NPASS Compound

Structure

NPC470977 OpenBabel07101718312D 22 23 0 0 1 0 0 0 0 0999 V2000 -6.0878 -1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 -1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.9230 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -1.7891 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 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 5 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 13 1 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 15 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 18 1 0 0 0 0 13 14 1 0 0 0 0 13 19 2 0 0 0 0 15 16 2 0 0 0 0 16 22 1 0 0 0 0 17 12 1 1 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.27
Volume:	469.272
LogP:	4.337
LogD:	3.159
LogS:	-3.901
# Rotatable Bonds:	9
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	5.005
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.524
MDCK Permeability:	1.6286088794004172e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.147
30% Bioavailability (F30%):	0.911

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.392
Plasma Protein Binding (PPB):	95.45404815673828%
Volume Distribution (VD):	1.914
Pgp-substrate:	4.138559341430664%

ADMET: Metabolism

CYP1A2-inhibitor:	0.275
CYP1A2-substrate:	0.189
CYP2C19-inhibitor:	0.924
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.936
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.026
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.91
CYP3A4-substrate:	0.634

ADMET: Excretion

Clearance (CL):	4.352
Half-life (T1/2):	0.099

ADMET: Toxicity

hERG Blockers:	0.269
Human Hepatotoxicity (H-HT):	0.858
Drug-inuced Liver Injury (DILI):	0.821
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.262
Maximum Recommended Daily Dose:	0.863
Skin Sensitization:	0.454
Carcinogencity:	0.127
Eye Corrosion:	0.043
Eye Irritation:	0.03
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC470977

Natural Product ID:	NPC470977
*Common Name:**	2-((R)-5-Acetyl-2,3-Dihydrobenzofuran-2-Yl)Allyl 2-Methylbutanoate
IUPAC Name:	2-[(2R)-5-acetyl-2,3-dihydro-1-benzofuran-2-yl]prop-2-enyl 2-methylbutanoate
Synonyms:
Standard InCHIKey:	OJROQMJYULMMBP-DFDFJRDNSA-N
Standard InCHI:	InChI=1S/C18H22O4/c1-5-11(2)18(20)21-10-12(3)17-9-15-8-14(13(4)19)6-7-16(15)22-17/h6-8,11,17H,3,5,9-10H2,1-2,4H3/t11?,17-/m1/s1
SMILES:	CCC(C)C(=O)OCC(=C)C1CC2=C(O1)C=CC(=C2)C(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334418
PubChem CID:	71720040
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000119] Acetophenones

*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
NPO25148.1	Helichrysum italicum	Under-species	n.a.	n.a.	Flowered aerial parts	Arzana, Sardinia	2010-Jul	PMID[23265253]

☑ 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
MIC	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128.0	ug.mL-1	PMID[450638]

