NPASS Compound

Structure

CID262328 OpenBabel06191716062D 30 33 0 0 1 0 0 0 0 0999 V2000 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 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 -4.3301 -2.5000 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 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 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 -1.7321 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 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 2 4 1 0 0 0 0 2 10 2 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 11 2 0 0 0 0 5 11 1 0 0 0 0 6 12 2 0 0 0 0 6 14 1 0 0 0 0 7 12 1 0 0 0 0 7 15 2 0 0 0 0 8 13 1 0 0 0 0 8 16 1 0 0 0 0 9 1 1 1 0 0 0 9 17 1 0 0 0 0 9 28 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 14 2 0 0 0 0 13 15 1 0 0 0 0 14 24 1 0 0 0 0 15 29 1 0 0 0 0 16 20 1 0 0 0 0 16 30 1 6 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 1 0 0 0 20 10 1 6 0 0 0 20 29 1 0 0 0 0 21 28 1 0 0 0 0 21 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.14
Volume:	400.84
LogP:	1.281
LogD:	1.178
LogS:	-3.178
# Rotatable Bonds:	3
TPSA:	149.07
# H-Bond Aceptor:	9
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.422
Synthetic Accessibility Score:	4.19
Fsp3:	0.429
Lipinski Rule-of-5:	Accepted
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:	-6.482
MDCK Permeability:	6.133963324828073e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.953
Human Intestinal Absorption (HIA):	0.523
20% Bioavailability (F20%):	0.209
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	91.41707611083984%
Volume Distribution (VD):	0.524
Pgp-substrate:	7.795610427856445%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.124
CYP2C9-substrate:	0.919
CYP2D6-inhibitor:	0.139
CYP2D6-substrate:	0.246
CYP3A4-inhibitor:	0.166
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	3.787
Half-life (T1/2):	0.727

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.138
AMES Toxicity:	0.513
Rat Oral Acute Toxicity:	0.156
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.94
Carcinogencity:	0.209
Eye Corrosion:	0.003
Eye Irritation:	0.457
Respiratory Toxicity:	0.12

Download Data

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

Natural Product: NPC262328

Natural Product ID:	NPC262328
*Common Name:**	Engeletin
IUPAC Name:	(2S,3R,4R,5R,6S)-2-[[(2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl]oxy]-6-methyloxane-3,4,5-triol
Synonyms:	Engeletin
Standard InCHIKey:	SQJLTDFIOMWZDE-LPKHTLNGSA-N
Standard InCHI:	InChI=1S/C21H24O9/c1-9-17(25)18(26)19(27)21(28-9)30-16-8-13-14(24)6-12(23)7-15(13)29-20(16)10-2-4-11(22)5-3-10/h2-7,9,16-27H,8H2,1H3/t9-,16+,17-,18+,19+,20+,21-/m0/s1
SMILES:	Oc1ccc(cc1)[C@H]1Oc2cc(O)cc(c2C[C@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517484
PubChem CID:	44584103
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003531] Flavonoid-3-O-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
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	bark and twigs	Tewah, Central Kalimantan, Indonesia (N 38 57.003; W 094 44.767)	1999-Oct	PMID[11858749]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17944538]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22823026]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	leaves and stems	Ha Long, Quang Ninh province, Vietnam	2014-Jul	PMID[25769817]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29792702]
NPO14105.2	Panax pseudo-ginseng var. notoginseng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14148.1	Panax pseudo - ginseng var. notoginseng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14105.2	Panax pseudo-ginseng var. notoginseng	Varieties	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14254	Kandelia candel	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14254	Kandelia candel	Species	Rhizophoraceae	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	5

Activity Type	# Activity
Individual Protein	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[489412]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[489412]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[489413]

