NPASS Compound

Structure

NPC71205 OpenBabel07101719512D 36 41 0 0 1 0 0 0 0 0999 V2000 -3.6128 -1.0648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3721 -0.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0261 -0.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1191 -3.3016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9745 -1.8390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0386 -1.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3191 0.0418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8838 -0.0702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3191 -0.7408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8838 -0.6288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1394 -0.7690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8487 -2.2275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4272 -1.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2047 0.7813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3062 0.8622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4806 -1.0276 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7447 -0.9351 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3212 -2.3557 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6414 0.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0774 -1.7351 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6414 -1.1321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5635 -0.0702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3212 -1.1321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8845 -1.4803 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8920 -2.0232 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6913 -1.3600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5635 -0.6288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3399 -1.6046 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7563 -0.6031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0326 -1.6187 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3399 0.9056 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 -2.5066 -0.8440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6695 -2.5357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2663 1.8701 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2047 -1.4803 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 4 18 1 0 0 0 0 5 30 1 0 0 0 0 7 9 1 0 0 0 0 7 19 2 0 0 0 0 8 10 2 0 0 0 0 8 19 1 0 0 0 0 9 21 2 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 16 1 0 0 0 0 13 30 1 0 0 0 0 14 19 1 0 0 0 0 14 31 1 0 0 0 0 15 22 2 0 0 0 0 15 31 1 0 0 0 0 16 2 1 6 0 0 0 17 3 1 6 0 0 0 17 26 1 0 0 0 0 18 25 1 0 0 0 0 20 6 1 1 0 0 0 20 23 1 0 0 0 0 21 36 1 0 0 0 0 22 27 1 0 0 0 0 22 29 1 0 0 0 0 23 24 1 0 0 0 0 23 27 1 6 0 0 0 24 25 1 0 0 0 0 24 28 1 0 0 0 0 25 30 1 0 0 0 0 26 28 1 0 0 0 0 26 30 1 0 0 0 0 27 33 2 0 0 0 0 28 36 1 0 0 0 0 29 32 2 0 0 0 0 29 34 1 0 0 0 0 31 32 1 0 0 0 0 31 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.08
Volume:	293.909
LogP:	1.873
LogD:	1.802
LogS:	-2.723
# Rotatable Bonds:	3
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.797
Synthetic Accessibility Score:	3.167
Fsp3:	0.188
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:	-4.761
MDCK Permeability:	1.2821328709833324e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.079
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.254
30% Bioavailability (F30%):	0.715

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.093
Plasma Protein Binding (PPB):	90.17261505126953%
Volume Distribution (VD):	0.73
Pgp-substrate:	6.533562183380127%

ADMET: Metabolism

CYP1A2-inhibitor:	0.846
CYP1A2-substrate:	0.661
CYP2C19-inhibitor:	0.335
CYP2C19-substrate:	0.287
CYP2C9-inhibitor:	0.382
CYP2C9-substrate:	0.92
CYP2D6-inhibitor:	0.551
CYP2D6-substrate:	0.865
CYP3A4-inhibitor:	0.733
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	13.24
Half-life (T1/2):	0.846

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.033
Drug-inuced Liver Injury (DILI):	0.876
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.06
Maximum Recommended Daily Dose:	0.039
Skin Sensitization:	0.514
Carcinogencity:	0.081
Eye Corrosion:	0.003
Eye Irritation:	0.058
Respiratory Toxicity:	0.122

Download Data

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

Natural Product: NPC71205

Natural Product ID:	NPC71205
*Common Name:**	Pyrrospirone C
IUPAC Name:	n.a.
Synonyms:	Pyrrospirone C
Standard InCHIKey:	KXMGXXHZDLJDBH-UHLMFRFDSA-N
Standard InCHI:	InChI=1S/C31H37NO4/c1-6-20-12-18(4)25-24-23(20)27(33)22-15-31(35,32-29(22)34)14-19-7-9-21(10-8-19)36-28(24)26-17(3)11-16(2)13-30(25,26)5/h6-10,12,15-17,20,23-26,28,35H,1,11,13-14H2,2-5H3,(H,32,34)/t16-,17+,20-,23+,24-,25+,26+,28+,30+,31-/m1/s1
SMILES:	C=C[C@@H]1C=C(C)[C@H]2[C@H]3[C@H]1C(=O)C1=C[C@](N=C1O)(O)Cc1ccc(O[C@@H]3[C@H]3[C@@]2(C)C[C@@H](C[C@@H]3C)C)cc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520703
PubChem CID:	10907072
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000064] Macrolactams

