NPASS Compound

Structure

NPC7797 OpenBabel07101718202D 26 28 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 -6.2788 -0.2024 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 -5.4128 0.2976 0.0000 C 0 0 1 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 -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 -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 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 10 1 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 5 10 2 0 0 0 0 5 15 1 0 0 0 0 6 12 1 0 0 0 0 6 16 1 0 0 0 0 7 13 1 0 0 0 0 7 14 1 0 0 0 0 8 11 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 11 21 1 6 0 0 0 12 14 1 6 0 0 0 12 18 1 0 0 0 0 13 20 1 1 0 0 0 14 23 1 1 0 0 0 15 17 1 0 0 0 0 15 24 2 0 0 0 0 16 22 2 0 0 0 0 16 25 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 1 0 0 0 18 22 1 0 0 0 0 18 26 2 0 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	381.17
Volume:	379.63
LogP:	3.225
LogD:	2.459
LogS:	-3.318
# Rotatable Bonds:	3
TPSA:	93.55
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.466
Synthetic Accessibility Score:	5.047
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.427
MDCK Permeability:	1.3475391824613325e-05
Pgp-inhibitor:	0.103
Pgp-substrate:	0.974
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.912
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.379
Plasma Protein Binding (PPB):	59.94560241699219%
Volume Distribution (VD):	1.872
Pgp-substrate:	30.251047134399414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.412
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.208
CYP2C9-inhibitor:	0.095
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.199
CYP3A4-inhibitor:	0.213
CYP3A4-substrate:	0.261

ADMET: Excretion

Clearance (CL):	14.715
Half-life (T1/2):	0.585

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.75
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.894
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.298
Carcinogencity:	0.939
Eye Corrosion:	0.005
Eye Irritation:	0.025
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: NPC7797

Natural Product ID:	NPC7797
*Common Name:**	Haterumaimide H
IUPAC Name:	(3R)-3-[(1S)-2-[(1S,4aS,7S,8aR)-7-chloro-2,5,5,8a-tetramethyl-4-oxo-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]-1-hydroxyethyl]pyrrolidine-2,5-dione
Synonyms:	Haterumaimide H
Standard InCHIKey:	QHHLSHYRRUPUFX-KHVISUPTSA-N
Standard InCHI:	InChI=1S/C20H28ClNO4/c1-10-5-15(24)17-19(2,3)8-11(21)9-20(17,4)13(10)7-14(23)12-6-16(25)22-18(12)26/h5,11-14,17,23H,6-9H2,1-4H3,(H,22,25,26)/t11-,12+,13-,14-,17-,20+/m0/s1
SMILES:	Cl[C@H]1CC(C)(C)[C@H]2[C@@](C1)(C)[C@@H](C[C@@H]([C@H]1CC(=NC1=O)O)O)C(=CC2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465666
PubChem CID:	10091265
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
NPO33282	lissoclinum sp.	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575950]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	2.7	ug.mL-1	PMID[509124]

☑ 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 NPC7797 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	98
0.1-0.2	747
0.2-0.3	5611
0.3-0.4	19853
0.4-0.5	10287
0.5-0.6	5632
0.6-0.7	451
0.7-0.8	11
0.8-0.85	3
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9626	High Similarity	NPC216335
0.9135	High Similarity	NPC259476
0.8704	High Similarity	NPC168733
0.8545	High Similarity	NPC92829
0.8319	Intermediate Similarity	NPC122404
0.8246	Intermediate Similarity	NPC24462
