NPASS Compound

Structure

CID325346 OpenBabel06191716182D 36 37 0 0 1 0 0 0 0 0999 V2000 -2.0655 2.0655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8730 3.2580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7459 -3.8947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5891 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8996 0.3726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4365 1.6290 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9026 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6885 0.6885 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0594 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0594 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1250 2.3175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7459 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0594 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.0594 1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9026 0.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 0.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 -2.4342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 28 1 0 0 0 0 8 10 1 0 0 0 0 8 14 2 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 28 1 0 0 0 0 11 36 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 2 0 0 0 0 13 21 1 0 0 0 0 16 22 1 0 0 0 0 16 29 2 0 0 0 0 17 23 1 0 0 0 0 17 30 2 0 0 0 0 18 21 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 19 26 2 0 0 0 0 20 22 1 0 0 0 0 20 31 1 0 0 0 0 21 36 1 0 0 0 0 22 24 2 0 0 0 0 23 25 1 0 0 0 0 23 27 2 0 0 0 0 24 32 1 0 0 0 0 25 33 2 0 0 0 0 26 28 1 0 0 0 0 26 34 1 0 0 0 0 27 28 1 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.23
Volume:	519.688
LogP:	5.001
LogD:	0.989
LogS:	-2.548
# Rotatable Bonds:	9
TPSA:	135.04
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.295
Synthetic Accessibility Score:	4.495
Fsp3:	0.464
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.721
MDCK Permeability:	1.2806809536414221e-05
Pgp-inhibitor:	0.782
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.082
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	96.49239349365234%
Volume Distribution (VD):	1.278
Pgp-substrate:	2.5174269676208496%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.422
CYP2C19-inhibitor:	0.196
CYP2C19-substrate:	0.59
CYP2C9-inhibitor:	0.398
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.139
CYP2D6-substrate:	0.089
CYP3A4-inhibitor:	0.738
CYP3A4-substrate:	0.706

ADMET: Excretion

Clearance (CL):	17.698
Half-life (T1/2):	0.145

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.436
Drug-inuced Liver Injury (DILI):	0.923
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.981
Maximum Recommended Daily Dose:	0.029
Skin Sensitization:	0.065
Carcinogencity:	0.32
Eye Corrosion:	0.021
Eye Irritation:	0.371
Respiratory Toxicity:	0.829

Download Data

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

Natural Product: NPC325346

Natural Product ID:	NPC325346
*Common Name:**	Drummondin E
IUPAC Name:	n.a.
Synonyms:	Drummondin E
Standard InCHIKey:	LACABBHUBUCHAU-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H34O8/c1-14(2)8-10-28(7)26(34)19(25(33)23(17(6)30)27(28)35)12-18-21(36-11-9-15(3)4)13-20(31)22(16(5)29)24(18)32/h8-9,13,31-32,34-35H,10-12H2,1-7H3
SMILES:	CC(=CCOc1cc(O)c(c(c1CC1=C(O)C(C(=C(C1=O)C(=O)C)O)(C)CC=C(C)C)O)C(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL483236
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*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
NPO28558	Hypericum drummondii	Species	Hypericaceae	Eukaryota	n.a.	root	n.a.	PMID[1800634]
NPO28558	Hypericum drummondii	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2746258]
NPO28558	Hypericum drummondii	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28558	Hypericum drummondii	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28558	Hypericum drummondii	Species	Hypericaceae	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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.39	ug.mL-1	PMID[518784]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.2	ug.mL-1	PMID[518784]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	3.12	ug.mL-1	PMID[518784]

