NPASS Compound

Structure

CID279589 OpenBabel06191716082D 37 44 0 0 1 0 0 0 0 0999 V2000 -0.8140 -1.0305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5477 0.1426 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0665 2.6917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0666 1.7038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2115 3.1854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2116 1.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1686 1.2416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1383 1.9125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1638 0.9765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3560 2.6916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4181 1.0091 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3561 1.7037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9030 1.1719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2893 2.5137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5011 0.5012 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3545 2.6915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3306 1.7731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0650 1.7035 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2101 3.1852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0651 2.6914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3545 1.7036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2100 1.2098 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0237 2.4440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8064 0.5745 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4155 4.1509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7989 3.3520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7087 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8145 1.9661 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3974 4.2540 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5011 1.2099 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.2099 0.5011 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.1416 3.4556 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6240 3.2881 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7225 4.9207 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8120 3.1365 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8018 0.8612 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 2 36 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 10 2 0 0 0 0 6 12 2 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 24 1 0 0 0 0 11 28 1 6 0 0 0 12 30 1 0 0 0 0 13 17 2 0 0 0 0 13 31 1 0 0 0 0 14 23 2 0 0 0 0 14 32 1 0 0 0 0 15 9 1 1 0 0 0 15 30 1 0 0 0 0 15 37 1 0 0 0 0 16 19 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 26 1 0 0 0 0 21 22 2 0 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 33 1 0 0 0 0 24 27 1 6 0 0 0 24 36 1 0 0 0 0 25 29 2 0 0 0 0 25 34 1 0 0 0 0 26 29 1 0 0 0 0 26 35 2 0 0 0 0 27 1 1 1 0 0 0 27 31 1 0 0 0 0 27 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.15
Volume:	474.824
LogP:	3.378
LogD:	2.531
LogS:	-7.544
# Rotatable Bonds:	1
TPSA:	140.97
# H-Bond Aceptor:	10
# H-Bond Donor:	5
# Rings:	8
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.206
Synthetic Accessibility Score:	5.224
Fsp3:	0.259
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.961
MDCK Permeability:	3.660918309833505e-06
Pgp-inhibitor:	0.054
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.797
20% Bioavailability (F20%):	0.221
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	97.04749298095703%
Volume Distribution (VD):	0.616
Pgp-substrate:	2.5265493392944336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.689
CYP1A2-substrate:	0.813
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.142
CYP2C9-inhibitor:	0.808
CYP2C9-substrate:	0.605
CYP2D6-inhibitor:	0.39
CYP2D6-substrate:	0.158
CYP3A4-inhibitor:	0.261
CYP3A4-substrate:	0.856

ADMET: Excretion

Clearance (CL):	8.416
Half-life (T1/2):	0.28

ADMET: Toxicity

hERG Blockers:	0.101
Human Hepatotoxicity (H-HT):	0.792
Drug-inuced Liver Injury (DILI):	0.97
AMES Toxicity:	0.706
Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.98
Skin Sensitization:	0.716
Carcinogencity:	0.963
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.703

Download Data

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

Natural Product: NPC279589

Natural Product ID:	NPC279589
*Common Name:**	MPFXTYXHOXVKPU-YWVZRHFBSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MPFXTYXHOXVKPU-YWVZRHFBSA-N
Standard InCHI:	InChI=1S/C27H22N4O6/c1-27-24(36-2)11(28)9-15(37-27)30-12-6-4-3-5-10(12)16-19-20(26(35)29-25(19)34)18-17-13(7-8-14(32)23(17)33)31(27)22(18)21(16)30/h3-8,11,15,24,32-33H,9,28H2,1-2H3,(H,29,34,35)/t11-,15-,24-,27+/m1/s1
SMILES:	C[C@]12[C@@H]([C@@H](C[C@H](n3c4ccccc4c4c5c(c6c7c(ccc(c7O)O)n1c6c34)C(=O)N=C5O)O2)N)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491461
PubChem CID:	24899411
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles [CHEMONTID:0001865] Pyrrolocarbazoles [CHEMONTID:0001866] Indolocarbazoles

