NPASS Compound

Structure

NPC471395 OpenBabel07101718292D 40 47 0 0 1 0 0 0 0 0999 V2000 4.9739 -1.0740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5680 -3.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4488 1.1657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0209 0.6864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5511 -0.4108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3598 -1.8904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4127 -2.2544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4558 -3.1849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1970 -2.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0157 -3.2269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1167 -2.1612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5987 -1.2344 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4792 -0.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3466 -2.4404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1253 -1.5483 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5816 -2.4603 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7660 0.2467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2449 0.1007 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6322 -0.7280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0304 -2.9042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5383 -3.0218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0636 -1.5334 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0550 -2.1464 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5370 -1.2196 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0019 -1.5186 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2540 -0.3999 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6857 -1.0548 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0856 -2.0738 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1995 -0.7741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3142 -0.9200 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1131 -1.5812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7808 -0.5632 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4303 -1.8852 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6396 -0.7321 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.4518 -2.2939 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4860 0.1549 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0783 -1.6973 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4025 -1.8865 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9201 -2.6102 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 3 17 1 0 0 0 0 5 19 1 0 0 0 0 6 32 1 0 0 0 0 7 9 1 0 0 0 0 7 20 2 0 0 0 0 8 10 2 0 0 0 0 8 20 1 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 15 1 0 0 0 0 13 17 2 0 0 0 0 13 32 1 0 0 0 0 14 20 1 0 0 0 0 14 33 1 0 0 0 0 15 1 1 1 0 0 0 16 2 1 1 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 18 4 1 6 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 19 26 2 0 0 0 0 21 39 1 0 0 0 0 22 12 1 1 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 28 1 0 0 0 0 24 25 1 0 0 0 0 25 27 1 0 0 0 0 25 28 1 0 0 0 0 26 32 1 0 0 0 0 27 29 1 0 0 0 0 27 32 1 0 0 0 0 28 39 1 0 0 0 0 29 34 1 0 0 0 0 29 36 2 0 0 0 0 30 33 1 0 0 0 0 30 34 1 0 0 0 0 30 40 1 0 0 0 0 31 34 1 0 0 0 0 31 35 2 0 0 0 0 31 37 1 0 0 0 0 33 35 1 0 0 0 0 33 38 1 0 0 0 0 34 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	543.3
Volume:	564.661
LogP:	5.974
LogD:	5.034
LogS:	-4.236
# Rotatable Bonds:	0
TPSA:	88.16
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	9
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.284
Synthetic Accessibility Score:	7.517
Fsp3:	0.647
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.155
MDCK Permeability:	4.296367842471227e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.064
30% Bioavailability (F30%):	0.733

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.406
Plasma Protein Binding (PPB):	98.3361587524414%
Volume Distribution (VD):	2.195
Pgp-substrate:	3.126389265060425%

ADMET: Metabolism

CYP1A2-inhibitor:	0.056
CYP1A2-substrate:	0.882
CYP2C19-inhibitor:	0.729
CYP2C19-substrate:	0.882
CYP2C9-inhibitor:	0.382
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.968
CYP3A4-substrate:	0.844

ADMET: Excretion

Clearance (CL):	13.41
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.699
Drug-inuced Liver Injury (DILI):	0.969
AMES Toxicity:	0.308
Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.274
Carcinogencity:	0.683
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC471395

Natural Product ID:	NPC471395
*Common Name:**	NQFJAFJMOUIAAX-IIOHNVOSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NQFJAFJMOUIAAX-IIOHNVOSSA-N
Standard InCHI:	InChI=1S/C34H41NO5/c1-15-11-16(2)23-22(12-15)24-19(5)26-18(4)17(3)13-32(26,6)27-25(24)28(23)39-21-9-7-20(8-10-21)14-33(38)30-34(40-30,29(27)36)31(37)35-33/h7-10,13,15-16,18,22-25,27-28,30,38H,11-12,14H2,1-6H3,(H,35,37)/t15-,16+,18-,22-,23-,24-,25+,27+,28-,30+,32-,33?,34?/m0/s1
SMILES:	C[C@H]1C[C@@H](C)[C@H]2[C@H](C1)[C@@H]1C(=C3[C@@H](C)C(=C[C@@]3([C@@H]3[C@@H]1[C@H]2Oc1ccc(cc1)CC1([C@@H]2C(C3=O)(O2)C(=N1)O)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2431661
PubChem CID:	73353877
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related compounds

