NPASS Compound

Structure

NPC473591 OpenBabel07101718192D 45 50 0 0 1 0 0 0 0 0999 V2000 -2.5471 -4.4118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 -3.4314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0569 2.3196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0373 2.3196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4904 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7924 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3395 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9433 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8490 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5471 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5471 -0.4902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 -2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6414 2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3962 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5471 -3.4314 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6981 -2.9412 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6414 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8490 -1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3395 2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4904 2.9412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 0.9804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8490 -0.4902 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3962 -1.9608 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3962 0.9804 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0943 0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6981 -1.9608 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5471 1.4706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6981 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8490 -0.4902 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5471 -1.4706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1885 2.9412 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4904 3.9216 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2452 -1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0943 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2452 1.4706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 35 1 0 0 0 0 4 35 1 0 0 0 0 6 37 1 0 0 0 0 8 11 2 0 0 0 0 8 25 1 0 0 0 0 9 13 2 0 0 0 0 9 25 1 0 0 0 0 10 12 1 0 0 0 0 10 26 2 0 0 0 0 11 27 1 0 0 0 0 12 30 1 0 0 0 0 13 33 1 0 0 0 0 14 17 1 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 15 32 1 0 0 0 0 16 36 1 0 0 0 0 17 38 1 0 0 0 0 18 19 1 0 0 0 0 18 37 1 0 0 0 0 19 39 1 0 0 0 0 20 23 1 0 0 0 0 20 31 1 0 0 0 0 21 25 2 0 0 0 0 21 28 1 0 0 0 0 22 40 1 0 0 0 0 23 1 1 6 0 0 0 23 24 1 0 0 0 0 24 2 1 1 0 0 0 24 34 1 0 0 0 0 26 34 1 0 0 0 0 26 37 1 0 0 0 0 27 28 2 0 0 0 0 27 41 1 0 0 0 0 28 42 1 0 0 0 0 29 35 1 0 0 0 0 29 36 1 1 0 0 0 30 36 1 1 0 0 0 30 38 1 0 0 0 0 31 39 1 1 0 0 0 31 43 1 0 0 0 0 32 35 1 0 0 0 0 32 45 1 1 0 0 0 33 44 2 0 0 0 0 33 45 1 0 0 0 0 34 39 1 6 0 0 0 36 5 1 1 0 0 0 37 38 1 1 0 0 0 38 7 1 1 0 0 0 39 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	620.41
Volume:	668.684
LogP:	6.753
LogD:	5.001
LogS:	-4.811
# Rotatable Bonds:	5
TPSA:	107.22
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.119
Synthetic Accessibility Score:	5.208
Fsp3:	0.718
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.21
MDCK Permeability:	2.355859942326788e-05
Pgp-inhibitor:	0.799
Pgp-substrate:	0.066
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.528
30% Bioavailability (F30%):	0.771

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.61
Plasma Protein Binding (PPB):	99.55469512939453%
Volume Distribution (VD):	1.234
Pgp-substrate:	2.581084966659546%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.127
CYP2C19-inhibitor:	0.12
CYP2C19-substrate:	0.494
CYP2C9-inhibitor:	0.287
CYP2C9-substrate:	0.907
CYP2D6-inhibitor:	0.464
CYP2D6-substrate:	0.58
CYP3A4-inhibitor:	0.375
CYP3A4-substrate:	0.565

ADMET: Excretion

Clearance (CL):	7.498
Half-life (T1/2):	0.273

ADMET: Toxicity

hERG Blockers:	0.414
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.486
Maximum Recommended Daily Dose:	0.984
Skin Sensitization:	0.909
Carcinogencity:	0.039
Eye Corrosion:	0.007
Eye Irritation:	0.531
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC473591

