NPASS Compound

Structure

NPC472581 OpenBabel07101718292D 25 28 0 0 1 0 0 0 0 0999 V2000 -4.3005 2.4487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3005 1.4487 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 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 -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 0.8660 -1.5000 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 3.4641 1.0000 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 -1.7321 0.0000 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 -2.5981 -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 1 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4345 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 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 -2.9345 2.8147 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 20 1 0 0 0 0 2 20 1 0 0 0 0 3 5 1 0 0 0 0 3 11 2 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 12 2 0 0 0 0 6 12 1 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 18 2 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 19 2 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 15 22 2 0 0 0 0 16 24 1 0 0 0 0 17 11 1 6 0 0 0 17 25 1 0 0 0 0 18 20 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.12
Volume:	343.11
LogP:	3.558
LogD:	2.901
LogS:	-4.48
# Rotatable Bonds:	2
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	3.239
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.673
MDCK Permeability:	1.7484295312897302e-05
Pgp-inhibitor:	0.273
Pgp-substrate:	0.013
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.342

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.047
Plasma Protein Binding (PPB):	91.43781280517578%
Volume Distribution (VD):	0.57
Pgp-substrate:	10.82447338104248%

ADMET: Metabolism

CYP1A2-inhibitor:	0.731
CYP1A2-substrate:	0.769
CYP2C19-inhibitor:	0.912
CYP2C19-substrate:	0.172
CYP2C9-inhibitor:	0.879
CYP2C9-substrate:	0.935
CYP2D6-inhibitor:	0.666
CYP2D6-substrate:	0.769
CYP3A4-inhibitor:	0.447
CYP3A4-substrate:	0.356

ADMET: Excretion

Clearance (CL):	10.058
Half-life (T1/2):	0.288

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.465
Drug-inuced Liver Injury (DILI):	0.934
AMES Toxicity:	0.199
Rat Oral Acute Toxicity:	0.803
Maximum Recommended Daily Dose:	0.409
Skin Sensitization:	0.142
Carcinogencity:	0.812
Eye Corrosion:	0.003
Eye Irritation:	0.183
Respiratory Toxicity:	0.643

Download Data

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

Natural Product: NPC472581

Natural Product ID:	NPC472581
*Common Name:**	NNTNZSXIELRUQM-KRWDZBQOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NNTNZSXIELRUQM-KRWDZBQOSA-N
Standard InCHI:	InChI=1S/C20H18O5/c1-20(2,23)18-9-14-16(24-18)8-7-13-15(22)10-17(25-19(13)14)11-3-5-12(21)6-4-11/h3-9,17,21,23H,10H2,1-2H3/t17-/m0/s1
SMILES:	Oc1ccc(cc1)[C@@H]1CC(=O)c2c(O1)c1cc(oc1cc2)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577244
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002614] Furanoflavonoids and dihydrofuranoflavonoids

*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
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[18359631]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[25710081]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[3069958]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[8759164]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30150	Psoralea corylifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[529657]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	10000.0	nM	PMID[529657]
NPT2	Others	Unspecified		IC50	=	134600.0	nM	PMID[529657]

