NPASS Compound

Structure

NPC470245 OpenBabel07101718232D 42 46 0 0 1 0 0 0 0 0999 V2000 -2.3970 -0.5603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2630 -0.3402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4803 -0.1332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5997 -1.1261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7176 -0.9613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8531 -1.4117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1804 3.6598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6305 -0.4368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1200 -2.0919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1804 2.6598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3143 4.1598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6750 -0.1421 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1644 -1.7972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3143 2.1598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4483 3.6598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9863 -0.5275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7638 0.4474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5988 -1.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7880 -1.4132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0752 0.0620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5310 -0.0603 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -3.2630 0.6598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9419 -0.8222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4483 2.6598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1932 -1.6065 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.8083 0.7422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3866 -0.3234 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9074 1.0198 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.5310 0.6598 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.2837 0.6598 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5823 2.1598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6802 -0.7331 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2837 -0.0603 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9074 -0.4204 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.1291 1.1598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5857 1.7171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9074 2.0198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2837 2.6598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1196 0.3568 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3970 1.1598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5823 1.1598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 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 33 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 23 2 0 0 0 0 13 23 1 0 0 0 0 14 24 2 0 0 0 0 15 24 1 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 18 27 1 0 0 0 0 19 25 1 0 0 0 0 19 34 1 0 0 0 0 20 26 1 0 0 0 0 20 39 1 0 0 0 0 21 29 1 0 0 0 0 21 34 1 0 0 0 0 22 35 2 0 0 0 0 22 40 1 0 0 0 0 24 31 1 0 0 0 0 25 32 1 0 0 0 0 26 36 2 0 0 0 0 27 33 1 0 0 0 0 27 39 1 0 0 0 0 28 29 1 0 0 0 0 28 30 1 0 0 0 0 28 37 1 0 0 0 0 29 40 1 0 0 0 0 30 33 1 0 0 0 0 30 41 1 0 0 0 0 31 38 2 0 0 0 0 31 41 1 0 0 0 0 32 42 1 0 0 0 0 33 34 1 0 0 0 0 34 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.27
Volume:	597.795
LogP:	4.059
LogD:	3.705
LogS:	-4.941
# Rotatable Bonds:	10
TPSA:	108.36
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.353
Synthetic Accessibility Score:	5.863
Fsp3:	0.5
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:	-5.079
MDCK Permeability:	3.060975723201409e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.863

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.818
Plasma Protein Binding (PPB):	95.56008911132812%
Volume Distribution (VD):	1.287
Pgp-substrate:	3.118166923522949%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.099
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.442
CYP2C9-substrate:	0.204
CYP2D6-inhibitor:	0.055
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.488
CYP3A4-substrate:	0.496

ADMET: Excretion

Clearance (CL):	10.23
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.113
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.488
Maximum Recommended Daily Dose:	0.073
Skin Sensitization:	0.097
Carcinogencity:	0.211
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.767

Download Data

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

Natural Product: NPC470245

Natural Product ID:	NPC470245
*Common Name:**	QHGRJGHURLLBFR-WUKNDPDISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QHGRJGHURLLBFR-WUKNDPDISA-N
Standard InCHI:	InChI=1S/C34H40O8/c1-21-29(40-22(2)35)28(37)30(41-31(38)24-14-10-7-11-15-24)33(5)27(18-25-19-34(21,33)42-32(25,3)4)39-20-26(36)17-16-23-12-8-6-9-13-23/h6-17,21,25,27-30,37H,18-20H2,1-5H3/b17-16+
SMILES:	CC1C(C(C(C2(C13CC(CC2OCC(=O)C=CC4=CC=CC=C4)C(O3)(C)C)C)OC(=O)C5=CC=CC=C5)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL191520
PubChem CID:	44398619
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002051] Agarofurans

*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
NPO33107	zinowiewia costaricensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974580]

☑ 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
Ki	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT886	Cell Line	NIH3T3	Mus musculus	Ki	=	4247.0	nM	PMID[514076]

☑ 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 NPC470245 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	308
0.1-0.2	1044
0.2-0.3	2342
0.3-0.4	4185
0.4-0.5	8697
0.5-0.6	11721
0.6-0.7	11805
0.7-0.8	2048
0.8-0.85	245
0.85-0.9	119
0.9-0.95	116
0.95-1	67

