NPASS Compound

Structure

NPC49583 OpenBabel07101718242D 35 41 0 0 1 0 0 0 0 0999 V2000 -6.8382 1.3874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5677 2.3361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1497 -3.0009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5343 -2.6575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2930 -0.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3757 -0.1334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7326 -1.7249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0843 0.5046 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7326 -0.1821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6552 0.7506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4689 0.1613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8535 -0.1821 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3638 1.3886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8257 -1.4302 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7603 -0.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2706 1.0939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7326 -0.1821 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8257 -0.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8535 -1.7249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8860 1.4373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7326 -1.7249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8257 -1.4302 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2930 -0.9535 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8257 -0.4767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1656 2.3212 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.7603 -1.4302 0.0000 N 0 0 0 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 0.8257 -0.4767 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0272 0.7247 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4772 0.4767 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5588 -2.6317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9792 1.7319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 7 1 0 0 0 0 5 9 1 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 24 1 0 0 0 0 8 22 1 0 0 0 0 9 30 1 0 0 0 0 10 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 1 0 0 0 0 11 24 1 0 0 0 0 12 16 2 0 0 0 0 12 17 1 0 0 0 0 13 16 1 0 0 0 0 14 17 2 0 0 0 0 14 27 1 0 0 0 0 15 23 1 0 0 0 0 15 26 1 1 0 0 0 16 28 1 0 0 0 0 17 35 1 0 0 0 0 18 25 1 6 0 0 0 18 26 1 0 0 0 0 18 31 1 0 0 0 0 19 29 2 0 0 0 0 19 32 1 0 0 0 0 20 25 1 0 0 0 0 20 28 2 0 0 0 0 20 33 1 0 0 0 0 21 30 1 0 0 0 0 21 34 2 0 0 0 0 22 35 1 0 0 0 0 23 25 1 0 0 0 0 24 19 1 6 0 0 0 24 30 1 0 0 0 0 25 13 1 1 0 0 0 26 21 1 1 0 0 0 26 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	497.17
Volume:	472.054
LogP:	3.713
LogD:	3.299
LogS:	-4.104
# Rotatable Bonds:	0
TPSA:	107.97
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.51
Synthetic Accessibility Score:	6.81
Fsp3:	0.577
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.075
MDCK Permeability:	2.1879761334275827e-05
Pgp-inhibitor:	0.972
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.062
20% Bioavailability (F20%):	0.19
30% Bioavailability (F30%):	0.588

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.638
Plasma Protein Binding (PPB):	90.34809875488281%
Volume Distribution (VD):	0.956
Pgp-substrate:	4.96560525894165%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.434
CYP2C19-inhibitor:	0.154
CYP2C19-substrate:	0.894
CYP2C9-inhibitor:	0.475
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.917
CYP3A4-substrate:	0.907

ADMET: Excretion

Clearance (CL):	6.124
Half-life (T1/2):	0.212

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.809
Drug-inuced Liver Injury (DILI):	0.87
AMES Toxicity:	0.363
Rat Oral Acute Toxicity:	0.989
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.228
Carcinogencity:	0.958
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.873

Download Data

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

Natural Product: NPC49583

Natural Product ID:	NPC49583
*Common Name:**	TVZRVAVYSDCSKC-ZUTUFOHQSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	TVZRVAVYSDCSKC-ZUTUFOHQSA-N
Standard InCHI:	InChI=1S/C26H28ClN3O5/c1-22(2)8-6-12-16-13(10-14(27)17(12)35-22)25(20(33)28-16)18(31)26-15(23(25,3)4)11-24(19(32)29-26)7-5-9-30(24)21(26)34/h6,8,10,15,18,31H,5,7,9,11H2,1-4H3,(H,28,33)(H,29,32)/t15-,18-,24-,25-,26+/m0/s1
SMILES:	CC1(C)C=Cc2c3c(cc(c2O1)Cl)[C@]1([C@@H]([C@]24[C@@H](C[C@@]5(CCCN5C2=O)C(=N4)O)C1(C)C)O)C(=N3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2375803
PubChem CID:	71712814
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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
NPO32643	aspergillus westerdijkiae dffscs013	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23701598]

