NPASS Compound

Structure

NPC472407 OpenBabel07101718182D 22 26 0 0 0 0 0 0 0 0999 V2000 2.5981 -1.5000 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 -1.0000 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 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 2.0000 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 -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 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 -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 0.0000 3.0000 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 2.5981 1.5000 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 10 2 0 0 0 0 4 14 2 0 0 0 0 5 6 2 0 0 0 0 5 12 1 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 21 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 16 1 0 0 0 0 12 17 2 0 0 0 0 13 16 1 0 0 0 0 13 18 2 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 16 19 2 0 0 0 0 17 22 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	290.06
Volume:	288.535
LogP:	3.709
LogD:	2.873
LogS:	-5.301
# Rotatable Bonds:	0
TPSA:	52.58
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.489
Synthetic Accessibility Score:	2.613
Fsp3:	0.056
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.861
MDCK Permeability:	2.4074246539385058e-05
Pgp-inhibitor:	0.717
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.446

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	95.05326843261719%
Volume Distribution (VD):	1.126
Pgp-substrate:	5.095646858215332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.967
CYP1A2-substrate:	0.36
CYP2C19-inhibitor:	0.665
CYP2C19-substrate:	0.069
CYP2C9-inhibitor:	0.634
CYP2C9-substrate:	0.891
CYP2D6-inhibitor:	0.124
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.445
CYP3A4-substrate:	0.135

ADMET: Excretion

Clearance (CL):	3.864
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.669
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.747
Rat Oral Acute Toxicity:	0.888
Maximum Recommended Daily Dose:	0.051
Skin Sensitization:	0.126
Carcinogencity:	0.806
Eye Corrosion:	0.005
Eye Irritation:	0.763
Respiratory Toxicity:	0.447

Download Data

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

Natural Product: NPC472407

Natural Product ID:	NPC472407
*Common Name:**	JHNMBFUZKBERHM-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JHNMBFUZKBERHM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H10O4/c19-16-12-5-6-15-11(7-8-20-15)17(12)22-18-10-3-1-2-4-14(10)21-9-13(16)18/h1-8H,9H2
SMILES:	O=c1c2COc3c(c2oc2c1ccc1c2cco1)cccc3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3401057
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
NPO19856	Millettia pulchra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25630222]
NPO19856	Millettia pulchra	Species	Fabaceae	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
Others	2

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT365	Individual Protein	NAD(P)H dehydrogenase [quinone] 1	Mus musculus	Ratio	=	1.67	n.a.	PMID[539151]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	97.0	%	PMID[539151]

