NPASS Compound

Structure

CID320088 OpenBabel06191716152D 31 33 0 0 0 0 0 0 0 0999 V2000 5.5815 -6.0597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4214 -5.5599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7708 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4020 -3.6332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4062 -4.5992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8823 -5.1053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2098 -5.1289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5496 -2.1742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1740 -3.1728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5567 -3.1452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0479 -4.6243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0299 -3.6463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7222 -4.6146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3539 -4.6554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3359 -3.6774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7104 -1.6965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7218 -3.6330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8698 -3.1556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8755 -2.1843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5713 -5.0870 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 0.5219 -5.1563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4861 -3.2073 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0336 -1.6979 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 4.7049 -0.7308 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2078 -1.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3658 -1.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3936 -1.4583 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 7.8797 -2.3003 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 8.3658 -0.4861 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 9.2078 -2.9167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0497 -1.4583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 24 1 0 0 0 0 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 20 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 14 2 0 0 0 0 8 10 2 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 15 2 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 12 18 2 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 19 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 19 23 1 0 0 0 0 25 26 1 0 0 0 0 25 30 2 0 0 0 0 25 31 1 0 0 0 0 26 27 1 0 0 0 0 26 28 1 0 0 0 0 26 29 1 0 0 0 0 M CHG 2 20 1 23 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	325.13
Volume:	330.657
LogP:	0.261
LogD:	1.104
LogS:	-1.914
# Rotatable Bonds:	1
TPSA:	72.75
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	3.716
Fsp3:	0.263
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.774
MDCK Permeability:	5.720228728023358e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.867
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	73.37187194824219%
Volume Distribution (VD):	1.477
Pgp-substrate:	19.312305450439453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.876
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.407
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.725
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	8.388
Half-life (T1/2):	0.942

ADMET: Toxicity

hERG Blockers:	0.21
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.595
Rat Oral Acute Toxicity:	0.574
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.918
Carcinogencity:	0.057
Eye Corrosion:	0.007
Eye Irritation:	0.404
Respiratory Toxicity:	0.804

Download Data

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

Natural Product: NPC320088

Natural Product ID:	NPC320088
*Common Name:**	SBKNQDPIZMRYQD-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SBKNQDPIZMRYQD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H19NO4.C2HF3O2/c1-20(2)5-4-10-8-16(24-3)19(23)18-12-9-15(22)14(21)7-11(12)6-13(20)17(10)18;3-2(4,5)1(6)7/h6-9H,4-5H2,1-3H3,(H2-,21,22,23);(H,6,7)
SMILES:	C[N+]1(CCC2=CC(=C(C3=C4C=C(C(=CC4=CC1=C23)O)O)O)OC)C.C(=O)(C(F)(F)F)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1923424
PubChem CID:	56833652
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000381] 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
NPO16026	Gnetum montanum	Species	Gnetaceae	Eukaryota	leaves	Guangxi Province, China	2000-JAN	PMID[22040053]
NPO16026	Gnetum montanum	Species	Gnetaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22040053]
NPO16026	Gnetum montanum	Species	Gnetaceae	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
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	GI	=	59.0	%	PMID[534824]

