NPASS Compound

Structure

NPC303374 OpenBabel07101718182D 27 32 0 0 0 0 0 0 0 0999 V2000 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0898 -2.2226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2654 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6232 -2.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2709 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0844 -2.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6722 -1.5181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6722 -3.1361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6232 -1.8271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 3 2 0 0 0 0 2 10 1 0 0 0 0 3 12 1 0 0 0 0 4 5 1 0 0 0 0 4 11 1 0 0 0 0 5 23 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 15 2 0 0 0 0 8 17 1 0 0 0 0 9 26 1 0 0 0 0 9 27 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 18 2 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 23 1 0 0 0 0 20 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	361.11
Volume:	347.56
LogP:	3.9
LogD:	3.336
LogS:	-6.537
# Rotatable Bonds:	1
TPSA:	78.37
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.564
Synthetic Accessibility Score:	2.624
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.255
MDCK Permeability:	1.54291537910467e-05
Pgp-inhibitor:	0.237
Pgp-substrate:	0.027
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.177

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	93.0223388671875%
Volume Distribution (VD):	0.593
Pgp-substrate:	2.639036178588867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.581
CYP2C19-inhibitor:	0.945
CYP2C19-substrate:	0.09
CYP2C9-inhibitor:	0.858
CYP2C9-substrate:	0.913
CYP2D6-inhibitor:	0.885
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.941
CYP3A4-substrate:	0.31

ADMET: Excretion

Clearance (CL):	10.258
Half-life (T1/2):	0.208

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.484
Drug-inuced Liver Injury (DILI):	0.535
AMES Toxicity:	0.918
Rat Oral Acute Toxicity:	0.061
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.157
Carcinogencity:	0.964
Eye Corrosion:	0.003
Eye Irritation:	0.198
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC303374

Natural Product ID:	NPC303374
*Common Name:**	Orisuaveoline B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XQLMMQLYXOMQKO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H15N3O4/c1-25-10-2-3-12-14(6-10)22-19-18-11(4-5-23(19)20(12)24)13-7-16-17(27-9-26-16)8-15(13)21-18/h2-3,6-8,21H,4-5,9H2,1H3
SMILES:	COc1ccc2c(c1)nc1n(c2=O)CCc2c1[nH]c1c2cc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL574332
PubChem CID:	25157868
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
NPO20206	Oricia suaveolens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18950230]
NPO20206	Oricia suaveolens	Species	Rutaceae	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
IC50	2

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	31800.0	nM	PMID[484976]
NPT2	Others	Unspecified		IC50	=	22400.0	nM	PMID[484976]

