NPASS Compound

Structure

NPC113093 OpenBabel07101718312D 28 31 0 0 1 0 0 0 0 0999 V2000 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4142 1.4142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1213 2.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6390 0.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 -0.2588 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 -4.7031 1.7778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0872 1.8625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 0.8966 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 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 0.1305 0.9914 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9259 2.4071 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3447 0.8442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 11 1 0 0 0 0 8 20 1 0 0 0 0 9 20 1 0 0 0 0 9 26 1 0 0 0 0 10 27 1 0 0 0 0 10 28 1 0 0 0 0 12 13 2 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 26 1 0 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 21 2 0 0 0 0 20 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.12
Volume:	372.117
LogP:	2.06
LogD:	2.815
LogS:	-4.679
# Rotatable Bonds:	5
TPSA:	92.68
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.831
Synthetic Accessibility Score:	3.265
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.758
MDCK Permeability:	3.2488540455233306e-05
Pgp-inhibitor:	0.563
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	94.64420318603516%
Volume Distribution (VD):	0.589
Pgp-substrate:	6.122653007507324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.733
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.906
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.778
CYP2C9-substrate:	0.889
CYP2D6-inhibitor:	0.853
CYP2D6-substrate:	0.903
CYP3A4-inhibitor:	0.961
CYP3A4-substrate:	0.894

ADMET: Excretion

Clearance (CL):	5.206
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.242
Human Hepatotoxicity (H-HT):	0.157
Drug-inuced Liver Injury (DILI):	0.343
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.065
Skin Sensitization:	0.106
Carcinogencity:	0.922
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.028

Download Data

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

Natural Product: NPC113093

Natural Product ID:	NPC113093
*Common Name:**	Urgineanin D
IUPAC Name:	(3R)-3-(1,3-benzodioxol-5-ylmethyl)-3-hydroxy-5,6,7-trimethoxy-2H-chromen-4-one
Synonyms:
Standard InCHIKey:	IXIPQIDMKALZTH-HXUWFJFHSA-N
Standard InCHI:	InChI=1S/C20H20O8/c1-23-15-7-14-16(18(25-3)17(15)24-2)19(21)20(22,9-26-14)8-11-4-5-12-13(6-11)28-10-27-12/h4-7,22H,8-10H2,1-3H3/t20-/m1/s1
SMILES:	COc1cc2c(c(c1OC)OC)C(=O)[C@@](Cc1ccc3c(c1)OCO3)(CO2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375657
PubChem CID:	71713108
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids [CHEMONTID:0002508] Homoisoflavans

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO27354	Urginea depressa	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23659371]
NPO27354	Urginea depressa	Species	Hyacinthaceae	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
IC50	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	350.0	nM	PMID[540239]
NPT1383	Cell Line	A2058	Homo sapiens	IC50	=	380.0	nM	PMID[540239]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	430.0	nM	PMID[540239]