*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
NPO32615	phoma sp. nrrl 46751	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24079882]

☑ 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
MIC	2

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	35700.0	nM	PMID[464980]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	5.2	ug.mL-1	PMID[464980]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	13.4	ug.mL-1	PMID[464980]

☑ 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 NPC471395 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	287
0.1-0.2	1160
0.2-0.3	2810
0.3-0.4	7535
0.4-0.5	12050
0.5-0.6	13761
0.6-0.7	5048
0.7-0.8	34
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.875	High Similarity	NPC67080
0.8621	High Similarity	NPC88378
0.8621	High Similarity	NPC211713
0.8372	Intermediate Similarity	NPC471394
0.8372	Intermediate Similarity	NPC293164
0.8324	Intermediate Similarity	NPC71205
0.7514	Intermediate Similarity	NPC477115
0.7418	Intermediate Similarity	NPC471396
0.7351	Intermediate Similarity	NPC327694
0.7326	Intermediate Similarity	NPC471859
0.7312	Intermediate Similarity	NPC318472
0.7297	Intermediate Similarity	NPC326278
0.7278	Intermediate Similarity	NPC212699
0.7278	Intermediate Similarity	NPC207675
0.724	Intermediate Similarity	NPC206061
0.7234	Intermediate Similarity	NPC471860
0.7228	Intermediate Similarity	NPC15506
0.7216	Intermediate Similarity	NPC186746
0.7173	Intermediate Similarity	NPC167340
0.7173	Intermediate Similarity	NPC195972
0.7135	Intermediate Similarity	NPC475244
0.7113	Intermediate Similarity	NPC254588
0.7112	Intermediate Similarity	NPC471850
0.7111	Intermediate Similarity	NPC253591
0.7088	Intermediate Similarity	NPC28724
0.7085	Intermediate Similarity	NPC308709
0.7081	Intermediate Similarity	NPC476340
0.7081	Intermediate Similarity	NPC116639
0.7076	Intermediate Similarity	NPC477680
0.7073	Intermediate Similarity	NPC79130
0.7065	Intermediate Similarity	NPC156348
0.7059	Intermediate Similarity	NPC471858
0.7049	Intermediate Similarity	NPC87363
0.7043	Intermediate Similarity	NPC209473
0.7043	Intermediate Similarity	NPC469479
0.7043	Intermediate Similarity	NPC329743
0.7041	Intermediate Similarity	NPC247563
0.7041	Intermediate Similarity	NPC242068
0.7037	Intermediate Similarity	NPC478179
0.7033	Intermediate Similarity	NPC261659
0.7022	Intermediate Similarity	NPC313414
0.7021	Intermediate Similarity	NPC261184
0.7005	Intermediate Similarity	NPC310399
0.7005	Intermediate Similarity	NPC293347
0.7005	Intermediate Similarity	NPC73422
0.7	Intermediate Similarity	NPC476338
0.7	Intermediate Similarity	NPC476359
0.6995	Remote Similarity	NPC56635
