NPASS Compound

Structure

NPC476393 OpenBabel07101718292D 36 40 0 0 1 0 0 0 0 0999 V2000 -2.0517 -0.6435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5113 -1.5760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5910 0.2440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0032 0.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5103 -1.6209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9543 0.9000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5890 0.1543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4680 2.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2508 -0.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0507 -0.6884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5920 0.2889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0486 -0.7781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1622 1.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5880 0.1095 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4190 2.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4577 -0.4738 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 2 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 -1.2321 4.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 4.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0476 -0.8230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1132 2.1871 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1264 0.9522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6270 3.5254 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7238 -1.4377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 1 13 1 0 0 0 0 2 5 2 0 0 0 0 2 13 1 0 0 0 0 3 15 1 0 0 0 0 4 6 2 0 0 0 0 4 14 1 0 0 0 0 5 19 1 0 0 0 0 6 20 1 0 0 0 0 7 13 2 0 0 0 0 7 21 1 0 0 0 0 8 16 2 0 0 0 0 8 17 1 0 0 0 0 9 16 1 0 0 0 0 9 18 2 0 0 0 0 10 14 2 0 0 0 0 10 22 1 0 0 0 0 11 15 2 0 0 0 0 11 23 1 0 0 0 0 12 17 2 0 0 0 0 12 18 1 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 21 2 0 0 0 0 19 31 1 0 0 0 0 20 22 2 0 0 0 0 20 32 1 0 0 0 0 21 33 1 0 0 0 0 22 34 1 0 0 0 0 23 35 2 0 0 0 0 24 14 1 1 0 0 0 24 25 1 0 0 0 0 24 27 1 0 0 0 0 25 16 1 6 0 0 0 25 26 1 0 0 0 0 26 15 1 1 0 0 0 26 28 1 0 0 0 0 27 23 1 1 0 0 0 27 28 1 0 0 0 0 28 36 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.13
Volume:	486.11
LogP:	4.144
LogD:	2.686
LogS:	-3.026
# Rotatable Bonds:	4
TPSA:	161.84
# H-Bond Aceptor:	8
# H-Bond Donor:	8
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.151
Synthetic Accessibility Score:	4.464
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:	-6.12
MDCK Permeability:	5.889011845283676e-06
Pgp-inhibitor:	0.423
Pgp-substrate:	0.062
Human Intestinal Absorption (HIA):	0.39
20% Bioavailability (F20%):	0.464
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	93.681640625%
Volume Distribution (VD):	0.525
Pgp-substrate:	4.15179443359375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.53
CYP1A2-substrate:	0.731
CYP2C19-inhibitor:	0.064
CYP2C19-substrate:	0.042
CYP2C9-inhibitor:	0.64
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.772
CYP3A4-inhibitor:	0.12
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	16.748
Half-life (T1/2):	0.769

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.614
Drug-inuced Liver Injury (DILI):	0.685
AMES Toxicity:	0.44
Rat Oral Acute Toxicity:	0.221
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.98
Carcinogencity:	0.066
Eye Corrosion:	0.003
Eye Irritation:	0.93
