NPASS Compound

Structure

NPC472833 OpenBabel07101719512D 32 34 0 0 1 0 0 0 0 0999 V2000 4.1379 2.7019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7918 1.8053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7803 1.3041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0483 -1.6959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1210 -0.8047 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7771 -0.6293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2060 3.2195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4648 2.2536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2401 3.4783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6896 1.0288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 3.0300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6555 0.7700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1401 2.3229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6464 -0.1959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7803 -1.6959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4185 -1.2022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0523 0.9986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4307 1.9948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5330 2.7712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7803 0.3041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9143 -1.1959 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6464 -1.1959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5106 0.5799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5092 0.5275 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 4.9143 -0.1959 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0538 1.3662 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9632 -0.3635 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.4199 -1.1498 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 -0.8812 1.3570 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.5124 -1.6959 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 6 30 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 18 2 0 0 0 0 9 19 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 19 2 0 0 0 0 12 26 1 0 0 0 0 13 31 1 0 0 0 0 14 20 2 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 15 22 1 0 0 0 0 16 28 2 0 0 0 0 16 29 1 0 0 0 0 17 30 2 0 0 0 0 17 31 1 0 0 0 0 20 26 1 0 0 0 0 21 26 1 6 0 0 0 22 32 2 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 26 5 1 6 0 0 0 M CHG 1 30 1 M END $$$$

Physi-Chem Properties

Molecular Weight:	436.31
Volume:	476.583
LogP:	3.206
LogD:	3.606
LogS:	-2.961
# Rotatable Bonds:	8
TPSA:	78.41
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.465
Synthetic Accessibility Score:	4.785
Fsp3:	0.538
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:	-5.453
MDCK Permeability:	4.131379228056176e-06
Pgp-inhibitor:	0.785
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.947
20% Bioavailability (F20%):	0.922
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.63
Plasma Protein Binding (PPB):	79.85760498046875%
Volume Distribution (VD):	1.258
Pgp-substrate:	31.06209373474121%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.093
CYP2C19-inhibitor:	0.158
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.252
CYP2D6-inhibitor:	0.98
CYP2D6-substrate:	0.255
CYP3A4-inhibitor:	0.047
CYP3A4-substrate:	0.145

ADMET: Excretion

Clearance (CL):	6.977
Half-life (T1/2):	0.927

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.918
Drug-inuced Liver Injury (DILI):	0.175
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.16
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.903
Carcinogencity:	0.181
Eye Corrosion:	0.003
Eye Irritation:	0.027
Respiratory Toxicity:	0.897

Download Data

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

Natural Product: NPC472833

Natural Product ID:	NPC472833
*Common Name:**	VNHUAACDBKEOPD-DQBDHREDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VNHUAACDBKEOPD-DQBDHREDSA-N
Standard InCHI:	InChI=1S/C26H38N5O/c1-18(10-12-26(5)20(3)14-22(32)15-21(26)4)8-7-9-19(2)11-13-31-17-30(6)25-23(31)24(27)28-16-29-25/h8,11,14,16-17,21H,7,9-10,12-13,15H2,1-6H3,(H2,27,28,29)/q+1/b18-8+,19-11+/t21-,26-/m0/s1
SMILES:	C/C(=CCC/C(=C/Cn1c[n+](c2c1c(N)ncn2)C)/C)/CC[C@]1(C)[C@@H](C)CC(=O)C=C1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3586407
PubChem CID:	n.a.
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

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[508197]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[508197]

