NPASS Compound

Structure

NPC216335 OpenBabel07101718282D 27 29 0 0 1 0 0 0 0 0999 V2000 -2.8147 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7788 -2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2788 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 -1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 -1.2024 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6808 -1.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4128 0.2976 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9487 -1.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4128 -2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4128 -1.7024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2788 -0.2024 0.0000 C 0 0 1 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 -6.2788 -1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 -1.2024 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4128 1.2976 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -7.1449 0.2976 0.0000 Cl 0 0 0 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 -1.9487 -2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 -3.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7213 0.4612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 15 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 20 1 0 0 0 0 9 11 1 0 0 0 0 10 13 1 6 0 0 0 10 18 1 0 0 0 0 11 20 1 1 0 0 0 12 17 1 0 0 0 0 12 21 1 6 0 0 0 13 24 1 1 0 0 0 14 16 1 0 0 0 0 14 25 2 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 1 0 0 0 17 19 1 0 0 0 0 17 22 1 1 0 0 0 18 23 1 0 0 0 0 18 27 2 0 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	415.13
Volume:	394.841
LogP:	3.677
LogD:	3.44
LogS:	-3.464
# Rotatable Bonds:	3
TPSA:	93.55
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	5.249
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.42
MDCK Permeability:	1.1308234206808265e-05
Pgp-inhibitor:	0.367
Pgp-substrate:	0.981
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.834
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.904
Plasma Protein Binding (PPB):	92.4773178100586%
Volume Distribution (VD):	1.414
Pgp-substrate:	7.205720901489258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.532
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.196
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.961
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.301
CYP3A4-inhibitor:	0.199
CYP3A4-substrate:	0.286

ADMET: Excretion

Clearance (CL):	12.494
Half-life (T1/2):	0.601

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.236
Drug-inuced Liver Injury (DILI):	0.62
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.893
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.341
Carcinogencity:	0.388
Eye Corrosion:	0.029
Eye Irritation:	0.058
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC216335

Natural Product ID:	NPC216335
*Common Name:**	Haterumaimide D
IUPAC Name:	(3R)-3-[(1S)-2-[(1S,4aR,6R,7R,8aR)-6,7-dichloro-2,5,5,8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]pyrrolidine-2,5-dione
Synonyms:	Haterumaimide D
Standard InCHIKey:	WOZCGGONMQVWED-YUYNUPNTSA-N
Standard InCHI:	InChI=1S/C20H27Cl2NO4/c1-9-5-14(25)16-19(2,3)17(22)12(21)8-20(16,4)11(9)7-13(24)10-6-15(26)23-18(10)27/h5,10-13,16-17,24H,6-8H2,1-4H3,(H,23,26,27)/t10-,11+,12-,13+,16+,17+,20-/m1/s1
SMILES:	CC1=CC(=O)[C@H]2C(C)(C)[C@H]([C@@H](C[C@]2(C)[C@H]1C[C@@H]([C@H]1CC(=NC1=O)O)O)Cl)Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456739
PubChem CID:	9801980
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO32802	Pleurobranchus forskalii	Species	Pleurobranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332867]
NPO18522	Pleurobranchus albiguttatus	Species	Pleurobranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332867]
NPO32802	Pleurobranchus forskalii	Species	Pleurobranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23848233]
NPO32802	Pleurobranchus forskalii	Species	Pleurobranchidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8786369]
NPO18522	Pleurobranchus albiguttatus	Species	Pleurobranchidae	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
GI50	1
Others	2

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	977.24	nM	PMID[502964]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TGI	=	12302.69	nM	PMID[502964]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	44668.36	nM	PMID[502964]

