NPASS Compound

Structure

CID18135 OpenBabel06191715342D 36 40 0 0 1 0 0 0 0 0999 V2000 4.3552 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4040 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7142 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8205 -3.4146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6654 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8205 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5125 -1.1065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4668 -0.9036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6654 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4016 -0.8846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6775 0.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1307 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4878 -0.8449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5103 -1.4634 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5591 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7142 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9756 -2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0247 -0.2616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0544 -0.1596 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6654 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9756 0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8205 -1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6123 0.4825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5103 -0.4878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8205 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9756 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5591 -2.4390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5591 1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1307 -3.4146 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8873 1.1353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5687 0.0666 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7142 -0.9756 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 0.1307 1.4634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9756 -1.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5666 0.6853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 17 1 0 0 0 0 5 6 1 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 8 2 0 0 0 0 7 18 1 0 0 0 0 8 31 1 0 0 0 0 9 14 1 0 0 0 0 9 22 1 0 0 0 0 10 19 1 0 0 0 0 11 18 2 0 0 0 0 11 31 1 0 0 0 0 12 25 1 0 0 0 0 12 32 1 0 0 0 0 13 33 1 0 0 0 0 14 24 1 6 0 0 0 15 27 2 0 0 0 0 15 32 1 0 0 0 0 16 28 2 0 0 0 0 16 34 1 0 0 0 0 17 29 2 0 0 0 0 17 35 1 0 0 0 0 19 18 1 1 0 0 0 19 36 1 0 0 0 0 20 24 1 6 0 0 0 20 25 1 0 0 0 0 21 26 1 1 0 0 0 21 34 1 0 0 0 0 22 25 1 6 0 0 0 22 35 1 0 0 0 0 23 24 1 0 0 0 0 23 30 2 0 0 0 0 23 36 1 0 0 0 0 24 10 1 1 0 0 0 25 26 1 1 0 0 0 26 13 1 1 0 0 0 26 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	504.2
Volume:	487.553
LogP:	2.11
LogD:	1.412
LogS:	-4.385
# Rotatable Bonds:	8
TPSA:	130.87
# H-Bond Aceptor:	10
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.335
Synthetic Accessibility Score:	5.766
Fsp3:	0.692
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.232
MDCK Permeability:	7.31856853235513e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.438
30% Bioavailability (F30%):	0.847

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.781
Plasma Protein Binding (PPB):	78.42153930664062%
Volume Distribution (VD):	1.659
Pgp-substrate:	20.747163772583008%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.081
CYP2C9-inhibitor:	0.104
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.095
CYP2D6-substrate:	0.11
CYP3A4-inhibitor:	0.714
CYP3A4-substrate:	0.349

ADMET: Excretion

Clearance (CL):	3.486
Half-life (T1/2):	0.709

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.677
Drug-inuced Liver Injury (DILI):	0.878
AMES Toxicity:	0.868
Rat Oral Acute Toxicity:	0.983
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.27
Carcinogencity:	0.411
Eye Corrosion:	0.006
Eye Irritation:	0.14
Respiratory Toxicity:	0.908

Download Data

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

Natural Product: NPC18135

Natural Product ID:	NPC18135
*Common Name:**	RCVVNRBNRKRZGL-BMQMGEQGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RCVVNRBNRKRZGL-BMQMGEQGSA-N
Standard InCHI:	InChI=1S/C26H32O10/c1-14-9-22(35-17(4)29)25(12-32-15(2)27)20(5-6-21(34-16(3)28)26(25)13-33-26)24(14)10-19(36-23(24)30)18-7-8-31-11-18/h7-8,11,14,19-22H,5-6,9-10,12-13H2,1-4H3/t14-,19-,20-,21+,22+,24-,25+,26-/m1/s1
SMILES:	CC(=O)OC[C@@]12[C@@H](OC(=O)C)C[C@H]([C@@]3([C@H]1CC[C@@H]([C@@]12CO1)OC(=O)C)C[C@@H](OC3=O)c1cocc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269291
PubChem CID:	45033618
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO4508	Crotalaria axillaris	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5302	Verticillium biguttatum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT454	Organism	Tenebrio molitor	Tenebrio molitor	Inhibition	=	30.63	%	PMID[533709]