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473214
0.9929	High Similarity	NPC476975
0.9929	High Similarity	NPC473215
0.9714	High Similarity	NPC476973
0.9714	High Similarity	NPC472575
0.9714	High Similarity	NPC472571
0.9714	High Similarity	NPC171525
0.9714	High Similarity	NPC29704
0.9714	High Similarity	NPC96903
0.9714	High Similarity	NPC473088
0.9714	High Similarity	NPC200471
0.9714	High Similarity	NPC158663
0.9714	High Similarity	NPC472572
0.9714	High Similarity	NPC184817
0.9714	High Similarity	NPC174982
0.9714	High Similarity	NPC472568
0.9714	High Similarity	NPC470157
0.9714	High Similarity	NPC471104
0.9714	High Similarity	NPC70403
0.9714	High Similarity	NPC470159
0.9714	High Similarity	NPC177940
0.9714	High Similarity	NPC469349
0.9655	High Similarity	NPC106895
0.965	High Similarity	NPC470153
0.9643	High Similarity	NPC470231
0.9643	High Similarity	NPC57628
0.9643	High Similarity	NPC11685
0.9643	High Similarity	NPC472569
0.9643	High Similarity	NPC472570
0.9643	High Similarity	NPC472573
0.9643	High Similarity	NPC470152
0.9643	High Similarity	NPC95810
0.9643	High Similarity	NPC70716
0.9643	High Similarity	NPC241951
0.9643	High Similarity	NPC163719
0.9643	High Similarity	NPC475122
0.9643	High Similarity	NPC25768
0.9643	High Similarity	NPC125106
0.9643	High Similarity	NPC95265
0.9643	High Similarity	NPC476974
0.9643	High Similarity	NPC188865
0.9643	High Similarity	NPC475759
0.9586	High Similarity	NPC282239
0.9571	High Similarity	NPC163087
0.951	High Similarity	NPC92293
0.951	High Similarity	NPC270590
0.951	High Similarity	NPC266265
0.951	High Similarity	NPC301556
0.951	High Similarity	NPC471101
0.9456	High Similarity	NPC472393
0.9441	High Similarity	NPC281717
0.9437	High Similarity	NPC472556
0.9429	High Similarity	NPC87448
0.9429	High Similarity	NPC16912
0.9429	High Similarity	NPC118080
0.9429	High Similarity	NPC97947
0.9429	High Similarity	NPC27377
0.9429	High Similarity	NPC472576
0.9429	High Similarity	NPC41481
0.9429	High Similarity	NPC291599
0.9392	High Similarity	NPC471102
0.9388	High Similarity	NPC217091
0.9379	High Similarity	NPC471103
0.9379	High Similarity	NPC51602
0.9371	High Similarity	NPC474935
0.9357	High Similarity	NPC43241
0.9357	High Similarity	NPC473758
0.9357	High Similarity	NPC171207
0.9357	High Similarity	NPC473085
0.9357	High Similarity	NPC97667
0.9357	High Similarity	NPC473109
0.9357	High Similarity	NPC200592
0.9357	High Similarity	NPC48017
0.9357	High Similarity	NPC473112
0.9357	High Similarity	NPC100913
0.9357	High Similarity	NPC473060
0.9357	High Similarity	NPC476094
0.9357	High Similarity	NPC275592
0.9357	High Similarity	NPC473081
0.9357	High Similarity	NPC90614
0.9357	High Similarity	NPC4341
0.9357	High Similarity	NPC211137
0.9357	High Similarity	NPC473613
0.9357	High Similarity	NPC147880
0.9357	High Similarity	NPC184747
0.932	High Similarity	NPC26033
0.932	High Similarity	NPC228204
0.931	High Similarity	NPC7095
0.931	High Similarity	NPC254558
0.9286	High Similarity	NPC210591
0.9286	High Similarity	NPC214550
0.9286	High Similarity	NPC475652
0.9252	High Similarity	NPC472022
0.9252	High Similarity	NPC265395
0.9252	High Similarity	NPC237549
0.9252	High Similarity	NPC158333
0.9252	High Similarity	NPC257213
0.9252	High Similarity	NPC1173
0.9252	High Similarity	NPC472005
0.9252	High Similarity	NPC242262
