NPASS Compound

Structure

NPC473009 OpenBabel07101718332D 49 54 0 0 1 0 0 0 0 0999 V2000 0.0850 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2810 -3.5570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2190 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7810 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 3.3122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.6910 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 4.2633 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5962 3.7281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7810 -2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 -1.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7202 5.0064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 3.9360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6470 -3.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 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 19 2 0 0 0 0 2 19 1 0 0 0 0 3 39 1 0 0 0 0 4 39 1 0 0 0 0 5 7 1 0 0 0 0 5 20 2 0 0 0 0 6 8 2 0 0 0 0 6 20 1 0 0 0 0 7 23 2 0 0 0 0 8 23 1 0 0 0 0 9 10 2 0 0 0 0 9 24 1 0 0 0 0 10 27 1 0 0 0 0 11 12 1 0 0 0 0 11 21 1 0 0 0 0 12 39 1 0 0 0 0 13 22 2 0 0 0 0 13 25 1 0 0 0 0 14 22 1 0 0 0 0 14 26 2 0 0 0 0 15 21 1 0 0 0 0 15 28 1 0 0 0 0 16 25 2 0 0 0 0 16 26 1 0 0 0 0 17 24 2 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 18 31 1 0 0 0 0 19 21 1 0 0 0 0 23 40 1 0 0 0 0 24 41 1 0 0 0 0 25 42 1 0 0 0 0 26 43 1 0 0 0 0 27 29 2 0 0 0 0 28 37 1 0 0 0 0 28 38 2 0 0 0 0 29 44 1 0 0 0 0 30 33 1 0 0 0 0 30 45 2 0 0 0 0 31 27 1 1 0 0 0 31 48 1 0 0 0 0 32 22 1 1 0 0 0 32 34 1 0 0 0 0 32 36 1 0 0 0 0 33 35 1 0 0 0 0 33 37 2 0 0 0 0 34 35 2 0 0 0 0 34 38 1 0 0 0 0 35 46 1 0 0 0 0 36 20 1 6 0 0 0 36 49 1 0 0 0 0 37 48 1 0 0 0 0 38 49 1 0 0 0 0 39 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	668.26
Volume:	682.753
LogP:	6.449
LogD:	3.537
LogS:	-3.378
# Rotatable Bonds:	9
TPSA:	177.14
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.09
Synthetic Accessibility Score:	4.773
Fsp3:	0.308
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.139
MDCK Permeability:	1.2050157238263637e-05
Pgp-inhibitor:	0.125
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.618
30% Bioavailability (F30%):	0.127

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	95.40926361083984%
Volume Distribution (VD):	0.605
Pgp-substrate:	3.446042537689209%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.52
CYP2C19-inhibitor:	0.782
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.918
CYP2C9-substrate:	0.992
CYP2D6-inhibitor:	0.525
CYP2D6-substrate:	0.745
CYP3A4-inhibitor:	0.419
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	12.171
Half-life (T1/2):	0.327

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.442
Drug-inuced Liver Injury (DILI):	0.883
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.955
Carcinogencity:	0.088
Eye Corrosion:	0.003
Eye Irritation:	0.887
Respiratory Toxicity:	0.505

Download Data

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

Natural Product: NPC473009

Natural Product ID:	NPC473009
*Common Name:**	MBBVSWDIGPICDG-CMDBODPZSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MBBVSWDIGPICDG-CMDBODPZSA-N
Standard InCHI:	InChI=1S/C39H40O10/c1-19(2)21(11-12-39(3,4)47)15-28-37-33(30(45)18-31(48-37)27-10-9-24(41)17-29(27)44)35(46)34-32(22-13-25(42)16-26(43)14-22)36(49-38(28)34)20-5-7-23(40)8-6-20/h5-10,13-14,16-17,21,31-32,36,40-44,46-47H,1,11-12,15,18H2,2-4H3/t21?,31-,32-,36+/m0/s1
SMILES:	CC(=C)C(CCC(C)(C)O)CC1=C2C(=C(C3=C1OC(CC3=O)C4=C(C=C(C=C4)O)O)O)C(C(O2)C5=CC=C(C=C5)O)C6=CC(=CC(=C6)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3600402
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	root bark	Mongolian	n.a.	PMID[26073007]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[31747283]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20471	Sophora alopecuroides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20471	Sophora alopecuroides	Species	Fabaceae	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	=	32700.0	nM	PMID[463807]

