NPASS Compound

Structure

NPC114147 OpenBabel07101718332D 39 43 0 0 1 0 0 0 0 0999 V2000 8.3637 -2.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7627 -3.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3637 -1.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4977 -2.9837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7627 -3.8314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2627 -2.9654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7762 -0.9837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4977 -0.9837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6317 -2.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2627 -2.9654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7627 -2.0993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7762 0.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1884 -1.7927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7656 -0.9837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7656 0.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2627 -1.2333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2627 -1.2333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7627 1.1343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1676 -1.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5254 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6317 -1.4837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7627 -2.0993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7137 0.8253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1884 0.8253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8996 0.5163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0336 -0.9837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3015 -0.9837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7627 -2.1018 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3015 0.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0336 0.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1676 0.5163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7627 -0.3673 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8996 1.5163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8996 -1.4837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7627 -3.1018 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1676 1.5163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2627 -1.2333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7137 -1.7927 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 3 2 0 0 0 0 1 4 1 0 0 0 0 2 5 2 0 0 0 0 2 6 1 0 0 0 0 3 8 1 0 0 0 0 4 9 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 7 12 1 0 0 0 0 7 13 1 0 0 0 0 8 21 2 0 0 0 0 9 21 1 0 0 0 0 10 22 2 0 0 0 0 11 22 1 0 0 0 0 13 28 1 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 25 1 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 32 1 0 0 0 0 18 24 1 0 0 0 0 19 26 2 0 0 0 0 19 27 1 0 0 0 0 20 23 1 0 0 0 0 20 32 1 0 0 0 0 23 18 1 1 0 0 0 23 29 1 0 0 0 0 24 12 1 6 0 0 0 24 39 1 0 0 0 0 25 30 1 0 0 0 0 25 33 2 0 0 0 0 26 30 1 0 0 0 0 26 34 1 0 0 0 0 27 29 2 0 0 0 0 27 38 1 0 0 0 0 28 35 2 0 0 0 0 28 38 1 0 0 0 0 29 31 1 0 0 0 0 30 31 2 0 0 0 0 31 36 1 0 0 0 0 32 37 1 1 0 0 0 32 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	526.2
Volume:	546.503
LogP:	5.54
LogD:	3.805
LogS:	-4.936
# Rotatable Bonds:	5
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.168
Synthetic Accessibility Score:	5.32
Fsp3:	0.25
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.961
MDCK Permeability:	1.1683951925078873e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.047
Human Intestinal Absorption (HIA):	0.222
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.1
Plasma Protein Binding (PPB):	101.50035858154297%
Volume Distribution (VD):	0.381
Pgp-substrate:	0.2304014265537262%

ADMET: Metabolism

CYP1A2-inhibitor:	0.846
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.943
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.963
CYP2C9-substrate:	0.983
CYP2D6-inhibitor:	0.756
CYP2D6-substrate:	0.224
CYP3A4-inhibitor:	0.846
CYP3A4-substrate:	0.515

ADMET: Excretion

Clearance (CL):	4.479
Half-life (T1/2):	0.256

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.966
AMES Toxicity:	0.815
Rat Oral Acute Toxicity:	0.631
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.958
Carcinogencity:	0.59
Eye Corrosion:	0.003
Eye Irritation:	0.799
Respiratory Toxicity:	0.756

Download Data

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

Natural Product: NPC114147

Natural Product ID:	NPC114147
*Common Name:**	Kurzichalcolactone
IUPAC Name:	n.a.
Synonyms:	Kurzichalcolactone
Standard InCHIKey:	GHCSEVTXYYGHAC-JLGPYDEYSA-N
Standard InCHI:	InChI=1S/C32H30O7/c33-25(15-14-21-8-3-1-4-9-21)30-26(34)19-27-29(31(30)36)23-18-24(12-7-13-28(35)38-27)39-32(37,20-23)17-16-22-10-5-2-6-11-22/h1-6,8-11,14-17,19,23-24,34,36-37H,7,12-13,18,20H2/b15-14+,17-16+/t23-,24-,32+/m1/s1
SMILES:	O=C1CCC[C@@H]2C[C@@H](c3c(O1)cc(O)c(c3O)C(=O)/C=C/c1ccccc1)C[C@](O2)(O)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462973
PubChem CID:	21578952
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO29196	Cryptocarya kurzii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377019]
NPO29196	Cryptocarya kurzii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	15.0	ug.mL-1	PMID[513580]

