NPASS Compound

Structure

NPC311492 OpenBabel07101718272D 41 43 0 0 1 0 0 0 0 0999 V2000 1.3747 3.1439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1708 -1.2971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0084 3.0644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3457 2.5624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6864 2.3893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2427 3.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8342 -1.0747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7784 1.7947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9321 2.2833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7784 0.8174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0857 1.7947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9321 0.3288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9136 1.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6116 0.5551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8571 1.6822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1271 3.4687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5551 2.6116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4446 -0.6432 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5647 3.9352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0948 1.6900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0857 0.8174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6539 0.7263 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1711 3.2655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0565 3.1667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5467 0.3288 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4886 -0.8463 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2394 0.3288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9294 -0.3020 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7104 2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8854 -0.0988 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0970 4.7548 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0463 1.5806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2725 4.1363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0911 -1.7391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2394 -0.6485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8783 -1.2779 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7050 -0.6311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5888 3.9863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3930 0.8174 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4405 0.8724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 3 19 1 0 0 0 0 4 20 1 0 0 0 0 5 29 1 0 0 0 0 6 29 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 14 2 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 17 2 0 0 0 0 15 22 1 0 0 0 0 16 23 1 0 0 0 0 16 24 1 0 0 0 0 17 23 1 0 0 0 0 18 2 1 1 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 19 32 2 0 0 0 0 19 39 1 0 0 0 0 20 33 2 0 0 0 0 20 41 1 0 0 0 0 21 27 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 1 0 0 0 23 34 1 1 0 0 0 24 29 1 0 0 0 0 24 39 1 1 0 0 0 25 40 1 1 0 0 0 26 31 1 6 0 0 0 26 35 1 0 0 0 0 27 36 2 0 0 0 0 27 40 1 0 0 0 0 28 30 1 6 0 0 0 28 31 1 0 0 0 0 28 37 1 0 0 0 0 30 7 1 6 0 0 0 30 38 1 0 0 0 0 31 41 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	574.28
Volume:	585.873
LogP:	3.191
LogD:	2.054
LogS:	-4.046
# Rotatable Bonds:	7
TPSA:	159.82
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.239
Synthetic Accessibility Score:	5.552
Fsp3:	0.581
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:	-5.532
