	High Similarity	NPC233956
0.8765	High Similarity	NPC267091
0.8765	High Similarity	NPC131866
0.8765	High Similarity	NPC476641
0.8765	High Similarity	NPC78830
0.8765	High Similarity	NPC218533
0.8757	High Similarity	NPC243877
0.8757	High Similarity	NPC295436
0.8757	High Similarity	NPC470704
0.875	High Similarity	NPC39306
0.875	High Similarity	NPC45449
0.875	High Similarity	NPC37183
0.875	High Similarity	NPC291110
0.875	High Similarity	NPC248315
0.8743	High Similarity	NPC154527
0.8743	High Similarity	NPC144843
0.8743	High Similarity	NPC272722
0.8743	High Similarity	NPC144557
0.8735	High Similarity	NPC472962
0.8735	High Similarity	NPC472961
0.8735	High Similarity	NPC130955
0.8727	High Similarity	NPC475267
0.8727	High Similarity	NPC210084
0.8727	High Similarity	NPC245758
0.8727	High Similarity	NPC472910
0.8727	High Similarity	NPC222814
0.8727	High Similarity	NPC48208
0.8727	High Similarity	NPC162869
0.8727	High Similarity	NPC470402
0.8727	High Similarity	NPC472914
0.8727	High Similarity	NPC474836
0.8727	High Similarity	NPC99597
0.8727	High Similarity	NPC474208
0.8727	High Similarity	NPC96167
0.8727	High Similarity	NPC472911
0.8727	High Similarity	NPC156057
0.8727	High Similarity	NPC472913
0.8721	High Similarity	NPC227906
0.872	High Similarity	NPC138360
0.872	High Similarity	NPC201136
0.872	High Similarity	NPC213622
0.872	High Similarity	NPC50715
0.872	High Similarity	NPC20830
0.872	High Similarity	NPC183597
0.872	High Similarity	NPC208197
0.872	High Similarity	NPC163780
0.872	High Similarity	NPC128863
0.872	High Similarity	NPC256612
0.872	High Similarity	NPC196439
0.872	High Similarity	NPC2476
0.872	High Similarity	NPC227325
0.872	High Similarity	NPC280339
0.872	High Similarity	NPC167815
0.872	High Similarity	NPC92659
0.872	High Similarity	NPC4455
0.872	High Similarity	NPC146165
0.8713	High Similarity	NPC158226
0.8706	High Similarity	NPC476279
0.8706	High Similarity	NPC280493
0.8698	High Similarity	NPC207575
0.8698	High Similarity	NPC13481
0.8693	High Similarity	NPC226725
0.869	High Similarity	NPC263092
0.869	High Similarity	NPC39305
0.869	High Similarity	NPC45943
0.869	High Similarity	NPC1706
0.869	High Similarity	NPC1755
0.869	High Similarity	NPC59295
0.8683	High Similarity	NPC266314
0.8683	High Similarity	NPC269117
0.8671	High Similarity	NPC107244
0.8667	High Similarity	NPC235165
0.8667	High Similarity	NPC317383
0.8667	High Similarity	NPC255106
0.8667	High Similarity	NPC472916
0.8663	High Similarity	NPC65885
0.8659	High Similarity	NPC124714
0.8659	High Similarity	NPC250822
0.8659	High Similarity	NPC280937
0.8659	High Similarity	NPC231018
0.8659	High Similarity	NPC274327
0.8659	High Similarity	NPC47781
0.8659	High Similarity	NPC69394
0.8659	High Similarity	NPC255350
0.8659	High Similarity	NPC183878
0.8659	High Similarity	NPC75279
0.8659	High Similarity	NPC22519
0.8659	High Similarity	NPC160951
0.8659	High Similarity	NPC145379
0.8659	High Similarity	NPC176775
0.8659	High Similarity	NPC250557
0.8659	High Similarity	NPC276409
0.8655	High Similarity	NPC124470
0.8655	High Similarity	NPC109827
0.8655	High Similarity	NPC281835
0.8647	High Similarity	NPC14662
0.8647	High Similarity	NPC186392
0.8647	High Similarity	NPC50394
0.8639	High Similarity	NPC474301
0.8639	High Similarity	NPC142614
0.8636	High Similarity	NPC71260
0.8634	High Similarity	NPC472969
0.8631	High Similarity	NPC238995
0.8629	High Similarity	NPC97523
0.8623	High Similarity	NPC53889
