NPASS Compound

Structure

CID198401 OpenBabel06191715582D 26 30 0 0 1 0 0 0 0 0999 V2000 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1422 -2.0896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1672 -2.3121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6117 3.0125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4369 -1.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4871 -1.5791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6922 2.6195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2697 2.2594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 -0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 1.6235 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 1.4010 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 -3.1906 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 3 2 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 4 7 1 0 0 0 0 4 10 1 0 0 0 0 5 13 2 0 0 0 0 6 16 2 0 0 0 0 8 9 2 0 0 0 0 8 12 1 0 0 0 0 9 15 1 0 0 0 0 10 22 1 0 0 0 0 11 12 2 0 0 0 0 11 14 1 0 0 0 0 12 26 1 0 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 7 1 1 0 0 0 17 18 1 0 0 0 0 17 22 1 0 0 0 0 18 21 2 0 0 0 0 18 23 1 0 0 0 0 19 22 1 0 0 0 0 19 24 2 0 0 0 0 20 23 1 0 0 0 0 20 25 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	347.13
Volume:	347.327
LogP:	1.945
LogD:	1.703
LogS:	-5.071
# Rotatable Bonds:	1
TPSA:	64.43
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.679
Synthetic Accessibility Score:	2.732
Fsp3:	0.25
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:	-4.726
MDCK Permeability:	1.8245113096782006e-05
Pgp-inhibitor:	0.061
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.082

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.973
Plasma Protein Binding (PPB):	78.04375457763672%
Volume Distribution (VD):	0.815
Pgp-substrate:	15.19129467010498%

ADMET: Metabolism

CYP1A2-inhibitor:	0.112
CYP1A2-substrate:	0.863
CYP2C19-inhibitor:	0.489
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.647
CYP2C9-substrate:	0.768
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.702
CYP3A4-inhibitor:	0.725
CYP3A4-substrate:	0.915

ADMET: Excretion

Clearance (CL):	2.473
Half-life (T1/2):	0.417

ADMET: Toxicity

hERG Blockers:	0.142
Human Hepatotoxicity (H-HT):	0.965
Drug-inuced Liver Injury (DILI):	0.894
AMES Toxicity:	0.232
Rat Oral Acute Toxicity:	0.13
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.119
Carcinogencity:	0.905
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.66

Download Data

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

Natural Product: NPC198401

Natural Product ID:	NPC198401
*Common Name:**	MLEAYJRUKNTODR-KRWDZBQOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MLEAYJRUKNTODR-KRWDZBQOSA-N
Standard InCHI:	InChI=1S/C20H17N3O3/c1-26-12-8-9-15-14(11-12)20(25)23-16-6-3-2-5-13(16)19(24)22-10-4-7-17(22)18(23)21-15/h2-3,5-6,8-9,11,17H,4,7,10H2,1H3/t17-/m0/s1
SMILES:	COc1ccc2c(c1)c(=O)n1c(n2)[C@@H]2CCCN2C(=O)c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2435957
PubChem CID:	46184995
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001132] Pyrimidodiazepines

*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
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11170686]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16156520]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21043476]
NPO14094	Aspergillus ochraceus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	1500.0	nM	PMID[451824]

