NPASS Compound

Structure

NPC296437 OpenBabel07101718282D 31 33 0 0 1 0 0 0 0 0999 V2000 2.4602 4.2859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1141 1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1805 0.8975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1889 2.9335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2379 3.2425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5039 3.8701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8059 0.5702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1731 3.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4742 3.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8277 0.3623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8203 2.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7985 2.7996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7614 2.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1149 1.5213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0704 1.5522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 -2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1512 3.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7832 2.7111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1586 1.1054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4676 2.0565 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 -0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4458 2.2644 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 -0.1691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -1.6691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -1.6691 0.0000 N 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 -1.4013 0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 20 1 0 0 0 0 3 21 2 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 30 1 0 0 0 0 7 9 1 0 0 0 0 7 10 1 0 0 0 0 8 11 1 0 0 0 0 8 15 1 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 0 0 0 0 14 16 1 0 0 0 0 14 20 2 0 0 0 0 15 26 1 0 0 0 0 16 31 1 0 0 0 0 17 28 2 0 0 0 0 17 29 1 0 0 0 0 18 30 2 0 0 0 0 18 31 1 0 0 0 0 21 22 1 0 0 0 0 22 13 1 6 0 0 0 22 26 1 0 0 0 0 23 24 2 0 0 0 0 23 25 1 0 0 0 0 23 31 1 0 0 0 0 24 27 1 0 0 0 0 24 28 1 0 0 0 0 25 29 2 0 0 0 0 25 30 1 0 0 0 0 M CHG 1 30 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.33
Volume:	470.43
LogP:	4.193
LogD:	4.953
LogS:	-2.727
# Rotatable Bonds:	8
TPSA:	61.34
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.428
Synthetic Accessibility Score:	4.425
Fsp3:	0.577
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:	-5.477
MDCK Permeability:	3.8102427879493916e-06
Pgp-inhibitor:	0.351
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.848
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.379
Plasma Protein Binding (PPB):	80.05135345458984%
Volume Distribution (VD):	1.04
Pgp-substrate:	20.627687454223633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.136
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.486
CYP2D6-inhibitor:	0.982
CYP2D6-substrate:	0.415
CYP3A4-inhibitor:	0.086
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	5.855
Half-life (T1/2):	0.841

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.924
Drug-inuced Liver Injury (DILI):	0.144
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.333
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.111
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.584

Download Data

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

Natural Product: NPC296437

Natural Product ID:	NPC296437
*Common Name:**	Agelasine E
IUPAC Name:	7-[(2E,6E)-9-[(1R)-2,2-dimethyl-6-methylidenecyclohexyl]-3,7-dimethylnona-2,6-dienyl]-9-methylpurin-9-ium-6-amine
Synonyms:
Standard InCHIKey:	PPCBHTAMQFLZHZ-VTUSAZOXSA-N
Standard InCHI:	InChI=1S/C26H40N5/c1-19(12-13-22-21(3)11-8-15-26(22,4)5)9-7-10-20(2)14-16-31-18-30(6)25-23(31)24(27)28-17-29-25/h9,14,17-18,22H,3,7-8,10-13,15-16H2,1-2,4-6H3,(H2,27,28,29)/q+1/b19-9+,20-14+/t22-/m0/s1
SMILES:	C/C(=CCC/C(=C/Cn1c[n+](C)c2c1c(N)ncn2)/C)/CC[C@H]1C(=C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586410
PubChem CID:	6478429
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	at a depth of 14 m near the island of Ambon (Seram Seilale), Indonesia	1997-AUG	PMID[10514317]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14677933]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[26083682]
NPO11199	Agelas nakamurai	Species	Agelasidae	Eukaryota	n.a.	papua new guinean	n.a.	PMID[9784179]
NPO11199	Agelas nakamurai	Species	Agelasidae	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	3
Others	2

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	2
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>	24000.0	nM	PMID[454621]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	IZ	=	14.0	mm	PMID[454621]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	IZ	=	10.0	mm	PMID[454621]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[454621]

