NPASS Compound

Structure

NPC122365 OpenBabel07101718242D 27 30 0 0 1 0 0 0 0 0999 V2000 -1.8171 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 3.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 2.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0132 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8793 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -4.3090 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 -4.4152 -1.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 4 1 0 0 0 0 3 12 2 0 0 0 0 4 13 1 0 0 0 0 5 6 2 0 0 0 0 5 14 1 0 0 0 0 6 26 1 0 0 0 0 7 13 1 0 0 0 0 7 15 2 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 9 17 1 0 0 0 0 10 16 1 0 0 0 0 10 20 2 0 0 0 0 11 18 1 0 0 0 0 11 19 1 0 0 0 0 13 22 2 0 0 0 0 14 22 1 0 0 0 0 16 23 1 0 0 0 0 17 21 2 0 0 0 0 17 24 1 0 0 0 0 18 21 1 0 0 0 0 18 25 2 0 0 0 0 19 15 1 6 0 0 0 19 27 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.13
Volume:	375.065
LogP:	5.322
LogD:	3.936
LogS:	-4.215
# Rotatable Bonds:	3
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.635
Synthetic Accessibility Score:	3.463
Fsp3:	0.227
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.773
MDCK Permeability:	1.4671848475700244e-05
Pgp-inhibitor:	0.046
Pgp-substrate:	0.129
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.674
30% Bioavailability (F30%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	93.08110809326172%
Volume Distribution (VD):	0.956
Pgp-substrate:	7.56279993057251%

ADMET: Metabolism

CYP1A2-inhibitor:	0.903
CYP1A2-substrate:	0.343
CYP2C19-inhibitor:	0.97
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.914
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.908
CYP2D6-substrate:	0.585
CYP3A4-inhibitor:	0.797
CYP3A4-substrate:	0.134

ADMET: Excretion

Clearance (CL):	17.369
Half-life (T1/2):	0.429

ADMET: Toxicity

hERG Blockers:	0.064
Human Hepatotoxicity (H-HT):	0.85
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.079
Rat Oral Acute Toxicity:	0.804
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.648
Carcinogencity:	0.579
Eye Corrosion:	0.003
Eye Irritation:	0.501
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC122365

Natural Product ID:	NPC122365
*Common Name:**	Abyssinoflavanone Vi
IUPAC Name:	(2S)-5,7-dihydroxy-2-[7-(3-methylbut-2-enyl)-1-benzofuran-5-yl]-2,3-dihydrochromen-4-one
Synonyms:	Abyssinoflavanone VI
Standard InCHIKey:	MXJNLOCPZJNQMY-IBGZPJMESA-N
Standard InCHI:	InChI=1S/C22H20O5/c1-12(2)3-4-13-7-15(8-14-5-6-26-22(13)14)19-11-18(25)21-17(24)9-16(23)10-20(21)27-19/h3,5-10,19,23-24H,4,11H2,1-2H3/t19-/m0/s1
SMILES:	CC(=CCc1cc(cc2c1occ2)[C@@H]1CC(=O)c2c(O1)cc(cc2O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL389650
PubChem CID:	16737096
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003643] 3'-prenylated flavans [CHEMONTID:0003506] 3'-prenylated flavanones

*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
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17489632]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	PMID[18484536]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	stem bark	Mukono, Uganda	2005-JUN	PMID[19008110]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19836230]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20337486]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21116437]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8526	Erythrina abyssinica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8526	Erythrina abyssinica	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	18900.0	nM	PMID[491533]