*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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	450.0	nM	PMID[450640]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	120.0	nM	PMID[450640]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	480.0	nM	PMID[450640]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	120.0	nM	PMID[450641]

☑ 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 NPC71205 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	243
0.1-0.2	1096
0.2-0.3	2365
0.3-0.4	6289
0.4-0.5	11730
0.5-0.6	11949
0.6-0.7	8878
0.7-0.8	134
0.8-0.85	5
0.85-0.9	5
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9351	High Similarity	NPC67080
0.8834	High Similarity	NPC88378
0.8834	High Similarity	NPC211713
0.8805	High Similarity	NPC471394
0.8805	High Similarity	NPC293164
0.8324	Intermediate Similarity	NPC471395
0.7974	Intermediate Similarity	NPC169766
0.7751	Intermediate Similarity	NPC471396
0.7547	Intermediate Similarity	NPC471201
0.7515	Intermediate Similarity	NPC476336
0.7485	Intermediate Similarity	NPC470273
0.7452	Intermediate Similarity	NPC328070
0.7438	Intermediate Similarity	NPC21797
0.7438	Intermediate Similarity	NPC322526
0.7438	Intermediate Similarity	NPC194847
0.7425	Intermediate Similarity	NPC253591
0.7394	Intermediate Similarity	NPC247221
0.7375	Intermediate Similarity	NPC473052
0.7375	Intermediate Similarity	NPC473055
0.7365	Intermediate Similarity	NPC93666
0.7346	Intermediate Similarity	NPC234548
0.7346	Intermediate Similarity	NPC248287
0.7337	Intermediate Similarity	NPC261659
0.7337	Intermediate Similarity	NPC178048
0.7325	Intermediate Similarity	NPC288290
0.7312	Intermediate Similarity	NPC208725
0.7308	Intermediate Similarity	NPC116057
0.7305	Intermediate Similarity	NPC470019
0.7305	Intermediate Similarity	NPC476338
0.7305	Intermediate Similarity	NPC476359
0.729	Intermediate Similarity	NPC137416
0.7284	Intermediate Similarity	NPC98804
0.7278	Intermediate Similarity	NPC146014
0.7256	Intermediate Similarity	NPC205765
0.7251	Intermediate Similarity	NPC205392
0.7251	Intermediate Similarity	NPC105942
0.7247	Intermediate Similarity	NPC198075
0.7235	Intermediate Similarity	NPC140133
0.7233	Intermediate Similarity	NPC470392
0.7225	Intermediate Similarity	NPC469507
0.7222	Intermediate Similarity	NPC471316
0.7219	Intermediate Similarity	NPC146388
0.7219	Intermediate Similarity	NPC478189
0.7205	Intermediate Similarity	NPC194970
0.7202	Intermediate Similarity	NPC273798
0.7193	Intermediate Similarity	NPC246164
0.7188	Intermediate Similarity	NPC251549
0.7188	Intermediate Similarity	NPC132308
0.7186	Intermediate Similarity	NPC280717
0.7186	Intermediate Similarity	NPC185456
0.7186	Intermediate Similarity	NPC56731
0.7186	Intermediate Similarity	NPC271607
0.7184	Intermediate Similarity	NPC116639
0.7182	Intermediate Similarity	NPC195972
0.7178	Intermediate Similarity	NPC119542
