NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	508.16
Volume:	470.542
LogP:	0.588
LogD:	0.222
LogS:	-2.731
# Rotatable Bonds:	8
TPSA:	187.9
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.141
Synthetic Accessibility Score:	5.001
Fsp3:	0.542
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:	-6.317
MDCK Permeability:	7.13482077117078e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.735
Human Intestinal Absorption (HIA):	0.773
20% Bioavailability (F20%):	0.91
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.162
Plasma Protein Binding (PPB):	66.23603057861328%
Volume Distribution (VD):	0.439
Pgp-substrate:	28.694835662841797%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.052
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.075
CYP3A4-substrate:	0.1

ADMET: Excretion

Clearance (CL):	1.725
Half-life (T1/2):	0.888

ADMET: Toxicity

hERG Blockers:	0.112
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.081
Rat Oral Acute Toxicity:	0.469
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.835
Carcinogencity:	0.462
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC46644

Natural Product ID:	NPC46644
*Common Name:**	Specioside
IUPAC Name:	[(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:	Specioside
Standard InCHIKey:	SKNVKBJSSSJNCI-UIBFFPKISA-N
Standard InCHI:	InChI=1S/C24H28O12/c25-9-14-17(29)18(30)19(31)23(33-14)35-22-16-13(7-8-32-22)20(21-24(16,10-26)36-21)34-15(28)6-3-11-1-4-12(27)5-2-11/h1-8,13-14,16-23,25-27,29-31H,9-10H2/b6-3+/t13-,14-,16-,17-,18+,19-,20+,21+,22+,23+,24-/m1/s1
SMILES:	C1=CO[C@H]([C@H]2[C@@H]1[C@@H]([C@H]3[C@@]2(O3)CO)OC(=O)/C=C/C4=CC=C(C=C4)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11948661
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

*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

Activity Type	# Activity
IC50	1
Kd	1

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT992	Organism	Entamoeba histolytica	Entamoeba histolytica	IC50	=	0.1981	ug/ml	DOI[10.1007/s00044-011-9767-1]
NPT918	Individual Protein	Heat shock protein HSP 90-alpha	Homo sapiens	Kd	=	26	nM	PMID[23362862]

