NPASS Compound

Structure

NPC472633 OpenBabel07101718182D 31 34 0 0 1 0 0 0 0 0999 V2000 -3.9533 1.3625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1780 0.1378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 -0.0517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5050 -0.3105 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 -1.8320 -0.7588 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 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2121 0.3966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 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 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 1 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 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.7942 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 25 1 0 0 0 0 4 5 1 0 0 0 0 4 7 1 0 0 0 0 5 14 2 0 0 0 0 6 8 2 0 0 0 0 6 18 1 0 0 0 0 7 25 1 0 0 0 0 8 25 1 0 0 0 0 9 15 2 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 10 17 2 0 0 0 0 11 16 2 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 13 22 1 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 21 1 0 0 0 0 18 24 2 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 30 1 0 0 0 0 21 31 1 0 0 0 0 22 23 2 0 0 0 0 22 30 1 0 0 0 0 23 24 1 0 0 0 0 24 29 1 0 0 0 0 25 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.17
Volume:	435.743
LogP:	5.441
LogD:	3.865
LogS:	-3.45
# Rotatable Bonds:	4
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	4.009
Fsp3:	0.32
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:	-4.786
MDCK Permeability:	1.633838655834552e-05
Pgp-inhibitor:	0.115
Pgp-substrate:	0.053
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.396
30% Bioavailability (F30%):	0.438

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	98.55671691894531%
Volume Distribution (VD):	1.176
Pgp-substrate:	2.710888624191284%

ADMET: Metabolism

CYP1A2-inhibitor:	0.797
CYP1A2-substrate:	0.43
CYP2C19-inhibitor:	0.885
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.872
CYP2C9-substrate:	0.944
CYP2D6-inhibitor:	0.934
CYP2D6-substrate:	0.2
CYP3A4-inhibitor:	0.856
CYP3A4-substrate:	0.154

ADMET: Excretion

Clearance (CL):	16.61
Half-life (T1/2):	0.505

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.893
Drug-inuced Liver Injury (DILI):	0.748
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.856
Maximum Recommended Daily Dose:	0.925
Skin Sensitization:	0.934
Carcinogencity:	0.771
Eye Corrosion:	0.003
Eye Irritation:	0.335
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC472633

Natural Product ID:	NPC472633
*Common Name:**	OMWKLHZQLGFNOZ-JINQPTGOSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	OMWKLHZQLGFNOZ-JINQPTGOSA-N
Standard InCHI:	InChI=1S/C25H26O6/c1-14(2)5-4-7-25(3)8-6-18-21(31-25)13-22-23(24(18)29)19(28)12-20(30-22)15-9-16(26)11-17(27)10-15/h5-6,8-11,13,20,26-27,29H,4,7,12H2,1-3H3/t20-,25?/m0/s1
SMILES:	CC(=CCCC1(C)C=Cc2c(O1)cc1c(c2O)C(=O)C[C@H](O1)c1cc(O)cc(c1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581353
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0003520] Pyranoflavonoids

*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	2

Activity Type	# Activity
Cell Line	1
Individual Protein	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[447440]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	350.0	nM	PMID[447441]

☑ 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 NPC472633 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	381
0.1-0.2	1564
0.2-0.3	3709
0.3-0.4	9467
0.4-0.5	8989
0.5-0.6	3408
0.6-0.7	5212
0.7-0.8	5534
0.8-0.85	2486
0.85-0.9	1363
0.9-0.95	515
0.95-1	69