0.6989	Remote Similarity	NPC472823
0.6983	Remote Similarity	NPC132771
0.6979	Remote Similarity	NPC313717
0.6979	Remote Similarity	NPC315306
0.6973	Remote Similarity	NPC159692
0.6968	Remote Similarity	NPC470936
0.6968	Remote Similarity	NPC90336
0.6965	Remote Similarity	NPC66909
0.6963	Remote Similarity	NPC470995
0.6963	Remote Similarity	NPC302392
0.6954	Remote Similarity	NPC105395
0.6949	Remote Similarity	NPC136649
0.6943	Remote Similarity	NPC236004
0.6943	Remote Similarity	NPC118128
0.6943	Remote Similarity	NPC94763
0.694	Remote Similarity	NPC178048
0.6931	Remote Similarity	NPC476244
0.6927	Remote Similarity	NPC475237
0.6927	Remote Similarity	NPC475641
0.6927	Remote Similarity	NPC159232
0.6919	Remote Similarity	NPC476194
0.6915	Remote Similarity	NPC197596
0.6911	Remote Similarity	NPC476277
0.691	Remote Similarity	NPC262216
0.6907	Remote Similarity	NPC473467
0.6907	Remote Similarity	NPC475197
0.6907	Remote Similarity	NPC469633
0.6907	Remote Similarity	NPC469393
0.6907	Remote Similarity	NPC475080
0.6906	Remote Similarity	NPC185404
0.6902	Remote Similarity	NPC51543
0.6902	Remote Similarity	NPC476335
0.6895	Remote Similarity	NPC161151
0.6895	Remote Similarity	NPC478178
0.6895	Remote Similarity	NPC471861
0.6891	Remote Similarity	NPC469848
0.6884	Remote Similarity	NPC299855
0.6884	Remote Similarity	NPC96194
0.6882	Remote Similarity	NPC471116
0.6878	Remote Similarity	NPC469505
0.6878	Remote Similarity	NPC316457
0.6872	Remote Similarity	NPC478177
0.6868	Remote Similarity	NPC95990
0.6868	Remote Similarity	NPC4108
0.6865	Remote Similarity	NPC327225
0.6865	Remote Similarity	NPC275878
0.6862	Remote Similarity	NPC475095
0.6859	Remote Similarity	NPC314653
0.6859	Remote Similarity	NPC310572
0.6859	Remote Similarity	NPC473908
0.6859	Remote Similarity	NPC473753
0.6859	Remote Similarity	NPC473766
0.6859	Remote Similarity	NPC316262
0.6856	Remote Similarity	NPC149502
0.6856	Remote Similarity	NPC271755
0.6856	Remote Similarity	NPC254071
0.6856	Remote Similarity	NPC472639
0.6856	Remote Similarity	NPC469576
0.6856	Remote Similarity	NPC472638
0.6856	Remote Similarity	NPC222665
0.6851	Remote Similarity	NPC212697
0.685	Remote Similarity	NPC189704
0.6848	Remote Similarity	NPC231668
0.6842	Remote Similarity	NPC475106
0.6842	Remote Similarity	NPC196091
0.6839	Remote Similarity	NPC285227
0.6839	Remote Similarity	NPC54903
0.6839	Remote Similarity	NPC286074
0.6833	Remote Similarity	NPC122491
0.6833	Remote Similarity	NPC32
0.6829	Remote Similarity	NPC64576
0.6829	Remote Similarity	NPC254045
0.6829	Remote Similarity	NPC151470
0.6829	Remote Similarity	NPC201055
0.6828	Remote Similarity	NPC477299
0.6828	Remote Similarity	NPC100134
