NPASS Compound

Structure

NPC233692 OpenBabel07101718322D 36 38 0 0 1 0 0 0 0 0999 V2000 -2.3221 0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3706 -3.1345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1643 1.2932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6778 1.6281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6754 -2.3822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2330 -3.2504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7612 -1.7893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9174 -2.2765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7612 -0.8150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0736 -1.7893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9174 -0.3278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6038 -0.5535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9049 -1.4801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8546 -1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1237 -3.4584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4872 0.8438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8797 0.0985 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5535 -2.6038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4402 0.6412 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8606 2.1588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0736 -0.8150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6520 -0.7241 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1706 -3.2558 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0504 -3.1573 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5421 -0.3278 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9267 0.3011 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2297 -0.3278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7023 -2.4332 0.0000 C 0 0 0 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 0.9116 3.1318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2717 -4.1240 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5810 -3.9745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2297 0.6466 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4392 -0.8698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8757 1.2741 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3859 -0.8150 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 18 1 0 0 0 0 4 20 1 0 0 0 0 5 28 1 0 0 0 0 6 28 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 21 2 0 0 0 0 11 21 1 0 0 0 0 12 13 2 0 0 0 0 12 17 1 0 0 0 0 13 28 1 0 0 0 0 14 18 2 0 0 0 0 14 22 1 0 0 0 0 15 23 1 0 0 0 0 15 24 1 0 0 0 0 16 19 1 0 0 0 0 16 29 1 0 0 0 0 17 1 1 6 0 0 0 17 26 1 0 0 0 0 18 23 1 0 0 0 0 19 3 1 6 0 0 0 19 25 1 0 0 0 0 20 30 2 0 0 0 0 20 35 1 0 0 0 0 21 27 1 0 0 0 0 22 25 1 0 0 0 0 22 29 1 6 0 0 0 23 31 1 6 0 0 0 24 28 1 0 0 0 0 24 32 1 1 0 0 0 25 36 1 6 0 0 0 26 29 1 6 0 0 0 26 35 1 0 0 0 0 27 33 2 0 0 0 0 27 36 1 0 0 0 0 29 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.28
Volume:	527.547
LogP:	3.703
LogD:	2.382
LogS:	-4.271
# Rotatable Bonds:	5
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.427
Synthetic Accessibility Score:	5.262
Fsp3:	0.586
Lipinski Rule-of-5:	Accepted
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:	-5.086
MDCK Permeability:	3.750935502466746e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.874
Human Intestinal Absorption (HIA):	0.971
20% Bioavailability (F20%):	0.075
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.126
Plasma Protein Binding (PPB):	96.11544799804688%
Volume Distribution (VD):	1.762
Pgp-substrate:	4.360591888427734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.105
CYP1A2-substrate:	0.05
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.346
CYP2C9-inhibitor:	0.109
CYP2C9-substrate:	0.679
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.659
CYP3A4-substrate:	0.338

ADMET: Excretion

Clearance (CL):	3.952
Half-life (T1/2):	0.086

ADMET: Toxicity

hERG Blockers:	0.293
Human Hepatotoxicity (H-HT):	0.942
Drug-inuced Liver Injury (DILI):	0.801
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.891
Maximum Recommended Daily Dose:	0.995
Skin Sensitization:	0.347
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.032
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC233692