☑ 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 NPC113093 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	398
0.1-0.2	1709
0.2-0.3	4187
0.3-0.4	9866
0.4-0.5	8358
0.5-0.6	3772
0.6-0.7	5184
0.7-0.8	5903
0.8-0.85	2418
0.85-0.9	863
0.9-0.95	37
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9487	High Similarity	NPC303255
0.9451	High Similarity	NPC156635
0.9441	High Similarity	NPC76482
0.9441	High Similarity	NPC42892
0.9427	High Similarity	NPC258644
0.9375	High Similarity	NPC470178
0.9367	High Similarity	NPC257914
0.9367	High Similarity	NPC152904
0.9367	High Similarity	NPC238405
0.9367	High Similarity	NPC104459
0.9325	High Similarity	NPC212748
0.9321	High Similarity	NPC135345
0.9313	High Similarity	NPC469575
0.9277	High Similarity	NPC67302
0.9268	High Similarity	NPC476405
0.9268	High Similarity	NPC223375
0.9268	High Similarity	NPC117260
0.9268	High Similarity	NPC475825
0.9264	High Similarity	NPC472381
0.9264	High Similarity	NPC472383
0.925	High Similarity	NPC162668
0.9236	High Similarity	NPC244371
0.9217	High Similarity	NPC472380
0.9217	High Similarity	NPC472382
0.9217	High Similarity	NPC472384
0.9212	High Similarity	NPC101026
0.9212	High Similarity	NPC169977
0.9212	High Similarity	NPC21666
0.9212	High Similarity	NPC24043
0.9212	High Similarity	NPC42773
0.9212	High Similarity	NPC45522
0.9207	High Similarity	NPC183357
0.9207	High Similarity	NPC21190
0.9207	High Similarity	NPC84265
0.9207	High Similarity	NPC72249
0.9207	High Similarity	NPC282987
0.9207	High Similarity	NPC22195
0.9207	High Similarity	NPC44558
0.9207	High Similarity	NPC105511
0.9207	High Similarity	NPC293004
0.9207	High Similarity	NPC245014
0.9202	High Similarity	NPC93099
0.9198	High Similarity	NPC88243
0.9193	High Similarity	NPC125991
0.9187	High Similarity	NPC131557
0.9172	High Similarity	NPC292460
0.9172	High Similarity	NPC134677
0.9167	High Similarity	NPC473071
0.9167	High Similarity	NPC473073
0.9162	High Similarity	NPC168584
0.9157	High Similarity	NPC108202
0.9157	High Similarity	NPC472607
0.9157	High Similarity	NPC264735
0.9157	High Similarity	NPC477848
0.9152	High Similarity	NPC267254
0.9152	High Similarity	NPC121333
0.9152	High Similarity	NPC261254
0.9152	High Similarity	NPC475155
0.9152	High Similarity	NPC205076
0.9152	High Similarity	NPC245452
0.9152	High Similarity	NPC472386
0.9152	High Similarity	NPC307518
0.9152	High Similarity	NPC48773
0.9152	High Similarity	NPC235575
0.9146	High Similarity	NPC476771
0.9146	High Similarity	NPC95855
0.9146	High Similarity	NPC58053
0.9146	High Similarity	NPC210042
0.9146	High Similarity	NPC226294
0.9146	High Similarity	NPC242395
0.9146	High Similarity	NPC475942
0.9146	High Similarity	NPC112755
0.9146	High Similarity	NPC152477
0.9146	High Similarity	NPC469931
0.9146	High Similarity	NPC45638
0.9146	High Similarity	NPC471457
0.9146	High Similarity	NPC186807
0.9146	High Similarity	NPC105025
0.9146	High Similarity	NPC170675
0.9146	High Similarity	NPC201292
0.9146	High Similarity	NPC93337
0.9141	High Similarity	NPC254306
0.9136	High Similarity	NPC41301
0.913	High Similarity	NPC182045
0.913	High Similarity	NPC260640
0.913	High Similarity	NPC295009
0.9125	High Similarity	NPC62518
0.9125	High Similarity	NPC215375
0.9119	High Similarity	NPC155063
0.9114	High Similarity	NPC478213
0.9114	High Similarity	NPC57211
0.9112	High Similarity	NPC473072
0.9112	High Similarity	NPC473883
0.9102	High Similarity	NPC211532
0.9102	High Similarity	NPC198324
