NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	478.15
Volume:	456.296
LogP:	1.357
LogD:	1.75
LogS:	-2.431
# Rotatable Bonds:	9
TPSA:	164.37
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.266
Synthetic Accessibility Score:	3.742
Fsp3:	0.348
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.258
MDCK Permeability:	2.257026244478766e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.287
Human Intestinal Absorption (HIA):	0.81
20% Bioavailability (F20%):	0.502
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.187
Plasma Protein Binding (PPB):	97.27655792236328%
Volume Distribution (VD):	0.373
Pgp-substrate:	5.592138290405273%

ADMET: Metabolism

CYP1A2-inhibitor:	0.07
CYP1A2-substrate:	0.387
CYP2C19-inhibitor:	0.093
CYP2C19-substrate:	0.363
CYP2C9-inhibitor:	0.08
CYP2C9-substrate:	0.889
CYP2D6-inhibitor:	0.2
CYP2D6-substrate:	0.793
CYP3A4-inhibitor:	0.102
CYP3A4-substrate:	0.128

ADMET: Excretion

Clearance (CL):	9.919
Half-life (T1/2):	0.946

ADMET: Toxicity

hERG Blockers:	0.143
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.462
Rat Oral Acute Toxicity:	0.182
Maximum Recommended Daily Dose:	0.025
Skin Sensitization:	0.919
Carcinogencity:	0.322
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.043

Download Data

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

Natural Product: NPC478237

Natural Product ID:	NPC478237
*Common Name:**	Ovatoside C
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PCTNEFCKNGGWDK-VFHGWZCLSA-N
Standard InCHI:	InChI=1S/C23H26O11/c1-30-16-9-12(3-6-14(16)25)4-8-19(26)32-11-18-20(27)21(28)22(29)23(34-18)33-15-7-5-13(24)10-17(15)31-2/h3-10,18,20-25,27-29H,11H2,1-2H3/b8-4+/t18?,20-,21?,22+,23-/m1/s1
SMILES:	COC1=CC(O)=CC=C1O[C@@H]1OC(COC(=O)/C=C/C2=CC(OC)=C(O)C=C2)[C@@H](O)C(O)[C@@H]1O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds]

