NPASS Compound

Structure

NPC474936 OpenBabel07101718232D 36 39 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 4.3301 4.5000 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 -3.5491 2.8090 0.0000 C 0 0 2 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 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 -3.8581 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 3.4641 4.0000 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 32 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 14 1 0 0 0 0 6 7 2 0 0 0 0 7 33 1 0 0 0 0 8 11 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 9 24 1 0 0 0 0 10 34 1 0 0 0 0 11 21 1 0 0 0 0 12 6 1 6 0 0 0 12 13 1 0 0 0 0 12 17 1 0 0 0 0 13 25 1 1 0 0 0 14 15 2 0 0 0 0 14 31 1 0 0 0 0 15 32 1 0 0 0 0 16 10 1 6 0 0 0 16 18 1 0 0 0 0 16 35 1 0 0 0 0 17 22 1 0 0 0 0 17 24 1 6 0 0 0 18 19 1 0 0 0 0 18 26 1 1 0 0 0 19 20 1 0 0 0 0 19 27 1 6 0 0 0 20 23 1 0 0 0 0 20 28 1 1 0 0 0 21 29 2 0 0 0 0 21 34 1 0 0 0 0 22 33 1 0 0 0 0 22 36 1 1 0 0 0 23 35 1 0 0 0 0 23 36 1 6 0 0 0 24 1 1 6 0 0 0 24 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.19
Volume:	481.735
LogP:	0.837
LogD:	0.794
LogS:	-3.001
# Rotatable Bonds:	8
TPSA:	173.6
# H-Bond Aceptor:	12
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.291
Synthetic Accessibility Score:	4.699
Fsp3:	0.625
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:	-5.947
MDCK Permeability:	7.982688839547336e-05
Pgp-inhibitor:	0.048
Pgp-substrate:	0.929
Human Intestinal Absorption (HIA):	0.85
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.215
Plasma Protein Binding (PPB):	33.05801010131836%
Volume Distribution (VD):	0.41
Pgp-substrate:	27.560096740722656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.388
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.716
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.044
CYP3A4-substrate:	0.122

ADMET: Excretion

Clearance (CL):	2.725
Half-life (T1/2):	0.887

ADMET: Toxicity

hERG Blockers:	0.189
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.146
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.077
Carcinogencity:	0.875
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.48

Download Data

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

Natural Product: NPC474936

Natural Product ID:	NPC474936
*Common Name:**	6-O-3',4'-Dimethoxybenzoyl 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 3,4-dimethoxybenzoate
Synonyms:
Standard InCHIKey:	MHLBJQVZNLCHBZ-NPWFAMOPSA-N
Standard InCHI:	InChI=1S/C24H32O12/c1-24(30)9-13(25)12-6-7-33-22(17(12)24)36-23-20(28)19(27)18(26)16(35-23)10-34-21(29)11-4-5-14(31-2)15(8-11)32-3/h4-8,12-13,16-20,22-23,25-28,30H,9-10H2,1-3H3/t12-,13+,16+,17+,18+,19-,20+,22-,23-,24-/m0/s1
SMILES:	COc1cc(ccc1OC)C(=O)OC[C@H]1O[C@@H](O[C@@H]2OC=C[C@@H]3[C@H]2[C@@](C)(O)C[C@H]3O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488723
PubChem CID:	44575706
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	=	12.6	pg/ml	PMID[564015]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	27.2	pg/ml	PMID[564015]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	38.1	pg/ml	PMID[564015]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	849.5	pg/ml	PMID[564015]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[564015]

