NPASS Compound

Structure

CID185103 OpenBabel06191715562D 30 32 0 0 1 0 0 0 0 0999 V2000 6.9282 -2.0000 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 7.7942 -1.5000 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 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -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 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 8.6603 0.0000 0.0000 O 0 0 0 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 12 1 0 0 0 0 3 14 2 0 0 0 0 4 7 2 0 0 0 0 4 11 1 0 0 0 0 5 8 1 0 0 0 0 5 11 2 0 0 0 0 6 9 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 9 13 1 0 0 0 0 10 22 1 0 0 0 0 12 16 2 0 0 0 0 13 29 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 10 1 6 0 0 0 15 17 1 0 0 0 0 15 30 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 1 0 0 0 18 19 1 0 0 0 0 18 25 1 6 0 0 0 19 21 1 0 0 0 0 19 26 1 1 0 0 0 20 27 2 0 0 0 0 20 28 1 0 0 0 0 21 29 1 6 0 0 0 21 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	418.13
Volume:	404.123
LogP:	1.411
LogD:	0.583
LogS:	-3.523
# Rotatable Bonds:	6
TPSA:	156.91
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.366
Synthetic Accessibility Score:	3.703
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.079
MDCK Permeability:	5.402092938311398e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.681
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.102
Plasma Protein Binding (PPB):	96.12285614013672%
Volume Distribution (VD):	0.414
Pgp-substrate:	1.8082506656646729%

ADMET: Metabolism

CYP1A2-inhibitor:	0.313
CYP1A2-substrate:	0.015
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.121
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.05
CYP3A4-substrate:	0.016

ADMET: Excretion

Clearance (CL):	1.421
Half-life (T1/2):	0.725

ADMET: Toxicity

hERG Blockers:	0.257
Human Hepatotoxicity (H-HT):	0.19
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.097
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.177
Carcinogencity:	0.729
Eye Corrosion:	0.003
Eye Irritation:	0.086
Respiratory Toxicity:	0.07

Download Data

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

Natural Product: NPC185103

Natural Product ID:	NPC185103
*Common Name:**	Hydrangeic Acid 4'-O-Beta-D-Glucopyranoside
IUPAC Name:	2-hydroxy-6-[(E)-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethenyl]benzoic acid
Synonyms:
Standard InCHIKey:	NHIDPRPJJPJNAB-PQMYGHKGSA-N
Standard InCHI:	InChI=1S/C21H22O9/c22-10-15-17(24)18(25)19(26)21(30-15)29-13-8-5-11(6-9-13)4-7-12-2-1-3-14(23)16(12)20(27)28/h1-9,15,17-19,21-26H,10H2,(H,27,28)/b7-4+/t15-,17-,18+,19-,21-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(cc2)/C=C/c2cccc(c2C(=O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1813263
PubChem CID:	53359461
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
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21650157]
NPO16745	Scorzonera judaica	Species	Asteraceae	Eukaryota	roots	Daba desert reserve (50 km South of Amman), Jordan	2009-APR	PMID[21650157]
NPO16745	Scorzonera judaica	Species	Asteraceae	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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	100000.0	nM	PMID[515901]
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	=	100000.0	nM	PMID[515901]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	100000.0	nM	PMID[515901]