☑ 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
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[448245]
NPT111	Cell Line	K562	Homo sapiens	IC50	=	44000.0	nM	PMID[448245]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[448245]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[448245]

☑ 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 NPC49583 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	420
0.1-0.2	2047
0.2-0.3	7917
0.3-0.4	12059
0.4-0.5	16956
0.5-0.6	3035
0.6-0.7	228
0.7-0.8	28
0.8-0.85	3
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9104	High Similarity	NPC37957
0.8925	High Similarity	NPC153923
0.8458	Intermediate Similarity	NPC205926
0.7883	Intermediate Similarity	NPC476651
0.7639	Intermediate Similarity	NPC266994
0.7574	Intermediate Similarity	NPC74216
0.7511	Intermediate Similarity	NPC250960
0.7511	Intermediate Similarity	NPC71539
0.7403	Intermediate Similarity	NPC470002
0.7403	Intermediate Similarity	NPC470001
0.7397	Intermediate Similarity	NPC204970
0.7395	Intermediate Similarity	NPC470821
0.7143	Intermediate Similarity	NPC189079
0.7103	Intermediate Similarity	NPC133609
0.7072	Intermediate Similarity	NPC174629
0.7017	Intermediate Similarity	NPC219397
0.6941	Remote Similarity	NPC39822
0.6888	Remote Similarity	NPC46259
0.6773	Remote Similarity	NPC131486
0.6752	Remote Similarity	NPC14339
0.6741	Remote Similarity	NPC473007
0.6696	Remote Similarity	NPC473008
0.6667	Remote Similarity	NPC28510
0.6654	Remote Similarity	NPC244543
0.6652	Remote Similarity	NPC67904
0.6638	Remote Similarity	NPC473004
0.6625	Remote Similarity	NPC127996
0.6623	Remote Similarity	NPC473569
0.6583	Remote Similarity	NPC82541
0.6569	Remote Similarity	NPC477160
0.6531	Remote Similarity	NPC288110
0.6531	Remote Similarity	NPC222046
0.6525	Remote Similarity	NPC473005
0.6504	Remote Similarity	NPC10653
0.6504	Remote Similarity	NPC318525
0.6504	Remote Similarity	NPC274268
0.6502	Remote Similarity	NPC189661
0.6496	Remote Similarity	NPC100863
0.6494	Remote Similarity	NPC477397
0.6481	Remote Similarity	NPC473371
0.6475	Remote Similarity	NPC234772
0.6466	Remote Similarity	NPC122886
0.6445	Remote Similarity	NPC474183
0.6445	Remote Similarity	NPC470784
0.6444	Remote Similarity	NPC477161
0.6438	Remote Similarity	NPC230313
0.6423	Remote Similarity	NPC77777
0.642	Remote Similarity	NPC159815
0.6417	Remote Similarity	NPC194699
0.6417	Remote Similarity	NPC219350
0.6414	Remote Similarity	NPC473458
0.6414	Remote Similarity	NPC471513
0.6411	Remote Similarity	NPC329830
0.6385	Remote Similarity	NPC477393
0.6384	Remote Similarity	NPC329480
0.6381	Remote Similarity	NPC470785
0.6381	Remote Similarity	NPC151171
0.6374	Remote Similarity	NPC323858
0.6371	Remote Similarity	NPC469722
0.6371	Remote Similarity	NPC477395
0.6371	Remote Similarity	NPC138830
0.6368	Remote Similarity	NPC243626
0.636	Remote Similarity	NPC473460
0.6352	Remote Similarity	NPC10732
0.6349	Remote Similarity	NPC79130
0.6349	Remote Similarity	NPC470480
0.6342	Remote Similarity	NPC213529
0.6342	Remote Similarity	NPC184680
0.6339	Remote Similarity	NPC298851
0.6339	Remote Similarity	NPC210415
0.6339	Remote Similarity	NPC21752
0.6339	Remote Similarity	NPC276993
0.6339	Remote Similarity	NPC293255
0.6339	Remote Similarity	NPC181138
0.6337	Remote Similarity	NPC14390
0.6336	Remote Similarity	NPC477396
0.6333	Remote Similarity	NPC87714
0.6318	Remote Similarity	NPC474077
0.6311	Remote Similarity	NPC469442
0.6311	Remote Similarity	NPC277306
0.6303	Remote Similarity	NPC127178
0.6298	Remote Similarity	NPC264938
0.629	Remote Similarity	NPC303658
0.6271	Remote Similarity	NPC308709
0.6266	Remote Similarity	NPC283207
0.6266	Remote Similarity	NPC474059
0.6265	Remote Similarity	NPC108826
0.626	Remote Similarity	NPC217903
0.626	Remote Similarity	NPC25539
0.626	Remote Similarity	NPC473006
