NPASS Compound

Structure

NPC30043 OpenBabel07101719252D 34 35 0 0 1 0 0 0 0 0999 V2000 -6.0622 -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 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 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 -5.1962 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 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 2 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 31 1 0 0 0 0 3 32 1 0 0 0 0 4 5 1 0 0 0 0 4 8 1 0 0 0 0 5 15 1 0 0 0 0 6 7 2 0 0 0 0 6 16 1 0 0 0 0 7 18 1 0 0 0 0 8 25 1 0 0 0 0 9 15 2 0 0 0 0 9 20 1 0 0 0 0 10 15 1 0 0 0 0 10 21 2 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 17 1 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 16 23 1 0 0 0 0 17 33 1 0 0 0 0 18 19 2 0 0 0 0 18 33 1 0 0 0 0 19 30 1 0 0 0 0 20 24 2 0 0 0 0 20 31 1 0 0 0 0 21 24 1 0 0 0 0 21 32 1 0 0 0 0 22 14 1 1 0 0 0 22 23 1 0 0 0 0 22 34 1 0 0 0 0 23 29 1 1 0 0 0 24 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.22
Volume:	478.631
LogP:	0.155
LogD:	0.843
LogS:	-2.393
# Rotatable Bonds:	15
TPSA:	147.3
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	2
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.247
Synthetic Accessibility Score:	3.474
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.269
MDCK Permeability:	0.0001367907243547961
Pgp-inhibitor:	0.028
Pgp-substrate:	0.15
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.249
Plasma Protein Binding (PPB):	30.021892547607422%
Volume Distribution (VD):	0.73
Pgp-substrate:	27.30144500732422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.113
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.834
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.259
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.523
CYP3A4-inhibitor:	0.317
CYP3A4-substrate:	0.717

ADMET: Excretion

Clearance (CL):	5.33
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.259
Human Hepatotoxicity (H-HT):	0.204
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.125
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.001

Download Data

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

Natural Product: NPC30043

Natural Product ID:	NPC30043
*Common Name:**	(7S,8R)-4-O-(Glycer-2-Yl)-7,9,9'-Trihydroxy-3,3',5'-Trimethoxy-8-O-4'-Neolignan
IUPAC Name:	(1S,2R)-1-[4-(1,3-dihydroxypropan-2-yloxy)-3-methoxyphenyl]-2-[4-(3-hydroxypropyl)-2,6-dimethoxyphenoxy]propane-1,3-diol
Synonyms:
Standard InCHIKey:	IXRLOIQOINZSOU-PKTZIBPZSA-N
Standard InCHI:	InChI=1S/C24H34O10/c1-30-19-11-16(6-7-18(19)33-17(12-26)13-27)23(29)22(14-28)34-24-20(31-2)9-15(5-4-8-25)10-21(24)32-3/h6-7,9-11,17,22-23,25-29H,4-5,8,12-14H2,1-3H3/t22-,23+/m1/s1
SMILES:	OCCCc1cc(OC)c(c(c1)OC)O[C@@H]([C@H](c1ccc(c(c1)OC)OC(CO)CO)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094140
PubChem CID:	46834547
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	stem bark	n.a.	n.a.	PMID[20411974]
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11871	Illicium difengpi	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1620.0	nM	PMID[527898]

☑ 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 NPC30043 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	381
0.1-0.2	1465
0.2-0.3	4707
0.3-0.4	12187
0.4-0.5	5870
0.5-0.6	4341
0.6-0.7	6960
0.7-0.8	4987
0.8-0.85	1039
0.85-0.9	558
0.9-0.95	168
0.95-1	34