☑ 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 NPC320088 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	359
0.1-0.2	2054
0.2-0.3	9500
0.3-0.4	8259
0.4-0.5	7561
0.5-0.6	12534
0.6-0.7	1910
0.7-0.8	451
0.8-0.85	55
0.85-0.9	10
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC276674
0.9762	High Similarity	NPC33902
0.9524	High Similarity	NPC190461
0.9345	High Similarity	NPC285941
0.9314	High Similarity	NPC78284
0.9143	High Similarity	NPC312531
0.9143	High Similarity	NPC474904
0.8929	High Similarity	NPC324144
0.8914	High Similarity	NPC249405
0.8895	High Similarity	NPC17677
0.8876	High Similarity	NPC96603
0.8876	High Similarity	NPC212794
0.8876	High Similarity	NPC306843
0.8876	High Similarity	NPC13504
0.8876	High Similarity	NPC136508
0.8876	High Similarity	NPC253043
0.8876	High Similarity	NPC196447
0.8876	High Similarity	NPC477563
0.8876	High Similarity	NPC78222
0.8772	High Similarity	NPC81218
0.8772	High Similarity	NPC145832
0.8772	High Similarity	NPC117188
0.8772	High Similarity	NPC306555
0.8772	High Similarity	NPC205421
0.8772	High Similarity	NPC158376
0.8772	High Similarity	NPC12053
0.8772	High Similarity	NPC474931
0.875	High Similarity	NPC179704
0.8698	High Similarity	NPC166014
0.8698	High Similarity	NPC27410
0.8686	High Similarity	NPC287588
0.8649	High Similarity	NPC471489
0.8647	High Similarity	NPC60186
0.8621	High Similarity	NPC239775
0.8596	High Similarity	NPC1229
0.8579	High Similarity	NPC162653
0.8563	High Similarity	NPC26240
0.8563	High Similarity	NPC69712
0.8563	High Similarity	NPC477562
0.8556	High Similarity	NPC477186
0.8523	High Similarity	NPC199465
0.8523	High Similarity	NPC128560
0.8523	High Similarity	NPC229166
0.8492	Intermediate Similarity	NPC28425
0.8483	Intermediate Similarity	NPC311936
0.8466	Intermediate Similarity	NPC66341
0.8466	Intermediate Similarity	NPC192135
0.8466	Intermediate Similarity	NPC477020
0.8462	Intermediate Similarity	NPC325871
0.8462	Intermediate Similarity	NPC99659
0.8457	Intermediate Similarity	NPC168753
0.8457	Intermediate Similarity	NPC118274
0.8436	Intermediate Similarity	NPC119579
0.8427	Intermediate Similarity	NPC114364
0.8427	Intermediate Similarity	NPC320223
0.8391	Intermediate Similarity	NPC476573
0.8391	Intermediate Similarity	NPC35627
0.8391	Intermediate Similarity	NPC81247
0.838	Intermediate Similarity	NPC215747
0.838	Intermediate Similarity	NPC192939
0.837	Intermediate Similarity	NPC302001
0.8363	Intermediate Similarity	NPC476572
0.8324	Intermediate Similarity	NPC260118
0.8304	Intermediate Similarity	NPC186063
0.8287	Intermediate Similarity	NPC116284
0.8284	Intermediate Similarity	NPC81733
0.8284	Intermediate Similarity	NPC326316
0.8281	Intermediate Similarity	NPC100573
0.8281	Intermediate Similarity	NPC207873
0.8278	Intermediate Similarity	NPC474507
0.8268	Intermediate Similarity	NPC265383
0.8251	Intermediate Similarity	NPC22928
0.8245	Intermediate Similarity	NPC212163
0.8239	Intermediate Similarity	NPC298979
0.8232	Intermediate Similarity	NPC155442
0.8232	Intermediate Similarity	NPC312918
0.8232	Intermediate Similarity	NPC476574
0.8232	Intermediate Similarity	NPC477561
0.822	Intermediate Similarity	NPC156728
0.822	Intermediate Similarity	NPC244606
0.8197	Intermediate Similarity	NPC180253
0.8197	Intermediate Similarity	NPC219170
0.8191	Intermediate Similarity	NPC23080
0.8191	Intermediate Similarity	NPC193906
0.8167	Intermediate Similarity	NPC476577
0.8167	Intermediate Similarity	NPC173416
0.8167	Intermediate Similarity	NPC148709
0.8158	Intermediate Similarity	NPC295676
0.8142	Intermediate Similarity	NPC135772
0.814	Intermediate Similarity	NPC469817
0.814	Intermediate Similarity	NPC39701
0.814	Intermediate Similarity	NPC2413
0.814	Intermediate Similarity	NPC193949
0.814	Intermediate Similarity	NPC276588
0.814	Intermediate Similarity	NPC249797
0.814	Intermediate Similarity	NPC127674
0.814	Intermediate Similarity	NPC184026
0.814	Intermediate Similarity	NPC189266
0.814	Intermediate Similarity	NPC295691
0.814	Intermediate Similarity	NPC110416
0.814	Intermediate Similarity	NPC207757
