NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	468.16
Volume:	438.352
LogP:	0.538
LogD:	0.543
LogS:	-2.26
# Rotatable Bonds:	6
TPSA:	175.37
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.292
Synthetic Accessibility Score:	4.71
Fsp3:	0.591
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-6.169
MDCK Permeability:	8.41056535136886e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.276
Human Intestinal Absorption (HIA):	0.854
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.245
Plasma Protein Binding (PPB):	44.022186279296875%
Volume Distribution (VD):	0.399
Pgp-substrate:	37.263916015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.141
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.435
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.111
CYP3A4-inhibitor:	0.061
CYP3A4-substrate:	0.071

ADMET: Excretion

Clearance (CL):	1.448
Half-life (T1/2):	0.851

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.158
Drug-inuced Liver Injury (DILI):	0.499
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.049
Carcinogencity:	0.868
Eye Corrosion:	0.003
Eye Irritation:	0.015
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: NPC478234

Natural Product ID:	NPC478234
*Common Name:**	6-O-(4-hydroxybenzoyl)ajugol
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MYLAQALEHHPXFU-HQFICVKKSA-N
Standard InCHI:	InChI=1S/C22H28O11/c1-22(29)8-13(31-19(28)10-2-4-11(24)5-3-10)12-6-7-30-20(15(12)22)33-21-18(27)17(26)16(25)14(9-23)32-21/h2-7,12-18,20-21,23-27,29H,8-9H2,1H3/t12-,13+,14?,15+,16?,17?,18-,20-,21-,22-/m0/s1
SMILES:	[H][C@]12[C@H](O[C@@H]3OC(CO)C(O)C(O)[C@@H]3O)OC=C[C@@]1([H])[C@H](OC(=O)C1=CC=C(O)C=C1)C[C@]2(C)O
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 NPC478234 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	311
0.1-0.2	1128
0.2-0.3	2746
0.3-0.4	5940
0.4-0.5	10823
0.5-0.6	8084
0.6-0.7	10334
0.7-0.8	3115
0.8-0.85	136
0.85-0.9	55
0.9-0.95	22
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC478236
0.9722	High Similarity	NPC158546
0.9722	High Similarity	NPC289021
0.9655	High Similarity	NPC194705
0.9507	High Similarity	NPC77922
0.9507	High Similarity	NPC473281
0.9392	High Similarity	NPC478232
0.9388	High Similarity	NPC478235
0.9384	High Similarity	NPC240592
0.9384	High Similarity	NPC117346
0.9324	High Similarity	NPC229354
0.931	High Similarity	NPC473149
0.9216	High Similarity	NPC476011
0.9211	High Similarity	NPC138993
0.9184	High Similarity	NPC96599
0.9155	High Similarity	NPC49597
0.9103	High Similarity	NPC296659
0.9103	High Similarity	NPC202391
0.9085	High Similarity	NPC474936
0.9038	High Similarity	NPC130730
0.9038	High Similarity	NPC301910
0.9032	High Similarity	NPC109990
0.9021	High Similarity	NPC31745
0.9021	High Similarity	NPC220936
0.9013	High Similarity	NPC475378
0.8973	High Similarity	NPC184464
0.8973	High Similarity	NPC251062
0.8968	High Similarity	NPC206815
0.8968	High Similarity	NPC145847
0.8936	High Similarity	NPC114116
0.8933	High Similarity	NPC474620
0.8933	High Similarity	NPC475379
0.8926	High Similarity	NPC161955
0.8904	High Similarity	NPC263397
0.8904	High Similarity	NPC237872
0.8904	High Similarity	NPC302286
0.8904	High Similarity	NPC88754
0.8904	High Similarity	NPC186296
0.8904	High Similarity	NPC116104
0.8904	High Similarity	NPC478250
0.8897	High Similarity	NPC137501
0.8897	High Similarity	NPC7518
0.8897	High Similarity	NPC159387
0.8897	High Similarity	NPC46644
0.8897	High Similarity	NPC154262
0.8851	High Similarity	NPC474268
0.8851	High Similarity	NPC475539
