NPASS Compound

Structure

CID45048 OpenBabel06191715382D 39 46 0 0 1 0 0 0 0 0999 V2000 -1.2409 -0.4323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5106 2.7566 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1033 1.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7925 1.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9265 0.6603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2100 1.0849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8965 1.4649 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9265 2.6603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6729 0.8155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7925 2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0605 2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1522 1.1564 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0605 1.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5378 1.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9107 2.2493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7310 0.1959 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1094 2.4693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5519 2.2739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8796 2.6784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7027 3.3829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2918 3.4874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5216 1.6603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4729 1.7648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2384 2.6538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4389 0.9619 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1094 4.2964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4997 4.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6554 0.3784 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2828 2.1478 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3663 4.9655 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.1094 0.8513 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8513 1.1094 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.6586 2.6603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7856 2.7336 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2564 3.6537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0876 4.5043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4133 4.8723 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1327 1.6821 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 29 1 0 0 0 0 3 38 1 0 0 0 0 4 5 2 0 0 0 0 4 10 1 0 0 0 0 5 13 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 10 2 0 0 0 0 8 11 1 0 0 0 0 9 12 1 0 0 0 0 10 33 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 25 1 0 0 0 0 12 29 1 6 0 0 0 13 31 1 0 0 0 0 14 18 2 0 0 0 0 14 32 1 0 0 0 0 15 24 2 0 0 0 0 15 34 1 0 0 0 0 16 9 1 1 0 0 0 16 31 1 0 0 0 0 16 39 1 0 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 21 2 0 0 0 0 19 23 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 27 1 0 0 0 0 22 23 2 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 35 1 0 0 0 0 25 28 1 6 0 0 0 25 38 1 0 0 0 0 26 30 2 0 0 0 0 26 36 1 0 0 0 0 27 30 1 0 0 0 0 27 37 2 0 0 0 0 28 1 1 1 0 0 0 28 32 1 0 0 0 0 28 39 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.16
Volume:	500.91
LogP:	2.909
LogD:	2.357
LogS:	-7.126
# Rotatable Bonds:	2
TPSA:	147.21
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	8
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.174
Synthetic Accessibility Score:	5.318
Fsp3:	0.286
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.11
MDCK Permeability:	3.546382913555135e-06
Pgp-inhibitor:	0.043
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.842
20% Bioavailability (F20%):	0.289
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	95.7013931274414%
Volume Distribution (VD):	1.369
Pgp-substrate:	3.2497477531433105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.648
CYP1A2-substrate:	0.895
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.084
CYP2C9-inhibitor:	0.728
CYP2C9-substrate:	0.735
CYP2D6-inhibitor:	0.142
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.242
CYP3A4-substrate:	0.903

ADMET: Excretion

Clearance (CL):	8.2
Half-life (T1/2):	0.373

ADMET: Toxicity

hERG Blockers:	0.174
Human Hepatotoxicity (H-HT):	0.761
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.496
Rat Oral Acute Toxicity:	0.029
Maximum Recommended Daily Dose:	0.985
Skin Sensitization:	0.411
Carcinogencity:	0.939
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.69

Download Data

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

Natural Product: NPC45048

Natural Product ID:	NPC45048
*Common Name:**	VDHMIDRUYQWJMP-WSDGDUIDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VDHMIDRUYQWJMP-WSDGDUIDSA-N
Standard InCHI:	InChI=1S/C28H24N4O7/c1-28-25(38-3)12(29-2)9-16(39-28)31-13-5-4-10(33)8-11(13)17-20-21(27(37)30-26(20)36)19-18-14(6-7-15(34)24(18)35)32(28)23(19)22(17)31/h4-8,12,16,25,29,33-35H,9H2,1-3H3,(H,30,36,37)/t12-,16-,25-,28+/m1/s1
SMILES:	C[C@]12[C@@H]([C@@H](C[C@H](n3c4ccc(cc4c4c5c(c6c7c(ccc(c7O)O)n1c6c34)C(=O)N=C5O)O)O2)NC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489653
PubChem CID:	24899660
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	=	26.6	nM	PMID[456278]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	68.1	nM	PMID[456278]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	=	28.4	nM	PMID[456278]