0.814	Intermediate Similarity	NPC54379
0.814	Intermediate Similarity	NPC5238
0.814	Intermediate Similarity	NPC278799
0.814	Intermediate Similarity	NPC204828
0.814	Intermediate Similarity	NPC172765
0.8136	Intermediate Similarity	NPC210140
0.8125	Intermediate Similarity	NPC167546
0.8125	Intermediate Similarity	NPC16805
0.8125	Intermediate Similarity	NPC302527
0.8122	Intermediate Similarity	NPC298449
0.8118	Intermediate Similarity	NPC88249
0.8118	Intermediate Similarity	NPC151895
0.8118	Intermediate Similarity	NPC97221
0.8118	Intermediate Similarity	NPC192768
0.8118	Intermediate Similarity	NPC220858
0.8114	Intermediate Similarity	NPC24954
0.8107	Intermediate Similarity	NPC428
0.8107	Intermediate Similarity	NPC24233
0.8107	Intermediate Similarity	NPC135538
0.8107	Intermediate Similarity	NPC476571
0.8107	Intermediate Similarity	NPC147390
0.8107	Intermediate Similarity	NPC246587
0.8105	Intermediate Similarity	NPC25897
0.8093	Intermediate Similarity	NPC90185
0.8087	Intermediate Similarity	NPC276060
0.8079	Intermediate Similarity	NPC24264
0.8079	Intermediate Similarity	NPC476432
0.8075	Intermediate Similarity	NPC478093
0.8065	Intermediate Similarity	NPC82763
0.8059	Intermediate Similarity	NPC103379
0.8059	Intermediate Similarity	NPC477565
0.8047	Intermediate Similarity	NPC191376
0.8047	Intermediate Similarity	NPC179825
0.8047	Intermediate Similarity	NPC321505
0.8041	Intermediate Similarity	NPC308943
0.8035	Intermediate Similarity	NPC244112
0.8034	Intermediate Similarity	NPC247389
0.8034	Intermediate Similarity	NPC210918
0.8034	Intermediate Similarity	NPC150879
0.8032	Intermediate Similarity	NPC478092
0.8032	Intermediate Similarity	NPC478091
0.8032	Intermediate Similarity	NPC30182
0.8032	Intermediate Similarity	NPC473589
0.8023	Intermediate Similarity	NPC26601
0.8023	Intermediate Similarity	NPC225774
0.8023	Intermediate Similarity	NPC24465
0.8023	Intermediate Similarity	NPC134858
0.8021	Intermediate Similarity	NPC294244
0.8011	Intermediate Similarity	NPC296742
0.8011	Intermediate Similarity	NPC112676
0.8011	Intermediate Similarity	NPC476576
0.8011	Intermediate Similarity	NPC186546
0.8	Intermediate Similarity	NPC221864
0.7989	Intermediate Similarity	NPC126519
0.7989	Intermediate Similarity	NPC203784
0.7989	Intermediate Similarity	NPC248642
0.7989	Intermediate Similarity	NPC170503
0.7978	Intermediate Similarity	NPC219341
0.7978	Intermediate Similarity	NPC13916
0.7978	Intermediate Similarity	NPC264850
0.7978	Intermediate Similarity	NPC126284
0.7966	Intermediate Similarity	NPC233650
0.7957	Intermediate Similarity	NPC224293
0.7956	Intermediate Similarity	NPC477187
0.7955	Intermediate Similarity	NPC235143
0.7955	Intermediate Similarity	NPC119649
0.7955	Intermediate Similarity	NPC232924
0.7955	Intermediate Similarity	NPC230956
0.7955	Intermediate Similarity	NPC306902
0.7955	Intermediate Similarity	NPC477559
0.7955	Intermediate Similarity	NPC160298
0.7955	Intermediate Similarity	NPC266753
0.7955	Intermediate Similarity	NPC205255
0.7955	Intermediate Similarity	NPC271388
0.7946	Intermediate Similarity	NPC156576
0.7941	Intermediate Similarity	NPC476151
0.7933	Intermediate Similarity	NPC204947
0.7931	Intermediate Similarity	NPC122463
0.7929	Intermediate Similarity	NPC185838
0.7921	Intermediate Similarity	NPC169743
0.7912	Intermediate Similarity	NPC477558
0.791	Intermediate Similarity	NPC80759
0.791	Intermediate Similarity	NPC79402
0.7903	Intermediate Similarity	NPC69213
0.7901	Intermediate Similarity	NPC149090
0.7901	Intermediate Similarity	NPC19520
0.7895	Intermediate Similarity	NPC130941
0.7889	Intermediate Similarity	NPC477185
0.788	Intermediate Similarity	NPC32154
0.7861	Intermediate Similarity	NPC57036
0.7853	Intermediate Similarity	NPC205167
0.7849	Intermediate Similarity	NPC219162
0.7849	Intermediate Similarity	NPC92541
0.7845	Intermediate Similarity	NPC152212
0.7845	Intermediate Similarity	NPC6152
0.7842	Intermediate Similarity	NPC29472
0.7821	Intermediate Similarity	NPC238530
0.7821	Intermediate Similarity	NPC276944
0.7821	Intermediate Similarity	NPC232514

