NPASS Compound

Structure

NPC210192 OpenBabel07101719152D 30 32 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 -8.6603 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 -5.1962 2.0000 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 -6.0622 1.5000 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 -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 -6.9282 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 -7.7942 1.5000 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 28 1 0 0 0 0 3 4 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 7 1 0 0 0 0 5 13 2 0 0 0 0 6 8 2 0 0 0 0 6 13 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 17 2 0 0 0 0 11 23 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 15 28 1 0 0 0 0 16 24 1 0 0 0 0 17 29 1 0 0 0 0 18 11 1 1 0 0 0 18 19 1 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 6 0 0 0 20 21 1 0 0 0 0 20 26 1 1 0 0 0 21 22 1 0 0 0 0 21 27 1 6 0 0 0 22 29 1 1 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.18
Volume:	417.902
LogP:	1.763
LogD:	2.179
LogS:	-3.575
# Rotatable Bonds:	7
TPSA:	128.84
# H-Bond Aceptor:	8
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.442
Synthetic Accessibility Score:	3.586
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.424
MDCK Permeability:	8.688623893249314e-06
Pgp-inhibitor:	0.038
Pgp-substrate:	0.285
Human Intestinal Absorption (HIA):	0.609
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.238

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.12
Plasma Protein Binding (PPB):	96.13314056396484%
Volume Distribution (VD):	0.707
Pgp-substrate:	2.022965908050537%

ADMET: Metabolism

CYP1A2-inhibitor:	0.287
CYP1A2-substrate:	0.435
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.386
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.816
CYP2D6-inhibitor:	0.911
CYP2D6-substrate:	0.884
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	9.372
Half-life (T1/2):	0.704

ADMET: Toxicity

hERG Blockers:	0.24
Human Hepatotoxicity (H-HT):	0.139
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.226
Rat Oral Acute Toxicity:	0.025
Maximum Recommended Daily Dose:	0.038
Skin Sensitization:	0.852
Carcinogencity:	0.062
Eye Corrosion:	0.004
Eye Irritation:	0.11
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC210192

Natural Product ID:	NPC210192
*Common Name:**	Stilbostemin H 3'-Beta-D-Glucopyranoside
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[2-(4-methoxyphenyl)ethyl]-2-methylphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	IELQQKDOYFODON-QMCAAQAGSA-N
Standard InCHI:	InChI=1S/C22H28O8/c1-12-16(24)9-14(4-3-13-5-7-15(28-2)8-6-13)10-17(12)29-22-21(27)20(26)19(25)18(11-23)30-22/h5-10,18-27H,3-4,11H2,1-2H3/t18-,19-,20+,21-,22-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2cc(CCc3ccc(cc3)OC)cc(c2C)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495844
PubChem CID:	11625932
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	=	31.0	%	PMID[508265]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	Activity	=	65.6	%	PMID[508265]