☑ 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 NPC472581 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	407
0.1-0.2	1662
0.2-0.3	3892
0.3-0.4	9603
0.4-0.5	8766
0.5-0.6	4022
0.6-0.7	5518
0.7-0.8	4461
0.8-0.85	2436
0.85-0.9	1720
0.9-0.95	209
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9806	High Similarity	NPC219861
0.956	High Similarity	NPC476459
0.949	High Similarity	NPC30655
0.949	High Similarity	NPC74854
0.949	High Similarity	NPC45124
0.9416	High Similarity	NPC473996
0.9371	High Similarity	NPC109180
0.9355	High Similarity	NPC1477
0.9355	High Similarity	NPC213608
0.9351	High Similarity	NPC472580
0.9351	High Similarity	NPC472636
0.9304	High Similarity	NPC304839
0.9304	High Similarity	NPC220582
0.9299	High Similarity	NPC65504
0.929	High Similarity	NPC476238
0.929	High Similarity	NPC210597
0.929	High Similarity	NPC243171
0.929	High Similarity	NPC5871
0.929	High Similarity	NPC171651
0.929	High Similarity	NPC327269
0.929	High Similarity	NPC35567
0.929	High Similarity	NPC31627
0.929	High Similarity	NPC477957
0.9286	High Similarity	NPC472421
0.9241	High Similarity	NPC40583
0.9231	High Similarity	NPC122365
0.9231	High Similarity	NPC209760
0.9231	High Similarity	NPC100134
0.9231	High Similarity	NPC293286
0.9226	High Similarity	NPC262039
0.9226	High Similarity	NPC262038
0.9226	High Similarity	NPC319910
0.9226	High Similarity	NPC254412
0.9226	High Similarity	NPC474744
0.9226	High Similarity	NPC472420
0.9226	High Similarity	NPC472422
0.9226	High Similarity	NPC474772
0.9226	High Similarity	NPC471676
0.9226	High Similarity	NPC263384
0.9226	High Similarity	NPC472423
0.9226	High Similarity	NPC278476
0.9226	High Similarity	NPC244577
0.9226	High Similarity	NPC471675
0.9226	High Similarity	NPC471229
0.9221	High Similarity	NPC37226
0.9221	High Similarity	NPC226644
0.9202	High Similarity	NPC120220
0.9193	High Similarity	NPC259007
0.9193	High Similarity	NPC204088
0.9193	High Similarity	NPC329215
0.9187	High Similarity	NPC193998
0.9172	High Similarity	NPC48579
0.9172	High Similarity	NPC471116
0.9172	High Similarity	NPC259710
0.9172	High Similarity	NPC476169
0.9172	High Similarity	NPC217706
0.9172	High Similarity	NPC207809
0.9172	High Similarity	NPC304207
0.9167	High Similarity	NPC263676
0.9167	High Similarity	NPC285623
0.9167	High Similarity	NPC138288
0.9167	High Similarity	NPC216035
0.9167	High Similarity	NPC217149
0.9161	High Similarity	NPC105136
0.9161	High Similarity	NPC267117
0.9146	High Similarity	NPC472584
0.9136	High Similarity	NPC53640
0.9136	High Similarity	NPC323137
0.9114	High Similarity	NPC10754
0.9114	High Similarity	NPC20530
0.9114	High Similarity	NPC215917
0.9108	High Similarity	NPC223701
0.9108	High Similarity	NPC244250
0.9108	High Similarity	NPC236756
0.9108	High Similarity	NPC20907
0.9108	High Similarity	NPC311579
0.9108	High Similarity	NPC472462
0.9108	High Similarity	NPC7989
0.9108	High Similarity	NPC469405
0.9108	High Similarity	NPC248793
0.9108	High Similarity	NPC180301
0.9108	High Similarity	NPC472583
0.9108	High Similarity	NPC203080
0.9103	High Similarity	NPC170169
0.9103	High Similarity	NPC471677
0.9103	High Similarity	NPC116604
0.9102	High Similarity	NPC104682
0.9097	High Similarity	NPC37208
0.9097	High Similarity	NPC39929
0.9097	High Similarity	NPC277032
0.9097	High Similarity	NPC221868
0.9097	High Similarity	NPC296030
0.9097	High Similarity	NPC317492
0.9091	High Similarity	NPC130581
0.9091	High Similarity	NPC14875