*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
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	stem bark	Medicinal Plant Garden, College of Pharmacy, Ewha Womans University	2013-DEC	PMID[28787158]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9599262]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9835	Catalpa ovata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9835	Catalpa ovata	Species	Bignoniaceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC478237 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	337
0.1-0.2	1643
0.2-0.3	4545
0.3-0.4	10330
0.4-0.5	7776
0.5-0.6	4728
0.6-0.7	6809
0.7-0.8	5260
0.8-0.85	964
0.85-0.9	240
0.9-0.95	59
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.965	High Similarity	NPC106138
0.9571	High Similarity	NPC157816
0.9517	High Similarity	NPC213197
0.9504	High Similarity	NPC478239
0.9441	High Similarity	NPC199928
0.9379	High Similarity	NPC212670
0.9379	High Similarity	NPC90896
0.9379	High Similarity	NPC283839
0.9379	High Similarity	NPC313334
0.9379	High Similarity	NPC206264
0.9362	High Similarity	NPC186406
0.9357	High Similarity	NPC212770
0.9357	High Similarity	NPC98777
0.9357	High Similarity	NPC100389
0.931	High Similarity	NPC93924
0.931	High Similarity	NPC96294
0.9306	High Similarity	NPC476865
0.9301	High Similarity	NPC292443
0.9301	High Similarity	NPC297342
0.9301	High Similarity	NPC232228
0.9296	High Similarity	NPC140502
0.9291	High Similarity	NPC202700
0.9286	High Similarity	NPC65530
0.9286	High Similarity	NPC124149
0.9286	High Similarity	NPC59324
0.9257	High Similarity	NPC150442
0.9241	High Similarity	NPC41844
0.9236	High Similarity	NPC476864
0.9236	High Similarity	NPC476869
0.9236	High Similarity	NPC476868
0.9236	High Similarity	NPC476866
0.9231	High Similarity	NPC252169
0.9214	High Similarity	NPC157554
0.9214	High Similarity	NPC37468
0.9214	High Similarity	NPC203230
0.9214	High Similarity	NPC242028
0.9214	High Similarity	NPC186418
0.9211	High Similarity	NPC311803
0.9211	High Similarity	NPC472859
0.9211	High Similarity	NPC25389
0.9189	High Similarity	NPC289967
0.9189	High Similarity	NPC176186
0.9189	High Similarity	NPC169404
0.9189	High Similarity	NPC53587
0.9189	High Similarity	NPC472611
0.9189	High Similarity	NPC472612
0.9184	High Similarity	NPC21184
0.9184	High Similarity	NPC294522
0.9184	High Similarity	NPC205727
0.9184	High Similarity	NPC114740
0.9184	High Similarity	NPC120426
0.9167	High Similarity	NPC476867
0.9167	High Similarity	NPC110063
0.9161	High Similarity	NPC469559
0.9161	High Similarity	NPC145319
0.9161	High Similarity	NPC189115
0.9161	High Similarity	NPC475084
0.9155	High Similarity	NPC210478
0.9145	High Similarity	NPC119125
0.9145	High Similarity	NPC166277
0.9143	High Similarity	NPC185778
0.9116	High Similarity	NPC176903
0.9116	High Similarity	NPC30688
0.911	High Similarity	NPC227902
0.9103	High Similarity	NPC287615
0.9103	High Similarity	NPC476382
0.9103	High Similarity	NPC100998
0.9103	High Similarity	NPC34587
0.9103	High Similarity	NPC252292
0.9103	High Similarity	NPC262182
0.9103	High Similarity	NPC83743
0.9103	High Similarity	NPC34927
0.9103	High Similarity	NPC216819
0.9091	High Similarity	NPC469661
0.9085	High Similarity	NPC226005
0.9079	High Similarity	NPC289811
0.9079	High Similarity	NPC160780
0.9079	High Similarity	NPC287872
0.9079	High Similarity	NPC74319
0.9073	High Similarity	NPC284810
0.906	High Similarity	NPC215060
0.906	High Similarity	NPC476352
0.9048	High Similarity	NPC476348
0.9048	High Similarity	NPC175976
0.9048	High Similarity	NPC187398
0.9034	High Similarity	NPC473045
0.9034	High Similarity	NPC25292
0.9028	High Similarity	NPC193722
