NPASS Compound

Structure

NPC279566 OpenBabel07101719522D 33 34 0 0 0 0 0 0 0 0999 V2000 3.3651 -3.8857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 -3.4000 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 -2.5238 1.4571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5238 2.4286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6826 2.9143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2064 -3.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.9143 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 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 0.4857 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 2.5238 0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3651 -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 3.3651 -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 4.2064 -0.4857 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 2.5238 -0.4857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3651 0.9714 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 -2.4286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6826 -1.9429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0477 -0.9714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5238 -0.4857 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6826 -0.9714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8413 -0.4857 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3651 1.9429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8413 2.4286 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 12 1 0 0 0 0 4 13 1 0 0 0 0 5 32 1 0 0 0 0 6 33 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 15 1 0 0 0 0 12 20 1 0 0 0 0 12 24 2 0 0 0 0 13 21 1 0 0 0 0 13 25 2 0 0 0 0 14 22 2 0 0 0 0 14 24 1 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 26 2 0 0 0 0 17 19 1 0 0 0 0 17 27 2 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 32 1 0 0 0 0 25 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.21
Volume:	473.073
LogP:	6.415
LogD:	3.07
LogS:	-3.939
# Rotatable Bonds:	10
TPSA:	133.52
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	3.116
Fsp3:	0.44
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:	-5.341
MDCK Permeability:	1.4444111911871005e-05
Pgp-inhibitor:	0.628
Pgp-substrate:	0.341
Human Intestinal Absorption (HIA):	0.071
20% Bioavailability (F20%):	0.207
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	98.29744720458984%
Volume Distribution (VD):	0.429
Pgp-substrate:	1.7932472229003906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.944
CYP2C19-inhibitor:	0.392
CYP2C19-substrate:	0.702
CYP2C9-inhibitor:	0.739
CYP2C9-substrate:	0.854
CYP2D6-inhibitor:	0.058
CYP2D6-substrate:	0.224
CYP3A4-inhibitor:	0.157
CYP3A4-substrate:	0.285

ADMET: Excretion

Clearance (CL):	5.615
Half-life (T1/2):	0.144

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.901
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.118
Maximum Recommended Daily Dose:	0.213
Skin Sensitization:	0.947
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.892
Respiratory Toxicity:	0.085

Download Data

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

Natural Product: NPC279566

Natural Product ID:	NPC279566
*Common Name:**	Methylene-Bis-Aspidinol
IUPAC Name:	1-[3-[(3-butanoyl-2,4-dihydroxy-6-methoxy-5-methylphenyl)methyl]-2,6-dihydroxy-4-methoxy-5-methylphenyl]butan-1-one
Synonyms:	Methylene-Bis-Aspidinol
Standard InCHIKey:	KSPJWSCWSGSJRH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C25H32O8/c1-7-9-16(26)18-20(28)12(3)24(32-5)14(22(18)30)11-15-23(31)19(17(27)10-8-2)21(29)13(4)25(15)33-6/h28-31H,7-11H2,1-6H3
SMILES:	CCCC(=O)c1c(c(C)c(c(Cc2c(c(C(=O)CCC)c(c(C)c2OC)O)O)c1O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482041
PubChem CID:	617027
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO24313	Calyptranthes pallens	Species	Myrtaceae	Eukaryota	leaves and twigs	Southern Florida	n.a.	PMID[15844953]
NPO24313	Calyptranthes pallens	Species	Myrtaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	19.4	ug ml-1	PMID[521533]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	6.6	ug ml-1	PMID[521533]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	=	7.3	ug ml-1	PMID[521533]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.7	ug ml-1	PMID[521533]
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	=	6.1	ug ml-1	PMID[521533]

