NPASS Compound

Structure

NPC116057 OpenBabel07101719132D 33 36 0 0 1 0 0 0 0 0999 V2000 4.7343 -3.2955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8073 -3.8533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4406 -1.9562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3662 -1.4420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4961 -1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3742 -0.4420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1805 -3.5272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2464 -0.7780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1603 -3.3272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3268 -1.7748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6342 -1.4280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5123 0.0650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2200 -3.2490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7119 0.0672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8467 0.6074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9432 0.1787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1644 -3.3048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7803 0.0789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9349 -2.6948 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1442 -3.1048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4608 -2.1562 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6422 -0.4280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4988 -2.5563 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8459 0.5672 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9102 -0.4141 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3425 -0.6207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7977 -1.4077 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6751 -0.7377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1821 -1.6078 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1241 1.5277 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5775 -0.2287 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6687 -0.6252 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 7 9 1 0 0 0 0 7 13 2 0 0 0 0 8 10 1 0 0 0 0 8 14 1 0 0 0 0 9 19 1 0 0 0 0 10 19 1 0 0 0 0 11 22 2 0 0 0 0 12 22 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 15 16 2 0 0 0 0 15 24 1 0 0 0 0 16 26 1 0 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 19 1 1 1 0 0 0 20 21 1 0 0 0 0 21 3 1 1 0 0 0 21 27 1 0 0 0 0 23 29 1 1 0 0 0 24 31 1 6 0 0 0 25 18 1 6 0 0 0 25 27 1 0 0 0 0 25 30 1 0 0 0 0 26 32 2 0 0 0 0 27 29 1 1 0 0 0 28 29 1 0 0 0 0 28 30 2 0 0 0 0 28 33 1 0 0 0 0 29 26 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	447.28
Volume:	492.19
LogP:	4.905
LogD:	4.358
LogS:	-4.564
# Rotatable Bonds:	2
TPSA:	63.24
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.499
Synthetic Accessibility Score:	5.387
Fsp3:	0.552
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:	-4.718
MDCK Permeability:	3.158062099828385e-05
Pgp-inhibitor:	0.977
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.119
20% Bioavailability (F20%):	0.04
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978
Plasma Protein Binding (PPB):	98.74825286865234%
Volume Distribution (VD):	0.792
Pgp-substrate:	1.5528651475906372%

ADMET: Metabolism

CYP1A2-inhibitor:	0.151
CYP1A2-substrate:	0.369
CYP2C19-inhibitor:	0.953
CYP2C19-substrate:	0.635
CYP2C9-inhibitor:	0.908
CYP2C9-substrate:	0.485
CYP2D6-inhibitor:	0.237
CYP2D6-substrate:	0.397
CYP3A4-inhibitor:	0.955
CYP3A4-substrate:	0.403

ADMET: Excretion

Clearance (CL):	9.954
Half-life (T1/2):	0.478

ADMET: Toxicity

hERG Blockers:	0.104
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.148
AMES Toxicity:	0.475
Rat Oral Acute Toxicity:	0.912
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.51
Carcinogencity:	0.585
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC116057

Natural Product ID:	NPC116057
*Common Name:**	Deoxaphomin C
IUPAC Name:	n.a.
Synonyms:	Deoxaphomin C
Standard InCHIKey:	QSSICOOAJDSOCS-YKNYXAGUSA-N
Standard InCHI:	InChI=1S/C29H37NO3/c1-19-9-7-13-23-17-20(2)21(3)27-25(18-22-11-5-4-6-12-22)30-28(33)29(23,27)26(32)16-15-24(31)14-8-10-19/h4-7,11-13,15-17,19,21,23-25,27,31H,8-10,14,18H2,1-3H3,(H,30,33)/b13-7+,16-15+/t19-,21+,23-,24+,25-,27-,29+/m0/s1
SMILES:	C[C@@H]1CCC[C@@H](O)/C=C/C(=O)[C@@]23[C@@H](/C=C/C1)C=C(C)[C@H]([C@H]3[C@@H](N=C2O)Cc1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2018717
PubChem CID:	60150679
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001819] Isoindoles and derivatives [CHEMONTID:0002496] Isoindolines [CHEMONTID:0001820] Isoindolones

