NPASS Compound

Structure

NPC302169 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 1.5000 2.5981 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 2.3660 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 1.7321 0.0000 N 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 -2.2321 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 0.3660 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 22 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 12 2 0 0 0 0 9 12 1 0 0 0 0 10 12 1 0 0 0 0 11 19 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 13 20 2 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 14 21 2 0 0 0 0 15 10 1 1 0 0 0 15 17 1 0 0 0 0 15 22 1 0 0 0 0 16 11 1 1 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	354.11
Volume:	340.379
LogP:	2.247
LogD:	2.069
LogS:	-3.674
# Rotatable Bonds:	5
TPSA:	60.85
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.863
Synthetic Accessibility Score:	4.172
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.829
MDCK Permeability:	2.913605931098573e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.595
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.991
Plasma Protein Binding (PPB):	92.26853942871094%
Volume Distribution (VD):	0.852
Pgp-substrate:	18.979129791259766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.084
CYP1A2-substrate:	0.657
CYP2C19-inhibitor:	0.925
CYP2C19-substrate:	0.962
CYP2C9-inhibitor:	0.941
CYP2C9-substrate:	0.124
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.078
CYP3A4-inhibitor:	0.382
CYP3A4-substrate:	0.967

ADMET: Excretion

Clearance (CL):	8.14
Half-life (T1/2):	0.927

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.045
Rat Oral Acute Toxicity:	0.174
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.632
Carcinogencity:	0.09
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.0

Download Data

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

Natural Product: NPC302169

Natural Product ID:	NPC302169
*Common Name:**	Bisdethiodi(Methylthio)Hyalodendrin
IUPAC Name:	(3R,6R)-3-benzyl-6-(hydroxymethyl)-1,4-dimethyl-3,6-bis(methylsulfanyl)piperazine-2,5-dione
Synonyms:	Bisdethiodi(Methylthio)Hyalodendrin
Standard InCHIKey:	WXIJHVRXTHDGKV-HZPDHXFCSA-N
Standard InCHI:	InChI=1S/C16H22N2O3S2/c1-17-14(21)16(11-19,23-4)18(2)13(20)15(17,22-3)10-12-8-6-5-7-9-12/h5-9,19H,10-11H2,1-4H3/t15-,16-/m1/s1
SMILES:	CN1C(=O)[C@](CO)(N(C)C(=O)[C@@]1(Cc1ccccc1)SC)SC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL562045
PubChem CID:	13942399
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives

*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
NPO10809	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	Cordyceps-colonizing isolate of Isaria farinosa	n.a.	n.a.	PMID[19572613]
NPO10809	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21158423]
NPO10809	Isaria farinosa	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21495659]
NPO10809	Isaria farinosa	Species	Cordycipitaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	GI50	>	112900.0	nM	PMID[530422]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	112900.0	nM	PMID[530422]