☑ 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 NPC198401 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	636
0.1-0.2	5285
0.2-0.3	12014
0.3-0.4	10127
0.4-0.5	10588
0.5-0.6	2885
0.6-0.7	1008
0.7-0.8	138
0.8-0.85	12
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8251	Intermediate Similarity	NPC314659
0.8229	Intermediate Similarity	NPC93653
0.8197	Intermediate Similarity	NPC197335
0.8138	Intermediate Similarity	NPC92803
0.8032	Intermediate Similarity	NPC18890
0.802	Intermediate Similarity	NPC16249
0.8019	Intermediate Similarity	NPC157931
0.8	Intermediate Similarity	NPC270301
0.7933	Intermediate Similarity	NPC257851
0.7831	Intermediate Similarity	NPC87391
0.7692	Intermediate Similarity	NPC471130
0.7585	Intermediate Similarity	NPC313327
0.7582	Intermediate Similarity	NPC88970
0.7566	Intermediate Similarity	NPC85613
0.7566	Intermediate Similarity	NPC5167
0.7559	Intermediate Similarity	NPC471762
0.7477	Intermediate Similarity	NPC66777
0.7405	Intermediate Similarity	NPC299582
0.7371	Intermediate Similarity	NPC150308
0.7299	Intermediate Similarity	NPC248601
0.7259	Intermediate Similarity	NPC471195
0.7259	Intermediate Similarity	NPC471196
0.7251	Intermediate Similarity	NPC244425
0.7251	Intermediate Similarity	NPC471197
0.7251	Intermediate Similarity	NPC15384
0.7249	Intermediate Similarity	NPC303374
0.7233	Intermediate Similarity	NPC478075
0.7225	Intermediate Similarity	NPC300299
0.7225	Intermediate Similarity	NPC475607
0.722	Intermediate Similarity	NPC163829
0.7217	Intermediate Similarity	NPC471198
0.7202	Intermediate Similarity	NPC283810
0.7188	Intermediate Similarity	NPC474081
0.7178	Intermediate Similarity	NPC71124
0.7173	Intermediate Similarity	NPC475594
0.7171	Intermediate Similarity	NPC295548
0.7164	Intermediate Similarity	NPC472539
0.7164	Intermediate Similarity	NPC472540
0.7164	Intermediate Similarity	NPC470787
0.7159	Intermediate Similarity	NPC207554
0.7158	Intermediate Similarity	NPC471648
0.7151	Intermediate Similarity	NPC207428
0.7129	Intermediate Similarity	NPC472541
0.7129	Intermediate Similarity	NPC472542
0.7129	Intermediate Similarity	NPC471304
0.7115	Intermediate Similarity	NPC285192
0.711	Intermediate Similarity	NPC478078
0.7101	Intermediate Similarity	NPC225400
0.7097	Intermediate Similarity	NPC154478
0.7097	Intermediate Similarity	NPC301163
0.7081	Intermediate Similarity	NPC84317
0.7071	Intermediate Similarity	NPC473815
0.7071	Intermediate Similarity	NPC21425
0.7067	Intermediate Similarity	NPC471155
0.7067	Intermediate Similarity	NPC470786
0.7067	Intermediate Similarity	NPC472538
0.7065	Intermediate Similarity	NPC254957
0.7062	Intermediate Similarity	NPC474041
0.7062	Intermediate Similarity	NPC475761
0.7059	Intermediate Similarity	NPC5374
0.7053	Intermediate Similarity	NPC268077
0.7044	Intermediate Similarity	NPC316282
0.7033	Intermediate Similarity	NPC270241
0.7026	Intermediate Similarity	NPC475685
0.7024	Intermediate Similarity	NPC138830
0.7019	Intermediate Similarity	NPC158551
0.7006	Intermediate Similarity	NPC83214
0.7005	Intermediate Similarity	NPC207971
0.7	Intermediate Similarity	NPC45389
0.6995	Remote Similarity	NPC144691
0.6991	Remote Similarity	NPC323969
0.6977	Remote Similarity	NPC96321
0.6973	Remote Similarity	NPC471132
0.6971	Remote Similarity	NPC266425
0.6965	Remote Similarity	NPC1820
0.6931	Remote Similarity	NPC257763
0.6927	Remote Similarity	NPC100863
0.6923	Remote Similarity	NPC9373
0.6923	Remote Similarity	NPC324445
0.6923	Remote Similarity	NPC311906
0.6923	Remote Similarity	NPC41216
0.6915	Remote Similarity	NPC174629
0.6897	Remote Similarity	NPC203972
0.6891	Remote Similarity	NPC85482
0.6872	Remote Similarity	NPC82548
0.6849	Remote Similarity	NPC220851
0.6847	Remote Similarity	NPC473004
0.6845	Remote Similarity	NPC112937
0.6842	Remote Similarity	NPC473460
0.6832	Remote Similarity	NPC5630
