NPASS Compound

Structure

NPC134260 OpenBabel07101719242D 28 30 0 0 1 0 0 0 0 0999 V2000 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 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 3.4641 0.0000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 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 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 12 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 13 2 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 22 1 0 0 0 0 12 15 2 0 0 0 0 12 16 1 0 0 0 0 15 23 1 0 0 0 0 16 27 1 0 0 0 0 17 11 1 1 0 0 0 17 18 1 0 0 0 0 17 28 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 6 0 0 0 19 20 1 0 0 0 0 19 25 1 1 0 0 0 20 21 1 0 0 0 0 20 26 1 6 0 0 0 21 27 1 1 0 0 0 21 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.17
Volume:	391.816
LogP:	1.85
LogD:	2.253
LogS:	-3.259
# Rotatable Bonds:	6
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.492
Synthetic Accessibility Score:	3.542
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.471
MDCK Permeability:	7.169041964516509e-06
Pgp-inhibitor:	0.012
Pgp-substrate:	0.033
Human Intestinal Absorption (HIA):	0.775
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.469

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	95.8191146850586%
Volume Distribution (VD):	0.692
Pgp-substrate:	1.9005253314971924%

ADMET: Metabolism

CYP1A2-inhibitor:	0.215
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.171
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.517
CYP2D6-inhibitor:	0.871
CYP2D6-substrate:	0.362
CYP3A4-inhibitor:	0.027
CYP3A4-substrate:	0.131

ADMET: Excretion

Clearance (CL):	7.818
Half-life (T1/2):	0.781

ADMET: Toxicity

hERG Blockers:	0.143
Human Hepatotoxicity (H-HT):	0.102
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.261
Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.902
Carcinogencity:	0.072
Eye Corrosion:	0.004
Eye Irritation:	0.23
Respiratory Toxicity:	0.02

Download Data

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

Natural Product: NPC134260

Natural Product ID:	NPC134260
*Common Name:**	Stilbostemin B 3'-Beta-D-Glucopyranoside
IUPAC Name:	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-hydroxy-2-methyl-5-(2-phenylethyl)phenoxy]oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	WTRYYJMNPMGQFI-YMQHIKHWSA-N
Standard InCHI:	InChI=1S/C21H26O7/c1-12-15(23)9-14(8-7-13-5-3-2-4-6-13)10-16(12)27-21-20(26)19(25)18(24)17(11-22)28-21/h2-6,9-10,17-26H,7-8,11H2,1H3/t17-,18-,19+,20-,21-/m1/s1
SMILES:	Cc1c(cc(CCc2ccccc2)cc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495642
PubChem CID:	11560189
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes [CHEMONTID:0000142] Stilbene glycosides

*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
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679323]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	roots	n.a.	n.a.	PMID[16643052]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	Roots; Stems; Tubers	n.a.	n.a.	PMID[16872143]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	roots	n.a.	n.a.	PMID[18452334]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21902195]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21902195]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19620	Stemona tuberosa	Species	Stemonaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	50.9	%	PMID[569878]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	72.4	%	PMID[569878]