☑ 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 NPC470977 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	314
0.1-0.2	1466
0.2-0.3	3535
0.3-0.4	8586
0.4-0.5	9996
0.5-0.6	4290
0.6-0.7	8624
0.7-0.8	5470
0.8-0.85	385
0.85-0.9	17
0.9-0.95	5
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470976
1.0	High Similarity	NPC196979
0.9919	High Similarity	NPC282230
0.9919	High Similarity	NPC183348
0.984	High Similarity	NPC15083
0.9839	High Similarity	NPC170546
0.9839	High Similarity	NPC66246
0.9516	High Similarity	NPC470858
0.9355	High Similarity	NPC141252
0.9355	High Similarity	NPC11799
0.907	High Similarity	NPC939
0.8971	High Similarity	NPC470856
0.8864	High Similarity	NPC470859
0.8786	High Similarity	NPC286038
0.8769	High Similarity	NPC293387
0.8769	High Similarity	NPC37512
0.8731	High Similarity	NPC247743
0.8723	High Similarity	NPC66991
0.872	High Similarity	NPC293424
0.8686	High Similarity	NPC36414
0.8647	High Similarity	NPC279596
0.8623	High Similarity	NPC472515
0.8615	High Similarity	NPC165556
0.8613	High Similarity	NPC253616
0.8561	High Similarity	NPC184053
0.8561	High Similarity	NPC50583
0.856	High Similarity	NPC470860
0.854	High Similarity	NPC268081
0.8519	High Similarity	NPC55147
0.8519	High Similarity	NPC54503
0.8496	Intermediate Similarity	NPC473019
0.8485	Intermediate Similarity	NPC121104
0.8451	Intermediate Similarity	NPC171656
0.8451	Intermediate Similarity	NPC294365
0.8433	Intermediate Similarity	NPC327457
0.8433	Intermediate Similarity	NPC86774
0.8433	Intermediate Similarity	NPC109778
0.8417	Intermediate Similarity	NPC473988
0.8414	Intermediate Similarity	NPC191104
0.8409	Intermediate Similarity	NPC237868
0.8406	Intermediate Similarity	NPC472516
0.8397	Intermediate Similarity	NPC221798
0.8397	Intermediate Similarity	NPC89630
0.838	Intermediate Similarity	NPC213900
0.838	Intermediate Similarity	NPC184702
0.837	Intermediate Similarity	NPC125153
0.8369	Intermediate Similarity	NPC254010
0.8369	Intermediate Similarity	NPC171870
0.8357	Intermediate Similarity	NPC473209
0.8357	Intermediate Similarity	NPC137009
0.8357	Intermediate Similarity	NPC37206
0.8357	Intermediate Similarity	NPC136095
0.8357	Intermediate Similarity	NPC11566
0.8356	Intermediate Similarity	NPC290671
0.8346	Intermediate Similarity	NPC469954
0.8345	Intermediate Similarity	NPC259685
0.8345	Intermediate Similarity	NPC104172
0.8345	Intermediate Similarity	NPC88886
0.8345	Intermediate Similarity	NPC88445
0.8333	Intermediate Similarity	NPC14875
0.8322	Intermediate Similarity	NPC208584
0.8321	Intermediate Similarity	NPC209858
0.831	Intermediate Similarity	NPC472344
0.8306	Intermediate Similarity	NPC23332
0.8298	Intermediate Similarity	NPC16455
0.8298	Intermediate Similarity	NPC307990
0.8295	Intermediate Similarity	NPC230951
0.8284	Intermediate Similarity	NPC473744
0.8284	Intermediate Similarity	NPC2401
0.8276	Intermediate Similarity	NPC95526
0.8276	Intermediate Similarity	NPC168085
0.8276	Intermediate Similarity	NPC266743
0.8273	Intermediate Similarity	NPC156910
0.8273	Intermediate Similarity	NPC254741
0.8271	Intermediate Similarity	NPC475236
0.8271	Intermediate Similarity	NPC474737
0.8261	Intermediate Similarity	NPC470844
0.8261	Intermediate Similarity	NPC229128
0.8258	Intermediate Similarity	NPC184219
0.8255	Intermediate Similarity	NPC470625
0.8254	Intermediate Similarity	NPC252004
0.8252	Intermediate Similarity	NPC290038
0.8248	Intermediate Similarity	NPC222036
0.8248	Intermediate Similarity	NPC229646
0.8248	Intermediate Similarity	NPC7526
0.8244	Intermediate Similarity	NPC69403
0.8244	Intermediate Similarity	NPC291189
0.8243	Intermediate Similarity	NPC131725
0.8239	Intermediate Similarity	NPC229916
0.8239	Intermediate Similarity	NPC201820
0.8239	Intermediate Similarity	NPC297985
0.8227	Intermediate Similarity	NPC262635
0.8226	Intermediate Similarity	NPC473809
0.8226	Intermediate Similarity	NPC183648
0.8219	Intermediate Similarity	NPC472298
0.8219	Intermediate Similarity	NPC317492
0.8219	Intermediate Similarity	NPC164299
0.8214	Intermediate Similarity	NPC62735
0.8214	Intermediate Similarity	NPC103001
0.8214	Intermediate Similarity	NPC38153