☑ 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 NPC262328 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	385
0.1-0.2	1486
0.2-0.3	4179
0.3-0.4	10802
0.4-0.5	7747
0.5-0.6	4931
0.6-0.7	7316
0.7-0.8	4807
0.8-0.85	812
0.85-0.9	187
0.9-0.95	36
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC87777
0.9701	High Similarity	NPC139976
0.9701	High Similarity	NPC230718
0.9701	High Similarity	NPC128337
0.9701	High Similarity	NPC84207
0.9701	High Similarity	NPC49542
0.9701	High Similarity	NPC5253
0.9559	High Similarity	NPC225445
0.9556	High Similarity	NPC472353
0.9485	High Similarity	NPC116922
0.9481	High Similarity	NPC108674
0.9481	High Similarity	NPC210192
0.942	High Similarity	NPC125755
0.942	High Similarity	NPC107120
0.942	High Similarity	NPC74320
0.9416	High Similarity	NPC177597
0.9416	High Similarity	NPC168579
0.9416	High Similarity	NPC76176
0.9416	High Similarity	NPC138227
0.9416	High Similarity	NPC469313
0.9398	High Similarity	NPC238243
0.9353	High Similarity	NPC15538
0.9353	High Similarity	NPC473480
0.9348	High Similarity	NPC226722
0.9348	High Similarity	NPC277867
0.9348	High Similarity	NPC161700
0.9343	High Similarity	NPC37793
0.9328	High Similarity	NPC197723
0.9328	High Similarity	NPC3293
0.9328	High Similarity	NPC165482
0.9328	High Similarity	NPC40664
0.9328	High Similarity	NPC138350
0.9323	High Similarity	NPC130496
0.9323	High Similarity	NPC188555
0.9259	High Similarity	NPC134260
0.9248	High Similarity	NPC215037
0.9248	High Similarity	NPC115022
0.9248	High Similarity	NPC294166
0.9209	High Similarity	NPC475096
0.9173	High Similarity	NPC85799
0.9173	High Similarity	NPC303422
0.9173	High Similarity	NPC26080
0.9173	High Similarity	NPC165686
0.916	High Similarity	NPC222572
0.916	High Similarity	NPC87224
0.9149	High Similarity	NPC280945
0.9143	High Similarity	NPC99515
0.9143	High Similarity	NPC190714
0.913	High Similarity	NPC475084
0.913	High Similarity	NPC189115
0.9111	High Similarity	NPC79957
0.9098	High Similarity	NPC103799
0.9098	High Similarity	NPC121376
0.9098	High Similarity	NPC475067
0.9091	High Similarity	NPC473621
0.9078	High Similarity	NPC227902
0.9077	High Similarity	NPC278552
0.9077	High Similarity	NPC167571
0.9077	High Similarity	NPC207179
0.9065	High Similarity	NPC473044
0.9058	High Similarity	NPC257095
0.9058	High Similarity	NPC469661
0.9058	High Similarity	NPC273932
0.9058	High Similarity	NPC89686
0.9014	High Similarity	NPC175976
0.9007	High Similarity	NPC248053
0.9007	High Similarity	NPC155564
0.9007	High Similarity	NPC102280
0.9	High Similarity	NPC473045
0.9	High Similarity	NPC25292
0.8993	High Similarity	NPC469559
0.8978	High Similarity	NPC124149
0.8958	High Similarity	NPC259707
0.8947	High Similarity	NPC218003
0.8929	High Similarity	NPC252169
0.8923	High Similarity	NPC76465
0.8923	High Similarity	NPC38761
0.8921	High Similarity	NPC5155
0.8913	High Similarity	NPC212770
0.8913	High Similarity	NPC475836
0.8913	High Similarity	NPC98777
0.8905	High Similarity	NPC166180
0.8905	High Similarity	NPC203230
0.8905	High Similarity	NPC242028
0.8897	High Similarity	NPC176186
0.8897	High Similarity	NPC169404
0.8897	High Similarity	NPC53587
0.8897	High Similarity	NPC21902
0.8881	High Similarity	NPC474491
0.8881	High Similarity	NPC262606
0.8872	High Similarity	NPC274717
0.8864	High Similarity	NPC276212
0.8849	High Similarity	NPC106944
0.8846	High Similarity	NPC476142
0.8846	High Similarity	NPC36016
0.8846	High Similarity	NPC100099
