NPASS Compound

Structure

CID117717 OpenBabel06191715472D 23 27 0 0 1 0 0 0 0 0999 V2000 -0.7949 1.3757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9088 -1.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7080 -0.7626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0973 -0.7839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6957 0.1673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4855 2.9245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2813 3.3831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3739 -0.8398 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0850 0.1461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8842 0.6216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4808 1.9966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2769 1.5369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2841 0.6085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0874 1.9997 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8883 1.5373 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6823 1.5333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4793 0.1555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6832 0.6151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0774 2.9234 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.6895 1.9976 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1135 1.9911 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2882 -0.7437 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 21 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 9 2 0 0 0 0 5 10 2 0 0 0 0 6 7 1 0 0 0 0 6 11 1 0 0 0 0 7 19 1 0 0 0 0 8 22 1 0 0 0 0 8 23 1 0 0 0 0 9 10 1 0 0 0 0 9 13 1 0 0 0 0 10 15 1 0 0 0 0 11 12 2 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 13 17 2 0 0 0 0 14 12 1 6 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 6 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	311.12
Volume:	307.441
LogP:	1.336
LogD:	1.936
LogS:	-2.98
# Rotatable Bonds:	1
TPSA:	59.95
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.846
Synthetic Accessibility Score:	3.704
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.951
MDCK Permeability:	2.112328184011858e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.969
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983
Plasma Protein Binding (PPB):	89.22840118408203%
Volume Distribution (VD):	2.682
Pgp-substrate:	4.279299259185791%

ADMET: Metabolism

CYP1A2-inhibitor:	0.589
CYP1A2-substrate:	0.797
CYP2C19-inhibitor:	0.247
CYP2C19-substrate:	0.881
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.856
CYP2D6-inhibitor:	0.735
CYP2D6-substrate:	0.821
CYP3A4-inhibitor:	0.675
CYP3A4-substrate:	0.665

ADMET: Excretion

Clearance (CL):	4.965
Half-life (T1/2):	0.117

ADMET: Toxicity

hERG Blockers:	0.127
Human Hepatotoxicity (H-HT):	0.336
Drug-inuced Liver Injury (DILI):	0.201
AMES Toxicity:	0.793
Rat Oral Acute Toxicity:	0.604
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.133
Carcinogencity:	0.243
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.906

Download Data

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

Natural Product: NPC117717

Natural Product ID:	NPC117717
*Common Name:**	Artabonatine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	INJOIUDEEULGCE-LSDHHAIUSA-N
Standard InCHI:	InChI=1S/C18H17NO4/c1-21-16-11-6-7-19-14-12(11)13(17-18(16)23-8-22-17)9-4-2-3-5-10(9)15(14)20/h2-5,14-15,19-20H,6-8H2,1H3/t14-,15+/m0/s1
SMILES:	COc1c2OCOc2c2c3c1CCN[C@@H]3[C@@H](c1c2cccc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458523
PubChem CID:	10614948
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] Aporphines [CHEMONTID:0003021] Hydroxy-7-aporphines

*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
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[11141125]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398544]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18419154]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296389]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21910504]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	seeds	n.a.	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	seed	n.a.	PMID[22011319]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Barks	n.a.	n.a.	PMID[2348205]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[8786370]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	bark	n.a.	n.a.	PMID[9214729]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2884	Annona squamosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2884	Annona squamosa	Species	Annonaceae	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	9.1	ug.mL-1	PMID[460264]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11.0	ug.mL-1	PMID[460264]