0.9102	High Similarity	NPC233994
0.9102	High Similarity	NPC268533
0.9102	High Similarity	NPC472385
0.9102	High Similarity	NPC257714
0.9102	High Similarity	NPC169733
0.9096	High Similarity	NPC236191
0.9096	High Similarity	NPC239549
0.9096	High Similarity	NPC51774
0.9091	High Similarity	NPC474434
0.9091	High Similarity	NPC52353
0.9091	High Similarity	NPC224462
0.9091	High Similarity	NPC471416
0.9091	High Similarity	NPC34287
0.9091	High Similarity	NPC194483
0.9085	High Similarity	NPC58716
0.9085	High Similarity	NPC146792
0.9085	High Similarity	NPC48640
0.9085	High Similarity	NPC45618
0.9085	High Similarity	NPC149244
0.908	High Similarity	NPC165720
0.908	High Similarity	NPC224280
0.908	High Similarity	NPC234052
0.9074	High Similarity	NPC127782
0.9074	High Similarity	NPC300537
0.9074	High Similarity	NPC273021
0.9074	High Similarity	NPC478199
0.9074	High Similarity	NPC18284
0.9068	High Similarity	NPC225624
0.9068	High Similarity	NPC263449
0.9068	High Similarity	NPC110349
0.9068	High Similarity	NPC269906
0.9068	High Similarity	NPC285973
0.9062	High Similarity	NPC474836
0.9062	High Similarity	NPC67876
0.9062	High Similarity	NPC222814
0.9062	High Similarity	NPC96167
0.9062	High Similarity	NPC472913
0.9062	High Similarity	NPC224137
0.9062	High Similarity	NPC475267
0.9062	High Similarity	NPC474208
0.9062	High Similarity	NPC156057
0.9062	High Similarity	NPC189179
0.9062	High Similarity	NPC162869
0.9062	High Similarity	NPC472910
0.9062	High Similarity	NPC472911
0.9062	High Similarity	NPC48208
0.9062	High Similarity	NPC93376
0.9062	High Similarity	NPC167595
0.9062	High Similarity	NPC75215
0.9062	High Similarity	NPC227192
0.9062	High Similarity	NPC472914
0.9062	High Similarity	NPC245758
0.9057	High Similarity	NPC472909
0.9057	High Similarity	NPC37392
0.9057	High Similarity	NPC284353
0.9051	High Similarity	NPC52623
0.9051	High Similarity	NPC153008
0.9051	High Similarity	NPC68882
0.9051	High Similarity	NPC148497
0.9042	High Similarity	NPC102028
0.9042	High Similarity	NPC237435
0.9042	High Similarity	NPC210094
0.9042	High Similarity	NPC49344
0.9042	High Similarity	NPC135277
0.9042	High Similarity	NPC43211
0.9042	High Similarity	NPC101191
0.9042	High Similarity	NPC115760
0.9036	High Similarity	NPC254540
0.9036	High Similarity	NPC211594
0.9036	High Similarity	NPC476772
0.9036	High Similarity	NPC301683
0.9036	High Similarity	NPC172807
0.9036	High Similarity	NPC156977
0.903	High Similarity	NPC203050
0.903	High Similarity	NPC223747
0.903	High Similarity	NPC219904
0.903	High Similarity	NPC270578
0.903	High Similarity	NPC183036
0.903	High Similarity	NPC225434
0.903	High Similarity	NPC471287
0.903	High Similarity	NPC61791
0.903	High Similarity	NPC229687
0.903	High Similarity	NPC120099
0.903	High Similarity	NPC52382
0.9024	High Similarity	NPC255615
0.9024	High Similarity	NPC5778
0.9024	High Similarity	NPC197285
0.9024	High Similarity	NPC236934
0.9024	High Similarity	NPC173292
0.9024	High Similarity	NPC21100
0.9024	High Similarity	NPC67037
0.9018	High Similarity	NPC88023
0.9018	High Similarity	NPC88043
0.9018	High Similarity	NPC475985
0.9018	High Similarity	NPC309025
0.9018	High Similarity	NPC243930
0.9018	High Similarity	NPC94777
0.9012	High Similarity	NPC308992
0.9012	High Similarity	NPC94155
0.9012	High Similarity	NPC266314
0.9012	High Similarity	NPC34376
0.9006	High Similarity	NPC22472
0.9006	High Similarity	NPC115798
0.9006	High Similarity	NPC143828
0.9006	High Similarity	NPC18607