☑ 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 NPC134260 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	388
0.1-0.2	1481
0.2-0.3	3833
0.3-0.4	10118
0.4-0.5	8646
0.5-0.6	4453
0.6-0.7	7785
0.7-0.8	4897
0.8-0.85	857
0.85-0.9	192
0.9-0.95	45
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9774	High Similarity	NPC210192
0.9389	High Similarity	NPC475067
0.9385	High Similarity	NPC218003
0.9313	High Similarity	NPC262606
0.9259	High Similarity	NPC262328
0.9259	High Similarity	NPC87777
0.9248	High Similarity	NPC294166
0.9248	High Similarity	NPC115022
0.9242	High Similarity	NPC121376
0.9209	High Similarity	NPC475096
0.9191	High Similarity	NPC183781
0.9173	High Similarity	NPC85799
0.9173	High Similarity	NPC303422
0.9173	High Similarity	NPC26080
0.9173	High Similarity	NPC165686
0.9143	High Similarity	NPC125755
0.9143	High Similarity	NPC99515
0.9143	High Similarity	NPC190714
0.9137	High Similarity	NPC168579
0.9137	High Similarity	NPC469313
0.9137	High Similarity	NPC76176
0.9137	High Similarity	NPC138227
0.913	High Similarity	NPC475084
0.913	High Similarity	NPC189115
0.9111	High Similarity	NPC238243
0.9091	High Similarity	NPC97326
0.9078	High Similarity	NPC227902
0.9078	High Similarity	NPC15538
0.9078	High Similarity	NPC473480
0.9077	High Similarity	NPC12308
0.9071	High Similarity	NPC161700
0.9071	High Similarity	NPC277867
0.9065	High Similarity	NPC37793
0.9065	High Similarity	NPC473044
0.9058	High Similarity	NPC469661
0.9044	High Similarity	NPC197723
0.9044	High Similarity	NPC138350
0.9044	High Similarity	NPC165482
0.9044	High Similarity	NPC3293
0.9044	High Similarity	NPC40664
0.9037	High Similarity	NPC188555
0.9037	High Similarity	NPC130496
0.9014	High Similarity	NPC175976
0.9	High Similarity	NPC25292
0.9	High Similarity	NPC473045
0.8993	High Similarity	NPC469559
0.8993	High Similarity	NPC5253
0.8993	High Similarity	NPC128337
0.8993	High Similarity	NPC472353
0.8993	High Similarity	NPC139976
0.8993	High Similarity	NPC84207
0.8993	High Similarity	NPC230718
0.8993	High Similarity	NPC49542
0.8978	High Similarity	NPC124149
0.8971	High Similarity	NPC61946
0.8966	High Similarity	NPC78809
0.8963	High Similarity	NPC215037
0.8955	High Similarity	NPC103799
0.8929	High Similarity	NPC252169
0.8929	High Similarity	NPC81638
0.8921	High Similarity	NPC108674
0.8913	High Similarity	NPC212770
0.8913	High Similarity	NPC292487
0.8913	High Similarity	NPC98777
0.8905	High Similarity	NPC306441
0.8905	High Similarity	NPC242028
0.8905	High Similarity	NPC104167
0.8905	High Similarity	NPC203230
0.8905	High Similarity	NPC16435
0.8897	High Similarity	NPC21902
0.8881	High Similarity	NPC280945
0.8872	High Similarity	NPC222572
0.8872	High Similarity	NPC40377
0.8872	High Similarity	NPC87224
0.8865	High Similarity	NPC225445
0.8846	High Similarity	NPC18128
0.8846	High Similarity	NPC77789
0.8841	High Similarity	NPC59324
0.8841	High Similarity	NPC65530
0.8832	High Similarity	NPC470356
0.8832	High Similarity	NPC121812
0.8832	High Similarity	NPC260898
0.8832	High Similarity	NPC234333
0.8832	High Similarity	NPC47398
0.8832	High Similarity	NPC94750
0.8832	High Similarity	NPC79957
0.8832	High Similarity	NPC164787
0.8832	High Similarity	NPC112246
0.8832	High Similarity	NPC112939
0.8832	High Similarity	NPC474206
0.8832	High Similarity	NPC151224
0.8828	High Similarity	NPC473621
0.8824	High Similarity	NPC263064
0.8824	High Similarity	NPC11060
0.8811	High Similarity	NPC39657