☑ 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 NPC117717 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	332
0.1-0.2	1644
0.2-0.3	7239
0.3-0.4	10770
0.4-0.5	6513
0.5-0.6	11802
0.6-0.7	3571
0.7-0.8	644
0.8-0.85	114
0.85-0.9	46
0.9-0.95	19
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9651	High Similarity	NPC214116
0.9477	High Similarity	NPC476575
0.9425	High Similarity	NPC57036
0.9371	High Similarity	NPC476576
0.9371	High Similarity	NPC186546
0.9357	High Similarity	NPC112575
0.9306	High Similarity	NPC32413
0.9306	High Similarity	NPC474506
0.9302	High Similarity	NPC23219
0.9253	High Similarity	NPC248642
0.9249	High Similarity	NPC126284
0.9249	High Similarity	NPC258695
0.9249	High Similarity	NPC267408
0.9249	High Similarity	NPC470879
0.92	High Similarity	NPC156576
0.9091	High Similarity	NPC135772
0.9086	High Similarity	NPC477561
0.9086	High Similarity	NPC476574
0.9086	High Similarity	NPC155442
0.9086	High Similarity	NPC312918
0.9075	High Similarity	NPC477558
0.9029	High Similarity	NPC474507
0.9023	High Similarity	NPC476577
0.9023	High Similarity	NPC148709
0.9023	High Similarity	NPC173416
0.9012	High Similarity	NPC6152
0.896	High Similarity	NPC149090
0.896	High Similarity	NPC19520
0.8944	High Similarity	NPC475754
0.8927	High Similarity	NPC275132
0.8902	High Similarity	NPC152212
0.8895	High Similarity	NPC204947
0.8837	High Similarity	NPC86144
0.8837	High Similarity	NPC304659
0.8785	High Similarity	NPC82763
0.8757	High Similarity	NPC320223
0.8757	High Similarity	NPC114364
0.875	High Similarity	NPC128560
0.875	High Similarity	NPC229166
0.875	High Similarity	NPC199465
0.8728	High Similarity	NPC476432
0.8728	High Similarity	NPC24264
0.8721	High Similarity	NPC189470
0.8693	High Similarity	NPC477020
0.8693	High Similarity	NPC66341
0.8693	High Similarity	NPC192135
0.8686	High Similarity	NPC477562
0.8686	High Similarity	NPC118274
0.8686	High Similarity	NPC26240
0.8686	High Similarity	NPC168753
0.8686	High Similarity	NPC69712
0.8678	High Similarity	NPC247389
0.8678	High Similarity	NPC298979
0.8671	High Similarity	NPC167546
0.8671	High Similarity	NPC16805
0.8671	High Similarity	NPC302527
0.8671	High Similarity	NPC225774
0.8652	High Similarity	NPC118633
0.8652	High Similarity	NPC148693
0.8652	High Similarity	NPC294790
0.8639	High Similarity	NPC46990
0.8636	High Similarity	NPC239775
0.8621	High Similarity	NPC219341
0.8588	High Similarity	NPC2314
0.8571	High Similarity	NPC210918
0.8525	High Similarity	NPC237579
0.8514	High Similarity	NPC81247
0.8514	High Similarity	NPC35627
0.8514	High Similarity	NPC476573
0.8508	High Similarity	NPC116284
0.8508	High Similarity	NPC233718