☑ 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 NPC302169 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	91
0.1-0.2	1307
0.2-0.3	8339
0.3-0.4	21256
0.4-0.5	10063
0.5-0.6	1296
0.6-0.7	314
0.7-0.8	30
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7863	Intermediate Similarity	NPC473418
0.7626	Intermediate Similarity	NPC471680
0.7609	Intermediate Similarity	NPC470301
0.7456	Intermediate Similarity	NPC71140
0.74	Intermediate Similarity	NPC328270
0.7328	Intermediate Similarity	NPC474082
0.7328	Intermediate Similarity	NPC175726
0.7239	Intermediate Similarity	NPC319766
0.7222	Intermediate Similarity	NPC105717
0.7209	Intermediate Similarity	NPC220698
0.7188	Intermediate Similarity	NPC315276
0.7188	Intermediate Similarity	NPC14672
0.7188	Intermediate Similarity	NPC285926
0.7165	Intermediate Similarity	NPC33742
0.7132	Intermediate Similarity	NPC470545
0.7132	Intermediate Similarity	NPC300315
0.7103	Intermediate Similarity	NPC189908
0.7099	Intermediate Similarity	NPC27833
0.7099	Intermediate Similarity	NPC200964
0.7087	Intermediate Similarity	NPC276949
0.7087	Intermediate Similarity	NPC35850
0.7077	Intermediate Similarity	NPC470546
0.7068	Intermediate Similarity	NPC6975
0.7059	Intermediate Similarity	NPC469666
0.7054	Intermediate Similarity	NPC470544
0.7045	Intermediate Similarity	NPC71684
0.7027	Intermediate Similarity	NPC286551
0.7021	Intermediate Similarity	NPC89489
0.7015	Intermediate Similarity	NPC222466
0.6963	Remote Similarity	NPC101719
0.6939	Remote Similarity	NPC283783
0.6935	Remote Similarity	NPC45033
0.6934	Remote Similarity	NPC473322
0.6929	Remote Similarity	NPC248283
0.6923	Remote Similarity	NPC473661
0.6923	Remote Similarity	NPC239357
0.6917	Remote Similarity	NPC202521
0.6897	Remote Similarity	NPC322878
0.6875	Remote Similarity	NPC468984
0.6857	Remote Similarity	NPC287401
0.6853	Remote Similarity	NPC476259
0.6853	Remote Similarity	NPC307357
0.6853	Remote Similarity	NPC46098
0.6853	Remote Similarity	NPC268841
0.6853	Remote Similarity	NPC239762
0.6853	Remote Similarity	NPC163392
0.6842	Remote Similarity	NPC476990
0.6835	Remote Similarity	NPC130309
0.6812	Remote Similarity	NPC111428
0.6786	Remote Similarity	NPC257390
0.6783	Remote Similarity	NPC470884
0.6783	Remote Similarity	NPC178662
0.6783	Remote Similarity	NPC98424
0.6783	Remote Similarity	NPC476133
0.6783	Remote Similarity	NPC92784
0.6777	Remote Similarity	NPC322598
0.6768	Remote Similarity	NPC302235
0.6763	Remote Similarity	NPC200589
0.6741	Remote Similarity	NPC213126
0.6741	Remote Similarity	NPC252878
0.6741	Remote Similarity	NPC84281
0.6741	Remote Similarity	NPC169485
0.6741	Remote Similarity	NPC317474
0.6741	Remote Similarity	NPC291027
0.6726	Remote Similarity	NPC474088
0.6714	Remote Similarity	NPC255447
0.6691	Remote Similarity	NPC46427
0.669	Remote Similarity	NPC263493
0.669	Remote Similarity	NPC269398
0.6667	Remote Similarity	NPC209509
0.6667	Remote Similarity	NPC136453
0.6667	Remote Similarity	NPC256452
0.6646	Remote Similarity	NPC318930
0.6646	Remote Similarity	NPC317362
0.6644	Remote Similarity	NPC161069
0.6644	Remote Similarity	NPC176226
0.6644	Remote Similarity	NPC139326
0.6643	Remote Similarity	NPC69496
0.6642	Remote Similarity	NPC22746
0.6622	Remote Similarity	NPC314358
0.6619	Remote Similarity	NPC152850
0.6619	Remote Similarity	NPC89923
0.6619	Remote Similarity	NPC71933
0.6619	Remote Similarity	NPC105114
0.6619	Remote Similarity	NPC239990
0.66	Remote Similarity	NPC13470
0.6599	Remote Similarity	NPC52748
0.6599	Remote Similarity	NPC314388
0.6599	Remote Similarity	NPC315283
0.6594	Remote Similarity	NPC474847
0.6587	Remote Similarity	NPC67043
0.6575	Remote Similarity	NPC469427
0.6575	Remote Similarity	NPC469426
0.6554	Remote Similarity	NPC477217