Natural Product ID:	NPC233692
*Common Name:**	14Beta-Acetoxy-3Beta-Benzoyloxy-7Beta,9Alpha,15Beta-Trihydroxyjatropha-5E,11Ediene
IUPAC Name:	[(1S,2S,3aR,4S,5S,6E,9R,11R,12E,13aS)-4-acetyloxy-3a,9,11-trihydroxy-2,5,8,8,12-pentamethyl-2,3,4,5,9,10,11,13a-octahydro-1H-cyclopenta[12]annulen-1-yl] benzoate
Synonyms:
Standard InCHIKey:	ZUNZFMCDLSCUGC-AJKKUMOQSA-N
Standard InCHI:	InChI=1S/C29H40O7/c1-17-12-13-28(5,6)24(32)15-23(31)18(2)14-22-25(36-27(33)21-10-8-7-9-11-21)19(3)16-29(22,34)26(17)35-20(4)30/h7-14,17,19,22-26,31-32,34H,15-16H2,1-6H3/b13-12+,18-14+/t17-,19-,22-,23+,24+,25-,26-,29+/m0/s1
SMILES:	CC(=O)O[C@H]1[C@@H](C)/C=C/C(C)(C)[C@H](O)C[C@H](/C(=C/[C@@H]2[C@]1(O)C[C@@H]([C@@H]2OC(=O)c1ccccc1)C)/C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465867
PubChem CID:	24879540
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002877] Jatrophane and cyclojatrophane diterpenoids

*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
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18321057]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19099222]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724086]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31550154]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12682	Euphorbia helioscopia	Species	Euphorbiaceae	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	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[448452]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000.0	nM	PMID[448452]

