NPASS Compound

Structure

NPC18308 OpenBabel07101718312D 32 35 0 0 1 0 0 0 0 0999 V2000 1.5884 1.1675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3522 3.4440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2182 -1.0560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6167 2.9354 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2182 -0.0560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3584 -0.9336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8131 2.3923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2182 1.9440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1401 2.8406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5202 1.6852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2182 0.9440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1741 2.5817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4861 -1.0560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6201 0.4440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6956 0.1682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5446 0.8387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8472 2.1335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3522 2.4440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3522 -0.5560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6201 -0.5560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4861 0.9440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0183 1.2574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9093 1.7114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 0.2588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4861 1.9440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3522 0.4440 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9616 2.7101 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7479 1.1668 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8046 -0.2858 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 -0.0847 1.6158 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7541 -1.0560 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 6 30 1 0 0 0 0 7 10 1 0 0 0 0 7 17 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 17 2 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 31 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 20 1 0 0 0 0 14 21 1 0 0 0 0 15 28 2 0 0 0 0 15 29 1 0 0 0 0 16 30 2 0 0 0 0 16 31 1 0 0 0 0 18 25 1 6 0 0 0 19 26 1 0 0 0 0 20 32 2 0 0 0 0 21 25 1 6 0 0 0 21 26 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 22 31 1 0 0 0 0 23 27 1 0 0 0 0 23 28 1 0 0 0 0 24 29 2 0 0 0 0 24 30 1 0 0 0 0 25 4 1 6 0 0 0 26 5 1 6 0 0 0 M CHG 1 30 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.31
Volume:	470.663
LogP:	2.189
LogD:	3.203
LogS:	-3.337
# Rotatable Bonds:	5
TPSA:	78.41
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.539
Synthetic Accessibility Score:	5.074
Fsp3:	0.615
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.46
MDCK Permeability:	2.873083758458961e-06
Pgp-inhibitor:	0.093
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.819
20% Bioavailability (F20%):	0.963
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.477
Plasma Protein Binding (PPB):	68.22454071044922%
Volume Distribution (VD):	1.156
Pgp-substrate:	44.564453125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.097
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.122
CYP2D6-inhibitor:	0.934
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.069
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	7.022
Half-life (T1/2):	0.929

ADMET: Toxicity

hERG Blockers:	0.425
Human Hepatotoxicity (H-HT):	0.856
Drug-inuced Liver Injury (DILI):	0.187
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.841
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.561
Carcinogencity:	0.089
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.875

Download Data

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

Natural Product: NPC18308

Natural Product ID:	NPC18308
*Common Name:**	2-Oxoagelasine B
IUPAC Name:	(4aR,7R,8S,8aR)-8-[(E)-5-(6-amino-9-methylpurin-9-ium-7-yl)-3-methylpent-3-enyl]-4,4a,7,8-tetramethyl-5,6,7,8a-tetrahydro-1H-naphthalen-2-one
Synonyms:
Standard InCHIKey:	RZRLKYGESQIOSC-BYPOXNEWSA-N
Standard InCHI:	InChI=1S/C26H38N5O/c1-17(9-12-31-16-30(6)24-22(31)23(27)28-15-29-24)7-10-25(4)18(2)8-11-26(5)19(3)13-20(32)14-21(25)26/h9,13,15-16,18,21H,7-8,10-12,14H2,1-6H3,(H2,27,28,29)/q+1/b17-9+/t18-,21-,25+,26+/m1/s1
SMILES:	C/C(=CCn1c[n+](c2c1c(N)ncn2)C)/CC[C@@]1(C)[C@H](C)CC[C@@]2([C@@H]1CC(=O)C=C2C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586409
PubChem CID:	46703740
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	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	>	23000.0	nM	PMID[559286]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[559286]