Respiratory Toxicity:	0.053

Download Data

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

Natural Product: NPC476393

Natural Product ID:	NPC476393
*Common Name:**	Jezonodione
IUPAC Name:	(1S,5R,6R,7R)-7-(3,4-dihydroxyphenyl)-6-(3,5-dihydroxyphenyl)-4-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]bicyclo[3.2.1]oct-3-ene-2,8-dione
Synonyms:	Jezonodione
Standard InCHIKey:	CHMRNIGJIJLNNX-UIBOKMEBSA-N
Standard InCHI:	InChI=1S/C28H22O8/c29-17-8-16(9-18(30)12-17)25-24(14-4-6-20(32)22(34)10-14)27-23(35)11-15(26(25)28(27)36)3-1-13-2-5-19(31)21(33)7-13/h1-12,24-27,29-34H/b3-1+/t24-,25-,26+,27-/m1/s1
SMILES:	C1=CC(=C(C=C1C=CC2=CC(=O)C3C(C(C2C3=O)C4=CC(=CC(=C4)O)O)C5=CC(=C(C=C5)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL593355
PubChem CID:	46226501
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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	=	2.2	n.a.	PMID[528164]

☑ 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 NPC476393 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	378
0.1-0.2	1453
0.2-0.3	3017
0.3-0.4	9119
0.4-0.5	10652
0.5-0.6	5734
0.6-0.7	10196
0.7-0.8	2133
0.8-0.85	12
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8523	High Similarity	NPC473365
0.8519	High Similarity	NPC156539
0.8511	High Similarity	NPC20210
0.8333	Intermediate Similarity	NPC244441
0.8296	Intermediate Similarity	NPC15127
0.8248	Intermediate Similarity	NPC107672
0.8182	Intermediate Similarity	NPC290030
0.8168	Intermediate Similarity	NPC277394
0.8168	Intermediate Similarity	NPC61062
0.8168	Intermediate Similarity	NPC299252
0.8162	Intermediate Similarity	NPC471927
0.8148	Intermediate Similarity	NPC120172
0.8146	Intermediate Similarity	NPC35
0.8138	Intermediate Similarity	NPC203063
0.8099	Intermediate Similarity	NPC471913
0.8071	Intermediate Similarity	NPC233056
0.8069	Intermediate Similarity	NPC472903
0.8043	Intermediate Similarity	NPC145659
0.8043	Intermediate Similarity	NPC9292
0.8042	Intermediate Similarity	NPC43353
0.8029	Intermediate Similarity	NPC97578
0.8	Intermediate Similarity	NPC294361
0.8	Intermediate Similarity	NPC236520
0.7986	Intermediate Similarity	NPC264112
0.7986	Intermediate Similarity	NPC65005
0.7986	Intermediate Similarity	NPC194764
0.7973	Intermediate Similarity	NPC238629
0.7959	Intermediate Similarity	NPC91019
0.7959	Intermediate Similarity	NPC472904
0.7959	Intermediate Similarity	NPC472410
0.7959	Intermediate Similarity	NPC277784
0.7959	Intermediate Similarity	NPC106519
0.7958	Intermediate Similarity	NPC135801
0.7958	Intermediate Similarity	NPC175738
0.7943	Intermediate Similarity	NPC26697
0.7931	Intermediate Similarity	NPC471152
0.7929	Intermediate Similarity	NPC234175
0.7926	Intermediate Similarity	NPC318552
0.7926	Intermediate Similarity	NPC190501
0.7926	Intermediate Similarity	NPC69006
0.7923	Intermediate Similarity	NPC268032
0.7911	Intermediate Similarity	NPC149389
0.791	Intermediate Similarity	NPC144343
0.7908	Intermediate Similarity	NPC476434
0.7899	Intermediate Similarity	NPC224342
0.7887	Intermediate Similarity	NPC34070
0.7887	Intermediate Similarity	NPC469526
0.7883	Intermediate Similarity	NPC86900
0.7877	Intermediate Similarity	NPC471974
0.7877	Intermediate Similarity	NPC469680
0.7877	Intermediate Similarity	NPC469681
0.7871	Intermediate Similarity	NPC203757
0.7868	Intermediate Similarity	NPC248363
0.7863	Intermediate Similarity	NPC51698
0.7862	Intermediate Similarity	NPC7464
0.7852	Intermediate Similarity	NPC451542
