NPASS Compound

Structure

NPC470127 OpenBabel07101719512D 22 25 0 0 0 0 0 0 0 0999 V2000 -5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9890 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 3 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 13 1 0 0 0 0 3 4 1 0 0 0 0 3 5 2 0 0 0 0 4 6 2 0 0 0 0 5 15 1 0 0 0 0 6 17 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 13 2 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 19 1 0 0 0 0 17 20 2 0 0 0 0 18 19 2 0 0 0 0 18 21 1 0 0 0 0 19 20 1 0 0 0 0 M CHG 1 20 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.14
Volume:	312.646
LogP:	4.369
LogD:	3.565
LogS:	-5.296
# Rotatable Bonds:	3
TPSA:	37.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	2.609
Fsp3:	0.211
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:	-4.681
MDCK Permeability:	2.4540291633456945e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.931
30% Bioavailability (F30%):	0.121

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.963
Plasma Protein Binding (PPB):	94.78759765625%
Volume Distribution (VD):	1.582
Pgp-substrate:	2.178572177886963%

ADMET: Metabolism

CYP1A2-inhibitor:	0.988
CYP1A2-substrate:	0.516
CYP2C19-inhibitor:	0.715
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.702
CYP2C9-substrate:	0.312
CYP2D6-inhibitor:	0.802
CYP2D6-substrate:	0.23
CYP3A4-inhibitor:	0.799
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	9.109
Half-life (T1/2):	0.263

ADMET: Toxicity

hERG Blockers:	0.12
Human Hepatotoxicity (H-HT):	0.651
Drug-inuced Liver Injury (DILI):	0.407
AMES Toxicity:	0.394
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.148
Carcinogencity:	0.847
Eye Corrosion:	0.003
Eye Irritation:	0.091
Respiratory Toxicity:	0.067

Download Data

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

Natural Product: NPC470127

Natural Product ID:	NPC470127
*Common Name:**	Nicalaterine A
IUPAC Name:	2-(3-ethyl-12H-indolo[2,3-a]quinolizin-5-ium-2-yl)ethanol
Synonyms:	Nicalaterine A
Standard InCHIKey:	XHUIUBANZNHJEL-UHFFFAOYSA-O
Standard InCHI:	InChI=1S/C19H18N2O/c1-2-13-12-21-9-7-16-15-5-3-4-6-17(15)20-19(16)18(21)11-14(13)8-10-22/h3-7,9,11-12,22H,2,8,10H2,1H3/p+1
SMILES:	CCC1=C[N+]2=C(C=C1CCO)C3=C(C=C2)C4=CC=CC=C4N3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1778843
PubChem CID:	54580815
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19388660]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21524573]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28362501]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15819	Hunteria zeylanica	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	2
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[549114]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	110.0	nM	PMID[549114]
NPT2	Others	Unspecified		Ratio IC50	>	450.0	n.a.	PMID[549114]