☑ 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 NPC325346 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	367
0.1-0.2	1488
0.2-0.3	3781
0.3-0.4	9262
0.4-0.5	9603
0.5-0.6	3901
0.6-0.7	6466
0.7-0.8	5146
0.8-0.85	1671
0.85-0.9	798
0.9-0.95	210
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC477055
0.9706	High Similarity	NPC477056
0.9424	High Similarity	NPC471587
0.9416	High Similarity	NPC156910
0.9416	High Similarity	NPC174999
0.9357	High Similarity	NPC316911
0.9357	High Similarity	NPC316560
0.9353	High Similarity	NPC23257
0.9353	High Similarity	NPC139554
0.9343	High Similarity	NPC60667
0.9291	High Similarity	NPC321148
0.9291	High Similarity	NPC321629
0.9291	High Similarity	NPC323884
0.9291	High Similarity	NPC326193
0.9281	High Similarity	NPC131130
0.927	High Similarity	NPC236974
0.927	High Similarity	NPC125920
0.927	High Similarity	NPC144027
0.9265	High Similarity	NPC203817
0.9225	High Similarity	NPC185276
0.922	High Similarity	NPC96408
0.922	High Similarity	NPC156190
0.922	High Similarity	NPC279650
0.922	High Similarity	NPC258630
0.922	High Similarity	NPC17170
0.922	High Similarity	NPC166689
0.9197	High Similarity	NPC108113
0.9197	High Similarity	NPC93756
0.9167	High Similarity	NPC10990
0.9167	High Similarity	NPC300988
0.9161	High Similarity	NPC197252
0.9161	High Similarity	NPC236766
0.9161	High Similarity	NPC235217
0.9161	High Similarity	NPC473014
0.9155	High Similarity	NPC37496
0.9155	High Similarity	NPC78
0.9155	High Similarity	NPC166482
0.9155	High Similarity	NPC306829
0.9155	High Similarity	NPC76372
0.9155	High Similarity	NPC76338
0.9155	High Similarity	NPC177354
0.9155	High Similarity	NPC166934
0.9155	High Similarity	NPC125855
0.9155	High Similarity	NPC167624
0.9155	High Similarity	NPC194432
0.9155	High Similarity	NPC1089
0.9155	High Similarity	NPC107572
0.9155	High Similarity	NPC220998
0.9155	High Similarity	NPC40833
0.9155	High Similarity	NPC328164
0.9155	High Similarity	NPC32739
0.9155	High Similarity	NPC64915
0.9155	High Similarity	NPC227579
0.9155	High Similarity	NPC10937
0.9155	High Similarity	NPC265040
0.9155	High Similarity	NPC324436
0.9155	High Similarity	NPC223500
0.9155	High Similarity	NPC296917
0.9155	High Similarity	NPC148757
0.9155	High Similarity	NPC182852
0.9155	High Similarity	NPC66515
0.9155	High Similarity	NPC161506
0.9155	High Similarity	NPC324134
0.9155	High Similarity	NPC228504
0.9149	High Similarity	NPC159275
0.9149	High Similarity	NPC16455
0.9149	High Similarity	NPC477272
0.9149	High Similarity	NPC241100
0.9149	High Similarity	NPC307990
0.9143	High Similarity	NPC54820
0.9143	High Similarity	NPC470669
0.9143	High Similarity	NPC474487
0.9143	High Similarity	NPC180501
0.9143	High Similarity	NPC474504
0.9143	High Similarity	NPC470671
0.9143	High Similarity	NPC470672
0.9143	High Similarity	NPC470668
0.9143	High Similarity	NPC124269
0.9143	High Similarity	NPC268178
0.9137	High Similarity	NPC470397
0.9137	High Similarity	NPC470398
0.9137	High Similarity	NPC187826
0.9124	High Similarity	NPC10971
0.911	High Similarity	NPC188403
0.9097	High Similarity	NPC285630
0.9097	High Similarity	NPC127059
0.9091	High Similarity	NPC473812
0.9091	High Similarity	NPC478086
0.9091	High Similarity	NPC175504
0.9091	High Similarity	NPC223812
0.9091	High Similarity	NPC149026
0.9091	High Similarity	NPC39329
0.9091	High Similarity	NPC214166
0.9091	High Similarity	NPC310130
0.9091	High Similarity	NPC91560