0.7852	Intermediate Similarity	NPC313047
0.7852	Intermediate Similarity	NPC174905
0.7852	Intermediate Similarity	NPC293545
0.7852	Intermediate Similarity	NPC474203
0.7852	Intermediate Similarity	NPC217174
0.7852	Intermediate Similarity	NPC295712
0.7847	Intermediate Similarity	NPC248150
0.7843	Intermediate Similarity	NPC48949
0.782	Intermediate Similarity	NPC472893
0.7815	Intermediate Similarity	NPC110882
0.7815	Intermediate Similarity	NPC476535
0.7815	Intermediate Similarity	NPC85393
0.7815	Intermediate Similarity	NPC271944
0.781	Intermediate Similarity	NPC39029
0.781	Intermediate Similarity	NPC237667
0.78	Intermediate Similarity	NPC10764
0.7794	Intermediate Similarity	NPC34634
0.7794	Intermediate Similarity	NPC265454
0.7786	Intermediate Similarity	NPC297657
0.7778	Intermediate Similarity	NPC4170
0.7778	Intermediate Similarity	NPC471749
0.777	Intermediate Similarity	NPC169452
0.777	Intermediate Similarity	NPC181560
0.777	Intermediate Similarity	NPC9218
0.7755	Intermediate Similarity	NPC477849
0.7755	Intermediate Similarity	NPC91887
0.7755	Intermediate Similarity	NPC157284
0.7755	Intermediate Similarity	NPC469857
0.7755	Intermediate Similarity	NPC23667
0.7755	Intermediate Similarity	NPC50615
0.7755	Intermediate Similarity	NPC473779
0.7755	Intermediate Similarity	NPC473479
0.7755	Intermediate Similarity	NPC42384
0.7755	Intermediate Similarity	NPC245760
0.7755	Intermediate Similarity	NPC51531
0.7755	Intermediate Similarity	NPC473622
0.7755	Intermediate Similarity	NPC149773
0.7755	Intermediate Similarity	NPC5014
0.7755	Intermediate Similarity	NPC297797
0.7755	Intermediate Similarity	NPC165191
0.7755	Intermediate Similarity	NPC28592
0.7755	Intermediate Similarity	NPC114333
0.7755	Intermediate Similarity	NPC46242
0.7755	Intermediate Similarity	NPC289358
0.7748	Intermediate Similarity	NPC472560
0.7748	Intermediate Similarity	NPC66894
0.7748	Intermediate Similarity	NPC8102
0.7746	Intermediate Similarity	NPC92624
0.7746	Intermediate Similarity	NPC470747
0.774	Intermediate Similarity	NPC223836
0.774	Intermediate Similarity	NPC191976
0.7737	Intermediate Similarity	NPC98305
0.7737	Intermediate Similarity	NPC24125
0.7733	Intermediate Similarity	NPC16353
0.7724	Intermediate Similarity	NPC44437
0.7721	Intermediate Similarity	NPC258366
0.7721	Intermediate Similarity	NPC79933
0.7721	Intermediate Similarity	NPC473974
0.7721	Intermediate Similarity	NPC191866
0.7721	Intermediate Similarity	NPC31296
0.7718	Intermediate Similarity	NPC477275
0.7712	Intermediate Similarity	NPC471907
0.7704	Intermediate Similarity	NPC277588
0.7703	Intermediate Similarity	NPC242994
0.7703	Intermediate Similarity	NPC294330
0.7703	Intermediate Similarity	NPC138099
0.7703	Intermediate Similarity	NPC191280
0.7698	Intermediate Similarity	NPC53567
0.7697	Intermediate Similarity	NPC30720
0.7692	Intermediate Similarity	NPC105727
0.7692	Intermediate Similarity	NPC259942
0.7692	Intermediate Similarity	NPC58427
0.7692	Intermediate Similarity	NPC114392
0.7692	Intermediate Similarity	NPC34864
0.7687	Intermediate Similarity	NPC474110
0.7687	Intermediate Similarity	NPC44960
0.7687	Intermediate Similarity	NPC277559
0.7687	Intermediate Similarity	NPC170742
0.7682	Intermediate Similarity	NPC53520
0.7682	Intermediate Similarity	NPC227841
0.7681	Intermediate Similarity	NPC472271
0.7681	Intermediate Similarity	NPC196976
0.7677	Intermediate Similarity	NPC78505
0.7677	Intermediate Similarity	NPC270268
0.7676	Intermediate Similarity	NPC24869