*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
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18484775]
NPO22004	Cystodytes solitus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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
GI50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	GI50	=	17.5	nM	PMID[501226]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	90.3	nM	PMID[501226]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	32.1	nM	PMID[501226]

☑ 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 NPC279589 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	533
0.1-0.2	2595
0.2-0.3	13128
0.3-0.4	8615
0.4-0.5	12870
0.5-0.6	3357
0.6-0.7	1477
0.7-0.8	109
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9959	High Similarity	NPC45048
0.8462	Intermediate Similarity	NPC160898
0.8394	Intermediate Similarity	NPC107836
0.8182	Intermediate Similarity	NPC313884
0.8182	Intermediate Similarity	NPC98371
0.8057	Intermediate Similarity	NPC132329
0.7803	Intermediate Similarity	NPC1203
0.7782	Intermediate Similarity	NPC472842
0.7725	Intermediate Similarity	NPC472207
0.7708	Intermediate Similarity	NPC94428
0.7708	Intermediate Similarity	NPC263937
0.766	Intermediate Similarity	NPC89549
0.7551	Intermediate Similarity	NPC31700
0.7528	Intermediate Similarity	NPC472846
0.7509	Intermediate Similarity	NPC132385
0.739	Intermediate Similarity	NPC227824
0.7368	Intermediate Similarity	NPC294620
0.7348	Intermediate Similarity	NPC218388
0.7323	Intermediate Similarity	NPC472843
0.7258	Intermediate Similarity	NPC9894
0.7256	Intermediate Similarity	NPC270515
0.7241	Intermediate Similarity	NPC473183
0.7236	Intermediate Similarity	NPC53344
0.718	Intermediate Similarity	NPC178858
0.718	Intermediate Similarity	NPC469734
0.7165	Intermediate Similarity	NPC39370
0.7165	Intermediate Similarity	NPC473184
0.716	Intermediate Similarity	NPC227908
0.7159	Intermediate Similarity	NPC475844
0.7154	Intermediate Similarity	NPC264285
0.7153	Intermediate Similarity	NPC472845
0.7148	Intermediate Similarity	NPC329982
0.7143	Intermediate Similarity	NPC472844
0.7138	Intermediate Similarity	NPC67401
0.7138	Intermediate Similarity	NPC473188
0.7132	Intermediate Similarity	NPC478081
0.7126	Intermediate Similarity	NPC473182
0.7122	Intermediate Similarity	NPC478080
0.7117	Intermediate Similarity	NPC195788
0.7117	Intermediate Similarity	NPC237901
0.7115	Intermediate Similarity	NPC474701
0.7112	Intermediate Similarity	NPC478010
0.7107	Intermediate Similarity	NPC471303
0.7094	Intermediate Similarity	NPC81175
0.7094	Intermediate Similarity	NPC477066
0.7088	Intermediate Similarity	NPC473186
0.7088	Intermediate Similarity	NPC207686
0.7078	Intermediate Similarity	NPC474188
