NPASS Compound

Structure

NPC182249 OpenBabel07101719512D 44 49 0 0 1 0 0 0 0 0999 V2000 2.5461 -4.4100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 -3.4300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0361 2.3187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0561 2.3187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0922 -1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9409 -0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0922 -2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0922 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3948 -2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8487 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3948 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5461 -0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3948 -1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6974 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5461 -0.4900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7896 -1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3948 -0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5461 -3.4300 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6974 -2.9400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9409 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8487 -1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9409 -3.4300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7896 -2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 0.9800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8487 -0.4900 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3948 0.9800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0922 0.9800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6974 -1.9600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5461 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6974 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8487 -0.4900 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 2.5461 -1.4700 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2435 -1.4700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9409 -4.4100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6383 -3.4300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9409 1.4700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2435 1.4700 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 26 1 0 0 0 0 9 13 2 0 0 0 0 9 26 1 0 0 0 0 10 12 1 0 0 0 0 10 27 2 0 0 0 0 11 28 1 0 0 0 0 12 31 1 0 0 0 0 13 33 1 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 18 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 32 1 0 0 0 0 17 36 1 0 0 0 0 18 38 1 0 0 0 0 19 39 1 0 0 0 0 20 21 1 0 0 0 0 20 37 1 0 0 0 0 21 39 1 0 0 0 0 22 26 2 0 0 0 0 22 29 1 0 0 0 0 23 40 1 0 0 0 0 24 1 1 1 0 0 0 24 25 1 0 0 0 0 25 2 1 6 0 0 0 25 34 1 0 0 0 0 27 34 1 0 0 0 0 27 37 1 0 0 0 0 28 29 2 0 0 0 0 28 41 1 0 0 0 0 29 42 1 0 0 0 0 30 35 1 0 0 0 0 30 36 1 6 0 0 0 31 36 1 6 0 0 0 31 38 1 0 0 0 0 32 35 1 0 0 0 0 32 44 1 6 0 0 0 33 43 2 0 0 0 0 33 44 1 0 0 0 0 34 39 1 1 0 0 0 36 5 1 6 0 0 0 37 38 1 6 0 0 0 38 7 1 6 0 0 0 39 23 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	604.41
Volume:	659.894
LogP:	7.825
LogD:	5.527
LogS:	-5.243
# Rotatable Bonds:	5
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.139
Synthetic Accessibility Score:	5.026
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:	-5.121
MDCK Permeability:	2.3082466213963926e-05
Pgp-inhibitor:	0.334
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.45
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	99.9312744140625%