0.7671	Intermediate Similarity	NPC252343
0.7671	Intermediate Similarity	NPC153088
0.7669	Intermediate Similarity	NPC188079
0.7667	Intermediate Similarity	NPC291078
0.7667	Intermediate Similarity	NPC193555
0.7667	Intermediate Similarity	NPC477697
0.7667	Intermediate Similarity	NPC137649
0.7667	Intermediate Similarity	NPC273657
0.7667	Intermediate Similarity	NPC106920
0.7667	Intermediate Similarity	NPC477696
0.7667	Intermediate Similarity	NPC470811
0.7665	Intermediate Similarity	NPC120102
0.7664	Intermediate Similarity	NPC472071
0.7655	Intermediate Similarity	NPC267205
0.7655	Intermediate Similarity	NPC473665
0.7655	Intermediate Similarity	NPC294226
0.7651	Intermediate Similarity	NPC19158
0.7651	Intermediate Similarity	NPC38473
0.7651	Intermediate Similarity	NPC473527
0.7647	Intermediate Similarity	NPC162751
0.7647	Intermediate Similarity	NPC77598
0.7647	Intermediate Similarity	NPC52161
0.7639	Intermediate Similarity	NPC238168
0.7639	Intermediate Similarity	NPC237424
0.7639	Intermediate Similarity	NPC243305
0.7635	Intermediate Similarity	NPC61398
0.7635	Intermediate Similarity	NPC230811
0.7635	Intermediate Similarity	NPC175552
0.7635	Intermediate Similarity	NPC416
0.7634	Intermediate Similarity	NPC88141
0.7634	Intermediate Similarity	NPC254833
0.7634	Intermediate Similarity	NPC228343
0.7632	Intermediate Similarity	NPC68441
0.7628	Intermediate Similarity	NPC473544
0.7628	Intermediate Similarity	NPC475162
0.7628	Intermediate Similarity	NPC178574
0.7628	Intermediate Similarity	NPC475595
0.7628	Intermediate Similarity	NPC476533
0.7628	Intermediate Similarity	NPC83663
0.7628	Intermediate Similarity	NPC266084
0.7628	Intermediate Similarity	NPC475216
0.7628	Intermediate Similarity	NPC65591
0.7628	Intermediate Similarity	NPC475145
0.7622	Intermediate Similarity	NPC109123
0.7622	Intermediate Similarity	NPC304622
0.7616	Intermediate Similarity	NPC296752
0.7616	Intermediate Similarity	NPC183824
0.7615	Intermediate Similarity	NPC176527
0.7613	Intermediate Similarity	NPC85131
0.7613	Intermediate Similarity	NPC474191
0.7613	Intermediate Similarity	NPC476532
0.7613	Intermediate Similarity	NPC280295
0.7612	Intermediate Similarity	NPC120280
0.761	Intermediate Similarity	NPC46736
0.761	Intermediate Similarity	NPC197856
0.7603	Intermediate Similarity	NPC166480
0.7603	Intermediate Similarity	NPC475088
0.7603	Intermediate Similarity	NPC282780
0.76	Intermediate Similarity	NPC246638

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 NPC476393 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	321
0.1-0.2	856
0.2-0.3	1390
0.3-0.4	2925
0.4-0.5	2209
0.5-0.6	1123
0.6-0.7	282
0.7-0.8	44
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7958	Intermediate Similarity	NPD943	Approved
0.7926	Intermediate Similarity	NPD2932	Approved
0.7926	Intermediate Similarity	NPD3019	Approved
0.7718	Intermediate Similarity	NPD8166	Discontinued
0.7682	Intermediate Similarity	NPD7390	Discontinued
0.7634	Intermediate Similarity	NPD3021	Approved
0.7634	Intermediate Similarity	NPD3022	Approved
0.7632	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD3026	Approved
0.7482	Intermediate Similarity	NPD3023	Approved
0.7464	Intermediate Similarity	NPD3025	Approved
0.7464	Intermediate Similarity	NPD3024	Approved
0.745	Intermediate Similarity	NPD5405	Approved
0.745	Intermediate Similarity	NPD5404	Approved
0.745	Intermediate Similarity	NPD5406	Approved
0.745	Intermediate Similarity	NPD5408	Approved
0.7429	Intermediate Similarity	NPD1201	Approved