0.9252	High Similarity	NPC304876
0.9252	High Similarity	NPC256142
0.9252	High Similarity	NPC472030
0.9252	High Similarity	NPC249471
0.9252	High Similarity	NPC473414
0.9241	High Similarity	NPC81698
0.9241	High Similarity	NPC60509
0.9241	High Similarity	NPC250046
0.9225	High Similarity	NPC472546
0.9214	High Similarity	NPC283375
0.9214	High Similarity	NPC183122
0.9189	High Similarity	NPC472549
0.9189	High Similarity	NPC112523
0.9189	High Similarity	NPC114410
0.9189	High Similarity	NPC473670
0.9189	High Similarity	NPC21410
0.9184	High Similarity	NPC477905
0.9178	High Similarity	NPC161239
0.9178	High Similarity	NPC165260
0.9178	High Similarity	NPC198455
0.9178	High Similarity	NPC112216
0.9161	High Similarity	NPC177340
0.9161	High Similarity	NPC191082
0.9161	High Similarity	NPC270498
0.9161	High Similarity	NPC139067
0.9161	High Similarity	NPC475429
0.9161	High Similarity	NPC473673
0.9161	High Similarity	NPC246480
0.9161	High Similarity	NPC147217
0.9155	High Similarity	NPC224491
0.9122	High Similarity	NPC77719
0.9103	High Similarity	NPC473602
0.9097	High Similarity	NPC51314
0.9097	High Similarity	NPC67777
0.9091	High Similarity	NPC182869
0.9091	High Similarity	NPC34012
0.9085	High Similarity	NPC472547
0.9071	High Similarity	NPC66761
0.9071	High Similarity	NPC472577
0.9071	High Similarity	NPC291638
0.9071	High Similarity	NPC195647
0.9071	High Similarity	NPC17877
0.9067	High Similarity	NPC469771
0.9054	High Similarity	NPC472548
0.9034	High Similarity	NPC471107
0.9034	High Similarity	NPC471100
0.9034	High Similarity	NPC127857
0.9028	High Similarity	NPC91703
0.9	High Similarity	NPC474608
0.8986	High Similarity	NPC306799
0.8986	High Similarity	NPC101043
0.8944	High Similarity	NPC39549
0.8933	High Similarity	NPC473632
0.8933	High Similarity	NPC34066
0.8933	High Similarity	NPC469730
0.8933	High Similarity	NPC132599
0.8933	High Similarity	NPC473611
0.8919	High Similarity	NPC31829
0.8919	High Similarity	NPC469448
0.8912	High Similarity	NPC473760
0.8889	High Similarity	NPC476077
0.8873	High Similarity	NPC472551
0.8873	High Similarity	NPC472545
0.8867	High Similarity	NPC219419
0.8857	High Similarity	NPC476976
0.8844	High Similarity	NPC240115
0.8844	High Similarity	NPC48599
0.8844	High Similarity	NPC209592
0.8836	High Similarity	NPC34943
0.8836	High Similarity	NPC38696
0.8808	High Similarity	NPC469422
0.8808	High Similarity	NPC155329
0.8808	High Similarity	NPC114357
0.8808	High Similarity	NPC259144
0.88	High Similarity	NPC469648
0.88	High Similarity	NPC138641
0.88	High Similarity	NPC22571
0.88	High Similarity	NPC145649
0.88	High Similarity	NPC233581
0.88	High Similarity	NPC469647
0.88	High Similarity	NPC283875
0.8786	High Similarity	NPC476977
0.8784	High Similarity	NPC217918
0.8776	High Similarity	NPC277053
0.8776	High Similarity	NPC301946
0.8774	High Similarity	NPC66193
0.8767	High Similarity	NPC477894
0.8759	High Similarity	NPC266374
0.8758	High Similarity	NPC469399
0.875	High Similarity	NPC11410
0.875	High Similarity	NPC70344
0.8742	High Similarity	NPC472658
0.8742	High Similarity	NPC472657
0.8742	High Similarity	NPC248265
0.8742	High Similarity	NPC229545
0.8742	High Similarity	NPC11588
0.8742	High Similarity	NPC134685
0.8734	High Similarity	NPC477473
0.8734	High Similarity	NPC477466
0.8734	High Similarity	NPC477471

