NPASS Compound

Structure

CID260604 OpenBabel06191716062D 32 34 0 0 1 0 0 0 0 0999 V2000 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 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 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 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 -2.5000 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 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 12 1 0 0 0 0 4 14 2 0 0 0 0 5 6 1 0 0 0 0 5 11 2 0 0 0 0 6 13 2 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 30 1 0 0 0 0 10 13 1 0 0 0 0 11 23 1 0 0 0 0 12 16 2 0 0 0 0 12 24 1 0 0 0 0 13 31 1 0 0 0 0 14 16 1 0 0 0 0 14 29 1 0 0 0 0 15 8 1 1 0 0 0 15 17 1 0 0 0 0 15 32 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 6 0 0 0 18 19 1 0 0 0 0 18 26 1 1 0 0 0 19 21 1 0 0 0 0 19 27 1 6 0 0 0 20 28 2 0 0 0 0 20 30 1 0 0 0 0 21 31 1 1 0 0 0 21 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.13
Volume:	424.34
LogP:	0.773
LogD:	0.492
LogS:	-2.28
# Rotatable Bonds:	8
TPSA:	175.37
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.303
Synthetic Accessibility Score:	3.728
Fsp3:	0.381
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.494
MDCK Permeability:	1.1404756151023321e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.06
Human Intestinal Absorption (HIA):	0.568
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.185
Plasma Protein Binding (PPB):	87.24913024902344%
Volume Distribution (VD):	0.504
Pgp-substrate:	13.260711669921875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.238
CYP1A2-substrate:	0.075
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.089
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.526
CYP2D6-inhibitor:	0.481
CYP2D6-substrate:	0.275
CYP3A4-inhibitor:	0.053
CYP3A4-substrate:	0.068

ADMET: Excretion

Clearance (CL):	8.355
Half-life (T1/2):	0.946

ADMET: Toxicity

hERG Blockers:	0.234
Human Hepatotoxicity (H-HT):	0.031
Drug-inuced Liver Injury (DILI):	0.651
AMES Toxicity:	0.519
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.001
Skin Sensitization:	0.611
Carcinogencity:	0.513
Eye Corrosion:	0.003
Eye Irritation:	0.377
Respiratory Toxicity:	0.014

Download Data

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

Natural Product: NPC260604

Natural Product ID:	NPC260604
*Common Name:**	Curculigoside B
IUPAC Name:	[5-hydroxy-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl 2-hydroxy-6-methoxybenzoate
Synonyms:
Standard InCHIKey:	DIZYHORWVKHYCQ-PEVLUNPASA-N
Standard InCHI:	InChI=1S/C21H24O11/c1-29-14-4-2-3-12(24)16(14)20(28)30-9-10-7-11(23)5-6-13(10)31-21-19(27)18(26)17(25)15(8-22)32-21/h2-7,15,17-19,21-27H,8-9H2,1H3/t15-,17-,18+,19-,21-/m1/s1
SMILES:	COc1cccc(c1C(=O)OCc1cc(ccc1O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL403237
PubChem CID:	132567
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

*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
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20524638]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19963	Curculigo orchioides	Species	Hypoxidaceae	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
EC50	1
Others	1

Activity Type	# Activity
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	=	53.0	%	PMID[463445]
NPT2	Others	Unspecified		EC50	=	8500.0	nM	PMID[463445]