☑ 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 NPC470127 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	403
0.1-0.2	3970
0.2-0.3	16270
0.3-0.4	14786
0.4-0.5	3167
0.5-0.6	1846
0.6-0.7	1508
0.7-0.8	675
0.8-0.85	64
0.85-0.9	5
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8317	Intermediate Similarity	NPC476160
0.8151	Intermediate Similarity	NPC477163
0.6977	Remote Similarity	NPC476249
0.6618	Remote Similarity	NPC184437
0.6609	Remote Similarity	NPC311242
0.6579	Remote Similarity	NPC303045
0.6579	Remote Similarity	NPC161972
0.6518	Remote Similarity	NPC172128
0.648	Remote Similarity	NPC187036
0.6466	Remote Similarity	NPC33168
0.646	Remote Similarity	NPC226438
0.6435	Remote Similarity	NPC58674
0.6434	Remote Similarity	NPC473804
0.6429	Remote Similarity	NPC470877
0.6417	Remote Similarity	NPC275467
0.6406	Remote Similarity	NPC313449
0.6404	Remote Similarity	NPC265521
0.6389	Remote Similarity	NPC119569
0.6383	Remote Similarity	NPC243162
0.6372	Remote Similarity	NPC316108
0.6372	Remote Similarity	NPC159178
0.6372	Remote Similarity	NPC209764
0.6372	Remote Similarity	NPC471307
0.6372	Remote Similarity	NPC78041
0.6372	Remote Similarity	NPC74936
0.6372	Remote Similarity	NPC141139
0.6372	Remote Similarity	NPC121872
0.6364	Remote Similarity	NPC211551
0.635	Remote Similarity	NPC476685
0.635	Remote Similarity	NPC476687
0.635	Remote Similarity	NPC476689
0.6349	Remote Similarity	NPC296163
0.6341	Remote Similarity	NPC77294
0.6339	Remote Similarity	NPC262393
0.6333	Remote Similarity	NPC178681
0.6324	Remote Similarity	NPC226662
0.6311	Remote Similarity	NPC471447
0.6299	Remote Similarity	NPC205652
0.6299	Remote Similarity	NPC470550
0.6281	Remote Similarity	NPC113326
0.6281	Remote Similarity	NPC194390
0.6281	Remote Similarity	NPC224610
0.6281	Remote Similarity	NPC88267
0.6279	Remote Similarity	NPC192209
0.625	Remote Similarity	NPC198747
0.6239	Remote Similarity	NPC25565
0.6207	Remote Similarity	NPC472103
0.6207	Remote Similarity	NPC471309
0.6207	Remote Similarity	NPC476483
0.6204	Remote Similarity	NPC192623
0.6202	Remote Similarity	NPC147957
0.619	Remote Similarity	NPC275410
0.6186	Remote Similarity	NPC475439
0.6186	Remote Similarity	NPC473501
0.6182	Remote Similarity	NPC15839
0.6174	Remote Similarity	NPC245259
0.6167	Remote Similarity	NPC469457
0.6148	Remote Similarity	NPC474479
0.6119	Remote Similarity	NPC283130
0.6119	Remote Similarity	NPC328683
0.6115	Remote Similarity	NPC325479
0.6106	Remote Similarity	NPC471638
0.6091	Remote Similarity	NPC14326
0.6058	Remote Similarity	NPC478079
0.6053	Remote Similarity	NPC12429
0.6048	Remote Similarity	NPC473498
0.6047	Remote Similarity	NPC33742
0.6014	Remote Similarity	NPC101372
0.6014	Remote Similarity	NPC472100
0.6014	Remote Similarity	NPC77992
0.6	Remote Similarity	NPC307456
0.6	Remote Similarity	NPC188010
0.6	Remote Similarity	NPC37584
0.5971	Remote Similarity	NPC9856
0.5969	Remote Similarity	NPC1986
0.5969	Remote Similarity	NPC474544
0.5965	Remote Similarity	NPC473031
0.5962	Remote Similarity	NPC476231
0.5959	Remote Similarity	NPC477155
0.5948	Remote Similarity	NPC258627
0.5948	Remote Similarity	NPC78154
0.5929	Remote Similarity	NPC3210
0.5926	Remote Similarity	NPC109151
0.592	Remote Similarity	NPC474973
0.592	Remote Similarity	NPC474804
0.592	Remote Similarity	NPC327481
0.592	Remote Similarity	NPC130898
0.5917	Remote Similarity	NPC472258
0.5913	Remote Similarity	NPC325441
0.5912	Remote Similarity	NPC474926
0.5912	Remote Similarity	NPC325013
0.5909	Remote Similarity	NPC477156
0.5909	Remote Similarity	NPC477157
0.5906	Remote Similarity	NPC292758
0.5906	Remote Similarity	NPC65855
0.5902	Remote Similarity	NPC228400