☑ 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 NPC472833 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	385
0.1-0.2	5523
0.2-0.3	27219
0.3-0.4	6643
0.4-0.5	2366
0.5-0.6	491
0.6-0.7	44
0.7-0.8	11
0.8-0.85	8
0.85-0.9	4
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9793	High Similarity	NPC472832
0.9793	High Similarity	NPC18308
0.9014	High Similarity	NPC470266
0.8828	High Similarity	NPC476522
0.8828	High Similarity	NPC474986
0.8828	High Similarity	NPC476013
0.8828	High Similarity	NPC476520
0.8811	High Similarity	NPC296437
0.8767	High Similarity	NPC476521
0.8759	High Similarity	NPC476433
0.8759	High Similarity	NPC476528
0.8742	High Similarity	NPC472834
0.8649	High Similarity	NPC476408
0.7987	Intermediate Similarity	NPC244700
0.7661	Intermediate Similarity	NPC473585
0.7532	Intermediate Similarity	NPC226184
0.7532	Intermediate Similarity	NPC76544
0.7532	Intermediate Similarity	NPC167285
0.75	Intermediate Similarity	NPC217656
0.7486	Intermediate Similarity	NPC265111
0.7342	Intermediate Similarity	NPC89139
0.7283	Intermediate Similarity	NPC164845
0.6646	Remote Similarity	NPC57279
0.6549	Remote Similarity	NPC87981
0.6549	Remote Similarity	NPC174114
0.6541	Remote Similarity	NPC477118
0.6505	Remote Similarity	NPC477120
0.6464	Remote Similarity	NPC317054
0.6341	Remote Similarity	NPC33996
0.6327	Remote Similarity	NPC276373
0.6312	Remote Similarity	NPC246193
0.6304	Remote Similarity	NPC477119
0.6303	Remote Similarity	NPC129756
0.6301	Remote Similarity	NPC476564
0.6294	Remote Similarity	NPC5802
0.6286	Remote Similarity	NPC239737
0.6263	Remote Similarity	NPC157821
0.6243	Remote Similarity	NPC290959
0.6211	Remote Similarity	NPC104011
0.6168	Remote Similarity	NPC317821
0.6139	Remote Similarity	NPC116555
0.6138	Remote Similarity	NPC24589
0.6135	Remote Similarity	NPC267811
0.6127	Remote Similarity	NPC150853
0.6126	Remote Similarity	NPC313514
0.6108	Remote Similarity	NPC313897
0.6102	Remote Similarity	NPC93365
0.6093	Remote Similarity	NPC4837
0.6093	Remote Similarity	NPC312187
0.6081	Remote Similarity	NPC18335
0.6071	Remote Similarity	NPC209525
0.6071	Remote Similarity	NPC161659
0.6042	Remote Similarity	NPC282458
0.6042	Remote Similarity	NPC78941
0.6	Remote Similarity	NPC314152
0.6	Remote Similarity	NPC229974
0.5988	Remote Similarity	NPC189068
0.5962	Remote Similarity	NPC68938
0.5954	Remote Similarity	NPC309832
0.5954	Remote Similarity	NPC219313
0.5938	Remote Similarity	NPC476341
0.593	Remote Similarity	NPC107374
0.593	Remote Similarity	NPC21448
0.593	Remote Similarity	NPC156461
0.5896	Remote Similarity	NPC164665
0.5886	Remote Similarity	NPC136349
0.5876	Remote Similarity	NPC133782
0.5876	Remote Similarity	NPC527
0.5876	Remote Similarity	NPC144474
0.587	Remote Similarity	NPC325906
0.5862	Remote Similarity	NPC269827
0.5829	Remote Similarity	NPC121222
0.582	Remote Similarity	NPC189261
0.5819	Remote Similarity	NPC161224
0.5815	Remote Similarity	NPC324484
0.581	Remote Similarity	NPC469975
0.5802	Remote Similarity	NPC248007
0.5801	Remote Similarity	NPC195140
0.5799	Remote Similarity	NPC470323
0.5787	Remote Similarity	NPC328479
0.5773	Remote Similarity	NPC267078
0.5773	Remote Similarity	NPC101676
0.5773	Remote Similarity	NPC935
0.5754	Remote Similarity	NPC212551
0.5754	Remote Similarity	NPC302778
0.5754	Remote Similarity	NPC473878
0.5747	Remote Similarity	NPC474357
0.5742	Remote Similarity	NPC477419
0.5742	Remote Similarity	NPC477417
0.573	Remote Similarity	NPC85689
0.573	Remote Similarity	NPC185991
0.573	Remote Similarity	NPC211025
0.5722	Remote Similarity	NPC174802
0.5721	Remote Similarity	NPC158055
0.5705	Remote Similarity	NPC256849
0.5698	Remote Similarity	NPC472816
0.5698	Remote Similarity	NPC321814
0.5691	Remote Similarity	NPC224076
0.5683	Remote Similarity	NPC124276
0.5682	Remote Similarity	NPC115595
0.5672	Remote Similarity	NPC300139
0.5672	Remote Similarity	NPC233431
0.5667	Remote Similarity	NPC130586
0.5667	Remote Similarity	NPC164952
0.566	Remote Similarity	NPC189314
0.5659	Remote Similarity	NPC226245
0.5658	Remote Similarity	NPC476099
0.5644	Remote Similarity	NPC109322
0.5635	Remote Similarity	NPC217021
0.5635	Remote Similarity	NPC470679
0.5633	Remote Similarity	NPC477420
0.5633	Remote Similarity	NPC477418
0.5632	Remote Similarity	NPC8590
0.5628	Remote Similarity	NPC250178
0.5619	Remote Similarity	NPC191415
0.5617	Remote Similarity	NPC139776
0.5611	Remote Similarity	NPC207633
0.561	Remote Similarity	NPC180493
0.561	Remote Similarity	NPC469308