☑ 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 NPC260604 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	342
0.1-0.2	1473
0.2-0.3	3689
0.3-0.4	8533
0.4-0.5	9945
0.5-0.6	4200
0.6-0.7	5510
0.7-0.8	7191
0.8-0.85	1463
0.85-0.9	299
0.9-0.95	48
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC299435
0.9605	High Similarity	NPC217950
0.9589	High Similarity	NPC302989
0.9467	High Similarity	NPC92153
0.9467	High Similarity	NPC230439
0.9467	High Similarity	NPC299761
0.9467	High Similarity	NPC279281
0.9456	High Similarity	NPC92054
0.9456	High Similarity	NPC4958
0.9456	High Similarity	NPC140722
0.94	High Similarity	NPC215811
0.9324	High Similarity	NPC83975
0.9272	High Similarity	NPC34965
0.9272	High Similarity	NPC183536
0.9267	High Similarity	NPC93619
0.9216	High Similarity	NPC127406
0.9211	High Similarity	NPC185103
0.9182	High Similarity	NPC199079
0.9182	High Similarity	NPC210808
0.9156	High Similarity	NPC474398
0.9156	High Similarity	NPC43638
0.9156	High Similarity	NPC474441
0.9156	High Similarity	NPC476026
0.9156	High Similarity	NPC474401
0.9156	High Similarity	NPC60966
0.9125	High Similarity	NPC211594
0.9125	High Similarity	NPC472386
0.9125	High Similarity	NPC137871
0.9125	High Similarity	NPC172807
0.9125	High Similarity	NPC254540
0.9125	High Similarity	NPC9002
0.9125	High Similarity	NPC288152
0.9125	High Similarity	NPC257011
0.9114	High Similarity	NPC70441
0.9108	High Similarity	NPC127415
0.9097	High Similarity	NPC231475
0.9097	High Similarity	NPC57072
0.9091	High Similarity	NPC261866
0.9085	High Similarity	NPC106625
0.9057	High Similarity	NPC116745
0.9051	High Similarity	NPC7752
0.9048	High Similarity	NPC31081
0.9048	High Similarity	NPC245219
0.9048	High Similarity	NPC65833
0.9045	High Similarity	NPC127782
0.9045	High Similarity	NPC300537
0.9032	High Similarity	NPC177742
0.9026	High Similarity	NPC95090
0.9026	High Similarity	NPC27408
0.9026	High Similarity	NPC99233
0.902	High Similarity	NPC121001
0.902	High Similarity	NPC259767
0.902	High Similarity	NPC88484
0.902	High Similarity	NPC259182
0.9012	High Similarity	NPC477848
0.9012	High Similarity	NPC264735
0.9	High Similarity	NPC226294
0.9	High Similarity	NPC186807
0.9	High Similarity	NPC58053
0.9	High Similarity	NPC472381
0.9	High Similarity	NPC105025
0.9	High Similarity	NPC93337
0.9	High Similarity	NPC201292
0.9	High Similarity	NPC45638
0.9	High Similarity	NPC475942
0.9	High Similarity	NPC469931
0.9	High Similarity	NPC472383
0.8987	High Similarity	NPC88023
0.8987	High Similarity	NPC19709
0.8987	High Similarity	NPC243930
0.8987	High Similarity	NPC309025
0.8981	High Similarity	NPC129217
0.8981	High Similarity	NPC472859
0.8981	High Similarity	NPC259957
0.8981	High Similarity	NPC311803
0.8981	High Similarity	NPC132737
0.8981	High Similarity	NPC85707
0.8981	High Similarity	NPC25389
0.8981	High Similarity	NPC101636
0.8981	High Similarity	NPC48093
0.8981	High Similarity	NPC216496
0.8981	High Similarity	NPC159579
0.8981	High Similarity	NPC224530
0.8974	High Similarity	NPC287872
0.8974	High Similarity	NPC73511
0.8974	High Similarity	NPC74319
0.8974	High Similarity	NPC43761
0.8968	High Similarity	NPC206378
0.8961	High Similarity	NPC143851
0.8961	High Similarity	NPC29763
0.8961	High Similarity	NPC39360
0.8961	High Similarity	NPC83283
0.8961	High Similarity	NPC210003
0.8957	High Similarity	NPC198324
0.8957	High Similarity	NPC472382
0.8957	High Similarity	NPC472380