☑ 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 NPC46644 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	332
0.1-0.2	1272
0.2-0.3	3087
0.3-0.4	7243
0.4-0.5	10696
0.5-0.6	11947
0.6-0.7	7033
0.7-0.8	953
0.8-0.85	78
0.85-0.9	34
0.9-0.95	18
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC49597
0.9568	High Similarity	NPC18789
0.9493	High Similarity	NPC478240
0.9353	High Similarity	NPC184464
0.9353	High Similarity	NPC251062
0.9323	High Similarity	NPC475824
0.9281	High Similarity	NPC88754
0.9281	High Similarity	NPC116104
0.9281	High Similarity	NPC302286
0.9281	High Similarity	NPC237872
0.9281	High Similarity	NPC263397
0.9275	High Similarity	NPC154262
0.9275	High Similarity	NPC137501
0.9275	High Similarity	NPC7518
0.9275	High Similarity	NPC159387
0.9236	High Similarity	NPC194705
0.9179	High Similarity	NPC254819
0.9172	High Similarity	NPC478241
0.9172	High Similarity	NPC229548
0.9172	High Similarity	NPC89693
0.9143	High Similarity	NPC186296
0.9085	High Similarity	NPC37838
0.9028	High Similarity	NPC478236
0.9023	High Similarity	NPC175333
0.8986	High Similarity	NPC475378
0.8966	High Similarity	NPC117346
0.8966	High Similarity	NPC240592
0.8966	High Similarity	NPC147224
0.8912	High Similarity	NPC229354
0.8904	High Similarity	NPC478249
0.8904	High Similarity	NPC269914
0.8897	High Similarity	NPC96599
0.8897	High Similarity	NPC478234
0.8859	High Similarity	NPC478248
0.8851	High Similarity	NPC478232
0.8828	High Similarity	NPC308178
0.8811	High Similarity	NPC296659
0.8811	High Similarity	NPC202391
0.8808	High Similarity	NPC138993
0.8808	High Similarity	NPC478265
0.8806	High Similarity	NPC276047
0.8806	High Similarity	NPC267733
0.8776	High Similarity	NPC289021
0.8776	High Similarity	NPC158546
0.8723	High Similarity	NPC220936
0.8723	High Similarity	NPC31745
0.869	High Similarity	NPC474234
0.8667	High Similarity	NPC252114
0.8657	High Similarity	NPC145287
0.8647	High Similarity	NPC52097
0.8623	High Similarity	NPC478255
0.8613	High Similarity	NPC253595
0.8603	High Similarity	NPC106677
0.8603	High Similarity	NPC288416
0.8593	High Similarity	NPC126991
0.8593	High Similarity	NPC83218
0.8591	High Similarity	NPC478235
0.8582	High Similarity	NPC472132
0.8571	High Similarity	NPC11724
0.8552	High Similarity	NPC77922
0.8552	High Similarity	NPC473281
0.8543	High Similarity	NPC475484
0.854	High Similarity	NPC225307
0.8529	High Similarity	NPC471157
0.8526	High Similarity	NPC130730
0.8526	High Similarity	NPC301910
0.8523	High Similarity	NPC475379
0.8496	Intermediate Similarity	NPC476872
0.8493	Intermediate Similarity	NPC475528
0.8487	Intermediate Similarity	NPC478266
0.8483	Intermediate Similarity	NPC293154
0.8467	Intermediate Similarity	NPC173150
0.8467	Intermediate Similarity	NPC35288
0.8467	Intermediate Similarity	NPC471882
0.8467	Intermediate Similarity	NPC471881
0.8467	Intermediate Similarity	NPC156692
0.8467	Intermediate Similarity	NPC45224
0.8452	Intermediate Similarity	NPC206815
0.844	Intermediate Similarity	NPC169398
0.8435	Intermediate Similarity	NPC474268
0.8435	Intermediate Similarity	NPC475539
0.8435	Intermediate Similarity	NPC143246
0.8435	Intermediate Similarity	NPC119773
0.8429	Intermediate Similarity	NPC473924
0.8425	Intermediate Similarity	NPC63304
0.8394	Intermediate Similarity	NPC61181
0.838	Intermediate Similarity	NPC476870
0.8369	Intermediate Similarity	NPC254398
0.8357	Intermediate Similarity	NPC225384
0.8357	Intermediate Similarity	NPC46137
0.8357	Intermediate Similarity	NPC219677
0.8357	Intermediate Similarity	NPC246869
0.8357	Intermediate Similarity	NPC235294
0.8357	Intermediate Similarity	NPC138777
0.8356	Intermediate Similarity	NPC475213
0.8356	Intermediate Similarity	NPC152796
0.8345	Intermediate Similarity	NPC477293
0.8345	Intermediate Similarity	NPC477294
0.8345	Intermediate Similarity	NPC229784
0.8333	Intermediate Similarity	NPC171134
0.8333	Intermediate Similarity	NPC103533
0.8333	Intermediate Similarity	NPC476011
0.8333	Intermediate Similarity	NPC328273
