NPASS Compound

Structure

NPC220851 OpenBabel07101719152D 23 27 0 0 0 0 0 0 0 0999 V2000 -4.0575 -2.3736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6508 -3.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4697 -1.5646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6562 -3.3917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4752 -1.6691 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0685 -2.5827 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 -0.0000 -1.0000 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 -1.0739 -2.4781 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 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 11 2 0 0 0 0 4 14 2 0 0 0 0 5 6 2 0 0 0 0 5 10 1 0 0 0 0 6 13 1 0 0 0 0 7 8 1 0 0 0 0 7 12 1 0 0 0 0 8 21 1 0 0 0 0 9 10 2 0 0 0 0 9 15 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 16 2 0 0 0 0 13 15 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 17 1 0 0 0 0 16 19 1 0 0 0 0 17 20 2 0 0 0 0 17 21 1 0 0 0 0 18 21 1 0 0 0 0 18 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	303.1
Volume:	303.945
LogP:	3.205
LogD:	3.206
LogS:	-5.152
# Rotatable Bonds:	0
TPSA:	70.91
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.525
Synthetic Accessibility Score:	2.446
Fsp3:	0.111
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:	-5.176
MDCK Permeability:	1.2723990039376076e-05
Pgp-inhibitor:	0.062
Pgp-substrate:	0.126
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.274
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.345
Plasma Protein Binding (PPB):	95.0486068725586%
Volume Distribution (VD):	0.504
Pgp-substrate:	2.5841445922851562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.259
CYP2C19-inhibitor:	0.795
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.647
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.818
CYP2D6-substrate:	0.909
CYP3A4-inhibitor:	0.783
CYP3A4-substrate:	0.232

ADMET: Excretion

Clearance (CL):	6.178
Half-life (T1/2):	0.428

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.738
Drug-inuced Liver Injury (DILI):	0.117
AMES Toxicity:	0.874
Rat Oral Acute Toxicity:	0.181
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.661
Carcinogencity:	0.868
Eye Corrosion:	0.004
Eye Irritation:	0.74
Respiratory Toxicity:	0.945

Download Data

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

Natural Product: NPC220851

Natural Product ID:	NPC220851
*Common Name:**	Orisuaveoline A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	HZSWRGHOTULQJO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H13N3O2/c22-10-5-6-13-15(9-10)20-17-16-12(7-8-21(17)18(13)23)11-3-1-2-4-14(11)19-16/h1-6,9,19,22H,7-8H2
SMILES:	Oc1ccc2c(c1)nc1n(c2=O)CCc2c1[nH]c1c2cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL575438
PubChem CID:	n.a.
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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[464573]