Natural Product ID:	NPC473591
*Common Name:**	28-Hydroxy-12-Ursene-3Beta-Yl-Caffeate
IUPAC Name:	[(3S,4aR,6aR,6bS,8aR,9R,11R,12S,12aS,14aR,14bR)-9-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:	uvaol-3beta-yl-caffeate
Standard InCHIKey:	HVTRDYCUOUZNAP-XVVDDNTPSA-N
Standard InCHI:	InChI=1S/C39H56O6/c1-23-20-31(43)39(22-40)19-18-37(6)26(34(39)24(23)2)10-12-30-36(5)16-15-32(35(3,4)29(36)14-17-38(30,37)7)45-33(44)13-9-25-8-11-27(41)28(42)21-25/h8-11,13,21,23-24,29-32,34,40-43H,12,14-20,22H2,1-7H3/b13-9+/t23-,24+,29+,30-,31-,32+,34+,36+,37-,38-,39-/m1/s1
SMILES:	OC[C@]12CC[C@@]3(C(=CC[C@H]4[C@@]3(C)CC[C@@H]3[C@]4(C)CC[C@@H](C3(C)C)OC(=O)/C=C/c3ccc(c(c3)O)O)[C@@H]2[C@H]([C@@H](C[C@H]1O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446603
PubChem CID:	44575772
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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	=	27.9	pg/ml	PMID[531299]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	28.5	pg/ml	PMID[531299]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	=	607.1	pg/ml	PMID[531299]
NPT927	Cell Line	PBMC	Homo sapiens	Activity	<	7.8	pg/ml	PMID[531299]