0.85	High Similarity	NPC244554
0.8497	Intermediate Similarity	NPC306902
0.8497	Intermediate Similarity	NPC266753
0.8497	Intermediate Similarity	NPC160298
0.8497	Intermediate Similarity	NPC232924
0.8497	Intermediate Similarity	NPC477559
0.8466	Intermediate Similarity	NPC150879
0.8436	Intermediate Similarity	NPC329969
0.843	Intermediate Similarity	NPC126519
0.843	Intermediate Similarity	NPC203784
0.843	Intermediate Similarity	NPC170503
0.8409	Intermediate Similarity	NPC56887
0.8409	Intermediate Similarity	NPC193853
0.8409	Intermediate Similarity	NPC223077
0.8362	Intermediate Similarity	NPC81218
0.8362	Intermediate Similarity	NPC158376
0.8362	Intermediate Similarity	NPC306555
0.8362	Intermediate Similarity	NPC12053
0.8362	Intermediate Similarity	NPC205421
0.8362	Intermediate Similarity	NPC145832
0.8362	Intermediate Similarity	NPC117188
0.8362	Intermediate Similarity	NPC474931
0.8352	Intermediate Similarity	NPC306843
0.8352	Intermediate Similarity	NPC196447
0.8352	Intermediate Similarity	NPC253043
0.8352	Intermediate Similarity	NPC96603
0.8352	Intermediate Similarity	NPC477563
0.8352	Intermediate Similarity	NPC209377
0.8352	Intermediate Similarity	NPC212794
0.8352	Intermediate Similarity	NPC136508
0.8352	Intermediate Similarity	NPC78222
0.8352	Intermediate Similarity	NPC13504
0.8305	Intermediate Similarity	NPC195392
0.8295	Intermediate Similarity	NPC233650
0.8295	Intermediate Similarity	NPC324144
0.828	Intermediate Similarity	NPC281581
0.8276	Intermediate Similarity	NPC476572
0.8266	Intermediate Similarity	NPC325871
0.8266	Intermediate Similarity	NPC99659
0.8249	Intermediate Similarity	NPC134858
0.8232	Intermediate Similarity	NPC187678
0.8229	Intermediate Similarity	NPC7393
0.8216	Intermediate Similarity	NPC9867
0.8212	Intermediate Similarity	NPC241055
0.8197	Intermediate Similarity	NPC220961
0.8192	Intermediate Similarity	NPC1229
0.8182	Intermediate Similarity	NPC166014
0.8182	Intermediate Similarity	NPC27410
0.8167	Intermediate Similarity	NPC75958
0.8156	Intermediate Similarity	NPC210140
0.8148	Intermediate Similarity	NPC256124
0.8146	Intermediate Similarity	NPC168409
0.8146	Intermediate Similarity	NPC169743
0.8122	Intermediate Similarity	NPC470739
0.8122	Intermediate Similarity	NPC225597
0.8122	Intermediate Similarity	NPC477640
0.8111	Intermediate Similarity	NPC266176
0.8111	Intermediate Similarity	NPC475686
0.8111	Intermediate Similarity	NPC58766
0.8111	Intermediate Similarity	NPC82533
0.8111	Intermediate Similarity	NPC290759
0.8111	Intermediate Similarity	NPC158148
0.8101	Intermediate Similarity	NPC264850
0.8101	Intermediate Similarity	NPC13916
0.8101	Intermediate Similarity	NPC68328