☑ 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 NPC303374 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	757
0.1-0.2	4871
0.2-0.3	12664
0.3-0.4	8807
0.4-0.5	11346
0.5-0.6	2913
0.6-0.7	1156
0.7-0.8	167
0.8-0.85	12
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9058	High Similarity	NPC66777
0.9058	High Similarity	NPC471762
0.9013	High Similarity	NPC157931
0.8515	High Similarity	NPC257851
0.8421	Intermediate Similarity	NPC220851
0.8067	Intermediate Similarity	NPC253675
0.7932	Intermediate Similarity	NPC194740
0.7888	Intermediate Similarity	NPC305984
0.7806	Intermediate Similarity	NPC21638
0.7804	Intermediate Similarity	NPC100734
0.7804	Intermediate Similarity	NPC88923
0.7804	Intermediate Similarity	NPC315634
0.7778	Intermediate Similarity	NPC303658
0.7778	Intermediate Similarity	NPC235685
0.7746	Intermediate Similarity	NPC101350
0.7741	Intermediate Similarity	NPC478078
0.7737	Intermediate Similarity	NPC477549
0.7712	Intermediate Similarity	NPC323969
0.7708	Intermediate Similarity	NPC311906
0.7689	Intermediate Similarity	NPC122436
0.7647	Intermediate Similarity	NPC191489
0.7633	Intermediate Similarity	NPC184680
0.7629	Intermediate Similarity	NPC471304
0.7627	Intermediate Similarity	NPC473041
0.7627	Intermediate Similarity	NPC96321
0.7623	Intermediate Similarity	NPC208898
0.7617	Intermediate Similarity	NPC152768
0.7617	Intermediate Similarity	NPC148183
0.7608	Intermediate Similarity	NPC284685
0.7602	Intermediate Similarity	NPC470785
0.7576	Intermediate Similarity	NPC4687
0.7572	Intermediate Similarity	NPC260434
0.7571	Intermediate Similarity	NPC475816
0.7571	Intermediate Similarity	NPC168922
0.757	Intermediate Similarity	NPC270515
0.7563	Intermediate Similarity	NPC472099
0.7553	Intermediate Similarity	NPC46561
0.7532	Intermediate Similarity	NPC300156
0.753	Intermediate Similarity	NPC1608
0.753	Intermediate Similarity	NPC470784
0.7529	Intermediate Similarity	NPC478083
0.751	Intermediate Similarity	NPC22481
0.75	Intermediate Similarity	NPC41501
0.75	Intermediate Similarity	NPC91868
0.75	Intermediate Similarity	NPC280272
0.75	Intermediate Similarity	NPC63971
0.75	Intermediate Similarity	NPC249583
0.7478	Intermediate Similarity	NPC135887
0.7478	Intermediate Similarity	NPC295898
0.7478	Intermediate Similarity	NPC199277
0.7469	Intermediate Similarity	NPC474192
0.7469	Intermediate Similarity	NPC475720
0.7459	Intermediate Similarity	NPC278525
0.7457	Intermediate Similarity	NPC45190
0.7451	Intermediate Similarity	NPC244543
0.7449	Intermediate Similarity	NPC108342
0.7449	Intermediate Similarity	NPC473187
0.7447	Intermediate Similarity	NPC87413
0.7442	Intermediate Similarity	NPC89549
0.7437	Intermediate Similarity	NPC169402
0.7419	Intermediate Similarity	NPC189903
0.7419	Intermediate Similarity	NPC182907
0.7415	Intermediate Similarity	NPC264176
0.7384	Intermediate Similarity	NPC236668
0.7381	Intermediate Similarity	NPC81939
0.7373	Intermediate Similarity	NPC473188
0.7368	Intermediate Similarity	NPC473105
0.7368	Intermediate Similarity	NPC172222
0.7362	Intermediate Similarity	NPC174758
0.7362	Intermediate Similarity	NPC9729
0.7356	Intermediate Similarity	NPC132385
0.7353	Intermediate Similarity	NPC146976
0.7353	Intermediate Similarity	NPC116238
0.7352	Intermediate Similarity	NPC178858
0.7352	Intermediate Similarity	NPC475666
0.735	Intermediate Similarity	NPC270918
0.7348	Intermediate Similarity	NPC5374
0.7344	Intermediate Similarity	NPC128115
0.7342	Intermediate Similarity	NPC171409
0.7342	Intermediate Similarity	NPC310211
0.7342	Intermediate Similarity	NPC308137
0.7342	Intermediate Similarity	NPC96405
0.7339	Intermediate Similarity	NPC268077
0.7339	Intermediate Similarity	NPC285558
0.7333	Intermediate Similarity	NPC51854
0.7321	Intermediate Similarity	NPC204385
0.732	Intermediate Similarity	NPC166722
0.7319	Intermediate Similarity	NPC82548
0.7316	Intermediate Similarity	NPC329747
0.7315	Intermediate Similarity	NPC329982
0.7314	Intermediate Similarity	NPC280799
0.7314	Intermediate Similarity	NPC60621
0.7314	Intermediate Similarity	NPC198503
0.7311	Intermediate Similarity	NPC469592
0.7311	Intermediate Similarity	NPC471080
0.7309	Intermediate Similarity	NPC84478
0.7309	Intermediate Similarity	NPC21429