MDCK Permeability:	8.947498281486332e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.984
Human Intestinal Absorption (HIA):	0.674
20% Bioavailability (F20%):	0.067
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.464
Plasma Protein Binding (PPB):	80.19998168945312%
Volume Distribution (VD):	1.415
Pgp-substrate:	15.477429389953613%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.147
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.14
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.059
CYP3A4-inhibitor:	0.431
CYP3A4-substrate:	0.293

ADMET: Excretion

Clearance (CL):	2.474
Half-life (T1/2):	0.387

ADMET: Toxicity

hERG Blockers:	0.708
Human Hepatotoxicity (H-HT):	0.983
Drug-inuced Liver Injury (DILI):	0.714
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.743
Maximum Recommended Daily Dose:	0.986
Skin Sensitization:	0.171
Carcinogencity:	0.032
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC311492

Natural Product ID:	NPC311492
*Common Name:**	1Alpha,7Beta,13Beta,14Alpha-Tetrahydroxy-3Beta-Benzoyloxy-9Beta,15Beta-Diacetoxyjatropha-5,11 E-Diene
IUPAC Name:	[(1S,2S,3S,3aS,4R,5S,6E,9S,11R,12Z,13aS)-3a,9-diacetyloxy-3,4,5,11-tetrahydroxy-2,5,8,8,12-pentamethyl-1,2,3,4,9,10,11,13a-octahydrocyclopenta[12]annulen-1-yl] benzoate
Synonyms:
Standard InCHIKey:	DVFBOMVAFAYEHO-IPYPLBDFSA-N
Standard InCHI:	InChI=1S/C31H42O10/c1-17-15-22-25(40-27(36)21-11-9-8-10-12-21)18(2)26(35)31(22,41-20(4)33)28(37)30(7,38)14-13-29(5,6)24(16-23(17)34)39-19(3)32/h8-15,18,22-26,28,34-35,37-38H,16H2,1-7H3/b14-13+,17-15-/t18-,22+,23-,24+,25+,26+,28-,30+,31+/m1/s1
SMILES:	C/C/1=C/[C@H]2[C@H]([C@@H](C)[C@@H]([C@@]2([C@@H]([C@](C)(/C=C/C(C)(C)[C@H](C[C@H]1O)OC(=O)C)O)O)OC(=O)C)O)OC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400942
PubChem CID:	23642403
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
NPO31109	Pedilanthus tithymaloides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17844996]
NPO31109	Pedilanthus tithymaloides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31109	Pedilanthus tithymaloides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	100.0	ug.mL-1	PMID[455255]

☑ 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 NPC311492 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	263
0.1-0.2	894
0.2-0.3	2168
0.3-0.4	5071
0.4-0.5	10086
0.5-0.6	14545
0.6-0.7	8379
0.7-0.8	1006
0.8-0.85	160
0.85-0.9	66
0.9-0.95	38
0.95-1	21

Similarity Score	Similarity Level	Natural Product ID
0.9843	High Similarity	NPC28836
0.9841	High Similarity	NPC239358
0.9841	High Similarity	NPC233692
0.9767	High Similarity	NPC27721
0.9764	High Similarity	NPC472248
0.9692	High Similarity	NPC473301
0.969	High Similarity	NPC202729
0.9685	High Similarity	NPC233860
0.9612	High Similarity	NPC200154
0.9254	High Similarity	NPC242355
0.9225	High Similarity	NPC475508
0.9118	High Similarity	NPC45307
0.9111	High Similarity	NPC474303
0.9111	High Similarity	NPC475413
0.9023	High Similarity	NPC149401
0.9023	High Similarity	NPC279637
0.9023	High Similarity	NPC79699
0.9	High Similarity	NPC477097
0.9	High Similarity	NPC477101
0.9	High Similarity	NPC477099
0.8993	High Similarity	NPC205389
0.8971	High Similarity	NPC473497
0.8955	High Similarity	NPC285221
0.8955	High Similarity	NPC194769
0.8947	High Similarity	NPC134937
0.8947	High Similarity	NPC324898
0.8947	High Similarity	NPC153617
0.8947	High Similarity	NPC298547
0.8947	High Similarity	NPC472250
0.8881	High Similarity	NPC472247
0.8881	High Similarity	NPC290833
0.8881	High Similarity	NPC265459
0.8881	High Similarity	NPC475262
0.8865	High Similarity	NPC232583
0.8865	High Similarity	NPC25484
0.8824	High Similarity	NPC53361
0.8824	High Similarity	NPC272523
