NPASS Compound

Structure

NPC471620 OpenBabel07101718292D 24 25 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 4.3301 -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 3.4641 0.0000 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 1.0000 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 2.5981 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 -0.0000 1.0000 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 0.0000 -0.0000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 24 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 2 0 0 0 0 6 11 2 0 0 0 0 7 11 1 0 0 0 0 8 13 1 0 0 0 0 8 14 2 0 0 0 0 9 12 1 0 0 0 0 9 19 2 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 12 17 1 0 0 0 0 12 18 2 0 0 0 0 13 20 2 0 0 0 0 14 15 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 17 2 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	331.785
LogP:	3.645
LogD:	1.917
LogS:	-4.069
# Rotatable Bonds:	6
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.48
Synthetic Accessibility Score:	2.579
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.842
MDCK Permeability:	1.9441558833932504e-05
Pgp-inhibitor:	0.016
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	96.90081787109375%
Volume Distribution (VD):	0.845
Pgp-substrate:	2.2432663440704346%

ADMET: Metabolism

CYP1A2-inhibitor:	0.734
CYP1A2-substrate:	0.347
CYP2C19-inhibitor:	0.522
CYP2C19-substrate:	0.14
CYP2C9-inhibitor:	0.757
CYP2C9-substrate:	0.789
CYP2D6-inhibitor:	0.182
CYP2D6-substrate:	0.188
CYP3A4-inhibitor:	0.528
CYP3A4-substrate:	0.17

ADMET: Excretion

Clearance (CL):	2.943
Half-life (T1/2):	0.562

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.028
Drug-inuced Liver Injury (DILI):	0.922
AMES Toxicity:	0.317
Rat Oral Acute Toxicity:	0.194
Maximum Recommended Daily Dose:	0.077
Skin Sensitization:	0.524
Carcinogencity:	0.231
Eye Corrosion:	0.017
Eye Irritation:	0.937
Respiratory Toxicity:	0.898

Download Data

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

Natural Product: NPC471620

Natural Product ID:	NPC471620
*Common Name:**	NDXOLILIMMVXLG-ZSOIEALJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NDXOLILIMMVXLG-ZSOIEALJSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-10-16(22)15(17(23)12(9-19)18(10)24-2)14(21)8-13(20)11-6-4-3-5-7-11/h3-9,21-23H,1-2H3/b14-8-
SMILES:	O=Cc1c(O)c(/C(=C/C(=O)c2ccccc2)/O)c(c(c1OC)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL299341
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003474] Retrochalcones

*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
NPO33071	desmos spp.	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12729671]

☑ 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
EC50	1
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	10.7	ug.mL-1	PMID[516262]
NPT759	Cell Line	H9	Homo sapiens	EC50	=	0.022	ug.mL-1	PMID[516262]
NPT27	Others	Unspecified		Therapeutic index	=	489.0	n.a.	PMID[516262]