0.7304	Intermediate Similarity	NPC71124
0.7303	Intermediate Similarity	NPC208084
0.7303	Intermediate Similarity	NPC288987
0.7302	Intermediate Similarity	NPC473540
0.7302	Intermediate Similarity	NPC207620
0.7287	Intermediate Similarity	NPC217176
0.7281	Intermediate Similarity	NPC254957
0.728	Intermediate Similarity	NPC6786
0.7277	Intermediate Similarity	NPC135549
0.7277	Intermediate Similarity	NPC243850
0.7276	Intermediate Similarity	NPC169716
0.7273	Intermediate Similarity	NPC174760
0.7269	Intermediate Similarity	NPC53069
0.7269	Intermediate Similarity	NPC202768
0.7269	Intermediate Similarity	NPC39370
0.7269	Intermediate Similarity	NPC296482
0.7269	Intermediate Similarity	NPC472098
0.7265	Intermediate Similarity	NPC176127
0.7262	Intermediate Similarity	NPC477066
0.7262	Intermediate Similarity	NPC148889
0.7262	Intermediate Similarity	NPC210296
0.7261	Intermediate Similarity	NPC469594
0.7258	Intermediate Similarity	NPC473186
0.7258	Intermediate Similarity	NPC207686
0.7255	Intermediate Similarity	NPC17437
0.7249	Intermediate Similarity	NPC131017
0.7249	Intermediate Similarity	NPC198401
0.7246	Intermediate Similarity	NPC39679
0.7244	Intermediate Similarity	NPC124313
0.7241	Intermediate Similarity	NPC234197
0.7238	Intermediate Similarity	NPC266931
0.7237	Intermediate Similarity	NPC67401
0.7237	Intermediate Similarity	NPC473800
0.7235	Intermediate Similarity	NPC315467
0.7234	Intermediate Similarity	NPC471191
0.7233	Intermediate Similarity	NPC477067
0.7233	Intermediate Similarity	NPC207283
0.7233	Intermediate Similarity	NPC478082
0.7233	Intermediate Similarity	NPC84164
0.7233	Intermediate Similarity	NPC478081
0.7232	Intermediate Similarity	NPC260909
0.7231	Intermediate Similarity	NPC74360
0.7222	Intermediate Similarity	NPC207971
0.7222	Intermediate Similarity	NPC162484
0.7222	Intermediate Similarity	NPC223427
0.722	Intermediate Similarity	NPC206201
0.7215	Intermediate Similarity	NPC174672
0.7213	Intermediate Similarity	NPC210434
0.7208	Intermediate Similarity	NPC478009
0.7203	Intermediate Similarity	NPC313189
0.7202	Intermediate Similarity	NPC150239
0.7202	Intermediate Similarity	NPC276657
0.7198	Intermediate Similarity	NPC26543
0.7197	Intermediate Similarity	NPC316981
0.7194	Intermediate Similarity	NPC99891
0.7192	Intermediate Similarity	NPC53534
0.719	Intermediate Similarity	NPC247803
0.7185	Intermediate Similarity	NPC123976
0.7185	Intermediate Similarity	NPC167860
0.7178	Intermediate Similarity	NPC330009
0.7178	Intermediate Similarity	NPC274982
0.7178	Intermediate Similarity	NPC322064
0.7178	Intermediate Similarity	NPC469928
0.7171	Intermediate Similarity	NPC133609
0.7171	Intermediate Similarity	NPC295228
0.7167	Intermediate Similarity	NPC316181
0.7167	Intermediate Similarity	NPC74562
0.7167	Intermediate Similarity	NPC477019
0.7167	Intermediate Similarity	NPC151781
0.7167	Intermediate Similarity	NPC329793
0.716	Intermediate Similarity	NPC329631
0.716	Intermediate Similarity	NPC46451
0.716	Intermediate Similarity	NPC173250
0.7159	Intermediate Similarity	NPC152620
0.7154	Intermediate Similarity	NPC179287
0.7149	Intermediate Similarity	NPC474688
0.7149	Intermediate Similarity	NPC313327
0.7148	Intermediate Similarity	NPC195788
0.7148	Intermediate Similarity	NPC237901
0.7143	Intermediate Similarity	NPC189079
0.7143	Intermediate Similarity	NPC473183
0.7137	Intermediate Similarity	NPC188400
0.7137	Intermediate Similarity	NPC232727
0.7137	Intermediate Similarity	NPC208364
0.7137	Intermediate Similarity	NPC478006
0.7132	Intermediate Similarity	NPC165964
0.7131	Intermediate Similarity	NPC321428
0.7126	Intermediate Similarity	NPC120513
0.7126	Intermediate Similarity	NPC475844
0.7119	Intermediate Similarity	NPC475147
0.7115	Intermediate Similarity	NPC82472
0.7109	Intermediate Similarity	NPC160898
0.7108	Intermediate Similarity	NPC24019
0.7104	Intermediate Similarity	NPC183537
0.7104	Intermediate Similarity	NPC181081
0.7101	Intermediate Similarity	NPC475910
0.71	Intermediate Similarity	NPC276517
0.7098	Intermediate Similarity	NPC5167
0.7097	Intermediate Similarity	NPC74575
0.7095	Intermediate Similarity	NPC39500
0.7094	Intermediate Similarity	NPC176538
0.709	Intermediate Similarity	NPC193267
0.709	Intermediate Similarity	NPC213530