0.9091	High Similarity	NPC11700
0.9091	High Similarity	NPC125894
0.9091	High Similarity	NPC81697
0.9091	High Similarity	NPC77794
0.9091	High Similarity	NPC85162
0.9091	High Similarity	NPC143896
0.9091	High Similarity	NPC107177
0.9091	High Similarity	NPC257097
0.9091	High Similarity	NPC169591
0.9091	High Similarity	NPC68104
0.9091	High Similarity	NPC278249
0.9091	High Similarity	NPC75049
0.9091	High Similarity	NPC473813
0.9091	High Similarity	NPC164980
0.9091	High Similarity	NPC221432
0.9091	High Similarity	NPC150408
0.9091	High Similarity	NPC316816
0.9085	High Similarity	NPC324386
0.9085	High Similarity	NPC312391
0.9085	High Similarity	NPC110969
0.9085	High Similarity	NPC248372
0.9085	High Similarity	NPC282300
0.9085	High Similarity	NPC3188
0.9085	High Similarity	NPC4743
0.9085	High Similarity	NPC110038
0.9085	High Similarity	NPC213322
0.9078	High Similarity	NPC220062
0.9078	High Similarity	NPC18260
0.9078	High Similarity	NPC270913
0.9078	High Similarity	NPC53181
0.9078	High Similarity	NPC301217
0.9078	High Similarity	NPC303633
0.9078	High Similarity	NPC471697
0.9078	High Similarity	NPC55018
0.9078	High Similarity	NPC217186
0.9078	High Similarity	NPC140890
0.9078	High Similarity	NPC96565
0.9078	High Similarity	NPC216978
0.9078	High Similarity	NPC78913
0.9071	High Similarity	NPC188879
0.9065	High Similarity	NPC101752
0.9065	High Similarity	NPC13575
0.9058	High Similarity	NPC16197
0.9058	High Similarity	NPC223457
0.9051	High Similarity	NPC31872
0.9051	High Similarity	NPC473584
0.9051	High Similarity	NPC475589
0.9044	High Similarity	NPC84772
0.9041	High Similarity	NPC471114
0.9034	High Similarity	NPC283234
0.9034	High Similarity	NPC91902
0.9028	High Similarity	NPC131568
0.9028	High Similarity	NPC224714
0.9028	High Similarity	NPC319752
0.9028	High Similarity	NPC473015
0.9028	High Similarity	NPC271288
0.9028	High Similarity	NPC209040
0.9028	High Similarity	NPC470890
0.9028	High Similarity	NPC473013
0.9028	High Similarity	NPC472447
0.9028	High Similarity	NPC131579
0.9028	High Similarity	NPC472446
0.9021	High Similarity	NPC226636
0.9021	High Similarity	NPC204469
0.9021	High Similarity	NPC11561
0.9014	High Similarity	NPC270883
0.9014	High Similarity	NPC150522
0.9014	High Similarity	NPC164697
0.9014	High Similarity	NPC284550
0.9014	High Similarity	NPC261227
0.9014	High Similarity	NPC289660
0.9014	High Similarity	NPC11056
0.9014	High Similarity	NPC82920
0.9014	High Similarity	NPC110228
0.9014	High Similarity	NPC69769
0.9014	High Similarity	NPC76445
0.9014	High Similarity	NPC129853
0.9014	High Similarity	NPC188243
0.9014	High Similarity	NPC6407
0.9014	High Similarity	NPC172986
0.9007	High Similarity	NPC470399
0.9007	High Similarity	NPC201395
0.9	High Similarity	NPC168105
0.9	High Similarity	NPC12165
0.9	High Similarity	NPC1486
0.9	High Similarity	NPC150399
0.9	High Similarity	NPC98115
0.9	High Similarity	NPC186838
0.9	High Similarity	NPC249606
0.9	High Similarity	NPC477243
0.9	High Similarity	NPC477244
0.9	High Similarity	NPC25287
0.9	High Similarity	NPC121243
0.9	High Similarity	NPC66349
0.9	High Similarity	NPC240593
0.9	High Similarity	NPC274109
0.9	High Similarity	NPC240147
0.9	High Similarity	NPC41461
0.9	High Similarity	NPC477242
0.8993	High Similarity	NPC103842
0.8993	High Similarity	NPC164136
0.8986	High Similarity	NPC25937
0.8986	High Similarity	NPC215875
0.8986	High Similarity	NPC15834
0.8986	High Similarity	NPC470353