☑ 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 NPC473009 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	409
0.1-0.2	1543
0.2-0.3	3211
0.3-0.4	8656
0.4-0.5	10237
0.5-0.6	3606
0.6-0.7	5484
0.7-0.8	5730
0.8-0.85	2432
0.85-0.9	1180
0.9-0.95	193
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC473012
0.9935	High Similarity	NPC473010
0.987	High Similarity	NPC301256
0.987	High Similarity	NPC312273
0.9554	High Similarity	NPC473011
0.9548	High Similarity	NPC1796
0.9548	High Similarity	NPC257166
0.9497	High Similarity	NPC251336
0.9487	High Similarity	NPC15815
0.9487	High Similarity	NPC51247
0.9481	High Similarity	NPC121568
0.9427	High Similarity	NPC42965
0.9427	High Similarity	NPC98023
0.9427	High Similarity	NPC226462
0.9427	High Similarity	NPC195136
0.9427	High Similarity	NPC121647
0.9423	High Similarity	NPC475184
0.9419	High Similarity	NPC37253
0.9419	High Similarity	NPC79375
0.9383	High Similarity	NPC477529
0.9363	High Similarity	NPC105584
0.9359	High Similarity	NPC32867
0.9359	High Similarity	NPC69531
0.9351	High Similarity	NPC178484
0.9299	High Similarity	NPC323627
0.9299	High Similarity	NPC324358
0.9299	High Similarity	NPC287789
0.9299	High Similarity	NPC322459
0.9299	High Similarity	NPC208258
0.9299	High Similarity	NPC318527
0.9299	High Similarity	NPC271741
0.9295	High Similarity	NPC182555
0.9295	High Similarity	NPC134171
0.9295	High Similarity	NPC66441
0.9295	High Similarity	NPC300668
0.929	High Similarity	NPC115601
0.929	High Similarity	NPC78324
0.929	High Similarity	NPC208011
0.929	High Similarity	NPC39154
0.9245	High Similarity	NPC137232
0.9245	High Similarity	NPC18380
0.9241	High Similarity	NPC51760
0.9241	High Similarity	NPC295090
0.9236	High Similarity	NPC61112
0.9236	High Similarity	NPC198489
0.9221	High Similarity	NPC3642
0.9198	High Similarity	NPC253730
0.9198	High Similarity	NPC286230
0.9187	High Similarity	NPC15374
0.9182	High Similarity	NPC292863
0.9182	High Similarity	NPC184326
0.9172	High Similarity	NPC258474
0.9172	High Similarity	NPC186227
0.9172	High Similarity	NPC215203
0.9172	High Similarity	NPC52611
0.9172	High Similarity	NPC150908
0.9172	High Similarity	NPC159707
0.9172	High Similarity	NPC158027
0.9172	High Similarity	NPC14606
0.9172	High Similarity	NPC100049
0.9172	High Similarity	NPC265624
0.9172	High Similarity	NPC205026
0.9172	High Similarity	NPC201227
0.9172	High Similarity	NPC121649
0.9172	High Similarity	NPC248739
0.9167	High Similarity	NPC43345
0.9167	High Similarity	NPC174086
0.9161	High Similarity	NPC472633
0.9156	High Similarity	NPC122894
0.9136	High Similarity	NPC171985
0.9136	High Similarity	NPC82330
0.9136	High Similarity	NPC320741
0.9136	High Similarity	NPC224851
0.913	High Similarity	NPC38591
0.9119	High Similarity	NPC55443
0.9119	High Similarity	NPC18699
0.9119	High Similarity	NPC195167
0.9114	High Similarity	NPC56049
0.9114	High Similarity	NPC54830
0.9114	High Similarity	NPC309648
0.9108	High Similarity	NPC71061
0.9108	High Similarity	NPC303485
0.9108	High Similarity	NPC194593
0.9108	High Similarity	NPC290830
0.9108	High Similarity	NPC72425
0.9108	High Similarity	NPC324447
0.9107	High Similarity	NPC150977
0.9103	High Similarity	NPC476551
0.9103	High Similarity	NPC476553
0.9103	High Similarity	NPC476552
0.9097	High Similarity	NPC473016
0.9097	High Similarity	NPC132345
0.9091	High Similarity	NPC475348
0.9091	High Similarity	NPC261271
0.9074	High Similarity	NPC469664
0.9074	High Similarity	NPC169471