0.8623	High Similarity	NPC328102
0.8623	High Similarity	NPC476980
0.8623	High Similarity	NPC47623
0.8621	High Similarity	NPC475783
0.8614	High Similarity	NPC108456
0.8614	High Similarity	NPC75215
0.8614	High Similarity	NPC129684
0.8614	High Similarity	NPC227192
0.8614	High Similarity	NPC189179
0.8614	High Similarity	NPC224137
0.8614	High Similarity	NPC93376
0.8614	High Similarity	NPC469584
0.8614	High Similarity	NPC299520
0.8614	High Similarity	NPC181960
0.8613	High Similarity	NPC53917
0.8606	High Similarity	NPC472909
0.8606	High Similarity	NPC80489
0.8606	High Similarity	NPC2928
0.8606	High Similarity	NPC37392
0.8606	High Similarity	NPC268008
0.8605	High Similarity	NPC205076
0.8605	High Similarity	NPC211594
0.8605	High Similarity	NPC307518
0.8605	High Similarity	NPC212038
0.8605	High Similarity	NPC81332
0.8605	High Similarity	NPC254540
0.8605	High Similarity	NPC262580
0.8605	High Similarity	NPC271848
0.8605	High Similarity	NPC48773
0.8605	High Similarity	NPC172807
0.8605	High Similarity	NPC289396
0.8598	High Similarity	NPC71334
0.8598	High Similarity	NPC289968
0.8598	High Similarity	NPC212678
0.8598	High Similarity	NPC35763
0.8598	High Similarity	NPC142540
0.8598	High Similarity	NPC60972
0.8598	High Similarity	NPC187498
0.8598	High Similarity	NPC301323
0.8598	High Similarity	NPC291802
0.8598	High Similarity	NPC156222
0.8598	High Similarity	NPC275722
0.8598	High Similarity	NPC245382
0.8598	High Similarity	NPC188203
0.8598	High Similarity	NPC121522
0.8598	High Similarity	NPC293183
0.8598	High Similarity	NPC241498
0.8598	High Similarity	NPC100263
0.8598	High Similarity	NPC120163
0.8598	High Similarity	NPC100887
0.8598	High Similarity	NPC222830
0.8598	High Similarity	NPC83508
0.8598	High Similarity	NPC256283
0.8598	High Similarity	NPC275836
0.8598	High Similarity	NPC209487

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 NPC247964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	897
0.2-0.3	1772
0.3-0.4	2534
0.4-0.5	1952
0.5-0.6	1028
0.6-0.7	456
0.7-0.8	155
0.8-0.85	25
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8659	High Similarity	NPD2801	Approved
0.8647	High Similarity	NPD3818	Discontinued
0.8485	Intermediate Similarity	NPD1934	Approved
0.848	Intermediate Similarity	NPD7473	Discontinued
0.8443	Intermediate Similarity	NPD3882	Suspended
0.8443	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8412	Intermediate Similarity	NPD6232	Discontinued
0.84	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD3817	Phase 2
0.8343	Intermediate Similarity	NPD6559	Discontinued
0.8324	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8314	Intermediate Similarity	NPD6166	Phase 2
0.8294	Intermediate Similarity	NPD5494	Approved
0.8276	Intermediate Similarity	NPD5844	Phase 1
0.8171	Intermediate Similarity	NPD7054	Approved
0.8125	Intermediate Similarity	NPD7074	Phase 3
0.8125	Intermediate Similarity	NPD7472	Approved
0.811	Intermediate Similarity	NPD1511	Approved
0.807	Intermediate Similarity	NPD7075	Discontinued
0.8059	Intermediate Similarity	NPD5402	Approved
0.8046	Intermediate Similarity	NPD3926	Phase 2
0.8035	Intermediate Similarity	NPD1247	Approved
0.8023	Intermediate Similarity	NPD919	Approved
0.8012	Intermediate Similarity	NPD1512	Approved
0.8011	Intermediate Similarity	NPD8434	Phase 2
0.7978	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD6797	Phase 2
0.7965	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD2344	Approved
