NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	295.12
Volume:	298.651
LogP:	-0.191
LogD:	1.31
LogS:	-1.167
# Rotatable Bonds:	0
TPSA:	41.52
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.553
Synthetic Accessibility Score:	3.869
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:	-5.396
MDCK Permeability:	3.15E-05
Pgp-inhibitor:	0.001
Pgp-substrate:	1
Human Intestinal Absorption (HIA):	0.054
20% Bioavailability (F20%):	0.989
30% Bioavailability (F30%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.549
Plasma Protein Binding (PPB):	75.69%
Volume Distribution (VD):	2.524
Pgp-substrate:	32.90%

ADMET: Metabolism

CYP1A2-inhibitor:	0.652
CYP1A2-substrate:	0.665
CYP2C19-inhibitor:	0.189
CYP2C19-substrate:	0.793
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.759
CYP2D6-inhibitor:	0.795
CYP2D6-substrate:	0.869
CYP3A4-inhibitor:	0.749
CYP3A4-substrate:	0.798

ADMET: Excretion

Clearance (CL):	11.791
Half-life (T1/2):	0.916

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.111
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.892
Rat Oral Acute Toxicity:	0.133
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.09
Carcinogencity:	0.915
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.135

Download Data

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

Natural Product: NPC477560

Natural Product ID:	NPC477560
*Common Name:**	(11R,12R)-11-methyl-11-oxido-3,5-dioxa-11-azoniapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene;2,2,2-trifluoroacetic acid
IUPAC Name:	(11R,12R)-11-methyl-11-oxido-3,5-dioxa-11-azoniapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene;2,2,2-trifluoroacetic acid
Synonyms:
Standard InCHIKey:	OXPULTLJRYLGDW-HNJSCFAESA-N
Standard InCHI:	InChI=1S/C18H17NO3.C2HF3O2/c1-19(20)7-6-12-9-15-18(22-10-21-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17;3-2(4,5)1(6)7/h2-5,9,14H,6-8,10H2,1H3;(H,6,7)/t14-,19-;/m1./s1
SMILES:	C[N@+]1(CCC2=CC3=C(C4=C2[C@H]1CC5=CC=CC=C54)OCO3)[O-].C(=O)(C(F)(F)F)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118718876
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
NPO11152	Neolitsea dealbata	Species	Lauraceae	Eukaryota	Barks	Thomas Road, 1.5km West of Yungaburra, Australia	1998-MAY	PMID[20732809]
NPO11152	Neolitsea dealbata	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	10
Others	4

Activity Type	# Activity
Cell Line	12
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000	nM	PMID[20732809]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000	nM	PMID[20732809]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000	nM	PMID[20732809]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	100000	nM	PMID[20732809]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	100000	nM	PMID[20732809]
NPT1523	Cell Line	NFF	Homo sapiens	Inhibition	=	83	%	PMID[20732809]
NPT1523	Cell Line	NFF	Homo sapiens	Inhibition	=	66	%	PMID[20732809]
NPT27	Others	Unspecified		Inhibition	<=	61	%	PMID[20732809]
NPT27	Others	Unspecified		Inhibition	=	49	%	PMID[20732809]