☑ 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 NPC45048 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	541
0.1-0.2	2645
0.2-0.3	13161
0.3-0.4	8740
0.4-0.5	12667
0.5-0.6	3302
0.6-0.7	1504
0.7-0.8	125
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9959	High Similarity	NPC279589
0.8502	High Similarity	NPC160898
0.8434	Intermediate Similarity	NPC107836
0.8223	Intermediate Similarity	NPC98371
0.8223	Intermediate Similarity	NPC313884
0.8097	Intermediate Similarity	NPC132329
0.7841	Intermediate Similarity	NPC1203
0.7818	Intermediate Similarity	NPC472842
0.7765	Intermediate Similarity	NPC472207
0.7698	Intermediate Similarity	NPC89549
0.7677	Intermediate Similarity	NPC94428
0.7677	Intermediate Similarity	NPC263937
0.7592	Intermediate Similarity	NPC31700
0.7566	Intermediate Similarity	NPC472846
0.7546	Intermediate Similarity	NPC132385
0.7409	Intermediate Similarity	NPC294620
0.7363	Intermediate Similarity	NPC227824
0.7361	Intermediate Similarity	NPC472843
0.7321	Intermediate Similarity	NPC218388
0.7298	Intermediate Similarity	NPC9894
0.728	Intermediate Similarity	NPC473183
0.7228	Intermediate Similarity	NPC270515
0.7218	Intermediate Similarity	NPC178858
0.7218	Intermediate Similarity	NPC469734
0.7206	Intermediate Similarity	NPC53344
0.7203	Intermediate Similarity	NPC39370
0.7203	Intermediate Similarity	NPC473184
0.7198	Intermediate Similarity	NPC227908
0.7197	Intermediate Similarity	NPC475844
0.7194	Intermediate Similarity	NPC264285
0.7189	Intermediate Similarity	NPC472845
0.7185	Intermediate Similarity	NPC329982
0.7181	Intermediate Similarity	NPC472844
0.7175	Intermediate Similarity	NPC473188
0.7175	Intermediate Similarity	NPC67401
0.717	Intermediate Similarity	NPC478081
0.7165	Intermediate Similarity	NPC473182
0.7159	Intermediate Similarity	NPC478080
0.7154	Intermediate Similarity	NPC474701
0.7153	Intermediate Similarity	NPC195788
0.7153	Intermediate Similarity	NPC237901
0.7148	Intermediate Similarity	NPC478010
0.7143	Intermediate Similarity	NPC471303
0.7132	Intermediate Similarity	NPC81175
0.7132	Intermediate Similarity	NPC477066
0.7126	Intermediate Similarity	NPC207686
0.7126	Intermediate Similarity	NPC473186
0.7115	Intermediate Similarity	NPC469928
0.7113	Intermediate Similarity	NPC260909
0.711	Intermediate Similarity	NPC473187
0.711	Intermediate Similarity	NPC477549
0.7105	Intermediate Similarity	NPC473540
0.7083	Intermediate Similarity	NPC15801
0.7083	Intermediate Similarity	NPC6786
0.7082	Intermediate Similarity	NPC16352
0.7076	Intermediate Similarity	NPC88923
0.7076	Intermediate Similarity	NPC100734