Volume Distribution (VD):	1.954
Pgp-substrate:	2.3192362785339355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.095
CYP1A2-substrate:	0.164
CYP2C19-inhibitor:	0.226
CYP2C19-substrate:	0.557
CYP2C9-inhibitor:	0.201
CYP2C9-substrate:	0.799
CYP2D6-inhibitor:	0.722
CYP2D6-substrate:	0.591
CYP3A4-inhibitor:	0.67
CYP3A4-substrate:	0.625

ADMET: Excretion

Clearance (CL):	7.84
Half-life (T1/2):	0.104

ADMET: Toxicity

hERG Blockers:	0.138
Human Hepatotoxicity (H-HT):	0.435
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.657
Carcinogencity:	0.052
Eye Corrosion:	0.008
Eye Irritation:	0.221
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC182249

Natural Product ID:	NPC182249
*Common Name:**	Uvaol-3-Caffeate
IUPAC Name:	[(3S,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-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-3-Caffeate
Standard InCHIKey:	VAVKRHSGFFQRKW-APPDBDSJSA-N
Standard InCHI:	InChI=1S/C39H56O5/c1-24-14-19-39(23-40)21-20-37(6)27(34(39)25(24)2)10-12-31-36(5)17-16-32(35(3,4)30(36)15-18-38(31,37)7)44-33(43)13-9-26-8-11-28(41)29(42)22-26/h8-11,13,22,24-25,30-32,34,40-42H,12,14-21,23H2,1-7H3/b13-9+/t24-,25+,30+,31-,32+,34+,36+,37-,38-,39-/m1/s1
SMILES:	OC[C@@]12CC[C@H]([C@@H]([C@H]2C2=CC[C@H]3[C@@]([C@@]2(CC1)C)(C)CC[C@@H]1[C@]3(C)CC[C@@H](C1(C)C)OC(=O)/C=C/c1ccc(c(c1)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL444208
PubChem CID:	11376945
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
NPO18922	Maytenus ilicifolia	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043435]
NPO18922	Maytenus ilicifolia	Species	Celastraceae	Eukaryota	root bark	n.a.	n.a.	PMID[17555350]
NPO18922	Maytenus ilicifolia	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22559947]
NPO18922	Maytenus ilicifolia	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[486887]

☑ 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 NPC182249 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	1376
0.2-0.3	2842
0.3-0.4	6293
0.4-0.5	9446
0.5-0.6	11848
0.6-0.7	9174
0.7-0.8	1206
0.8-0.85	91
0.85-0.9	48
0.9-0.95	53
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC271494
0.9924	High Similarity	NPC473591
0.9924	High Similarity	NPC155192
0.963	High Similarity	NPC35212
0.9559	High Similarity	NPC235557
0.9559	High Similarity	NPC477873
0.9559	High Similarity	NPC310621
0.9559	High Similarity	NPC252133
0.9559	High Similarity	NPC469447
0.9556	High Similarity	NPC473612
0.9489	High Similarity	NPC26045
0.942	High Similarity	NPC53520
0.942	High Similarity	NPC307205
0.9313	High Similarity	NPC86257
0.927	High Similarity	NPC304110
0.927	High Similarity	NPC27518
0.9265	High Similarity	NPC116742
0.9265	High Similarity	NPC139243
0.9214	High Similarity	NPC8102
0.9214	High Similarity	NPC66894
0.9197	High Similarity	NPC470616
0.9197	High Similarity	NPC470617
0.9161	High Similarity	NPC118033
0.9118	High Similarity	NPC249817
0.9111	High Similarity	NPC11266
0.9097	High Similarity	NPC475579
0.9097	High Similarity	NPC473773
0.9091	High Similarity	NPC208785
0.9091	High Similarity	NPC470619
0.9091	High Similarity	NPC470618
0.9091	High Similarity	NPC145527
0.9071	High Similarity	NPC25491
0.9051	High Similarity	NPC22676
0.9051	High Similarity	NPC475482
0.9051	High Similarity	NPC216940
0.9051	High Similarity	NPC198621
0.9051	High Similarity	NPC471152
0.9044	High Similarity	NPC477874
0.9044	High Similarity	NPC173569
0.9028	High Similarity	NPC473579
0.9028	High Similarity	NPC475311
0.9028	High Similarity	NPC475454
0.9028	High Similarity	NPC473680
0.8921	High Similarity	NPC471875