*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
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562839]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16643061]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	giant jellyfish Nemopilema nomurai	n.a.	n.a.	PMID[22483395]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26651221]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30785282]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31120749]
NPO32661	Phoma sp.	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7561907]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	8580.0	nM	PMID[453548]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	=	5480.0	nM	PMID[453548]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	6660.0	nM	PMID[453548]
NPT148	Cell Line	HCT-15	Homo sapiens	IC50	=	8430.0	nM	PMID[453548]

☑ 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 NPC116057 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	111
0.1-0.2	707
0.2-0.3	2224
0.3-0.4	6891
0.4-0.5	21902
0.5-0.6	9657
0.6-0.7	1111
0.7-0.8	80
0.8-0.85	9
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9449	High Similarity	NPC208725
0.92	High Similarity	NPC472413
0.88	High Similarity	NPC472415
0.876	High Similarity	NPC183722
0.8661	High Similarity	NPC472414
0.8462	Intermediate Similarity	NPC71271
0.8306	Intermediate Similarity	NPC188010
0.8271	Intermediate Similarity	NPC42423
0.8088	Intermediate Similarity	NPC279045
0.8088	Intermediate Similarity	NPC113325
0.8015	Intermediate Similarity	NPC228511
0.7917	Intermediate Similarity	NPC474563
0.7857	Intermediate Similarity	NPC239770
0.781	Intermediate Similarity	NPC328070
0.7786	Intermediate Similarity	NPC322526
0.7761	Intermediate Similarity	NPC278097
0.7754	Intermediate Similarity	NPC90693
0.7754	Intermediate Similarity	NPC64897
0.7714	Intermediate Similarity	NPC473052
0.7714	Intermediate Similarity	NPC473055
0.771	Intermediate Similarity	NPC478016
0.771	Intermediate Similarity	NPC478015
0.771	Intermediate Similarity	NPC478014
0.7676	Intermediate Similarity	NPC108852
0.7676	Intermediate Similarity	NPC261709
0.7676	Intermediate Similarity	NPC111586
0.7661	Intermediate Similarity	NPC307903
0.7661	Intermediate Similarity	NPC140251
0.766	Intermediate Similarity	NPC471201
0.766	Intermediate Similarity	NPC153007
0.7643	Intermediate Similarity	NPC175870
0.7576	Intermediate Similarity	NPC80150
0.7576	Intermediate Similarity	NPC190663
0.7517	Intermediate Similarity	NPC49565
0.7517	Intermediate Similarity	NPC262216
0.7463	Intermediate Similarity	NPC160493
0.7438	Intermediate Similarity	NPC317280
0.7438	Intermediate Similarity	NPC329387
0.7391	Intermediate Similarity	NPC295478
0.7347	Intermediate Similarity	NPC31171
0.7347	Intermediate Similarity	NPC237240
0.7308	Intermediate Similarity	NPC71205
0.7267	Intermediate Similarity	NPC470274
