NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	552.18
Volume:	519.844
LogP:	0.65
LogD:	0.778
LogS:	-2.717
# Rotatable Bonds:	11
TPSA:	204.83
# H-Bond Aceptor:	13
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.173
Synthetic Accessibility Score:	4.412
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.35
MDCK Permeability:	1.543759208288975e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.179
Human Intestinal Absorption (HIA):	0.981
20% Bioavailability (F20%):	0.964
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.166
Plasma Protein Binding (PPB):	88.17931365966797%
Volume Distribution (VD):	0.358
Pgp-substrate:	22.430055618286133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.027
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.415
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.166
CYP3A4-substrate:	0.079

ADMET: Excretion

Clearance (CL):	1.393
Half-life (T1/2):	0.823

ADMET: Toxicity

hERG Blockers:	0.279
Human Hepatotoxicity (H-HT):	0.045
Drug-inuced Liver Injury (DILI):	0.164
AMES Toxicity:	0.156
Rat Oral Acute Toxicity:	0.057
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.699
Carcinogencity:	0.34
Eye Corrosion:	0.003
Eye Irritation:	0.039
Respiratory Toxicity:	0.009

Download Data

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

Natural Product: NPC478250

Natural Product ID:	NPC478250
*Common Name:**	2-(4-hydroxyphenyl)ethyl[5-O-(4-hydroxybenzoyl)]-O--D-apiofuranosyl-(1?2)--D-glucopyranoside
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MWVDTRFZEALNIG-ZFAXPZJCSA-N
Standard InCHI:	InChI=1S/C26H32O13/c27-11-18-19(30)20(31)21(24(38-18)35-10-9-14-1-5-16(28)6-2-14)39-25-22(32)26(34,13-37-25)12-36-23(33)15-3-7-17(29)8-4-15/h1-8,18-22,24-25,27-32,34H,9-13H2/t18?,19?,20-,21+,22-,24-,25+,26+/m1/s1
SMILES:	[H]C1=CC(C(=O)OC[C@]2(O)CO[C@@H](O[C@@H]3[C@H](OCCC4=CC=C(O)C=C4)OC(CO)C(O)[C@H]3O)[C@H]2O)=CC=C1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds]