0.6554	Remote Similarity	NPC201244
0.6554	Remote Similarity	NPC313867
0.6554	Remote Similarity	NPC316008
0.6552	Remote Similarity	NPC132636
0.6543	Remote Similarity	NPC326407
0.6543	Remote Similarity	NPC317725
0.6531	Remote Similarity	NPC197682
0.6528	Remote Similarity	NPC474855
0.6528	Remote Similarity	NPC49577
0.6528	Remote Similarity	NPC76785
0.6528	Remote Similarity	NPC9687
0.6528	Remote Similarity	NPC475318
0.6528	Remote Similarity	NPC476102
0.6528	Remote Similarity	NPC118099
0.6528	Remote Similarity	NPC79465
0.6528	Remote Similarity	NPC273907
0.6528	Remote Similarity	NPC151706
0.6528	Remote Similarity	NPC475598
0.6528	Remote Similarity	NPC474811
0.6528	Remote Similarity	NPC474787
0.6528	Remote Similarity	NPC90194
0.6528	Remote Similarity	NPC293377
0.6528	Remote Similarity	NPC260045
0.651	Remote Similarity	NPC262077
0.6503	Remote Similarity	NPC233910
0.6503	Remote Similarity	NPC245836
0.6496	Remote Similarity	NPC17497
0.6496	Remote Similarity	NPC305602
0.6493	Remote Similarity	NPC470788
0.6486	Remote Similarity	NPC476978
0.6483	Remote Similarity	NPC127741
0.6483	Remote Similarity	NPC471264
0.6483	Remote Similarity	NPC68865
0.6483	Remote Similarity	NPC471265
0.6479	Remote Similarity	NPC157311
0.6467	Remote Similarity	NPC135121
0.6467	Remote Similarity	NPC138775
0.6467	Remote Similarity	NPC145113
0.6463	Remote Similarity	NPC168113
0.6457	Remote Similarity	NPC167336
0.6443	Remote Similarity	NPC315266
0.6443	Remote Similarity	NPC5620
0.6434	Remote Similarity	NPC8761
0.6434	Remote Similarity	NPC44805
0.6424	Remote Similarity	NPC471820
0.6424	Remote Similarity	NPC471821
0.6418	Remote Similarity	NPC476155
0.6418	Remote Similarity	NPC17581
0.6406	Remote Similarity	NPC471447
0.6403	Remote Similarity	NPC285394
0.6382	Remote Similarity	NPC2501
0.6364	Remote Similarity	NPC122590
0.6364	Remote Similarity	NPC473341
0.6352	Remote Similarity	NPC471053
0.6352	Remote Similarity	NPC471051
0.6352	Remote Similarity	NPC471052
0.6349	Remote Similarity	NPC329375
0.6345	Remote Similarity	NPC474473
0.6345	Remote Similarity	NPC141050
0.6328	Remote Similarity	NPC476198
0.632	Remote Similarity	NPC12730
0.6319	Remote Similarity	NPC325479
0.6316	Remote Similarity	NPC240848
0.6312	Remote Similarity	NPC65310
0.6309	Remote Similarity	NPC251439
0.6299	Remote Similarity	NPC162104
0.6289	Remote Similarity	NPC73655
0.6288	Remote Similarity	NPC475013
0.6287	Remote Similarity	NPC166169
0.6279	Remote Similarity	NPC473498
0.6275	Remote Similarity	NPC129666
0.626	Remote Similarity	NPC158854
0.626	Remote Similarity	NPC292758
0.626	Remote Similarity	NPC65855
0.625	Remote Similarity	NPC329761
0.625	Remote Similarity	NPC225648
0.6234	Remote Similarity	NPC473491
0.6232	Remote Similarity	NPC478016
0.6232	Remote Similarity	NPC478015
0.6232	Remote Similarity	NPC478014
0.6226	Remote Similarity	NPC471527
0.6224	Remote Similarity	NPC81092
0.6224	Remote Similarity	NPC103605
0.6222	Remote Similarity	NPC473573
0.6216	Remote Similarity	NPC313694
0.6216	Remote Similarity	NPC242159
0.6214	Remote Similarity	NPC35996
0.6212	Remote Similarity	NPC319579
0.6207	Remote Similarity	NPC246079
0.6203	Remote Similarity	NPC197743
0.6203	Remote Similarity	NPC297145
0.6203	Remote Similarity	NPC324850
0.6194	Remote Similarity	NPC476048
0.6185	Remote Similarity	NPC128582
0.6181	Remote Similarity	NPC179224
0.6179	Remote Similarity	NPC474974
0.6172	Remote Similarity	NPC164859
0.6164	Remote Similarity	NPC1390
0.6164	Remote Similarity	NPC62104
0.616	Remote Similarity	NPC293628
0.616	Remote Similarity	NPC472258
0.616	Remote Similarity	NPC10781
0.616	Remote Similarity	NPC122493
0.6149	Remote Similarity	NPC477526
0.6148	Remote Similarity	NPC187725
0.6148	Remote Similarity	NPC141607

