NPASS Compound

Structure

NPC211713 OpenBabel07101718202D 37 43 0 0 1 0 0 0 0 0999 V2000 -1.0704 -0.3699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8920 -2.4688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8491 -0.3984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1400 -0.3497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3051 0.3978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9009 0.1685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5164 -0.3832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0517 -0.3889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5907 -1.3862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4795 -0.4876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2834 -1.1721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0066 0.8350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -0.6078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5363 0.5078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4989 -1.1904 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4672 -1.5636 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0531 -0.8297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5232 0.6053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9457 -0.9566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0129 -0.6078 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7738 -0.1685 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0129 -1.4864 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4830 -1.7161 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0546 -1.3764 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2517 -1.5453 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0940 -1.6931 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3906 -1.0496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5919 -0.8060 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1599 -1.3495 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5414 -0.4921 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5836 0.8120 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7738 0.8315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2736 -1.5189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2877 -1.7586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7706 1.7944 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6039 -1.4220 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 17 1 0 0 0 0 4 29 1 0 0 0 0 5 7 1 0 0 0 0 5 18 2 0 0 0 0 6 8 2 0 0 0 0 6 18 1 0 0 0 0 7 19 2 0 0 0 0 8 19 1 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 15 1 0 0 0 0 11 29 1 0 0 0 0 12 18 1 0 0 0 0 12 31 1 0 0 0 0 13 21 1 0 0 0 0 13 30 1 0 0 0 0 14 30 1 0 0 0 0 14 31 1 0 0 0 0 15 1 1 1 0 0 0 16 2 1 1 0 0 0 16 25 1 0 0 0 0 17 24 1 0 0 0 0 19 37 1 0 0 0 0 20 10 1 6 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 21 33 1 6 0 0 0 22 23 1 0 0 0 0 22 27 1 6 0 0 0 23 24 1 0 0 0 0 23 26 1 0 0 0 0 24 29 1 0 0 0 0 25 26 1 0 0 0 0 25 29 1 0 0 0 0 26 37 1 0 0 0 0 27 30 1 0 0 0 0 27 34 2 0 0 0 0 28 30 1 0 0 0 0 28 32 2 0 0 0 0 28 35 1 0 0 0 0 31 32 1 0 0 0 0 31 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	505.28
Volume:	523.966
LogP:	4.094
LogD:	4.249
LogS:	-3.835
# Rotatable Bonds:	0
TPSA:	95.86
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.37
Synthetic Accessibility Score:	7.854
Fsp3:	0.677
Lipinski Rule-of-5:	Accepted
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:	-5.374
MDCK Permeability:	9.217091246682685e-06
Pgp-inhibitor:	0.166
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.762

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.761
Plasma Protein Binding (PPB):	87.66653442382812%
Volume Distribution (VD):	1.916
Pgp-substrate:	5.961291313171387%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.84
CYP2C19-inhibitor:	0.641
CYP2C19-substrate:	0.868
CYP2C9-inhibitor:	0.423
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.981
CYP3A4-substrate:	0.845

ADMET: Excretion

Clearance (CL):	15.689
Half-life (T1/2):	0.241

ADMET: Toxicity

hERG Blockers:	0.298
Human Hepatotoxicity (H-HT):	0.582
Drug-inuced Liver Injury (DILI):	0.858
AMES Toxicity:	0.077
Rat Oral Acute Toxicity:	0.86
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.04
Carcinogencity:	0.204
Eye Corrosion:	0.003
Eye Irritation:	0.007
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC211713

Natural Product ID:	NPC211713
*Common Name:**	Pyrrospirone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HECJLRHOFZNKOS-JAYQBPHDSA-N
Standard InCHI:	InChI=1S/C31H39NO5/c1-15-9-16(2)25-26-23-22-20(10-17(3)24(23)29(25,4)11-15)21(33)13-30(27(22)34)14-31(36,32-28(30)35)12-18-5-7-19(37-26)8-6-18/h5-8,10,15-16,20-26,33,36H,9,11-14H2,1-4H3,(H,32,35)/t15-,16+,20-,21-,22+,23-,24-,25+,26+,29+,30+,31-/m1/s1
SMILES:	C[C@@H]1C[C@H](C)[C@@H]2[C@](C1)(C)[C@@H]1C(=C[C@H]3[C@H]4[C@H]1[C@@H]2Oc1ccc(cc1)C[C@]1(C[C@](C4=O)(C[C@H]3O)C(=N1)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL507377
PubChem CID:	25168441
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
NPO33492	neonectria ramulariae wollenw ks-246	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18952424]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	14910.0	nM	PMID[463112]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	9960.0	nM	PMID[463112]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	17970.0	nM	PMID[463112]