☑ 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 NPC185103 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	358
0.1-0.2	1441
0.2-0.3	3278
0.3-0.4	7637
0.4-0.5	10054
0.5-0.6	4630
0.6-0.7	5510
0.7-0.8	7969
0.8-0.85	1467
0.85-0.9	313
0.9-0.95	38
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9669	High Similarity	NPC328093
0.9542	High Similarity	NPC22324
0.9419	High Similarity	NPC99216
0.9408	High Similarity	NPC177742
0.9299	High Similarity	NPC298847
0.9295	High Similarity	NPC7752
0.9211	High Similarity	NPC92153
0.9211	High Similarity	NPC279281
0.9211	High Similarity	NPC299435
0.9211	High Similarity	NPC260604
0.9211	High Similarity	NPC230439
0.9211	High Similarity	NPC299761
0.9195	High Similarity	NPC140722
0.9195	High Similarity	NPC4958
0.9195	High Similarity	NPC92054
0.9195	High Similarity	NPC302989
0.9177	High Similarity	NPC249977
0.9167	High Similarity	NPC61594
0.9167	High Similarity	NPC56735
0.9145	High Similarity	NPC215811
0.9108	High Similarity	NPC147596
0.9091	High Similarity	NPC127406
0.9091	High Similarity	NPC261866
0.9067	High Similarity	NPC83975
0.9062	High Similarity	NPC298778
0.9051	High Similarity	NPC178281
0.9048	High Similarity	NPC31081
0.9048	High Similarity	NPC245219
0.9045	High Similarity	NPC216752
0.9032	High Similarity	NPC43638
0.902	High Similarity	NPC121001
0.902	High Similarity	NPC259767
0.902	High Similarity	NPC88484
0.902	High Similarity	NPC259182
0.9013	High Similarity	NPC93619
0.9	High Similarity	NPC222455
0.8994	High Similarity	NPC178851
0.8974	High Similarity	NPC279732
0.8974	High Similarity	NPC308265
0.8961	High Similarity	NPC143851
0.8961	High Similarity	NPC29763
0.8961	High Similarity	NPC210003
0.8961	High Similarity	NPC106625
0.8961	High Similarity	NPC39360
0.8961	High Similarity	NPC83283
0.8938	High Similarity	NPC116745
0.8924	High Similarity	NPC300537
0.8924	High Similarity	NPC278329
0.8924	High Similarity	NPC212099
0.8924	High Similarity	NPC189142
0.8924	High Similarity	NPC101116
0.8924	High Similarity	NPC146837
0.8924	High Similarity	NPC77660
0.8924	High Similarity	NPC127782
0.8917	High Similarity	NPC271479
0.891	High Similarity	NPC474398
0.891	High Similarity	NPC257309
0.891	High Similarity	NPC161749
0.891	High Similarity	NPC476026
0.891	High Similarity	NPC156457
0.891	High Similarity	NPC474441
0.891	High Similarity	NPC313163
0.891	High Similarity	NPC474401
0.891	High Similarity	NPC197896
0.891	High Similarity	NPC258035
0.8903	High Similarity	NPC26195
0.8903	High Similarity	NPC39351
0.8903	High Similarity	NPC169248
0.8903	High Similarity	NPC97052
0.8903	High Similarity	NPC27408
0.8903	High Similarity	NPC99233
0.8903	High Similarity	NPC72649
0.8903	High Similarity	NPC95090
0.8896	High Similarity	NPC470454
0.8896	High Similarity	NPC183536
0.8896	High Similarity	NPC34965
0.8896	High Similarity	NPC199533
0.8896	High Similarity	NPC63105
0.8896	High Similarity	NPC68381
0.8896	High Similarity	NPC474345
0.8882	High Similarity	NPC259905
0.8882	High Similarity	NPC22137
0.8882	High Similarity	NPC111785
0.8868	High Similarity	NPC191306
0.8868	High Similarity	NPC19709
0.8868	High Similarity	NPC270335
0.8868	High Similarity	NPC88023
0.8868	High Similarity	NPC88043
0.8868	High Similarity	NPC168822
0.8868	High Similarity	NPC243930
0.8868	High Similarity	NPC17432
0.8868	High Similarity	NPC309025
0.8868	High Similarity	NPC29830
0.8861	High Similarity	NPC216496
0.8861	High Similarity	NPC477629
