NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	426.17
Volume:	429.874
LogP:	3.876
LogD:	2.983
LogS:	-4.941
# Rotatable Bonds:	4
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.585
Synthetic Accessibility Score:	4.985
Fsp3:	0.458
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.979
MDCK Permeability:	1.9884530047420412e-05
Pgp-inhibitor:	0.973
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.081
20% Bioavailability (F20%):	0.866
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.567
Plasma Protein Binding (PPB):	81.43608856201172%
Volume Distribution (VD):	1.699
Pgp-substrate:	11.222272872924805%

ADMET: Metabolism

CYP1A2-inhibitor:	0.162
CYP1A2-substrate:	0.828
CYP2C19-inhibitor:	0.713
CYP2C19-substrate:	0.804
CYP2C9-inhibitor:	0.559
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.206
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.63
CYP3A4-substrate:	0.872

ADMET: Excretion

Clearance (CL):	10.315
Half-life (T1/2):	0.14

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.937
Drug-inuced Liver Injury (DILI):	0.838
AMES Toxicity:	0.887
Rat Oral Acute Toxicity:	0.909
Maximum Recommended Daily Dose:	0.399
Skin Sensitization:	0.321
Carcinogencity:	0.951
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC476930

Natural Product ID:	NPC476930
*Common Name:**	methyl (1S,14S,17S)-7-hydroxy-15,15-dimethyl-17-(3-methylbut-2-enyl)-9,12-dioxo-2,16-dioxatetracyclo[8.7.0.01,14.03,8]heptadeca-3,5,7,10-tetraene-17-carboxylate
IUPAC Name:	methyl (1S,14S,17S)-7-hydroxy-15,15-dimethyl-17-(3-methylbut-2-enyl)-9,12-dioxo-2,16-dioxatetracyclo[8.7.0.01,14.03,8]heptadeca-3,5,7,10-tetraene-17-carboxylate
Synonyms:
Standard InCHIKey:	DPUFUNVIVYLFPP-NTUVXCKYSA-N
Standard InCHI:	InChI=1S/C24H26O7/c1-13(2)9-10-23(21(28)29-5)24-15(11-14(25)12-18(24)22(3,4)31-23)20(27)19-16(26)7-6-8-17(19)30-24/h6-9,11,18,26H,10,12H2,1-5H3/t18-,23+,24+/m0/s1
SMILES:	CC(=CC[C@]1([C@]23[C@@H](CC(=O)C=C2C(=O)C4=C(C=CC=C4O3)O)C(O1)(C)C)C(=O)OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	118707565
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO20443	Cratoxylum pruniflorum	Species	Hypericaceae	Eukaryota	roots	n.a.	n.a.	PMID[24940955]
NPO20443	Cratoxylum pruniflorum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO20443	Cratoxylum pruniflorum	Species	Hypericaceae	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
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	5	ug/ml	PMID[24940955]