☑ 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 NPC216335 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	106
0.1-0.2	812
0.2-0.3	6650
0.3-0.4	20038
0.4-0.5	10365
0.5-0.6	4551
0.6-0.7	167
0.7-0.8	2
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9626	High Similarity	NPC7797
0.8796	High Similarity	NPC259476
0.8596	High Similarity	NPC24462
0.8393	Intermediate Similarity	NPC168733
0.8246	Intermediate Similarity	NPC92829
0.8034	Intermediate Similarity	NPC122404
0.7373	Intermediate Similarity	NPC42590
0.7119	Intermediate Similarity	NPC474563
0.7083	Intermediate Similarity	NPC475800
0.7025	Intermediate Similarity	NPC307903
0.7025	Intermediate Similarity	NPC140251
0.6967	Remote Similarity	NPC474725
0.6911	Remote Similarity	NPC328052
0.6911	Remote Similarity	NPC476290
0.6911	Remote Similarity	NPC46764
0.68	Remote Similarity	NPC476269
0.6612	Remote Similarity	NPC469598
0.6589	Remote Similarity	NPC476190
0.6587	Remote Similarity	NPC12270
0.6549	Remote Similarity	NPC194417
0.6545	Remote Similarity	NPC116797
0.6541	Remote Similarity	NPC16709
0.6496	Remote Similarity	NPC474807
0.6449	Remote Similarity	NPC96425
0.6417	Remote Similarity	NPC125771
0.6417	Remote Similarity	NPC218902
0.641	Remote Similarity	NPC314500
0.6397	Remote Similarity	NPC287903
0.6393	Remote Similarity	NPC77703
0.6379	Remote Similarity	NPC477943
0.6372	Remote Similarity	NPC321187
0.6372	Remote Similarity	NPC161423
0.6372	Remote Similarity	NPC85774
0.6372	Remote Similarity	NPC58841
0.6372	Remote Similarity	NPC214043
0.6372	Remote Similarity	NPC329043
0.6372	Remote Similarity	NPC473246
0.6372	Remote Similarity	NPC227064
0.6364	Remote Similarity	NPC234542
0.6364	Remote Similarity	NPC323532
0.6357	Remote Similarity	NPC106479
0.6348	Remote Similarity	NPC136548
0.6333	Remote Similarity	NPC247220
0.6333	Remote Similarity	NPC472734
0.6333	Remote Similarity	NPC472733
0.633	Remote Similarity	NPC197659
0.6316	Remote Similarity	NPC474853
0.6316	Remote Similarity	NPC179006
0.6311	Remote Similarity	NPC477964
0.6311	Remote Similarity	NPC473224
0.6306	Remote Similarity	NPC2482
0.6306	Remote Similarity	NPC172013
0.6281	Remote Similarity	NPC472732
0.6281	Remote Similarity	NPC472731
0.6277	Remote Similarity	NPC156797
0.6273	Remote Similarity	NPC178852
0.6271	Remote Similarity	NPC19114
0.627	Remote Similarity	NPC169375
0.6261	Remote Similarity	NPC145879
0.6261	Remote Similarity	NPC470955
0.6261	Remote Similarity	NPC474778
0.6261	Remote Similarity	NPC474732
0.6261	Remote Similarity	NPC327115
0.6261	Remote Similarity	NPC153699
0.6261	Remote Similarity	NPC94666
0.6261	Remote Similarity	NPC474733
0.6261	Remote Similarity	NPC31564
0.6261	Remote Similarity	NPC76164
0.625	Remote Similarity	NPC263347
0.625	Remote Similarity	NPC121984
0.625	Remote Similarity	NPC14151
0.625	Remote Similarity	NPC280725
0.625	Remote Similarity	NPC44963
0.625	Remote Similarity	NPC208725
0.625	Remote Similarity	NPC472684
0.624	Remote Similarity	NPC119329
0.6239	Remote Similarity	NPC1015
0.6239	Remote Similarity	NPC263582
0.6239	Remote Similarity	NPC472983
0.6239	Remote Similarity	NPC119416
0.6239	Remote Similarity	NPC5509
0.6239	Remote Similarity	NPC31985
0.623	Remote Similarity	NPC472729
0.623	Remote Similarity	NPC153776
0.623	Remote Similarity	NPC472730
0.623	Remote Similarity	NPC177680
0.6228	Remote Similarity	NPC237712
0.622	Remote Similarity	NPC476276
0.6218	Remote Similarity	NPC115021
0.6218	Remote Similarity	NPC475255
0.6216	Remote Similarity	NPC308038
0.6214	Remote Similarity	NPC116057
0.6214	Remote Similarity	NPC477996
0.6207	Remote Similarity	NPC96496
0.6207	Remote Similarity	NPC58063
0.6207	Remote Similarity	NPC38885