☑ 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 NPC474936 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	345
0.1-0.2	1330
0.2-0.3	3009
0.3-0.4	6502
0.4-0.5	10434
0.5-0.6	7212
0.6-0.7	8611
0.7-0.8	4938
0.8-0.85	248
0.85-0.9	52
0.9-0.95	12
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.974	High Similarity	NPC206815
0.974	High Similarity	NPC476011
0.9679	High Similarity	NPC282551
0.9554	High Similarity	NPC130730
0.9554	High Similarity	NPC301910
0.9437	High Similarity	NPC470685
0.9313	High Similarity	NPC21956
0.9295	High Similarity	NPC179914
0.9286	High Similarity	NPC478232
0.9272	High Similarity	NPC308178
0.9236	High Similarity	NPC138993
0.915	High Similarity	NPC147224
0.9091	High Similarity	NPC475379
0.9091	High Similarity	NPC269914
0.9091	High Similarity	NPC478249
0.9085	High Similarity	NPC478234
0.9085	High Similarity	NPC478236
0.9062	High Similarity	NPC109990
0.9032	High Similarity	NPC203664
0.9	High Similarity	NPC145847
0.8987	High Similarity	NPC226759
0.8981	High Similarity	NPC475484
0.8968	High Similarity	NPC289021
0.8968	High Similarity	NPC158546
0.8954	High Similarity	NPC473149
0.891	High Similarity	NPC194705
0.891	High Similarity	NPC36130
0.891	High Similarity	NPC134905
0.8903	High Similarity	NPC240592
0.8903	High Similarity	NPC117346
0.8889	High Similarity	NPC180586
0.8868	High Similarity	NPC187205
0.8854	High Similarity	NPC89693
0.8854	High Similarity	NPC229548
0.8854	High Similarity	NPC137813
0.8854	High Similarity	NPC478241
0.8812	High Similarity	NPC469384
0.8797	High Similarity	NPC191046
0.8797	High Similarity	NPC194095
0.8797	High Similarity	NPC327032
0.8782	High Similarity	NPC227980
0.875	High Similarity	NPC286919
0.875	High Similarity	NPC475663
0.8742	High Similarity	NPC10205
0.8718	High Similarity	NPC111785
0.8718	High Similarity	NPC96599
0.8713	High Similarity	NPC96194
0.8713	High Similarity	NPC299855
0.8693	High Similarity	NPC302286
0.8693	High Similarity	NPC237872
0.8693	High Similarity	NPC88754
0.8693	High Similarity	NPC263397
0.8693	High Similarity	NPC116104
0.8693	High Similarity	NPC475213
0.8693	High Similarity	NPC152796
0.8688	High Similarity	NPC471405
0.8688	High Similarity	NPC478248
0.8671	High Similarity	NPC478235
0.8663	High Similarity	NPC189704
0.865	High Similarity	NPC41009
0.8645	High Similarity	NPC473867
0.8642	High Similarity	NPC478265
0.8636	High Similarity	NPC77922
0.8636	High Similarity	NPC473281
0.8636	High Similarity	NPC478240
0.8634	High Similarity	NPC472860
0.8634	High Similarity	NPC133984
0.8616	High Similarity	NPC229354
0.8613	High Similarity	NPC476067
0.8613	High Similarity	NPC475121
0.8599	High Similarity	NPC478242
0.8596	High Similarity	NPC473205
0.8596	High Similarity	NPC473776
0.858	High Similarity	NPC160780
0.858	High Similarity	NPC289811
0.8571	High Similarity	NPC242756
0.8553	High Similarity	NPC289438
0.8544	High Similarity	NPC229882
0.8544	High Similarity	NPC158635
0.8544	High Similarity	NPC205054
0.8528	High Similarity	NPC203020
0.8528	High Similarity	NPC239966
0.8526	High Similarity	NPC37838
0.8519	High Similarity	NPC104275
0.8519	High Similarity	NPC4747
0.8519	High Similarity	NPC49173
0.8519	High Similarity	NPC1913
0.8516	High Similarity	NPC296659
0.8516	High Similarity	NPC202391
0.8509	High Similarity	NPC172920
0.8509	High Similarity	NPC156624
0.85	High Similarity	NPC310661
0.85	High Similarity	NPC105827
0.85	High Similarity	NPC157898
0.8485	Intermediate Similarity	NPC100420
0.8476	Intermediate Similarity	NPC472859
0.8476	Intermediate Similarity	NPC311803
0.8476	Intermediate Similarity	NPC25389
0.8471	Intermediate Similarity	NPC18789
0.8466	Intermediate Similarity	NPC76211
0.8466	Intermediate Similarity	NPC475299
0.8462	Intermediate Similarity	NPC195972
0.8462	Intermediate Similarity	NPC316539
0.8457	Intermediate Similarity	NPC71385
0.8457	Intermediate Similarity	NPC230670
0.8457	Intermediate Similarity	NPC475378