☑ 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 NPC476930 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	346
0.1-0.2	1436
0.2-0.3	3296
0.3-0.4	7535
0.4-0.5	10570
0.5-0.6	5209
0.6-0.7	6044
0.7-0.8	6951
0.8-0.85	1209
0.85-0.9	99
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9299	High Similarity	NPC476931
0.9231	High Similarity	NPC43490
0.9231	High Similarity	NPC475107
0.9125	High Similarity	NPC193222
0.9114	High Similarity	NPC94796
0.9062	High Similarity	NPC476255
0.9062	High Similarity	NPC476056
0.9062	High Similarity	NPC62444
0.9051	High Similarity	NPC476929
0.9	High Similarity	NPC189689
0.8951	High Similarity	NPC75141
0.8951	High Similarity	NPC47634
0.8951	High Similarity	NPC158329
0.8951	High Similarity	NPC40089
0.8951	High Similarity	NPC55422
0.8951	High Similarity	NPC476146
0.8924	High Similarity	NPC125969
0.8902	High Similarity	NPC476229
0.8902	High Similarity	NPC476152
0.8896	High Similarity	NPC476196
0.8868	High Similarity	NPC286422
0.8839	High Similarity	NPC116822
0.8839	High Similarity	NPC475717
0.8834	High Similarity	NPC476216
0.8834	High Similarity	NPC41598
0.8831	High Similarity	NPC211811
0.8827	High Similarity	NPC323137
0.882	High Similarity	NPC131578
0.8788	High Similarity	NPC475080
0.8788	High Similarity	NPC476139
0.8782	High Similarity	NPC295650
0.8782	High Similarity	NPC471229
0.8773	High Similarity	NPC223413
0.8758	High Similarity	NPC475106
0.8758	High Similarity	NPC316535
0.8742	High Similarity	NPC161650
0.8735	High Similarity	NPC162248
0.8734	High Similarity	NPC237560
0.8727	High Similarity	NPC118128
0.8726	High Similarity	NPC210597
0.8726	High Similarity	NPC288534
0.8726	High Similarity	NPC275878
0.8718	High Similarity	NPC180351
0.8718	High Similarity	NPC267117
0.8704	High Similarity	NPC472581
0.8701	High Similarity	NPC477955
0.8696	High Similarity	NPC92589
0.8688	High Similarity	NPC264932
0.8688	High Similarity	NPC311574
0.8675	High Similarity	NPC476311
0.8671	High Similarity	NPC301233
0.8671	High Similarity	NPC209760
0.8671	High Similarity	NPC100134
0.8662	High Similarity	NPC476162
0.8662	High Similarity	NPC472580
0.8654	High Similarity	NPC198927
0.8654	High Similarity	NPC477941
0.8654	High Similarity	NPC277032
0.865	High Similarity	NPC329215
0.865	High Similarity	NPC204088
0.865	High Similarity	NPC259007
0.8645	High Similarity	NPC129650
0.8642	High Similarity	NPC219861
0.8634	High Similarity	NPC172687
0.8634	High Similarity	NPC243701
0.8631	High Similarity	NPC233978
0.8631	High Similarity	NPC476199
0.8631	High Similarity	NPC476210
0.8625	High Similarity	NPC210048
0.8616	High Similarity	NPC471116
0.8616	High Similarity	NPC469934
0.8616	High Similarity	NPC476169
0.8614	High Similarity	NPC476159
0.8608	High Similarity	NPC473996
0.8608	High Similarity	NPC477957
0.8608	High Similarity	NPC256141
0.8606	High Similarity	NPC63514
0.8599	High Similarity	NPC150928
0.859	High Similarity	NPC39195
0.8589	High Similarity	NPC109180
0.8581	High Similarity	NPC329678
0.8581	High Similarity	NPC82534
0.8581	High Similarity	NPC299011
0.858	High Similarity	NPC473607
0.8571	High Similarity	NPC18585
0.8571	High Similarity	NPC106985
0.8571	High Similarity	NPC166138
0.8562	High Similarity	NPC469936
0.8562	High Similarity	NPC472050
0.8562	High Similarity	NPC474738
0.8562	High Similarity	NPC475797
0.8562	High Similarity	NPC129053
0.8562	High Similarity	NPC109967
0.8562	High Similarity	NPC321372
0.8562	High Similarity	NPC474609
0.8562	High Similarity	NPC78554
0.8553	High Similarity	NPC311579
0.8553	High Similarity	NPC192189
0.8553	High Similarity	NPC472799
0.8553	High Similarity	NPC230902
0.8553	High Similarity	NPC203080
0.8553	High Similarity	NPC236756
0.8545	High Similarity	NPC476459
0.8545	High Similarity	NPC292233
0.8544	High Similarity	NPC472636
0.8537	High Similarity	NPC473908
0.8535	High Similarity	NPC4423
0.8535	High Similarity	NPC77325
0.8526	High Similarity	NPC308200
0.8526	High Similarity	NPC472918
0.8521	High Similarity	NPC5671
0.8519	High Similarity	NPC115432
0.8519	High Similarity	NPC306978
0.8519	High Similarity	NPC260296
0.8516	High Similarity	NPC184649
0.8516	High Similarity	NPC312789
0.8516	High Similarity	NPC469953
0.8516	High Similarity	NPC303185
0.8516	High Similarity	NPC311144
0.8516	High Similarity	NPC311741
0.8516	High Similarity	NPC234629
