NPASS Compound

Structure

NPC476391 OpenBabel07101718292D 36 42 0 0 1 0 0 0 0 0999 V2000 4.2931 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9510 -2.3087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1737 0.2647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8170 -2.8087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1139 -1.7344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8170 -0.8087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2196 0.0194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2654 -2.7922 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7388 -3.7027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2426 0.6231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2632 -1.2087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9510 -1.3087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8765 0.5565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7392 -3.6728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0136 -0.5838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7910 -1.9416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0244 -0.2610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -2.3087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9945 -1.2605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2645 -2.8521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7954 0.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7906 -1.9715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2019 -0.5351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4817 -1.2487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6578 -1.1394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3826 -1.6826 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0850 -0.8087 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4022 1.4071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2135 -4.5235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9050 0.2129 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8452 -1.7862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.8087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2484 -2.6735 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 3 2 0 0 0 0 1 11 1 0 0 0 0 2 4 2 0 0 0 0 2 12 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 11 2 0 0 0 0 5 19 1 0 0 0 0 6 12 2 0 0 0 0 6 20 1 0 0 0 0 7 13 2 0 0 0 0 7 15 1 0 0 0 0 8 14 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 21 2 0 0 0 0 10 13 1 0 0 0 0 10 22 2 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 24 1 0 0 0 0 15 25 2 0 0 0 0 16 23 2 0 0 0 0 16 26 1 0 0 0 0 17 19 2 0 0 0 0 17 31 1 0 0 0 0 18 20 2 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 34 1 0 0 0 0 21 23 1 0 0 0 0 21 35 1 0 0 0 0 22 24 1 0 0 0 0 22 36 1 0 0 0 0 23 25 1 0 0 0 0 24 26 2 0 0 0 0 25 27 1 0 0 0 0 26 28 1 0 0 0 0 27 11 1 1 0 0 0 27 35 1 0 0 0 0 28 12 1 1 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	482.1
Volume:	468.997
LogP:	4.169
LogD:	3.102
LogS:	-5.421
# Rotatable Bonds:	2
TPSA:	139.84
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.149
Synthetic Accessibility Score:	4.011
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.424
MDCK Permeability:	4.589900072460296e-06
Pgp-inhibitor:	0.019
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.857
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	94.13489532470703%
Volume Distribution (VD):	0.402
Pgp-substrate:	6.5849609375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.289
CYP1A2-substrate:	0.123
CYP2C19-inhibitor:	0.268
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.783
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.276
CYP3A4-inhibitor:	0.198
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	4.861
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.196
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.673
Rat Oral Acute Toxicity:	0.882
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.964
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.947
Respiratory Toxicity:	0.235

Download Data

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

Natural Product: NPC476391

Natural Product ID:	NPC476391
*Common Name:**	Jezonofol
IUPAC Name:	n.a.
Synonyms:	Jezonofol
Standard InCHIKey:	GALBTJBRHHLUOS-VSGBNLITSA-N
Standard InCHI:	InChI=1S/C28H18O8/c29-13-7-15-24-22(10-13)36-28(12-2-4-18(32)20(34)6-12)26(24)16-8-14(30)9-21-23(16)25(15)27(35-21)11-1-3-17(31)19(33)5-11/h1-10,27-34H/t27-,28-/m1/s1
SMILES:	C1=CC(=C(C=C1C2C3=C4C=C(C=C5C4=C(C(O5)C6=CC(=C(C=C6)O)O)C7=C3C(=CC(=C7)O)O2)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL593138
PubChem CID:	46226510
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17907781]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[19646881]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	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	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.	Ratio	=	2.3	n.a.	PMID[529432]

