NPASS Compound

Structure

NPC476011 OpenBabel07101719252D 35 38 0 0 1 0 0 0 0 0999 V2000 4.2923 -0.5219 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 -3.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -0.2128 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 31 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 12 1 0 0 0 0 5 6 2 0 0 0 0 6 32 1 0 0 0 0 7 10 2 0 0 0 0 7 14 1 0 0 0 0 8 13 1 0 0 0 0 8 23 1 0 0 0 0 9 33 1 0 0 0 0 10 20 1 0 0 0 0 11 5 1 6 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 14 2 0 0 0 0 12 24 1 0 0 0 0 13 25 1 1 0 0 0 14 31 1 0 0 0 0 15 9 1 6 0 0 0 15 17 1 0 0 0 0 15 34 1 0 0 0 0 16 21 1 0 0 0 0 16 23 1 6 0 0 0 17 18 1 0 0 0 0 17 26 1 1 0 0 0 18 19 1 0 0 0 0 18 27 1 6 0 0 0 19 22 1 0 0 0 0 19 28 1 1 0 0 0 20 29 2 0 0 0 0 20 33 1 0 0 0 0 21 32 1 0 0 0 0 21 35 1 1 0 0 0 22 34 1 0 0 0 0 22 35 1 6 0 0 0 23 1 1 6 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.17
Volume:	464.439
LogP:	0.614
LogD:	0.345
LogS:	-2.708
# Rotatable Bonds:	7
TPSA:	184.6
# H-Bond Aceptor:	12
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.263
Synthetic Accessibility Score:	4.779
Fsp3:	0.609
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.242
MDCK Permeability:	7.601268589496613e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.915
Human Intestinal Absorption (HIA):	0.879
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.23
Plasma Protein Binding (PPB):	42.900794982910156%
Volume Distribution (VD):	0.353
Pgp-substrate:	33.11619567871094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.103
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.264
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.138
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.068

ADMET: Excretion

Clearance (CL):	1.973
Half-life (T1/2):	0.907

ADMET: Toxicity

hERG Blockers:	0.135
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.113
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.075
Skin Sensitization:	0.08
Carcinogencity:	0.878
Eye Corrosion:	0.003
Eye Irritation:	0.026
Respiratory Toxicity:	0.463

Download Data

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

Natural Product: NPC476011

Natural Product ID:	NPC476011
*Common Name:**	6-O-4''-Hydroxy-3''-Methoxybenzoyl Ajugol
IUPAC Name:	[(2R,3S,4S,5R,6S)-6-[[(1S,4aR,5R,7S,7aS)-5,7-dihydroxy-7-methyl-4a,5,6,7a-tetrahydro-1H-cyclopenta[c]pyran-1-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate
Synonyms:
Standard InCHIKey:	UATKLEJGJXQCCG-CLYWGZERSA-N
Standard InCHI:	InChI=1S/C23H30O12/c1-23(30)8-13(25)11-5-6-32-21(16(11)23)35-22-19(28)18(27)17(26)15(34-22)9-33-20(29)10-3-4-12(24)14(7-10)31-2/h3-7,11,13,15-19,21-22,24-28,30H,8-9H2,1-2H3/t11-,13+,15+,16+,17+,18-,19+,21-,22-,23-/m0/s1
SMILES:	CC1(CC(C2C1C(OC=C2)OC3C(C(C(C(O3)COC(=O)C4=CC(=C(C=C4)O)OC)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521494
PubChem CID:	44575707
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO14242	Maytenus laevis	Species	Celastraceae	Eukaryota	bark	Leticia, Colombia	n.a.	PMID[15568791]
NPO14242	Maytenus laevis	Species	Celastraceae	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
Others	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT927	Cell Line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[538498]