☑ 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 NPC211713 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	267
0.1-0.2	1141
0.2-0.3	2474
0.3-0.4	6016
0.4-0.5	11740
0.5-0.6	12423
0.6-0.7	8424
0.7-0.8	201
0.8-0.85	6
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC88378
0.9304	High Similarity	NPC67080
0.8834	High Similarity	NPC71205
0.8621	High Similarity	NPC471395
0.8545	High Similarity	NPC293164
0.8545	High Similarity	NPC471394
0.7751	Intermediate Similarity	NPC261659
0.7738	Intermediate Similarity	NPC253591
0.7543	Intermediate Similarity	NPC471396
0.7542	Intermediate Similarity	NPC477115
0.7515	Intermediate Similarity	NPC221134
0.7472	Intermediate Similarity	NPC327694
0.7446	Intermediate Similarity	NPC206061
0.743	Intermediate Similarity	NPC318472
0.7427	Intermediate Similarity	NPC146388
0.7416	Intermediate Similarity	NPC326278
0.7396	Intermediate Similarity	NPC169942
0.7384	Intermediate Similarity	NPC146014
0.7348	Intermediate Similarity	NPC471859
0.7317	Intermediate Similarity	NPC208725
0.7299	Intermediate Similarity	NPC48671
0.7288	Intermediate Similarity	NPC474611
0.7283	Intermediate Similarity	NPC195972
0.7278	Intermediate Similarity	NPC469395
0.7278	Intermediate Similarity	NPC214279
0.7277	Intermediate Similarity	NPC308709
0.7273	Intermediate Similarity	NPC156348
0.7267	Intermediate Similarity	NPC95990
0.7259	Intermediate Similarity	NPC79130
0.7257	Intermediate Similarity	NPC87363
0.7253	Intermediate Similarity	NPC198075
0.7247	Intermediate Similarity	NPC209473
0.7243	Intermediate Similarity	NPC475244
0.7241	Intermediate Similarity	NPC140133
0.7229	Intermediate Similarity	NPC194847
0.7229	Intermediate Similarity	NPC21797
0.7209	Intermediate Similarity	NPC476359
0.7209	Intermediate Similarity	NPC476338
0.7207	Intermediate Similarity	NPC73422
0.7207	Intermediate Similarity	NPC310399
0.7198	Intermediate Similarity	NPC469394
0.7189	Intermediate Similarity	NPC167340
0.7186	Intermediate Similarity	NPC98804
0.7182	Intermediate Similarity	NPC161151
0.7176	Intermediate Similarity	NPC470273
0.7167	Intermediate Similarity	NPC470936
0.7158	Intermediate Similarity	NPC471860
0.7151	Intermediate Similarity	NPC329743
0.7151	Intermediate Similarity	NPC15506
0.715	Intermediate Similarity	NPC66909
0.7143	Intermediate Similarity	NPC265335
0.7136	Intermediate Similarity	NPC476495
0.7136	Intermediate Similarity	NPC106840
0.7136	Intermediate Similarity	NPC94687
0.7135	Intermediate Similarity	NPC469507
0.7126	Intermediate Similarity	NPC322526
0.7126	Intermediate Similarity	NPC474610
0.7126	Intermediate Similarity	NPC279442
0.7126	Intermediate Similarity	NPC262324
0.7121	Intermediate Similarity	NPC476500
0.712	Intermediate Similarity	NPC475237
