NPASS Compound

Structure

NPC472627 OpenBabel07101718292D 32 34 0 0 1 0 0 0 0 0999 V2000 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -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 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 10 1 0 0 0 0 4 14 2 0 0 0 0 5 11 1 0 0 0 0 5 14 1 0 0 0 0 6 8 1 0 0 0 0 6 15 2 0 0 0 0 7 9 2 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 22 1 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 24 2 0 0 0 0 18 27 1 0 0 0 0 19 23 1 0 0 0 0 19 28 2 0 0 0 0 20 15 1 6 0 0 0 20 32 1 0 0 0 0 21 23 2 0 0 0 0 21 32 1 0 0 0 0 22 25 1 0 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 24 30 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.2
Volume:	455.727
LogP:	3.279
LogD:	2.497
LogS:	-3.534
# Rotatable Bonds:	7
TPSA:	127.45
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.411
Synthetic Accessibility Score:	3.782
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.121
MDCK Permeability:	1.3139949260221329e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.952
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.285
30% Bioavailability (F30%):	0.907

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	96.90450286865234%
Volume Distribution (VD):	0.418
Pgp-substrate:	1.9874762296676636%

ADMET: Metabolism

CYP1A2-inhibitor:	0.095
CYP1A2-substrate:	0.128
CYP2C19-inhibitor:	0.47
CYP2C19-substrate:	0.071
CYP2C9-inhibitor:	0.852
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.865
CYP2D6-substrate:	0.579
CYP3A4-inhibitor:	0.159
CYP3A4-substrate:	0.22

ADMET: Excretion

Clearance (CL):	11.036
Half-life (T1/2):	0.701

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.219
Drug-inuced Liver Injury (DILI):	0.668
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.629
Maximum Recommended Daily Dose:	0.245
Skin Sensitization:	0.747
Carcinogencity:	0.203
Eye Corrosion:	0.003
Eye Irritation:	0.159
Respiratory Toxicity:	0.561

Download Data

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

Natural Product: NPC472627

Natural Product ID:	NPC472627
*Common Name:**	CNRLXVAPOXIIJK-XMVXEKSUSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CNRLXVAPOXIIJK-XMVXEKSUSA-N
Standard InCHI:	InChI=1S/C25H30O7/c1-14(5-11-22(29)25(2,3)31)4-10-17-18(27)12-21-23(24(17)30)19(28)13-20(32-21)15-6-8-16(26)9-7-15/h4,6-9,12,20,22,26-27,29-31H,5,10-11,13H2,1-3H3/b14-4+/t20-,22?/m0/s1
SMILES:	C/C(=CCc1c(O)cc2c(c1O)C(=O)C[C@H](O2)c1ccc(cc1)O)/CCC(C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581347
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003646] 6-prenylated flavans [CHEMONTID:0003507] 6-prenylated flavanones

*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
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[17625893]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[18293924]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20192247]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21319773]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22445674]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23623680]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	n.a.	n.a.	PMID[25735399]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28322565]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[28968119]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	>	10000.0	nM	PMID[557158]

☑ 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 NPC472627 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	360
0.1-0.2	1387
0.2-0.3	3611
0.3-0.4	9027
0.4-0.5	9556
0.5-0.6	3590
0.6-0.7	5463
0.7-0.8	5443
0.8-0.85	2300
0.85-0.9	1245
0.9-0.95	543
0.95-1	172