☑ 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 NPC473591 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	317
0.1-0.2	1359
0.2-0.3	2859
0.3-0.4	6169
0.4-0.5	9404
0.5-0.6	11475
0.6-0.7	9592
0.7-0.8	1319
0.8-0.85	100
0.85-0.9	42
0.9-0.95	53
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC271494
1.0	High Similarity	NPC155192
0.9924	High Similarity	NPC182249
0.9632	High Similarity	NPC235557
0.9632	High Similarity	NPC310621
0.9562	High Similarity	NPC26045
0.9559	High Similarity	NPC35212
0.9489	High Similarity	NPC477873
0.9489	High Similarity	NPC252133
0.9489	High Similarity	NPC469447
0.9485	High Similarity	NPC473612
0.9353	High Similarity	NPC53520
0.9353	High Similarity	NPC307205
0.9338	High Similarity	NPC116742
0.9338	High Similarity	NPC139243
0.927	High Similarity	NPC470617
0.927	High Similarity	NPC470616
0.9242	High Similarity	NPC86257
0.9203	High Similarity	NPC304110
0.9203	High Similarity	NPC27518
0.9167	High Similarity	NPC475579
0.9167	High Similarity	NPC473773
0.9161	High Similarity	NPC145527
0.9161	High Similarity	NPC470619
0.9161	High Similarity	NPC208785
0.9161	High Similarity	NPC470618
0.9149	High Similarity	NPC8102
0.9149	High Similarity	NPC66894
0.9124	High Similarity	NPC22676
0.9124	High Similarity	NPC216940
0.9124	High Similarity	NPC198621
0.9124	High Similarity	NPC475482
0.9097	High Similarity	NPC118033
0.9051	High Similarity	NPC249817
0.9044	High Similarity	NPC11266
0.9007	High Similarity	NPC25491
0.8993	High Similarity	NPC471875
0.8986	High Similarity	NPC471152
0.8978	High Similarity	NPC173569
0.8978	High Similarity	NPC477874
0.8966	High Similarity	NPC473680
0.8966	High Similarity	NPC475311
0.8966	High Similarity	NPC473579
0.8966	High Similarity	NPC475454
0.8841	High Similarity	NPC43353
0.8828	High Similarity	NPC298647
0.8828	High Similarity	NPC273358
0.8811	High Similarity	NPC235195
0.8811	High Similarity	NPC271607
0.8811	High Similarity	NPC280717
0.8811	High Similarity	NPC19862
0.8794	High Similarity	NPC472801
0.8786	High Similarity	NPC132723
0.8786	High Similarity	NPC76032
0.8759	High Similarity	NPC32017
0.8759	High Similarity	NPC96930
0.8722	High Similarity	NPC10154
0.8722	High Similarity	NPC474532
0.8722	High Similarity	NPC265413
0.8716	High Similarity	NPC205392
0.8716	High Similarity	NPC105942
0.8699	High Similarity	NPC292206
0.8696	High Similarity	NPC475627
0.8696	High Similarity	NPC18982
0.8696	High Similarity	NPC475346
0.8696	High Similarity	NPC475457
0.8676	High Similarity	NPC30174
0.8662	High Similarity	NPC172311
0.8652	High Similarity	NPC248287
0.8652	High Similarity	NPC234548
0.8643	High Similarity	NPC476699
0.8562	High Similarity	NPC266365
0.8511	High Similarity	NPC471872
0.8511	High Similarity	NPC154485
0.8503	High Similarity	NPC325032
0.8503	High Similarity	NPC477483
0.844	Intermediate Similarity	NPC472804
0.8433	Intermediate Similarity	NPC478058
0.8429	Intermediate Similarity	NPC476282
0.8421	Intermediate Similarity	NPC470848
0.8421	Intermediate Similarity	NPC470849
0.8414	Intermediate Similarity	NPC204644
0.8389	Intermediate Similarity	NPC327962
0.838	Intermediate Similarity	NPC470733
0.8367	Intermediate Similarity	NPC320734
0.8356	Intermediate Similarity	NPC471876
0.8355	Intermediate Similarity	NPC472807
0.8344	Intermediate Similarity	NPC471874
0.8333	Intermediate Similarity	NPC106055
0.8333	Intermediate Similarity	NPC110699
0.8333	Intermediate Similarity	NPC309434
0.8333	Intermediate Similarity	NPC203124
0.8286	Intermediate Similarity	NPC243305
0.8276	Intermediate Similarity	NPC470035
0.8273	Intermediate Similarity	NPC470747
0.8271	Intermediate Similarity	NPC470214
0.8271	Intermediate Similarity	NPC109371
0.8271	Intermediate Similarity	NPC470215
0.8271	Intermediate Similarity	NPC141791
0.8271	Intermediate Similarity	NPC263386
0.8264	Intermediate Similarity	NPC474640
0.8264	Intermediate Similarity	NPC475757
0.8252	Intermediate Similarity	NPC120852
0.825	Intermediate Similarity	NPC469776
