NPASS Compound

Structure

NPC268178 OpenBabel07101719252D 32 34 0 0 0 0 0 0 0 0999 V2000 2.5238 -1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4128 1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8127 0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3270 -0.3556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4033 -0.3556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3747 -0.3556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2064 2.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6826 -0.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5715 2.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8413 1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5238 1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0477 1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6826 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7303 1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6826 1.9429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5238 0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8890 2.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8413 0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0477 0.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7303 0.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8890 0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8413 -1.4571 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5715 3.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6826 2.9143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3651 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8890 3.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2064 0.4857 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5715 0.4857 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 10 1 0 0 0 0 2 11 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 7 8 2 0 0 0 0 7 12 1 0 0 0 0 8 23 1 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 25 2 0 0 0 0 11 16 1 0 0 0 0 11 26 2 0 0 0 0 12 17 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 18 2 0 0 0 0 14 19 1 0 0 0 0 14 21 2 0 0 0 0 15 18 1 0 0 0 0 15 20 2 0 0 0 0 16 19 1 0 0 0 0 16 22 2 0 0 0 0 17 27 1 0 0 0 0 18 28 1 0 0 0 0 19 29 2 0 0 0 0 20 32 1 0 0 0 0 21 24 1 0 0 0 0 21 30 1 0 0 0 0 22 24 1 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.16
Volume:	444.584
LogP:	3.278
LogD:	0.444
LogS:	-2.177
# Rotatable Bonds:	4
TPSA:	135.04
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.537
Synthetic Accessibility Score:	4.343
Fsp3:	0.458
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:	-4.709
MDCK Permeability:	2.58740947174374e-05
Pgp-inhibitor:	0.217
Pgp-substrate:	0.854
Human Intestinal Absorption (HIA):	0.229
20% Bioavailability (F20%):	0.038
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	93.86055755615234%
Volume Distribution (VD):	0.487
Pgp-substrate:	2.8410370349884033%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.589
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.656
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.932
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.762
CYP3A4-substrate:	0.777

ADMET: Excretion

Clearance (CL):	6.627
Half-life (T1/2):	0.228

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.124
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.934
Maximum Recommended Daily Dose:	0.054
Skin Sensitization:	0.088
Carcinogencity:	0.511
Eye Corrosion:	0.008
Eye Irritation:	0.416
Respiratory Toxicity:	0.717

Download Data

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

Natural Product: NPC268178

Natural Product ID:	NPC268178
*Common Name:**	Drummondin C
IUPAC Name:	n.a.
Synonyms:	Drummondin C
Standard InCHIKey:	CBIZWUUGEINUSE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C24H26O8/c1-10(25)15-18(28)13(17(27)12-7-8-23(3,4)32-20(12)15)9-14-19(29)16(11(2)26)22(31)24(5,6)21(14)30/h7-8,27-28,30-31H,9H2,1-6H3
SMILES:	CC(=O)C1=C(O)C(C(=C(C1=O)Cc1c(O)c2C=CC(Oc2c(c1O)C(=O)C)(C)C)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484443
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
ED50	6
MIC	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	4
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.8	ug ml-1	PMID[505864]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	8.6	ug ml-1	PMID[505864]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.12	ug.mL-1	PMID[505864]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.78	ug.mL-1	PMID[505864]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	6.25	ug.mL-1	PMID[505864]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[505864]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[505864]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	5.1	ug ml-1	PMID[505864]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	11.0	ug ml-1	PMID[505864]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	8.7	ug ml-1	PMID[505864]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	12.0	ug ml-1	PMID[505864]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3120.0	nM	PMID[505865]