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC472628
0.9786	High Similarity	NPC478086
0.9786	High Similarity	NPC316816
0.9786	High Similarity	NPC214166
0.9722	High Similarity	NPC471677
0.9722	High Similarity	NPC263384
0.9722	High Similarity	NPC472422
0.9722	High Similarity	NPC472420
0.9722	High Similarity	NPC471676
0.9722	High Similarity	NPC244577
0.9716	High Similarity	NPC131579
0.9716	High Similarity	NPC131568
0.9716	High Similarity	NPC209040
0.9714	High Similarity	NPC40833
0.9714	High Similarity	NPC1089
0.9714	High Similarity	NPC161506
0.9714	High Similarity	NPC220998
0.9714	High Similarity	NPC182852
0.9714	High Similarity	NPC194432
0.9714	High Similarity	NPC296917
0.9714	High Similarity	NPC32739
0.9714	High Similarity	NPC37496
0.9714	High Similarity	NPC166934
0.9714	High Similarity	NPC177354
0.9714	High Similarity	NPC148757
0.9714	High Similarity	NPC76338
0.9714	High Similarity	NPC324134
0.9714	High Similarity	NPC227579
0.9714	High Similarity	NPC228504
0.9714	High Similarity	NPC107572
0.9714	High Similarity	NPC306829
0.9714	High Similarity	NPC64915
0.9714	High Similarity	NPC10937
0.9714	High Similarity	NPC324436
0.9714	High Similarity	NPC125855
0.9714	High Similarity	NPC167624
0.9714	High Similarity	NPC76372
0.9714	High Similarity	NPC265040
0.9714	High Similarity	NPC78
0.9714	High Similarity	NPC66515
0.9714	High Similarity	NPC166482
0.9714	High Similarity	NPC223500
0.9714	High Similarity	NPC328164
0.9655	High Similarity	NPC475790
0.9648	High Similarity	NPC176229
0.9648	High Similarity	NPC285630
0.9648	High Similarity	NPC475052
0.9648	High Similarity	NPC111786
0.9648	High Similarity	NPC312973
0.9648	High Similarity	NPC470647
0.9648	High Similarity	NPC267375
0.9648	High Similarity	NPC54577
0.9648	High Similarity	NPC246948
0.9648	High Similarity	NPC88964
0.9648	High Similarity	NPC67805
0.9648	High Similarity	NPC301276
0.9648	High Similarity	NPC195621
0.9648	High Similarity	NPC472629
0.9648	High Similarity	NPC142405
0.9648	High Similarity	NPC20488
0.9648	High Similarity	NPC127059
0.9648	High Similarity	NPC83357
0.9648	High Similarity	NPC214774
0.9645	High Similarity	NPC107177
0.9645	High Similarity	NPC223812
0.9645	High Similarity	NPC257097
0.9645	High Similarity	NPC85162
0.9645	High Similarity	NPC91560
0.9645	High Similarity	NPC169591
0.9645	High Similarity	NPC150408
0.9645	High Similarity	NPC39329
0.9645	High Similarity	NPC68104
0.9645	High Similarity	NPC185276
0.9645	High Similarity	NPC164980
0.9645	High Similarity	NPC143896
0.9645	High Similarity	NPC149026
0.9645	High Similarity	NPC310130
0.9645	High Similarity	NPC125894
0.9645	High Similarity	NPC77794
0.9645	High Similarity	NPC81697
0.9645	High Similarity	NPC75049
0.9645	High Similarity	NPC175504
0.9645	High Similarity	NPC221432
0.9645	High Similarity	NPC278249
0.9643	High Similarity	NPC17170
0.9643	High Similarity	NPC110038
0.9643	High Similarity	NPC324386
0.9643	High Similarity	NPC258630
0.9643	High Similarity	NPC248372
0.9643	High Similarity	NPC312391
0.9643	High Similarity	NPC96408
0.9643	High Similarity	NPC279650
0.9643	High Similarity	NPC156190
0.9643	High Similarity	NPC166689
0.9643	High Similarity	NPC4743
0.9643	High Similarity	NPC213322
0.9589	High Similarity	NPC223701
0.9589	High Similarity	NPC7989
0.9589	High Similarity	NPC472583