0.8824	High Similarity	NPC325805
0.8824	High Similarity	NPC9905
0.8824	High Similarity	NPC121268
0.8811	High Similarity	NPC477098
0.8811	High Similarity	NPC477100
0.8788	High Similarity	NPC272946
0.8786	High Similarity	NPC312393
0.8786	High Similarity	NPC170668
0.8768	High Similarity	NPC192658
0.8759	High Similarity	NPC475660
0.8759	High Similarity	NPC162613
0.8759	High Similarity	NPC87934
0.875	High Similarity	NPC327511
0.875	High Similarity	NPC86772
0.875	High Similarity	NPC205305
0.8741	High Similarity	NPC232888
0.8741	High Similarity	NPC477367
0.8702	High Similarity	NPC472706
0.8667	High Similarity	NPC477368
0.8652	High Similarity	NPC478263
0.8643	High Similarity	NPC34943
0.8636	High Similarity	NPC472707
0.8603	High Similarity	NPC270364
0.8593	High Similarity	NPC477364
0.8592	High Similarity	NPC327031
0.8582	High Similarity	NPC25043
0.8582	High Similarity	NPC134131
0.8582	High Similarity	NPC478264
0.8582	High Similarity	NPC311825
0.8582	High Similarity	NPC92867
0.8571	High Similarity	NPC477094
0.8571	High Similarity	NPC477096
0.8571	High Similarity	NPC153214
0.8561	High Similarity	NPC187566
0.854	High Similarity	NPC52523
0.854	High Similarity	NPC217673
0.8529	High Similarity	NPC477359
0.8521	High Similarity	NPC20255
0.8521	High Similarity	NPC240115
0.8493	Intermediate Similarity	NPC469456
0.8489	Intermediate Similarity	NPC472547
0.8472	Intermediate Similarity	NPC476173
0.8451	Intermediate Similarity	NPC125882
0.8444	Intermediate Similarity	NPC72915
0.844	Intermediate Similarity	NPC95449
0.844	Intermediate Similarity	NPC82467
0.844	Intermediate Similarity	NPC131966
0.844	Intermediate Similarity	NPC191387
0.8429	Intermediate Similarity	NPC266374
0.8429	Intermediate Similarity	NPC27377
0.8429	Intermediate Similarity	NPC41481
0.8429	Intermediate Similarity	NPC291599
0.8429	Intermediate Similarity	NPC97947
0.8429	Intermediate Similarity	NPC472576
0.8429	Intermediate Similarity	NPC87448
0.8429	Intermediate Similarity	NPC118080
0.8417	Intermediate Similarity	NPC276652
0.8414	Intermediate Similarity	NPC161955
0.8397	Intermediate Similarity	NPC472703
0.8392	Intermediate Similarity	NPC473602
0.8392	Intermediate Similarity	NPC477095
0.837	Intermediate Similarity	NPC42234
0.8357	Intermediate Similarity	NPC275592
0.8357	Intermediate Similarity	NPC90614
0.8357	Intermediate Similarity	NPC171207
0.8357	Intermediate Similarity	NPC97667
0.8357	Intermediate Similarity	NPC251294
0.8357	Intermediate Similarity	NPC100913
0.8345	Intermediate Similarity	NPC39549
0.8333	Intermediate Similarity	NPC472704
0.8322	Intermediate Similarity	NPC472556
0.8311	Intermediate Similarity	NPC70344
0.8299	Intermediate Similarity	NPC471135
0.8298	Intermediate Similarity	NPC16912
0.8298	Intermediate Similarity	NPC473654
0.8288	Intermediate Similarity	NPC96308
0.8286	Intermediate Similarity	NPC170718
0.8286	Intermediate Similarity	NPC475195
0.8284	Intermediate Similarity	NPC477365
0.8276	Intermediate Similarity	NPC76103
0.8273	Intermediate Similarity	NPC472551
0.8273	Intermediate Similarity	NPC472545
0.8273	Intermediate Similarity	NPC472374
0.8273	Intermediate Similarity	NPC472372
0.8261	Intermediate Similarity	NPC38420
0.8261	Intermediate Similarity	NPC48929
0.8261	Intermediate Similarity	NPC136608
0.8252	Intermediate Similarity	NPC470152
0.8252	Intermediate Similarity	NPC38696
0.8252	Intermediate Similarity	NPC475759
0.8252	Intermediate Similarity	NPC241951
0.8248	Intermediate Similarity	NPC477360
0.8239	Intermediate Similarity	NPC34012
0.8239	Intermediate Similarity	NPC475135
0.8235	Intermediate Similarity	NPC82712
0.8222	Intermediate Similarity	NPC477370
0.8219	Intermediate Similarity	NPC125033