0.9038	High Similarity	NPC29777
0.9038	High Similarity	NPC471115
0.9036	High Similarity	NPC300657
0.9032	High Similarity	NPC145467
0.9032	High Similarity	NPC152233
0.9026	High Similarity	NPC290133
0.9026	High Similarity	NPC285630
0.9026	High Similarity	NPC109183
0.9026	High Similarity	NPC228779
0.9026	High Similarity	NPC473078
0.9026	High Similarity	NPC470134
0.9026	High Similarity	NPC470131
0.9026	High Similarity	NPC470133
0.9026	High Similarity	NPC127059
0.9026	High Similarity	NPC470132
0.9026	High Similarity	NPC24136
0.9026	High Similarity	NPC187282
0.9024	High Similarity	NPC107627
0.9024	High Similarity	NPC475212
0.9012	High Similarity	NPC63438
0.9012	High Similarity	NPC290160
0.9012	High Similarity	NPC159508
0.9006	High Similarity	NPC273467
0.9006	High Similarity	NPC92589
0.9006	High Similarity	NPC189552
0.9	High Similarity	NPC123544
0.9	High Similarity	NPC472617
0.8994	High Similarity	NPC78492
0.8994	High Similarity	NPC208152
0.8988	High Similarity	NPC121888
0.8982	High Similarity	NPC101991
0.8981	High Similarity	NPC222713
0.8981	High Similarity	NPC309512
0.8981	High Similarity	NPC316960
0.8981	High Similarity	NPC67322
0.8981	High Similarity	NPC148945
0.8981	High Similarity	NPC111112
0.8981	High Similarity	NPC204561
0.8981	High Similarity	NPC78835
0.8981	High Similarity	NPC472636
0.8981	High Similarity	NPC317715
0.8981	High Similarity	NPC138299
0.8976	High Similarity	NPC17105
0.8976	High Similarity	NPC147363
0.8976	High Similarity	NPC73899
0.8976	High Similarity	NPC474276
0.897	High Similarity	NPC102277
0.897	High Similarity	NPC287884
0.897	High Similarity	NPC8704
0.897	High Similarity	NPC279209
0.8968	High Similarity	NPC296998
0.8968	High Similarity	NPC308200
0.8968	High Similarity	NPC283234
0.8968	High Similarity	NPC473077
0.8961	High Similarity	NPC131579
0.8961	High Similarity	NPC470136
0.8961	High Similarity	NPC473014
0.8961	High Similarity	NPC39045
0.8961	High Similarity	NPC271288
0.8961	High Similarity	NPC282957
0.8961	High Similarity	NPC470135
0.8961	High Similarity	NPC235217
0.8961	High Similarity	NPC131568
0.8961	High Similarity	NPC194949
0.8957	High Similarity	NPC477840
0.8951	High Similarity	NPC261896
0.8951	High Similarity	NPC310603
0.8947	High Similarity	NPC139683
0.8947	High Similarity	NPC73929
0.8947	High Similarity	NPC47905
0.8944	High Similarity	NPC312993
0.8944	High Similarity	NPC186325
0.8938	High Similarity	NPC281137
0.8938	High Similarity	NPC65504
0.8938	High Similarity	NPC282390
0.8938	High Similarity	NPC196448
0.8931	High Similarity	NPC254351
0.8924	High Similarity	NPC473996
0.8924	High Similarity	NPC477957
0.8917	High Similarity	NPC476509
0.8917	High Similarity	NPC476185
0.8917	High Similarity	NPC321896
0.8916	High Similarity	NPC186847
0.8916	High Similarity	NPC257667
0.8916	High Similarity	NPC472454
0.891	High Similarity	NPC35150
0.891	High Similarity	NPC168085
0.891	High Similarity	NPC39195
0.891	High Similarity	NPC160821
0.891	High Similarity	NPC132592
0.891	High Similarity	NPC106328
0.891	High Similarity	NPC161191
0.8909	High Similarity	NPC53252
0.8909	High Similarity	NPC300307
0.8903	High Similarity	NPC472629
0.8903	High Similarity	NPC246948
0.8903	High Similarity	NPC267375
0.8903	High Similarity	NPC83357
0.8903	High Similarity	NPC20488
0.8903	High Similarity	NPC142405
0.8903	High Similarity	NPC111786
0.8903	High Similarity	NPC475052
0.8903	High Similarity	NPC214774
0.8903	High Similarity	NPC301276

