NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	409.19
Volume:	417.37
LogP:	3.192
LogD:	2.568
LogS:	-2.107
# Rotatable Bonds:	4
TPSA:	59.98
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	3.86
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.66
MDCK Permeability:	3.413038211874664e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.218
20% Bioavailability (F20%):	0.563
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.185
Plasma Protein Binding (PPB):	71.90797424316406%
Volume Distribution (VD):	1.575
Pgp-substrate:	21.109819412231445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.136
CYP1A2-substrate:	0.975
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.754
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.887
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	9.911
Half-life (T1/2):	0.902

ADMET: Toxicity

hERG Blockers:	0.05
Human Hepatotoxicity (H-HT):	0.13
Drug-inuced Liver Injury (DILI):	0.257
AMES Toxicity:	0.486
Rat Oral Acute Toxicity:	0.575
Maximum Recommended Daily Dose:	0.968
Skin Sensitization:	0.869
Carcinogencity:	0.055
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.891

Download Data

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

Natural Product: NPC477133

Natural Product ID:	NPC477133
*Common Name:**	(10S,13aR)-3,4,6,7-tetramethoxy-10-oxido-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-10-ium
IUPAC Name:	(10S,13aR)-3,4,6,7-tetramethoxy-10-oxido-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizin-10-ium
Synonyms:	10S,13Ar-Isotylocrebrine N-Oxide
Standard InCHIKey:	DMXRQESJIQTZCZ-PWECECGKSA-N
Standard InCHI:	InChI=1S/C24H27NO5/c1-27-20-8-7-15-16-10-14-6-5-9-25(14,26)13-19(16)17-11-21(28-2)22(29-3)12-18(17)23(15)24(20)30-4/h7-8,11-12,14H,5-6,9-10,13H2,1-4H3/t14-,25+/m1/s1
SMILES:	COC1=C(C2=C(C=C1)C3=C(C[N@+]4(CCC[C@@H]4C3)[O-])C5=CC(=C(C=C52)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11407207
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0001906] Phenanthroindolizidines

*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
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	Stems	Tainan Hsien, Taiwan, Republic of China	2000-JAN	PMID[16038551]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19938815]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6257	Ficus septica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6257	Ficus septica	Species	Moraceae	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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4162	Cell Line	NUGC	Homo sapiens	Inhibition	=	93	%	PMID[16038551]
NPT2	Others	Unspecified		Inhibition	=	87	%	PMID[16038551]

