NPASS Compound

Structure

NPC193998 OpenBabel07101719512D 25 28 0 0 0 0 0 0 0 0999 V2000 -5.1962 0.0000 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 1.7321 -2.0000 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 1.9400 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9345 1.0827 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 -2.5981 -0.5000 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 -1.7321 0.0000 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 -3.4641 0.0000 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 0.8660 -1.5000 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 -0.0000 -2.0000 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 0.1691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 6 2 0 0 0 0 5 13 1 0 0 0 0 6 24 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 10 1 0 0 0 0 8 12 2 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 14 18 2 0 0 0 0 15 24 1 0 0 0 0 16 19 1 0 0 0 0 16 21 2 0 0 0 0 17 19 2 0 0 0 0 17 25 1 0 0 0 0 18 25 1 0 0 0 0 19 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.08
Volume:	331.968
LogP:	3.798
LogD:	2.903
LogS:	-4.249
# Rotatable Bonds:	3
TPSA:	82.04
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.609
Synthetic Accessibility Score:	2.59
Fsp3:	0.105
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:	-4.776
MDCK Permeability:	2.784003117994871e-05
Pgp-inhibitor:	0.834
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	87.05170440673828%
Volume Distribution (VD):	0.692
Pgp-substrate:	10.684833526611328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.902
CYP2C19-inhibitor:	0.93
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.804
CYP2C9-substrate:	0.918
CYP2D6-inhibitor:	0.767
CYP2D6-substrate:	0.905
CYP3A4-inhibitor:	0.898
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	6.754
Half-life (T1/2):	0.632

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.413
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.216
Rat Oral Acute Toxicity:	0.307
Maximum Recommended Daily Dose:	0.689
Skin Sensitization:	0.249
Carcinogencity:	0.239
Eye Corrosion:	0.003
Eye Irritation:	0.451
Respiratory Toxicity:	0.786

Download Data

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

Natural Product: NPC193998

Natural Product ID:	NPC193998
*Common Name:**	WMVUNKYYHUBTIU-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	WMVUNKYYHUBTIU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H14O6/c1-22-12-8-10(7-11(20)9-12)17-19(23-2)16(21)14-3-4-15-13(5-6-24-15)18(14)25-17/h3-9,20H,1-2H3
SMILES:	COc1cc(O)cc(c1)c1oc2c(c(=O)c1OC)ccc1c2cco1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581065
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001759] Furanoflavones

*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
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	stem bark	Indonesia	1999-SEP	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[14510596]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	dry stem	n.a.	n.a.	PMID[25466192]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29482940]
NPO30165	Pongamia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
NPT34	Cell Line	BV-2	Mus musculus	IC50	>	100000.0	nM	PMID[469576]