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 NPC303374 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	363
0.1-0.2	676
0.2-0.3	1010
0.3-0.4	1996
0.4-0.5	2531
0.5-0.6	1752
0.6-0.7	739
0.7-0.8	80
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
0.8528	High Similarity	NPD4885	Approved
0.8465	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD5658	Approved
0.7992	Intermediate Similarity	NPD8091	Phase 3
0.7804	Intermediate Similarity	NPD7803	Approved
0.7787	Intermediate Similarity	NPD6228	Discontinued
0.7716	Intermediate Similarity	NPD7225	Discontinued
0.7647	Intermediate Similarity	NPD7708	Approved
0.7642	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD4558	Phase 2
0.7637	Intermediate Similarity	NPD5070	Clinical (unspecified phase)
0.7637	Intermediate Similarity	NPD6242	Discontinued
0.7619	Intermediate Similarity	NPD7690	Clinical (unspecified phase)
0.7608	Intermediate Similarity	NPD7956	Approved
0.7608	Intermediate Similarity	NPD7955	Approved
0.7597	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD6517	Phase 3
0.7531	Intermediate Similarity	NPD4952	Phase 3
0.7479	Intermediate Similarity	NPD5632	Approved
0.747	Intermediate Similarity	NPD7588	Discontinued
0.7439	Intermediate Similarity	NPD4373	Phase 2
0.7409	Intermediate Similarity	NPD6963	Approved
0.7409	Intermediate Similarity	NPD6964	Approved
0.7381	Intermediate Similarity	NPD6230	Discontinued
0.7375	Intermediate Similarity	NPD5519	Discontinued
0.7355	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7620	Phase 2
0.7333	Intermediate Similarity	NPD6243	Phase 3
0.7333	Intermediate Similarity	NPD6244	Phase 3
0.7331	Intermediate Similarity	NPD6790	Phase 1
0.7329	Intermediate Similarity	NPD6745	Discontinued
0.732	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD3442	Approved
0.7287	Intermediate Similarity	NPD3441	Approved
0.728	Intermediate Similarity	NPD5293	Phase 2
0.7273	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD3815	Phase 1
0.7269	Intermediate Similarity	NPD3816	Phase 1
0.7255	Intermediate Similarity	NPD8358	Approved
0.7245	Intermediate Similarity	NPD8363	Approved
0.7245	Intermediate Similarity	NPD8364	Approved
0.7232	Intermediate Similarity	NPD8460	Approved
0.7232	Intermediate Similarity	NPD8459	Approved
0.7218	Intermediate Similarity	NPD5459	Phase 2
0.7218	Intermediate Similarity	NPD6962	Phase 2
0.7213	Intermediate Similarity	NPD1954	Phase 1
0.7211	Intermediate Similarity	NPD4368	Phase 2
0.7211	Intermediate Similarity	NPD5805	Approved
0.7208	Intermediate Similarity	NPD4897	Phase 2
0.7208	Intermediate Similarity	NPD3257	Approved
0.7208	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6046	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8463	Approved
0.7171	Intermediate Similarity	NPD3006	Discontinued
0.7166	Intermediate Similarity	NPD3259	Approved
0.7165	Intermediate Similarity	NPD6716	Phase 1
0.716	Intermediate Similarity	NPD3763	Approved
0.716	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD8016	Phase 3
0.7154	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7148	Intermediate Similarity	NPD8467	Approved
0.7148	Intermediate Similarity	NPD8465	Approved
0.7148	Intermediate Similarity	NPD8466	Approved
0.7143	Intermediate Similarity	NPD3591	Approved
0.7143	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3592	Approved
0.7137	Intermediate Similarity	NPD5902	Approved
0.7137	Intermediate Similarity	NPD5903	Approved
0.7132	Intermediate Similarity	NPD5482	Discontinued
0.7131	Intermediate Similarity	NPD5930	Phase 3
0.712	Intermediate Similarity	NPD7796	Approved
0.712	Intermediate Similarity	NPD7797	Approved
0.711	Intermediate Similarity	NPD5867	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD3258	Approved
0.7085	Intermediate Similarity	NPD4132	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5416	Discontinued
0.7082	Intermediate Similarity	NPD5071	Phase 2
0.708	Intermediate Similarity	NPD4995	Approved
0.708	Intermediate Similarity	NPD4996	Approved
0.7075	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6216	Approved
0.7066	Intermediate Similarity	NPD7559	Phase 2
0.7049	Intermediate Similarity	NPD4429	Discontinued
0.7049	Intermediate Similarity	NPD3313	Phase 2
0.7047	Intermediate Similarity	NPD7660	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD8426	Approved
0.7044	Intermediate Similarity	NPD8425	Approved
0.7042	Intermediate Similarity	NPD4997	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD4925	Approved
