NPASS Compound

Structure

NPC469647 OpenBabel07101718312D 43 47 0 0 1 0 0 0 0 0999 V2000 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5663 3.9874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4242 2.6195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5139 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9227 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1123 -1.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3438 3.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4888 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5139 1.6235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0017 2.2594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4888 1.4010 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 -3.7470 -2.1137 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9977 2.3491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2954 0.1738 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6433 0.4130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 22 1 0 0 0 0 3 32 1 0 0 0 0 4 32 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 13 1 0 0 0 0 10 11 2 0 0 0 0 10 12 1 0 0 0 0 11 14 1 0 0 0 0 12 15 2 0 0 0 0 13 16 1 0 0 0 0 14 24 2 0 0 0 0 15 24 1 0 0 0 0 16 28 1 0 0 0 0 17 22 2 0 0 0 0 17 26 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 19 34 1 0 0 0 0 20 27 1 0 0 0 0 20 33 1 0 0 0 0 21 23 1 0 0 0 0 21 36 1 0 0 0 0 22 30 1 0 0 0 0 24 31 1 0 0 0 0 25 29 1 0 0 0 0 25 33 1 6 0 0 0 26 33 1 1 0 0 0 26 34 1 0 0 0 0 27 35 1 1 0 0 0 27 42 1 0 0 0 0 28 37 2 0 0 0 0 28 43 1 0 0 0 0 29 32 1 0 0 0 0 29 35 1 1 0 0 0 30 34 1 0 0 0 0 30 38 2 0 0 0 0 31 39 2 0 0 0 0 31 42 1 0 0 0 0 32 35 1 0 0 0 0 33 40 1 6 0 0 0 34 41 1 1 0 0 0 35 43 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	594.32
Volume:	620.364
LogP:	5.854
LogD:	3.709
LogS:	-4.741
# Rotatable Bonds:	13
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.188
Synthetic Accessibility Score:	4.874
Fsp3:	0.629
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:	-4.715
MDCK Permeability:	2.406486419204157e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.052
20% Bioavailability (F20%):	0.635
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.839
Plasma Protein Binding (PPB):	97.24823760986328%
Volume Distribution (VD):	2.29
Pgp-substrate:	2.0182623863220215%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.09
CYP2C19-inhibitor:	0.691
CYP2C19-substrate:	0.085
CYP2C9-inhibitor:	0.934
CYP2C9-substrate:	0.514
CYP2D6-inhibitor:	0.095
CYP2D6-substrate:	0.033
CYP3A4-inhibitor:	0.882
CYP3A4-substrate:	0.164

ADMET: Excretion

Clearance (CL):	7.514
Half-life (T1/2):	0.09

ADMET: Toxicity

hERG Blockers:	0.691
Human Hepatotoxicity (H-HT):	0.753
Drug-inuced Liver Injury (DILI):	0.905
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.798
Maximum Recommended Daily Dose:	0.978
Skin Sensitization:	0.889
Carcinogencity:	0.29
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC469647

Natural Product ID:	NPC469647
*Common Name:**	XCZMBPWIQJRZDE-VSHBPWGQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XCZMBPWIQJRZDE-VSHBPWGQSA-N
Standard InCHI:	InChI=1S/C35H46O8/c1-5-6-7-8-9-13-16-28(37)43-35-27(42-31(39)24-14-11-10-12-15-24)20-33(40)25(29(35)32(35,3)4)18-23(21-36)19-34(41)26(33)17-22(2)30(34)38/h10-12,14-15,17-18,25-27,29,36,40-41H,5-9,13,16,19-21H2,1-4H3/t25-,26-,27+,29+,33+,34+,35-/m0/s1
SMILES:	CCCCCCCCC(=O)O[C@@]12[C@H](OC(=O)c3ccccc3)C[C@]3([C@H]([C@@H]1C2(C)C)C=C(CO)C[C@]1([C@H]3C=C(C1=O)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1096215
PubChem CID:	46886773
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO2035	Daphne aurantiaca	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192236]
NPO2035	Daphne aurantiaca	Species	Thymelaeaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	10.0	nM	PMID[524815]