0.7077	Intermediate Similarity	NPC260909
0.7075	Intermediate Similarity	NPC469928
0.7072	Intermediate Similarity	NPC473187
0.7072	Intermediate Similarity	NPC477549
0.7068	Intermediate Similarity	NPC473540
0.7045	Intermediate Similarity	NPC15801
0.7045	Intermediate Similarity	NPC6786
0.7043	Intermediate Similarity	NPC16352
0.704	Intermediate Similarity	NPC100734
0.704	Intermediate Similarity	NPC88923
0.704	Intermediate Similarity	NPC315634
0.7031	Intermediate Similarity	NPC276657
0.7027	Intermediate Similarity	NPC214980
0.7026	Intermediate Similarity	NPC17437
0.7019	Intermediate Similarity	NPC41679
0.7015	Intermediate Similarity	NPC78609
0.7015	Intermediate Similarity	NPC208522
0.7011	Intermediate Similarity	NPC181081
0.7011	Intermediate Similarity	NPC473800
0.7004	Intermediate Similarity	NPC477067
0.7004	Intermediate Similarity	NPC478082
0.7	Intermediate Similarity	NPC473185
0.6989	Remote Similarity	NPC478009
0.6982	Remote Similarity	NPC478006
0.6981	Remote Similarity	NPC184680
0.6973	Remote Similarity	NPC253580
0.6973	Remote Similarity	NPC252251
0.6971	Remote Similarity	NPC478083
0.6965	Remote Similarity	NPC86078
0.6955	Remote Similarity	NPC470785
0.6955	Remote Similarity	NPC82472
0.6941	Remote Similarity	NPC330009
0.6935	Remote Similarity	NPC470126
0.6932	Remote Similarity	NPC329631
0.6929	Remote Similarity	NPC478074
0.6929	Remote Similarity	NPC41501
0.6929	Remote Similarity	NPC475816
0.692	Remote Similarity	NPC129897
0.692	Remote Similarity	NPC474688
0.692	Remote Similarity	NPC477531
0.6917	Remote Similarity	NPC28945
0.6917	Remote Similarity	NPC23294
0.6917	Remote Similarity	NPC285343
0.6914	Remote Similarity	NPC293151
0.6911	Remote Similarity	NPC162748
0.6908	Remote Similarity	NPC194740
0.6906	Remote Similarity	NPC325976
0.6899	Remote Similarity	NPC472099
0.6895	Remote Similarity	NPC191489
0.6894	Remote Similarity	NPC474192
0.6894	Remote Similarity	NPC475720
0.6893	Remote Similarity	NPC315467
0.6892	Remote Similarity	NPC270918
0.6891	Remote Similarity	NPC470784
0.6886	Remote Similarity	NPC133609
0.6885	Remote Similarity	NPC51388
0.6882	Remote Similarity	NPC326363
0.6882	Remote Similarity	NPC209174
0.6879	Remote Similarity	NPC101312
0.6877	Remote Similarity	NPC303951
0.6877	Remote Similarity	NPC124086
0.6873	Remote Similarity	NPC303374
0.687	Remote Similarity	NPC478078
0.6866	Remote Similarity	NPC478012
0.6866	Remote Similarity	NPC477861
0.6863	Remote Similarity	NPC475666
0.6861	Remote Similarity	NPC189079
0.6859	Remote Similarity	NPC284685
0.6857	Remote Similarity	NPC195314
0.6852	Remote Similarity	NPC142385
0.685	Remote Similarity	NPC294375
0.6848	Remote Similarity	NPC246658
0.6842	Remote Similarity	NPC253675
0.6836	Remote Similarity	NPC244543