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 NPC302169 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	91
0.1-0.2	446
0.2-0.3	943
0.3-0.4	2925
0.4-0.5	3255
0.5-0.6	1187
0.6-0.7	291
0.7-0.8	12
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
0.7797	Intermediate Similarity	NPD7130	Phase 3
0.7744	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD6792	Phase 3
0.7328	Intermediate Similarity	NPD6408	Phase 1
0.7308	Intermediate Similarity	NPD5187	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6552	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4677	Discontinued
0.7266	Intermediate Similarity	NPD4126	Approved
0.7259	Intermediate Similarity	NPD4125	Approved
0.7254	Intermediate Similarity	NPD5264	Approved
0.7254	Intermediate Similarity	NPD5265	Approved
0.7252	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4803	Discontinued
0.7165	Intermediate Similarity	NPD3551	Approved
0.7122	Intermediate Similarity	NPD3577	Discontinued
0.7077	Intermediate Similarity	NPD6343	Approved
0.7077	Intermediate Similarity	NPD6345	Approved
0.7063	Intermediate Similarity	NPD2436	Approved
0.7063	Intermediate Similarity	NPD2437	Approved
0.704	Intermediate Similarity	NPD3581	Discontinued
0.7037	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5581	Approved
0.7021	Intermediate Similarity	NPD6294	Approved
0.7021	Intermediate Similarity	NPD6295	Approved
0.7	Intermediate Similarity	NPD5991	Approved
0.7	Intermediate Similarity	NPD5990	Approved
0.6986	Remote Similarity	NPD3509	Approved
0.6986	Remote Similarity	NPD3510	Approved
0.6985	Remote Similarity	NPD5339	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5638	Approved
0.6957	Remote Similarity	NPD2045	Approved
0.6957	Remote Similarity	NPD2047	Approved
0.6957	Remote Similarity	NPD21	Approved
0.6957	Remote Similarity	NPD2046	Approved
0.6957	Remote Similarity	NPD2043	Approved
0.6957	Remote Similarity	NPD2048	Approved
0.6957	Remote Similarity	NPD2044	Approved
0.6957	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2051	Approved
0.695	Remote Similarity	NPD8173	Phase 2
0.695	Remote Similarity	NPD5004	Approved
0.695	Remote Similarity	NPD8172	Phase 2
0.694	Remote Similarity	NPD2584	Suspended
0.694	Remote Similarity	NPD3071	Approved
0.694	Remote Similarity	NPD3072	Approved
0.694	Remote Similarity	NPD3073	Approved
0.6939	Remote Similarity	NPD5614	Approved
0.6939	Remote Similarity	NPD5613	Approved
0.6934	Remote Similarity	NPD3626	Phase 3
0.6934	Remote Similarity	NPD4177	Approved
0.6934	Remote Similarity	NPD4175	Approved
0.6929	Remote Similarity	NPD5296	Approved
0.6906	Remote Similarity	NPD5299	Approved
0.6879	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2022	Approved
0.6875	Remote Similarity	NPD2088	Approved
0.6875	Remote Similarity	NPD480	Approved
0.6875	Remote Similarity	NPD2087	Approved
0.6866	Remote Similarity	NPD4762	Approved
0.6866	Remote Similarity	NPD4761	Approved
0.6866	Remote Similarity	NPD3624	Phase 2
0.6861	Remote Similarity	NPD4151	Approved
0.6861	Remote Similarity	NPD3604	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3648	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6806	Phase 1
0.6838	Remote Similarity	NPD5367	Discontinued
0.6838	Remote Similarity	NPD2634	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3040	Approved
0.6809	Remote Similarity	NPD6623	Phase 3
0.6809	Remote Similarity	NPD5323	Approved
0.6809	Remote Similarity	NPD4153	Approved
0.6797	Remote Similarity	NPD2124	Approved
0.6783	Remote Similarity	NPD4705	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3508	Approved
0.6763	Remote Similarity	NPD5263	Approved
0.6761	Remote Similarity	NPD7622	Phase 2
0.6761	Remote Similarity	NPD7733	Phase 2
0.6741	Remote Similarity	NPD4217	Approved
0.6741	Remote Similarity	NPD4478	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD2612	Approved
0.6741	Remote Similarity	NPD2609	Approved
0.6741	Remote Similarity	NPD2608	Approved
0.6741	Remote Similarity	NPD2611	Approved
0.6741	Remote Similarity	NPD3132	Approved
0.6741	Remote Similarity	NPD2610	Approved
0.6741	Remote Similarity	NPD3131	Approved
0.6741	Remote Similarity	NPD4215	Approved
0.6741	Remote Similarity	NPD4218	Approved
0.6741	Remote Similarity	NPD4216	Approved
0.6736	Remote Similarity	NPD3480	Approved
0.672	Remote Similarity	NPD1576	Approved
0.6715	Remote Similarity	NPD2031	Discontinued
0.6713	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD6073	Approved
