NPASS Compound

Structure

NPC472408 OpenBabel07101718182D 25 28 0 0 0 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 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 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 21 1 0 0 0 0 2 21 1 0 0 0 0 3 23 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 13 2 0 0 0 0 8 13 1 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 21 1 0 0 0 0 11 15 2 0 0 0 0 11 18 1 0 0 0 0 12 16 1 0 0 0 0 12 17 2 0 0 0 0 13 17 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 22 2 0 0 0 0 17 24 1 0 0 0 0 18 20 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.12
Volume:	348.979
LogP:	4.986
LogD:	4.148
LogS:	-5.36
# Rotatable Bonds:	2
TPSA:	48.67
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.684
Synthetic Accessibility Score:	2.637
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.654
MDCK Permeability:	1.494202297180891e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.222

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	95.14199829101562%
Volume Distribution (VD):	0.615
Pgp-substrate:	3.7904646396636963%

ADMET: Metabolism

CYP1A2-inhibitor:	0.901
CYP1A2-substrate:	0.745
CYP2C19-inhibitor:	0.927
CYP2C19-substrate:	0.222
CYP2C9-inhibitor:	0.898
CYP2C9-substrate:	0.864
CYP2D6-inhibitor:	0.739
CYP2D6-substrate:	0.624
CYP3A4-inhibitor:	0.822
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	3.222
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.903
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.268
Rat Oral Acute Toxicity:	0.934
Maximum Recommended Daily Dose:	0.773
Skin Sensitization:	0.253
Carcinogencity:	0.828
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.935

Download Data

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

Natural Product: NPC472408

Natural Product ID:	NPC472408
*Common Name:**	MRVXYFIPOKCCMI-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MRVXYFIPOKCCMI-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C21H18O4/c1-21(2)10-9-14-19-15(11-18(23-3)20(14)25-21)16(22)12-17(24-19)13-7-5-4-6-8-13/h4-12H,1-3H3
SMILES:	COc1cc2c(=O)cc(oc2c2c1OC(C)(C)C=C2)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3401059
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0003520] Pyranoflavonoids

*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	=	1.4	n.a.	PMID[564489]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	106.0	%	PMID[564489]

