NPASS Compound

Structure

NPC473188 OpenBabel07101718292D 38 43 0 0 0 0 0 0 0 0999 V2000 -1.9444 2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8080 -3.5497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3015 -2.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5695 0.7909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4355 0.2909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3457 1.5135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -2.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5695 -2.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3511 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7035 0.2909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7524 0.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5695 -1.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4355 -0.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1701 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7035 -0.7091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1646 -0.2091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7634 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9890 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7524 -1.0181 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 -6.4355 -2.7091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7688 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9836 -1.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3015 -1.2091 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 36 1 0 0 0 0 4 37 1 0 0 0 0 5 38 1 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 13 2 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 19 1 0 0 0 0 12 33 2 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 15 24 2 0 0 0 0 16 18 1 0 0 0 0 16 27 2 0 0 0 0 17 25 2 0 0 0 0 18 26 2 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 36 1 0 0 0 0 21 30 2 0 0 0 0 21 37 1 0 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 22 28 2 0 0 0 0 23 26 1 0 0 0 0 23 29 2 0 0 0 0 24 31 1 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 27 30 1 0 0 0 0 27 32 1 0 0 0 0 28 34 1 0 0 0 0 29 35 1 0 0 0 0 30 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	510.18
Volume:	516.558
LogP:	6.377
LogD:	3.497
LogS:	-4.858
# Rotatable Bonds:	5
TPSA:	116.8
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.197
Synthetic Accessibility Score:	3.219
Fsp3:	0.167
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.945
MDCK Permeability:	9.680866241978947e-06
Pgp-inhibitor:	0.332
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.703
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	89.84222412109375%
Volume Distribution (VD):	0.332
Pgp-substrate:	10.885296821594238%

ADMET: Metabolism

CYP1A2-inhibitor:	0.847
CYP1A2-substrate:	0.987
CYP2C19-inhibitor:	0.801
CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.836
CYP2C9-substrate:	0.726
CYP2D6-inhibitor:	0.07
CYP2D6-substrate:	0.894
CYP3A4-inhibitor:	0.11
CYP3A4-substrate:	0.378

ADMET: Excretion

Clearance (CL):	3.133
Half-life (T1/2):	0.104

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.104
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.597
Rat Oral Acute Toxicity:	0.981
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.742
Carcinogencity:	0.099
Eye Corrosion:	0.003
Eye Irritation:	0.452
Respiratory Toxicity:	0.865

Download Data

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

Natural Product: NPC473188

Natural Product ID:	NPC473188
*Common Name:**	VINTVEBLWZRPQG-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VINTVEBLWZRPQG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H26N2O6/c1-13-10-17-15-6-8-20(36-3)19(12-33)24(15)31-25(17)22(28(13)34)23-26-18(11-14(2)29(23)35)16-7-9-21(37-4)30(38-5)27(16)32-26/h6-12,31-32,34-35H,1-5H3
SMILES:	COc1c(OC)ccc2c1[nH]c1c2cc(c(c1c1c(O)c(C)cc2c1[nH]c1c2ccc(c1C=O)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3633084
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO33199	murraya tetramera	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26327273]

☑ 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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Activity	<	80.0	%	PMID[549429]

