NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	419.14
Volume:	412.331
LogP:	-1.606
LogD:	1.24
LogS:	-2.573
# Rotatable Bonds:	0
TPSA:	124.21
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.282
Synthetic Accessibility Score:	5.288
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.348
MDCK Permeability:	5.706108368030982e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.986
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	81.12593841552734%
Volume Distribution (VD):	0.613
Pgp-substrate:	12.35952377319336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.023
CYP1A2-substrate:	0.08
CYP2C19-inhibitor:	0.047
CYP2C19-substrate:	0.036
CYP2C9-inhibitor:	0.393
CYP2C9-substrate:	0.409
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.189
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.219

ADMET: Excretion

Clearance (CL):	3.607
Half-life (T1/2):	0.963

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.466
Drug-inuced Liver Injury (DILI):	0.294
AMES Toxicity:	0.619
Rat Oral Acute Toxicity:	0.27
Maximum Recommended Daily Dose:	0.998
Skin Sensitization:	0.962
Carcinogencity:	0.135
Eye Corrosion:	0.003
Eye Irritation:	0.575
Respiratory Toxicity:	0.645

Download Data

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

Natural Product: NPC477187

Natural Product ID:	NPC477187
*Common Name:**	CID 57399479
IUPAC Name:	(9R,17R)-1-azoniahexacyclo[15.8.0.01,9.02,7.011,16.018,23]pentacosa-2,4,6,11(16),12,14,18,20,22-nonaene-4,5,12,13,20,21-hexol;2,2,2-trifluoroacetate
Synonyms:	(-)-Latifolian A
Standard InCHIKey:	YMJCRHXVHGDWNI-XZOLHLNOSA-N
Standard InCHI:	InChI=1S/C24H21NO6.C2HF3O2/c26-18-2-1-14-16(24(18)31)8-13-5-12-7-20(28)22(30)10-17(12)25(13)4-3-11-6-19(27)21(29)9-15(11)23(14)25;3-2(4,5)1(6)7/h1-2,6-7,9-10,13,23H,3-5,8H2,(H5-,26,27,28,29,30,31);(H,6,7)/t13-,23+,25?;/m1./s1
SMILES:	C1C[N+]23[C@H](CC4=CC(=C(C=C42)O)O)CC5=C([C@H]3C6=CC(=C(C=C61)O)O)C=CC(=C5O)O.C(=O)(C(F)(F)F)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	57399479
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002955] Tetrahydroisoquinolines

*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
IC50	1
MIC	1
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	IC50	=	9800	nM	PMID[22040053]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	GI	=	55	%	PMID[22040053]
NPT1548	Organism	Pseudomonas aeruginosa PAO1	Pseudomonas aeruginosa PAO1	MIC	=	35000	nM	PMID[22040053]

