NPASS Compound

Structure

NPC244454 OpenBabel07101719252D 43 46 0 0 1 0 0 0 0 0999 V2000 -5.5367 -0.5870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5708 -0.3282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7956 -1.5529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8637 -1.0353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0884 -2.2600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4368 -1.1718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3029 0.3282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5426 2.6390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6766 4.1390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5708 -0.6718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4368 0.8282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6766 2.1390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1895 3.6390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4154 -2.7083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6049 0.0694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4483 1.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6730 -0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1225 -2.0012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3029 -0.6718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5426 3.6390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7071 -0.7071 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4495 -2.4495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8978 0.7765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4142 1.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4483 -1.6730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5176 -1.9319 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2247 -1.2247 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9659 -0.2588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5708 0.3282 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.1895 2.6390 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.1689 -1.1718 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4086 4.1390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7424 -3.1566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1566 1.7424 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1213 2.1213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1554 -2.3801 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7765 -2.8978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7013 1.3196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9828 3.2477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9319 0.5176 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 -2.1907 -1.4836 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 18 2 0 0 0 0 5 18 1 0 0 0 0 6 10 2 0 0 0 0 6 19 1 0 0 0 0 7 11 2 0 0 0 0 7 19 1 0 0 0 0 8 12 2 0 0 0 0 8 20 1 0 0 0 0 9 13 2 0 0 0 0 9 20 1 0 0 0 0 10 29 1 0 0 0 0 11 29 1 0 0 0 0 12 30 1 0 0 0 0 13 30 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 15 29 1 0 0 0 0 16 24 1 0 0 0 0 16 30 1 0 0 0 0 17 40 1 0 0 0 0 19 31 2 0 0 0 0 20 32 2 0 0 0 0 21 17 1 6 0 0 0 21 25 1 0 0 0 0 21 41 1 0 0 0 0 22 33 2 0 0 0 0 22 42 1 0 0 0 0 23 34 2 0 0 0 0 23 40 1 0 0 0 0 24 35 2 0 0 0 0 24 43 1 0 0 0 0 25 26 1 0 0 0 0 25 36 1 1 0 0 0 26 27 1 0 0 0 0 26 37 1 6 0 0 0 27 28 1 0 0 0 0 27 42 1 1 0 0 0 28 41 1 0 0 0 0 28 43 1 6 0 0 0 29 38 1 0 0 0 0 30 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	598.17
Volume:	575.846
LogP:	0.975
LogD:	0.276
LogS:	-3.708
# Rotatable Bonds:	13
TPSA:	203.19
# H-Bond Aceptor:	13
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.195
Synthetic Accessibility Score:	4.695
Fsp3:	0.367
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:	-5.386
MDCK Permeability:	2.1998783267918043e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.97
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	84.10718536376953%
Volume Distribution (VD):	0.314
Pgp-substrate:	9.047961235046387%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.069
CYP2D6-inhibitor:	0.584
CYP2D6-substrate:	0.025
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.162

ADMET: Excretion

Clearance (CL):	2.196
Half-life (T1/2):	0.948

ADMET: Toxicity

hERG Blockers:	0.18
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.028
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.243
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.945
Carcinogencity:	0.73
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC244454

Natural Product ID:	NPC244454
*Common Name:**	Jacaglabroside B
IUPAC Name:	[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetyl]oxy-6-[[2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetyl]oxymethyl]oxan-3-yl] 2-phenylacetate
Synonyms:	jacaglabroside B
Standard InCHIKey:	AIFVFVGRWAMEBM-GSQIWVKLSA-N
Standard InCHI:	InChI=1S/C30H30O13/c31-19-6-10-29(38,11-7-19)15-23(34)40-17-21-25(36)26(37)27(42-22(33)14-18-4-2-1-3-5-18)28(41-21)43-24(35)16-30(39)12-8-20(32)9-13-30/h1-13,21,25-28,36-39H,14-17H2/t21-,25-,26+,27-,28+/m1/s1
SMILES:	O=C1C=CC(C=C1)(O)CC(=O)OC[C@H]1O[C@@H](OC(=O)CC2(O)C=CC(=O)C=C2)[C@@H]([C@H]([C@@H]1O)O)OC(=O)Cc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094580
PubChem CID:	45360280
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

