NPASS Compound

Structure

CID65504 OpenBabel06191715402D 26 30 0 0 0 0 0 0 0 0999 V2000 0.5077 -1.8481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0157 -0.9684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1536 -2.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6767 1.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8383 1.4531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6772 -0.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8388 -1.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8716 -1.4513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7098 0.0013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0323 1.9382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7100 -0.9669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5158 1.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6771 0.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1934 1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8385 0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0329 -0.9674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8711 0.4853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0327 0.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5160 0.4846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1936 0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 -0.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5899 -1.4746 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1533 -1.4755 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8709 1.4541 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3546 0.0006 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 21 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 15 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 21 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 11 1 0 0 0 0 9 17 2 0 0 0 0 10 14 1 0 0 0 0 10 24 1 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 19 2 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 20 2 0 0 0 0 15 26 1 0 0 0 0 16 18 2 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.12
Volume:	351.849
LogP:	4.454
LogD:	4.236
LogS:	-5.074
# Rotatable Bonds:	1
TPSA:	61.06
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.677
Synthetic Accessibility Score:	3.155
Fsp3:	0.238
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.992
MDCK Permeability:	1.955991865543183e-05
Pgp-inhibitor:	0.397
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	96.91000366210938%
Volume Distribution (VD):	0.592
Pgp-substrate:	4.018455982208252%

ADMET: Metabolism

CYP1A2-inhibitor:	0.927
CYP1A2-substrate:	0.861
CYP2C19-inhibitor:	0.791
CYP2C19-substrate:	0.357
CYP2C9-inhibitor:	0.802
CYP2C9-substrate:	0.91
CYP2D6-inhibitor:	0.714
CYP2D6-substrate:	0.911
CYP3A4-inhibitor:	0.634
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	9.184
Half-life (T1/2):	0.248

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.975
Drug-inuced Liver Injury (DILI):	0.983
AMES Toxicity:	0.519
Rat Oral Acute Toxicity:	0.868
Maximum Recommended Daily Dose:	0.749
Skin Sensitization:	0.33
Carcinogencity:	0.839
Eye Corrosion:	0.003
Eye Irritation:	0.097
Respiratory Toxicity:	0.864

Download Data

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

Natural Product: NPC65504

Natural Product ID:	NPC65504
*Common Name:**	Glycyrrhizol B
IUPAC Name:	n.a.
Synonyms:	glycyrrhizol B
Standard InCHIKey:	BKLGAGSBCOUJGV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H18O5/c1-21(2)7-6-13-15(26-21)5-4-12-14-10-24-17-9-11(22)8-16(23-3)18(17)20(14)25-19(12)13/h4-9,22H,10H2,1-3H3
SMILES:	COc1cc(O)cc2c1c1oc3c(c1CO2)ccc1c3C=CC(O1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495062
PubChem CID:	11609971
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7786	Lentinus tigrinus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	Activity	=	32.0	ug ml-1	PMID[476515]