☑ 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 NPC476011 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	356
0.1-0.2	1363
0.2-0.3	3112
0.3-0.4	6740
0.4-0.5	10314
0.5-0.6	6837
0.6-0.7	8040
0.7-0.8	5508
0.8-0.85	320
0.85-0.9	86
0.9-0.95	17
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC301910
0.9808	High Similarity	NPC130730
0.974	High Similarity	NPC474936
0.9615	High Similarity	NPC206815
0.9487	High Similarity	NPC138993
0.9437	High Similarity	NPC21956
0.9434	High Similarity	NPC282551
0.9423	High Similarity	NPC179914
0.9221	High Similarity	NPC478249
0.9221	High Similarity	NPC269914
0.9216	High Similarity	NPC478236
0.9216	High Similarity	NPC478234
0.9202	High Similarity	NPC470685
0.9187	High Similarity	NPC109990
0.9167	High Similarity	NPC478232
0.9161	High Similarity	NPC203664
0.913	High Similarity	NPC180586
0.9125	High Similarity	NPC145847
0.9114	High Similarity	NPC226759
0.9108	High Similarity	NPC475484
0.9103	High Similarity	NPC89693
0.9103	High Similarity	NPC478241
0.9103	High Similarity	NPC229548
0.9097	High Similarity	NPC289021
0.9097	High Similarity	NPC158546
0.9045	High Similarity	NPC327032
0.9045	High Similarity	NPC191046
0.9045	High Similarity	NPC194095
0.9038	High Similarity	NPC194705
0.9032	High Similarity	NPC147224
0.9026	High Similarity	NPC308178
0.8994	High Similarity	NPC286919
0.8994	High Similarity	NPC475663
0.8994	High Similarity	NPC187205
0.8961	High Similarity	NPC473149
0.8938	High Similarity	NPC469384
0.8931	High Similarity	NPC471405
0.8917	High Similarity	NPC36130
0.8917	High Similarity	NPC134905
0.891	High Similarity	NPC117346
0.891	High Similarity	NPC240592
0.8896	High Similarity	NPC473867
0.8889	High Similarity	NPC41009
0.8875	High Similarity	NPC472860
0.8875	High Similarity	NPC133984
0.8868	High Similarity	NPC10205
0.8854	High Similarity	NPC475379
0.882	High Similarity	NPC289811
0.882	High Similarity	NPC160780
0.8812	High Similarity	NPC478248
0.8797	High Similarity	NPC289438
0.8797	High Similarity	NPC478235
0.879	High Similarity	NPC205054
0.8766	High Similarity	NPC473281
0.8766	High Similarity	NPC77922
0.8765	High Similarity	NPC239966
0.8765	High Similarity	NPC478265
0.8765	High Similarity	NPC203020
0.8758	High Similarity	NPC1913
0.8742	High Similarity	NPC310661
0.8742	High Similarity	NPC229354
0.8742	High Similarity	NPC157898
0.8742	High Similarity	NPC105827
0.8742	High Similarity	NPC137813
0.8726	High Similarity	NPC478242
0.8726	High Similarity	NPC96599
0.8726	High Similarity	NPC111785
0.8718	High Similarity	NPC18789
0.8712	High Similarity	NPC472859
0.8712	High Similarity	NPC25389
0.8712	High Similarity	NPC311803
0.8704	High Similarity	NPC76211
0.8671	High Similarity	NPC227980
0.8659	High Similarity	NPC33298
0.8659	High Similarity	NPC285108
0.8654	High Similarity	NPC474234
0.865	High Similarity	NPC119125
0.865	High Similarity	NPC166277
0.8642	High Similarity	NPC49173
0.8642	High Similarity	NPC4747
0.8642	High Similarity	NPC104275
0.8639	High Similarity	NPC469438
0.8634	High Similarity	NPC172920
0.8634	High Similarity	NPC156624
0.8625	High Similarity	NPC44730
0.8608	High Similarity	NPC98809
0.8608	High Similarity	NPC476394
0.8606	High Similarity	NPC100420
0.8589	High Similarity	NPC287872
0.8589	High Similarity	NPC74319
0.8581	High Similarity	NPC116104
0.8581	High Similarity	NPC88754
0.8581	High Similarity	NPC302286
0.8581	High Similarity	NPC475213
0.8581	High Similarity	NPC237872
0.8581	High Similarity	NPC152796
0.8581	High Similarity	NPC263397
0.858	High Similarity	NPC316539
0.858	High Similarity	NPC475378
0.858	High Similarity	NPC475299
0.8571	High Similarity	NPC472128
0.8571	High Similarity	NPC472127
0.8562	High Similarity	NPC267091
0.8554	High Similarity	NPC475738
0.8553	High Similarity	NPC69367