0.704	Intermediate Similarity	NPD1900	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD8149	Discontinued
0.7033	Intermediate Similarity	NPD5506	Approved
0.7033	Intermediate Similarity	NPD5507	Approved
0.7028	Intermediate Similarity	NPD7994	Phase 2
0.7028	Intermediate Similarity	NPD4328	Approved
0.7027	Intermediate Similarity	NPD8102	Discontinued
0.7026	Intermediate Similarity	NPD4418	Discontinued
0.7026	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8428	Approved
0.7022	Intermediate Similarity	NPD7198	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD8427	Approved
0.7022	Intermediate Similarity	NPD8429	Approved
0.7016	Intermediate Similarity	NPD5488	Discontinued
0.7016	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD683	Approved
0.7009	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5559	Phase 2
0.6996	Remote Similarity	NPD8255	Phase 2
0.6983	Remote Similarity	NPD3631	Phase 3
0.6983	Remote Similarity	NPD1304	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD5479	Discontinued
0.6969	Remote Similarity	NPD7853	Phase 2
0.6969	Remote Similarity	NPD5861	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD5561	Approved
0.6967	Remote Similarity	NPD5562	Approved
0.6962	Remote Similarity	NPD3106	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD956	Clinical (unspecified phase)
0.696	Remote Similarity	NPD4845	Discontinued
0.6958	Remote Similarity	NPD2510	Approved
0.6958	Remote Similarity	NPD4859	Phase 1
0.6958	Remote Similarity	NPD2509	Approved
0.6953	Remote Similarity	NPD5905	Phase 1
0.6951	Remote Similarity	NPD7194	Discontinued
0.6947	Remote Similarity	NPD7859	Phase 2
0.6946	Remote Similarity	NPD3003	Approved
0.692	Remote Similarity	NPD7426	Phase 1
0.6917	Remote Similarity	NPD6531	Approved
0.6917	Remote Similarity	NPD6530	Approved
0.6914	Remote Similarity	NPD5447	Phase 2
0.6911	Remote Similarity	NPD7206	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD8279	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5022	Discontinued
0.6904	Remote Similarity	NPD4795	Phase 2
0.6903	Remote Similarity	NPD3920	Phase 2
0.6901	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD5914	Approved
0.6899	Remote Similarity	NPD5051	Phase 1
0.6897	Remote Similarity	NPD6172	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6494	Phase 2
0.689	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4501	Approved
0.6878	Remote Similarity	NPD4500	Approved
0.6867	Remote Similarity	NPD3923	Approved
0.6867	Remote Similarity	NPD3921	Approved
0.6867	Remote Similarity	NPD6209	Approved
0.6867	Remote Similarity	NPD3924	Approved
0.6867	Remote Similarity	NPD2285	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3922	Approved
0.6865	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD6176	Phase 1
0.6846	Remote Similarity	NPD7222	Phase 2
0.6838	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1038	Approved
0.6836	Remote Similarity	NPD5469	Phase 3
0.6834	Remote Similarity	NPD4875	Phase 3
0.6834	Remote Similarity	NPD4876	Phase 3
0.6832	Remote Similarity	NPD7013	Phase 3
0.6832	Remote Similarity	NPD7012	Phase 3
0.6832	Remote Similarity	NPD5007	Approved
0.6829	Remote Similarity	NPD5612	Discontinued
0.6822	Remote Similarity	NPD5515	Phase 2
0.6815	Remote Similarity	NPD6770	Approved
0.6815	Remote Similarity	NPD5450	Discontinued
0.6813	Remote Similarity	NPD7689	Approved
0.6807	Remote Similarity	NPD8524	Approved
0.6807	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3507	Phase 2
0.6805	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3949	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD6877	Discontinued
0.6792	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD5116	Phase 1
0.679	Remote Similarity	NPD4506	Discontinued
0.6789	Remote Similarity	NPD5148	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5149	Phase 2
0.6787	Remote Similarity	NPD7858	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD3263	Phase 3
0.6784	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6727	Phase 2
0.6781	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5008	Approved
0.6776	Remote Similarity	NPD5866	Approved
0.6774	Remote Similarity	NPD7395	Discontinued
0.6774	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8489	Phase 1
0.6771	Remote Similarity	NPD8421	Discontinued
0.6769	Remote Similarity	NPD5833	Phase 1
0.6768	Remote Similarity	NPD7397	Approved
0.6768	Remote Similarity	NPD7398	Approved
0.6765	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3393	Approved
0.6761	Remote Similarity	NPD3394	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