☑ 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 NPC210192 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	410
0.1-0.2	1516
0.2-0.3	3959
0.3-0.4	10036
0.4-0.5	8462
0.5-0.6	4241
0.6-0.7	7241
0.7-0.8	5442
0.8-0.85	1040
0.85-0.9	279
0.9-0.95	69
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9774	High Similarity	NPC134260
0.9481	High Similarity	NPC87777
0.9481	High Similarity	NPC262328
0.9474	High Similarity	NPC115022
0.9474	High Similarity	NPC294166
0.9424	High Similarity	NPC475096
0.9398	High Similarity	NPC26080
0.9398	High Similarity	NPC303422
0.9398	High Similarity	NPC85799
0.9398	High Similarity	NPC165686
0.9357	High Similarity	NPC99515
0.9357	High Similarity	NPC190714
0.9357	High Similarity	NPC125755
0.9353	High Similarity	NPC76176
0.9353	High Similarity	NPC138227
0.9353	High Similarity	NPC469313
0.9353	High Similarity	NPC168579
0.9348	High Similarity	NPC189115
0.9348	High Similarity	NPC475084
0.9333	High Similarity	NPC238243
0.9323	High Similarity	NPC475067
0.9323	High Similarity	NPC121376
0.9291	High Similarity	NPC227902
0.9291	High Similarity	NPC15538
0.9291	High Similarity	NPC473480
0.9286	High Similarity	NPC161700
0.9286	High Similarity	NPC277867
0.9281	High Similarity	NPC37793
0.9281	High Similarity	NPC473044
0.9275	High Similarity	NPC469661
0.9265	High Similarity	NPC165482
0.9265	High Similarity	NPC197723
0.9265	High Similarity	NPC3293
0.9265	High Similarity	NPC40664
0.9265	High Similarity	NPC138350
0.9259	High Similarity	NPC130496
0.9259	High Similarity	NPC188555
0.9225	High Similarity	NPC175976
0.9214	High Similarity	NPC25292
0.9214	High Similarity	NPC473045
0.9209	High Similarity	NPC139976
0.9209	High Similarity	NPC472353
0.9209	High Similarity	NPC5253
0.9209	High Similarity	NPC84207
0.9209	High Similarity	NPC469559
0.9209	High Similarity	NPC230718
0.9209	High Similarity	NPC49542
0.9209	High Similarity	NPC128337
0.9197	High Similarity	NPC124149
0.9173	High Similarity	NPC218003
0.9172	High Similarity	NPC78809
0.9143	High Similarity	NPC252169
0.9137	High Similarity	NPC108674
0.913	High Similarity	NPC98777
0.913	High Similarity	NPC212770
0.9124	High Similarity	NPC242028
0.9124	High Similarity	NPC203230
0.9104	High Similarity	NPC262606
0.9103	High Similarity	NPC21902
0.9091	High Similarity	NPC280945
0.9078	High Similarity	NPC225445
0.9058	High Similarity	NPC59324
0.9058	High Similarity	NPC65530
0.9051	High Similarity	NPC61946
0.9051	High Similarity	NPC79957
0.9044	High Similarity	NPC215037
0.9037	High Similarity	NPC103799
0.9034	High Similarity	NPC473621
0.9021	High Similarity	NPC39657
0.9014	High Similarity	NPC226722
0.9007	High Similarity	NPC81638
0.9007	High Similarity	NPC116922
0.9	High Similarity	NPC257095
0.9	High Similarity	NPC273932
0.9	High Similarity	NPC89686
0.8993	High Similarity	NPC292487
0.8993	High Similarity	NPC183781
0.8986	High Similarity	NPC306441
0.8986	High Similarity	NPC16435
0.8978	High Similarity	NPC13745
0.8978	High Similarity	NPC251981
0.8978	High Similarity	NPC48863
0.8973	High Similarity	NPC169404
0.8973	High Similarity	NPC53587
0.8973	High Similarity	NPC176186
0.8966	High Similarity	NPC472709
0.8966	High Similarity	NPC472710
0.8958	High Similarity	NPC270751
0.8955	High Similarity	NPC87224
0.8955	High Similarity	NPC222572
0.8951	High Similarity	NPC107120
0.8951	High Similarity	NPC74320
0.8944	High Similarity	NPC177597
0.8936	High Similarity	NPC472714
0.8936	High Similarity	NPC5262
0.8921	High Similarity	NPC138738