*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
NPO12408	Jacaranda glabra	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20307077]
NPO12408	Jacaranda glabra	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	2

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	>	90.0	ug.mL-1	PMID[565810]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.56	ug.mL-1	PMID[565810]

☑ 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 NPC244454 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	271
0.1-0.2	954
0.2-0.3	2281
0.3-0.4	6311
0.4-0.5	10804
0.5-0.6	14761
0.6-0.7	6432
0.7-0.8	849
0.8-0.85	29
0.85-0.9	3
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.959	High Similarity	NPC11025
0.8731	High Similarity	NPC148080
0.8731	High Similarity	NPC469623
0.8655	High Similarity	NPC474641
0.8583	High Similarity	NPC114096
0.856	High Similarity	NPC141970
0.856	High Similarity	NPC140561
0.8516	High Similarity	NPC148026
0.8462	Intermediate Similarity	NPC319995
0.8462	Intermediate Similarity	NPC289415
0.845	Intermediate Similarity	NPC301857
0.8425	Intermediate Similarity	NPC87153
0.8425	Intermediate Similarity	NPC162925
0.8359	Intermediate Similarity	NPC28069
0.8359	Intermediate Similarity	NPC77651
0.8321	Intermediate Similarity	NPC17567
0.8295	Intermediate Similarity	NPC231888
0.8295	Intermediate Similarity	NPC63404
0.8295	Intermediate Similarity	NPC147032
0.8295	Intermediate Similarity	NPC204214
0.8295	Intermediate Similarity	NPC198918
0.8295	Intermediate Similarity	NPC124878
0.8295	Intermediate Similarity	NPC92283
0.8295	Intermediate Similarity	NPC10121
0.8295	Intermediate Similarity	NPC35338
0.8295	Intermediate Similarity	NPC290276
0.8295	Intermediate Similarity	NPC10883
0.8281	Intermediate Similarity	NPC57607
0.8279	Intermediate Similarity	NPC29607
0.8235	Intermediate Similarity	NPC184633
0.8231	Intermediate Similarity	NPC471025
0.8231	Intermediate Similarity	NPC231627
0.8182	Intermediate Similarity	NPC470825
0.8168	Intermediate Similarity	NPC226101
0.8168	Intermediate Similarity	NPC471024
0.8168	Intermediate Similarity	NPC237182
0.8154	Intermediate Similarity	NPC471026
0.814	Intermediate Similarity	NPC317163
0.811	Intermediate Similarity	NPC229600
0.8106	Intermediate Similarity	NPC27712
0.8099	Intermediate Similarity	NPC43584
0.8095	Intermediate Similarity	NPC476096
0.8088	Intermediate Similarity	NPC471345
0.8045	Intermediate Similarity	NPC17968
0.8045	Intermediate Similarity	NPC470122
0.8045	Intermediate Similarity	NPC469705
0.803	Intermediate Similarity	NPC158673
0.8015	Intermediate Similarity	NPC252114
0.8	Intermediate Similarity	NPC470143
0.8	Intermediate Similarity	NPC164172
0.8	Intermediate Similarity	NPC322503
0.797	Intermediate Similarity	NPC469549
0.7956	Intermediate Similarity	NPC472132
0.7939	Intermediate Similarity	NPC123704
0.7931	Intermediate Similarity	NPC131874
0.7926	Intermediate Similarity	NPC471066
0.7926	Intermediate Similarity	NPC471095
