NPASS Compound

Structure

NPC472894 OpenBabel07101719242D 28 29 0 0 0 0 0 0 0 0999 V2000 1.7321 3.0000 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 -2.5981 2.5000 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 -5.1962 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 -5.1962 1.0000 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 -1.7321 0.0000 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 -3.4641 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 -2.5981 -0.5000 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 0.0000 -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 -0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 28 1 0 0 0 0 6 7 2 0 0 0 0 7 14 1 0 0 0 0 8 11 2 0 0 0 0 8 12 1 0 0 0 0 9 11 1 0 0 0 0 9 15 2 0 0 0 0 10 13 2 0 0 0 0 10 21 1 0 0 0 0 11 25 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 17 22 2 0 0 0 0 18 19 1 0 0 0 0 18 23 2 0 0 0 0 19 27 1 0 0 0 0 20 24 2 0 0 0 0 20 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	387.13
Volume:	386.163
LogP:	2.631
LogD:	1.982
LogS:	-4.268
# Rotatable Bonds:	8
TPSA:	103.92
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.575
Synthetic Accessibility Score:	2.874
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.89
MDCK Permeability:	1.2524673365987837e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.436
Plasma Protein Binding (PPB):	73.46179962158203%
Volume Distribution (VD):	1.01
Pgp-substrate:	14.799129486083984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.819
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.766
CYP2C19-substrate:	0.563
CYP2C9-inhibitor:	0.765
CYP2C9-substrate:	0.897
CYP2D6-inhibitor:	0.209
CYP2D6-substrate:	0.883
CYP3A4-inhibitor:	0.715
CYP3A4-substrate:	0.542

ADMET: Excretion

Clearance (CL):	6.276
Half-life (T1/2):	0.503

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.816
Drug-inuced Liver Injury (DILI):	0.822
AMES Toxicity:	0.226
Rat Oral Acute Toxicity:	0.886
Maximum Recommended Daily Dose:	0.54
Skin Sensitization:	0.62
Carcinogencity:	0.107
Eye Corrosion:	0.003
Eye Irritation:	0.085
Respiratory Toxicity:	0.694

Download Data

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

Natural Product: NPC472894

Natural Product ID:	NPC472894
*Common Name:**	QBVKMDADEIDLEW-VOTSOKGWSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QBVKMDADEIDLEW-VOTSOKGWSA-N
Standard InCHI:	InChI=1S/C20H21NO7/c1-6-7-14-19(27-4)18(23)13(10-21-14)17(22)16-12(20(24)28-5)8-11(25-2)9-15(16)26-3/h6-10H,1-5H3,(H,21,23)/b7-6+
SMILES:	C/C=C/c1[nH]cc(c(=O)c1OC)C(=O)c1c(OC)cc(cc1C(=O)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3593569
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004297] Aryl-phenylketones

*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
NPO33336	Penicillium sp. HN29-3B1	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26230970]

☑ 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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT60	Individual Protein	Lysosomal alpha-glucosidase	Homo sapiens	IC50	>	100000.0	nM	PMID[554478]