0.712	Intermediate Similarity	NPC475641
0.712	Intermediate Similarity	NPC54903
0.712	Intermediate Similarity	NPC286074
0.7118	Intermediate Similarity	NPC262216
0.7112	Intermediate Similarity	NPC115906
0.7111	Intermediate Similarity	NPC472618
0.711	Intermediate Similarity	NPC476336
0.7108	Intermediate Similarity	NPC471864
0.7105	Intermediate Similarity	NPC283207
0.7104	Intermediate Similarity	NPC85047
0.7104	Intermediate Similarity	NPC120857
0.7104	Intermediate Similarity	NPC17274
0.7104	Intermediate Similarity	NPC200726
0.7102	Intermediate Similarity	NPC28724
0.7102	Intermediate Similarity	NPC246164
0.7102	Intermediate Similarity	NPC51543
0.7101	Intermediate Similarity	NPC76312
0.71	Intermediate Similarity	NPC476496
0.71	Intermediate Similarity	NPC293347
0.7097	Intermediate Similarity	NPC473467
0.7097	Intermediate Similarity	NPC475197
0.7095	Intermediate Similarity	NPC472823
0.7091	Intermediate Similarity	NPC169766
0.7085	Intermediate Similarity	NPC326895
0.7083	Intermediate Similarity	NPC239770
0.7073	Intermediate Similarity	NPC196193
0.7072	Intermediate Similarity	NPC90336
0.7072	Intermediate Similarity	NPC471858
0.7069	Intermediate Similarity	NPC478163
0.7068	Intermediate Similarity	NPC299855
0.7068	Intermediate Similarity	NPC96194
0.7066	Intermediate Similarity	NPC473055
0.7066	Intermediate Similarity	NPC473052
0.7065	Intermediate Similarity	NPC177362
0.7056	Intermediate Similarity	NPC472299
0.7056	Intermediate Similarity	NPC186113
0.7056	Intermediate Similarity	NPC472617
0.7053	Intermediate Similarity	NPC186746
0.7049	Intermediate Similarity	NPC314653
0.7049	Intermediate Similarity	NPC472784
0.7049	Intermediate Similarity	NPC316262
0.7049	Intermediate Similarity	NPC310572
0.7047	Intermediate Similarity	NPC289223
0.7045	Intermediate Similarity	NPC119252
0.7045	Intermediate Similarity	NPC231668
0.7043	Intermediate Similarity	NPC118128
0.7043	Intermediate Similarity	NPC149502
0.7043	Intermediate Similarity	NPC222665
0.7043	Intermediate Similarity	NPC254071
0.7043	Intermediate Similarity	NPC271755
0.7041	Intermediate Similarity	NPC79921
0.7041	Intermediate Similarity	NPC234548
0.7041	Intermediate Similarity	NPC248287
0.7039	Intermediate Similarity	NPC304692
0.7039	Intermediate Similarity	NPC55463
0.7039	Intermediate Similarity	NPC166116
0.7039	Intermediate Similarity	NPC478223
0.7035	Intermediate Similarity	NPC474599
0.7035	Intermediate Similarity	NPC313414
0.7033	Intermediate Similarity	NPC471850
0.7033	Intermediate Similarity	NPC475106
0.7031	Intermediate Similarity	NPC189704
0.7029	Intermediate Similarity	NPC472654
0.7029	Intermediate Similarity	NPC290695
0.7029	Intermediate Similarity	NPC106524
0.7027	Intermediate Similarity	NPC266545