☑ 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 NPC193998 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	464
0.1-0.2	1995
0.2-0.3	4762
0.3-0.4	11148
0.4-0.5	6732
0.5-0.6	4238
0.6-0.7	5643
0.7-0.8	4240
0.8-0.85	2343
0.85-0.9	1066
0.9-0.95	64
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9542	High Similarity	NPC41719
0.9497	High Similarity	NPC241820
0.9477	High Similarity	NPC263676
0.9477	High Similarity	NPC38361
0.9477	High Similarity	NPC130015
0.9477	High Similarity	NPC253872
0.9412	High Similarity	NPC116604
0.9371	High Similarity	NPC38914
0.9367	High Similarity	NPC219861
0.9355	High Similarity	NPC233776
0.9346	High Similarity	NPC135303
0.9346	High Similarity	NPC148423
0.9308	High Similarity	NPC109180
0.9304	High Similarity	NPC304387
0.929	High Similarity	NPC472462
0.9286	High Similarity	NPC170169
0.9231	High Similarity	NPC198490
0.9221	High Similarity	NPC78335
0.9221	High Similarity	NPC230713
0.9216	High Similarity	NPC306788
0.9187	High Similarity	NPC472581
0.9172	High Similarity	NPC247677
0.9172	High Similarity	NPC160015
0.9167	High Similarity	NPC213608
0.9167	High Similarity	NPC183874
0.9167	High Similarity	NPC1477
0.9167	High Similarity	NPC122365
0.9161	High Similarity	NPC472407
0.9156	High Similarity	NPC226644
0.9156	High Similarity	NPC37226
0.9156	High Similarity	NPC178202
0.915	High Similarity	NPC17816
0.915	High Similarity	NPC198427
0.9114	High Similarity	NPC268360
0.9114	High Similarity	NPC296957
0.9114	High Similarity	NPC260902
0.9114	High Similarity	NPC65504
0.9108	High Similarity	NPC148938
0.9103	High Similarity	NPC5871
0.9103	High Similarity	NPC67654
0.9085	High Similarity	NPC190572
0.9057	High Similarity	NPC476349
0.9057	High Similarity	NPC476350
0.9057	High Similarity	NPC472877
0.9045	High Similarity	NPC235333
0.9045	High Similarity	NPC72370
0.9038	High Similarity	NPC115324
0.9038	High Similarity	NPC156244
0.9032	High Similarity	NPC37208
0.9032	High Similarity	NPC39929
0.9032	High Similarity	NPC221868
0.9032	High Similarity	NPC317492
0.9032	High Similarity	NPC296030
0.9026	High Similarity	NPC12148
0.9026	High Similarity	NPC130581
0.902	High Similarity	NPC155144
0.902	High Similarity	NPC98926
0.8994	High Similarity	NPC164110
0.8994	High Similarity	NPC96342
0.8994	High Similarity	NPC246647
0.8994	High Similarity	NPC212967
0.8987	High Similarity	NPC297531
0.8987	High Similarity	NPC99199
0.8987	High Similarity	NPC213936
0.8981	High Similarity	NPC207624
0.8974	High Similarity	NPC167576
0.8974	High Similarity	NPC472406
0.8968	High Similarity	NPC135325
0.8968	High Similarity	NPC168085
0.8968	High Similarity	NPC272194
0.8961	High Similarity	NPC51641
0.8961	High Similarity	NPC178343
0.8961	High Similarity	NPC5820
0.8961	High Similarity	NPC306488
0.8961	High Similarity	NPC300267
0.8961	High Similarity	NPC210826
0.8957	High Similarity	NPC323137
0.8954	High Similarity	NPC302181
0.8954	High Similarity	NPC225884
0.8951	High Similarity	NPC65846
0.8944	High Similarity	NPC74854
0.8944	High Similarity	NPC45124
0.8944	High Similarity	NPC264293
0.8944	High Similarity	NPC30655
0.8938	High Similarity	NPC40583
0.8931	High Similarity	NPC180924
0.8917	High Similarity	NPC193976
0.8917	High Similarity	NPC58668
0.8917	High Similarity	NPC23668
0.8917	High Similarity	NPC106372
0.8916	High Similarity	NPC277510
0.8916	High Similarity	NPC62640
0.891	High Similarity	NPC470461
0.8909	High Similarity	NPC131866
0.8896	High Similarity	NPC230943
