NPASS Compound

Structure

NPC472918 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 1.7321 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 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 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5000 0.8660 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 2.5981 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 1.7321 -0.0000 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 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5000 0.8660 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 O 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 4 1 0 0 0 0 2 10 2 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 17 1 0 0 0 0 9 23 1 0 0 0 0 11 18 1 0 0 0 0 12 22 1 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 15 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 16 20 2 0 0 0 0 17 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.09
Volume:	311.205
LogP:	2.619
LogD:	2.715
LogS:	-3.515
# Rotatable Bonds:	3
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.797
Synthetic Accessibility Score:	3.158
Fsp3:	0.235
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.816
MDCK Permeability:	1.106486888602376e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.087
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.486
30% Bioavailability (F30%):	0.819

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066
Plasma Protein Binding (PPB):	96.50016021728516%
Volume Distribution (VD):	1.032
Pgp-substrate:	2.957432508468628%

ADMET: Metabolism

CYP1A2-inhibitor:	0.962
CYP1A2-substrate:	0.622
CYP2C19-inhibitor:	0.794
CYP2C19-substrate:	0.189
CYP2C9-inhibitor:	0.553
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.724
CYP2D6-substrate:	0.693
CYP3A4-inhibitor:	0.937
CYP3A4-substrate:	0.307

ADMET: Excretion

Clearance (CL):	15.011
Half-life (T1/2):	0.416

ADMET: Toxicity

hERG Blockers:	0.054
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.591
AMES Toxicity:	0.464
Rat Oral Acute Toxicity:	0.093
Maximum Recommended Daily Dose:	0.484
Skin Sensitization:	0.165
Carcinogencity:	0.426
Eye Corrosion:	0.003
Eye Irritation:	0.344
Respiratory Toxicity:	0.113

Download Data

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

Natural Product: NPC472918

Natural Product ID:	NPC472918
*Common Name:**	MYJSUEBYZUYQNB-KRWDZBQOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MYJSUEBYZUYQNB-KRWDZBQOSA-N
Standard InCHI:	InChI=1S/C17H16O6/c1-22-12-6-13(19)15-14(7-12)23-9-17(21,16(15)20)8-10-2-4-11(18)5-3-10/h2-7,18-19,21H,8-9H2,1H3/t17-/m0/s1
SMILES:	COc1cc(O)c2c(c1)OC[C@@](C2=O)(O)Cc1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3594096
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans

*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
NPO33045	bellevalia eigii	Species	Hyacinthaceae	Eukaryota	Bulbs	Irbid, Jordan	n.a.	PMID[26147490]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	20000.0	nM	PMID[564323]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	20000.0	nM	PMID[564323]

☑ 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 NPC472918 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	374
0.1-0.2	1514
0.2-0.3	4126
0.3-0.4	10284
0.4-0.5	7821
0.5-0.6	3711
0.6-0.7	5410
0.7-0.8	5125
0.8-0.85	2468
0.85-0.9	1403
0.9-0.95	423
0.95-1	38