☑ 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 NPC220851 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	727
0.1-0.2	5558
0.2-0.3	11922
0.3-0.4	14346
0.4-0.5	5964
0.5-0.6	2568
0.6-0.7	1374
0.7-0.8	206
0.8-0.85	27
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9275	High Similarity	NPC66777
0.9091	High Similarity	NPC471762
0.8598	High Similarity	NPC157931
0.8421	Intermediate Similarity	NPC303374
0.8389	Intermediate Similarity	NPC322064
0.8341	Intermediate Similarity	NPC257851
0.8326	Intermediate Similarity	NPC477549
0.8274	Intermediate Similarity	NPC21429
0.8221	Intermediate Similarity	NPC471191
0.8178	Intermediate Similarity	NPC27041
0.8116	Intermediate Similarity	NPC471944
0.8095	Intermediate Similarity	NPC270918
0.8009	Intermediate Similarity	NPC183777
0.7963	Intermediate Similarity	NPC330009
0.7944	Intermediate Similarity	NPC72956
0.7907	Intermediate Similarity	NPC471194
0.7907	Intermediate Similarity	NPC471193
0.7907	Intermediate Similarity	NPC6865
0.7907	Intermediate Similarity	NPC153980
0.7892	Intermediate Similarity	NPC194740
0.7885	Intermediate Similarity	NPC306376
0.7867	Intermediate Similarity	NPC53144
0.7867	Intermediate Similarity	NPC134848
0.7818	Intermediate Similarity	NPC323969
0.7808	Intermediate Similarity	NPC264285
0.7808	Intermediate Similarity	NPC303658
0.7804	Intermediate Similarity	NPC86834
0.7804	Intermediate Similarity	NPC210828
0.7804	Intermediate Similarity	NPC39679
0.78	Intermediate Similarity	NPC72980
0.7798	Intermediate Similarity	NPC471192
0.7788	Intermediate Similarity	NPC207686
0.7778	Intermediate Similarity	NPC23294
0.774	Intermediate Similarity	NPC276517
0.7731	Intermediate Similarity	NPC63109
0.7731	Intermediate Similarity	NPC303951
0.7725	Intermediate Similarity	NPC178858
0.7709	Intermediate Similarity	NPC200553
0.7709	Intermediate Similarity	NPC279189
0.77	Intermediate Similarity	NPC200836
0.7682	Intermediate Similarity	NPC305984
0.7673	Intermediate Similarity	NPC88110
0.7661	Intermediate Similarity	NPC12344
0.7658	Intermediate Similarity	NPC276657
0.765	Intermediate Similarity	NPC85273
0.7634	Intermediate Similarity	NPC122436
0.7615	Intermediate Similarity	NPC87413
0.7609	Intermediate Similarity	NPC162002
0.76	Intermediate Similarity	NPC21638
0.7598	Intermediate Similarity	NPC284888
0.7589	Intermediate Similarity	NPC16352
0.7585	Intermediate Similarity	NPC63971
0.7585	Intermediate Similarity	NPC221873
0.7585	Intermediate Similarity	NPC91868
0.758	Intermediate Similarity	NPC219087
0.7576	Intermediate Similarity	NPC235685
0.7573	Intermediate Similarity	NPC141612
0.7573	Intermediate Similarity	NPC17273
0.7573	Intermediate Similarity	NPC135601
0.7566	Intermediate Similarity	NPC24370
0.7566	Intermediate Similarity	NPC319232
0.7566	Intermediate Similarity	NPC214142
0.7565	Intermediate Similarity	NPC174489
0.7558	Intermediate Similarity	NPC171787
0.7557	Intermediate Similarity	NPC3207
0.7557	Intermediate Similarity	NPC469928
0.7555	Intermediate Similarity	NPC132329
0.7543	Intermediate Similarity	NPC101350
0.7533	Intermediate Similarity	NPC124920
0.7533	Intermediate Similarity	NPC34580
0.7533	Intermediate Similarity	NPC261251
0.7533	Intermediate Similarity	NPC118559
0.7533	Intermediate Similarity	NPC304307
0.7524	Intermediate Similarity	NPC133003
0.7512	Intermediate Similarity	NPC474409
0.75	Intermediate Similarity	NPC150239
0.75	Intermediate Similarity	NPC26641
0.75	Intermediate Similarity	NPC100547
0.7489	Intermediate Similarity	NPC473041
0.7489	Intermediate Similarity	NPC247803
0.7488	Intermediate Similarity	NPC150308
0.7477	Intermediate Similarity	NPC183407
0.7467	Intermediate Similarity	NPC326363
0.7467	Intermediate Similarity	NPC223409
0.7467	Intermediate Similarity	NPC322135
0.7467	Intermediate Similarity	NPC95240
0.7458	Intermediate Similarity	NPC244543
0.7457	Intermediate Similarity	NPC473187
0.7455	Intermediate Similarity	NPC48317
0.7454	Intermediate Similarity	NPC476098
0.7453	Intermediate Similarity	NPC242209
0.7452	Intermediate Similarity	NPC46580
0.744	Intermediate Similarity	NPC94943
0.7436	Intermediate Similarity	NPC37152
0.7435	Intermediate Similarity	NPC14288
0.7435	Intermediate Similarity	NPC260434
0.7431	Intermediate Similarity	NPC243850