☑ 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 NPC268178 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	376
0.1-0.2	1604
0.2-0.3	4192
0.3-0.4	10624
0.4-0.5	8466
0.5-0.6	4672
0.6-0.7	6374
0.7-0.8	4692
0.8-0.85	1114
0.85-0.9	515
0.9-0.95	57
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC180501
1.0	High Similarity	NPC54820
0.9778	High Similarity	NPC316911
0.9778	High Similarity	NPC316560
0.9706	High Similarity	NPC321148
0.9706	High Similarity	NPC326193
0.9706	High Similarity	NPC323884
0.9706	High Similarity	NPC321629
0.9556	High Similarity	NPC254168
0.9556	High Similarity	NPC272844
0.9556	High Similarity	NPC248995
0.9485	High Similarity	NPC240305
0.9478	High Similarity	NPC101752
0.9343	High Similarity	NPC472343
0.9275	High Similarity	NPC221173
0.927	High Similarity	NPC470668
0.927	High Similarity	NPC470669
0.9209	High Similarity	NPC118840
0.9209	High Similarity	NPC64908
0.9209	High Similarity	NPC147688
0.9209	High Similarity	NPC470555
0.9209	High Similarity	NPC205006
0.9209	High Similarity	NPC156590
0.9203	High Similarity	NPC55018
0.9203	High Similarity	NPC220062
0.9203	High Similarity	NPC301217
0.9203	High Similarity	NPC303633
0.9203	High Similarity	NPC53181
0.9203	High Similarity	NPC23257
0.9203	High Similarity	NPC96565
0.9203	High Similarity	NPC270913
0.9203	High Similarity	NPC217186
0.9203	High Similarity	NPC216978
0.9149	High Similarity	NPC257236
0.9149	High Similarity	NPC71184
0.9149	High Similarity	NPC278175
0.9149	High Similarity	NPC206212
0.9143	High Similarity	NPC217083
0.9143	High Similarity	NPC325346
0.9143	High Similarity	NPC299080
0.9143	High Similarity	NPC11561
0.9143	High Similarity	NPC78803
0.9143	High Similarity	NPC59739
0.9143	High Similarity	NPC62840
0.9143	High Similarity	NPC293852
0.9143	High Similarity	NPC214236
0.9143	High Similarity	NPC226636
0.9137	High Similarity	NPC475680
0.9137	High Similarity	NPC471587
0.9137	High Similarity	NPC289660
0.9137	High Similarity	NPC270883
0.9137	High Similarity	NPC82920
0.9137	High Similarity	NPC241100
0.9137	High Similarity	NPC159275
0.9137	High Similarity	NPC172986
0.9137	High Similarity	NPC305355
0.9137	High Similarity	NPC150522
0.9137	High Similarity	NPC164697
0.9137	High Similarity	NPC235239
0.9137	High Similarity	NPC261227
0.913	High Similarity	NPC131130
0.913	High Similarity	NPC201395
0.9124	High Similarity	NPC174999
0.9124	High Similarity	NPC470982
0.9124	High Similarity	NPC470983
0.9085	High Similarity	NPC329678
0.9078	High Similarity	NPC11700
0.9078	High Similarity	NPC219915
0.9078	High Similarity	NPC38219
0.9071	High Similarity	NPC103362
0.9071	High Similarity	NPC110969
0.9071	High Similarity	NPC111201
0.9071	High Similarity	NPC282300
0.9065	High Similarity	NPC78913
0.9065	High Similarity	NPC473076
0.9065	High Similarity	NPC18260
0.9058	High Similarity	NPC474624
0.9058	High Similarity	NPC138047
0.9058	High Similarity	NPC131782
0.9051	High Similarity	NPC151113
0.9044	High Similarity	NPC93756
0.9044	High Similarity	NPC108113
0.9014	High Similarity	NPC234629
0.9014	High Similarity	NPC469953
0.9014	High Similarity	NPC311741
0.9007	High Similarity	NPC36181
0.9007	High Similarity	NPC144499
0.9007	High Similarity	NPC200694
0.9007	High Similarity	NPC204469
0.9	High Similarity	NPC69769
0.8993	High Similarity	NPC199458
0.8993	High Similarity	NPC219584
0.8993	High Similarity	NPC474504
0.8993	High Similarity	NPC477056
0.8993	High Similarity	NPC470083
0.8993	High Similarity	NPC470672