☑ 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 NPC65504 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	393
0.1-0.2	1733
0.2-0.3	3894
0.3-0.4	10036
0.4-0.5	8417
0.5-0.6	3861
0.6-0.7	5795
0.7-0.8	4693
0.8-0.85	2337
0.85-0.9	1263
0.9-0.95	268
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9799	High Similarity	NPC1477
0.9799	High Similarity	NPC213608
0.9732	High Similarity	NPC5871
0.9542	High Similarity	NPC40583
0.9536	High Similarity	NPC472462
0.953	High Similarity	NPC226644
0.953	High Similarity	NPC37226
0.953	High Similarity	NPC221868
0.953	High Similarity	NPC37208
0.9477	High Similarity	NPC268360
0.9477	High Similarity	NPC296957
0.9477	High Similarity	NPC260902
0.9467	High Similarity	NPC471115
0.9467	High Similarity	NPC29777
0.9463	High Similarity	NPC135325
0.9463	High Similarity	NPC272194
0.9423	High Similarity	NPC155640
0.9412	High Similarity	NPC247677
0.9412	High Similarity	NPC160015
0.9408	High Similarity	NPC122365
0.9404	High Similarity	NPC170169
0.94	High Similarity	NPC296030
0.94	High Similarity	NPC39929
0.94	High Similarity	NPC317492
0.9396	High Similarity	NPC12148
0.9396	High Similarity	NPC130581
0.9359	High Similarity	NPC219861
0.9355	High Similarity	NPC115432
0.9355	High Similarity	NPC260296
0.9346	High Similarity	NPC148938
0.9346	High Similarity	NPC99199
0.9346	High Similarity	NPC198490
0.9338	High Similarity	NPC230713
0.9338	High Similarity	NPC78335
0.9333	High Similarity	NPC266572
0.9333	High Similarity	NPC168085
0.9333	High Similarity	NPC39195
0.9329	High Similarity	NPC51641
0.9329	High Similarity	NPC300267
0.9329	High Similarity	NPC210826
0.9299	High Similarity	NPC38591
0.9299	High Similarity	NPC472581
0.9295	High Similarity	NPC30655
0.9295	High Similarity	NPC45124
0.9295	High Similarity	NPC74854
0.929	High Similarity	NPC476349
0.929	High Similarity	NPC476350
0.929	High Similarity	NPC244750
0.9281	High Similarity	NPC235333
0.9281	High Similarity	NPC72370
0.9281	High Similarity	NPC183874
0.9272	High Similarity	NPC178202
0.9267	High Similarity	NPC201731
0.9267	High Similarity	NPC23728
0.9267	High Similarity	NPC308200
0.9267	High Similarity	NPC237635
0.9267	High Similarity	NPC79469
0.9267	High Similarity	NPC296998
0.9267	High Similarity	NPC24673
0.9267	High Similarity	NPC110303
0.9267	High Similarity	NPC473077
0.9267	High Similarity	NPC97716
0.9267	High Similarity	NPC104406
0.9262	High Similarity	NPC234629
0.9262	High Similarity	NPC311741
0.9262	High Similarity	NPC230943
0.9255	High Similarity	NPC310794
0.9245	High Similarity	NPC476459
0.9226	High Similarity	NPC246647
0.9226	High Similarity	NPC212967
0.9226	High Similarity	NPC164110
0.9226	High Similarity	NPC96342
0.9221	High Similarity	NPC213936
0.9221	High Similarity	NPC297531
0.9221	High Similarity	NPC476169
0.9216	High Similarity	NPC473996
0.9216	High Similarity	NPC207624
0.9216	High Similarity	NPC263676
0.9216	High Similarity	NPC327269
0.9216	High Similarity	NPC476238
0.9216	High Similarity	NPC31627
0.9216	High Similarity	NPC67654
0.9211	High Similarity	NPC321896
0.9211	High Similarity	NPC476185
0.9211	High Similarity	NPC472633
0.9205	High Similarity	NPC160821
0.9205	High Similarity	NPC145467
0.9205	High Similarity	NPC6511
0.9205	High Similarity	NPC296869
0.9205	High Similarity	NPC132592
0.92	High Similarity	NPC299011
0.92	High Similarity	NPC475052
0.92	High Similarity	NPC142405
0.92	High Similarity	NPC176229
0.92	High Similarity	NPC246948