0.6255	Remote Similarity	NPC203972
0.6245	Remote Similarity	NPC476436
0.624	Remote Similarity	NPC128115
0.623	Remote Similarity	NPC471561
0.623	Remote Similarity	NPC293347
0.6227	Remote Similarity	NPC97380
0.6227	Remote Similarity	NPC310403
0.6227	Remote Similarity	NPC263709
0.6227	Remote Similarity	NPC148468
0.6227	Remote Similarity	NPC63210
0.6227	Remote Similarity	NPC243673
0.622	Remote Similarity	NPC116178
0.6214	Remote Similarity	NPC198160
0.6211	Remote Similarity	NPC211713
0.6211	Remote Similarity	NPC88378
0.6208	Remote Similarity	NPC232600
0.6207	Remote Similarity	NPC262725
0.6206	Remote Similarity	NPC115588
0.6194	Remote Similarity	NPC321166
0.6188	Remote Similarity	NPC469479
0.6188	Remote Similarity	NPC254700
0.6188	Remote Similarity	NPC470069
0.6188	Remote Similarity	NPC52059
0.6183	Remote Similarity	NPC311357
0.6178	Remote Similarity	NPC291173
0.6169	Remote Similarity	NPC316297
0.6169	Remote Similarity	NPC66191
0.6169	Remote Similarity	NPC314817
0.6164	Remote Similarity	NPC315542
0.6163	Remote Similarity	NPC168250
0.6154	Remote Similarity	NPC217294
0.6154	Remote Similarity	NPC264176
0.6154	Remote Similarity	NPC3921
0.6142	Remote Similarity	NPC477394
0.614	Remote Similarity	NPC476441
0.6138	Remote Similarity	NPC197125
0.6135	Remote Similarity	NPC260909
0.6133	Remote Similarity	NPC194740
0.6132	Remote Similarity	NPC473422
0.6132	Remote Similarity	NPC470484
0.6129	Remote Similarity	NPC30749
0.6128	Remote Similarity	NPC51047
0.6126	Remote Similarity	NPC148124
0.6124	Remote Similarity	NPC476429
0.612	Remote Similarity	NPC126556
0.6118	Remote Similarity	NPC470485
0.6114	Remote Similarity	NPC127082
0.6111	Remote Similarity	NPC4910
0.6111	Remote Similarity	NPC329731
0.6109	Remote Similarity	NPC211525
0.6109	Remote Similarity	NPC272706
0.6109	Remote Similarity	NPC153694
0.6109	Remote Similarity	NPC161804
0.6107	Remote Similarity	NPC195787
0.6107	Remote Similarity	NPC246140
0.6102	Remote Similarity	NPC22476
0.61	Remote Similarity	NPC475489
0.6099	Remote Similarity	NPC67080
0.6099	Remote Similarity	NPC472121
0.6094	Remote Similarity	NPC206061
0.6094	Remote Similarity	NPC248903
0.6091	Remote Similarity	NPC161827
0.6091	Remote Similarity	NPC41216
0.6089	Remote Similarity	NPC305542
0.6089	Remote Similarity	NPC470482
0.6089	Remote Similarity	NPC470481
0.6087	Remote Similarity	NPC99724
0.6087	Remote Similarity	NPC475421
0.6085	Remote Similarity	NPC172355
0.6078	Remote Similarity	NPC470112
0.6078	Remote Similarity	NPC167763
0.6078	Remote Similarity	NPC231924
0.6078	Remote Similarity	NPC470903
0.6068	Remote Similarity	NPC291759
0.6067	Remote Similarity	NPC303214
0.6064	Remote Similarity	NPC326027
0.6063	Remote Similarity	NPC106593
0.6062	Remote Similarity	NPC475316
0.6062	Remote Similarity	NPC473486
0.6061	Remote Similarity	NPC469452
0.6059	Remote Similarity	NPC105055
0.6059	Remote Similarity	NPC22689
0.6056	Remote Similarity	NPC305984
0.6055	Remote Similarity	NPC26928
0.6053	Remote Similarity	NPC476425
0.605	Remote Similarity	NPC237901
0.605	Remote Similarity	NPC471825
0.605	Remote Similarity	NPC195788
0.6049	Remote Similarity	NPC471436
0.6049	Remote Similarity	NPC15987
0.6048	Remote Similarity	NPC326333
0.6047	Remote Similarity	NPC476069
0.6045	Remote Similarity	NPC314743
0.6044	Remote Similarity	NPC71205
0.6043	Remote Similarity	NPC21425
0.6039	Remote Similarity	NPC475292
0.6039	Remote Similarity	NPC473667
0.6039	Remote Similarity	NPC475565
0.6039	Remote Similarity	NPC475349
0.6034	Remote Similarity	NPC470728
0.6034	Remote Similarity	NPC470483
0.6033	Remote Similarity	NPC469443
0.6032	Remote Similarity	NPC475133
0.6026	Remote Similarity	NPC133591
0.6025	Remote Similarity	NPC59827
0.6025	Remote Similarity	NPC184933
0.6024	Remote Similarity	NPC128476
0.6023	Remote Similarity	NPC470631
0.6023	Remote Similarity	NPC35390
0.6023	Remote Similarity	NPC473781