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469625
1.0	High Similarity	NPC469613
0.9919	High Similarity	NPC469612
0.9919	High Similarity	NPC469614
0.9839	High Similarity	NPC202582
0.9839	High Similarity	NPC210623
0.9839	High Similarity	NPC222004
0.9839	High Similarity	NPC226788
0.9839	High Similarity	NPC273295
0.9839	High Similarity	NPC3439
0.9839	High Similarity	NPC218856
0.9839	High Similarity	NPC470258
0.9839	High Similarity	NPC285339
0.9839	High Similarity	NPC190629
0.9762	High Similarity	NPC184447
0.9762	High Similarity	NPC7903
0.9762	High Similarity	NPC35932
0.9762	High Similarity	NPC160991
0.9762	High Similarity	NPC16208
0.9683	High Similarity	NPC472597
0.9683	High Similarity	NPC470096
0.9683	High Similarity	NPC470095
0.9677	High Similarity	NPC474119
0.9612	High Similarity	NPC471719
0.9609	High Similarity	NPC170694
0.9609	High Similarity	NPC310854
0.9606	High Similarity	NPC470752
0.9603	High Similarity	NPC472338
0.9528	High Similarity	NPC309787
0.9457	High Similarity	NPC309744
0.9435	High Similarity	NPC109822
0.9435	High Similarity	NPC94276
0.9394	High Similarity	NPC266197
0.9394	High Similarity	NPC291101
0.9385	High Similarity	NPC61946
0.9385	High Similarity	NPC472337
0.938	High Similarity	NPC475840
0.938	High Similarity	NPC263064
0.937	High Similarity	NPC170844
0.937	High Similarity	NPC476968
0.9365	High Similarity	NPC147821
0.9365	High Similarity	NPC163332
0.9365	High Similarity	NPC118787
0.9365	High Similarity	NPC183181
0.9365	High Similarity	NPC111247
0.9365	High Similarity	NPC319625
0.9365	High Similarity	NPC210355
0.9365	High Similarity	NPC41706
0.9365	High Similarity	NPC292056
0.9318	High Similarity	NPC22517
0.9313	High Similarity	NPC25695
0.9313	High Similarity	NPC306441
0.9313	High Similarity	NPC172818
0.9313	High Similarity	NPC16435
0.9313	High Similarity	NPC472336
0.9313	High Similarity	NPC472334
0.9302	High Similarity	NPC201587
0.9302	High Similarity	NPC253105
0.9291	High Similarity	NPC98631
0.9291	High Similarity	NPC470213
0.9291	High Similarity	NPC206615
0.9291	High Similarity	NPC186843
0.9286	High Similarity	NPC191037
0.9286	High Similarity	NPC178284
0.9286	High Similarity	NPC58607
0.928	High Similarity	NPC48990
0.928	High Similarity	NPC114901
0.928	High Similarity	NPC293701
0.9274	High Similarity	NPC71090
0.9274	High Similarity	NPC261661
0.9254	High Similarity	NPC469559
0.9248	High Similarity	NPC267291
0.9237	High Similarity	NPC234333
0.9237	High Similarity	NPC94750
0.9237	High Similarity	NPC47398
0.9237	High Similarity	NPC121812
0.9237	High Similarity	NPC470356
0.9237	High Similarity	NPC112246
0.9237	High Similarity	NPC474206
0.9237	High Similarity	NPC112939
0.9237	High Similarity	NPC260898
0.9231	High Similarity	NPC168059
0.9231	High Similarity	NPC229442
0.9225	High Similarity	NPC474017
0.9219	High Similarity	NPC86030
0.9219	High Similarity	NPC5851
0.9213	High Similarity	NPC242032
0.9213	High Similarity	NPC470699
0.9206	High Similarity	NPC194519
0.9167	High Similarity	NPC227503
0.9167	High Similarity	NPC230734
0.9167	High Similarity	NPC474639
0.9167	High Similarity	NPC302701
0.9167	High Similarity	NPC269091
0.916	High Similarity	NPC244983
0.916	High Similarity	NPC326095
0.916	High Similarity	NPC13745
0.916	High Similarity	NPC251981
0.916	High Similarity	NPC48863
0.916	High Similarity	NPC287745