0.92	High Similarity	NPC301276
0.92	High Similarity	NPC214774
0.92	High Similarity	NPC54577
0.92	High Similarity	NPC312973
0.92	High Similarity	NPC83357
0.92	High Similarity	NPC267375
0.92	High Similarity	NPC470647
0.92	High Similarity	NPC111786
0.92	High Similarity	NPC195621
0.92	High Similarity	NPC20488
0.92	High Similarity	NPC88964
0.92	High Similarity	NPC67805
0.92	High Similarity	NPC477955
0.9195	High Similarity	NPC17262
0.9195	High Similarity	NPC38219
0.9195	High Similarity	NPC225884
0.9195	High Similarity	NPC302181
0.9195	High Similarity	NPC18585
0.9195	High Similarity	NPC166138
0.9195	High Similarity	NPC106985
0.9195	High Similarity	NPC219915
0.9182	High Similarity	NPC277480
0.9177	High Similarity	NPC109180
0.9177	High Similarity	NPC159508
0.9161	High Similarity	NPC180924
0.9156	High Similarity	NPC7989
0.9156	High Similarity	NPC472583
0.9156	High Similarity	NPC223701
0.9156	High Similarity	NPC469405
0.915	High Similarity	NPC472580
0.915	High Similarity	NPC156244
0.915	High Similarity	NPC472636
0.915	High Similarity	NPC115324
0.915	High Similarity	NPC23668
0.915	High Similarity	NPC193976
0.915	High Similarity	NPC58668
0.915	High Similarity	NPC471675
0.915	High Similarity	NPC116604
0.915	High Similarity	NPC106372
0.9145	High Similarity	NPC5173
0.9145	High Similarity	NPC471114
0.9145	High Similarity	NPC473016
0.9139	High Similarity	NPC283234
0.9139	High Similarity	NPC17816
0.9133	High Similarity	NPC271288
0.9133	High Similarity	NPC303185
0.9133	High Similarity	NPC184649
0.9133	High Similarity	NPC311144
0.9133	High Similarity	NPC209040
0.913	High Similarity	NPC120220
0.9128	High Similarity	NPC11561
0.9128	High Similarity	NPC53192
0.9128	High Similarity	NPC226636
0.9128	High Similarity	NPC144499
0.9119	High Similarity	NPC136641
0.9119	High Similarity	NPC37183
0.9114	High Similarity	NPC193998
0.9108	High Similarity	NPC304839
0.9108	High Similarity	NPC220582
0.9103	High Similarity	NPC196448
0.9097	High Similarity	NPC182555
0.9097	High Similarity	NPC66441
0.9091	High Similarity	NPC210597
0.9091	High Similarity	NPC477957
0.9091	High Similarity	NPC142308
0.9091	High Similarity	NPC285623
0.9085	High Similarity	NPC120105
0.9085	High Similarity	NPC167576
0.9085	High Similarity	NPC148423
0.9085	High Similarity	NPC472421
0.9085	High Similarity	NPC61258
0.9085	High Similarity	NPC188403
0.9085	High Similarity	NPC101957
0.9085	High Similarity	NPC135303
0.9079	High Similarity	NPC161191
0.9079	High Similarity	NPC244407
0.9074	High Similarity	NPC472584
0.9073	High Similarity	NPC124729
0.9073	High Similarity	NPC473078
0.9073	High Similarity	NPC470134
0.9073	High Similarity	NPC470131
0.9073	High Similarity	NPC470132
0.9073	High Similarity	NPC470133
0.9073	High Similarity	NPC109183
0.9073	High Similarity	NPC472629
0.9068	High Similarity	NPC53252
0.9067	High Similarity	NPC91560
0.9067	High Similarity	NPC113770
0.9067	High Similarity	NPC316816
0.9067	High Similarity	NPC75049
0.9067	High Similarity	NPC164980
0.9067	High Similarity	NPC169591
0.9067	High Similarity	NPC175504
0.9067	High Similarity	NPC221432
0.9067	High Similarity	NPC478086
0.9067	High Similarity	NPC150408
0.9067	High Similarity	NPC68104
0.9067	High Similarity	NPC149026
0.9067	High Similarity	NPC257097
0.9067	High Similarity	NPC39329
0.9067	High Similarity	NPC214166
0.9067	High Similarity	NPC143896
0.9067	High Similarity	NPC310130
0.9062	High Similarity	NPC323137
0.9062	High Similarity	NPC53640