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 NPC49583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	237
0.1-0.2	657
0.2-0.3	1028
0.3-0.4	2451
0.4-0.5	3503
0.5-0.6	1220
0.6-0.7	54
0.7-0.8	0
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
0.7098	Intermediate Similarity	NPD4771	Phase 2
0.6784	Remote Similarity	NPD3601	Discontinued
0.6756	Remote Similarity	NPD3119	Phase 1
0.6756	Remote Similarity	NPD3120	Approved
0.6652	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5496	Approved
0.6579	Remote Similarity	NPD1339	Discontinued
0.6545	Remote Similarity	NPD7805	Phase 3
0.6527	Remote Similarity	NPD8027	Approved
0.6459	Remote Similarity	NPD7432	Phase 2
0.6444	Remote Similarity	NPD6905	Phase 2
0.6444	Remote Similarity	NPD8161	Suspended
0.6444	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5587	Approved
0.6406	Remote Similarity	NPD6982	Phase 2
0.6398	Remote Similarity	NPD7810	Phase 3
0.6398	Remote Similarity	NPD7811	Phase 3
0.6379	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.636	Remote Similarity	NPD2166	Phase 3
0.636	Remote Similarity	NPD7132	Clinical (unspecified phase)
0.634	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.634	Remote Similarity	NPD4361	Phase 2
0.6324	Remote Similarity	NPD6983	Approved
0.6314	Remote Similarity	NPD5650	Approved
0.6314	Remote Similarity	NPD5652	Approved
0.6314	Remote Similarity	NPD2941	Discontinued
0.6314	Remote Similarity	NPD5651	Approved
0.6298	Remote Similarity	NPD6312	Discontinued
0.6298	Remote Similarity	NPD4360	Phase 2
0.6298	Remote Similarity	NPD4363	Phase 3
0.6293	Remote Similarity	NPD4113	Discontinued
0.6282	Remote Similarity	NPD3819	Phase 2
0.6272	Remote Similarity	NPD3227	Phase 2
0.6255	Remote Similarity	NPD7391	Discontinued
0.6255	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3065	Discontinued
0.625	Remote Similarity	NPD2498	Approved
0.6234	Remote Similarity	NPD5542	Phase 2
0.6229	Remote Similarity	NPD4523	Approved
0.6223	Remote Similarity	NPD6608	Clinical (unspecified phase)
0.6217	Remote Similarity	NPD8463	Approved
0.6216	Remote Similarity	NPD4064	Discontinued
0.6199	Remote Similarity	NPD5967	Approved
0.6164	Remote Similarity	NPD5617	Suspended
0.6157	Remote Similarity	NPD1716	Phase 3
0.6151	Remote Similarity	NPD6560	Approved
0.6148	Remote Similarity	NPD8461	Discontinued
0.6142	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6141	Remote Similarity	NPD3416	Discontinued
0.6137	Remote Similarity	NPD5565	Discontinued
0.6135	Remote Similarity	NPD8459	Approved
0.6135	Remote Similarity	NPD8460	Approved
0.6133	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD3298	Approved
0.613	Remote Similarity	NPD1717	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD5984	Phase 2
0.6107	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD7820	Phase 3
0.6098	Remote Similarity	NPD3591	Approved
0.6098	Remote Similarity	NPD3592	Approved
0.6089	Remote Similarity	NPD2042	Clinical (unspecified phase)
0.6089	Remote Similarity	NPD2904	Discontinued
0.6089	Remote Similarity	NPD2041	Clinical (unspecified phase)
0.6079	Remote Similarity	NPD2216	Approved