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC229190
0.9722	High Similarity	NPC471229
0.972	High Similarity	NPC277032
0.9718	High Similarity	NPC40086
0.9718	High Similarity	NPC44721
0.9718	High Similarity	NPC3779
0.9718	High Similarity	NPC176869
0.9718	High Similarity	NPC122828
0.9718	High Similarity	NPC476182
0.9718	High Similarity	NPC211466
0.9655	High Similarity	NPC210597
0.9653	High Similarity	NPC267117
0.9589	High Similarity	NPC209760
0.9589	High Similarity	NPC100134
0.9586	High Similarity	NPC262039
0.9586	High Similarity	NPC262038
0.9586	High Similarity	NPC278476
0.9586	High Similarity	NPC254412
0.9586	High Similarity	NPC319910
0.9577	High Similarity	NPC208176
0.9577	High Similarity	NPC279417
0.9577	High Similarity	NPC326506
0.9577	High Similarity	NPC142731
0.9577	High Similarity	NPC62290
0.9577	High Similarity	NPC4152
0.9577	High Similarity	NPC306607
0.9577	High Similarity	NPC49130
0.9524	High Similarity	NPC304207
0.9524	High Similarity	NPC476169
0.9524	High Similarity	NPC48579
0.9524	High Similarity	NPC471116
0.9524	High Similarity	NPC217706
0.9524	High Similarity	NPC207809
0.9524	High Similarity	NPC259710
0.9521	High Similarity	NPC35567
0.9521	High Similarity	NPC217149
0.9521	High Similarity	NPC216035
0.9521	High Similarity	NPC243171
0.9521	High Similarity	NPC138288
0.9521	High Similarity	NPC171651
0.9517	High Similarity	NPC105136
0.951	High Similarity	NPC148011
0.951	High Similarity	NPC1940
0.9459	High Similarity	NPC10754
0.9459	High Similarity	NPC215917
0.9459	High Similarity	NPC20530
0.9456	High Similarity	NPC203080
0.9456	High Similarity	NPC180301
0.9456	High Similarity	NPC236756
0.9456	High Similarity	NPC311579
0.9456	High Similarity	NPC248793
0.9456	High Similarity	NPC293286
0.9452	High Similarity	NPC471676
0.9452	High Similarity	NPC472422
0.9452	High Similarity	NPC295650
0.9452	High Similarity	NPC472636
0.9452	High Similarity	NPC472420
0.9452	High Similarity	NPC471677
0.9452	High Similarity	NPC244577
0.9452	High Similarity	NPC263384
0.9448	High Similarity	NPC472628
0.9448	High Similarity	NPC477941
0.9444	High Similarity	NPC472627
0.9433	High Similarity	NPC188243
0.9433	High Similarity	NPC6407
0.9433	High Similarity	NPC76445
0.9433	High Similarity	NPC129853
0.9433	High Similarity	NPC284550
0.9433	High Similarity	NPC110228
0.9396	High Similarity	NPC67876
0.9392	High Similarity	NPC304745
0.9392	High Similarity	NPC111341
0.9388	High Similarity	NPC473996
0.9388	High Similarity	NPC475790
0.9379	High Similarity	NPC296869
0.9379	High Similarity	NPC218569
0.9375	High Similarity	NPC124729
0.9371	High Similarity	NPC478086
0.9371	High Similarity	NPC214166
0.9371	High Similarity	NPC316816
0.9366	High Similarity	NPC262094
0.9366	High Similarity	NPC90582
0.9362	High Similarity	NPC241838
0.9362	High Similarity	NPC310135
0.9362	High Similarity	NPC222342
0.9362	High Similarity	NPC329203
0.9362	High Similarity	NPC150648
0.9362	High Similarity	NPC225153
0.9362	High Similarity	NPC152042
0.9362	High Similarity	NPC143799
0.9362	High Similarity	NPC274784
0.9362	High Similarity	NPC20709
0.9362	High Similarity	NPC265871
0.9362	High Similarity	NPC140890
0.9333	High Similarity	NPC152904
0.9329	High Similarity	NPC146636
0.9329	High Similarity	NPC471500
0.9324	High Similarity	NPC7989
0.9324	High Similarity	NPC472583