*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
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9835	Catalpa ovata	Species	Bignoniaceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC478250 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	305
0.1-0.2	1229
0.2-0.3	2757
0.3-0.4	6495
0.4-0.5	10913
0.5-0.6	6840
0.6-0.7	9246
0.7-0.8	4461
0.8-0.85	388
0.85-0.9	58
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC471345
0.9191	High Similarity	NPC114116
0.9185	High Similarity	NPC478255
0.9091	High Similarity	NPC473867
0.9091	High Similarity	NPC291153
0.9085	High Similarity	NPC473281
0.9085	High Similarity	NPC77922
0.906	High Similarity	NPC226759
0.8973	High Similarity	NPC182350
0.8963	High Similarity	NPC225307
0.8912	High Similarity	NPC289021
0.8912	High Similarity	NPC158546
0.8912	High Similarity	NPC140151
0.8904	High Similarity	NPC478234
0.8904	High Similarity	NPC478236
0.8889	High Similarity	NPC288416
0.8873	High Similarity	NPC80098
0.8851	High Similarity	NPC478235
0.8819	High Similarity	NPC471028
0.8811	High Similarity	NPC469623
0.8811	High Similarity	NPC65833
0.8811	High Similarity	NPC148080
0.8808	High Similarity	NPC187205
0.8792	High Similarity	NPC229354
0.8784	High Similarity	NPC474620
0.8777	High Similarity	NPC164172
0.8776	High Similarity	NPC75945
0.8776	High Similarity	NPC92117
0.8768	High Similarity	NPC225384
0.8768	High Similarity	NPC138777
0.8768	High Similarity	NPC235294
0.8768	High Similarity	NPC46137
0.8768	High Similarity	NPC246869
0.8767	High Similarity	NPC473149
0.8759	High Similarity	NPC475528
0.8742	High Similarity	NPC265480
0.8742	High Similarity	NPC149368
0.8732	High Similarity	NPC171134
0.8732	High Similarity	NPC321638
0.8732	High Similarity	NPC321184
0.8732	High Similarity	NPC328273
0.8725	High Similarity	NPC194705
0.8716	High Similarity	NPC116292
0.8716	High Similarity	NPC87630
0.8716	High Similarity	NPC179128
0.8716	High Similarity	NPC35097
0.8716	High Similarity	NPC267469
0.8714	High Similarity	NPC169398
0.8707	High Similarity	NPC120728
0.8707	High Similarity	NPC120621
0.8707	High Similarity	NPC248257
0.8705	High Similarity	NPC471095
0.8705	High Similarity	NPC471066
0.8699	High Similarity	NPC143246
0.8699	High Similarity	NPC474268
0.8699	High Similarity	NPC208293
0.8699	High Similarity	NPC475539
0.8699	High Similarity	NPC119773
0.869	High Similarity	NPC296659
0.869	High Similarity	NPC202391
0.8681	High Similarity	NPC245219
0.8681	High Similarity	NPC31081
0.8675	High Similarity	NPC10205
0.8667	High Similarity	NPC257847
0.8667	High Similarity	NPC157898
0.8662	High Similarity	NPC302583
0.8662	High Similarity	NPC310252
0.8662	High Similarity	NPC100558
0.8662	High Similarity	NPC84789
0.8654	High Similarity	NPC469419
0.8654	High Similarity	NPC469396
0.8654	High Similarity	NPC469459
0.8654	High Similarity	NPC149002
0.8654	High Similarity	NPC469458
0.8654	High Similarity	NPC88176
0.8645	High Similarity	NPC109990
0.8643	High Similarity	NPC28637
0.8636	High Similarity	NPC477627
0.8633	High Similarity	NPC281798
0.8618	High Similarity	NPC471405
0.8613	High Similarity	NPC106677
0.8613	High Similarity	NPC35288
0.8613	High Similarity	NPC148026
0.8613	High Similarity	NPC173150
0.8613	High Similarity	NPC45224
0.8613	High Similarity	NPC471881
0.8613	High Similarity	NPC156692
0.8613	High Similarity	NPC471882
0.8611	High Similarity	NPC79908
0.8609	High Similarity	NPC327032
0.8609	High Similarity	NPC191046
0.8609	High Similarity	NPC194095
0.8603	High Similarity	NPC83218
0.8603	High Similarity	NPC126991
0.86	High Similarity	NPC134905
0.86	High Similarity	NPC36130
0.8591	High Similarity	NPC162569
0.8591	High Similarity	NPC35160
0.8591	High Similarity	NPC240592
0.8591	High Similarity	NPC117346
0.8581	High Similarity	NPC145847