☑ 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 NPC472894 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	469
0.1-0.2	3168
0.2-0.3	11020
0.3-0.4	6248
0.4-0.5	10152
0.5-0.6	10001
0.6-0.7	1411
0.7-0.8	223
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8679	High Similarity	NPC52106
0.8148	Intermediate Similarity	NPC184702
0.8025	Intermediate Similarity	NPC297985
0.7952	Intermediate Similarity	NPC2569
0.7952	Intermediate Similarity	NPC172329
0.7927	Intermediate Similarity	NPC470932
0.7879	Intermediate Similarity	NPC474446
0.7866	Intermediate Similarity	NPC215451
0.7866	Intermediate Similarity	NPC277369
0.7857	Intermediate Similarity	NPC295036
0.7844	Intermediate Similarity	NPC153417
0.7805	Intermediate Similarity	NPC471640
0.7805	Intermediate Similarity	NPC250755
0.7805	Intermediate Similarity	NPC49108
0.7805	Intermediate Similarity	NPC471644
0.7798	Intermediate Similarity	NPC84142
0.7791	Intermediate Similarity	NPC109007
0.7778	Intermediate Similarity	NPC99381
0.7771	Intermediate Similarity	NPC49282
0.7758	Intermediate Similarity	NPC471643
0.7758	Intermediate Similarity	NPC472006
0.7758	Intermediate Similarity	NPC471639
0.7758	Intermediate Similarity	NPC167663
0.7751	Intermediate Similarity	NPC470107
0.7751	Intermediate Similarity	NPC164762
0.7751	Intermediate Similarity	NPC474660
0.7738	Intermediate Similarity	NPC215711
0.7738	Intermediate Similarity	NPC73411
0.7725	Intermediate Similarity	NPC472033
0.7725	Intermediate Similarity	NPC107625
0.7706	Intermediate Similarity	NPC91809
0.7697	Intermediate Similarity	NPC469579
0.7688	Intermediate Similarity	NPC263483
0.7684	Intermediate Similarity	NPC472895
0.7683	Intermediate Similarity	NPC472515
0.7679	Intermediate Similarity	NPC472036
0.7679	Intermediate Similarity	NPC259632
0.7679	Intermediate Similarity	NPC210320
0.7674	Intermediate Similarity	NPC317585
0.7669	Intermediate Similarity	NPC253616
0.7665	Intermediate Similarity	NPC312789
0.7665	Intermediate Similarity	NPC472034
0.7665	Intermediate Similarity	NPC28632
0.7651	Intermediate Similarity	NPC51106
0.765	Intermediate Similarity	NPC18306
0.7647	Intermediate Similarity	NPC473466
0.764	Intermediate Similarity	NPC223354
0.7636	Intermediate Similarity	NPC1704
0.7636	Intermediate Similarity	NPC475730
0.7636	Intermediate Similarity	NPC67650
0.7636	Intermediate Similarity	NPC474037
0.7622	Intermediate Similarity	NPC52358
0.7622	Intermediate Similarity	NPC36414
0.7619	Intermediate Similarity	NPC163846
0.7619	Intermediate Similarity	NPC225173
0.7619	Intermediate Similarity	NPC473927
0.7607	Intermediate Similarity	NPC61546
0.7607	Intermediate Similarity	NPC301341
0.7607	Intermediate Similarity	NPC284184
0.7607	Intermediate Similarity	NPC72452
0.7607	Intermediate Similarity	NPC268081
0.7605	Intermediate Similarity	NPC475201
0.7602	Intermediate Similarity	NPC472535
0.7602	Intermediate Similarity	NPC189773
0.7602	Intermediate Similarity	NPC474170
0.7602	Intermediate Similarity	NPC215921
0.7602	Intermediate Similarity	NPC474388
0.7602	Intermediate Similarity	NPC70016
0.7593	Intermediate Similarity	NPC182496
0.7593	Intermediate Similarity	NPC180905
0.759	Intermediate Similarity	NPC474385
0.7588	Intermediate Similarity	NPC4423
0.7588	Intermediate Similarity	NPC77325
0.7588	Intermediate Similarity	NPC198927
0.7586	Intermediate Similarity	NPC246466
0.7578	Intermediate Similarity	NPC182428
0.7576	Intermediate Similarity	NPC49242
0.7576	Intermediate Similarity	NPC136095
0.7574	Intermediate Similarity	NPC299923
0.7574	Intermediate Similarity	NPC474999
0.7574	Intermediate Similarity	NPC125801
0.7572	Intermediate Similarity	NPC241774
0.7572	Intermediate Similarity	NPC34725
0.7572	Intermediate Similarity	NPC276059
0.7572	Intermediate Similarity	NPC122623
0.7561	Intermediate Similarity	NPC103001
0.756	Intermediate Similarity	NPC134621
0.7547	Intermediate Similarity	NPC211120
0.7545	Intermediate Similarity	NPC478202
0.7545	Intermediate Similarity	NPC469542
0.7544	Intermediate Similarity	NPC56204
0.7544	Intermediate Similarity	NPC158866
0.7544	Intermediate Similarity	NPC177839
0.7544	Intermediate Similarity	NPC469619
0.7544	Intermediate Similarity	NPC469670
0.753	Intermediate Similarity	NPC158634