0.6822	Remote Similarity	NPC472098
0.6816	Remote Similarity	NPC471316
0.681	Remote Similarity	NPC475147
0.68	Remote Similarity	NPC473007
0.6798	Remote Similarity	NPC22476
0.6794	Remote Similarity	NPC295898
0.6792	Remote Similarity	NPC207873
0.6792	Remote Similarity	NPC100573
0.6791	Remote Similarity	NPC295021
0.678	Remote Similarity	NPC162417
0.678	Remote Similarity	NPC316104
0.6777	Remote Similarity	NPC477161
0.6774	Remote Similarity	NPC126556
0.6765	Remote Similarity	NPC204970
0.6758	Remote Similarity	NPC472099
0.6758	Remote Similarity	NPC308197
0.6757	Remote Similarity	NPC242000
0.6749	Remote Similarity	NPC473569
0.6745	Remote Similarity	NPC53344
0.674	Remote Similarity	NPC2823
0.6734	Remote Similarity	NPC472163
0.6734	Remote Similarity	NPC28368
0.6731	Remote Similarity	NPC106118
0.673	Remote Similarity	NPC14339
0.6726	Remote Similarity	NPC172222
0.6725	Remote Similarity	NPC475816
0.672	Remote Similarity	NPC470708
0.6718	Remote Similarity	NPC355
0.6715	Remote Similarity	NPC471199
0.6713	Remote Similarity	NPC74562
0.6713	Remote Similarity	NPC316181
0.6713	Remote Similarity	NPC151781
0.6712	Remote Similarity	NPC122886
0.6702	Remote Similarity	NPC27904
0.6699	Remote Similarity	NPC127178
0.6699	Remote Similarity	NPC230313
0.6696	Remote Similarity	NPC194740
0.6683	Remote Similarity	NPC116007
0.6683	Remote Similarity	NPC262725
0.6682	Remote Similarity	NPC471561
0.6682	Remote Similarity	NPC475133
0.6667	Remote Similarity	NPC315498
0.6667	Remote Similarity	NPC10732
0.6667	Remote Similarity	NPC473008
0.6667	Remote Similarity	NPC250476
0.6667	Remote Similarity	NPC230942
0.665	Remote Similarity	NPC288305
0.6649	Remote Similarity	NPC471652
0.6649	Remote Similarity	NPC117032
0.6648	Remote Similarity	NPC29650
0.6638	Remote Similarity	NPC314702
0.6637	Remote Similarity	NPC115588
0.6635	Remote Similarity	NPC474077
0.6632	Remote Similarity	NPC189116
0.662	Remote Similarity	NPC45190
0.662	Remote Similarity	NPC82541
0.662	Remote Similarity	NPC471191
0.662	Remote Similarity	NPC300156
0.6619	Remote Similarity	NPC67904
0.6619	Remote Similarity	NPC329793
0.6618	Remote Similarity	NPC243626
0.6615	Remote Similarity	NPC471651
0.6611	Remote Similarity	NPC138365
0.661	Remote Similarity	NPC231382
0.6608	Remote Similarity	NPC474192
0.6608	Remote Similarity	NPC475720
0.66	Remote Similarity	NPC39822
0.6599	Remote Similarity	NPC73280
0.6598	Remote Similarity	NPC70172
0.6594	Remote Similarity	NPC477549
0.6591	Remote Similarity	NPC303658
0.6591	Remote Similarity	NPC473041
0.659	Remote Similarity	NPC159815
0.659	Remote Similarity	NPC264176
0.659	Remote Similarity	NPC119722
0.6589	Remote Similarity	NPC308943
0.6589	Remote Similarity	NPC243850
0.6579	Remote Similarity	NPC329631
0.6575	Remote Similarity	NPC122553
0.6567	Remote Similarity	NPC116096
0.656	Remote Similarity	NPC473006
0.6558	Remote Similarity	NPC329567
0.6558	Remote Similarity	NPC330683
0.6557	Remote Similarity	NPC471574
0.6555	Remote Similarity	NPC470021
0.6546	Remote Similarity	NPC113056
0.6546	Remote Similarity	NPC138293
0.6545	Remote Similarity	NPC471649
0.6545	Remote Similarity	NPC305984
0.6544	Remote Similarity	NPC295479
0.6544	Remote Similarity	NPC220241
0.6533	Remote Similarity	NPC476436
0.6533	Remote Similarity	NPC8467
0.653	Remote Similarity	NPC16066
0.653	Remote Similarity	NPC55470
0.6524	Remote Similarity	NPC234933
0.652	Remote Similarity	NPC83511
0.6517	Remote Similarity	NPC70092
0.6516	Remote Similarity	NPC87560
0.6516	Remote Similarity	NPC195120
0.6512	Remote Similarity	NPC198160
0.6512	Remote Similarity	NPC193238
0.6503	Remote Similarity	NPC204156
0.6502	Remote Similarity	NPC280799
0.6502	Remote Similarity	NPC21429
0.65	Remote Similarity	NPC469928
0.6495	Remote Similarity	NPC133470
0.6495	Remote Similarity	NPC191863
0.6495	Remote Similarity	NPC289776
0.649	Remote Similarity	NPC471825