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 NPC325346 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	977
0.2-0.3	1720
0.3-0.4	2637
0.4-0.5	1869
0.5-0.6	1074
0.6-0.7	402
0.7-0.8	110
0.8-0.85	25
0.85-0.9	10
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9197	High Similarity	NPD6651	Approved
0.8944	High Similarity	NPD2800	Approved
0.8897	High Similarity	NPD4378	Clinical (unspecified phase)
0.8803	High Similarity	NPD1550	Clinical (unspecified phase)
0.8803	High Similarity	NPD1552	Clinical (unspecified phase)
0.8767	High Similarity	NPD7410	Clinical (unspecified phase)
0.8742	High Similarity	NPD8443	Clinical (unspecified phase)
0.8741	High Similarity	NPD1549	Phase 2
0.8667	High Similarity	NPD7411	Suspended
0.8643	High Similarity	NPD1240	Approved
0.8627	High Similarity	NPD7075	Discontinued
0.8553	High Similarity	NPD7819	Suspended
0.8553	High Similarity	NPD2393	Clinical (unspecified phase)
0.8531	High Similarity	NPD1510	Phase 2
0.8521	High Similarity	NPD1607	Approved
0.8477	Intermediate Similarity	NPD4380	Phase 2
0.8472	Intermediate Similarity	NPD2796	Approved
0.8431	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8366	Intermediate Similarity	NPD6801	Discontinued
0.8355	Intermediate Similarity	NPD6599	Discontinued
0.8322	Intermediate Similarity	NPD6799	Approved
0.8247	Intermediate Similarity	NPD1934	Approved
0.8239	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6959	Discontinued
0.8205	Intermediate Similarity	NPD7768	Phase 2
0.8187	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8153	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8148	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD2532	Approved
0.8146	Intermediate Similarity	NPD2534	Approved
0.8146	Intermediate Similarity	NPD2533	Approved
0.8089	Intermediate Similarity	NPD3882	Suspended
0.8079	Intermediate Similarity	NPD1511	Approved
0.8077	Intermediate Similarity	NPD2801	Approved
0.8054	Intermediate Similarity	NPD1243	Approved
0.8	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3750	Approved
0.7974	Intermediate Similarity	NPD1512	Approved
0.7973	Intermediate Similarity	NPD1551	Phase 2
0.7973	Intermediate Similarity	NPD6100	Approved
0.7973	Intermediate Similarity	NPD6099	Approved
0.7963	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD6166	Phase 2
0.7939	Intermediate Similarity	NPD5953	Discontinued
0.7927	Intermediate Similarity	NPD7286	Phase 2
0.7922	Intermediate Similarity	NPD920	Approved
0.7911	Intermediate Similarity	NPD3817	Phase 2
0.7895	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7074	Phase 3
0.7852	Intermediate Similarity	NPD2935	Discontinued
0.7847	Intermediate Similarity	NPD6832	Phase 2
0.7818	Intermediate Similarity	NPD7054	Approved
0.7806	Intermediate Similarity	NPD5403	Approved
0.7805	Intermediate Similarity	NPD7473	Discontinued
0.78	Intermediate Similarity	NPD2344	Approved
0.7792	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD2799	Discontinued
0.7771	Intermediate Similarity	NPD7472	Approved
0.7763	Intermediate Similarity	NPD4628	Phase 3
0.7758	Intermediate Similarity	NPD3818	Discontinued
0.775	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6232	Discontinued
0.7716	Intermediate Similarity	NPD5494	Approved
0.7702	Intermediate Similarity	NPD3749	Approved
0.7697	Intermediate Similarity	NPD2654	Approved
0.7679	Intermediate Similarity	NPD7251	Discontinued
0.7679	Intermediate Similarity	NPD6559	Discontinued
0.7677	Intermediate Similarity	NPD5401	Approved
0.7676	Intermediate Similarity	NPD9717	Approved
0.7667	Intermediate Similarity	NPD3748	Approved
0.7639	Intermediate Similarity	NPD1203	Approved
0.7633	Intermediate Similarity	NPD7808	Phase 3
0.7619	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6797	Phase 2
0.7619	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD422	Phase 1
0.7597	Intermediate Similarity	NPD2309	Approved
0.7574	Intermediate Similarity	NPD6104	Discontinued
0.7552	Intermediate Similarity	NPD3972	Approved
0.755	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD919	Approved
0.7515	Intermediate Similarity	NPD5710	Approved
0.7515	Intermediate Similarity	NPD5711	Approved
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD7390	Discontinued
0.7484	Intermediate Similarity	NPD3226	Approved