☑ 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 NPC279566 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	330
0.1-0.2	1603
0.2-0.3	4557
0.3-0.4	11908
0.4-0.5	6954
0.5-0.6	5083
0.6-0.7	5877
0.7-0.8	4670
0.8-0.85	1099
0.85-0.9	512
0.9-0.95	93
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9919	High Similarity	NPC186628
0.9764	High Similarity	NPC16197
0.9685	High Similarity	NPC215875
0.9685	High Similarity	NPC15834
0.9466	High Similarity	NPC322301
0.9466	High Similarity	NPC255801
0.9385	High Similarity	NPC103842
0.9313	High Similarity	NPC156092
0.9313	High Similarity	NPC13575
0.9248	High Similarity	NPC272844
0.9248	High Similarity	NPC254168
0.9248	High Similarity	NPC248995
0.9242	High Similarity	NPC477242
0.9242	High Similarity	NPC12165
0.9242	High Similarity	NPC477244
0.9242	High Similarity	NPC249606
0.9242	High Similarity	NPC41461
0.9242	High Similarity	NPC25287
0.9242	High Similarity	NPC150399
0.9242	High Similarity	NPC168105
0.9242	High Similarity	NPC186838
0.9242	High Similarity	NPC274109
0.9242	High Similarity	NPC66349
0.9242	High Similarity	NPC98115
0.9242	High Similarity	NPC1486
0.9242	High Similarity	NPC477243
0.9185	High Similarity	NPC476508
0.9179	High Similarity	NPC240305
0.9173	High Similarity	NPC317119
0.9173	High Similarity	NPC153979
0.9173	High Similarity	NPC472419
0.9167	High Similarity	NPC131039
0.916	High Similarity	NPC18877
0.916	High Similarity	NPC82225
0.916	High Similarity	NPC28753
0.916	High Similarity	NPC20560
0.916	High Similarity	NPC144051
0.916	High Similarity	NPC204960
0.916	High Similarity	NPC294593
0.916	High Similarity	NPC159623
0.9147	High Similarity	NPC84772
0.9113	High Similarity	NPC229649
0.9104	High Similarity	NPC21350
0.9104	High Similarity	NPC477056
0.9104	High Similarity	NPC471620
0.9104	High Similarity	NPC251681
0.9104	High Similarity	NPC243528
0.9104	High Similarity	NPC477055
0.9091	High Similarity	NPC286336
0.9084	High Similarity	NPC285054
0.9077	High Similarity	NPC324482
0.9077	High Similarity	NPC250057
0.907	High Similarity	NPC230818
0.9037	High Similarity	NPC472366
0.9037	High Similarity	NPC477956
0.9037	High Similarity	NPC53181
0.9037	High Similarity	NPC217186
0.9037	High Similarity	NPC470211
0.9037	High Similarity	NPC283429
0.9023	High Similarity	NPC101752
0.9015	High Similarity	NPC472365
0.9015	High Similarity	NPC139813
0.9015	High Similarity	NPC175098
0.9015	High Similarity	NPC188646
0.9015	High Similarity	NPC312318
0.9015	High Similarity	NPC192304
0.9015	High Similarity	NPC242294
0.9015	High Similarity	NPC337373
0.9015	High Similarity	NPC56031
0.9015	High Similarity	NPC27643
0.9015	High Similarity	NPC263670
0.9008	High Similarity	NPC186097
0.9008	High Similarity	NPC475009
0.9008	High Similarity	NPC475008
0.9008	High Similarity	NPC27490
0.8986	High Similarity	NPC282957
0.8986	High Similarity	NPC194949
0.8986	High Similarity	NPC328623
0.8978	High Similarity	NPC297600
0.8971	High Similarity	NPC204985
0.8971	High Similarity	NPC253822
0.8971	High Similarity	NPC172250
0.8971	High Similarity	NPC215311
0.8971	High Similarity	NPC326109
0.8971	High Similarity	NPC213659
0.8971	High Similarity	NPC159275
0.8971	High Similarity	NPC48624
0.8971	High Similarity	NPC259166
0.8971	High Similarity	NPC144118
0.8971	High Similarity	NPC80962
0.8971	High Similarity	NPC241100
0.8971	High Similarity	NPC219917
0.8971	High Similarity	NPC11056
0.8968	High Similarity	NPC232708
0.8955	High Similarity	NPC174999