0.6207	Remote Similarity	NPC475740
0.6198	Remote Similarity	NPC472806
0.6198	Remote Similarity	NPC167193
0.6195	Remote Similarity	NPC212083
0.6195	Remote Similarity	NPC151519
0.6195	Remote Similarity	NPC103486
0.6186	Remote Similarity	NPC51486
0.6186	Remote Similarity	NPC134321
0.6186	Remote Similarity	NPC128672
0.6183	Remote Similarity	NPC476814
0.6183	Remote Similarity	NPC476813
0.6179	Remote Similarity	NPC472727
0.6179	Remote Similarity	NPC472728
0.6179	Remote Similarity	NPC110897
0.6174	Remote Similarity	NPC476426
0.6174	Remote Similarity	NPC470574
0.6174	Remote Similarity	NPC469948
0.6174	Remote Similarity	NPC474218
0.6174	Remote Similarity	NPC79573
0.6167	Remote Similarity	NPC477290
0.6167	Remote Similarity	NPC473314
0.6167	Remote Similarity	NPC111015
0.6165	Remote Similarity	NPC476956
0.6161	Remote Similarity	NPC148685
0.6161	Remote Similarity	NPC157895
0.6161	Remote Similarity	NPC45495
0.6161	Remote Similarity	NPC104120
0.6161	Remote Similarity	NPC472478
0.6154	Remote Similarity	NPC471722
0.6154	Remote Similarity	NPC471793
0.6154	Remote Similarity	NPC471791
0.6154	Remote Similarity	NPC472802
0.6154	Remote Similarity	NPC328539
0.6154	Remote Similarity	NPC470417
0.6154	Remote Similarity	NPC474854
0.6154	Remote Similarity	NPC473229
0.6154	Remote Similarity	NPC471724
0.6154	Remote Similarity	NPC34754
0.6154	Remote Similarity	NPC328313
0.6148	Remote Similarity	NPC27105
0.6148	Remote Similarity	NPC473161
0.6148	Remote Similarity	NPC273269
0.6148	Remote Similarity	NPC167380
0.6148	Remote Similarity	NPC89225
0.6147	Remote Similarity	NPC114236
0.6143	Remote Similarity	NPC471691
0.614	Remote Similarity	NPC64600
0.6134	Remote Similarity	NPC185936
0.6134	Remote Similarity	NPC168027
0.6134	Remote Similarity	NPC154101
0.6134	Remote Similarity	NPC473998
0.6127	Remote Similarity	NPC78189
0.6126	Remote Similarity	NPC62336
0.6121	Remote Similarity	NPC475022
0.6121	Remote Similarity	NPC262085
0.6121	Remote Similarity	NPC118648
0.6121	Remote Similarity	NPC72133
0.6121	Remote Similarity	NPC222613
0.6121	Remote Similarity	NPC475181
0.6116	Remote Similarity	NPC472485
0.6116	Remote Similarity	NPC88310
0.6116	Remote Similarity	NPC148523
0.6111	Remote Similarity	NPC230889
0.6111	Remote Similarity	NPC14537
0.6111	Remote Similarity	NPC472616
0.6106	Remote Similarity	NPC226068
0.6106	Remote Similarity	NPC136150
0.6106	Remote Similarity	NPC189237
0.6102	Remote Similarity	NPC309603
0.6102	Remote Similarity	NPC26959
0.6102	Remote Similarity	NPC86319
0.6102	Remote Similarity	NPC472970
0.6102	Remote Similarity	NPC473999
0.6102	Remote Similarity	NPC310010
0.6102	Remote Similarity	NPC54689
0.6102	Remote Similarity	NPC268406
0.6102	Remote Similarity	NPC472971
0.6102	Remote Similarity	NPC275740
0.6102	Remote Similarity	NPC477973
0.6102	Remote Similarity	NPC472475
0.6102	Remote Similarity	NPC186688
0.6102	Remote Similarity	NPC326627
0.6102	Remote Similarity	NPC472477
0.6099	Remote Similarity	NPC139585
0.6099	Remote Similarity	NPC472413
0.6098	Remote Similarity	NPC472687
0.6098	Remote Similarity	NPC203388
0.6098	Remote Similarity	NPC471331
0.6098	Remote Similarity	NPC99657
0.6098	Remote Similarity	NPC471330
0.6098	Remote Similarity	NPC147954
0.6091	Remote Similarity	NPC180886
0.6091	Remote Similarity	NPC470525
0.6087	Remote Similarity	NPC59453
0.6087	Remote Similarity	NPC470812
0.6087	Remote Similarity	NPC221758
0.6087	Remote Similarity	NPC82902
0.6083	Remote Similarity	NPC472930
0.6083	Remote Similarity	NPC152897
0.6083	Remote Similarity	NPC134826
0.6083	Remote Similarity	NPC233118
0.6083	Remote Similarity	NPC66429
0.6071	Remote Similarity	NPC474113
0.6071	Remote Similarity	NPC7232