0.8212	Intermediate Similarity	NPC43971
0.8212	Intermediate Similarity	NPC74749
0.8212	Intermediate Similarity	NPC19554
0.8207	Intermediate Similarity	NPC218300
0.8207	Intermediate Similarity	NPC471285
0.8207	Intermediate Similarity	NPC282335
0.8207	Intermediate Similarity	NPC74539
0.8207	Intermediate Similarity	NPC304443
0.8203	Intermediate Similarity	NPC45104
0.8203	Intermediate Similarity	NPC217423
0.8201	Intermediate Similarity	NPC163029
0.8201	Intermediate Similarity	NPC170604
0.8201	Intermediate Similarity	NPC215109
0.8201	Intermediate Similarity	NPC46869
0.8201	Intermediate Similarity	NPC307401
0.8201	Intermediate Similarity	NPC99854
0.8201	Intermediate Similarity	NPC283331
0.82	Intermediate Similarity	NPC269495
0.8194	Intermediate Similarity	NPC473015
0.8194	Intermediate Similarity	NPC473013
0.8194	Intermediate Similarity	NPC474044
0.8189	Intermediate Similarity	NPC220540
0.8188	Intermediate Similarity	NPC55149
0.8188	Intermediate Similarity	NPC307412
0.8188	Intermediate Similarity	NPC311339
0.8182	Intermediate Similarity	NPC51146
0.8182	Intermediate Similarity	NPC313036
0.8182	Intermediate Similarity	NPC471643
0.8182	Intermediate Similarity	NPC471639
0.8182	Intermediate Similarity	NPC470556
0.8182	Intermediate Similarity	NPC147145
0.8182	Intermediate Similarity	NPC166858
0.8182	Intermediate Similarity	NPC130206
0.8176	Intermediate Similarity	NPC10429
0.8175	Intermediate Similarity	NPC14248
0.8175	Intermediate Similarity	NPC183103
0.8175	Intermediate Similarity	NPC302844
0.8175	Intermediate Similarity	NPC293253
0.8175	Intermediate Similarity	NPC175159
0.8169	Intermediate Similarity	NPC472409
0.8163	Intermediate Similarity	NPC472421
0.8163	Intermediate Similarity	NPC474735
0.8163	Intermediate Similarity	NPC140133
0.8163	Intermediate Similarity	NPC180351
0.8162	Intermediate Similarity	NPC136340
0.8162	Intermediate Similarity	NPC245395
0.8158	Intermediate Similarity	NPC92589
0.8148	Intermediate Similarity	NPC2596
0.8148	Intermediate Similarity	NPC125887
0.8146	Intermediate Similarity	NPC50430
0.8143	Intermediate Similarity	NPC24394
0.8143	Intermediate Similarity	NPC470397
0.8143	Intermediate Similarity	NPC29638
0.8143	Intermediate Similarity	NPC161196
0.8143	Intermediate Similarity	NPC470398
0.8143	Intermediate Similarity	NPC187826
0.8138	Intermediate Similarity	NPC154217
0.8138	Intermediate Similarity	NPC71821
0.8138	Intermediate Similarity	NPC471346
0.8138	Intermediate Similarity	NPC470322
0.8134	Intermediate Similarity	NPC188327
0.8134	Intermediate Similarity	NPC234109
0.8134	Intermediate Similarity	NPC474476
0.8133	Intermediate Similarity	NPC109967
0.8133	Intermediate Similarity	NPC474738
0.8133	Intermediate Similarity	NPC78554
0.8133	Intermediate Similarity	NPC261484
0.8133	Intermediate Similarity	NPC469936
0.8133	Intermediate Similarity	NPC321372
0.8133	Intermediate Similarity	NPC474609
0.8133	Intermediate Similarity	NPC475797
0.8133	Intermediate Similarity	NPC129053
0.8129	Intermediate Similarity	NPC125269
0.8129	Intermediate Similarity	NPC61499
0.8129	Intermediate Similarity	NPC236974
0.8129	Intermediate Similarity	NPC144027
0.8125	Intermediate Similarity	NPC96216
0.8125	Intermediate Similarity	NPC164980
0.8125	Intermediate Similarity	NPC149026
0.8125	Intermediate Similarity	NPC91560
0.8125	Intermediate Similarity	NPC307895
0.8125	Intermediate Similarity	NPC470553
0.8125	Intermediate Similarity	NPC125894
0.8125	Intermediate Similarity	NPC470932
0.8125	Intermediate Similarity	NPC75049
0.8125	Intermediate Similarity	NPC17262
0.8125	Intermediate Similarity	NPC310130
0.8125	Intermediate Similarity	NPC68104
0.8125	Intermediate Similarity	NPC107177
0.8125	Intermediate Similarity	NPC474939
0.8125	Intermediate Similarity	NPC39329
0.8125	Intermediate Similarity	NPC169591
0.8125	Intermediate Similarity	NPC175504
0.8125	Intermediate Similarity	NPC77794
0.8125	Intermediate Similarity	NPC85162
0.8125	Intermediate Similarity	NPC470909
0.8125	Intermediate Similarity	NPC257097
0.8125	Intermediate Similarity	NPC221432
0.8125	Intermediate Similarity	NPC59522
0.8125	Intermediate Similarity	NPC223812