0.8993	High Similarity	NPC474487
0.8993	High Similarity	NPC477055
0.8993	High Similarity	NPC470671
0.8993	High Similarity	NPC183639
0.8986	High Similarity	NPC13408
0.8978	High Similarity	NPC125920
0.8971	High Similarity	NPC215875
0.8971	High Similarity	NPC15834
0.8971	High Similarity	NPC10971
0.8963	High Similarity	NPC250057
0.8951	High Similarity	NPC214774
0.8951	High Similarity	NPC57470
0.8951	High Similarity	NPC301276
0.8951	High Similarity	NPC176229
0.8951	High Similarity	NPC475052
0.8951	High Similarity	NPC312973
0.8951	High Similarity	NPC111786
0.8951	High Similarity	NPC54577
0.8951	High Similarity	NPC20488
0.8951	High Similarity	NPC82534
0.8951	High Similarity	NPC88964
0.8951	High Similarity	NPC470647
0.8951	High Similarity	NPC246948
0.8951	High Similarity	NPC195621
0.8951	High Similarity	NPC83357
0.8951	High Similarity	NPC267375
0.8951	High Similarity	NPC220418
0.8951	High Similarity	NPC142405
0.8951	High Similarity	NPC124729
0.8951	High Similarity	NPC67805
0.8944	High Similarity	NPC478086
0.8944	High Similarity	NPC24821
0.8944	High Similarity	NPC5990
0.8944	High Similarity	NPC470296
0.8944	High Similarity	NPC293053
0.8944	High Similarity	NPC188632
0.8944	High Similarity	NPC18585
0.8944	High Similarity	NPC214166
0.8944	High Similarity	NPC87609
0.8944	High Similarity	NPC316816
0.8944	High Similarity	NPC9117
0.8944	High Similarity	NPC212932
0.8944	High Similarity	NPC166138
0.8944	High Similarity	NPC112791
0.8944	High Similarity	NPC106985
0.8944	High Similarity	NPC190637
0.8944	High Similarity	NPC94794
0.8944	High Similarity	NPC196459
0.8936	High Similarity	NPC14871
0.8936	High Similarity	NPC248372
0.8936	High Similarity	NPC110038
0.8929	High Similarity	NPC241975
0.8929	High Similarity	NPC19476
0.8929	High Similarity	NPC139554
0.8919	High Similarity	NPC470354
0.8913	High Similarity	NPC60667
0.8913	High Similarity	NPC46869
0.8905	High Similarity	NPC16197
0.8904	High Similarity	NPC81474
0.8889	High Similarity	NPC237635
0.8889	High Similarity	NPC296998
0.8889	High Similarity	NPC180477
0.8889	High Similarity	NPC110303
0.8889	High Similarity	NPC166757
0.8889	High Similarity	NPC297886
0.8889	High Similarity	NPC283234
0.8889	High Similarity	NPC23728
0.8889	High Similarity	NPC14001
0.8889	High Similarity	NPC285748
0.8889	High Similarity	NPC79469
0.8889	High Similarity	NPC249942
0.8889	High Similarity	NPC24673
0.8889	High Similarity	NPC177995
0.8889	High Similarity	NPC97716
0.8889	High Similarity	NPC186628
0.8889	High Similarity	NPC473077
0.8889	High Similarity	NPC474108
0.8889	High Similarity	NPC201731
0.8889	High Similarity	NPC140120
0.8889	High Similarity	NPC104406
0.8881	High Similarity	NPC216538
0.8881	High Similarity	NPC117716
0.8881	High Similarity	NPC196137
0.8881	High Similarity	NPC131568
0.8881	High Similarity	NPC131579
0.8881	High Similarity	NPC273538
0.8881	High Similarity	NPC319752
0.8881	High Similarity	NPC209040
0.8881	High Similarity	NPC470673
0.8881	High Similarity	NPC178627
0.8881	High Similarity	NPC470674
0.8881	High Similarity	NPC1886
0.8881	High Similarity	NPC326500
0.8881	High Similarity	NPC469935
0.8873	High Similarity	NPC125855
0.8873	High Similarity	NPC228504
0.8873	High Similarity	NPC107572
0.8873	High Similarity	NPC167624
0.8873	High Similarity	NPC227579
0.8873	High Similarity	NPC324436
0.8873	High Similarity	NPC220998
0.8873	High Similarity	NPC223500
0.8873	High Similarity	NPC266725
0.8873	High Similarity	NPC166934