0.7923	Intermediate Similarity	NPC138798
0.7917	Intermediate Similarity	NPC22137
0.791	Intermediate Similarity	NPC305162
0.7899	Intermediate Similarity	NPC47286
0.7899	Intermediate Similarity	NPC475195
0.7887	Intermediate Similarity	NPC475528
0.7872	Intermediate Similarity	NPC478250
0.7868	Intermediate Similarity	NPC136608
0.7868	Intermediate Similarity	NPC38420
0.7852	Intermediate Similarity	NPC476407
0.7852	Intermediate Similarity	NPC281798
0.7832	Intermediate Similarity	NPC475539
0.7832	Intermediate Similarity	NPC212808
0.7832	Intermediate Similarity	NPC119773
0.7832	Intermediate Similarity	NPC474268
0.7832	Intermediate Similarity	NPC143246
0.782	Intermediate Similarity	NPC288416
0.7808	Intermediate Similarity	NPC474620
0.7803	Intermediate Similarity	NPC79608
0.7786	Intermediate Similarity	NPC473881
0.7786	Intermediate Similarity	NPC77493
0.7778	Intermediate Similarity	NPC262826
0.777	Intermediate Similarity	NPC156393
0.777	Intermediate Similarity	NPC469696
0.7762	Intermediate Similarity	NPC477737
0.776	Intermediate Similarity	NPC87069
0.7754	Intermediate Similarity	NPC123988
0.7744	Intermediate Similarity	NPC267733
0.7744	Intermediate Similarity	NPC276047
0.7737	Intermediate Similarity	NPC114116
0.7727	Intermediate Similarity	NPC145287
0.7724	Intermediate Similarity	NPC473138
0.7724	Intermediate Similarity	NPC276061
0.7724	Intermediate Similarity	NPC474148
0.7724	Intermediate Similarity	NPC28776
0.7721	Intermediate Similarity	NPC235294
0.7721	Intermediate Similarity	NPC46137
0.7721	Intermediate Similarity	NPC478255
0.771	Intermediate Similarity	NPC52097
0.7705	Intermediate Similarity	NPC20485
0.7703	Intermediate Similarity	NPC87403
0.7687	Intermediate Similarity	NPC106677
0.7681	Intermediate Similarity	NPC169398
0.7676	Intermediate Similarity	NPC65833
0.7676	Intermediate Similarity	NPC245219
0.7676	Intermediate Similarity	NPC284957
0.7676	Intermediate Similarity	NPC31081
0.7669	Intermediate Similarity	NPC83218
0.7669	Intermediate Similarity	NPC126991
0.7669	Intermediate Similarity	NPC476033
0.7667	Intermediate Similarity	NPC469527
0.7661	Intermediate Similarity	NPC264784
0.7661	Intermediate Similarity	NPC30563
0.7655	Intermediate Similarity	NPC470330
0.7651	Intermediate Similarity	NPC469417
0.7651	Intermediate Similarity	NPC477735
0.7643	Intermediate Similarity	NPC100558
0.7643	Intermediate Similarity	NPC101686
0.7643	Intermediate Similarity	NPC310252
0.7643	Intermediate Similarity	NPC469364
0.7643	Intermediate Similarity	NPC84789
0.7643	Intermediate Similarity	NPC302583
0.7643	Intermediate Similarity	NPC65262
0.7635	Intermediate Similarity	NPC5115
0.7635	Intermediate Similarity	NPC106818
0.7634	Intermediate Similarity	NPC11724
0.7626	Intermediate Similarity	NPC158325
0.7626	Intermediate Similarity	NPC103398
0.7626	Intermediate Similarity	NPC180171
0.7619	Intermediate Similarity	NPC474363
0.7619	Intermediate Similarity	NPC172525