0.8806	High Similarity	NPC472797
0.8803	High Similarity	NPC226722
0.8794	High Similarity	NPC116922
0.8788	High Similarity	NPC131397
0.8788	High Similarity	NPC207179
0.8788	High Similarity	NPC278552
0.8788	High Similarity	NPC476254
0.8788	High Similarity	NPC167571
0.8786	High Similarity	NPC257095
0.8786	High Similarity	NPC89686
0.8786	High Similarity	NPC273932
0.8769	High Similarity	NPC226712
0.8768	High Similarity	NPC470802
0.8768	High Similarity	NPC474639
0.8768	High Similarity	NPC475628
0.8768	High Similarity	NPC172818
0.8768	High Similarity	NPC227503
0.8768	High Similarity	NPC476698
0.8768	High Similarity	NPC472800
0.8768	High Similarity	NPC25695
0.8768	High Similarity	NPC269091
0.8768	High Similarity	NPC302701
0.8768	High Similarity	NPC230734
0.8767	High Similarity	NPC169404
0.8767	High Similarity	NPC176186
0.8767	High Similarity	NPC53587
0.8759	High Similarity	NPC472710
0.8759	High Similarity	NPC48863
0.8759	High Similarity	NPC472709
0.8759	High Similarity	NPC87696
0.8759	High Similarity	NPC251981
0.8759	High Similarity	NPC13745
0.875	High Similarity	NPC219876
0.875	High Similarity	NPC270751
0.875	High Similarity	NPC78770
0.875	High Similarity	NPC185604
0.875	High Similarity	NPC261619
0.875	High Similarity	NPC61477
0.875	High Similarity	NPC15658
0.875	High Similarity	NPC126029
0.8741	High Similarity	NPC74320
0.8741	High Similarity	NPC107120
0.8732	High Similarity	NPC177597
0.8731	High Similarity	NPC274717
0.8731	High Similarity	NPC38604
0.8731	High Similarity	NPC211179
0.8723	High Similarity	NPC472714
0.8723	High Similarity	NPC5262
0.8707	High Similarity	NPC150442
0.8705	High Similarity	NPC474282
0.8705	High Similarity	NPC103976
0.8705	High Similarity	NPC211549
0.8705	High Similarity	NPC326797
0.8705	High Similarity	NPC107551
0.8705	High Similarity	NPC470413
0.8705	High Similarity	NPC138738
0.8705	High Similarity	NPC102904
0.8705	High Similarity	NPC176051
0.8696	High Similarity	NPC185778
0.8696	High Similarity	NPC473413
0.869	High Similarity	NPC55158
0.869	High Similarity	NPC286235
0.869	High Similarity	NPC51328
0.8686	High Similarity	NPC49074
0.8686	High Similarity	NPC215833
0.8686	High Similarity	NPC69513
0.8686	High Similarity	NPC475840
0.8676	High Similarity	NPC42760
0.8676	High Similarity	NPC268266
0.8676	High Similarity	NPC220825
0.8676	High Similarity	NPC162801
0.8676	High Similarity	NPC472590
0.8676	High Similarity	NPC268342
0.8676	High Similarity	NPC166168
0.8671	High Similarity	NPC307466
0.8667	High Similarity	NPC472795
0.8667	High Similarity	NPC472796
0.8652	High Similarity	NPC265075
0.8652	High Similarity	NPC5155
0.8652	High Similarity	NPC471389
0.8643	High Similarity	NPC471388
0.8639	High Similarity	NPC233467
0.8639	High Similarity	NPC59692
0.8636	High Similarity	NPC76465
0.8636	High Similarity	NPC38761
0.8633	High Similarity	NPC270456
0.8633	High Similarity	NPC199459
0.8633	High Similarity	NPC164857
0.8633	High Similarity	NPC265433
0.8633	High Similarity	NPC472336
0.8633	High Similarity	NPC472334
0.8633	High Similarity	NPC162659
0.8633	High Similarity	NPC327735
0.8633	High Similarity	NPC126101
0.8633	High Similarity	NPC177035
0.8633	High Similarity	NPC234952
0.8633	High Similarity	NPC52277
0.8633	High Similarity	NPC248727
0.863	High Similarity	NPC145979
0.863	High Similarity	NPC469706
0.863	High Similarity	NPC218041
0.863	High Similarity	NPC182368
0.863	High Similarity	NPC214326
0.863	High Similarity	NPC469707
0.863	High Similarity	NPC225815