0.8921	High Similarity	NPC470413
0.8913	High Similarity	NPC234333
0.8913	High Similarity	NPC112939
0.8913	High Similarity	NPC94750
0.8913	High Similarity	NPC121812
0.8913	High Similarity	NPC151224
0.8913	High Similarity	NPC260898
0.8913	High Similarity	NPC164787
0.8913	High Similarity	NPC112246
0.8913	High Similarity	NPC474206
0.8913	High Similarity	NPC47398
0.8913	High Similarity	NPC470356
0.8912	High Similarity	NPC150442
0.8905	High Similarity	NPC215833
0.8905	High Similarity	NPC263064
0.8905	High Similarity	NPC49074
0.8905	High Similarity	NPC11060
0.8905	High Similarity	NPC69513
0.8897	High Similarity	NPC51328
0.8897	High Similarity	NPC55158
0.8897	High Similarity	NPC286235
0.8889	High Similarity	NPC97326
0.8872	High Similarity	NPC12308
0.8872	High Similarity	NPC167571
0.8872	High Similarity	NPC207179
0.8872	High Similarity	NPC278552
0.8849	High Similarity	NPC164857
0.8849	High Similarity	NPC230734
0.8849	High Similarity	NPC52277
0.8849	High Similarity	NPC269091
0.8849	High Similarity	NPC177035
0.8849	High Similarity	NPC104167
0.8849	High Similarity	NPC199459
0.8849	High Similarity	NPC227503
0.8849	High Similarity	NPC470802
0.8849	High Similarity	NPC25695
0.8849	High Similarity	NPC474639
0.8849	High Similarity	NPC302701
0.8849	High Similarity	NPC172818
0.8844	High Similarity	NPC233467
0.8844	High Similarity	NPC59692
0.8841	High Similarity	NPC187194
0.8841	High Similarity	NPC107478
0.8841	High Similarity	NPC170694
0.8841	High Similarity	NPC476411
0.8836	High Similarity	NPC225815
0.8836	High Similarity	NPC185955
0.8836	High Similarity	NPC260781
0.8836	High Similarity	NPC214326
0.8836	High Similarity	NPC469706
0.8836	High Similarity	NPC218041
0.8836	High Similarity	NPC182368
0.8836	High Similarity	NPC9933
0.8836	High Similarity	NPC145979
0.8836	High Similarity	NPC469707
0.8832	High Similarity	NPC162093
0.8832	High Similarity	NPC61477
0.8832	High Similarity	NPC219876
0.8832	High Similarity	NPC126029
0.8832	High Similarity	NPC78770
0.8832	High Similarity	NPC185604
0.8832	High Similarity	NPC299144
0.8832	High Similarity	NPC261619
0.8832	High Similarity	NPC15658
0.8828	High Similarity	NPC93924
0.8828	High Similarity	NPC130449
0.8828	High Similarity	NPC248132
0.8815	High Similarity	NPC40377
0.8815	High Similarity	NPC274717
0.8811	High Similarity	NPC473046
0.8811	High Similarity	NPC472712
0.8811	High Similarity	NPC187774
0.8811	High Similarity	NPC472713
0.8811	High Similarity	NPC118385
0.8803	High Similarity	NPC145319
0.8794	High Similarity	NPC106944
0.8786	High Similarity	NPC107551
0.8786	High Similarity	NPC102904
0.8786	High Similarity	NPC176051
0.8786	High Similarity	NPC326797
0.8786	High Similarity	NPC211549
0.8786	High Similarity	NPC103976
0.8786	High Similarity	NPC474282
0.8777	High Similarity	NPC473413
0.8777	High Similarity	NPC470236
0.8768	High Similarity	NPC475840
0.8768	High Similarity	NPC132895
0.8767	High Similarity	NPC106138
0.8759	High Similarity	NPC213074
0.8759	High Similarity	NPC193473
0.8759	High Similarity	NPC42760
0.8759	High Similarity	NPC15956
0.8759	High Similarity	NPC268266
0.8759	High Similarity	NPC224674
0.8759	High Similarity	NPC162801
0.8759	High Similarity	NPC114505
0.8759	High Similarity	NPC275284
0.8759	High Similarity	NPC220825
0.8759	High Similarity	NPC31325
0.8759	High Similarity	NPC268342
0.875	High Similarity	NPC43508
0.875	High Similarity	NPC476301
0.875	High Similarity	NPC307466
0.8741	High Similarity	NPC185307

