NPASS Compound

Structure

CID257851 OpenBabel06191716062D 24 28 0 0 0 0 0 0 0 0999 V2000 0.8796 -4.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0385 0.9690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0383 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6798 -2.9077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1992 1.4539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6795 -1.9383 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1988 -0.4856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8404 -3.3926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 1.4545 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3591 0.9693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6796 0.9696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8399 -1.4538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3589 -0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0008 -2.9081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0005 -1.9387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6794 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8394 -0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8396 -0.4845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5193 -0.4852 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8391 -1.4543 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 -1.7203 0.0243 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8799 -3.4168 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 24 1 0 0 0 0 2 3 2 0 0 0 0 2 5 1 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 11 2 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 8 15 2 0 0 0 0 9 10 1 0 0 0 0 9 12 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 17 2 0 0 0 0 13 16 2 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 22 1 0 0 0 0 19 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	317.12
Volume:	321.24
LogP:	3.544
LogD:	3.392
LogS:	-5.384
# Rotatable Bonds:	1
TPSA:	59.91
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.587
Synthetic Accessibility Score:	2.38
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.101
MDCK Permeability:	1.62337273650337e-05
Pgp-inhibitor:	0.927
Pgp-substrate:	0.322
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.103
30% Bioavailability (F30%):	0.108

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.766
Plasma Protein Binding (PPB):	95.54358673095703%
Volume Distribution (VD):	0.537
Pgp-substrate:	1.5742050409317017%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.901
CYP2C19-substrate:	0.238
CYP2C9-inhibitor:	0.891
CYP2C9-substrate:	0.911
CYP2D6-inhibitor:	0.701
CYP2D6-substrate:	0.915
CYP3A4-inhibitor:	0.846
CYP3A4-substrate:	0.64

ADMET: Excretion

Clearance (CL):	6.132
Half-life (T1/2):	0.265

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.44
Drug-inuced Liver Injury (DILI):	0.362
AMES Toxicity:	0.903
Rat Oral Acute Toxicity:	0.239
Maximum Recommended Daily Dose:	0.841
Skin Sensitization:	0.342
Carcinogencity:	0.913
Eye Corrosion:	0.003
Eye Irritation:	0.236
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC257851

Natural Product ID:	NPC257851
*Common Name:**	HUQHSJJIKVPMHA-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HUQHSJJIKVPMHA-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H15N3O2/c1-24-15-8-4-6-13-16(15)21-18-17-12(9-10-22(18)19(13)23)11-5-2-3-7-14(11)20-17/h2-8,20H,9-10H2,1H3
SMILES:	COc1cccc2c1nc1c3[nH]c4c(c3CCn1c2=O)cccc4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL314132
PubChem CID:	5319487
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO30399	Zanthoxylum sp	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24692	Zanthoxylum sp.	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	5

Activity Type	# Activity
Individual Protein	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	IC50	=	450.0	nM	PMID[465789]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	IC50	=	11.0	nM	PMID[465789]
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	IC50	=	71.0	nM	PMID[465789]
NPT27	Others	Unspecified		IC50	=	45.0	nM	PMID[465789]
NPT27	Others	Unspecified		IC50	=	7.0	nM	PMID[465789]