0.7431	Intermediate Similarity	NPC249583
0.7431	Intermediate Similarity	NPC4687
0.7427	Intermediate Similarity	NPC212535
0.7426	Intermediate Similarity	NPC469734
0.7418	Intermediate Similarity	NPC74153
0.7407	Intermediate Similarity	NPC295898
0.7407	Intermediate Similarity	NPC211813
0.7403	Intermediate Similarity	NPC54803
0.7403	Intermediate Similarity	NPC321592
0.7399	Intermediate Similarity	NPC148183
0.7399	Intermediate Similarity	NPC152768
0.7395	Intermediate Similarity	NPC249040
0.7393	Intermediate Similarity	NPC324149
0.7393	Intermediate Similarity	NPC470784
0.7391	Intermediate Similarity	NPC190007
0.7378	Intermediate Similarity	NPC74360
0.7371	Intermediate Similarity	NPC323752
0.7371	Intermediate Similarity	NPC323198
0.7371	Intermediate Similarity	NPC473105
0.7358	Intermediate Similarity	NPC473821
0.735	Intermediate Similarity	NPC184680
0.7345	Intermediate Similarity	NPC128115
0.7345	Intermediate Similarity	NPC174760
0.7342	Intermediate Similarity	NPC264176
0.7339	Intermediate Similarity	NPC245055
0.7339	Intermediate Similarity	NPC182222
0.7339	Intermediate Similarity	NPC325976
0.7339	Intermediate Similarity	NPC33064
0.7331	Intermediate Similarity	NPC77101
0.7319	Intermediate Similarity	NPC470785
0.7317	Intermediate Similarity	NPC96890
0.7314	Intermediate Similarity	NPC314882
0.7313	Intermediate Similarity	NPC60621
0.7306	Intermediate Similarity	NPC175602
0.7304	Intermediate Similarity	NPC478078
0.7303	Intermediate Similarity	NPC181081
0.7302	Intermediate Similarity	NPC474916
0.7301	Intermediate Similarity	NPC213530
0.7301	Intermediate Similarity	NPC193267
0.7299	Intermediate Similarity	NPC324091
0.7298	Intermediate Similarity	NPC315467
0.7297	Intermediate Similarity	NPC9894
0.7293	Intermediate Similarity	NPC179287
0.7285	Intermediate Similarity	NPC61038
0.7285	Intermediate Similarity	NPC476116
0.7285	Intermediate Similarity	NPC174758
0.7277	Intermediate Similarity	NPC184225
0.7273	Intermediate Similarity	NPC283117
0.7273	Intermediate Similarity	NPC53344
0.7269	Intermediate Similarity	NPC478009
0.7265	Intermediate Similarity	NPC308137
0.7265	Intermediate Similarity	NPC74619
0.7265	Intermediate Similarity	NPC310211
0.726	Intermediate Similarity	NPC285558
0.726	Intermediate Similarity	NPC475070
0.726	Intermediate Similarity	NPC470205
0.7256	Intermediate Similarity	NPC78767
0.7256	Intermediate Similarity	NPC141454
0.7256	Intermediate Similarity	NPC473814
0.7252	Intermediate Similarity	NPC309845
0.7251	Intermediate Similarity	NPC18890
0.7249	Intermediate Similarity	NPC229893
0.7246	Intermediate Similarity	NPC82472
0.7244	Intermediate Similarity	NPC62995
0.7244	Intermediate Similarity	NPC74969
0.7241	Intermediate Similarity	NPC471943
0.724	Intermediate Similarity	NPC475910
0.7238	Intermediate Similarity	NPC160898
0.7237	Intermediate Similarity	NPC198503
0.7235	Intermediate Similarity	NPC329747
0.7232	Intermediate Similarity	NPC469592
0.7232	Intermediate Similarity	NPC471080
0.723	Intermediate Similarity	NPC99666
0.7225	Intermediate Similarity	NPC84478
0.7225	Intermediate Similarity	NPC269270
0.722	Intermediate Similarity	NPC294375
0.7217	Intermediate Similarity	NPC472112
0.7217	Intermediate Similarity	NPC473449
0.7215	Intermediate Similarity	NPC165599
0.7215	Intermediate Similarity	NPC475816
0.7212	Intermediate Similarity	NPC169402
0.7212	Intermediate Similarity	NPC469727
0.7212	Intermediate Similarity	NPC293151
0.721	Intermediate Similarity	NPC474701
0.7207	Intermediate Similarity	NPC325297
0.7204	Intermediate Similarity	NPC278434
0.7203	Intermediate Similarity	NPC6786
0.72	Intermediate Similarity	NPC116238
0.72	Intermediate Similarity	NPC237740
0.7195	Intermediate Similarity	NPC471155
0.7195	Intermediate Similarity	NPC478006
0.7193	Intermediate Similarity	NPC14686
0.7193	Intermediate Similarity	NPC272174
0.7191	Intermediate Similarity	NPC97902
0.7191	Intermediate Similarity	NPC208898
0.7188	Intermediate Similarity	NPC294620
0.7188	Intermediate Similarity	NPC110182
0.7183	Intermediate Similarity	NPC92803
0.7182	Intermediate Similarity	NPC470500
0.7176	Intermediate Similarity	NPC153042
0.7176	Intermediate Similarity	NPC243834
0.7176	Intermediate Similarity	NPC70956
0.7175	Intermediate Similarity	NPC471304