☑ 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 NPC233692 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	256
0.1-0.2	876
0.2-0.3	2111
0.3-0.4	4939
0.4-0.5	9880
0.5-0.6	14296
0.6-0.7	8926
0.7-0.8	1118
0.8-0.85	174
0.85-0.9	71
0.9-0.95	29
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9841	High Similarity	NPC28836
0.9841	High Similarity	NPC311492
0.984	High Similarity	NPC239358
0.9762	High Similarity	NPC472248
0.9683	High Similarity	NPC233860
0.9612	High Similarity	NPC27721
0.9609	High Similarity	NPC200154
0.9538	High Similarity	NPC473301
0.9535	High Similarity	NPC202729
0.9248	High Similarity	NPC242355
0.9219	High Similarity	NPC475508
0.9104	High Similarity	NPC475413
0.9104	High Similarity	NPC474303
0.8971	High Similarity	NPC45307
0.8963	High Similarity	NPC473497
0.8939	High Similarity	NPC298547
0.8939	High Similarity	NPC472250
0.8939	High Similarity	NPC134937
0.8939	High Similarity	NPC153617
0.8939	High Similarity	NPC324898
0.8872	High Similarity	NPC279637
0.8872	High Similarity	NPC265459
0.8872	High Similarity	NPC79699
0.8872	High Similarity	NPC477367
0.8872	High Similarity	NPC149401
0.8872	High Similarity	NPC475262
0.8872	High Similarity	NPC472247
0.8872	High Similarity	NPC232888
0.8872	High Similarity	NPC290833
0.8857	High Similarity	NPC477099
0.8857	High Similarity	NPC477101
0.8857	High Similarity	NPC477097
0.8849	High Similarity	NPC205389
0.8837	High Similarity	NPC472706
0.8815	High Similarity	NPC9905
0.8806	High Similarity	NPC194769
0.8806	High Similarity	NPC285221
0.8797	High Similarity	NPC477368
0.8779	High Similarity	NPC272946
0.8777	High Similarity	NPC170668
0.8777	High Similarity	NPC478263
0.8769	High Similarity	NPC472707
0.8759	High Similarity	NPC192658
0.875	High Similarity	NPC162613
0.875	High Similarity	NPC87934
0.8741	High Similarity	NPC205305
0.8741	High Similarity	NPC86772
0.8741	High Similarity	NPC327511
0.8723	High Similarity	NPC25484
0.8723	High Similarity	NPC232583
0.8722	High Similarity	NPC477364
0.8705	High Similarity	NPC25043
0.8705	High Similarity	NPC134131
0.8705	High Similarity	NPC478264
0.8676	High Similarity	NPC53361
0.8676	High Similarity	NPC121268
0.8676	High Similarity	NPC325805
0.8676	High Similarity	NPC272523
0.8671	High Similarity	NPC477100
0.8671	High Similarity	NPC477098
0.8667	High Similarity	NPC217673
0.8667	High Similarity	NPC52523
0.8657	High Similarity	NPC477359
0.8643	High Similarity	NPC312393
0.8633	High Similarity	NPC34943
0.8613	High Similarity	NPC475660
0.8593	High Similarity	NPC270364
0.8571	High Similarity	NPC92867
0.8571	High Similarity	NPC311825
0.8571	High Similarity	NPC72915
0.8561	High Similarity	NPC153214
0.8551	High Similarity	NPC187566
0.8531	High Similarity	NPC161955
0.8527	High Similarity	NPC472703
0.8511	High Similarity	NPC240115
0.8511	High Similarity	NPC20255
0.8496	Intermediate Similarity	NPC42234
0.8483	Intermediate Similarity	NPC469456
0.8478	Intermediate Similarity	NPC275592
0.8478	Intermediate Similarity	NPC100913
0.8478	Intermediate Similarity	NPC472547
0.8467	Intermediate Similarity	NPC39549
0.8462	Intermediate Similarity	NPC476173
0.8462	Intermediate Similarity	NPC472704
0.8451	Intermediate Similarity	NPC327031
0.844	Intermediate Similarity	NPC125882
0.8429	Intermediate Similarity	NPC131966
0.8429	Intermediate Similarity	NPC95449
0.8429	Intermediate Similarity	NPC191387
0.8429	Intermediate Similarity	NPC477094
0.8429	Intermediate Similarity	NPC477096
0.8429	Intermediate Similarity	NPC82467
0.8417	Intermediate Similarity	NPC291599
0.8417	Intermediate Similarity	NPC97947
0.8417	Intermediate Similarity	NPC472576
0.8417	Intermediate Similarity	NPC118080
0.8417	Intermediate Similarity	NPC266374
0.8417	Intermediate Similarity	NPC41481
0.8417	Intermediate Similarity	NPC27377
0.8417	Intermediate Similarity	NPC87448
0.8409	Intermediate Similarity	NPC477365
0.8406	Intermediate Similarity	NPC170718
0.8406	Intermediate Similarity	NPC276652
0.8394	Intermediate Similarity	NPC472551