0.8896	High Similarity	NPC136641
0.8896	High Similarity	NPC216538
0.8896	High Similarity	NPC273538
0.8889	High Similarity	NPC272722
0.8889	High Similarity	NPC473042
0.8889	High Similarity	NPC53192
0.8882	High Similarity	NPC220582
0.8882	High Similarity	NPC304839
0.8875	High Similarity	NPC269495
0.8875	High Similarity	NPC270044
0.8861	High Similarity	NPC142308
0.8855	High Similarity	NPC157522
0.8854	High Similarity	NPC61258
0.8854	High Similarity	NPC155882
0.8846	High Similarity	NPC470460
0.8844	High Similarity	NPC60848
0.8841	High Similarity	NPC277480
0.8839	High Similarity	NPC470458
0.8839	High Similarity	NPC124729
0.8831	High Similarity	NPC212932
0.8831	High Similarity	NPC158874
0.8831	High Similarity	NPC190637
0.8831	High Similarity	NPC9117
0.8831	High Similarity	NPC24821
0.8831	High Similarity	NPC293053
0.8824	High Similarity	NPC136840
0.882	High Similarity	NPC250076
0.8817	High Similarity	NPC104682
0.8805	High Similarity	NPC193200
0.8802	High Similarity	NPC233956
0.8802	High Similarity	NPC65885
0.879	High Similarity	NPC266499
0.879	High Similarity	NPC88445
0.879	High Similarity	NPC269420
0.8788	High Similarity	NPC476459
0.878	High Similarity	NPC259007
0.878	High Similarity	NPC204088
0.878	High Similarity	NPC36320
0.878	High Similarity	NPC37183
0.878	High Similarity	NPC329215
0.8774	High Similarity	NPC311741
0.8774	High Similarity	NPC271590
0.8774	High Similarity	NPC326500
0.8774	High Similarity	NPC234629
0.8774	High Similarity	NPC110776
0.8766	High Similarity	NPC200694
0.8765	High Similarity	NPC115432
0.8765	High Similarity	NPC260296
0.8765	High Similarity	NPC169
0.8758	High Similarity	NPC184536
0.8758	High Similarity	NPC101366
0.8758	High Similarity	NPC230285
0.8758	High Similarity	NPC269652
0.8758	High Similarity	NPC59951
0.8758	High Similarity	NPC281207
0.8758	High Similarity	NPC103342
0.8758	High Similarity	NPC28337
0.8758	High Similarity	NPC103904
0.8758	High Similarity	NPC146679
0.875	High Similarity	NPC133392
0.8743	High Similarity	NPC248593
0.8743	High Similarity	NPC28589
0.8742	High Similarity	NPC31627
0.8742	High Similarity	NPC476238
0.8742	High Similarity	NPC327269
0.8735	High Similarity	NPC202470
0.8735	High Similarity	NPC41853
0.8734	High Similarity	NPC321896
0.8734	High Similarity	NPC120105
0.8734	High Similarity	NPC101957
0.8734	High Similarity	NPC37348
0.8734	High Similarity	NPC191104
0.8734	High Similarity	NPC476185
0.8734	High Similarity	NPC472633
0.8727	High Similarity	NPC53640
0.8726	High Similarity	NPC266572
0.8726	High Similarity	NPC244407
0.8726	High Similarity	NPC296869
0.8726	High Similarity	NPC37135
0.8726	High Similarity	NPC39195
0.8726	High Similarity	NPC186397
0.872	High Similarity	NPC1755
0.872	High Similarity	NPC1706
0.872	High Similarity	NPC263092
0.872	High Similarity	NPC59295
0.872	High Similarity	NPC39305
0.8718	High Similarity	NPC290133
0.8718	High Similarity	NPC24136
0.8718	High Similarity	NPC215885
0.8718	High Similarity	NPC476153
0.8718	High Similarity	NPC2416
0.8718	High Similarity	NPC187282
0.8712	High Similarity	NPC472346
0.871	High Similarity	NPC17262
0.8704	High Similarity	NPC244750
0.8701	High Similarity	NPC90582
0.8701	High Similarity	NPC55832
0.8701	High Similarity	NPC26051
0.8701	High Similarity	NPC52789
0.8701	High Similarity	NPC469404
0.8701	High Similarity	NPC262094
0.8701	High Similarity	NPC268204
0.8701	High Similarity	NPC3188
0.8701	High Similarity	NPC110969
0.8698	High Similarity	NPC107244