☑ 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 NPC18308 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	419
0.1-0.2	4390
0.2-0.3	25001
0.3-0.4	9655
0.4-0.5	2725
0.5-0.6	452
0.6-0.7	28
0.7-0.8	10
0.8-0.85	5
0.85-0.9	9
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472832
0.9793	High Similarity	NPC472833
0.9034	High Similarity	NPC476013
0.9034	High Similarity	NPC476522
0.9034	High Similarity	NPC474986
0.8973	High Similarity	NPC476521
0.8904	High Similarity	NPC476520
0.8836	High Similarity	NPC476528
0.8836	High Similarity	NPC476433
0.8828	High Similarity	NPC470266
0.8759	High Similarity	NPC296437
0.8725	High Similarity	NPC476408
0.8571	High Similarity	NPC472834
0.8182	Intermediate Similarity	NPC244700
0.7836	Intermediate Similarity	NPC473585
0.7692	Intermediate Similarity	NPC217656
0.7657	Intermediate Similarity	NPC265111
0.7532	Intermediate Similarity	NPC89139
0.7389	Intermediate Similarity	NPC226184
0.7389	Intermediate Similarity	NPC167285
0.7389	Intermediate Similarity	NPC76544
0.7356	Intermediate Similarity	NPC164845
0.6613	Remote Similarity	NPC477118
0.6578	Remote Similarity	NPC477120
0.6522	Remote Similarity	NPC57279
0.6448	Remote Similarity	NPC317054
0.6414	Remote Similarity	NPC87981
0.6414	Remote Similarity	NPC174114
0.6378	Remote Similarity	NPC477119
0.6313	Remote Similarity	NPC276373
0.6281	Remote Similarity	NPC5802
0.625	Remote Similarity	NPC157821
0.6228	Remote Similarity	NPC33996
0.6196	Remote Similarity	NPC246193
0.619	Remote Similarity	NPC129756
0.618	Remote Similarity	NPC239737
0.6174	Remote Similarity	NPC476564
0.6141	Remote Similarity	NPC290959
0.6127	Remote Similarity	NPC116555
0.6126	Remote Similarity	NPC24589
0.6124	Remote Similarity	NPC267811
0.6098	Remote Similarity	NPC104011
0.6059	Remote Similarity	NPC317821
0.6031	Remote Similarity	NPC313514
0.6031	Remote Similarity	NPC78941
0.6031	Remote Similarity	NPC282458
0.6023	Remote Similarity	NPC150853
0.6011	Remote Similarity	NPC313897
0.6	Remote Similarity	NPC93365
0.5974	Remote Similarity	NPC4837
0.5974	Remote Similarity	NPC312187
0.5965	Remote Similarity	NPC209525
0.5965	Remote Similarity	NPC161659
0.596	Remote Similarity	NPC18335
0.5928	Remote Similarity	NPC476341
0.5896	Remote Similarity	NPC229974
0.5896	Remote Similarity	NPC314152
0.5886	Remote Similarity	NPC189068
0.5867	Remote Similarity	NPC133782
0.5867	Remote Similarity	NPC144474
0.5867	Remote Similarity	NPC527
0.5852	Remote Similarity	NPC219313
0.5852	Remote Similarity	NPC309832
0.5849	Remote Similarity	NPC68938
0.5829	Remote Similarity	NPC21448
0.5829	Remote Similarity	NPC107374
0.5829	Remote Similarity	NPC156461
0.5801	Remote Similarity	NPC469975
0.5795	Remote Similarity	NPC164665
0.5792	Remote Similarity	NPC470323
0.5787	Remote Similarity	NPC136349
0.5785	Remote Similarity	NPC158055
0.5775	Remote Similarity	NPC325906
0.5766	Remote Similarity	NPC267078
0.5766	Remote Similarity	NPC935
0.5765	Remote Similarity	NPC101676
0.5763	Remote Similarity	NPC269827
0.574	Remote Similarity	NPC474357
0.5735	Remote Similarity	NPC477419
0.5735	Remote Similarity	NPC477417
0.573	Remote Similarity	NPC121222
0.5729	Remote Similarity	NPC189261
0.5722	Remote Similarity	NPC324484
0.5722	Remote Similarity	NPC161224
0.5707	Remote Similarity	NPC195140
0.5697	Remote Similarity	NPC248007
0.5691	Remote Similarity	NPC328479
0.568	Remote Similarity	NPC469308
0.5676	Remote Similarity	NPC115595
0.5665	Remote Similarity	NPC233431
0.5665	Remote Similarity	NPC300139
0.5659	Remote Similarity	NPC473878
0.5659	Remote Similarity	NPC302778
0.5659	Remote Similarity	NPC212551
0.5652	Remote Similarity	NPC476219
0.5652	Remote Similarity	NPC120070
0.5638	Remote Similarity	NPC478184
0.5638	Remote Similarity	NPC478182
0.5635	Remote Similarity	NPC467063
0.5635	Remote Similarity	NPC211025
0.5635	Remote Similarity	NPC185991
0.5635	Remote Similarity	NPC85689
0.5628	Remote Similarity	NPC477418
0.5628	Remote Similarity	NPC174802
0.5628	Remote Similarity	NPC477420
0.5622	Remote Similarity	NPC250178
0.5612	Remote Similarity	NPC191415
0.5604	Remote Similarity	NPC321814
0.5604	Remote Similarity	NPC472816