0.8841	High Similarity	NPC59324
0.8841	High Similarity	NPC65530
0.8841	High Similarity	NPC211549
0.8836	High Similarity	NPC78809
0.8836	High Similarity	NPC150442
0.8832	High Similarity	NPC61946
0.8824	High Similarity	NPC92805
0.8815	High Similarity	NPC162801
0.8811	High Similarity	NPC39657
0.8811	High Similarity	NPC87950
0.8811	High Similarity	NPC471764
0.8794	High Similarity	NPC81638
0.8788	High Similarity	NPC188022
0.8788	High Similarity	NPC102540
0.8788	High Similarity	NPC17809
0.8788	High Similarity	NPC285040
0.8788	High Similarity	NPC103420
0.8786	High Similarity	NPC100482
0.8786	High Similarity	NPC277331
0.8784	High Similarity	NPC206378
0.8777	High Similarity	NPC292487
0.8769	High Similarity	NPC226712
0.8769	High Similarity	NPC190454
0.8769	High Similarity	NPC97432
0.8768	High Similarity	NPC262585
0.8768	High Similarity	NPC469383
0.8768	High Similarity	NPC306441
0.8768	High Similarity	NPC16435
0.8768	High Similarity	NPC18189
0.8768	High Similarity	NPC20829
0.8768	High Similarity	NPC164857
0.8767	High Similarity	NPC59692
0.8767	High Similarity	NPC233467
0.8759	High Similarity	NPC472710
0.8759	High Similarity	NPC48863
0.8759	High Similarity	NPC124085
0.8759	High Similarity	NPC13745
0.8759	High Similarity	NPC251981
0.8759	High Similarity	NPC472709
0.8759	High Similarity	NPC238140
0.8759	High Similarity	NPC100818
0.8759	High Similarity	NPC117048
0.875	High Similarity	NPC270751
0.8723	High Similarity	NPC472714
0.8723	High Similarity	NPC5262
0.8722	High Similarity	NPC50315
0.8722	High Similarity	NPC26879
0.8722	High Similarity	NPC283049
0.8722	High Similarity	NPC230479
0.8716	High Similarity	NPC72649
0.8716	High Similarity	NPC26195
0.8716	High Similarity	NPC39351
0.8716	High Similarity	NPC169248
0.8716	High Similarity	NPC97052
0.8712	High Similarity	NPC197351
0.8712	High Similarity	NPC246648
0.8712	High Similarity	NPC134195
0.8712	High Similarity	NPC86502
0.8712	High Similarity	NPC106914
0.8705	High Similarity	NPC470413
0.8705	High Similarity	NPC138738
0.8699	High Similarity	NPC471403
0.8696	High Similarity	NPC260898
0.8696	High Similarity	NPC112939
0.8696	High Similarity	NPC151224
0.8696	High Similarity	NPC94750
0.8696	High Similarity	NPC112246
0.8696	High Similarity	NPC474206
0.8696	High Similarity	NPC234333
0.8696	High Similarity	NPC470236
0.8696	High Similarity	NPC47398
0.8696	High Similarity	NPC121812
0.8696	High Similarity	NPC164787
0.8696	High Similarity	NPC470356
0.8692	High Similarity	NPC469412
0.8692	High Similarity	NPC198734
0.8692	High Similarity	NPC269242
0.869	High Similarity	NPC286235
0.869	High Similarity	NPC287294
0.869	High Similarity	NPC55158
0.869	High Similarity	NPC51328
0.8686	High Similarity	NPC85435
0.8686	High Similarity	NPC11060
0.8686	High Similarity	NPC49074
0.8686	High Similarity	NPC215833
0.8686	High Similarity	NPC69513
0.8686	High Similarity	NPC263064
0.8671	High Similarity	NPC85624
0.8667	High Similarity	NPC97326
0.8658	High Similarity	NPC170475
0.8657	High Similarity	NPC149796
0.8652	High Similarity	NPC178054
0.8649	High Similarity	NPC106625
0.8647	High Similarity	NPC470510
0.8647	High Similarity	NPC12308
0.8639	High Similarity	NPC44192
0.8639	High Similarity	NPC469944
0.8639	High Similarity	NPC215060
0.8639	High Similarity	NPC476352
0.8639	High Similarity	NPC226108
0.8639	High Similarity	NPC272552
0.8639	High Similarity	NPC46283
0.8639	High Similarity	NPC322899
0.8639	High Similarity	NPC134911