☑ 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 NPC114147 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	376
0.1-0.2	1533
0.2-0.3	3394
0.3-0.4	8013
0.4-0.5	10711
0.5-0.6	3949
0.6-0.7	5844
0.7-0.8	5650
0.8-0.85	2348
0.85-0.9	828
0.9-0.95	48
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC114652
0.9548	High Similarity	NPC175513
0.9536	High Similarity	NPC78835
0.9536	High Similarity	NPC309512
0.9536	High Similarity	NPC316960
0.9536	High Similarity	NPC204561
0.9536	High Similarity	NPC317715
0.9536	High Similarity	NPC148945
0.9281	High Similarity	NPC178484
0.9281	High Similarity	NPC312549
0.9281	High Similarity	NPC209142
0.9231	High Similarity	NPC322459
0.9231	High Similarity	NPC323627
0.9231	High Similarity	NPC324358
0.9231	High Similarity	NPC318527
0.9177	High Similarity	NPC97812
0.9161	High Similarity	NPC121568
0.915	High Similarity	NPC19238
0.9139	High Similarity	NPC470135
0.9139	High Similarity	NPC39045
0.9139	High Similarity	NPC470136
0.9079	High Similarity	NPC25844
0.9079	High Similarity	NPC470132
0.9079	High Similarity	NPC470134
0.9079	High Similarity	NPC470131
0.9079	High Similarity	NPC470133
0.9079	High Similarity	NPC109183
0.9079	High Similarity	NPC473078
0.9051	High Similarity	NPC15815
0.9051	High Similarity	NPC105584
0.9026	High Similarity	NPC104236
0.9026	High Similarity	NPC164205
0.9026	High Similarity	NPC473016
0.9013	High Similarity	NPC473015
0.9013	High Similarity	NPC271288
0.9013	High Similarity	NPC473013
0.9	High Similarity	NPC310603
0.8994	High Similarity	NPC195136
0.8994	High Similarity	NPC226462
0.8994	High Similarity	NPC98023
0.8987	High Similarity	NPC1796
0.8987	High Similarity	NPC257166
0.8981	High Similarity	NPC79375
0.8981	High Similarity	NPC37253
0.8968	High Similarity	NPC474735
0.8961	High Similarity	NPC122894
0.8961	High Similarity	NPC39195
0.8954	High Similarity	NPC228779
0.8954	High Similarity	NPC470322
0.8954	High Similarity	NPC477955
0.8954	High Similarity	NPC154217
0.8947	High Similarity	NPC175504
0.8947	High Similarity	NPC77794
0.8947	High Similarity	NPC278249
0.8947	High Similarity	NPC223812
0.8947	High Similarity	NPC150408
0.8947	High Similarity	NPC85162
0.8947	High Similarity	NPC149026
0.8947	High Similarity	NPC125894
0.8947	High Similarity	NPC91560
0.8947	High Similarity	NPC143896
0.8947	High Similarity	NPC310130
0.8947	High Similarity	NPC75049
0.8947	High Similarity	NPC81697
0.8947	High Similarity	NPC107177
0.8947	High Similarity	NPC257097
0.8947	High Similarity	NPC39329
0.8947	High Similarity	NPC221432
0.8947	High Similarity	NPC68104
0.8947	High Similarity	NPC164980
0.8947	High Similarity	NPC169591
0.8938	High Similarity	NPC92589
0.8931	High Similarity	NPC51247
0.8924	High Similarity	NPC32867
0.8924	High Similarity	NPC471787
0.8924	High Similarity	NPC69531
0.891	High Similarity	NPC476552
0.891	High Similarity	NPC290671
0.891	High Similarity	NPC325429
0.891	High Similarity	NPC476553
0.891	High Similarity	NPC476551
0.8903	High Similarity	NPC3642
0.8902	High Similarity	NPC76047
0.8896	High Similarity	NPC473077
0.8896	High Similarity	NPC300988
0.8896	High Similarity	NPC140120
0.8896	High Similarity	NPC308200
0.8896	High Similarity	NPC110303
0.8896	High Similarity	NPC296998
0.8896	High Similarity	NPC10990
0.8896	High Similarity	NPC23728
0.8889	High Similarity	NPC196137
0.8889	High Similarity	NPC473014
0.8889	High Similarity	NPC131568
0.8889	High Similarity	NPC131579
0.8889	High Similarity	NPC235217