☑ 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 NPC122365 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	376
0.1-0.2	1544
0.2-0.3	3690
0.3-0.4	9695
0.4-0.5	8930
0.5-0.6	3755
0.6-0.7	5749
0.7-0.8	4982
0.8-0.85	2216
0.85-0.9	1177
0.9-0.95	555
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.9597	High Similarity	NPC213608
0.9597	High Similarity	NPC1477
0.9592	High Similarity	NPC39929
0.9592	High Similarity	NPC296030
0.9589	High Similarity	NPC12148
0.9589	High Similarity	NPC130581
0.953	High Similarity	NPC5871
0.9524	High Similarity	NPC135325
0.9521	High Similarity	NPC300267
0.9521	High Similarity	NPC51641
0.9521	High Similarity	NPC210826
0.9474	High Similarity	NPC476350
0.9474	High Similarity	NPC476349
0.9474	High Similarity	NPC40583
0.947	High Similarity	NPC247677
0.947	High Similarity	NPC160015
0.9459	High Similarity	NPC226644
0.9459	High Similarity	NPC37226
0.9459	High Similarity	NPC37208
0.9459	High Similarity	NPC221868
0.9408	High Similarity	NPC260902
0.9408	High Similarity	NPC65504
0.9408	High Similarity	NPC296957
0.94	High Similarity	NPC263676
0.9392	High Similarity	NPC168085
0.9392	High Similarity	NPC272194
0.9384	High Similarity	NPC302181
0.9384	High Similarity	NPC310130
0.9384	High Similarity	NPC75049
0.9384	High Similarity	NPC143896
0.9384	High Similarity	NPC164980
0.9384	High Similarity	NPC149026
0.9384	High Similarity	NPC225884
0.9384	High Similarity	NPC169591
0.9384	High Similarity	NPC257097
0.9384	High Similarity	NPC91560
0.9384	High Similarity	NPC39329
0.9384	High Similarity	NPC175504
0.9384	High Similarity	NPC221432
0.9384	High Similarity	NPC68104
0.9384	High Similarity	NPC150408
0.9333	High Similarity	NPC170169
0.9333	High Similarity	NPC156244
0.9333	High Similarity	NPC472580
0.9333	High Similarity	NPC116604
0.9329	High Similarity	NPC317492
0.932	High Similarity	NPC209040
0.932	High Similarity	NPC236766
0.932	High Similarity	NPC473015
0.932	High Similarity	NPC473013
0.932	High Similarity	NPC197252
0.932	High Similarity	NPC230943
0.9315	High Similarity	NPC228504
0.9315	High Similarity	NPC220998
0.9315	High Similarity	NPC182852
0.9315	High Similarity	NPC40833
0.9315	High Similarity	NPC167624
0.9315	High Similarity	NPC107572
0.9315	High Similarity	NPC37496
0.9315	High Similarity	NPC64915
0.9315	High Similarity	NPC227579
0.9315	High Similarity	NPC265040
0.9315	High Similarity	NPC10937
0.9315	High Similarity	NPC76338
0.9315	High Similarity	NPC223500
0.9315	High Similarity	NPC1089
0.9315	High Similarity	NPC161506
0.9315	High Similarity	NPC53192
0.9315	High Similarity	NPC78
0.9315	High Similarity	NPC66515
0.9315	High Similarity	NPC166482
0.9315	High Similarity	NPC32739
0.9315	High Similarity	NPC324436
0.9315	High Similarity	NPC328164
0.9315	High Similarity	NPC177354
0.9315	High Similarity	NPC306829
0.9315	High Similarity	NPC76372
0.9315	High Similarity	NPC125855
0.9315	High Similarity	NPC194432
0.9315	High Similarity	NPC296917
0.9315	High Similarity	NPC166934
0.9315	High Similarity	NPC148757
0.9315	High Similarity	NPC324134
0.9276	High Similarity	NPC198490
0.9272	High Similarity	NPC67654
0.9272	High Similarity	NPC477957
0.9272	High Similarity	NPC473996
0.9267	High Similarity	NPC230713
0.9267	High Similarity	NPC78335
0.9257	High Similarity	NPC470134
0.9257	High Similarity	NPC109183
0.9257	High Similarity	NPC2416
0.9257	High Similarity	NPC473078
0.9257	High Similarity	NPC476153
0.9257	High Similarity	NPC472629
0.9257	High Similarity	NPC470131