0.8333	Intermediate Similarity	NPC321184
0.8333	Intermediate Similarity	NPC321638
0.831	Intermediate Similarity	NPC287597
0.831	Intermediate Similarity	NPC34293
0.831	Intermediate Similarity	NPC886
0.8299	Intermediate Similarity	NPC194938
0.8298	Intermediate Similarity	NPC473285
0.8273	Intermediate Similarity	NPC232880
0.8264	Intermediate Similarity	NPC469364
0.8264	Intermediate Similarity	NPC65262
0.8264	Intermediate Similarity	NPC101686
0.8258	Intermediate Similarity	NPC179914
0.8255	Intermediate Similarity	NPC473149
0.8239	Intermediate Similarity	NPC28637
0.8227	Intermediate Similarity	NPC281798
0.8214	Intermediate Similarity	NPC295970
0.8212	Intermediate Similarity	NPC69367
0.8212	Intermediate Similarity	NPC35097
0.8205	Intermediate Similarity	NPC474936
0.8201	Intermediate Similarity	NPC476873
0.82	Intermediate Similarity	NPC120728
0.8194	Intermediate Similarity	NPC166180
0.8188	Intermediate Similarity	NPC473147
0.8182	Intermediate Similarity	NPC471883
0.817	Intermediate Similarity	NPC469699
0.8165	Intermediate Similarity	NPC109990
0.8163	Intermediate Similarity	NPC296643
0.8158	Intermediate Similarity	NPC474620
0.8138	Intermediate Similarity	NPC476376
0.8138	Intermediate Similarity	NPC78363
0.8138	Intermediate Similarity	NPC260425
0.8125	Intermediate Similarity	NPC263829
0.8125	Intermediate Similarity	NPC208818
0.8112	Intermediate Similarity	NPC322503
0.8112	Intermediate Similarity	NPC470143
0.8108	Intermediate Similarity	NPC105005
0.8108	Intermediate Similarity	NPC204644
0.8108	Intermediate Similarity	NPC40305
0.8105	Intermediate Similarity	NPC203664
0.8101	Intermediate Similarity	NPC145847
0.8095	Intermediate Similarity	NPC215512
0.8095	Intermediate Similarity	NPC186406
0.8095	Intermediate Similarity	NPC476442
0.8089	Intermediate Similarity	NPC269668
0.8082	Intermediate Similarity	NPC81515
0.8082	Intermediate Similarity	NPC205195
0.8082	Intermediate Similarity	NPC197316
0.8082	Intermediate Similarity	NPC226005
0.8082	Intermediate Similarity	NPC476383
0.8082	Intermediate Similarity	NPC89105
0.8082	Intermediate Similarity	NPC64141
0.8082	Intermediate Similarity	NPC472350
0.8082	Intermediate Similarity	NPC68092
0.8079	Intermediate Similarity	NPC189631
0.8077	Intermediate Similarity	NPC187205
0.8077	Intermediate Similarity	NPC329997
0.8069	Intermediate Similarity	NPC471345
0.8069	Intermediate Similarity	NPC157554
0.8069	Intermediate Similarity	NPC470572
0.8054	Intermediate Similarity	NPC196063
0.8054	Intermediate Similarity	NPC300894
0.8054	Intermediate Similarity	NPC110063
0.8054	Intermediate Similarity	NPC141455
0.8054	Intermediate Similarity	NPC296954
0.8052	Intermediate Similarity	NPC257847
0.8041	Intermediate Similarity	NPC145319
0.8041	Intermediate Similarity	NPC140502
0.8039	Intermediate Similarity	NPC77310
0.8027	Intermediate Similarity	NPC202700
0.8026	Intermediate Similarity	NPC161955
0.8014	Intermediate Similarity	NPC146540
0.8013	Intermediate Similarity	NPC97240
0.7987	Intermediate Similarity	NPC478250
0.7987	Intermediate Similarity	NPC478239
0.7985	Intermediate Similarity	NPC175771
0.7975	Intermediate Similarity	NPC130489
0.7975	Intermediate Similarity	NPC208676
0.7973	Intermediate Similarity	NPC134405
0.7973	Intermediate Similarity	NPC476385
0.7973	Intermediate Similarity	NPC47471
0.7973	Intermediate Similarity	NPC476377
0.797	Intermediate Similarity	NPC313193
0.7963	Intermediate Similarity	NPC21956
0.7961	Intermediate Similarity	NPC169510
0.7959	Intermediate Similarity	NPC100389
0.7959	Intermediate Similarity	NPC220942
0.7956	Intermediate Similarity	NPC476445
0.7956	Intermediate Similarity	NPC476448
0.7956	Intermediate Similarity	NPC469548
0.795	Intermediate Similarity	NPC282551
0.7947	Intermediate Similarity	NPC320734
0.7947	Intermediate Similarity	NPC212808
0.7947	Intermediate Similarity	NPC229505
0.7945	Intermediate Similarity	NPC186418
0.7945	Intermediate Similarity	NPC103409
0.7945	Intermediate Similarity	NPC37468
0.7933	Intermediate Similarity	NPC292443