0.8544	High Similarity	NPC472969
0.8537	High Similarity	NPC289346
0.8529	High Similarity	NPC169645
0.8529	High Similarity	NPC84482
0.8529	High Similarity	NPC469354
0.8526	High Similarity	NPC202391
0.8526	High Similarity	NPC296659
0.8526	High Similarity	NPC478240
0.8519	High Similarity	NPC38699
0.8509	High Similarity	NPC245615
0.8509	High Similarity	NPC115466
0.8509	High Similarity	NPC61604
0.8509	High Similarity	NPC299706
0.8506	High Similarity	NPC299855
0.8506	High Similarity	NPC96194
0.85	High Similarity	NPC243891
0.85	High Similarity	NPC140151
0.8491	Intermediate Similarity	NPC92117
0.8471	Intermediate Similarity	NPC108455
0.8466	Intermediate Similarity	NPC478266
0.8466	Intermediate Similarity	NPC163635
0.8462	Intermediate Similarity	NPC242756
0.8457	Intermediate Similarity	NPC189704
0.8452	Intermediate Similarity	NPC116745
0.8452	Intermediate Similarity	NPC208818
0.8443	Intermediate Similarity	NPC472131
0.8443	Intermediate Similarity	NPC472130
0.8442	Intermediate Similarity	NPC220936
0.8442	Intermediate Similarity	NPC49597
0.8442	Intermediate Similarity	NPC226005
0.8442	Intermediate Similarity	NPC31745
0.8439	Intermediate Similarity	NPC188217
0.8434	Intermediate Similarity	NPC246024
0.8434	Intermediate Similarity	NPC4013
0.8434	Intermediate Similarity	NPC90905
0.8431	Intermediate Similarity	NPC157554
0.8428	Intermediate Similarity	NPC120621
0.8428	Intermediate Similarity	NPC248257
0.8418	Intermediate Similarity	NPC37838
0.8418	Intermediate Similarity	NPC98356
0.8409	Intermediate Similarity	NPC475121
0.8409	Intermediate Similarity	NPC476067
0.8408	Intermediate Similarity	NPC251062
0.8408	Intermediate Similarity	NPC229036
0.8408	Intermediate Similarity	NPC184464
0.8408	Intermediate Similarity	NPC110063
0.8405	Intermediate Similarity	NPC145425
0.8402	Intermediate Similarity	NPC658
0.8402	Intermediate Similarity	NPC197708
0.8397	Intermediate Similarity	NPC140502
0.8397	Intermediate Similarity	NPC296643
0.8391	Intermediate Similarity	NPC473776
0.8391	Intermediate Similarity	NPC473205
0.8385	Intermediate Similarity	NPC474620
0.8375	Intermediate Similarity	NPC75945
0.8375	Intermediate Similarity	NPC161955
0.8372	Intermediate Similarity	NPC473713
0.8363	Intermediate Similarity	NPC163165
0.8354	Intermediate Similarity	NPC469683
0.8354	Intermediate Similarity	NPC478055
0.8353	Intermediate Similarity	NPC43434
0.8353	Intermediate Similarity	NPC212748
0.8353	Intermediate Similarity	NPC472129
0.8344	Intermediate Similarity	NPC186296
0.8344	Intermediate Similarity	NPC476364
0.8344	Intermediate Similarity	NPC478239
0.8343	Intermediate Similarity	NPC298847
0.8333	Intermediate Similarity	NPC46644
0.8333	Intermediate Similarity	NPC154262
0.8333	Intermediate Similarity	NPC159387
0.8333	Intermediate Similarity	NPC75695
0.8333	Intermediate Similarity	NPC80098
0.8333	Intermediate Similarity	NPC137501
0.8333	Intermediate Similarity	NPC7518
0.8323	Intermediate Similarity	NPC148273
0.8323	Intermediate Similarity	NPC100389
0.8323	Intermediate Similarity	NPC158635
0.8323	Intermediate Similarity	NPC229882
0.8323	Intermediate Similarity	NPC22324
0.8313	Intermediate Similarity	NPC239818
0.8313	Intermediate Similarity	NPC44507
0.8313	Intermediate Similarity	NPC218471
0.8304	Intermediate Similarity	NPC235575
0.8304	Intermediate Similarity	NPC254540
0.8304	Intermediate Similarity	NPC211594
0.8304	Intermediate Similarity	NPC172807
0.8304	Intermediate Similarity	NPC102851
0.8304	Intermediate Similarity	NPC5786
0.8303	Intermediate Similarity	NPC40920
0.8303	Intermediate Similarity	NPC223335
0.8302	Intermediate Similarity	NPC291153
0.8302	Intermediate Similarity	NPC475539
0.8302	Intermediate Similarity	NPC119773
0.8302	Intermediate Similarity	NPC143246
0.8302	Intermediate Similarity	NPC474268