0.9257	High Similarity	NPC470133
0.9257	High Similarity	NPC215885
0.9257	High Similarity	NPC470132
0.9252	High Similarity	NPC471621
0.9252	High Similarity	NPC316816
0.9252	High Similarity	NPC106985
0.9252	High Similarity	NPC478086
0.9252	High Similarity	NPC166138
0.9252	High Similarity	NPC185276
0.9252	High Similarity	NPC107177
0.9252	High Similarity	NPC18585
0.9252	High Similarity	NPC223812
0.9252	High Similarity	NPC214166
0.9252	High Similarity	NPC85162
0.9252	High Similarity	NPC81697
0.9252	High Similarity	NPC77794
0.9252	High Similarity	NPC278249
0.9252	High Similarity	NPC125894
0.9247	High Similarity	NPC166689
0.9247	High Similarity	NPC279650
0.9247	High Similarity	NPC312391
0.9247	High Similarity	NPC3188
0.9247	High Similarity	NPC110038
0.9247	High Similarity	NPC324386
0.9247	High Similarity	NPC4743
0.9247	High Similarity	NPC258630
0.9247	High Similarity	NPC17170
0.9247	High Similarity	NPC248372
0.9247	High Similarity	NPC156190
0.9247	High Similarity	NPC213322
0.9247	High Similarity	NPC96408
0.9231	High Similarity	NPC472581
0.9226	High Similarity	NPC74854
0.9226	High Similarity	NPC30655
0.9226	High Similarity	NPC45124
0.9211	High Similarity	NPC183874
0.9211	High Similarity	NPC472462
0.9205	High Similarity	NPC472636
0.92	High Similarity	NPC214493
0.92	High Similarity	NPC178202
0.9195	High Similarity	NPC23728
0.9195	High Similarity	NPC296998
0.9195	High Similarity	NPC110303
0.9195	High Similarity	NPC10990
0.9195	High Similarity	NPC473077
0.9195	High Similarity	NPC300988
0.9189	High Similarity	NPC110776
0.9189	High Similarity	NPC235217
0.9189	High Similarity	NPC470136
0.9189	High Similarity	NPC131568
0.9189	High Similarity	NPC473014
0.9189	High Similarity	NPC271590
0.9189	High Similarity	NPC124780
0.9189	High Similarity	NPC131579
0.9189	High Similarity	NPC271288
0.9189	High Similarity	NPC39045
0.9189	High Similarity	NPC470135
0.9189	High Similarity	NPC470890
0.9189	High Similarity	NPC87486
0.9184	High Similarity	NPC144499
0.9184	High Similarity	NPC147145
0.9178	High Similarity	NPC188243
0.9178	High Similarity	NPC69769
0.9178	High Similarity	NPC6407
0.9178	High Similarity	NPC110228
0.9167	High Similarity	NPC193998
0.9161	High Similarity	NPC260296
0.9161	High Similarity	NPC115432
0.9156	High Similarity	NPC269495
0.915	High Similarity	NPC148938
0.9145	High Similarity	NPC285623
0.9145	High Similarity	NPC327269
0.9145	High Similarity	NPC31627
0.9145	High Similarity	NPC476238
0.9145	High Similarity	NPC253872
0.9139	High Similarity	NPC135303
0.9139	High Similarity	NPC321896
0.9139	High Similarity	NPC476185
0.9139	High Similarity	NPC148423
0.9139	High Similarity	NPC472421
0.9133	High Similarity	NPC39195
0.9133	High Similarity	NPC160821
0.9133	High Similarity	NPC132592
0.9128	High Similarity	NPC301276
0.9128	High Similarity	NPC214774
0.9128	High Similarity	NPC67805
0.9128	High Similarity	NPC290133
0.9128	High Similarity	NPC187282
0.9128	High Similarity	NPC24136
0.9128	High Similarity	NPC20488
0.9128	High Similarity	NPC475052
0.9128	High Similarity	NPC312973
0.9128	High Similarity	NPC285630
0.9128	High Similarity	NPC267375
0.9128	High Similarity	NPC54577
0.9128	High Similarity	NPC246948
0.9128	High Similarity	NPC142405
0.9128	High Similarity	NPC470647
0.9128	High Similarity	NPC83357
0.9128	High Similarity	NPC127059
0.9128	High Similarity	NPC73320
0.9128	High Similarity	NPC195621
0.9128	High Similarity	NPC228779
0.9128	High Similarity	NPC176229

