NPASS Compound

Structure

NPC470178 OpenBabel07101719242D 23 26 0 0 1 0 0 0 0 0999 V2000 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 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 3.5491 1.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 7 1 0 0 0 0 3 8 2 0 0 0 0 4 9 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 5 12 1 0 0 0 0 6 21 1 0 0 0 0 6 22 1 0 0 0 0 7 10 1 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 18 2 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 14 19 1 0 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.06
Volume:	294.143
LogP:	2.426
LogD:	1.986
LogS:	-3.712
# Rotatable Bonds:	1
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.693
Synthetic Accessibility Score:	3.289
Fsp3:	0.188
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.249
MDCK Permeability:	1.6589137885603122e-05
Pgp-inhibitor:	0.075
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.142

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01
Plasma Protein Binding (PPB):	98.64722442626953%
Volume Distribution (VD):	0.421
Pgp-substrate:	3.4236199855804443%

ADMET: Metabolism

CYP1A2-inhibitor:	0.883
CYP1A2-substrate:	0.275
CYP2C19-inhibitor:	0.778
CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.849
CYP2C9-substrate:	0.823
CYP2D6-inhibitor:	0.833
CYP2D6-substrate:	0.319
CYP3A4-inhibitor:	0.811
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	19.552
Half-life (T1/2):	0.613

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.105
Drug-inuced Liver Injury (DILI):	0.937
AMES Toxicity:	0.248
Rat Oral Acute Toxicity:	0.573
Maximum Recommended Daily Dose:	0.123
Skin Sensitization:	0.931
Carcinogencity:	0.88
Eye Corrosion:	0.003
Eye Irritation:	0.902
Respiratory Toxicity:	0.405

Download Data

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

Natural Product: NPC470178

Natural Product ID:	NPC470178
*Common Name:**	5,2',3'-Trihydroxy-6,7-Methylenedioxyflavanone
IUPAC Name:	6-(2,3-dihydroxyphenyl)-9-hydroxy-6,7-dihydro-[1,3]dioxolo[4,5-g]chromen-8-one
Synonyms:
Standard InCHIKey:	KGKAAUBCGDPTDT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O7/c17-8-3-1-2-7(14(8)19)10-4-9(18)13-11(23-10)5-12-16(15(13)20)22-6-21-12/h1-3,5,10,17,19-20H,4,6H2
SMILES:	C1C(OC2=CC3=C(C(=C2C1=O)O)OCO3)C4=C(C(=CC=C4)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1807889
PubChem CID:	42608091
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0001632] Flavanones

*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
NPO8206	Iris tenuifolia	Species	Iridaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18472117]
NPO8206	Iris tenuifolia	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21737268]
NPO8206	Iris tenuifolia	Species	Iridaceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	61.7	%	PMID[520912]