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 NPC113093 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	936
0.2-0.3	1873
0.3-0.4	2699
0.4-0.5	1809
0.5-0.6	928
0.6-0.7	391
0.7-0.8	123
0.8-0.85	27
0.85-0.9	13
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9085	High Similarity	NPD3818	Discontinued
0.9042	High Similarity	NPD4338	Clinical (unspecified phase)
0.8938	High Similarity	NPD3817	Phase 2
0.8882	High Similarity	NPD3882	Suspended
0.8875	High Similarity	NPD2801	Approved
0.8862	High Similarity	NPD7074	Phase 3
0.8817	High Similarity	NPD7808	Phase 3
0.8812	High Similarity	NPD1934	Approved
0.881	High Similarity	NPD6797	Phase 2
0.8802	High Similarity	NPD7054	Approved
0.8757	High Similarity	NPD7251	Discontinued
0.875	High Similarity	NPD7472	Approved
0.8735	High Similarity	NPD6166	Phase 2
0.8735	High Similarity	NPD6167	Clinical (unspecified phase)
0.8735	High Similarity	NPD6168	Clinical (unspecified phase)
0.872	High Similarity	NPD5494	Approved
0.8642	High Similarity	NPD2393	Clinical (unspecified phase)
0.8598	High Similarity	NPD4381	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD1512	Approved
0.8415	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7075	Discontinued
0.8343	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1247	Approved
0.8324	Intermediate Similarity	NPD6559	Discontinued
0.8313	Intermediate Similarity	NPD6799	Approved
0.8313	Intermediate Similarity	NPD1511	Approved
0.8313	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8253	Intermediate Similarity	NPD5402	Approved
0.8235	Intermediate Similarity	NPD3926	Phase 2
0.8225	Intermediate Similarity	NPD7199	Phase 2
0.8193	Intermediate Similarity	NPD7819	Suspended
0.8133	Intermediate Similarity	NPD6801	Discontinued
0.8121	Intermediate Similarity	NPD6599	Discontinued
0.8121	Intermediate Similarity	NPD4380	Phase 2
0.8107	Intermediate Similarity	NPD919	Approved
0.807	Intermediate Similarity	NPD6232	Discontinued
0.807	Intermediate Similarity	NPD3787	Discontinued
0.8057	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD5844	Phase 1
0.8035	Intermediate Similarity	NPD7473	Discontinued
0.8034	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1549	Phase 2
0.7989	Intermediate Similarity	NPD3751	Discontinued
0.7987	Intermediate Similarity	NPD2796	Approved
0.7975	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7411	Suspended
0.7917	Intermediate Similarity	NPD37	Approved
0.7895	Intermediate Similarity	NPD6234	Discontinued
0.7882	Intermediate Similarity	NPD4967	Phase 2
0.7882	Intermediate Similarity	NPD4965	Approved
0.7882	Intermediate Similarity	NPD4966	Approved
0.787	Intermediate Similarity	NPD1465	Phase 2
0.7831	Intermediate Similarity	NPD5403	Approved
0.7824	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD5401	Approved
0.7818	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD1510	Phase 2
0.7784	Intermediate Similarity	NPD1653	Approved
0.7736	Intermediate Similarity	NPD1933	Approved
0.7733	Intermediate Similarity	NPD3749	Approved
0.7713	Intermediate Similarity	NPD6776	Approved
0.7713	Intermediate Similarity	NPD6780	Approved
0.7713	Intermediate Similarity	NPD6781	Approved
0.7713	Intermediate Similarity	NPD6782	Approved
0.7713	Intermediate Similarity	NPD6779	Approved
0.7713	Intermediate Similarity	NPD6777	Approved
0.7713	Intermediate Similarity	NPD6778	Approved
0.7705	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD6959	Discontinued
0.7684	Intermediate Similarity	NPD7228	Approved
0.7673	Intermediate Similarity	NPD1240	Approved
0.7619	Intermediate Similarity	NPD920	Approved
0.7611	Intermediate Similarity	NPD7685	Pre-registration
0.7605	Intermediate Similarity	NPD2532	Approved
0.7605	Intermediate Similarity	NPD2534	Approved
0.7605	Intermediate Similarity	NPD2533	Approved
0.7596	Intermediate Similarity	NPD8434	Phase 2
0.7592	Intermediate Similarity	NPD7435	Discontinued
0.7578	Intermediate Similarity	NPD1607	Approved
0.7571	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD943	Approved
0.7547	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD2935	Discontinued
0.753	Intermediate Similarity	NPD6190	Approved
0.7516	Intermediate Similarity	NPD447	Suspended
0.7515	Intermediate Similarity	NPD2800	Approved
0.7514	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD7697	Approved