☑ 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 NPC296437 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	846
0.1-0.2	18523
0.2-0.3	17938
0.3-0.4	3285
0.4-0.5	1682
0.5-0.6	352
0.6-0.7	45
0.7-0.8	9
0.8-0.85	0
0.85-0.9	7
0.9-0.95	2
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9769	High Similarity	NPC476528
0.9769	High Similarity	NPC476433
0.9767	High Similarity	NPC470266
0.9695	High Similarity	NPC474986
0.9695	High Similarity	NPC476013
0.9695	High Similarity	NPC476522
0.9621	High Similarity	NPC476521
0.9545	High Similarity	NPC476520
0.9478	High Similarity	NPC476408
0.8873	High Similarity	NPC472834
0.8849	High Similarity	NPC244700
0.8811	High Similarity	NPC472833
0.8759	High Similarity	NPC472832
0.8759	High Similarity	NPC18308
0.8298	Intermediate Similarity	NPC217656
0.7986	Intermediate Similarity	NPC89139
0.7937	Intermediate Similarity	NPC473585
0.7744	Intermediate Similarity	NPC265111
0.7323	Intermediate Similarity	NPC87981
0.7323	Intermediate Similarity	NPC174114
0.7114	Intermediate Similarity	NPC167285
0.7048	Intermediate Similarity	NPC317054
0.7	Intermediate Similarity	NPC226184
0.7	Intermediate Similarity	NPC76544
0.6986	Remote Similarity	NPC57279
0.6767	Remote Similarity	NPC18335
0.6767	Remote Similarity	NPC476564
0.6706	Remote Similarity	NPC164845
0.6622	Remote Similarity	NPC104011
0.6596	Remote Similarity	NPC68938
0.6536	Remote Similarity	NPC33996
0.6522	Remote Similarity	NPC312187
0.6522	Remote Similarity	NPC4837
0.6494	Remote Similarity	NPC129756
0.6463	Remote Similarity	NPC239737
0.6346	Remote Similarity	NPC317821
0.6296	Remote Similarity	NPC150853
0.6291	Remote Similarity	NPC246193
0.6278	Remote Similarity	NPC313514
0.6265	Remote Similarity	NPC93365
0.6264	Remote Similarity	NPC313897
0.625	Remote Similarity	NPC189314
0.6242	Remote Similarity	NPC209525
0.6242	Remote Similarity	NPC161659
0.6168	Remote Similarity	NPC476297
0.6168	Remote Similarity	NPC476219
0.6164	Remote Similarity	NPC229974
0.6164	Remote Similarity	NPC314152
0.6154	Remote Similarity	NPC300238
0.6149	Remote Similarity	NPC189068
0.6145	Remote Similarity	NPC469975
0.6111	Remote Similarity	NPC309832
0.6111	Remote Similarity	NPC219313
0.6102	Remote Similarity	NPC477119
0.6087	Remote Similarity	NPC107374