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 NPC472833 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	738
0.2-0.3	2855
0.3-0.4	2704
0.4-0.5	1798
0.5-0.6	744
0.6-0.7	94
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
0.7176	Intermediate Similarity	NPD8120	Approved
0.7176	Intermediate Similarity	NPD8121	Phase 3
0.6845	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1058	Discontinued
0.6765	Remote Similarity	NPD5969	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD3431	Approved
0.6684	Remote Similarity	NPD3430	Approved
0.6646	Remote Similarity	NPD4240	Approved
0.6615	Remote Similarity	NPD7323	Phase 2
0.6606	Remote Similarity	NPD7158	Phase 1
0.6595	Remote Similarity	NPD5684	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD5683	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD5682	Phase 3
0.6582	Remote Similarity	NPD3905	Phase 3
0.6552	Remote Similarity	NPD516	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD4924	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD2879	Approved
0.6546	Remote Similarity	NPD2881	Approved
0.6497	Remote Similarity	NPD870	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD1313	Approved
0.6456	Remote Similarity	NPD9633	Phase 3
0.6455	Remote Similarity	NPD1658	Discontinued
0.645	Remote Similarity	NPD4863	Approved
0.6422	Remote Similarity	NPD6470	Phase 3
0.642	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD248	Discontinued
0.6412	Remote Similarity	NPD3708	Phase 2
0.641	Remote Similarity	NPD6837	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4854	Phase 3
0.6393	Remote Similarity	NPD3041	Approved
0.6382	Remote Similarity	NPD6521	Phase 3
0.6382	Remote Similarity	NPD6520	Phase 3
0.6382	Remote Similarity	NPD2443	Approved
0.6382	Remote Similarity	NPD2442	Approved
0.6373	Remote Similarity	NPD2880	Discontinued
0.6369	Remote Similarity	NPD9408	Phase 3
0.6364	Remote Similarity	NPD3696	Approved
0.6364	Remote Similarity	NPD3695	Approved
0.6353	Remote Similarity	NPD4709	Approved
0.635	Remote Similarity	NPD2408	Discontinued
0.6347	Remote Similarity	NPD3706	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD6229	Phase 2
0.6313	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD1333	Phase 3
0.6294	Remote Similarity	NPD4183	Phase 3
0.6294	Remote Similarity	NPD4182	Phase 3
0.6293	Remote Similarity	NPD5643	Phase 2
0.6263	Remote Similarity	NPD5016	Approved
0.6256	Remote Similarity	NPD1982	Phase 1
0.625	Remote Similarity	NPD3839	Phase 2
0.625	Remote Similarity	NPD3840	Phase 2
0.6243	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD3362	Clinical (unspecified phase)
0.6236	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD4446	Approved
0.6226	Remote Similarity	NPD1775	Approved
0.6226	Remote Similarity	NPD1085	Approved
0.6223	Remote Similarity	NPD2456	Phase 2
0.6223	Remote Similarity	NPD2457	Phase 2
0.6218	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6418	Phase 1
0.6202	Remote Similarity	NPD5827	Discontinued
0.6201	Remote Similarity	NPD1015	Phase 2
0.6201	Remote Similarity	NPD1016	Phase 2