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 NPC476011 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	294
0.1-0.2	810
0.2-0.3	1865
0.3-0.4	2602
0.4-0.5	2093
0.5-0.6	1044
0.6-0.7	365
0.7-0.8	75
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9503	High Similarity	NPD7685	Pre-registration
0.8235	Intermediate Similarity	NPD3818	Discontinued
0.8171	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7054	Approved
0.8035	Intermediate Similarity	NPD7472	Approved
0.7931	Intermediate Similarity	NPD7074	Phase 3
0.7927	Intermediate Similarity	NPD1653	Approved
0.7917	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6190	Approved
0.7886	Intermediate Similarity	NPD6797	Phase 2
0.7862	Intermediate Similarity	NPD7266	Discontinued
0.7841	Intermediate Similarity	NPD7251	Discontinued
0.7836	Intermediate Similarity	NPD7199	Phase 2
0.7824	Intermediate Similarity	NPD6234	Discontinued
0.7816	Intermediate Similarity	NPD7228	Approved
0.7797	Intermediate Similarity	NPD7808	Phase 3
0.7771	Intermediate Similarity	NPD230	Phase 1
0.7765	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD37	Approved
0.7706	Intermediate Similarity	NPD4966	Approved
0.7706	Intermediate Similarity	NPD4967	Phase 2
0.7706	Intermediate Similarity	NPD4965	Approved
0.7644	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD1934	Approved
0.7613	Intermediate Similarity	NPD9494	Approved
0.7607	Intermediate Similarity	NPD4628	Phase 3
0.7588	Intermediate Similarity	NPD2801	Approved
0.7544	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7472	Intermediate Similarity	NPD5844	Phase 1
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6559	Discontinued
0.7429	Intermediate Similarity	NPD8127	Discontinued
0.7412	Intermediate Similarity	NPD4380	Phase 2
0.7412	Intermediate Similarity	NPD7028	Phase 2
0.7391	Intermediate Similarity	NPD6653	Approved
0.7386	Intermediate Similarity	NPD6232	Discontinued
0.7374	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8312	Approved
0.7363	Intermediate Similarity	NPD8313	Approved
0.736	Intermediate Similarity	NPD7473	Discontinued
0.7348	Intermediate Similarity	NPD7240	Approved
0.7341	Intermediate Similarity	NPD5353	Approved
0.7278	Intermediate Similarity	NPD6273	Approved
0.7273	Intermediate Similarity	NPD5494	Approved
0.7273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1511	Approved
0.7257	Intermediate Similarity	NPD7075	Discontinued
0.7222	Intermediate Similarity	NPD447	Suspended
0.719	Intermediate Similarity	NPD9545	Approved
0.7186	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD8455	Phase 2
0.7176	Intermediate Similarity	NPD1512	Approved
0.7168	Intermediate Similarity	NPD6385	Approved
0.7168	Intermediate Similarity	NPD6386	Approved
0.7151	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD5402	Approved
0.7134	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6801	Discontinued
0.7118	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD1933	Approved
0.7108	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6005	Phase 3
0.7108	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6004	Phase 3
0.7108	Intermediate Similarity	NPD6002	Phase 3
0.7107	Intermediate Similarity	NPD5647	Approved
0.7086	Intermediate Similarity	NPD5761	Phase 2
0.7086	Intermediate Similarity	NPD5760	Phase 2
0.7086	Intermediate Similarity	NPD7819	Suspended
0.7086	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4110	Phase 3
0.7081	Intermediate Similarity	NPD3027	Phase 3
0.7077	Intermediate Similarity	NPD7435	Discontinued
0.707	Intermediate Similarity	NPD9269	Phase 2
0.7059	Intermediate Similarity	NPD8434	Phase 2
0.7055	Intermediate Similarity	NPD3620	Phase 2
0.7055	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD3764	Approved
0.7033	Intermediate Similarity	NPD3751	Discontinued
0.7033	Intermediate Similarity	NPD7799	Discontinued
0.7024	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2532	Approved
0.7018	Intermediate Similarity	NPD2534	Approved
0.7018	Intermediate Similarity	NPD2533	Approved
0.701	Intermediate Similarity	NPD6780	Approved
0.701	Intermediate Similarity	NPD6779	Approved