0.8209	Intermediate Similarity	NPC477366
0.8207	Intermediate Similarity	NPC473760
0.8201	Intermediate Similarity	NPC477893
0.8201	Intermediate Similarity	NPC477896
0.82	Intermediate Similarity	NPC476784
0.82	Intermediate Similarity	NPC319404
0.8194	Intermediate Similarity	NPC469349
0.8194	Intermediate Similarity	NPC177940
0.8194	Intermediate Similarity	NPC473088
0.8194	Intermediate Similarity	NPC29704
0.8194	Intermediate Similarity	NPC471104
0.8194	Intermediate Similarity	NPC200471
0.8194	Intermediate Similarity	NPC472572
0.8194	Intermediate Similarity	NPC472575
0.8194	Intermediate Similarity	NPC470159
0.8194	Intermediate Similarity	NPC70403
0.8194	Intermediate Similarity	NPC96903
0.8194	Intermediate Similarity	NPC472568
0.8194	Intermediate Similarity	NPC174982
0.8194	Intermediate Similarity	NPC184817
0.8194	Intermediate Similarity	NPC470157
0.8194	Intermediate Similarity	NPC158663
0.8194	Intermediate Similarity	NPC171525
0.8194	Intermediate Similarity	NPC476973
0.8194	Intermediate Similarity	NPC472571
0.8188	Intermediate Similarity	NPC475548
0.8188	Intermediate Similarity	NPC229354
0.8188	Intermediate Similarity	NPC475638
0.8188	Intermediate Similarity	NPC290683
0.8182	Intermediate Similarity	NPC477894
0.8182	Intermediate Similarity	NPC91703
0.8182	Intermediate Similarity	NPC163087
0.8176	Intermediate Similarity	NPC472658
0.8176	Intermediate Similarity	NPC158546
0.8176	Intermediate Similarity	NPC289021
0.8176	Intermediate Similarity	NPC472657
0.8138	Intermediate Similarity	NPC48599
0.8138	Intermediate Similarity	NPC209592
0.8134	Intermediate Similarity	NPC246166
0.8133	Intermediate Similarity	NPC318447
0.8133	Intermediate Similarity	NPC322048
0.8129	Intermediate Similarity	NPC470143
0.8129	Intermediate Similarity	NPC322503
0.8125	Intermediate Similarity	NPC95265
0.8125	Intermediate Similarity	NPC163719
0.8125	Intermediate Similarity	NPC188865
0.8125	Intermediate Similarity	NPC475122
0.8125	Intermediate Similarity	NPC25768
0.8125	Intermediate Similarity	NPC11685
0.8125	Intermediate Similarity	NPC472573
0.8125	Intermediate Similarity	NPC57628
0.8125	Intermediate Similarity	NPC472569
0.8125	Intermediate Similarity	NPC70716
0.8125	Intermediate Similarity	NPC95810
0.8125	Intermediate Similarity	NPC472570
0.8125	Intermediate Similarity	NPC476974
0.8125	Intermediate Similarity	NPC186296
0.8125	Intermediate Similarity	NPC125106
0.8121	Intermediate Similarity	NPC469730
0.8121	Intermediate Similarity	NPC132599
0.8121	Intermediate Similarity	NPC478235
0.8121	Intermediate Similarity	NPC473632
0.8112	Intermediate Similarity	NPC51181
0.8112	Intermediate Similarity	NPC472546
0.8108	Intermediate Similarity	NPC283875
0.8108	Intermediate Similarity	NPC469647

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 NPC311492 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	221
0.1-0.2	669
0.2-0.3	1618
0.3-0.4	2815
0.4-0.5	2203
0.5-0.6	1278
0.6-0.7	312
0.7-0.8	33
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
0.8284	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD7236	Approved
0.78	Intermediate Similarity	NPD7239	Suspended
0.7778	Intermediate Similarity	NPD6685	Approved
0.7688	Intermediate Similarity	NPD7799	Discontinued
0.7589	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2629	Approved
0.7568	Intermediate Similarity	NPD4628	Phase 3
0.7552	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD5765	Approved
0.754	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6005	Phase 3
0.7483	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6002	Phase 3
0.7483	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6004	Phase 3
0.7481	Intermediate Similarity	NPD6912	Phase 3