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 NPC473009 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	933
0.2-0.3	1544
0.3-0.4	2598
0.4-0.5	1968
0.5-0.6	1088
0.6-0.7	446
0.7-0.8	168
0.8-0.85	28
0.85-0.9	17
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9295	High Similarity	NPD8443	Clinical (unspecified phase)
0.9125	High Similarity	NPD6959	Discontinued
0.8841	High Similarity	NPD7852	Clinical (unspecified phase)
0.875	High Similarity	NPD7819	Suspended
0.875	High Similarity	NPD2393	Clinical (unspecified phase)
0.8718	High Similarity	NPD7410	Clinical (unspecified phase)
0.8642	High Similarity	NPD7768	Phase 2
0.8625	High Similarity	NPD7411	Suspended
0.8614	High Similarity	NPD6166	Phase 2
0.8614	High Similarity	NPD6168	Clinical (unspecified phase)
0.8614	High Similarity	NPD6167	Clinical (unspecified phase)
0.8599	High Similarity	NPD4378	Clinical (unspecified phase)
0.8562	High Similarity	NPD4380	Phase 2
0.8506	High Similarity	NPD1552	Clinical (unspecified phase)
0.8506	High Similarity	NPD1550	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD5494	Approved
0.8476	Intermediate Similarity	NPD7075	Discontinued
0.8462	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8457	Intermediate Similarity	NPD1934	Approved
0.8452	Intermediate Similarity	NPD1549	Phase 2
0.8364	Intermediate Similarity	NPD3749	Approved
0.8304	Intermediate Similarity	NPD7074	Phase 3
0.8293	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8246	Intermediate Similarity	NPD7054	Approved
0.8235	Intermediate Similarity	NPD7473	Discontinued
0.8208	Intermediate Similarity	NPD6559	Discontinued
0.8205	Intermediate Similarity	NPD2796	Approved
0.8198	Intermediate Similarity	NPD7472	Approved
0.8193	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD7390	Discontinued
0.8161	Intermediate Similarity	NPD7808	Phase 3
0.815	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1510	Phase 2
0.8114	Intermediate Similarity	NPD8313	Approved
0.8114	Intermediate Similarity	NPD8312	Approved
0.8103	Intermediate Similarity	NPD7251	Discontinued
0.8084	Intermediate Similarity	NPD3882	Suspended
0.8081	Intermediate Similarity	NPD3818	Discontinued
0.8075	Intermediate Similarity	NPD1511	Approved
0.8072	Intermediate Similarity	NPD2801	Approved
0.8059	Intermediate Similarity	NPD6232	Discontinued
0.805	Intermediate Similarity	NPD2800	Approved
0.8046	Intermediate Similarity	NPD6797	Phase 2
0.8035	Intermediate Similarity	NPD5844	Phase 1
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.8	Intermediate Similarity	NPD1240	Approved
0.8	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1512	Approved
0.7937	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3817	Phase 2
0.7898	Intermediate Similarity	NPD1607	Approved
0.7875	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6099	Approved
0.7862	Intermediate Similarity	NPD6100	Approved
0.7857	Intermediate Similarity	NPD4908	Phase 1
0.7853	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.779	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6651	Approved
0.7778	Intermediate Similarity	NPD3750	Approved
0.7753	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD8455	Phase 2
0.775	Intermediate Similarity	NPD2935	Discontinued
0.7746	Intermediate Similarity	NPD7229	Phase 3
0.7744	Intermediate Similarity	NPD6799	Approved
0.7725	Intermediate Similarity	NPD3226	Approved
0.7711	Intermediate Similarity	NPD920	Approved
0.7706	Intermediate Similarity	NPD5402	Approved
0.7702	Intermediate Similarity	NPD2344	Approved
0.7679	Intermediate Similarity	NPD6599	Discontinued
0.7669	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7870	Phase 2
0.7632	Intermediate Similarity	NPD7871	Phase 2
0.7624	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD4363	Phase 3
0.7622	Intermediate Similarity	NPD4360	Phase 2
0.7619	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD1243	Approved
0.7605	Intermediate Similarity	NPD5403	Approved
0.76	Intermediate Similarity	NPD3926	Phase 2
0.759	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD8150	Discontinued
0.7579	Intermediate Similarity	NPD7698	Approved
0.7579	Intermediate Similarity	NPD7697	Approved
0.7579	Intermediate Similarity	NPD7696	Phase 3
0.7578	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2799	Discontinued
0.7576	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD8151	Discontinued
0.7543	Intermediate Similarity	NPD5710	Approved
0.7543	Intermediate Similarity	NPD5711	Approved