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 NPC220851 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	351
0.1-0.2	676
0.2-0.3	848
0.3-0.4	1865
0.4-0.5	2450
0.5-0.6	1837
0.6-0.7	1028
0.7-0.8	95
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
0.7721	Intermediate Similarity	NPD2916	Discontinued
0.7647	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD4845	Discontinued
0.7594	Intermediate Similarity	NPD3814	Phase 1
0.7558	Intermediate Similarity	NPD6376	Discontinued
0.7534	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD4511	Phase 1
0.7466	Intermediate Similarity	NPD3243	Approved
0.7446	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5901	Discontinued
0.7412	Intermediate Similarity	NPD7603	Discontinued
0.7368	Intermediate Similarity	NPD4948	Discontinued
0.7366	Intermediate Similarity	NPD8091	Phase 3
0.7357	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD6165	Phase 2
0.7304	Intermediate Similarity	NPD6164	Phase 2
0.7286	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4368	Phase 2
0.7277	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7878	Phase 2
0.724	Intermediate Similarity	NPD5658	Approved
0.7238	Intermediate Similarity	NPD3962	Phase 2
0.7238	Intermediate Similarity	NPD3959	Phase 2
0.7222	Intermediate Similarity	NPD4373	Phase 2
0.722	Intermediate Similarity	NPD4558	Phase 2
0.7202	Intermediate Similarity	NPD7817	Phase 1
0.7202	Intermediate Similarity	NPD6724	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5293	Phase 2
0.72	Intermediate Similarity	NPD4897	Phase 2
0.7193	Intermediate Similarity	NPD6242	Discontinued
0.719	Intermediate Similarity	NPD2762	Phase 2
0.7185	Intermediate Similarity	NPD6790	Phase 1
0.7181	Intermediate Similarity	NPD5632	Approved
0.7179	Intermediate Similarity	NPD4885	Approved
0.7176	Intermediate Similarity	NPD7948	Phase 1
0.7172	Intermediate Similarity	NPD4926	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD4952	Phase 3
0.715	Intermediate Similarity	NPD5937	Approved
0.7143	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3986	Discontinued
0.711	Intermediate Similarity	NPD5882	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD5591	Approved
0.7083	Intermediate Similarity	NPD6716	Phase 1
0.7082	Intermediate Similarity	NPD3259	Approved
0.7078	Intermediate Similarity	NPD4501	Approved
0.7078	Intermediate Similarity	NPD484	Approved
0.7078	Intermediate Similarity	NPD4500	Approved
0.7067	Intermediate Similarity	NPD5416	Discontinued
0.7064	Intermediate Similarity	NPD6962	Phase 2
0.7059	Intermediate Similarity	NPD6176	Phase 1
0.7051	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD5552	Discontinued
0.7035	Intermediate Similarity	NPD2794	Discontinued
0.7034	Intermediate Similarity	NPD3960	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7853	Phase 2
0.7013	Intermediate Similarity	NPD5507	Approved
0.7013	Intermediate Similarity	NPD5506	Approved
0.7009	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5445	Approved
0.7	Intermediate Similarity	NPD5473	Discontinued
0.6996	Remote Similarity	NPD4403	Phase 3
0.6996	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6996	Remote Similarity	NPD4401	Phase 2
0.6987	Remote Similarity	NPD4958	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD7803	Approved
0.6982	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD1571	Phase 2
0.6978	Remote Similarity	NPD5593	Approved
0.6978	Remote Similarity	NPD5594	Approved
0.6977	Remote Similarity	NPD4499	Approved
0.6971	Remote Similarity	NPD5065	Approved
0.6966	Remote Similarity	NPD7426	Phase 1
0.6962	Remote Similarity	NPD1572	Phase 2
0.696	Remote Similarity	NPD7225	Discontinued
0.696	Remote Similarity	NPD8093	Discontinued
0.696	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD6249	Phase 2
0.6955	Remote Similarity	NPD6248	Phase 2
0.6953	Remote Similarity	NPD6752	Phase 1
0.6953	Remote Similarity	NPD6753	Phase 1
0.6952	Remote Similarity	NPD3239	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7181	Phase 3
0.6947	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6204	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7726	Phase 1
0.6936	Remote Similarity	NPD7994	Phase 2
0.6933	Remote Similarity	NPD2442	Approved
0.6933	Remote Similarity	NPD2509	Approved
0.6933	Remote Similarity	NPD2443	Approved