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 NPC65504 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	982
0.2-0.3	1481
0.3-0.4	2636
0.4-0.5	2014
0.5-0.6	1152
0.6-0.7	356
0.7-0.8	129
0.8-0.85	44
0.85-0.9	14
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9007	High Similarity	NPD4378	Clinical (unspecified phase)
0.9007	High Similarity	NPD7410	Clinical (unspecified phase)
0.8981	High Similarity	NPD3749	Approved
0.8854	High Similarity	NPD8443	Clinical (unspecified phase)
0.8839	High Similarity	NPD4380	Phase 2
0.8782	High Similarity	NPD7411	Suspended
0.8733	High Similarity	NPD1549	Phase 2
0.8671	High Similarity	NPD2393	Clinical (unspecified phase)
0.8667	High Similarity	NPD1550	Clinical (unspecified phase)
0.8667	High Similarity	NPD1552	Clinical (unspecified phase)
0.8658	High Similarity	NPD1510	Phase 2
0.865	High Similarity	NPD7852	Clinical (unspecified phase)
0.8645	High Similarity	NPD920	Approved
0.86	High Similarity	NPD2796	Approved
0.858	High Similarity	NPD6959	Discontinued
0.8562	High Similarity	NPD7768	Phase 2
0.8553	High Similarity	NPD7819	Suspended
0.8543	High Similarity	NPD2344	Approved
0.8519	High Similarity	NPD5494	Approved
0.8516	High Similarity	NPD642	Clinical (unspecified phase)
0.8509	High Similarity	NPD4381	Clinical (unspecified phase)
0.8509	High Similarity	NPD7075	Discontinued
0.8452	Intermediate Similarity	NPD6559	Discontinued
0.8438	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD2800	Approved
0.8431	Intermediate Similarity	NPD1243	Approved
0.8389	Intermediate Similarity	NPD1240	Approved
0.8387	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD1934	Approved
0.8333	Intermediate Similarity	NPD3882	Suspended
0.8323	Intermediate Similarity	NPD2309	Approved
0.8323	Intermediate Similarity	NPD2801	Approved
0.8278	Intermediate Similarity	NPD1607	Approved
0.8274	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6801	Discontinued
0.8258	Intermediate Similarity	NPD3750	Approved
0.8217	Intermediate Similarity	NPD1511	Approved
0.8214	Intermediate Similarity	NPD3818	Discontinued
0.8204	Intermediate Similarity	NPD6166	Phase 2
0.8204	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD2533	Approved
0.8165	Intermediate Similarity	NPD2532	Approved
0.8165	Intermediate Similarity	NPD2534	Approved
0.8133	Intermediate Similarity	NPD1247	Approved
0.8113	Intermediate Similarity	NPD1512	Approved
0.811	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6799	Approved
0.8084	Intermediate Similarity	NPD6232	Discontinued
0.8081	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD5844	Phase 1
0.8047	Intermediate Similarity	NPD7473	Discontinued
0.8036	Intermediate Similarity	NPD3926	Phase 2
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8013	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD919	Approved
0.7953	Intermediate Similarity	NPD7054	Approved
0.7949	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD3817	Phase 2
0.7935	Intermediate Similarity	NPD2799	Discontinued
0.7935	Intermediate Similarity	NPD3748	Approved
0.791	Intermediate Similarity	NPD4287	Approved
0.7907	Intermediate Similarity	NPD7472	Approved
0.7907	Intermediate Similarity	NPD7074	Phase 3
0.7898	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2313	Discontinued
0.7885	Intermediate Similarity	NPD2935	Discontinued
0.7885	Intermediate Similarity	NPD1551	Phase 2
0.7881	Intermediate Similarity	NPD4908	Phase 1
0.7861	Intermediate Similarity	NPD6797	Phase 2
0.7861	Intermediate Similarity	NPD5953	Discontinued
0.7849	Intermediate Similarity	NPD7286	Phase 2
0.784	Intermediate Similarity	NPD5403	Approved
0.7831	Intermediate Similarity	NPD5402	Approved
0.7816	Intermediate Similarity	NPD7251	Discontinued
0.7799	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7808	Phase 3
0.7764	Intermediate Similarity	NPD7390	Discontinued
0.7744	Intermediate Similarity	NPD3226	Approved
0.7735	Intermediate Similarity	NPD4363	Phase 3
0.7735	Intermediate Similarity	NPD4360	Phase 2
0.7725	Intermediate Similarity	NPD2296	Approved
0.7722	Intermediate Similarity	NPD2346	Discontinued
0.7716	Intermediate Similarity	NPD5401	Approved
0.7707	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6651	Approved
0.7688	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1465	Phase 2
0.7661	Intermediate Similarity	NPD5710	Approved