0.8571	High Similarity	NPC200708
0.8562	High Similarity	NPC4747
0.8562	High Similarity	NPC472860
0.8562	High Similarity	NPC43638
0.8562	High Similarity	NPC63304
0.8562	High Similarity	NPC194938
0.8562	High Similarity	NPC122809
0.8562	High Similarity	NPC104275
0.8561	High Similarity	NPC17968
0.8561	High Similarity	NPC469705
0.8561	High Similarity	NPC470122
0.8551	High Similarity	NPC301857
0.8543	High Similarity	NPC16024
0.8543	High Similarity	NPC61152
0.8543	High Similarity	NPC88484
0.8543	High Similarity	NPC137813
0.8543	High Similarity	NPC205037
0.8543	High Similarity	NPC3746
0.8543	High Similarity	NPC259767
0.8543	High Similarity	NPC44260
0.854	High Similarity	NPC252114
0.854	High Similarity	NPC471157
0.854	High Similarity	NPC114096
0.854	High Similarity	NPC61181
0.8531	High Similarity	NPC469696
0.8531	High Similarity	NPC101686
0.8531	High Similarity	NPC469364
0.8531	High Similarity	NPC65262
0.8523	High Similarity	NPC111785
0.8523	High Similarity	NPC161955
0.8523	High Similarity	NPC96599
0.8521	High Similarity	NPC123988
0.8521	High Similarity	NPC263829
0.8519	High Similarity	NPC52097
0.8516	High Similarity	NPC293568
0.8516	High Similarity	NPC117943
0.8503	High Similarity	NPC108455
0.8497	Intermediate Similarity	NPC127406
0.8493	Intermediate Similarity	NPC105005
0.8493	Intermediate Similarity	NPC242756
0.8493	Intermediate Similarity	NPC40305
0.8489	Intermediate Similarity	NPC469549
0.8478	Intermediate Similarity	NPC103533
0.8472	Intermediate Similarity	NPC220936
0.8472	Intermediate Similarity	NPC31745
0.8471	Intermediate Similarity	NPC72016
0.8467	Intermediate Similarity	NPC88886
0.8467	Intermediate Similarity	NPC123704
0.8467	Intermediate Similarity	NPC104172
0.8462	Intermediate Similarity	NPC294470
0.8462	Intermediate Similarity	NPC472132
0.8456	Intermediate Similarity	NPC470907
0.8456	Intermediate Similarity	NPC178449
0.8456	Intermediate Similarity	NPC232454
0.8456	Intermediate Similarity	NPC140722
0.8456	Intermediate Similarity	NPC92054
0.8456	Intermediate Similarity	NPC4958
0.8452	Intermediate Similarity	NPC239966
0.8452	Intermediate Similarity	NPC203020
0.8452	Intermediate Similarity	NPC130489
0.8452	Intermediate Similarity	NPC208676
0.8451	Intermediate Similarity	NPC34293
0.8451	Intermediate Similarity	NPC886
0.8451	Intermediate Similarity	NPC287597
0.8446	Intermediate Similarity	NPC474044
0.8446	Intermediate Similarity	NPC212808
0.8446	Intermediate Similarity	NPC473147
0.8444	Intermediate Similarity	NPC11724
0.8442	Intermediate Similarity	NPC257309
0.8442	Intermediate Similarity	NPC49173
0.8442	Intermediate Similarity	NPC133984
0.844	Intermediate Similarity	NPC302844
0.8438	Intermediate Similarity	NPC477617
0.8438	Intermediate Similarity	NPC148185
0.8435	Intermediate Similarity	NPC121573
0.8435	Intermediate Similarity	NPC229036
0.8435	Intermediate Similarity	NPC190587
0.8435	Intermediate Similarity	NPC22176
0.8435	Intermediate Similarity	NPC300894
0.8435	Intermediate Similarity	NPC141455
0.8435	Intermediate Similarity	NPC296954
0.8435	Intermediate Similarity	NPC196063
0.8435	Intermediate Similarity	NPC226738
0.8431	Intermediate Similarity	NPC172920
0.8431	Intermediate Similarity	NPC156624
0.8431	Intermediate Similarity	NPC203757
0.8431	Intermediate Similarity	NPC99233
0.8428	Intermediate Similarity	NPC21956
0.8421	Intermediate Similarity	NPC44730
0.8421	Intermediate Similarity	NPC259182
0.8421	Intermediate Similarity	NPC121001
0.8417	Intermediate Similarity	NPC158673
0.8403	Intermediate Similarity	NPC260425
0.8403	Intermediate Similarity	NPC78363
0.84	Intermediate Similarity	NPC22137
0.84	Intermediate Similarity	NPC478242
0.8397	Intermediate Similarity	NPC477628
0.8397	Intermediate Similarity	NPC210961
0.8397	Intermediate Similarity	NPC195685