☑ 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 NPC477187 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	351
0.1-0.2	1905
0.2-0.3	11617
0.3-0.4	6818
0.4-0.5	13738
0.5-0.6	7054
0.6-0.7	1116
0.7-0.8	95
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.981	High Similarity	NPC477185
0.9118	High Similarity	NPC477186
0.8045	Intermediate Similarity	NPC33902
0.8045	Intermediate Similarity	NPC276674
0.7956	Intermediate Similarity	NPC320088
0.7824	Intermediate Similarity	NPC207757
0.7824	Intermediate Similarity	NPC110416
0.7824	Intermediate Similarity	NPC469817
0.7824	Intermediate Similarity	NPC39701
0.7824	Intermediate Similarity	NPC249797
0.7824	Intermediate Similarity	NPC5238
0.7824	Intermediate Similarity	NPC193949
0.7824	Intermediate Similarity	NPC127674
0.7824	Intermediate Similarity	NPC189266
0.7824	Intermediate Similarity	NPC276588
0.7824	Intermediate Similarity	NPC54379
0.7824	Intermediate Similarity	NPC204828
0.7824	Intermediate Similarity	NPC2413
0.7824	Intermediate Similarity	NPC295691
0.7824	Intermediate Similarity	NPC184026
0.7824	Intermediate Similarity	NPC172765
0.7824	Intermediate Similarity	NPC278799
0.773	Intermediate Similarity	NPC323123
0.7717	Intermediate Similarity	NPC474904
0.7714	Intermediate Similarity	NPC238530
0.7714	Intermediate Similarity	NPC276944
0.7714	Intermediate Similarity	NPC232514
0.7713	Intermediate Similarity	NPC17677
0.7669	Intermediate Similarity	NPC211468
0.7669	Intermediate Similarity	NPC170170
0.7669	Intermediate Similarity	NPC219233
0.7654	Intermediate Similarity	NPC285941
0.7637	Intermediate Similarity	NPC179704
0.7635	Intermediate Similarity	NPC214980
0.7588	Intermediate Similarity	NPC88249
0.7588	Intermediate Similarity	NPC151895
0.7588	Intermediate Similarity	NPC220858
0.7588	Intermediate Similarity	NPC97221
0.7588	Intermediate Similarity	NPC192768
0.7529	Intermediate Similarity	NPC103379
0.7529	Intermediate Similarity	NPC477565
0.7527	Intermediate Similarity	NPC190461
0.7513	Intermediate Similarity	NPC162653
0.75	Intermediate Similarity	NPC471489
0.75	Intermediate Similarity	NPC249405
0.75	Intermediate Similarity	NPC24954
0.7486	Intermediate Similarity	NPC111485
0.7473	Intermediate Similarity	NPC287588
0.7472	Intermediate Similarity	NPC250846
0.7472	Intermediate Similarity	NPC240841
0.7472	Intermediate Similarity	NPC317272
0.7472	Intermediate Similarity	NPC42549
0.7472	Intermediate Similarity	NPC13916
0.7472	Intermediate Similarity	NPC264850
0.7472	Intermediate Similarity	NPC268503
0.7472	Intermediate Similarity	NPC256012
0.7471	Intermediate Similarity	NPC428
0.7471	Intermediate Similarity	NPC246587
0.7471	Intermediate Similarity	NPC24233
0.7471	Intermediate Similarity	NPC476571
0.7471	Intermediate Similarity	NPC135538
0.7471	Intermediate Similarity	NPC147390
0.7448	Intermediate Similarity	NPC127178
0.7443	Intermediate Similarity	NPC166014
0.7443	Intermediate Similarity	NPC27410
0.7433	Intermediate Similarity	NPC312531
0.7416	Intermediate Similarity	NPC24465
0.7412	Intermediate Similarity	NPC106295
0.7412	Intermediate Similarity	NPC321505
0.7412	Intermediate Similarity	NPC191376
0.7412	Intermediate Similarity	NPC51957
0.7412	Intermediate Similarity	NPC476151
0.7412	Intermediate Similarity	NPC476144
0.7412	Intermediate Similarity	NPC16107
0.7412	Intermediate Similarity	NPC179825
0.7412	Intermediate Similarity	NPC210437
0.7407	Intermediate Similarity	NPC78284
0.7371	Intermediate Similarity	NPC186063
0.7368	Intermediate Similarity	NPC7467
0.736	Intermediate Similarity	NPC1229
0.736	Intermediate Similarity	NPC324144
0.7333	Intermediate Similarity	NPC117188
0.7333	Intermediate Similarity	NPC306555
0.7333	Intermediate Similarity	NPC205421
0.7333	Intermediate Similarity	NPC474931
0.7333	Intermediate Similarity	NPC12053
0.7333	Intermediate Similarity	NPC81218
0.7333	Intermediate Similarity	NPC158376
0.7333	Intermediate Similarity	NPC145832
0.7333	Intermediate Similarity	NPC210140
0.7318	Intermediate Similarity	NPC477563
0.7318	Intermediate Similarity	NPC196447
0.7318	Intermediate Similarity	NPC306843
0.7318	Intermediate Similarity	NPC78222
0.7318	Intermediate Similarity	NPC96603
0.7318	Intermediate Similarity	NPC13504
0.7318	Intermediate Similarity	NPC136508