☑ 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 NPC477133 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	383
0.1-0.2	1796
0.2-0.3	7645
0.3-0.4	10329
0.4-0.5	6470
0.5-0.6	12123
0.6-0.7	3134
0.7-0.8	597
0.8-0.85	184
0.85-0.9	25
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477132
0.9456	High Similarity	NPC44869
0.9359	High Similarity	NPC329911
0.9172	High Similarity	NPC160570
0.8981	High Similarity	NPC76116
0.8896	High Similarity	NPC244112
0.8812	High Similarity	NPC164429
0.8776	High Similarity	NPC210086
0.8766	High Similarity	NPC470924
0.8571	High Similarity	NPC475828
0.8506	High Similarity	NPC130941
0.8452	Intermediate Similarity	NPC219162
0.8323	Intermediate Similarity	NPC253883
0.8323	Intermediate Similarity	NPC95075
0.8323	Intermediate Similarity	NPC90844
0.8313	Intermediate Similarity	NPC476572
0.8302	Intermediate Similarity	NPC325871
0.8302	Intermediate Similarity	NPC99659
0.8235	Intermediate Similarity	NPC233718
0.8232	Intermediate Similarity	NPC24264
0.8232	Intermediate Similarity	NPC476432
0.8182	Intermediate Similarity	NPC150879
0.8182	Intermediate Similarity	NPC247389
0.8171	Intermediate Similarity	NPC16805
0.8171	Intermediate Similarity	NPC225774
0.8171	Intermediate Similarity	NPC302527
0.8171	Intermediate Similarity	NPC167546
0.8144	Intermediate Similarity	NPC10871
0.8137	Intermediate Similarity	NPC186063
0.8121	Intermediate Similarity	NPC219341
0.8113	Intermediate Similarity	NPC81733
0.8113	Intermediate Similarity	NPC326316
0.8101	Intermediate Similarity	NPC211296
0.8101	Intermediate Similarity	NPC92541
0.8079	Intermediate Similarity	NPC11147
0.8072	Intermediate Similarity	NPC210918
0.8063	Intermediate Similarity	NPC26601
0.8063	Intermediate Similarity	NPC37272
0.8059	Intermediate Similarity	NPC477560
0.8049	Intermediate Similarity	NPC60186
0.8	Intermediate Similarity	NPC233650
0.7988	Intermediate Similarity	NPC232924
0.7988	Intermediate Similarity	NPC477559
0.7988	Intermediate Similarity	NPC160298
0.7988	Intermediate Similarity	NPC306902
0.7988	Intermediate Similarity	NPC266753
0.7975	Intermediate Similarity	NPC16107
0.7975	Intermediate Similarity	NPC476144
0.7975	Intermediate Similarity	NPC144863
0.7975	Intermediate Similarity	NPC210437
0.7975	Intermediate Similarity	NPC106295
0.7975	Intermediate Similarity	NPC51957
0.7964	Intermediate Similarity	NPC158376
0.7964	Intermediate Similarity	NPC205421
0.7964	Intermediate Similarity	NPC145832
0.7964	Intermediate Similarity	NPC474931
0.7964	Intermediate Similarity	NPC306555
0.7964	Intermediate Similarity	NPC12053
0.7964	Intermediate Similarity	NPC81218
0.7964	Intermediate Similarity	NPC117188
0.7963	Intermediate Similarity	NPC76079
0.7952	Intermediate Similarity	NPC78222
0.7952	Intermediate Similarity	NPC13504
0.7952	Intermediate Similarity	NPC196447
0.7952	Intermediate Similarity	NPC136508
0.7952	Intermediate Similarity	NPC253043
0.7952	Intermediate Similarity	NPC212794
0.7952	Intermediate Similarity	NPC134858
0.7952	Intermediate Similarity	NPC477563
0.7952	Intermediate Similarity	NPC306843
0.7952	Intermediate Similarity	NPC96603
0.7935	Intermediate Similarity	NPC328750
0.7935	Intermediate Similarity	NPC213206
0.7935	Intermediate Similarity	NPC188163
0.7935	Intermediate Similarity	NPC474915
0.7929	Intermediate Similarity	NPC19520
0.7929	Intermediate Similarity	NPC149090
0.7925	Intermediate Similarity	NPC7467
0.7914	Intermediate Similarity	NPC323443
0.7914	Intermediate Similarity	NPC180756
0.7892	Intermediate Similarity	NPC324144
0.7881	Intermediate Similarity	NPC118419
0.7871	Intermediate Similarity	NPC314682
0.787	Intermediate Similarity	NPC6152
0.7866	Intermediate Similarity	NPC475326
0.7857	Intermediate Similarity	NPC210140
0.7853	Intermediate Similarity	NPC138487
0.7853	Intermediate Similarity	NPC216459
0.7853	Intermediate Similarity	NPC41178
0.7853	Intermediate Similarity	NPC93593
0.7853	Intermediate Similarity	NPC123323
0.7849	Intermediate Similarity	NPC114364
0.7849	Intermediate Similarity	NPC320223
0.7848	Intermediate Similarity	NPC145304
0.7836	Intermediate Similarity	NPC128560
0.7836	Intermediate Similarity	NPC229166
0.7836	Intermediate Similarity	NPC199465
0.7834	Intermediate Similarity	NPC476567