0.8889	High Similarity	NPC209040
0.8889	High Similarity	NPC236766
0.8889	High Similarity	NPC1886
0.8889	High Similarity	NPC197252
0.8882	High Similarity	NPC328164
0.8882	High Similarity	NPC161506
0.8882	High Similarity	NPC148757
0.8882	High Similarity	NPC10937
0.8882	High Similarity	NPC37496
0.8882	High Similarity	NPC194432
0.8882	High Similarity	NPC40833
0.8882	High Similarity	NPC324134
0.8882	High Similarity	NPC64915
0.8882	High Similarity	NPC76338
0.8882	High Similarity	NPC182852
0.8882	High Similarity	NPC296917
0.8882	High Similarity	NPC76372
0.8882	High Similarity	NPC228504
0.8882	High Similarity	NPC78
0.8882	High Similarity	NPC166482
0.8882	High Similarity	NPC227579
0.8882	High Similarity	NPC1089
0.8882	High Similarity	NPC177354
0.8882	High Similarity	NPC66515
0.8882	High Similarity	NPC223500
0.8882	High Similarity	NPC107572
0.8882	High Similarity	NPC167624
0.8882	High Similarity	NPC306829
0.8882	High Similarity	NPC265040
0.8882	High Similarity	NPC324436
0.8882	High Similarity	NPC125855
0.8882	High Similarity	NPC166934
0.8882	High Similarity	NPC220998
0.8882	High Similarity	NPC266725
0.8882	High Similarity	NPC202981
0.8882	High Similarity	NPC32739
0.8875	High Similarity	NPC42965
0.8875	High Similarity	NPC121647
0.8868	High Similarity	NPC475184
0.8868	High Similarity	NPC208258
0.8861	High Similarity	NPC66441
0.8861	High Similarity	NPC134171
0.8861	High Similarity	NPC300668
0.8861	High Similarity	NPC182555
0.8854	High Similarity	NPC115601
0.8854	High Similarity	NPC78324
0.8854	High Similarity	NPC208011
0.8854	High Similarity	NPC43345
0.8854	High Similarity	NPC174086
0.8854	High Similarity	NPC39154
0.8854	High Similarity	NPC166067
0.8846	High Similarity	NPC151973
0.8846	High Similarity	NPC471115
0.8846	High Similarity	NPC29777
0.8839	High Similarity	NPC160821
0.8839	High Similarity	NPC145467
0.8839	High Similarity	NPC161864
0.8839	High Similarity	NPC132592
0.8839	High Similarity	NPC152233
0.8839	High Similarity	NPC208303
0.8839	High Similarity	NPC106328
0.8839	High Similarity	NPC35150
0.8831	High Similarity	NPC127059
0.8831	High Similarity	NPC181388
0.8831	High Similarity	NPC20488
0.8831	High Similarity	NPC67805
0.8831	High Similarity	NPC142405
0.8831	High Similarity	NPC301276
0.8831	High Similarity	NPC176229
0.8831	High Similarity	NPC88964
0.8831	High Similarity	NPC476088
0.8831	High Similarity	NPC111786
0.8831	High Similarity	NPC285630
0.8831	High Similarity	NPC83357
0.8831	High Similarity	NPC246948
0.8831	High Similarity	NPC312973
0.8831	High Similarity	NPC54577
0.8831	High Similarity	NPC474161
0.8831	High Similarity	NPC195621
0.8831	High Similarity	NPC472629
0.8831	High Similarity	NPC470647
0.8831	High Similarity	NPC299011
0.8831	High Similarity	NPC267375
0.8831	High Similarity	NPC475052
0.8831	High Similarity	NPC214774
0.8824	High Similarity	NPC188632
0.8824	High Similarity	NPC196459
0.8824	High Similarity	NPC316816
0.8824	High Similarity	NPC470296
0.8824	High Similarity	NPC166138
0.8824	High Similarity	NPC106985
0.8824	High Similarity	NPC18585
0.8824	High Similarity	NPC94794
0.8824	High Similarity	NPC112791
0.8824	High Similarity	NPC478086
0.8824	High Similarity	NPC214166
0.8824	High Similarity	NPC185276
0.8824	High Similarity	NPC87609
0.882	High Similarity	NPC312273
0.882	High Similarity	NPC301256
0.8816	High Similarity	NPC213322
0.8816	High Similarity	NPC96408
0.8816	High Similarity	NPC4743
0.8816	High Similarity	NPC279650