0.7956	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6801	Discontinued
0.7933	Intermediate Similarity	NPD7251	Discontinued
0.7929	Intermediate Similarity	NPD4380	Phase 2
0.7927	Intermediate Similarity	NPD4628	Phase 3
0.7895	Intermediate Similarity	NPD1465	Phase 2
0.7895	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7889	Intermediate Similarity	NPD7808	Phase 3
0.787	Intermediate Similarity	NPD3226	Approved
0.7861	Intermediate Similarity	NPD3749	Approved
0.7824	Intermediate Similarity	NPD6599	Discontinued
0.7791	Intermediate Similarity	NPD2935	Discontinued
0.7791	Intermediate Similarity	NPD7819	Suspended
0.7784	Intermediate Similarity	NPD6799	Approved
0.7784	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7411	Suspended
0.7771	Intermediate Similarity	NPD2309	Approved
0.7758	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD920	Approved
0.7751	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD8312	Approved
0.7747	Intermediate Similarity	NPD8313	Approved
0.7742	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7735	Intermediate Similarity	NPD7685	Pre-registration
0.7727	Intermediate Similarity	NPD6959	Discontinued
0.7714	Intermediate Similarity	NPD6234	Discontinued
0.7697	Intermediate Similarity	NPD1549	Phase 2
0.7683	Intermediate Similarity	NPD2796	Approved
0.7665	Intermediate Similarity	NPD6190	Approved
0.7654	Intermediate Similarity	NPD447	Suspended
0.7647	Intermediate Similarity	NPD5403	Approved
0.7644	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD2533	Approved
0.7633	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD2534	Approved
0.7633	Intermediate Similarity	NPD2532	Approved
0.7627	Intermediate Similarity	NPD7199	Phase 2
0.7622	Intermediate Similarity	NPD1510	Phase 2
0.7611	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1243	Approved
0.7542	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD2346	Discontinued
0.7529	Intermediate Similarity	NPD5401	Approved
0.7529	Intermediate Similarity	NPD37	Approved
0.7515	Intermediate Similarity	NPD2799	Discontinued
0.7515	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD4966	Approved
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1551	Phase 2
0.7469	Intermediate Similarity	NPD2313	Discontinued
0.7439	Intermediate Similarity	NPD230	Phase 1
0.7433	Intermediate Similarity	NPD8150	Discontinued
0.7427	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7228	Approved
0.741	Intermediate Similarity	NPD7033	Discontinued
0.7396	Intermediate Similarity	NPD3750	Approved
0.7389	Intermediate Similarity	NPD6808	Phase 2
0.7378	Intermediate Similarity	NPD943	Approved
0.7378	Intermediate Similarity	NPD1240	Approved
0.7356	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7435	Discontinued
0.7333	Intermediate Similarity	NPD1933	Approved
0.7333	Intermediate Similarity	NPD8127	Discontinued
0.7322	Intermediate Similarity	NPD3751	Discontinued
0.7317	Intermediate Similarity	NPD6233	Phase 2
0.7297	Intermediate Similarity	NPD5953	Discontinued
0.7294	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD9494	Approved
0.7282	Intermediate Similarity	NPD6779	Approved
0.7282	Intermediate Similarity	NPD6780	Approved
0.7282	Intermediate Similarity	NPD6778	Approved
0.7282	Intermediate Similarity	NPD6776	Approved
0.7282	Intermediate Similarity	NPD6777	Approved
0.7282	Intermediate Similarity	NPD6781	Approved
0.7282	Intermediate Similarity	NPD6782	Approved