0.7616	Intermediate Similarity	NPC476026
0.7616	Intermediate Similarity	NPC474398
0.7616	Intermediate Similarity	NPC474441
0.7616	Intermediate Similarity	NPC474401
0.7612	Intermediate Similarity	NPC471157
0.7606	Intermediate Similarity	NPC80098
0.7603	Intermediate Similarity	NPC469448
0.76	Intermediate Similarity	NPC3449
0.76	Intermediate Similarity	NPC477736
0.7591	Intermediate Similarity	NPC209851
0.7591	Intermediate Similarity	NPC246869
0.7591	Intermediate Similarity	NPC225384
0.7591	Intermediate Similarity	NPC138777
0.7589	Intermediate Similarity	NPC476643
0.7589	Intermediate Similarity	NPC474250
0.7586	Intermediate Similarity	NPC291153
0.7582	Intermediate Similarity	NPC471493
0.7574	Intermediate Similarity	NPC253595
0.7569	Intermediate Similarity	NPC77922
0.7569	Intermediate Similarity	NPC471028
0.7569	Intermediate Similarity	NPC202391
0.7569	Intermediate Similarity	NPC296659
0.7569	Intermediate Similarity	NPC473281
0.7569	Intermediate Similarity	NPC63304
0.7568	Intermediate Similarity	NPC133430
0.7568	Intermediate Similarity	NPC473966
0.7568	Intermediate Similarity	NPC469477
0.7566	Intermediate Similarity	NPC57072
0.7566	Intermediate Similarity	NPC231475
0.7557	Intermediate Similarity	NPC476872
0.7556	Intermediate Similarity	NPC175333
0.7541	Intermediate Similarity	NPC37714
0.7541	Intermediate Similarity	NPC152384
0.7535	Intermediate Similarity	NPC213567
0.7533	Intermediate Similarity	NPC205172
0.7533	Intermediate Similarity	NPC209393
0.75	Intermediate Similarity	NPC225307
0.75	Intermediate Similarity	NPC210531
0.75	Intermediate Similarity	NPC111466
0.75	Intermediate Similarity	NPC208651
0.75	Intermediate Similarity	NPC242756
0.75	Intermediate Similarity	NPC206641
0.75	Intermediate Similarity	NPC263829
0.75	Intermediate Similarity	NPC320259
0.7483	Intermediate Similarity	NPC303429
0.7483	Intermediate Similarity	NPC222102
0.7483	Intermediate Similarity	NPC79908
0.7483	Intermediate Similarity	NPC469399
0.7483	Intermediate Similarity	NPC302989
0.7468	Intermediate Similarity	NPC71780
0.7466	Intermediate Similarity	NPC473867
0.7465	Intermediate Similarity	NPC220942
0.7465	Intermediate Similarity	NPC31745
0.7465	Intermediate Similarity	NPC220936
0.7465	Intermediate Similarity	NPC62800
0.7465	Intermediate Similarity	NPC324262
0.7464	Intermediate Similarity	NPC80599
0.746	Intermediate Similarity	NPC234376
0.746	Intermediate Similarity	NPC158282
0.745	Intermediate Similarity	NPC289021
0.745	Intermediate Similarity	NPC158546
0.7448	Intermediate Similarity	NPC194938
0.7448	Intermediate Similarity	NPC264270
0.7448	Intermediate Similarity	NPC40085
0.7447	Intermediate Similarity	NPC470572
0.7445	Intermediate Similarity	NPC472388
0.7445	Intermediate Similarity	NPC473443
0.7444	Intermediate Similarity	NPC223351
0.7444	Intermediate Similarity	NPC108286
0.7434	Intermediate Similarity	NPC283480
0.7434	Intermediate Similarity	NPC148323
0.7432	Intermediate Similarity	NPC478236