0.6835	Remote Similarity	NPC185197
0.6834	Remote Similarity	NPC132642
0.6832	Remote Similarity	NPC470018
0.6828	Remote Similarity	NPC474183
0.6827	Remote Similarity	NPC81939
0.6824	Remote Similarity	NPC472098
0.6815	Remote Similarity	NPC72905
0.6811	Remote Similarity	NPC5145
0.6808	Remote Similarity	NPC280799
0.6805	Remote Similarity	NPC323752
0.6805	Remote Similarity	NPC220852
0.6802	Remote Similarity	NPC153042
0.6798	Remote Similarity	NPC210828
0.6798	Remote Similarity	NPC86834
0.6797	Remote Similarity	NPC250448
0.679	Remote Similarity	NPC188400
0.679	Remote Similarity	NPC15406
0.6783	Remote Similarity	NPC312645
0.678	Remote Similarity	NPC33949
0.678	Remote Similarity	NPC274640
0.6779	Remote Similarity	NPC277351
0.6775	Remote Similarity	NPC314882
0.6773	Remote Similarity	NPC476098
0.6772	Remote Similarity	NPC476116
0.677	Remote Similarity	NPC239763
0.677	Remote Similarity	NPC190401
0.6769	Remote Similarity	NPC150239
0.6768	Remote Similarity	NPC24370
0.6768	Remote Similarity	NPC202503
0.6768	Remote Similarity	NPC319232
0.6767	Remote Similarity	NPC49547
0.6767	Remote Similarity	NPC9482
0.6767	Remote Similarity	NPC315499
0.6765	Remote Similarity	NPC284141
0.6764	Remote Similarity	NPC137353
0.6762	Remote Similarity	NPC152620
0.6761	Remote Similarity	NPC473639
0.6757	Remote Similarity	NPC303658
0.6754	Remote Similarity	NPC272549
0.6753	Remote Similarity	NPC473312
0.6752	Remote Similarity	NPC63971
0.6752	Remote Similarity	NPC91868
0.6748	Remote Similarity	NPC478011
0.6746	Remote Similarity	NPC475070
0.6745	Remote Similarity	NPC207620
0.6744	Remote Similarity	NPC322064
0.6744	Remote Similarity	NPC183407
0.6743	Remote Similarity	NPC121069
0.6742	Remote Similarity	NPC6215
0.6732	Remote Similarity	NPC100573
0.6732	Remote Similarity	NPC316181
0.6732	Remote Similarity	NPC39679
0.6732	Remote Similarity	NPC151781
0.6732	Remote Similarity	NPC207873
0.6732	Remote Similarity	NPC74562
0.6731	Remote Similarity	NPC473179
0.673	Remote Similarity	NPC179287
0.6727	Remote Similarity	NPC53534
0.6725	Remote Similarity	NPC314176
0.6722	Remote Similarity	NPC169716
0.6718	Remote Similarity	NPC476041
0.6718	Remote Similarity	NPC304926
0.6718	Remote Similarity	NPC303384
0.6718	Remote Similarity	NPC191088
0.6718	Remote Similarity	NPC298840
0.6718	Remote Similarity	NPC220851
0.6718	Remote Similarity	NPC268393
0.6718	Remote Similarity	NPC3214
0.6718	Remote Similarity	NPC13599
0.6717	Remote Similarity	NPC311906
0.6716	Remote Similarity	NPC217554
0.6716	Remote Similarity	NPC210296
0.6715	Remote Similarity	NPC471891
0.6706	Remote Similarity	NPC200836
0.6706	Remote Similarity	NPC469589
0.6706	Remote Similarity	NPC325297
0.6705	Remote Similarity	NPC298449
0.6705	Remote Similarity	NPC118228