0.62	Remote Similarity	NPD2008	Discontinued
0.6188	Remote Similarity	NPD1215	Discontinued
0.6188	Remote Similarity	NPD2647	Phase 3
0.6176	Remote Similarity	NPD2411	Approved
0.6175	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.6175	Remote Similarity	NPD3347	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD1506	Discontinued
0.6158	Remote Similarity	NPD2591	Phase 2
0.615	Remote Similarity	NPD5962	Phase 2
0.615	Remote Similarity	NPD5508	Phase 1
0.615	Remote Similarity	NPD7103	Approved
0.6133	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD7138	Phase 2
0.6124	Remote Similarity	NPD5321	Phase 3
0.6118	Remote Similarity	NPD171	Discontinued
0.6115	Remote Similarity	NPD2221	Clinical (unspecified phase)
0.6114	Remote Similarity	NPD3107	Discontinued
0.6114	Remote Similarity	NPD6849	Phase 2
0.6114	Remote Similarity	NPD6850	Phase 2
0.6108	Remote Similarity	NPD3860	Discontinued
0.6108	Remote Similarity	NPD7297	Phase 2
0.6102	Remote Similarity	NPD546	Clinical (unspecified phase)
0.6096	Remote Similarity	NPD3432	Approved
0.6096	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD2179	Discontinued
0.609	Remote Similarity	NPD580	Discontinued
0.6082	Remote Similarity	NPD6619	Phase 3
0.6081	Remote Similarity	NPD8836	Approved
0.6073	Remote Similarity	NPD4940	Approved
0.6071	Remote Similarity	NPD193	Suspended
0.6071	Remote Similarity	NPD4765	Approved
0.6071	Remote Similarity	NPD4764	Approved
0.6068	Remote Similarity	NPD2363	Discontinued
0.605	Remote Similarity	NPD2807	Discontinued
0.6048	Remote Similarity	NPD6579	Phase 2
0.6043	Remote Similarity	NPD4155	Approved
0.6041	Remote Similarity	NPD1952	Discontinued
0.604	Remote Similarity	NPD2876	Phase 3
0.604	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6271	Approved
0.6033	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD2523	Phase 2
0.6032	Remote Similarity	NPD2526	Phase 2
0.6031	Remote Similarity	NPD7434	Approved
0.602	Remote Similarity	NPD5464	Approved
0.6019	Remote Similarity	NPD7656	Approved
0.6019	Remote Similarity	NPD7657	Approved
0.6011	Remote Similarity	NPD2646	Discontinued
0.6011	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.601	Remote Similarity	NPD2453	Phase 2
0.601	Remote Similarity	NPD2450	Phase 2
0.601	Remote Similarity	NPD2451	Phase 2
0.601	Remote Similarity	NPD2452	Phase 2
0.6	Remote Similarity	NPD185	Approved
0.6	Remote Similarity	NPD5072	Discontinued
0.6	Remote Similarity	NPD7722	Suspended
0.5991	Remote Similarity	NPD7173	Approved
0.5991	Remote Similarity	NPD7172	Approved
0.599	Remote Similarity	NPD4902	Discontinued
0.5989	Remote Similarity	NPD2524	Discontinued
0.5988	Remote Similarity	NPD1730	Discontinued
0.598	Remote Similarity	NPD4612	Discontinued
0.598	Remote Similarity	NPD2824	Phase 2
0.5979	Remote Similarity	NPD4716	Approved
0.5978	Remote Similarity	NPD2333	Discontinued
0.5972	Remote Similarity	NPD6210	Phase 3
0.5969	Remote Similarity	NPD460	Discontinued
0.5968	Remote Similarity	NPD1037	Clinical (unspecified phase)
0.5967	Remote Similarity	NPD3083	Approved
0.5962	Remote Similarity	NPD4395	Phase 1