☑ 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 NPC469647 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	321
0.1-0.2	1137
0.2-0.3	2371
0.3-0.4	5124
0.4-0.5	9618
0.5-0.6	11119
0.6-0.7	10883
0.7-0.8	1774
0.8-0.85	267
0.85-0.9	64
0.9-0.95	5
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469648
1.0	High Similarity	NPC138641
1.0	High Similarity	NPC283875
1.0	High Similarity	NPC22571
0.986	High Similarity	NPC145649
0.986	High Similarity	NPC233581
0.9793	High Similarity	NPC11410
0.979	High Similarity	NPC472398
0.9444	High Similarity	NPC132652
0.9366	High Similarity	NPC183540
0.9366	High Similarity	NPC140021
0.9324	High Similarity	NPC251139
0.9034	High Similarity	NPC95449
0.8973	High Similarity	NPC34943
0.8926	High Similarity	NPC125033
0.8912	High Similarity	NPC125882
0.8904	High Similarity	NPC477894
0.8867	High Similarity	NPC471103
0.8867	High Similarity	NPC51602
0.8851	High Similarity	NPC312393
0.8851	High Similarity	NPC20255
0.8851	High Similarity	NPC240115
0.8839	High Similarity	NPC477190
0.8839	High Similarity	NPC477188
0.8839	High Similarity	NPC43304
0.8836	High Similarity	NPC192658
0.8828	High Similarity	NPC87934
0.8828	High Similarity	NPC90614
0.8828	High Similarity	NPC162613
0.8816	High Similarity	NPC469730
0.8816	High Similarity	NPC132599
0.8816	High Similarity	NPC21410
0.8816	High Similarity	NPC473611
0.8816	High Similarity	NPC473670
0.8816	High Similarity	NPC473632
0.88	High Similarity	NPC470245
0.88	High Similarity	NPC7095
0.88	High Similarity	NPC473214
0.8784	High Similarity	NPC311825
0.8784	High Similarity	NPC92867
0.8784	High Similarity	NPC127857
0.8767	High Similarity	NPC27377
0.8767	High Similarity	NPC472576
0.8767	High Similarity	NPC41481
0.8767	High Similarity	NPC97947
0.8767	High Similarity	NPC87448
0.8767	High Similarity	NPC291599
0.8767	High Similarity	NPC16912
0.8767	High Similarity	NPC118080
0.8759	High Similarity	NPC9905
0.8758	High Similarity	NPC70344
0.8758	High Similarity	NPC106895
0.875	High Similarity	NPC134685
0.875	High Similarity	NPC248265
0.875	High Similarity	NPC229545
0.875	High Similarity	NPC11588
0.8742	High Similarity	NPC470153
0.8733	High Similarity	NPC250046
0.8733	High Similarity	NPC476975
0.8733	High Similarity	NPC60509
0.8733	High Similarity	NPC473215
0.8733	High Similarity	NPC81698
0.8725	High Similarity	NPC473602
0.8707	High Similarity	NPC472546
0.8707	High Similarity	NPC182869
0.8707	High Similarity	NPC34012
0.8699	High Similarity	NPC100913
0.8699	High Similarity	NPC275592
0.8699	High Similarity	NPC472547
0.8699	High Similarity	NPC97667
0.8699	High Similarity	NPC171207
0.8693	High Similarity	NPC26033
0.8693	High Similarity	NPC282239
0.8693	High Similarity	NPC114357
0.8693	High Similarity	NPC228204
0.8693	High Similarity	NPC155329
0.8693	High Similarity	NPC259144
0.8675	High Similarity	NPC165260
0.8675	High Similarity	NPC112216
0.8675	High Similarity	NPC161239
0.8675	High Similarity	NPC198455
0.8671	High Similarity	NPC61891
0.8667	High Similarity	NPC473760
0.8667	High Similarity	NPC327031
0.8662	High Similarity	NPC66193
0.8658	High Similarity	NPC200471
0.8658	High Similarity	NPC476973
0.8658	High Similarity	NPC470157
0.8658	High Similarity	NPC469349
0.8658	High Similarity	NPC472575
0.8658	High Similarity	NPC158663
0.8658	High Similarity	NPC171525
0.8658	High Similarity	NPC473088
0.8658	High Similarity	NPC472556
0.8658	High Similarity	NPC471104
0.8658	High Similarity	NPC174982
0.8658	High Similarity	NPC70403
0.8658	High Similarity	NPC25043
0.8658	High Similarity	NPC472572