0.8861	High Similarity	NPC217950
0.8861	High Similarity	NPC48093
0.8861	High Similarity	NPC159579
0.8861	High Similarity	NPC101636
0.8861	High Similarity	NPC210961
0.8861	High Similarity	NPC472994
0.8861	High Similarity	NPC224530
0.8861	High Similarity	NPC195685
0.8861	High Similarity	NPC129217
0.8861	High Similarity	NPC85707
0.8861	High Similarity	NPC270675
0.8861	High Similarity	NPC282169
0.8861	High Similarity	NPC477628
0.8861	High Similarity	NPC259957
0.8854	High Similarity	NPC57072
0.8854	High Similarity	NPC73511
0.8854	High Similarity	NPC43761
0.8854	High Similarity	NPC231475
0.8846	High Similarity	NPC206378
0.8846	High Similarity	NPC265480
0.8846	High Similarity	NPC149368
0.8846	High Similarity	NPC307938
0.8846	High Similarity	NPC323593
0.8846	High Similarity	NPC170475
0.8846	High Similarity	NPC203500
0.8831	High Similarity	NPC215921
0.8831	High Similarity	NPC70016
0.8827	High Similarity	NPC204937
0.8827	High Similarity	NPC235260
0.8827	High Similarity	NPC244776
0.8827	High Similarity	NPC149011
0.8827	High Similarity	NPC210808
0.8827	High Similarity	NPC199079
0.8827	High Similarity	NPC155763
0.8827	High Similarity	NPC20505
0.8827	High Similarity	NPC116864
0.8824	High Similarity	NPC100818
0.8812	High Similarity	NPC22832
0.8812	High Similarity	NPC165720
0.8812	High Similarity	NPC311830
0.8812	High Similarity	NPC277205
0.8808	High Similarity	NPC291153
0.8805	High Similarity	NPC472876
0.8805	High Similarity	NPC298171
0.8805	High Similarity	NPC27942
0.8805	High Similarity	NPC473043
0.8797	High Similarity	NPC472320
0.8795	High Similarity	NPC475161
0.8795	High Similarity	NPC477860
0.8792	High Similarity	NPC65833
0.8792	High Similarity	NPC145319
0.879	High Similarity	NPC135391
0.879	High Similarity	NPC182634
0.879	High Similarity	NPC60966
0.879	High Similarity	NPC133671
0.879	High Similarity	NPC122809
0.879	High Similarity	NPC44931
0.879	High Similarity	NPC108831
0.879	High Similarity	NPC78263
0.879	High Similarity	NPC197304
0.879	High Similarity	NPC77672
0.879	High Similarity	NPC129827
0.879	High Similarity	NPC6985
0.879	High Similarity	NPC23817
0.879	High Similarity	NPC54802
0.879	High Similarity	NPC65003
0.879	High Similarity	NPC473512
0.8782	High Similarity	NPC10205
0.878	High Similarity	NPC3718
0.8774	High Similarity	NPC157898
0.8774	High Similarity	NPC295646
0.8773	High Similarity	NPC288152
0.8773	High Similarity	NPC153755
0.8773	High Similarity	NPC472386
0.8773	High Similarity	NPC257011
0.8773	High Similarity	NPC76128
0.8773	High Similarity	NPC111536
0.8773	High Similarity	NPC172807
0.8773	High Similarity	NPC30432
0.8773	High Similarity	NPC137871
0.8773	High Similarity	NPC175107
0.8773	High Similarity	NPC47140
0.8773	High Similarity	NPC211594
0.8773	High Similarity	NPC67134
0.8773	High Similarity	NPC5029
0.8773	High Similarity	NPC9002
0.8773	High Similarity	NPC190003
0.8773	High Similarity	NPC271385
0.8773	High Similarity	NPC254540
0.8766	High Similarity	NPC191154
0.8766	High Similarity	NPC131874
0.8765	High Similarity	NPC138927
0.8758	High Similarity	NPC5778
0.8758	High Similarity	NPC8856
0.8758	High Similarity	NPC118284
0.8758	High Similarity	NPC281131
0.8758	High Similarity	NPC70441
0.8758	High Similarity	NPC274618
0.8758	High Similarity	NPC308404
0.8758	High Similarity	NPC276222
0.8758	High Similarity	NPC210073
0.8758	High Similarity	NPC145038
0.8758	High Similarity	NPC253662
0.8758	High Similarity	NPC179950
0.8758	High Similarity	NPC21100