0.9147	High Similarity	NPC307042
0.9147	High Similarity	NPC79184
0.9141	High Similarity	NPC72529
0.9134	High Similarity	NPC181361
0.9127	High Similarity	NPC228972
0.9127	High Similarity	NPC122792
0.9118	High Similarity	NPC470097
0.9118	High Similarity	NPC114119
0.9118	High Similarity	NPC471415
0.9113	High Similarity	NPC199023
0.9113	High Similarity	NPC472596
0.9111	High Similarity	NPC193722
0.9111	High Similarity	NPC189115
0.9111	High Similarity	NPC278469
0.9098	High Similarity	NPC107551
0.9098	High Similarity	NPC326797
0.9098	High Similarity	NPC477938
0.9098	High Similarity	NPC474282
0.9098	High Similarity	NPC211549
0.9098	High Similarity	NPC102904
0.9098	High Similarity	NPC176051
0.9098	High Similarity	NPC474390
0.9098	High Similarity	NPC103976
0.9091	High Similarity	NPC164787
0.9091	High Similarity	NPC151224
0.9084	High Similarity	NPC69513
0.9084	High Similarity	NPC158331
0.9084	High Similarity	NPC49074
0.9084	High Similarity	NPC215833
0.9084	High Similarity	NPC11060
0.907	High Similarity	NPC469951
0.907	High Similarity	NPC212015
0.907	High Similarity	NPC469963
0.9055	High Similarity	NPC251855
0.9055	High Similarity	NPC298757
0.9055	High Similarity	NPC475169
0.9055	High Similarity	NPC117214
0.9055	High Similarity	NPC203133
0.9055	High Similarity	NPC233410
0.9055	High Similarity	NPC17943
0.9055	High Similarity	NPC57490
0.9055	High Similarity	NPC472093
0.9055	High Similarity	NPC208950
0.9055	High Similarity	NPC193544
0.9055	High Similarity	NPC221077
0.9055	High Similarity	NPC116907
0.9051	High Similarity	NPC181615
0.9051	High Similarity	NPC475096
0.9048	High Similarity	NPC165375
0.9048	High Similarity	NPC233526
0.9048	High Similarity	NPC282496
0.9048	High Similarity	NPC220598
0.9037	High Similarity	NPC471389
0.9037	High Similarity	NPC83375
0.9037	High Similarity	NPC87725
0.9037	High Similarity	NPC224876
0.9037	High Similarity	NPC263261
0.9037	High Similarity	NPC311530
0.9037	High Similarity	NPC469661
0.903	High Similarity	NPC471388
0.903	High Similarity	NPC212770
0.903	High Similarity	NPC98777
0.9023	High Similarity	NPC265433
0.9023	High Similarity	NPC248727
0.9023	High Similarity	NPC270456
0.9023	High Similarity	NPC164857
0.9023	High Similarity	NPC162659
0.9023	High Similarity	NPC470802
0.9015	High Similarity	NPC187194
0.9015	High Similarity	NPC317380
0.9008	High Similarity	NPC185604
0.9008	High Similarity	NPC219876
0.9008	High Similarity	NPC204215
0.9008	High Similarity	NPC261619
0.9008	High Similarity	NPC61477
0.9008	High Similarity	NPC202762
0.9008	High Similarity	NPC78770
0.9008	High Similarity	NPC15658
0.9008	High Similarity	NPC126029
0.9008	High Similarity	NPC127624
0.9008	High Similarity	NPC162093
0.9008	High Similarity	NPC175067
0.9008	High Similarity	NPC86655
0.9008	High Similarity	NPC299144
0.9	High Similarity	NPC91291
0.9	High Similarity	NPC214860
0.8992	High Similarity	NPC474178
0.8992	High Similarity	NPC210674
0.8992	High Similarity	NPC252307
0.8992	High Similarity	NPC245826
0.8992	High Similarity	NPC31707
0.8992	High Similarity	NPC470084
0.8986	High Similarity	NPC260397
0.8986	High Similarity	NPC317053
0.8986	High Similarity	NPC324492
0.8984	High Similarity	NPC44748
0.8984	High Similarity	NPC78974
0.8984	High Similarity	NPC28730
0.8984	High Similarity	NPC223136
0.8984	High Similarity	NPC103823