☑ 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 NPC473188 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	525
0.1-0.2	2802
0.2-0.3	13166
0.3-0.4	4543
0.4-0.5	12348
0.5-0.6	7664
0.6-0.7	1304
0.7-0.8	316
0.8-0.85	25
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9107	High Similarity	NPC473187
0.8782	High Similarity	NPC89549
0.8522	High Similarity	NPC473182
0.8491	Intermediate Similarity	NPC473183
0.8482	Intermediate Similarity	NPC473179
0.8405	Intermediate Similarity	NPC473184
0.8341	Intermediate Similarity	NPC202503
0.8304	Intermediate Similarity	NPC473185
0.8297	Intermediate Similarity	NPC179287
0.8282	Intermediate Similarity	NPC150239
0.8248	Intermediate Similarity	NPC39370
0.824	Intermediate Similarity	NPC473186
0.8194	Intermediate Similarity	NPC247803
0.8158	Intermediate Similarity	NPC208084
0.8093	Intermediate Similarity	NPC277351
0.8072	Intermediate Similarity	NPC132385
0.8035	Intermediate Similarity	NPC46561
0.8025	Intermediate Similarity	NPC6786
0.7974	Intermediate Similarity	NPC308137
0.7974	Intermediate Similarity	NPC310211
0.7965	Intermediate Similarity	NPC132642
0.7931	Intermediate Similarity	NPC198503
0.793	Intermediate Similarity	NPC23294
0.792	Intermediate Similarity	NPC209769
0.7888	Intermediate Similarity	NPC225279
0.7888	Intermediate Similarity	NPC174760
0.7885	Intermediate Similarity	NPC303951
0.7881	Intermediate Similarity	NPC274640
0.7879	Intermediate Similarity	NPC184408
0.7854	Intermediate Similarity	NPC477532
0.7851	Intermediate Similarity	NPC475844
0.7851	Intermediate Similarity	NPC187501
0.7822	Intermediate Similarity	NPC470930
0.7815	Intermediate Similarity	NPC475253
0.7807	Intermediate Similarity	NPC199667
0.7806	Intermediate Similarity	NPC252251
0.7805	Intermediate Similarity	NPC270515
0.7797	Intermediate Similarity	NPC210828
0.7797	Intermediate Similarity	NPC86834
0.7787	Intermediate Similarity	NPC160100
0.7763	Intermediate Similarity	NPC473181
0.7759	Intermediate Similarity	NPC169402
0.7753	Intermediate Similarity	NPC249583
0.7745	Intermediate Similarity	NPC144452
0.7741	Intermediate Similarity	NPC477531
0.7739	Intermediate Similarity	NPC473180
0.7739	Intermediate Similarity	NPC94157
0.7724	Intermediate Similarity	NPC58209
0.7716	Intermediate Similarity	NPC3207
0.7712	Intermediate Similarity	NPC51388
0.7706	Intermediate Similarity	NPC39500
0.7699	Intermediate Similarity	NPC209174
0.7696	Intermediate Similarity	NPC87413
0.7682	Intermediate Similarity	NPC293151
0.7672	Intermediate Similarity	NPC116238
0.7672	Intermediate Similarity	NPC118228
0.7667	Intermediate Similarity	NPC474688
0.7645	Intermediate Similarity	NPC34770
0.7636	Intermediate Similarity	NPC101312
0.7619	Intermediate Similarity	NPC294375
0.7611	Intermediate Similarity	NPC208522
0.7602	Intermediate Similarity	NPC166712
0.76	Intermediate Similarity	NPC128823
0.7598	Intermediate Similarity	NPC283117
0.7593	Intermediate Similarity	NPC474701
0.759	Intermediate Similarity	NPC63971
0.759	Intermediate Similarity	NPC91868
0.7589	Intermediate Similarity	NPC70956
0.7589	Intermediate Similarity	NPC243834
0.7571	Intermediate Similarity	NPC208364
0.7565	Intermediate Similarity	NPC39679
0.756	Intermediate Similarity	NPC203373
0.7555	Intermediate Similarity	NPC45190
0.7522	Intermediate Similarity	NPC4687
0.7522	Intermediate Similarity	NPC193777
0.7519	Intermediate Similarity	NPC227824
0.7511	Intermediate Similarity	NPC477533
0.75	Intermediate Similarity	NPC135887
0.75	Intermediate Similarity	NPC200888
0.75	Intermediate Similarity	NPC199277
0.749	Intermediate Similarity	NPC195788
0.749	Intermediate Similarity	NPC237901
0.748	Intermediate Similarity	NPC472589
0.747	Intermediate Similarity	NPC472588
0.7468	Intermediate Similarity	NPC9894
0.746	Intermediate Similarity	NPC133609
0.745	Intermediate Similarity	NPC173250
0.7449	Intermediate Similarity	NPC41501
0.7444	Intermediate Similarity	NPC260909
0.7431	Intermediate Similarity	NPC189079
0.7424	Intermediate Similarity	NPC66815
0.7424	Intermediate Similarity	NPC291535
0.7424	Intermediate Similarity	NPC475112
0.7424	Intermediate Similarity	NPC475085
0.7417	Intermediate Similarity	NPC205372
0.7417	Intermediate Similarity	NPC94842
0.7412	Intermediate Similarity	NPC120513