0.5902	Remote Similarity	NPC214200
0.5896	Remote Similarity	NPC476990
0.5893	Remote Similarity	NPC146703
0.5887	Remote Similarity	NPC150254
0.5887	Remote Similarity	NPC304761
0.5887	Remote Similarity	NPC226778
0.5887	Remote Similarity	NPC147000
0.5878	Remote Similarity	NPC136002
0.5878	Remote Similarity	NPC288232
0.5877	Remote Similarity	NPC203076
0.5865	Remote Similarity	NPC314992
0.5865	Remote Similarity	NPC264580
0.5859	Remote Similarity	NPC319579
0.5854	Remote Similarity	NPC327226
0.5852	Remote Similarity	NPC202521
0.5852	Remote Similarity	NPC273830
0.5852	Remote Similarity	NPC71684
0.584	Remote Similarity	NPC143516
0.5833	Remote Similarity	NPC258992
0.5833	Remote Similarity	NPC2265
0.5833	Remote Similarity	NPC3371
0.5833	Remote Similarity	NPC82963
0.5827	Remote Similarity	NPC476950
0.5813	Remote Similarity	NPC317430
0.5809	Remote Similarity	NPC252878
0.5806	Remote Similarity	NPC469785
0.5806	Remote Similarity	NPC471317
0.5806	Remote Similarity	NPC471310
0.5806	Remote Similarity	NPC202613
0.5804	Remote Similarity	NPC132847
0.5802	Remote Similarity	NPC118202
0.5797	Remote Similarity	NPC4974
0.5789	Remote Similarity	NPC38458
0.5789	Remote Similarity	NPC311737
0.5786	Remote Similarity	NPC197680
0.5786	Remote Similarity	NPC259098
0.5769	Remote Similarity	NPC474584
0.5769	Remote Similarity	NPC469762
0.5767	Remote Similarity	NPC275305
0.5767	Remote Similarity	NPC37423
0.5766	Remote Similarity	NPC175726
0.5766	Remote Similarity	NPC35996
0.5766	Remote Similarity	NPC46427
0.5766	Remote Similarity	NPC6975
0.5766	Remote Similarity	NPC474082
0.5759	Remote Similarity	NPC472121
0.5758	Remote Similarity	NPC37302
0.5758	Remote Similarity	NPC303370
0.5758	Remote Similarity	NPC101139
0.5746	Remote Similarity	NPC5932
0.5746	Remote Similarity	NPC220698
0.5742	Remote Similarity	NPC470507
0.5738	Remote Similarity	NPC164514
0.5738	Remote Similarity	NPC303611
0.5738	Remote Similarity	NPC226096
0.5738	Remote Similarity	NPC108606
0.5738	Remote Similarity	NPC290515
0.5735	Remote Similarity	NPC86966
0.5735	Remote Similarity	NPC324702
0.5733	Remote Similarity	NPC116519
0.5726	Remote Similarity	NPC318154
0.5725	Remote Similarity	NPC276949
0.5725	Remote Similarity	NPC35850
0.5725	Remote Similarity	NPC314141
0.5723	Remote Similarity	NPC311276
0.5714	Remote Similarity	NPC285926
0.5714	Remote Similarity	NPC14672
0.5714	Remote Similarity	NPC117032
0.5714	Remote Similarity	NPC470544
0.5714	Remote Similarity	NPC315276
0.5706	Remote Similarity	NPC34508
0.5706	Remote Similarity	NPC472123
0.5705	Remote Similarity	NPC285469
0.5705	Remote Similarity	NPC84317
0.5705	Remote Similarity	NPC473922
0.5704	Remote Similarity	NPC256369
0.5703	Remote Similarity	NPC114741
0.5703	Remote Similarity	NPC182549
0.5703	Remote Similarity	NPC164802
0.5702	Remote Similarity	NPC471320
0.5702	Remote Similarity	NPC471319
0.5697	Remote Similarity	NPC68354
0.5687	Remote Similarity	NPC470508
0.5685	Remote Similarity	NPC287358
0.5683	Remote Similarity	NPC472414
0.568	Remote Similarity	NPC164859
0.568	Remote Similarity	NPC474430
0.5678	Remote Similarity	NPC92689
0.5677	Remote Similarity	NPC469763
0.5677	Remote Similarity	NPC73952
0.5677	Remote Similarity	NPC259644
0.5677	Remote Similarity	NPC469765
0.5677	Remote Similarity	NPC469760
0.5677	Remote Similarity	NPC25008
0.5677	Remote Similarity	NPC469786
0.5676	Remote Similarity	NPC471574
0.5672	Remote Similarity	NPC470545
0.5672	Remote Similarity	NPC323948
0.5671	Remote Similarity	NPC329688
0.5671	Remote Similarity	NPC189812
0.5669	Remote Similarity	NPC231705
0.5662	Remote Similarity	NPC41801
0.5662	Remote Similarity	NPC112823
0.5662	Remote Similarity	NPC477061