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 NPC262328 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	856
0.2-0.3	1740
0.3-0.4	2793
0.4-0.5	1760
0.5-0.6	1036
0.6-0.7	551
0.7-0.8	100
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8769	High Similarity	NPD1091	Approved
0.8613	High Similarity	NPD1612	Clinical (unspecified phase)
0.8613	High Similarity	NPD1613	Approved
0.8593	High Similarity	NPD4908	Phase 1
0.8477	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8346	Intermediate Similarity	NPD1610	Phase 2
0.8321	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD1548	Phase 1
0.8261	Intermediate Similarity	NPD3027	Phase 3
0.8248	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD1653	Approved
0.8176	Intermediate Similarity	NPD7074	Phase 3
0.8113	Intermediate Similarity	NPD7054	Approved
0.8063	Intermediate Similarity	NPD7472	Approved
0.8039	Intermediate Similarity	NPD8455	Phase 2
0.8012	Intermediate Similarity	NPD6797	Phase 2
0.8	Intermediate Similarity	NPD7266	Discontinued
0.7963	Intermediate Similarity	NPD7251	Discontinued
0.7914	Intermediate Similarity	NPD7808	Phase 3
0.7902	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD5124	Phase 1
0.7891	Intermediate Similarity	NPD6674	Discontinued
0.7891	Intermediate Similarity	NPD1652	Phase 2
0.7857	Intermediate Similarity	NPD2861	Phase 2
0.7853	Intermediate Similarity	NPD6559	Discontinued
0.7852	Intermediate Similarity	NPD5058	Phase 3
0.7843	Intermediate Similarity	NPD4380	Phase 2
0.7826	Intermediate Similarity	NPD7228	Approved
0.7826	Intermediate Similarity	NPD3818	Discontinued
0.7817	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD7212	Phase 2
0.78	Intermediate Similarity	NPD7213	Phase 3
0.7746	Intermediate Similarity	NPD4625	Phase 3
0.7727	Intermediate Similarity	NPD7843	Approved
0.7707	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6166	Phase 2
0.7698	Intermediate Similarity	NPD4749	Approved
0.7697	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2684	Approved
0.7681	Intermediate Similarity	NPD422	Phase 1
0.7671	Intermediate Similarity	NPD4538	Approved
0.7671	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD4536	Approved
0.7671	Intermediate Similarity	NPD7097	Phase 1
0.7658	Intermediate Similarity	NPD7075	Discontinued
0.7651	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD7447	Phase 1
0.7628	Intermediate Similarity	NPD1934	Approved
0.7628	Intermediate Similarity	NPD37	Approved
0.7625	Intermediate Similarity	NPD7199	Phase 2
0.7615	Intermediate Similarity	NPD290	Approved
0.761	Intermediate Similarity	NPD6234	Discontinued
0.7595	Intermediate Similarity	NPD4967	Phase 2
0.7595	Intermediate Similarity	NPD4966	Approved
0.7595	Intermediate Similarity	NPD4965	Approved
0.7584	Intermediate Similarity	NPD1549	Phase 2
0.758	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6798	Discontinued
0.7556	Intermediate Similarity	NPD7157	Approved
0.7532	Intermediate Similarity	NPD5403	Approved
0.7518	Intermediate Similarity	NPD8651	Approved
0.7516	Intermediate Similarity	NPD6801	Discontinued
0.75	Intermediate Similarity	NPD5588	Approved
0.75	Intermediate Similarity	NPD5960	Phase 3
0.7468	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4060	Phase 1
0.7452	Intermediate Similarity	NPD7411	Suspended
0.7452	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD7240	Approved
0.7423	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5846	Approved
0.741	Intermediate Similarity	NPD6516	Phase 2
0.7403	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5401	Approved
0.7397	Intermediate Similarity	NPD6233	Phase 2
0.7383	Intermediate Similarity	NPD7033	Discontinued
0.7368	Intermediate Similarity	NPD3750	Approved
0.7365	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3787	Discontinued
0.7361	Intermediate Similarity	NPD3018	Phase 2
0.7338	Intermediate Similarity	NPD6799	Approved
0.7312	Intermediate Similarity	NPD5402	Approved
0.7299	Intermediate Similarity	NPD6671	Approved
0.7297	Intermediate Similarity	NPD6355	Discontinued
0.729	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5125	Phase 3
0.7286	Intermediate Similarity	NPD5126	Approved
0.7273	Intermediate Similarity	NPD968	Approved
0.7255	Intermediate Similarity	NPD4628	Phase 3
0.725	Intermediate Similarity	NPD2801	Approved