0.825	Intermediate Similarity	NPC469778
0.825	Intermediate Similarity	NPC135334
0.825	Intermediate Similarity	NPC469772
0.825	Intermediate Similarity	NPC469775
0.825	Intermediate Similarity	NPC469777
0.825	Intermediate Similarity	NPC100925
0.825	Intermediate Similarity	NPC32723
0.825	Intermediate Similarity	NPC469773
0.825	Intermediate Similarity	NPC469774
0.825	Intermediate Similarity	NPC295941
0.8248	Intermediate Similarity	NPC137416
0.8228	Intermediate Similarity	NPC200726
0.82	Intermediate Similarity	NPC279442
0.8195	Intermediate Similarity	NPC86198
0.8188	Intermediate Similarity	NPC171007
0.8188	Intermediate Similarity	NPC190849
0.8188	Intermediate Similarity	NPC472938
0.8188	Intermediate Similarity	NPC472936
0.8188	Intermediate Similarity	NPC472937
0.8187	Intermediate Similarity	NPC472803
0.8182	Intermediate Similarity	NPC281277
0.8182	Intermediate Similarity	NPC103082
0.8176	Intermediate Similarity	NPC286809
0.8176	Intermediate Similarity	NPC177362
0.8163	Intermediate Similarity	NPC184935
0.8143	Intermediate Similarity	NPC288290
0.8134	Intermediate Similarity	NPC70084
0.8125	Intermediate Similarity	NPC266545
0.8125	Intermediate Similarity	NPC471870
0.8125	Intermediate Similarity	NPC202428
0.812	Intermediate Similarity	NPC145023
0.812	Intermediate Similarity	NPC175799
0.812	Intermediate Similarity	NPC200988
0.812	Intermediate Similarity	NPC610
0.8112	Intermediate Similarity	NPC194970
0.8108	Intermediate Similarity	NPC96447
0.8106	Intermediate Similarity	NPC474967
0.8106	Intermediate Similarity	NPC233669
0.8105	Intermediate Similarity	NPC475162
0.8105	Intermediate Similarity	NPC473544
0.8105	Intermediate Similarity	NPC223720
0.8105	Intermediate Similarity	NPC83663
0.8105	Intermediate Similarity	NPC475145
0.8105	Intermediate Similarity	NPC475216
0.8105	Intermediate Similarity	NPC475595
0.8105	Intermediate Similarity	NPC266084
0.8105	Intermediate Similarity	NPC115203
0.8092	Intermediate Similarity	NPC77310
0.8088	Intermediate Similarity	NPC147654
0.8079	Intermediate Similarity	NPC46549
0.8079	Intermediate Similarity	NPC264229
0.806	Intermediate Similarity	NPC275519
0.8054	Intermediate Similarity	NPC274960
0.8054	Intermediate Similarity	NPC473909
0.8054	Intermediate Similarity	NPC143120
0.8052	Intermediate Similarity	NPC268484
0.8041	Intermediate Similarity	NPC476378
0.8041	Intermediate Similarity	NPC175214
0.8041	Intermediate Similarity	NPC119537
0.8041	Intermediate Similarity	NPC205864
0.8041	Intermediate Similarity	NPC269141
0.8041	Intermediate Similarity	NPC247032
0.8041	Intermediate Similarity	NPC112
0.8041	Intermediate Similarity	NPC76406
0.8041	Intermediate Similarity	NPC476380
0.8041	Intermediate Similarity	NPC476384
0.8041	Intermediate Similarity	NPC264632
0.8041	Intermediate Similarity	NPC476375
0.8041	Intermediate Similarity	NPC298257
0.8041	Intermediate Similarity	NPC476397
0.8041	Intermediate Similarity	NPC476381
0.8041	Intermediate Similarity	NPC96795
0.803	Intermediate Similarity	NPC328593
0.803	Intermediate Similarity	NPC33749
0.803	Intermediate Similarity	NPC261453
0.8029	Intermediate Similarity	NPC471794
0.8028	Intermediate Similarity	NPC312341
0.8027	Intermediate Similarity	NPC47471
0.8027	Intermediate Similarity	NPC476377
0.8026	Intermediate Similarity	NPC472939
0.8014	Intermediate Similarity	NPC64141
0.8014	Intermediate Similarity	NPC476383
0.8014	Intermediate Similarity	NPC89105
0.8014	Intermediate Similarity	NPC472350
0.8014	Intermediate Similarity	NPC68092
0.8014	Intermediate Similarity	NPC197316
0.8014	Intermediate Similarity	NPC83062
0.8014	Intermediate Similarity	NPC81515
0.8	Intermediate Similarity	NPC470038
0.8	Intermediate Similarity	NPC75295
0.8	Intermediate Similarity	NPC258856
0.7987	Intermediate Similarity	NPC477207
0.7987	Intermediate Similarity	NPC64195
0.7986	Intermediate Similarity	NPC471913
0.7975	Intermediate Similarity	NPC471871
0.7973	Intermediate Similarity	NPC222433