0.8957	High Similarity	NPC233994
0.8957	High Similarity	NPC472385
0.8957	High Similarity	NPC472384
0.8957	High Similarity	NPC211532
0.8944	High Similarity	NPC116864
0.8944	High Similarity	NPC44558
0.8944	High Similarity	NPC105511
0.8944	High Similarity	NPC21190
0.8944	High Similarity	NPC183357
0.8944	High Similarity	NPC22195
0.8944	High Similarity	NPC244776
0.8938	High Similarity	NPC249977
0.8938	High Similarity	NPC58716
0.8938	High Similarity	NPC146792
0.8938	High Similarity	NPC93099
0.8938	High Similarity	NPC45618
0.8931	High Similarity	NPC311830
0.8931	High Similarity	NPC22832
0.8924	High Similarity	NPC473043
0.8924	High Similarity	NPC298171
0.8924	High Similarity	NPC189142
0.8924	High Similarity	NPC77660
0.8924	High Similarity	NPC27942
0.8917	High Similarity	NPC166277
0.8917	High Similarity	NPC328093
0.8917	High Similarity	NPC119125
0.891	High Similarity	NPC44931
0.891	High Similarity	NPC65003
0.891	High Similarity	NPC473512
0.891	High Similarity	NPC108831
0.891	High Similarity	NPC182634
0.891	High Similarity	NPC161749
0.891	High Similarity	NPC156457
0.891	High Similarity	NPC6985
0.891	High Similarity	NPC129827
0.891	High Similarity	NPC313163
0.891	High Similarity	NPC197896
0.891	High Similarity	NPC23817
0.891	High Similarity	NPC258035
0.8903	High Similarity	NPC39351
0.8903	High Similarity	NPC26195
0.8903	High Similarity	NPC169248
0.8903	High Similarity	NPC97052
0.8903	High Similarity	NPC72649
0.8902	High Similarity	NPC472387
0.8896	High Similarity	NPC470454
0.8896	High Similarity	NPC237435
0.8896	High Similarity	NPC135277
0.8896	High Similarity	NPC43211
0.8896	High Similarity	NPC101191
0.8896	High Similarity	NPC199533
0.8896	High Similarity	NPC210094
0.8896	High Similarity	NPC115760
0.8896	High Similarity	NPC49344
0.8889	High Similarity	NPC307518
0.8889	High Similarity	NPC476405
0.8889	High Similarity	NPC225129
0.8889	High Similarity	NPC153755
0.8889	High Similarity	NPC190003
0.8889	High Similarity	NPC267254
0.8889	High Similarity	NPC301683
0.8889	High Similarity	NPC205076
0.8889	High Similarity	NPC175107
0.8889	High Similarity	NPC48773
0.8889	High Similarity	NPC191154
0.8889	High Similarity	NPC117260
0.8882	High Similarity	NPC170675
0.8882	High Similarity	NPC199335
0.8882	High Similarity	NPC95855
0.8882	High Similarity	NPC112755
0.8882	High Similarity	NPC471457
0.8882	High Similarity	NPC210042
0.8882	High Similarity	NPC22137
0.8875	High Similarity	NPC115674
0.8875	High Similarity	NPC5778
0.8875	High Similarity	NPC236934
0.8875	High Similarity	NPC210073
0.8868	High Similarity	NPC191306
0.8868	High Similarity	NPC94777
0.8868	High Similarity	NPC270335
0.8868	High Similarity	NPC88043
0.8868	High Similarity	NPC29830
0.8868	High Similarity	NPC284960
0.8868	High Similarity	NPC168822
0.8868	High Similarity	NPC222936
0.8868	High Similarity	NPC121703
0.8868	High Similarity	NPC475183
0.8861	High Similarity	NPC282169
0.8861	High Similarity	NPC477629
0.8861	High Similarity	NPC210961
0.8861	High Similarity	NPC472994
0.8861	High Similarity	NPC195685
0.8861	High Similarity	NPC270675
0.8861	High Similarity	NPC182045
0.8861	High Similarity	NPC477628
0.8861	High Similarity	NPC303913
0.8854	High Similarity	NPC22062
0.8854	High Similarity	NPC472459
0.8854	High Similarity	NPC160780
0.8854	High Similarity	NPC308265
0.8854	High Similarity	NPC320283
0.8854	High Similarity	NPC289811
0.8854	High Similarity	NPC111929
0.8854	High Similarity	NPC473634