☑ 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 NPC257851 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	791
0.1-0.2	5454
0.2-0.3	11918
0.3-0.4	12672
0.4-0.5	7816
0.5-0.6	2539
0.6-0.7	1283
0.7-0.8	205
0.8-0.85	13
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.942	High Similarity	NPC157931
0.91	High Similarity	NPC471762
0.9009	High Similarity	NPC66777
0.8515	High Similarity	NPC303374
0.8341	Intermediate Similarity	NPC220851
0.8333	Intermediate Similarity	NPC323969
0.8109	Intermediate Similarity	NPC21429
0.7974	Intermediate Similarity	NPC39370
0.7965	Intermediate Similarity	NPC473186
0.7963	Intermediate Similarity	NPC187501
0.7955	Intermediate Similarity	NPC288987
0.7933	Intermediate Similarity	NPC198401
0.7917	Intermediate Similarity	NPC471304
0.789	Intermediate Similarity	NPC39500
0.7867	Intermediate Similarity	NPC478078
0.7788	Intermediate Similarity	NPC74575
0.7783	Intermediate Similarity	NPC477549
0.7778	Intermediate Similarity	NPC243850
0.7758	Intermediate Similarity	NPC225279
0.7753	Intermediate Similarity	NPC194740
0.7748	Intermediate Similarity	NPC96321
0.7748	Intermediate Similarity	NPC184408
0.7738	Intermediate Similarity	NPC322064
0.7731	Intermediate Similarity	NPC45190
0.7731	Intermediate Similarity	NPC471191
0.7731	Intermediate Similarity	NPC300156
0.7729	Intermediate Similarity	NPC49547
0.7713	Intermediate Similarity	NPC208084
0.7708	Intermediate Similarity	NPC53534
0.7703	Intermediate Similarity	NPC305984
0.7696	Intermediate Similarity	NPC329631
0.7689	Intermediate Similarity	NPC144452
0.7675	Intermediate Similarity	NPC311906
0.7668	Intermediate Similarity	NPC303658
0.7655	Intermediate Similarity	NPC122436
0.765	Intermediate Similarity	NPC148889
0.7647	Intermediate Similarity	NPC26543
0.7615	Intermediate Similarity	NPC270918
0.761	Intermediate Similarity	NPC88110
0.7609	Intermediate Similarity	NPC474688
0.7609	Intermediate Similarity	NPC260434
0.7602	Intermediate Similarity	NPC153980
0.7602	Intermediate Similarity	NPC6865
0.76	Intermediate Similarity	NPC472099
0.7597	Intermediate Similarity	NPC235685
0.7588	Intermediate Similarity	NPC470018
0.758	Intermediate Similarity	NPC287208
0.758	Intermediate Similarity	NPC82548
0.7578	Intermediate Similarity	NPC148183
0.7578	Intermediate Similarity	NPC152768
0.7576	Intermediate Similarity	NPC196718
0.7564	Intermediate Similarity	NPC101350
0.7557	Intermediate Similarity	NPC72956
0.7546	Intermediate Similarity	NPC471944
0.7536	Intermediate Similarity	NPC176127
0.7523	Intermediate Similarity	NPC471194
0.7523	Intermediate Similarity	NPC471193
0.7523	Intermediate Similarity	NPC94157
0.7522	Intermediate Similarity	NPC274640
0.752	Intermediate Similarity	NPC152620
0.7512	Intermediate Similarity	NPC17273
0.7512	Intermediate Similarity	NPC141612
0.7512	Intermediate Similarity	NPC135601
0.7511	Intermediate Similarity	NPC473041
0.75	Intermediate Similarity	NPC471192
0.75	Intermediate Similarity	NPC102593
0.749	Intermediate Similarity	NPC478083
0.7489	Intermediate Similarity	NPC280799
0.7479	Intermediate Similarity	NPC208522
0.7477	Intermediate Similarity	NPC476138
0.7477	Intermediate Similarity	NPC245816
0.7469	Intermediate Similarity	NPC67401
0.7467	Intermediate Similarity	NPC179287
0.7467	Intermediate Similarity	NPC21638
0.7464	Intermediate Similarity	NPC133003
0.7458	Intermediate Similarity	NPC475816
0.7455	Intermediate Similarity	NPC477979
0.7455	Intermediate Similarity	NPC4687
0.7455	Intermediate Similarity	NPC249583
0.7455	Intermediate Similarity	NPC118228
0.7452	Intermediate Similarity	NPC314659
0.7441	Intermediate Similarity	NPC242928
0.7437	Intermediate Similarity	NPC142385
0.7431	Intermediate Similarity	NPC295898
0.7419	Intermediate Similarity	NPC329793
0.7404	Intermediate Similarity	NPC197335
0.7395	Intermediate Similarity	NPC72905
0.7376	Intermediate Similarity	NPC321428
0.7373	Intermediate Similarity	NPC184680
0.7373	Intermediate Similarity	NPC470022
0.7371	Intermediate Similarity	NPC92803
0.7364	Intermediate Similarity	NPC132539
0.7362	Intermediate Similarity	NPC182222
0.7358	Intermediate Similarity	NPC18890
0.7357	Intermediate Similarity	NPC46561
0.7354	Intermediate Similarity	NPC470020
0.7353	Intermediate Similarity	NPC475844