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 NPC320088 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	772
0.2-0.3	1042
0.3-0.4	1668
0.4-0.5	2734
0.5-0.6	2123
0.6-0.7	561
0.7-0.8	39
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8011	Intermediate Similarity	NPD7479	Phase 2
0.7988	Intermediate Similarity	NPD2420	Approved
0.7988	Intermediate Similarity	NPD2421	Approved
0.7979	Intermediate Similarity	NPD7262	Phase 1
0.779	Intermediate Similarity	NPD27	Approved
0.779	Intermediate Similarity	NPD2489	Approved
0.7747	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD4584	Approved
0.7701	Intermediate Similarity	NPD8053	Approved
0.7701	Intermediate Similarity	NPD8054	Approved
0.7692	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD3051	Approved
0.7647	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD2970	Approved
0.7637	Intermediate Similarity	NPD2969	Approved
0.7596	Intermediate Similarity	NPD6607	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7906	Approved
0.7569	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD5938	Phase 3
0.7541	Intermediate Similarity	NPD4083	Discontinued
0.7512	Intermediate Similarity	NPD7922	Phase 1
0.75	Intermediate Similarity	NPD2898	Approved
0.7487	Intermediate Similarity	NPD7238	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD6496	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4010	Discontinued
0.746	Intermediate Similarity	NPD7312	Approved
0.746	Intermediate Similarity	NPD4578	Approved
0.746	Intermediate Similarity	NPD7311	Approved
0.746	Intermediate Similarity	NPD7310	Approved
0.746	Intermediate Similarity	NPD7313	Approved
0.746	Intermediate Similarity	NPD4577	Approved
0.7457	Intermediate Similarity	NPD3301	Approved
0.7435	Intermediate Similarity	NPD4663	Approved
0.7421	Intermediate Similarity	NPD7309	Approved
0.7414	Intermediate Similarity	NPD3845	Phase 1
0.7389	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6612	Phase 2
0.7363	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7831	Phase 2
0.7363	Intermediate Similarity	NPD7833	Phase 2
0.7363	Intermediate Similarity	NPD5530	Phase 1
0.7356	Intermediate Similarity	NPD5241	Discontinued
0.7356	Intermediate Similarity	NPD3763	Approved
0.7345	Intermediate Similarity	NPD6031	Approved
0.7345	Intermediate Similarity	NPD6030	Approved
0.734	Intermediate Similarity	NPD3920	Phase 2
0.7326	Intermediate Similarity	NPD8251	Approved
0.7326	Intermediate Similarity	NPD8252	Approved
0.7326	Intermediate Similarity	NPD8099	Discontinued
0.732	Intermediate Similarity	NPD2490	Approved
0.732	Intermediate Similarity	NPD2488	Approved
0.7316	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD3398	Discontinued
0.7295	Intermediate Similarity	NPD8149	Discontinued
0.7291	Intermediate Similarity	NPD4859	Phase 1
0.7287	Intermediate Similarity	NPD8156	Discontinued
0.7283	Intermediate Similarity	NPD6037	Discontinued
0.7282	Intermediate Similarity	NPD3924	Approved
0.7282	Intermediate Similarity	NPD3923	Approved
0.7282	Intermediate Similarity	NPD3921	Approved
0.7282	Intermediate Similarity	NPD3922	Approved
0.7277	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD5582	Discontinued
0.7258	Intermediate Similarity	NPD3975	Discontinued
0.7249	Intermediate Similarity	NPD5900	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7298	Approved
0.7231	Intermediate Similarity	NPD5641	Discontinued
0.7219	Intermediate Similarity	NPD4481	Phase 3
0.7213	Intermediate Similarity	NPD6788	Approved
0.7196	Intermediate Similarity	NPD5521	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5810	Discontinued
0.7189	Intermediate Similarity	NPD6723	Discontinued
0.7182	Intermediate Similarity	NPD4772	Phase 2
0.7182	Intermediate Similarity	NPD4773	Phase 2
0.7181	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4017	Approved
0.7167	Intermediate Similarity	NPD6357	Discontinued
0.7157	Intermediate Similarity	NPD7263	Phase 2
0.7136	Intermediate Similarity	NPD7034	Discontinued
0.7136	Intermediate Similarity	NPD6284	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD6527	Approved
0.7135	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD3515	Approved
0.7129	Intermediate Similarity	NPD3516	Approved
0.7124	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD6071	Discontinued
0.711	Intermediate Similarity	NPD6494	Phase 2
0.7092	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD3452	Approved
0.7079	Intermediate Similarity	NPD2494	Approved