0.7076	Intermediate Similarity	NPC315634
0.707	Intermediate Similarity	NPC276657
0.7063	Intermediate Similarity	NPC17437
0.7057	Intermediate Similarity	NPC41679
0.7052	Intermediate Similarity	NPC78609
0.7052	Intermediate Similarity	NPC208522
0.7049	Intermediate Similarity	NPC474188
0.7048	Intermediate Similarity	NPC473800
0.7048	Intermediate Similarity	NPC181081
0.7041	Intermediate Similarity	NPC477067
0.7041	Intermediate Similarity	NPC478082
0.7038	Intermediate Similarity	NPC473185
0.7025	Intermediate Similarity	NPC478009
0.7019	Intermediate Similarity	NPC184680
0.7018	Intermediate Similarity	NPC478006
0.7011	Intermediate Similarity	NPC253580
0.7011	Intermediate Similarity	NPC252251
0.7007	Intermediate Similarity	NPC478083
0.7004	Intermediate Similarity	NPC86078
0.7	Intermediate Similarity	NPC214980
0.6992	Remote Similarity	NPC470785
0.6992	Remote Similarity	NPC82472
0.698	Remote Similarity	NPC330009
0.6973	Remote Similarity	NPC470126
0.6969	Remote Similarity	NPC478074
0.6966	Remote Similarity	NPC475816
0.6966	Remote Similarity	NPC41501
0.6958	Remote Similarity	NPC477531
0.6958	Remote Similarity	NPC474688
0.6957	Remote Similarity	NPC23294
0.6953	Remote Similarity	NPC293151
0.695	Remote Similarity	NPC162748
0.6947	Remote Similarity	NPC194740
0.6943	Remote Similarity	NPC325976
0.6938	Remote Similarity	NPC472099
0.6932	Remote Similarity	NPC270918
0.6932	Remote Similarity	NPC474192
0.6932	Remote Similarity	NPC475720
0.6931	Remote Similarity	NPC191489
0.6929	Remote Similarity	NPC315467
0.6929	Remote Similarity	NPC470784
0.6923	Remote Similarity	NPC133609
0.6923	Remote Similarity	NPC51388
0.692	Remote Similarity	NPC209174
0.692	Remote Similarity	NPC326363
0.6917	Remote Similarity	NPC303951
0.6909	Remote Similarity	NPC303374
0.6908	Remote Similarity	NPC478078
0.6906	Remote Similarity	NPC329631
0.6903	Remote Similarity	NPC477861
0.6901	Remote Similarity	NPC478012
0.69	Remote Similarity	NPC475666
0.6898	Remote Similarity	NPC189079
0.6898	Remote Similarity	NPC195314
0.6895	Remote Similarity	NPC129897
0.6895	Remote Similarity	NPC284685
0.6891	Remote Similarity	NPC285343
0.6891	Remote Similarity	NPC28945
0.689	Remote Similarity	NPC294375
0.6889	Remote Similarity	NPC142385
0.6873	Remote Similarity	NPC132642
0.6873	Remote Similarity	NPC244543
0.6863	Remote Similarity	NPC81939
0.6855	Remote Similarity	NPC101312
0.685	Remote Similarity	NPC124086
0.685	Remote Similarity	NPC5145
0.6846	Remote Similarity	NPC280799
0.6842	Remote Similarity	NPC153042
0.6842	Remote Similarity	NPC323752