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 NPC198401 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	714
0.2-0.3	823
0.3-0.4	1519
0.4-0.5	2688
0.5-0.6	1982
0.6-0.7	998
0.7-0.8	104
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8503	High Similarity	NPD5515	Phase 2
0.837	Intermediate Similarity	NPD4515	Suspended
0.809	Intermediate Similarity	NPD7225	Discontinued
0.7688	Intermediate Similarity	NPD3802	Phase 3
0.7594	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7488	Intermediate Similarity	NPD7559	Phase 2
0.7474	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD5183	Approved
0.7473	Intermediate Similarity	NPD5186	Approved
0.7436	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD3631	Phase 3
0.7394	Intermediate Similarity	NPD5078	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD4154	Approved
0.7358	Intermediate Similarity	NPD5923	Phase 1
0.7343	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6021	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5071	Phase 2
0.7258	Intermediate Similarity	NPD6533	Clinical (unspecified phase)
0.7243	Intermediate Similarity	NPD8311	Discontinued
0.7212	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7660	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD6654	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD5966	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD3416	Discontinued
0.7151	Intermediate Similarity	NPD1920	Approved
0.7151	Intermediate Similarity	NPD1919	Approved
0.715	Intermediate Similarity	NPD6046	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6874	Approved
0.7123	Intermediate Similarity	NPD5025	Approved
0.7122	Intermediate Similarity	NPD6511	Phase 1
0.7122	Intermediate Similarity	NPD6510	Phase 1
0.7097	Intermediate Similarity	NPD6737	Phase 2
0.7097	Intermediate Similarity	NPD6738	Phase 2
0.7091	Intermediate Similarity	NPD3442	Approved
0.7091	Intermediate Similarity	NPD3441	Approved
0.7039	Intermediate Similarity	NPD7071	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7255	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6478	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3591	Approved
0.7	Intermediate Similarity	NPD3592	Approved
0.6995	Remote Similarity	NPD7449	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6242	Discontinued
0.6986	Remote Similarity	NPD5143	Clinical (unspecified phase)
0.698	Remote Similarity	NPD4539	Phase 1
0.6968	Remote Similarity	NPD6199	Discontinued
0.6967	Remote Similarity	NPD5860	Discontinued
0.6963	Remote Similarity	NPD2821	Approved
0.6963	Remote Similarity	NPD6379	Discontinued
0.6959	Remote Similarity	NPD4020	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4558	Phase 2
0.694	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5600	Discontinued
0.6915	Remote Similarity	NPD5294	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD6720	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8149	Discontinued
0.6883	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5871	Discontinued
0.6881	Remote Similarity	NPD5042	Phase 1
0.6878	Remote Similarity	NPD5967	Approved
0.6875	Remote Similarity	NPD3983	Phase 3
0.6875	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6457	Approved
0.6875	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4491	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5293	Phase 2
0.6837	Remote Similarity	NPD3793	Phase 3
0.6837	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6238	Discontinued
0.6825	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7032	Approved
0.6818	Remote Similarity	NPD2950	Approved
0.6818	Remote Similarity	NPD2949	Approved
0.6814	Remote Similarity	NPD5469	Phase 3
0.6809	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD5562	Approved
0.6806	Remote Similarity	NPD5561	Approved
0.6798	Remote Similarity	NPD7560	Approved
0.6796	Remote Similarity	NPD4423	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD6795	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD4082	Approved
0.6787	Remote Similarity	NPD7545	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD7588	Discontinued
0.6777	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6017	Discontinued
0.6774	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5513	Phase 2
0.6759	Remote Similarity	NPD3257	Approved
0.6757	Remote Similarity	NPD4942	Approved
0.6757	Remote Similarity	NPD7186	Phase 3