0.7834	Intermediate Similarity	NPC128019
0.7834	Intermediate Similarity	NPC136860
0.7812	Intermediate Similarity	NPC475959
0.7805	Intermediate Similarity	NPC170503
0.7805	Intermediate Similarity	NPC146288
0.7805	Intermediate Similarity	NPC203784
0.7805	Intermediate Similarity	NPC126519
0.7784	Intermediate Similarity	NPC1229
0.7771	Intermediate Similarity	NPC205167
0.7771	Intermediate Similarity	NPC166014
0.7771	Intermediate Similarity	NPC249274
0.7771	Intermediate Similarity	NPC27410
0.7765	Intermediate Similarity	NPC75958
0.7765	Intermediate Similarity	NPC471113
0.7751	Intermediate Similarity	NPC298979
0.7751	Intermediate Similarity	NPC204947
0.775	Intermediate Similarity	NPC476151
0.7746	Intermediate Similarity	NPC23219
0.7738	Intermediate Similarity	NPC169743
0.7736	Intermediate Similarity	NPC130926
0.7719	Intermediate Similarity	NPC239775
0.7714	Intermediate Similarity	NPC248642
0.7711	Intermediate Similarity	NPC477080
0.7711	Intermediate Similarity	NPC118804
0.7706	Intermediate Similarity	NPC241055
0.7701	Intermediate Similarity	NPC126284
0.7697	Intermediate Similarity	NPC234392
0.7697	Intermediate Similarity	NPC31311
0.7692	Intermediate Similarity	NPC304659
0.7692	Intermediate Similarity	NPC86144
0.7674	Intermediate Similarity	NPC192135
0.7674	Intermediate Similarity	NPC477020
0.7674	Intermediate Similarity	NPC66341
0.767	Intermediate Similarity	NPC156576
0.7669	Intermediate Similarity	NPC476568
0.7665	Intermediate Similarity	NPC235143
0.7665	Intermediate Similarity	NPC119649
0.7665	Intermediate Similarity	NPC271388
0.7665	Intermediate Similarity	NPC205255
0.7665	Intermediate Similarity	NPC230956
0.7661	Intermediate Similarity	NPC26240
0.7661	Intermediate Similarity	NPC69712
0.7661	Intermediate Similarity	NPC118274
0.7661	Intermediate Similarity	NPC168753
0.7661	Intermediate Similarity	NPC477562
0.7657	Intermediate Similarity	NPC474506
0.7657	Intermediate Similarity	NPC32413
0.7654	Intermediate Similarity	NPC477565
0.7654	Intermediate Similarity	NPC103379
0.7651	Intermediate Similarity	NPC148014
0.7651	Intermediate Similarity	NPC40389
0.7651	Intermediate Similarity	NPC65490
0.7651	Intermediate Similarity	NPC78359
0.7651	Intermediate Similarity	NPC315707
0.7647	Intermediate Similarity	NPC474324
0.7647	Intermediate Similarity	NPC57812
0.7644	Intermediate Similarity	NPC118633
0.7644	Intermediate Similarity	NPC148693
0.7644	Intermediate Similarity	NPC294790
0.7636	Intermediate Similarity	NPC172765
0.7636	Intermediate Similarity	NPC127674
0.7636	Intermediate Similarity	NPC39701
0.7636	Intermediate Similarity	NPC189266
0.7636	Intermediate Similarity	NPC278799
0.7636	Intermediate Similarity	NPC207757
0.7636	Intermediate Similarity	NPC78733
0.7636	Intermediate Similarity	NPC204828
0.7636	Intermediate Similarity	NPC249797
0.7636	Intermediate Similarity	NPC469817
0.7636	Intermediate Similarity	NPC276588
0.7636	Intermediate Similarity	NPC5238
0.7636	Intermediate Similarity	NPC54379
0.7636	Intermediate Similarity	NPC184026
0.7636	Intermediate Similarity	NPC295691
0.7636	Intermediate Similarity	NPC193949
0.7636	Intermediate Similarity	NPC110416
0.7636	Intermediate Similarity	NPC2413
0.7633	Intermediate Similarity	NPC247972
0.7633	Intermediate Similarity	NPC168409
0.7633	Intermediate Similarity	NPC180306
0.7632	Intermediate Similarity	NPC160193
0.7628	Intermediate Similarity	NPC193528
0.7625	Intermediate Similarity	NPC185838
0.7622	Intermediate Similarity	NPC114124
0.7622	Intermediate Similarity	NPC233029
0.7622	Intermediate Similarity	NPC210148
0.7619	Intermediate Similarity	NPC80759
0.7619	Intermediate Similarity	NPC79402
0.7614	Intermediate Similarity	NPC116284
0.7605	Intermediate Similarity	NPC92191
0.7605	Intermediate Similarity	NPC7393
0.7605	Intermediate Similarity	NPC59028
0.7605	Intermediate Similarity	NPC221864
0.7602	Intermediate Similarity	NPC290759
0.7602	Intermediate Similarity	NPC475845
0.7602	Intermediate Similarity	NPC158148
0.7602	Intermediate Similarity	NPC266176
0.7602	Intermediate Similarity	NPC82533
0.76	Intermediate Similarity	NPC470879
0.76	Intermediate Similarity	NPC267408
0.76	Intermediate Similarity	NPC220961
0.76	Intermediate Similarity	NPC258695