0.7246	Intermediate Similarity	NPD5844	Phase 1
0.7237	Intermediate Similarity	NPD2424	Discontinued
0.7235	Intermediate Similarity	NPD8313	Approved
0.7235	Intermediate Similarity	NPD8312	Approved
0.7231	Intermediate Similarity	NPD940	Approved
0.7231	Intermediate Similarity	NPD846	Approved
0.7222	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2796	Approved
0.7206	Intermediate Similarity	NPD5535	Approved
0.7205	Intermediate Similarity	NPD3817	Phase 2
0.7203	Intermediate Similarity	NPD6582	Phase 2
0.7203	Intermediate Similarity	NPD2982	Phase 2
0.7203	Intermediate Similarity	NPD2983	Phase 2
0.7203	Intermediate Similarity	NPD6583	Phase 3
0.7203	Intermediate Similarity	NPD3685	Discontinued
0.7195	Intermediate Similarity	NPD6959	Discontinued
0.7186	Intermediate Similarity	NPD3751	Discontinued
0.7183	Intermediate Similarity	NPD3705	Approved
0.7181	Intermediate Similarity	NPD4340	Discontinued
0.7179	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6599	Discontinued
0.716	Intermediate Similarity	NPD7768	Phase 2
0.7153	Intermediate Similarity	NPD3225	Approved
0.7152	Intermediate Similarity	NPD1510	Phase 2
0.7143	Intermediate Similarity	NPD7466	Approved
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD7819	Suspended
0.7143	Intermediate Similarity	NPD4535	Phase 3
0.7133	Intermediate Similarity	NPD2981	Phase 2
0.7115	Intermediate Similarity	NPD1511	Approved
0.7114	Intermediate Similarity	NPD1240	Approved
0.7107	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6100	Approved
0.7105	Intermediate Similarity	NPD6099	Approved
0.7103	Intermediate Similarity	NPD2797	Approved
0.7092	Intermediate Similarity	NPD1357	Approved
0.7078	Intermediate Similarity	NPD5061	Approved
0.7078	Intermediate Similarity	NPD5062	Approved
0.7078	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5763	Approved
0.7059	Intermediate Similarity	NPD5762	Approved
0.7055	Intermediate Similarity	NPD3882	Suspended
0.7055	Intermediate Similarity	NPD6584	Phase 3
0.7047	Intermediate Similarity	NPD4062	Phase 3
0.7045	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4108	Discontinued
0.7039	Intermediate Similarity	NPD3748	Approved
0.7032	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3892	Phase 2
0.7032	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5494	Approved
0.7027	Intermediate Similarity	NPD7095	Approved
0.7025	Intermediate Similarity	NPD1512	Approved
0.702	Intermediate Similarity	NPD1607	Approved
0.7011	Intermediate Similarity	NPD7584	Approved
0.7006	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1551	Phase 2
0.6987	Remote Similarity	NPD2677	Approved
0.6981	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.698	Remote Similarity	NPD3268	Approved
0.6974	Remote Similarity	NPD2200	Suspended
0.6973	Remote Similarity	NPD7585	Approved
0.6971	Remote Similarity	NPD6842	Approved
0.6971	Remote Similarity	NPD6841	Approved
0.6971	Remote Similarity	NPD6843	Phase 3
0.6966	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3536	Discontinued
0.6954	Remote Similarity	NPD5735	Approved
0.694	Remote Similarity	NPD7680	Approved
0.6919	Remote Similarity	NPD7583	Approved
0.6919	Remote Similarity	NPD7685	Pre-registration
0.6914	Remote Similarity	NPD6072	Discontinued
0.6913	Remote Similarity	NPD3179	Approved
0.6913	Remote Similarity	NPD3180	Approved
0.6908	Remote Similarity	NPD3054	Approved
0.6908	Remote Similarity	NPD3052	Approved
0.6906	Remote Similarity	NPD5283	Phase 1
0.689	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2238	Phase 2
0.6884	Remote Similarity	NPD228	Approved
0.6883	Remote Similarity	NPD6032	Approved
0.6879	Remote Similarity	NPD7549	Discontinued
0.6875	Remote Similarity	NPD3496	Discontinued
0.6871	Remote Similarity	NPD4433	Discontinued
0.6871	Remote Similarity	NPD3384	Approved
0.6871	Remote Similarity	NPD3382	Approved
0.6871	Remote Similarity	NPD3383	Approved
0.6861	Remote Similarity	NPD5451	Approved
0.686	Remote Similarity	NPD7007	Discovery
0.6859	Remote Similarity	NPD5177	Phase 3
0.6857	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4675	Approved
0.6852	Remote Similarity	NPD4678	Approved
0.6846	Remote Similarity	NPD2859	Approved
0.6846	Remote Similarity	NPD2860	Approved
0.6846	Remote Similarity	NPD1008	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