0.596	Remote Similarity	NPD5446	Phase 2
0.5956	Remote Similarity	NPD2135	Approved
0.5956	Remote Similarity	NPD7988	Suspended
0.5956	Remote Similarity	NPD2136	Approved
0.5956	Remote Similarity	NPD2134	Approved
0.5952	Remote Similarity	NPD4541	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD799	Phase 1
0.5951	Remote Similarity	NPD2295	Clinical (unspecified phase)
0.5951	Remote Similarity	NPD1600	Suspended
0.595	Remote Similarity	NPD6816	Phase 3
0.5949	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD4744	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD7164	Discontinued
0.5941	Remote Similarity	NPD2364	Suspended
0.5936	Remote Similarity	NPD5666	Phase 2
0.5933	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.593	Remote Similarity	NPD249	Approved
0.593	Remote Similarity	NPD6469	Phase 3
0.593	Remote Similarity	NPD166	Approved
0.593	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.593	Remote Similarity	NPD250	Approved
0.5924	Remote Similarity	NPD578	Discontinued
0.5924	Remote Similarity	NPD6794	Approved
0.5918	Remote Similarity	NPD5973	Phase 2
0.5918	Remote Similarity	NPD4615	Phase 2
0.5918	Remote Similarity	NPD5974	Approved
0.5913	Remote Similarity	NPD5679	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD6721	Phase 1
0.59	Remote Similarity	NPD5854	Approved
0.5893	Remote Similarity	NPD2602	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD6129	Phase 2
0.5889	Remote Similarity	NPD2927	Phase 3
0.5886	Remote Similarity	NPD548	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5324	Clinical (unspecified phase)
0.588	Remote Similarity	NPD7694	Discontinued
0.5876	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.5875	Remote Similarity	NPD4262	Discontinued
0.5874	Remote Similarity	NPD2819	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7111	Discontinued
0.587	Remote Similarity	NPD1777	Approved
0.587	Remote Similarity	NPD1776	Approved
0.5868	Remote Similarity	NPD4763	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD4352	Phase 1
0.5865	Remote Similarity	NPD2902	Phase 2
0.5865	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.5864	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD4714	Approved
0.5862	Remote Similarity	NPD4713	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD195	Approved
0.5862	Remote Similarity	NPD186	Discovery
0.5862	Remote Similarity	NPD34	Approved
0.5862	Remote Similarity	NPD7531	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD4715	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD7445	Phase 1
0.5854	Remote Similarity	NPD6328	Clinical (unspecified phase)
0.5853	Remote Similarity	NPD1571	Phase 2
0.5853	Remote Similarity	NPD7887	Approved
0.5853	Remote Similarity	NPD7888	Approved
0.5851	Remote Similarity	NPD7006	Approved
0.5848	Remote Similarity	NPD2253	Discontinued
0.5846	Remote Similarity	NPD7504	Discontinued
0.5845	Remote Similarity	NPD6192	Phase 3
0.5842	Remote Similarity	NPD5730	Phase 2
0.5842	Remote Similarity	NPD40	Phase 2
0.5842	Remote Similarity	NPD4142	Discontinued

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