0.7407	Intermediate Similarity	NPD7199	Phase 2
0.7391	Intermediate Similarity	NPD6234	Discontinued
0.7376	Intermediate Similarity	NPD9269	Phase 2
0.7375	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD1470	Approved
0.7338	Intermediate Similarity	NPD1511	Approved
0.7333	Intermediate Similarity	NPD7473	Discontinued
0.732	Intermediate Similarity	NPD6190	Approved
0.7317	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD37	Approved
0.7273	Intermediate Similarity	NPD6166	Phase 2
0.7273	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6232	Discontinued
0.7255	Intermediate Similarity	NPD3750	Approved
0.725	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1512	Approved
0.7239	Intermediate Similarity	NPD4750	Phase 3
0.7222	Intermediate Similarity	NPD3094	Phase 2
0.7211	Intermediate Similarity	NPD3764	Approved
0.7203	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD1934	Approved
0.7186	Intermediate Similarity	NPD7228	Approved
0.7183	Intermediate Similarity	NPD3092	Approved
0.717	Intermediate Similarity	NPD7028	Phase 2
0.7162	Intermediate Similarity	NPD6663	Approved
0.716	Intermediate Similarity	NPD4966	Approved
0.716	Intermediate Similarity	NPD4967	Phase 2
0.716	Intermediate Similarity	NPD4965	Approved
0.7154	Intermediate Similarity	NPD1242	Phase 1
0.7143	Intermediate Similarity	NPD3027	Phase 3
0.7143	Intermediate Similarity	NPD2801	Approved
0.7123	Intermediate Similarity	NPD5736	Approved
0.7092	Intermediate Similarity	NPD9268	Approved
0.7075	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD230	Phase 1
0.7055	Intermediate Similarity	NPD3882	Suspended
0.7052	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3300	Phase 2
0.7042	Intermediate Similarity	NPD4059	Approved
0.7037	Intermediate Similarity	NPD1465	Phase 2
0.7021	Intermediate Similarity	NPD3091	Approved
0.7007	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD6099	Approved
0.6993	Remote Similarity	NPD6100	Approved
0.6988	Remote Similarity	NPD8127	Discontinued
0.6982	Remote Similarity	NPD3818	Discontinued
0.6962	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4908	Phase 1
0.6957	Remote Similarity	NPD4380	Phase 2
0.6948	Remote Similarity	NPD7266	Discontinued
0.6947	Remote Similarity	NPD3020	Approved
0.6941	Remote Similarity	NPD5844	Phase 1
0.6928	Remote Similarity	NPD3748	Approved
0.6928	Remote Similarity	NPD1510	Phase 2
0.6923	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1876	Approved
0.6901	Remote Similarity	NPD7074	Phase 3
0.6887	Remote Similarity	NPD1613	Approved
0.6887	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3620	Phase 2
0.6887	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6959	Discontinued
0.6867	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD846	Approved
0.6842	Remote Similarity	NPD940	Approved
0.6842	Remote Similarity	NPD7054	Approved
0.6807	Remote Similarity	NPD3749	Approved
0.6806	Remote Similarity	NPD3095	Discontinued
0.6802	Remote Similarity	NPD7472	Approved
0.6797	Remote Similarity	NPD1607	Approved
0.6788	Remote Similarity	NPD3817	Phase 2
0.6776	Remote Similarity	NPD1240	Approved
0.6763	Remote Similarity	NPD6797	Phase 2
0.6761	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7819	Suspended
0.6726	Remote Similarity	NPD5494	Approved
0.6724	Remote Similarity	NPD7240	Approved
0.6724	Remote Similarity	NPD7251	Discontinued
0.6724	Remote Similarity	NPD7685	Pre-registration
0.6718	Remote Similarity	NPD2859	Approved
0.6718	Remote Similarity	NPD2860	Approved