☑ 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 NPC472408 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	543
0.1-0.2	2105
0.2-0.3	5257
0.3-0.4	12143
0.4-0.5	5066
0.5-0.6	4172
0.6-0.7	5695
0.7-0.8	4527
0.8-0.85	1930
0.85-0.9	999
0.9-0.95	246
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9864	High Similarity	NPC128961
0.9796	High Similarity	NPC166201
0.9732	High Similarity	NPC180340
0.9667	High Similarity	NPC19097
0.966	High Similarity	NPC5840
0.966	High Similarity	NPC189270
0.9589	High Similarity	NPC205522
0.9536	High Similarity	NPC476981
0.953	High Similarity	NPC40033
0.9524	High Similarity	NPC63256
0.9524	High Similarity	NPC10304
0.9521	High Similarity	NPC14958
0.9521	High Similarity	NPC110639
0.9521	High Similarity	NPC215932
0.9521	High Similarity	NPC40818
0.9521	High Similarity	NPC106461
0.9477	High Similarity	NPC165549
0.9477	High Similarity	NPC259456
0.9456	High Similarity	NPC85233
0.9452	High Similarity	NPC136278
0.9416	High Similarity	NPC18284
0.9416	High Similarity	NPC273021
0.9416	High Similarity	NPC472448
0.9416	High Similarity	NPC83922
0.9416	High Similarity	NPC261470
0.9412	High Similarity	NPC476980
0.9388	High Similarity	NPC302408
0.9388	High Similarity	NPC216314
0.9388	High Similarity	NPC283002
0.9388	High Similarity	NPC120924
0.9388	High Similarity	NPC195919
0.9388	High Similarity	NPC231013
0.9384	High Similarity	NPC113089
0.9384	High Similarity	NPC23955
0.9351	High Similarity	NPC167678
0.9351	High Similarity	NPC29876
0.9351	High Similarity	NPC40037
0.9342	High Similarity	NPC248299
0.9338	High Similarity	NPC186507
0.9329	High Similarity	NPC238366
0.9329	High Similarity	NPC69752
0.932	High Similarity	NPC471590
0.932	High Similarity	NPC165512
0.9315	High Similarity	NPC9966
0.9315	High Similarity	NPC70853
0.9295	High Similarity	NPC50960
0.929	High Similarity	NPC229632
0.9286	High Similarity	NPC204290
0.9286	High Similarity	NPC298093
0.9281	High Similarity	NPC78071
0.9267	High Similarity	NPC259058
0.9267	High Similarity	NPC201547
0.9262	High Similarity	NPC476342
0.9252	High Similarity	NPC182842
0.9247	High Similarity	NPC29536
0.9247	High Similarity	NPC214919
0.9247	High Similarity	NPC124467
0.9226	High Similarity	NPC258331
0.9221	High Similarity	NPC74178
0.9221	High Similarity	NPC204879
0.9221	High Similarity	NPC184755
0.9221	High Similarity	NPC113055
0.9221	High Similarity	NPC187792
0.9216	High Similarity	NPC472455
0.9216	High Similarity	NPC471985
0.9216	High Similarity	NPC276444
0.9211	High Similarity	NPC280937
0.9205	High Similarity	NPC208043
0.9205	High Similarity	NPC308451
0.9205	High Similarity	NPC226973
0.92	High Similarity	NPC181250
0.9195	High Similarity	NPC299923
0.9184	High Similarity	NPC476054
0.9178	High Similarity	NPC58229
0.9172	High Similarity	NPC472450
0.9172	High Similarity	NPC275780
0.9172	High Similarity	NPC239752
0.9172	High Similarity	NPC475369
0.9167	High Similarity	NPC302741
0.9156	High Similarity	NPC218871
0.9156	High Similarity	NPC284820
0.9156	High Similarity	NPC36852
0.9156	High Similarity	NPC262286
0.9156	High Similarity	NPC476630
0.9156	High Similarity	NPC78225
0.9156	High Similarity	NPC310206
0.9156	High Similarity	NPC218313
0.9156	High Similarity	NPC473272
0.9156	High Similarity	NPC474681
0.915	High Similarity	NPC256612
0.915	High Similarity	NPC472280
0.915	High Similarity	NPC234255
0.915	High Similarity	NPC20830
0.9145	High Similarity	NPC134677
0.9139	High Similarity	NPC306821