0.9324	High Similarity	NPC268193
0.9324	High Similarity	NPC141212
0.9324	High Similarity	NPC223701
0.9324	High Similarity	NPC244250
0.9324	High Similarity	NPC20907
0.932	High Similarity	NPC472580
0.932	High Similarity	NPC474023
0.932	High Similarity	NPC474021
0.932	High Similarity	NPC471675
0.931	High Similarity	NPC21835
0.9306	High Similarity	NPC131568
0.9306	High Similarity	NPC216538
0.9306	High Similarity	NPC311144
0.9306	High Similarity	NPC273538
0.9306	High Similarity	NPC131579
0.9306	High Similarity	NPC209040
0.9301	High Similarity	NPC78
0.9301	High Similarity	NPC66515
0.9301	High Similarity	NPC166482
0.9301	High Similarity	NPC32739
0.9301	High Similarity	NPC324436
0.9301	High Similarity	NPC177354
0.9301	High Similarity	NPC328164
0.9301	High Similarity	NPC306829
0.9301	High Similarity	NPC125855
0.9301	High Similarity	NPC194432
0.9301	High Similarity	NPC296917
0.9301	High Similarity	NPC166934
0.9301	High Similarity	NPC148757
0.9301	High Similarity	NPC10937
0.9301	High Similarity	NPC324134
0.9301	High Similarity	NPC228504
0.9301	High Similarity	NPC265040
0.9301	High Similarity	NPC220998
0.9301	High Similarity	NPC182852
0.9301	High Similarity	NPC40833
0.9301	High Similarity	NPC167624
0.9301	High Similarity	NPC107572
0.9301	High Similarity	NPC227579
0.9301	High Similarity	NPC37496
0.9301	High Similarity	NPC64915
0.9301	High Similarity	NPC76338
0.9301	High Similarity	NPC223500
0.9301	High Similarity	NPC76372
0.9301	High Similarity	NPC1089
0.9301	High Similarity	NPC161506
0.9301	High Similarity	NPC200694
0.9296	High Similarity	NPC184536
0.9296	High Similarity	NPC103342
0.9296	High Similarity	NPC103904
0.9296	High Similarity	NPC59951
0.9296	High Similarity	NPC281207
0.9296	High Similarity	NPC269652
0.9296	High Similarity	NPC146679
0.9296	High Similarity	NPC230285
0.9291	High Similarity	NPC99333
0.9291	High Similarity	NPC276905
0.9291	High Similarity	NPC280284
0.9291	High Similarity	NPC124269
0.9291	High Similarity	NPC118813
0.9291	High Similarity	NPC188947
0.9272	High Similarity	NPC470183
0.9267	High Similarity	NPC471479
0.9267	High Similarity	NPC6985
0.9267	High Similarity	NPC471515
0.9262	High Similarity	NPC477958
0.9257	High Similarity	NPC477957
0.9257	High Similarity	NPC31627
0.9257	High Similarity	NPC10807
0.9257	High Similarity	NPC150123
0.9257	High Similarity	NPC244583
0.9257	High Similarity	NPC327269
0.9257	High Similarity	NPC476238
0.9257	High Similarity	NPC161881
0.9257	High Similarity	NPC56232
0.9252	High Similarity	NPC472421
0.9252	High Similarity	NPC61258
0.9247	High Similarity	NPC244407
0.9241	High Similarity	NPC246948
0.9241	High Similarity	NPC472629
0.9241	High Similarity	NPC301276
0.9241	High Similarity	NPC470458
0.9241	High Similarity	NPC475052
0.9241	High Similarity	NPC306488
0.9241	High Similarity	NPC5820
0.9241	High Similarity	NPC214774
0.9241	High Similarity	NPC267375
0.9241	High Similarity	NPC312973
0.9241	High Similarity	NPC20488
0.9241	High Similarity	NPC127059
0.9241	High Similarity	NPC285630
0.9241	High Similarity	NPC176229
0.9241	High Similarity	NPC142405
0.9241	High Similarity	NPC299011
0.9241	High Similarity	NPC54577
0.9241	High Similarity	NPC67805
0.9241	High Similarity	NPC88964
0.9241	High Similarity	NPC470647
0.9241	High Similarity	NPC83357
0.9241	High Similarity	NPC178343
0.9241	High Similarity	NPC111786