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 NPC46644 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	261
0.1-0.2	751
0.2-0.3	1796
0.3-0.4	2957
0.4-0.5	2071
0.5-0.6	1122
0.6-0.7	185
0.7-0.8	6
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD7685	Pre-registration
0.8082	Intermediate Similarity	NPD7266	Discontinued
0.7677	Intermediate Similarity	NPD1653	Approved
0.7394	Intermediate Similarity	NPD1091	Approved
0.729	Intermediate Similarity	NPD6190	Approved
0.7219	Intermediate Similarity	NPD6653	Approved
0.7195	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD3094	Phase 2
0.7032	Intermediate Similarity	NPD5763	Approved
0.7032	Intermediate Similarity	NPD5762	Approved
0.7027	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD8455	Phase 2
0.698	Remote Similarity	NPD2861	Phase 2
0.6978	Remote Similarity	NPD969	Suspended
0.6948	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1652	Phase 2
0.6932	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD5124	Phase 1
0.6923	Remote Similarity	NPD6005	Phase 3
0.6923	Remote Similarity	NPD6002	Phase 3
0.6923	Remote Similarity	NPD6004	Phase 3
0.6923	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3092	Approved
0.6899	Remote Similarity	NPD4628	Phase 3
0.6867	Remote Similarity	NPD5736	Approved
0.6864	Remote Similarity	NPD7199	Phase 2
0.6863	Remote Similarity	NPD4140	Approved
0.686	Remote Similarity	NPD7228	Approved
0.686	Remote Similarity	NPD3818	Discontinued
0.6848	Remote Similarity	NPD37	Approved
0.6846	Remote Similarity	NPD6362	Approved
0.6845	Remote Similarity	NPD6234	Discontinued
0.6842	Remote Similarity	NPD3764	Approved
0.6839	Remote Similarity	NPD7097	Phase 1
0.6829	Remote Similarity	NPD4380	Phase 2
0.6826	Remote Similarity	NPD4966	Approved
0.6826	Remote Similarity	NPD4965	Approved
0.6826	Remote Similarity	NPD4967	Phase 2
0.6818	Remote Similarity	NPD4340	Discontinued
0.6813	Remote Similarity	NPD5058	Phase 3
0.6812	Remote Similarity	NPD1358	Approved
0.68	Remote Similarity	NPD5647	Approved
0.68	Remote Similarity	NPD6559	Discontinued
0.6781	Remote Similarity	NPD5126	Approved
0.6781	Remote Similarity	NPD5125	Phase 3
0.677	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD9545	Approved
0.6753	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3134	Approved
0.6724	Remote Similarity	NPD7054	Approved
0.6724	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD8313	Approved
0.6723	Remote Similarity	NPD8312	Approved
0.671	Remote Similarity	NPD5735	Approved
0.671	Remote Similarity	NPD6355	Discontinued
0.6689	Remote Similarity	NPD422	Phase 1
0.6689	Remote Similarity	NPD3705	Approved
0.6688	Remote Similarity	NPD6663	Approved
0.6688	Remote Similarity	NPD7033	Discontinued
0.6687	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7472	Approved
0.6667	Remote Similarity	NPD3027	Phase 3
0.6667	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD7799	Discontinued
0.6648	Remote Similarity	NPD6797	Phase 2
0.6645	Remote Similarity	NPD3620	Phase 2
0.6645	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4060	Phase 1
0.6645	Remote Similarity	NPD1613	Approved
0.6644	Remote Similarity	NPD3091	Approved
0.6627	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7028	Phase 2
0.6625	Remote Similarity	NPD6674	Discontinued
0.661	Remote Similarity	NPD7251	Discontinued
0.6603	Remote Similarity	NPD230	Phase 1
0.6601	Remote Similarity	NPD4908	Phase 1
0.6599	Remote Similarity	NPD1357	Approved
0.6591	Remote Similarity	NPD7074	Phase 3
0.6588	Remote Similarity	NPD7075	Discontinued
0.6585	Remote Similarity	NPD6273	Approved
0.6584	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD6233	Phase 2
0.6577	Remote Similarity	NPD1610	Phase 2
0.6573	Remote Similarity	NPD7808	Phase 3
0.6571	Remote Similarity	NPD3751	Discontinued
0.6562	Remote Similarity	NPD2424	Discontinued
0.6557	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7157	Approved
0.6545	Remote Similarity	NPD5403	Approved
0.6531	Remote Similarity	NPD7741	Discontinued