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 NPC30043 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	323
0.1-0.2	854
0.2-0.3	1935
0.3-0.4	2690
0.4-0.5	1597
0.5-0.6	923
0.6-0.7	648
0.7-0.8	165
0.8-0.85	12
0.85-0.9	0
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.937	High Similarity	NPD3027	Phase 3
0.9008	High Similarity	NPD1612	Clinical (unspecified phase)
0.9008	High Similarity	NPD1613	Approved
0.8702	High Similarity	NPD1529	Clinical (unspecified phase)
0.8626	High Similarity	NPD1530	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD2983	Phase 2
0.8462	Intermediate Similarity	NPD2982	Phase 2
0.8385	Intermediate Similarity	NPD2981	Phase 2
0.8346	Intermediate Similarity	NPD3018	Phase 2
0.8148	Intermediate Similarity	NPD4908	Phase 1
0.814	Intermediate Similarity	NPD1548	Phase 1
0.8095	Intermediate Similarity	NPD7843	Approved
0.8054	Intermediate Similarity	NPD1934	Approved
0.8047	Intermediate Similarity	NPD7157	Approved
0.8031	Intermediate Similarity	NPD5283	Phase 1
0.803	Intermediate Similarity	NPD1610	Phase 2
0.8029	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8027	Intermediate Similarity	NPD1653	Approved
0.8016	Intermediate Similarity	NPD228	Approved
0.7947	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.792	Intermediate Similarity	NPD2684	Approved
0.7919	Intermediate Similarity	NPD4678	Approved
0.7919	Intermediate Similarity	NPD4675	Approved
0.7899	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1091	Approved
0.7885	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6166	Phase 2
0.7881	Intermediate Similarity	NPD2801	Approved
0.7881	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7054	Approved
0.7832	Intermediate Similarity	NPD7266	Discontinued
0.7829	Intermediate Similarity	NPD3817	Phase 2
0.7815	Intermediate Similarity	NPD37	Approved
0.781	Intermediate Similarity	NPD2861	Phase 2
0.7799	Intermediate Similarity	NPD7074	Phase 3
0.7799	Intermediate Similarity	NPD7472	Approved
0.7786	Intermediate Similarity	NPD1558	Phase 1
0.7778	Intermediate Similarity	NPD3882	Suspended
0.7778	Intermediate Similarity	NPD4967	Phase 2
0.7778	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4966	Approved
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4965	Approved
0.777	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD3705	Approved
0.7746	Intermediate Similarity	NPD4538	Approved
0.7746	Intermediate Similarity	NPD4536	Approved
0.7746	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6674	Discontinued
0.7724	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD3540	Phase 1
0.7698	Intermediate Similarity	NPD290	Approved
0.7698	Intermediate Similarity	NPD4625	Phase 3
0.7692	Intermediate Similarity	NPD7199	Phase 2
0.7677	Intermediate Similarity	NPD6234	Discontinued
0.7673	Intermediate Similarity	NPD3818	Discontinued
0.7669	Intermediate Similarity	NPD1357	Approved
0.7654	Intermediate Similarity	NPD7808	Phase 3
0.7647	Intermediate Similarity	NPD4749	Approved
0.7639	Intermediate Similarity	NPD3539	Phase 1
0.7635	Intermediate Similarity	NPD1511	Approved
0.7626	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD4162	Approved
0.7603	Intermediate Similarity	NPD4237	Approved
0.7603	Intermediate Similarity	NPD3060	Approved
0.7603	Intermediate Similarity	NPD1652	Phase 2
0.7603	Intermediate Similarity	NPD4236	Phase 3
0.7593	Intermediate Similarity	NPD7251	Discontinued
0.7591	Intermediate Similarity	NPD8651	Approved
0.7584	Intermediate Similarity	NPD4123	Phase 3
0.7581	Intermediate Similarity	NPD291	Approved
0.7569	Intermediate Similarity	NPD5960	Phase 3
0.7569	Intermediate Similarity	NPD5588	Approved
0.7562	Intermediate Similarity	NPD7228	Approved
0.7535	Intermediate Similarity	NPD4060	Phase 1
0.7535	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3620	Phase 2
0.7533	Intermediate Similarity	NPD1512	Approved
0.7531	Intermediate Similarity	NPD6797	Phase 2
0.7519	Intermediate Similarity	NPD5536	Phase 2
0.7517	Intermediate Similarity	NPD4357	Discontinued
0.7516	Intermediate Similarity	NPD5844	Phase 1
0.75	Intermediate Similarity	NPD2677	Approved
0.75	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD6671	Approved
0.75	Intermediate Similarity	NPD4005	Discontinued
0.7484	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD5735	Approved
0.7481	Intermediate Similarity	NPD5846	Approved
0.7481	Intermediate Similarity	NPD6516	Phase 2