0.6838	Remote Similarity	NPC86834
0.6838	Remote Similarity	NPC210828
0.6822	Remote Similarity	NPC246658
0.6822	Remote Similarity	NPC312645
0.6818	Remote Similarity	NPC274640
0.6818	Remote Similarity	NPC33949
0.6816	Remote Similarity	NPC253675
0.6816	Remote Similarity	NPC277351
0.6813	Remote Similarity	NPC476098
0.6812	Remote Similarity	NPC314882
0.6811	Remote Similarity	NPC476116
0.681	Remote Similarity	NPC185197
0.6808	Remote Similarity	NPC150239
0.6806	Remote Similarity	NPC202503
0.6806	Remote Similarity	NPC470018
0.6806	Remote Similarity	NPC24370
0.6806	Remote Similarity	NPC319232
0.6805	Remote Similarity	NPC49547
0.6803	Remote Similarity	NPC474183
0.6801	Remote Similarity	NPC284141
0.68	Remote Similarity	NPC9482
0.68	Remote Similarity	NPC315499
0.6797	Remote Similarity	NPC472098
0.6797	Remote Similarity	NPC152620
0.6796	Remote Similarity	NPC473639
0.6795	Remote Similarity	NPC303658
0.6791	Remote Similarity	NPC272549
0.679	Remote Similarity	NPC473312
0.679	Remote Similarity	NPC72905
0.6788	Remote Similarity	NPC63971
0.6788	Remote Similarity	NPC91868
0.6786	Remote Similarity	NPC475070
0.6783	Remote Similarity	NPC322064
0.6783	Remote Similarity	NPC478011
0.6783	Remote Similarity	NPC183407
0.678	Remote Similarity	NPC6215
0.6779	Remote Similarity	NPC207620
0.6779	Remote Similarity	NPC220852
0.6772	Remote Similarity	NPC39679
0.677	Remote Similarity	NPC250448
0.6769	Remote Similarity	NPC473179
0.6768	Remote Similarity	NPC179287
0.6765	Remote Similarity	NPC188400
0.6765	Remote Similarity	NPC15406
0.6763	Remote Similarity	NPC53534
0.676	Remote Similarity	NPC314176
0.6757	Remote Similarity	NPC476041
0.6757	Remote Similarity	NPC304926
0.6756	Remote Similarity	NPC169716
0.6756	Remote Similarity	NPC220851
0.6755	Remote Similarity	NPC311906
0.6753	Remote Similarity	NPC217554
0.6752	Remote Similarity	NPC471891
0.6745	Remote Similarity	NPC325297
0.6744	Remote Similarity	NPC118228
0.6744	Remote Similarity	NPC298449
0.6744	Remote Similarity	NPC190401
0.6744	Remote Similarity	NPC239763
0.6741	Remote Similarity	NPC101350
0.6741	Remote Similarity	NPC11408
0.6739	Remote Similarity	NPC137353
0.6738	Remote Similarity	NPC258048
0.6732	Remote Similarity	NPC475778
0.6732	Remote Similarity	NPC283117
0.6732	Remote Similarity	NPC193777
0.6731	Remote Similarity	NPC247803
0.6731	Remote Similarity	NPC46561
0.6731	Remote Similarity	NPC96321
0.6729	Remote Similarity	NPC295228
0.6728	Remote Similarity	NPC171393
0.6728	Remote Similarity	NPC295452
0.6719	Remote Similarity	NPC471304
0.6718	Remote Similarity	NPC3207
0.6718	Remote Similarity	NPC121069