0.7027	Intermediate Similarity	NPC202428
0.7027	Intermediate Similarity	NPC20734
0.7024	Intermediate Similarity	NPC243893
0.7022	Intermediate Similarity	NPC476364
0.7022	Intermediate Similarity	NPC472785
0.7018	Intermediate Similarity	NPC20631
0.7018	Intermediate Similarity	NPC263337
0.7018	Intermediate Similarity	NPC93640
0.7017	Intermediate Similarity	NPC471003
0.7011	Intermediate Similarity	NPC470019
0.7011	Intermediate Similarity	NPC296558
0.7011	Intermediate Similarity	NPC286038
0.7011	Intermediate Similarity	NPC216755
0.7011	Intermediate Similarity	NPC471174
0.7006	Intermediate Similarity	NPC470675
0.7006	Intermediate Similarity	NPC476335
0.7006	Intermediate Similarity	NPC121615
0.7006	Intermediate Similarity	NPC477276
0.7006	Intermediate Similarity	NPC294511
0.7006	Intermediate Similarity	NPC473131
0.7005	Intermediate Similarity	NPC469393
0.7	Intermediate Similarity	NPC116639
0.7	Intermediate Similarity	NPC79372
0.7	Intermediate Similarity	NPC214629
0.6995	Remote Similarity	NPC100849
0.6995	Remote Similarity	NPC476295
0.6995	Remote Similarity	NPC475779
0.6995	Remote Similarity	NPC476067
0.6995	Remote Similarity	NPC475121
0.6995	Remote Similarity	NPC471861
0.6994	Remote Similarity	NPC186889
0.6989	Remote Similarity	NPC313717
0.6989	Remote Similarity	NPC12854
0.6989	Remote Similarity	NPC212257
0.6989	Remote Similarity	NPC471114
0.6989	Remote Similarity	NPC315306
0.6989	Remote Similarity	NPC193698
0.6988	Remote Similarity	NPC64897
0.6988	Remote Similarity	NPC90693
0.6988	Remote Similarity	NPC165612
0.6983	Remote Similarity	NPC104736
0.6983	Remote Similarity	NPC41880
0.6983	Remote Similarity	NPC478159
0.6983	Remote Similarity	NPC159692
0.6983	Remote Similarity	NPC478161
0.6978	Remote Similarity	NPC165218
0.6977	Remote Similarity	NPC197461
0.6973	Remote Similarity	NPC472660
0.6971	Remote Similarity	NPC52161
0.6971	Remote Similarity	NPC93666
0.6971	Remote Similarity	NPC162751
0.6971	Remote Similarity	NPC66991
0.6971	Remote Similarity	NPC471007
0.697	Remote Similarity	NPC475102
0.697	Remote Similarity	NPC42423
0.6966	Remote Similarity	NPC44606
0.6966	Remote Similarity	NPC178932
0.6966	Remote Similarity	NPC205392
0.6966	Remote Similarity	NPC105942
0.6964	Remote Similarity	NPC472804
0.6961	Remote Similarity	NPC239118
0.6961	Remote Similarity	NPC226287
0.6961	Remote Similarity	NPC287559
0.6961	Remote Similarity	NPC218818
0.6961	Remote Similarity	NPC4950
0.6959	Remote Similarity	NPC472801
0.6959	Remote Similarity	NPC138149
0.6959	Remote Similarity	NPC155552
0.6959	Remote Similarity	NPC136649
0.6957	Remote Similarity	NPC478179
0.6954	Remote Similarity	NPC471608
0.6952	Remote Similarity	NPC478002
0.6952	Remote Similarity	NPC472638