0.753	Intermediate Similarity	NPC244923
0.753	Intermediate Similarity	NPC90411
0.7529	Intermediate Similarity	NPC471642
0.7529	Intermediate Similarity	NPC240253
0.7529	Intermediate Similarity	NPC240622
0.7529	Intermediate Similarity	NPC474983
0.7529	Intermediate Similarity	NPC37139
0.7529	Intermediate Similarity	NPC472050
0.7529	Intermediate Similarity	NPC471641
0.7529	Intermediate Similarity	NPC257277
0.7516	Intermediate Similarity	NPC65041
0.7515	Intermediate Similarity	NPC92655
0.7515	Intermediate Similarity	NPC195919
0.7515	Intermediate Similarity	NPC237208
0.7515	Intermediate Similarity	NPC310259
0.7515	Intermediate Similarity	NPC120924
0.7515	Intermediate Similarity	NPC472368
0.7515	Intermediate Similarity	NPC216314
0.7515	Intermediate Similarity	NPC25427
0.7514	Intermediate Similarity	NPC186507
0.7514	Intermediate Similarity	NPC473664
0.75	Intermediate Similarity	NPC476333
0.75	Intermediate Similarity	NPC474414
0.75	Intermediate Similarity	NPC472367
0.75	Intermediate Similarity	NPC135837
0.75	Intermediate Similarity	NPC473732
0.75	Intermediate Similarity	NPC200773
0.75	Intermediate Similarity	NPC470216
0.75	Intermediate Similarity	NPC243701
0.75	Intermediate Similarity	NPC277426
0.75	Intermediate Similarity	NPC254741
0.75	Intermediate Similarity	NPC240768
0.75	Intermediate Similarity	NPC19896
0.75	Intermediate Similarity	NPC472364
0.75	Intermediate Similarity	NPC313368
0.75	Intermediate Similarity	NPC27106
0.75	Intermediate Similarity	NPC210425
0.75	Intermediate Similarity	NPC86373
0.75	Intermediate Similarity	NPC472516
0.75	Intermediate Similarity	NPC473391
0.75	Intermediate Similarity	NPC66404
0.75	Intermediate Similarity	NPC189650
0.75	Intermediate Similarity	NPC280404
0.75	Intermediate Similarity	NPC95123
0.7486	Intermediate Similarity	NPC472889
0.7485	Intermediate Similarity	NPC65775
0.7485	Intermediate Similarity	NPC69752
0.7485	Intermediate Similarity	NPC10027
0.7485	Intermediate Similarity	NPC185607
0.7485	Intermediate Similarity	NPC470844
0.7485	Intermediate Similarity	NPC80370
0.7485	Intermediate Similarity	NPC24075
0.7471	Intermediate Similarity	NPC471746
0.7471	Intermediate Similarity	NPC14098
0.7471	Intermediate Similarity	NPC478221
0.7471	Intermediate Similarity	NPC117463
0.7471	Intermediate Similarity	NPC170189
0.7471	Intermediate Similarity	NPC137296
0.7471	Intermediate Similarity	NPC472890
0.7471	Intermediate Similarity	NPC289042
0.7471	Intermediate Similarity	NPC56786
0.7471	Intermediate Similarity	NPC190648
0.7471	Intermediate Similarity	NPC118027
0.7471	Intermediate Similarity	NPC245584
0.7471	Intermediate Similarity	NPC126767
0.7471	Intermediate Similarity	NPC56433
0.7471	Intermediate Similarity	NPC80534
0.7471	Intermediate Similarity	NPC312929
0.7471	Intermediate Similarity	NPC208173
0.7471	Intermediate Similarity	NPC38898
0.747	Intermediate Similarity	NPC472366
0.747	Intermediate Similarity	NPC165172
0.7458	Intermediate Similarity	NPC317544
0.7457	Intermediate Similarity	NPC76041
0.7457	Intermediate Similarity	NPC207624
0.7457	Intermediate Similarity	NPC184284
0.7457	Intermediate Similarity	NPC271681
0.7457	Intermediate Similarity	NPC175978
0.7457	Intermediate Similarity	NPC115249
0.7457	Intermediate Similarity	NPC475116
0.7456	Intermediate Similarity	NPC136278
0.7456	Intermediate Similarity	NPC29577
0.7456	Intermediate Similarity	NPC171656
0.7455	Intermediate Similarity	NPC44573
0.7455	Intermediate Similarity	NPC33144
0.7455	Intermediate Similarity	NPC470962
0.7455	Intermediate Similarity	NPC478200
0.7455	Intermediate Similarity	NPC191835
0.7444	Intermediate Similarity	NPC283041
0.7443	Intermediate Similarity	NPC477410
0.7442	Intermediate Similarity	NPC255641
0.7442	Intermediate Similarity	NPC472891
0.7442	Intermediate Similarity	NPC290954
0.7442	Intermediate Similarity	NPC60413
0.7442	Intermediate Similarity	NPC201547
0.7442	Intermediate Similarity	NPC85131
0.7442	Intermediate Similarity	NPC147735
0.7442	Intermediate Similarity	NPC470568
0.7442	Intermediate Similarity	NPC294646
0.7442	Intermediate Similarity	NPC216917
0.7442	Intermediate Similarity	NPC259058
0.7442	Intermediate Similarity	NPC191104
0.743	Intermediate Similarity	NPC191930
0.7427	Intermediate Similarity	NPC472056