0.8851	High Similarity	NPC119773
0.8851	High Similarity	NPC143246
0.8831	High Similarity	NPC187205
0.8824	High Similarity	NPC475484
0.8805	High Similarity	NPC21956
0.8797	High Similarity	NPC282551
0.8784	High Similarity	NPC475528
0.8776	High Similarity	NPC152796
0.8776	High Similarity	NPC293154
0.8776	High Similarity	NPC475213
0.8774	High Similarity	NPC179914
0.875	High Similarity	NPC471345
0.8733	High Similarity	NPC189631
0.8725	High Similarity	NPC37838
0.8716	High Similarity	NPC63304
0.8716	High Similarity	NPC478240
0.8662	High Similarity	NPC254819
0.8639	High Similarity	NPC80098
0.8621	High Similarity	NPC472132
0.8611	High Similarity	NPC169398
0.86	High Similarity	NPC473867
0.86	High Similarity	NPC291153
0.8599	High Similarity	NPC208676
0.8599	High Similarity	NPC130489
0.859	High Similarity	NPC329997
0.858	High Similarity	NPC470685
0.8571	High Similarity	NPC257847
0.8562	High Similarity	NPC269914
0.8562	High Similarity	NPC478249
0.8543	High Similarity	NPC18789
0.8542	High Similarity	NPC322503
0.8542	High Similarity	NPC470143
0.8497	Intermediate Similarity	NPC147224
0.8497	Intermediate Similarity	NPC182350
0.8497	Intermediate Similarity	NPC35097
0.8487	Intermediate Similarity	NPC308178
0.8477	Intermediate Similarity	NPC473147
0.8477	Intermediate Similarity	NPC212808
0.8467	Intermediate Similarity	NPC194938
0.8452	Intermediate Similarity	NPC229548
0.8452	Intermediate Similarity	NPC478241
0.8452	Intermediate Similarity	NPC89693
0.8435	Intermediate Similarity	NPC170718
0.8435	Intermediate Similarity	NPC101686
0.8435	Intermediate Similarity	NPC65262
0.8435	Intermediate Similarity	NPC469364
0.8389	Intermediate Similarity	NPC79908
0.8387	Intermediate Similarity	NPC203664
0.8385	Intermediate Similarity	NPC180586
0.8377	Intermediate Similarity	NPC69367
0.8366	Intermediate Similarity	NPC120728
0.8354	Intermediate Similarity	NPC49173
0.8354	Intermediate Similarity	NPC475663
0.8354	Intermediate Similarity	NPC4747
0.8354	Intermediate Similarity	NPC226759
0.8354	Intermediate Similarity	NPC104275
0.8354	Intermediate Similarity	NPC286919
0.8344	Intermediate Similarity	NPC172920
0.8344	Intermediate Similarity	NPC471028
0.8344	Intermediate Similarity	NPC156624
0.8333	Intermediate Similarity	NPC65833
0.8313	Intermediate Similarity	NPC117943
0.8313	Intermediate Similarity	NPC477627
0.8313	Intermediate Similarity	NPC293568
0.831	Intermediate Similarity	NPC276047
0.831	Intermediate Similarity	NPC267733
0.8303	Intermediate Similarity	NPC195972
0.8302	Intermediate Similarity	NPC469384
0.8298	Intermediate Similarity	NPC145287
0.8289	Intermediate Similarity	NPC210330
0.828	Intermediate Similarity	NPC472127
0.828	Intermediate Similarity	NPC194095
0.828	Intermediate Similarity	NPC327032
0.828	Intermediate Similarity	NPC472128
0.828	Intermediate Similarity	NPC191046
0.8278	Intermediate Similarity	NPC242756
0.8276	Intermediate Similarity	NPC475824
0.8276	Intermediate Similarity	NPC281798
0.8269	Intermediate Similarity	NPC134905
0.8269	Intermediate Similarity	NPC36130
0.8258	Intermediate Similarity	NPC87630
0.8258	Intermediate Similarity	NPC116292
0.8258	Intermediate Similarity	NPC179128
0.8258	Intermediate Similarity	NPC267469
0.8252	Intermediate Similarity	NPC106677
0.8243	Intermediate Similarity	NPC294470
0.8235	Intermediate Similarity	NPC474044
0.8235	Intermediate Similarity	NPC208293
0.8228	Intermediate Similarity	NPC10205
0.8217	Intermediate Similarity	NPC157898
0.8212	Intermediate Similarity	NPC31081
0.8212	Intermediate Similarity	NPC245219
0.8212	Intermediate Similarity	NPC296643