0.8658	High Similarity	NPC134131
0.8658	High Similarity	NPC470159
0.8658	High Similarity	NPC29704
0.8658	High Similarity	NPC184817
0.8658	High Similarity	NPC472571
0.8658	High Similarity	NPC471107
0.8658	High Similarity	NPC96903
0.8658	High Similarity	NPC471100
0.8658	High Similarity	NPC177940
0.8658	High Similarity	NPC472568
0.8649	High Similarity	NPC163087
0.8645	High Similarity	NPC49297
0.8645	High Similarity	NPC159692
0.8627	High Similarity	NPC304876
0.8627	High Similarity	NPC472022
0.8627	High Similarity	NPC472030
0.8627	High Similarity	NPC257213
0.8627	High Similarity	NPC249471
0.8627	High Similarity	NPC219419
0.8627	High Similarity	NPC473414
0.8627	High Similarity	NPC242262
0.8627	High Similarity	NPC265395
0.8627	High Similarity	NPC237549
0.8627	High Similarity	NPC158333
0.8627	High Similarity	NPC1173
0.8627	High Similarity	NPC256142
0.8627	High Similarity	NPC472005
0.8618	High Similarity	NPC197037
0.86	High Similarity	NPC478263
0.86	High Similarity	NPC48599
0.86	High Similarity	NPC209592
0.8591	High Similarity	NPC472573
0.8591	High Similarity	NPC11685
0.8591	High Similarity	NPC25768
0.8591	High Similarity	NPC475759
0.8591	High Similarity	NPC241951
0.8591	High Similarity	NPC163719
0.8591	High Similarity	NPC472569
0.8591	High Similarity	NPC38696
0.8591	High Similarity	NPC70716
0.8591	High Similarity	NPC188865
0.8591	High Similarity	NPC125106
0.8591	High Similarity	NPC476974
0.8591	High Similarity	NPC470152
0.8591	High Similarity	NPC57628
0.8591	High Similarity	NPC95265
0.8591	High Similarity	NPC95810
0.8591	High Similarity	NPC472570
0.8591	High Similarity	NPC470231
0.8591	High Similarity	NPC475122
0.8581	High Similarity	NPC181924
0.8581	High Similarity	NPC472393
0.8571	High Similarity	NPC114410
0.8571	High Similarity	NPC112523
0.8571	High Similarity	NPC472549
0.8562	High Similarity	NPC39549
0.8553	High Similarity	NPC476173
0.8553	High Similarity	NPC254558
0.8553	High Similarity	NPC91730
0.8552	High Similarity	NPC195647
0.8552	High Similarity	NPC291638
0.8552	High Similarity	NPC66761
0.8552	High Similarity	NPC472577
0.8552	High Similarity	NPC477893
0.8552	High Similarity	NPC17877
0.8544	High Similarity	NPC322420
0.8543	High Similarity	NPC217918
0.8535	High Similarity	NPC476077
0.8533	High Similarity	NPC478264
0.8526	High Similarity	NPC471102
0.8523	High Similarity	NPC191387
0.8523	High Similarity	NPC131966
0.8516	High Similarity	NPC217091
0.8514	High Similarity	NPC266374
0.8506	High Similarity	NPC77719
0.8497	Intermediate Similarity	NPC306799
0.8497	Intermediate Similarity	NPC101043
0.8493	Intermediate Similarity	NPC472374
0.8493	Intermediate Similarity	NPC472545
0.8493	Intermediate Similarity	NPC472372
0.8493	Intermediate Similarity	NPC472551
0.8491	Intermediate Similarity	NPC471134
0.8487	Intermediate Similarity	NPC76103
0.8487	Intermediate Similarity	NPC266265
0.8487	Intermediate Similarity	NPC301556
0.8487	Intermediate Similarity	NPC471101
0.8487	Intermediate Similarity	NPC92293
0.8487	Intermediate Similarity	NPC270590
0.8483	Intermediate Similarity	NPC474608
0.8481	Intermediate Similarity	NPC275477
0.8477	Intermediate Similarity	NPC474935
0.8477	Intermediate Similarity	NPC475552
0.8462	Intermediate Similarity	NPC469771
0.8447	Intermediate Similarity	NPC40138
0.8446	Intermediate Similarity	NPC473060
0.8446	Intermediate Similarity	NPC473081
0.8446	Intermediate Similarity	NPC184747
0.8446	Intermediate Similarity	NPC211137
0.8446	Intermediate Similarity	NPC4341
0.8446	Intermediate Similarity	NPC476094
0.8446	Intermediate Similarity	NPC200592