0.7318	Intermediate Similarity	NPC253043
0.7318	Intermediate Similarity	NPC212794
0.7316	Intermediate Similarity	NPC302001
0.7314	Intermediate Similarity	NPC138487
0.7314	Intermediate Similarity	NPC216459
0.7314	Intermediate Similarity	NPC469428
0.7314	Intermediate Similarity	NPC41178
0.7312	Intermediate Similarity	NPC90998
0.7312	Intermediate Similarity	NPC279228
0.7312	Intermediate Similarity	NPC239824
0.7312	Intermediate Similarity	NPC290582
0.7312	Intermediate Similarity	NPC258657
0.7312	Intermediate Similarity	NPC104196
0.7312	Intermediate Similarity	NPC271013
0.7312	Intermediate Similarity	NPC223690
0.7312	Intermediate Similarity	NPC8836
0.7312	Intermediate Similarity	NPC217748
0.7312	Intermediate Similarity	NPC7715
0.7312	Intermediate Similarity	NPC222661
0.7312	Intermediate Similarity	NPC49075
0.7312	Intermediate Similarity	NPC15414
0.7312	Intermediate Similarity	NPC285931
0.7312	Intermediate Similarity	NPC328155
0.7312	Intermediate Similarity	NPC290005
0.7312	Intermediate Similarity	NPC182052
0.7312	Intermediate Similarity	NPC185639
0.7312	Intermediate Similarity	NPC181796
0.7312	Intermediate Similarity	NPC229373
0.7312	Intermediate Similarity	NPC54654
0.7312	Intermediate Similarity	NPC251735
0.7312	Intermediate Similarity	NPC42663
0.7312	Intermediate Similarity	NPC311973
0.7303	Intermediate Similarity	NPC60186
0.73	Intermediate Similarity	NPC202605
0.73	Intermediate Similarity	NPC112206
0.7294	Intermediate Similarity	NPC185838
0.7292	Intermediate Similarity	NPC161804
0.7273	Intermediate Similarity	NPC167116
0.7273	Intermediate Similarity	NPC31311
0.7273	Intermediate Similarity	NPC146288
0.7273	Intermediate Similarity	NPC147091
0.7273	Intermediate Similarity	NPC234392
0.7273	Intermediate Similarity	NPC274716
0.7273	Intermediate Similarity	NPC254441
0.7258	Intermediate Similarity	NPC286119
0.7257	Intermediate Similarity	NPC477564
0.7257	Intermediate Similarity	NPC2295
0.7254	Intermediate Similarity	NPC193906
0.7254	Intermediate Similarity	NPC23080
0.7247	Intermediate Similarity	NPC205167
0.7243	Intermediate Similarity	NPC114364
0.7243	Intermediate Similarity	NPC320223
0.7238	Intermediate Similarity	NPC298979
0.7235	Intermediate Similarity	NPC125852
0.7228	Intermediate Similarity	NPC128560
0.7228	Intermediate Similarity	NPC229166
0.7228	Intermediate Similarity	NPC199465
0.7225	Intermediate Similarity	NPC24260
0.7222	Intermediate Similarity	NPC284183
0.7222	Intermediate Similarity	NPC134858
0.7222	Intermediate Similarity	NPC121275
0.7222	Intermediate Similarity	NPC4138
0.7219	Intermediate Similarity	NPC30779
0.7216	Intermediate Similarity	NPC212163
0.7213	Intermediate Similarity	NPC475215
0.7213	Intermediate Similarity	NPC108434
0.7202	Intermediate Similarity	NPC474188
0.72	Intermediate Similarity	NPC26601
0.72	Intermediate Similarity	NPC269449
0.7196	Intermediate Similarity	NPC212237
0.7196	Intermediate Similarity	NPC116465
0.7195	Intermediate Similarity	NPC33338
0.7195	Intermediate Similarity	NPC300020
0.7195	Intermediate Similarity	NPC302171
0.7182	Intermediate Similarity	NPC35627
0.7182	Intermediate Similarity	NPC81247
0.7182	Intermediate Similarity	NPC476573
0.7176	Intermediate Similarity	NPC128019
0.7176	Intermediate Similarity	NPC136860
0.7176	Intermediate Similarity	NPC476567
0.7174	Intermediate Similarity	NPC2314
0.7167	Intermediate Similarity	NPC233650
0.7158	Intermediate Similarity	NPC275680
0.7158	Intermediate Similarity	NPC22115
0.7151	Intermediate Similarity	NPC249274
0.715	Intermediate Similarity	NPC280272
0.715	Intermediate Similarity	NPC472193
0.7143	Intermediate Similarity	NPC76213
0.7143	Intermediate Similarity	NPC295676
0.7143	Intermediate Similarity	NPC277669
0.7136	Intermediate Similarity	NPC10653
0.7136	Intermediate Similarity	NPC318525
0.7129	Intermediate Similarity	NPC119722
0.7127	Intermediate Similarity	NPC33507
0.712	Intermediate Similarity	NPC175890
0.712	Intermediate Similarity	NPC206900
0.712	Intermediate Similarity	NPC11296
0.712	Intermediate Similarity	NPC274661
0.712	Intermediate Similarity	NPC48490
0.712	Intermediate Similarity	NPC239775
0.712	Intermediate Similarity	NPC82457
0.7119	Intermediate Similarity	NPC93593
0.7113	Intermediate Similarity	NPC153042