Similarity Score	Similarity Level	Natural Product ID
0.979	High Similarity	NPC296998
0.979	High Similarity	NPC473077
0.972	High Similarity	NPC195621
0.972	High Similarity	NPC24136
0.972	High Similarity	NPC88964
0.972	High Similarity	NPC246948
0.972	High Similarity	NPC301276
0.972	High Similarity	NPC475052
0.972	High Similarity	NPC176229
0.972	High Similarity	NPC20488
0.972	High Similarity	NPC187282
0.972	High Similarity	NPC111786
0.972	High Similarity	NPC142405
0.972	High Similarity	NPC83357
0.972	High Similarity	NPC67805
0.972	High Similarity	NPC54577
0.972	High Similarity	NPC312973
0.972	High Similarity	NPC214774
0.972	High Similarity	NPC290133
0.972	High Similarity	NPC470647
0.972	High Similarity	NPC267375
0.9655	High Similarity	NPC5173
0.9653	High Similarity	NPC283234
0.9653	High Similarity	NPC110303
0.9653	High Similarity	NPC23728
0.9597	High Similarity	NPC281137
0.9597	High Similarity	NPC473272
0.9597	High Similarity	NPC282390
0.9597	High Similarity	NPC284820
0.9589	High Similarity	NPC37348
0.9589	High Similarity	NPC471115
0.9589	High Similarity	NPC29777
0.9586	High Similarity	NPC296869
0.9586	High Similarity	NPC160821
0.9586	High Similarity	NPC132592
0.9586	High Similarity	NPC161191
0.9583	High Similarity	NPC472629
0.958	High Similarity	NPC214166
0.958	High Similarity	NPC478086
0.958	High Similarity	NPC219915
0.958	High Similarity	NPC316816
0.9527	High Similarity	NPC223701
0.9527	High Similarity	NPC472583
0.9527	High Similarity	NPC7989
0.9527	High Similarity	NPC236756
0.9527	High Similarity	NPC311579
0.9521	High Similarity	NPC473016
0.9517	High Similarity	NPC97716
0.9517	High Similarity	NPC79469
0.9517	High Similarity	NPC201731
0.9517	High Similarity	NPC237635
0.9517	High Similarity	NPC104406
0.9517	High Similarity	NPC24673
0.9514	High Similarity	NPC209040
0.9514	High Similarity	NPC470890
0.9514	High Similarity	NPC319752
0.9514	High Similarity	NPC124780
0.9514	High Similarity	NPC224714
0.9514	High Similarity	NPC131579
0.9514	High Similarity	NPC131568
0.9514	High Similarity	NPC87486
0.951	High Similarity	NPC194432
0.951	High Similarity	NPC265040
0.951	High Similarity	NPC64915
0.951	High Similarity	NPC166482
0.951	High Similarity	NPC76372
0.951	High Similarity	NPC223500
0.951	High Similarity	NPC73028
0.951	High Similarity	NPC32739
0.951	High Similarity	NPC107572
0.951	High Similarity	NPC227579
0.951	High Similarity	NPC78
0.951	High Similarity	NPC161506
0.951	High Similarity	NPC228504
0.951	High Similarity	NPC324134
0.951	High Similarity	NPC125855
0.951	High Similarity	NPC10937
0.951	High Similarity	NPC148757
0.951	High Similarity	NPC324436
0.951	High Similarity	NPC167624
0.951	High Similarity	NPC328164
0.951	High Similarity	NPC37496
0.951	High Similarity	NPC182852
0.951	High Similarity	NPC76338
0.951	High Similarity	NPC177354
0.951	High Similarity	NPC296917
0.951	High Similarity	NPC66515
0.951	High Similarity	NPC40833
0.951	High Similarity	NPC220998
0.951	High Similarity	NPC1089
0.951	High Similarity	NPC166934
0.951	High Similarity	NPC306829
0.947	High Similarity	NPC119209
0.947	High Similarity	NPC475784
0.947	High Similarity	NPC192686
0.947	High Similarity	NPC118256
0.9467	High Similarity	NPC471209
0.9463	High Similarity	NPC217706
0.9463	High Similarity	NPC207809
0.9463	High Similarity	NPC259710