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 NPC279589 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	622
0.2-0.3	1039
0.3-0.4	1903
0.4-0.5	2783
0.5-0.6	1961
0.6-0.7	526
0.7-0.8	50
0.8-0.85	5
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD7921	Approved
0.8398	Intermediate Similarity	NPD6456	Discontinued
0.8365	Intermediate Similarity	NPD7181	Phase 3
0.8189	Intermediate Similarity	NPD6978	Phase 2
0.8189	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD3746	Discontinued
0.7737	Intermediate Similarity	NPD7073	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7713	Intermediate Similarity	NPD5488	Discontinued
0.7683	Intermediate Similarity	NPD6455	Phase 3
0.7598	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD6995	Phase 1
0.7358	Intermediate Similarity	NPD7769	Phase 3
0.7347	Intermediate Similarity	NPD2916	Discontinued
0.7315	Intermediate Similarity	NPD7688	Phase 1
0.7259	Intermediate Similarity	NPD8091	Phase 3
0.7197	Intermediate Similarity	NPD6716	Phase 1
0.7197	Intermediate Similarity	NPD7770	Phase 3
0.7132	Intermediate Similarity	NPD7772	Phase 3
0.7126	Intermediate Similarity	NPD4373	Phase 2
0.7126	Intermediate Similarity	NPD7001	Phase 3
0.7121	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD8016	Phase 3
0.7121	Intermediate Similarity	NPD4561	Discontinued
0.7117	Intermediate Similarity	NPD8467	Approved
0.7117	Intermediate Similarity	NPD8466	Approved
0.7117	Intermediate Similarity	NPD8465	Approved
0.7086	Intermediate Similarity	NPD8363	Approved
0.7086	Intermediate Similarity	NPD8364	Approved
0.7085	Intermediate Similarity	NPD8463	Approved
0.7085	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6531	Approved
0.708	Intermediate Similarity	NPD6530	Approved
0.7077	Intermediate Similarity	NPD8460	Approved
0.7077	Intermediate Similarity	NPD8459	Approved
0.7066	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7057	Intermediate Similarity	NPD8428	Approved
0.7057	Intermediate Similarity	NPD8429	Approved
0.7057	Intermediate Similarity	NPD8427	Approved
0.7056	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD7803	Approved
0.7037	Intermediate Similarity	NPD3986	Discontinued
0.7036	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7417	Discontinued
0.7026	Intermediate Similarity	NPD8358	Approved
0.7023	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8426	Approved
0.7018	Intermediate Similarity	NPD8425	Approved
0.7015	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4952	Phase 3
0.7004	Intermediate Similarity	NPD5507	Approved
0.7004	Intermediate Similarity	NPD5506	Approved
0.6988	Remote Similarity	NPD5530	Phase 1
0.6985	Remote Similarity	NPD6724	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5482	Discontinued
0.6932	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7708	Approved
0.6886	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6877	Remote Similarity	NPD6517	Phase 3
0.6866	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD7665	Phase 2
0.6865	Remote Similarity	NPD7666	Phase 3
0.6859	Remote Similarity	NPD7955	Approved
0.6859	Remote Similarity	NPD7956	Approved
0.6858	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.685	Remote Similarity	NPD3809	Discontinued
0.6842	Remote Similarity	NPD6142	Phase 3
0.6836	Remote Similarity	NPD5902	Approved
0.6836	Remote Similarity	NPD5903	Approved
0.6832	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7603	Discontinued
0.6805	Remote Similarity	NPD6494	Phase 2
0.6791	Remote Similarity	NPD8524	Approved
0.6783	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD2951	Discontinued
0.677	Remote Similarity	NPD4897	Phase 2
0.6769	Remote Similarity	NPD5930	Phase 3
0.6765	Remote Similarity	NPD3962	Phase 2
0.6765	Remote Similarity	NPD3959	Phase 2
0.6759	Remote Similarity	NPD7452	Approved
0.6759	Remote Similarity	NPD7453	Approved
0.6757	Remote Similarity	NPD5632	Approved
0.6757	Remote Similarity	NPD8489	Phase 1
0.6749	Remote Similarity	NPD7925	Phase 2
0.6749	Remote Similarity	NPD7924	Phase 2
0.6747	Remote Similarity	NPD6999	Discontinued
0.6747	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD7726	Phase 1
0.6742	Remote Similarity	NPD4845	Discontinued
0.6738	Remote Similarity	NPD5450	Discontinued