0.8905	High Similarity	NPC43353
0.8889	High Similarity	NPC273358
0.8889	High Similarity	NPC298647
0.8873	High Similarity	NPC280717
0.8873	High Similarity	NPC235195
0.8873	High Similarity	NPC271607
0.8873	High Similarity	NPC19862
0.8849	High Similarity	NPC76032
0.8849	High Similarity	NPC132723
0.8819	High Similarity	NPC32017
0.8819	High Similarity	NPC96930
0.8788	High Similarity	NPC265413
0.8788	High Similarity	NPC10154
0.8776	High Similarity	NPC205392
0.8776	High Similarity	NPC105942
0.8759	High Similarity	NPC475627
0.8759	High Similarity	NPC18982
0.8759	High Similarity	NPC475346
0.8759	High Similarity	NPC292206
0.8759	High Similarity	NPC475457
0.8741	High Similarity	NPC30174
0.8723	High Similarity	NPC172311
0.8723	High Similarity	NPC472801
0.8714	High Similarity	NPC248287
0.8714	High Similarity	NPC234548
0.8705	High Similarity	NPC476699
0.8647	High Similarity	NPC474532
0.8497	Intermediate Similarity	NPC266365
0.8496	Intermediate Similarity	NPC478058
0.8489	Intermediate Similarity	NPC476282
0.8485	Intermediate Similarity	NPC470849
0.8485	Intermediate Similarity	NPC470848
0.8446	Intermediate Similarity	NPC327962
0.844	Intermediate Similarity	NPC471872
0.844	Intermediate Similarity	NPC154485
0.8435	Intermediate Similarity	NPC477483
0.8435	Intermediate Similarity	NPC325032
0.8397	Intermediate Similarity	NPC203124
0.8397	Intermediate Similarity	NPC309434
0.8392	Intermediate Similarity	NPC110699
0.8392	Intermediate Similarity	NPC106055
0.8369	Intermediate Similarity	NPC472804
0.8345	Intermediate Similarity	NPC243305
0.8345	Intermediate Similarity	NPC204644
0.8333	Intermediate Similarity	NPC263386
0.8333	Intermediate Similarity	NPC470747
0.8333	Intermediate Similarity	NPC141791
0.8333	Intermediate Similarity	NPC470035
0.831	Intermediate Similarity	NPC470733
0.831	Intermediate Similarity	NPC120852
0.8309	Intermediate Similarity	NPC137416
0.8299	Intermediate Similarity	NPC320734
0.8289	Intermediate Similarity	NPC472807
0.8288	Intermediate Similarity	NPC471876
0.828	Intermediate Similarity	NPC200726
0.8278	Intermediate Similarity	NPC471874
0.8255	Intermediate Similarity	NPC279442
0.8248	Intermediate Similarity	NPC190849
0.8248	Intermediate Similarity	NPC171007
0.8244	Intermediate Similarity	NPC281277
0.8239	Intermediate Similarity	NPC103082
0.8228	Intermediate Similarity	NPC177362
0.8219	Intermediate Similarity	NPC184935
0.8201	Intermediate Similarity	NPC288290
0.8195	Intermediate Similarity	NPC470214
0.8195	Intermediate Similarity	NPC470215
0.8195	Intermediate Similarity	NPC109371
0.8194	Intermediate Similarity	NPC474640
0.8194	Intermediate Similarity	NPC475757
0.8187	Intermediate Similarity	NPC469773
0.8187	Intermediate Similarity	NPC469772
0.8187	Intermediate Similarity	NPC100925
0.8187	Intermediate Similarity	NPC469777
0.8187	Intermediate Similarity	NPC469775
0.8187	Intermediate Similarity	NPC469774
0.8187	Intermediate Similarity	NPC135334
0.8187	Intermediate Similarity	NPC32723
0.8187	Intermediate Similarity	NPC469778
0.8187	Intermediate Similarity	NPC469776
0.8187	Intermediate Similarity	NPC295941
0.8182	Intermediate Similarity	NPC175799
0.8182	Intermediate Similarity	NPC200988
0.8182	Intermediate Similarity	NPC145023
0.8182	Intermediate Similarity	NPC610
0.8176	Intermediate Similarity	NPC202428
0.8176	Intermediate Similarity	NPC266545
0.8169	Intermediate Similarity	NPC194970
0.8168	Intermediate Similarity	NPC474967
0.8168	Intermediate Similarity	NPC233669
0.8158	Intermediate Similarity	NPC475216
0.8158	Intermediate Similarity	NPC475595
0.8158	Intermediate Similarity	NPC266084
0.8158	Intermediate Similarity	NPC475162