0.7661	Intermediate Similarity	NPD5711	Approved
0.7661	Intermediate Similarity	NPD7229	Phase 3
0.7658	Intermediate Similarity	NPD6100	Approved
0.7658	Intermediate Similarity	NPD6099	Approved
0.7657	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD6279	Approved
0.7605	Intermediate Similarity	NPD6280	Approved
0.7596	Intermediate Similarity	NPD4361	Phase 2
0.7596	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD7033	Discontinued
0.7578	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4628	Phase 3
0.756	Intermediate Similarity	NPD5761	Phase 2
0.756	Intermediate Similarity	NPD5760	Phase 2
0.7548	Intermediate Similarity	NPD3764	Approved
0.7533	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1610	Phase 2
0.753	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5124	Phase 1
0.7516	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD1729	Discontinued
0.75	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD8434	Phase 2
0.7486	Intermediate Similarity	NPD3751	Discontinued
0.7484	Intermediate Similarity	NPD4625	Phase 3
0.7459	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD6808	Phase 2
0.7452	Intermediate Similarity	NPD943	Approved
0.7451	Intermediate Similarity	NPD1203	Approved
0.744	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD3268	Approved
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7419	Intermediate Similarity	NPD6832	Phase 2
0.741	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1548	Phase 1
0.7382	Intermediate Similarity	NPD7584	Approved
0.7375	Intermediate Similarity	NPD4308	Phase 3
0.7362	Intermediate Similarity	NPD7003	Approved
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.734	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2797	Approved
0.7329	Intermediate Similarity	NPD5406	Approved
0.7329	Intermediate Similarity	NPD5408	Approved
0.7329	Intermediate Similarity	NPD5405	Approved
0.7329	Intermediate Similarity	NPD5404	Approved
0.7322	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7458	Discontinued
0.731	Intermediate Similarity	NPD4288	Approved
0.7301	Intermediate Similarity	NPD2654	Approved
0.7294	Intermediate Similarity	NPD6844	Discontinued
0.7273	Intermediate Similarity	NPD2403	Approved
0.7255	Intermediate Similarity	NPD9717	Approved
0.7253	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD8455	Phase 2
0.7249	Intermediate Similarity	NPD6776	Approved
0.7249	Intermediate Similarity	NPD6782	Approved
0.7249	Intermediate Similarity	NPD6780	Approved
0.7249	Intermediate Similarity	NPD6778	Approved
0.7249	Intermediate Similarity	NPD6777	Approved
0.7249	Intermediate Similarity	NPD6779	Approved
0.7249	Intermediate Similarity	NPD6781	Approved
0.7239	Intermediate Similarity	NPD2424	Discontinued
0.7235	Intermediate Similarity	NPD5890	Approved
0.7235	Intermediate Similarity	NPD5889	Approved
0.7216	Intermediate Similarity	NPD8151	Discontinued
0.72	Intermediate Similarity	NPD7199	Phase 2
0.7193	Intermediate Similarity	NPD7577	Discontinued
0.7191	Intermediate Similarity	NPD7177	Discontinued
0.719	Intermediate Similarity	NPD422	Phase 1
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7188	Intermediate Similarity	NPD230	Phase 1
0.7188	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6585	Discontinued
0.7175	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3225	Approved
0.7143	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD7435	Discontinued
0.7135	Intermediate Similarity	NPD7698	Approved
0.7135	Intermediate Similarity	NPD7697	Approved
0.7135	Intermediate Similarity	NPD3446	Phase 1
0.7134	Intermediate Similarity	NPD2861	Phase 2
0.7127	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4307	Phase 2
0.7125	Intermediate Similarity	NPD1613	Approved
0.712	Intermediate Similarity	NPD8150	Discontinued
0.7119	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1470	Approved
0.7115	Intermediate Similarity	NPD3267	Approved
0.7115	Intermediate Similarity	NPD3266	Approved
0.7115	Intermediate Similarity	NPD1164	Approved
0.7108	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4749	Approved
0.7093	Intermediate Similarity	NPD37	Approved
0.7089	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6234	Discontinued
0.7083	Intermediate Similarity	NPD7447	Phase 1
0.7083	Intermediate Similarity	NPD7422	Clinical (unspecified phase)

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