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 NPC477133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	771
0.2-0.3	944
0.3-0.4	2172
0.4-0.5	2682
0.5-0.6	1684
0.6-0.7	558
0.7-0.8	111
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7975	Intermediate Similarity	NPD4584	Approved
0.7935	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2563	Approved
0.7651	Intermediate Similarity	NPD2560	Approved
0.7602	Intermediate Similarity	NPD4481	Phase 3
0.7562	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2970	Approved
0.7544	Intermediate Similarity	NPD2969	Approved
0.7516	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6071	Discontinued
0.7485	Intermediate Similarity	NPD3051	Approved
0.7414	Intermediate Similarity	NPD8099	Discontinued
0.7414	Intermediate Similarity	NPD8251	Approved
0.7414	Intermediate Similarity	NPD8252	Approved
0.7399	Intermediate Similarity	NPD2489	Approved
0.7399	Intermediate Similarity	NPD2898	Approved
0.7399	Intermediate Similarity	NPD27	Approved
0.7396	Intermediate Similarity	NPD6788	Approved
0.7371	Intermediate Similarity	NPD8156	Discontinued
0.736	Intermediate Similarity	NPD7312	Approved
0.736	Intermediate Similarity	NPD7313	Approved
0.736	Intermediate Similarity	NPD7310	Approved
0.736	Intermediate Similarity	NPD7311	Approved
0.7349	Intermediate Similarity	NPD4017	Approved
0.7333	Intermediate Similarity	NPD3639	Approved
0.7333	Intermediate Similarity	NPD3641	Approved
0.7333	Intermediate Similarity	NPD3640	Phase 3
0.7321	Intermediate Similarity	NPD7298	Approved
0.7318	Intermediate Similarity	NPD7309	Approved
0.7296	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7831	Phase 2
0.7251	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7833	Phase 2
0.7239	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6030	Approved
0.7229	Intermediate Similarity	NPD6031	Approved
0.7229	Intermediate Similarity	NPD5976	Discontinued
0.7222	Intermediate Similarity	NPD4237	Approved
0.7222	Intermediate Similarity	NPD4236	Phase 3
0.7209	Intermediate Similarity	NPD7400	Phase 3
0.7193	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4773	Phase 2
0.716	Intermediate Similarity	NPD4772	Phase 2
0.7152	Intermediate Similarity	NPD2421	Approved
0.7152	Intermediate Similarity	NPD2420	Approved
0.7143	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5718	Phase 2
0.7134	Intermediate Similarity	NPD5241	Discontinued
0.7127	Intermediate Similarity	NPD8053	Approved
0.7127	Intermediate Similarity	NPD8054	Approved
0.7125	Intermediate Similarity	NPD6896	Approved
0.7125	Intermediate Similarity	NPD6895	Approved
0.7115	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1424	Approved
0.7104	Intermediate Similarity	NPD7906	Approved
0.7091	Intermediate Similarity	NPD7124	Phase 2
0.7089	Intermediate Similarity	NPD4474	Approved
0.7089	Intermediate Similarity	NPD4475	Approved
0.7086	Intermediate Similarity	NPD4166	Phase 2
0.7083	Intermediate Similarity	NPD4210	Discontinued
0.7072	Intermediate Similarity	NPD2971	Approved
0.7072	Intermediate Similarity	NPD2968	Approved
0.7052	Intermediate Similarity	NPD4055	Discovery
0.7048	Intermediate Similarity	NPD3124	Discontinued
0.7044	Intermediate Similarity	NPD3110	Approved
0.7044	Intermediate Similarity	NPD3109	Approved
0.6978	Remote Similarity	NPD4578	Approved
0.6978	Remote Similarity	NPD4577	Approved
0.697	Remote Similarity	NPD5754	Discontinued
0.697	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4482	Phase 3
0.6957	Remote Similarity	NPD4663	Approved
0.6941	Remote Similarity	NPD4005	Discontinued
0.6932	Remote Similarity	NPD7802	Discontinued
0.6932	Remote Similarity	NPD6107	Approved
0.6918	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6911	Remote Similarity	NPD4107	Approved
0.6893	Remote Similarity	NPD4010	Discontinued
0.6886	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5772	Approved
0.6879	Remote Similarity	NPD4585	Approved
0.6879	Remote Similarity	NPD5773	Approved
0.6875	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6331	Phase 2
0.6864	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6523	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD2972	Approved
0.6839	Remote Similarity	NPD5977	Approved
0.6839	Remote Similarity	NPD5978	Approved
0.6839	Remote Similarity	NPD3533	Approved
0.6837	Remote Similarity	NPD4859	Phase 1