☑ 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 NPC471620 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	333
0.1-0.2	1587
0.2-0.3	4166
0.3-0.4	10727
0.4-0.5	7556
0.5-0.6	3876
0.6-0.7	6263
0.7-0.8	5287
0.8-0.85	1725
0.85-0.9	780
0.9-0.95	370
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC156092
0.9699	High Similarity	NPC186838
0.9699	High Similarity	NPC1486
0.9699	High Similarity	NPC66349
0.9699	High Similarity	NPC12165
0.9699	High Similarity	NPC41461
0.9699	High Similarity	NPC25287
0.9699	High Similarity	NPC477244
0.9699	High Similarity	NPC477242
0.9699	High Similarity	NPC249606
0.9699	High Similarity	NPC150399
0.9699	High Similarity	NPC477243
0.9699	High Similarity	NPC274109
0.9699	High Similarity	NPC168105
0.9699	High Similarity	NPC98115
0.9697	High Similarity	NPC103842
0.963	High Similarity	NPC470211
0.963	High Similarity	NPC283429
0.9627	High Similarity	NPC153979
0.9627	High Similarity	NPC317119
0.9627	High Similarity	NPC472419
0.9624	High Similarity	NPC13575
0.9624	High Similarity	NPC131039
0.9559	High Similarity	NPC215311
0.9559	High Similarity	NPC204985
0.9559	High Similarity	NPC172250
0.9559	High Similarity	NPC259166
0.9559	High Similarity	NPC326109
0.9559	High Similarity	NPC219917
0.9559	High Similarity	NPC213659
0.9559	High Similarity	NPC48624
0.9559	High Similarity	NPC144118
0.9559	High Similarity	NPC80962
0.9556	High Similarity	NPC21350
0.9549	High Similarity	NPC286336
0.9489	High Similarity	NPC268204
0.9489	High Similarity	NPC469404
0.9489	High Similarity	NPC470089
0.9489	High Similarity	NPC52789
0.9489	High Similarity	NPC26051
0.9489	High Similarity	NPC470087
0.9489	High Similarity	NPC321980
0.9489	High Similarity	NPC55832
0.9485	High Similarity	NPC472366
0.9485	High Similarity	NPC295384
0.9485	High Similarity	NPC477956
0.9474	High Similarity	NPC20560
0.9474	High Similarity	NPC472365
0.9474	High Similarity	NPC159623
0.9474	High Similarity	NPC28753
0.9474	High Similarity	NPC188646
0.9474	High Similarity	NPC139813
0.9474	High Similarity	NPC144051
0.9474	High Similarity	NPC242294
0.9474	High Similarity	NPC192304
0.9474	High Similarity	NPC294593
0.9474	High Similarity	NPC337373
0.9474	High Similarity	NPC27643
0.9474	High Similarity	NPC312318
0.9474	High Similarity	NPC175098
0.9474	High Similarity	NPC82225
0.9474	High Similarity	NPC263670
0.9474	High Similarity	NPC56031
0.9474	High Similarity	NPC18877
0.9474	High Similarity	NPC204960
0.9416	High Similarity	NPC253822
0.9416	High Similarity	NPC101366
0.9416	High Similarity	NPC11056
0.9412	High Similarity	NPC251681
0.9412	High Similarity	NPC243528
0.9412	High Similarity	NPC124269
0.9407	High Similarity	NPC222633
0.9403	High Similarity	NPC164136
0.9398	High Similarity	NPC87231
0.9398	High Similarity	NPC15834
0.9398	High Similarity	NPC129132
0.9398	High Similarity	NPC205468
0.9398	High Similarity	NPC212631
0.9398	High Similarity	NPC257756
0.9398	High Similarity	NPC215875
0.9357	High Similarity	NPC2416
0.9357	High Similarity	NPC476153
0.9357	High Similarity	NPC215885
0.9353	High Similarity	NPC169591
0.9353	High Similarity	NPC39329
0.9353	High Similarity	NPC257097
0.9353	High Similarity	NPC310130
0.9353	High Similarity	NPC150408
0.9353	High Similarity	NPC301751
0.9353	High Similarity	NPC475705
0.9353	High Similarity	NPC68104
0.9353	High Similarity	NPC476178
0.9353	High Similarity	NPC149026
0.9353	High Similarity	NPC51887
0.9353	High Similarity	NPC91560
0.9353	High Similarity	NPC75049