0.8939	High Similarity	NPC257756
0.8939	High Similarity	NPC212631
0.8939	High Similarity	NPC129132
0.8939	High Similarity	NPC103105
0.8939	High Similarity	NPC87231
0.8939	High Similarity	NPC205468
0.8913	High Similarity	NPC112749
0.8913	High Similarity	NPC185276
0.8905	High Similarity	NPC52789
0.8905	High Similarity	NPC17170
0.8905	High Similarity	NPC469404
0.8905	High Similarity	NPC166689
0.8905	High Similarity	NPC470089
0.8905	High Similarity	NPC156190
0.8905	High Similarity	NPC157497
0.8905	High Similarity	NPC26051
0.8905	High Similarity	NPC81337
0.8905	High Similarity	NPC110038
0.8905	High Similarity	NPC26238
0.8905	High Similarity	NPC282300
0.8905	High Similarity	NPC258630
0.8905	High Similarity	NPC268204
0.8905	High Similarity	NPC285659
0.8905	High Similarity	NPC321980
0.8905	High Similarity	NPC470087
0.8905	High Similarity	NPC96408
0.8905	High Similarity	NPC279650
0.8905	High Similarity	NPC110969
0.8905	High Similarity	NPC55832
0.8905	High Similarity	NPC248372
0.8897	High Similarity	NPC295384
0.8897	High Similarity	NPC96565
0.8897	High Similarity	NPC303633
0.8897	High Similarity	NPC216978
0.8897	High Similarity	NPC220062
0.8897	High Similarity	NPC301217
0.8897	High Similarity	NPC55018
0.8897	High Similarity	NPC18260
0.8897	High Similarity	NPC78913
0.8864	High Similarity	NPC66384
0.8864	High Similarity	NPC262359
0.8864	High Similarity	NPC64359
0.8864	High Similarity	NPC164236
0.8864	High Similarity	NPC128348
0.8864	High Similarity	NPC313618
0.8864	High Similarity	NPC189106
0.8864	High Similarity	NPC308037
0.8864	High Similarity	NPC309717
0.8864	High Similarity	NPC112192
0.8849	High Similarity	NPC197252
0.8849	High Similarity	NPC473014
0.8849	High Similarity	NPC236766
0.8849	High Similarity	NPC235217
0.8841	High Similarity	NPC76338
0.8841	High Similarity	NPC10937
0.8841	High Similarity	NPC328164
0.8841	High Similarity	NPC182852
0.8841	High Similarity	NPC78
0.8841	High Similarity	NPC148757
0.8841	High Similarity	NPC166482
0.8841	High Similarity	NPC125855
0.8841	High Similarity	NPC194432
0.8841	High Similarity	NPC40833
0.8841	High Similarity	NPC76372
0.8841	High Similarity	NPC177354
0.8841	High Similarity	NPC66515
0.8841	High Similarity	NPC306829
0.8841	High Similarity	NPC228504
0.8841	High Similarity	NPC227579
0.8841	High Similarity	NPC167624
0.8841	High Similarity	NPC107572
0.8841	High Similarity	NPC220998
0.8841	High Similarity	NPC266725
0.8841	High Similarity	NPC324436
0.8841	High Similarity	NPC296917
0.8841	High Similarity	NPC223500
0.8841	High Similarity	NPC11561
0.8841	High Similarity	NPC265040
0.8841	High Similarity	NPC64915
0.8841	High Similarity	NPC166934
0.8841	High Similarity	NPC1089
0.8841	High Similarity	NPC325346
0.8841	High Similarity	NPC161506
0.8841	High Similarity	NPC37496
0.8841	High Similarity	NPC226636
0.8841	High Similarity	NPC324134
0.8841	High Similarity	NPC32739
0.8832	High Similarity	NPC172986
0.8832	High Similarity	NPC261227
0.8832	High Similarity	NPC101366
0.8832	High Similarity	NPC265178
0.8832	High Similarity	NPC471587
0.8832	High Similarity	NPC150522
0.8832	High Similarity	NPC69769
0.8832	High Similarity	NPC270883
0.8824	High Similarity	NPC472368
0.8824	High Similarity	NPC131130
0.8824	High Similarity	NPC201395
0.8824	High Similarity	NPC180501
0.8824	High Similarity	NPC219584
0.8824	High Similarity	NPC124269
0.8824	High Similarity	NPC268178
0.8824	High Similarity	NPC54820
0.8824	High Similarity	NPC470083
0.8815	High Similarity	NPC473391