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 NPC210192 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	849
0.2-0.3	1811
0.3-0.4	2739
0.4-0.5	1718
0.5-0.6	958
0.6-0.7	604
0.7-0.8	123
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8832	High Similarity	NPD1613	Approved
0.8832	High Similarity	NPD1612	Clinical (unspecified phase)
0.8571	High Similarity	NPD1091	Approved
0.854	High Similarity	NPD1529	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD3027	Phase 3
0.8467	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8406	Intermediate Similarity	NPD4908	Phase 1
0.8389	Intermediate Similarity	NPD1653	Approved
0.8312	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD1610	Phase 2
0.8286	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6559	Discontinued
0.8219	Intermediate Similarity	NPD6674	Discontinued
0.8214	Intermediate Similarity	NPD4625	Phase 3
0.8175	Intermediate Similarity	NPD4749	Approved
0.8156	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7074	Phase 3
0.8134	Intermediate Similarity	NPD1548	Phase 1
0.8095	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7054	Approved
0.8071	Intermediate Similarity	NPD2861	Phase 2
0.8025	Intermediate Similarity	NPD7472	Approved
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.7975	Intermediate Similarity	NPD6797	Phase 2
0.7963	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD7266	Discontinued
0.7935	Intermediate Similarity	NPD37	Approved
0.7927	Intermediate Similarity	NPD7251	Discontinued
0.7911	Intermediate Similarity	NPD6234	Discontinued
0.7901	Intermediate Similarity	NPD7228	Approved
0.7898	Intermediate Similarity	NPD4966	Approved
0.7898	Intermediate Similarity	NPD4967	Phase 2
0.7898	Intermediate Similarity	NPD4965	Approved
0.7879	Intermediate Similarity	NPD7808	Phase 3
0.7821	Intermediate Similarity	NPD1934	Approved
0.7815	Intermediate Similarity	NPD5058	Phase 3
0.7812	Intermediate Similarity	NPD7199	Phase 2
0.7785	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD8455	Phase 2
0.7771	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1652	Phase 2
0.7692	Intermediate Similarity	NPD4380	Phase 2
0.7671	Intermediate Similarity	NPD4060	Phase 1
0.7669	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6166	Phase 2
0.7669	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4538	Approved
0.7635	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4536	Approved
0.7625	Intermediate Similarity	NPD7075	Discontinued
0.7622	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5124	Phase 1
0.7619	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3018	Phase 2
0.7556	Intermediate Similarity	NPD7843	Approved
0.7533	Intermediate Similarity	NPD6100	Approved
0.7533	Intermediate Similarity	NPD6099	Approved
0.7532	Intermediate Similarity	NPD7213	Phase 3
0.7532	Intermediate Similarity	NPD7212	Phase 2
0.753	Intermediate Similarity	NPD5844	Phase 1
0.7519	Intermediate Similarity	NPD2684	Approved
0.7518	Intermediate Similarity	NPD422	Phase 1
0.7518	Intermediate Similarity	NPD6671	Approved
0.7518	Intermediate Similarity	NPD7157	Approved
0.75	Intermediate Similarity	NPD5126	Approved
0.75	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD5125	Phase 3
0.7484	Intermediate Similarity	NPD7447	Phase 1
0.7484	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD8651	Approved
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5588	Approved
0.7467	Intermediate Similarity	NPD5960	Phase 3
0.7451	Intermediate Similarity	NPD4628	Phase 3
0.7451	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD290	Approved
0.7439	Intermediate Similarity	NPD3787	Discontinued
0.7438	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2801	Approved
0.7434	Intermediate Similarity	NPD1549	Phase 2
0.7415	Intermediate Similarity	NPD6798	Discontinued
0.7413	Intermediate Similarity	NPD2983	Phase 2
0.7413	Intermediate Similarity	NPD2982	Phase 2
0.7412	Intermediate Similarity	NPD8313	Approved
0.7412	Intermediate Similarity	NPD8312	Approved
0.7407	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7097	Phase 1
0.7394	Intermediate Similarity	NPD3705	Approved
0.7391	Intermediate Similarity	NPD3817	Phase 2
0.7391	Intermediate Similarity	NPD5402	Approved
0.7378	Intermediate Similarity	NPD6959	Discontinued
0.7375	Intermediate Similarity	NPD6801	Discontinued
0.7372	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5762	Approved
0.7368	Intermediate Similarity	NPD5763	Approved