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 NPC211713 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	626
0.2-0.3	1089
0.3-0.4	2174
0.4-0.5	2772
0.5-0.6	1728
0.6-0.7	531
0.7-0.8	28
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
0.7816	Intermediate Similarity	NPD7315	Approved
0.741	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD5735	Approved
0.736	Intermediate Similarity	NPD8127	Discontinued
0.7314	Intermediate Similarity	NPD5761	Phase 2
0.7314	Intermediate Similarity	NPD5760	Phase 2
0.731	Intermediate Similarity	NPD6273	Approved
0.7301	Intermediate Similarity	NPD4140	Approved
0.7212	Intermediate Similarity	NPD6353	Approved
0.7212	Intermediate Similarity	NPD2157	Approved
0.72	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2161	Phase 2
0.7174	Intermediate Similarity	NPD5557	Phase 1
0.717	Intermediate Similarity	NPD5327	Phase 3
0.7158	Intermediate Similarity	NPD3909	Discontinued
0.715	Intermediate Similarity	NPD2973	Approved
0.715	Intermediate Similarity	NPD2975	Approved
0.715	Intermediate Similarity	NPD2974	Approved
0.7134	Intermediate Similarity	NPD8032	Phase 2
0.7128	Intermediate Similarity	NPD4580	Approved
0.7127	Intermediate Similarity	NPD3051	Approved
0.7112	Intermediate Similarity	NPD2968	Approved
0.7112	Intermediate Similarity	NPD2971	Approved
0.7107	Intermediate Similarity	NPD7497	Discontinued
0.7088	Intermediate Similarity	NPD2969	Approved
0.7088	Intermediate Similarity	NPD2970	Approved
0.7068	Intermediate Similarity	NPD2488	Approved
0.7068	Intermediate Similarity	NPD2490	Approved
0.7052	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6002	Phase 3
0.7041	Intermediate Similarity	NPD6005	Phase 3
0.7041	Intermediate Similarity	NPD5762	Approved
0.7041	Intermediate Similarity	NPD5763	Approved
0.7041	Intermediate Similarity	NPD6004	Phase 3
0.7041	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6663	Approved
0.7022	Intermediate Similarity	NPD7972	Discontinued
0.7018	Intermediate Similarity	NPD6331	Phase 2
0.7018	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4110	Phase 3
0.7005	Intermediate Similarity	NPD2494	Approved
0.7005	Intermediate Similarity	NPD2493	Approved
0.6985	Remote Similarity	NPD4582	Approved
0.6985	Remote Similarity	NPD4583	Approved
0.6982	Remote Similarity	NPD5712	Approved
0.6977	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2489	Approved
0.6957	Remote Similarity	NPD4481	Phase 3
0.6957	Remote Similarity	NPD27	Approved
0.6954	Remote Similarity	NPD7019	Approved
0.6954	Remote Similarity	NPD7020	Approved
0.6949	Remote Similarity	NPD6502	Phase 2
0.6949	Remote Similarity	NPD7028	Phase 2
0.6936	Remote Similarity	NPD6667	Approved
0.6936	Remote Similarity	NPD6666	Approved
0.6935	Remote Similarity	NPD4002	Approved
0.6935	Remote Similarity	NPD4004	Approved
0.6923	Remote Similarity	NPD6746	Phase 2
0.6919	Remote Similarity	NPD3450	Approved
0.6919	Remote Similarity	NPD3452	Approved
0.6906	Remote Similarity	NPD7833	Phase 2
0.6906	Remote Similarity	NPD7831	Phase 2
0.6906	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD5811	Approved
0.689	Remote Similarity	NPD5736	Approved
0.6872	Remote Similarity	NPD6844	Discontinued
0.6851	Remote Similarity	NPD7773	Phase 2
0.6845	Remote Similarity	NPD6355	Discontinued
0.6842	Remote Similarity	NPD7312	Approved
0.6842	Remote Similarity	NPD7313	Approved
0.6842	Remote Similarity	NPD7311	Approved
0.6842	Remote Similarity	NPD7310	Approved
0.6829	Remote Similarity	NPD5647	Approved
0.6829	Remote Similarity	NPD4624	Approved
0.6826	Remote Similarity	NPD7477	Discontinued
0.6818	Remote Similarity	NPD52	Approved
0.6818	Remote Similarity	NPD7526	Approved
0.6818	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6677	Suspended
0.6806	Remote Similarity	NPD7309	Approved
0.68	Remote Similarity	NPD3057	Approved
0.6796	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2861	Phase 2
0.6784	Remote Similarity	NPD6099	Approved
0.6784	Remote Similarity	NPD6100	Approved
0.678	Remote Similarity	NPD7427	Discontinued
0.6779	Remote Similarity	NPD8404	Phase 2
0.6761	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4965	Approved
0.6758	Remote Similarity	NPD4967	Phase 2
0.6758	Remote Similarity	NPD4966	Approved
0.6744	Remote Similarity	NPD1375	Discontinued
0.6743	Remote Similarity	NPD7236	Approved