0.6524	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD7240	Approved
0.6516	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6685	Approved
0.649	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD7503	Approved
0.6481	Remote Similarity	NPD8166	Discontinued
0.6481	Remote Similarity	NPD3750	Approved
0.6481	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD5960	Phase 3
0.6478	Remote Similarity	NPD5588	Approved
0.6471	Remote Similarity	NPD5402	Approved
0.6467	Remote Similarity	NPD7458	Discontinued
0.6458	Remote Similarity	NPD7843	Approved
0.6452	Remote Similarity	NPD7095	Approved
0.645	Remote Similarity	NPD6801	Discontinued
0.6447	Remote Similarity	NPD3225	Approved
0.6446	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD3095	Discontinued
0.6437	Remote Similarity	NPD3787	Discontinued
0.6424	Remote Similarity	NPD5401	Approved
0.6424	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD1548	Phase 1
0.6415	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4538	Approved
0.6415	Remote Similarity	NPD4536	Approved
0.6412	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6798	Discontinued
0.6408	Remote Similarity	NPD2684	Approved
0.6405	Remote Similarity	NPD2797	Approved
0.6403	Remote Similarity	NPD5765	Approved
0.64	Remote Similarity	NPD3496	Discontinued
0.6396	Remote Similarity	NPD7930	Approved
0.6395	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6912	Phase 3
0.6387	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4624	Approved
0.6358	Remote Similarity	NPD5958	Discontinued
0.6358	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6352	Remote Similarity	NPD6353	Approved
0.634	Remote Similarity	NPD8651	Approved
0.6338	Remote Similarity	NPD290	Approved
0.6333	Remote Similarity	NPD4626	Approved
0.6333	Remote Similarity	NPD4059	Approved
0.6327	Remote Similarity	NPD4198	Discontinued
0.6323	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7999	Approved
0.6319	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD3268	Approved
0.6304	Remote Similarity	NPD3020	Approved
0.6303	Remote Similarity	NPD7236	Approved
0.6299	Remote Similarity	NPD987	Approved
0.628	Remote Similarity	NPD4110	Phase 3
0.628	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD3817	Phase 2
0.6278	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4749	Approved
0.6275	Remote Similarity	NPD5327	Phase 3
0.6273	Remote Similarity	NPD4108	Discontinued
0.6273	Remote Similarity	NPD1510	Phase 2
0.6267	Remote Similarity	NPD5585	Approved
0.6267	Remote Similarity	NPD5691	Approved
0.6266	Remote Similarity	NPD4062	Phase 3
0.6265	Remote Similarity	NPD6799	Approved
0.6258	Remote Similarity	NPD1549	Phase 2
0.6257	Remote Similarity	NPD5844	Phase 1
0.6257	Remote Similarity	NPD1934	Approved
0.625	Remote Similarity	NPD3022	Approved
0.625	Remote Similarity	NPD3021	Approved
0.6242	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD2935	Discontinued
0.6235	Remote Similarity	NPD1551	Phase 2
0.6233	Remote Similarity	NPD5535	Approved
0.6228	Remote Similarity	NPD3536	Discontinued
0.6224	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD5761	Phase 2
0.6221	Remote Similarity	NPD7819	Suspended
0.6221	Remote Similarity	NPD5760	Phase 2
0.6221	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7435	Discontinued
0.6218	Remote Similarity	NPD7497	Discontinued
0.6213	Remote Similarity	NPD7239	Suspended
0.6209	Remote Similarity	NPD7549	Discontinued
0.6199	Remote Similarity	NPD7411	Suspended
0.6199	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD9697	Approved
0.6196	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD1933	Approved
0.6186	Remote Similarity	NPD8320	Phase 1
0.6186	Remote Similarity	NPD8319	Approved
0.6185	Remote Similarity	NPD2415	Discontinued
0.6185	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6166	Phase 2
0.6178	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5808	Clinical (unspecified phase)

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