0.9463	High Similarity	NPC48579
0.9463	High Similarity	NPC304207
0.9459	High Similarity	NPC56232
0.9459	High Similarity	NPC142527
0.9459	High Similarity	NPC475790
0.9459	High Similarity	NPC150123
0.9459	High Similarity	NPC161881
0.9459	High Similarity	NPC10807
0.9459	High Similarity	NPC244583
0.9456	High Similarity	NPC101957
0.9456	High Similarity	NPC61258
0.9456	High Similarity	NPC120105
0.9452	High Similarity	NPC244407
0.9452	High Similarity	NPC189087
0.9452	High Similarity	NPC321623
0.9452	High Similarity	NPC6511
0.9452	High Similarity	NPC168085
0.9452	High Similarity	NPC266572
0.9448	High Similarity	NPC476088
0.9448	High Similarity	NPC474161
0.9448	High Similarity	NPC124729
0.9448	High Similarity	NPC285630
0.9448	High Similarity	NPC127059
0.9448	High Similarity	NPC470131
0.9448	High Similarity	NPC470133
0.9448	High Similarity	NPC473078
0.9448	High Similarity	NPC470132
0.9448	High Similarity	NPC470134
0.9448	High Similarity	NPC109183
0.9444	High Similarity	NPC38219
0.9444	High Similarity	NPC143896
0.9444	High Similarity	NPC149026
0.9444	High Similarity	NPC91560
0.9444	High Similarity	NPC77794
0.9444	High Similarity	NPC223812
0.9444	High Similarity	NPC75049
0.9444	High Similarity	NPC185276
0.9444	High Similarity	NPC39329
0.9444	High Similarity	NPC310130
0.9444	High Similarity	NPC107177
0.9444	High Similarity	NPC18585
0.9444	High Similarity	NPC169591
0.9444	High Similarity	NPC68104
0.9444	High Similarity	NPC257097
0.9444	High Similarity	NPC85162
0.9444	High Similarity	NPC81697
0.9444	High Similarity	NPC166138
0.9444	High Similarity	NPC150408
0.9444	High Similarity	NPC164980
0.9444	High Similarity	NPC125894
0.9444	High Similarity	NPC106985
0.9444	High Similarity	NPC175504
0.9444	High Similarity	NPC278249
0.9444	High Similarity	NPC221432
0.9441	High Similarity	NPC17170
0.9441	High Similarity	NPC213322
0.9441	High Similarity	NPC110038
0.9441	High Similarity	NPC258630
0.9441	High Similarity	NPC156190
0.9441	High Similarity	NPC4743
0.9441	High Similarity	NPC324386
0.9441	High Similarity	NPC248372
0.9441	High Similarity	NPC96408
0.9441	High Similarity	NPC279650
0.9441	High Similarity	NPC166689
0.9441	High Similarity	NPC312391
0.9408	High Similarity	NPC474038
0.94	High Similarity	NPC208152
0.94	High Similarity	NPC78492
0.9396	High Similarity	NPC192083
0.9396	High Similarity	NPC469405
0.9396	High Similarity	NPC178964
0.9396	High Similarity	NPC95842
0.9396	High Similarity	NPC280530
0.9396	High Similarity	NPC248793
0.9396	High Similarity	NPC180301
0.9396	High Similarity	NPC74924
0.9396	High Similarity	NPC213896
0.9396	High Similarity	NPC193200
0.9392	High Similarity	NPC474021
0.9392	High Similarity	NPC244577
0.9392	High Similarity	NPC289774
0.9392	High Similarity	NPC471677
0.9392	High Similarity	NPC472420
0.9392	High Similarity	NPC474023
0.9392	High Similarity	NPC472636
0.9392	High Similarity	NPC477897
0.9392	High Similarity	NPC472422
0.9392	High Similarity	NPC471675
0.9392	High Similarity	NPC471676
0.9392	High Similarity	NPC263384
0.9392	High Similarity	NPC328740
0.9392	High Similarity	NPC209846
0.9388	High Similarity	NPC266499
0.9388	High Similarity	NPC104236
0.9388	High Similarity	NPC317492
0.9388	High Similarity	NPC474052
0.9388	High Similarity	NPC164205
0.9384	High Similarity	NPC300988
0.9384	High Similarity	NPC472627