☑ 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 NPC476391 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	641
0.1-0.2	2028
0.2-0.3	5486
0.3-0.4	11989
0.4-0.5	5406
0.5-0.6	4549
0.6-0.7	7412
0.7-0.8	4405
0.8-0.85	534
0.85-0.9	198
0.9-0.95	47
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9463	High Similarity	NPC157333
0.931	High Similarity	NPC304894
0.931	High Similarity	NPC15659
0.9272	High Similarity	NPC202104
0.9241	High Similarity	NPC163508
0.9241	High Similarity	NPC173203
0.9189	High Similarity	NPC20757
0.9189	High Similarity	NPC227516
0.9184	High Similarity	NPC14468
0.9054	High Similarity	NPC126291
0.8993	High Similarity	NPC204770
0.8993	High Similarity	NPC236202
0.8993	High Similarity	NPC58190
0.8993	High Similarity	NPC263940
0.8993	High Similarity	NPC108811
0.8993	High Similarity	NPC70409
0.8993	High Similarity	NPC202742
0.8993	High Similarity	NPC82917
0.8993	High Similarity	NPC6702
0.8993	High Similarity	NPC112819
0.8993	High Similarity	NPC294558
0.8993	High Similarity	NPC133209
0.8993	High Similarity	NPC262297
0.8993	High Similarity	NPC111134
0.8993	High Similarity	NPC262911
0.8993	High Similarity	NPC18185
0.8993	High Similarity	NPC170103
0.8973	High Similarity	NPC265075
0.8947	High Similarity	NPC120633
0.8947	High Similarity	NPC473018
0.894	High Similarity	NPC218801
0.8933	High Similarity	NPC329836
0.8926	High Similarity	NPC96576
0.8912	High Similarity	NPC183709
0.8904	High Similarity	NPC20520
0.8904	High Similarity	NPC61783
0.8882	High Similarity	NPC324517
0.8882	High Similarity	NPC329343
0.8882	High Similarity	NPC321972
0.8874	High Similarity	NPC211561
0.8874	High Similarity	NPC321657
0.8874	High Similarity	NPC318373
0.8859	High Similarity	NPC149633
0.8836	High Similarity	NPC32630
0.8828	High Similarity	NPC170328
0.8828	High Similarity	NPC191462
0.8828	High Similarity	NPC133463
0.8828	High Similarity	NPC206525
0.8828	High Similarity	NPC472647
0.8828	High Similarity	NPC472648
0.8828	High Similarity	NPC141717
0.8828	High Similarity	NPC472649
0.8824	High Similarity	NPC279406
0.8824	High Similarity	NPC226809
0.8816	High Similarity	NPC477612
0.88	High Similarity	NPC215678
0.88	High Similarity	NPC260397
0.88	High Similarity	NPC324492
0.88	High Similarity	NPC71686
0.88	High Similarity	NPC176804
0.88	High Similarity	NPC274454
0.88	High Similarity	NPC317053
0.88	High Similarity	NPC233980
0.8792	High Similarity	NPC171932
0.8792	High Similarity	NPC28440
0.8792	High Similarity	NPC473845
0.8776	High Similarity	NPC12668
0.8776	High Similarity	NPC22317
0.8776	High Similarity	NPC262189
0.8776	High Similarity	NPC308768
0.8776	High Similarity	NPC273623
0.8767	High Similarity	NPC71465
0.8767	High Similarity	NPC472646
0.8766	High Similarity	NPC224161
0.8759	High Similarity	NPC37410
0.8759	High Similarity	NPC11727
0.8759	High Similarity	NPC258780
0.8759	High Similarity	NPC125579
0.8759	High Similarity	NPC15109
0.8758	High Similarity	NPC105073
0.8758	High Similarity	NPC224528
0.8758	High Similarity	NPC157081
0.8758	High Similarity	NPC233886
0.875	High Similarity	NPC148516
0.875	High Similarity	NPC177172
0.875	High Similarity	NPC473266
0.875	High Similarity	NPC107862
0.875	High Similarity	NPC470826
0.875	High Similarity	NPC470098
0.875	High Similarity	NPC122980
0.875	High Similarity	NPC180605
0.8742	High Similarity	NPC237546
0.8742	High Similarity	NPC224921
0.8742	High Similarity	NPC328567
0.8742	High Similarity	NPC320970
0.8742	High Similarity	NPC320671