0.7176	Intermediate Similarity	NPC237441
0.716	Intermediate Similarity	NPC173569
0.716	Intermediate Similarity	NPC478163
0.716	Intermediate Similarity	NPC477874
0.7152	Intermediate Similarity	NPC472801
0.7152	Intermediate Similarity	NPC155552
0.7152	Intermediate Similarity	NPC51181
0.7151	Intermediate Similarity	NPC471863
0.7135	Intermediate Similarity	NPC314653
0.7135	Intermediate Similarity	NPC316262
0.7134	Intermediate Similarity	NPC269598
0.7134	Intermediate Similarity	NPC202260
0.7126	Intermediate Similarity	NPC313414
0.7126	Intermediate Similarity	NPC476750
0.7125	Intermediate Similarity	NPC125153
0.7119	Intermediate Similarity	NPC261184
0.7118	Intermediate Similarity	NPC46549
0.7118	Intermediate Similarity	NPC264229
0.7118	Intermediate Similarity	NPC470998
0.7118	Intermediate Similarity	NPC132810
0.7117	Intermediate Similarity	NPC249817
0.711	Intermediate Similarity	NPC476194
0.711	Intermediate Similarity	NPC305710
0.711	Intermediate Similarity	NPC25351
0.711	Intermediate Similarity	NPC476364
0.7101	Intermediate Similarity	NPC470274
0.7101	Intermediate Similarity	NPC302987
0.7093	Intermediate Similarity	NPC476335
0.7093	Intermediate Similarity	NPC56635
0.7091	Intermediate Similarity	NPC221134
0.7089	Intermediate Similarity	NPC472413
0.7086	Intermediate Similarity	NPC472823
0.7083	Intermediate Similarity	NPC132771
0.7083	Intermediate Similarity	NPC235195
0.7083	Intermediate Similarity	NPC19862
0.7083	Intermediate Similarity	NPC169942
0.7081	Intermediate Similarity	NPC165612
0.7079	Intermediate Similarity	NPC469395
0.7076	Intermediate Similarity	NPC12854
0.7076	Intermediate Similarity	NPC471114
0.7073	Intermediate Similarity	NPC150712
0.7073	Intermediate Similarity	NPC472376
0.7073	Intermediate Similarity	NPC118366
0.7073	Intermediate Similarity	NPC471152
0.7073	Intermediate Similarity	NPC475482
0.7073	Intermediate Similarity	NPC198621
0.7073	Intermediate Similarity	NPC216940
0.7073	Intermediate Similarity	NPC22676
0.7069	Intermediate Similarity	NPC478161
0.7069	Intermediate Similarity	NPC478159
0.7063	Intermediate Similarity	NPC477645
0.7059	Intermediate Similarity	NPC66991
0.7059	Intermediate Similarity	NPC10990
0.7059	Intermediate Similarity	NPC300988
0.7056	Intermediate Similarity	NPC471859
0.7055	Intermediate Similarity	NPC252343
0.7052	Intermediate Similarity	NPC44606
0.7048	Intermediate Similarity	NPC78987
0.7048	Intermediate Similarity	NPC82336
0.7044	Intermediate Similarity	NPC469930
0.7041	Intermediate Similarity	NPC8102
0.7041	Intermediate Similarity	NPC189054
0.7041	Intermediate Similarity	NPC66894
0.7037	Intermediate Similarity	NPC327410
0.7037	Intermediate Similarity	NPC203486
0.7035	Intermediate Similarity	NPC472787
0.7035	Intermediate Similarity	NPC58661
0.7035	Intermediate Similarity	NPC473579
0.7035	Intermediate Similarity	NPC475454
0.7035	Intermediate Similarity	NPC473680