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 NPC216335 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	98
0.1-0.2	683
0.2-0.3	3830
0.3-0.4	3635
0.4-0.5	680
0.5-0.6	205
0.6-0.7	19
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
0.7008	Intermediate Similarity	NPD4522	Approved
0.672	Remote Similarity	NPD5215	Approved
0.6693	Remote Similarity	NPD5167	Approved
0.6587	Remote Similarity	NPD1719	Phase 1
0.6496	Remote Similarity	NPD5956	Approved
0.648	Remote Similarity	NPD5168	Approved
0.6457	Remote Similarity	NPD5217	Approved
0.6457	Remote Similarity	NPD5216	Approved
0.6404	Remote Similarity	NPD3618	Phase 1
0.6378	Remote Similarity	NPD5169	Approved
0.6372	Remote Similarity	NPD3133	Approved
0.6372	Remote Similarity	NPD3665	Phase 1
0.6372	Remote Similarity	NPD3666	Approved
0.6364	Remote Similarity	NPD7100	Approved
0.6328	Remote Similarity	NPD5127	Approved
0.6294	Remote Similarity	NPD6333	Approved
0.6294	Remote Similarity	NPD6334	Approved
0.621	Remote Similarity	NPD5091	Approved
0.6195	Remote Similarity	NPD3667	Approved
0.6143	Remote Similarity	NPD6914	Discontinued
0.6136	Remote Similarity	NPD6868	Approved
0.6121	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5279	Phase 3
0.6119	Remote Similarity	NPD7101	Approved
0.6102	Remote Similarity	NPD4753	Phase 2
0.6102	Remote Similarity	NPD5328	Approved
0.6094	Remote Similarity	NPD5128	Approved
0.6087	Remote Similarity	NPD4786	Approved
0.6083	Remote Similarity	NPD4202	Approved
0.6066	Remote Similarity	NPD4697	Phase 3
0.6048	Remote Similarity	NPD6404	Discontinued
0.6045	Remote Similarity	NPD6314	Approved
0.6045	Remote Similarity	NPD6313	Approved
0.6045	Remote Similarity	NPD6335	Approved
0.6016	Remote Similarity	NPD4755	Approved
0.6	Remote Similarity	NPD6420	Discontinued
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD7515	Phase 2
0.5984	Remote Similarity	NPD4629	Approved
0.5984	Remote Similarity	NPD5210	Approved
0.595	Remote Similarity	NPD6399	Phase 3
0.595	Remote Similarity	NPD5133	Approved
0.5935	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5935	Remote Similarity	NPD5222	Approved
0.5935	Remote Similarity	NPD5221	Approved
0.592	Remote Similarity	NPD4700	Approved
0.592	Remote Similarity	NPD5285	Approved
0.592	Remote Similarity	NPD5286	Approved
0.592	Remote Similarity	NPD4696	Approved
0.5913	Remote Similarity	NPD4223	Phase 3
0.5913	Remote Similarity	NPD4221	Approved
0.5887	Remote Similarity	NPD7902	Approved
0.5887	Remote Similarity	NPD5173	Approved
0.5887	Remote Similarity	NPD6033	Approved
0.5877	Remote Similarity	NPD4695	Discontinued
0.5873	Remote Similarity	NPD5223	Approved
0.5868	Remote Similarity	NPD5284	Approved
0.5868	Remote Similarity	NPD5281	Approved
0.5857	Remote Similarity	NPD6336	Discontinued
0.5827	Remote Similarity	NPD5225	Approved
0.5827	Remote Similarity	NPD5226	Approved