0.6087	Remote Similarity	NPC156461
0.6087	Remote Similarity	NPC21448
0.6082	Remote Similarity	NPC470203
0.6067	Remote Similarity	NPC248007
0.6053	Remote Similarity	NPC469308
0.6049	Remote Similarity	NPC164665
0.6037	Remote Similarity	NPC136349
0.6023	Remote Similarity	NPC470204
0.6012	Remote Similarity	NPC269827
0.5976	Remote Similarity	NPC121222
0.5964	Remote Similarity	NPC161224
0.5964	Remote Similarity	NPC114209
0.5955	Remote Similarity	NPC189261
0.5941	Remote Similarity	NPC195140
0.5929	Remote Similarity	NPC476099
0.5928	Remote Similarity	NPC328479
0.5902	Remote Similarity	NPC477118
0.5893	Remote Similarity	NPC212551
0.5893	Remote Similarity	NPC302778
0.5882	Remote Similarity	NPC120070
0.587	Remote Similarity	NPC477120
0.5868	Remote Similarity	NPC185991
0.5868	Remote Similarity	NPC85689
0.5868	Remote Similarity	NPC211025
0.5867	Remote Similarity	NPC139776
0.5864	Remote Similarity	NPC8590
0.5858	Remote Similarity	NPC174802
0.5833	Remote Similarity	NPC321814
0.5833	Remote Similarity	NPC472816
0.5829	Remote Similarity	NPC158055
0.5824	Remote Similarity	NPC224076
0.5813	Remote Similarity	NPC250178
0.5806	Remote Similarity	NPC14330
0.5799	Remote Similarity	NPC130586
0.5799	Remote Similarity	NPC164952
0.5789	Remote Similarity	NPC226245
0.5786	Remote Similarity	NPC476561
0.5769	Remote Similarity	NPC287876
0.5763	Remote Similarity	NPC290959
0.5747	Remote Similarity	NPC122141
0.574	Remote Similarity	NPC207633
0.5722	Remote Similarity	NPC276373
0.5714	Remote Similarity	NPC326248
0.5714	Remote Similarity	NPC187191
0.5714	Remote Similarity	NPC225018
0.5714	Remote Similarity	NPC115595
0.5698	Remote Similarity	NPC316618
0.5692	Remote Similarity	NPC5802
0.5687	Remote Similarity	NPC160666
0.568	Remote Similarity	NPC201380
0.568	Remote Similarity	NPC179787
0.568	Remote Similarity	NPC470111
0.5676	Remote Similarity	NPC24589
0.5674	Remote Similarity	NPC326082
0.5663	Remote Similarity	NPC197068
0.5663	Remote Similarity	NPC157821
0.5655	Remote Similarity	NPC204141
0.5652	Remote Similarity	NPC307191
0.565	Remote Similarity	NPC325906
0.5647	Remote Similarity	NPC282531
0.5647	Remote Similarity	NPC321911
0.5644	Remote Similarity	NPC216159
0.5625	Remote Similarity	NPC323091
0.5621	Remote Similarity	NPC63545
0.5614	Remote Similarity	NPC40070