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 NPC260604 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	854
0.2-0.3	1788
0.3-0.4	2643
0.4-0.5	1919
0.5-0.6	1086
0.6-0.7	396
0.7-0.8	151
0.8-0.85	21
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.891	High Similarity	NPD4381	Clinical (unspecified phase)
0.8896	High Similarity	NPD4338	Clinical (unspecified phase)
0.8782	High Similarity	NPD5402	Approved
0.8765	High Similarity	NPD7054	Approved
0.872	High Similarity	NPD6559	Discontinued
0.8712	High Similarity	NPD7074	Phase 3
0.8712	High Similarity	NPD7472	Approved
0.8659	High Similarity	NPD6797	Phase 2
0.8606	High Similarity	NPD7251	Discontinued
0.8589	High Similarity	NPD3818	Discontinued
0.8554	High Similarity	NPD7808	Phase 3
0.8537	High Similarity	NPD7804	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD5403	Approved
0.8438	Intermediate Similarity	NPD7075	Discontinued
0.8418	Intermediate Similarity	NPD1934	Approved
0.8397	Intermediate Similarity	NPD1653	Approved
0.8365	Intermediate Similarity	NPD2801	Approved
0.8365	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD5401	Approved
0.8313	Intermediate Similarity	NPD3817	Phase 2
0.8291	Intermediate Similarity	NPD4380	Phase 2
0.8278	Intermediate Similarity	NPD1551	Phase 2
0.8261	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6166	Phase 2
0.8242	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6801	Discontinued
0.8182	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD8312	Approved
0.8176	Intermediate Similarity	NPD8313	Approved
0.8161	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD6799	Approved
0.8137	Intermediate Similarity	NPD7819	Suspended
0.8105	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1549	Phase 2
0.8039	Intermediate Similarity	NPD2935	Discontinued
0.8025	Intermediate Similarity	NPD1511	Approved
0.8013	Intermediate Similarity	NPD1933	Approved
0.8012	Intermediate Similarity	NPD7411	Suspended
0.7988	Intermediate Similarity	NPD5844	Phase 1
0.7975	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD3882	Suspended
0.7925	Intermediate Similarity	NPD1512	Approved
0.7866	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6599	Discontinued
0.7838	Intermediate Similarity	NPD1203	Approved
0.7821	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7768	Phase 2
0.7808	Intermediate Similarity	NPD1091	Approved
0.7806	Intermediate Similarity	NPD2796	Approved
0.7805	Intermediate Similarity	NPD8455	Phase 2
0.78	Intermediate Similarity	NPD6832	Phase 2
0.7798	Intermediate Similarity	NPD6232	Discontinued
0.7791	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD5494	Approved
0.7778	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD447	Suspended
0.7744	Intermediate Similarity	NPD37	Approved
0.7742	Intermediate Similarity	NPD1510	Phase 2
0.7738	Intermediate Similarity	NPD6959	Discontinued
0.7738	Intermediate Similarity	NPD7199	Phase 2
0.7725	Intermediate Similarity	NPD6234	Discontinued
0.7722	Intermediate Similarity	NPD3750	Approved
0.7722	Intermediate Similarity	NPD4628	Phase 3
0.7719	Intermediate Similarity	NPD7228	Approved
0.7719	Intermediate Similarity	NPD3751	Discontinued
0.7717	Intermediate Similarity	NPD7435	Discontinued
0.7711	Intermediate Similarity	NPD4967	Phase 2
0.7711	Intermediate Similarity	NPD4966	Approved
0.7711	Intermediate Similarity	NPD4965	Approved
0.7706	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3787	Discontinued
0.7661	Intermediate Similarity	NPD7473	Discontinued
0.7654	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD6782	Approved
0.765	Intermediate Similarity	NPD6777	Approved
0.765	Intermediate Similarity	NPD6781	Approved
0.765	Intermediate Similarity	NPD6776	Approved
0.765	Intermediate Similarity	NPD6778	Approved
0.765	Intermediate Similarity	NPD6780	Approved
0.765	Intermediate Similarity	NPD6779	Approved
0.7644	Intermediate Similarity	NPD7685	Pre-registration
0.7643	Intermediate Similarity	NPD7266	Discontinued
0.764	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD9717	Approved
0.7619	Intermediate Similarity	NPD7783	Phase 2
0.7619	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1613	Approved
0.7597	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1240	Approved
0.759	Intermediate Similarity	NPD1465	Phase 2
0.7568	Intermediate Similarity	NPD6823	Phase 2
0.7561	Intermediate Similarity	NPD3226	Approved