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 NPC472918 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	338
0.1-0.2	894
0.2-0.3	1645
0.3-0.4	2641
0.4-0.5	1825
0.5-0.6	1135
0.6-0.7	466
0.7-0.8	153
0.8-0.85	29
0.85-0.9	17
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9306	High Similarity	NPD4378	Clinical (unspecified phase)
0.922	High Similarity	NPD1550	Clinical (unspecified phase)
0.922	High Similarity	NPD1552	Clinical (unspecified phase)
0.9155	High Similarity	NPD1549	Phase 2
0.9139	High Similarity	NPD7075	Discontinued
0.9128	High Similarity	NPD1934	Approved
0.9103	High Similarity	NPD6799	Approved
0.9067	High Similarity	NPD7096	Clinical (unspecified phase)
0.9067	High Similarity	NPD2393	Clinical (unspecified phase)
0.8993	High Similarity	NPD4380	Phase 2
0.891	High Similarity	NPD6167	Clinical (unspecified phase)
0.891	High Similarity	NPD6168	Clinical (unspecified phase)
0.891	High Similarity	NPD6166	Phase 2
0.8889	High Similarity	NPD4381	Clinical (unspecified phase)
0.8874	High Similarity	NPD6801	Discontinued
0.8867	High Similarity	NPD6599	Discontinued
0.8851	High Similarity	NPD1512	Approved
0.8824	High Similarity	NPD3882	Suspended
0.8816	High Similarity	NPD2801	Approved
0.8811	High Similarity	NPD1510	Phase 2
0.8794	High Similarity	NPD1240	Approved
0.8784	High Similarity	NPD7410	Clinical (unspecified phase)
0.8758	High Similarity	NPD3817	Phase 2
0.875	High Similarity	NPD2796	Approved
0.8742	High Similarity	NPD7804	Clinical (unspecified phase)
0.8716	High Similarity	NPD1511	Approved
0.8684	High Similarity	NPD7411	Suspended
0.8671	High Similarity	NPD1607	Approved
0.8636	High Similarity	NPD8443	Clinical (unspecified phase)
0.8543	High Similarity	NPD5403	Approved
0.8519	High Similarity	NPD6797	Phase 2
0.8466	Intermediate Similarity	NPD7251	Discontinued
0.8457	Intermediate Similarity	NPD7074	Phase 3
0.8452	Intermediate Similarity	NPD7819	Suspended
0.8415	Intermediate Similarity	NPD7808	Phase 3
0.8411	Intermediate Similarity	NPD5401	Approved
0.8395	Intermediate Similarity	NPD7054	Approved
0.8344	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD7472	Approved
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8303	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD5402	Approved
0.8264	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD6959	Discontinued
0.821	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD5494	Approved
0.8176	Intermediate Similarity	NPD3749	Approved
0.8146	Intermediate Similarity	NPD3750	Approved
0.8133	Intermediate Similarity	NPD6559	Discontinued
0.8121	Intermediate Similarity	NPD1551	Phase 2
0.8113	Intermediate Similarity	NPD7768	Phase 2
0.8079	Intermediate Similarity	NPD2800	Approved
0.8072	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD4628	Phase 3
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6232	Discontinued
0.7939	Intermediate Similarity	NPD7473	Discontinued
0.7919	Intermediate Similarity	NPD6651	Approved
0.7891	Intermediate Similarity	NPD6798	Discontinued
0.7887	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2935	Discontinued
0.7881	Intermediate Similarity	NPD6100	Approved
0.7881	Intermediate Similarity	NPD6099	Approved
0.7877	Intermediate Similarity	NPD4908	Phase 1
0.7844	Intermediate Similarity	NPD5844	Phase 1
0.7844	Intermediate Similarity	NPD7286	Phase 2
0.7834	Intermediate Similarity	NPD920	Approved
0.7829	Intermediate Similarity	NPD2344	Approved
0.7821	Intermediate Similarity	NPD2533	Approved
0.7821	Intermediate Similarity	NPD2532	Approved
0.7821	Intermediate Similarity	NPD2534	Approved
0.7818	Intermediate Similarity	NPD3926	Phase 2
0.7815	Intermediate Similarity	NPD7033	Discontinued
0.7815	Intermediate Similarity	NPD3748	Approved
0.7805	Intermediate Similarity	NPD1247	Approved
0.7793	Intermediate Similarity	NPD1203	Approved
0.7792	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD919	Approved
0.7785	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD943	Approved
0.7785	Intermediate Similarity	NPD1613	Approved
0.7784	Intermediate Similarity	NPD3751	Discontinued
0.777	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD1465	Phase 2
0.7762	Intermediate Similarity	NPD1610	Phase 2
0.7758	Intermediate Similarity	NPD3787	Discontinued
0.7755	Intermediate Similarity	NPD6832	Phase 2
0.7755	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD5953	Discontinued
0.774	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1548	Phase 1
0.7727	Intermediate Similarity	NPD1243	Approved