☑ 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 NPC477560 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	281
0.1-0.2	1582
0.2-0.3	7351
0.3-0.4	10827
0.4-0.5	6939
0.5-0.6	12926
0.6-0.7	2070
0.7-0.8	542
0.8-0.85	114
0.85-0.9	57
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8895	High Similarity	NPC233718
0.8882	High Similarity	NPC470924
0.8452	Intermediate Similarity	NPC477559
0.8452	Intermediate Similarity	NPC266753
0.8452	Intermediate Similarity	NPC160298
0.8452	Intermediate Similarity	NPC232924
0.8452	Intermediate Similarity	NPC306902
0.8421	Intermediate Similarity	NPC298979
0.8372	Intermediate Similarity	NPC241055
0.8363	Intermediate Similarity	NPC24264
0.8363	Intermediate Similarity	NPC476432
0.8314	Intermediate Similarity	NPC247389
0.8304	Intermediate Similarity	NPC16805
0.8304	Intermediate Similarity	NPC302527
0.8304	Intermediate Similarity	NPC167546
0.8304	Intermediate Similarity	NPC225774
0.8256	Intermediate Similarity	NPC219341
0.8208	Intermediate Similarity	NPC210918
0.8198	Intermediate Similarity	NPC168409
0.8192	Intermediate Similarity	NPC114364
0.8192	Intermediate Similarity	NPC320223
0.8182	Intermediate Similarity	NPC229166
0.8182	Intermediate Similarity	NPC199465
0.8182	Intermediate Similarity	NPC128560
0.8156	Intermediate Similarity	NPC116284
0.815	Intermediate Similarity	NPC86144
0.815	Intermediate Similarity	NPC304659
0.8144	Intermediate Similarity	NPC326316
0.8144	Intermediate Similarity	NPC81733
0.8107	Intermediate Similarity	NPC41178
0.8107	Intermediate Similarity	NPC216459
0.8107	Intermediate Similarity	NPC138487
0.8095	Intermediate Similarity	NPC37272
0.8077	Intermediate Similarity	NPC237579
0.8072	Intermediate Similarity	NPC475959
0.8068	Intermediate Similarity	NPC19520
0.8068	Intermediate Similarity	NPC149090
0.8059	Intermediate Similarity	NPC477133
0.8059	Intermediate Similarity	NPC146288
0.8059	Intermediate Similarity	NPC477132
0.8056	Intermediate Similarity	NPC248642
0.8045	Intermediate Similarity	NPC126284
0.8035	Intermediate Similarity	NPC189470
0.8035	Intermediate Similarity	NPC59567
0.8024	Intermediate Similarity	NPC44869
0.8023	Intermediate Similarity	NPC27410
0.8023	Intermediate Similarity	NPC166014
0.8012	Intermediate Similarity	NPC475326
0.8012	Intermediate Similarity	NPC476572
0.8011	Intermediate Similarity	NPC6152
0.8011	Intermediate Similarity	NPC156576
0.8011	Intermediate Similarity	NPC152212
0.8	Intermediate Similarity	NPC474324
0.8	Intermediate Similarity	NPC325871
0.8	Intermediate Similarity	NPC99659
0.8	Intermediate Similarity	NPC57812
0.7989	Intermediate Similarity	NPC118633
0.7989	Intermediate Similarity	NPC232514
0.7989	Intermediate Similarity	NPC148693
0.7989	Intermediate Similarity	NPC276944
0.7989	Intermediate Similarity	NPC76116
0.7989	Intermediate Similarity	NPC238530