0.6753	Remote Similarity	NPD7206	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD6136	Phase 2
0.6746	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6321	Discontinued
0.6733	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5882	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1880	Phase 3
0.6716	Remote Similarity	NPD6557	Phase 2
0.6715	Remote Similarity	NPD5591	Approved
0.6714	Remote Similarity	NPD956	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4356	Discontinued
0.6712	Remote Similarity	NPD3258	Approved
0.6711	Remote Similarity	NPD8157	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.67	Remote Similarity	NPD7291	Discontinued
0.67	Remote Similarity	NPD7855	Clinical (unspecified phase)
0.67	Remote Similarity	NPD2792	Approved
0.6698	Remote Similarity	NPD4493	Discontinued
0.6698	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5601	Phase 2
0.6698	Remote Similarity	NPD683	Approved
0.6697	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5271	Approved
0.6696	Remote Similarity	NPD5273	Approved
0.6695	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD1861	Discovery
0.6684	Remote Similarity	NPD4796	Discontinued
0.6682	Remote Similarity	NPD4897	Phase 2
0.6682	Remote Similarity	NPD5149	Phase 2
0.6682	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7064	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6681	Remote Similarity	NPD7797	Approved
0.6681	Remote Similarity	NPD7796	Approved
0.6667	Remote Similarity	NPD4492	Approved
0.6667	Remote Similarity	NPD1743	Approved
0.6667	Remote Similarity	NPD3964	Approved
0.6667	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD19	Approved
0.6667	Remote Similarity	NPD4429	Discontinued
0.6667	Remote Similarity	NPD743	Approved
0.6667	Remote Similarity	NPD7546	Discontinued
0.6667	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4494	Approved
0.6667	Remote Similarity	NPD5670	Approved
0.6667	Remote Similarity	NPD1742	Approved
0.6652	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD8016	Phase 3
0.6652	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD3392	Approved
0.6649	Remote Similarity	NPD3248	Phase 1
0.6649	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD2791	Discontinued
0.6636	Remote Similarity	NPD7467	Discontinued
0.6636	Remote Similarity	NPD6366	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5994	Discontinued
0.6634	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD795	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD1165	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3789	Approved
0.6632	Remote Similarity	NPD2366	Approved
0.663	Remote Similarity	NPD5481	Discontinued
0.6619	Remote Similarity	NPD6612	Phase 2
0.6619	Remote Similarity	NPD8164	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD6645	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD1544	Phase 1
0.6606	Remote Similarity	NPD3437	Discontinued
0.6605	Remote Similarity	NPD3874	Discontinued
0.6602	Remote Similarity	NPD7569	Approved
0.6602	Remote Similarity	NPD7570	Approved
0.6599	Remote Similarity	NPD6894	Phase 1
0.6599	Remote Similarity	NPD7443	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD1670	Discontinued
0.6592	Remote Similarity	NPD7278	Phase 2
0.6592	Remote Similarity	NPD7279	Phase 2
0.659	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.659	Remote Similarity	NPD3888	Discontinued
0.6589	Remote Similarity	NPD7043	Discontinued
0.6588	Remote Similarity	NPD5552	Discontinued
0.6585	Remote Similarity	NPD5114	Approved
0.6585	Remote Similarity	NPD4258	Approved
0.6585	Remote Similarity	NPD4259	Approved
0.6585	Remote Similarity	NPD2410	Phase 2
0.6585	Remote Similarity	NPD5112	Approved
0.6585	Remote Similarity	NPD5113	Approved
0.6582	Remote Similarity	NPD5847	Phase 1
0.6581	Remote Similarity	NPD6397	Phase 3
0.6579	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7072	Phase 2
0.6578	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD2341	Discontinued
0.6562	Remote Similarity	NPD4132	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD950	Clinical (unspecified phase)
0.656	Remote Similarity	NPD3945	Discontinued
0.656	Remote Similarity	NPD4455	Discontinued
0.6559	Remote Similarity	NPD1524	Phase 1
0.6558	Remote Similarity	NPD3472	Approved
0.6558	Remote Similarity	NPD2906	Approved
0.6558	Remote Similarity	NPD2907	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