☑ 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 NPC18135 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	398
0.1-0.2	1432
0.2-0.3	3138
0.3-0.4	5948
0.4-0.5	10842
0.5-0.6	9868
0.6-0.7	9374
0.7-0.8	1205
0.8-0.85	287
0.85-0.9	177
0.9-0.95	26
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC221809
0.9408	High Similarity	NPC469846
0.94	High Similarity	NPC299038
0.9392	High Similarity	NPC476201
0.9333	High Similarity	NPC126723
0.9276	High Similarity	NPC472653
0.9272	High Similarity	NPC286722
0.9267	High Similarity	NPC476262
0.9262	High Similarity	NPC268905
0.9226	High Similarity	NPC472651
0.9216	High Similarity	NPC472668
0.9211	High Similarity	NPC473473
0.9211	High Similarity	NPC475295
0.9205	High Similarity	NPC209364
0.9205	High Similarity	NPC107646
0.9167	High Similarity	NPC472652
0.9167	High Similarity	NPC271235
0.9156	High Similarity	NPC476197
0.9156	High Similarity	NPC471168
0.9156	High Similarity	NPC472669
0.915	High Similarity	NPC305016
0.915	High Similarity	NPC475381
0.915	High Similarity	NPC191828
0.9145	High Similarity	NPC167142
0.9139	High Similarity	NPC469850
0.9133	High Similarity	NPC75906
0.9128	High Similarity	NPC476122
0.9128	High Similarity	NPC156189
0.9103	High Similarity	NPC476861
0.9103	High Similarity	NPC476850
0.9097	High Similarity	NPC123088
0.9091	High Similarity	NPC470939
0.9091	High Similarity	NPC471167
0.9091	High Similarity	NPC471166
0.9085	High Similarity	NPC475967
0.9085	High Similarity	NPC475226
0.9085	High Similarity	NPC237155
0.9073	High Similarity	NPC57998
0.906	High Similarity	NPC470790
0.906	High Similarity	NPC470791
0.906	High Similarity	NPC195325
0.9054	High Similarity	NPC470941
0.9054	High Similarity	NPC255414
0.9041	High Similarity	NPC223415
0.9038	High Similarity	NPC472141
0.9032	High Similarity	NPC134254
0.9032	High Similarity	NPC39986
0.9032	High Similarity	NPC302369
0.9026	High Similarity	NPC335761
0.9026	High Similarity	NPC25255
0.902	High Similarity	NPC187149
0.902	High Similarity	NPC472776
0.902	High Similarity	NPC472778
0.902	High Similarity	NPC472777
0.9013	High Similarity	NPC214541
0.9013	High Similarity	NPC44675
0.9007	High Similarity	NPC182427
0.9007	High Similarity	NPC308205
0.9007	High Similarity	NPC322546
0.9007	High Similarity	NPC29695
0.9	High Similarity	NPC469335
0.9	High Similarity	NPC159927
0.9	High Similarity	NPC477404
0.9	High Similarity	NPC196864
0.8981	High Similarity	NPC173516
0.898	High Similarity	NPC251865
0.8974	High Similarity	NPC476857
0.8974	High Similarity	NPC476856
0.8974	High Similarity	NPC476858
0.8968	High Similarity	NPC82851
0.8968	High Similarity	NPC5079
0.8968	High Similarity	NPC200782
0.8968	High Similarity	NPC193798
0.8968	High Similarity	NPC472771
0.8954	High Similarity	NPC263265
0.8954	High Similarity	NPC60973
0.8947	High Similarity	NPC282445
0.894	High Similarity	NPC116717
0.8933	High Similarity	NPC125182
0.8933	High Similarity	NPC472654
0.8933	High Similarity	NPC69647
0.8933	High Similarity	NPC471001
0.8924	High Similarity	NPC160651
0.8924	High Similarity	NPC471397
0.8912	High Similarity	NPC470741
0.891	High Similarity	NPC469338
0.891	High Similarity	NPC472139
0.891	High Similarity	NPC472773
0.891	High Similarity	NPC51568
0.891	High Similarity	NPC292389
0.891	High Similarity	NPC234660
0.8904	High Similarity	NPC20500
0.8896	High Similarity	NPC36655
0.8896	High Similarity	NPC261597
0.8896	High Similarity	NPC472283
0.8896	High Similarity	NPC470118