0.9091	High Similarity	NPC472918
0.9091	High Similarity	NPC12148
0.908	High Similarity	NPC241820
0.9062	High Similarity	NPC306978
0.9057	High Similarity	NPC260902
0.9057	High Similarity	NPC296957
0.9051	High Similarity	NPC111341
0.9051	High Similarity	NPC304745
0.9051	High Similarity	NPC477958
0.9051	High Similarity	NPC198490
0.9045	High Similarity	NPC475790
0.9038	High Similarity	NPC230713
0.9038	High Similarity	NPC78335
0.9038	High Similarity	NPC61258
0.9032	High Similarity	NPC168085
0.9032	High Similarity	NPC135325
0.9032	High Similarity	NPC272194
0.9026	High Similarity	NPC300267
0.9026	High Similarity	NPC210826
0.9026	High Similarity	NPC229190
0.9026	High Similarity	NPC51641
0.9024	High Similarity	NPC53252
0.9018	High Similarity	NPC277480
0.9012	High Similarity	NPC124038
0.9006	High Similarity	NPC92589
0.9	High Similarity	NPC476350
0.9	High Similarity	NPC476349
0.8994	High Similarity	NPC160015
0.8994	High Similarity	NPC146636
0.8994	High Similarity	NPC208152
0.8994	High Similarity	NPC78492
0.8994	High Similarity	NPC247677
0.8987	High Similarity	NPC268193
0.8987	High Similarity	NPC183874
0.8987	High Similarity	NPC41719
0.8981	High Similarity	NPC474021
0.8981	High Similarity	NPC474023
0.8976	High Similarity	NPC310794
0.8974	High Similarity	NPC472628
0.8974	High Similarity	NPC178202
0.8974	High Similarity	NPC89442
0.897	High Similarity	NPC131866
0.8968	High Similarity	NPC472627
0.8968	High Similarity	NPC40086
0.8968	High Similarity	NPC476182
0.8968	High Similarity	NPC122828
0.8968	High Similarity	NPC211466
0.8968	High Similarity	NPC176869
0.8968	High Similarity	NPC3779
0.8968	High Similarity	NPC44721
0.8961	High Similarity	NPC209040
0.8957	High Similarity	NPC37183
0.8957	High Similarity	NPC300053
0.8957	High Similarity	NPC38914
0.8957	High Similarity	NPC108433
0.8951	High Similarity	NPC272722
0.8944	High Similarity	NPC328102
0.8944	High Similarity	NPC115432
0.8944	High Similarity	NPC471976
0.8944	High Similarity	NPC472624
0.8944	High Similarity	NPC260296
0.8938	High Similarity	NPC268360
0.8938	High Similarity	NPC210048
0.8938	High Similarity	NPC161650
0.8931	High Similarity	NPC470681
0.8931	High Similarity	NPC108937
0.8931	High Similarity	NPC477530
0.8931	High Similarity	NPC279218
0.8931	High Similarity	NPC148938
0.8924	High Similarity	NPC150123
0.8924	High Similarity	NPC56232
0.8924	High Similarity	NPC161881
0.8924	High Similarity	NPC244583
0.8924	High Similarity	NPC253872
0.8924	High Similarity	NPC10807
0.8917	High Similarity	NPC135303
0.8917	High Similarity	NPC148423
0.8916	High Similarity	NPC248593
0.8916	High Similarity	NPC28589
0.891	High Similarity	NPC39195
0.891	High Similarity	NPC296869
0.8909	High Similarity	NPC152477
0.8903	High Similarity	NPC472629
0.8903	High Similarity	NPC1940
0.8903	High Similarity	NPC148011
0.8903	High Similarity	NPC316769
0.8903	High Similarity	NPC124729
0.8902	High Similarity	NPC119589
0.8902	High Similarity	NPC82330
0.8896	High Similarity	NPC214166
0.8896	High Similarity	NPC150408
0.8896	High Similarity	NPC166138
0.8896	High Similarity	NPC472582
0.8896	High Similarity	NPC38591
0.8896	High Similarity	NPC39329
0.8896	High Similarity	NPC221432
0.8896	High Similarity	NPC478086
0.8896	High Similarity	NPC257097
0.8896	High Similarity	NPC225884
0.8896	High Similarity	NPC106985
0.8896	High Similarity	NPC91560
0.8896	High Similarity	NPC316816
0.8896	High Similarity	NPC175504
0.8896	High Similarity	NPC302181
0.8896	High Similarity	NPC164980