0.7035	Intermediate Similarity	NPC321896
0.7035	Intermediate Similarity	NPC475311
0.7035	Intermediate Similarity	NPC476185
0.7035	Intermediate Similarity	NPC118033
0.703	Intermediate Similarity	NPC475104
0.703	Intermediate Similarity	NPC307883
0.7025	Intermediate Similarity	NPC71610
0.7025	Intermediate Similarity	NPC471929
0.7025	Intermediate Similarity	NPC471935
0.7025	Intermediate Similarity	NPC471930
0.7024	Intermediate Similarity	NPC251372
0.7024	Intermediate Similarity	NPC316691
0.7022	Intermediate Similarity	NPC475106
0.7022	Intermediate Similarity	NPC476749
0.7018	Intermediate Similarity	NPC279442
0.7018	Intermediate Similarity	NPC234494
0.7018	Intermediate Similarity	NPC39195
0.7018	Intermediate Similarity	NPC145467
0.7013	Intermediate Similarity	NPC263835
0.7012	Intermediate Similarity	NPC471670
0.7012	Intermediate Similarity	NPC153007
0.7012	Intermediate Similarity	NPC474610
0.7012	Intermediate Similarity	NPC476699
0.7011	Intermediate Similarity	NPC179170
0.7006	Intermediate Similarity	NPC474532
0.7006	Intermediate Similarity	NPC323965
0.7006	Intermediate Similarity	NPC75432
0.7006	Intermediate Similarity	NPC130489
0.7006	Intermediate Similarity	NPC208676
0.7006	Intermediate Similarity	NPC472618
0.7006	Intermediate Similarity	NPC263337
0.7	Intermediate Similarity	NPC472938
0.7	Intermediate Similarity	NPC472937
0.7	Intermediate Similarity	NPC85047
0.7	Intermediate Similarity	NPC286038
0.7	Intermediate Similarity	NPC476751
0.7	Intermediate Similarity	NPC17274
0.7	Intermediate Similarity	NPC120857
0.7	Intermediate Similarity	NPC471174
0.7	Intermediate Similarity	NPC299011
0.7	Intermediate Similarity	NPC472936
0.7	Intermediate Similarity	NPC469758
0.6995	Remote Similarity	NPC167340
0.6994	Remote Similarity	NPC477210
0.6994	Remote Similarity	NPC196708
0.6994	Remote Similarity	NPC473773
0.6994	Remote Similarity	NPC33938
0.6994	Remote Similarity	NPC212699
0.6994	Remote Similarity	NPC207675
0.6994	Remote Similarity	NPC475579
0.6994	Remote Similarity	NPC470996
0.6994	Remote Similarity	NPC48671
0.6994	Remote Similarity	NPC11266
0.6989	Remote Similarity	NPC474611
0.6989	Remote Similarity	NPC84349
0.6988	Remote Similarity	NPC56197
0.6988	Remote Similarity	NPC477408
0.6988	Remote Similarity	NPC76312
0.6983	Remote Similarity	NPC327694
0.6983	Remote Similarity	NPC161151
0.6982	Remote Similarity	NPC290404
0.6982	Remote Similarity	NPC471600
0.6981	Remote Similarity	NPC262936
0.6981	Remote Similarity	NPC30491
0.6981	Remote Similarity	NPC329707
0.6978	Remote Similarity	NPC313717
0.6978	Remote Similarity	NPC315306
0.6977	Remote Similarity	NPC470997
0.6977	Remote Similarity	NPC317492
0.6977	Remote Similarity	NPC196846
0.6977	Remote Similarity	NPC212257
0.6975	Remote Similarity	NPC477407
0.6974	Remote Similarity	NPC19290
0.6973	Remote Similarity	NPC206061
0.6971	Remote Similarity	NPC156348