0.7343	Intermediate Similarity	NPD2981	Phase 2
0.7337	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7819	Suspended
0.7314	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1511	Approved
0.7305	Intermediate Similarity	NPD1357	Approved
0.7285	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5403	Approved
0.7267	Intermediate Similarity	NPD6355	Discontinued
0.7267	Intermediate Similarity	NPD5735	Approved
0.7262	Intermediate Similarity	NPD3751	Discontinued
0.726	Intermediate Similarity	NPD6584	Phase 3
0.7254	Intermediate Similarity	NPD6516	Phase 2
0.7254	Intermediate Similarity	NPD5846	Approved
0.725	Intermediate Similarity	NPD6599	Discontinued
0.7248	Intermediate Similarity	NPD6233	Phase 2
0.7239	Intermediate Similarity	NPD3882	Suspended
0.7237	Intermediate Similarity	NPD7033	Discontinued
0.7237	Intermediate Similarity	NPD4108	Discontinued
0.723	Intermediate Similarity	NPD7095	Approved
0.7229	Intermediate Similarity	NPD6232	Discontinued
0.7226	Intermediate Similarity	NPD3892	Phase 2
0.7226	Intermediate Similarity	NPD3750	Approved
0.7215	Intermediate Similarity	NPD1512	Approved
0.7208	Intermediate Similarity	NPD2424	Discontinued
0.7206	Intermediate Similarity	NPD4750	Phase 3
0.7205	Intermediate Similarity	NPD7411	Suspended
0.7197	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6799	Approved
0.719	Intermediate Similarity	NPD2796	Approved
0.719	Intermediate Similarity	NPD1551	Phase 2
0.7179	Intermediate Similarity	NPD2677	Approved
0.7172	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5401	Approved
0.7143	Intermediate Similarity	NPD6842	Approved
0.7143	Intermediate Similarity	NPD6841	Approved
0.7143	Intermediate Similarity	NPD6843	Phase 3
0.7133	Intermediate Similarity	NPD1778	Approved
0.7124	Intermediate Similarity	NPD1510	Phase 2
0.7123	Intermediate Similarity	NPD6696	Suspended
0.7122	Intermediate Similarity	NPD5283	Phase 1
0.7117	Intermediate Similarity	NPD1465	Phase 2
0.7115	Intermediate Similarity	NPD4535	Phase 3
0.7111	Intermediate Similarity	NPD968	Approved
0.7108	Intermediate Similarity	NPD4666	Phase 3
0.7105	Intermediate Similarity	NPD1607	Approved
0.7101	Intermediate Similarity	NPD228	Approved
0.7101	Intermediate Similarity	NPD7473	Discontinued
0.7086	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2238	Phase 2
0.7086	Intermediate Similarity	NPD4140	Approved
0.7086	Intermediate Similarity	NPD3620	Phase 2
0.7083	Intermediate Similarity	NPD3496	Discontinued
0.7078	Intermediate Similarity	NPD6032	Approved
0.7073	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD846	Approved
0.7068	Intermediate Similarity	NPD940	Approved
0.7055	Intermediate Similarity	NPD6582	Phase 2
0.7055	Intermediate Similarity	NPD3685	Discontinued
0.7055	Intermediate Similarity	NPD6583	Phase 3
0.7051	Intermediate Similarity	NPD5177	Phase 3
0.705	Intermediate Similarity	NPD5535	Approved
0.7048	Intermediate Similarity	NPD5709	Phase 3
0.7044	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4340	Discontinued
0.7037	Intermediate Similarity	NPD4675	Approved
0.7037	Intermediate Similarity	NPD4678	Approved
0.7033	Intermediate Similarity	NPD6780	Approved
0.7033	Intermediate Similarity	NPD6777	Approved
0.7033	Intermediate Similarity	NPD6779	Approved
0.7033	Intermediate Similarity	NPD6781	Approved
0.7033	Intermediate Similarity	NPD6778	Approved
0.7033	Intermediate Similarity	NPD6782	Approved
0.7033	Intermediate Similarity	NPD6776	Approved
0.7032	Intermediate Similarity	NPD3540	Phase 1
0.7032	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7768	Phase 2
0.7029	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4626	Approved
0.7012	Intermediate Similarity	NPD5929	Approved
0.7012	Intermediate Similarity	NPD2978	Approved
0.7012	Intermediate Similarity	NPD2977	Approved
0.7011	Intermediate Similarity	NPD7680	Approved
0.7006	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7466	Approved
0.7006	Intermediate Similarity	NPD5494	Approved
0.6994	Remote Similarity	NPD7685	Pre-registration
0.6993	Remote Similarity	NPD6653	Approved
0.6992	Remote Similarity	NPD1242	Phase 1
0.6986	Remote Similarity	NPD2235	Phase 2
0.6986	Remote Similarity	NPD2231	Phase 2
0.6975	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1240	Approved
0.6974	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1558	Phase 1
0.6968	Remote Similarity	NPD3539	Phase 1

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