0.8158	Intermediate Similarity	NPC473544
0.8158	Intermediate Similarity	NPC475145
0.8158	Intermediate Similarity	NPC83663
0.8148	Intermediate Similarity	NPC147654
0.8133	Intermediate Similarity	NPC264229
0.8133	Intermediate Similarity	NPC46549
0.8125	Intermediate Similarity	NPC472803
0.8121	Intermediate Similarity	NPC472936
0.8121	Intermediate Similarity	NPC472938
0.8121	Intermediate Similarity	NPC472937
0.812	Intermediate Similarity	NPC86198
0.812	Intermediate Similarity	NPC275519
0.8113	Intermediate Similarity	NPC286809
0.8092	Intermediate Similarity	NPC33749
0.8092	Intermediate Similarity	NPC261453
0.8092	Intermediate Similarity	NPC328593
0.8088	Intermediate Similarity	NPC471794
0.8085	Intermediate Similarity	NPC312341
0.8071	Intermediate Similarity	NPC83062
0.8063	Intermediate Similarity	NPC471870
0.806	Intermediate Similarity	NPC70084
0.8054	Intermediate Similarity	NPC75295
0.8054	Intermediate Similarity	NPC258856
0.8054	Intermediate Similarity	NPC470038
0.8042	Intermediate Similarity	NPC471913
0.8041	Intermediate Similarity	NPC96447
0.8041	Intermediate Similarity	NPC477207
0.8039	Intermediate Similarity	NPC223720
0.8039	Intermediate Similarity	NPC115203
0.8028	Intermediate Similarity	NPC59239
0.8026	Intermediate Similarity	NPC77310
0.8015	Intermediate Similarity	NPC95381
0.8013	Intermediate Similarity	NPC471750
0.8013	Intermediate Similarity	NPC473719
0.8013	Intermediate Similarity	NPC477206
0.8	Intermediate Similarity	NPC474991
0.7987	Intermediate Similarity	NPC268484
0.7987	Intermediate Similarity	NPC143120
0.7987	Intermediate Similarity	NPC274960
0.7987	Intermediate Similarity	NPC473909
0.7986	Intermediate Similarity	NPC120225
0.7986	Intermediate Similarity	NPC213552
0.7973	Intermediate Similarity	NPC96795
0.7973	Intermediate Similarity	NPC476384
0.7973	Intermediate Similarity	NPC471972
0.7973	Intermediate Similarity	NPC76406
0.7973	Intermediate Similarity	NPC175214
0.7973	Intermediate Similarity	NPC119537
0.7973	Intermediate Similarity	NPC269141
0.7973	Intermediate Similarity	NPC476381
0.7973	Intermediate Similarity	NPC112
0.7973	Intermediate Similarity	NPC247032
0.7973	Intermediate Similarity	NPC476375
0.7973	Intermediate Similarity	NPC264632
0.7973	Intermediate Similarity	NPC471971
0.7973	Intermediate Similarity	NPC469855
0.7973	Intermediate Similarity	NPC476378
0.7973	Intermediate Similarity	NPC476380
0.7973	Intermediate Similarity	NPC205864
0.7973	Intermediate Similarity	NPC30846
0.7973	Intermediate Similarity	NPC298257
0.7973	Intermediate Similarity	NPC476397
0.7971	Intermediate Similarity	NPC60517

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 NPC182249 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	865
0.2-0.3	1561
0.3-0.4	2831
0.4-0.5	2053
0.5-0.6	1208
0.6-0.7	346
0.7-0.8	21
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
0.9343	High Similarity	NPD8166	Discontinued
0.7945	Intermediate Similarity	NPD7266	Discontinued
0.7929	Intermediate Similarity	NPD5736	Approved
0.7799	Intermediate Similarity	NPD8127	Discontinued
0.7778	Intermediate Similarity	NPD3620	Phase 2
0.7778	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6663	Approved
0.7655	Intermediate Similarity	NPD4140	Approved
0.7626	Intermediate Similarity	NPD3092	Approved
0.7591	Intermediate Similarity	NPD3091	Approved
0.7576	Intermediate Similarity	NPD3021	Approved
0.7576	Intermediate Similarity	NPD3022	Approved
0.755	Intermediate Similarity	NPD7003	Approved
0.7535	Intermediate Similarity	NPD3094	Phase 2
0.7534	Intermediate Similarity	NPD4060	Phase 1
0.7532	Intermediate Similarity	NPD6273	Approved