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 NPC71205 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	648
0.2-0.3	917
0.3-0.4	1829
0.4-0.5	2918
0.5-0.6	1983
0.6-0.7	660
0.7-0.8	21
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
0.7616	Intermediate Similarity	NPD7315	Approved
0.7515	Intermediate Similarity	NPD6273	Approved
0.7407	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6353	Approved
0.7312	Intermediate Similarity	NPD2157	Approved
0.7296	Intermediate Similarity	NPD4140	Approved
0.7284	Intermediate Similarity	NPD5712	Approved
0.7273	Intermediate Similarity	NPD5327	Phase 3
0.725	Intermediate Similarity	NPD5735	Approved
0.7235	Intermediate Similarity	NPD6502	Phase 2
0.7235	Intermediate Similarity	NPD7028	Phase 2
0.7233	Intermediate Similarity	NPD6663	Approved
0.7233	Intermediate Similarity	NPD8032	Phase 2
0.7222	Intermediate Similarity	NPD3823	Discontinued
0.7212	Intermediate Similarity	NPD4110	Phase 3
0.7212	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5760	Phase 2
0.7209	Intermediate Similarity	NPD5761	Phase 2
0.7193	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2161	Phase 2
0.7159	Intermediate Similarity	NPD8127	Discontinued
0.7134	Intermediate Similarity	NPD5647	Approved
0.7117	Intermediate Similarity	NPD2799	Discontinued
0.711	Intermediate Similarity	NPD7972	Discontinued
0.7108	Intermediate Similarity	NPD6331	Phase 2
0.7089	Intermediate Similarity	NPD5736	Approved
0.7076	Intermediate Similarity	NPD5811	Approved
0.7072	Intermediate Similarity	NPD5557	Phase 1
0.7066	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7131	Phase 3
0.7056	Intermediate Similarity	NPD3909	Discontinued
0.7037	Intermediate Similarity	NPD6355	Discontinued
0.7019	Intermediate Similarity	NPD3058	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2932	Approved
0.7006	Intermediate Similarity	NPD4628	Phase 3
0.7006	Intermediate Similarity	NPD1876	Approved
0.6971	Remote Similarity	NPD7318	Phase 3
0.6954	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7577	Discontinued
0.6954	Remote Similarity	NPD6844	Discontinued
0.6937	Remote Similarity	NPD2614	Approved
0.6932	Remote Similarity	NPD7773	Phase 2
0.6918	Remote Similarity	NPD4624	Approved
0.6914	Remote Similarity	NPD7477	Discontinued
0.6905	Remote Similarity	NPD8166	Discontinued
0.6905	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3019	Approved
0.6902	Remote Similarity	NPD6104	Discontinued
0.6901	Remote Similarity	NPD6390	Discontinued
0.6893	Remote Similarity	NPD7831	Phase 2
0.6893	Remote Similarity	NPD7833	Phase 2
0.6893	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.689	Remote Similarity	NPD4097	Suspended
0.6887	Remote Similarity	NPD1241	Discontinued
0.6882	Remote Similarity	NPD4357	Discontinued
0.6879	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5977	Approved
0.6875	Remote Similarity	NPD5978	Approved
0.6867	Remote Similarity	NPD4477	Approved
0.6867	Remote Similarity	NPD4476	Approved
0.6865	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.686	Remote Similarity	NPD3869	Phase 3
0.686	Remote Similarity	NPD7427	Discontinued
0.686	Remote Similarity	NPD3873	Phase 3
0.6857	Remote Similarity	NPD7317	Phase 3
0.6854	Remote Similarity	NPD6862	Phase 2
0.6851	Remote Similarity	NPD6894	Phase 1
0.6842	Remote Similarity	NPD7020	Approved
0.6842	Remote Similarity	NPD3819	Phase 2
0.6842	Remote Similarity	NPD7019	Approved
0.6828	Remote Similarity	NPD7546	Discontinued
0.6826	Remote Similarity	NPD2344	Approved
0.6826	Remote Similarity	NPD5762	Approved
0.6826	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD5763	Approved
0.6826	Remote Similarity	NPD6002	Phase 3
0.6826	Remote Similarity	NPD6005	Phase 3
0.6826	Remote Similarity	NPD6004	Phase 3
0.6826	Remote Similarity	NPD2346	Discontinued
0.6807	Remote Similarity	NPD3846	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7003	Approved
0.68	Remote Similarity	NPD6677	Suspended
0.6798	Remote Similarity	NPD6971	Discontinued
0.6791	Remote Similarity	NPD6556	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2424	Discontinued
0.6786	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7458	Discontinued