0.7989	Intermediate Similarity	NPC294790
0.7978	Intermediate Similarity	NPC304675
0.7955	Intermediate Similarity	NPC475845
0.7953	Intermediate Similarity	NPC234392
0.7953	Intermediate Similarity	NPC31311
0.7935	Intermediate Similarity	NPC82763
0.7933	Intermediate Similarity	NPC237044
0.7931	Intermediate Similarity	NPC324144
0.7912	Intermediate Similarity	NPC135772
0.791	Intermediate Similarity	NPC474708
0.791	Intermediate Similarity	NPC329911
0.7901	Intermediate Similarity	NPC155442
0.7901	Intermediate Similarity	NPC476574
0.7901	Intermediate Similarity	NPC477561
0.7901	Intermediate Similarity	NPC312918
0.7898	Intermediate Similarity	NPC306555
0.7898	Intermediate Similarity	NPC474931
0.7898	Intermediate Similarity	NPC81218
0.7898	Intermediate Similarity	NPC12053
0.7898	Intermediate Similarity	NPC145832
0.7898	Intermediate Similarity	NPC158376
0.7898	Intermediate Similarity	NPC117188
0.7898	Intermediate Similarity	NPC205421
0.7889	Intermediate Similarity	NPC474325
0.7886	Intermediate Similarity	NPC78222
0.7886	Intermediate Similarity	NPC136508
0.7886	Intermediate Similarity	NPC477563
0.7886	Intermediate Similarity	NPC13504
0.7886	Intermediate Similarity	NPC96603
0.7886	Intermediate Similarity	NPC253043
0.7886	Intermediate Similarity	NPC196447
0.7886	Intermediate Similarity	NPC306843
0.7886	Intermediate Similarity	NPC212794
0.7882	Intermediate Similarity	NPC148898
0.7882	Intermediate Similarity	NPC210148
0.7882	Intermediate Similarity	NPC233029
0.7882	Intermediate Similarity	NPC223124
0.7877	Intermediate Similarity	NPC477558
0.7861	Intermediate Similarity	NPC477080
0.7861	Intermediate Similarity	NPC106786
0.7861	Intermediate Similarity	NPC111485
0.7853	Intermediate Similarity	NPC160570
0.7853	Intermediate Similarity	NPC210086
0.7853	Intermediate Similarity	NPC164429
0.7849	Intermediate Similarity	NPC203784
0.7849	Intermediate Similarity	NPC170503
0.7849	Intermediate Similarity	NPC126519
0.7845	Intermediate Similarity	NPC220961
0.7845	Intermediate Similarity	NPC474745
0.7833	Intermediate Similarity	NPC474470
0.7826	Intermediate Similarity	NPC214116
0.7802	Intermediate Similarity	NPC474506
0.7802	Intermediate Similarity	NPC32413
0.7798	Intermediate Similarity	NPC106295
0.7798	Intermediate Similarity	NPC51957
0.7798	Intermediate Similarity	NPC16107
0.7798	Intermediate Similarity	NPC476144
0.7798	Intermediate Similarity	NPC210437
0.7791	Intermediate Similarity	NPC78733
0.7791	Intermediate Similarity	NPC93593
0.779	Intermediate Similarity	NPC23219
0.7784	Intermediate Similarity	NPC231198
0.7765	Intermediate Similarity	NPC223125
0.7759	Intermediate Similarity	NPC118804
0.7758	Intermediate Similarity	NPC213206
0.7758	Intermediate Similarity	NPC328750
0.7758	Intermediate Similarity	NPC188163
0.7758	Intermediate Similarity	NPC474915
0.7751	Intermediate Similarity	NPC7467