0.8447	Intermediate Similarity	NPC476364
0.8442	Intermediate Similarity	NPC80098
0.8434	Intermediate Similarity	NPC475738
0.8428	Intermediate Similarity	NPC69367
0.8424	Intermediate Similarity	NPC33298
0.8424	Intermediate Similarity	NPC285108
0.8415	Intermediate Similarity	NPC119125
0.8415	Intermediate Similarity	NPC166277
0.8412	Intermediate Similarity	NPC469354
0.8412	Intermediate Similarity	NPC469438
0.8412	Intermediate Similarity	NPC169645
0.8412	Intermediate Similarity	NPC84482
0.8409	Intermediate Similarity	NPC112708
0.8408	Intermediate Similarity	NPC474234
0.8397	Intermediate Similarity	NPC184464
0.8397	Intermediate Similarity	NPC251062
0.8395	Intermediate Similarity	NPC38699
0.8385	Intermediate Similarity	NPC245615
0.8385	Intermediate Similarity	NPC61604
0.8385	Intermediate Similarity	NPC299706
0.8385	Intermediate Similarity	NPC44730
0.8385	Intermediate Similarity	NPC115466
0.8365	Intermediate Similarity	NPC98809
0.8365	Intermediate Similarity	NPC476394
0.8362	Intermediate Similarity	NPC473711
0.8354	Intermediate Similarity	NPC74319
0.8354	Intermediate Similarity	NPC287872
0.8344	Intermediate Similarity	NPC478266
0.8344	Intermediate Similarity	NPC163635
0.8333	Intermediate Similarity	NPC208818
0.8333	Intermediate Similarity	NPC472128
0.8333	Intermediate Similarity	NPC186296
0.8333	Intermediate Similarity	NPC472127
0.8324	Intermediate Similarity	NPC188217
0.8323	Intermediate Similarity	NPC472130
0.8323	Intermediate Similarity	NPC472131
0.8323	Intermediate Similarity	NPC267091
0.8313	Intermediate Similarity	NPC246024
0.8313	Intermediate Similarity	NPC148273
0.8312	Intermediate Similarity	NPC31745
0.8312	Intermediate Similarity	NPC49597
0.8312	Intermediate Similarity	NPC220936
0.8303	Intermediate Similarity	NPC289346
0.8303	Intermediate Similarity	NPC239818
0.8303	Intermediate Similarity	NPC218471
0.8303	Intermediate Similarity	NPC476337
0.8302	Intermediate Similarity	NPC472969
0.8284	Intermediate Similarity	NPC197708
0.8284	Intermediate Similarity	NPC658
0.828	Intermediate Similarity	NPC110063
0.828	Intermediate Similarity	NPC471028
0.828	Intermediate Similarity	NPC473090
0.8274	Intermediate Similarity	NPC476277
0.8272	Intermediate Similarity	NPC308555
0.8269	Intermediate Similarity	NPC296643
0.8263	Intermediate Similarity	NPC100425
0.8263	Intermediate Similarity	NPC120012
0.8261	Intermediate Similarity	NPC474620
0.8261	Intermediate Similarity	NPC243891
0.8261	Intermediate Similarity	NPC140151
0.825	Intermediate Similarity	NPC161955
0.825	Intermediate Similarity	NPC92117
0.8246	Intermediate Similarity	NPC163165
0.8242	Intermediate Similarity	NPC469654
0.8239	Intermediate Similarity	NPC476338
0.8239	Intermediate Similarity	NPC24257
0.8239	Intermediate Similarity	NPC476359
0.8239	Intermediate Similarity	NPC153620
0.8235	Intermediate Similarity	NPC43434
0.8235	Intermediate Similarity	NPC472129
0.8228	Intermediate Similarity	NPC108455
0.8228	Intermediate Similarity	NPC469683
0.8225	Intermediate Similarity	NPC116745
0.8217	Intermediate Similarity	NPC478250
0.821	Intermediate Similarity	NPC228662
0.8205	Intermediate Similarity	NPC137501
0.8205	Intermediate Similarity	NPC46644
0.8205	Intermediate Similarity	NPC154262
0.8205	Intermediate Similarity	NPC79908
0.8205	Intermediate Similarity	NPC159387
0.8205	Intermediate Similarity	NPC7518
0.8204	Intermediate Similarity	NPC90905
0.8204	Intermediate Similarity	NPC4013
0.8199	Intermediate Similarity	NPC473091
0.8199	Intermediate Similarity	NPC182350
0.8198	Intermediate Similarity	NPC107739
0.8194	Intermediate Similarity	NPC226005
0.8193	Intermediate Similarity	NPC208676
0.8193	Intermediate Similarity	NPC130489
0.8187	Intermediate Similarity	NPC120621
0.8187	Intermediate Similarity	NPC5786
0.8187	Intermediate Similarity	NPC248257
0.8187	Intermediate Similarity	NPC102851
0.8187	Intermediate Similarity	NPC189631