0.7266	Intermediate Similarity	NPC476290
0.7254	Intermediate Similarity	NPC477680
0.7241	Intermediate Similarity	NPC150712
0.7231	Intermediate Similarity	NPC306977
0.7231	Intermediate Similarity	NPC287055
0.7231	Intermediate Similarity	NPC242957
0.7231	Intermediate Similarity	NPC206414
0.72	Intermediate Similarity	NPC201692
0.72	Intermediate Similarity	NPC202613
0.72	Intermediate Similarity	NPC471317
0.7179	Intermediate Similarity	NPC67080
0.7177	Intermediate Similarity	NPC469457
0.7165	Intermediate Similarity	NPC274089
0.7165	Intermediate Similarity	NPC191215
0.7164	Intermediate Similarity	NPC310467
0.7154	Intermediate Similarity	NPC218855
0.7154	Intermediate Similarity	NPC471188
0.7154	Intermediate Similarity	NPC476269
0.7133	Intermediate Similarity	NPC146097
0.7133	Intermediate Similarity	NPC339338
0.7133	Intermediate Similarity	NPC227905
0.7121	Intermediate Similarity	NPC215419
0.7101	Intermediate Similarity	NPC285394
0.7099	Intermediate Similarity	NPC470253
0.709	Intermediate Similarity	NPC169328
0.7077	Intermediate Similarity	NPC265513
0.707	Intermediate Similarity	NPC476750
0.7067	Intermediate Similarity	NPC173934
0.7054	Intermediate Similarity	NPC475282
0.7049	Intermediate Similarity	NPC206764
0.7045	Intermediate Similarity	NPC234637
0.7045	Intermediate Similarity	NPC130591
0.7039	Intermediate Similarity	NPC185404
0.7029	Intermediate Similarity	NPC35996
0.7014	Intermediate Similarity	NPC132847
0.7008	Intermediate Similarity	NPC113326
0.7008	Intermediate Similarity	NPC194390
0.7008	Intermediate Similarity	NPC224610
0.7008	Intermediate Similarity	NPC88267
0.7007	Intermediate Similarity	NPC472981
0.7	Intermediate Similarity	NPC328824
0.7	Intermediate Similarity	NPC294050
0.7	Intermediate Similarity	NPC328997
0.6978	Remote Similarity	NPC473938
0.697	Remote Similarity	NPC471481
0.6968	Remote Similarity	NPC114808
0.6963	Remote Similarity	NPC61651
0.6957	Remote Similarity	NPC213126
0.6957	Remote Similarity	NPC84281
0.6957	Remote Similarity	NPC169485
0.6957	Remote Similarity	NPC317474
0.6957	Remote Similarity	NPC291027
0.6953	Remote Similarity	NPC471186
0.6944	Remote Similarity	NPC313663
0.6943	Remote Similarity	NPC476194
0.694	Remote Similarity	NPC476190
0.6935	Remote Similarity	NPC289201
0.6934	Remote Similarity	NPC45777
0.6934	Remote Similarity	NPC477061
0.6929	Remote Similarity	NPC477249
0.6929	Remote Similarity	NPC247976
0.6929	Remote Similarity	NPC47667
0.6929	Remote Similarity	NPC477248
0.6923	Remote Similarity	NPC93343
0.6917	Remote Similarity	NPC294458
0.6912	Remote Similarity	NPC314992
0.6911	Remote Similarity	NPC58674
0.6905	Remote Similarity	NPC264728
0.6901	Remote Similarity	NPC316553
0.6899	Remote Similarity	NPC475800
0.6899	Remote Similarity	NPC244933
0.6899	Remote Similarity	NPC85560
0.689	Remote Similarity	NPC88378
0.689	Remote Similarity	NPC211713
0.6887	Remote Similarity	NPC475578