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4908	Phase 1
0.747	Intermediate Similarity	NPD3926	Phase 2
0.7469	Intermediate Similarity	NPD5402	Approved
0.7467	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5124	Phase 1
0.7464	Intermediate Similarity	NPD1241	Discontinued
0.7456	Intermediate Similarity	NPD1729	Discontinued
0.7455	Intermediate Similarity	NPD1247	Approved
0.7447	Intermediate Similarity	NPD1548	Phase 1
0.7447	Intermediate Similarity	NPD9545	Approved
0.7434	Intermediate Similarity	NPD7033	Discontinued
0.7427	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD943	Approved
0.7396	Intermediate Similarity	NPD5844	Phase 1
0.7394	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD3268	Approved
0.7375	Intermediate Similarity	NPD7458	Discontinued
0.7361	Intermediate Similarity	NPD1610	Phase 2
0.7351	Intermediate Similarity	NPD230	Phase 1
0.7347	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD9493	Approved
0.7303	Intermediate Similarity	NPD4360	Phase 2
0.7303	Intermediate Similarity	NPD4363	Phase 3
0.7279	Intermediate Similarity	NPD2797	Approved
0.7267	Intermediate Similarity	NPD1296	Phase 2
0.7263	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4361	Phase 2
0.726	Intermediate Similarity	NPD4749	Approved
0.7233	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1019	Discontinued
0.723	Intermediate Similarity	NPD2798	Approved
0.7226	Intermediate Similarity	NPD2346	Discontinued
0.7219	Intermediate Similarity	NPD2403	Approved
0.7211	Intermediate Similarity	NPD8651	Approved
0.7198	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1465	Phase 2
0.7159	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD411	Approved
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD447	Suspended
0.7124	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD1778	Approved
0.7101	Intermediate Similarity	NPD7229	Phase 3
0.7097	Intermediate Similarity	NPD4308	Phase 3
0.7095	Intermediate Similarity	NPD3225	Approved
0.7095	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5760	Phase 2
0.7091	Intermediate Similarity	NPD5761	Phase 2
0.7089	Intermediate Similarity	NPD7003	Approved
0.7086	Intermediate Similarity	NPD4625	Phase 3
0.7075	Intermediate Similarity	NPD1608	Approved
0.707	Intermediate Similarity	NPD2424	Discontinued
0.7069	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7584	Approved
0.7059	Intermediate Similarity	NPD3140	Approved
0.7059	Intermediate Similarity	NPD3142	Approved
0.7048	Intermediate Similarity	NPD2296	Approved
0.7048	Intermediate Similarity	NPD4288	Approved
0.7047	Intermediate Similarity	NPD3267	Approved
0.7047	Intermediate Similarity	NPD3266	Approved
0.7039	Intermediate Similarity	NPD6798	Discontinued
0.7018	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1933	Approved
0.7013	Intermediate Similarity	NPD6355	Discontinued
0.7006	Intermediate Similarity	NPD6002	Phase 3
0.7006	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1471	Phase 3
0.7006	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6005	Phase 3
0.7006	Intermediate Similarity	NPD6004	Phase 3
0.6993	Remote Similarity	NPD7157	Approved
0.6989	Remote Similarity	NPD8312	Approved
0.6989	Remote Similarity	NPD8313	Approved
0.6987	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5890	Approved
0.697	Remote Similarity	NPD5889	Approved
0.6954	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1613	Approved
0.6943	Remote Similarity	NPD4477	Approved
0.6943	Remote Similarity	NPD4476	Approved
0.6941	Remote Similarity	NPD7199	Phase 2
0.6933	Remote Similarity	NPD1164	Approved
0.6928	Remote Similarity	NPD6279	Approved
0.6928	Remote Similarity	NPD6280	Approved
0.6923	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1652	Phase 2
0.6914	Remote Similarity	NPD4662	Approved
0.6914	Remote Similarity	NPD4661	Approved
0.6908	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7843	Approved
0.6892	Remote Similarity	NPD1201	Approved
0.6886	Remote Similarity	NPD8455	Phase 2
0.6871	Remote Similarity	NPD6273	Approved
0.6871	Remote Similarity	NPD5049	Phase 3
0.6871	Remote Similarity	NPD17	Approved
0.6867	Remote Similarity	NPD1876	Approved
0.6867	Remote Similarity	NPD6696	Suspended
0.6863	Remote Similarity	NPD3027	Phase 3
0.686	Remote Similarity	NPD7184	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