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 NPC478250 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	247
0.1-0.2	705
0.2-0.3	1479
0.3-0.4	2624
0.4-0.5	2382
0.5-0.6	1217
0.6-0.7	417
0.7-0.8	76
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8345	Intermediate Similarity	NPD7266	Discontinued
0.8323	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD7685	Pre-registration
0.8121	Intermediate Similarity	NPD6190	Approved
0.8054	Intermediate Similarity	NPD4628	Phase 3
0.8042	Intermediate Similarity	NPD3764	Approved
0.8025	Intermediate Similarity	NPD3818	Discontinued
0.8015	Intermediate Similarity	NPD9545	Approved
0.7935	Intermediate Similarity	NPD4380	Phase 2
0.7895	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7054	Approved
0.7862	Intermediate Similarity	NPD7075	Discontinued
0.7831	Intermediate Similarity	NPD6559	Discontinued
0.7818	Intermediate Similarity	NPD7472	Approved
0.7818	Intermediate Similarity	NPD7074	Phase 3
0.7799	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD8455	Phase 2
0.7784	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7251	Discontinued
0.7679	Intermediate Similarity	NPD7808	Phase 3
0.7673	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD6797	Phase 2
0.7647	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD230	Phase 1
0.7632	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6801	Discontinued
0.7566	Intermediate Similarity	NPD1549	Phase 2
0.7548	Intermediate Similarity	NPD6799	Approved
0.7532	Intermediate Similarity	NPD7458	Discontinued
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7516	Intermediate Similarity	NPD5403	Approved
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7228	Approved
0.745	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD7411	Suspended
0.7432	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD37	Approved
0.7391	Intermediate Similarity	NPD1934	Approved
0.7389	Intermediate Similarity	NPD5401	Approved
0.7383	Intermediate Similarity	NPD6233	Phase 2
0.7378	Intermediate Similarity	NPD6234	Discontinued
0.7368	Intermediate Similarity	NPD1510	Phase 2
0.7368	Intermediate Similarity	NPD7033	Discontinued
0.7365	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD4965	Approved
0.7362	Intermediate Similarity	NPD4967	Phase 2
0.7362	Intermediate Similarity	NPD4966	Approved
0.7358	Intermediate Similarity	NPD1653	Approved
0.7353	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD7819	Suspended
0.7346	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3817	Phase 2
0.7301	Intermediate Similarity	NPD5402	Approved
0.7292	Intermediate Similarity	NPD1091	Approved
0.7289	Intermediate Similarity	NPD7199	Phase 2
0.7279	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6599	Discontinued
0.7262	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6166	Phase 2
0.7256	Intermediate Similarity	NPD3882	Suspended
0.7244	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3750	Approved
0.7235	Intermediate Similarity	NPD5844	Phase 1
0.7219	Intermediate Similarity	NPD1240	Approved
0.7213	Intermediate Similarity	NPD7435	Discontinued
0.7212	Intermediate Similarity	NPD3749	Approved
0.7208	Intermediate Similarity	NPD2935	Discontinued
0.72	Intermediate Similarity	NPD6798	Discontinued
0.72	Intermediate Similarity	NPD8150	Discontinued
0.72	Intermediate Similarity	NPD8434	Phase 2
0.7195	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7097	Phase 1
0.7181	Intermediate Similarity	NPD6832	Phase 2
0.7176	Intermediate Similarity	NPD7799	Discontinued
0.7174	Intermediate Similarity	NPD8320	Phase 1
0.7174	Intermediate Similarity	NPD8319	Approved
0.7171	Intermediate Similarity	NPD6355	Discontinued
0.7171	Intermediate Similarity	NPD1933	Approved
0.717	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7440	Discontinued
0.7151	Intermediate Similarity	NPD7585	Approved
0.7151	Intermediate Similarity	NPD6535	Approved
0.7151	Intermediate Similarity	NPD6534	Approved
0.7135	Intermediate Similarity	NPD7999	Approved
0.7134	Intermediate Similarity	NPD2801	Approved
0.7134	Intermediate Similarity	NPD1465	Phase 2
0.7127	Intermediate Similarity	NPD7700	Phase 2
0.7127	Intermediate Similarity	NPD7699	Phase 2
0.7124	Intermediate Similarity	NPD1607	Approved