0.8095	Intermediate Similarity	NPC24260
0.8095	Intermediate Similarity	NPC478093
0.8092	Intermediate Similarity	NPC81733
0.8092	Intermediate Similarity	NPC326316
0.8079	Intermediate Similarity	NPC205255
0.8079	Intermediate Similarity	NPC235143
0.8079	Intermediate Similarity	NPC271388
0.8079	Intermediate Similarity	NPC119649
0.8079	Intermediate Similarity	NPC230956
0.8068	Intermediate Similarity	NPC79328
0.8066	Intermediate Similarity	NPC474475
0.8056	Intermediate Similarity	NPC190332
0.8056	Intermediate Similarity	NPC181653
0.8053	Intermediate Similarity	NPC478092
0.8053	Intermediate Similarity	NPC478091
0.8053	Intermediate Similarity	NPC30182
0.8053	Intermediate Similarity	NPC473589
0.8046	Intermediate Similarity	NPC114124
0.8045	Intermediate Similarity	NPC232514
0.8045	Intermediate Similarity	NPC276944
0.8045	Intermediate Similarity	NPC24465
0.8045	Intermediate Similarity	NPC238530
0.8034	Intermediate Similarity	NPC80759
0.8034	Intermediate Similarity	NPC79402
0.8023	Intermediate Similarity	NPC221864
0.8022	Intermediate Similarity	NPC231371
0.8011	Intermediate Similarity	NPC299990
0.8011	Intermediate Similarity	NPC73492
0.801	Intermediate Similarity	NPC162653
0.7989	Intermediate Similarity	NPC320104
0.7989	Intermediate Similarity	NPC48490
0.7989	Intermediate Similarity	NPC274661
0.7989	Intermediate Similarity	NPC11296
0.7989	Intermediate Similarity	NPC82457
0.7989	Intermediate Similarity	NPC175890
0.7977	Intermediate Similarity	NPC207824
0.7977	Intermediate Similarity	NPC60538
0.797	Intermediate Similarity	NPC11708
0.7968	Intermediate Similarity	NPC302275
0.7967	Intermediate Similarity	NPC311991
0.7956	Intermediate Similarity	NPC100566
0.7955	Intermediate Similarity	NPC244112
0.7955	Intermediate Similarity	NPC138487
0.7955	Intermediate Similarity	NPC216459
0.7955	Intermediate Similarity	NPC41178
0.7947	Intermediate Similarity	NPC60295
0.7947	Intermediate Similarity	NPC191132
0.7946	Intermediate Similarity	NPC15919
0.7944	Intermediate Similarity	NPC180306
0.7937	Intermediate Similarity	NPC474904
0.7933	Intermediate Similarity	NPC60186
0.7926	Intermediate Similarity	NPC95426
0.7926	Intermediate Similarity	NPC16357
0.7926	Intermediate Similarity	NPC302245
0.7921	Intermediate Similarity	NPC111485
0.7919	Intermediate Similarity	NPC475959
0.7912	Intermediate Similarity	NPC204908
0.7912	Intermediate Similarity	NPC83198
0.791	Intermediate Similarity	NPC29647
0.791	Intermediate Similarity	NPC146288
0.7903	Intermediate Similarity	NPC243454
0.7903	Intermediate Similarity	NPC475479
0.7898	Intermediate Similarity	NPC2295
0.7898	Intermediate Similarity	NPC477564