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 NPC472633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	946
0.2-0.3	1555
0.3-0.4	2575
0.4-0.5	1891
0.5-0.6	1153
0.6-0.7	472
0.7-0.8	166
0.8-0.85	38
0.85-0.9	14
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9396	High Similarity	NPD2393	Clinical (unspecified phase)
0.9379	High Similarity	NPD4378	Clinical (unspecified phase)
0.9195	High Similarity	NPD4380	Phase 2
0.9161	High Similarity	NPD1552	Clinical (unspecified phase)
0.9161	High Similarity	NPD1550	Clinical (unspecified phase)
0.9116	High Similarity	NPD7410	Clinical (unspecified phase)
0.9097	High Similarity	NPD1549	Phase 2
0.9079	High Similarity	NPD8443	Clinical (unspecified phase)
0.9073	High Similarity	NPD1934	Approved
0.8958	High Similarity	NPD2796	Approved
0.891	High Similarity	NPD6959	Discontinued
0.8889	High Similarity	NPD1510	Phase 2
0.8889	High Similarity	NPD7819	Suspended
0.8882	High Similarity	NPD7411	Suspended
0.8839	High Similarity	NPD7075	Discontinued
0.8839	High Similarity	NPD4381	Clinical (unspecified phase)
0.8792	High Similarity	NPD1511	Approved
0.8766	High Similarity	NPD2801	Approved
0.8766	High Similarity	NPD7096	Clinical (unspecified phase)
0.8742	High Similarity	NPD6166	Phase 2
0.8742	High Similarity	NPD6168	Clinical (unspecified phase)
0.8742	High Similarity	NPD6167	Clinical (unspecified phase)
0.8696	High Similarity	NPD7804	Clinical (unspecified phase)
0.8675	High Similarity	NPD1512	Approved
0.8611	High Similarity	NPD1240	Approved
0.8608	High Similarity	NPD5494	Approved
0.8581	High Similarity	NPD6801	Discontinued
0.858	High Similarity	NPD7054	Approved
0.8528	High Similarity	NPD7074	Phase 3
0.8528	High Similarity	NPD7472	Approved
0.8509	High Similarity	NPD7852	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1607	Approved
0.8476	Intermediate Similarity	NPD6797	Phase 2
0.8471	Intermediate Similarity	NPD3817	Phase 2
0.8424	Intermediate Similarity	NPD7251	Discontinued
0.8418	Intermediate Similarity	NPD7768	Phase 2
0.8418	Intermediate Similarity	NPD3882	Suspended
0.8418	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD3818	Discontinued
0.8373	Intermediate Similarity	NPD7808	Phase 3
0.8344	Intermediate Similarity	NPD3750	Approved
0.8333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD2935	Discontinued
0.8313	Intermediate Similarity	NPD6559	Discontinued
0.8301	Intermediate Similarity	NPD6799	Approved
0.8278	Intermediate Similarity	NPD2800	Approved
0.8278	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD3749	Approved
0.8247	Intermediate Similarity	NPD2532	Approved
0.8247	Intermediate Similarity	NPD2534	Approved
0.8247	Intermediate Similarity	NPD2533	Approved
0.8242	Intermediate Similarity	NPD5844	Phase 1
0.8239	Intermediate Similarity	NPD5402	Approved
0.816	Intermediate Similarity	NPD6232	Discontinued
0.8141	Intermediate Similarity	NPD5403	Approved
0.8141	Intermediate Similarity	NPD920	Approved
0.8121	Intermediate Similarity	NPD7473	Discontinued
0.8101	Intermediate Similarity	NPD6599	Discontinued
0.8095	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8079	Intermediate Similarity	NPD6100	Approved
0.8079	Intermediate Similarity	NPD6099	Approved
0.8079	Intermediate Similarity	NPD1551	Phase 2
0.8047	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD1243	Approved
0.8013	Intermediate Similarity	NPD5401	Approved
0.8013	Intermediate Similarity	NPD3748	Approved
0.8013	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6651	Approved
0.8	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4363	Phase 3
0.8	Intermediate Similarity	NPD4360	Phase 2
0.7973	Intermediate Similarity	NPD2313	Discontinued
0.7959	Intermediate Similarity	NPD4908	Phase 1
0.7949	Intermediate Similarity	NPD7390	Discontinued
0.7933	Intermediate Similarity	NPD5124	Phase 1
0.7933	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD5953	Discontinued
0.7925	Intermediate Similarity	NPD3226	Approved
0.7917	Intermediate Similarity	NPD7286	Phase 2
0.7908	Intermediate Similarity	NPD2346	Discontinued
0.7895	Intermediate Similarity	NPD2799	Discontinued
0.7895	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7033	Discontinued
0.7879	Intermediate Similarity	NPD1247	Approved
0.7871	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD919	Approved
0.7847	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2344	Approved
0.7785	Intermediate Similarity	NPD4625	Phase 3
0.7785	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7748	Intermediate Similarity	NPD943	Approved
0.7748	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1613	Approved