0.674	Remote Similarity	NPD5772	Approved
0.674	Remote Similarity	NPD5773	Approved
0.6737	Remote Similarity	NPD6764	Approved
0.6737	Remote Similarity	NPD6765	Approved
0.6737	Remote Similarity	NPD6104	Discontinued
0.6736	Remote Similarity	NPD4663	Approved
0.6734	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD3058	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7033	Discontinued
0.6724	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD4628	Phase 3
0.6722	Remote Similarity	NPD6072	Discontinued
0.6722	Remote Similarity	NPD7193	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6971	Discontinued
0.6716	Remote Similarity	NPD2972	Approved
0.6716	Remote Similarity	NPD3533	Approved
0.6708	Remote Similarity	NPD2932	Approved
0.6708	Remote Similarity	NPD3019	Approved
0.6706	Remote Similarity	NPD4097	Suspended
0.6705	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD7199	Phase 2
0.6702	Remote Similarity	NPD6620	Discovery
0.6701	Remote Similarity	NPD7906	Approved
0.67	Remote Similarity	NPD8161	Suspended
0.6687	Remote Similarity	NPD1712	Approved
0.6686	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD2238	Phase 2
0.6686	Remote Similarity	NPD4476	Approved
0.6686	Remote Similarity	NPD3620	Phase 2
0.6686	Remote Similarity	NPD4477	Approved
0.6686	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5699	Approved
0.6685	Remote Similarity	NPD6315	Phase 2
0.6685	Remote Similarity	NPD7248	Discontinued
0.6685	Remote Similarity	NPD37	Approved
0.6684	Remote Similarity	NPD3823	Discontinued
0.6667	Remote Similarity	NPD6042	Phase 2
0.6667	Remote Similarity	NPD42	Phase 2
0.6667	Remote Similarity	NPD5617	Suspended
0.6667	Remote Similarity	NPD7097	Phase 1
0.6667	Remote Similarity	NPD4578	Approved
0.6667	Remote Similarity	NPD4577	Approved
0.665	Remote Similarity	NPD4040	Phase 1
0.6649	Remote Similarity	NPD8434	Phase 2
0.6648	Remote Similarity	NPD7819	Suspended
0.6648	Remote Similarity	NPD7239	Suspended
0.6648	Remote Similarity	NPD5929	Approved
0.6647	Remote Similarity	NPD2614	Approved
0.6635	Remote Similarity	NPD4665	Approved
0.6635	Remote Similarity	NPD4111	Phase 1
0.6634	Remote Similarity	NPD2491	Approved
0.663	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6390	Discontinued
0.6629	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3400	Discontinued
0.6629	Remote Similarity	NPD4319	Phase 2
0.6628	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD2799	Discontinued
0.6617	Remote Similarity	NPD4107	Approved
0.6616	Remote Similarity	NPD4363	Phase 3
0.6616	Remote Similarity	NPD4360	Phase 2
0.6614	Remote Similarity	NPD7177	Discontinued
0.6614	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7228	Approved
0.6614	Remote Similarity	NPD7799	Discontinued
0.6614	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6959	Discontinued
0.6612	Remote Similarity	NPD2563	Approved
0.6612	Remote Similarity	NPD2560	Approved
0.6612	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD4005	Discontinued
0.6611	Remote Similarity	NPD3226	Approved
0.6609	Remote Similarity	NPD2424	Discontinued
0.6608	Remote Similarity	NPD6653	Approved
0.6606	Remote Similarity	NPD8651	Approved
0.6605	Remote Similarity	NPD3095	Discontinued
0.6598	Remote Similarity	NPD5036	Approved
0.6598	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6785	Approved
0.6598	Remote Similarity	NPD6784	Approved
0.6595	Remote Similarity	NPD6234	Discontinued
0.6593	Remote Similarity	NPD7577	Discontinued
0.6592	Remote Similarity	NPD7131	Phase 3
0.6591	Remote Similarity	NPD3692	Discontinued
0.6584	Remote Similarity	NPD3091	Approved
0.6583	Remote Similarity	NPD4361	Phase 2
0.6583	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.658	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.658	Remote Similarity	NPD5035	Approved
0.6578	Remote Similarity	NPD7608	Discontinued
0.6578	Remote Similarity	NPD7229	Phase 3
0.6578	Remote Similarity	NPD6071	Discontinued
0.6573	Remote Similarity	NPD7907	Approved
0.6573	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.657	Remote Similarity	NPD696	Discontinued
0.6568	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6798	Discontinued
0.6568	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD7810	Phase 3
0.6567	Remote Similarity	NPD7811	Phase 3

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