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 NPC470977 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	956
0.2-0.3	1490
0.3-0.4	2462
0.4-0.5	1989
0.5-0.6	1242
0.6-0.7	547
0.7-0.8	185
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8489	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD2799	Discontinued
0.8284	Intermediate Similarity	NPD6832	Phase 2
0.8273	Intermediate Similarity	NPD2796	Approved
0.8227	Intermediate Similarity	NPD1243	Approved
0.8214	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD920	Approved
0.8182	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8175	Intermediate Similarity	NPD1241	Discontinued
0.8121	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8069	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD3267	Approved
0.806	Intermediate Similarity	NPD3266	Approved
0.8042	Intermediate Similarity	NPD4628	Phase 3
0.803	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8029	Intermediate Similarity	NPD2313	Discontinued
0.8014	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD1019	Discontinued
0.8	Intermediate Similarity	NPD7819	Suspended
0.7987	Intermediate Similarity	NPD7411	Suspended
0.7986	Intermediate Similarity	NPD6355	Discontinued
0.7986	Intermediate Similarity	NPD3887	Approved
0.797	Intermediate Similarity	NPD9717	Approved
0.797	Intermediate Similarity	NPD3972	Approved
0.7961	Intermediate Similarity	NPD7075	Discontinued
0.7943	Intermediate Similarity	NPD3748	Approved
0.7939	Intermediate Similarity	NPD5691	Approved
0.7933	Intermediate Similarity	NPD6801	Discontinued
0.7914	Intermediate Similarity	NPD4307	Phase 2
0.7903	Intermediate Similarity	NPD3134	Approved
0.7899	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7899	Intermediate Similarity	NPD3268	Approved
0.7857	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5494	Approved
0.7852	Intermediate Similarity	NPD7458	Discontinued
0.7852	Intermediate Similarity	NPD1876	Approved
0.7832	Intermediate Similarity	NPD2344	Approved
0.7832	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD6002	Phase 3
0.7832	Intermediate Similarity	NPD6005	Phase 3
0.7832	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7832	Intermediate Similarity	NPD6004	Phase 3
0.7823	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6599	Discontinued
0.7794	Intermediate Similarity	NPD2797	Approved
0.7792	Intermediate Similarity	NPD919	Approved
0.7786	Intermediate Similarity	NPD3140	Approved
0.7786	Intermediate Similarity	NPD3142	Approved
0.7778	Intermediate Similarity	NPD1549	Phase 2
0.777	Intermediate Similarity	NPD6273	Approved
0.777	Intermediate Similarity	NPD6798	Discontinued
0.7756	Intermediate Similarity	NPD6808	Phase 2
0.7744	Intermediate Similarity	NPD17	Approved
0.7737	Intermediate Similarity	NPD2798	Approved
0.7733	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD9545	Approved
0.7712	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD2353	Approved
0.7708	Intermediate Similarity	NPD2346	Discontinued
0.7703	Intermediate Similarity	NPD2532	Approved
0.7703	Intermediate Similarity	NPD2533	Approved
0.7703	Intermediate Similarity	NPD2534	Approved
0.7698	Intermediate Similarity	NPD1358	Approved
0.7692	Intermediate Similarity	NPD4308	Phase 3
0.7673	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD3750	Approved
0.7671	Intermediate Similarity	NPD7003	Approved
0.7664	Intermediate Similarity	NPD1203	Approved
0.766	Intermediate Similarity	NPD2979	Phase 3
0.7656	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4477	Approved
0.7639	Intermediate Similarity	NPD4476	Approved
0.7639	Intermediate Similarity	NPD2438	Suspended
0.763	Intermediate Similarity	NPD1281	Approved
0.7619	Intermediate Similarity	NPD2309	Approved
0.7612	Intermediate Similarity	NPD4626	Approved
0.7606	Intermediate Similarity	NPD1933	Approved
0.76	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD8032	Phase 2
0.7586	Intermediate Similarity	NPD1471	Phase 3
0.7584	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD1608	Approved
0.7569	Intermediate Similarity	NPD1510	Phase 2
0.7569	Intermediate Similarity	NPD7033	Discontinued
0.7566	Intermediate Similarity	NPD4380	Phase 2
0.7556	Intermediate Similarity	NPD3496	Discontinued
0.7548	Intermediate Similarity	NPD7768	Phase 2
0.7547	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD5535	Approved
0.7535	Intermediate Similarity	NPD1240	Approved
0.7534	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD2424	Discontinued
0.7533	Intermediate Similarity	NPD5049	Phase 3
