NPASS Compound

Structure

CID217918 OpenBabel06191716012D 42 46 0 0 1 0 0 0 0 0999 V2000 -3.0141 0.5400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5693 -0.6510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9104 1.9104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4152 3.0477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5224 3.1652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2152 0.8320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0479 2.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7033 2.1430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4997 3.6895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8104 2.0255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6068 3.5720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7799 -1.3509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0663 1.3628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9006 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3893 1.1886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1175 0.0634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0405 2.1435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2622 2.7399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6858 0.9571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5598 -0.9006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.9006 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6469 1.8829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8800 1.0130 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7799 0.4503 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4297 0.2331 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5468 1.3202 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3693 2.6224 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8670 2.3332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5598 0.0000 0.0000 C 0 0 1 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 -0.9971 2.1001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0104 -0.0541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5743 3.8833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5683 0.0642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3398 -1.3509 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9780 -0.4814 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8210 3.3369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6768 2.9418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9006 -0.9006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7729 0.8955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0246 1.7904 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2331 0.8699 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 28 1 0 0 0 0 5 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 18 2 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 31 1 0 0 0 0 14 30 1 0 0 0 0 14 39 1 0 0 0 0 15 19 1 0 0 0 0 15 22 2 0 0 0 0 16 32 2 0 0 0 0 16 40 1 0 0 0 0 17 33 2 0 0 0 0 17 42 1 0 0 0 0 18 27 1 0 0 0 0 19 34 2 0 0 0 0 20 29 1 6 0 0 0 20 35 1 0 0 0 0 21 30 1 6 0 0 0 21 39 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 25 1 0 0 0 0 23 40 1 6 0 0 0 24 26 1 0 0 0 0 24 29 1 6 0 0 0 24 30 1 0 0 0 0 25 29 1 1 0 0 0 25 36 1 0 0 0 0 26 31 1 1 0 0 0 26 41 1 0 0 0 0 27 37 2 0 0 0 0 27 41 1 0 0 0 0 28 31 1 0 0 0 0 29 6 1 6 0 0 0 30 42 1 1 0 0 0 31 38 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	586.24
Volume:	577.551
LogP:	2.228
LogD:	1.29
LogS:	-4.548
# Rotatable Bonds:	7
TPSA:	165.89
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.348
Synthetic Accessibility Score:	5.76
Fsp3:	0.613
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.372
MDCK Permeability:	7.68658792367205e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.091
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.611
Plasma Protein Binding (PPB):	67.6173324584961%
Volume Distribution (VD):	0.669
Pgp-substrate:	30.53596305847168%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.041
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.17
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.131
CYP3A4-substrate:	0.382

ADMET: Excretion

Clearance (CL):	3.456
Half-life (T1/2):	0.45

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.77
Drug-inuced Liver Injury (DILI):	0.85
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.29
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.222
Carcinogencity:	0.012
Eye Corrosion:	0.003
Eye Irritation:	0.013
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: NPC217918

Natural Product ID:	NPC217918
*Common Name:**	GERGUKHEZFJMEB-NGHSAJJSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GERGUKHEZFJMEB-NGHSAJJSSA-N
Standard InCHI:	InChI=1S/C31H38O11/c1-15-19(34)13-31(38)26(41-27(37)18-10-8-7-9-11-18)24-29(6,20(35)12-21-30(24,14-39-21)42-17(3)33)25(36)23(40-16(2)32)22(15)28(31,4)5/h7-11,20-21,23-26,35-36,38H,12-14H2,1-6H3/t20-,21+,23+,24-,25-,26-,29+,30-,31+/m0/s1
SMILES:	CC1=C2[C@H]([C@@H]([C@]3(C)[C@H](C[C@@H]4[C@@](CO4)([C@H]3[C@@H]([C@](CC1=O)(C2(C)C)O)OC(=O)c1ccccc1)OC(=O)C)O)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL265977
PubChem CID:	5321736
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0000676] Taxanes and derivatives

*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
NPO32489	Taxus	Genus	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10543916]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[14987066]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844936]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	Japan	n.a.	PMID[15974623]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24820	Taxus cuspidata	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24820	Taxus cuspidata	Species	Taxaceae	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
NPT168	Cell Line	P388	Mus musculus	IC50	=	47863009.23	nM	PMID[512669]
NPT168	Cell Line	P388	Mus musculus	IC50	=	21.0	ug.mL-1	PMID[512670]