0.7632	Intermediate Similarity	NPC42590
0.7368	Intermediate Similarity	NPC474563
0.7328	Intermediate Similarity	NPC475800
0.7265	Intermediate Similarity	NPC140251
0.7265	Intermediate Similarity	NPC307903
0.7203	Intermediate Similarity	NPC474725
0.7143	Intermediate Similarity	NPC46764
0.7143	Intermediate Similarity	NPC476290
0.7143	Intermediate Similarity	NPC328052
0.7025	Intermediate Similarity	NPC476269
0.6838	Remote Similarity	NPC469598
0.6803	Remote Similarity	NPC12270
0.68	Remote Similarity	NPC476190
0.6792	Remote Similarity	NPC116797
0.6789	Remote Similarity	NPC194417
0.6726	Remote Similarity	NPC474807
0.6637	Remote Similarity	NPC314500
0.6615	Remote Similarity	NPC16709
0.661	Remote Similarity	NPC77703
0.6607	Remote Similarity	NPC477943
0.6606	Remote Similarity	NPC321187
0.6606	Remote Similarity	NPC161423
0.6606	Remote Similarity	NPC85774
0.6606	Remote Similarity	NPC227064
0.6606	Remote Similarity	NPC214043
0.6606	Remote Similarity	NPC329043
0.6606	Remote Similarity	NPC473246
0.6606	Remote Similarity	NPC58841
0.6581	Remote Similarity	NPC234542
0.6577	Remote Similarity	NPC136548
0.6571	Remote Similarity	NPC197659
0.6562	Remote Similarity	NPC323532
0.656	Remote Similarity	NPC106479
0.6552	Remote Similarity	NPC472734
0.6552	Remote Similarity	NPC247220
0.6552	Remote Similarity	NPC472733
0.6545	Remote Similarity	NPC179006
0.6545	Remote Similarity	NPC474853
0.6542	Remote Similarity	NPC172013
0.6542	Remote Similarity	NPC2482
0.6525	Remote Similarity	NPC477964
0.6525	Remote Similarity	NPC473224
0.6519	Remote Similarity	NPC96425
0.6509	Remote Similarity	NPC178852
0.6496	Remote Similarity	NPC472732
0.6496	Remote Similarity	NPC472731
0.6491	Remote Similarity	NPC19114
0.6486	Remote Similarity	NPC94666
0.6486	Remote Similarity	NPC145879
0.6486	Remote Similarity	NPC474778
0.6486	Remote Similarity	NPC327115
0.6486	Remote Similarity	NPC474733
0.6486	Remote Similarity	NPC474732
0.6486	Remote Similarity	NPC470955
0.6486	Remote Similarity	NPC31564
0.6481	Remote Similarity	NPC14151
0.6481	Remote Similarity	NPC121984
0.6481	Remote Similarity	NPC472684
0.6481	Remote Similarity	NPC44963
0.6476	Remote Similarity	NPC263582
0.6475	Remote Similarity	NPC169375
0.6466	Remote Similarity	NPC280725
0.6466	Remote Similarity	NPC263347
0.6466	Remote Similarity	NPC287903
0.646	Remote Similarity	NPC5509
0.646	Remote Similarity	NPC1015
0.646	Remote Similarity	NPC472983
0.646	Remote Similarity	NPC119416
0.646	Remote Similarity	NPC31985
0.6455	Remote Similarity	NPC237712
0.6449	Remote Similarity	NPC308038
0.6446	Remote Similarity	NPC119329
0.6441	Remote Similarity	NPC472730
0.6441	Remote Similarity	NPC153776
0.6441	Remote Similarity	NPC177680
0.6441	Remote Similarity	NPC472729
0.6435	Remote Similarity	NPC115021
0.6435	Remote Similarity	NPC475255
0.6429	Remote Similarity	NPC38885
0.6429	Remote Similarity	NPC208725
0.6429	Remote Similarity	NPC475740
0.6429	Remote Similarity	NPC58063
0.6429	Remote Similarity	NPC96496
0.6423	Remote Similarity	NPC476276
0.6422	Remote Similarity	NPC151519
0.6422	Remote Similarity	NPC212083
0.6422	Remote Similarity	NPC103486
0.641	Remote Similarity	NPC167193
0.641	Remote Similarity	NPC472806
0.6404	Remote Similarity	NPC51486
0.6404	Remote Similarity	NPC134321
0.6404	Remote Similarity	NPC128672
0.6397	Remote Similarity	NPC116057
0.6396	Remote Similarity	NPC476426
0.6396	Remote Similarity	NPC469948
0.6396	Remote Similarity	NPC474218
0.6396	Remote Similarity	NPC79573
0.6396	Remote Similarity	NPC470574
0.6389	Remote Similarity	NPC148685