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 NPC45048 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	620
0.2-0.3	1032
0.3-0.4	1916
0.4-0.5	2774
0.5-0.6	1958
0.6-0.7	526
0.7-0.8	55
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
0.8438	Intermediate Similarity	NPD6456	Discontinued
0.8427	Intermediate Similarity	NPD7921	Approved
0.8403	Intermediate Similarity	NPD7181	Phase 3
0.823	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.823	Intermediate Similarity	NPD6978	Phase 2
0.8223	Intermediate Similarity	NPD6976	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD3746	Discontinued
0.7778	Intermediate Similarity	NPD7073	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6717	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD5488	Discontinued
0.7652	Intermediate Similarity	NPD6455	Phase 3
0.7638	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.749	Intermediate Similarity	NPD6995	Phase 1
0.7354	Intermediate Similarity	NPD7688	Phase 1
0.7331	Intermediate Similarity	NPD7769	Phase 3
0.7317	Intermediate Similarity	NPD2916	Discontinued
0.7296	Intermediate Similarity	NPD8091	Phase 3
0.717	Intermediate Similarity	NPD6716	Phase 1
0.717	Intermediate Similarity	NPD7770	Phase 3
0.7169	Intermediate Similarity	NPD7772	Phase 3
0.7159	Intermediate Similarity	NPD4561	Discontinued
0.7153	Intermediate Similarity	NPD8465	Approved
0.7153	Intermediate Similarity	NPD8467	Approved
0.7153	Intermediate Similarity	NPD8466	Approved
0.7122	Intermediate Similarity	NPD8363	Approved
0.7122	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD8364	Approved
0.7117	Intermediate Similarity	NPD6530	Approved
0.7117	Intermediate Similarity	NPD6531	Approved
0.7113	Intermediate Similarity	NPD8460	Approved
0.7113	Intermediate Similarity	NPD8459	Approved
0.7099	Intermediate Similarity	NPD4373	Phase 2
0.7097	Intermediate Similarity	NPD7001	Phase 3
0.7094	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD8016	Phase 3
0.7092	Intermediate Similarity	NPD8428	Approved
0.7092	Intermediate Similarity	NPD8427	Approved
0.7092	Intermediate Similarity	NPD8429	Approved
0.7076	Intermediate Similarity	NPD7803	Approved
0.7074	Intermediate Similarity	NPD3986	Discontinued
0.7071	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD8358	Approved
0.7061	Intermediate Similarity	NPD5151	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8463	Approved
0.7053	Intermediate Similarity	NPD8426	Approved
0.7053	Intermediate Similarity	NPD8425	Approved
0.7052	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7038	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6724	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5482	Discontinued
0.7004	Intermediate Similarity	NPD7417	Discontinued
0.6985	Remote Similarity	NPD4952	Phase 3
0.6977	Remote Similarity	NPD5506	Approved
0.6977	Remote Similarity	NPD5507	Approved
0.696	Remote Similarity	NPD5530	Phase 1
0.6931	Remote Similarity	NPD7708	Approved
0.6923	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6517	Phase 3
0.6906	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7955	Approved
0.6895	Remote Similarity	NPD7956	Approved
0.6892	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5902	Approved
0.6875	Remote Similarity	NPD5903	Approved
0.687	Remote Similarity	NPD7603	Discontinued
0.6865	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7666	Phase 3
0.6838	Remote Similarity	NPD7665	Phase 2
0.6825	Remote Similarity	NPD3809	Discontinued
0.6824	Remote Similarity	NPD8524	Approved
0.6816	Remote Similarity	NPD6142	Phase 3
0.6816	Remote Similarity	NPD2951	Discontinued
0.6808	Remote Similarity	NPD5930	Phase 3
0.6801	Remote Similarity	NPD3959	Phase 2
0.6801	Remote Similarity	NPD3962	Phase 2
0.6795	Remote Similarity	NPD5632	Approved
0.6791	Remote Similarity	NPD8489	Phase 1
0.6782	Remote Similarity	NPD7726	Phase 1
0.678	Remote Similarity	NPD4845	Discontinued
0.6779	Remote Similarity	NPD6494	Phase 2
0.6773	Remote Similarity	NPD5450	Discontinued
0.6757	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6756	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4897	Phase 2
0.6742	Remote Similarity	NPD4885	Approved
0.6732	Remote Similarity	NPD7452	Approved
0.6732	Remote Similarity	NPD7453	Approved
0.6731	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD7925	Phase 2
0.6725	Remote Similarity	NPD7924	Phase 2