0.735	Intermediate Similarity	NPC475720
0.735	Intermediate Similarity	NPC474192
0.7342	Intermediate Similarity	NPC470785
0.7342	Intermediate Similarity	NPC266249
0.7339	Intermediate Similarity	NPC19872
0.7339	Intermediate Similarity	NPC176538
0.7333	Intermediate Similarity	NPC476287
0.7321	Intermediate Similarity	NPC87413
0.7321	Intermediate Similarity	NPC474798
0.7318	Intermediate Similarity	NPC223427
0.7314	Intermediate Similarity	NPC91868
0.7314	Intermediate Similarity	NPC270515
0.7314	Intermediate Similarity	NPC63971
0.7313	Intermediate Similarity	NPC27041
0.7311	Intermediate Similarity	NPC41501
0.7309	Intermediate Similarity	NPC174758
0.7309	Intermediate Similarity	NPC185782
0.7309	Intermediate Similarity	NPC174672
0.7297	Intermediate Similarity	NPC283117
0.7293	Intermediate Similarity	NPC132642
0.7289	Intermediate Similarity	NPC26679
0.7289	Intermediate Similarity	NPC264176
0.7289	Intermediate Similarity	NPC310211
0.7289	Intermediate Similarity	NPC308137
0.7289	Intermediate Similarity	NPC472098
0.7288	Intermediate Similarity	NPC253675
0.7285	Intermediate Similarity	NPC285558
0.7277	Intermediate Similarity	NPC123839
0.7273	Intermediate Similarity	NPC51388
0.7273	Intermediate Similarity	NPC161801
0.7269	Intermediate Similarity	NPC470784
0.7269	Intermediate Similarity	NPC469928
0.7265	Intermediate Similarity	NPC244543
0.7261	Intermediate Similarity	NPC198503
0.726	Intermediate Similarity	NPC329747
0.7258	Intermediate Similarity	NPC191489
0.7257	Intermediate Similarity	NPC151781
0.7257	Intermediate Similarity	NPC316181
0.7257	Intermediate Similarity	NPC74562
0.7254	Intermediate Similarity	NPC137353
0.7251	Intermediate Similarity	NPC84478
0.7249	Intermediate Similarity	NPC74360
0.7246	Intermediate Similarity	NPC141053
0.7244	Intermediate Similarity	NPC294375
0.7243	Intermediate Similarity	NPC324091
0.7237	Intermediate Similarity	NPC169402
0.7235	Intermediate Similarity	NPC102592
0.7235	Intermediate Similarity	NPC79356
0.7234	Intermediate Similarity	NPC477112
0.7234	Intermediate Similarity	NPC474701
0.7229	Intermediate Similarity	NPC216612
0.7225	Intermediate Similarity	NPC116238
0.7222	Intermediate Similarity	NPC475190
0.7215	Intermediate Similarity	NPC128823
0.7209	Intermediate Similarity	NPC138370
0.7209	Intermediate Similarity	NPC92111
0.7208	Intermediate Similarity	NPC477066
0.7205	Intermediate Similarity	NPC131885
0.7203	Intermediate Similarity	NPC101543
0.7203	Intermediate Similarity	NPC469554
0.7203	Intermediate Similarity	NPC207686
0.72	Intermediate Similarity	NPC199667
0.7196	Intermediate Similarity	NPC296527
0.7189	Intermediate Similarity	NPC276517
0.7186	Intermediate Similarity	NPC60621
0.7185	Intermediate Similarity	NPC470017
0.7185	Intermediate Similarity	NPC473187
0.7178	Intermediate Similarity	NPC473540
0.7178	Intermediate Similarity	NPC478082
0.7178	Intermediate Similarity	NPC477067
0.7178	Intermediate Similarity	NPC478081
0.7173	Intermediate Similarity	NPC172222
0.7163	Intermediate Similarity	NPC76748
0.7162	Intermediate Similarity	NPC293151
0.7162	Intermediate Similarity	NPC476098
0.7156	Intermediate Similarity	NPC473181
0.7155	Intermediate Similarity	NPC280272
0.7149	Intermediate Similarity	NPC16066
0.7149	Intermediate Similarity	NPC50562
0.7143	Intermediate Similarity	NPC276657
0.7143	Intermediate Similarity	NPC100734
0.7143	Intermediate Similarity	NPC307963
0.7143	Intermediate Similarity	NPC230403
0.7143	Intermediate Similarity	NPC315634
0.7143	Intermediate Similarity	NPC128115
0.7143	Intermediate Similarity	NPC208898
0.7143	Intermediate Similarity	NPC198673
0.7143	Intermediate Similarity	NPC193238
0.7143	Intermediate Similarity	NPC150239
0.7143	Intermediate Similarity	NPC88923
0.7137	Intermediate Similarity	NPC473180
0.7131	Intermediate Similarity	NPC17437
0.713	Intermediate Similarity	NPC247803
0.7126	Intermediate Similarity	NPC329982
0.7124	Intermediate Similarity	NPC322482
0.7124	Intermediate Similarity	NPC269367
0.7124	Intermediate Similarity	NPC167860
0.7124	Intermediate Similarity	NPC123976
0.7123	Intermediate Similarity	NPC470205
0.7118	Intermediate Similarity	NPC274982
0.7118	Intermediate Similarity	NPC67658
0.7118	Intermediate Similarity	NPC470799
0.7118	Intermediate Similarity	NPC8022