0.8889	High Similarity	NPC264943
0.8882	High Similarity	NPC469503
0.8875	High Similarity	NPC469848
0.8868	High Similarity	NPC82602
0.8867	High Similarity	NPC19747
0.8861	High Similarity	NPC473766
0.8861	High Similarity	NPC473753
0.8861	High Similarity	NPC476853
0.8861	High Similarity	NPC472282
0.8854	High Similarity	NPC276551
0.8854	High Similarity	NPC470940
0.8854	High Similarity	NPC276735
0.8854	High Similarity	NPC470182
0.8854	High Similarity	NPC271657
0.8854	High Similarity	NPC469849
0.8854	High Similarity	NPC476860
0.8851	High Similarity	NPC86935
0.8846	High Similarity	NPC329938
0.8846	High Similarity	NPC149896
0.8846	High Similarity	NPC18347
0.8846	High Similarity	NPC117986
0.8846	High Similarity	NPC188649
0.8844	High Similarity	NPC121158
0.8839	High Similarity	NPC474932
0.8839	High Similarity	NPC307383
0.8797	High Similarity	NPC470875
0.8797	High Similarity	NPC23387
0.879	High Similarity	NPC288602
0.879	High Similarity	NPC477405
0.879	High Similarity	NPC88841
0.8782	High Similarity	NPC470789
0.8774	High Similarity	NPC249021
0.8774	High Similarity	NPC45101
0.8774	High Similarity	NPC472772
0.8774	High Similarity	NPC214495
0.8774	High Similarity	NPC475066
0.8774	High Similarity	NPC470119
0.8774	High Similarity	NPC469847
0.8766	High Similarity	NPC469336
0.8759	High Similarity	NPC470742
0.8758	High Similarity	NPC84063
0.875	High Similarity	NPC470995
0.8742	High Similarity	NPC472774
0.8742	High Similarity	NPC472775
0.8733	High Similarity	NPC346
0.8733	High Similarity	NPC470999
0.8726	High Similarity	NPC69028
0.8726	High Similarity	NPC290400
0.8726	High Similarity	NPC96443
0.8726	High Similarity	NPC470792
0.8726	High Similarity	NPC197596
0.8718	High Similarity	NPC472671
0.8718	High Similarity	NPC477403
0.871	High Similarity	NPC204663
0.8701	High Similarity	NPC30222
0.8701	High Similarity	NPC178932
0.8699	High Similarity	NPC476943
0.8696	High Similarity	NPC285227
0.8696	High Similarity	NPC159232
0.8693	High Similarity	NPC291150
0.8688	High Similarity	NPC327922
0.8679	High Similarity	NPC93172
0.8679	High Similarity	NPC97574
0.8675	High Similarity	NPC250228
0.8675	High Similarity	NPC71821
0.8671	High Similarity	NPC285567
0.8671	High Similarity	NPC419
0.8667	High Similarity	NPC5676
0.8662	High Similarity	NPC477402
0.8658	High Similarity	NPC476946
0.8654	High Similarity	NPC197137
0.8654	High Similarity	NPC88007
0.8654	High Similarity	NPC195954
0.8654	High Similarity	NPC195131
0.8645	High Similarity	NPC471175
0.8645	High Similarity	NPC296807
0.8645	High Similarity	NPC155939
0.8645	High Similarity	NPC35000
0.8645	High Similarity	NPC141538
0.8636	High Similarity	NPC472672
0.8636	High Similarity	NPC471002
0.8634	High Similarity	NPC302392
0.863	High Similarity	NPC310830
0.8627	High Similarity	NPC5180
0.8625	High Similarity	NPC472764
0.8625	High Similarity	NPC100333
0.8625	High Similarity	NPC476224
0.8621	High Similarity	NPC92941
0.8609	High Similarity	NPC262198
0.8609	High Similarity	NPC62799
0.8608	High Similarity	NPC263432
0.8608	High Similarity	NPC207978
0.8608	High Similarity	NPC211777
0.8608	High Similarity	NPC68848
0.86	High Similarity	NPC84479
0.86	High Similarity	NPC476944
0.859	High Similarity	NPC175964
0.859	High Similarity	NPC471169
0.859	High Similarity	NPC469485
0.8581	High Similarity	NPC98206
0.8581	High Similarity	NPC34421
0.8581	High Similarity	NPC114880
0.8581	High Similarity	NPC67003
0.8581	High Similarity	NPC302054