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 NPC473591 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	264
0.1-0.2	850
0.2-0.3	1591
0.3-0.4	2845
0.4-0.5	2023
0.5-0.6	1208
0.6-0.7	348
0.7-0.8	20
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
0.9275	High Similarity	NPD8166	Discontinued
0.8014	Intermediate Similarity	NPD7266	Discontinued
0.7872	Intermediate Similarity	NPD5736	Approved
0.775	Intermediate Similarity	NPD8127	Discontinued
0.7724	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3620	Phase 2
0.7655	Intermediate Similarity	NPD6663	Approved
0.7606	Intermediate Similarity	NPD3094	Phase 2
0.7603	Intermediate Similarity	NPD4140	Approved
0.7571	Intermediate Similarity	NPD3092	Approved
0.7536	Intermediate Similarity	NPD3091	Approved
0.7519	Intermediate Similarity	NPD3022	Approved
0.7519	Intermediate Similarity	NPD3021	Approved
0.75	Intermediate Similarity	NPD7003	Approved
0.7484	Intermediate Similarity	NPD6273	Approved
0.7483	Intermediate Similarity	NPD4060	Phase 1
0.7452	Intermediate Similarity	NPD7458	Discontinued
0.7451	Intermediate Similarity	NPD6190	Approved
0.7419	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD5735	Approved
0.7305	Intermediate Similarity	NPD7228	Approved
0.7305	Intermediate Similarity	NPD4626	Approved
0.7305	Intermediate Similarity	NPD3095	Discontinued
0.7279	Intermediate Similarity	NPD7095	Approved
0.7267	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5691	Approved
0.7222	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7097	Phase 1
0.7208	Intermediate Similarity	NPD6674	Discontinued
0.7195	Intermediate Similarity	NPD6234	Discontinued
0.719	Intermediate Similarity	NPD5762	Approved
0.719	Intermediate Similarity	NPD5763	Approved
0.7183	Intermediate Similarity	NPD3019	Approved
0.7183	Intermediate Similarity	NPD2932	Approved
0.7174	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD3027	Phase 3
0.7161	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4628	Phase 3
0.7161	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4110	Phase 3
0.7125	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5327	Phase 3
0.7099	Intermediate Similarity	NPD37	Approved
0.7089	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4967	Phase 2
0.7073	Intermediate Similarity	NPD4966	Approved
0.7073	Intermediate Similarity	NPD4965	Approved
0.7071	Intermediate Similarity	NPD4198	Discontinued
0.707	Intermediate Similarity	NPD7236	Approved
0.7067	Intermediate Similarity	NPD8032	Phase 2
0.7059	Intermediate Similarity	NPD5844	Phase 1
0.7052	Intermediate Similarity	NPD8313	Approved
0.7052	Intermediate Similarity	NPD8312	Approved
0.7029	Intermediate Similarity	NPD8150	Discontinued
0.702	Intermediate Similarity	NPD1613	Approved
0.702	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5404	Approved
0.7013	Intermediate Similarity	NPD5405	Approved
0.7013	Intermediate Similarity	NPD5408	Approved
0.7013	Intermediate Similarity	NPD5406	Approved
0.7	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7028	Phase 2
0.6974	Remote Similarity	NPD230	Phase 1
0.6974	Remote Similarity	NPD6355	Discontinued
0.6959	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1653	Approved
0.695	Remote Similarity	NPD7157	Approved
0.6944	Remote Similarity	NPD4059	Approved
0.6939	Remote Similarity	NPD8651	Approved
0.6929	Remote Similarity	NPD5283	Phase 1
0.6928	Remote Similarity	NPD6353	Approved
0.6923	Remote Similarity	NPD7741	Discontinued
0.6914	Remote Similarity	NPD3455	Phase 2
0.6906	Remote Similarity	NPD228	Approved
0.6903	Remote Similarity	NPD2935	Discontinued
0.6897	Remote Similarity	NPD3496	Discontinued
0.6887	Remote Similarity	NPD3764	Approved
0.6887	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6798	Discontinued
0.6879	Remote Similarity	NPD2629	Approved
0.6871	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7768	Phase 2
0.6867	Remote Similarity	NPD4908	Phase 1
0.6863	Remote Similarity	NPD3657	Discovery
0.6863	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5124	Phase 1
0.6859	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7239	Suspended
0.6848	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD8455	Phase 2
0.6846	Remote Similarity	NPD4624	Approved