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 NPC472894 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	708
0.2-0.3	963
0.3-0.4	1900
0.4-0.5	2744
0.5-0.6	2031
0.6-0.7	506
0.7-0.8	35
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7622	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5711	Approved
0.7514	Intermediate Similarity	NPD7819	Suspended
0.7514	Intermediate Similarity	NPD5710	Approved
0.75	Intermediate Similarity	NPD6799	Approved
0.7471	Intermediate Similarity	NPD3817	Phase 2
0.747	Intermediate Similarity	NPD2654	Approved
0.7442	Intermediate Similarity	NPD6599	Discontinued
0.743	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD4585	Approved
0.7394	Intermediate Similarity	NPD2796	Approved
0.7374	Intermediate Similarity	NPD5242	Approved
0.7353	Intermediate Similarity	NPD2533	Approved
0.7353	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2534	Approved
0.7353	Intermediate Similarity	NPD2532	Approved
0.7337	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3748	Approved
0.7318	Intermediate Similarity	NPD6232	Discontinued
0.7314	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD8366	Approved
0.7293	Intermediate Similarity	NPD7473	Discontinued
0.7282	Intermediate Similarity	NPD7435	Discontinued
0.7267	Intermediate Similarity	NPD920	Approved
0.7257	Intermediate Similarity	NPD6801	Discontinued
0.7247	Intermediate Similarity	NPD919	Approved
0.7229	Intermediate Similarity	NPD1510	Phase 2
0.7219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6779	Approved
0.7216	Intermediate Similarity	NPD6777	Approved
0.7216	Intermediate Similarity	NPD6780	Approved
0.7216	Intermediate Similarity	NPD6776	Approved
0.7216	Intermediate Similarity	NPD6781	Approved
0.7216	Intermediate Similarity	NPD6778	Approved
0.7216	Intermediate Similarity	NPD6782	Approved
0.7195	Intermediate Similarity	NPD1240	Approved
0.7191	Intermediate Similarity	NPD7075	Discontinued
0.7182	Intermediate Similarity	NPD3926	Phase 2
0.7175	Intermediate Similarity	NPD5402	Approved
0.7175	Intermediate Similarity	NPD5353	Approved
0.7163	Intermediate Similarity	NPD8491	Approved
0.716	Intermediate Similarity	NPD1243	Approved
0.7158	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD3882	Suspended
0.7127	Intermediate Similarity	NPD6808	Phase 2
0.7118	Intermediate Similarity	NPD3750	Approved
0.7108	Intermediate Similarity	NPD1607	Approved
0.7107	Intermediate Similarity	NPD7696	Phase 3
0.7107	Intermediate Similarity	NPD7698	Approved
0.7107	Intermediate Similarity	NPD7697	Approved
0.7102	Intermediate Similarity	NPD6386	Approved
0.7102	Intermediate Similarity	NPD6385	Approved
0.7086	Intermediate Similarity	NPD2651	Approved
0.7086	Intermediate Similarity	NPD2649	Approved
0.7085	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2935	Discontinued
0.7072	Intermediate Similarity	NPD1247	Approved
0.7071	Intermediate Similarity	NPD7870	Phase 2
0.7071	Intermediate Similarity	NPD7871	Phase 2
0.7035	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD2801	Approved
0.7017	Intermediate Similarity	NPD5494	Approved
0.7011	Intermediate Similarity	NPD1512	Approved
0.7011	Intermediate Similarity	NPD2186	Approved
0.7006	Intermediate Similarity	NPD7411	Suspended
0.7	Intermediate Similarity	NPD3749	Approved
0.6989	Remote Similarity	NPD3226	Approved
0.6971	Remote Similarity	NPD5403	Approved
0.6971	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6280	Approved
0.6966	Remote Similarity	NPD6279	Approved
0.6959	Remote Similarity	NPD6534	Approved
0.6959	Remote Similarity	NPD6535	Approved
0.6954	Remote Similarity	NPD5401	Approved
0.6949	Remote Similarity	NPD4380	Phase 2
0.6946	Remote Similarity	NPD7801	Approved
0.6941	Remote Similarity	NPD1471	Phase 3
0.6927	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.691	Remote Similarity	NPD5090	Approved
0.691	Remote Similarity	NPD5089	Approved
0.6906	Remote Similarity	NPD1309	Phase 2
0.6906	Remote Similarity	NPD1307	Phase 2
0.6901	Remote Similarity	NPD1549	Phase 2
0.6897	Remote Similarity	NPD1511	Approved
0.6897	Remote Similarity	NPD7874	Approved
0.6897	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD5006	Approved
0.6884	Remote Similarity	NPD5005	Approved
0.6882	Remote Similarity	NPD2163	Approved