0.7079	Intermediate Similarity	NPD3450	Approved
0.7079	Intermediate Similarity	NPD2493	Approved
0.7075	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD3815	Phase 1
0.7067	Intermediate Similarity	NPD3816	Phase 1
0.7065	Intermediate Similarity	NPD2563	Approved
0.7065	Intermediate Similarity	NPD2560	Approved
0.7059	Intermediate Similarity	NPD4986	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD3640	Phase 3
0.7056	Intermediate Similarity	NPD3641	Approved
0.7056	Intermediate Similarity	NPD3639	Approved
0.7053	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4502	Phase 2
0.7015	Intermediate Similarity	NPD5071	Phase 2
0.7011	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6090	Discontinued
0.7	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7222	Phase 2
0.6986	Remote Similarity	NPD7225	Discontinued
0.6985	Remote Similarity	NPD6526	Approved
0.6977	Remote Similarity	NPD3110	Approved
0.6977	Remote Similarity	NPD3109	Approved
0.6976	Remote Similarity	NPD4582	Approved
0.6976	Remote Similarity	NPD4583	Approved
0.6973	Remote Similarity	NPD6063	Approved
0.6971	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7802	Discontinued
0.6963	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7686	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2899	Discontinued
0.6943	Remote Similarity	NPD6211	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD4004	Approved
0.6927	Remote Similarity	NPD4002	Approved
0.6927	Remote Similarity	NPD5600	Discontinued
0.6923	Remote Similarity	NPD2971	Approved
0.6923	Remote Similarity	NPD2968	Approved
0.6923	Remote Similarity	NPD5895	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6737	Phase 2
0.6919	Remote Similarity	NPD2845	Phase 2
0.6919	Remote Similarity	NPD6738	Phase 2
0.6919	Remote Similarity	NPD2843	Phase 2
0.6904	Remote Similarity	NPD4951	Discontinued
0.69	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6621	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD2975	Approved
0.6881	Remote Similarity	NPD2974	Approved
0.6881	Remote Similarity	NPD2973	Approved
0.6878	Remote Similarity	NPD3983	Phase 3
0.6878	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5658	Approved
0.6872	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.686	Remote Similarity	NPD5718	Phase 2
0.6856	Remote Similarity	NPD6996	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD5177	Phase 3
0.6854	Remote Similarity	NPD3060	Approved
0.6853	Remote Similarity	NPD6340	Approved
0.6853	Remote Similarity	NPD6339	Approved
0.6848	Remote Similarity	NPD3296	Phase 1
0.6848	Remote Similarity	NPD5617	Suspended
0.6839	Remote Similarity	NPD3793	Phase 3
0.6835	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2883	Discontinued
0.6828	Remote Similarity	NPD6283	Phase 2
0.6828	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2674	Phase 3
0.6821	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6874	Approved
0.6812	Remote Similarity	NPD4040	Phase 1
0.6811	Remote Similarity	NPD3778	Approved
0.6809	Remote Similarity	NPD4055	Discovery
0.6809	Remote Similarity	NPD3453	Discontinued
0.6808	Remote Similarity	NPD7047	Phase 3
0.6806	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5155	Approved
0.6802	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5156	Approved
0.6798	Remote Similarity	NPD4604	Approved
0.6798	Remote Similarity	NPD4605	Approved
0.6791	Remote Similarity	NPD3557	Approved
0.6791	Remote Similarity	NPD3560	Approved
0.6791	Remote Similarity	NPD3558	Approved
0.6791	Remote Similarity	NPD3559	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD3556	Approved
0.6786	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.678	Remote Similarity	NPD4580	Approved
0.6774	Remote Similarity	NPD6997	Phase 2
0.6774	Remote Similarity	NPD3784	Discontinued
0.6769	Remote Similarity	NPD6184	Discontinued
0.6769	Remote Similarity	NPD6297	Approved
0.6761	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5930	Phase 3
0.6759	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6747	Phase 1
0.6753	Remote Similarity	NPD42	Phase 2
0.6753	Remote Similarity	NPD6042	Phase 2
0.675	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7453	Approved
0.6746	Remote Similarity	NPD7452	Approved
0.6744	Remote Similarity	NPD2606	Approved
0.6744	Remote Similarity	NPD2605	Approved
0.6744	Remote Similarity	NPD3594	Approved
0.6744	Remote Similarity	NPD3595	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