0.8742	High Similarity	NPC231712
0.8742	High Similarity	NPC242774
0.8742	High Similarity	NPC327412
0.8742	High Similarity	NPC153182
0.8742	High Similarity	NPC174251
0.8742	High Similarity	NPC474397
0.8716	High Similarity	NPC178054
0.871	High Similarity	NPC188578
0.871	High Similarity	NPC80918
0.871	High Similarity	NPC46335
0.8707	High Similarity	NPC275061
0.8707	High Similarity	NPC105847
0.8707	High Similarity	NPC220344
0.8707	High Similarity	NPC55947
0.8707	High Similarity	NPC243996
0.8707	High Similarity	NPC132804
0.8707	High Similarity	NPC218131
0.8707	High Similarity	NPC243759
0.8701	High Similarity	NPC134911
0.8701	High Similarity	NPC44192
0.8701	High Similarity	NPC469944
0.8701	High Similarity	NPC160196
0.8701	High Similarity	NPC272552
0.8701	High Similarity	NPC322899
0.8701	High Similarity	NPC226108
0.8701	High Similarity	NPC46283
0.8699	High Similarity	NPC234952
0.8667	High Similarity	NPC470097
0.8667	High Similarity	NPC114119
0.8667	High Similarity	NPC471415
0.8667	High Similarity	NPC473108
0.8658	High Similarity	NPC175838
0.8658	High Similarity	NPC472088
0.8658	High Similarity	NPC472087
0.8649	High Similarity	NPC174787
0.8649	High Similarity	NPC213607
0.8649	High Similarity	NPC182509
0.8645	High Similarity	NPC20050
0.8645	High Similarity	NPC306267
0.8639	High Similarity	NPC56329
0.8639	High Similarity	NPC266453
0.8639	High Similarity	NPC22902
0.8639	High Similarity	NPC151656
0.8639	High Similarity	NPC230919
0.8639	High Similarity	NPC266006
0.8639	High Similarity	NPC200935
0.8639	High Similarity	NPC474390
0.8639	High Similarity	NPC242715
0.863	High Similarity	NPC473413
0.8627	High Similarity	NPC476969
0.8609	High Similarity	NPC181615
0.8609	High Similarity	NPC221318
0.8609	High Similarity	NPC469557
0.86	High Similarity	NPC258083
0.8591	High Similarity	NPC100482
0.8591	High Similarity	NPC472089
0.8591	High Similarity	NPC263261
0.8591	High Similarity	NPC277331
0.8591	High Similarity	NPC87725
0.8581	High Similarity	NPC474442
0.8581	High Similarity	NPC22517
0.8581	High Similarity	NPC21902
0.8571	High Similarity	NPC30632
0.8571	High Similarity	NPC143139
0.8571	High Similarity	NPC202846
0.8562	High Similarity	NPC66840
0.8562	High Similarity	NPC281549
0.8562	High Similarity	NPC256307
0.8553	High Similarity	NPC150714
0.8553	High Similarity	NPC95652
0.8552	High Similarity	NPC303144
0.8544	High Similarity	NPC470827
0.8544	High Similarity	NPC73517
0.8544	High Similarity	NPC125495
0.8544	High Similarity	NPC147743
0.8544	High Similarity	NPC4809
0.8543	High Similarity	NPC12641
0.8543	High Similarity	NPC280092
0.8543	High Similarity	NPC45257
0.8543	High Similarity	NPC50250
0.8543	High Similarity	NPC93323
0.8533	High Similarity	NPC186033
0.8523	High Similarity	NPC309124
0.8523	High Similarity	NPC55793
0.8523	High Similarity	NPC295719
0.8523	High Similarity	NPC73505
0.8523	High Similarity	NPC165026
0.8523	High Similarity	NPC472091
0.8523	High Similarity	NPC34431
0.8523	High Similarity	NPC472090
0.8523	High Similarity	NPC472092
0.8523	High Similarity	NPC184797
0.8516	High Similarity	NPC2745
0.8514	High Similarity	NPC35550
0.8514	High Similarity	NPC48956
0.8503	High Similarity	NPC241241
0.8503	High Similarity	NPC108198
0.8503	High Similarity	NPC200557
0.8503	High Similarity	NPC294884
0.8503	High Similarity	NPC158142
0.8503	High Similarity	NPC69029
0.8503	High Similarity	NPC10314
0.85	High Similarity	NPC177100
0.85	High Similarity	NPC139540