0.7403	Intermediate Similarity	NPC476106
0.7402	Intermediate Similarity	NPC244543
0.74	Intermediate Similarity	NPC160898
0.7393	Intermediate Similarity	NPC185197
0.7391	Intermediate Similarity	NPC67401
0.7388	Intermediate Similarity	NPC329631
0.7375	Intermediate Similarity	NPC152620
0.7373	Intermediate Similarity	NPC303374
0.7368	Intermediate Similarity	NPC184680
0.7366	Intermediate Similarity	NPC194740
0.7362	Intermediate Similarity	NPC48353
0.7352	Intermediate Similarity	NPC165964
0.7347	Intermediate Similarity	NPC49547
0.7346	Intermediate Similarity	NPC100734
0.7346	Intermediate Similarity	NPC315634
0.7346	Intermediate Similarity	NPC88923
0.7345	Intermediate Similarity	NPC131017
0.7344	Intermediate Similarity	NPC53534
0.7339	Intermediate Similarity	NPC470785
0.7328	Intermediate Similarity	NPC300156
0.7322	Intermediate Similarity	NPC288987
0.7319	Intermediate Similarity	NPC207620
0.7318	Intermediate Similarity	NPC474798
0.7316	Intermediate Similarity	NPC162484
0.7311	Intermediate Similarity	NPC314552
0.7302	Intermediate Similarity	NPC475666
0.7292	Intermediate Similarity	NPC169716
0.7291	Intermediate Similarity	NPC188400
0.7288	Intermediate Similarity	NPC203168
0.7287	Intermediate Similarity	NPC284685
0.7283	Intermediate Similarity	NPC471303
0.728	Intermediate Similarity	NPC131885
0.728	Intermediate Similarity	NPC148889
0.7277	Intermediate Similarity	NPC242928
0.7277	Intermediate Similarity	NPC219664
0.7276	Intermediate Similarity	NPC132329
0.7273	Intermediate Similarity	NPC314633
0.7269	Intermediate Similarity	NPC470784
0.7269	Intermediate Similarity	NPC101350
0.7262	Intermediate Similarity	NPC81939
0.7262	Intermediate Similarity	NPC284141
0.7261	Intermediate Similarity	NPC280799
0.7254	Intermediate Similarity	NPC74575
0.7249	Intermediate Similarity	NPC72211
0.7229	Intermediate Similarity	NPC15801
0.7229	Intermediate Similarity	NPC235685
0.7225	Intermediate Similarity	NPC475190
0.7218	Intermediate Similarity	NPC208898
0.7211	Intermediate Similarity	NPC217554
0.7208	Intermediate Similarity	NPC303658
0.7203	Intermediate Similarity	NPC11464
0.7192	Intermediate Similarity	NPC191489
0.719	Intermediate Similarity	NPC7560
0.7185	Intermediate Similarity	NPC469592
0.7185	Intermediate Similarity	NPC471080
0.7179	Intermediate Similarity	NPC304183
0.7178	Intermediate Similarity	NPC148409
0.7175	Intermediate Similarity	NPC45048
0.7171	Intermediate Similarity	NPC478080
0.7167	Intermediate Similarity	NPC223427
0.7166	Intermediate Similarity	NPC260434
0.7166	Intermediate Similarity	NPC217176
0.7162	Intermediate Similarity	NPC70259
0.7161	Intermediate Similarity	NPC201697
0.7155	Intermediate Similarity	NPC267423
0.7154	Intermediate Similarity	NPC471762
0.7149	Intermediate Similarity	NPC321428
0.7148	Intermediate Similarity	NPC51854
0.7143	Intermediate Similarity	NPC94943
0.7143	Intermediate Similarity	NPC285254
0.7138	Intermediate Similarity	NPC279589
0.7137	Intermediate Similarity	NPC469594
0.7131	Intermediate Similarity	NPC474366
0.7131	Intermediate Similarity	NPC131486
0.7131	Intermediate Similarity	NPC11408
0.713	Intermediate Similarity	NPC153042
0.7126	Intermediate Similarity	NPC78609
0.7121	Intermediate Similarity	NPC302807
0.7118	Intermediate Similarity	NPC43787
0.7118	Intermediate Similarity	NPC205934
0.7115	Intermediate Similarity	NPC258048
0.7114	Intermediate Similarity	NPC140296
0.7114	Intermediate Similarity	NPC13249
0.7113	Intermediate Similarity	NPC266931
0.7109	Intermediate Similarity	NPC9729
0.7103	Intermediate Similarity	NPC168922
0.7102	Intermediate Similarity	NPC97746
0.7098	Intermediate Similarity	NPC190007
0.7094	Intermediate Similarity	NPC134848
0.7089	Intermediate Similarity	NPC325297
0.7088	Intermediate Similarity	NPC129897
0.7077	Intermediate Similarity	NPC478083
0.7075	Intermediate Similarity	NPC49672
0.7073	Intermediate Similarity	NPC470018
0.7072	Intermediate Similarity	NPC209981
0.7072	Intermediate Similarity	NPC230683
0.7071	Intermediate Similarity	NPC12344
0.7071	Intermediate Similarity	NPC316981
0.707	Intermediate Similarity	NPC1608
0.7069	Intermediate Similarity	NPC18487
0.7066	Intermediate Similarity	NPC473041
0.7061	Intermediate Similarity	NPC122436
0.7054	Intermediate Similarity	NPC170114