0.6389	Remote Similarity	NPC104120
0.6389	Remote Similarity	NPC472478
0.6389	Remote Similarity	NPC45495
0.6389	Remote Similarity	NPC157895
0.6387	Remote Similarity	NPC472728
0.6387	Remote Similarity	NPC472727
0.6381	Remote Similarity	NPC114236
0.6379	Remote Similarity	NPC111015
0.6379	Remote Similarity	NPC473314
0.6379	Remote Similarity	NPC477290
0.6378	Remote Similarity	NPC476813
0.6378	Remote Similarity	NPC476814
0.6372	Remote Similarity	NPC471722
0.6372	Remote Similarity	NPC471793
0.6372	Remote Similarity	NPC472802
0.6372	Remote Similarity	NPC471724
0.6372	Remote Similarity	NPC470417
0.6372	Remote Similarity	NPC328539
0.6372	Remote Similarity	NPC328313
0.6372	Remote Similarity	NPC34754
0.6372	Remote Similarity	NPC474854
0.6372	Remote Similarity	NPC471791
0.6372	Remote Similarity	NPC473229
0.6364	Remote Similarity	NPC64600
0.6357	Remote Similarity	NPC476956
0.6356	Remote Similarity	NPC27105
0.6356	Remote Similarity	NPC167380
0.6356	Remote Similarity	NPC125771
0.6356	Remote Similarity	NPC273269
0.6356	Remote Similarity	NPC218902
0.6356	Remote Similarity	NPC89225
0.6356	Remote Similarity	NPC473161
0.6355	Remote Similarity	NPC62336
0.6348	Remote Similarity	NPC473998
0.6348	Remote Similarity	NPC185936
0.6348	Remote Similarity	NPC168027
0.6348	Remote Similarity	NPC154101
0.6343	Remote Similarity	NPC156797
0.6339	Remote Similarity	NPC262085
0.6339	Remote Similarity	NPC222613
0.6339	Remote Similarity	NPC475181
0.6339	Remote Similarity	NPC72133
0.6339	Remote Similarity	NPC76164
0.6339	Remote Similarity	NPC118648
0.6339	Remote Similarity	NPC475022
0.6339	Remote Similarity	NPC153699
0.633	Remote Similarity	NPC226068
0.633	Remote Similarity	NPC189237
0.633	Remote Similarity	NPC136150
0.6325	Remote Similarity	NPC148523
0.6325	Remote Similarity	NPC472485
0.6325	Remote Similarity	NPC88310
0.6321	Remote Similarity	NPC470525
0.6321	Remote Similarity	NPC180886
0.6316	Remote Similarity	NPC472477
0.6316	Remote Similarity	NPC472475
0.6316	Remote Similarity	NPC86319
0.6316	Remote Similarity	NPC54689
0.6316	Remote Similarity	NPC275740
0.6316	Remote Similarity	NPC26959
0.6316	Remote Similarity	NPC477973
0.6316	Remote Similarity	NPC309603
0.6316	Remote Similarity	NPC310010
0.6316	Remote Similarity	NPC326627
0.6316	Remote Similarity	NPC472971
0.6316	Remote Similarity	NPC472970
0.6316	Remote Similarity	NPC186688
0.6316	Remote Similarity	NPC473999
0.6316	Remote Similarity	NPC268406
0.6311	Remote Similarity	NPC14537
0.6311	Remote Similarity	NPC472616
0.6306	Remote Similarity	NPC82902
0.6306	Remote Similarity	NPC221758
0.6306	Remote Similarity	NPC59453
0.6306	Remote Similarity	NPC470812
0.6303	Remote Similarity	NPC472687
0.6303	Remote Similarity	NPC471330
0.6303	Remote Similarity	NPC471331
0.6303	Remote Similarity	NPC99657
0.6303	Remote Similarity	NPC203388
0.6303	Remote Similarity	NPC147954
0.6296	Remote Similarity	NPC474113
0.6296	Remote Similarity	NPC7232
0.6296	Remote Similarity	NPC472490
0.6293	Remote Similarity	NPC134826
0.6293	Remote Similarity	NPC66429
0.6293	Remote Similarity	NPC233118
0.6293	Remote Similarity	NPC152897
0.6293	Remote Similarity	NPC472930
0.6283	Remote Similarity	NPC141292
0.6283	Remote Similarity	NPC158141
0.6283	Remote Similarity	NPC312215
0.6283	Remote Similarity	NPC317590
0.6283	Remote Similarity	NPC173089
0.6283	Remote Similarity	NPC472481

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 NPC7797 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	93
0.1-0.2	622
0.2-0.3	3585
0.3-0.4	3805