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 NPC296437 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	356
0.1-0.2	1125
0.2-0.3	3255
0.3-0.4	2104
0.4-0.5	1526
0.5-0.6	676
0.6-0.7	107
0.7-0.8	1
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
0.7535	Intermediate Similarity	NPD1058	Discontinued
0.7205	Intermediate Similarity	NPD1313	Approved
0.689	Remote Similarity	NPD1333	Phase 3
0.6828	Remote Similarity	NPD870	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7158	Phase 1
0.681	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD5962	Phase 2
0.6768	Remote Similarity	NPD1015	Phase 2
0.6768	Remote Similarity	NPD1016	Phase 2
0.6767	Remote Similarity	NPD8836	Approved
0.6748	Remote Similarity	NPD516	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.669	Remote Similarity	NPD9408	Phase 3
0.6686	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD9633	Phase 3
0.6648	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1215	Discontinued
0.6645	Remote Similarity	NPD4240	Approved
0.6628	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD248	Discontinued
0.6607	Remote Similarity	NPD2333	Discontinued
0.6575	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD2456	Phase 2
0.6571	Remote Similarity	NPD2457	Phase 2
0.6559	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD799	Phase 1
0.6536	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD2927	Phase 3
0.6522	Remote Similarity	NPD6816	Phase 3
0.6457	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3695	Approved
0.6452	Remote Similarity	NPD3696	Approved
0.645	Remote Similarity	NPD2647	Phase 3
0.6442	Remote Similarity	NPD2524	Discontinued
0.6409	Remote Similarity	NPD3431	Approved
0.6409	Remote Similarity	NPD3430	Approved
0.6404	Remote Similarity	NPD2793	Discontinued
0.6404	Remote Similarity	NPD2591	Phase 2
0.6398	Remote Similarity	NPD4568	Phase 2
0.6395	Remote Similarity	NPD5324	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD171	Discontinued
0.6391	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD3041	Approved
0.6379	Remote Similarity	NPD7111	Discontinued
0.6364	Remote Similarity	NPD6129	Phase 2
0.6364	Remote Similarity	NPD1637	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2523	Phase 2
0.6364	Remote Similarity	NPD2526	Phase 2
0.6353	Remote Similarity	NPD6794	Approved
0.6343	Remote Similarity	NPD5730	Phase 2
0.6343	Remote Similarity	NPD40	Phase 2
0.6321	Remote Similarity	NPD4352	Phase 1
0.6319	Remote Similarity	NPD2839	Phase 2
0.6319	Remote Similarity	NPD7722	Suspended
0.6313	Remote Similarity	NPD4902	Discontinued
0.6307	Remote Similarity	NPD5508	Phase 1
0.6294	Remote Similarity	NPD8121	Phase 3
0.6294	Remote Similarity	NPD8120	Approved
0.6292	Remote Similarity	NPD5463	Clinical (unspecified phase)
0.628	Remote Similarity	NPD3107	Discontinued
0.6278	Remote Similarity	NPD7138	Phase 2
0.627	Remote Similarity	NPD5462	Discontinued
0.6265	Remote Similarity	NPD546	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD2646	Discontinued
0.6264	Remote Similarity	NPD3799	Suspended
0.6264	Remote Similarity	NPD7006	Approved
0.6264	Remote Similarity	NPD6761	Discontinued
0.6263	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD2876	Phase 3
0.6263	Remote Similarity	NPD7323	Phase 2
0.6259	Remote Similarity	NPD306	Approved
0.6257	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3409	Phase 1
0.625	Remote Similarity	NPD8833	Approved
0.625	Remote Similarity	NPD1892	Phase 2
0.625	Remote Similarity	NPD1893	Phase 2
0.625	Remote Similarity	NPD8831	Approved
0.6242	Remote Similarity	NPD193	Suspended
0.6242	Remote Similarity	NPD1257	Approved
0.623	Remote Similarity	NPD2453	Phase 2
0.623	Remote Similarity	NPD2451	Phase 2
0.623	Remote Similarity	NPD2452	Phase 2
0.623	Remote Similarity	NPD2450	Phase 2
0.623	Remote Similarity	NPD4615	Phase 2
0.6229	Remote Similarity	NPD5843	Discontinued
0.6229	Remote Similarity	NPD2406	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD174	Discontinued
0.6222	Remote Similarity	NPD6721	Phase 1
0.6222	Remote Similarity	NPD5683	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5642	Approved
0.6222	Remote Similarity	NPD5684	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5682	Phase 3
0.6216	Remote Similarity	NPD3362	Clinical (unspecified phase)
0.6209	Remote Similarity	NPD2818	Discontinued
0.6199	Remote Similarity	NPD509	Phase 3
0.6198	Remote Similarity	NPD4612	Discontinued
0.6198	Remote Similarity	NPD2824	Phase 2
0.6196	Remote Similarity	NPD3708	Phase 2
0.619	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6418	Phase 1