0.9128	High Similarity	NPC310259
0.9122	High Similarity	NPC293201
0.9116	High Similarity	NPC185607
0.9114	High Similarity	NPC173292
0.9114	High Similarity	NPC39091
0.9114	High Similarity	NPC120593
0.9108	High Similarity	NPC23298
0.9108	High Similarity	NPC306321
0.9108	High Similarity	NPC65846
0.9108	High Similarity	NPC189473
0.9108	High Similarity	NPC303460
0.9103	High Similarity	NPC198829
0.9103	High Similarity	NPC34376
0.9091	High Similarity	NPC5322
0.9091	High Similarity	NPC68093
0.9091	High Similarity	NPC138243
0.9091	High Similarity	NPC6633
0.9091	High Similarity	NPC133970
0.9091	High Similarity	NPC303255
0.9091	High Similarity	NPC282307
0.9091	High Similarity	NPC170026
0.9091	High Similarity	NPC191146
0.9085	High Similarity	NPC160951
0.9085	High Similarity	NPC274327
0.9085	High Similarity	NPC183878
0.9085	High Similarity	NPC472915
0.9085	High Similarity	NPC255350
0.9085	High Similarity	NPC86485
0.9085	High Similarity	NPC69394
0.9085	High Similarity	NPC170492
0.9085	High Similarity	NPC231018
0.9085	High Similarity	NPC47781
0.9085	High Similarity	NPC176775
0.9085	High Similarity	NPC145379
0.9085	High Similarity	NPC22519
0.9079	High Similarity	NPC262623
0.9079	High Similarity	NPC474663
0.9079	High Similarity	NPC117579
0.9079	High Similarity	NPC149614
0.9079	High Similarity	NPC198615
0.9073	High Similarity	NPC328119
0.9067	High Similarity	NPC470511
0.906	High Similarity	NPC179970
0.9057	High Similarity	NPC8965
0.9045	High Similarity	NPC329760
0.9045	High Similarity	NPC474150
0.9045	High Similarity	NPC194427
0.9045	High Similarity	NPC474162
0.9045	High Similarity	NPC81679
0.9041	High Similarity	NPC17848
0.9038	High Similarity	NPC118256
0.9038	High Similarity	NPC475784
0.9038	High Similarity	NPC119209
0.9038	High Similarity	NPC246478
0.9038	High Similarity	NPC192686
0.9032	High Similarity	NPC52889
0.9032	High Similarity	NPC165977
0.9032	High Similarity	NPC217677
0.9032	High Similarity	NPC181960
0.9026	High Similarity	NPC138360
0.9026	High Similarity	NPC128863
0.9026	High Similarity	NPC280339
0.9026	High Similarity	NPC34725
0.9026	High Similarity	NPC39184
0.9026	High Similarity	NPC113906
0.9026	High Similarity	NPC50715
0.9026	High Similarity	NPC241774
0.9026	High Similarity	NPC472909
0.9026	High Similarity	NPC200246
0.9026	High Similarity	NPC196439
0.9026	High Similarity	NPC122623
0.9026	High Similarity	NPC134287
0.9026	High Similarity	NPC208197
0.9026	High Similarity	NPC163780
0.9026	High Similarity	NPC227325
0.9026	High Similarity	NPC152951
0.9026	High Similarity	NPC37392
0.9026	High Similarity	NPC117992
0.9026	High Similarity	NPC4455
0.9026	High Similarity	NPC230149
0.9026	High Similarity	NPC276059
0.9026	High Similarity	NPC213622
0.9026	High Similarity	NPC92659
0.9026	High Similarity	NPC130589
0.9026	High Similarity	NPC2476
0.9026	High Similarity	NPC478238
0.9026	High Similarity	NPC189960
0.9026	High Similarity	NPC183597
0.9026	High Similarity	NPC201136
0.9026	High Similarity	NPC167815
0.9026	High Similarity	NPC146165
0.9026	High Similarity	NPC256925
0.9026	High Similarity	NPC57674
0.9026	High Similarity	NPC32557
0.9026	High Similarity	NPC168247
0.902	High Similarity	NPC156222
0.902	High Similarity	NPC222830
0.902	High Similarity	NPC301323
0.902	High Similarity	NPC292460
0.902	High Similarity	NPC162313
0.902	High Similarity	NPC293183
0.902	High Similarity	NPC256283
0.902	High Similarity	NPC275836
0.902	High Similarity	NPC471982
0.902	High Similarity	NPC237994