0.6079	Remote Similarity	NPD2215	Approved
0.6078	Remote Similarity	NPD1381	Clinical (unspecified phase)
0.6074	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD2167	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD2169	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD2168	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD3297	Approved
0.6055	Remote Similarity	NPD7426	Phase 1
0.6052	Remote Similarity	NPD8255	Phase 2
0.605	Remote Similarity	NPD8467	Approved
0.605	Remote Similarity	NPD8466	Approved
0.605	Remote Similarity	NPD8465	Approved
0.6047	Remote Similarity	NPD4981	Phase 2
0.6018	Remote Similarity	NPD3579	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD3365	Discontinued
0.6016	Remote Similarity	NPD5562	Approved
0.6016	Remote Similarity	NPD5561	Approved
0.6015	Remote Similarity	NPD8492	Approved
0.6009	Remote Similarity	NPD4012	Approved
0.6009	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6008	Remote Similarity	NPD6321	Discontinued
0.6007	Remote Similarity	NPD8363	Approved
0.6007	Remote Similarity	NPD8364	Approved
0.5993	Remote Similarity	NPD8427	Approved
0.5993	Remote Similarity	NPD8429	Approved
0.5993	Remote Similarity	NPD8428	Approved
0.5992	Remote Similarity	NPD5545	Phase 2
0.5984	Remote Similarity	NPD6510	Phase 1
0.5984	Remote Similarity	NPD6511	Phase 1
0.5983	Remote Similarity	NPD5858	Discontinued
0.5983	Remote Similarity	NPD4591	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4590	Approved
0.5982	Remote Similarity	NPD6063	Approved
0.5977	Remote Similarity	NPD3912	Discontinued
0.5975	Remote Similarity	NPD2975	Approved
0.5975	Remote Similarity	NPD4605	Approved
0.5975	Remote Similarity	NPD4604	Approved
0.5975	Remote Similarity	NPD2973	Approved
0.5975	Remote Similarity	NPD2974	Approved
0.597	Remote Similarity	NPD7048	Phase 3
0.5967	Remote Similarity	NPD4580	Approved
0.5965	Remote Similarity	NPD8425	Approved
0.5965	Remote Similarity	NPD8426	Approved
0.5964	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD7792	Phase 1
0.5951	Remote Similarity	NPD8107	Approved
0.5949	Remote Similarity	NPD779	Phase 2
0.5948	Remote Similarity	NPD8102	Discontinued
0.5948	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD1414	Approved
0.5947	Remote Similarity	NPD1413	Approved
0.5944	Remote Similarity	NPD5645	Phase 3
0.594	Remote Similarity	NPD6461	Clinical (unspecified phase)
0.5939	Remote Similarity	NPD2388	Discontinued
0.5936	Remote Similarity	NPD8108	Approved
0.5935	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.5933	Remote Similarity	NPD8359	Phase 2
0.593	Remote Similarity	NPD7186	Phase 3
0.5926	Remote Similarity	NPD8367	Approved
0.5923	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD3437	Discontinued
0.5921	Remote Similarity	NPD5649	Clinical (unspecified phase)
0.5919	Remote Similarity	NPD7963	Phase 3
0.5919	Remote Similarity	NPD4424	Discontinued
0.5918	Remote Similarity	NPD4946	Phase 2
0.5915	Remote Similarity	NPD7877	Suspended
0.5915	Remote Similarity	NPD8064	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD7542	Phase 3
0.5909	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD3259	Approved