0.6173	Remote Similarity	NPD4183	Phase 3
0.6173	Remote Similarity	NPD4182	Phase 3
0.6171	Remote Similarity	NPD7297	Phase 2
0.6168	Remote Similarity	NPD5969	Clinical (unspecified phase)
0.6164	Remote Similarity	NPD185	Approved
0.6158	Remote Similarity	NPD2364	Suspended
0.615	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.615	Remote Similarity	NPD6469	Phase 3
0.6149	Remote Similarity	NPD6828	Phase 2
0.6149	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD3612	Phase 2
0.6141	Remote Similarity	NPD6577	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD6619	Phase 3
0.6138	Remote Similarity	NPD4142	Discontinued
0.6135	Remote Similarity	NPD1690	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6192	Phase 3
0.6133	Remote Similarity	NPD2963	Phase 1
0.6129	Remote Similarity	NPD4763	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD5012	Phase 2
0.6124	Remote Similarity	NPD1873	Clinical (unspecified phase)
0.6124	Remote Similarity	NPD4716	Approved
0.6118	Remote Similarity	NPD1807	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD1288	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD6521	Phase 3
0.6114	Remote Similarity	NPD6520	Phase 3
0.6114	Remote Similarity	NPD5996	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD1303	Phase 1
0.6105	Remote Similarity	NPD7988	Suspended
0.6105	Remote Similarity	NPD3889	Approved
0.6102	Remote Similarity	NPD2731	Phase 2
0.6102	Remote Similarity	NPD1272	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD2880	Discontinued
0.6089	Remote Similarity	NPD1674	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD1675	Phase 1
0.6089	Remote Similarity	NPD4744	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD249	Approved
0.6087	Remote Similarity	NPD166	Approved
0.6087	Remote Similarity	NPD250	Approved
0.6084	Remote Similarity	NPD1027	Approved
0.6084	Remote Similarity	NPD1030	Approved
0.6084	Remote Similarity	NPD1029	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD3860	Discontinued
0.6071	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD2902	Phase 2
0.6071	Remote Similarity	NPD3405	Phase 3
0.6069	Remote Similarity	NPD4213	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD9084	Phase 2
0.6067	Remote Similarity	NPD3432	Approved
0.6066	Remote Similarity	NPD7504	Discontinued
0.6062	Remote Similarity	NPD7445	Phase 1
0.6058	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.6056	Remote Similarity	NPD4441	Phase 2
0.6053	Remote Similarity	NPD6151	Phase 2
0.6053	Remote Similarity	NPD4318	Clinical (unspecified phase)
0.6048	Remote Similarity	NPD2128	Phase 1
0.6044	Remote Similarity	NPD5757	Discontinued
0.6037	Remote Similarity	NPD548	Clinical (unspecified phase)
0.6036	Remote Similarity	NPD2150	Discontinued
0.6034	Remote Similarity	NPD702	Clinical (unspecified phase)
0.6033	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD9484	Clinical (unspecified phase)
0.6025	Remote Similarity	NPD3706	Clinical (unspecified phase)
0.6021	Remote Similarity	NPD2807	Discontinued
0.602	Remote Similarity	NPD4863	Approved
0.6012	Remote Similarity	NPD186	Discovery
0.6012	Remote Similarity	NPD195	Approved
0.6011	Remote Similarity	NPD4155	Approved
0.6011	Remote Similarity	NPD3002	Clinical (unspecified phase)
0.601	Remote Similarity	NPD6849	Phase 2
0.601	Remote Similarity	NPD6271	Approved
0.601	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.601	Remote Similarity	NPD6850	Phase 2
0.6	Remote Similarity	NPD1895	Discontinued
0.6	Remote Similarity	NPD757	Phase 3
0.6	Remote Similarity	NPD1658	Discontinued
0.6	Remote Similarity	NPD6470	Phase 3
0.6	Remote Similarity	NPD1869	Phase 2
0.599	Remote Similarity	NPD4854	Phase 3
0.5989	Remote Similarity	NPD2868	Clinical (unspecified phase)
0.5989	Remote Similarity	NPD5666	Phase 2
0.5988	Remote Similarity	NPD2149	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5079	Phase 2
0.5979	Remote Similarity	NPD5885	Approved
0.5978	Remote Similarity	NPD2729	Approved
0.5978	Remote Similarity	NPD2730	Approved
0.5978	Remote Similarity	NPD2728	Approved
0.5977	Remote Similarity	NPD3361	Phase 1
0.5976	Remote Similarity	NPD2624	Phase 2
0.5962	Remote Similarity	NPD9083	Clinical (unspecified phase)
0.5959	Remote Similarity	NPD4446	Approved
0.5956	Remote Similarity	NPD3913	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD5943	Clinical (unspecified phase)
0.595	Remote Similarity	NPD5080	Phase 2
0.5949	Remote Similarity	NPD2443	Approved
0.5949	Remote Similarity	NPD2442	Approved
0.5948	Remote Similarity	NPD1354	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