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 NPC114147 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	897
0.2-0.3	1613
0.3-0.4	2512
0.4-0.5	2069
0.5-0.6	1126
0.6-0.7	383
0.7-0.8	162
0.8-0.85	37
0.85-0.9	15
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9103	High Similarity	NPD8443	Clinical (unspecified phase)
0.9032	High Similarity	NPD7411	Suspended
0.8889	High Similarity	NPD7852	Clinical (unspecified phase)
0.8805	High Similarity	NPD7768	Phase 2
0.8797	High Similarity	NPD7819	Suspended
0.875	High Similarity	NPD7075	Discontinued
0.8742	High Similarity	NPD1549	Phase 2
0.8679	High Similarity	NPD7096	Clinical (unspecified phase)
0.8675	High Similarity	NPD1550	Clinical (unspecified phase)
0.8675	High Similarity	NPD1552	Clinical (unspecified phase)
0.8645	High Similarity	NPD7410	Clinical (unspecified phase)
0.8634	High Similarity	NPD4381	Clinical (unspecified phase)
0.8634	High Similarity	NPD3749	Approved
0.8608	High Similarity	NPD4380	Phase 2
0.8526	High Similarity	NPD4378	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1510	Phase 2
0.8393	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD3750	Approved
0.8385	Intermediate Similarity	NPD6801	Discontinued
0.8366	Intermediate Similarity	NPD2796	Approved
0.8364	Intermediate Similarity	NPD6959	Discontinued
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8284	Intermediate Similarity	NPD5844	Phase 1
0.8228	Intermediate Similarity	NPD6799	Approved
0.816	Intermediate Similarity	NPD1934	Approved
0.8158	Intermediate Similarity	NPD1240	Approved
0.8148	Intermediate Similarity	NPD6599	Discontinued
0.814	Intermediate Similarity	NPD6559	Discontinued
0.8129	Intermediate Similarity	NPD1551	Phase 2
0.8107	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD6166	Phase 2
0.8084	Intermediate Similarity	NPD5494	Approved
0.8075	Intermediate Similarity	NPD5403	Approved
0.8065	Intermediate Similarity	NPD3748	Approved
0.8065	Intermediate Similarity	NPD2799	Discontinued
0.8059	Intermediate Similarity	NPD7473	Discontinued
0.8052	Intermediate Similarity	NPD1607	Approved
0.805	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD8313	Approved
0.8046	Intermediate Similarity	NPD8312	Approved
0.8026	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7074	Phase 3
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.7989	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD6232	Discontinued
0.7977	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1243	Approved
0.7965	Intermediate Similarity	NPD7054	Approved
0.7963	Intermediate Similarity	NPD920	Approved
0.795	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD5401	Approved
0.795	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD7472	Approved
0.7908	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD2935	Discontinued
0.7895	Intermediate Similarity	NPD4908	Phase 1
0.7888	Intermediate Similarity	NPD1511	Approved
0.7886	Intermediate Similarity	NPD7808	Phase 3
0.7874	Intermediate Similarity	NPD5953	Discontinued
0.7874	Intermediate Similarity	NPD6797	Phase 2
0.7866	Intermediate Similarity	NPD3226	Approved
0.7866	Intermediate Similarity	NPD7458	Discontinued
0.7844	Intermediate Similarity	NPD5402	Approved
0.7844	Intermediate Similarity	NPD3817	Phase 2
0.784	Intermediate Similarity	NPD2533	Approved
0.784	Intermediate Similarity	NPD2532	Approved
0.784	Intermediate Similarity	NPD2534	Approved
0.7833	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7251	Discontinued
0.7815	Intermediate Similarity	NPD1203	Approved
0.7812	Intermediate Similarity	NPD4628	Phase 3
0.7798	Intermediate Similarity	NPD3882	Suspended
0.7792	Intermediate Similarity	NPD2313	Discontinued
0.7791	Intermediate Similarity	NPD1512	Approved
0.7784	Intermediate Similarity	NPD8455	Phase 2
0.7784	Intermediate Similarity	NPD2801	Approved
0.776	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD7286	Phase 2
0.7756	Intermediate Similarity	NPD5124	Phase 1
0.7756	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD2800	Approved
0.7722	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1465	Phase 2
0.7677	Intermediate Similarity	NPD3268	Approved
0.7662	Intermediate Similarity	NPD6832	Phase 2
0.7647	Intermediate Similarity	NPD2798	Approved
0.7636	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2346	Discontinued
0.7625	Intermediate Similarity	NPD2344	Approved
0.7624	Intermediate Similarity	NPD4287	Approved
0.7602	Intermediate Similarity	NPD919	Approved