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 NPC279566 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	1056
0.2-0.3	1891
0.3-0.4	2845
0.4-0.5	1735
0.5-0.6	947
0.6-0.7	266
0.7-0.8	86
0.8-0.85	12
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9457	High Similarity	NPD6651	Approved
0.8864	High Similarity	NPD1240	Approved
0.8731	High Similarity	NPD1607	Approved
0.8714	High Similarity	NPD4378	Clinical (unspecified phase)
0.8714	High Similarity	NPD7410	Clinical (unspecified phase)
0.8603	High Similarity	NPD1510	Phase 2
0.8489	Intermediate Similarity	NPD2800	Approved
0.8478	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8478	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD1549	Phase 2
0.8414	Intermediate Similarity	NPD4380	Phase 2
0.8356	Intermediate Similarity	NPD7411	Suspended
0.8322	Intermediate Similarity	NPD7075	Discontinued
0.8243	Intermediate Similarity	NPD7819	Suspended
0.8243	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2533	Approved
0.8194	Intermediate Similarity	NPD2532	Approved
0.8194	Intermediate Similarity	NPD2534	Approved
0.8176	Intermediate Similarity	NPD6801	Discontinued
0.8143	Intermediate Similarity	NPD2796	Approved
0.8121	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD6959	Discontinued
0.8028	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD2935	Discontinued
0.8	Intermediate Similarity	NPD6799	Approved
0.7949	Intermediate Similarity	NPD7473	Discontinued
0.7933	Intermediate Similarity	NPD1934	Approved
0.7899	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7768	Phase 2
0.7885	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD2801	Approved
0.7877	Intermediate Similarity	NPD1511	Approved
0.7871	Intermediate Similarity	NPD6232	Discontinued
0.7848	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD3882	Suspended
0.777	Intermediate Similarity	NPD1512	Approved
0.7736	Intermediate Similarity	NPD7286	Phase 2
0.7724	Intermediate Similarity	NPD1243	Approved
0.7692	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD3750	Approved
0.7658	Intermediate Similarity	NPD6166	Phase 2
0.7658	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5953	Discontinued
0.7639	Intermediate Similarity	NPD1551	Phase 2
0.7635	Intermediate Similarity	NPD7390	Discontinued
0.7603	Intermediate Similarity	NPD2654	Approved
0.76	Intermediate Similarity	NPD920	Approved
0.7597	Intermediate Similarity	NPD3817	Phase 2
0.7578	Intermediate Similarity	NPD7074	Phase 3
0.7569	Intermediate Similarity	NPD2799	Discontinued
0.7535	Intermediate Similarity	NPD943	Approved
0.7532	Intermediate Similarity	NPD5710	Approved
0.7532	Intermediate Similarity	NPD5711	Approved
0.7516	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD3749	Approved
0.75	Intermediate Similarity	NPD6832	Phase 2
0.7483	Intermediate Similarity	NPD5403	Approved
0.7469	Intermediate Similarity	NPD7472	Approved
0.7466	Intermediate Similarity	NPD2344	Approved
0.7453	Intermediate Similarity	NPD3818	Discontinued
0.745	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1203	Approved
0.7405	Intermediate Similarity	NPD5494	Approved
0.7397	Intermediate Similarity	NPD6099	Approved
0.7397	Intermediate Similarity	NPD6100	Approved
0.7394	Intermediate Similarity	NPD2313	Discontinued
0.7378	Intermediate Similarity	NPD7251	Discontinued
0.7378	Intermediate Similarity	NPD6559	Discontinued
0.7357	Intermediate Similarity	NPD2798	Approved
0.7351	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD5401	Approved
0.7333	Intermediate Similarity	NPD7808	Phase 3
0.7329	Intermediate Similarity	NPD3748	Approved
0.7319	Intermediate Similarity	NPD3972	Approved
0.7317	Intermediate Similarity	NPD6797	Phase 2
0.7273	Intermediate Similarity	NPD3226	Approved
0.7273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2309	Approved
0.7255	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5124	Phase 1
0.72	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4628	Phase 3
0.7194	Intermediate Similarity	NPD9717	Approved
0.7185	Intermediate Similarity	NPD9493	Approved
0.7161	Intermediate Similarity	NPD7458	Discontinued
0.716	Intermediate Similarity	NPD3926	Phase 2