0.6883	Remote Similarity	NPC4108
0.6875	Remote Similarity	NPC246913
0.6875	Remote Similarity	NPC15506
0.6867	Remote Similarity	NPC473922
0.6866	Remote Similarity	NPC93181
0.686	Remote Similarity	NPC316108
0.6857	Remote Similarity	NPC12881
0.6857	Remote Similarity	NPC140118
0.6852	Remote Similarity	NPC476749
0.685	Remote Similarity	NPC469598
0.6849	Remote Similarity	NPC474787
0.6849	Remote Similarity	NPC9687
0.6849	Remote Similarity	NPC475318
0.6849	Remote Similarity	NPC49577
0.6849	Remote Similarity	NPC260045
0.6849	Remote Similarity	NPC476102
0.6849	Remote Similarity	NPC273907
0.6849	Remote Similarity	NPC90194
0.6849	Remote Similarity	NPC475598
0.6849	Remote Similarity	NPC79465
0.6849	Remote Similarity	NPC293377
0.6849	Remote Similarity	NPC76785
0.6849	Remote Similarity	NPC474811
0.6849	Remote Similarity	NPC118099
0.6849	Remote Similarity	NPC474855
0.6849	Remote Similarity	NPC151706
0.6842	Remote Similarity	NPC474584
0.6831	Remote Similarity	NPC71610
0.6831	Remote Similarity	NPC146239
0.6829	Remote Similarity	NPC120667
0.6829	Remote Similarity	NPC278272
0.6828	Remote Similarity	NPC3202
0.6826	Remote Similarity	NPC475345
0.6825	Remote Similarity	NPC54647
0.6825	Remote Similarity	NPC12730
0.6822	Remote Similarity	NPC211551
0.6818	Remote Similarity	NPC474057
0.6815	Remote Similarity	NPC9274
0.6812	Remote Similarity	NPC472679
0.6812	Remote Similarity	NPC474223
0.6812	Remote Similarity	NPC475827
0.6812	Remote Similarity	NPC475804
0.6812	Remote Similarity	NPC470585
0.6812	Remote Similarity	NPC474222
0.6812	Remote Similarity	NPC472680
0.6806	Remote Similarity	NPC316746
0.6806	Remote Similarity	NPC472388
0.6803	Remote Similarity	NPC187725
0.6803	Remote Similarity	NPC141607
0.68	Remote Similarity	NPC471516
0.6797	Remote Similarity	NPC476757
0.6797	Remote Similarity	NPC94602
0.6794	Remote Similarity	NPC474725
0.6792	Remote Similarity	NPC156348
0.6788	Remote Similarity	NPC237420
0.6786	Remote Similarity	NPC475649
0.6783	Remote Similarity	NPC40488
0.6781	Remote Similarity	NPC15850
0.6776	Remote Similarity	NPC44649
0.6769	Remote Similarity	NPC100767
0.6767	Remote Similarity	NPC471189
0.6765	Remote Similarity	NPC2265
0.6763	Remote Similarity	NPC476234
0.6761	Remote Similarity	NPC119326
0.6761	Remote Similarity	NPC236405
0.6748	Remote Similarity	NPC314693
0.6746	Remote Similarity	NPC120393
0.6746	Remote Similarity	NPC476120
0.6744	Remote Similarity	NPC329282
0.6741	Remote Similarity	NPC33742
0.6736	Remote Similarity	NPC225103
0.6736	Remote Similarity	NPC478147
0.6732	Remote Similarity	NPC473541
0.6732	Remote Similarity	NPC470579
0.672	Remote Similarity	NPC25565
0.6718	Remote Similarity	NPC112903
0.6716	Remote Similarity	NPC477475
0.6716	Remote Similarity	NPC477476
0.6715	Remote Similarity	NPC222968
0.6715	Remote Similarity	NPC80605
0.6715	Remote Similarity	NPC323440
0.6714	Remote Similarity	NPC109151