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7468	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6190	Approved
0.7384	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD5735	Approved
0.7357	Intermediate Similarity	NPD4626	Approved
0.7357	Intermediate Similarity	NPD3095	Discontinued
0.7329	Intermediate Similarity	NPD7095	Approved
0.7286	Intermediate Similarity	NPD5691	Approved
0.7273	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7097	Phase 1
0.7246	Intermediate Similarity	NPD7228	Approved
0.7237	Intermediate Similarity	NPD5763	Approved
0.7237	Intermediate Similarity	NPD5762	Approved
0.7234	Intermediate Similarity	NPD2932	Approved
0.7234	Intermediate Similarity	NPD3019	Approved
0.7226	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4628	Phase 3
0.7208	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4110	Phase 3
0.7153	Intermediate Similarity	NPD5327	Phase 3
0.7143	Intermediate Similarity	NPD6674	Discontinued
0.7134	Intermediate Similarity	NPD6234	Discontinued
0.7134	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4198	Discontinued
0.7114	Intermediate Similarity	NPD8032	Phase 2
0.7097	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3027	Phase 3
0.7063	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD37	Approved
0.702	Intermediate Similarity	NPD6355	Discontinued
0.7019	Intermediate Similarity	NPD7028	Phase 2
0.7012	Intermediate Similarity	NPD4965	Approved
0.7012	Intermediate Similarity	NPD4967	Phase 2
0.7012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD4966	Approved
0.7006	Intermediate Similarity	NPD7236	Approved
0.7	Intermediate Similarity	NPD5844	Phase 1
0.7	Intermediate Similarity	NPD7157	Approved
0.6994	Remote Similarity	NPD8313	Approved
0.6994	Remote Similarity	NPD8312	Approved
0.6993	Remote Similarity	NPD4059	Approved
0.6986	Remote Similarity	NPD8651	Approved
0.6978	Remote Similarity	NPD5283	Phase 1
0.6974	Remote Similarity	NPD6353	Approved
0.6971	Remote Similarity	NPD8150	Discontinued
0.6957	Remote Similarity	NPD228	Approved
0.6957	Remote Similarity	NPD3455	Phase 2
0.6954	Remote Similarity	NPD1613	Approved
0.6954	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5404	Approved
0.6948	Remote Similarity	NPD5405	Approved
0.6948	Remote Similarity	NPD5406	Approved
0.6948	Remote Similarity	NPD5408	Approved
0.6944	Remote Similarity	NPD3496	Discontinued
0.6933	Remote Similarity	NPD3764	Approved
0.6933	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6798	Discontinued
0.6929	Remote Similarity	NPD2629	Approved
0.6919	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD230	Phase 1
0.6908	Remote Similarity	NPD3657	Discovery
0.6903	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3020	Approved
0.6894	Remote Similarity	NPD1653	Approved
0.6892	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD4624	Approved
0.6883	Remote Similarity	NPD7742	Approved
0.6883	Remote Similarity	NPD7743	Approved
0.6871	Remote Similarity	NPD1283	Approved
0.6867	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD7833	Phase 2
0.6867	Remote Similarity	NPD7831	Phase 2
0.6867	Remote Similarity	NPD7008	Discontinued
0.6867	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7741	Discontinued
0.6842	Remote Similarity	NPD826	Approved
0.6842	Remote Similarity	NPD825	Approved
0.6839	Remote Similarity	NPD2935	Discontinued
0.6838	Remote Similarity	NPD3134	Approved
0.6835	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3026	Approved
0.6828	Remote Similarity	NPD3023	Approved
0.6824	Remote Similarity	NPD2489	Approved
0.6824	Remote Similarity	NPD27	Approved