0.6842	Remote Similarity	NPD3020	Approved
0.6842	Remote Similarity	NPD7473	Discontinued
0.6839	Remote Similarity	NPD7742	Approved
0.6839	Remote Similarity	NPD7685	Pre-registration
0.6839	Remote Similarity	NPD7743	Approved
0.6839	Remote Similarity	NPD7240	Approved
0.6826	Remote Similarity	NPD7833	Phase 2
0.6826	Remote Similarity	NPD7831	Phase 2
0.6826	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD1283	Approved
0.6821	Remote Similarity	NPD7008	Discontinued
0.6821	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD4097	Suspended
0.6818	Remote Similarity	NPD6653	Approved
0.6813	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD826	Approved
0.6797	Remote Similarity	NPD825	Approved
0.6795	Remote Similarity	NPD2438	Suspended
0.6792	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3134	Approved
0.6784	Remote Similarity	NPD2489	Approved
0.6784	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6166	Phase 2
0.6784	Remote Similarity	NPD27	Approved
0.6784	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3023	Approved
0.6781	Remote Similarity	NPD3026	Approved
0.6779	Remote Similarity	NPD2797	Approved
0.6778	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.677	Remote Similarity	NPD3645	Discontinued
0.6765	Remote Similarity	NPD6232	Discontinued
0.6759	Remote Similarity	NPD1357	Approved
0.6759	Remote Similarity	NPD3024	Approved
0.6759	Remote Similarity	NPD3025	Approved
0.6755	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7819	Suspended
0.6742	Remote Similarity	NPD8434	Phase 2
0.6739	Remote Similarity	NPD1358	Approved
0.6738	Remote Similarity	NPD5535	Approved
0.6738	Remote Similarity	NPD7843	Approved
0.6738	Remote Similarity	NPD7635	Approved
0.6736	Remote Similarity	NPD5536	Phase 2
0.6735	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD6233	Phase 2
0.6731	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.673	Remote Similarity	NPD3750	Approved
0.6728	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD6677	Suspended
0.6724	Remote Similarity	NPD7074	Phase 3
0.671	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7041	Phase 2
0.6708	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7199	Phase 2
0.6689	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2861	Phase 2
0.6688	Remote Similarity	NPD2979	Phase 3
0.6687	Remote Similarity	NPD1934	Approved
0.6687	Remote Similarity	NPD8131	Suspended
0.6667	Remote Similarity	NPD7054	Approved
0.6667	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7313	Approved
0.6667	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7312	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD7311	Approved
0.6667	Remote Similarity	NPD7310	Approved
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD5585	Approved
0.6643	Remote Similarity	NPD4750	Phase 3
0.6629	Remote Similarity	NPD7472	Approved
0.6629	Remote Similarity	NPD7309	Approved
0.6628	Remote Similarity	NPD2970	Approved
0.6628	Remote Similarity	NPD2969	Approved
0.6627	Remote Similarity	NPD7075	Discontinued
0.6625	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD2799	Discontinued
0.6622	Remote Similarity	NPD1281	Approved
0.6619	Remote Similarity	NPD2342	Discontinued
0.6617	Remote Similarity	NPD2859	Approved
0.6617	Remote Similarity	NPD2860	Approved
0.661	Remote Similarity	NPD7549	Discontinued
0.6607	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD7390	Discontinued
0.6604	Remote Similarity	NPD7037	Approved
0.6599	Remote Similarity	NPD1778	Approved
0.6596	Remote Similarity	NPD7680	Approved
0.659	Remote Similarity	NPD4481	Phase 3
0.659	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD5699	Approved
0.6582	Remote Similarity	NPD6099	Approved
0.6582	Remote Similarity	NPD6100	Approved
0.6581	Remote Similarity	NPD943	Approved
0.6579	Remote Similarity	NPD9494	Approved
0.6575	Remote Similarity	NPD9545	Approved
0.6573	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2684	Approved
0.657	Remote Similarity	NPD3051	Approved
0.6567	Remote Similarity	NPD288	Approved
0.6566	Remote Similarity	NPD4380	Phase 2
0.6559	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD7985	Registered

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