0.748	Intermediate Similarity	NPD968	Approved
0.7465	Intermediate Similarity	NPD6233	Phase 2
0.7451	Intermediate Similarity	NPD4380	Phase 2
0.745	Intermediate Similarity	NPD5058	Phase 3
0.745	Intermediate Similarity	NPD7124	Phase 2
0.7447	Intermediate Similarity	NPD7095	Approved
0.7445	Intermediate Similarity	NPD2235	Phase 2
0.7445	Intermediate Similarity	NPD2231	Phase 2
0.7442	Intermediate Similarity	NPD3021	Approved
0.7442	Intermediate Similarity	NPD3022	Approved
0.7439	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD3686	Approved
0.7434	Intermediate Similarity	NPD3687	Approved
0.7432	Intermediate Similarity	NPD4628	Phase 3
0.7431	Intermediate Similarity	NPD6653	Approved
0.7419	Intermediate Similarity	NPD5773	Approved
0.7419	Intermediate Similarity	NPD5772	Approved
0.7417	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD7075	Discontinued
0.7389	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD6190	Approved
0.7383	Intermediate Similarity	NPD2219	Phase 1
0.7372	Intermediate Similarity	NPD5402	Approved
0.7365	Intermediate Similarity	NPD5177	Phase 3
0.7361	Intermediate Similarity	NPD5124	Phase 1
0.7361	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD6355	Discontinued
0.736	Intermediate Similarity	NPD1242	Phase 1
0.7357	Intermediate Similarity	NPD6584	Phase 3
0.7351	Intermediate Similarity	NPD7447	Phase 1
0.7347	Intermediate Similarity	NPD1375	Discontinued
0.7347	Intermediate Similarity	NPD5762	Approved
0.7347	Intermediate Similarity	NPD5763	Approved
0.7343	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3892	Phase 2
0.7315	Intermediate Similarity	NPD6331	Phase 2
0.7315	Intermediate Similarity	NPD4110	Phase 3
0.7315	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD52	Approved
0.7303	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD7526	Approved
0.7303	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD5494	Approved
0.7292	Intermediate Similarity	NPD2238	Phase 2
0.7285	Intermediate Similarity	NPD1774	Approved
0.7285	Intermediate Similarity	NPD6799	Approved
0.7285	Intermediate Similarity	NPD7212	Phase 2
0.7285	Intermediate Similarity	NPD7213	Phase 3
0.7285	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7273	Intermediate Similarity	NPD7240	Approved
0.726	Intermediate Similarity	NPD6111	Discontinued
0.7255	Intermediate Similarity	NPD5403	Approved
0.7255	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6801	Discontinued
0.7241	Intermediate Similarity	NPD4340	Discontinued
0.7241	Intermediate Similarity	NPD230	Phase 1
0.7237	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4062	Phase 3
0.7205	Intermediate Similarity	NPD6232	Discontinued
0.7203	Intermediate Similarity	NPD3180	Approved
0.7203	Intermediate Similarity	NPD3179	Approved
0.72	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4535	Phase 3
0.7197	Intermediate Similarity	NPD1465	Phase 2
0.7197	Intermediate Similarity	NPD2978	Approved
0.7197	Intermediate Similarity	NPD2977	Approved
0.7197	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7819	Suspended
0.7195	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD1549	Phase 2
0.7181	Intermediate Similarity	NPD2424	Discontinued
0.7179	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7473	Discontinued
0.7174	Intermediate Similarity	NPD3496	Discontinued
0.7172	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6559	Discontinued
0.7162	Intermediate Similarity	NPD2796	Approved
0.7162	Intermediate Similarity	NPD6099	Approved
0.7162	Intermediate Similarity	NPD6100	Approved
0.7162	Intermediate Similarity	NPD2161	Phase 2
0.7152	Intermediate Similarity	NPD5241	Discontinued
0.7152	Intermediate Similarity	NPD2563	Approved
0.7152	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2560	Approved
0.7143	Intermediate Similarity	NPD821	Approved
0.7143	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD5327	Phase 3
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD6583	Phase 3
0.7143	Intermediate Similarity	NPD7097	Phase 1
0.7143	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6582	Phase 2
0.7126	Intermediate Similarity	NPD7549	Discontinued
0.7124	Intermediate Similarity	NPD5401	Approved
0.7114	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2674	Phase 3
0.7099	Intermediate Similarity	NPD3787	Discontinued
0.7095	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7033	Discontinued

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