0.6828	Remote Similarity	NPC209760
0.6828	Remote Similarity	NPC476364
0.6827	Remote Similarity	NPC258128
0.6827	Remote Similarity	NPC326895
0.6825	Remote Similarity	NPC5079
0.6825	Remote Similarity	NPC96443
0.6825	Remote Similarity	NPC290400
0.6823	Remote Similarity	NPC475109
0.6823	Remote Similarity	NPC469394
0.6818	Remote Similarity	NPC34780
0.6816	Remote Similarity	NPC475121
0.6816	Remote Similarity	NPC476067
0.6811	Remote Similarity	NPC246164
0.6806	Remote Similarity	NPC469395
0.6806	Remote Similarity	NPC475779
0.6806	Remote Similarity	NPC214279
0.6804	Remote Similarity	NPC475421
0.68	Remote Similarity	NPC473400
0.68	Remote Similarity	NPC471629
0.68	Remote Similarity	NPC306001
0.68	Remote Similarity	NPC206211
0.68	Remote Similarity	NPC275170
0.68	Remote Similarity	NPC324251
0.6798	Remote Similarity	NPC221134
0.6796	Remote Similarity	NPC227905
0.6796	Remote Similarity	NPC339338
0.6796	Remote Similarity	NPC146097
0.6794	Remote Similarity	NPC476495
0.6794	Remote Similarity	NPC94687
0.6794	Remote Similarity	NPC106840
0.6791	Remote Similarity	NPC478161
0.6791	Remote Similarity	NPC478159
0.6789	Remote Similarity	NPC663
0.6789	Remote Similarity	NPC478134
0.6789	Remote Similarity	NPC224394
0.6789	Remote Similarity	NPC234660
0.6789	Remote Similarity	NPC51568
0.6788	Remote Similarity	NPC472659
0.6788	Remote Similarity	NPC193222
0.6786	Remote Similarity	NPC470112
0.6786	Remote Similarity	NPC470903
0.6786	Remote Similarity	NPC167763
0.6786	Remote Similarity	NPC475398
0.6784	Remote Similarity	NPC475148
0.6784	Remote Similarity	NPC475656
0.6782	Remote Similarity	NPC289223
0.6776	Remote Similarity	NPC232583
0.6776	Remote Similarity	NPC25484
0.6774	Remote Similarity	NPC154675
0.6774	Remote Similarity	NPC210597
0.6772	Remote Similarity	NPC472653
0.6772	Remote Similarity	NPC470789
0.6772	Remote Similarity	NPC55744
0.6769	Remote Similarity	NPC471437
0.6769	Remote Similarity	NPC477529
0.6769	Remote Similarity	NPC169018
0.6766	Remote Similarity	NPC33372
0.6766	Remote Similarity	NPC67246
0.6766	Remote Similarity	NPC319549
0.6763	Remote Similarity	NPC235698
0.6762	Remote Similarity	NPC476496
0.6757	Remote Similarity	NPC475379
0.6757	Remote Similarity	NPC119252
0.6755	Remote Similarity	NPC10754
0.6755	Remote Similarity	NPC20530
0.6755	Remote Similarity	NPC10945
0.6755	Remote Similarity	NPC475378
0.6755	Remote Similarity	NPC164427
0.6755	Remote Similarity	NPC215917
0.6754	Remote Similarity	NPC164937
0.6754	Remote Similarity	NPC259943
0.6753	Remote Similarity	NPC294512
0.6751	Remote Similarity	NPC477816
0.6751	Remote Similarity	NPC227275
0.6751	Remote Similarity	NPC98943
0.6751	Remote Similarity	NPC469345