0.75	Intermediate Similarity	NPD7698	Approved
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7696	Phase 3
0.747	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7870	Phase 2
0.7461	Intermediate Similarity	NPD7871	Phase 2
0.7455	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD1613	Approved
0.7453	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6534	Approved
0.7447	Intermediate Similarity	NPD6535	Approved
0.7436	Intermediate Similarity	NPD7701	Phase 2
0.7432	Intermediate Similarity	NPD8313	Approved
0.7432	Intermediate Similarity	NPD8312	Approved
0.7421	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1243	Approved
0.7407	Intermediate Similarity	NPD230	Phase 1
0.7381	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD2403	Approved
0.7371	Intermediate Similarity	NPD7768	Phase 2
0.7365	Intermediate Similarity	NPD3750	Approved
0.7365	Intermediate Similarity	NPD4628	Phase 3
0.736	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7874	Approved
0.7358	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1551	Phase 2
0.733	Intermediate Similarity	NPD7699	Phase 2
0.733	Intermediate Similarity	NPD7700	Phase 2
0.7326	Intermediate Similarity	NPD3226	Approved
0.7323	Intermediate Similarity	NPD7783	Phase 2
0.7323	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7801	Approved
0.7296	Intermediate Similarity	NPD7584	Approved
0.7289	Intermediate Similarity	NPD2346	Discontinued
0.7289	Intermediate Similarity	NPD2344	Approved
0.7284	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2799	Discontinued
0.7273	Intermediate Similarity	NPD3748	Approved
0.7268	Intermediate Similarity	NPD5953	Discontinued
0.7268	Intermediate Similarity	NPD5006	Approved
0.7268	Intermediate Similarity	NPD6823	Phase 2
0.7268	Intermediate Similarity	NPD5005	Approved
0.7267	Intermediate Similarity	NPD3027	Phase 3
0.7257	Intermediate Similarity	NPD8455	Phase 2
0.7229	Intermediate Similarity	NPD6100	Approved
0.7229	Intermediate Similarity	NPD6099	Approved
0.7222	Intermediate Similarity	NPD2313	Discontinued
0.7222	Intermediate Similarity	NPD8151	Discontinued
0.7222	Intermediate Similarity	NPD6798	Discontinued
0.7222	Intermediate Similarity	NPD5242	Approved
0.7219	Intermediate Similarity	NPD8150	Discontinued
0.7205	Intermediate Similarity	NPD6832	Phase 2
0.7195	Intermediate Similarity	NPD6355	Discontinued
0.7189	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2798	Approved
0.7169	Intermediate Similarity	NPD7033	Discontinued
0.7167	Intermediate Similarity	NPD5710	Approved
0.7167	Intermediate Similarity	NPD5711	Approved
0.7167	Intermediate Similarity	NPD7229	Phase 3
0.7158	Intermediate Similarity	NPD7286	Phase 2
0.715	Intermediate Similarity	NPD4420	Approved
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7119	Intermediate Similarity	NPD5353	Approved
0.7118	Intermediate Similarity	NPD2309	Approved
0.7102	Intermediate Similarity	NPD6844	Discontinued
0.7098	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7028	Phase 2
0.7083	Intermediate Similarity	NPD7266	Discontinued
0.7059	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6651	Approved
0.7045	Intermediate Similarity	NPD6386	Approved
0.7045	Intermediate Similarity	NPD6385	Approved
0.7041	Intermediate Similarity	NPD2424	Discontinued
0.7037	Intermediate Similarity	NPD9494	Approved
0.7021	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD8319	Approved
0.702	Intermediate Similarity	NPD8320	Phase 1
0.7018	Intermediate Similarity	NPD2354	Approved
0.7011	Intermediate Similarity	NPD2163	Approved
0.7005	Intermediate Similarity	NPD7549	Discontinued
0.7005	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2654	Approved
0.7	Intermediate Similarity	NPD6674	Discontinued
0.6995	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD4908	Phase 1
0.6985	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1471	Phase 3
0.6981	Remote Similarity	NPD3705	Approved
0.6964	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7095	Approved
0.695	Remote Similarity	NPD7583	Approved
0.6949	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6213	Phase 3
0.6943	Remote Similarity	NPD6212	Phase 3
0.6939	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1608	Approved
0.6936	Remote Similarity	NPD7390	Discontinued
0.6933	Remote Similarity	NPD3018	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