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 NPC472408 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	474
0.1-0.2	1052
0.2-0.3	1785
0.3-0.4	2734
0.4-0.5	1732
0.5-0.6	897
0.6-0.7	331
0.7-0.8	109
0.8-0.85	24
0.85-0.9	9
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9286	High Similarity	NPD5494	Approved
0.9085	High Similarity	NPD2801	Approved
0.8742	High Similarity	NPD1247	Approved
0.8718	High Similarity	NPD2393	Clinical (unspecified phase)
0.8662	High Similarity	NPD3817	Phase 2
0.8654	High Similarity	NPD1934	Approved
0.8649	High Similarity	NPD2796	Approved
0.8562	High Similarity	NPD4378	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD1511	Approved
0.8491	Intermediate Similarity	NPD3882	Suspended
0.8442	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD4380	Phase 2
0.8387	Intermediate Similarity	NPD1512	Approved
0.8385	Intermediate Similarity	NPD919	Approved
0.8364	Intermediate Similarity	NPD3818	Discontinued
0.8354	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6166	Phase 2
0.8354	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD5402	Approved
0.8313	Intermediate Similarity	NPD5844	Phase 1
0.8293	Intermediate Similarity	NPD3926	Phase 2
0.825	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD7819	Suspended
0.8232	Intermediate Similarity	NPD6232	Discontinued
0.8225	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7054	Approved
0.8193	Intermediate Similarity	NPD7473	Discontinued
0.8187	Intermediate Similarity	NPD6801	Discontinued
0.8155	Intermediate Similarity	NPD7074	Phase 3
0.8155	Intermediate Similarity	NPD7472	Approved
0.8148	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD6799	Approved
0.8125	Intermediate Similarity	NPD7411	Suspended
0.8101	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD920	Approved
0.8098	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD7075	Discontinued
0.8092	Intermediate Similarity	NPD1510	Phase 2
0.8052	Intermediate Similarity	NPD1549	Phase 2
0.8012	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD1243	Approved
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7987	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD3748	Approved
0.7953	Intermediate Similarity	NPD7251	Discontinued
0.795	Intermediate Similarity	NPD6599	Discontinued
0.7947	Intermediate Similarity	NPD1240	Approved
0.7922	Intermediate Similarity	NPD2935	Discontinued
0.7882	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD5403	Approved
0.7862	Intermediate Similarity	NPD5401	Approved
0.7848	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6959	Discontinued
0.7843	Intermediate Similarity	NPD1607	Approved
0.7805	Intermediate Similarity	NPD1465	Phase 2
0.7778	Intermediate Similarity	NPD1933	Approved
0.7722	Intermediate Similarity	NPD3750	Approved
0.7712	Intermediate Similarity	NPD943	Approved
0.7711	Intermediate Similarity	NPD7768	Phase 2
0.7706	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2313	Discontinued
0.7688	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD3749	Approved
0.7662	Intermediate Similarity	NPD447	Suspended
0.7658	Intermediate Similarity	NPD2800	Approved
0.7658	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD6559	Discontinued
0.7628	Intermediate Similarity	NPD2799	Discontinued
0.7595	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3226	Approved
0.7544	Intermediate Similarity	NPD5242	Approved
0.7542	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.7531	Intermediate Similarity	NPD2533	Approved
0.7531	Intermediate Similarity	NPD2534	Approved
0.7531	Intermediate Similarity	NPD2532	Approved
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6832	Phase 2
0.745	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.7405	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD2403	Approved
0.7386	Intermediate Similarity	NPD5953	Discontinued
0.7384	Intermediate Similarity	NPD3787	Discontinued
0.7371	Intermediate Similarity	NPD7286	Phase 2
0.7365	Intermediate Similarity	NPD6385	Approved
0.7365	Intermediate Similarity	NPD6386	Approved
0.7362	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1551	Phase 2
0.7347	Intermediate Similarity	NPD5536	Phase 2
0.7338	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5353	Approved
0.7326	Intermediate Similarity	NPD7199	Phase 2