0.7718	Intermediate Similarity	NPD6233	Phase 2
0.7714	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD2799	Discontinued
0.7692	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2313	Discontinued
0.7651	Intermediate Similarity	NPD3268	Approved
0.7628	Intermediate Similarity	NPD2354	Approved
0.7628	Intermediate Similarity	NPD2309	Approved
0.7616	Intermediate Similarity	NPD1933	Approved
0.7616	Intermediate Similarity	NPD6355	Discontinued
0.7586	Intermediate Similarity	NPD9717	Approved
0.7564	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD2403	Approved
0.7551	Intermediate Similarity	NPD2797	Approved
0.7531	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4360	Phase 2
0.7528	Intermediate Similarity	NPD4363	Phase 3
0.7517	Intermediate Similarity	NPD422	Phase 1
0.7516	Intermediate Similarity	NPD3887	Approved
0.7516	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD5124	Phase 1
0.75	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2654	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1652	Phase 2
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7468	Intermediate Similarity	NPD4308	Phase 3
0.7468	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD3027	Phase 3
0.7459	Intermediate Similarity	NPD7584	Approved
0.7456	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD5049	Phase 3
0.7436	Intermediate Similarity	NPD2424	Discontinued
0.7421	Intermediate Similarity	NPD7390	Discontinued
0.7418	Intermediate Similarity	NPD6782	Approved
0.7418	Intermediate Similarity	NPD6776	Approved
0.7418	Intermediate Similarity	NPD6778	Approved
0.7418	Intermediate Similarity	NPD6777	Approved
0.7418	Intermediate Similarity	NPD6780	Approved
0.7418	Intermediate Similarity	NPD6779	Approved
0.7418	Intermediate Similarity	NPD6781	Approved
0.7405	Intermediate Similarity	NPD6190	Approved
0.7386	Intermediate Similarity	NPD447	Suspended
0.7386	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7199	Phase 2
0.7375	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4662	Approved
0.7375	Intermediate Similarity	NPD4661	Approved
0.7372	Intermediate Similarity	NPD2353	Approved
0.7372	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4062	Phase 3
0.7365	Intermediate Similarity	NPD3225	Approved
0.7361	Intermediate Similarity	NPD9545	Approved
0.7351	Intermediate Similarity	NPD4625	Phase 3
0.7347	Intermediate Similarity	NPD3972	Approved
0.7337	Intermediate Similarity	NPD5710	Approved
0.7337	Intermediate Similarity	NPD5711	Approved
0.733	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4060	Phase 1
0.7315	Intermediate Similarity	NPD3266	Approved
0.7315	Intermediate Similarity	NPD3267	Approved
0.7314	Intermediate Similarity	NPD8312	Approved
0.7314	Intermediate Similarity	NPD8313	Approved
0.7312	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7458	Discontinued
0.7299	Intermediate Similarity	NPD6104	Discontinued
0.7297	Intermediate Similarity	NPD7435	Discontinued
0.7297	Intermediate Similarity	NPD4749	Approved
0.7293	Intermediate Similarity	NPD4361	Phase 2
0.7293	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD8150	Discontinued
0.7283	Intermediate Similarity	NPD1729	Discontinued
0.7273	Intermediate Similarity	NPD4340	Discontinued
0.7267	Intermediate Similarity	NPD1019	Discontinued
0.7254	Intermediate Similarity	NPD1241	Discontinued
0.7241	Intermediate Similarity	NPD3823	Discontinued
0.7237	Intermediate Similarity	NPD7095	Approved
0.723	Intermediate Similarity	NPD1608	Approved
0.7229	Intermediate Similarity	NPD8455	Phase 2
0.7222	Intermediate Similarity	NPD9493	Approved
0.7219	Intermediate Similarity	NPD2861	Phase 2
0.7208	Intermediate Similarity	NPD4307	Phase 2
0.7207	Intermediate Similarity	NPD4287	Approved
0.7204	Intermediate Similarity	NPD7697	Approved
0.7204	Intermediate Similarity	NPD7696	Phase 3
0.7204	Intermediate Similarity	NPD7698	Approved
0.719	Intermediate Similarity	NPD3764	Approved
0.719	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1296	Phase 2
0.7186	Intermediate Similarity	NPD4288	Approved
0.7169	Intermediate Similarity	NPD6844	Discontinued
0.7169	Intermediate Similarity	NPD7577	Discontinued
0.7166	Intermediate Similarity	NPD7871	Phase 2
0.7166	Intermediate Similarity	NPD7870	Phase 2
0.7162	Intermediate Similarity	NPD1091	Approved
0.716	Intermediate Similarity	NPD6234	Discontinued
0.7152	Intermediate Similarity	NPD1471	Phase 3
0.7151	Intermediate Similarity	NPD4575	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