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 NPC18135 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	318
0.1-0.2	963
0.2-0.3	2185
0.3-0.4	2691
0.4-0.5	1880
0.5-0.6	836
0.6-0.7	263
0.7-0.8	12
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8526	High Similarity	NPD5760	Phase 2
0.8526	High Similarity	NPD5761	Phase 2
0.807	Intermediate Similarity	NPD8434	Phase 2
0.7975	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6764	Approved
0.7471	Intermediate Similarity	NPD6765	Approved
0.7469	Intermediate Similarity	NPD920	Approved
0.7421	Intermediate Similarity	NPD4628	Phase 3
0.7396	Intermediate Similarity	NPD5494	Approved
0.7346	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD919	Approved
0.7333	Intermediate Similarity	NPD6599	Discontinued
0.7305	Intermediate Similarity	NPD7819	Suspended
0.7303	Intermediate Similarity	NPD6785	Approved
0.7303	Intermediate Similarity	NPD6784	Approved
0.7222	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7075	Discontinued
0.7175	Intermediate Similarity	NPD6559	Discontinued
0.7151	Intermediate Similarity	NPD1247	Approved
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7125	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1471	Phase 3
0.7086	Intermediate Similarity	NPD7473	Discontinued
0.7073	Intermediate Similarity	NPD6799	Approved
0.7069	Intermediate Similarity	NPD3926	Phase 2
0.7063	Intermediate Similarity	NPD2796	Approved
0.7059	Intermediate Similarity	NPD3817	Phase 2
0.7052	Intermediate Similarity	NPD8127	Discontinued
0.7045	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6801	Discontinued
0.7037	Intermediate Similarity	NPD1243	Approved
0.703	Intermediate Similarity	NPD2532	Approved
0.703	Intermediate Similarity	NPD2534	Approved
0.703	Intermediate Similarity	NPD2533	Approved
0.7018	Intermediate Similarity	NPD4965	Approved
0.7018	Intermediate Similarity	NPD4967	Phase 2
0.7018	Intermediate Similarity	NPD4966	Approved
0.7018	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6232	Discontinued
0.7006	Intermediate Similarity	NPD5844	Phase 1
0.7005	Intermediate Similarity	NPD8404	Phase 2
0.6988	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3749	Approved
0.6964	Remote Similarity	NPD3226	Approved
0.6949	Remote Similarity	NPD3818	Discontinued
0.6946	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6234	Discontinued
0.6928	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3882	Suspended
0.6901	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2799	Discontinued
0.689	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6273	Approved
0.6882	Remote Similarity	NPD7411	Suspended
0.686	Remote Similarity	NPD5402	Approved
0.686	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1551	Phase 2
0.6842	Remote Similarity	NPD37	Approved
0.6842	Remote Similarity	NPD1934	Approved
0.6829	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4380	Phase 2
0.6813	Remote Similarity	NPD8312	Approved
0.6813	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD8313	Approved
0.681	Remote Similarity	NPD2346	Discontinued
0.6796	Remote Similarity	NPD7685	Pre-registration
0.679	Remote Similarity	NPD3748	Approved
0.6789	Remote Similarity	NPD8285	Discontinued
0.6782	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD17	Approved
0.6768	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7458	Discontinued
0.6761	Remote Similarity	NPD7199	Phase 2
0.676	Remote Similarity	NPD7228	Approved
0.676	Remote Similarity	NPD7799	Discontinued
0.6748	Remote Similarity	NPD2935	Discontinued
0.6748	Remote Similarity	NPD2438	Suspended
0.6746	Remote Similarity	NPD5403	Approved
0.673	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD2800	Approved
0.6726	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD5401	Approved
0.6724	Remote Similarity	NPD7768	Phase 2
0.6723	Remote Similarity	NPD6808	Phase 2
0.6708	Remote Similarity	NPD6355	Discontinued
0.6708	Remote Similarity	NPD1933	Approved
0.6708	Remote Similarity	NPD447	Suspended
0.6707	Remote Similarity	NPD2344	Approved
0.6705	Remote Similarity	NPD2801	Approved
0.6703	Remote Similarity	NPD8150	Discontinued