0.7518	Intermediate Similarity	NPD411	Approved
0.7516	Intermediate Similarity	NPD5890	Approved
0.7516	Intermediate Similarity	NPD5889	Approved
0.75	Intermediate Similarity	NPD2354	Approved
0.7484	Intermediate Similarity	NPD3817	Phase 2
0.7483	Intermediate Similarity	NPD447	Suspended
0.7483	Intermediate Similarity	NPD2800	Approved
0.7481	Intermediate Similarity	NPD1778	Approved
0.7468	Intermediate Similarity	NPD6280	Approved
0.7468	Intermediate Similarity	NPD6279	Approved
0.7467	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD6233	Phase 2
0.7464	Intermediate Similarity	NPD1283	Approved
0.7463	Intermediate Similarity	NPD1894	Discontinued
0.7444	Intermediate Similarity	NPD9493	Approved
0.7436	Intermediate Similarity	NPD3882	Suspended
0.7436	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD1607	Approved
0.7413	Intermediate Similarity	NPD4060	Phase 1
0.7407	Intermediate Similarity	NPD5585	Approved
0.7407	Intermediate Similarity	NPD5844	Phase 1
0.7407	Intermediate Similarity	NPD1651	Approved
0.7402	Intermediate Similarity	NPD9697	Approved
0.7397	Intermediate Similarity	NPD1551	Phase 2
0.7397	Intermediate Similarity	NPD2531	Phase 2
0.7394	Intermediate Similarity	NPD1296	Phase 2
0.7389	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3749	Approved
0.7386	Intermediate Similarity	NPD3226	Approved
0.7368	Intermediate Similarity	NPD5403	Approved
0.7365	Intermediate Similarity	NPD2654	Approved
0.7361	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD4618	Approved
0.7361	Intermediate Similarity	NPD5124	Phase 1
0.7361	Intermediate Similarity	NPD4622	Approved
0.7358	Intermediate Similarity	NPD1247	Approved
0.7357	Intermediate Similarity	NPD5647	Approved
0.7355	Intermediate Similarity	NPD1934	Approved
0.7351	Intermediate Similarity	NPD5401	Approved
0.7343	Intermediate Similarity	NPD4062	Phase 3
0.7338	Intermediate Similarity	NPD6585	Discontinued
0.7317	Intermediate Similarity	NPD5953	Discontinued
0.7315	Intermediate Similarity	NPD4110	Phase 3
0.7315	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2186	Approved
0.7286	Intermediate Similarity	NPD6362	Approved
0.7285	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6559	Discontinued
0.7273	Intermediate Similarity	NPD3764	Approved
0.726	Intermediate Similarity	NPD5688	Approved
0.726	Intermediate Similarity	NPD5689	Approved
0.726	Intermediate Similarity	NPD7097	Phase 1
0.7254	Intermediate Similarity	NPD2614	Approved
0.7239	Intermediate Similarity	NPD3818	Discontinued
0.7231	Intermediate Similarity	NPD2684	Approved
0.7231	Intermediate Similarity	NPD2182	Approved
0.7226	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7440	Discontinued
0.7214	Intermediate Similarity	NPD3225	Approved
0.7208	Intermediate Similarity	NPD957	Approved
0.7205	Intermediate Similarity	NPD7229	Phase 3
0.7195	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7286	Phase 2
0.7194	Intermediate Similarity	NPD1481	Phase 2
0.7192	Intermediate Similarity	NPD6651	Approved
0.7192	Intermediate Similarity	NPD6653	Approved
0.7183	Intermediate Similarity	NPD9494	Approved
0.7181	Intermediate Similarity	NPD2897	Discontinued
0.7181	Intermediate Similarity	NPD5958	Discontinued
0.7179	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3847	Discontinued
0.7172	Intermediate Similarity	NPD4140	Approved
0.716	Intermediate Similarity	NPD3926	Phase 2
0.7152	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5402	Approved
0.7143	Intermediate Similarity	NPD6959	Discontinued
0.7143	Intermediate Similarity	NPD7843	Approved
0.7143	Intermediate Similarity	NPD7427	Discontinued
0.7143	Intermediate Similarity	NPD5586	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4359	Approved
0.7132	Intermediate Similarity	NPD5536	Phase 2
0.7126	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD4661	Approved
0.7124	Intermediate Similarity	NPD4662	Approved
0.7123	Intermediate Similarity	NPD230	Phase 1
0.7122	Intermediate Similarity	NPD1535	Discovery
0.7122	Intermediate Similarity	NPD422	Phase 1
0.7122	Intermediate Similarity	NPD1611	Approved
0.7113	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7157	Approved
0.7109	Intermediate Similarity	NPD9261	Approved
0.7105	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2801	Approved
0.7089	Intermediate Similarity	NPD8455	Phase 2
0.7073	Intermediate Similarity	NPD7473	Discontinued
0.707	Intermediate Similarity	NPD958	Approved
0.707	Intermediate Similarity	NPD6385	Approved
0.707	Intermediate Similarity	NPD6386	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