0.8205	Intermediate Similarity	NPC140151
0.8194	Intermediate Similarity	NPC111785
0.8194	Intermediate Similarity	NPC92117
0.8182	Intermediate Similarity	NPC471157
0.8182	Intermediate Similarity	NPC252114
0.8176	Intermediate Similarity	NPC478248
0.8176	Intermediate Similarity	NPC212729
0.8176	Intermediate Similarity	NPC471405
0.817	Intermediate Similarity	NPC108455
0.816	Intermediate Similarity	NPC265600
0.816	Intermediate Similarity	NPC294722
0.8156	Intermediate Similarity	NPC52097
0.8153	Intermediate Similarity	NPC469456
0.8153	Intermediate Similarity	NPC134819
0.8151	Intermediate Similarity	NPC478255
0.8151	Intermediate Similarity	NPC225384
0.8151	Intermediate Similarity	NPC246869
0.8151	Intermediate Similarity	NPC138777
0.8148	Intermediate Similarity	NPC41009
0.8146	Intermediate Similarity	NPC51181
0.8141	Intermediate Similarity	NPC104172
0.8141	Intermediate Similarity	NPC88886
0.8141	Intermediate Similarity	NPC162569
0.8141	Intermediate Similarity	NPC35160
0.8138	Intermediate Similarity	NPC253595
0.8137	Intermediate Similarity	NPC478265
0.8129	Intermediate Similarity	NPC120621
0.8129	Intermediate Similarity	NPC248257
0.8125	Intermediate Similarity	NPC471882
0.8125	Intermediate Similarity	NPC472860
0.8125	Intermediate Similarity	NPC35288
0.8125	Intermediate Similarity	NPC173150
0.8125	Intermediate Similarity	NPC43638
0.8125	Intermediate Similarity	NPC45224
0.8125	Intermediate Similarity	NPC133984
0.8125	Intermediate Similarity	NPC288416
0.8125	Intermediate Similarity	NPC156692
0.8125	Intermediate Similarity	NPC471881
0.8121	Intermediate Similarity	NPC27721
0.8112	Intermediate Similarity	NPC126991
0.8112	Intermediate Similarity	NPC83218
0.811	Intermediate Similarity	NPC469396
0.811	Intermediate Similarity	NPC88176
0.811	Intermediate Similarity	NPC149002
0.811	Intermediate Similarity	NPC469458
0.811	Intermediate Similarity	NPC469459
0.811	Intermediate Similarity	NPC469419
0.8105	Intermediate Similarity	NPC229036
0.8101	Intermediate Similarity	NPC137813
0.8098	Intermediate Similarity	NPC120012
0.8098	Intermediate Similarity	NPC161151
0.8092	Intermediate Similarity	NPC284957
0.8089	Intermediate Similarity	NPC191154
0.8085	Intermediate Similarity	NPC11724
0.8082	Intermediate Similarity	NPC17567
0.8077	Intermediate Similarity	NPC75945
0.8075	Intermediate Similarity	NPC289811
0.8075	Intermediate Similarity	NPC160780
0.8069	Intermediate Similarity	NPC225307
0.8067	Intermediate Similarity	NPC475195

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 NPC478234 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	723
0.2-0.3	1653
0.3-0.4	2686
0.4-0.5	2259
0.5-0.6	1161
0.6-0.7	363
0.7-0.8	47
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8758	High Similarity	NPD7685	Pre-registration
0.7901	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD9545	Approved
0.7742	Intermediate Similarity	NPD4628	Phase 3
0.7662	Intermediate Similarity	NPD7266	Discontinued
0.758	Intermediate Similarity	NPD6190	Approved
0.7568	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4380	Phase 2
0.7529	Intermediate Similarity	NPD3818	Discontinued
0.7486	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7054	Approved
0.7485	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD230	Phase 1
0.7442	Intermediate Similarity	NPD7472	Approved
0.7414	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD6797	Phase 2
0.7375	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3764	Approved
0.7365	Intermediate Similarity	NPD7075	Discontinued