0.7747	Intermediate Similarity	NPC258695
0.7747	Intermediate Similarity	NPC267408
0.7747	Intermediate Similarity	NPC470879
0.774	Intermediate Similarity	NPC35627
0.774	Intermediate Similarity	NPC81247
0.774	Intermediate Similarity	NPC476573
0.7735	Intermediate Similarity	NPC241704
0.7735	Intermediate Similarity	NPC112575
0.773	Intermediate Similarity	NPC57036
0.7727	Intermediate Similarity	NPC1229
0.7727	Intermediate Similarity	NPC320104
0.7722	Intermediate Similarity	NPC2314
0.7717	Intermediate Similarity	NPC475981
0.7717	Intermediate Similarity	NPC474746
0.7714	Intermediate Similarity	NPC97072
0.7714	Intermediate Similarity	NPC215829
0.7713	Intermediate Similarity	NPC471113
0.7705	Intermediate Similarity	NPC179704
0.7697	Intermediate Similarity	NPC314682
0.7697	Intermediate Similarity	NPC190332
0.7697	Intermediate Similarity	NPC181653
0.7692	Intermediate Similarity	NPC476151
0.7688	Intermediate Similarity	NPC110416
0.7688	Intermediate Similarity	NPC193949
0.7688	Intermediate Similarity	NPC204828
0.7688	Intermediate Similarity	NPC469817
0.7688	Intermediate Similarity	NPC172765
0.7688	Intermediate Similarity	NPC249797
0.7688	Intermediate Similarity	NPC127674
0.7688	Intermediate Similarity	NPC39701
0.7688	Intermediate Similarity	NPC76079
0.7688	Intermediate Similarity	NPC476576
0.7688	Intermediate Similarity	NPC295691
0.7688	Intermediate Similarity	NPC278799
0.7688	Intermediate Similarity	NPC474904
0.7688	Intermediate Similarity	NPC207757
0.7688	Intermediate Similarity	NPC276588
0.7688	Intermediate Similarity	NPC54379
0.7688	Intermediate Similarity	NPC184026
0.7688	Intermediate Similarity	NPC189266
0.7688	Intermediate Similarity	NPC186546
0.7688	Intermediate Similarity	NPC5238
0.7688	Intermediate Similarity	NPC2413
0.7679	Intermediate Similarity	NPC185838
0.7679	Intermediate Similarity	NPC130926
0.7667	Intermediate Similarity	NPC239775
0.7667	Intermediate Similarity	NPC10871
0.7665	Intermediate Similarity	NPC128019
0.7665	Intermediate Similarity	NPC136860
0.7665	Intermediate Similarity	NPC476567
0.7663	Intermediate Similarity	NPC275132
0.7663	Intermediate Similarity	NPC476575
0.7661	Intermediate Similarity	NPC274026
0.7654	Intermediate Similarity	NPC82533
0.7654	Intermediate Similarity	NPC266176
0.7654	Intermediate Similarity	NPC158148
0.7654	Intermediate Similarity	NPC290759
0.7654	Intermediate Similarity	NPC470324
0.765	Intermediate Similarity	NPC32154
0.7647	Intermediate Similarity	NPC246587
0.7647	Intermediate Similarity	NPC24233
0.7647	Intermediate Similarity	NPC428
0.7647	Intermediate Similarity	NPC476571
0.7647	Intermediate Similarity	NPC135538
0.7647	Intermediate Similarity	NPC147390
0.7637	Intermediate Similarity	NPC287588
0.7634	Intermediate Similarity	NPC230098
0.7624	Intermediate Similarity	NPC66341
0.7624	Intermediate Similarity	NPC477020