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 NPC116057 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	105
0.1-0.2	483
0.2-0.3	833
0.3-0.4	2083
0.4-0.5	3457
0.5-0.6	1844
0.6-0.7	335
0.7-0.8	10
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
0.748	Intermediate Similarity	NPD3642	Approved
0.748	Intermediate Similarity	NPD3644	Approved
0.748	Intermediate Similarity	NPD3643	Approved
0.7426	Intermediate Similarity	NPD6325	Discontinued
0.7368	Intermediate Similarity	NPD5981	Approved
0.7347	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6330	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5157	Phase 1
0.7101	Intermediate Similarity	NPD5159	Phase 2
0.709	Intermediate Similarity	NPD7522	Discontinued
0.7077	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7084	Phase 3
0.6992	Remote Similarity	NPD1711	Phase 2
0.6957	Remote Similarity	NPD4217	Approved
0.6957	Remote Similarity	NPD2608	Approved
0.6957	Remote Similarity	NPD4218	Approved
0.6957	Remote Similarity	NPD4215	Approved
0.6957	Remote Similarity	NPD2609	Approved
0.6957	Remote Similarity	NPD2612	Approved
0.6957	Remote Similarity	NPD3132	Approved
0.6957	Remote Similarity	NPD3131	Approved
0.6957	Remote Similarity	NPD2610	Approved
0.6957	Remote Similarity	NPD2611	Approved
0.6957	Remote Similarity	NPD4216	Approved
0.6953	Remote Similarity	NPD1018	Approved
0.6944	Remote Similarity	NPD7714	Approved
0.6944	Remote Similarity	NPD7715	Approved
0.6929	Remote Similarity	NPD6647	Phase 2
0.6918	Remote Similarity	NPD8172	Phase 2
0.6918	Remote Similarity	NPD8173	Phase 2
0.6912	Remote Similarity	NPD2217	Approved
0.6912	Remote Similarity	NPD2218	Phase 2
0.6911	Remote Similarity	NPD4814	Discontinued
0.6889	Remote Similarity	NPD3123	Discovery
0.685	Remote Similarity	NPD4719	Phase 2
0.6846	Remote Similarity	NPD6406	Approved
0.6842	Remote Similarity	NPD7094	Approved
0.6842	Remote Similarity	NPD6858	Approved
0.6806	Remote Similarity	NPD6919	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD8265	Approved
0.6776	Remote Similarity	NPD7295	Approved
0.6772	Remote Similarity	NPD4760	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD467	Phase 1
0.6716	Remote Similarity	NPD2607	Approved
0.6714	Remote Similarity	NPD5618	Discontinued
0.6694	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7725	Approved
0.669	Remote Similarity	NPD4738	Phase 2
0.6667	Remote Similarity	NPD4655	Approved
0.6667	Remote Similarity	NPD7011	Discontinued
0.6667	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4657	Approved
0.6667	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4479	Discontinued
0.6643	Remote Similarity	NPD2956	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD2613	Approved
0.662	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD253	Approved
0.6613	Remote Similarity	NPD6690	Approved
0.6601	Remote Similarity	NPD3400	Discontinued
0.6599	Remote Similarity	NPD7713	Phase 3
0.6594	Remote Similarity	NPD7610	Discontinued
0.6565	Remote Similarity	NPD5717	Approved
0.6562	Remote Similarity	NPD2066	Phase 3
0.6554	Remote Similarity	NPD8416	Discontinued
0.6547	Remote Similarity	NPD7009	Phase 2
0.6547	Remote Similarity	NPD998	Approved
0.6544	Remote Similarity	NPD2652	Approved
0.6544	Remote Similarity	NPD2650	Approved
0.6544	Remote Similarity	NPD3598	Phase 3
0.6544	Remote Similarity	NPD6010	Discontinued
0.6536	Remote Similarity	NPD7082	Approved
0.6529	Remote Similarity	NPD5030	Phase 2
0.6528	Remote Similarity	NPD2160	Approved
0.6528	Remote Similarity	NPD2628	Approved
0.6528	Remote Similarity	NPD2625	Approved
0.6528	Remote Similarity	NPD2626	Approved
0.6528	Remote Similarity	NPD2627	Approved
0.6528	Remote Similarity	NPD2159	Approved
0.6525	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD5706	Approved
0.6515	Remote Similarity	NPD5705	Approved
0.6515	Remote Similarity	NPD5704	Approved
0.6513	Remote Similarity	NPD7720	Phase 2
0.6508	Remote Similarity	NPD4094	Approved
0.6503	Remote Similarity	NPD1755	Approved
0.65	Remote Similarity	NPD1710	Approved
0.6496	Remote Similarity	NPD5951	Approved
0.6496	Remote Similarity	NPD2629	Approved
0.6494	Remote Similarity	NPD7259	Approved
0.6494	Remote Similarity	NPD6676	Phase 2
0.6493	Remote Similarity	NPD1752	Approved
0.6493	Remote Similarity	NPD1756	Approved