0.7356	Intermediate Similarity	NPD7251	Discontinued
0.7356	Intermediate Similarity	NPD6559	Discontinued
0.7341	Intermediate Similarity	NPD7074	Phase 3
0.7337	Intermediate Similarity	NPD7199	Phase 2
0.7333	Intermediate Similarity	NPD6801	Discontinued
0.7326	Intermediate Similarity	NPD7799	Discontinued
0.7314	Intermediate Similarity	NPD7808	Phase 3
0.7305	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1653	Approved
0.729	Intermediate Similarity	NPD6653	Approved
0.7289	Intermediate Similarity	NPD8455	Phase 2
0.7278	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7458	Discontinued
0.7239	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5647	Approved
0.7215	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6002	Phase 3
0.7215	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6004	Phase 3
0.7215	Intermediate Similarity	NPD6005	Phase 3
0.7197	Intermediate Similarity	NPD7033	Discontinued
0.7188	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6273	Approved
0.7175	Intermediate Similarity	NPD8312	Approved
0.7175	Intermediate Similarity	NPD8313	Approved
0.717	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6799	Approved
0.7151	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5403	Approved
0.7126	Intermediate Similarity	NPD7228	Approved
0.7126	Intermediate Similarity	NPD37	Approved
0.7118	Intermediate Similarity	NPD6234	Discontinued
0.7114	Intermediate Similarity	NPD1091	Approved
0.7101	Intermediate Similarity	NPD4965	Approved
0.7101	Intermediate Similarity	NPD4966	Approved
0.7101	Intermediate Similarity	NPD4967	Phase 2
0.7099	Intermediate Similarity	NPD7236	Approved
0.7066	Intermediate Similarity	NPD7411	Suspended
0.7063	Intermediate Similarity	NPD1549	Phase 2
0.7041	Intermediate Similarity	NPD3817	Phase 2
0.7039	Intermediate Similarity	NPD6362	Approved
0.7024	Intermediate Similarity	NPD1934	Approved
0.7021	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD5401	Approved
0.7006	Intermediate Similarity	NPD6599	Discontinued
0.7006	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5844	Phase 1
0.6988	Remote Similarity	NPD7239	Suspended
0.6987	Remote Similarity	NPD6233	Phase 2
0.6982	Remote Similarity	NPD5761	Phase 2
0.6982	Remote Similarity	NPD7819	Suspended
0.6982	Remote Similarity	NPD5760	Phase 2
0.6982	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1510	Phase 2
0.6975	Remote Similarity	NPD3750	Approved
0.6941	Remote Similarity	NPD5402	Approved
0.6941	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD9493	Approved
0.6936	Remote Similarity	NPD8127	Discontinued
0.6923	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7097	Phase 1
0.6914	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6166	Phase 2
0.691	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7028	Phase 2
0.6899	Remote Similarity	NPD1933	Approved
0.6895	Remote Similarity	NPD7435	Discontinued
0.6888	Remote Similarity	NPD7930	Approved
0.6882	Remote Similarity	NPD2801	Approved
0.6879	Remote Similarity	NPD6663	Approved
0.6872	Remote Similarity	NPD6765	Approved
0.6872	Remote Similarity	NPD6764	Approved
0.6868	Remote Similarity	NPD8150	Discontinued
0.6868	Remote Similarity	NPD8434	Phase 2
0.6859	Remote Similarity	NPD8319	Approved
0.6859	Remote Similarity	NPD8320	Phase 1
0.6859	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5736	Approved
0.6839	Remote Similarity	NPD9494	Approved
0.6839	Remote Similarity	NPD7585	Approved
0.6835	Remote Similarity	NPD1240	Approved
0.6832	Remote Similarity	NPD2935	Discontinued
0.6832	Remote Similarity	NPD2796	Approved