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 NPC476391 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	507
0.1-0.2	962
0.2-0.3	2004
0.3-0.4	2727
0.4-0.5	1528
0.5-0.6	878
0.6-0.7	469
0.7-0.8	69
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8299	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8299	Intermediate Similarity	NPD1613	Approved
0.8163	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD4625	Phase 3
0.8082	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD6234	Discontinued
0.8027	Intermediate Similarity	NPD4908	Phase 1
0.7973	Intermediate Similarity	NPD3027	Phase 3
0.7939	Intermediate Similarity	NPD6959	Discontinued
0.7917	Intermediate Similarity	NPD7228	Approved
0.7805	Intermediate Similarity	NPD4965	Approved
0.7805	Intermediate Similarity	NPD4966	Approved
0.7805	Intermediate Similarity	NPD4967	Phase 2
0.7765	Intermediate Similarity	NPD5844	Phase 1
0.7756	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1610	Phase 2
0.7643	Intermediate Similarity	NPD6674	Discontinued
0.7622	Intermediate Similarity	NPD37	Approved
0.7619	Intermediate Similarity	NPD7199	Phase 2
0.76	Intermediate Similarity	NPD2861	Phase 2
0.7588	Intermediate Similarity	NPD6166	Phase 2
0.7588	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7588	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD6232	Discontinued
0.7529	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1548	Phase 1
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4749	Approved
0.7442	Intermediate Similarity	NPD7473	Discontinued
0.743	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD7240	Approved
0.741	Intermediate Similarity	NPD1934	Approved
0.7365	Intermediate Similarity	NPD8455	Phase 2
0.7355	Intermediate Similarity	NPD3620	Phase 2
0.7355	Intermediate Similarity	NPD4060	Phase 1
0.7355	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6559	Discontinued
0.7308	Intermediate Similarity	NPD5735	Approved
0.7303	Intermediate Similarity	NPD8053	Approved
0.7303	Intermediate Similarity	NPD8054	Approved
0.7301	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3818	Discontinued
0.7285	Intermediate Similarity	NPD6696	Suspended
0.7278	Intermediate Similarity	NPD7768	Phase 2
0.7273	Intermediate Similarity	NPD1653	Approved
0.7267	Intermediate Similarity	NPD7229	Phase 3
0.7262	Intermediate Similarity	NPD1465	Phase 2
0.725	Intermediate Similarity	NPD7037	Approved
0.7247	Intermediate Similarity	NPD8312	Approved
0.7247	Intermediate Similarity	NPD8313	Approved
0.7239	Intermediate Similarity	NPD7390	Discontinued
0.7239	Intermediate Similarity	NPD1511	Approved
0.7239	Intermediate Similarity	NPD7213	Phase 3
0.7239	Intermediate Similarity	NPD7212	Phase 2
0.7219	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7074	Phase 3
0.7195	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7447	Phase 1
0.719	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4380	Phase 2
0.7184	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7906	Approved
0.7176	Intermediate Similarity	NPD3882	Suspended
0.7168	Intermediate Similarity	NPD3787	Discontinued
0.716	Intermediate Similarity	NPD2801	Approved
0.7159	Intermediate Similarity	NPD7054	Approved
0.7152	Intermediate Similarity	NPD1512	Approved
0.7151	Intermediate Similarity	NPD4577	Approved
0.7151	Intermediate Similarity	NPD5494	Approved
0.7151	Intermediate Similarity	NPD4578	Approved
0.7143	Intermediate Similarity	NPD7680	Approved
0.7143	Intermediate Similarity	NPD3018	Phase 2
0.7127	Intermediate Similarity	NPD4663	Approved
0.7126	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7472	Approved
0.7112	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6797	Phase 2
0.7072	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5588	Approved
0.7059	Intermediate Similarity	NPD7819	Suspended
0.7056	Intermediate Similarity	NPD7313	Approved
0.7056	Intermediate Similarity	NPD7310	Approved
0.7056	Intermediate Similarity	NPD7311	Approved
0.7056	Intermediate Similarity	NPD7312	Approved
0.7055	Intermediate Similarity	NPD3750	Approved
0.7055	Intermediate Similarity	NPD3892	Phase 2