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 NPC122365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	945
0.2-0.3	1489
0.3-0.4	2567
0.4-0.5	2003
0.5-0.6	1219
0.6-0.7	411
0.7-0.8	131
0.8-0.85	36
0.85-0.9	21
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9041	High Similarity	NPD1549	Phase 2
0.8973	High Similarity	NPD1550	Clinical (unspecified phase)
0.8973	High Similarity	NPD1552	Clinical (unspecified phase)
0.8933	High Similarity	NPD4378	Clinical (unspecified phase)
0.8903	High Similarity	NPD8443	Clinical (unspecified phase)
0.8839	High Similarity	NPD2393	Clinical (unspecified phase)
0.8834	High Similarity	NPD6559	Discontinued
0.8831	High Similarity	NPD7411	Suspended
0.8808	High Similarity	NPD7410	Clinical (unspecified phase)
0.879	High Similarity	NPD7075	Discontinued
0.8776	High Similarity	NPD2796	Approved
0.8766	High Similarity	NPD4380	Phase 2
0.8718	High Similarity	NPD7096	Clinical (unspecified phase)
0.8707	High Similarity	NPD1510	Phase 2
0.8693	High Similarity	NPD920	Approved
0.8675	High Similarity	NPD643	Clinical (unspecified phase)
0.8671	High Similarity	NPD3749	Approved
0.8599	High Similarity	NPD7819	Suspended
0.858	High Similarity	NPD7852	Clinical (unspecified phase)
0.8562	High Similarity	NPD642	Clinical (unspecified phase)
0.8562	High Similarity	NPD1240	Approved
0.8535	High Similarity	NPD1934	Approved
0.8509	High Similarity	NPD6959	Discontinued
0.8491	Intermediate Similarity	NPD7768	Phase 2
0.8477	Intermediate Similarity	NPD1243	Approved
0.8467	Intermediate Similarity	NPD2344	Approved
0.8446	Intermediate Similarity	NPD1607	Approved
0.8438	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD6801	Discontinued
0.8375	Intermediate Similarity	NPD3882	Suspended
0.8355	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD5494	Approved
0.8278	Intermediate Similarity	NPD1551	Phase 2
0.8272	Intermediate Similarity	NPD919	Approved
0.8258	Intermediate Similarity	NPD6799	Approved
0.8247	Intermediate Similarity	NPD2309	Approved
0.8242	Intermediate Similarity	NPD6166	Phase 2
0.8242	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD2800	Approved
0.8204	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD1247	Approved
0.8144	Intermediate Similarity	NPD3818	Discontinued
0.8141	Intermediate Similarity	NPD1511	Approved
0.8137	Intermediate Similarity	NPD2801	Approved
0.8065	Intermediate Similarity	NPD3750	Approved
0.8063	Intermediate Similarity	NPD6599	Discontinued
0.8038	Intermediate Similarity	NPD1512	Approved
0.8037	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7987	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD2532	Approved
0.7975	Intermediate Similarity	NPD2534	Approved
0.7975	Intermediate Similarity	NPD2533	Approved
0.7964	Intermediate Similarity	NPD3926	Phase 2
0.7941	Intermediate Similarity	NPD7074	Phase 3
0.7933	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD2935	Discontinued
0.7904	Intermediate Similarity	NPD6232	Discontinued
0.7895	Intermediate Similarity	NPD5953	Discontinued
0.7882	Intermediate Similarity	NPD7054	Approved
0.7875	Intermediate Similarity	NPD5403	Approved
0.787	Intermediate Similarity	NPD7473	Discontinued
0.7866	Intermediate Similarity	NPD3817	Phase 2
0.7857	Intermediate Similarity	NPD2799	Discontinued
0.7843	Intermediate Similarity	NPD6651	Approved
0.7836	Intermediate Similarity	NPD7472	Approved
0.7821	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD4908	Phase 1
0.7791	Intermediate Similarity	NPD6797	Phase 2
0.7778	Intermediate Similarity	NPD7286	Phase 2
0.775	Intermediate Similarity	NPD5401	Approved
0.7746	Intermediate Similarity	NPD7251	Discontinued
0.7742	Intermediate Similarity	NPD3748	Approved
0.7722	Intermediate Similarity	NPD4628	Phase 3
0.7722	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7808	Phase 3
0.7697	Intermediate Similarity	NPD2313	Discontinued
0.7651	Intermediate Similarity	NPD5402	Approved
0.7651	Intermediate Similarity	NPD2296	Approved
0.764	Intermediate Similarity	NPD4287	Approved
0.764	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1729	Discontinued
0.7628	Intermediate Similarity	NPD7033	Discontinued
0.7628	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1203	Approved
0.76	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5761	Phase 2
0.759	Intermediate Similarity	NPD5760	Phase 2
0.7586	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD6100	Approved
0.758	Intermediate Similarity	NPD6099	Approved