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 NPC472581 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	360
0.1-0.2	903
0.2-0.3	1684
0.3-0.4	2660
0.4-0.5	1917
0.5-0.6	1075
0.6-0.7	363
0.7-0.8	125
0.8-0.85	39
0.85-0.9	23
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8938	High Similarity	NPD7075	Discontinued
0.8868	High Similarity	NPD7096	Clinical (unspecified phase)
0.8839	High Similarity	NPD4378	Clinical (unspecified phase)
0.8797	High Similarity	NPD4380	Phase 2
0.875	High Similarity	NPD2393	Clinical (unspecified phase)
0.8696	High Similarity	NPD8443	Clinical (unspecified phase)
0.8642	High Similarity	NPD3882	Suspended
0.8639	High Similarity	NPD6559	Discontinued
0.8625	High Similarity	NPD7411	Suspended
0.8571	High Similarity	NPD6801	Discontinued
0.8571	High Similarity	NPD1549	Phase 2
0.8571	High Similarity	NPD1934	Approved
0.8506	High Similarity	NPD1552	Clinical (unspecified phase)
0.8506	High Similarity	NPD1550	Clinical (unspecified phase)
0.8503	High Similarity	NPD6168	Clinical (unspecified phase)
0.8503	High Similarity	NPD6166	Phase 2
0.8503	High Similarity	NPD6167	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD3749	Approved
0.8476	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD1247	Approved
0.8418	Intermediate Similarity	NPD6799	Approved
0.8393	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD5494	Approved
0.8323	Intermediate Similarity	NPD2796	Approved
0.8294	Intermediate Similarity	NPD3818	Discontinued
0.8293	Intermediate Similarity	NPD2801	Approved
0.8261	Intermediate Similarity	NPD920	Approved
0.8258	Intermediate Similarity	NPD1510	Phase 2
0.8221	Intermediate Similarity	NPD6599	Discontinued
0.8214	Intermediate Similarity	NPD6959	Discontinued
0.8199	Intermediate Similarity	NPD1512	Approved
0.8193	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7819	Suspended
0.8165	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD2344	Approved
0.8137	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD3817	Phase 2
0.8118	Intermediate Similarity	NPD3926	Phase 2
0.8117	Intermediate Similarity	NPD1240	Approved
0.8095	Intermediate Similarity	NPD919	Approved
0.8084	Intermediate Similarity	NPD7768	Phase 2
0.8075	Intermediate Similarity	NPD1511	Approved
0.805	Intermediate Similarity	NPD1243	Approved
0.805	Intermediate Similarity	NPD2800	Approved
0.8046	Intermediate Similarity	NPD6797	Phase 2
0.8037	Intermediate Similarity	NPD5403	Approved
0.8024	Intermediate Similarity	NPD5402	Approved
0.8013	Intermediate Similarity	NPD1607	Approved
0.8012	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7251	Discontinued
0.7989	Intermediate Similarity	NPD7074	Phase 3
0.7955	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD7808	Phase 3
0.7953	Intermediate Similarity	NPD6232	Discontinued
0.795	Intermediate Similarity	NPD2309	Approved
0.7943	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD5844	Phase 1
0.7931	Intermediate Similarity	NPD7054	Approved
0.7919	Intermediate Similarity	NPD7473	Discontinued
0.7914	Intermediate Similarity	NPD5401	Approved
0.7886	Intermediate Similarity	NPD7472	Approved
0.7877	Intermediate Similarity	NPD8434	Phase 2
0.7805	Intermediate Similarity	NPD2533	Approved
0.7805	Intermediate Similarity	NPD2532	Approved
0.7805	Intermediate Similarity	NPD2534	Approved
0.7705	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD3751	Discontinued
0.7669	Intermediate Similarity	NPD3750	Approved
0.7669	Intermediate Similarity	NPD4628	Phase 3
0.7654	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2935	Discontinued
0.764	Intermediate Similarity	NPD1551	Phase 2
0.764	Intermediate Similarity	NPD5953	Discontinued
0.7634	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7627	Intermediate Similarity	NPD7286	Phase 2
0.7619	Intermediate Similarity	NPD3226	Approved
0.7593	Intermediate Similarity	NPD1471	Phase 3
0.7593	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2799	Discontinued
0.7557	Intermediate Similarity	NPD2403	Approved
0.7544	Intermediate Similarity	NPD1465	Phase 2
0.7543	Intermediate Similarity	NPD3787	Discontinued
0.7532	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD4287	Approved
0.7458	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6651	Approved
0.7443	Intermediate Similarity	NPD6808	Phase 2
0.7439	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2424	Discontinued
0.7438	Intermediate Similarity	NPD943	Approved
0.7432	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6798	Discontinued