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 NPC469647 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	267
0.1-0.2	777
0.2-0.3	1613
0.3-0.4	2832
0.4-0.5	2252
0.5-0.6	1045
0.6-0.7	341
0.7-0.8	23
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.817	Intermediate Similarity	NPD7236	Approved
0.8025	Intermediate Similarity	NPD7239	Suspended
0.7904	Intermediate Similarity	NPD7799	Discontinued
0.7849	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD8368	Discontinued
0.7803	Intermediate Similarity	NPD8434	Phase 2
0.7791	Intermediate Similarity	NPD8407	Phase 2
0.7647	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD8361	Approved
0.7614	Intermediate Similarity	NPD8360	Approved
0.76	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7058	Phase 2
0.7576	Intermediate Similarity	NPD7057	Phase 3
0.7514	Intermediate Similarity	NPD8435	Approved
0.7368	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD8485	Approved
0.7343	Intermediate Similarity	NPD2629	Approved
0.7338	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8150	Discontinued
0.7285	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7961	Discontinued
0.725	Intermediate Similarity	NPD4628	Phase 3
0.7243	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6190	Approved
0.7143	Intermediate Similarity	NPD7741	Discontinued
0.7143	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD8127	Discontinued
0.7022	Intermediate Similarity	NPD6764	Approved
0.7022	Intermediate Similarity	NPD7685	Pre-registration
0.7022	Intermediate Similarity	NPD6765	Approved
0.7018	Intermediate Similarity	NPD7075	Discontinued
0.6966	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6599	Discontinued
0.6949	Remote Similarity	NPD5844	Phase 1
0.6944	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5761	Phase 2
0.6941	Remote Similarity	NPD7819	Suspended
0.6941	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5760	Phase 2
0.6939	Remote Similarity	NPD4198	Discontinued
0.6933	Remote Similarity	NPD8166	Discontinued
0.6933	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD7473	Discontinued
0.6923	Remote Similarity	NPD7008	Discontinued
0.6901	Remote Similarity	NPD5402	Approved
0.6882	Remote Similarity	NPD37	Approved
0.6882	Remote Similarity	NPD6801	Discontinued
0.6879	Remote Similarity	NPD3764	Approved
0.6871	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6784	Approved
0.6868	Remote Similarity	NPD6785	Approved
0.686	Remote Similarity	NPD4966	Approved
0.686	Remote Similarity	NPD4965	Approved
0.686	Remote Similarity	NPD4967	Phase 2
0.6837	Remote Similarity	NPD8462	Phase 1
0.6826	Remote Similarity	NPD6273	Approved
0.6806	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD2182	Approved
0.6805	Remote Similarity	NPD7458	Discontinued
0.6788	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8404	Phase 2
0.6776	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7699	Phase 2
0.6772	Remote Similarity	NPD7700	Phase 2
0.6766	Remote Similarity	NPD2533	Approved
0.6766	Remote Similarity	NPD2532	Approved
0.6766	Remote Similarity	NPD2534	Approved
0.6765	Remote Similarity	NPD4380	Phase 2
0.6763	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6232	Discontinued
0.6758	Remote Similarity	NPD8313	Approved
0.6758	Remote Similarity	NPD8312	Approved
0.6757	Remote Similarity	NPD5951	Approved
0.6757	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.675	Remote Similarity	NPD230	Phase 1
0.6748	Remote Similarity	NPD5762	Approved
0.6748	Remote Similarity	NPD5763	Approved
0.6736	Remote Similarity	NPD8320	Phase 1
0.6736	Remote Similarity	NPD8319	Approved
0.6728	Remote Similarity	NPD7305	Phase 1
0.6727	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6799	Approved
0.6706	Remote Similarity	NPD3226	Approved
0.6706	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3817	Phase 2
0.6702	Remote Similarity	NPD6534	Approved
0.6702	Remote Similarity	NPD6535	Approved
0.669	Remote Similarity	NPD6647	Phase 2
0.6686	Remote Similarity	NPD6234	Discontinued
0.6686	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD5403	Approved
0.6684	Remote Similarity	NPD7435	Discontinued