0.5827	Remote Similarity	NPD4633	Approved
0.5827	Remote Similarity	NPD5211	Phase 2
0.5827	Remote Similarity	NPD5224	Approved
0.5812	Remote Similarity	NPD3668	Phase 3
0.5812	Remote Similarity	NPD4197	Approved
0.5797	Remote Similarity	NPD5983	Phase 2
0.5785	Remote Similarity	NPD4096	Approved
0.5781	Remote Similarity	NPD5175	Approved
0.5781	Remote Similarity	NPD4754	Approved
0.5781	Remote Similarity	NPD5174	Approved
0.5772	Remote Similarity	NPD7748	Approved
0.5763	Remote Similarity	NPD5329	Approved
0.576	Remote Similarity	NPD6083	Phase 2
0.576	Remote Similarity	NPD6084	Phase 2
0.5758	Remote Similarity	NPD4634	Approved
0.5746	Remote Similarity	NPD4632	Approved
0.5736	Remote Similarity	NPD5141	Approved
0.5726	Remote Similarity	NPD5695	Phase 3
0.5714	Remote Similarity	NPD7146	Approved
0.5714	Remote Similarity	NPD5690	Phase 2
0.5714	Remote Similarity	NPD4693	Phase 3
0.5714	Remote Similarity	NPD6684	Approved
0.5714	Remote Similarity	NPD6409	Approved
0.5714	Remote Similarity	NPD4690	Approved
0.5714	Remote Similarity	NPD4689	Approved
0.5714	Remote Similarity	NPD5205	Approved
0.5714	Remote Similarity	NPD4138	Approved
0.5714	Remote Similarity	NPD5696	Approved
0.5714	Remote Similarity	NPD7521	Approved
0.5714	Remote Similarity	NPD5330	Approved
0.5714	Remote Similarity	NPD4694	Approved
0.5714	Remote Similarity	NPD4519	Discontinued
0.5714	Remote Similarity	NPD4688	Approved
0.5714	Remote Similarity	NPD7334	Approved
0.5714	Remote Similarity	NPD4623	Approved
0.5714	Remote Similarity	NPD5280	Approved
0.5702	Remote Similarity	NPD3617	Approved
0.5692	Remote Similarity	NPD5739	Approved
0.5692	Remote Similarity	NPD4768	Approved
0.5692	Remote Similarity	NPD6402	Approved
0.5692	Remote Similarity	NPD6675	Approved
0.5692	Remote Similarity	NPD7128	Approved
0.5692	Remote Similarity	NPD4767	Approved
0.5691	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD6373	Approved
0.5682	Remote Similarity	NPD6372	Approved
0.5656	Remote Similarity	NPD790	Approved
0.5649	Remote Similarity	NPD6614	Approved
0.5649	Remote Similarity	NPD5697	Approved
0.5649	Remote Similarity	NPD6412	Phase 2
0.5649	Remote Similarity	NPD5701	Approved
0.5645	Remote Similarity	NPD7900	Approved
0.5645	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD5282	Discontinued
0.562	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.562	Remote Similarity	NPD6903	Approved
0.562	Remote Similarity	NPD5737	Approved
0.562	Remote Similarity	NPD6672	Approved
0.562	Remote Similarity	NPD6009	Approved
0.5606	Remote Similarity	NPD6881	Approved
0.5606	Remote Similarity	NPD7320	Approved
0.5606	Remote Similarity	NPD4730	Approved
0.5606	Remote Similarity	NPD6899	Approved
0.5606	Remote Similarity	NPD6011	Approved
0.5606	Remote Similarity	NPD4729	Approved
0.56	Remote Similarity	NPD5654	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