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 NPC477560 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	746
0.2-0.3	1062
0.3-0.4	1999
0.4-0.5	2739
0.5-0.6	1850
0.6-0.7	487
0.7-0.8	92
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
0.7853	Intermediate Similarity	NPD4481	Phase 3
0.7798	Intermediate Similarity	NPD4584	Approved
0.7758	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2898	Approved
0.7627	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2970	Approved
0.75	Intermediate Similarity	NPD2969	Approved
0.7459	Intermediate Similarity	NPD27	Approved
0.7459	Intermediate Similarity	NPD2489	Approved
0.7444	Intermediate Similarity	NPD3051	Approved
0.7429	Intermediate Similarity	NPD4773	Phase 2
0.7429	Intermediate Similarity	NPD4772	Phase 2
0.7399	Intermediate Similarity	NPD3639	Approved
0.7399	Intermediate Similarity	NPD3641	Approved
0.7399	Intermediate Similarity	NPD3640	Phase 3
0.7326	Intermediate Similarity	NPD7310	Approved
0.7326	Intermediate Similarity	NPD7311	Approved
0.7326	Intermediate Similarity	NPD7312	Approved
0.7326	Intermediate Similarity	NPD2421	Approved
0.7326	Intermediate Similarity	NPD2420	Approved
0.7326	Intermediate Similarity	NPD7313	Approved
0.731	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6107	Approved
0.7287	Intermediate Similarity	NPD7309	Approved
0.7234	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4017	Approved
0.72	Intermediate Similarity	NPD1914	Approved
0.72	Intermediate Similarity	NPD4727	Phase 1
0.7191	Intermediate Similarity	NPD7298	Approved
0.7167	Intermediate Similarity	NPD6788	Approved
0.7166	Intermediate Similarity	NPD6297	Approved
0.7158	Intermediate Similarity	NPD4166	Phase 2
0.7143	Intermediate Similarity	NPD7281	Phase 3
0.7143	Intermediate Similarity	NPD4420	Approved
0.7143	Intermediate Similarity	NPD7280	Phase 3
0.7143	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD4482	Phase 3
0.711	Intermediate Similarity	NPD5241	Discontinued
0.7083	Intermediate Similarity	NPD7906	Approved
0.7071	Intermediate Similarity	NPD4107	Approved
0.7069	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD6747	Phase 1
0.7065	Intermediate Similarity	NPD6071	Discontinued
0.7059	Intermediate Similarity	NPD5312	Approved
0.7059	Intermediate Similarity	NPD5313	Approved
0.7053	Intermediate Similarity	NPD2968	Approved
0.7053	Intermediate Similarity	NPD2971	Approved
0.7048	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7831	Phase 2
0.7033	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7833	Phase 2
0.7024	Intermediate Similarity	NPD3109	Approved
0.7024	Intermediate Similarity	NPD3110	Approved
0.7017	Intermediate Similarity	NPD2563	Approved
0.7017	Intermediate Similarity	NPD2560	Approved
0.7016	Intermediate Similarity	NPD6851	Approved
0.7016	Intermediate Similarity	NPD6853	Approved
0.701	Intermediate Similarity	NPD2488	Approved
0.701	Intermediate Similarity	NPD2490	Approved
0.7006	Intermediate Similarity	NPD6031	Approved
0.7006	Intermediate Similarity	NPD6030	Approved
0.7005	Intermediate Similarity	NPD8099	Discontinued
0.7005	Intermediate Similarity	NPD8252	Approved
0.7005	Intermediate Similarity	NPD8251	Approved
0.7	Intermediate Similarity	NPD5005	Approved
0.7	Intermediate Similarity	NPD5006	Approved
0.6995	Remote Similarity	NPD7400	Phase 3
0.6979	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD4010	Discontinued
0.6968	Remote Similarity	NPD8156	Discontinued
0.6963	Remote Similarity	NPD4578	Approved
0.6963	Remote Similarity	NPD4577	Approved
0.6959	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5754	Discontinued
0.6943	Remote Similarity	NPD4663	Approved
0.6934	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8054	Approved
0.6927	Remote Similarity	NPD8053	Approved
0.6919	Remote Similarity	NPD2974	Approved
0.6919	Remote Similarity	NPD2975	Approved
0.6919	Remote Similarity	NPD2973	Approved
0.6915	Remote Similarity	NPD2972	Approved
0.6915	Remote Similarity	NPD3448	Approved
0.6915	Remote Similarity	NPD3533	Approved
0.6915	Remote Similarity	NPD2491	Approved
0.6893	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2492	Phase 1
0.6842	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD3124	Discontinued
0.6832	Remote Similarity	NPD3057	Approved
0.6829	Remote Similarity	NPD4859	Phase 1