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 NPC257851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	403
0.1-0.2	637
0.2-0.3	872
0.3-0.4	1744
0.4-0.5	2517
0.5-0.6	1811
0.6-0.7	1038
0.7-0.8	125
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8131	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.8073	Intermediate Similarity	NPD4429	Discontinued
0.8	Intermediate Similarity	NPD6242	Discontinued
0.7906	Intermediate Similarity	NPD4558	Phase 2
0.7854	Intermediate Similarity	NPD5293	Phase 2
0.7816	Intermediate Similarity	NPD4515	Suspended
0.7778	Intermediate Similarity	NPD7206	Clinical (unspecified phase)
0.7729	Intermediate Similarity	NPD4885	Approved
0.7719	Intermediate Similarity	NPD5022	Discontinued
0.7696	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7689	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7689	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD3006	Discontinued
0.7623	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD7225	Discontinued
0.7565	Intermediate Similarity	NPD5479	Discontinued
0.7557	Intermediate Similarity	NPD5416	Discontinued
0.7553	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7511	Intermediate Similarity	NPD5632	Approved
0.75	Intermediate Similarity	NPD5658	Approved
0.7489	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7489	Intermediate Similarity	NPD3945	Discontinued
0.7479	Intermediate Similarity	NPD7853	Phase 2
0.7478	Intermediate Similarity	NPD7994	Phase 2
0.7468	Intermediate Similarity	NPD6223	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD2285	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4368	Phase 2
0.7446	Intermediate Similarity	NPD5559	Phase 2
0.7445	Intermediate Similarity	NPD5850	Phase 3
0.7398	Intermediate Similarity	NPD5867	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5999	Phase 2
0.7362	Intermediate Similarity	NPD2951	Discontinued
0.7359	Intermediate Similarity	NPD7603	Discontinued
0.7354	Intermediate Similarity	NPD3392	Approved
0.7347	Intermediate Similarity	NPD6961	Discontinued
0.7342	Intermediate Similarity	NPD7660	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7467	Discontinued
0.7342	Intermediate Similarity	NPD6376	Discontinued
0.7336	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5116	Phase 1
0.7327	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD6176	Phase 1
0.7314	Intermediate Similarity	NPD6172	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD4897	Phase 2
0.7301	Intermediate Similarity	NPD3257	Approved
0.7294	Intermediate Similarity	NPD4548	Discontinued
0.7284	Intermediate Similarity	NPD7588	Discontinued
0.7284	Intermediate Similarity	NPD5482	Discontinued
0.7281	Intermediate Similarity	NPD5515	Phase 2
0.7269	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD2510	Approved
0.7265	Intermediate Similarity	NPD6366	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD4952	Phase 3
0.7265	Intermediate Similarity	NPD2509	Approved
0.7265	Intermediate Similarity	NPD8463	Approved
0.7258	Intermediate Similarity	NPD7708	Approved
0.7253	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD6716	Phase 1
0.7247	Intermediate Similarity	NPD8091	Phase 3
0.7243	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5603	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD6790	Phase 1
0.7205	Intermediate Similarity	NPD7395	Discontinued
0.7203	Intermediate Similarity	NPD7797	Approved
0.7203	Intermediate Similarity	NPD7796	Approved
0.7198	Intermediate Similarity	NPD7872	Phase 2
0.7198	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD3389	Approved
0.7193	Intermediate Similarity	NPD3393	Approved
0.7193	Intermediate Similarity	NPD3394	Approved
0.719	Intermediate Similarity	NPD3962	Phase 2
0.719	Intermediate Similarity	NPD3959	Phase 2
0.7185	Intermediate Similarity	NPD5469	Phase 3
0.7174	Intermediate Similarity	NPD3258	Approved
0.7173	Intermediate Similarity	NPD4850	Phase 1
0.7173	Intermediate Similarity	NPD4373	Phase 2
0.7167	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD8016	Phase 3
0.7155	Intermediate Similarity	NPD6209	Approved
0.7149	Intermediate Similarity	NPD4511	Phase 1
0.7149	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1038	Approved
0.7143	Intermediate Similarity	NPD7803	Approved
0.7137	Intermediate Similarity	NPD3263	Phase 3
0.7136	Intermediate Similarity	NPD3825	Phase 3
0.7131	Intermediate Similarity	NPD8358	Approved
0.713	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4442	Phase 2
0.7113	Intermediate Similarity	NPD5861	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5507	Approved