0.9586	High Similarity	NPC278476
0.9586	High Similarity	NPC472580
0.9586	High Similarity	NPC474021
0.9586	High Similarity	NPC262039
0.9586	High Similarity	NPC474023
0.9586	High Similarity	NPC262038
0.9586	High Similarity	NPC254412
0.9586	High Similarity	NPC319910
0.9586	High Similarity	NPC472636
0.958	High Similarity	NPC296998
0.958	High Similarity	NPC23728
0.958	High Similarity	NPC110303
0.958	High Similarity	NPC283234
0.958	High Similarity	NPC473077
0.9577	High Similarity	NPC235217
0.9577	High Similarity	NPC197252
0.9577	High Similarity	NPC473015
0.9577	High Similarity	NPC87486
0.9577	High Similarity	NPC236766
0.9577	High Similarity	NPC473013
0.9577	High Similarity	NPC470890
0.9577	High Similarity	NPC124780
0.9577	High Similarity	NPC473014
0.9574	High Similarity	NPC147145
0.9571	High Similarity	NPC6407
0.9571	High Similarity	NPC110228
0.9571	High Similarity	NPC188243
0.9524	High Similarity	NPC304207
0.9524	High Similarity	NPC477958
0.9524	High Similarity	NPC48579
0.9524	High Similarity	NPC217706
0.9524	High Similarity	NPC259710
0.9524	High Similarity	NPC207809
0.9521	High Similarity	NPC161881
0.9521	High Similarity	NPC473996
0.9521	High Similarity	NPC35567
0.9521	High Similarity	NPC217149
0.9521	High Similarity	NPC477957
0.9521	High Similarity	NPC150123
0.9521	High Similarity	NPC216035
0.9521	High Similarity	NPC10807
0.9521	High Similarity	NPC243171
0.9521	High Similarity	NPC285623
0.9521	High Similarity	NPC138288
0.9521	High Similarity	NPC56232
0.9521	High Similarity	NPC244583
0.9521	High Similarity	NPC171651
0.9517	High Similarity	NPC105136
0.9514	High Similarity	NPC161191
0.9514	High Similarity	NPC132592
0.9514	High Similarity	NPC160821
0.951	High Similarity	NPC109183
0.951	High Similarity	NPC470131
0.951	High Similarity	NPC473078
0.951	High Similarity	NPC470133
0.951	High Similarity	NPC470132
0.951	High Similarity	NPC470134
0.9507	High Similarity	NPC106985
0.9507	High Similarity	NPC18585
0.9507	High Similarity	NPC166138
0.9507	High Similarity	NPC471621
0.9504	High Similarity	NPC3188
0.95	High Similarity	NPC274784
0.95	High Similarity	NPC265871
0.95	High Similarity	NPC222342
0.95	High Similarity	NPC329203
0.95	High Similarity	NPC20709
0.95	High Similarity	NPC310135
0.95	High Similarity	NPC150648
0.95	High Similarity	NPC225153
0.95	High Similarity	NPC140890
0.9459	High Similarity	NPC215917
0.9459	High Similarity	NPC10754
0.9459	High Similarity	NPC20530
0.9456	High Similarity	NPC469405
0.9456	High Similarity	NPC180301
0.9456	High Similarity	NPC248793
0.9456	High Similarity	NPC293286
0.9452	High Similarity	NPC474744
0.9452	High Similarity	NPC209846
0.9452	High Similarity	NPC474772
0.9452	High Similarity	NPC472423
0.9452	High Similarity	NPC328740
0.9452	High Similarity	NPC289774
0.9452	High Similarity	NPC471675
0.9452	High Similarity	NPC477897
0.9448	High Similarity	NPC5173
0.9448	High Similarity	NPC473016
0.9448	High Similarity	NPC89442
0.9444	High Similarity	NPC40086
0.9444	High Similarity	NPC44721
0.9444	High Similarity	NPC10990
0.9444	High Similarity	NPC222298
0.9444	High Similarity	NPC85773
0.9444	High Similarity	NPC51070
0.9444	High Similarity	NPC91902
0.9444	High Similarity	NPC176869
0.9444	High Similarity	NPC3779
0.9444	High Similarity	NPC470670
0.9444	High Similarity	NPC47388
0.9444	High Similarity	NPC472918