0.6715	Remote Similarity	NPD2342	Discontinued
0.6713	Remote Similarity	NPD5536	Phase 2
0.6711	Remote Similarity	NPD8032	Phase 2
0.6711	Remote Similarity	NPD258	Approved
0.6711	Remote Similarity	NPD257	Approved
0.6708	Remote Similarity	NPD6273	Approved
0.6707	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7411	Suspended
0.6705	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD1549	Phase 2
0.6686	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7768	Phase 2
0.6645	Remote Similarity	NPD3268	Approved
0.6644	Remote Similarity	NPD2797	Approved
0.6644	Remote Similarity	NPD1164	Approved
0.6641	Remote Similarity	NPD2934	Approved
0.6641	Remote Similarity	NPD2933	Approved
0.6629	Remote Similarity	NPD6559	Discontinued
0.6628	Remote Similarity	NPD5033	Approved
0.6622	Remote Similarity	NPD4749	Approved
0.6621	Remote Similarity	NPD1651	Approved
0.6609	Remote Similarity	NPD4956	Approved
0.6608	Remote Similarity	NPD3926	Phase 2
0.6607	Remote Similarity	NPD7075	Discontinued
0.6604	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4110	Phase 3
0.6604	Remote Similarity	NPD7003	Approved
0.6599	Remote Similarity	NPD1610	Phase 2
0.6591	Remote Similarity	NPD7808	Phase 3
0.6585	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD4357	Discontinued
0.6579	Remote Similarity	NPD4625	Phase 3
0.6577	Remote Similarity	NPD1283	Approved
0.6575	Remote Similarity	NPD2286	Discontinued
0.657	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2935	Discontinued
0.6558	Remote Similarity	NPD826	Approved
0.6558	Remote Similarity	NPD825	Approved
0.6556	Remote Similarity	NPD9569	Approved
0.6556	Remote Similarity	NPD2861	Phase 2
0.6554	Remote Similarity	NPD5035	Approved
0.6554	Remote Similarity	NPD4878	Approved
0.6549	Remote Similarity	NPD5283	Phase 1
0.6549	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD5039	Approved
0.6516	Remote Similarity	NPD6355	Discontinued
0.651	Remote Similarity	NPD2983	Phase 2
0.651	Remote Similarity	NPD2982	Phase 2
0.6507	Remote Similarity	NPD4093	Discontinued
0.65	Remote Similarity	NPD4628	Phase 3
0.6497	Remote Similarity	NPD5032	Approved
0.6494	Remote Similarity	NPD3751	Discontinued
0.649	Remote Similarity	NPD4624	Approved
0.6489	Remote Similarity	NPD7680	Approved
0.6488	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5402	Approved
0.6483	Remote Similarity	NPD7610	Discontinued
0.6479	Remote Similarity	NPD7635	Approved
0.6475	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6651	Approved
0.6471	Remote Similarity	NPD7095	Approved
0.6463	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5403	Approved
0.6456	Remote Similarity	NPD2796	Approved
0.6456	Remote Similarity	NPD9570	Approved
0.6454	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7229	Phase 3
0.6452	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD9494	Approved
0.6447	Remote Similarity	NPD3018	Phase 2
0.6446	Remote Similarity	NPD6599	Discontinued
0.6444	Remote Similarity	NPD8150	Discontinued
0.6443	Remote Similarity	NPD2981	Phase 2
0.6443	Remote Similarity	NPD1608	Approved
0.6443	Remote Similarity	NPD3972	Approved
0.6442	Remote Similarity	NPD2532	Approved
0.6442	Remote Similarity	NPD2534	Approved
0.6442	Remote Similarity	NPD2533	Approved
0.6438	Remote Similarity	NPD2800	Approved
0.6438	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6798	Discontinued
0.6424	Remote Similarity	NPD1653	Approved
0.6418	Remote Similarity	NPD288	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