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 NPC470245 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	689
0.2-0.3	1423
0.3-0.4	2730
0.4-0.5	2433
0.5-0.6	1128
0.6-0.7	442
0.7-0.8	47
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD7236	Approved
0.8247	Intermediate Similarity	NPD7239	Suspended
0.8221	Intermediate Similarity	NPD7799	Discontinued
0.8095	Intermediate Similarity	NPD8407	Phase 2
0.8061	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD8368	Discontinued
0.8012	Intermediate Similarity	NPD8435	Approved
0.8	Intermediate Similarity	NPD8434	Phase 2
0.7907	Intermediate Similarity	NPD8360	Approved
0.7907	Intermediate Similarity	NPD8361	Approved
0.7895	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD8485	Approved
0.7823	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7058	Phase 2
0.7778	Intermediate Similarity	NPD7057	Phase 3
0.7733	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD7961	Discontinued
0.7709	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD8150	Discontinued
0.755	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4198	Discontinued
0.7516	Intermediate Similarity	NPD6190	Approved
0.7485	Intermediate Similarity	NPD8127	Discontinued
0.7467	Intermediate Similarity	NPD7008	Discontinued
0.7452	Intermediate Similarity	NPD8166	Discontinued
0.7447	Intermediate Similarity	NPD2629	Approved
0.7342	Intermediate Similarity	NPD4628	Phase 3
0.7333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6273	Approved
0.7305	Intermediate Similarity	NPD7075	Discontinued
0.7289	Intermediate Similarity	NPD5402	Approved
0.7267	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6599	Discontinued
0.7241	Intermediate Similarity	NPD7741	Discontinued
0.7225	Intermediate Similarity	NPD5844	Phase 1
0.7216	Intermediate Similarity	NPD8312	Approved
0.7216	Intermediate Similarity	NPD8313	Approved
0.7195	Intermediate Similarity	NPD7458	Discontinued
0.719	Intermediate Similarity	NPD3764	Approved
0.7178	Intermediate Similarity	NPD5403	Approved
0.7173	Intermediate Similarity	NPD8462	Phase 1
0.7169	Intermediate Similarity	NPD6801	Discontinued
0.7169	Intermediate Similarity	NPD37	Approved
0.7166	Intermediate Similarity	NPD8320	Phase 1
0.7166	Intermediate Similarity	NPD8319	Approved
0.716	Intermediate Similarity	NPD5401	Approved
0.7152	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4965	Approved
0.7143	Intermediate Similarity	NPD5126	Approved
0.7143	Intermediate Similarity	NPD5125	Phase 3
0.7143	Intermediate Similarity	NPD4967	Phase 2
0.7126	Intermediate Similarity	NPD7819	Suspended
0.712	Intermediate Similarity	NPD7700	Phase 2
0.712	Intermediate Similarity	NPD7699	Phase 2
0.7112	Intermediate Similarity	NPD7435	Discontinued
0.7111	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD6765	Approved
0.7102	Intermediate Similarity	NPD6764	Approved
0.7083	Intermediate Similarity	NPD3817	Phase 2
0.7083	Intermediate Similarity	NPD5951	Approved
0.7083	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD7228	Approved
0.7059	Intermediate Similarity	NPD6234	Discontinued
0.7051	Intermediate Similarity	NPD6355	Discontinued
0.7049	Intermediate Similarity	NPD6534	Approved
0.7049	Intermediate Similarity	NPD6535	Approved
0.7048	Intermediate Similarity	NPD4380	Phase 2
0.7042	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD8455	Phase 2
0.7019	Intermediate Similarity	NPD7003	Approved
0.7011	Intermediate Similarity	NPD7473	Discontinued
0.6994	Remote Similarity	NPD6799	Approved
0.698	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7874	Approved
0.6979	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6166	Phase 2
0.6954	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6784	Approved
0.6944	Remote Similarity	NPD6785	Approved
0.6941	Remote Similarity	NPD7768	Phase 2
0.6939	Remote Similarity	NPD8404	Phase 2
0.6939	Remote Similarity	NPD7610	Discontinued
0.6936	Remote Similarity	NPD3787	Discontinued
0.6931	Remote Similarity	NPD7497	Discontinued
0.6923	Remote Similarity	NPD6233	Phase 2
0.6919	Remote Similarity	NPD5494	Approved