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 NPC472627 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	850
0.2-0.3	1596
0.3-0.4	2581
0.4-0.5	1931
0.5-0.6	1144
0.6-0.7	505
0.7-0.8	165
0.8-0.85	25
0.85-0.9	18
0.9-0.95	8
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9357	High Similarity	NPD1552	Clinical (unspecified phase)
0.9357	High Similarity	NPD1550	Clinical (unspecified phase)
0.9324	High Similarity	NPD2393	Clinical (unspecified phase)
0.9291	High Similarity	NPD1549	Phase 2
0.9252	High Similarity	NPD4380	Phase 2
0.9172	High Similarity	NPD4378	Clinical (unspecified phase)
0.9139	High Similarity	NPD7075	Discontinued
0.9067	High Similarity	NPD7096	Clinical (unspecified phase)
0.9041	High Similarity	NPD7410	Clinical (unspecified phase)
0.9007	High Similarity	NPD8443	Clinical (unspecified phase)
0.9	High Similarity	NPD1934	Approved
0.9	High Similarity	NPD6801	Discontinued
0.8933	High Similarity	NPD7411	Suspended
0.8889	High Similarity	NPD4381	Clinical (unspecified phase)
0.8881	High Similarity	NPD2796	Approved
0.8811	High Similarity	NPD1510	Phase 2
0.8794	High Similarity	NPD1240	Approved
0.8742	High Similarity	NPD7804	Clinical (unspecified phase)
0.8716	High Similarity	NPD6799	Approved
0.8693	High Similarity	NPD7819	Suspended
0.8671	High Similarity	NPD6167	Clinical (unspecified phase)
0.8671	High Similarity	NPD6168	Clinical (unspecified phase)
0.8671	High Similarity	NPD1607	Approved
0.8671	High Similarity	NPD6166	Phase 2
0.8591	High Similarity	NPD1511	Approved
0.8571	High Similarity	NPD2801	Approved
0.8497	Intermediate Similarity	NPD6599	Discontinued
0.8481	Intermediate Similarity	NPD6959	Discontinued
0.8477	Intermediate Similarity	NPD1512	Approved
0.8462	Intermediate Similarity	NPD3882	Suspended
0.8457	Intermediate Similarity	NPD7074	Phase 3
0.8446	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD5403	Approved
0.8395	Intermediate Similarity	NPD7054	Approved
0.8354	Intermediate Similarity	NPD6559	Discontinued
0.8344	Intermediate Similarity	NPD7472	Approved
0.8344	Intermediate Similarity	NPD7768	Phase 2
0.8333	Intermediate Similarity	NPD3818	Discontinued
0.8302	Intermediate Similarity	NPD5494	Approved
0.8293	Intermediate Similarity	NPD6797	Phase 2
0.8289	Intermediate Similarity	NPD5401	Approved
0.828	Intermediate Similarity	NPD3817	Phase 2
0.8264	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7251	Discontinued
0.8228	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD2800	Approved
0.8193	Intermediate Similarity	NPD7808	Phase 3
0.8176	Intermediate Similarity	NPD3749	Approved
0.8163	Intermediate Similarity	NPD6651	Approved
0.8146	Intermediate Similarity	NPD3750	Approved
0.8146	Intermediate Similarity	NPD4628	Phase 3
0.8121	Intermediate Similarity	NPD1551	Phase 2
0.8084	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5844	Phase 1
0.8054	Intermediate Similarity	NPD7033	Discontinued
0.805	Intermediate Similarity	NPD5402	Approved
0.8014	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2935	Discontinued
0.7975	Intermediate Similarity	NPD6232	Discontinued
0.7973	Intermediate Similarity	NPD5124	Phase 1
0.7973	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD5953	Discontinued
0.7961	Intermediate Similarity	NPD1243	Approved
0.7952	Intermediate Similarity	NPD7286	Phase 2
0.7949	Intermediate Similarity	NPD920	Approved
0.7939	Intermediate Similarity	NPD7473	Discontinued
0.7935	Intermediate Similarity	NPD2534	Approved
0.7935	Intermediate Similarity	NPD2533	Approved
0.7935	Intermediate Similarity	NPD2532	Approved
0.7933	Intermediate Similarity	NPD2799	Discontinued
0.7922	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6100	Approved
0.7881	Intermediate Similarity	NPD6099	Approved
0.7877	Intermediate Similarity	NPD4908	Phase 1
0.7857	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD4363	Phase 3
0.7829	Intermediate Similarity	NPD2344	Approved
0.7829	Intermediate Similarity	NPD4360	Phase 2
0.7821	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD3748	Approved
0.7793	Intermediate Similarity	NPD1203	Approved
0.7785	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD943	Approved
0.7785	Intermediate Similarity	NPD1613	Approved
0.777	Intermediate Similarity	NPD2313	Discontinued
0.7762	Intermediate Similarity	NPD1610	Phase 2
0.7755	Intermediate Similarity	NPD6832	Phase 2
0.775	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1548	Phase 1
0.7714	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD919	Approved
0.7677	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2424	Discontinued