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 NPC134260 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	840
0.2-0.3	1731
0.3-0.4	2778
0.4-0.5	1744
0.5-0.6	1017
0.6-0.7	602
0.7-0.8	108
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8769	High Similarity	NPD1091	Approved
0.875	High Similarity	NPD1613	Approved
0.875	High Similarity	NPD1612	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD3027	Phase 3
0.8394	Intermediate Similarity	NPD4625	Phase 3
0.8382	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD4749	Approved
0.8333	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD4908	Phase 1
0.8209	Intermediate Similarity	NPD1610	Phase 2
0.8201	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1653	Approved
0.8138	Intermediate Similarity	NPD6674	Discontinued
0.8117	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD6559	Discontinued
0.8045	Intermediate Similarity	NPD1548	Phase 1
0.8014	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD2861	Phase 2
0.795	Intermediate Similarity	NPD7074	Phase 3
0.7888	Intermediate Similarity	NPD7054	Approved
0.784	Intermediate Similarity	NPD7472	Approved
0.7826	Intermediate Similarity	NPD3818	Discontinued
0.7791	Intermediate Similarity	NPD6797	Phase 2
0.7786	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD7266	Discontinued
0.7744	Intermediate Similarity	NPD7251	Discontinued
0.7742	Intermediate Similarity	NPD37	Approved
0.7742	Intermediate Similarity	NPD1934	Approved
0.7733	Intermediate Similarity	NPD5058	Phase 3
0.7722	Intermediate Similarity	NPD6234	Discontinued
0.7716	Intermediate Similarity	NPD7228	Approved
0.7707	Intermediate Similarity	NPD4966	Approved
0.7707	Intermediate Similarity	NPD4967	Phase 2
0.7707	Intermediate Similarity	NPD4965	Approved
0.7697	Intermediate Similarity	NPD7808	Phase 3
0.7692	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD6100	Approved
0.7687	Intermediate Similarity	NPD6671	Approved
0.7687	Intermediate Similarity	NPD6099	Approved
0.7664	Intermediate Similarity	NPD5125	Phase 3
0.7664	Intermediate Similarity	NPD5126	Approved
0.7651	Intermediate Similarity	NPD1652	Phase 2
0.7632	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7199	Phase 2
0.7615	Intermediate Similarity	NPD290	Approved
0.76	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4060	Phase 1
0.758	Intermediate Similarity	NPD8455	Phase 2
0.7569	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4536	Approved
0.7551	Intermediate Similarity	NPD4538	Approved
0.7534	Intermediate Similarity	NPD5124	Phase 1
0.7534	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD5762	Approved
0.7517	Intermediate Similarity	NPD5763	Approved
0.75	Intermediate Similarity	NPD4380	Phase 2
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD3787	Discontinued
0.7455	Intermediate Similarity	NPD5844	Phase 1
0.7451	Intermediate Similarity	NPD7213	Phase 3
0.7451	Intermediate Similarity	NPD7212	Phase 2
0.744	Intermediate Similarity	NPD8312	Approved
0.744	Intermediate Similarity	NPD8313	Approved
0.7438	Intermediate Similarity	NPD7075	Discontinued
0.7432	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD422	Phase 1
0.7424	Intermediate Similarity	NPD2684	Approved
0.7423	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD5402	Approved
0.7403	Intermediate Similarity	NPD7447	Phase 1
0.74	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD8651	Approved
0.7383	Intermediate Similarity	NPD5588	Approved
0.7383	Intermediate Similarity	NPD5960	Phase 3
0.7383	Intermediate Similarity	NPD7033	Discontinued
0.7368	Intermediate Similarity	NPD3892	Phase 2
0.7368	Intermediate Similarity	NPD4750	Phase 3
0.7368	Intermediate Similarity	NPD4628	Phase 3
0.7361	Intermediate Similarity	NPD3018	Phase 2
0.7358	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2801	Approved
0.7351	Intermediate Similarity	NPD1549	Phase 2
0.7333	Intermediate Similarity	NPD7843	Approved
0.7333	Intermediate Similarity	NPD1551	Phase 2
0.7329	Intermediate Similarity	NPD6798	Discontinued
0.7321	Intermediate Similarity	NPD7240	Approved
0.7308	Intermediate Similarity	NPD5403	Approved
0.7305	Intermediate Similarity	NPD3705	Approved
0.7299	Intermediate Similarity	NPD7157	Approved
0.729	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3751	Discontinued