0.6913	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6559	Discontinued
0.691	Remote Similarity	NPD7685	Pre-registration
0.691	Remote Similarity	NPD7240	Approved
0.6903	Remote Similarity	NPD7095	Approved
0.6897	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3751	Discontinued
0.6872	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7808	Phase 3
0.6871	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD6778	Approved
0.6862	Remote Similarity	NPD6782	Approved
0.6862	Remote Similarity	NPD6777	Approved
0.6862	Remote Similarity	NPD6781	Approved
0.6862	Remote Similarity	NPD6779	Approved
0.6862	Remote Similarity	NPD6776	Approved
0.6862	Remote Similarity	NPD6780	Approved
0.686	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6798	Discontinued
0.6852	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7697	Approved
0.6842	Remote Similarity	NPD7696	Phase 3
0.6842	Remote Similarity	NPD7698	Approved
0.6842	Remote Similarity	NPD3882	Suspended
0.6839	Remote Similarity	NPD6232	Discontinued
0.6832	Remote Similarity	NPD5762	Approved
0.6832	Remote Similarity	NPD7266	Discontinued
0.6832	Remote Similarity	NPD5763	Approved
0.6828	Remote Similarity	NPD7094	Approved
0.6828	Remote Similarity	NPD6858	Approved
0.6824	Remote Similarity	NPD5761	Phase 2
0.6824	Remote Similarity	NPD5760	Phase 2
0.6821	Remote Similarity	NPD6287	Discontinued
0.6816	Remote Similarity	NPD7251	Discontinued
0.681	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.681	Remote Similarity	NPD3750	Approved
0.6806	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7871	Phase 2
0.6806	Remote Similarity	NPD7870	Phase 2
0.6805	Remote Similarity	NPD7411	Suspended
0.6802	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7701	Phase 2
0.6786	Remote Similarity	NPD3226	Approved
0.6783	Remote Similarity	NPD2182	Approved
0.6783	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7199	Phase 2
0.678	Remote Similarity	NPD3818	Discontinued
0.677	Remote Similarity	NPD5405	Approved
0.677	Remote Similarity	NPD5406	Approved
0.677	Remote Similarity	NPD5408	Approved
0.677	Remote Similarity	NPD5404	Approved
0.6769	Remote Similarity	NPD7801	Approved
0.6761	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6797	Phase 2
0.6747	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD1237	Approved
0.6736	Remote Similarity	NPD2067	Discontinued
0.6728	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD2346	Discontinued
0.6725	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD7713	Phase 3
0.6709	Remote Similarity	NPD6663	Approved
0.6709	Remote Similarity	NPD7714	Approved
0.6709	Remote Similarity	NPD7715	Approved
0.6708	Remote Similarity	NPD3748	Approved
0.6704	Remote Similarity	NPD7074	Phase 3
0.6702	Remote Similarity	NPD6823	Phase 2
0.6687	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD1930	Approved
0.6667	Remote Similarity	NPD1929	Approved
0.6667	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6648	Remote Similarity	NPD7054	Approved
0.6647	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2534	Approved
0.6647	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD2532	Approved
0.6647	Remote Similarity	NPD2533	Approved
0.6646	Remote Similarity	NPD7097	Phase 1
0.6634	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD230	Phase 1
0.6614	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7472	Approved
0.6609	Remote Similarity	NPD3749	Approved
0.6607	Remote Similarity	NPD5049	Phase 3
0.6605	Remote Similarity	NPD2799	Discontinued
0.6604	Remote Similarity	NPD8032	Phase 2
0.6601	Remote Similarity	NPD4807	Approved
0.6601	Remote Similarity	NPD4806	Approved
0.6582	Remote Similarity	NPD8151	Discontinued
0.6581	Remote Similarity	NPD5667	Approved
0.6579	Remote Similarity	NPD5305	Approved
0.6579	Remote Similarity	NPD5306	Approved
0.6571	Remote Similarity	NPD919	Approved
0.6571	Remote Similarity	NPD1238	Approved
0.6564	Remote Similarity	NPD2438	Suspended
0.6562	Remote Similarity	NPD4060	Phase 1
0.6561	Remote Similarity	NPD5204	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