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 NPC193998 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	424
0.1-0.2	1003
0.2-0.3	1839
0.3-0.4	2701
0.4-0.5	1804
0.5-0.6	940
0.6-0.7	293
0.7-0.8	98
0.8-0.85	34
0.85-0.9	12
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8944	High Similarity	NPD1247	Approved
0.8896	High Similarity	NPD4378	Clinical (unspecified phase)
0.8662	High Similarity	NPD920	Approved
0.8589	High Similarity	NPD919	Approved
0.858	High Similarity	NPD3882	Suspended
0.8535	High Similarity	NPD642	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6559	Discontinued
0.8457	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD7411	Suspended
0.8431	Intermediate Similarity	NPD1510	Phase 2
0.8418	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7075	Discontinued
0.8408	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD1549	Phase 2
0.8365	Intermediate Similarity	NPD1512	Approved
0.8344	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD3749	Approved
0.8282	Intermediate Similarity	NPD6801	Discontinued
0.8282	Intermediate Similarity	NPD1934	Approved
0.8272	Intermediate Similarity	NPD4380	Phase 2
0.8258	Intermediate Similarity	NPD2796	Approved
0.8239	Intermediate Similarity	NPD1511	Approved
0.8232	Intermediate Similarity	NPD2801	Approved
0.8232	Intermediate Similarity	NPD7819	Suspended
0.8225	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD1243	Approved
0.8205	Intermediate Similarity	NPD2344	Approved
0.8182	Intermediate Similarity	NPD3817	Phase 2
0.817	Intermediate Similarity	NPD1240	Approved
0.8155	Intermediate Similarity	NPD6959	Discontinued
0.8129	Intermediate Similarity	NPD3818	Discontinued
0.8125	Intermediate Similarity	NPD6799	Approved
0.8118	Intermediate Similarity	NPD6166	Phase 2
0.8118	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD2800	Approved
0.8095	Intermediate Similarity	NPD5494	Approved
0.8081	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1607	Approved
0.8059	Intermediate Similarity	NPD3926	Phase 2
0.8024	Intermediate Similarity	NPD7768	Phase 2
0.8	Intermediate Similarity	NPD2309	Approved
0.7976	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD5402	Approved
0.7963	Intermediate Similarity	NPD2533	Approved
0.7963	Intermediate Similarity	NPD2532	Approved
0.7963	Intermediate Similarity	NPD2534	Approved
0.7939	Intermediate Similarity	NPD6599	Discontinued
0.7911	Intermediate Similarity	NPD1551	Phase 2
0.7895	Intermediate Similarity	NPD6232	Discontinued
0.7886	Intermediate Similarity	NPD6797	Phase 2
0.7879	Intermediate Similarity	NPD3226	Approved
0.7862	Intermediate Similarity	NPD1471	Phase 3
0.7862	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD7473	Discontinued
0.7841	Intermediate Similarity	NPD7251	Discontinued
0.7826	Intermediate Similarity	NPD3750	Approved
0.7812	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD2935	Discontinued
0.7797	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7808	Phase 3
0.7758	Intermediate Similarity	NPD5403	Approved
0.7744	Intermediate Similarity	NPD5401	Approved
0.7697	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2313	Discontinued
0.767	Intermediate Similarity	NPD5844	Phase 1
0.767	Intermediate Similarity	NPD7054	Approved
0.7627	Intermediate Similarity	NPD7074	Phase 3
0.7627	Intermediate Similarity	NPD7472	Approved
0.7625	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD8434	Phase 2
0.7607	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD5953	Discontinued
0.7584	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD7286	Phase 2
0.7531	Intermediate Similarity	NPD2346	Discontinued
0.7516	Intermediate Similarity	NPD3748	Approved
0.7516	Intermediate Similarity	NPD2799	Discontinued
0.7514	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7229	Phase 3
0.7484	Intermediate Similarity	NPD943	Approved
0.747	Intermediate Similarity	NPD7390	Discontinued
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD2296	Approved
0.7416	Intermediate Similarity	NPD3751	Discontinued
0.7394	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6651	Approved
0.7386	Intermediate Similarity	NPD5711	Approved
0.7386	Intermediate Similarity	NPD5710	Approved
0.7384	Intermediate Similarity	NPD5761	Phase 2