☑ 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 NPC217918 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	330
0.1-0.2	1165
0.2-0.3	2515
0.3-0.4	5539
0.4-0.5	10097
0.5-0.6	10875
0.6-0.7	10547
0.7-0.8	1321
0.8-0.85	243
0.85-0.9	51
0.9-0.95	2
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9857	High Similarity	NPC91730
0.9787	High Similarity	NPC197037
0.965	High Similarity	NPC229545
0.965	High Similarity	NPC248265
0.965	High Similarity	NPC11588
0.965	High Similarity	NPC134685
0.965	High Similarity	NPC219419
0.964	High Similarity	NPC38696
0.9583	High Similarity	NPC114357
0.9583	High Similarity	NPC259144
0.9583	High Similarity	NPC155329
0.9496	High Similarity	NPC34012
0.9214	High Similarity	NPC472547
0.9161	High Similarity	NPC127857
0.9149	High Similarity	NPC472576
0.9149	High Similarity	NPC27377
0.9149	High Similarity	NPC118080
0.9149	High Similarity	NPC41481
0.9149	High Similarity	NPC97947
0.9149	High Similarity	NPC87448
0.9149	High Similarity	NPC291599
0.911	High Similarity	NPC471103
0.9103	High Similarity	NPC60509
0.9103	High Similarity	NPC250046
0.9103	High Similarity	NPC81698
0.9097	High Similarity	NPC474935
0.9079	High Similarity	NPC471493
0.9078	High Similarity	NPC171207
0.9078	High Similarity	NPC90614
0.9078	High Similarity	NPC100913
0.9078	High Similarity	NPC275592
0.9078	High Similarity	NPC97667
0.9071	High Similarity	NPC39549
0.9054	High Similarity	NPC21410
0.9054	High Similarity	NPC473670
0.9041	High Similarity	NPC198455
0.9041	High Similarity	NPC161239
0.9041	High Similarity	NPC7095
0.9041	High Similarity	NPC165260
0.9014	High Similarity	NPC16912
0.9	High Similarity	NPC472545
0.9	High Similarity	NPC472551
0.9	High Similarity	NPC472372
0.9	High Similarity	NPC472374
0.8986	High Similarity	NPC80599
0.898	High Similarity	NPC51602
0.898	High Similarity	NPC101043
0.898	High Similarity	NPC306799
0.8958	High Similarity	NPC241951
0.8958	High Similarity	NPC475759
0.8958	High Similarity	NPC470152
0.8944	High Similarity	NPC183270
0.8944	High Similarity	NPC477904
0.8933	High Similarity	NPC472393
0.8926	High Similarity	NPC228204
0.8926	High Similarity	NPC26033
0.8919	High Similarity	NPC472548
0.8912	High Similarity	NPC112216
0.8904	High Similarity	NPC132652
0.8897	High Similarity	NPC472571
0.8897	High Similarity	NPC184817
0.8897	High Similarity	NPC70403
0.8897	High Similarity	NPC177940
0.8897	High Similarity	NPC476973
0.8897	High Similarity	NPC171525
0.8897	High Similarity	NPC472572
0.8897	High Similarity	NPC158663
0.8897	High Similarity	NPC472575
0.8897	High Similarity	NPC311825
0.8897	High Similarity	NPC29704
0.8897	High Similarity	NPC96903
0.8897	High Similarity	NPC470157
0.8897	High Similarity	NPC200471
0.8897	High Similarity	NPC470159
0.8897	High Similarity	NPC472568
0.8897	High Similarity	NPC174982
0.8897	High Similarity	NPC471104
0.8897	High Similarity	NPC473088
0.8897	High Similarity	NPC469349
0.8897	High Similarity	NPC92867
0.8889	High Similarity	NPC477894
0.8889	High Similarity	NPC163087
0.8867	High Similarity	NPC106895
0.8867	High Similarity	NPC217091
0.8859	High Similarity	NPC265395
0.8859	High Similarity	NPC304876
0.8859	High Similarity	NPC472030
0.8859	High Similarity	NPC1173
0.8859	High Similarity	NPC472022
0.8859	High Similarity	NPC473414
0.8859	High Similarity	NPC249471
0.8859	High Similarity	NPC158333
0.8859	High Similarity	NPC257213
0.8859	High Similarity	NPC472005
0.8859	High Similarity	NPC237549