0.7264	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD7783	Phase 2
0.7258	Intermediate Similarity	NPD7039	Approved
0.7258	Intermediate Similarity	NPD7038	Approved
0.7257	Intermediate Similarity	NPD7458	Discontinued
0.7256	Intermediate Similarity	NPD6798	Discontinued
0.725	Intermediate Similarity	NPD8151	Discontinued
0.7247	Intermediate Similarity	NPD2296	Approved
0.7239	Intermediate Similarity	NPD6832	Phase 2
0.7229	Intermediate Similarity	NPD6355	Discontinued
0.7222	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4308	Phase 3
0.7193	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD4110	Phase 3
0.7175	Intermediate Similarity	NPD6386	Approved
0.7175	Intermediate Similarity	NPD6385	Approved
0.7169	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1613	Approved
0.716	Intermediate Similarity	NPD1203	Approved
0.7152	Intermediate Similarity	NPD3268	Approved
0.7152	Intermediate Similarity	NPD3764	Approved
0.7152	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7870	Phase 2
0.7136	Intermediate Similarity	NPD7871	Phase 2
0.7135	Intermediate Similarity	NPD2800	Approved
0.7135	Intermediate Similarity	NPD6279	Approved
0.7135	Intermediate Similarity	NPD2163	Approved
0.7135	Intermediate Similarity	NPD6844	Discontinued
0.7135	Intermediate Similarity	NPD6280	Approved
0.7129	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7874	Approved
0.7128	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD7266	Discontinued
0.7118	Intermediate Similarity	NPD1471	Phase 3
0.7117	Intermediate Similarity	NPD2798	Approved
0.7104	Intermediate Similarity	NPD5710	Approved
0.7104	Intermediate Similarity	NPD5711	Approved
0.7104	Intermediate Similarity	NPD7229	Phase 3
0.7104	Intermediate Similarity	NPD3787	Discontinued
0.7101	Intermediate Similarity	NPD3748	Approved
0.7097	Intermediate Similarity	NPD7286	Phase 2
0.7095	Intermediate Similarity	NPD5760	Phase 2
0.7095	Intermediate Similarity	NPD8455	Phase 2
0.7095	Intermediate Similarity	NPD5761	Phase 2
0.7093	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7003	Approved
0.7091	Intermediate Similarity	NPD3027	Phase 3
0.7086	Intermediate Similarity	NPD6273	Approved
0.7085	Intermediate Similarity	NPD7697	Approved
0.7085	Intermediate Similarity	NPD7698	Approved
0.7085	Intermediate Similarity	NPD7696	Phase 3
0.7081	Intermediate Similarity	NPD1608	Approved
0.7073	Intermediate Similarity	NPD2861	Phase 2
0.7059	Intermediate Similarity	NPD5406	Approved
0.7059	Intermediate Similarity	NPD5404	Approved
0.7059	Intermediate Similarity	NPD5408	Approved
0.7059	Intermediate Similarity	NPD5405	Approved
0.7055	Intermediate Similarity	NPD2797	Approved
0.7048	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD411	Approved
0.7048	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD7177	Discontinued
0.7037	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7701	Phase 2
0.703	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6535	Approved
0.7026	Intermediate Similarity	NPD6534	Approved
0.702	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7801	Approved
0.7005	Intermediate Similarity	NPD8404	Phase 2
0.7	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4287	Approved
0.6994	Remote Similarity	NPD8166	Discontinued
0.6984	Remote Similarity	NPD7240	Approved
0.6975	Remote Similarity	NPD9717	Approved
0.6973	Remote Similarity	NPD5242	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