0.6727	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD7767	Approved
0.6714	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD7426	Phase 1
0.6704	Remote Similarity	NPD4885	Approved
0.6693	Remote Similarity	NPD7222	Phase 2
0.6692	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD7395	Discontinued
0.6692	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD7398	Approved
0.6691	Remote Similarity	NPD7397	Approved
0.6689	Remote Similarity	NPD8357	Approved
0.668	Remote Similarity	NPD5426	Phase 3
0.6679	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6679	Remote Similarity	NPD7558	Phase 2
0.6678	Remote Similarity	NPD8349	Phase 1
0.6667	Remote Similarity	NPD7194	Discontinued
0.6667	Remote Similarity	NPD6376	Discontinued
0.6655	Remote Similarity	NPD6228	Discontinued
0.6628	Remote Similarity	NPD8093	Discontinued
0.6628	Remote Similarity	NPD7878	Phase 2
0.6619	Remote Similarity	NPD6742	Phase 2
0.6619	Remote Similarity	NPD6743	Phase 2
0.6604	Remote Similarity	NPD6962	Phase 2
0.6602	Remote Similarity	NPD5658	Approved
0.6598	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6594	Remote Similarity	NPD7996	Phase 2
0.6593	Remote Similarity	NPD6790	Phase 1
0.6589	Remote Similarity	NPD5936	Approved
0.6589	Remote Similarity	NPD5939	Approved
0.6588	Remote Similarity	NPD3003	Approved
0.6577	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.657	Remote Similarity	NPD8102	Discontinued
0.6569	Remote Similarity	NPD5821	Approved
0.6567	Remote Similarity	NPD5479	Discontinued
0.6564	Remote Similarity	NPD4852	Phase 2
0.6564	Remote Similarity	NPD7301	Phase 3
0.6559	Remote Similarity	NPD7859	Phase 2
0.6558	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7953	Approved
0.6556	Remote Similarity	NPD7950	Approved
0.6556	Remote Similarity	NPD7951	Approved
0.6556	Remote Similarity	NPD7790	Approved
0.6556	Remote Similarity	NPD7952	Approved
0.6556	Remote Similarity	NPD7791	Approved
0.6556	Remote Similarity	NPD7789	Approved
0.6554	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD4328	Approved
0.6543	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.654	Remote Similarity	NPD3763	Approved
0.6537	Remote Similarity	NPD7300	Phase 3
0.6537	Remote Similarity	NPD7302	Phase 3
0.652	Remote Similarity	NPD8525	Approved
0.6519	Remote Similarity	NPD7797	Approved
0.6519	Remote Similarity	NPD7796	Approved
0.6516	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8247	Approved
0.6512	Remote Similarity	NPD8246	Approved
0.6508	Remote Similarity	NPD8046	Discontinued
0.6507	Remote Similarity	NPD7853	Phase 2
0.6506	Remote Similarity	NPD8512	Phase 3
0.6502	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5866	Approved
0.6498	Remote Similarity	NPD5807	Phase 2
0.6494	Remote Similarity	NPD7922	Phase 1
0.6487	Remote Similarity	NPD7588	Discontinued
0.6486	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD4951	Discontinued
0.6477	Remote Similarity	NPD3258	Approved
0.6471	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7221	Approved
0.6466	Remote Similarity	NPD5050	Approved
0.6466	Remote Similarity	NPD7219	Approved
0.6464	Remote Similarity	NPD5164	Discontinued
0.6462	Remote Similarity	NPD7927	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD5416	Discontinued
0.6462	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD8289	Discontinued
0.6454	Remote Similarity	NPD8442	Discontinued
0.6453	Remote Similarity	NPD6242	Discontinued
0.645	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5891	Approved
0.6444	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD6985	Discontinued
0.6439	Remote Similarity	NPD7292	Approved
0.6434	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD4080	Discontinued
0.6434	Remote Similarity	NPD5429	Discontinued
0.6431	Remote Similarity	NPD7731	Approved
0.6431	Remote Similarity	NPD7730	Approved
0.6431	Remote Similarity	NPD4511	Phase 1
0.6431	Remote Similarity	NPD8430	Approved
0.6429	Remote Similarity	NPD8101	Phase 3
0.6426	Remote Similarity	NPD5612	Discontinued
0.6426	Remote Similarity	NPD8149	Discontinued
0.6426	Remote Similarity	NPD6733	Discontinued
0.6421	Remote Similarity	NPD7923	Phase 2
0.6421	Remote Similarity	NPD5116	Phase 1
0.642	Remote Similarity	NPD4795	Phase 2
0.642	Remote Similarity	NPD8114	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