0.6687	Remote Similarity	NPD4110	Phase 3
0.6687	Remote Similarity	NPD7033	Discontinued
0.6687	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD8032	Phase 2
0.6686	Remote Similarity	NPD6385	Approved
0.6686	Remote Similarity	NPD6386	Approved
0.6685	Remote Similarity	NPD7074	Phase 3
0.6685	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1549	Phase 2
0.6667	Remote Similarity	NPD6959	Discontinued
0.6667	Remote Similarity	NPD3751	Discontinued
0.6667	Remote Similarity	NPD5353	Approved
0.6667	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6166	Phase 2
0.6648	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3887	Approved
0.6646	Remote Similarity	NPD4307	Phase 2
0.6646	Remote Similarity	NPD6100	Approved
0.6646	Remote Similarity	NPD6099	Approved
0.6645	Remote Similarity	NPD1608	Approved
0.6645	Remote Similarity	NPD3972	Approved
0.6631	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7054	Approved
0.6629	Remote Similarity	NPD3787	Discontinued
0.6629	Remote Similarity	NPD7229	Phase 3
0.6627	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD2313	Discontinued
0.6612	Remote Similarity	NPD7240	Approved
0.6609	Remote Similarity	NPD1465	Phase 2
0.6607	Remote Similarity	NPD7236	Approved
0.6606	Remote Similarity	NPD6005	Phase 3
0.6606	Remote Similarity	NPD6004	Phase 3
0.6606	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6002	Phase 3
0.6606	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD5585	Approved
0.6595	Remote Similarity	NPD8407	Phase 2
0.6593	Remote Similarity	NPD7472	Approved
0.6592	Remote Similarity	NPD5242	Approved
0.6587	Remote Similarity	NPD3750	Approved
0.6582	Remote Similarity	NPD1019	Discontinued
0.658	Remote Similarity	NPD4107	Approved
0.6576	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7497	Discontinued
0.6557	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2403	Approved
0.6548	Remote Similarity	NPD2309	Approved
0.6543	Remote Similarity	NPD2979	Phase 3
0.6536	Remote Similarity	NPD5711	Approved
0.6536	Remote Similarity	NPD7315	Approved
0.6536	Remote Similarity	NPD5710	Approved
0.6524	Remote Similarity	NPD7097	Phase 1
0.6522	Remote Similarity	NPD7251	Discontinued
0.6522	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3764	Approved
0.6522	Remote Similarity	NPD8368	Discontinued
0.6519	Remote Similarity	NPD3267	Approved
0.6519	Remote Similarity	NPD3266	Approved
0.6512	Remote Similarity	NPD7239	Suspended
0.6506	Remote Similarity	NPD5763	Approved
0.6506	Remote Similarity	NPD5762	Approved
0.6488	Remote Similarity	NPD7003	Approved
0.6486	Remote Similarity	NPD7808	Phase 3
0.6485	Remote Similarity	NPD1510	Phase 2
0.6485	Remote Similarity	NPD4308	Phase 3
0.648	Remote Similarity	NPD7435	Discontinued
0.6477	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1511	Approved
0.6467	Remote Similarity	NPD6797	Phase 2
0.6467	Remote Similarity	NPD5953	Discontinued
0.6463	Remote Similarity	NPD1607	Approved
0.6462	Remote Similarity	NPD4482	Phase 3
0.6457	Remote Similarity	NPD6279	Approved
0.6457	Remote Similarity	NPD6280	Approved
0.6448	Remote Similarity	NPD7286	Phase 2
0.6442	Remote Similarity	NPD1240	Approved
0.6433	Remote Similarity	NPD9717	Approved
0.642	Remote Similarity	NPD3268	Approved
0.642	Remote Similarity	NPD8455	Phase 2
0.6415	Remote Similarity	NPD1203	Approved
0.6415	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD2797	Approved
0.6407	Remote Similarity	NPD2353	Approved
0.6407	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD7930	Approved
0.6402	Remote Similarity	NPD230	Phase 1
0.64	Remote Similarity	NPD6873	Phase 2
0.64	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD1512	Approved
0.6392	Remote Similarity	NPD4420	Approved
0.6392	Remote Similarity	NPD4359	Approved
0.6391	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD7907	Approved
0.6375	Remote Similarity	NPD2798	Approved
0.6375	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD1281	Approved
0.6364	Remote Similarity	NPD6651	Approved
0.6359	Remote Similarity	NPD4111	Phase 1
0.6358	Remote Similarity	NPD7095	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