0.7651	Intermediate Similarity	NPD6798	Discontinued
0.7651	Intermediate Similarity	NPD3268	Approved
0.765	Intermediate Similarity	NPD7584	Approved
0.7628	Intermediate Similarity	NPD2309	Approved
0.7625	Intermediate Similarity	NPD3226	Approved
0.7597	Intermediate Similarity	NPD2346	Discontinued
0.7595	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD1247	Approved
0.7586	Intermediate Similarity	NPD9717	Approved
0.7584	Intermediate Similarity	NPD4625	Phase 3
0.7584	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD4361	Phase 2
0.7574	Intermediate Similarity	NPD3751	Discontinued
0.7551	Intermediate Similarity	NPD2797	Approved
0.7546	Intermediate Similarity	NPD1465	Phase 2
0.7545	Intermediate Similarity	NPD3787	Discontinued
0.7532	Intermediate Similarity	NPD7390	Discontinued
0.7517	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD422	Phase 1
0.7516	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8313	Approved
0.7514	Intermediate Similarity	NPD8312	Approved
0.75	Intermediate Similarity	NPD2798	Approved
0.75	Intermediate Similarity	NPD2654	Approved
0.75	Intermediate Similarity	NPD3926	Phase 2
0.75	Intermediate Similarity	NPD1652	Phase 2
0.75	Intermediate Similarity	NPD1933	Approved
0.7485	Intermediate Similarity	NPD1729	Discontinued
0.7484	Intermediate Similarity	NPD4661	Approved
0.7484	Intermediate Similarity	NPD4662	Approved
0.7468	Intermediate Similarity	NPD4308	Phase 3
0.7467	Intermediate Similarity	NPD3027	Phase 3
0.745	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3823	Discontinued
0.744	Intermediate Similarity	NPD5710	Approved
0.744	Intermediate Similarity	NPD5711	Approved
0.7439	Intermediate Similarity	NPD8455	Phase 2
0.7418	Intermediate Similarity	NPD6779	Approved
0.7418	Intermediate Similarity	NPD6782	Approved
0.7418	Intermediate Similarity	NPD6776	Approved
0.7418	Intermediate Similarity	NPD6778	Approved
0.7418	Intermediate Similarity	NPD6777	Approved
0.7418	Intermediate Similarity	NPD6780	Approved
0.7418	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD6781	Approved
0.7417	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7458	Discontinued
0.7391	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8434	Phase 2
0.7386	Intermediate Similarity	NPD6355	Discontinued
0.7386	Intermediate Similarity	NPD230	Phase 1
0.7381	Intermediate Similarity	NPD7199	Phase 2
0.7368	Intermediate Similarity	NPD6233	Phase 2
0.7365	Intermediate Similarity	NPD3225	Approved
0.7361	Intermediate Similarity	NPD9545	Approved
0.7347	Intermediate Similarity	NPD3972	Approved
0.7329	Intermediate Similarity	NPD5049	Phase 3
0.7317	Intermediate Similarity	NPD5889	Approved
0.7317	Intermediate Similarity	NPD5890	Approved
0.7315	Intermediate Similarity	NPD3266	Approved
0.7315	Intermediate Similarity	NPD3267	Approved
0.7299	Intermediate Similarity	NPD6104	Discontinued
0.7297	Intermediate Similarity	NPD7435	Discontinued
0.7297	Intermediate Similarity	NPD4749	Approved
0.7296	Intermediate Similarity	NPD3887	Approved
0.7296	Intermediate Similarity	NPD2354	Approved
0.7288	Intermediate Similarity	NPD8150	Discontinued
0.7278	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6844	Discontinued
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6585	Discontinued
0.7254	Intermediate Similarity	NPD1241	Discontinued
0.7251	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7229	Phase 3
0.7234	Intermediate Similarity	NPD7585	Approved
0.723	Intermediate Similarity	NPD1608	Approved
0.7229	Intermediate Similarity	NPD5761	Phase 2
0.7229	Intermediate Similarity	NPD5760	Phase 2
0.7222	Intermediate Similarity	NPD9493	Approved
0.7219	Intermediate Similarity	NPD2861	Phase 2
0.7211	Intermediate Similarity	NPD7783	Phase 2
0.7211	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD4307	Phase 2
0.7208	Intermediate Similarity	NPD4060	Phase 1
0.7207	Intermediate Similarity	NPD4287	Approved
0.7207	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7213	Phase 3
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD7212	Phase 2
0.7204	Intermediate Similarity	NPD7697	Approved
0.7204	Intermediate Similarity	NPD7696	Phase 3
0.7204	Intermediate Similarity	NPD7698	Approved
0.7196	Intermediate Similarity	NPD8151	Discontinued
0.7193	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD3764	Approved
0.719	Intermediate Similarity	NPD1296	Phase 2
0.7188	Intermediate Similarity	NPD6190	Approved
0.7186	Intermediate Similarity	NPD4288	Approved
0.7181	Intermediate Similarity	NPD7583	Approved
0.7179	Intermediate Similarity	NPD4537	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