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7321	Intermediate Similarity	NPD6844	Discontinued
0.732	Intermediate Similarity	NPD2798	Approved
0.7312	Intermediate Similarity	NPD2344	Approved
0.7303	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4628	Phase 3
0.7278	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6651	Approved
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1613	Approved
0.7261	Intermediate Similarity	NPD4307	Phase 2
0.7261	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7390	Discontinued
0.725	Intermediate Similarity	NPD6100	Approved
0.725	Intermediate Similarity	NPD6099	Approved
0.7241	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2654	Approved
0.7219	Intermediate Similarity	NPD37	Approved
0.7205	Intermediate Similarity	NPD1471	Phase 3
0.7202	Intermediate Similarity	NPD6585	Discontinued
0.7193	Intermediate Similarity	NPD4967	Phase 2
0.7193	Intermediate Similarity	NPD4966	Approved
0.7193	Intermediate Similarity	NPD4965	Approved
0.7188	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1653	Approved
0.7181	Intermediate Similarity	NPD6777	Approved
0.7181	Intermediate Similarity	NPD6781	Approved
0.7181	Intermediate Similarity	NPD6778	Approved
0.7181	Intermediate Similarity	NPD6782	Approved
0.7181	Intermediate Similarity	NPD6780	Approved
0.7181	Intermediate Similarity	NPD6776	Approved
0.7181	Intermediate Similarity	NPD6779	Approved
0.7179	Intermediate Similarity	NPD3027	Phase 3
0.7178	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3972	Approved
0.7161	Intermediate Similarity	NPD3018	Phase 2
0.716	Intermediate Similarity	NPD5889	Approved
0.716	Intermediate Similarity	NPD5890	Approved
0.7143	Intermediate Similarity	NPD8434	Phase 2
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD3267	Approved
0.7134	Intermediate Similarity	NPD2309	Approved
0.7134	Intermediate Similarity	NPD6190	Approved
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7549	Discontinued
0.711	Intermediate Similarity	NPD6234	Discontinued
0.7107	Intermediate Similarity	NPD5124	Phase 1
0.7107	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4360	Phase 2
0.7097	Intermediate Similarity	NPD4363	Phase 3
0.7093	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD17	Approved
0.7086	Intermediate Similarity	NPD7229	Phase 3
0.7081	Intermediate Similarity	NPD4308	Phase 3
0.7081	Intermediate Similarity	NPD7033	Discontinued
0.7072	Intermediate Similarity	NPD8312	Approved
0.7072	Intermediate Similarity	NPD8313	Approved
0.7068	Intermediate Similarity	NPD7435	Discontinued
0.7068	Intermediate Similarity	NPD7697	Approved
0.7068	Intermediate Similarity	NPD7696	Phase 3
0.7068	Intermediate Similarity	NPD7698	Approved
0.7066	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7056	Intermediate Similarity	NPD7685	Pre-registration
0.7051	Intermediate Similarity	NPD9494	Approved
0.7049	Intermediate Similarity	NPD8150	Discontinued
0.7047	Intermediate Similarity	NPD7584	Approved
0.7041	Intermediate Similarity	NPD7458	Discontinued
0.7037	Intermediate Similarity	NPD8285	Discontinued
0.7035	Intermediate Similarity	NPD4288	Approved
0.7032	Intermediate Similarity	NPD1203	Approved
0.7031	Intermediate Similarity	NPD7870	Phase 2
0.7031	Intermediate Similarity	NPD7871	Phase 2
0.703	Intermediate Similarity	NPD3887	Approved
0.7025	Intermediate Similarity	NPD1296	Phase 2
0.7025	Intermediate Similarity	NPD3268	Approved
0.7022	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2983	Phase 2
0.7013	Intermediate Similarity	NPD2982	Phase 2
0.7006	Intermediate Similarity	NPD4908	Phase 1
0.6994	Remote Similarity	NPD2353	Approved
0.6994	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5710	Approved
0.6989	Remote Similarity	NPD5711	Approved
0.6987	Remote Similarity	NPD1019	Discontinued
0.6968	Remote Similarity	NPD3225	Approved
0.6962	Remote Similarity	NPD4625	Phase 3
0.6959	Remote Similarity	NPD5283	Phase 1
0.6959	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD1241	Discontinued
0.6951	Remote Similarity	NPD2424	Discontinued
0.6948	Remote Similarity	NPD1608	Approved
0.6948	Remote Similarity	NPD9717	Approved
0.6946	Remote Similarity	NPD4357	Discontinued
0.6941	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5978	Approved
0.6936	Remote Similarity	NPD5977	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