0.6821	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3645	Discontinued
0.6807	Remote Similarity	NPD7768	Phase 2
0.6806	Remote Similarity	NPD3024	Approved
0.6806	Remote Similarity	NPD3025	Approved
0.6806	Remote Similarity	NPD1357	Approved
0.68	Remote Similarity	NPD4908	Phase 1
0.6797	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5124	Phase 1
0.679	Remote Similarity	NPD7239	Suspended
0.6788	Remote Similarity	NPD8455	Phase 2
0.6788	Remote Similarity	NPD1358	Approved
0.6788	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7635	Approved
0.6786	Remote Similarity	NPD7843	Approved
0.6786	Remote Similarity	NPD5535	Approved
0.6784	Remote Similarity	NPD7473	Discontinued
0.6783	Remote Similarity	NPD5536	Phase 2
0.6782	Remote Similarity	NPD7685	Pre-registration
0.6782	Remote Similarity	NPD7240	Approved
0.6781	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6677	Suspended
0.6753	Remote Similarity	NPD6653	Approved
0.6753	Remote Similarity	NPD4097	Suspended
0.6753	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD2861	Phase 2
0.6732	Remote Similarity	NPD2979	Phase 3
0.6731	Remote Similarity	NPD2438	Suspended
0.673	Remote Similarity	NPD8131	Suspended
0.6725	Remote Similarity	NPD6166	Phase 2
0.6725	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD2797	Approved
0.6709	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6232	Discontinued
0.6705	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.669	Remote Similarity	NPD5585	Approved
0.6689	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7819	Suspended
0.6685	Remote Similarity	NPD8434	Phase 2
0.6667	Remote Similarity	NPD7074	Phase 3
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD2859	Approved
0.6667	Remote Similarity	NPD2342	Discontinued
0.6667	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2860	Approved
0.6667	Remote Similarity	NPD1281	Approved
0.6667	Remote Similarity	NPD2799	Discontinued
0.6667	Remote Similarity	NPD2970	Approved
0.6667	Remote Similarity	NPD2969	Approved
0.6647	Remote Similarity	NPD7199	Phase 2
0.6647	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7041	Phase 2
0.6646	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7037	Approved
0.6644	Remote Similarity	NPD1778	Approved
0.6628	Remote Similarity	NPD4481	Phase 3
0.6627	Remote Similarity	NPD1934	Approved
0.6626	Remote Similarity	NPD5699	Approved
0.6623	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD9494	Approved
0.6621	Remote Similarity	NPD9545	Approved
0.662	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6619	Remote Similarity	NPD2684	Approved
0.6617	Remote Similarity	NPD288	Approved
0.661	Remote Similarity	NPD7311	Approved
0.661	Remote Similarity	NPD7313	Approved
0.661	Remote Similarity	NPD7312	Approved
0.661	Remote Similarity	NPD7310	Approved
0.6609	Remote Similarity	NPD7054	Approved
0.6608	Remote Similarity	NPD3051	Approved
0.6601	Remote Similarity	NPD3268	Approved
0.6601	Remote Similarity	NPD7985	Registered
0.66	Remote Similarity	NPD1470	Approved
0.6596	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2933	Approved
0.6591	Remote Similarity	NPD2934	Approved
0.6588	Remote Similarity	NPD4666	Phase 3
0.6582	Remote Similarity	NPD2346	Discontinued
0.6581	Remote Similarity	NPD555	Phase 2
0.6579	Remote Similarity	NPD2606	Approved
0.6579	Remote Similarity	NPD2605	Approved
0.6575	Remote Similarity	NPD4093	Discontinued
0.6573	Remote Similarity	NPD5951	Approved
0.6573	Remote Similarity	NPD7309	Approved
0.6571	Remote Similarity	NPD4750	Phase 3
0.6571	Remote Similarity	NPD7472	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