0.9353	High Similarity	NPC143896
0.9353	High Similarity	NPC117836
0.9353	High Similarity	NPC221432
0.9353	High Similarity	NPC164980
0.9353	High Similarity	NPC175504
0.9353	High Similarity	NPC245482
0.9353	High Similarity	NPC471621
0.9348	High Similarity	NPC110038
0.9348	High Similarity	NPC110969
0.9348	High Similarity	NPC3188
0.9348	High Similarity	NPC248372
0.9343	High Similarity	NPC217186
0.9343	High Similarity	NPC53181
0.9338	High Similarity	NPC294409
0.9338	High Similarity	NPC162680
0.9338	High Similarity	NPC7013
0.9338	High Similarity	NPC181124
0.9338	High Similarity	NPC116632
0.9338	High Similarity	NPC188879
0.9338	High Similarity	NPC303644
0.9338	High Similarity	NPC209560
0.9328	High Similarity	NPC16197
0.9323	High Similarity	NPC112192
0.9323	High Similarity	NPC128348
0.9323	High Similarity	NPC66384
0.9323	High Similarity	NPC313618
0.9323	High Similarity	NPC262359
0.9323	High Similarity	NPC309717
0.9323	High Similarity	NPC164236
0.9323	High Similarity	NPC475008
0.9323	High Similarity	NPC308037
0.9323	High Similarity	NPC64359
0.9323	High Similarity	NPC186097
0.9323	High Similarity	NPC189106
0.9323	High Similarity	NPC475009
0.9296	High Similarity	NPC214493
0.9286	High Similarity	NPC476055
0.9286	High Similarity	NPC110776
0.9286	High Similarity	NPC197252
0.9286	High Similarity	NPC209040
0.9286	High Similarity	NPC473013
0.9286	High Similarity	NPC271590
0.9286	High Similarity	NPC236766
0.9286	High Similarity	NPC473015
0.9281	High Similarity	NPC32739
0.9281	High Similarity	NPC161506
0.9281	High Similarity	NPC306829
0.9281	High Similarity	NPC78
0.9281	High Similarity	NPC66515
0.9281	High Similarity	NPC166482
0.9281	High Similarity	NPC194432
0.9281	High Similarity	NPC265040
0.9281	High Similarity	NPC220998
0.9281	High Similarity	NPC177354
0.9281	High Similarity	NPC125855
0.9281	High Similarity	NPC182852
0.9281	High Similarity	NPC107572
0.9281	High Similarity	NPC11561
0.9281	High Similarity	NPC76372
0.9281	High Similarity	NPC228504
0.9281	High Similarity	NPC148757
0.9281	High Similarity	NPC148545
0.9281	High Similarity	NPC37496
0.9281	High Similarity	NPC166934
0.9281	High Similarity	NPC64915
0.9281	High Similarity	NPC324134
0.9281	High Similarity	NPC167624
0.9281	High Similarity	NPC227579
0.9281	High Similarity	NPC226636
0.9281	High Similarity	NPC324436
0.9281	High Similarity	NPC223500
0.9281	High Similarity	NPC328164
0.9281	High Similarity	NPC40833
0.9281	High Similarity	NPC1089
0.9281	High Similarity	NPC76338
0.9281	High Similarity	NPC10937
0.9281	High Similarity	NPC296917
0.9275	High Similarity	NPC69769
0.9275	High Similarity	NPC270883
0.9275	High Similarity	NPC159275
0.9275	High Similarity	NPC241100
0.9275	High Similarity	NPC172986
0.9275	High Similarity	NPC261227
0.927	High Similarity	NPC309154
0.927	High Similarity	NPC12175
0.927	High Similarity	NPC278323
0.927	High Similarity	NPC90665
0.927	High Similarity	NPC55162
0.927	High Similarity	NPC472368
0.927	High Similarity	NPC279668
0.9265	High Similarity	NPC472367
0.9265	High Similarity	NPC472364
0.9265	High Similarity	NPC240593
0.9265	High Similarity	NPC24394
0.9265	High Similarity	NPC213603
0.9265	High Similarity	NPC473391
0.9265	High Similarity	NPC476333
0.9254	High Similarity	NPC103105
0.9248	High Similarity	NPC250057
0.9242	High Similarity	NPC476119
0.922	High Similarity	NPC316769
0.9214	High Similarity	NPC278249
0.9214	High Similarity	NPC125894
0.9214	High Similarity	NPC316816