0.8859	High Similarity	NPC133430
0.8859	High Similarity	NPC256142
0.8859	High Similarity	NPC469477
0.8859	High Similarity	NPC242262
0.8851	High Similarity	NPC470153
0.8849	High Similarity	NPC209851
0.8849	High Similarity	NPC472394
0.8836	High Similarity	NPC20255
0.8828	High Similarity	NPC472573
0.8828	High Similarity	NPC476974
0.8828	High Similarity	NPC57628
0.8828	High Similarity	NPC472569
0.8828	High Similarity	NPC188865
0.8828	High Similarity	NPC475122
0.8828	High Similarity	NPC25768
0.8828	High Similarity	NPC11685
0.8828	High Similarity	NPC95810
0.8828	High Similarity	NPC95265
0.8828	High Similarity	NPC163719
0.8828	High Similarity	NPC472570
0.8828	High Similarity	NPC70716
0.8828	High Similarity	NPC125106
0.8819	High Similarity	NPC182869
0.8819	High Similarity	NPC472546
0.88	High Similarity	NPC112523
0.88	High Similarity	NPC473632
0.88	High Similarity	NPC472549
0.88	High Similarity	NPC282239
0.88	High Similarity	NPC132599
0.88	High Similarity	NPC114410
0.88	High Similarity	NPC469730
0.8794	High Similarity	NPC472577
0.8794	High Similarity	NPC291638
0.8794	High Similarity	NPC17877
0.8794	High Similarity	NPC195647
0.8794	High Similarity	NPC66761
0.8792	High Similarity	NPC477905
0.8784	High Similarity	NPC473214
0.8784	High Similarity	NPC470245
0.8776	High Similarity	NPC473760
0.8767	High Similarity	NPC471100
0.8767	High Similarity	NPC125882
0.8767	High Similarity	NPC472556
0.8767	High Similarity	NPC471107
0.875	High Similarity	NPC224491
0.875	High Similarity	NPC469399
0.8742	High Similarity	NPC11410
0.8733	High Similarity	NPC77719
0.8723	High Similarity	NPC474608
0.8716	High Similarity	NPC270590
0.8716	High Similarity	NPC266265
0.8716	High Similarity	NPC92293
0.8716	High Similarity	NPC471101
0.8716	High Similarity	NPC476975
0.8716	High Similarity	NPC473215
0.8716	High Similarity	NPC301556
0.8707	High Similarity	NPC478263
0.8707	High Similarity	NPC209592
0.8707	High Similarity	NPC48599
0.8705	High Similarity	NPC473443
0.8699	High Similarity	NPC34943
0.8684	High Similarity	NPC469417
0.8684	High Similarity	NPC469771
0.8675	High Similarity	NPC5115
0.8675	High Similarity	NPC473611
0.8662	High Similarity	NPC477896
0.8662	High Similarity	NPC477893
0.8649	High Similarity	NPC281717
0.8649	High Similarity	NPC327031
0.8639	High Similarity	NPC301946
0.8639	High Similarity	NPC277053
0.8639	High Similarity	NPC478264
0.8633	High Similarity	NPC225103
0.863	High Similarity	NPC91703
0.8627	High Similarity	NPC471102
0.86	High Similarity	NPC469415
0.8581	High Similarity	NPC469513
0.8581	High Similarity	NPC473602
0.8581	High Similarity	NPC240115
0.8571	High Similarity	NPC472388
0.8571	High Similarity	NPC80895
0.8571	High Similarity	NPC471912
0.8562	High Similarity	NPC192658
0.8561	High Similarity	NPC195224
0.8553	High Similarity	NPC34066
0.8553	High Similarity	NPC251139
0.8553	High Similarity	NPC469422
0.8552	High Similarity	NPC473081
0.8552	High Similarity	NPC200592
0.8552	High Similarity	NPC473060
0.8552	High Similarity	NPC473112
0.8552	High Similarity	NPC147880
0.8552	High Similarity	NPC43241
0.8552	High Similarity	NPC473109
0.8552	High Similarity	NPC4341
0.8552	High Similarity	NPC473085
0.8552	High Similarity	NPC184747
0.8552	High Similarity	NPC48017
0.8552	High Similarity	NPC476094
0.8552	High Similarity	NPC473613
0.8552	High Similarity	NPC473758
0.8552	High Similarity	NPC211137
0.8543	High Similarity	NPC283875
0.8543	High Similarity	NPC233581
0.8543	High Similarity	NPC22571