0.7544	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2346	Discontinued
0.7532	Intermediate Similarity	NPD6233	Phase 2
0.7531	Intermediate Similarity	NPD2533	Approved
0.7531	Intermediate Similarity	NPD2534	Approved
0.7531	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2532	Approved
0.7516	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD1607	Approved
0.7474	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7874	Approved
0.7469	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD411	Approved
0.7468	Intermediate Similarity	NPD2313	Discontinued
0.7456	Intermediate Similarity	NPD3749	Approved
0.7455	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6190	Approved
0.7438	Intermediate Similarity	NPD1652	Phase 2
0.7438	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD230	Phase 1
0.7433	Intermediate Similarity	NPD7697	Approved
0.7433	Intermediate Similarity	NPD7698	Approved
0.7433	Intermediate Similarity	NPD7696	Phase 3
0.7425	Intermediate Similarity	NPD6844	Discontinued
0.7421	Intermediate Similarity	NPD8151	Discontinued
0.7407	Intermediate Similarity	NPD7584	Approved
0.7405	Intermediate Similarity	NPD3748	Approved
0.7394	Intermediate Similarity	NPD7870	Phase 2
0.7394	Intermediate Similarity	NPD7871	Phase 2
0.7377	Intermediate Similarity	NPD6534	Approved
0.7377	Intermediate Similarity	NPD6535	Approved
0.7368	Intermediate Similarity	NPD7701	Phase 2
0.7368	Intermediate Similarity	NPD2797	Approved
0.7355	Intermediate Similarity	NPD6798	Discontinued
0.7345	Intermediate Similarity	NPD7240	Approved
0.7338	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD1019	Discontinued
0.732	Intermediate Similarity	NPD2798	Approved
0.7303	Intermediate Similarity	NPD3225	Approved
0.7299	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2799	Discontinued
0.7296	Intermediate Similarity	NPD4308	Phase 3
0.729	Intermediate Similarity	NPD3027	Phase 3
0.7288	Intermediate Similarity	NPD5953	Discontinued
0.7279	Intermediate Similarity	NPD9493	Approved
0.7278	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7585	Approved
0.7273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD3496	Discontinued
0.7262	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7699	Phase 2
0.7258	Intermediate Similarity	NPD7700	Phase 2
0.7254	Intermediate Similarity	NPD7801	Approved
0.725	Intermediate Similarity	NPD6100	Approved
0.725	Intermediate Similarity	NPD6099	Approved
0.7244	Intermediate Similarity	NPD3268	Approved
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.7238	Intermediate Similarity	NPD8150	Discontinued
0.7229	Intermediate Similarity	NPD920	Approved
0.7228	Intermediate Similarity	NPD6212	Phase 3
0.7228	Intermediate Similarity	NPD6213	Phase 3
0.7228	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD4908	Phase 1
0.7225	Intermediate Similarity	NPD7583	Approved
0.7219	Intermediate Similarity	NPD422	Phase 1
0.7215	Intermediate Similarity	NPD6355	Discontinued
0.7215	Intermediate Similarity	NPD5124	Phase 1
0.7215	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD919	Approved
0.7204	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7286	Phase 2
0.7171	Intermediate Similarity	NPD1608	Approved
0.7161	Intermediate Similarity	NPD2861	Phase 2
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1247	Approved
0.7125	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD8320	Phase 1
0.712	Intermediate Similarity	NPD8319	Approved
0.7117	Intermediate Similarity	NPD1243	Approved
0.7117	Intermediate Similarity	NPD2800	Approved
0.7108	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1610	Phase 2
0.71	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1778	Approved
0.7086	Intermediate Similarity	NPD5711	Approved
0.7086	Intermediate Similarity	NPD5710	Approved
0.707	Intermediate Similarity	NPD4625	Phase 3
0.7067	Intermediate Similarity	NPD1548	Phase 1
0.7063	Intermediate Similarity	NPD6653	Approved
0.7059	Intermediate Similarity	NPD1481	Phase 2
0.7056	Intermediate Similarity	NPD7930	Approved
0.7045	Intermediate Similarity	NPD3926	Phase 2
0.7044	Intermediate Similarity	NPD4307	Phase 2
0.7044	Intermediate Similarity	NPD943	Approved
0.7044	Intermediate Similarity	NPD4060	Phase 1
0.7025	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7097	Phase 1
0.7017	Intermediate Similarity	NPD4419	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