☑ 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 NPC472407 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	631
0.1-0.2	2276
0.2-0.3	5586
0.3-0.4	12447
0.4-0.5	5068
0.5-0.6	5339
0.6-0.7	5429
0.7-0.8	4338
0.8-0.85	1277
0.85-0.9	277
0.9-0.95	21
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9793	High Similarity	NPC135303
0.9793	High Similarity	NPC148423
0.9792	High Similarity	NPC306788
0.966	High Similarity	NPC38361
0.966	High Similarity	NPC130015
0.9595	High Similarity	NPC41719
0.9586	High Similarity	NPC198427
0.953	High Similarity	NPC233776
0.9517	High Similarity	NPC190572
0.9396	High Similarity	NPC263676
0.9392	High Similarity	NPC472406
0.9329	High Similarity	NPC116604
0.9195	High Similarity	NPC88445
0.9161	High Similarity	NPC193998
0.9139	High Similarity	NPC253872
0.9133	High Similarity	NPC191104
0.9116	High Similarity	NPC17262
0.9103	High Similarity	NPC65846
0.906	High Similarity	NPC74539
0.906	High Similarity	NPC304443
0.9054	High Similarity	NPC246903
0.9045	High Similarity	NPC38914
0.9026	High Similarity	NPC65504
0.8974	High Similarity	NPC304387
0.8961	High Similarity	NPC247677
0.8961	High Similarity	NPC160015
0.8954	High Similarity	NPC213608
0.8954	High Similarity	NPC122365
0.8954	High Similarity	NPC1477
0.894	High Similarity	NPC37226
0.894	High Similarity	NPC226644
0.8931	High Similarity	NPC167479
0.8931	High Similarity	NPC241820
0.8926	High Similarity	NPC179970
0.8919	High Similarity	NPC166858
0.8919	High Similarity	NPC51146
0.8917	High Similarity	NPC219861
0.8903	High Similarity	NPC260902
0.8903	High Similarity	NPC296957
0.8897	High Similarity	NPC29638
0.8889	High Similarity	NPC5871
0.8889	High Similarity	NPC67654
0.8875	High Similarity	NPC41853
0.8874	High Similarity	NPC266743
0.8851	High Similarity	NPC22467
0.8846	High Similarity	NPC476350
0.8846	High Similarity	NPC476349
0.8831	High Similarity	NPC472462
0.8824	High Similarity	NPC156244
0.8824	High Similarity	NPC170169
0.882	High Similarity	NPC190351
0.8816	High Similarity	NPC296030
0.8816	High Similarity	NPC317492
0.8816	High Similarity	NPC37208
0.8816	High Similarity	NPC39929
0.8816	High Similarity	NPC221868
0.8808	High Similarity	NPC12148
0.8808	High Similarity	NPC130581
0.88	High Similarity	NPC208584
0.8792	High Similarity	NPC313036
0.8782	High Similarity	NPC269495
0.8776	High Similarity	NPC17848
0.8774	High Similarity	NPC295608
0.8774	High Similarity	NPC198490
0.8774	High Similarity	NPC250769
0.8774	High Similarity	NPC278010
0.8767	High Similarity	NPC254741
0.8758	High Similarity	NPC230713
0.8758	High Similarity	NPC78335
0.8758	High Similarity	NPC155882
0.875	High Similarity	NPC272194
0.875	High Similarity	NPC266572
0.875	High Similarity	NPC135325
0.875	High Similarity	NPC168085
0.8742	High Similarity	NPC472581
0.8742	High Similarity	NPC210826
0.8742	High Similarity	NPC51641
0.8742	High Similarity	NPC109180
0.8742	High Similarity	NPC300267
0.8734	High Similarity	NPC264293
0.8733	High Similarity	NPC225884
0.8733	High Similarity	NPC302181
0.8733	High Similarity	NPC59522
0.8726	High Similarity	NPC472877
0.8726	High Similarity	NPC40583
0.8712	High Similarity	NPC62640
0.871	High Similarity	NPC131725
0.871	High Similarity	NPC183874
0.8707	High Similarity	NPC157855
0.8693	High Similarity	NPC178202
0.869	High Similarity	NPC292998
0.8684	High Similarity	NPC104406
0.8684	High Similarity	NPC24673
0.8684	High Similarity	NPC17816
0.8684	High Similarity	NPC79469
0.8684	High Similarity	NPC97716
0.8684	High Similarity	NPC237635
0.8684	High Similarity	NPC201731