0.9028	High Similarity	NPC278469
0.902	High Similarity	NPC239966
0.902	High Similarity	NPC203020
0.9014	High Similarity	NPC126206
0.9013	High Similarity	NPC1913
0.9	High Similarity	NPC294166
0.9	High Similarity	NPC115022
0.9	High Similarity	NPC49074
0.9	High Similarity	NPC132895
0.898	High Similarity	NPC232992
0.898	High Similarity	NPC15577
0.898	High Similarity	NPC52740
0.898	High Similarity	NPC476347
0.8973	High Similarity	NPC475096
0.8966	High Similarity	NPC473044
0.8958	High Similarity	NPC83375
0.8958	High Similarity	NPC224876
0.8944	High Similarity	NPC164857
0.8944	High Similarity	NPC471665
0.8944	High Similarity	NPC471664
0.8936	High Similarity	NPC111635
0.8933	High Similarity	NPC163598
0.8933	High Similarity	NPC264875
0.8933	High Similarity	NPC120774
0.8929	High Similarity	NPC26080
0.8929	High Similarity	NPC303422
0.8929	High Similarity	NPC165686
0.8929	High Similarity	NPC162093
0.8929	High Similarity	NPC85799
0.8926	High Similarity	NPC476871
0.8919	High Similarity	NPC3460
0.8919	High Similarity	NPC192763
0.8919	High Similarity	NPC215095
0.8919	High Similarity	NPC210611
0.8919	High Similarity	NPC300262
0.8919	High Similarity	NPC80732
0.8919	High Similarity	NPC201148
0.8919	High Similarity	NPC261122
0.8919	High Similarity	NPC28651
0.8919	High Similarity	NPC199311
0.8912	High Similarity	NPC125755
0.8912	High Similarity	NPC99515
0.8912	High Similarity	NPC190714
0.8903	High Similarity	NPC33298
0.8903	High Similarity	NPC4013
0.8903	High Similarity	NPC90905
0.8903	High Similarity	NPC285108
0.8889	High Similarity	NPC267291
0.8889	High Similarity	NPC472860
0.8881	High Similarity	NPC138738
0.8881	High Similarity	NPC470413
0.8873	High Similarity	NPC470236
0.8873	High Similarity	NPC238243
0.8873	High Similarity	NPC476870
0.8873	High Similarity	NPC55040
0.8859	High Similarity	NPC306890
0.8859	High Similarity	NPC473427
0.8859	High Similarity	NPC471062
0.8859	High Similarity	NPC111785
0.8859	High Similarity	NPC476386
0.8859	High Similarity	NPC259347
0.8859	High Similarity	NPC470933
0.8859	High Similarity	NPC94871
0.8859	High Similarity	NPC476398
0.8859	High Similarity	NPC475250
0.8857	High Similarity	NPC121376
0.8851	High Similarity	NPC39657
0.8844	High Similarity	NPC161700
0.8844	High Similarity	NPC277867
0.8839	High Similarity	NPC217950
0.8816	High Similarity	NPC327032
0.8816	High Similarity	NPC191046
0.8816	High Similarity	NPC194095
0.8811	High Similarity	NPC3293
0.8811	High Similarity	NPC104167
0.8811	High Similarity	NPC471719
0.8811	High Similarity	NPC138350
0.8811	High Similarity	NPC40664
0.8811	High Similarity	NPC165482
0.8811	High Similarity	NPC166180
0.8811	High Similarity	NPC197723
0.8803	High Similarity	NPC251981
0.8803	High Similarity	NPC188555
0.8803	High Similarity	NPC886
0.8803	High Similarity	NPC310854
0.8803	High Similarity	NPC107478
0.8803	High Similarity	NPC170694
0.8803	High Similarity	NPC48863
0.8803	High Similarity	NPC287597
0.8803	High Similarity	NPC130496
0.8803	High Similarity	NPC135127
0.8803	High Similarity	NPC34293
0.8803	High Similarity	NPC13745
0.88	High Similarity	NPC257970
0.88	High Similarity	NPC470934
0.88	High Similarity	NPC470927
0.88	High Similarity	NPC188393
0.8794	High Similarity	NPC299144
0.8794	High Similarity	NPC470270
0.8794	High Similarity	NPC473285
0.8794	High Similarity	NPC5423
0.8794	High Similarity	NPC245120
0.8784	High Similarity	NPC268515
0.8784	High Similarity	NPC40222
0.8776	High Similarity	NPC76176
0.8776	High Similarity	NPC138227
0.8776	High Similarity	NPC168579
0.8776	High Similarity	NPC469313
0.8774	High Similarity	NPC289346
0.8767	High Similarity	NPC472714
0.8767	High Similarity	NPC5262
0.875	High Similarity	NPC102851