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 NPC217918 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	774
0.2-0.3	1684
0.3-0.4	2850
0.4-0.5	2258
0.5-0.6	1026
0.6-0.7	269
0.7-0.8	12
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD8368	Discontinued
0.8415	Intermediate Similarity	NPD8407	Phase 2
0.8313	Intermediate Similarity	NPD8434	Phase 2
0.8272	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD8360	Approved
0.8214	Intermediate Similarity	NPD8361	Approved
0.8214	Intermediate Similarity	NPD8435	Approved
0.7931	Intermediate Similarity	NPD8485	Approved
0.7908	Intermediate Similarity	NPD7236	Approved
0.7882	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7239	Suspended
0.7771	Intermediate Similarity	NPD7799	Discontinued
0.7471	Intermediate Similarity	NPD8150	Discontinued
0.745	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD8462	Phase 1
0.7333	Intermediate Similarity	NPD7058	Phase 2
0.7333	Intermediate Similarity	NPD7057	Phase 3
0.7325	Intermediate Similarity	NPD4628	Phase 3
0.7305	Intermediate Similarity	NPD2629	Approved
0.7303	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD8166	Discontinued
0.7212	Intermediate Similarity	NPD7819	Suspended
0.7212	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7473	Discontinued
0.7188	Intermediate Similarity	NPD8404	Phase 2
0.7186	Intermediate Similarity	NPD7075	Discontinued
0.717	Intermediate Similarity	NPD6190	Approved
0.7169	Intermediate Similarity	NPD5402	Approved
0.7134	Intermediate Similarity	NPD6599	Discontinued
0.7134	Intermediate Similarity	NPD4380	Phase 2
0.7133	Intermediate Similarity	NPD4198	Discontinued
0.7133	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7008	Discontinued
0.7102	Intermediate Similarity	NPD8312	Approved
0.7102	Intermediate Similarity	NPD8313	Approved
0.7095	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8127	Discontinued
0.7048	Intermediate Similarity	NPD6801	Discontinued
0.7025	Intermediate Similarity	NPD2346	Discontinued
0.7021	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6232	Discontinued
0.7013	Intermediate Similarity	NPD7961	Discontinued
0.7011	Intermediate Similarity	NPD5844	Phase 1
0.7	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2182	Approved
0.6986	Remote Similarity	NPD7741	Discontinued
0.697	Remote Similarity	NPD3226	Approved
0.6964	Remote Similarity	NPD3817	Phase 2
0.6951	Remote Similarity	NPD5403	Approved
0.6948	Remote Similarity	NPD3764	Approved
0.6946	Remote Similarity	NPD37	Approved
0.6944	Remote Similarity	NPD5951	Approved
0.6933	Remote Similarity	NPD5401	Approved
0.6923	Remote Similarity	NPD4966	Approved
0.6923	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4965	Approved
0.6923	Remote Similarity	NPD4967	Phase 2
0.6905	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5761	Phase 2
0.6905	Remote Similarity	NPD5760	Phase 2
0.6901	Remote Similarity	NPD5494	Approved
0.6899	Remote Similarity	NPD2799	Discontinued
0.6893	Remote Similarity	NPD6559	Discontinued
0.6892	Remote Similarity	NPD5125	Phase 3
0.6892	Remote Similarity	NPD5126	Approved
0.689	Remote Similarity	NPD6273	Approved
0.6882	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD6799	Approved
0.6867	Remote Similarity	NPD7458	Discontinued
0.6857	Remote Similarity	NPD3818	Discontinued
0.6855	Remote Similarity	NPD2935	Discontinued
0.6852	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6535	Approved
0.6848	Remote Similarity	NPD6534	Approved
0.6846	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1934	Approved
0.6842	Remote Similarity	NPD6234	Discontinued
0.6842	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2313	Discontinued
0.6829	Remote Similarity	NPD2533	Approved
0.6829	Remote Similarity	NPD2534	Approved
0.6829	Remote Similarity	NPD2532	Approved
0.6829	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7699	Phase 2
0.6828	Remote Similarity	NPD7700	Phase 2
0.6825	Remote Similarity	NPD7435	Discontinued
0.6815	Remote Similarity	NPD230	Phase 1