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 NPC474936 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	284
0.1-0.2	807
0.2-0.3	1812
0.3-0.4	2612
0.4-0.5	2103
0.5-0.6	1062
0.6-0.7	386
0.7-0.8	83
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9379	High Similarity	NPD7685	Pre-registration
0.8057	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.7965	Intermediate Similarity	NPD7054	Approved
0.7929	Intermediate Similarity	NPD7199	Phase 2
0.7919	Intermediate Similarity	NPD7472	Approved
0.7888	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD7074	Phase 3
0.7784	Intermediate Similarity	NPD7808	Phase 3
0.7736	Intermediate Similarity	NPD7266	Discontinued
0.7733	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7251	Discontinued
0.7725	Intermediate Similarity	NPD37	Approved
0.7701	Intermediate Similarity	NPD7228	Approved
0.7697	Intermediate Similarity	NPD1653	Approved
0.7692	Intermediate Similarity	NPD4966	Approved
0.7692	Intermediate Similarity	NPD4967	Phase 2
0.7692	Intermediate Similarity	NPD4965	Approved
0.7692	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6797	Phase 2
0.7654	Intermediate Similarity	NPD6190	Approved
0.7647	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3817	Phase 2
0.7616	Intermediate Similarity	NPD8127	Discontinued
0.7602	Intermediate Similarity	NPD6234	Discontinued
0.7593	Intermediate Similarity	NPD4628	Phase 3
0.7532	Intermediate Similarity	NPD230	Phase 1
0.7529	Intermediate Similarity	NPD5353	Approved
0.7528	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD7028	Phase 2
0.7484	Intermediate Similarity	NPD6653	Approved
0.7458	Intermediate Similarity	NPD5844	Phase 1
0.7446	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD1934	Approved
0.7372	Intermediate Similarity	NPD9494	Approved
0.7368	Intermediate Similarity	NPD8455	Phase 2
0.7368	Intermediate Similarity	NPD2801	Approved
0.7365	Intermediate Similarity	NPD6273	Approved
0.736	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5494	Approved
0.7353	Intermediate Similarity	NPD6385	Approved
0.7353	Intermediate Similarity	NPD6386	Approved
0.7348	Intermediate Similarity	NPD8313	Approved
0.7348	Intermediate Similarity	NPD8312	Approved
0.7345	Intermediate Similarity	NPD7473	Discontinued
0.7337	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6559	Discontinued
0.7294	Intermediate Similarity	NPD4380	Phase 2
0.7288	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6166	Phase 2
0.7283	Intermediate Similarity	NPD3882	Suspended
0.7278	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6232	Discontinued
0.7267	Intermediate Similarity	NPD7819	Suspended
0.7267	Intermediate Similarity	NPD1465	Phase 2
0.7267	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7075	Discontinued
0.7235	Intermediate Similarity	NPD7458	Discontinued
0.7207	Intermediate Similarity	NPD7799	Discontinued
0.7205	Intermediate Similarity	NPD1933	Approved
0.7205	Intermediate Similarity	NPD447	Suspended
0.7169	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4110	Phase 3
0.7168	Intermediate Similarity	NPD5761	Phase 2
0.7168	Intermediate Similarity	NPD5760	Phase 2
0.7152	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8434	Phase 2
0.7126	Intermediate Similarity	NPD5402	Approved
0.711	Intermediate Similarity	NPD6801	Discontinued
0.7108	Intermediate Similarity	NPD6674	Discontinued
0.7101	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6355	Discontinued
0.7097	Intermediate Similarity	NPD3705	Approved
0.7091	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5762	Approved
0.7091	Intermediate Similarity	NPD6004	Phase 3
0.7091	Intermediate Similarity	NPD5763	Approved
0.7091	Intermediate Similarity	NPD6002	Phase 3
0.7091	Intermediate Similarity	NPD6005	Phase 3
0.7091	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD5647	Approved
0.7077	Intermediate Similarity	NPD7999	Approved
0.7066	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7435	Discontinued
0.7062	Intermediate Similarity	NPD7497	Discontinued
0.7059	Intermediate Similarity	NPD9545	Approved
0.7041	Intermediate Similarity	NPD1511	Approved
0.7041	Intermediate Similarity	NPD6799	Approved
0.7039	Intermediate Similarity	NPD5242	Approved
0.7037	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6362	Approved