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 NPC477187 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	701
0.2-0.3	1085
0.3-0.4	1341
0.4-0.5	3318
0.5-0.6	2196
0.6-0.7	303
0.7-0.8	6
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
0.7879	Intermediate Similarity	NPD2420	Approved
0.7879	Intermediate Similarity	NPD2421	Approved
0.7711	Intermediate Similarity	NPD3845	Phase 1
0.7611	Intermediate Similarity	NPD7479	Phase 2
0.7605	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD3975	Discontinued
0.7412	Intermediate Similarity	NPD4584	Approved
0.7312	Intermediate Similarity	NPD8054	Approved
0.7312	Intermediate Similarity	NPD8053	Approved
0.7302	Intermediate Similarity	NPD6656	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5610	Approved
0.7128	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3784	Discontinued
0.7059	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4498	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5600	Discontinued
0.6974	Remote Similarity	NPD5582	Discontinued
0.6973	Remote Similarity	NPD5938	Phase 3
0.6973	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7262	Phase 1
0.694	Remote Similarity	NPD3983	Phase 3
0.694	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8099	Discontinued
0.6935	Remote Similarity	NPD8252	Approved
0.6935	Remote Similarity	NPD8251	Approved
0.6931	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5658	Approved
0.6923	Remote Similarity	NPD7718	Clinical (unspecified phase)
0.691	Remote Similarity	NPD3296	Phase 1
0.6909	Remote Similarity	NPD3595	Approved
0.6909	Remote Similarity	NPD3594	Approved
0.6898	Remote Similarity	NPD8156	Discontinued
0.6897	Remote Similarity	NPD3141	Discontinued
0.6881	Remote Similarity	NPD7222	Phase 2
0.6878	Remote Similarity	NPD3815	Phase 1
0.6878	Remote Similarity	NPD3816	Phase 1
0.6875	Remote Similarity	NPD4951	Discontinued
0.6871	Remote Similarity	NPD6320	Approved
0.6867	Remote Similarity	NPD5156	Approved
0.6867	Remote Similarity	NPD5155	Approved
0.6847	Remote Similarity	NPD2916	Discontinued
0.6833	Remote Similarity	NPD7298	Approved
0.6829	Remote Similarity	NPD3055	Approved
0.6829	Remote Similarity	NPD3053	Approved
0.6828	Remote Similarity	NPD2898	Approved
0.6828	Remote Similarity	NPD27	Approved
0.6828	Remote Similarity	NPD2489	Approved
0.6826	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD4010	Discontinued
0.6807	Remote Similarity	NPD2606	Approved
0.6807	Remote Similarity	NPD2605	Approved
0.6804	Remote Similarity	NPD2843	Phase 2
0.6804	Remote Similarity	NPD2845	Phase 2
0.6796	Remote Similarity	NPD6738	Phase 2
0.6796	Remote Similarity	NPD6737	Phase 2
0.6793	Remote Similarity	NPD5823	Approved
0.6793	Remote Similarity	NPD7201	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD6767	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD313	Approved
0.6791	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD4773	Phase 2
0.6778	Remote Similarity	NPD4772	Phase 2
0.6778	Remote Similarity	NPD2789	Approved
0.6758	Remote Similarity	NPD5599	Discontinued
0.6747	Remote Similarity	NPD3637	Approved
0.6747	Remote Similarity	NPD3635	Approved
0.6747	Remote Similarity	NPD3636	Approved
0.6743	Remote Similarity	NPD3301	Approved
0.6739	Remote Similarity	NPD4796	Discontinued
0.6738	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD6877	Discontinued
0.6721	Remote Similarity	NPD19	Approved
0.6721	Remote Similarity	NPD1743	Approved
0.6721	Remote Similarity	NPD1742	Approved
0.672	Remote Similarity	NPD3051	Approved
0.6708	Remote Similarity	NPD4093	Discontinued
0.6705	Remote Similarity	NPD4721	Approved
0.6705	Remote Similarity	NPD4725	Approved
0.6705	Remote Similarity	NPD4726	Approved
0.6704	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6037	Discontinued
0.67	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5609	Approved
0.67	Remote Similarity	NPD5608	Approved
0.6686	Remote Similarity	NPD5819	Phase 2
0.6685	Remote Similarity	NPD6533	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD2970	Approved
0.6684	Remote Similarity	NPD4083	Discontinued
0.6684	Remote Similarity	NPD2969	Approved
0.6682	Remote Similarity	NPD2899	Discontinued