0.5907	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.5907	Remote Similarity	NPD7412	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.5902	Remote Similarity	NPD6790	Phase 1
0.5902	Remote Similarity	NPD8164	Clinical (unspecified phase)
0.59	Remote Similarity	NPD3441	Approved
0.59	Remote Similarity	NPD3442	Approved
0.59	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.5899	Remote Similarity	NPD5450	Discontinued
0.5897	Remote Similarity	NPD8014	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD6289	Clinical (unspecified phase)
0.5894	Remote Similarity	NPD7497	Discontinued
0.5894	Remote Similarity	NPD3804	Discontinued
0.5894	Remote Similarity	NPD3802	Phase 3
0.5889	Remote Similarity	NPD8149	Discontinued
0.5882	Remote Similarity	NPD7131	Phase 3
0.588	Remote Similarity	NPD7574	Phase 2
0.5878	Remote Similarity	NPD2494	Approved
0.5878	Remote Similarity	NPD3452	Approved
0.5878	Remote Similarity	NPD6238	Discontinued
0.5878	Remote Similarity	NPD3450	Approved
0.5878	Remote Similarity	NPD2493	Approved
0.5877	Remote Similarity	NPD6037	Discontinued
0.5875	Remote Similarity	NPD6997	Phase 2
0.5872	Remote Similarity	NPD7252	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD1361	Discontinued
0.587	Remote Similarity	NPD4582	Approved
0.587	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4583	Approved
0.587	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.587	Remote Similarity	NPD4040	Phase 1
0.587	Remote Similarity	NPD6644	Discontinued
0.5868	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.5866	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.5866	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7560	Approved
0.5864	Remote Similarity	NPD7019	Approved
0.5864	Remote Similarity	NPD7020	Approved
0.5861	Remote Similarity	NPD6874	Approved
0.5861	Remote Similarity	NPD5547	Clinical (unspecified phase)
0.5858	Remote Similarity	NPD2845	Phase 2
0.5858	Remote Similarity	NPD2843	Phase 2
0.5857	Remote Similarity	NPD1945	Phase 1
0.5855	Remote Similarity	NPD6878	Phase 2
0.5855	Remote Similarity	NPD7959	Clinical (unspecified phase)
0.5855	Remote Similarity	NPD6879	Phase 2
0.5855	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4971	Clinical (unspecified phase)
0.5853	Remote Similarity	NPD5566	Clinical (unspecified phase)
0.5853	Remote Similarity	NPD7548	Discontinued
0.5843	Remote Similarity	NPD1852	Discontinued
0.5843	Remote Similarity	NPD6568	Discontinued
0.584	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.584	Remote Similarity	NPD4917	Discontinued
0.584	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.5837	Remote Similarity	NPD7556	Discontinued
0.5837	Remote Similarity	NPD6519	Phase 2
0.5837	Remote Similarity	NPD5312	Approved
0.5837	Remote Similarity	NPD5313	Approved
0.5837	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7178	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD2490	Approved
0.5833	Remote Similarity	NPD2488	Approved
0.583	Remote Similarity	NPD5811	Approved
0.583	Remote Similarity	NPD7064	Clinical (unspecified phase)

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