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 NPC185103 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	848
0.2-0.3	1693
0.3-0.4	2566
0.4-0.5	1916
0.5-0.6	1105
0.6-0.7	507
0.7-0.8	185
0.8-0.85	16
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.891	High Similarity	NPD4381	Clinical (unspecified phase)
0.8667	High Similarity	NPD4338	Clinical (unspecified phase)
0.865	High Similarity	NPD7054	Approved
0.8614	High Similarity	NPD8313	Approved
0.8614	High Similarity	NPD8312	Approved
0.8606	High Similarity	NPD6559	Discontinued
0.8598	High Similarity	NPD7472	Approved
0.8598	High Similarity	NPD7074	Phase 3
0.8589	High Similarity	NPD3818	Discontinued
0.8545	High Similarity	NPD6797	Phase 2
0.8494	Intermediate Similarity	NPD7251	Discontinued
0.8443	Intermediate Similarity	NPD7808	Phase 3
0.8424	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7819	Suspended
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8313	Intermediate Similarity	NPD5402	Approved
0.8302	Intermediate Similarity	NPD1934	Approved
0.8291	Intermediate Similarity	NPD4380	Phase 2
0.8266	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD8455	Phase 2
0.825	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD5403	Approved
0.8199	Intermediate Similarity	NPD3817	Phase 2
0.8137	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD6166	Phase 2
0.8105	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD5401	Approved
0.8075	Intermediate Similarity	NPD6801	Discontinued
0.8065	Intermediate Similarity	NPD3750	Approved
0.8065	Intermediate Similarity	NPD4628	Phase 3
0.8052	Intermediate Similarity	NPD1549	Phase 2
0.8052	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1653	Approved
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8025	Intermediate Similarity	NPD2801	Approved
0.8025	Intermediate Similarity	NPD6799	Approved
0.8025	Intermediate Similarity	NPD1511	Approved
0.8012	Intermediate Similarity	NPD6232	Discontinued
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7963	Intermediate Similarity	NPD37	Approved
0.7952	Intermediate Similarity	NPD7199	Phase 2
0.7952	Intermediate Similarity	NPD6959	Discontinued
0.7939	Intermediate Similarity	NPD6234	Discontinued
0.7929	Intermediate Similarity	NPD7228	Approved
0.7929	Intermediate Similarity	NPD3751	Discontinued
0.7927	Intermediate Similarity	NPD4965	Approved
0.7927	Intermediate Similarity	NPD4966	Approved
0.7927	Intermediate Similarity	NPD4967	Phase 2
0.7925	Intermediate Similarity	NPD1512	Approved
0.7922	Intermediate Similarity	NPD1551	Phase 2
0.7914	Intermediate Similarity	NPD1465	Phase 2
0.7904	Intermediate Similarity	NPD3787	Discontinued
0.7901	Intermediate Similarity	NPD7411	Suspended
0.7895	Intermediate Similarity	NPD1933	Approved
0.7888	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD3226	Approved
0.7871	Intermediate Similarity	NPD7266	Discontinued
0.7871	Intermediate Similarity	NPD2346	Discontinued
0.787	Intermediate Similarity	NPD7473	Discontinued
0.7866	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7685	Pre-registration
0.7841	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6599	Discontinued
0.7838	Intermediate Similarity	NPD1203	Approved
0.7834	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7768	Phase 2
0.7818	Intermediate Similarity	NPD3882	Suspended
0.7814	Intermediate Similarity	NPD7435	Discontinued
0.7808	Intermediate Similarity	NPD1091	Approved
0.7807	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD7783	Phase 2
0.78	Intermediate Similarity	NPD6832	Phase 2
0.7791	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3749	Approved
0.7751	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2534	Approved
0.775	Intermediate Similarity	NPD2532	Approved
0.775	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2533	Approved
0.7747	Intermediate Similarity	NPD6780	Approved
0.7747	Intermediate Similarity	NPD6778	Approved
0.7747	Intermediate Similarity	NPD6781	Approved
0.7747	Intermediate Similarity	NPD6782	Approved
0.7747	Intermediate Similarity	NPD6779	Approved
0.7747	Intermediate Similarity	NPD6777	Approved
0.7747	Intermediate Similarity	NPD6776	Approved
0.7742	Intermediate Similarity	NPD3748	Approved
0.7742	Intermediate Similarity	NPD1510	Phase 2
0.7706	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2796	Approved
0.7688	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD6823	Phase 2
0.7662	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD447	Suspended