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 NPC471620 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	976
0.2-0.3	1489
0.3-0.4	2676
0.4-0.5	1937
0.5-0.6	1192
0.6-0.7	391
0.7-0.8	129
0.8-0.85	29
0.85-0.9	7
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9323	High Similarity	NPD1240	Approved
0.9191	High Similarity	NPD1510	Phase 2
0.9185	High Similarity	NPD1607	Approved
0.9014	High Similarity	NPD7410	Clinical (unspecified phase)
0.9014	High Similarity	NPD4378	Clinical (unspecified phase)
0.8993	High Similarity	NPD1549	Phase 2
0.8921	High Similarity	NPD1550	Clinical (unspecified phase)
0.8921	High Similarity	NPD1552	Clinical (unspecified phase)
0.8836	High Similarity	NPD4380	Phase 2
0.8776	High Similarity	NPD7411	Suspended
0.8714	High Similarity	NPD2796	Approved
0.8658	High Similarity	NPD2393	Clinical (unspecified phase)
0.8633	High Similarity	NPD6651	Approved
0.8609	High Similarity	NPD7075	Discontinued
0.86	High Similarity	NPD8443	Clinical (unspecified phase)
0.8552	High Similarity	NPD6799	Approved
0.8533	High Similarity	NPD7819	Suspended
0.8533	High Similarity	NPD7096	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD6801	Discontinued
0.8451	Intermediate Similarity	NPD1551	Phase 2
0.8451	Intermediate Similarity	NPD2935	Discontinued
0.8403	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8344	Intermediate Similarity	NPD1934	Approved
0.8333	Intermediate Similarity	NPD6599	Discontinued
0.8301	Intermediate Similarity	NPD3882	Suspended
0.8301	Intermediate Similarity	NPD7768	Phase 2
0.828	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD2800	Approved
0.8255	Intermediate Similarity	NPD920	Approved
0.8247	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD2532	Approved
0.8243	Intermediate Similarity	NPD2533	Approved
0.8243	Intermediate Similarity	NPD2534	Approved
0.8231	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD1511	Approved
0.817	Intermediate Similarity	NPD2801	Approved
0.8121	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD3750	Approved
0.8089	Intermediate Similarity	NPD6959	Discontinued
0.8067	Intermediate Similarity	NPD1512	Approved
0.8038	Intermediate Similarity	NPD6232	Discontinued
0.8027	Intermediate Similarity	NPD1243	Approved
0.8025	Intermediate Similarity	NPD5953	Discontinued
0.8012	Intermediate Similarity	NPD7286	Phase 2
0.8012	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7473	Discontinued
0.8	Intermediate Similarity	NPD2799	Discontinued
0.7975	Intermediate Similarity	NPD6559	Discontinued
0.7972	Intermediate Similarity	NPD943	Approved
0.7937	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD6166	Phase 2
0.7937	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD5494	Approved
0.7898	Intermediate Similarity	NPD3749	Approved
0.7895	Intermediate Similarity	NPD5403	Approved
0.7891	Intermediate Similarity	NPD2344	Approved
0.7885	Intermediate Similarity	NPD3817	Phase 2
0.7857	Intermediate Similarity	NPD1203	Approved
0.7848	Intermediate Similarity	NPD919	Approved
0.784	Intermediate Similarity	NPD3818	Discontinued
0.7832	Intermediate Similarity	NPD2313	Discontinued
0.7818	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD6832	Phase 2
0.7801	Intermediate Similarity	NPD2798	Approved
0.7785	Intermediate Similarity	NPD2654	Approved
0.777	Intermediate Similarity	NPD3972	Approved
0.7763	Intermediate Similarity	NPD5401	Approved
0.7755	Intermediate Similarity	NPD3748	Approved
0.775	Intermediate Similarity	NPD1247	Approved
0.7744	Intermediate Similarity	NPD7074	Phase 3
0.7733	Intermediate Similarity	NPD4628	Phase 3
0.7722	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7390	Discontinued
0.7683	Intermediate Similarity	NPD7054	Approved
0.7682	Intermediate Similarity	NPD2309	Approved
0.7664	Intermediate Similarity	NPD9545	Approved
0.7647	Intermediate Similarity	NPD9493	Approved
0.7643	Intermediate Similarity	NPD9717	Approved
0.7636	Intermediate Similarity	NPD7472	Approved
0.7593	Intermediate Similarity	NPD5711	Approved
0.7593	Intermediate Similarity	NPD5710	Approved
0.759	Intermediate Similarity	NPD6797	Phase 2
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7569	Intermediate Similarity	NPD4908	Phase 1
0.7564	Intermediate Similarity	NPD7458	Discontinued
0.7564	Intermediate Similarity	NPD3226	Approved
0.7548	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5402	Approved