0.7112	Intermediate Similarity	NPD5506	Approved
0.7107	Intermediate Similarity	NPD7022	Phase 2
0.7106	Intermediate Similarity	NPD4845	Discontinued
0.7101	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD4890	Phase 2
0.7093	Intermediate Similarity	NPD5475	Discontinued
0.7085	Intermediate Similarity	NPD5513	Phase 2
0.7083	Intermediate Similarity	NPD3488	Phase 1
0.708	Intermediate Similarity	NPD7955	Approved
0.708	Intermediate Similarity	NPD7956	Approved
0.7078	Intermediate Similarity	NPD5512	Phase 3
0.7074	Intermediate Similarity	NPD5148	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD5149	Phase 2
0.707	Intermediate Similarity	NPD6393	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7222	Phase 2
0.7067	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD2778	Approved
0.7056	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6228	Discontinued
0.7048	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD6643	Discontinued
0.7043	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4923	Phase 1
0.7035	Intermediate Similarity	NPD2187	Approved
0.7035	Intermediate Similarity	NPD2189	Approved
0.7034	Intermediate Similarity	NPD3259	Approved
0.7033	Intermediate Similarity	NPD5078	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8102	Discontinued
0.7026	Intermediate Similarity	NPD6770	Approved
0.7022	Intermediate Similarity	NPD3507	Phase 2
0.7009	Intermediate Similarity	NPD8311	Discontinued
0.7008	Intermediate Similarity	NPD3264	Phase 3
0.7008	Intermediate Similarity	NPD7592	Phase 2
0.7005	Intermediate Similarity	NPD2410	Phase 2
0.7004	Intermediate Similarity	NPD5014	Discontinued
0.7	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD7817	Phase 1
0.6996	Remote Similarity	NPD5399	Discovery
0.6996	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD5429	Discontinued
0.6988	Remote Similarity	NPD4353	Phase 2
0.6987	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6568	Discontinued
0.6983	Remote Similarity	NPD5948	Phase 2
0.6968	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6965	Remote Similarity	NPD7408	Phase 2
0.6964	Remote Similarity	NPD4896	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD2779	Approved
0.6964	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4328	Approved
0.6955	Remote Similarity	NPD4418	Discontinued
0.6953	Remote Similarity	NPD7924	Phase 2
0.6953	Remote Similarity	NPD7194	Discontinued
0.6953	Remote Similarity	NPD7925	Phase 2
0.6953	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4500	Approved
0.6951	Remote Similarity	NPD4501	Approved
0.6949	Remote Similarity	NPD4132	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD3003	Approved
0.6946	Remote Similarity	NPD5139	Phase 1
0.6943	Remote Similarity	NPD4502	Phase 2
0.6941	Remote Similarity	NPD5450	Discontinued
0.6939	Remote Similarity	NPD7067	Approved
0.6939	Remote Similarity	NPD7068	Approved
0.6938	Remote Similarity	NPD7689	Approved
0.6938	Remote Similarity	NPD5186	Approved
0.6938	Remote Similarity	NPD5183	Approved
0.6937	Remote Similarity	NPD772	Phase 3
0.6927	Remote Similarity	NPD4499	Approved
0.6926	Remote Similarity	NPD8363	Approved
0.6926	Remote Similarity	NPD8364	Approved
0.6923	Remote Similarity	NPD7180	Phase 3
0.6923	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.692	Remote Similarity	NPD7426	Phase 1
0.692	Remote Similarity	NPD7766	Phase 2
0.6917	Remote Similarity	NPD7031	Phase 1
0.6914	Remote Similarity	NPD4314	Approved
0.6914	Remote Similarity	NPD4313	Approved
0.6914	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6202	Discontinued
0.6909	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5882	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD6199	Discontinued
0.6904	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD3947	Discontinued
0.6902	Remote Similarity	NPD4894	Discontinued
0.69	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.69	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD3322	Phase 1
0.6897	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8149	Discontinued
0.6895	Remote Similarity	NPD7013	Phase 3
0.6895	Remote Similarity	NPD7012	Phase 3
0.6892	Remote Similarity	NPD5003	Discontinued
0.6892	Remote Similarity	NPD5591	Approved
0.6886	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5529	Phase 1
0.6886	Remote Similarity	NPD4154	Approved
0.6886	Remote Similarity	NPD2443	Approved
0.6886	Remote Similarity	NPD2442	Approved
0.6885	Remote Similarity	NPD4309	Approved
0.6885	Remote Similarity	NPD7025	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