☑ 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 NPC470178 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	431
0.1-0.2	1850
0.2-0.3	4558
0.3-0.4	10372
0.4-0.5	7404
0.5-0.6	3673
0.6-0.7	4744
0.7-0.8	5927
0.8-0.85	2395
0.85-0.9	1172
0.9-0.95	167
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9809	High Similarity	NPC42892
0.9742	High Similarity	NPC162668
0.9554	High Similarity	NPC469575
0.9551	High Similarity	NPC225624
0.9551	High Similarity	NPC285973
0.9506	High Similarity	NPC472607
0.95	High Similarity	NPC170675
0.95	High Similarity	NPC471457
0.95	High Similarity	NPC112755
0.949	High Similarity	NPC295009
0.949	High Similarity	NPC260640
0.9484	High Similarity	NPC255106
0.9484	High Similarity	NPC235165
0.9441	High Similarity	NPC22195
0.9441	High Similarity	NPC212748
0.9441	High Similarity	NPC471416
0.9441	High Similarity	NPC183357
0.9441	High Similarity	NPC21190
0.9441	High Similarity	NPC34287
0.9437	High Similarity	NPC45618
0.9437	High Similarity	NPC58716
0.9437	High Similarity	NPC146792
0.9434	High Similarity	NPC165720
0.9423	High Similarity	NPC156057
0.9423	High Similarity	NPC162869
0.9423	High Similarity	NPC48208
0.9423	High Similarity	NPC474208
0.9423	High Similarity	NPC474836
0.9423	High Similarity	NPC475267
0.9423	High Similarity	NPC210084
0.9423	High Similarity	NPC99597
0.9383	High Similarity	NPC205076
0.9383	High Similarity	NPC307518
0.9383	High Similarity	NPC48773
0.9379	High Similarity	NPC93337
0.9379	High Similarity	NPC58053
0.9379	High Similarity	NPC469931
0.9379	High Similarity	NPC105025
0.9379	High Similarity	NPC472383
0.9379	High Similarity	NPC472381
0.9379	High Similarity	NPC201292
0.9379	High Similarity	NPC226294
0.9379	High Similarity	NPC45638
0.9379	High Similarity	NPC95855
0.9379	High Similarity	NPC475942
0.9379	High Similarity	NPC210042
0.9379	High Similarity	NPC186807
0.9375	High Similarity	NPC113093
0.9371	High Similarity	NPC88043
0.9363	High Similarity	NPC62518
0.9363	High Similarity	NPC215375
0.9351	High Similarity	NPC204515
0.9325	High Similarity	NPC239549
0.9325	High Similarity	NPC236191
0.9325	High Similarity	NPC51774
0.9321	High Similarity	NPC44558
0.9321	High Similarity	NPC84265
0.9321	High Similarity	NPC245014
0.9321	High Similarity	NPC282987
0.9321	High Similarity	NPC105511
0.9321	High Similarity	NPC72249
0.9321	High Similarity	NPC224462
0.9321	High Similarity	NPC474434
0.9317	High Similarity	NPC45400
0.9317	High Similarity	NPC76482
0.9317	High Similarity	NPC93099
0.9308	High Similarity	NPC125991
0.9308	High Similarity	NPC127782
0.9308	High Similarity	NPC300537
0.9304	High Similarity	NPC263449
0.9299	High Similarity	NPC167595
0.9299	High Similarity	NPC258644
0.9299	High Similarity	NPC472910
0.9299	High Similarity	NPC472911
0.9299	High Similarity	NPC96167
0.9299	High Similarity	NPC245758
0.9299	High Similarity	NPC472913
0.9299	High Similarity	NPC472914
0.9299	High Similarity	NPC222814
0.9295	High Similarity	NPC2928
0.9295	High Similarity	NPC18954
0.9295	High Similarity	NPC37392
0.929	High Similarity	NPC120537
0.929	High Similarity	NPC236637
0.929	High Similarity	NPC302950
0.929	High Similarity	NPC180234
0.929	High Similarity	NPC199100
0.929	High Similarity	NPC219582
0.9286	High Similarity	NPC61620
0.9264	High Similarity	NPC254540
0.9264	High Similarity	NPC259152
0.9264	High Similarity	NPC476405
0.9264	High Similarity	NPC211594
0.9264	High Similarity	NPC472386
0.9264	High Similarity	NPC172807
0.9264	High Similarity	NPC223375