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 NPC471395 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	605
0.2-0.3	1278
0.3-0.4	2448
0.4-0.5	2764
0.5-0.6	1488
0.6-0.7	350
0.7-0.8	6
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
0.7391	Intermediate Similarity	NPD7315	Approved
0.7389	Intermediate Similarity	NPD7972	Discontinued
0.703	Intermediate Similarity	NPD4580	Approved
0.6976	Remote Similarity	NPD4582	Approved
0.6976	Remote Similarity	NPD4583	Approved
0.6965	Remote Similarity	NPD2973	Approved
0.6965	Remote Similarity	NPD2975	Approved
0.6965	Remote Similarity	NPD2974	Approved
0.6936	Remote Similarity	NPD6355	Discontinued
0.6934	Remote Similarity	NPD8404	Phase 2
0.6932	Remote Similarity	NPD5763	Approved
0.6932	Remote Similarity	NPD5762	Approved
0.6927	Remote Similarity	NPD4002	Approved
0.6927	Remote Similarity	NPD4004	Approved
0.6912	Remote Similarity	NPD2494	Approved
0.6912	Remote Similarity	NPD2493	Approved
0.6902	Remote Similarity	NPD6072	Discontinued
0.6902	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5735	Approved
0.6829	Remote Similarity	NPD3452	Approved
0.6829	Remote Similarity	NPD3450	Approved
0.6804	Remote Similarity	NPD5557	Phase 1
0.6789	Remote Similarity	NPD8127	Discontinued
0.6788	Remote Similarity	NPD3909	Discontinued
0.678	Remote Similarity	NPD2161	Phase 2
0.678	Remote Similarity	NPD5712	Approved
0.6766	Remote Similarity	NPD7296	Approved
0.6763	Remote Similarity	NPD7497	Discontinued
0.6738	Remote Similarity	NPD5761	Phase 2
0.6738	Remote Similarity	NPD5760	Phase 2
0.6735	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD8434	Phase 2
0.6732	Remote Similarity	NPD7565	Approved
0.6722	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4110	Phase 3
0.6717	Remote Similarity	NPD8407	Phase 2
0.6716	Remote Similarity	NPD2490	Approved
0.6716	Remote Similarity	NPD2488	Approved
0.6705	Remote Similarity	NPD6353	Approved
0.6699	Remote Similarity	NPD7999	Approved
0.6684	Remote Similarity	NPD3823	Discontinued
0.6684	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7930	Approved
0.6667	Remote Similarity	NPD2971	Approved
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD8435	Approved
0.6667	Remote Similarity	NPD2968	Approved
0.6651	Remote Similarity	NPD7907	Approved
0.665	Remote Similarity	NPD8368	Discontinued
0.665	Remote Similarity	NPD6764	Approved
0.665	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.665	Remote Similarity	NPD6765	Approved
0.6649	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD1375	Discontinued
0.6634	Remote Similarity	NPD8485	Approved
0.6631	Remote Similarity	NPD6677	Suspended
0.663	Remote Similarity	NPD6331	Phase 2
0.6629	Remote Similarity	NPD6233	Phase 2
0.6629	Remote Similarity	NPD8032	Phase 2
0.6628	Remote Similarity	NPD5647	Approved
0.662	Remote Similarity	NPD7801	Approved
0.6611	Remote Similarity	NPD2424	Discontinued
0.661	Remote Similarity	NPD2157	Approved
0.6609	Remote Similarity	NPD7095	Approved
0.6597	Remote Similarity	NPD6315	Phase 2
0.6591	Remote Similarity	NPD4140	Approved
0.6584	Remote Similarity	NPD8361	Approved
0.6584	Remote Similarity	NPD8360	Approved
0.6583	Remote Similarity	NPD7313	Approved
0.6583	Remote Similarity	NPD7312	Approved
0.6583	Remote Similarity	NPD7311	Approved
0.6583	Remote Similarity	NPD7310	Approved
0.658	Remote Similarity	NPD3787	Discontinued
0.6578	Remote Similarity	NPD6599	Discontinued
0.6576	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD7874	Approved
0.6571	Remote Similarity	NPD6798	Discontinued
0.6569	Remote Similarity	NPD4466	Phase 1
0.6566	Remote Similarity	NPD6104	Discontinued
0.656	Remote Similarity	NPD4111	Phase 1
0.6556	Remote Similarity	NPD6005	Phase 3
0.6556	Remote Similarity	NPD6002	Phase 3
0.6556	Remote Similarity	NPD6004	Phase 3
0.6556	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5327	Phase 3
0.655	Remote Similarity	NPD7309	Approved
0.6546	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7075	Discontinued
0.6541	Remote Similarity	NPD7526	Approved
0.6541	Remote Similarity	NPD6273	Approved
0.6541	Remote Similarity	NPD52	Approved