0.6933	Remote Similarity	NPD2510	Approved
0.6933	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.693	Remote Similarity	NPD8094	Discontinued
0.693	Remote Similarity	NPD4334	Discontinued
0.6929	Remote Similarity	NPD8016	Phase 3
0.6929	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD7194	Discontinued
0.6926	Remote Similarity	NPD6770	Approved
0.6926	Remote Similarity	NPD4312	Approved
0.6923	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7689	Approved
0.6912	Remote Similarity	NPD4922	Phase 2
0.6911	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6209	Approved
0.6895	Remote Similarity	NPD8463	Approved
0.6892	Remote Similarity	NPD5867	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD4515	Suspended
0.6881	Remote Similarity	NPD802	Phase 2
0.6878	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5479	Discontinued
0.6875	Remote Similarity	NPD8115	Approved
0.6875	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8114	Approved
0.6872	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.687	Remote Similarity	NPD3389	Approved
0.687	Remote Similarity	NPD3393	Approved
0.687	Remote Similarity	NPD3394	Approved
0.6866	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6664	Approved
0.6858	Remote Similarity	NPD7666	Phase 3
0.6858	Remote Similarity	NPD7665	Phase 2
0.6858	Remote Similarity	NPD7232	Discontinued
0.6853	Remote Similarity	NPD7203	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD7618	Phase 3
0.6849	Remote Similarity	NPD7619	Phase 3
0.6849	Remote Similarity	NPD8106	Phase 2
0.6847	Remote Similarity	NPD4601	Approved
0.6847	Remote Similarity	NPD4600	Approved
0.6844	Remote Similarity	NPD3003	Approved
0.6842	Remote Similarity	NPD8349	Phase 1
0.6842	Remote Similarity	NPD5482	Discontinued
0.684	Remote Similarity	NPD6458	Discontinued
0.6837	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7996	Phase 2
0.6825	Remote Similarity	NPD6530	Approved
0.6825	Remote Similarity	NPD6531	Approved
0.6825	Remote Similarity	NPD7708	Approved
0.6825	Remote Similarity	NPD6228	Discontinued
0.6822	Remote Similarity	NPD5923	Phase 1
0.682	Remote Similarity	NPD3746	Discontinued
0.682	Remote Similarity	NPD7031	Phase 1
0.6818	Remote Similarity	NPD7660	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7657	Approved
0.6812	Remote Similarity	NPD7656	Approved
0.6808	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD4988	Discontinued
0.6805	Remote Similarity	NPD5861	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8396	Approved
0.6802	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8395	Approved
0.6802	Remote Similarity	NPD6999	Discontinued
0.6802	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5426	Phase 3
0.68	Remote Similarity	NPD3947	Discontinued
0.6797	Remote Similarity	NPD7439	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7112	Discontinued
0.6793	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7415	Suspended
0.6791	Remote Similarity	NPD2814	Clinical (unspecified phase)
0.679	Remote Similarity	NPD4561	Discontinued
0.6789	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7955	Approved
0.6786	Remote Similarity	NPD7956	Approved
0.6786	Remote Similarity	NPD3773	Approved
0.6786	Remote Similarity	NPD3775	Approved
0.6786	Remote Similarity	NPD3774	Approved
0.6774	Remote Similarity	NPD7588	Discontinued
0.6773	Remote Similarity	NPD4400	Approved
0.6773	Remote Similarity	NPD8255	Phase 2
0.6771	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7568	Phase 1
0.677	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.677	Remote Similarity	NPD8364	Approved
0.677	Remote Similarity	NPD8363	Approved
0.6769	Remote Similarity	NPD5475	Discontinued
0.6769	Remote Similarity	NPD4863	Approved
0.6766	Remote Similarity	NPD1954	Phase 1
0.6766	Remote Similarity	NPD6995	Phase 1
0.6765	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD2951	Discontinued
0.6763	Remote Similarity	NPD6142	Phase 3
0.6759	Remote Similarity	NPD5809	Phase 3
0.6758	Remote Similarity	NPD4315	Phase 2
0.6756	Remote Similarity	NPD5487	Phase 1
0.6754	Remote Similarity	NPD2408	Discontinued
0.6754	Remote Similarity	NPD4506	Discontinued
0.6753	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD5850	Phase 3

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