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 NPC117717 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	698
0.2-0.3	1122
0.3-0.4	2285
0.4-0.5	2675
0.5-0.6	1539
0.6-0.7	535
0.7-0.8	105
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8075	Intermediate Similarity	NPD7906	Approved
0.8021	Intermediate Similarity	NPD4663	Approved
0.8011	Intermediate Similarity	NPD2977	Approved
0.8011	Intermediate Similarity	NPD2978	Approved
0.8	Intermediate Similarity	NPD3051	Approved
0.7957	Intermediate Similarity	NPD4578	Approved
0.7957	Intermediate Similarity	NPD4577	Approved
0.7956	Intermediate Similarity	NPD2969	Approved
0.7956	Intermediate Similarity	NPD2970	Approved
0.7921	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7827	Phase 1
0.7814	Intermediate Similarity	NPD27	Approved
0.7814	Intermediate Similarity	NPD2489	Approved
0.7807	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD8053	Approved
0.7725	Intermediate Similarity	NPD8054	Approved
0.7709	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD8156	Discontinued
0.7688	Intermediate Similarity	NPD5241	Discontinued
0.7634	Intermediate Similarity	NPD8099	Discontinued
0.7634	Intermediate Similarity	NPD8252	Approved
0.7634	Intermediate Similarity	NPD8251	Approved
0.7622	Intermediate Similarity	NPD4481	Phase 3
0.7614	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD2973	Approved
0.7602	Intermediate Similarity	NPD2974	Approved
0.7602	Intermediate Similarity	NPD2975	Approved
0.7588	Intermediate Similarity	NPD5006	Approved
0.7588	Intermediate Similarity	NPD5005	Approved
0.7579	Intermediate Similarity	NPD7312	Approved
0.7579	Intermediate Similarity	NPD7310	Approved
0.7579	Intermediate Similarity	NPD7313	Approved
0.7579	Intermediate Similarity	NPD7311	Approved
0.7572	Intermediate Similarity	NPD3060	Approved
0.7571	Intermediate Similarity	NPD4727	Phase 1
0.7557	Intermediate Similarity	NPD4584	Approved
0.7539	Intermediate Similarity	NPD7309	Approved
0.7538	Intermediate Similarity	NPD2493	Approved
0.7538	Intermediate Similarity	NPD3450	Approved
0.7538	Intermediate Similarity	NPD2494	Approved
0.7538	Intermediate Similarity	NPD3452	Approved
0.7527	Intermediate Similarity	NPD6788	Approved
0.7514	Intermediate Similarity	NPD6071	Discontinued
0.7514	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2420	Approved
0.75	Intermediate Similarity	NPD2421	Approved
0.7487	Intermediate Similarity	NPD4580	Approved
0.7475	Intermediate Similarity	NPD4420	Approved
0.7473	Intermediate Similarity	NPD2563	Approved
0.7473	Intermediate Similarity	NPD2560	Approved
0.7472	Intermediate Similarity	NPD6031	Approved
0.7472	Intermediate Similarity	NPD6030	Approved
0.7459	Intermediate Similarity	NPD7298	Approved
0.7458	Intermediate Similarity	NPD1424	Approved
0.7446	Intermediate Similarity	NPD5709	Phase 3
0.7443	Intermediate Similarity	NPD3845	Phase 1
0.7443	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD4582	Approved
0.7426	Intermediate Similarity	NPD4583	Approved
0.7407	Intermediate Similarity	NPD42	Phase 2
0.7407	Intermediate Similarity	NPD6042	Phase 2
0.7405	Intermediate Similarity	NPD4666	Phase 3
0.7405	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4004	Approved
0.7376	Intermediate Similarity	NPD4002	Approved
0.7374	Intermediate Similarity	NPD5976	Discontinued
0.7373	Intermediate Similarity	NPD6723	Discontinued
0.733	Intermediate Similarity	NPD6297	Approved
0.7297	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4055	Discovery
0.7293	Intermediate Similarity	NPD4005	Discontinued
0.7288	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5160	Discontinued
0.7268	Intermediate Similarity	NPD3383	Approved
0.7268	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD3382	Approved
0.7268	Intermediate Similarity	NPD3384	Approved
0.7268	Intermediate Similarity	NPD6851	Approved
0.7268	Intermediate Similarity	NPD6853	Approved
0.7259	Intermediate Similarity	NPD2490	Approved
0.7259	Intermediate Similarity	NPD2488	Approved
0.7257	Intermediate Similarity	NPD8153	Approved
0.7257	Intermediate Similarity	NPD8152	Approved
0.7238	Intermediate Similarity	NPD7047	Phase 3
0.7216	Intermediate Similarity	NPD2971	Approved
0.7216	Intermediate Similarity	NPD2968	Approved
0.7213	Intermediate Similarity	NPD4773	Phase 2
0.7213	Intermediate Similarity	NPD4772	Phase 2
0.7204	Intermediate Similarity	NPD7833	Phase 2
0.7204	Intermediate Similarity	NPD7831	Phase 2