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 NPC470127 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	646
0.2-0.3	923
0.3-0.4	1581
0.4-0.5	2611
0.5-0.6	1890
0.6-0.7	1082
0.7-0.8	187
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6693	Remote Similarity	NPD2212	Approved
0.6693	Remote Similarity	NPD2210	Approved
0.6549	Remote Similarity	NPD1814	Approved
0.6549	Remote Similarity	NPD1812	Approved
0.6519	Remote Similarity	NPD1001	Discontinued
0.648	Remote Similarity	NPD3148	Approved
0.648	Remote Similarity	NPD2659	Approved
0.648	Remote Similarity	NPD3150	Approved
0.648	Remote Similarity	NPD3149	Approved
0.648	Remote Similarity	NPD2658	Approved
0.648	Remote Similarity	NPD3147	Approved
0.6479	Remote Similarity	NPD6301	Phase 2
0.6475	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4814	Discontinued
0.6423	Remote Similarity	NPD1108	Approved
0.6423	Remote Similarity	NPD1107	Approved
0.6406	Remote Similarity	NPD7481	Approved
0.6406	Remote Similarity	NPD7480	Approved
0.6404	Remote Similarity	NPD6690	Approved
0.64	Remote Similarity	NPD1762	Approved
0.64	Remote Similarity	NPD1764	Approved
0.6395	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD2243	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4119	Approved
0.6378	Remote Similarity	NPD2622	Approved
0.6378	Remote Similarity	NPD2589	Approved
0.6378	Remote Similarity	NPD2588	Approved
0.6371	Remote Similarity	NPD2583	Phase 2
0.6364	Remote Similarity	NPD5717	Approved
0.6341	Remote Similarity	NPD2679	Approved
0.6341	Remote Similarity	NPD2678	Approved
0.6319	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD2131	Approved
0.6276	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD752	Approved
0.625	Remote Similarity	NPD995	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9538	Approved
0.625	Remote Similarity	NPD2841	Approved
0.623	Remote Similarity	NPD564	Approved
0.623	Remote Similarity	NPD563	Approved
0.6225	Remote Similarity	NPD2789	Approved
0.6224	Remote Similarity	NPD3520	Clinical (unspecified phase)
0.622	Remote Similarity	NPD1656	Phase 2
0.6207	Remote Similarity	NPD1394	Approved
0.6207	Remote Similarity	NPD1080	Approved
0.6202	Remote Similarity	NPD3123	Discovery
0.6198	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD1316	Discontinued
0.6174	Remote Similarity	NPD530	Approved
0.6172	Remote Similarity	NPD5631	Phase 3
0.6167	Remote Similarity	NPD1275	Phase 2
0.6154	Remote Similarity	NPD665	Phase 2
0.6154	Remote Similarity	NPD7522	Discontinued
0.6136	Remote Similarity	NPD7342	Discontinued
0.6134	Remote Similarity	NPD4117	Approved
0.6129	Remote Similarity	NPD6406	Approved
0.6119	Remote Similarity	NPD478	Approved
0.6116	Remote Similarity	NPD1737	Approved
0.6116	Remote Similarity	NPD1735	Approved
0.6116	Remote Similarity	NPD4719	Phase 2
0.6116	Remote Similarity	NPD1736	Approved
0.6116	Remote Similarity	NPD5716	Approved
0.6116	Remote Similarity	NPD1419	Approved
0.6116	Remote Similarity	NPD1417	Approved
0.6104	Remote Similarity	NPD5599	Discontinued
0.6102	Remote Similarity	NPD2507	Clinical (unspecified phase)
0.6099	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.609	Remote Similarity	NPD3421	Phase 3
0.609	Remote Similarity	NPD1236	Phase 3
0.6087	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD4431	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD720	Approved
0.6068	Remote Similarity	NPD719	Approved
0.6063	Remote Similarity	NPD4991	Discontinued
0.605	Remote Similarity	NPD1875	Phase 1
0.6048	Remote Similarity	NPD4778	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD2188	Approved
0.6017	Remote Similarity	NPD1081	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6014	Remote Similarity	NPD4993	Discontinued
0.6	Remote Similarity	NPD4031	Approved
0.6	Remote Similarity	NPD7508	Discontinued
0.6	Remote Similarity	NPD4032	Approved
0.6	Remote Similarity	NPD5546	Clinical (unspecified phase)
0.6	Remote Similarity	NPD458	Approved
0.5985	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD707	Approved
0.5968	Remote Similarity	NPD999	Phase 2
0.5942	Remote Similarity	NPD2146	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD7904	Phase 2
0.5935	Remote Similarity	NPD1542	Approved
0.5932	Remote Similarity	NPD1066	Discontinued
0.5929	Remote Similarity	NPD4857	Phase 1
0.5926	Remote Similarity	NPD7462	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD2173	Clinical (unspecified phase)
0.5915	Remote Similarity	NPD1106	Discontinued
0.5912	Remote Similarity	NPD1036	Approved