0.4-0.5	767
0.5-0.6	252
0.6-0.7	26
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
0.6803	Remote Similarity	NPD5215	Approved
0.6803	Remote Similarity	NPD1719	Phase 1
0.6693	Remote Similarity	NPD4522	Approved
0.664	Remote Similarity	NPD5167	Approved
0.6636	Remote Similarity	NPD3618	Phase 1
0.6606	Remote Similarity	NPD3666	Approved
0.6606	Remote Similarity	NPD3665	Phase 1
0.6606	Remote Similarity	NPD3133	Approved
0.6585	Remote Similarity	NPD5169	Approved
0.6557	Remote Similarity	NPD5168	Approved
0.6532	Remote Similarity	NPD5127	Approved
0.6532	Remote Similarity	NPD5216	Approved
0.6532	Remote Similarity	NPD5217	Approved
0.6475	Remote Similarity	NPD6334	Approved
0.6475	Remote Similarity	NPD6333	Approved
0.6434	Remote Similarity	NPD7100	Approved
0.6422	Remote Similarity	NPD3667	Approved
0.6417	Remote Similarity	NPD5091	Approved
0.6339	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5279	Phase 3
0.6324	Remote Similarity	NPD6914	Discontinued
0.6316	Remote Similarity	NPD4753	Phase 2
0.6316	Remote Similarity	NPD5328	Approved
0.6306	Remote Similarity	NPD4786	Approved
0.6293	Remote Similarity	NPD4202	Approved
0.629	Remote Similarity	NPD5128	Approved
0.6271	Remote Similarity	NPD4697	Phase 3
0.625	Remote Similarity	NPD6404	Discontinued
0.6231	Remote Similarity	NPD6313	Approved
0.6231	Remote Similarity	NPD6314	Approved
0.6231	Remote Similarity	NPD6335	Approved
0.6218	Remote Similarity	NPD4755	Approved
0.6207	Remote Similarity	NPD6079	Approved
0.6207	Remote Similarity	NPD7515	Phase 2
0.6204	Remote Similarity	NPD5956	Approved
0.6202	Remote Similarity	NPD6868	Approved
0.619	Remote Similarity	NPD6420	Discontinued
0.6186	Remote Similarity	NPD4629	Approved
0.6186	Remote Similarity	NPD5210	Approved
0.6183	Remote Similarity	NPD7101	Approved
0.6154	Remote Similarity	NPD5133	Approved
0.6154	Remote Similarity	NPD6399	Phase 3
0.6134	Remote Similarity	NPD5222	Approved
0.6134	Remote Similarity	NPD5221	Approved
0.6134	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD4223	Phase 3
0.6126	Remote Similarity	NPD4221	Approved
0.6116	Remote Similarity	NPD4700	Approved
0.6116	Remote Similarity	NPD5286	Approved
0.6116	Remote Similarity	NPD4696	Approved
0.6116	Remote Similarity	NPD5285	Approved
0.6091	Remote Similarity	NPD4695	Discontinued
0.6083	Remote Similarity	NPD5173	Approved
0.6083	Remote Similarity	NPD7902	Approved
0.6068	Remote Similarity	NPD5281	Approved
0.6068	Remote Similarity	NPD5284	Approved
0.6066	Remote Similarity	NPD5223	Approved
0.6058	Remote Similarity	NPD6033	Approved
0.6018	Remote Similarity	NPD3668	Phase 3
0.6018	Remote Similarity	NPD4197	Approved
0.6016	Remote Similarity	NPD5225	Approved
0.6016	Remote Similarity	NPD4633	Approved
0.6016	Remote Similarity	NPD5226	Approved
0.6016	Remote Similarity	NPD5224	Approved
0.6016	Remote Similarity	NPD5211	Phase 2
0.5983	Remote Similarity	NPD4096	Approved
0.5968	Remote Similarity	NPD5175	Approved
0.5968	Remote Similarity	NPD4754	Approved
0.5968	Remote Similarity	NPD5174	Approved
0.5966	Remote Similarity	NPD7748	Approved
0.5965	Remote Similarity	NPD5329	Approved
0.595	Remote Similarity	NPD6083	Phase 2
0.595	Remote Similarity	NPD6084	Phase 2
0.5938	Remote Similarity	NPD4634	Approved
0.5923	Remote Similarity	NPD4632	Approved
0.592	Remote Similarity	NPD5141	Approved
0.5917	Remote Similarity	NPD5695	Phase 3
0.5913	Remote Similarity	NPD6684	Approved
0.5913	Remote Similarity	NPD4693	Phase 3
0.5913	Remote Similarity	NPD4694	Approved
0.5913	Remote Similarity	NPD5330	Approved