0.7017	Intermediate Similarity	NPD3751	Discontinued
0.7012	Intermediate Similarity	NPD7097	Phase 1
0.7006	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3787	Discontinued
0.6982	Remote Similarity	NPD7236	Approved
0.6981	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7033	Discontinued
0.6965	Remote Similarity	NPD7930	Approved
0.6959	Remote Similarity	NPD1512	Approved
0.6957	Remote Similarity	NPD6765	Approved
0.6957	Remote Similarity	NPD6764	Approved
0.6943	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1608	Approved
0.6932	Remote Similarity	NPD5978	Approved
0.6932	Remote Similarity	NPD5977	Approved
0.6919	Remote Similarity	NPD5403	Approved
0.6914	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3764	Approved
0.691	Remote Similarity	NPD919	Approved
0.6907	Remote Similarity	NPD6781	Approved
0.6907	Remote Similarity	NPD6778	Approved
0.6907	Remote Similarity	NPD6782	Approved
0.6907	Remote Similarity	NPD6780	Approved
0.6907	Remote Similarity	NPD6777	Approved
0.6907	Remote Similarity	NPD6776	Approved
0.6907	Remote Similarity	NPD6779	Approved
0.6903	Remote Similarity	NPD1357	Approved
0.6901	Remote Similarity	NPD2532	Approved
0.6901	Remote Similarity	NPD2533	Approved
0.6901	Remote Similarity	NPD2534	Approved
0.6901	Remote Similarity	NPD5401	Approved
0.6899	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6599	Discontinued
0.6888	Remote Similarity	NPD7680	Approved
0.6884	Remote Similarity	NPD8151	Discontinued
0.6879	Remote Similarity	NPD7239	Suspended
0.6879	Remote Similarity	NPD1091	Approved
0.6871	Remote Similarity	NPD6233	Phase 2
0.6865	Remote Similarity	NPD7038	Approved
0.6865	Remote Similarity	NPD7039	Approved
0.6864	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD8150	Discontinued
0.6857	Remote Similarity	NPD7411	Suspended
0.6852	Remote Similarity	NPD3027	Phase 3
0.685	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.685	Remote Similarity	NPD7874	Approved
0.6845	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD9269	Phase 2
0.6829	Remote Similarity	NPD3620	Phase 2
0.6829	Remote Similarity	NPD4140	Approved
0.6829	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD2796	Approved
0.6826	Remote Similarity	NPD2935	Discontinued
0.6816	Remote Similarity	NPD7783	Phase 2
0.6816	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6785	Approved
0.6809	Remote Similarity	NPD6784	Approved
0.6806	Remote Similarity	NPD7296	Approved
0.6802	Remote Similarity	NPD7697	Approved
0.6802	Remote Similarity	NPD7696	Phase 3
0.6802	Remote Similarity	NPD7698	Approved
0.6795	Remote Similarity	NPD9268	Approved
0.6784	Remote Similarity	NPD7583	Approved
0.6774	Remote Similarity	NPD5536	Phase 2
0.677	Remote Similarity	NPD2798	Approved
0.6768	Remote Similarity	NPD8319	Approved
0.6768	Remote Similarity	NPD8320	Phase 1
0.6768	Remote Similarity	NPD7871	Phase 2
0.6768	Remote Similarity	NPD7870	Phase 2
0.6766	Remote Similarity	NPD1510	Phase 2
0.6766	Remote Similarity	NPD2799	Discontinued
0.6765	Remote Similarity	NPD8166	Discontinued
0.6765	Remote Similarity	NPD3750	Approved
0.6758	Remote Similarity	NPD3926	Phase 2
0.6752	Remote Similarity	NPD17	Approved
0.6751	Remote Similarity	NPD6823	Phase 2
0.675	Remote Similarity	NPD7701	Phase 2
0.675	Remote Similarity	NPD1876	Approved
0.675	Remote Similarity	NPD7585	Approved
0.6748	Remote Similarity	NPD7095	Approved
0.6746	Remote Similarity	NPD1549	Phase 2
0.6743	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD3226	Approved
0.674	Remote Similarity	NPD1247	Approved
0.6733	Remote Similarity	NPD7801	Approved
0.6726	Remote Similarity	NPD2438	Suspended
0.6718	Remote Similarity	NPD4420	Approved
0.6707	Remote Similarity	NPD6798	Discontinued
0.6706	Remote Similarity	NPD1652	Phase 2
0.6705	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3146	Approved
0.6705	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD6832	Phase 2
0.6687	Remote Similarity	NPD5735	Approved
0.6686	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2346	Discontinued
0.6686	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD6663	Approved
0.6667	Remote Similarity	NPD3749	Approved
0.6667	Remote Similarity	NPD6873	Phase 2

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