0.6541	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4628	Phase 3
0.6533	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6620	Discovery
0.6531	Remote Similarity	NPD7799	Discontinued
0.6517	Remote Similarity	NPD6785	Approved
0.6517	Remote Similarity	NPD6784	Approved
0.6503	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5035	Approved
0.6495	Remote Similarity	NPD7608	Discontinued
0.6493	Remote Similarity	NPD4040	Phase 1
0.6491	Remote Similarity	NPD7048	Phase 3
0.6485	Remote Similarity	NPD8150	Discontinued
0.6484	Remote Similarity	NPD4665	Approved
0.6482	Remote Similarity	NPD5030	Phase 2
0.6477	Remote Similarity	NPD6746	Phase 2
0.6477	Remote Similarity	NPD4666	Phase 3
0.6476	Remote Similarity	NPD3057	Approved
0.6471	Remote Similarity	NPD4003	Phase 3
0.6462	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD2970	Approved
0.6462	Remote Similarity	NPD2969	Approved
0.6458	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7833	Phase 2
0.6458	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7831	Phase 2
0.6453	Remote Similarity	NPD7906	Approved
0.6452	Remote Similarity	NPD6390	Discontinued
0.645	Remote Similarity	NPD5028	Approved
0.645	Remote Similarity	NPD5026	Approved
0.645	Remote Similarity	NPD36	Approved
0.645	Remote Similarity	NPD4954	Approved
0.645	Remote Similarity	NPD5034	Approved
0.645	Remote Similarity	NPD4955	Approved
0.6447	Remote Similarity	NPD3751	Discontinued
0.6441	Remote Similarity	NPD6663	Approved
0.6436	Remote Similarity	NPD5036	Approved
0.6436	Remote Similarity	NPD5811	Approved
0.6429	Remote Similarity	NPD2897	Discontinued
0.6429	Remote Similarity	NPD4534	Discontinued
0.6429	Remote Similarity	NPD5958	Discontinued
0.6425	Remote Similarity	NPD6653	Approved
0.6425	Remote Similarity	NPD5709	Phase 3
0.6418	Remote Similarity	NPD4578	Approved
0.6418	Remote Similarity	NPD4577	Approved
0.6417	Remote Similarity	NPD7131	Phase 3
0.6416	Remote Similarity	NPD8651	Approved
0.6414	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD8285	Discontinued
0.6411	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.641	Remote Similarity	NPD3051	Approved
0.6409	Remote Similarity	NPD6100	Approved
0.6409	Remote Similarity	NPD6099	Approved
0.6404	Remote Similarity	NPD5038	Approved
0.6404	Remote Similarity	NPD5037	Approved
0.6402	Remote Similarity	NPD6502	Phase 2
0.6402	Remote Similarity	NPD7701	Phase 2
0.64	Remote Similarity	NPD7685	Pre-registration
0.6398	Remote Similarity	NPD2972	Approved
0.6398	Remote Similarity	NPD6823	Phase 2
0.6398	Remote Similarity	NPD3533	Approved
0.6398	Remote Similarity	NPD3536	Discontinued
0.6398	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.639	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7783	Phase 2
0.6389	Remote Similarity	NPD5676	Approved
0.6389	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD5929	Approved
0.6387	Remote Similarity	NPD5772	Approved
0.6387	Remote Similarity	NPD5773	Approved
0.6378	Remote Similarity	NPD7236	Approved
0.6368	Remote Similarity	NPD3778	Approved
0.6368	Remote Similarity	NPD7696	Phase 3
0.6368	Remote Similarity	NPD7697	Approved
0.6368	Remote Similarity	NPD7698	Approved
0.6359	Remote Similarity	NPD7827	Phase 1
0.6359	Remote Similarity	NPD3819	Phase 2
0.6359	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD7199	Phase 2
0.6354	Remote Similarity	NPD7033	Discontinued
0.6354	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7007	Discovery
0.6348	Remote Similarity	NPD4062	Phase 3
0.6348	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD4481	Phase 3
0.6345	Remote Similarity	NPD27	Approved
0.6345	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD2489	Approved
0.6345	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD4357	Discontinued
0.6344	Remote Similarity	NPD6799	Approved
0.6344	Remote Similarity	NPD8067	Phase 3
0.6343	Remote Similarity	NPD4624	Approved
0.634	Remote Similarity	NPD6234	Discontinued
0.634	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD7870	Phase 2
0.6338	Remote Similarity	NPD7871	Phase 2
0.6338	Remote Similarity	NPD8320	Phase 1
0.6338	Remote Similarity	NPD8319	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