0.701	Intermediate Similarity	NPD6782	Approved
0.701	Intermediate Similarity	NPD6781	Approved
0.701	Intermediate Similarity	NPD6777	Approved
0.701	Intermediate Similarity	NPD6776	Approved
0.701	Intermediate Similarity	NPD6778	Approved
0.7006	Intermediate Similarity	NPD3705	Approved
0.7	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7680	Approved
0.6988	Remote Similarity	NPD7033	Discontinued
0.698	Remote Similarity	NPD7930	Approved
0.6961	Remote Similarity	NPD5242	Approved
0.6959	Remote Similarity	NPD6799	Approved
0.6952	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2935	Discontinued
0.6936	Remote Similarity	NPD5403	Approved
0.6923	Remote Similarity	NPD1357	Approved
0.6923	Remote Similarity	NPD6674	Discontinued
0.6919	Remote Similarity	NPD7999	Approved
0.6909	Remote Similarity	NPD6355	Discontinued
0.6906	Remote Similarity	NPD3787	Discontinued
0.6905	Remote Similarity	NPD5762	Approved
0.6905	Remote Similarity	NPD5763	Approved
0.6904	Remote Similarity	NPD7497	Discontinued
0.69	Remote Similarity	NPD8151	Discontinued
0.6899	Remote Similarity	NPD1091	Approved
0.6886	Remote Similarity	NPD1510	Phase 2
0.6882	Remote Similarity	NPD8166	Discontinued
0.6882	Remote Similarity	NPD6764	Approved
0.6882	Remote Similarity	NPD7039	Approved
0.6882	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7038	Approved
0.6882	Remote Similarity	NPD6765	Approved
0.6882	Remote Similarity	NPD3750	Approved
0.6878	Remote Similarity	NPD8150	Discontinued
0.6875	Remote Similarity	NPD7411	Suspended
0.6875	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7874	Approved
0.6866	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1549	Phase 2
0.6857	Remote Similarity	NPD3455	Phase 2
0.6855	Remote Similarity	NPD1608	Approved
0.6854	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5977	Approved
0.6854	Remote Similarity	NPD5978	Approved
0.6848	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD1613	Approved
0.6848	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD919	Approved
0.6832	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7783	Phase 2
0.6832	Remote Similarity	NPD6362	Approved
0.6826	Remote Similarity	NPD7097	Phase 1
0.6821	Remote Similarity	NPD5401	Approved
0.6821	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7696	Phase 3
0.6818	Remote Similarity	NPD7698	Approved
0.6818	Remote Similarity	NPD6599	Discontinued
0.6818	Remote Similarity	NPD7697	Approved
0.6815	Remote Similarity	NPD9268	Approved
0.6805	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7236	Approved
0.6788	Remote Similarity	NPD6233	Phase 2
0.6784	Remote Similarity	NPD7871	Phase 2
0.6784	Remote Similarity	NPD7870	Phase 2
0.6784	Remote Similarity	NPD8320	Phase 1
0.6784	Remote Similarity	NPD8319	Approved
0.6778	Remote Similarity	NPD3749	Approved
0.6768	Remote Similarity	NPD6823	Phase 2
0.6766	Remote Similarity	NPD7701	Phase 2
0.6766	Remote Similarity	NPD7585	Approved
0.6761	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3226	Approved
0.6753	Remote Similarity	NPD6535	Approved
0.6753	Remote Similarity	NPD6534	Approved
0.6749	Remote Similarity	NPD7801	Approved
0.6748	Remote Similarity	NPD2861	Phase 2
0.6747	Remote Similarity	NPD4140	Approved
0.6746	Remote Similarity	NPD2796	Approved
0.6739	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6784	Approved
0.6737	Remote Similarity	NPD6785	Approved
0.6727	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD7583	Approved
0.6705	Remote Similarity	NPD7239	Suspended
0.6688	Remote Similarity	NPD5536	Phase 2
0.6687	Remote Similarity	NPD6663	Approved
0.6687	Remote Similarity	NPD2798	Approved
0.6686	Remote Similarity	NPD2799	Discontinued
0.6685	Remote Similarity	NPD3926	Phase 2
0.6667	Remote Similarity	NPD824	Approved
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD1876	Approved
0.6667	Remote Similarity	NPD17	Approved
0.6667	Remote Similarity	NPD6959	Discontinued
0.665	Remote Similarity	NPD4420	Approved
0.665	Remote Similarity	NPD7700	Phase 2
0.665	Remote Similarity	NPD7699	Phase 2
0.6649	Remote Similarity	NPD7296	Approved
0.6647	Remote Similarity	NPD1240	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