0.7153	Intermediate Similarity	NPD3268	Approved
0.7153	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1729	Discontinued
0.7152	Intermediate Similarity	NPD5402	Approved
0.7133	Intermediate Similarity	NPD4908	Phase 1
0.7126	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD919	Approved
0.7122	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD422	Phase 1
0.7114	Intermediate Similarity	NPD2346	Discontinued
0.7095	Intermediate Similarity	NPD7033	Discontinued
0.7091	Intermediate Similarity	NPD5844	Phase 1
0.7089	Intermediate Similarity	NPD1465	Phase 2
0.708	Intermediate Similarity	NPD1548	Phase 1
0.708	Intermediate Similarity	NPD9545	Approved
0.707	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5406	Approved
0.7047	Intermediate Similarity	NPD5404	Approved
0.7047	Intermediate Similarity	NPD5408	Approved
0.7047	Intermediate Similarity	NPD5405	Approved
0.7042	Intermediate Similarity	NPD1164	Approved
0.7042	Intermediate Similarity	NPD2797	Approved
0.7037	Intermediate Similarity	NPD1247	Approved
0.7011	Intermediate Similarity	NPD4363	Phase 3
0.7011	Intermediate Similarity	NPD4360	Phase 2
0.7007	Intermediate Similarity	NPD230	Phase 1
0.7006	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1610	Phase 2
0.7	Intermediate Similarity	NPD1201	Approved
0.6994	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7003	Approved
0.6971	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4361	Phase 2
0.6964	Remote Similarity	NPD6104	Discontinued
0.6923	Remote Similarity	NPD1470	Approved
0.6918	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4308	Phase 3
0.6867	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1876	Approved
0.6853	Remote Similarity	NPD3225	Approved
0.6849	Remote Similarity	NPD4625	Phase 3
0.6849	Remote Similarity	NPD3027	Phase 3
0.6839	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1608	Approved
0.6813	Remote Similarity	NPD37	Approved
0.6807	Remote Similarity	NPD2403	Approved
0.6806	Remote Similarity	NPD3267	Approved
0.6806	Remote Similarity	NPD3266	Approved
0.6803	Remote Similarity	NPD1296	Phase 2
0.6803	Remote Similarity	NPD3764	Approved
0.6795	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD7229	Phase 3
0.6786	Remote Similarity	NPD1651	Approved
0.6782	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD1933	Approved
0.6779	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7584	Approved
0.6759	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5049	Phase 3
0.675	Remote Similarity	NPD5889	Approved
0.675	Remote Similarity	NPD5890	Approved
0.6736	Remote Similarity	NPD1283	Approved
0.6728	Remote Similarity	NPD4288	Approved
0.6728	Remote Similarity	NPD2296	Approved
0.6726	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1241	Discontinued
0.6712	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD6234	Discontinued
0.6703	Remote Similarity	NPD8151	Discontinued
0.669	Remote Similarity	NPD3847	Discontinued
0.6689	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD411	Approved
0.6689	Remote Similarity	NPD6798	Discontinued
0.6688	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD4965	Approved
0.6687	Remote Similarity	NPD4966	Approved
0.6687	Remote Similarity	NPD4967	Phase 2
0.6687	Remote Similarity	NPD6585	Discontinued
0.6686	Remote Similarity	NPD4287	Approved
0.6686	Remote Similarity	NPD8312	Approved
0.6686	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD1471	Phase 3
0.6667	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4749	Approved
0.6667	Remote Similarity	NPD447	Suspended
0.6667	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD1019	Discontinued
0.6641	Remote Similarity	NPD940	Approved
0.6641	Remote Similarity	NPD846	Approved
0.663	Remote Similarity	NPD6779	Approved
0.663	Remote Similarity	NPD6777	Approved
0.663	Remote Similarity	NPD6776	Approved
0.663	Remote Similarity	NPD6782	Approved
0.663	Remote Similarity	NPD6781	Approved
0.663	Remote Similarity	NPD6780	Approved
0.663	Remote Similarity	NPD6778	Approved
0.6627	Remote Similarity	NPD7199	Phase 2
0.6625	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.662	Remote Similarity	NPD4626	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