0.8394	Intermediate Similarity	NPC472545
0.8382	Intermediate Similarity	NPC48929
0.838	Intermediate Similarity	NPC473602
0.837	Intermediate Similarity	NPC477360
0.8358	Intermediate Similarity	NPC82712
0.8346	Intermediate Similarity	NPC477370
0.8345	Intermediate Similarity	NPC97667
0.8345	Intermediate Similarity	NPC90614
0.8345	Intermediate Similarity	NPC251294
0.8345	Intermediate Similarity	NPC171207
0.8333	Intermediate Similarity	NPC477366
0.8321	Intermediate Similarity	NPC477893
0.8321	Intermediate Similarity	NPC477896
0.831	Intermediate Similarity	NPC472556
0.8299	Intermediate Similarity	NPC70344
0.8298	Intermediate Similarity	NPC91703
0.8286	Intermediate Similarity	NPC473654
0.8286	Intermediate Similarity	NPC16912
0.8273	Intermediate Similarity	NPC475195
0.8261	Intermediate Similarity	NPC472374
0.8261	Intermediate Similarity	NPC472372
0.8258	Intermediate Similarity	NPC246166
0.8252	Intermediate Similarity	NPC477095
0.8248	Intermediate Similarity	NPC38420
0.8248	Intermediate Similarity	NPC136608
0.8239	Intermediate Similarity	NPC241951
0.8239	Intermediate Similarity	NPC475122
0.8239	Intermediate Similarity	NPC38696
0.8239	Intermediate Similarity	NPC470152
0.8239	Intermediate Similarity	NPC475759
0.8227	Intermediate Similarity	NPC51181
0.8227	Intermediate Similarity	NPC34012
0.8207	Intermediate Similarity	NPC125033
0.8195	Intermediate Similarity	NPC275576
0.8195	Intermediate Similarity	NPC477363
0.8194	Intermediate Similarity	NPC473760
0.8194	Intermediate Similarity	NPC132652
0.8188	Intermediate Similarity	NPC476784
0.8182	Intermediate Similarity	NPC472568
0.8182	Intermediate Similarity	NPC470157
0.8182	Intermediate Similarity	NPC96903
0.8182	Intermediate Similarity	NPC174982
0.8182	Intermediate Similarity	NPC477362
0.8182	Intermediate Similarity	NPC184817
0.8182	Intermediate Similarity	NPC158663
0.8182	Intermediate Similarity	NPC171525
0.8182	Intermediate Similarity	NPC476973
0.8182	Intermediate Similarity	NPC472571
0.8182	Intermediate Similarity	NPC177940
0.8182	Intermediate Similarity	NPC473088
0.8182	Intermediate Similarity	NPC469349
0.8182	Intermediate Similarity	NPC29704
0.8182	Intermediate Similarity	NPC471104
0.8182	Intermediate Similarity	NPC70403
0.8182	Intermediate Similarity	NPC200471
0.8182	Intermediate Similarity	NPC472575
0.8182	Intermediate Similarity	NPC472572
0.8182	Intermediate Similarity	NPC470159
0.8169	Intermediate Similarity	NPC163087
0.8169	Intermediate Similarity	NPC477894
0.8163	Intermediate Similarity	NPC472657
0.8163	Intermediate Similarity	NPC289021
0.8163	Intermediate Similarity	NPC472658
0.8163	Intermediate Similarity	NPC158546
0.8163	Intermediate Similarity	NPC471135
0.8156	Intermediate Similarity	NPC224491
0.8151	Intermediate Similarity	NPC96308
0.8148	Intermediate Similarity	NPC37968
0.8138	Intermediate Similarity	NPC76103
0.8134	Intermediate Similarity	NPC169913
0.8134	Intermediate Similarity	NPC477357
0.8129	Intermediate Similarity	NPC477358
0.8125	Intermediate Similarity	NPC48599
0.8125	Intermediate Similarity	NPC209592
0.8116	Intermediate Similarity	NPC322503
0.8116	Intermediate Similarity	NPC470143
0.8116	Intermediate Similarity	NPC474608
0.8112	Intermediate Similarity	NPC57628
0.8112	Intermediate Similarity	NPC472569
0.8112	Intermediate Similarity	NPC70716
0.8112	Intermediate Similarity	NPC472573
0.8112	Intermediate Similarity	NPC95810
0.8112	Intermediate Similarity	NPC472570
0.8112	Intermediate Similarity	NPC125106
0.8112	Intermediate Similarity	NPC476974
0.8112	Intermediate Similarity	NPC95265
0.8112	Intermediate Similarity	NPC163719
0.8112	Intermediate Similarity	NPC188865
0.8112	Intermediate Similarity	NPC11685
0.8112	Intermediate Similarity	NPC25768
0.8108	Intermediate Similarity	NPC132599
0.8108	Intermediate Similarity	NPC469730
0.8108	Intermediate Similarity	NPC478235
0.8108	Intermediate Similarity	NPC473632
0.8099	Intermediate Similarity	NPC472546
0.8099	Intermediate Similarity	NPC475135