0.6491	Remote Similarity	NPD5034	Approved
0.6491	Remote Similarity	NPD4955	Approved
0.6491	Remote Similarity	NPD5028	Approved
0.6491	Remote Similarity	NPD5026	Approved
0.6491	Remote Similarity	NPD36	Approved
0.6491	Remote Similarity	NPD4954	Approved
0.6489	Remote Similarity	NPD1237	Approved
0.6489	Remote Similarity	NPD179	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD3090	Approved
0.6486	Remote Similarity	NPD4746	Phase 3
0.6486	Remote Similarity	NPD2574	Discontinued
0.6486	Remote Similarity	NPD3087	Approved
0.6486	Remote Similarity	NPD3615	Approved
0.6486	Remote Similarity	NPD2571	Approved
0.6486	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD2570	Approved
0.6486	Remote Similarity	NPD3614	Approved
0.6486	Remote Similarity	NPD3088	Approved
0.6486	Remote Similarity	NPD3616	Approved
0.6486	Remote Similarity	NPD2573	Approved
0.6486	Remote Similarity	NPD4745	Approved
0.6486	Remote Similarity	NPD2566	Approved
0.6486	Remote Similarity	NPD3089	Approved
0.6483	Remote Similarity	NPD4980	Approved
0.648	Remote Similarity	NPD7631	Approved
0.6479	Remote Similarity	NPD3603	Phase 3
0.6475	Remote Similarity	NPD6065	Approved
0.6474	Remote Similarity	NPD8165	Discontinued
0.6466	Remote Similarity	NPD4095	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD3136	Phase 2
0.6462	Remote Similarity	NPD855	Approved
0.6462	Remote Similarity	NPD854	Approved
0.6462	Remote Similarity	NPD6024	Approved
0.6462	Remote Similarity	NPD6027	Approved
0.6458	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5578	Approved
0.6457	Remote Similarity	NPD8361	Approved
0.6457	Remote Similarity	NPD8360	Approved
0.6454	Remote Similarity	NPD2932	Approved
0.6454	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD7342	Discontinued
0.6453	Remote Similarity	NPD5035	Approved
0.6449	Remote Similarity	NPD1348	Approved
0.6447	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD2192	Approved
0.6439	Remote Similarity	NPD999	Phase 2
0.6439	Remote Similarity	NPD2197	Approved
0.6438	Remote Similarity	NPD3626	Phase 3
0.6429	Remote Similarity	NPD2617	Discontinued
0.6425	Remote Similarity	NPD8485	Approved
0.6416	Remote Similarity	NPD8407	Phase 2
0.6412	Remote Similarity	NPD1929	Approved
0.6412	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD1930	Approved
0.6406	Remote Similarity	NPD3495	Discontinued
0.6406	Remote Similarity	NPD2487	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD4152	Approved
0.6403	Remote Similarity	NPD6775	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7609	Phase 3
0.64	Remote Similarity	NPD4684	Phase 3
0.64	Remote Similarity	NPD8643	Discontinued
0.64	Remote Similarity	NPD4685	Phase 3
0.64	Remote Similarity	NPD4686	Approved
0.6398	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7487	Discontinued
0.6383	Remote Similarity	NPD4209	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD5036	Approved
0.6377	Remote Similarity	NPD4766	Approved
0.6376	Remote Similarity	NPD7086	Phase 2
0.6376	Remote Similarity	NPD8118	Discontinued
0.6375	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.637	Remote Similarity	NPD6914	Discontinued
0.6364	Remote Similarity	NPD6287	Discontinued
0.6364	Remote Similarity	NPD8435	Approved
0.6364	Remote Similarity	NPD4807	Approved
0.6364	Remote Similarity	NPD4806	Approved
0.6364	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD9609	Approved
0.6357	Remote Similarity	NPD9611	Approved
0.6357	Remote Similarity	NPD9612	Approved
0.6351	Remote Similarity	NPD6039	Approved
0.6346	Remote Similarity	NPD8323	Discontinued
0.6346	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD6038	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD5037	Approved
0.6343	Remote Similarity	NPD5038	Approved
0.6343	Remote Similarity	NPD7683	Discontinued
0.6338	Remote Similarity	NPD5306	Approved
0.6338	Remote Similarity	NPD3019	Approved
0.6338	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD5305	Approved
0.6338	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD4733	Approved
0.6337	Remote Similarity	NPD8368	Discontinued
0.6336	Remote Similarity	NPD5716	Approved
0.6336	Remote Similarity	NPD4119	Approved
0.6336	Remote Similarity	NPD2193	Phase 2
0.6336	Remote Similarity	NPD4817	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