0.9264	High Similarity	NPC261254
0.9264	High Similarity	NPC117260
0.9264	High Similarity	NPC235575
0.9264	High Similarity	NPC3583
0.9264	High Similarity	NPC267254
0.9264	High Similarity	NPC475825
0.9264	High Similarity	NPC301683
0.9259	High Similarity	NPC229687
0.9259	High Similarity	NPC471287
0.9259	High Similarity	NPC183036
0.9255	High Similarity	NPC236934
0.9255	High Similarity	NPC254306
0.9255	High Similarity	NPC5778
0.925	High Similarity	NPC94777
0.925	High Similarity	NPC475985
0.925	High Similarity	NPC29830
0.925	High Similarity	NPC270335
0.925	High Similarity	NPC191306
0.9245	High Similarity	NPC308992
0.9245	High Similarity	NPC470756
0.9241	High Similarity	NPC95936
0.9241	High Similarity	NPC250214
0.9236	High Similarity	NPC472916
0.9236	High Similarity	NPC201837
0.9231	High Similarity	NPC18727
0.9231	High Similarity	NPC292214
0.9231	High Similarity	NPC206238
0.9231	High Similarity	NPC271779
0.9231	High Similarity	NPC88645
0.9231	High Similarity	NPC167091
0.9231	High Similarity	NPC244371
0.9226	High Similarity	NPC251110
0.9226	High Similarity	NPC117579
0.9212	High Similarity	NPC257714
0.9212	High Similarity	NPC156635
0.9212	High Similarity	NPC268533
0.9207	High Similarity	NPC169977
0.9207	High Similarity	NPC204693
0.9207	High Similarity	NPC21666
0.9207	High Similarity	NPC45522
0.9207	High Similarity	NPC42773
0.9207	High Similarity	NPC101026
0.9207	High Similarity	NPC24043
0.9198	High Similarity	NPC229729
0.9198	High Similarity	NPC48640
0.9198	High Similarity	NPC471288
0.9198	High Similarity	NPC149244
0.9198	High Similarity	NPC116745
0.9198	High Similarity	NPC135345
0.9193	High Similarity	NPC22832
0.9193	High Similarity	NPC311830
0.9193	High Similarity	NPC326520
0.9187	High Similarity	NPC478199
0.9187	High Similarity	NPC81679
0.9187	High Similarity	NPC77660
0.9187	High Similarity	NPC189142
0.9182	High Similarity	NPC472624
0.9177	High Similarity	NPC223787
0.9177	High Similarity	NPC78225
0.9177	High Similarity	NPC469584
0.9177	High Similarity	NPC470402
0.9172	High Similarity	NPC213622
0.9172	High Similarity	NPC472909
0.9167	High Similarity	NPC39007
0.9167	High Similarity	NPC161277
0.9167	High Similarity	NPC212678
0.9167	High Similarity	NPC120163
0.9167	High Similarity	NPC101996
0.9167	High Similarity	NPC25270
0.9167	High Similarity	NPC57030
0.9167	High Similarity	NPC292460
0.9167	High Similarity	NPC100887
0.9167	High Similarity	NPC71334
0.9167	High Similarity	NPC35544
0.9167	High Similarity	NPC131624
0.9167	High Similarity	NPC239128
0.9167	High Similarity	NPC293183
0.9167	High Similarity	NPC187498
0.9167	High Similarity	NPC275836
0.9167	High Similarity	NPC104728
0.9167	High Similarity	NPC162313
0.9167	High Similarity	NPC188203
0.9167	High Similarity	NPC241498
0.9167	High Similarity	NPC275722
0.9167	High Similarity	NPC256283
0.9167	High Similarity	NPC156222
0.9167	High Similarity	NPC83508
0.9167	High Similarity	NPC301323
0.9167	High Similarity	NPC222830
0.9167	High Similarity	NPC198826
0.9162	High Similarity	NPC473071
0.9162	High Similarity	NPC473073
0.9161	High Similarity	NPC248102
0.9161	High Similarity	NPC62042
0.9157	High Similarity	NPC476622
0.9157	High Similarity	NPC476623
0.9157	High Similarity	NPC476620
0.9157	High Similarity	NPC476621
0.9157	High Similarity	NPC476618
0.9157	High Similarity	NPC168584
0.9157	High Similarity	NPC476619
0.9156	High Similarity	NPC321011
0.9156	High Similarity	NPC294852
0.9156	High Similarity	NPC276930