0.5913	Remote Similarity	NPD7521	Approved
0.5913	Remote Similarity	NPD7146	Approved
0.5913	Remote Similarity	NPD6409	Approved
0.5913	Remote Similarity	NPD4689	Approved
0.5913	Remote Similarity	NPD4688	Approved
0.5913	Remote Similarity	NPD4519	Discontinued
0.5913	Remote Similarity	NPD5690	Phase 2
0.5913	Remote Similarity	NPD5205	Approved
0.5913	Remote Similarity	NPD5280	Approved
0.5913	Remote Similarity	NPD7334	Approved
0.5913	Remote Similarity	NPD4690	Approved
0.5913	Remote Similarity	NPD4138	Approved
0.5913	Remote Similarity	NPD4623	Approved
0.5912	Remote Similarity	NPD6336	Discontinued
0.5909	Remote Similarity	NPD3617	Approved
0.5902	Remote Similarity	NPD5696	Approved
0.5882	Remote Similarity	NPD5781	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7128	Approved
0.5873	Remote Similarity	NPD6402	Approved
0.5873	Remote Similarity	NPD4767	Approved
0.5873	Remote Similarity	NPD4768	Approved
0.5873	Remote Similarity	NPD6675	Approved
0.5873	Remote Similarity	NPD5739	Approved
0.5859	Remote Similarity	NPD6372	Approved
0.5859	Remote Similarity	NPD6373	Approved
0.5852	Remote Similarity	NPD5983	Phase 2
0.5847	Remote Similarity	NPD790	Approved
0.5833	Remote Similarity	NPD5282	Discontinued
0.5833	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7900	Approved
0.5827	Remote Similarity	NPD5697	Approved
0.5827	Remote Similarity	NPD6614	Approved
0.5827	Remote Similarity	NPD6412	Phase 2
0.5827	Remote Similarity	NPD5701	Approved
0.5812	Remote Similarity	NPD5737	Approved
0.5812	Remote Similarity	NPD6672	Approved
0.5812	Remote Similarity	NPD6903	Approved
0.5812	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6009	Approved
0.5785	Remote Similarity	NPD5654	Approved
0.5781	Remote Similarity	NPD7320	Approved
0.5781	Remote Similarity	NPD4730	Approved
0.5781	Remote Similarity	NPD6899	Approved
0.5781	Remote Similarity	NPD6011	Approved
0.5781	Remote Similarity	NPD4729	Approved
0.5781	Remote Similarity	NPD6881	Approved
0.5769	Remote Similarity	NPD6650	Approved
0.5769	Remote Similarity	NPD6649	Approved
0.5738	Remote Similarity	NPD7614	Phase 1
0.5736	Remote Similarity	NPD6013	Approved
0.5736	Remote Similarity	NPD6014	Approved
0.5736	Remote Similarity	NPD6012	Approved
0.5735	Remote Similarity	NPD6909	Approved
0.5735	Remote Similarity	NPD6908	Approved
0.5702	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD7102	Approved
0.5692	Remote Similarity	NPD5247	Approved
0.5692	Remote Similarity	NPD5135	Approved
0.5692	Remote Similarity	NPD5248	Approved
0.5692	Remote Similarity	NPD5250	Approved
0.5692	Remote Similarity	NPD5249	Phase 3
0.5692	Remote Similarity	NPD6883	Approved
0.5692	Remote Similarity	NPD7290	Approved
0.5692	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD5251	Approved
0.5691	Remote Similarity	NPD5959	Approved
0.5672	Remote Similarity	NPD7500	Approved
0.5672	Remote Similarity	NPD7115	Discovery
0.5667	Remote Similarity	NPD6411	Approved
0.5656	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD4788	Approved
0.5649	Remote Similarity	NPD6869	Approved
0.5649	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5649	Remote Similarity	NPD6847	Approved
0.5649	Remote Similarity	NPD8130	Phase 1
0.5649	Remote Similarity	NPD6617	Approved
0.5645	Remote Similarity	NPD4225	Approved
0.563	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7333	Discontinued
0.5607	Remote Similarity	NPD4137	Phase 3
0.5606	Remote Similarity	NPD8297	Approved
0.5606	Remote Similarity	NPD6882	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