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 NPC18308 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	228
0.1-0.2	706
0.2-0.3	2702
0.3-0.4	2817
0.4-0.5	1830
0.5-0.6	789
0.6-0.7	78
0.7-0.8	0
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
0.7353	Intermediate Similarity	NPD8120	Approved
0.7353	Intermediate Similarity	NPD8121	Phase 3
0.6915	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5969	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD3431	Approved
0.6755	Remote Similarity	NPD3430	Approved
0.6687	Remote Similarity	NPD1058	Discontinued
0.6684	Remote Similarity	NPD7323	Phase 2
0.6667	Remote Similarity	NPD5682	Phase 3
0.6667	Remote Similarity	NPD5684	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5683	Clinical (unspecified phase)
0.665	Remote Similarity	NPD3905	Phase 3
0.6615	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6470	Phase 3
0.6531	Remote Similarity	NPD2881	Approved
0.6531	Remote Similarity	NPD2879	Approved
0.6527	Remote Similarity	NPD4240	Approved
0.6517	Remote Similarity	NPD4863	Approved
0.6488	Remote Similarity	NPD7158	Phase 1
0.648	Remote Similarity	NPD1313	Approved
0.6473	Remote Similarity	NPD4854	Phase 3
0.645	Remote Similarity	NPD6521	Phase 3
0.645	Remote Similarity	NPD6520	Phase 3
0.6441	Remote Similarity	NPD516	Clinical (unspecified phase)
0.644	Remote Similarity	NPD1658	Discontinued
0.6404	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD6229	Phase 2
0.6378	Remote Similarity	NPD3041	Approved
0.6375	Remote Similarity	NPD870	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD2443	Approved
0.6368	Remote Similarity	NPD2442	Approved
0.6359	Remote Similarity	NPD2880	Discontinued
0.6346	Remote Similarity	NPD5827	Discontinued
0.6337	Remote Similarity	NPD2408	Discontinued
0.6335	Remote Similarity	NPD5016	Approved
0.6335	Remote Similarity	NPD9633	Phase 3
0.6331	Remote Similarity	NPD3706	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD1982	Phase 1
0.6318	Remote Similarity	NPD3840	Phase 2
0.6318	Remote Similarity	NPD3839	Phase 2
0.6316	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD3708	Phase 2
0.63	Remote Similarity	NPD7103	Approved
0.63	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD248	Discontinued
0.6292	Remote Similarity	NPD5321	Phase 3
0.6279	Remote Similarity	NPD4183	Phase 3
0.6279	Remote Similarity	NPD4182	Phase 3
0.6256	Remote Similarity	NPD6849	Phase 2
0.6256	Remote Similarity	NPD6850	Phase 2
0.625	Remote Similarity	NPD9408	Phase 3
0.625	Remote Similarity	NPD3696	Approved
0.625	Remote Similarity	NPD3695	Approved
0.6243	Remote Similarity	NPD4709	Approved
0.6238	Remote Similarity	NPD1506	Discontinued
0.6237	Remote Similarity	NPD6619	Phase 3
0.6224	Remote Similarity	NPD3362	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD5508	Phase 1
0.6222	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6219	Remote Similarity	NPD4446	Approved
0.6209	Remote Similarity	NPD1333	Phase 3
0.6209	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6202	Remote Similarity	NPD5643	Phase 2
0.6198	Remote Similarity	NPD6418	Phase 1
0.6188	Remote Similarity	NPD2008	Discontinued
0.6183	Remote Similarity	NPD7297	Phase 2
0.6176	Remote Similarity	NPD3860	Discontinued
0.6175	Remote Similarity	NPD1215	Discontinued
0.6175	Remote Similarity	NPD2647	Phase 3
0.6173	Remote Similarity	NPD5464	Approved
0.617	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6165	Remote Similarity	NPD2411	Approved
0.6162	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4940	Approved
0.6146	Remote Similarity	NPD2591	Phase 2
0.6138	Remote Similarity	NPD5962	Phase 2
0.6129	Remote Similarity	NPD7173	Approved
0.6129	Remote Similarity	NPD7172	Approved
0.6126	Remote Similarity	NPD2456	Phase 2
0.6126	Remote Similarity	NPD2457	Phase 2
0.6111	Remote Similarity	NPD1085	Approved
0.6111	Remote Similarity	NPD5446	Phase 2
0.6111	Remote Similarity	NPD1775	Approved
0.6108	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD6271	Approved
0.6103	Remote Similarity	NPD7434	Approved
0.6099	Remote Similarity	NPD1015	Phase 2
0.6099	Remote Similarity	NPD1016	Phase 2
0.6087	Remote Similarity	NPD7657	Approved
0.6087	Remote Similarity	NPD7656	Approved
0.6085	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6085	Remote Similarity	NPD3432	Approved
0.608	Remote Similarity	NPD6469	Phase 3
0.608	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD2452	Phase 2
0.6078	Remote Similarity	NPD2451	Phase 2
0.6078	Remote Similarity	NPD2450	Phase 2