0.8675	High Similarity	NPC155144
0.8675	High Similarity	NPC230943
0.8671	High Similarity	NPC49009
0.8671	High Similarity	NPC169
0.8667	High Similarity	NPC53192
0.8662	High Similarity	NPC268360
0.8662	High Similarity	NPC270044
0.8662	High Similarity	NPC19097
0.8658	High Similarity	NPC472409
0.8654	High Similarity	NPC148938
0.8639	High Similarity	NPC161196
0.8627	High Similarity	NPC6511
0.8625	High Similarity	NPC38591
0.8621	High Similarity	NPC182428
0.8616	High Similarity	NPC14822
0.8608	High Similarity	NPC250076
0.86	High Similarity	NPC52576
0.86	High Similarity	NPC254010
0.8591	High Similarity	NPC262635
0.8591	High Similarity	NPC136095
0.8591	High Similarity	NPC11566
0.859	High Similarity	NPC72370
0.859	High Similarity	NPC235333
0.8581	High Similarity	NPC259685
0.8581	High Similarity	NPC115324
0.8571	High Similarity	NPC46869
0.8571	High Similarity	NPC136641
0.8571	High Similarity	NPC5173
0.8562	High Similarity	NPC223354
0.8562	High Similarity	NPC471285
0.8553	High Similarity	NPC234629
0.8553	High Similarity	NPC303210
0.8553	High Similarity	NPC319752
0.8553	High Similarity	NPC98926
0.8553	High Similarity	NPC115432
0.8553	High Similarity	NPC95472
0.8553	High Similarity	NPC311741
0.8553	High Similarity	NPC110776
0.8553	High Similarity	NPC260296
0.8553	High Similarity	NPC271590
0.8553	High Similarity	NPC239270
0.8552	High Similarity	NPC278556
0.8552	High Similarity	NPC284424
0.8545	High Similarity	NPC66804
0.8544	High Similarity	NPC164110
0.8544	High Similarity	NPC212967
0.8544	High Similarity	NPC246647
0.8544	High Similarity	NPC96342
0.8537	High Similarity	NPC157522
0.8537	High Similarity	NPC248593
0.8537	High Similarity	NPC28589
0.8535	High Similarity	NPC213936
0.8535	High Similarity	NPC477530
0.8535	High Similarity	NPC99199
0.8535	High Similarity	NPC297531
0.8533	High Similarity	NPC28337
0.8533	High Similarity	NPC101366
0.8526	High Similarity	NPC327269
0.8526	High Similarity	NPC207624
0.8526	High Similarity	NPC476238
0.8526	High Similarity	NPC31627
0.8516	High Similarity	NPC167576
0.8516	High Similarity	NPC5840
0.8516	High Similarity	NPC471115
0.8516	High Similarity	NPC188403
0.8516	High Similarity	NPC189270
0.8516	High Similarity	NPC29777
0.8516	High Similarity	NPC476185
0.8516	High Similarity	NPC321896
0.8509	High Similarity	NPC155640
0.8506	High Similarity	NPC244407
0.8506	High Similarity	NPC39195
0.8503	High Similarity	NPC125269
0.85	High Similarity	NPC45124
0.85	High Similarity	NPC74854
0.85	High Similarity	NPC30655
0.85	High Similarity	NPC472346
0.8497	Intermediate Similarity	NPC476088
0.8497	Intermediate Similarity	NPC476153
0.8497	Intermediate Similarity	NPC73320
0.8497	Intermediate Similarity	NPC2416
0.8497	Intermediate Similarity	NPC474161
0.8497	Intermediate Similarity	NPC215885
0.8493	Intermediate Similarity	NPC473655
0.8493	Intermediate Similarity	NPC101294
0.8491	Intermediate Similarity	NPC244750
0.8485	Intermediate Similarity	NPC72455
0.8481	Intermediate Similarity	NPC470625
0.8481	Intermediate Similarity	NPC137100
0.8481	Intermediate Similarity	NPC180924
0.8477	Intermediate Similarity	NPC26051
0.8477	Intermediate Similarity	NPC110969
0.8477	Intermediate Similarity	NPC268204
0.8477	Intermediate Similarity	NPC103362
0.8477	Intermediate Similarity	NPC14871
0.8477	Intermediate Similarity	NPC3188
0.8477	Intermediate Similarity	NPC55832
0.8477	Intermediate Similarity	NPC469404
0.8477	Intermediate Similarity	NPC52789
0.8476	Intermediate Similarity	NPC131866
0.8471	Intermediate Similarity	NPC194593
0.8471	Intermediate Similarity	NPC472408