0.6878	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD1934	Approved
0.6865	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.686	Remote Similarity	NPD2800	Approved
0.6857	Remote Similarity	NPD4661	Approved
0.6857	Remote Similarity	NPD4662	Approved
0.6857	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7700	Phase 2
0.6853	Remote Similarity	NPD7699	Phase 2
0.6847	Remote Similarity	NPD8151	Discontinued
0.6845	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2346	Discontinued
0.6842	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD2799	Discontinued
0.6824	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8285	Discontinued
0.6816	Remote Similarity	NPD8319	Approved
0.6816	Remote Similarity	NPD5889	Approved
0.6816	Remote Similarity	NPD8320	Phase 1
0.6816	Remote Similarity	NPD5890	Approved
0.6813	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6808	Remote Similarity	NPD8469	Approved
0.6798	Remote Similarity	NPD7701	Phase 2
0.6793	Remote Similarity	NPD6959	Discontinued
0.6791	Remote Similarity	NPD3818	Discontinued
0.6774	Remote Similarity	NPD6166	Phase 2
0.6774	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6797	Phase 2
0.6768	Remote Similarity	NPD4420	Approved
0.6766	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1296	Phase 2
0.6761	Remote Similarity	NPD3146	Approved
0.6761	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.676	Remote Similarity	NPD6585	Discontinued
0.6758	Remote Similarity	NPD7768	Phase 2
0.6758	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5844	Phase 1
0.6753	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6832	Phase 2
0.6737	Remote Similarity	NPD6104	Discontinued
0.6737	Remote Similarity	NPD7251	Discontinued
0.6736	Remote Similarity	NPD8150	Discontinued
0.6727	Remote Similarity	NPD2798	Approved
0.6716	Remote Similarity	NPD6823	Phase 2
0.6707	Remote Similarity	NPD1876	Approved
0.6706	Remote Similarity	NPD6651	Approved
0.6705	Remote Similarity	NPD2897	Discontinued
0.6703	Remote Similarity	NPD5977	Approved
0.6703	Remote Similarity	NPD5978	Approved
0.6703	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7177	Discontinued
0.6702	Remote Similarity	NPD7808	Phase 3
0.67	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7783	Phase 2
0.6687	Remote Similarity	NPD3972	Approved
0.6686	Remote Similarity	NPD3140	Approved
0.6686	Remote Similarity	NPD3142	Approved
0.6686	Remote Similarity	NPD4476	Approved
0.6686	Remote Similarity	NPD3295	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1551	Phase 2
0.6686	Remote Similarity	NPD4477	Approved
0.6685	Remote Similarity	NPD6844	Discontinued
0.6685	Remote Similarity	NPD5709	Phase 3
0.6684	Remote Similarity	NPD2403	Approved
0.6684	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5953	Discontinued
0.6683	Remote Similarity	NPD7930	Approved
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD7584	Approved
0.6667	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7038	Approved
0.6649	Remote Similarity	NPD4666	Phase 3
0.6649	Remote Similarity	NPD7039	Approved
0.6648	Remote Similarity	NPD1465	Phase 2
0.6647	Remote Similarity	NPD2344	Approved
0.6647	Remote Similarity	NPD230	Phase 1
0.6629	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1019	Discontinued
0.6616	Remote Similarity	NPD4363	Phase 3
0.6616	Remote Similarity	NPD4360	Phase 2
0.6614	Remote Similarity	NPD3751	Discontinued
0.6614	Remote Similarity	NPD5940	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD2249	Approved
0.6613	Remote Similarity	NPD2247	Approved
0.661	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4668	Phase 2
0.6597	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD943	Approved
0.6585	Remote Similarity	NPD6637	Approved
0.6583	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD4361	Phase 2
0.6579	Remote Similarity	NPD7054	Approved
0.6579	Remote Similarity	NPD7286	Phase 2
0.657	Remote Similarity	NPD5689	Approved
0.657	Remote Similarity	NPD5688	Approved
0.6559	Remote Similarity	NPD6746	Phase 2
0.655	Remote Similarity	NPD4622	Approved
0.655	Remote Similarity	NPD447	Suspended
0.655	Remote Similarity	NPD4618	Approved
0.6548	Remote Similarity	NPD7668	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