0.6831	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7291	Discontinued
0.6821	Remote Similarity	NPD7248	Discontinued
0.681	Remote Similarity	NPD6111	Discontinued
0.6807	Remote Similarity	NPD3060	Approved
0.6806	Remote Similarity	NPD4420	Approved
0.6805	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6090	Discontinued
0.6765	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6688	Approved
0.676	Remote Similarity	NPD6687	Approved
0.6755	Remote Similarity	NPD2488	Approved
0.6755	Remote Similarity	NPD2490	Approved
0.6754	Remote Similarity	NPD2975	Approved
0.6754	Remote Similarity	NPD2974	Approved
0.6754	Remote Similarity	NPD2973	Approved
0.6753	Remote Similarity	NPD3448	Approved
0.6753	Remote Similarity	NPD2491	Approved
0.6753	Remote Similarity	NPD3057	Approved
0.6747	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7598	Phase 2
0.6725	Remote Similarity	NPD1914	Approved
0.6725	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5709	Phase 3
0.6708	Remote Similarity	NPD1039	Discontinued
0.6706	Remote Similarity	NPD4123	Phase 3
0.6704	Remote Similarity	NPD6747	Phase 1
0.6703	Remote Similarity	NPD5313	Approved
0.6703	Remote Similarity	NPD5312	Approved
0.6688	Remote Similarity	NPD1669	Approved
0.6687	Remote Similarity	NPD1375	Discontinued
0.6686	Remote Similarity	NPD2978	Approved
0.6686	Remote Similarity	NPD3845	Phase 1
0.6686	Remote Similarity	NPD2977	Approved
0.6686	Remote Similarity	NPD6666	Approved
0.6686	Remote Similarity	NPD6667	Approved
0.6685	Remote Similarity	NPD4666	Phase 3
0.6684	Remote Similarity	NPD8095	Phase 1
0.6667	Remote Similarity	NPD5090	Approved
0.6667	Remote Similarity	NPD5005	Approved
0.6667	Remote Similarity	NPD5006	Approved
0.6667	Remote Similarity	NPD5089	Approved
0.6667	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7110	Phase 1
0.6667	Remote Similarity	NPD2674	Phase 3
0.665	Remote Similarity	NPD5676	Approved
0.6649	Remote Similarity	NPD4580	Approved
0.6647	Remote Similarity	NPD7037	Approved
0.6647	Remote Similarity	NPD5297	Approved
0.6646	Remote Similarity	NPD4579	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6297	Approved
0.6629	Remote Similarity	NPD5720	Discontinued
0.6626	Remote Similarity	NPD2238	Phase 2
0.6615	Remote Similarity	NPD2494	Approved
0.6615	Remote Similarity	NPD3452	Approved
0.6615	Remote Similarity	NPD3450	Approved
0.6615	Remote Similarity	NPD2493	Approved
0.6614	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7281	Phase 3
0.6613	Remote Similarity	NPD7280	Phase 3
0.6609	Remote Similarity	NPD6875	Approved
0.6609	Remote Similarity	NPD6876	Approved
0.6607	Remote Similarity	NPD5177	Phase 3
0.6607	Remote Similarity	NPD4162	Approved
0.6593	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD5677	Discontinued
0.658	Remote Similarity	NPD5564	Approved
0.6573	Remote Similarity	NPD5604	Discontinued
0.6571	Remote Similarity	NPD6385	Approved
0.6571	Remote Similarity	NPD6386	Approved
0.6568	Remote Similarity	NPD7466	Approved
0.6568	Remote Similarity	NPD6748	Discontinued
0.6562	Remote Similarity	NPD7905	Discontinued
0.6561	Remote Similarity	NPD3398	Discontinued
0.6561	Remote Similarity	NPD3705	Approved
0.6554	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.655	Remote Similarity	NPD1774	Approved
0.655	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD2653	Approved
0.6545	Remote Similarity	NPD2492	Phase 1
0.6543	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD8651	Approved
0.6538	Remote Similarity	NPD2667	Approved
0.6538	Remote Similarity	NPD2668	Approved
0.6532	Remote Similarity	NPD2122	Discontinued
0.6532	Remote Similarity	NPD4727	Phase 1
0.6529	Remote Similarity	NPD2677	Approved
0.6519	Remote Similarity	NPD2230	Approved
0.6519	Remote Similarity	NPD2233	Approved
0.6519	Remote Similarity	NPD2232	Approved
0.6515	Remote Similarity	NPD4583	Approved
0.6515	Remote Similarity	NPD4582	Approved
0.6514	Remote Similarity	NPD4675	Approved
0.6514	Remote Similarity	NPD4678	Approved
0.6513	Remote Similarity	NPD5283	Phase 1
0.6512	Remote Similarity	NPD7019	Approved
0.6512	Remote Similarity	NPD7020	Approved
0.6506	Remote Similarity	NPD2200	Suspended
0.6503	Remote Similarity	NPD3145	Approved
0.6503	Remote Similarity	NPD3144	Approved
0.65	Remote Similarity	NPD2041	Clinical (unspecified phase)

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