0.7384	Intermediate Similarity	NPD1465	Phase 2
0.7384	Intermediate Similarity	NPD5760	Phase 2
0.7366	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4287	Approved
0.7337	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2403	Approved
0.7288	Intermediate Similarity	NPD6808	Phase 2
0.7277	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1203	Approved
0.7256	Intermediate Similarity	NPD6099	Approved
0.7256	Intermediate Similarity	NPD6100	Approved
0.725	Intermediate Similarity	NPD3268	Approved
0.7249	Intermediate Similarity	NPD4361	Phase 2
0.7249	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD1729	Discontinued
0.7233	Intermediate Similarity	NPD4908	Phase 1
0.7226	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6280	Approved
0.7225	Intermediate Similarity	NPD6279	Approved
0.7222	Intermediate Similarity	NPD230	Phase 1
0.7222	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD4363	Phase 3
0.7196	Intermediate Similarity	NPD4360	Phase 2
0.7195	Intermediate Similarity	NPD7033	Discontinued
0.7195	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD3787	Discontinued
0.719	Intermediate Similarity	NPD1548	Phase 1
0.7186	Intermediate Similarity	NPD4628	Phase 3
0.7186	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3764	Approved
0.7125	Intermediate Similarity	NPD6832	Phase 2
0.7117	Intermediate Similarity	NPD447	Suspended
0.7115	Intermediate Similarity	NPD1610	Phase 2
0.7107	Intermediate Similarity	NPD2798	Approved
0.7091	Intermediate Similarity	NPD4308	Phase 3
0.7081	Intermediate Similarity	NPD8312	Approved
0.7081	Intermediate Similarity	NPD8313	Approved
0.7081	Intermediate Similarity	NPD4625	Phase 3
0.7074	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD9717	Approved
0.7069	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1613	Approved
0.7055	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5406	Approved
0.7048	Intermediate Similarity	NPD5404	Approved
0.7048	Intermediate Similarity	NPD5405	Approved
0.7048	Intermediate Similarity	NPD5408	Approved
0.7044	Intermediate Similarity	NPD1470	Approved
0.7044	Intermediate Similarity	NPD3266	Approved
0.7044	Intermediate Similarity	NPD3267	Approved
0.7039	Intermediate Similarity	NPD7199	Phase 2
0.7037	Intermediate Similarity	NPD6798	Discontinued
0.7033	Intermediate Similarity	NPD2163	Approved
0.7029	Intermediate Similarity	NPD6844	Discontinued
0.7024	Intermediate Similarity	NPD2654	Approved
0.7019	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD6779	Approved
0.701	Intermediate Similarity	NPD6780	Approved
0.701	Intermediate Similarity	NPD6782	Approved
0.701	Intermediate Similarity	NPD6781	Approved
0.701	Intermediate Similarity	NPD6776	Approved
0.701	Intermediate Similarity	NPD6777	Approved
0.701	Intermediate Similarity	NPD6778	Approved
0.7006	Intermediate Similarity	NPD422	Phase 1
0.7005	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7435	Discontinued
0.6981	Remote Similarity	NPD3225	Approved
0.6973	Remote Similarity	NPD6765	Approved
0.6973	Remote Similarity	NPD6764	Approved
0.6973	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD5890	Approved
0.6971	Remote Similarity	NPD5889	Approved
0.6962	Remote Similarity	NPD1608	Approved
0.6957	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9494	Approved
0.6954	Remote Similarity	NPD7871	Phase 2
0.6954	Remote Similarity	NPD7870	Phase 2
0.6951	Remote Similarity	NPD4060	Phase 1
0.6949	Remote Similarity	NPD4288	Approved
0.6949	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD6190	Approved
0.694	Remote Similarity	NPD7177	Discontinued
0.6937	Remote Similarity	NPD2797	Approved
0.6933	Remote Similarity	NPD411	Approved
0.6932	Remote Similarity	NPD37	Approved
0.6927	Remote Similarity	NPD6234	Discontinued
0.6923	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.691	Remote Similarity	NPD4965	Approved
0.691	Remote Similarity	NPD4967	Phase 2
0.691	Remote Similarity	NPD4966	Approved
0.6909	Remote Similarity	NPD5124	Phase 1
0.6909	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6355	Discontinued
0.6904	Remote Similarity	NPD7697	Approved
0.6904	Remote Similarity	NPD7696	Phase 3
0.6904	Remote Similarity	NPD7698	Approved
0.69	Remote Similarity	NPD8151	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