0.7286	Intermediate Similarity	NPD1778	Approved
0.7273	Intermediate Similarity	NPD6696	Suspended
0.7273	Intermediate Similarity	NPD968	Approved
0.7241	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD3496	Discontinued
0.7233	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1511	Approved
0.7222	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6032	Approved
0.7214	Intermediate Similarity	NPD1357	Approved
0.7208	Intermediate Similarity	NPD2677	Approved
0.7205	Intermediate Similarity	NPD3817	Phase 2
0.7203	Intermediate Similarity	NPD2983	Phase 2
0.7203	Intermediate Similarity	NPD2982	Phase 2
0.72	Intermediate Similarity	NPD7097	Phase 1
0.7195	Intermediate Similarity	NPD6959	Discontinued
0.719	Intermediate Similarity	NPD5177	Phase 3
0.7188	Intermediate Similarity	NPD6801	Discontinued
0.7181	Intermediate Similarity	NPD6355	Discontinued
0.7181	Intermediate Similarity	NPD5735	Approved
0.7179	Intermediate Similarity	NPD5401	Approved
0.7172	Intermediate Similarity	NPD6584	Phase 3
0.717	Intermediate Similarity	NPD6599	Discontinued
0.7163	Intermediate Similarity	NPD6516	Phase 2
0.7163	Intermediate Similarity	NPD5846	Approved
0.7162	Intermediate Similarity	NPD6233	Phase 2
0.716	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3882	Suspended
0.7152	Intermediate Similarity	NPD4108	Discontinued
0.7143	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD3750	Approved
0.7143	Intermediate Similarity	NPD7819	Suspended
0.7134	Intermediate Similarity	NPD1512	Approved
0.7133	Intermediate Similarity	NPD2231	Phase 2
0.7133	Intermediate Similarity	NPD2235	Phase 2
0.7133	Intermediate Similarity	NPD2981	Phase 2
0.7133	Intermediate Similarity	NPD6653	Approved
0.7124	Intermediate Similarity	NPD2424	Discontinued
0.7115	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6799	Approved
0.7114	Intermediate Similarity	NPD2238	Phase 2
0.7107	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2796	Approved
0.7103	Intermediate Similarity	NPD2797	Approved
0.7099	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1611	Approved
0.7048	Intermediate Similarity	NPD6232	Discontinued
0.7039	Intermediate Similarity	NPD1510	Phase 2
0.7034	Intermediate Similarity	NPD3225	Approved
0.7032	Intermediate Similarity	NPD4535	Phase 3
0.703	Intermediate Similarity	NPD4666	Phase 3
0.703	Intermediate Similarity	NPD6746	Phase 2
0.7029	Intermediate Similarity	NPD5283	Phase 1
0.7029	Intermediate Similarity	NPD1398	Phase 1
0.702	Intermediate Similarity	NPD1607	Approved
0.7019	Intermediate Similarity	NPD7411	Suspended
0.7014	Intermediate Similarity	NPD1608	Approved
0.7007	Intermediate Similarity	NPD228	Approved
0.7	Intermediate Similarity	NPD7340	Approved
0.7	Intermediate Similarity	NPD4140	Approved
0.7	Intermediate Similarity	NPD3620	Phase 2
0.7	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3268	Approved
0.6971	Remote Similarity	NPD6842	Approved
0.6971	Remote Similarity	NPD6841	Approved
0.6971	Remote Similarity	NPD6843	Phase 3
0.697	Remote Similarity	NPD940	Approved
0.697	Remote Similarity	NPD5709	Phase 3
0.697	Remote Similarity	NPD846	Approved
0.6968	Remote Similarity	NPD5061	Approved
0.6968	Remote Similarity	NPD5062	Approved
0.6966	Remote Similarity	NPD6582	Phase 2
0.6966	Remote Similarity	NPD6583	Phase 3
0.6966	Remote Similarity	NPD3685	Discontinued
0.6962	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD6777	Approved
0.6961	Remote Similarity	NPD6780	Approved
0.6961	Remote Similarity	NPD6776	Approved
0.6961	Remote Similarity	NPD6779	Approved
0.6961	Remote Similarity	NPD6781	Approved
0.6961	Remote Similarity	NPD6778	Approved
0.6961	Remote Similarity	NPD6782	Approved
0.6957	Remote Similarity	NPD4678	Approved
0.6957	Remote Similarity	NPD4675	Approved
0.6957	Remote Similarity	NPD5535	Approved
0.6954	Remote Similarity	NPD4340	Discontinued
0.6951	Remote Similarity	NPD7768	Phase 2
0.6948	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6004	Phase 3
0.6948	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD6002	Phase 3
0.6948	Remote Similarity	NPD6005	Phase 3
0.6933	Remote Similarity	NPD2977	Approved
0.6933	Remote Similarity	NPD5929	Approved
0.6933	Remote Similarity	NPD1465	Phase 2
0.6933	Remote Similarity	NPD2978	Approved
0.6929	Remote Similarity	NPD709	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