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 NPC244454 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	677
0.2-0.3	1534
0.3-0.4	3061
0.4-0.5	2429
0.5-0.6	941
0.6-0.7	278
0.7-0.8	7
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7794	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD5048	Discontinued
0.7347	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD7266	Discontinued
0.7273	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD6647	Phase 2
0.7226	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD9495	Approved
0.7154	Intermediate Similarity	NPD2629	Approved
0.7054	Intermediate Similarity	NPD969	Suspended
0.702	Intermediate Similarity	NPD5403	Approved
0.7019	Intermediate Similarity	NPD7799	Discontinued
0.6959	Remote Similarity	NPD2575	Approved
0.695	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6190	Approved
0.6905	Remote Similarity	NPD1237	Approved
0.6899	Remote Similarity	NPD2067	Discontinued
0.6894	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5401	Approved
0.6883	Remote Similarity	NPD4380	Phase 2
0.6871	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8313	Approved
0.6867	Remote Similarity	NPD8312	Approved
0.686	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD8455	Phase 2
0.6855	Remote Similarity	NPD2066	Phase 3
0.6855	Remote Similarity	NPD7798	Approved
0.6846	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5125	Phase 3
0.6838	Remote Similarity	NPD5126	Approved
0.6825	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6010	Discontinued
0.6815	Remote Similarity	NPD5402	Approved
0.6807	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7054	Approved
0.6761	Remote Similarity	NPD2613	Approved
0.6747	Remote Similarity	NPD6559	Discontinued
0.6739	Remote Similarity	NPD1091	Approved
0.6733	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7472	Approved
0.6727	Remote Similarity	NPD7074	Phase 3
0.6715	Remote Similarity	NPD5306	Approved
0.6715	Remote Similarity	NPD5305	Approved
0.6707	Remote Similarity	NPD3818	Discontinued
0.6692	Remote Similarity	NPD2182	Approved
0.6687	Remote Similarity	NPD6797	Phase 2
0.6686	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2626	Approved
0.6667	Remote Similarity	NPD2625	Approved
0.6667	Remote Similarity	NPD4136	Approved
0.6667	Remote Similarity	NPD4106	Approved
0.6667	Remote Similarity	NPD2160	Approved
0.6667	Remote Similarity	NPD2628	Approved
0.6667	Remote Similarity	NPD2627	Approved
0.6667	Remote Similarity	NPD2159	Approved
0.6667	Remote Similarity	NPD4135	Approved
0.6667	Remote Similarity	NPD6685	Approved
0.6647	Remote Similarity	NPD7685	Pre-registration
0.6647	Remote Similarity	NPD7251	Discontinued
0.6647	Remote Similarity	NPD8368	Discontinued
0.6643	Remote Similarity	NPD4620	Approved
0.6643	Remote Similarity	NPD5201	Approved
0.6643	Remote Similarity	NPD5203	Approved
0.6643	Remote Similarity	NPD4617	Approved
0.6641	Remote Similarity	NPD5909	Discontinued
0.6625	Remote Similarity	NPD7075	Discontinued
0.6623	Remote Similarity	NPD4628	Phase 3
0.6621	Remote Similarity	NPD3090	Approved
0.6621	Remote Similarity	NPD4745	Approved
0.6621	Remote Similarity	NPD2570	Approved
0.6621	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD3089	Approved
0.6621	Remote Similarity	NPD2571	Approved
0.6621	Remote Similarity	NPD2573	Approved
0.6621	Remote Similarity	NPD2574	Discontinued
0.6621	Remote Similarity	NPD3615	Approved
0.6621	Remote Similarity	NPD4746	Phase 3
0.6621	Remote Similarity	NPD3088	Approved
0.6621	Remote Similarity	NPD3087	Approved
0.6621	Remote Similarity	NPD3616	Approved
0.6621	Remote Similarity	NPD3614	Approved
0.6621	Remote Similarity	NPD2566	Approved
0.6619	Remote Similarity	NPD4807	Approved
0.6619	Remote Similarity	NPD4806	Approved
0.6612	Remote Similarity	NPD9258	Approved
0.6612	Remote Similarity	NPD9256	Approved
0.6607	Remote Similarity	NPD7808	Phase 3
0.6606	Remote Similarity	NPD3751	Discontinued
0.6591	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD1238	Approved
0.6582	Remote Similarity	NPD6801	Discontinued
0.6581	Remote Similarity	NPD9491	Approved
0.6575	Remote Similarity	NPD5121	Approved
0.6575	Remote Similarity	NPD5120	Approved
0.6575	Remote Similarity	NPD5119	Approved
0.6569	Remote Similarity	NPD9545	Approved