0.7204	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD6997	Phase 2
0.7181	Intermediate Similarity	NPD6107	Approved
0.7175	Intermediate Similarity	NPD4237	Approved
0.7175	Intermediate Similarity	NPD4236	Phase 3
0.7175	Intermediate Similarity	NPD4162	Approved
0.7158	Intermediate Similarity	NPD2898	Approved
0.7151	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4585	Approved
0.7126	Intermediate Similarity	NPD2568	Approved
0.7104	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD2677	Approved
0.7081	Intermediate Similarity	NPD37	Approved
0.7079	Intermediate Similarity	NPD5177	Phase 3
0.7071	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD3687	Approved
0.7049	Intermediate Similarity	NPD3686	Approved
0.7047	Intermediate Similarity	NPD5096	Phase 3
0.7047	Intermediate Similarity	NPD5095	Phase 3
0.7033	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5582	Discontinued
0.7026	Intermediate Similarity	NPD7039	Approved
0.7026	Intermediate Similarity	NPD7038	Approved
0.702	Intermediate Similarity	NPD3857	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7213	Phase 3
0.7017	Intermediate Similarity	NPD7212	Phase 2
0.7011	Intermediate Similarity	NPD4017	Approved
0.7006	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD4040	Phase 1
0.6986	Remote Similarity	NPD4859	Phase 1
0.6982	Remote Similarity	NPD6625	Approved
0.6978	Remote Similarity	NPD3157	Approved
0.6978	Remote Similarity	NPD3158	Phase 1
0.6978	Remote Similarity	NPD7447	Phase 1
0.6978	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4675	Approved
0.6973	Remote Similarity	NPD4678	Approved
0.6968	Remote Similarity	NPD4967	Phase 2
0.6968	Remote Similarity	NPD4965	Approved
0.6968	Remote Similarity	NPD4966	Approved
0.6966	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4010	Discontinued
0.6959	Remote Similarity	NPD3933	Discontinued
0.695	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD1753	Discontinued
0.6949	Remote Similarity	NPD2155	Approved
0.6949	Remote Similarity	NPD2156	Approved
0.6949	Remote Similarity	NPD2154	Approved
0.6947	Remote Similarity	NPD5677	Discontinued
0.694	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6072	Discontinued
0.6932	Remote Similarity	NPD823	Approved
0.6932	Remote Similarity	NPD817	Approved
0.6931	Remote Similarity	NPD5604	Discontinued
0.6927	Remote Similarity	NPD8095	Phase 1
0.6912	Remote Similarity	NPD7907	Approved
0.6908	Remote Similarity	NPD3057	Approved
0.6904	Remote Similarity	NPD3936	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD7549	Discontinued
0.6898	Remote Similarity	NPD4227	Discontinued
0.6898	Remote Similarity	NPD4665	Approved
0.6898	Remote Similarity	NPD4111	Phase 1
0.6895	Remote Similarity	NPD7400	Phase 3
0.689	Remote Similarity	NPD7999	Approved
0.6889	Remote Similarity	NPD6674	Discontinued
0.6885	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4166	Phase 2
0.6869	Remote Similarity	NPD7930	Approved
0.6869	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7124	Phase 2
0.6866	Remote Similarity	NPD2845	Phase 2
0.6866	Remote Similarity	NPD2843	Phase 2
0.6862	Remote Similarity	NPD5773	Approved
0.6862	Remote Similarity	NPD5772	Approved
0.6857	Remote Similarity	NPD6405	Approved
0.6857	Remote Similarity	NPD6407	Approved
0.6857	Remote Similarity	NPD7583	Approved
0.6854	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4083	Discontinued
0.6836	Remote Similarity	NPD3054	Approved
0.6836	Remote Similarity	NPD3052	Approved
0.6831	Remote Similarity	NPD7598	Phase 2
0.6831	Remote Similarity	NPD1774	Approved
0.6827	Remote Similarity	NPD2972	Approved
0.6827	Remote Similarity	NPD3533	Approved
0.6825	Remote Similarity	NPD7585	Approved
0.6821	Remote Similarity	NPD7228	Approved
0.6818	Remote Similarity	NPD3061	Approved
0.6818	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD3109	Approved
0.6818	Remote Similarity	NPD3110	Approved
0.6818	Remote Similarity	NPD3062	Approved
0.6818	Remote Similarity	NPD3059	Approved
0.6816	Remote Similarity	NPD6843	Phase 3
0.6816	Remote Similarity	NPD6841	Approved
0.6816	Remote Similarity	NPD6842	Approved
0.6812	Remote Similarity	NPD5457	Discontinued
0.6811	Remote Similarity	NPD3639	Approved
0.6811	Remote Similarity	NPD3640	Phase 3
0.6811	Remote Similarity	NPD3641	Approved
0.6808	Remote Similarity	NPD5676	Approved
0.6806	Remote Similarity	NPD6234	Discontinued
0.6802	Remote Similarity	NPD7007	Discovery

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