0.7543	Intermediate Similarity	NPD3787	Discontinued
0.7542	Intermediate Similarity	NPD5953	Discontinued
0.754	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1551	Phase 2
0.7528	Intermediate Similarity	NPD7286	Phase 2
0.7515	Intermediate Similarity	NPD7458	Discontinued
0.7515	Intermediate Similarity	NPD2309	Approved
0.7513	Intermediate Similarity	NPD6782	Approved
0.7513	Intermediate Similarity	NPD6777	Approved
0.7513	Intermediate Similarity	NPD6779	Approved
0.7513	Intermediate Similarity	NPD6778	Approved
0.7513	Intermediate Similarity	NPD6776	Approved
0.7513	Intermediate Similarity	NPD6780	Approved
0.7513	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7783	Phase 2
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7486	Intermediate Similarity	NPD7199	Phase 2
0.7486	Intermediate Similarity	NPD1247	Approved
0.7485	Intermediate Similarity	NPD5401	Approved
0.7485	Intermediate Similarity	NPD2346	Discontinued
0.7472	Intermediate Similarity	NPD7228	Approved
0.7472	Intermediate Similarity	NPD3751	Discontinued
0.7471	Intermediate Similarity	NPD919	Approved
0.7469	Intermediate Similarity	NPD3748	Approved
0.7442	Intermediate Similarity	NPD1465	Phase 2
0.7442	Intermediate Similarity	NPD5760	Phase 2
0.7442	Intermediate Similarity	NPD5761	Phase 2
0.7427	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7701	Phase 2
0.7423	Intermediate Similarity	NPD5406	Approved
0.7423	Intermediate Similarity	NPD5408	Approved
0.7423	Intermediate Similarity	NPD5404	Approved
0.7423	Intermediate Similarity	NPD5405	Approved
0.7405	Intermediate Similarity	NPD4287	Approved
0.7403	Intermediate Similarity	NPD1610	Phase 2
0.7401	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7801	Approved
0.7394	Intermediate Similarity	NPD4361	Phase 2
0.7394	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5124	Phase 1
0.7391	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD37	Approved
0.7381	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD6234	Discontinued
0.7362	Intermediate Similarity	NPD7033	Discontinued
0.7358	Intermediate Similarity	NPD4625	Phase 3
0.7356	Intermediate Similarity	NPD4965	Approved
0.7356	Intermediate Similarity	NPD4966	Approved
0.7356	Intermediate Similarity	NPD4967	Phase 2
0.7349	Intermediate Similarity	NPD4628	Phase 3
0.7349	Intermediate Similarity	NPD7003	Approved
0.7347	Intermediate Similarity	NPD7874	Approved
0.7347	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6823	Phase 2
0.7342	Intermediate Similarity	NPD2861	Phase 2
0.7337	Intermediate Similarity	NPD6273	Approved
0.733	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7699	Phase 2
0.7316	Intermediate Similarity	NPD7700	Phase 2
0.7312	Intermediate Similarity	NPD2313	Discontinued
0.7312	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6832	Phase 2
0.729	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7584	Approved
0.7278	Intermediate Similarity	NPD7177	Discontinued
0.7278	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD8319	Approved
0.7268	Intermediate Similarity	NPD8320	Phase 1
0.7249	Intermediate Similarity	NPD6534	Approved
0.7249	Intermediate Similarity	NPD6535	Approved
0.7246	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1613	Approved
0.7222	Intermediate Similarity	NPD943	Approved
0.7222	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD7685	Pre-registration
0.7205	Intermediate Similarity	NPD3268	Approved
0.7205	Intermediate Similarity	NPD3764	Approved
0.7197	Intermediate Similarity	NPD4749	Approved
0.7195	Intermediate Similarity	NPD7097	Phase 1
0.7191	Intermediate Similarity	NPD8127	Discontinued
0.7184	Intermediate Similarity	NPD7577	Discontinued
0.7184	Intermediate Similarity	NPD6844	Discontinued
0.717	Intermediate Similarity	NPD2798	Approved
0.7134	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD7240	Approved
0.7107	Intermediate Similarity	NPD2797	Approved
0.7107	Intermediate Similarity	NPD1203	Approved
0.7104	Intermediate Similarity	NPD1729	Discontinued
0.7098	Intermediate Similarity	NPD8285	Discontinued
0.7083	Intermediate Similarity	NPD2654	Approved
0.7081	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7447	Phase 1
0.7073	Intermediate Similarity	NPD6355	Discontinued
0.7073	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD2403	Approved
0.707	Intermediate Similarity	NPD1201	Approved
0.7066	Intermediate Similarity	NPD6004	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