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 NPC478237 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	889
0.2-0.3	1926
0.3-0.4	2866
0.4-0.5	1714
0.5-0.6	930
0.6-0.7	457
0.7-0.8	83
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9379	High Similarity	NPD1653	Approved
0.869	High Similarity	NPD7266	Discontinued
0.8415	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD3027	Phase 3
0.8282	Intermediate Similarity	NPD7054	Approved
0.8276	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1613	Approved
0.8232	Intermediate Similarity	NPD7472	Approved
0.8232	Intermediate Similarity	NPD7074	Phase 3
0.8221	Intermediate Similarity	NPD3818	Discontinued
0.8113	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6797	Phase 2
0.8024	Intermediate Similarity	NPD7251	Discontinued
0.8012	Intermediate Similarity	NPD6234	Discontinued
0.8	Intermediate Similarity	NPD7228	Approved
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7808	Phase 3
0.795	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD1934	Approved
0.7925	Intermediate Similarity	NPD37	Approved
0.7888	Intermediate Similarity	NPD4967	Phase 2
0.7888	Intermediate Similarity	NPD4966	Approved
0.7888	Intermediate Similarity	NPD4965	Approved
0.7875	Intermediate Similarity	NPD2801	Approved
0.7857	Intermediate Similarity	NPD6190	Approved
0.7844	Intermediate Similarity	NPD5844	Phase 1
0.7811	Intermediate Similarity	NPD7685	Pre-registration
0.7811	Intermediate Similarity	NPD6559	Discontinued
0.7805	Intermediate Similarity	NPD7199	Phase 2
0.7778	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6166	Phase 2
0.7771	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7762	Intermediate Similarity	NPD1091	Approved
0.7722	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD3817	Phase 2
0.7647	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD1652	Phase 2
0.7607	Intermediate Similarity	NPD5402	Approved
0.7605	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3882	Suspended
0.7546	Intermediate Similarity	NPD1465	Phase 2
0.7534	Intermediate Similarity	NPD2982	Phase 2
0.7534	Intermediate Similarity	NPD2983	Phase 2
0.7529	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD7240	Approved
0.75	Intermediate Similarity	NPD6674	Discontinued
0.75	Intermediate Similarity	NPD230	Phase 1
0.7466	Intermediate Similarity	NPD2981	Phase 2
0.7457	Intermediate Similarity	NPD7549	Discontinued
0.7431	Intermediate Similarity	NPD1357	Approved
0.7421	Intermediate Similarity	NPD1511	Approved
0.74	Intermediate Similarity	NPD4908	Phase 1
0.7397	Intermediate Similarity	NPD422	Phase 1
0.7386	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5124	Phase 1
0.7368	Intermediate Similarity	NPD6233	Phase 2
0.7362	Intermediate Similarity	NPD4380	Phase 2
0.7342	Intermediate Similarity	NPD4628	Phase 3
0.7333	Intermediate Similarity	NPD2861	Phase 2
0.7333	Intermediate Similarity	NPD3018	Phase 2
0.7333	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD8455	Phase 2
0.7329	Intermediate Similarity	NPD1512	Approved
0.7321	Intermediate Similarity	NPD5494	Approved
0.7312	Intermediate Similarity	NPD4357	Discontinued
0.7303	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD5536	Phase 2
0.7284	Intermediate Similarity	NPD5403	Approved
0.7279	Intermediate Similarity	NPD1610	Phase 2
0.7279	Intermediate Similarity	NPD3705	Approved
0.7273	Intermediate Similarity	NPD1933	Approved
0.7273	Intermediate Similarity	NPD6801	Discontinued
0.7267	Intermediate Similarity	NPD3751	Discontinued
0.7247	Intermediate Similarity	NPD6841	Approved
0.7247	Intermediate Similarity	NPD6842	Approved
0.7247	Intermediate Similarity	NPD6843	Phase 3
0.7241	Intermediate Similarity	NPD1548	Phase 1
0.7235	Intermediate Similarity	NPD6232	Discontinued
0.7229	Intermediate Similarity	NPD7819	Suspended
0.7222	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD3496	Discontinued
0.7208	Intermediate Similarity	NPD4060	Phase 1
0.7207	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6799	Approved
0.7174	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4340	Discontinued
0.716	Intermediate Similarity	NPD5401	Approved
0.7143	Intermediate Similarity	NPD5058	Phase 3