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 NPC233692 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	648
0.2-0.3	1567
0.3-0.4	2770
0.4-0.5	2212
0.5-0.6	1359
0.6-0.7	338
0.7-0.8	38
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8409	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD7236	Approved
0.7903	Intermediate Similarity	NPD6685	Approved
0.7785	Intermediate Similarity	NPD7239	Suspended
0.7698	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2629	Approved
0.7671	Intermediate Similarity	NPD4628	Phase 3
0.7661	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD5765	Approved
0.7656	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD7741	Discontinued
0.7586	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6002	Phase 3
0.7586	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6005	Phase 3
0.7586	Intermediate Similarity	NPD6004	Phase 3
0.7562	Intermediate Similarity	NPD7799	Discontinued
0.7557	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6653	Approved
0.7535	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2182	Approved
0.7482	Intermediate Similarity	NPD6085	Phase 2
0.7482	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD6912	Phase 3
0.7381	Intermediate Similarity	NPD6647	Phase 2
0.7364	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7058	Phase 2
0.7325	Intermediate Similarity	NPD7057	Phase 3
0.7299	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7137	Phase 2
0.7273	Intermediate Similarity	NPD7685	Pre-registration
0.7239	Intermediate Similarity	NPD4198	Discontinued
0.7234	Intermediate Similarity	NPD5647	Approved
0.7206	Intermediate Similarity	NPD9545	Approved
0.7203	Intermediate Similarity	NPD7008	Discontinued
0.719	Intermediate Similarity	NPD6273	Approved
0.7188	Intermediate Similarity	NPD164	Approved
0.7176	Intermediate Similarity	NPD2067	Discontinued
0.7163	Intermediate Similarity	NPD6362	Approved
0.7153	Intermediate Similarity	NPD3764	Approved
0.7089	Intermediate Similarity	NPD5761	Phase 2
0.7089	Intermediate Similarity	NPD5760	Phase 2
0.7063	Intermediate Similarity	NPD9495	Approved
0.7037	Intermediate Similarity	NPD5951	Approved
0.7015	Intermediate Similarity	NPD6858	Approved
0.7015	Intermediate Similarity	NPD7094	Approved
0.7008	Intermediate Similarity	NPD1238	Approved
0.7007	Intermediate Similarity	NPD230	Phase 1
0.7007	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD4806	Approved
0.7	Intermediate Similarity	NPD4807	Approved
0.7	Intermediate Similarity	NPD6287	Discontinued
0.7	Intermediate Similarity	NPD5763	Approved
0.6992	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7961	Discontinued
0.6986	Remote Similarity	NPD6663	Approved
0.6978	Remote Similarity	NPD5126	Approved
0.6978	Remote Similarity	NPD5306	Approved
0.6978	Remote Similarity	NPD5305	Approved
0.6978	Remote Similarity	NPD5125	Phase 3
0.6944	Remote Similarity	NPD3663	Approved
0.6944	Remote Similarity	NPD5736	Approved
0.6944	Remote Similarity	NPD3662	Phase 3
0.6944	Remote Similarity	NPD3664	Approved
0.6944	Remote Similarity	NPD3661	Approved
0.6933	Remote Similarity	NPD8127	Discontinued
0.6923	Remote Similarity	NPD1237	Approved
0.6903	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5048	Discontinued
0.6867	Remote Similarity	NPD7305	Phase 1
0.6864	Remote Similarity	NPD6764	Approved
0.6864	Remote Similarity	NPD8368	Discontinued
0.6864	Remote Similarity	NPD6765	Approved
0.6863	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2575	Approved
0.686	Remote Similarity	NPD8434	Phase 2
0.6857	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1930	Approved
0.6846	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD1929	Approved
0.6842	Remote Similarity	NPD8407	Phase 2
0.6835	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6190	Approved
0.6815	Remote Similarity	NPD969	Suspended
0.6812	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD9493	Approved
0.6809	Remote Similarity	NPD4136	Approved
0.6809	Remote Similarity	NPD4106	Approved
0.6809	Remote Similarity	NPD4135	Approved
0.6794	Remote Similarity	NPD5909	Discontinued
0.6792	Remote Similarity	NPD6599	Discontinued
0.6774	Remote Similarity	NPD9258	Approved
0.6774	Remote Similarity	NPD9256	Approved