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 NPC473188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	692
0.2-0.3	1133
0.3-0.4	1857
0.4-0.5	2777
0.5-0.6	1847
0.6-0.7	464
0.7-0.8	53
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
0.7821	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8363	Approved
0.7529	Intermediate Similarity	NPD8364	Approved
0.7521	Intermediate Similarity	NPD5902	Approved
0.7521	Intermediate Similarity	NPD5903	Approved
0.749	Intermediate Similarity	NPD3746	Discontinued
0.749	Intermediate Similarity	NPD8429	Approved
0.749	Intermediate Similarity	NPD8466	Approved
0.749	Intermediate Similarity	NPD8427	Approved
0.749	Intermediate Similarity	NPD8428	Approved
0.749	Intermediate Similarity	NPD8465	Approved
0.749	Intermediate Similarity	NPD8467	Approved
0.7471	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD8091	Phase 3
0.7444	Intermediate Similarity	NPD8459	Approved
0.7444	Intermediate Similarity	NPD8460	Approved
0.7426	Intermediate Similarity	NPD5632	Approved
0.7388	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD8425	Approved
0.7378	Intermediate Similarity	NPD8426	Approved
0.7375	Intermediate Similarity	NPD6456	Discontinued
0.7352	Intermediate Similarity	NPD3986	Discontinued
0.7346	Intermediate Similarity	NPD7803	Approved
0.7328	Intermediate Similarity	NPD3006	Discontinued
0.7323	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD5416	Discontinued
0.7311	Intermediate Similarity	NPD5164	Discontinued
0.7287	Intermediate Similarity	NPD7955	Approved
0.7287	Intermediate Similarity	NPD7956	Approved
0.728	Intermediate Similarity	NPD7395	Discontinued
0.7265	Intermediate Similarity	NPD5658	Approved
0.7258	Intermediate Similarity	NPD7853	Phase 2
0.7236	Intermediate Similarity	NPD6962	Phase 2
0.7216	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7708	Approved
0.7165	Intermediate Similarity	NPD5488	Discontinued
0.7158	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7148	Intermediate Similarity	NPD5482	Discontinued
0.7143	Intermediate Similarity	NPD6790	Phase 1
0.7137	Intermediate Similarity	NPD4885	Approved
0.7126	Intermediate Similarity	NPD5022	Discontinued
0.7126	Intermediate Similarity	NPD5479	Discontinued
0.7115	Intermediate Similarity	NPD6716	Phase 1
0.7108	Intermediate Similarity	NPD4373	Phase 2
0.7108	Intermediate Similarity	NPD6494	Phase 2
0.7108	Intermediate Similarity	NPD7558	Phase 2
0.7106	Intermediate Similarity	NPD3003	Approved
0.7086	Intermediate Similarity	NPD8489	Phase 1
0.7076	Intermediate Similarity	NPD5429	Discontinued
0.7075	Intermediate Similarity	NPD7417	Discontinued
0.7071	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4429	Discontinued
0.7059	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD4952	Phase 3
0.7036	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2564	Approved
0.7018	Intermediate Similarity	NPD2565	Phase 2
0.7004	Intermediate Similarity	NPD7222	Phase 2
0.6992	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD6773	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.698	Remote Similarity	NPD6517	Phase 3
0.6976	Remote Similarity	NPD7994	Phase 2
0.6976	Remote Similarity	NPD3259	Approved
0.6967	Remote Similarity	NPD2899	Discontinued
0.6964	Remote Similarity	NPD3925	Approved
0.696	Remote Similarity	NPD1505	Phase 2
0.6938	Remote Similarity	NPD8358	Approved
0.6935	Remote Similarity	NPD3263	Phase 3
0.6933	Remote Similarity	NPD7453	Approved
0.6933	Remote Similarity	NPD7452	Approved
0.6932	Remote Similarity	NPD6228	Discontinued
0.6926	Remote Similarity	NPD6985	Discontinued
0.6923	Remote Similarity	NPD7181	Phase 3
0.6914	Remote Similarity	NPD5612	Discontinued
0.691	Remote Similarity	NPD5003	Discontinued
0.6908	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD6974	Phase 3
0.6898	Remote Similarity	NPD3763	Approved
0.6898	Remote Similarity	NPD3875	Discontinued
0.6898	Remote Similarity	NPD7194	Discontinued
0.6897	Remote Similarity	NPD7859	Phase 2
0.6888	Remote Similarity	NPD4502	Phase 2
0.687	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6242	Discontinued
0.6868	Remote Similarity	NPD6531	Approved
0.6868	Remote Similarity	NPD6530	Approved
0.6867	Remote Similarity	NPD5512	Phase 3
0.6851	Remote Similarity	NPD1768	Approved