0.672	Remote Similarity	NPD6999	Discontinued
0.672	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD5426	Phase 3
0.6716	Remote Similarity	NPD7558	Phase 2
0.6712	Remote Similarity	NPD8349	Phase 1
0.6706	Remote Similarity	NPD6376	Discontinued
0.6705	Remote Similarity	NPD7194	Discontinued
0.6703	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD7767	Approved
0.668	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6679	Remote Similarity	NPD7426	Phase 1
0.6667	Remote Similarity	NPD7222	Phase 2
0.6667	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7397	Approved
0.6667	Remote Similarity	NPD8357	Approved
0.6667	Remote Similarity	NPD7398	Approved
0.6667	Remote Similarity	NPD7395	Discontinued
0.6667	Remote Similarity	NPD8093	Discontinued
0.6667	Remote Similarity	NPD7878	Phase 2
0.6654	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5658	Approved
0.6631	Remote Similarity	NPD6228	Discontinued
0.6628	Remote Similarity	NPD5939	Approved
0.6628	Remote Similarity	NPD5936	Approved
0.6627	Remote Similarity	NPD3003	Approved
0.6615	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5479	Discontinued
0.6602	Remote Similarity	NPD7301	Phase 3
0.6595	Remote Similarity	NPD6743	Phase 2
0.6595	Remote Similarity	NPD7859	Phase 2
0.6595	Remote Similarity	NPD6742	Phase 2
0.6593	Remote Similarity	NPD7791	Approved
0.6593	Remote Similarity	NPD7953	Approved
0.6593	Remote Similarity	NPD7950	Approved
0.6593	Remote Similarity	NPD7951	Approved
0.6593	Remote Similarity	NPD7952	Approved
0.6593	Remote Similarity	NPD7790	Approved
0.6593	Remote Similarity	NPD7789	Approved
0.6592	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.658	Remote Similarity	NPD6962	Phase 2
0.6576	Remote Similarity	NPD7300	Phase 3
0.6576	Remote Similarity	NPD7302	Phase 3
0.6571	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.657	Remote Similarity	NPD7996	Phase 2
0.6569	Remote Similarity	NPD6790	Phase 1
0.6554	Remote Similarity	NPD8525	Approved
0.6551	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD8102	Discontinued
0.6545	Remote Similarity	NPD5821	Approved
0.6544	Remote Similarity	NPD7853	Phase 2
0.6543	Remote Similarity	NPD8512	Phase 3
0.654	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4852	Phase 2
0.6534	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD5807	Phase 2
0.6531	Remote Similarity	NPD7922	Phase 1
0.653	Remote Similarity	NPD4328	Approved
0.652	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD4951	Discontinued
0.6515	Remote Similarity	NPD3763	Approved
0.6504	Remote Similarity	NPD7219	Approved
0.6504	Remote Similarity	NPD7221	Approved
0.6502	Remote Similarity	NPD5164	Discontinued
0.65	Remote Similarity	NPD5416	Discontinued
0.6494	Remote Similarity	NPD7797	Approved
0.6494	Remote Similarity	NPD7796	Approved
0.6493	Remote Similarity	NPD8289	Discontinued
0.6491	Remote Similarity	NPD6242	Discontinued
0.6489	Remote Similarity	NPD8246	Approved
0.6489	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD8442	Discontinued
0.6489	Remote Similarity	NPD4562	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD8247	Approved
0.6486	Remote Similarity	NPD8046	Discontinued
0.6486	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7292	Approved
0.6477	Remote Similarity	NPD6985	Discontinued
0.6475	Remote Similarity	NPD5866	Approved
0.6473	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4080	Discontinued
0.6471	Remote Similarity	NPD4511	Phase 1
0.6468	Remote Similarity	NPD7730	Approved
0.6468	Remote Similarity	NPD7731	Approved
0.6464	Remote Similarity	NPD8149	Discontinued
0.6464	Remote Similarity	NPD7588	Discontinued
0.6464	Remote Similarity	NPD5612	Discontinued
0.6462	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD5901	Discontinued
0.6459	Remote Similarity	NPD8115	Approved
0.6459	Remote Similarity	NPD8114	Approved
0.6459	Remote Similarity	NPD4795	Phase 2
0.6457	Remote Similarity	NPD8396	Approved
0.6457	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD8395	Approved
0.6456	Remote Similarity	NPD5116	Phase 1
0.6455	Remote Similarity	NPD7271	Approved
0.6453	Remote Similarity	NPD3258	Approved
0.6451	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD6964	Approved
0.6447	Remote Similarity	NPD6963	Approved
0.6445	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7781	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