0.677	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7033	Discontinued
0.6753	Remote Similarity	NPD8166	Discontinued
0.6748	Remote Similarity	NPD7075	Discontinued
0.6744	Remote Similarity	NPD2066	Phase 3
0.6738	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7458	Discontinued
0.6715	Remote Similarity	NPD2652	Approved
0.6715	Remote Similarity	NPD2650	Approved
0.6714	Remote Similarity	NPD7009	Phase 2
0.6712	Remote Similarity	NPD5204	Approved
0.671	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD5403	Approved
0.6705	Remote Similarity	NPD6784	Approved
0.6705	Remote Similarity	NPD6785	Approved
0.6693	Remote Similarity	NPD1693	Approved
0.669	Remote Similarity	NPD3094	Phase 2
0.6688	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4380	Phase 2
0.6686	Remote Similarity	NPD8360	Approved
0.6686	Remote Similarity	NPD8361	Approved
0.6667	Remote Similarity	NPD1088	Approved
0.6667	Remote Similarity	NPD4105	Approved
0.6667	Remote Similarity	NPD7266	Discontinued
0.6667	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4102	Approved
0.6667	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6371	Approved
0.6645	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD4110	Phase 3
0.6645	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7715	Approved
0.6644	Remote Similarity	NPD7714	Approved
0.6643	Remote Similarity	NPD7610	Discontinued
0.6626	Remote Similarity	NPD5402	Approved
0.6624	Remote Similarity	NPD6799	Approved
0.6621	Remote Similarity	NPD1876	Approved
0.6614	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7497	Discontinued
0.6609	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD6801	Discontinued
0.6601	Remote Similarity	NPD2935	Discontinued
0.66	Remote Similarity	NPD4140	Approved
0.6597	Remote Similarity	NPD1608	Approved
0.6597	Remote Similarity	NPD6637	Approved
0.6597	Remote Similarity	NPD9717	Approved
0.6591	Remote Similarity	NPD8435	Approved
0.6585	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD2533	Approved
0.6582	Remote Similarity	NPD2534	Approved
0.6582	Remote Similarity	NPD2532	Approved
0.6582	Remote Similarity	NPD5401	Approved
0.6579	Remote Similarity	NPD2567	Approved
0.6579	Remote Similarity	NPD2569	Approved
0.6575	Remote Similarity	NPD2625	Approved
0.6575	Remote Similarity	NPD2797	Approved
0.6575	Remote Similarity	NPD2626	Approved
0.6575	Remote Similarity	NPD2159	Approved
0.6575	Remote Similarity	NPD2627	Approved
0.6575	Remote Similarity	NPD2160	Approved
0.6575	Remote Similarity	NPD2628	Approved
0.6571	Remote Similarity	NPD8150	Discontinued
0.6569	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD447	Suspended
0.6554	Remote Similarity	NPD6832	Phase 2
0.6554	Remote Similarity	NPD4620	Approved
0.6554	Remote Similarity	NPD5201	Approved
0.6554	Remote Similarity	NPD5203	Approved
0.6554	Remote Similarity	NPD2613	Approved
0.6554	Remote Similarity	NPD4617	Approved
0.6547	Remote Similarity	NPD4766	Approved
0.6545	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD4234	Approved
0.6544	Remote Similarity	NPD4233	Approved
0.6538	Remote Similarity	NPD7003	Approved
0.6538	Remote Similarity	NPD3750	Approved
0.6538	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD4308	Phase 3
0.6536	Remote Similarity	NPD2799	Discontinued
0.6533	Remote Similarity	NPD6233	Phase 2
0.6522	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6406	Approved
0.6519	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD970	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7095	Approved
0.6508	Remote Similarity	NPD1089	Approved
0.6508	Remote Similarity	NPD1090	Approved
0.6508	Remote Similarity	NPD1086	Approved
0.6507	Remote Similarity	NPD5667	Approved
0.65	Remote Similarity	NPD7157	Approved
0.6494	Remote Similarity	NPD8312	Approved
0.6494	Remote Similarity	NPD1551	Phase 2
0.6494	Remote Similarity	NPD8313	Approved
0.6491	Remote Similarity	NPD5844	Phase 1
0.649	Remote Similarity	NPD5119	Approved
0.649	Remote Similarity	NPD5120	Approved
0.649	Remote Similarity	NPD5121	Approved
0.6489	Remote Similarity	NPD7798	Approved
0.6485	Remote Similarity	NPD7768	Phase 2
0.6484	Remote Similarity	NPD1202	Approved
0.6481	Remote Similarity	NPD7028	Phase 2
0.6475	Remote Similarity	NPD6010	Discontinued

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