0.6813	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2801	Approved
0.68	Remote Similarity	NPD6287	Discontinued
0.6798	Remote Similarity	NPD6764	Approved
0.6798	Remote Similarity	NPD6765	Approved
0.6792	Remote Similarity	NPD7305	Phase 1
0.679	Remote Similarity	NPD3750	Approved
0.6789	Remote Similarity	NPD8319	Approved
0.6789	Remote Similarity	NPD8320	Phase 1
0.6786	Remote Similarity	NPD7411	Suspended
0.678	Remote Similarity	NPD7074	Phase 3
0.6779	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3751	Discontinued
0.6761	Remote Similarity	NPD7228	Approved
0.676	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD6010	Discontinued
0.6743	Remote Similarity	NPD6166	Phase 2
0.6743	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7768	Phase 2
0.6723	Remote Similarity	NPD7054	Approved
0.6723	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD164	Approved
0.6712	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7266	Discontinued
0.6704	Remote Similarity	NPD7685	Pre-registration
0.669	Remote Similarity	NPD7094	Approved
0.669	Remote Similarity	NPD6858	Approved
0.6688	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6085	Phase 2
0.6687	Remote Similarity	NPD3748	Approved
0.6687	Remote Similarity	NPD7003	Approved
0.6687	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7472	Approved
0.6684	Remote Similarity	NPD6823	Phase 2
0.6667	Remote Similarity	NPD6777	Approved
0.6667	Remote Similarity	NPD6781	Approved
0.6667	Remote Similarity	NPD6780	Approved
0.6667	Remote Similarity	NPD6779	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6776	Approved
0.6667	Remote Similarity	NPD6782	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6778	Approved
0.6649	Remote Similarity	NPD7497	Discontinued
0.6648	Remote Similarity	NPD6784	Approved
0.6648	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6785	Approved
0.6646	Remote Similarity	NPD5404	Approved
0.6646	Remote Similarity	NPD5405	Approved
0.6646	Remote Similarity	NPD5406	Approved
0.6646	Remote Similarity	NPD2796	Approved
0.6646	Remote Similarity	NPD5408	Approved
0.6643	Remote Similarity	NPD1929	Approved
0.6643	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1930	Approved
0.6629	Remote Similarity	NPD3787	Discontinued
0.6628	Remote Similarity	NPD3882	Suspended
0.6627	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD1470	Approved
0.6615	Remote Similarity	NPD7874	Approved
0.6615	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7240	Approved
0.6611	Remote Similarity	NPD7251	Discontinued
0.6608	Remote Similarity	NPD8455	Phase 2
0.6606	Remote Similarity	NPD3300	Phase 2
0.6605	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6355	Discontinued
0.6603	Remote Similarity	NPD6832	Phase 2
0.6587	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD1510	Phase 2
0.6582	Remote Similarity	NPD6663	Approved
0.6581	Remote Similarity	NPD2798	Approved
0.6577	Remote Similarity	NPD7610	Discontinued
0.6575	Remote Similarity	NPD7808	Phase 3
0.6573	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD6959	Discontinued
0.6564	Remote Similarity	NPD1549	Phase 2
0.6562	Remote Similarity	NPD7698	Approved
0.6562	Remote Similarity	NPD7697	Approved
0.6562	Remote Similarity	NPD7696	Phase 3
0.6562	Remote Similarity	NPD6651	Approved
0.6556	Remote Similarity	NPD6797	Phase 2
0.6554	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5048	Discontinued
0.6548	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD1238	Approved
0.6547	Remote Similarity	NPD2066	Phase 3
0.6543	Remote Similarity	NPD1551	Phase 2
0.6543	Remote Similarity	NPD2438	Suspended
0.6543	Remote Similarity	NPD6100	Approved
0.6543	Remote Similarity	NPD6099	Approved
0.6538	Remote Similarity	NPD5736	Approved
0.6533	Remote Similarity	NPD9545	Approved
0.6528	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7870	Phase 2
0.6528	Remote Similarity	NPD7871	Phase 2
0.6525	Remote Similarity	NPD6647	Phase 2
0.6524	Remote Similarity	NPD6212	Phase 3

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