0.7595	Intermediate Similarity	NPD6651	Approved
0.7593	Intermediate Similarity	NPD7003	Approved
0.7582	Intermediate Similarity	NPD2797	Approved
0.7562	Intermediate Similarity	NPD5404	Approved
0.7562	Intermediate Similarity	NPD5408	Approved
0.7562	Intermediate Similarity	NPD5406	Approved
0.7562	Intermediate Similarity	NPD5405	Approved
0.756	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD4360	Phase 2
0.7554	Intermediate Similarity	NPD4363	Phase 3
0.755	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1610	Phase 2
0.7514	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD9717	Approved
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD3751	Discontinued
0.7471	Intermediate Similarity	NPD7229	Phase 3
0.747	Intermediate Similarity	NPD6273	Approved
0.7459	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD7390	Discontinued
0.7453	Intermediate Similarity	NPD6100	Approved
0.7453	Intermediate Similarity	NPD6099	Approved
0.7452	Intermediate Similarity	NPD3764	Approved
0.7439	Intermediate Similarity	NPD2309	Approved
0.7429	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD4288	Approved
0.7423	Intermediate Similarity	NPD7783	Phase 2
0.7423	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD1933	Approved
0.7407	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD3225	Approved
0.7401	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4308	Phase 3
0.7371	Intermediate Similarity	NPD5710	Approved
0.7371	Intermediate Similarity	NPD3787	Discontinued
0.7371	Intermediate Similarity	NPD5711	Approved
0.7355	Intermediate Similarity	NPD3266	Approved
0.7355	Intermediate Similarity	NPD3267	Approved
0.7349	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6798	Discontinued
0.733	Intermediate Similarity	NPD7435	Discontinued
0.7322	Intermediate Similarity	NPD8150	Discontinued
0.732	Intermediate Similarity	NPD422	Phase 1
0.7312	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD37	Approved
0.7306	Intermediate Similarity	NPD7584	Approved
0.7303	Intermediate Similarity	NPD7177	Discontinued
0.7299	Intermediate Similarity	NPD6234	Discontinued
0.7292	Intermediate Similarity	NPD7871	Phase 2
0.7292	Intermediate Similarity	NPD7870	Phase 2
0.7283	Intermediate Similarity	NPD4965	Approved
0.7283	Intermediate Similarity	NPD4967	Phase 2
0.7283	Intermediate Similarity	NPD4966	Approved
0.7273	Intermediate Similarity	NPD1608	Approved
0.7263	Intermediate Similarity	NPD6777	Approved
0.7263	Intermediate Similarity	NPD6781	Approved
0.7263	Intermediate Similarity	NPD6779	Approved
0.7263	Intermediate Similarity	NPD6776	Approved
0.7263	Intermediate Similarity	NPD6778	Approved
0.7263	Intermediate Similarity	NPD6780	Approved
0.7263	Intermediate Similarity	NPD6782	Approved
0.7251	Intermediate Similarity	NPD5890	Approved
0.7251	Intermediate Similarity	NPD5889	Approved
0.725	Intermediate Similarity	NPD943	Approved
0.7244	Intermediate Similarity	NPD1164	Approved
0.724	Intermediate Similarity	NPD7697	Approved
0.724	Intermediate Similarity	NPD7696	Phase 3
0.724	Intermediate Similarity	NPD7698	Approved
0.7234	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4361	Phase 2
0.7232	Intermediate Similarity	NPD3926	Phase 2
0.7228	Intermediate Similarity	NPD8434	Phase 2
0.7219	Intermediate Similarity	NPD7427	Discontinued
0.7207	Intermediate Similarity	NPD7228	Approved
0.7205	Intermediate Similarity	NPD6355	Discontinued
0.7194	Intermediate Similarity	NPD7874	Approved
0.7194	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7585	Approved
0.7176	Intermediate Similarity	NPD1653	Approved
0.7171	Intermediate Similarity	NPD9545	Approved
0.7171	Intermediate Similarity	NPD1548	Phase 1
0.7143	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD4307	Phase 2
0.7128	Intermediate Similarity	NPD7583	Approved
0.7125	Intermediate Similarity	NPD411	Approved
0.7125	Intermediate Similarity	NPD1296	Phase 2
0.7119	Intermediate Similarity	NPD1247	Approved
0.7117	Intermediate Similarity	NPD7097	Phase 1
0.7113	Intermediate Similarity	NPD8320	Phase 1
0.7113	Intermediate Similarity	NPD8319	Approved
0.711	Intermediate Similarity	NPD7577	Discontinued
0.7099	Intermediate Similarity	NPD447	Suspended
0.7099	Intermediate Similarity	NPD230	Phase 1
0.7093	Intermediate Similarity	NPD6585	Discontinued
0.7092	Intermediate Similarity	NPD7701	Phase 2
0.7091	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6002	Phase 3
0.7091	Intermediate Similarity	NPD6004	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data