0.678	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD7693	Approved
0.6772	Remote Similarity	NPD3972	Approved
0.677	Remote Similarity	NPD1712	Approved
0.6768	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD3142	Approved
0.6768	Remote Similarity	NPD3620	Phase 2
0.6768	Remote Similarity	NPD3140	Approved
0.6768	Remote Similarity	NPD8161	Suspended
0.676	Remote Similarity	NPD6315	Phase 2
0.6751	Remote Similarity	NPD7497	Discontinued
0.675	Remote Similarity	NPD2797	Approved
0.6748	Remote Similarity	NPD2313	Discontinued
0.6748	Remote Similarity	NPD3268	Approved
0.6747	Remote Similarity	NPD696	Discontinued
0.6746	Remote Similarity	NPD2976	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD5617	Suspended
0.6738	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.673	Remote Similarity	NPD1669	Approved
0.673	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7236	Approved
0.6725	Remote Similarity	NPD6666	Approved
0.6725	Remote Similarity	NPD6667	Approved
0.6723	Remote Similarity	NPD5929	Approved
0.6723	Remote Similarity	NPD7819	Suspended
0.6722	Remote Similarity	NPD6746	Phase 2
0.672	Remote Similarity	NPD6764	Approved
0.672	Remote Similarity	NPD6765	Approved
0.6709	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD2798	Approved
0.6705	Remote Similarity	NPD4319	Phase 2
0.6704	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD2667	Approved
0.6688	Remote Similarity	NPD2668	Approved
0.6687	Remote Similarity	NPD6653	Approved
0.6686	Remote Similarity	NPD1549	Phase 2
0.6685	Remote Similarity	NPD2379	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD5967	Approved
0.6685	Remote Similarity	NPD6620	Discovery
0.6685	Remote Similarity	NPD7493	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7291	Discontinued
0.6683	Remote Similarity	NPD8404	Phase 2
0.6667	Remote Similarity	NPD3091	Approved
0.6667	Remote Similarity	NPD6099	Approved
0.6667	Remote Similarity	NPD2898	Approved
0.6667	Remote Similarity	NPD6100	Approved
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD2309	Approved
0.6667	Remote Similarity	NPD3451	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5699	Approved
0.6649	Remote Similarity	NPD3965	Phase 1
0.6648	Remote Similarity	NPD7608	Discontinued
0.6647	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3026	Approved
0.6646	Remote Similarity	NPD6362	Approved
0.6646	Remote Similarity	NPD6798	Discontinued
0.6646	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3023	Approved
0.6633	Remote Similarity	NPD7565	Approved
0.6632	Remote Similarity	NPD8434	Phase 2
0.6629	Remote Similarity	NPD7239	Suspended
0.6629	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD654	Phase 3
0.6627	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3685	Discontinued
0.6624	Remote Similarity	NPD1651	Approved
0.6624	Remote Similarity	NPD3024	Approved
0.6624	Remote Similarity	NPD3025	Approved
0.6615	Remote Similarity	NPD2488	Approved
0.6615	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD2490	Approved
0.6611	Remote Similarity	NPD7075	Discontinued
0.661	Remote Similarity	NPD6072	Discontinued
0.661	Remote Similarity	NPD6873	Phase 2
0.6609	Remote Similarity	NPD52	Approved
0.6609	Remote Similarity	NPD4186	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD7526	Approved
0.6608	Remote Similarity	NPD3750	Approved
0.6607	Remote Similarity	NPD4108	Discontinued
0.6607	Remote Similarity	NPD7033	Discontinued
0.6601	Remote Similarity	NPD821	Approved
0.6595	Remote Similarity	NPD7177	Discontinued
0.6591	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD2651	Approved
0.6591	Remote Similarity	NPD3226	Approved
0.6591	Remote Similarity	NPD2649	Approved
0.6588	Remote Similarity	NPD7037	Approved
0.6585	Remote Similarity	NPD7095	Approved
0.6584	Remote Similarity	NPD1283	Approved
0.6582	Remote Similarity	NPD3095	Discontinued
0.6581	Remote Similarity	NPD7157	Approved
0.6579	Remote Similarity	NPD6784	Approved
0.6579	Remote Similarity	NPD6785	Approved
0.6573	Remote Similarity	NPD6280	Approved
0.6573	Remote Similarity	NPD6279	Approved
0.6568	Remote Similarity	NPD2935	Discontinued
0.6566	Remote Similarity	NPD2979	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