0.7658	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2799	Discontinued
0.7606	Intermediate Similarity	NPD8151	Discontinued
0.7597	Intermediate Similarity	NPD1613	Approved
0.7597	Intermediate Similarity	NPD4060	Phase 1
0.7597	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD6798	Discontinued
0.7582	Intermediate Similarity	NPD2313	Discontinued
0.7582	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5494	Approved
0.7566	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD7874	Approved
0.7548	Intermediate Similarity	NPD6355	Discontinued
0.7546	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD7240	Approved
0.7532	Intermediate Similarity	NPD6233	Phase 2
0.7531	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD7697	Approved
0.7527	Intermediate Similarity	NPD7696	Phase 3
0.7527	Intermediate Similarity	NPD7698	Approved
0.7517	Intermediate Similarity	NPD9717	Approved
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD7930	Approved
0.7487	Intermediate Similarity	NPD7870	Phase 2
0.7487	Intermediate Similarity	NPD7871	Phase 2
0.7485	Intermediate Similarity	NPD6273	Approved
0.7484	Intermediate Similarity	NPD1240	Approved
0.7483	Intermediate Similarity	NPD2797	Approved
0.7473	Intermediate Similarity	NPD6535	Approved
0.7473	Intermediate Similarity	NPD6534	Approved
0.7472	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3764	Approved
0.7468	Intermediate Similarity	NPD5405	Approved
0.7468	Intermediate Similarity	NPD5408	Approved
0.7468	Intermediate Similarity	NPD5406	Approved
0.7468	Intermediate Similarity	NPD5404	Approved
0.746	Intermediate Similarity	NPD7701	Phase 2
0.7455	Intermediate Similarity	NPD7458	Discontinued
0.7453	Intermediate Similarity	NPD6190	Approved
0.745	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6674	Discontinued
0.7434	Intermediate Similarity	NPD2798	Approved
0.743	Intermediate Similarity	NPD8150	Discontinued
0.7394	Intermediate Similarity	NPD8319	Approved
0.7394	Intermediate Similarity	NPD8320	Phase 1
0.7391	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD1607	Approved
0.7386	Intermediate Similarity	NPD2861	Phase 2
0.7355	Intermediate Similarity	NPD411	Approved
0.7355	Intermediate Similarity	NPD3268	Approved
0.7351	Intermediate Similarity	NPD7699	Phase 2
0.7351	Intermediate Similarity	NPD7700	Phase 2
0.7344	Intermediate Similarity	NPD7801	Approved
0.7338	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8434	Phase 2
0.7329	Intermediate Similarity	NPD1652	Phase 2
0.7329	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD6212	Phase 3
0.7322	Intermediate Similarity	NPD6213	Phase 3
0.7316	Intermediate Similarity	NPD7584	Approved
0.7303	Intermediate Similarity	NPD3225	Approved
0.7296	Intermediate Similarity	NPD4308	Phase 3
0.7285	Intermediate Similarity	NPD1608	Approved
0.7283	Intermediate Similarity	NPD5710	Approved
0.7283	Intermediate Similarity	NPD5711	Approved
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD4420	Approved
0.725	Intermediate Similarity	NPD2438	Suspended
0.7235	Intermediate Similarity	NPD4288	Approved
0.7233	Intermediate Similarity	NPD7097	Phase 1
0.7233	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4908	Phase 1
0.7225	Intermediate Similarity	NPD8127	Discontinued
0.7219	Intermediate Similarity	NPD1610	Phase 2
0.7219	Intermediate Similarity	NPD1201	Approved
0.7219	Intermediate Similarity	NPD6844	Discontinued
0.7215	Intermediate Similarity	NPD230	Phase 1
0.7208	Intermediate Similarity	NPD1019	Discontinued
0.7205	Intermediate Similarity	NPD2344	Approved
0.7205	Intermediate Similarity	NPD5763	Approved
0.7205	Intermediate Similarity	NPD5762	Approved
0.7197	Intermediate Similarity	NPD4062	Phase 3
0.7191	Intermediate Similarity	NPD5953	Discontinued
0.7188	Intermediate Similarity	NPD7585	Approved
0.7186	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7095	Approved
0.7179	Intermediate Similarity	NPD3027	Phase 3
0.7178	Intermediate Similarity	NPD7003	Approved
0.7171	Intermediate Similarity	NPD1481	Phase 2
0.717	Intermediate Similarity	NPD6653	Approved
0.7162	Intermediate Similarity	NPD9493	Approved
0.716	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD4476	Approved
0.7143	Intermediate Similarity	NPD6100	Approved
0.7143	Intermediate Similarity	NPD4477	Approved
0.7143	Intermediate Similarity	NPD6099	Approved
0.7135	Intermediate Similarity	NPD7583	Approved
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1699	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