0.7421	Intermediate Similarity	NPD6777	Approved
0.7421	Intermediate Similarity	NPD6781	Approved
0.7421	Intermediate Similarity	NPD6779	Approved
0.7421	Intermediate Similarity	NPD6776	Approved
0.7421	Intermediate Similarity	NPD6780	Approved
0.7421	Intermediate Similarity	NPD6778	Approved
0.7421	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD6782	Approved
0.7418	Intermediate Similarity	NPD8313	Approved
0.7418	Intermediate Similarity	NPD8312	Approved
0.7405	Intermediate Similarity	NPD4908	Phase 1
0.7403	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD2296	Approved
0.7396	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2346	Discontinued
0.7371	Intermediate Similarity	NPD7584	Approved
0.7371	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3748	Approved
0.7362	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7033	Discontinued
0.7345	Intermediate Similarity	NPD5710	Approved
0.7345	Intermediate Similarity	NPD5711	Approved
0.7345	Intermediate Similarity	NPD7229	Phase 3
0.7341	Intermediate Similarity	NPD5761	Phase 2
0.7341	Intermediate Similarity	NPD5760	Phase 2
0.734	Intermediate Similarity	NPD4363	Phase 3
0.734	Intermediate Similarity	NPD4360	Phase 2
0.7329	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1613	Approved
0.7326	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7390	Discontinued
0.7317	Intermediate Similarity	NPD6100	Approved
0.7317	Intermediate Similarity	NPD6099	Approved
0.7312	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7435	Discontinued
0.7303	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD8150	Discontinued
0.7293	Intermediate Similarity	NPD1729	Discontinued
0.7284	Intermediate Similarity	NPD6355	Discontinued
0.7283	Intermediate Similarity	NPD6279	Approved
0.7283	Intermediate Similarity	NPD6280	Approved
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7870	Phase 2
0.7268	Intermediate Similarity	NPD7871	Phase 2
0.7267	Intermediate Similarity	NPD6233	Phase 2
0.7246	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD8455	Phase 2
0.7216	Intermediate Similarity	NPD7698	Approved
0.7216	Intermediate Similarity	NPD7696	Phase 3
0.7216	Intermediate Similarity	NPD7697	Approved
0.7215	Intermediate Similarity	NPD1203	Approved
0.7211	Intermediate Similarity	NPD4361	Phase 2
0.7211	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8151	Discontinued
0.7205	Intermediate Similarity	NPD3268	Approved
0.7205	Intermediate Similarity	NPD3764	Approved
0.7202	Intermediate Similarity	NPD6190	Approved
0.7191	Intermediate Similarity	NPD7199	Phase 2
0.7188	Intermediate Similarity	NPD6832	Phase 2
0.7188	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD2163	Approved
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.7178	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5124	Phase 1
0.7178	Intermediate Similarity	NPD230	Phase 1
0.7175	Intermediate Similarity	NPD6234	Discontinued
0.7158	Intermediate Similarity	NPD6535	Approved
0.7158	Intermediate Similarity	NPD6534	Approved
0.7158	Intermediate Similarity	NPD3823	Discontinued
0.7157	Intermediate Similarity	NPD7701	Phase 2
0.7152	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4625	Phase 3
0.7136	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7783	Phase 2
0.7135	Intermediate Similarity	NPD5049	Phase 3
0.7125	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7458	Discontinued
0.7101	Intermediate Similarity	NPD3887	Approved
0.7101	Intermediate Similarity	NPD2354	Approved
0.7086	Intermediate Similarity	NPD37	Approved
0.7085	Intermediate Similarity	NPD7874	Approved
0.7085	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2654	Approved
0.7073	Intermediate Similarity	NPD447	Suspended
0.7073	Intermediate Similarity	NPD1933	Approved
0.7072	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2798	Approved
0.7062	Intermediate Similarity	NPD4965	Approved
0.7062	Intermediate Similarity	NPD4966	Approved
0.7062	Intermediate Similarity	NPD4967	Phase 2
0.705	Intermediate Similarity	NPD7801	Approved
0.7048	Intermediate Similarity	NPD4308	Phase 3
0.7047	Intermediate Similarity	NPD7699	Phase 2
0.7047	Intermediate Similarity	NPD7700	Phase 2
0.7037	Intermediate Similarity	NPD3027	Phase 3
0.7032	Intermediate Similarity	NPD1548	Phase 1
0.7029	Intermediate Similarity	NPD5889	Approved
0.7029	Intermediate Similarity	NPD5890	Approved
0.7027	Intermediate Similarity	NPD6764	Approved
0.7027	Intermediate Similarity	NPD6765	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