0.6828	Remote Similarity	NPD6534	Approved
0.6828	Remote Similarity	NPD6535	Approved
0.6825	Remote Similarity	NPD6782	Approved
0.6825	Remote Similarity	NPD6779	Approved
0.6825	Remote Similarity	NPD6777	Approved
0.6825	Remote Similarity	NPD6781	Approved
0.6825	Remote Similarity	NPD6780	Approved
0.6825	Remote Similarity	NPD6778	Approved
0.6825	Remote Similarity	NPD6776	Approved
0.6823	Remote Similarity	NPD7999	Approved
0.6818	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD2797	Approved
0.6815	Remote Similarity	NPD6798	Discontinued
0.6815	Remote Similarity	NPD3268	Approved
0.681	Remote Similarity	NPD1652	Phase 2
0.6807	Remote Similarity	NPD2532	Approved
0.6807	Remote Similarity	NPD2534	Approved
0.6807	Remote Similarity	NPD2533	Approved
0.6806	Remote Similarity	NPD7497	Discontinued
0.6802	Remote Similarity	NPD3882	Suspended
0.68	Remote Similarity	NPD6232	Discontinued
0.6793	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5124	Phase 1
0.679	Remote Similarity	NPD5763	Approved
0.679	Remote Similarity	NPD5762	Approved
0.6788	Remote Similarity	NPD7583	Approved
0.6784	Remote Similarity	NPD1465	Phase 2
0.678	Remote Similarity	NPD7473	Discontinued
0.6778	Remote Similarity	NPD7240	Approved
0.6774	Remote Similarity	NPD2798	Approved
0.6768	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3749	Approved
0.6753	Remote Similarity	NPD1876	Approved
0.675	Remote Similarity	NPD1607	Approved
0.6747	Remote Similarity	NPD1511	Approved
0.6744	Remote Similarity	NPD5353	Approved
0.6742	Remote Similarity	NPD3751	Discontinued
0.6732	Remote Similarity	NPD1608	Approved
0.6732	Remote Similarity	NPD9717	Approved
0.6732	Remote Similarity	NPD9269	Phase 2
0.6728	Remote Similarity	NPD1551	Phase 2
0.6727	Remote Similarity	NPD2354	Approved
0.6727	Remote Similarity	NPD3887	Approved
0.6721	Remote Similarity	NPD6784	Approved
0.6721	Remote Similarity	NPD6785	Approved
0.672	Remote Similarity	NPD7700	Phase 2
0.672	Remote Similarity	NPD7699	Phase 2
0.6712	Remote Similarity	NPD969	Suspended
0.671	Remote Similarity	NPD3094	Phase 2
0.671	Remote Similarity	NPD1203	Approved
0.6705	Remote Similarity	NPD7058	Phase 2
0.6705	Remote Similarity	NPD7768	Phase 2
0.6705	Remote Similarity	NPD7057	Phase 3
0.6704	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7584	Approved
0.6689	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6832	Phase 2
0.6686	Remote Similarity	NPD5494	Approved
0.6684	Remote Similarity	NPD7874	Approved
0.6684	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD4062	Phase 3
0.6667	Remote Similarity	NPD1512	Approved
0.6667	Remote Similarity	NPD4308	Phase 3
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD1358	Approved
0.6667	Remote Similarity	NPD2799	Discontinued
0.665	Remote Similarity	NPD7783	Phase 2
0.665	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3455	Phase 2
0.6647	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3225	Approved
0.6633	Remote Similarity	NPD8151	Discontinued
0.6632	Remote Similarity	NPD7698	Approved
0.6632	Remote Similarity	NPD7697	Approved
0.6632	Remote Similarity	NPD7696	Phase 3
0.6625	Remote Similarity	NPD4140	Approved
0.6624	Remote Similarity	NPD2861	Phase 2
0.6623	Remote Similarity	NPD3972	Approved
0.661	Remote Similarity	NPD3787	Discontinued
0.6598	Remote Similarity	NPD7870	Phase 2
0.6598	Remote Similarity	NPD7871	Phase 2
0.6597	Remote Similarity	NPD3134	Approved
0.6596	Remote Similarity	NPD6212	Phase 3
0.6596	Remote Similarity	NPD6213	Phase 3
0.6596	Remote Similarity	NPD6214	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