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 NPC472407 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	534
0.1-0.2	1028
0.2-0.3	1784
0.3-0.4	2804
0.4-0.5	1803
0.5-0.6	843
0.6-0.7	232
0.7-0.8	94
0.8-0.85	19
0.85-0.9	6
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.906	High Similarity	NPD920	Approved
0.9054	High Similarity	NPD642	Clinical (unspecified phase)
0.8919	High Similarity	NPD643	Clinical (unspecified phase)
0.8734	High Similarity	NPD1247	Approved
0.8639	High Similarity	NPD2796	Approved
0.8591	High Similarity	NPD1243	Approved
0.8462	Intermediate Similarity	NPD7411	Suspended
0.8431	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD919	Approved
0.8323	Intermediate Similarity	NPD5494	Approved
0.8322	Intermediate Similarity	NPD1510	Phase 2
0.8313	Intermediate Similarity	NPD3749	Approved
0.8312	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD4380	Phase 2
0.8278	Intermediate Similarity	NPD1549	Phase 2
0.8212	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD3748	Approved
0.8047	Intermediate Similarity	NPD6559	Discontinued
0.8012	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7819	Suspended
0.7987	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD2344	Approved
0.7952	Intermediate Similarity	NPD3926	Phase 2
0.795	Intermediate Similarity	NPD6801	Discontinued
0.7933	Intermediate Similarity	NPD1240	Approved
0.7914	Intermediate Similarity	NPD7768	Phase 2
0.7898	Intermediate Similarity	NPD6799	Approved
0.7898	Intermediate Similarity	NPD1511	Approved
0.7871	Intermediate Similarity	NPD2800	Approved
0.7866	Intermediate Similarity	NPD7075	Discontinued
0.7857	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD5401	Approved
0.784	Intermediate Similarity	NPD1934	Approved
0.7831	Intermediate Similarity	NPD6959	Discontinued
0.7829	Intermediate Similarity	NPD1607	Approved
0.7821	Intermediate Similarity	NPD3750	Approved
0.7811	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3818	Discontinued
0.7805	Intermediate Similarity	NPD3882	Suspended
0.78	Intermediate Similarity	NPD2313	Discontinued
0.7799	Intermediate Similarity	NPD1512	Approved
0.7792	Intermediate Similarity	NPD1551	Phase 2
0.7791	Intermediate Similarity	NPD2801	Approved
0.7771	Intermediate Similarity	NPD2309	Approved
0.775	Intermediate Similarity	NPD5403	Approved
0.7744	Intermediate Similarity	NPD5402	Approved
0.7744	Intermediate Similarity	NPD3817	Phase 2
0.7742	Intermediate Similarity	NPD1471	Phase 3
0.7716	Intermediate Similarity	NPD6599	Discontinued
0.7671	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6166	Phase 2
0.7588	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6808	Phase 2
0.7546	Intermediate Similarity	NPD3226	Approved
0.7516	Intermediate Similarity	NPD2532	Approved
0.7516	Intermediate Similarity	NPD2534	Approved
0.7516	Intermediate Similarity	NPD2533	Approved
0.7515	Intermediate Similarity	NPD6279	Approved
0.7515	Intermediate Similarity	NPD6280	Approved
0.75	Intermediate Similarity	NPD2799	Discontinued
0.7486	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6232	Discontinued
0.7457	Intermediate Similarity	NPD5844	Phase 1
0.7451	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD7473	Discontinued
0.7434	Intermediate Similarity	NPD6832	Phase 2
0.7423	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5953	Discontinued
0.7358	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7286	Phase 2
0.7356	Intermediate Similarity	NPD7054	Approved
0.7351	Intermediate Similarity	NPD3266	Approved
0.7351	Intermediate Similarity	NPD3267	Approved
0.7349	Intermediate Similarity	NPD5889	Approved
0.7349	Intermediate Similarity	NPD5890	Approved
0.7342	Intermediate Similarity	NPD2935	Discontinued
0.7333	Intermediate Similarity	NPD4287	Approved
0.7314	Intermediate Similarity	NPD7472	Approved
0.7314	Intermediate Similarity	NPD7074	Phase 3
0.7312	Intermediate Similarity	NPD2654	Approved
0.7308	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2346	Discontinued
0.7288	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2403	Approved
0.7273	Intermediate Similarity	NPD6797	Phase 2
0.7267	Intermediate Similarity	NPD7229	Phase 3