0.6667	Remote Similarity	NPD4120	Approved
0.6667	Remote Similarity	NPD5530	Phase 1
0.6667	Remote Similarity	NPD5310	Approved
0.6667	Remote Similarity	NPD7906	Approved
0.6667	Remote Similarity	NPD4121	Phase 3
0.6667	Remote Similarity	NPD5311	Approved
0.6651	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD6031	Approved
0.6648	Remote Similarity	NPD6030	Approved
0.6646	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7452	Approved
0.6634	Remote Similarity	NPD7453	Approved
0.6633	Remote Similarity	NPD5928	Phase 1
0.6632	Remote Similarity	NPD7311	Approved
0.6632	Remote Similarity	NPD7313	Approved
0.6632	Remote Similarity	NPD4577	Approved
0.6632	Remote Similarity	NPD4578	Approved
0.6632	Remote Similarity	NPD7310	Approved
0.6632	Remote Similarity	NPD7312	Approved
0.663	Remote Similarity	NPD5743	Approved
0.663	Remote Similarity	NPD5742	Approved
0.663	Remote Similarity	NPD5741	Approved
0.663	Remote Similarity	NPD5617	Suspended
0.6629	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6494	Phase 2
0.6616	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD4663	Approved
0.6612	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6283	Phase 2
0.66	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5641	Discontinued
0.6598	Remote Similarity	NPD7309	Approved
0.6597	Remote Similarity	NPD3920	Phase 2
0.6595	Remote Similarity	NPD7831	Phase 2
0.6595	Remote Similarity	NPD7833	Phase 2
0.6595	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD2469	Approved
0.6593	Remote Similarity	NPD2468	Approved
0.6585	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6493	Phase 3
0.658	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD4017	Approved
0.6575	Remote Similarity	NPD3229	Phase 2
0.6575	Remote Similarity	NPD6357	Discontinued
0.6571	Remote Similarity	NPD4256	Phase 2
0.6571	Remote Similarity	NPD4257	Approved
0.657	Remote Similarity	NPD817	Approved
0.657	Remote Similarity	NPD823	Approved
0.6566	Remote Similarity	NPD3921	Approved
0.6566	Remote Similarity	NPD3922	Approved
0.6566	Remote Similarity	NPD3924	Approved
0.6566	Remote Similarity	NPD5937	Approved
0.6566	Remote Similarity	NPD3923	Approved
0.6556	Remote Similarity	NPD3640	Phase 3
0.6556	Remote Similarity	NPD3641	Approved
0.6556	Remote Similarity	NPD3639	Approved
0.6555	Remote Similarity	NPD7301	Phase 3
0.6554	Remote Similarity	NPD5241	Discontinued
0.6548	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7630	Phase 3
0.6548	Remote Similarity	NPD7628	Phase 3
0.6547	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD7877	Suspended
0.6546	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6159	Phase 2
0.6545	Remote Similarity	NPD3793	Phase 3
0.6543	Remote Similarity	NPD5303	Approved
0.6543	Remote Similarity	NPD5304	Approved
0.6541	Remote Similarity	NPD6788	Approved
0.6536	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD4430	Phase 2
0.6526	Remote Similarity	NPD3763	Approved
0.6526	Remote Similarity	NPD7324	Discontinued
0.6517	Remote Similarity	NPD7948	Phase 1
0.6517	Remote Similarity	NPD7034	Discontinued
0.65	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4418	Discontinued
0.6497	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD3398	Discontinued
0.6495	Remote Similarity	NPD6461	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD1753	Discontinued
0.6493	Remote Similarity	NPD5902	Approved
0.6493	Remote Similarity	NPD5903	Approved
0.6471	Remote Similarity	NPD6723	Discontinued
0.6465	Remote Similarity	NPD5506	Approved
0.6465	Remote Similarity	NPD5507	Approved
0.6462	Remote Similarity	NPD8149	Discontinued
0.6462	Remote Similarity	NPD7112	Discontinued
0.6461	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD1294	Discontinued
0.6455	Remote Similarity	NPD6071	Discontinued
0.6453	Remote Similarity	NPD3061	Approved
0.6453	Remote Similarity	NPD3062	Approved
0.6453	Remote Similarity	NPD3059	Approved
0.6442	Remote Similarity	NPD7300	Phase 3
0.6442	Remote Similarity	NPD7302	Phase 3
0.6439	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6636	Phase 3
0.6436	Remote Similarity	NPD4605	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