0.6711	Remote Similarity	NPD7892	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD8323	Discontinued
0.6667	Remote Similarity	NPD7679	Phase 2
0.6667	Remote Similarity	NPD753	Approved
0.6645	Remote Similarity	NPD4648	Approved
0.6645	Remote Similarity	NPD4647	Approved
0.6645	Remote Similarity	NPD4646	Approved
0.6643	Remote Similarity	NPD2613	Approved
0.6643	Remote Similarity	NPD4676	Approved
0.6641	Remote Similarity	NPD5589	Approved
0.6641	Remote Similarity	NPD3867	Phase 2
0.6639	Remote Similarity	NPD466	Approved
0.6623	Remote Similarity	NPD5229	Approved
0.6623	Remote Similarity	NPD5230	Approved
0.662	Remote Similarity	NPD4680	Discontinued
0.6619	Remote Similarity	NPD3588	Discontinued
0.6617	Remote Similarity	NPD1713	Approved
0.66	Remote Similarity	NPD2014	Approved
0.66	Remote Similarity	NPD2013	Approved
0.66	Remote Similarity	NPD3988	Approved
0.66	Remote Similarity	NPD3987	Approved
0.66	Remote Similarity	NPD2016	Approved
0.6597	Remote Similarity	NPD5725	Approved
0.6585	Remote Similarity	NPD742	Approved
0.6567	Remote Similarity	NPD998	Approved
0.6558	Remote Similarity	NPD2891	Approved
0.6557	Remote Similarity	NPD1099	Approved
0.6557	Remote Similarity	NPD1100	Approved
0.6519	Remote Similarity	NPD4504	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD2508	Discontinued
0.6503	Remote Similarity	NPD3614	Approved
0.6503	Remote Similarity	NPD3090	Approved
0.6503	Remote Similarity	NPD3087	Approved
0.6503	Remote Similarity	NPD2573	Approved
0.6503	Remote Similarity	NPD3615	Approved
0.6503	Remote Similarity	NPD2566	Approved
0.6503	Remote Similarity	NPD3616	Approved
0.6503	Remote Similarity	NPD3088	Approved
0.6503	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD3089	Approved
0.6503	Remote Similarity	NPD2570	Approved
0.6503	Remote Similarity	NPD2574	Discontinued
0.6503	Remote Similarity	NPD2571	Approved
0.6503	Remote Similarity	NPD4746	Phase 3
0.6503	Remote Similarity	NPD4745	Approved
0.65	Remote Similarity	NPD3578	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD3806	Clinical (unspecified phase)
0.648	Remote Similarity	NPD6027	Approved
0.648	Remote Similarity	NPD6024	Approved
0.648	Remote Similarity	NPD6588	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD2056	Discontinued
0.6471	Remote Similarity	NPD3064	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4164	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD1323	Discontinued
0.6466	Remote Similarity	NPD1025	Discontinued
0.6458	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD8416	Discontinued
0.6457	Remote Similarity	NPD1765	Approved
0.6457	Remote Similarity	NPD1766	Approved
0.6457	Remote Similarity	NPD1761	Approved
0.6457	Remote Similarity	NPD1763	Approved
0.6457	Remote Similarity	NPD1767	Approved
0.6447	Remote Similarity	NPD4432	Discontinued
0.6444	Remote Similarity	NPD474	Approved
0.6443	Remote Similarity	NPD6860	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3598	Phase 3
0.6438	Remote Similarity	NPD6901	Phase 3
0.6434	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD4557	Approved
0.6429	Remote Similarity	NPD3029	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD3519	Discontinued
0.6419	Remote Similarity	NPD7720	Phase 2
0.6419	Remote Similarity	NPD4152	Approved
0.6418	Remote Similarity	NPD5549	Approved
0.6418	Remote Similarity	NPD5550	Approved
0.6418	Remote Similarity	NPD3123	Discovery
0.6414	Remote Similarity	NPD4686	Approved
0.6414	Remote Similarity	NPD5780	Phase 2
0.6414	Remote Similarity	NPD4684	Phase 3
0.6414	Remote Similarity	NPD4685	Phase 3
0.641	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7979	Clinical (unspecified phase)
0.6403	Remote Similarity	NPD5157	Phase 1
0.6403	Remote Similarity	NPD5159	Phase 2
0.6403	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD3543	Discontinued
0.6389	Remote Similarity	NPD7634	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5747	Discontinued
0.6389	Remote Similarity	NPD7086	Phase 2
0.6382	Remote Similarity	NPD6088	Approved
0.6377	Remote Similarity	NPD1948	Approved
0.6364	Remote Similarity	NPD4794	Discontinued
0.6357	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.635	Remote Similarity	NPD4733	Approved
0.635	Remote Similarity	NPD5723	Approved
0.6349	Remote Similarity	NPD2171	Approved
0.6349	Remote Similarity	NPD813	Approved
0.6349	Remote Similarity	NPD2193	Phase 2
0.6349	Remote Similarity	NPD2648	Phase 3
0.6345	Remote Similarity	NPD5272	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