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 NPC268178 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	339
0.1-0.2	1023
0.2-0.3	1855
0.3-0.4	2750
0.4-0.5	1852
0.5-0.6	939
0.6-0.7	275
0.7-0.8	97
0.8-0.85	17
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9149	High Similarity	NPD7410	Clinical (unspecified phase)
0.9065	High Similarity	NPD2800	Approved
0.9044	High Similarity	NPD6651	Approved
0.8881	High Similarity	NPD4378	Clinical (unspecified phase)
0.8521	High Similarity	NPD1550	Clinical (unspecified phase)
0.8521	High Similarity	NPD1552	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD1549	Phase 2
0.84	Intermediate Similarity	NPD7411	Suspended
0.838	Intermediate Similarity	NPD1510	Phase 2
0.8357	Intermediate Similarity	NPD1240	Approved
0.8355	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD4380	Phase 2
0.8322	Intermediate Similarity	NPD2796	Approved
0.8289	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD7075	Discontinued
0.8239	Intermediate Similarity	NPD1607	Approved
0.8176	Intermediate Similarity	NPD1511	Approved
0.817	Intermediate Similarity	NPD7819	Suspended
0.8095	Intermediate Similarity	NPD3750	Approved
0.8067	Intermediate Similarity	NPD1512	Approved
0.8052	Intermediate Similarity	NPD2801	Approved
0.8052	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2533	Approved
0.8	Intermediate Similarity	NPD2534	Approved
0.8	Intermediate Similarity	NPD2532	Approved
0.7987	Intermediate Similarity	NPD1934	Approved
0.7975	Intermediate Similarity	NPD6959	Discontinued
0.7959	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6799	Approved
0.7905	Intermediate Similarity	NPD1243	Approved
0.7905	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6599	Discontinued
0.7834	Intermediate Similarity	NPD7768	Phase 2
0.7793	Intermediate Similarity	NPD5124	Phase 1
0.7793	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD3749	Approved
0.7778	Intermediate Similarity	NPD920	Approved
0.7771	Intermediate Similarity	NPD3817	Phase 2
0.7755	Intermediate Similarity	NPD3748	Approved
0.7733	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD3882	Suspended
0.7716	Intermediate Similarity	NPD6166	Phase 2
0.7716	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD2313	Discontinued
0.7703	Intermediate Similarity	NPD6100	Approved
0.7703	Intermediate Similarity	NPD6099	Approved
0.7662	Intermediate Similarity	NPD5403	Approved
0.7651	Intermediate Similarity	NPD2344	Approved
0.7635	Intermediate Similarity	NPD2799	Discontinued
0.7632	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3818	Discontinued
0.7616	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6232	Discontinued
0.759	Intermediate Similarity	NPD5953	Discontinued
0.7584	Intermediate Similarity	NPD2935	Discontinued
0.7584	Intermediate Similarity	NPD1551	Phase 2
0.7576	Intermediate Similarity	NPD7054	Approved
0.7576	Intermediate Similarity	NPD7286	Phase 2
0.7571	Intermediate Similarity	NPD422	Phase 1
0.7561	Intermediate Similarity	NPD7473	Discontinued
0.7532	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD5401	Approved
0.753	Intermediate Similarity	NPD7472	Approved
0.753	Intermediate Similarity	NPD7074	Phase 3
0.7518	Intermediate Similarity	NPD9717	Approved
0.7485	Intermediate Similarity	NPD6797	Phase 2
0.7483	Intermediate Similarity	NPD1203	Approved
0.7469	Intermediate Similarity	NPD5494	Approved
0.7466	Intermediate Similarity	NPD3268	Approved
0.7452	Intermediate Similarity	NPD3226	Approved
0.7451	Intermediate Similarity	NPD2309	Approved
0.744	Intermediate Similarity	NPD7251	Discontinued
0.744	Intermediate Similarity	NPD6559	Discontinued
0.74	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7033	Discontinued
0.7396	Intermediate Similarity	NPD7808	Phase 3
0.7391	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5710	Approved
0.7378	Intermediate Similarity	NPD5711	Approved
0.7361	Intermediate Similarity	NPD2797	Approved
0.7355	Intermediate Similarity	NPD7390	Discontinued
0.7347	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6832	Phase 2
0.7329	Intermediate Similarity	NPD5402	Approved
0.732	Intermediate Similarity	NPD2654	Approved