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 NPC470178 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	394
0.1-0.2	939
0.2-0.3	1967
0.3-0.4	2667
0.4-0.5	1706
0.5-0.6	932
0.6-0.7	372
0.7-0.8	133
0.8-0.85	21
0.85-0.9	17
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9437	High Similarity	NPD3818	Discontinued
0.929	High Similarity	NPD1934	Approved
0.9152	High Similarity	NPD4338	Clinical (unspecified phase)
0.9108	High Similarity	NPD2801	Approved
0.9085	High Similarity	NPD7074	Phase 3
0.9024	High Similarity	NPD7054	Approved
0.8987	High Similarity	NPD2393	Clinical (unspecified phase)
0.897	High Similarity	NPD7472	Approved
0.8875	High Similarity	NPD3882	Suspended
0.882	High Similarity	NPD4381	Clinical (unspecified phase)
0.8802	High Similarity	NPD6797	Phase 2
0.8774	High Similarity	NPD1511	Approved
0.875	High Similarity	NPD7251	Discontinued
0.8727	High Similarity	NPD6168	Clinical (unspecified phase)
0.8727	High Similarity	NPD6166	Phase 2
0.8727	High Similarity	NPD6167	Clinical (unspecified phase)
0.8712	High Similarity	NPD5494	Approved
0.8698	High Similarity	NPD7808	Phase 3
0.8662	High Similarity	NPD1512	Approved
0.8642	High Similarity	NPD4868	Clinical (unspecified phase)
0.8506	High Similarity	NPD1552	Clinical (unspecified phase)
0.8506	High Similarity	NPD1550	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD3817	Phase 2
0.8452	Intermediate Similarity	NPD1549	Phase 2
0.8421	Intermediate Similarity	NPD6559	Discontinued
0.8353	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4380	Phase 2
0.8253	Intermediate Similarity	NPD7075	Discontinued
0.8182	Intermediate Similarity	NPD1465	Phase 2
0.8182	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD1510	Phase 2
0.814	Intermediate Similarity	NPD5844	Phase 1
0.8137	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD5402	Approved
0.8107	Intermediate Similarity	NPD1247	Approved
0.8098	Intermediate Similarity	NPD1653	Approved
0.8095	Intermediate Similarity	NPD6234	Discontinued
0.8059	Intermediate Similarity	NPD6232	Discontinued
0.8023	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD943	Approved
0.8	Intermediate Similarity	NPD7199	Phase 2
0.8	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1613	Approved
0.7977	Intermediate Similarity	NPD3751	Discontinued
0.7975	Intermediate Similarity	NPD2796	Approved
0.7964	Intermediate Similarity	NPD7819	Suspended
0.7963	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6799	Approved
0.7929	Intermediate Similarity	NPD3749	Approved
0.7921	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6801	Discontinued
0.7904	Intermediate Similarity	NPD37	Approved
0.7889	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD1240	Approved
0.7882	Intermediate Similarity	NPD919	Approved
0.7874	Intermediate Similarity	NPD7228	Approved
0.787	Intermediate Similarity	NPD4966	Approved
0.787	Intermediate Similarity	NPD4965	Approved
0.787	Intermediate Similarity	NPD4967	Phase 2
0.7857	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD3787	Discontinued
0.7844	Intermediate Similarity	NPD7411	Suspended
0.7803	Intermediate Similarity	NPD3926	Phase 2
0.7802	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6959	Discontinued
0.7785	Intermediate Similarity	NPD1607	Approved
0.7784	Intermediate Similarity	NPD6599	Discontinued
0.7722	Intermediate Similarity	NPD1933	Approved
0.7722	Intermediate Similarity	NPD230	Phase 1
0.7716	Intermediate Similarity	NPD2800	Approved
0.7711	Intermediate Similarity	NPD5403	Approved
0.7697	Intermediate Similarity	NPD7685	Pre-registration
0.7697	Intermediate Similarity	NPD2533	Approved
0.7697	Intermediate Similarity	NPD5401	Approved
0.7697	Intermediate Similarity	NPD2534	Approved
0.7697	Intermediate Similarity	NPD2532	Approved
0.7697	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD3750	Approved
0.7654	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD2935	Discontinued
0.764	Intermediate Similarity	NPD1551	Phase 2
0.7611	Intermediate Similarity	NPD8313	Approved
0.7611	Intermediate Similarity	NPD8312	Approved
0.761	Intermediate Similarity	NPD447	Suspended
0.7605	Intermediate Similarity	NPD920	Approved
0.759	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.758	Intermediate Similarity	NPD3027	Phase 3
0.7557	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD6190	Approved
0.7513	Intermediate Similarity	NPD6782	Approved
0.7513	Intermediate Similarity	NPD6777	Approved