0.6844	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD4561	Discontinued
0.6828	Remote Similarity	NPD5450	Discontinued
0.6824	Remote Similarity	NPD5805	Approved
0.6818	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD2951	Discontinued
0.6806	Remote Similarity	NPD5532	Phase 2
0.6803	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7180	Phase 3
0.68	Remote Similarity	NPD7603	Discontinued
0.6798	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD4898	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD7924	Phase 2
0.6778	Remote Similarity	NPD7925	Phase 2
0.6778	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD8149	Discontinued
0.6762	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD8244	Phase 2
0.6749	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD6964	Approved
0.6745	Remote Similarity	NPD6963	Approved
0.6742	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2920	Discontinued
0.6719	Remote Similarity	NPD4454	Phase 2
0.6709	Remote Similarity	NPD8395	Approved
0.6709	Remote Similarity	NPD8396	Approved
0.6696	Remote Similarity	NPD3920	Phase 2
0.6694	Remote Similarity	NPD5519	Discontinued
0.6694	Remote Similarity	NPD2916	Discontinued
0.6694	Remote Similarity	NPD3258	Approved
0.6694	Remote Similarity	NPD3945	Discontinued
0.6693	Remote Similarity	NPD4368	Phase 2
0.6693	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.668	Remote Similarity	NPD6995	Phase 1
0.6679	Remote Similarity	NPD3328	Phase 2
0.6679	Remote Similarity	NPD8463	Approved
0.6667	Remote Similarity	NPD5937	Approved
0.6667	Remote Similarity	NPD5459	Phase 2
0.6667	Remote Similarity	NPD7426	Phase 1
0.6667	Remote Similarity	NPD5293	Phase 2
0.6654	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD5924	Discontinued
0.6653	Remote Similarity	NPD5866	Approved
0.6653	Remote Similarity	NPD1392	Approved
0.6652	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD5857	Phase 3
0.6641	Remote Similarity	NPD8016	Phase 3
0.6641	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD5817	Discontinued
0.664	Remote Similarity	NPD4328	Approved
0.6639	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6244	Phase 3
0.6629	Remote Similarity	NPD6243	Phase 3
0.6612	Remote Similarity	NPD5530	Phase 1
0.6603	Remote Similarity	NPD7921	Approved
0.6588	Remote Similarity	NPD4981	Phase 2
0.6588	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6586	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6586	Remote Similarity	NPD1926	Approved
0.6585	Remote Similarity	NPD7069	Discontinued
0.6585	Remote Similarity	NPD3816	Phase 1
0.6585	Remote Similarity	NPD8349	Phase 1
0.6585	Remote Similarity	NPD3815	Phase 1
0.6576	Remote Similarity	NPD7922	Phase 1
0.6576	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD5914	Approved
0.6567	Remote Similarity	NPD4948	Discontinued
0.6566	Remote Similarity	NPD3809	Discontinued
0.6562	Remote Similarity	NPD7688	Phase 1
0.6562	Remote Similarity	NPD1867	Approved
0.6556	Remote Similarity	NPD2779	Approved
0.6554	Remote Similarity	NPD6252	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD5939	Approved
0.6545	Remote Similarity	NPD5936	Approved
0.6538	Remote Similarity	NPD2792	Approved
0.6537	Remote Similarity	NPD7031	Phase 1
0.6534	Remote Similarity	NPD5930	Phase 3
0.6534	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD5850	Phase 3
0.6532	Remote Similarity	NPD3257	Approved
0.6527	Remote Similarity	NPD7022	Phase 2
0.652	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD6550	Discontinued
0.6508	Remote Similarity	NPD7556	Discontinued
0.6507	Remote Similarity	NPD5399	Discovery
0.6505	Remote Similarity	NPD6745	Discontinued
0.6502	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6498	Remote Similarity	NPD1038	Approved
0.6496	Remote Similarity	NPD4442	Phase 2
0.6485	Remote Similarity	NPD7948	Phase 1
0.6483	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD5913	Phase 3
0.6482	Remote Similarity	NPD1954	Phase 1
0.6478	Remote Similarity	NPD5067	Phase 2
0.6478	Remote Similarity	NPD5066	Phase 2
0.6475	Remote Similarity	NPD8403	Phase 1
0.6475	Remote Similarity	NPD3507	Phase 2
0.6471	Remote Similarity	NPD4418	Discontinued
0.6471	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6590	Discontinued
0.6471	Remote Similarity	NPD6491	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