0.6078	Remote Similarity	NPD2453	Phase 2
0.6071	Remote Similarity	NPD7722	Suspended
0.6062	Remote Similarity	NPD4902	Discontinued
0.6059	Remote Similarity	NPD4765	Approved
0.6059	Remote Similarity	NPD4764	Approved
0.6058	Remote Similarity	NPD2363	Discontinued
0.604	Remote Similarity	NPD6129	Phase 2
0.604	Remote Similarity	NPD2807	Discontinued
0.6038	Remote Similarity	NPD6210	Phase 3
0.6038	Remote Similarity	NPD6579	Phase 2
0.6032	Remote Similarity	NPD4155	Approved
0.6031	Remote Similarity	NPD7138	Phase 2
0.603	Remote Similarity	NPD1952	Discontinued
0.6029	Remote Similarity	NPD2876	Phase 3
0.6029	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6021	Remote Similarity	NPD2523	Phase 2
0.6021	Remote Similarity	NPD2526	Phase 2
0.602	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.602	Remote Similarity	NPD6816	Phase 3
0.6019	Remote Similarity	NPD7694	Discontinued
0.6012	Remote Similarity	NPD171	Discontinued
0.6011	Remote Similarity	NPD3107	Discontinued
0.601	Remote Similarity	NPD7164	Discontinued
0.6	Remote Similarity	NPD546	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2221	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2646	Discontinued
0.6	Remote Similarity	NPD6794	Approved
0.599	Remote Similarity	NPD4615	Phase 2
0.599	Remote Similarity	NPD5072	Discontinued
0.5988	Remote Similarity	NPD2179	Discontinued
0.598	Remote Similarity	NPD7207	Approved
0.598	Remote Similarity	NPD7208	Approved
0.598	Remote Similarity	NPD7209	Approved
0.5979	Remote Similarity	NPD6721	Phase 1
0.5978	Remote Similarity	NPD2524	Discontinued
0.5975	Remote Similarity	NPD580	Discontinued
0.5971	Remote Similarity	NPD2824	Phase 2
0.5971	Remote Similarity	NPD4612	Discontinued
0.597	Remote Similarity	NPD5854	Approved
0.5968	Remote Similarity	NPD2333	Discontinued
0.5967	Remote Similarity	NPD2927	Phase 3
0.5965	Remote Similarity	NPD193	Suspended
0.596	Remote Similarity	NPD8836	Approved
0.5952	Remote Similarity	NPD4395	Phase 1
0.5952	Remote Similarity	NPD4763	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD7111	Discontinued
0.5943	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD1600	Suspended
0.5942	Remote Similarity	NPD2295	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.5933	Remote Similarity	NPD4352	Phase 1
0.5926	Remote Similarity	NPD7006	Approved
0.5926	Remote Similarity	NPD3799	Suspended
0.5924	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD7445	Phase 1
0.5918	Remote Similarity	NPD7504	Discontinued
0.5917	Remote Similarity	NPD7887	Approved
0.5917	Remote Similarity	NPD7888	Approved
0.5916	Remote Similarity	NPD5730	Phase 2
0.5916	Remote Similarity	NPD40	Phase 2
0.5913	Remote Similarity	NPD6192	Phase 3
0.5909	Remote Similarity	NPD5973	Phase 2
0.5909	Remote Similarity	NPD5974	Approved
0.5905	Remote Similarity	NPD5679	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD5000	Phase 2
0.5902	Remote Similarity	NPD5012	Phase 2
0.5902	Remote Similarity	NPD4299	Phase 1
0.5899	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.5896	Remote Similarity	NPD185	Approved
0.5895	Remote Similarity	NPD7851	Phase 1
0.5895	Remote Similarity	NPD5843	Discontinued
0.5895	Remote Similarity	NPD7850	Discontinued
0.5886	Remote Similarity	NPD1730	Discontinued
0.5885	Remote Similarity	NPD4716	Approved
0.5882	Remote Similarity	NPD2602	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7415	Suspended
0.5879	Remote Similarity	NPD460	Discontinued
0.5874	Remote Similarity	NPD4023	Clinical (unspecified phase)
0.5874	Remote Similarity	NPD7568	Phase 1
0.5873	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.587	Remote Similarity	NPD3083	Approved
0.5867	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.586	Remote Similarity	NPD2136	Approved
0.586	Remote Similarity	NPD7988	Suspended
0.586	Remote Similarity	NPD2135	Approved
0.586	Remote Similarity	NPD2134	Approved
0.5859	Remote Similarity	NPD6761	Discontinued
0.5857	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.5857	Remote Similarity	NPD2902	Phase 2
0.5856	Remote Similarity	NPD8159	Discontinued
0.5856	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD4744	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD34	Approved
0.5854	Remote Similarity	NPD4714	Approved
0.5854	Remote Similarity	NPD2364	Suspended
0.5854	Remote Similarity	NPD4715	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4713	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD4896	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