0.7481	Intermediate Similarity	NPD7741	Discontinued
0.7448	Intermediate Similarity	NPD6653	Approved
0.7444	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7685	Pre-registration
0.7385	Intermediate Similarity	NPD2182	Approved
0.7376	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD6085	Phase 2
0.7342	Intermediate Similarity	NPD7058	Phase 2
0.7342	Intermediate Similarity	NPD7057	Phase 3
0.7297	Intermediate Similarity	NPD7137	Phase 2
0.7266	Intermediate Similarity	NPD6647	Phase 2
0.7252	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5647	Approved
0.7132	Intermediate Similarity	NPD4198	Discontinued
0.7103	Intermediate Similarity	NPD7008	Discontinued
0.7101	Intermediate Similarity	NPD9545	Approved
0.7097	Intermediate Similarity	NPD6273	Approved
0.7077	Intermediate Similarity	NPD164	Approved
0.7068	Intermediate Similarity	NPD2067	Discontinued
0.7063	Intermediate Similarity	NPD6362	Approved
0.7055	Intermediate Similarity	NPD3764	Approved
0.7006	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5761	Phase 2
0.7	Intermediate Similarity	NPD5760	Phase 2
0.6953	Remote Similarity	NPD9495	Approved
0.6951	Remote Similarity	NPD8127	Discontinued
0.6934	Remote Similarity	NPD5951	Approved
0.6923	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6355	Discontinued
0.6913	Remote Similarity	NPD230	Phase 1
0.6912	Remote Similarity	NPD7094	Approved
0.6912	Remote Similarity	NPD6858	Approved
0.6908	Remote Similarity	NPD5762	Approved
0.6908	Remote Similarity	NPD5763	Approved
0.6901	Remote Similarity	NPD6287	Discontinued
0.6901	Remote Similarity	NPD4806	Approved
0.6901	Remote Similarity	NPD4807	Approved
0.6899	Remote Similarity	NPD1238	Approved
0.6892	Remote Similarity	NPD7961	Discontinued
0.6892	Remote Similarity	NPD6663	Approved
0.6889	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8368	Discontinued
0.6879	Remote Similarity	NPD5126	Approved
0.6879	Remote Similarity	NPD8434	Phase 2
0.6879	Remote Similarity	NPD5306	Approved
0.6879	Remote Similarity	NPD5305	Approved
0.6879	Remote Similarity	NPD5125	Phase 3
0.686	Remote Similarity	NPD8407	Phase 2
0.6849	Remote Similarity	NPD3663	Approved
0.6849	Remote Similarity	NPD3664	Approved
0.6849	Remote Similarity	NPD3661	Approved
0.6849	Remote Similarity	NPD5736	Approved
0.6849	Remote Similarity	NPD3662	Phase 3
0.6839	Remote Similarity	NPD6190	Approved
0.6818	Remote Similarity	NPD1237	Approved
0.6815	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6764	Approved
0.6784	Remote Similarity	NPD6765	Approved
0.6776	Remote Similarity	NPD7305	Phase 1
0.6774	Remote Similarity	NPD2575	Approved
0.6774	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7075	Discontinued
0.6767	Remote Similarity	NPD5048	Discontinued
0.6761	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD1930	Approved
0.6742	Remote Similarity	NPD1929	Approved
0.6742	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5403	Approved
0.6715	Remote Similarity	NPD969	Suspended
0.6714	Remote Similarity	NPD9493	Approved
0.6714	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4136	Approved
0.6713	Remote Similarity	NPD4135	Approved
0.6713	Remote Similarity	NPD4106	Approved
0.6712	Remote Similarity	NPD3094	Phase 2
0.6708	Remote Similarity	NPD4380	Phase 2
0.6708	Remote Similarity	NPD6599	Discontinued
0.6705	Remote Similarity	NPD8361	Approved
0.6705	Remote Similarity	NPD8360	Approved
0.6692	Remote Similarity	NPD5909	Discontinued
0.6688	Remote Similarity	NPD7266	Discontinued
0.6687	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9258	Approved
0.6667	Remote Similarity	NPD9256	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD8166	Discontinued
0.6646	Remote Similarity	NPD5402	Approved