0.7513	Intermediate Similarity	NPD6776	Approved
0.7513	Intermediate Similarity	NPD6779	Approved
0.7513	Intermediate Similarity	NPD6778	Approved
0.7513	Intermediate Similarity	NPD6780	Approved
0.7513	Intermediate Similarity	NPD6781	Approved
0.7485	Intermediate Similarity	NPD2344	Approved
0.747	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD7768	Phase 2
0.7455	Intermediate Similarity	NPD4628	Phase 3
0.7421	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7240	Approved
0.7396	Intermediate Similarity	NPD7435	Discontinued
0.7394	Intermediate Similarity	NPD1243	Approved
0.7394	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3748	Approved
0.7342	Intermediate Similarity	NPD9494	Approved
0.733	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD2313	Discontinued
0.731	Intermediate Similarity	NPD7783	Phase 2
0.731	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3226	Approved
0.7306	Intermediate Similarity	NPD7697	Approved
0.7306	Intermediate Similarity	NPD7698	Approved
0.7306	Intermediate Similarity	NPD7696	Phase 3
0.7305	Intermediate Similarity	NPD2309	Approved
0.7297	Intermediate Similarity	NPD8434	Phase 2
0.7296	Intermediate Similarity	NPD8151	Discontinued
0.729	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7584	Approved
0.7278	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD7266	Discontinued
0.7268	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7870	Phase 2
0.7268	Intermediate Similarity	NPD7871	Phase 2
0.7254	Intermediate Similarity	NPD6823	Phase 2
0.7254	Intermediate Similarity	NPD5005	Approved
0.7254	Intermediate Similarity	NPD5006	Approved
0.7253	Intermediate Similarity	NPD5953	Discontinued
0.7249	Intermediate Similarity	NPD6534	Approved
0.7249	Intermediate Similarity	NPD6535	Approved
0.7247	Intermediate Similarity	NPD5711	Approved
0.7247	Intermediate Similarity	NPD5710	Approved
0.7245	Intermediate Similarity	NPD7701	Phase 2
0.7241	Intermediate Similarity	NPD8455	Phase 2
0.7238	Intermediate Similarity	NPD7286	Phase 2
0.7233	Intermediate Similarity	NPD2861	Phase 2
0.7215	Intermediate Similarity	NPD1203	Approved
0.7212	Intermediate Similarity	NPD6099	Approved
0.7212	Intermediate Similarity	NPD6100	Approved
0.7189	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1610	Phase 2
0.7172	Intermediate Similarity	NPD7874	Approved
0.7172	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2799	Discontinued
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7152	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD7801	Approved
0.7135	Intermediate Similarity	NPD7699	Phase 2
0.7135	Intermediate Similarity	NPD7700	Phase 2
0.7135	Intermediate Similarity	NPD4420	Approved
0.7134	Intermediate Similarity	NPD9269	Phase 2
0.7111	Intermediate Similarity	NPD5242	Approved
0.711	Intermediate Similarity	NPD7458	Discontinued
0.7102	Intermediate Similarity	NPD5353	Approved
0.7098	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6844	Discontinued
0.7081	Intermediate Similarity	NPD4908	Phase 1
0.7073	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1091	Approved
0.7063	Intermediate Similarity	NPD2798	Approved
0.7056	Intermediate Similarity	NPD7229	Phase 3
0.7055	Intermediate Similarity	NPD6233	Phase 2
0.7041	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7680	Approved
0.7037	Intermediate Similarity	NPD4287	Approved
0.7032	Intermediate Similarity	NPD1548	Phase 1
0.703	Intermediate Similarity	NPD6651	Approved
0.7029	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD8150	Discontinued
0.7016	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD6213	Phase 3
0.7016	Intermediate Similarity	NPD6212	Phase 3
0.6995	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD3764	Approved
0.6994	Remote Similarity	NPD6798	Discontinued
0.6994	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6674	Discontinued
0.6979	Remote Similarity	NPD4363	Phase 3
0.6979	Remote Similarity	NPD4360	Phase 2
0.6978	Remote Similarity	NPD2403	Approved
0.6975	Remote Similarity	NPD6832	Phase 2
0.697	Remote Similarity	NPD6355	Discontinued
0.6966	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6386	Approved
0.6932	Remote Similarity	NPD6385	Approved
0.6923	Remote Similarity	NPD2424	Discontinued
0.6919	Remote Similarity	NPD7390	Discontinued
0.6918	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD9717	Approved
0.6914	Remote Similarity	NPD5808	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