0.731	Intermediate Similarity	NPD2798	Approved
0.7303	Intermediate Similarity	NPD2346	Discontinued
0.7301	Intermediate Similarity	NPD919	Approved
0.7294	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD1548	Phase 1
0.7285	Intermediate Similarity	NPD4308	Phase 3
0.7273	Intermediate Similarity	NPD4628	Phase 3
0.7248	Intermediate Similarity	NPD943	Approved
0.723	Intermediate Similarity	NPD1296	Phase 2
0.7229	Intermediate Similarity	NPD3926	Phase 2
0.7222	Intermediate Similarity	NPD4749	Approved
0.7219	Intermediate Similarity	NPD1729	Discontinued
0.7212	Intermediate Similarity	NPD1247	Approved
0.7211	Intermediate Similarity	NPD4908	Phase 1
0.7203	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4363	Phase 3
0.7175	Intermediate Similarity	NPD4360	Phase 2
0.7172	Intermediate Similarity	NPD3225	Approved
0.7162	Intermediate Similarity	NPD4625	Phase 3
0.716	Intermediate Similarity	NPD1465	Phase 2
0.716	Intermediate Similarity	NPD5844	Phase 1
0.7153	Intermediate Similarity	NPD3972	Approved
0.7135	Intermediate Similarity	NPD6104	Discontinued
0.7135	Intermediate Similarity	NPD4361	Phase 2
0.7135	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3266	Approved
0.7123	Intermediate Similarity	NPD3267	Approved
0.7117	Intermediate Similarity	NPD4288	Approved
0.7114	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1610	Phase 2
0.7083	Intermediate Similarity	NPD2403	Approved
0.7081	Intermediate Similarity	NPD6585	Discontinued
0.705	Intermediate Similarity	NPD1241	Discontinued
0.7042	Intermediate Similarity	NPD9545	Approved
0.7037	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD9493	Approved
0.702	Intermediate Similarity	NPD4307	Phase 2
0.7	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD411	Approved
0.6977	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD447	Suspended
0.6949	Remote Similarity	NPD4287	Approved
0.6937	Remote Similarity	NPD5049	Phase 3
0.6935	Remote Similarity	NPD7584	Approved
0.6933	Remote Similarity	NPD5890	Approved
0.6933	Remote Similarity	NPD5889	Approved
0.6918	Remote Similarity	NPD1608	Approved
0.6914	Remote Similarity	NPD7458	Discontinued
0.6909	Remote Similarity	NPD2296	Approved
0.6903	Remote Similarity	NPD5404	Approved
0.6903	Remote Similarity	NPD5405	Approved
0.6903	Remote Similarity	NPD5406	Approved
0.6903	Remote Similarity	NPD5408	Approved
0.6887	Remote Similarity	NPD3764	Approved
0.6885	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1933	Approved
0.6863	Remote Similarity	NPD230	Phase 1
0.6859	Remote Similarity	NPD1471	Phase 3
0.6849	Remote Similarity	NPD1201	Approved
0.6846	Remote Similarity	NPD1019	Discontinued
0.6839	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD8434	Phase 2
0.6835	Remote Similarity	NPD7003	Approved
0.6815	Remote Similarity	NPD2424	Discontinued
0.6802	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD2354	Approved
0.6786	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1164	Approved
0.6779	Remote Similarity	NPD1470	Approved
0.6776	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD6798	Discontinued
0.6772	Remote Similarity	NPD1652	Phase 2
0.6765	Remote Similarity	NPD7229	Phase 3
0.6753	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6002	Phase 3
0.6752	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6004	Phase 3
0.6752	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6005	Phase 3
0.6747	Remote Similarity	NPD5761	Phase 2
0.6747	Remote Similarity	NPD5760	Phase 2
0.6744	Remote Similarity	NPD3446	Phase 1
0.6712	Remote Similarity	NPD17	Approved
0.6711	Remote Similarity	NPD8651	Approved
0.6708	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7199	Phase 2
0.6705	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD3751	Discontinued
0.6689	Remote Similarity	NPD1481	Phase 2
0.6688	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3140	Approved
0.6688	Remote Similarity	NPD3142	Approved
0.6688	Remote Similarity	NPD1613	Approved
0.6667	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8312	Approved
0.6667	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8313	Approved
0.6646	Remote Similarity	NPD2353	Approved

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