0.7055	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4097	Suspended
0.7039	Intermediate Similarity	NPD7251	Discontinued
0.7035	Intermediate Similarity	NPD3749	Approved
0.7019	Intermediate Similarity	NPD6100	Approved
0.7019	Intermediate Similarity	NPD6099	Approved
0.7017	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7309	Approved
0.7006	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5327	Phase 3
0.6993	Remote Similarity	NPD2983	Phase 2
0.6993	Remote Similarity	NPD2982	Phase 2
0.6989	Remote Similarity	NPD27	Approved
0.6989	Remote Similarity	NPD2489	Approved
0.6988	Remote Similarity	NPD2532	Approved
0.6988	Remote Similarity	NPD2533	Approved
0.6988	Remote Similarity	NPD2534	Approved
0.6988	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5124	Phase 1
0.6975	Remote Similarity	NPD5762	Approved
0.6975	Remote Similarity	NPD5763	Approved
0.6974	Remote Similarity	NPD3705	Approved
0.6971	Remote Similarity	NPD3051	Approved
0.6966	Remote Similarity	NPD8156	Discontinued
0.6951	Remote Similarity	NPD7466	Approved
0.6951	Remote Similarity	NPD7003	Approved
0.6948	Remote Similarity	NPD8651	Approved
0.6946	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7411	Suspended
0.6937	Remote Similarity	NPD6353	Approved
0.6936	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7075	Discontinued
0.6932	Remote Similarity	NPD2970	Approved
0.6932	Remote Similarity	NPD2969	Approved
0.6928	Remote Similarity	NPD2981	Phase 2
0.6928	Remote Similarity	NPD7041	Phase 2
0.6928	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3817	Phase 2
0.6918	Remote Similarity	NPD4140	Approved
0.6914	Remote Similarity	NPD8127	Discontinued
0.691	Remote Similarity	NPD8252	Approved
0.691	Remote Similarity	NPD8251	Approved
0.691	Remote Similarity	NPD8099	Discontinued
0.691	Remote Similarity	NPD3751	Discontinued
0.6906	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD7549	Discontinued
0.6906	Remote Similarity	NPD7808	Phase 3
0.6903	Remote Similarity	NPD3094	Phase 2
0.6899	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4536	Approved
0.6894	Remote Similarity	NPD4538	Approved
0.6894	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2342	Discontinued
0.6872	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7266	Discontinued
0.6871	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5058	Phase 3
0.6863	Remote Similarity	NPD1091	Approved
0.6863	Remote Similarity	NPD1611	Approved
0.686	Remote Similarity	NPD5929	Approved
0.6859	Remote Similarity	NPD6584	Phase 3
0.6852	Remote Similarity	NPD5960	Phase 3
0.6848	Remote Similarity	NPD8166	Discontinued
0.6848	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5125	Phase 3
0.6842	Remote Similarity	NPD4626	Approved
0.6842	Remote Similarity	NPD5126	Approved
0.6829	Remote Similarity	NPD1549	Phase 2
0.6826	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5283	Phase 1
0.6824	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5404	Approved
0.681	Remote Similarity	NPD5408	Approved
0.681	Remote Similarity	NPD5406	Approved
0.681	Remote Similarity	NPD5405	Approved
0.6807	Remote Similarity	NPD2677	Approved
0.6803	Remote Similarity	NPD228	Approved
0.6792	Remote Similarity	NPD6798	Discontinued
0.6791	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.679	Remote Similarity	NPD7097	Phase 1
0.6786	Remote Similarity	NPD8151	Discontinued
0.6782	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD3021	Approved
0.6781	Remote Similarity	NPD3022	Approved
0.6776	Remote Similarity	NPD5691	Approved
0.6763	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD4666	Phase 3
0.6753	Remote Similarity	NPD3092	Approved
0.6753	Remote Similarity	NPD422	Phase 1
0.6748	Remote Similarity	NPD3748	Approved
0.6747	Remote Similarity	NPD6331	Phase 2
0.6746	Remote Similarity	NPD4319	Phase 2
0.6744	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7831	Phase 2
0.6743	Remote Similarity	NPD7833	Phase 2
0.6743	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6671	Approved
0.6733	Remote Similarity	NPD7157	Approved
0.6732	Remote Similarity	NPD5846	Approved
0.6732	Remote Similarity	NPD6516	Phase 2

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