0.6646	Remote Similarity	NPD7458	Discontinued
0.6645	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD2066	Phase 3
0.663	Remote Similarity	NPD7497	Discontinued
0.6629	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6785	Approved
0.6629	Remote Similarity	NPD6784	Approved
0.6626	Remote Similarity	NPD6801	Discontinued
0.6624	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD5204	Approved
0.662	Remote Similarity	NPD7009	Phase 2
0.6619	Remote Similarity	NPD2652	Approved
0.6619	Remote Similarity	NPD2650	Approved
0.661	Remote Similarity	NPD8435	Approved
0.6606	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5401	Approved
0.6603	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD8150	Discontinued
0.6589	Remote Similarity	NPD1693	Approved
0.6581	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6832	Phase 2
0.6573	Remote Similarity	NPD4105	Approved
0.6573	Remote Similarity	NPD4102	Approved
0.6569	Remote Similarity	NPD6371	Approved
0.6566	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1088	Approved
0.6561	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD4110	Phase 3
0.6556	Remote Similarity	NPD7715	Approved
0.6556	Remote Similarity	NPD7714	Approved
0.6549	Remote Similarity	NPD7610	Discontinued
0.6541	Remote Similarity	NPD6799	Approved
0.6531	Remote Similarity	NPD1876	Approved
0.6525	Remote Similarity	NPD7157	Approved
0.6516	Remote Similarity	NPD2935	Discontinued
0.6514	Remote Similarity	NPD8312	Approved
0.6514	Remote Similarity	NPD8313	Approved
0.6513	Remote Similarity	NPD4140	Approved
0.6512	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6507	Remote Similarity	NPD6637	Approved
0.6507	Remote Similarity	NPD9717	Approved
0.6507	Remote Similarity	NPD1608	Approved
0.65	Remote Similarity	NPD2532	Approved
0.65	Remote Similarity	NPD2534	Approved
0.65	Remote Similarity	NPD2533	Approved
0.6494	Remote Similarity	NPD2569	Approved
0.6494	Remote Similarity	NPD2567	Approved
0.6486	Remote Similarity	NPD2159	Approved
0.6486	Remote Similarity	NPD2628	Approved
0.6486	Remote Similarity	NPD2627	Approved
0.6486	Remote Similarity	NPD2626	Approved
0.6486	Remote Similarity	NPD2797	Approved
0.6486	Remote Similarity	NPD2625	Approved
0.6486	Remote Similarity	NPD2160	Approved
0.6485	Remote Similarity	NPD8455	Phase 2
0.6485	Remote Similarity	NPD7819	Suspended
0.6484	Remote Similarity	NPD8485	Approved
0.6475	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD447	Suspended
0.6471	Remote Similarity	NPD5735	Approved
0.6467	Remote Similarity	NPD4620	Approved
0.6467	Remote Similarity	NPD5201	Approved
0.6467	Remote Similarity	NPD5203	Approved
0.6467	Remote Similarity	NPD4617	Approved
0.6467	Remote Similarity	NPD2613	Approved
0.6456	Remote Similarity	NPD7003	Approved
0.6456	Remote Similarity	NPD3750	Approved
0.6456	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD4766	Approved
0.6452	Remote Similarity	NPD2799	Discontinued
0.6452	Remote Similarity	NPD4308	Phase 3
0.645	Remote Similarity	NPD7199	Phase 2
0.6449	Remote Similarity	NPD4233	Approved
0.6449	Remote Similarity	NPD4234	Approved
0.6447	Remote Similarity	NPD6233	Phase 2
0.6442	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD3092	Approved
0.6433	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD7095	Approved
0.6424	Remote Similarity	NPD37	Approved
0.6423	Remote Similarity	NPD6406	Approved
0.6419	Remote Similarity	NPD5667	Approved
0.6416	Remote Similarity	NPD5844	Phase 1
0.641	Remote Similarity	NPD1551	Phase 2
0.6407	Remote Similarity	NPD4967	Phase 2
0.6407	Remote Similarity	NPD7768	Phase 2
0.6407	Remote Similarity	NPD4966	Approved
0.6407	Remote Similarity	NPD4965	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