0.7135	Intermediate Similarity	NPD3787	Discontinued
0.7125	Intermediate Similarity	NPD3750	Approved
0.7125	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD8313	Approved
0.7119	Intermediate Similarity	NPD8312	Approved
0.7118	Intermediate Similarity	NPD5677	Discontinued
0.7113	Intermediate Similarity	NPD228	Approved
0.7112	Intermediate Similarity	NPD7680	Approved
0.711	Intermediate Similarity	NPD7473	Discontinued
0.7108	Intermediate Similarity	NPD7411	Suspended
0.7107	Intermediate Similarity	NPD1549	Phase 2
0.7089	Intermediate Similarity	NPD2935	Discontinued
0.7089	Intermediate Similarity	NPD1551	Phase 2
0.7079	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD8127	Discontinued
0.7071	Intermediate Similarity	NPD1358	Approved
0.707	Intermediate Similarity	NPD7097	Phase 1
0.7051	Intermediate Similarity	NPD447	Suspended
0.7048	Intermediate Similarity	NPD4678	Approved
0.7048	Intermediate Similarity	NPD4675	Approved
0.7044	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD3687	Approved
0.703	Intermediate Similarity	NPD3686	Approved
0.7024	Intermediate Similarity	NPD2978	Approved
0.7024	Intermediate Similarity	NPD2977	Approved
0.7019	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4625	Phase 3
0.7013	Intermediate Similarity	NPD7095	Approved
0.7012	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD9494	Approved
0.6987	Remote Similarity	NPD1558	Phase 1
0.6982	Remote Similarity	NPD5353	Approved
0.6968	Remote Similarity	NPD6798	Discontinued
0.6968	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD4536	Approved
0.6962	Remote Similarity	NPD4538	Approved
0.6957	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4749	Approved
0.6951	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6599	Discontinued
0.6941	Remote Similarity	NPD7768	Phase 2
0.6914	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4110	Phase 3
0.691	Remote Similarity	NPD7038	Approved
0.691	Remote Similarity	NPD7039	Approved
0.6908	Remote Similarity	NPD3225	Approved
0.6905	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6653	Approved
0.6897	Remote Similarity	NPD5283	Phase 1
0.6882	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD3134	Approved
0.6879	Remote Similarity	NPD968	Approved
0.6879	Remote Similarity	NPD3620	Phase 2
0.6879	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD2796	Approved
0.6875	Remote Similarity	NPD3454	Phase 3
0.6857	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7435	Discontinued
0.6835	Remote Similarity	NPD6355	Discontinued
0.6832	Remote Similarity	NPD5762	Approved
0.6832	Remote Similarity	NPD5763	Approved
0.6832	Remote Similarity	NPD3540	Phase 1
0.6828	Remote Similarity	NPD7843	Approved
0.6828	Remote Similarity	NPD5535	Approved
0.6821	Remote Similarity	NPD1535	Discovery
0.6815	Remote Similarity	NPD4062	Phase 3
0.6813	Remote Similarity	NPD5588	Approved
0.6813	Remote Similarity	NPD1510	Phase 2
0.6813	Remote Similarity	NPD3748	Approved
0.6813	Remote Similarity	NPD5960	Phase 3
0.6813	Remote Similarity	NPD7033	Discontinued
0.6803	Remote Similarity	NPD7157	Approved
0.6803	Remote Similarity	NPD6671	Approved
0.6802	Remote Similarity	NPD6971	Discontinued
0.68	Remote Similarity	NPD5242	Approved
0.679	Remote Similarity	NPD970	Clinical (unspecified phase)
0.679	Remote Similarity	NPD2424	Discontinued
0.6788	Remote Similarity	NPD7585	Approved
0.6788	Remote Similarity	NPD5297	Approved
0.6786	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD2684	Approved
0.6782	Remote Similarity	NPD6959	Discontinued
0.6776	Remote Similarity	NPD1481	Phase 2
0.6776	Remote Similarity	NPD9269	Phase 2
0.6772	Remote Similarity	NPD6779	Approved
0.6772	Remote Similarity	NPD6782	Approved
0.6772	Remote Similarity	NPD6777	Approved
0.6772	Remote Similarity	NPD6776	Approved
0.6772	Remote Similarity	NPD4140	Approved
0.6772	Remote Similarity	NPD6778	Approved
0.6772	Remote Similarity	NPD6781	Approved
0.6772	Remote Similarity	NPD6780	Approved
0.677	Remote Similarity	NPD3539	Phase 1
0.6769	Remote Similarity	NPD7783	Phase 2
0.6769	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD2219	Phase 1

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