0.6567	Remote Similarity	NPD2650	Approved
0.6567	Remote Similarity	NPD2652	Approved
0.6562	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1930	Approved
0.6562	Remote Similarity	NPD5765	Approved
0.6562	Remote Similarity	NPD1929	Approved
0.6554	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.655	Remote Similarity	NPD8150	Discontinued
0.6541	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6912	Phase 3
0.6538	Remote Similarity	NPD1653	Approved
0.6536	Remote Similarity	NPD7236	Approved
0.6531	Remote Similarity	NPD4684	Phase 3
0.6531	Remote Similarity	NPD4686	Approved
0.6531	Remote Similarity	NPD4685	Phase 3
0.6529	Remote Similarity	NPD689	Discontinued
0.6529	Remote Similarity	NPD8407	Phase 2
0.6528	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8513	Phase 3
0.6522	Remote Similarity	NPD4105	Approved
0.6522	Remote Similarity	NPD8517	Approved
0.6522	Remote Similarity	NPD8515	Approved
0.6522	Remote Similarity	NPD4102	Approved
0.6522	Remote Similarity	NPD8516	Approved
0.6519	Remote Similarity	NPD7411	Suspended
0.651	Remote Similarity	NPD7033	Discontinued
0.65	Remote Similarity	NPD4218	Approved
0.65	Remote Similarity	NPD2608	Approved
0.65	Remote Similarity	NPD2610	Approved
0.65	Remote Similarity	NPD4217	Approved
0.65	Remote Similarity	NPD2612	Approved
0.65	Remote Similarity	NPD2609	Approved
0.65	Remote Similarity	NPD3132	Approved
0.65	Remote Similarity	NPD4216	Approved
0.65	Remote Similarity	NPD3131	Approved
0.65	Remote Similarity	NPD4215	Approved
0.65	Remote Similarity	NPD2611	Approved
0.6494	Remote Similarity	NPD6799	Approved
0.6494	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.648	Remote Similarity	NPD1989	Approved
0.6474	Remote Similarity	NPD8361	Approved
0.6474	Remote Similarity	NPD8360	Approved
0.6471	Remote Similarity	NPD4198	Discontinued
0.6463	Remote Similarity	NPD6310	Approved
0.6463	Remote Similarity	NPD6309	Approved
0.6463	Remote Similarity	NPD6311	Approved
0.646	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5204	Approved
0.6452	Remote Similarity	NPD1202	Approved
0.6438	Remote Similarity	NPD3764	Approved
0.6433	Remote Similarity	NPD7239	Suspended
0.6423	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD9493	Approved
0.642	Remote Similarity	NPD6534	Approved
0.642	Remote Similarity	NPD6535	Approved
0.6419	Remote Similarity	NPD1933	Approved
0.6408	Remote Similarity	NPD5157	Phase 1
0.6408	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5159	Phase 2
0.64	Remote Similarity	NPD1693	Approved
0.6397	Remote Similarity	NPD5951	Approved
0.6395	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD6233	Phase 2
0.6393	Remote Similarity	NPD800	Approved
0.6389	Remote Similarity	NPD5647	Approved
0.6385	Remote Similarity	NPD164	Approved
0.6382	Remote Similarity	NPD1549	Phase 2
0.6379	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD8435	Approved
0.6378	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6858	Approved
0.637	Remote Similarity	NPD7008	Discontinued
0.637	Remote Similarity	NPD7094	Approved
0.6364	Remote Similarity	NPD9263	Approved
0.6364	Remote Similarity	NPD9264	Approved
0.6364	Remote Similarity	NPD3787	Discontinued
0.6364	Remote Similarity	NPD6686	Approved
0.6364	Remote Similarity	NPD9267	Approved
0.6357	Remote Similarity	NPD1932	Approved
0.6357	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD3662	Phase 3
0.6345	Remote Similarity	NPD3661	Approved
0.6345	Remote Similarity	NPD3663	Approved
0.6345	Remote Similarity	NPD3664	Approved
0.6341	Remote Similarity	NPD1086	Approved
0.6341	Remote Similarity	NPD1090	Approved
0.6341	Remote Similarity	NPD1089	Approved
0.634	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD7097	Phase 1
0.6327	Remote Similarity	NPD2313	Discontinued
0.6319	Remote Similarity	NPD7435	Discontinued
0.6316	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD74	Approved
0.6316	Remote Similarity	NPD9266	Approved
0.6316	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7700	Phase 2
0.6313	Remote Similarity	NPD7699	Phase 2
0.631	Remote Similarity	NPD7228	Approved
0.6309	Remote Similarity	NPD230	Phase 1
0.6301	Remote Similarity	NPD6832	Phase 2
0.6299	Remote Similarity	NPD3750	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