0.7122	Intermediate Similarity	NPD969	Suspended
0.7119	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD9493	Approved
0.711	Intermediate Similarity	NPD7240	Approved
0.7107	Intermediate Similarity	NPD1511	Approved
0.7101	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3455	Phase 2
0.7097	Intermediate Similarity	NPD7583	Approved
0.7097	Intermediate Similarity	NPD2796	Approved
0.7097	Intermediate Similarity	NPD1551	Phase 2
0.7095	Intermediate Similarity	NPD1203	Approved
0.7089	Intermediate Similarity	NPD2354	Approved
0.7089	Intermediate Similarity	NPD3887	Approved
0.7076	Intermediate Similarity	NPD3751	Discontinued
0.7059	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6777	Approved
0.7049	Intermediate Similarity	NPD6776	Approved
0.7049	Intermediate Similarity	NPD6778	Approved
0.7049	Intermediate Similarity	NPD6779	Approved
0.7049	Intermediate Similarity	NPD6780	Approved
0.7049	Intermediate Similarity	NPD6781	Approved
0.7049	Intermediate Similarity	NPD6782	Approved
0.7048	Intermediate Similarity	NPD7768	Phase 2
0.7044	Intermediate Similarity	NPD5058	Phase 3
0.7041	Intermediate Similarity	NPD6232	Discontinued
0.7039	Intermediate Similarity	NPD4062	Phase 3
0.7034	Intermediate Similarity	NPD5125	Phase 3
0.7034	Intermediate Similarity	NPD5126	Approved
0.7019	Intermediate Similarity	NPD1512	Approved
0.7018	Intermediate Similarity	NPD7473	Discontinued
0.7016	Intermediate Similarity	NPD7930	Approved
0.7012	Intermediate Similarity	NPD6385	Approved
0.7012	Intermediate Similarity	NPD6386	Approved
0.7007	Intermediate Similarity	NPD9269	Phase 2
0.7007	Intermediate Similarity	NPD1481	Phase 2
0.7006	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7584	Approved
0.6984	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7874	Approved
0.6957	Remote Similarity	NPD2533	Approved
0.6957	Remote Similarity	NPD2532	Approved
0.6957	Remote Similarity	NPD2534	Approved
0.6948	Remote Similarity	NPD4340	Discontinued
0.6947	Remote Similarity	NPD7783	Phase 2
0.6947	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3787	Discontinued
0.6939	Remote Similarity	NPD1535	Discovery
0.6936	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD7697	Approved
0.6935	Remote Similarity	NPD7696	Phase 3
0.6935	Remote Similarity	NPD7698	Approved
0.6931	Remote Similarity	NPD8151	Discontinued
0.6923	Remote Similarity	NPD4308	Phase 3
0.6923	Remote Similarity	NPD5494	Approved
0.6923	Remote Similarity	NPD3748	Approved
0.6918	Remote Similarity	NPD8166	Discontinued
0.6914	Remote Similarity	NPD6273	Approved
0.6913	Remote Similarity	NPD3225	Approved
0.6906	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6213	Phase 3
0.6906	Remote Similarity	NPD6212	Phase 3
0.6898	Remote Similarity	NPD7870	Phase 2
0.6898	Remote Similarity	NPD7871	Phase 2
0.6897	Remote Similarity	NPD1894	Discontinued
0.6892	Remote Similarity	NPD1608	Approved
0.6892	Remote Similarity	NPD3972	Approved
0.689	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD9494	Approved
0.6883	Remote Similarity	NPD943	Approved
0.6882	Remote Similarity	NPD6823	Phase 2
0.6878	Remote Similarity	NPD7701	Phase 2
0.6867	Remote Similarity	NPD2797	Approved
0.6863	Remote Similarity	NPD3268	Approved
0.6863	Remote Similarity	NPD2313	Discontinued
0.6855	Remote Similarity	NPD1652	Phase 2
0.6849	Remote Similarity	NPD9268	Approved
0.6835	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2344	Approved
0.6835	Remote Similarity	NPD2353	Approved
0.6832	Remote Similarity	NPD7236	Approved
0.6824	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2798	Approved
0.6815	Remote Similarity	NPD2799	Discontinued
0.6815	Remote Similarity	NPD1238	Approved
0.6813	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8407	Phase 2
0.6797	Remote Similarity	NPD3027	Phase 3
0.6797	Remote Similarity	NPD7095	Approved
0.6795	Remote Similarity	NPD6653	Approved
0.6793	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3226	Approved
0.6786	Remote Similarity	NPD5353	Approved
0.6784	Remote Similarity	NPD8127	Discontinued
0.6784	Remote Similarity	NPD6959	Discontinued
0.6779	Remote Similarity	NPD9717	Approved
0.6774	Remote Similarity	NPD1613	Approved
0.6774	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5404	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