0.5906	Remote Similarity	NPD9713	Approved
0.5906	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD4165	Phase 2
0.5891	Remote Similarity	NPD3066	Phase 2
0.5887	Remote Similarity	NPD10	Approved
0.5887	Remote Similarity	NPD314	Approved
0.5887	Remote Similarity	NPD309	Approved
0.5887	Remote Similarity	NPD315	Approved
0.5887	Remote Similarity	NPD311	Approved
0.5887	Remote Similarity	NPD310	Approved
0.5878	Remote Similarity	NPD224	Phase 2
0.5873	Remote Similarity	NPD6300	Approved
0.5873	Remote Similarity	NPD1401	Approved
0.5873	Remote Similarity	NPD6299	Approved
0.5865	Remote Similarity	NPD2217	Approved
0.5865	Remote Similarity	NPD2218	Phase 2
0.5862	Remote Similarity	NPD2003	Phase 1
0.5859	Remote Similarity	NPD2384	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD1540	Approved
0.5854	Remote Similarity	NPD854	Approved
0.5854	Remote Similarity	NPD855	Approved
0.584	Remote Similarity	NPD1040	Phase 2
0.5833	Remote Similarity	NPD3907	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2463	Approved
0.5833	Remote Similarity	NPD2467	Approved
0.5833	Remote Similarity	NPD2464	Approved
0.5828	Remote Similarity	NPD5423	Phase 2
0.5828	Remote Similarity	NPD4703	Approved
0.5828	Remote Similarity	NPD4702	Approved
0.5822	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD1922	Discontinued
0.5816	Remote Similarity	NPD4274	Approved
0.5816	Remote Similarity	NPD4275	Approved
0.5816	Remote Similarity	NPD3720	Discontinued
0.5814	Remote Similarity	NPD3651	Discontinued
0.5806	Remote Similarity	NPD1396	Approved
0.5806	Remote Similarity	NPD5103	Approved
0.5798	Remote Similarity	NPD3719	Approved
0.5798	Remote Similarity	NPD3718	Approved
0.5797	Remote Similarity	NPD1324	Clinical (unspecified phase)
0.5796	Remote Similarity	NPD5989	Phase 1
0.5794	Remote Similarity	NPD993	Approved
0.5794	Remote Similarity	NPD467	Phase 1
0.5794	Remote Similarity	NPD990	Approved
0.5793	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD6789	Approved
0.5776	Remote Similarity	NPD1101	Approved
0.5758	Remote Similarity	NPD4076	Approved
0.5758	Remote Similarity	NPD4079	Approved
0.5755	Remote Similarity	NPD2840	Approved
0.575	Remote Similarity	NPD3772	Phase 3
0.5748	Remote Similarity	NPD3420	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD6093	Discontinued
0.5745	Remote Similarity	NPD4019	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD9612	Approved
0.5738	Remote Similarity	NPD9609	Approved
0.5738	Remote Similarity	NPD9611	Approved
0.5735	Remote Similarity	NPD4651	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD23	Approved
0.5724	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.5724	Remote Similarity	NPD5556	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4639	Approved
0.5714	Remote Similarity	NPD7836	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD159	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4640	Approved
0.5714	Remote Similarity	NPD4638	Approved
0.5714	Remote Similarity	NPD5267	Discontinued
0.5714	Remote Similarity	NPD414	Discontinued
0.5714	Remote Similarity	NPD3248	Phase 1
0.5714	Remote Similarity	NPD6259	Discontinued
0.5714	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.5706	Remote Similarity	NPD4951	Discontinued
0.5705	Remote Similarity	NPD1592	Phase 3
0.5704	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.5703	Remote Similarity	NPD477	Phase 1
0.5702	Remote Similarity	NPD2895	Discontinued
0.5697	Remote Similarity	NPD3506	Approved
0.5697	Remote Similarity	NPD3505	Approved
0.5695	Remote Similarity	NPD4351	Clinical (unspecified phase)
0.5694	Remote Similarity	NPD7200	Approved
0.5691	Remote Similarity	NPD9712	Approved
0.569	Remote Similarity	NPD187	Approved
0.5683	Remote Similarity	NPD4985	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD2543	Discontinued
0.5676	Remote Similarity	NPD1953	Discontinued
0.5669	Remote Similarity	NPD2551	Approved
0.5669	Remote Similarity	NPD2559	Approved
0.5664	Remote Similarity	NPD864	Approved
0.5664	Remote Similarity	NPD865	Approved
0.5659	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.5658	Remote Similarity	NPD4402	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD528	Clinical (unspecified phase)
0.5655	Remote Similarity	NPD6086	Phase 2
0.5649	Remote Similarity	NPD181	Approved
0.5641	Remote Similarity	NPD7969	Clinical (unspecified phase)
0.5639	Remote Similarity	NPD1348	Approved
0.5638	Remote Similarity	NPD3513	Phase 3

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