0.7232	Intermediate Similarity	NPD7251	Discontinued
0.7226	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7219	Intermediate Similarity	NPD2296	Approved
0.7193	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7808	Phase 3
0.719	Intermediate Similarity	NPD2798	Approved
0.7186	Intermediate Similarity	NPD6585	Discontinued
0.7175	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3225	Approved
0.717	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD1465	Phase 2
0.716	Intermediate Similarity	NPD5761	Phase 2
0.716	Intermediate Similarity	NPD5760	Phase 2
0.7152	Intermediate Similarity	NPD6651	Approved
0.7134	Intermediate Similarity	NPD7390	Discontinued
0.7134	Intermediate Similarity	NPD943	Approved
0.7134	Intermediate Similarity	NPD4307	Phase 2
0.7124	Intermediate Similarity	NPD1203	Approved
0.7118	Intermediate Similarity	NPD4288	Approved
0.7115	Intermediate Similarity	NPD3268	Approved
0.7115	Intermediate Similarity	NPD1296	Phase 2
0.7097	Intermediate Similarity	NPD4908	Phase 1
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1933	Approved
0.7086	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4363	Phase 3
0.7081	Intermediate Similarity	NPD4360	Phase 2
0.7078	Intermediate Similarity	NPD1019	Discontinued
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7055	Intermediate Similarity	NPD4628	Phase 3
0.7055	Intermediate Similarity	NPD1241	Discontinued
0.7047	Intermediate Similarity	NPD1548	Phase 1
0.7043	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4361	Phase 2
0.7039	Intermediate Similarity	NPD3972	Approved
0.7024	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD1729	Discontinued
0.7018	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3764	Approved
0.7006	Intermediate Similarity	NPD3751	Discontinued
0.7005	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5124	Phase 1
0.6974	Remote Similarity	NPD1610	Phase 2
0.6971	Remote Similarity	NPD5711	Approved
0.6971	Remote Similarity	NPD5710	Approved
0.6957	Remote Similarity	NPD4308	Phase 3
0.6948	Remote Similarity	NPD1876	Approved
0.6941	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD9717	Approved
0.6901	Remote Similarity	NPD6844	Discontinued
0.6895	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3787	Discontinued
0.6868	Remote Similarity	NPD8313	Approved
0.6868	Remote Similarity	NPD8312	Approved
0.686	Remote Similarity	NPD8455	Phase 2
0.6848	Remote Similarity	NPD7003	Approved
0.6842	Remote Similarity	NPD17	Approved
0.6824	Remote Similarity	NPD7458	Discontinued
0.6818	Remote Similarity	NPD7199	Phase 2
0.681	Remote Similarity	NPD5406	Approved
0.681	Remote Similarity	NPD5404	Approved
0.681	Remote Similarity	NPD6099	Approved
0.681	Remote Similarity	NPD6100	Approved
0.681	Remote Similarity	NPD5408	Approved
0.681	Remote Similarity	NPD5405	Approved
0.6795	Remote Similarity	NPD2797	Approved
0.6791	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.677	Remote Similarity	NPD230	Phase 1
0.677	Remote Similarity	NPD447	Suspended
0.6769	Remote Similarity	NPD7584	Approved
0.6754	Remote Similarity	NPD8285	Discontinued
0.6753	Remote Similarity	NPD422	Phase 1
0.6747	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5242	Approved
0.6742	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD2424	Discontinued
0.6726	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD7177	Discontinued
0.671	Remote Similarity	NPD1608	Approved
0.6708	Remote Similarity	NPD3140	Approved
0.6708	Remote Similarity	NPD1613	Approved
0.6708	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD3142	Approved
0.6707	Remote Similarity	NPD3887	Approved
0.6704	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1470	Approved
0.6688	Remote Similarity	NPD1164	Approved
0.6687	Remote Similarity	NPD6798	Discontinued
0.6686	Remote Similarity	NPD4947	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2353	Approved
0.6667	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6104	Discontinued
0.6648	Remote Similarity	NPD6971	Discontinued
0.6647	Remote Similarity	NPD6273	Approved
0.6647	Remote Similarity	NPD7466	Approved
0.6646	Remote Similarity	NPD651	Clinical (unspecified phase)

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