0.6684	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5494	Approved
0.6646	Remote Similarity	NPD6355	Discontinued
0.6646	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD2067	Discontinued
0.6643	Remote Similarity	NPD1237	Approved
0.6626	Remote Similarity	NPD2799	Discontinued
0.6625	Remote Similarity	NPD6663	Approved
0.6624	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6085	Phase 2
0.6623	Remote Similarity	NPD6287	Discontinued
0.6612	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD3751	Discontinued
0.6611	Remote Similarity	NPD3818	Discontinued
0.6611	Remote Similarity	NPD7228	Approved
0.6609	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD5126	Approved
0.6601	Remote Similarity	NPD5125	Phase 3
0.6599	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7696	Phase 3
0.6598	Remote Similarity	NPD7697	Approved
0.6598	Remote Similarity	NPD7698	Approved
0.6592	Remote Similarity	NPD6166	Phase 2
0.6592	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD2935	Discontinued
0.6582	Remote Similarity	NPD5736	Approved
0.6579	Remote Similarity	NPD9545	Approved
0.6568	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD5401	Approved
0.6566	Remote Similarity	NPD7874	Approved
0.6566	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7870	Phase 2
0.6564	Remote Similarity	NPD7871	Phase 2
0.6557	Remote Similarity	NPD6559	Discontinued
0.6552	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6004	Phase 3
0.6545	Remote Similarity	NPD6002	Phase 3
0.6545	Remote Similarity	NPD6005	Phase 3
0.6545	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2346	Discontinued
0.6534	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7411	Suspended
0.6529	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD6776	Approved
0.6528	Remote Similarity	NPD6780	Approved
0.6528	Remote Similarity	NPD6782	Approved
0.6528	Remote Similarity	NPD6778	Approved
0.6528	Remote Similarity	NPD6779	Approved
0.6528	Remote Similarity	NPD164	Approved
0.6528	Remote Similarity	NPD6781	Approved
0.6528	Remote Similarity	NPD6777	Approved
0.6527	Remote Similarity	NPD7003	Approved
0.6527	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD3750	Approved
0.6522	Remote Similarity	NPD7808	Phase 3
0.6516	Remote Similarity	NPD4807	Approved
0.6516	Remote Similarity	NPD4806	Approved
0.6513	Remote Similarity	NPD7610	Discontinued
0.6512	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7094	Approved
0.651	Remote Similarity	NPD6858	Approved
0.6506	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD1934	Approved
0.6494	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5305	Approved
0.6494	Remote Similarity	NPD5306	Approved
0.6491	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6099	Approved
0.6485	Remote Similarity	NPD6100	Approved
0.648	Remote Similarity	NPD3787	Discontinued
0.6477	Remote Similarity	NPD7768	Phase 2
0.6471	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD7251	Discontinued
0.6465	Remote Similarity	NPD7701	Phase 2
0.6458	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD1929	Approved
0.6458	Remote Similarity	NPD1930	Approved
0.6457	Remote Similarity	NPD2801	Approved
0.645	Remote Similarity	NPD7801	Approved
0.6448	Remote Similarity	NPD7074	Phase 3
0.6446	Remote Similarity	NPD7266	Discontinued
0.6444	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD8297	Approved
0.6438	Remote Similarity	NPD6685	Approved
0.6429	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD2575	Approved
0.6429	Remote Similarity	NPD4110	Phase 3
0.6425	Remote Similarity	NPD7199	Phase 2
0.6424	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6371	Approved
0.6413	Remote Similarity	NPD6797	Phase 2
0.6412	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6409	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7054	Approved
0.6386	Remote Similarity	NPD2438	Suspended
0.6382	Remote Similarity	NPD7115	Discovery
0.6379	Remote Similarity	NPD7028	Phase 2
0.6378	Remote Similarity	NPD7240	Approved
0.6374	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.637	Remote Similarity	NPD5048	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