0.773	Intermediate Similarity	NPD1465	Phase 2
0.7725	Intermediate Similarity	NPD5710	Approved
0.7725	Intermediate Similarity	NPD5711	Approved
0.7724	Intermediate Similarity	NPD1610	Phase 2
0.7716	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1548	Phase 1
0.7669	Intermediate Similarity	NPD6844	Discontinued
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7635	Intermediate Similarity	NPD1203	Approved
0.7622	Intermediate Similarity	NPD7584	Approved
0.7619	Intermediate Similarity	NPD3787	Discontinued
0.7616	Intermediate Similarity	NPD3268	Approved
0.7611	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD6832	Phase 2
0.7595	Intermediate Similarity	NPD2309	Approved
0.7586	Intermediate Similarity	NPD8313	Approved
0.7586	Intermediate Similarity	NPD8312	Approved
0.7584	Intermediate Similarity	NPD2798	Approved
0.7582	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD3926	Phase 2
0.7556	Intermediate Similarity	NPD4361	Phase 2
0.7556	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD4308	Phase 3
0.7533	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2861	Phase 2
0.7517	Intermediate Similarity	NPD2797	Approved
0.7515	Intermediate Similarity	NPD7229	Phase 3
0.75	Intermediate Similarity	NPD4749	Approved
0.75	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6777	Approved
0.7486	Intermediate Similarity	NPD6779	Approved
0.7486	Intermediate Similarity	NPD6776	Approved
0.7486	Intermediate Similarity	NPD6778	Approved
0.7486	Intermediate Similarity	NPD6782	Approved
0.7486	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6780	Approved
0.7486	Intermediate Similarity	NPD6781	Approved
0.7483	Intermediate Similarity	NPD422	Phase 1
0.7469	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD230	Phase 1
0.745	Intermediate Similarity	NPD3225	Approved
0.7434	Intermediate Similarity	NPD3027	Phase 3
0.7432	Intermediate Similarity	NPD9717	Approved
0.7432	Intermediate Similarity	NPD1608	Approved
0.7405	Intermediate Similarity	NPD2424	Discontinued
0.7394	Intermediate Similarity	NPD5889	Approved
0.7394	Intermediate Similarity	NPD5890	Approved
0.7389	Intermediate Similarity	NPD5406	Approved
0.7389	Intermediate Similarity	NPD5405	Approved
0.7389	Intermediate Similarity	NPD5404	Approved
0.7389	Intermediate Similarity	NPD5408	Approved
0.7378	Intermediate Similarity	NPD7458	Discontinued
0.7374	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7435	Discontinued
0.7366	Intermediate Similarity	NPD7698	Approved
0.7366	Intermediate Similarity	NPD7696	Phase 3
0.7366	Intermediate Similarity	NPD7697	Approved
0.7365	Intermediate Similarity	NPD1201	Approved
0.7365	Intermediate Similarity	NPD4288	Approved
0.736	Intermediate Similarity	NPD8150	Discontinued
0.7358	Intermediate Similarity	NPD2654	Approved
0.7356	Intermediate Similarity	NPD1729	Discontinued
0.7355	Intermediate Similarity	NPD447	Suspended
0.7333	Intermediate Similarity	NPD6585	Discontinued
0.7326	Intermediate Similarity	NPD7870	Phase 2
0.7326	Intermediate Similarity	NPD7871	Phase 2
0.7305	Intermediate Similarity	NPD5761	Phase 2
0.7305	Intermediate Similarity	NPD5760	Phase 2
0.7305	Intermediate Similarity	NPD8455	Phase 2
0.7303	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6273	Approved
0.729	Intermediate Similarity	NPD4307	Phase 2
0.7285	Intermediate Similarity	NPD3266	Approved
0.7285	Intermediate Similarity	NPD1470	Approved
0.7285	Intermediate Similarity	NPD3267	Approved
0.7284	Intermediate Similarity	NPD7212	Phase 2
0.7284	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7213	Phase 3
0.7278	Intermediate Similarity	NPD4287	Approved
0.7277	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7783	Phase 2
0.7273	Intermediate Similarity	NPD411	Approved
0.7273	Intermediate Similarity	NPD6798	Discontinued
0.7263	Intermediate Similarity	NPD8151	Discontinued
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7251	Intermediate Similarity	NPD7199	Phase 2
0.725	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1652	Phase 2
0.7246	Intermediate Similarity	NPD37	Approved
0.7244	Intermediate Similarity	NPD1933	Approved
0.7241	Intermediate Similarity	NPD7177	Discontinued
0.7239	Intermediate Similarity	NPD7447	Phase 1
0.7235	Intermediate Similarity	NPD6234	Discontinued
0.7233	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD17	Approved
0.7225	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6823	Phase 2
0.7219	Intermediate Similarity	NPD4966	Approved
0.7219	Intermediate Similarity	NPD4967	Phase 2

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