0.7578	Intermediate Similarity	NPD7390	Discontinued
0.7569	Intermediate Similarity	NPD4363	Phase 3
0.7569	Intermediate Similarity	NPD4360	Phase 2
0.7568	Intermediate Similarity	NPD1610	Phase 2
0.7566	Intermediate Similarity	NPD6832	Phase 2
0.7561	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3226	Approved
0.7546	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.753	Intermediate Similarity	NPD6280	Approved
0.753	Intermediate Similarity	NPD6279	Approved
0.7528	Intermediate Similarity	NPD8434	Phase 2
0.7527	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4361	Phase 2
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5711	Approved
0.7485	Intermediate Similarity	NPD7229	Phase 3
0.7485	Intermediate Similarity	NPD6808	Phase 2
0.7485	Intermediate Similarity	NPD5710	Approved
0.7484	Intermediate Similarity	NPD943	Approved
0.747	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD2654	Approved
0.7436	Intermediate Similarity	NPD5124	Phase 1
0.7436	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2798	Approved
0.7421	Intermediate Similarity	NPD1471	Phase 3
0.7415	Intermediate Similarity	NPD1548	Phase 1
0.7403	Intermediate Similarity	NPD4625	Phase 3
0.74	Intermediate Similarity	NPD9717	Approved
0.7381	Intermediate Similarity	NPD1465	Phase 2
0.7355	Intermediate Similarity	NPD3764	Approved
0.7355	Intermediate Similarity	NPD3268	Approved
0.7299	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD4308	Phase 3
0.7284	Intermediate Similarity	NPD7003	Approved
0.7273	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD8312	Approved
0.7263	Intermediate Similarity	NPD8313	Approved
0.7261	Intermediate Similarity	NPD1613	Approved
0.7261	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2797	Approved
0.725	Intermediate Similarity	NPD5406	Approved
0.725	Intermediate Similarity	NPD5408	Approved
0.725	Intermediate Similarity	NPD5405	Approved
0.725	Intermediate Similarity	NPD5404	Approved
0.7246	Intermediate Similarity	NPD7458	Discontinued
0.7244	Intermediate Similarity	NPD6798	Discontinued
0.7225	Intermediate Similarity	NPD7199	Phase 2
0.7225	Intermediate Similarity	NPD7584	Approved
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7216	Intermediate Similarity	NPD3751	Discontinued
0.7215	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1933	Approved
0.7181	Intermediate Similarity	NPD9545	Approved
0.7176	Intermediate Similarity	NPD8455	Phase 2
0.7171	Intermediate Similarity	NPD3972	Approved
0.7161	Intermediate Similarity	NPD2861	Phase 2
0.716	Intermediate Similarity	NPD2424	Discontinued
0.716	Intermediate Similarity	NPD5889	Approved
0.716	Intermediate Similarity	NPD5890	Approved
0.7158	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6104	Discontinued
0.7143	Intermediate Similarity	NPD1164	Approved
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4288	Approved
0.7119	Intermediate Similarity	NPD7177	Discontinued
0.7118	Intermediate Similarity	NPD6844	Discontinued
0.7115	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6355	Discontinued
0.7107	Intermediate Similarity	NPD230	Phase 1
0.7099	Intermediate Similarity	NPD6005	Phase 3
0.7099	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6004	Phase 3
0.7099	Intermediate Similarity	NPD6002	Phase 3
0.7099	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3787	Discontinued
0.7078	Intermediate Similarity	NPD3225	Approved
0.7075	Intermediate Similarity	NPD1241	Discontinued
0.7066	Intermediate Similarity	NPD6273	Approved
0.7062	Intermediate Similarity	NPD8151	Discontinued
0.7059	Intermediate Similarity	NPD1608	Approved
0.7056	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6971	Discontinued
0.7051	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7213	Phase 3
0.7048	Intermediate Similarity	NPD7212	Phase 2
0.7047	Intermediate Similarity	NPD9493	Approved
0.7044	Intermediate Similarity	NPD4307	Phase 2
0.7032	Intermediate Similarity	NPD1470	Approved
0.7032	Intermediate Similarity	NPD3266	Approved
0.7032	Intermediate Similarity	NPD3267	Approved
0.7025	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD411	Approved
0.7018	Intermediate Similarity	NPD7577	Discontinued
0.7018	Intermediate Similarity	NPD37	Approved
0.7013	Intermediate Similarity	NPD4749	Approved
0.7011	Intermediate Similarity	NPD6234	Discontinued
0.7006	Intermediate Similarity	NPD4662	Approved
0.7006	Intermediate Similarity	NPD7784	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