0.6816	Remote Similarity	NPD4580	Approved
0.6805	Remote Similarity	NPD5718	Phase 2
0.68	Remote Similarity	NPD5177	Phase 3
0.6782	Remote Similarity	NPD2494	Approved
0.6782	Remote Similarity	NPD2493	Approved
0.6782	Remote Similarity	NPD3452	Approved
0.6782	Remote Similarity	NPD3450	Approved
0.678	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD2904	Discontinued
0.674	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5977	Approved
0.6739	Remote Similarity	NPD5978	Approved
0.6738	Remote Similarity	NPD7802	Discontinued
0.6731	Remote Similarity	NPD5676	Approved
0.6721	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3656	Approved
0.6685	Remote Similarity	NPD2978	Approved
0.6685	Remote Similarity	NPD3845	Phase 1
0.6685	Remote Similarity	NPD2977	Approved
0.6683	Remote Similarity	NPD4582	Approved
0.6683	Remote Similarity	NPD4583	Approved
0.6682	Remote Similarity	NPD6723	Discontinued
0.6667	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.665	Remote Similarity	NPD5457	Discontinued
0.665	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7549	Discontinued
0.6634	Remote Similarity	NPD4004	Approved
0.6634	Remote Similarity	NPD4002	Approved
0.6631	Remote Similarity	NPD5709	Phase 3
0.663	Remote Similarity	NPD7427	Discontinued
0.6619	Remote Similarity	NPD7827	Phase 1
0.6616	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD6146	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD1424	Approved
0.6609	Remote Similarity	NPD6896	Approved
0.6609	Remote Similarity	NPD6895	Approved
0.6596	Remote Similarity	NPD5677	Discontinued
0.6596	Remote Similarity	NPD4666	Phase 3
0.6592	Remote Similarity	NPD6667	Approved
0.6592	Remote Similarity	NPD6666	Approved
0.6588	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6618	Phase 2
0.6579	Remote Similarity	NPD6688	Approved
0.6579	Remote Similarity	NPD6687	Approved
0.6578	Remote Similarity	NPD5604	Discontinued
0.6578	Remote Similarity	NPD4055	Discovery
0.6576	Remote Similarity	NPD7110	Phase 1
0.6576	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6748	Discontinued
0.6573	Remote Similarity	NPD5980	Discovery
0.6571	Remote Similarity	NPD4108	Discontinued
0.6571	Remote Similarity	NPD1753	Discontinued
0.6566	Remote Similarity	NPD3349	Phase 2
0.6566	Remote Similarity	NPD7291	Discontinued
0.6552	Remote Similarity	NPD2653	Approved
0.655	Remote Similarity	NPD7296	Approved
0.6541	Remote Similarity	NPD4433	Discontinued
0.6535	Remote Similarity	NPD5582	Discontinued
0.6529	Remote Similarity	NPD3635	Approved
0.6529	Remote Similarity	NPD3637	Approved
0.6529	Remote Similarity	NPD3636	Approved
0.6522	Remote Similarity	NPD4040	Phase 1
0.6512	Remote Similarity	NPD3763	Approved
0.6497	Remote Similarity	NPD1375	Discontinued
0.6495	Remote Similarity	NPD3885	Approved
0.6491	Remote Similarity	NPD2605	Approved
0.6491	Remote Similarity	NPD3594	Approved
0.6491	Remote Similarity	NPD3595	Approved
0.6491	Remote Similarity	NPD2606	Approved
0.6488	Remote Similarity	NPD6612	Phase 2
0.6486	Remote Similarity	NPD6873	Phase 2
0.6484	Remote Similarity	NPD6090	Discontinued
0.6482	Remote Similarity	NPD3398	Discontinued
0.648	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD4474	Approved
0.6474	Remote Similarity	NPD4475	Approved
0.6474	Remote Similarity	NPD2674	Phase 3
0.6464	Remote Similarity	NPD7598	Phase 2
0.6453	Remote Similarity	NPD5155	Approved
0.6453	Remote Similarity	NPD5156	Approved
0.6452	Remote Similarity	NPD7248	Discontinued
0.6452	Remote Similarity	NPD7907	Approved
0.645	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7047	Phase 3
0.6448	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD3692	Discontinued
0.6444	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD6042	Phase 2
0.6443	Remote Similarity	NPD42	Phase 2
0.6441	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD7262	Phase 1
0.6435	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4739	Approved
0.6425	Remote Similarity	NPD4236	Phase 3
0.6425	Remote Similarity	NPD4237	Approved
0.6422	Remote Similarity	NPD6997	Phase 2
0.6421	Remote Similarity	NPD6037	Discontinued
0.6418	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6418	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4585	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