0.7545	Intermediate Similarity	NPD7251	Discontinued
0.7536	Intermediate Similarity	NPD1548	Phase 1
0.7533	Intermediate Similarity	NPD2346	Discontinued
0.7533	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD1729	Discontinued
0.7517	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD7808	Phase 3
0.7483	Intermediate Similarity	NPD1164	Approved
0.7482	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7467	Intermediate Similarity	NPD5405	Approved
0.7467	Intermediate Similarity	NPD6099	Approved
0.7467	Intermediate Similarity	NPD6100	Approved
0.7467	Intermediate Similarity	NPD5406	Approved
0.7467	Intermediate Similarity	NPD5404	Approved
0.7467	Intermediate Similarity	NPD5408	Approved
0.7466	Intermediate Similarity	NPD3268	Approved
0.7447	Intermediate Similarity	NPD422	Phase 1
0.7447	Intermediate Similarity	NPD1610	Phase 2
0.7439	Intermediate Similarity	NPD3926	Phase 2
0.7432	Intermediate Similarity	NPD5124	Phase 1
0.7432	Intermediate Similarity	NPD230	Phase 1
0.7432	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7003	Approved
0.7379	Intermediate Similarity	NPD9494	Approved
0.7371	Intermediate Similarity	NPD4363	Phase 3
0.7371	Intermediate Similarity	NPD4360	Phase 2
0.7361	Intermediate Similarity	NPD1470	Approved
0.7361	Intermediate Similarity	NPD2797	Approved
0.7358	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD4361	Phase 2
0.7324	Intermediate Similarity	NPD1201	Approved
0.7315	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1241	Discontinued
0.7292	Intermediate Similarity	NPD1876	Approved
0.7285	Intermediate Similarity	NPD4308	Phase 3
0.7285	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3027	Phase 3
0.7278	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5889	Approved
0.725	Intermediate Similarity	NPD5890	Approved
0.7235	Intermediate Similarity	NPD6104	Discontinued
0.723	Intermediate Similarity	NPD3764	Approved
0.72	Intermediate Similarity	NPD1933	Approved
0.7197	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1019	Discontinued
0.7172	Intermediate Similarity	NPD3225	Approved
0.7167	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4625	Phase 3
0.716	Intermediate Similarity	NPD1465	Phase 2
0.7153	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD5049	Phase 3
0.7134	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3267	Approved
0.7123	Intermediate Similarity	NPD3266	Approved
0.7117	Intermediate Similarity	NPD2296	Approved
0.7117	Intermediate Similarity	NPD4288	Approved
0.7115	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD1296	Phase 2
0.7114	Intermediate Similarity	NPD411	Approved
0.7114	Intermediate Similarity	NPD6798	Discontinued
0.7113	Intermediate Similarity	NPD1651	Approved
0.7103	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4661	Approved
0.7089	Intermediate Similarity	NPD4662	Approved
0.7086	Intermediate Similarity	NPD447	Suspended
0.7081	Intermediate Similarity	NPD6585	Discontinued
0.7078	Intermediate Similarity	NPD1471	Phase 3
0.7066	Intermediate Similarity	NPD7229	Phase 3
0.7059	Intermediate Similarity	NPD74	Approved
0.7059	Intermediate Similarity	NPD9266	Approved
0.7055	Intermediate Similarity	NPD5760	Phase 2
0.7055	Intermediate Similarity	NPD5761	Phase 2
0.7055	Intermediate Similarity	NPD1283	Approved
0.7045	Intermediate Similarity	NPD4287	Approved
0.7045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD1894	Discontinued
0.7029	Intermediate Similarity	NPD8434	Phase 2
0.7027	Intermediate Similarity	NPD7584	Approved
0.702	Intermediate Similarity	NPD4307	Phase 2
0.702	Intermediate Similarity	NPD1613	Approved
0.702	Intermediate Similarity	NPD3142	Approved
0.702	Intermediate Similarity	NPD3140	Approved
0.702	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD3847	Discontinued
0.7013	Intermediate Similarity	NPD4476	Approved
0.7013	Intermediate Similarity	NPD4477	Approved
0.7006	Intermediate Similarity	NPD3887	Approved
0.7006	Intermediate Similarity	NPD2354	Approved
0.6994	Remote Similarity	NPD6280	Approved
0.6994	Remote Similarity	NPD37	Approved
0.6994	Remote Similarity	NPD6279	Approved
0.6992	Remote Similarity	NPD940	Approved
0.6992	Remote Similarity	NPD846	Approved
0.6986	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9264	Approved
0.6985	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD9267	Approved
0.6985	Remote Similarity	NPD9263	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