0.8516	High Similarity	NPC271288
0.8509	High Similarity	NPC201127
0.8509	High Similarity	NPC246466
0.8506	High Similarity	NPC202981
0.8506	High Similarity	NPC144499
0.8503	High Similarity	NPC477529
0.8503	High Similarity	NPC169018
0.85	High Similarity	NPC279218
0.85	High Similarity	NPC471456
0.85	High Similarity	NPC474542
0.85	High Similarity	NPC108937
0.8497	Intermediate Similarity	NPC16455
0.8497	Intermediate Similarity	NPC477272
0.8497	Intermediate Similarity	NPC307990
0.8491	Intermediate Similarity	NPC217149
0.8491	Intermediate Similarity	NPC216035
0.8491	Intermediate Similarity	NPC476238
0.8491	Intermediate Similarity	NPC171651
0.8491	Intermediate Similarity	NPC243171
0.8491	Intermediate Similarity	NPC327269
0.8491	Intermediate Similarity	NPC285623
0.8491	Intermediate Similarity	NPC35567
0.8491	Intermediate Similarity	NPC31627
0.8487	Intermediate Similarity	NPC470671
0.8487	Intermediate Similarity	NPC473988
0.8487	Intermediate Similarity	NPC470672
0.8487	Intermediate Similarity	NPC474487
0.8487	Intermediate Similarity	NPC474504
0.8485	Intermediate Similarity	NPC475109
0.8481	Intermediate Similarity	NPC471115
0.8481	Intermediate Similarity	NPC470107
0.8481	Intermediate Similarity	NPC29777
0.8481	Intermediate Similarity	NPC472421
0.8481	Intermediate Similarity	NPC158866
0.8476	Intermediate Similarity	NPC91288
0.8476	Intermediate Similarity	NPC155640
0.8471	Intermediate Similarity	NPC145467
0.8471	Intermediate Similarity	NPC191634
0.8471	Intermediate Similarity	NPC296869
0.8471	Intermediate Similarity	NPC473729
0.8466	Intermediate Similarity	NPC117985
0.8462	Intermediate Similarity	NPC229190
0.8462	Intermediate Similarity	NPC227275
0.8462	Intermediate Similarity	NPC124729
0.8462	Intermediate Similarity	NPC472033
0.8462	Intermediate Similarity	NPC5820
0.8462	Intermediate Similarity	NPC470322
0.8462	Intermediate Similarity	NPC25844
0.8462	Intermediate Similarity	NPC306488
0.8462	Intermediate Similarity	NPC178343
0.8462	Intermediate Similarity	NPC154217
0.8457	Intermediate Similarity	NPC244750
0.8452	Intermediate Similarity	NPC105381
0.8452	Intermediate Similarity	NPC10302
0.8452	Intermediate Similarity	NPC470216
0.8452	Intermediate Similarity	NPC73899
0.8452	Intermediate Similarity	NPC5990
0.8452	Intermediate Similarity	NPC17105
0.8452	Intermediate Similarity	NPC474276
0.8452	Intermediate Similarity	NPC147363
0.8452	Intermediate Similarity	NPC113770
0.8447	Intermediate Similarity	NPC215917
0.8447	Intermediate Similarity	NPC10754
0.8447	Intermediate Similarity	NPC313922
0.8447	Intermediate Similarity	NPC146636
0.8447	Intermediate Similarity	NPC20530
0.8447	Intermediate Similarity	NPC164427
0.8443	Intermediate Similarity	NPC313717
0.8443	Intermediate Similarity	NPC120220
0.8443	Intermediate Similarity	NPC315306
0.8442	Intermediate Similarity	NPC232021
0.8442	Intermediate Similarity	NPC126534
0.8442	Intermediate Similarity	NPC171870
0.8442	Intermediate Similarity	NPC40118
0.8438	Intermediate Similarity	NPC213608
0.8438	Intermediate Similarity	NPC1477
0.8438	Intermediate Similarity	NPC293286
0.8428	Intermediate Similarity	NPC278476
0.8428	Intermediate Similarity	NPC81474

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 NPC476930 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	872
0.2-0.3	1701
0.3-0.4	2547
0.4-0.5	2114
0.5-0.6	1069
0.6-0.7	369
0.7-0.8	148
0.8-0.85	19
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8742	High Similarity	NPD7075	Discontinued
0.8671	High Similarity	NPD7096	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD6799	Approved
0.8428	Intermediate Similarity	NPD7411	Suspended
0.8397	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD3749	Approved
0.8375	Intermediate Similarity	NPD6801	Discontinued
0.8365	Intermediate Similarity	NPD6599	Discontinued
0.8333	Intermediate Similarity	NPD3882	Suspended
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8272	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD5403	Approved
0.8141	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD3750	Approved
0.8129	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD1549	Phase 2
0.8077	Intermediate Similarity	NPD2800	Approved
0.8065	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD2534	Approved
0.805	Intermediate Similarity	NPD2533	Approved
0.805	Intermediate Similarity	NPD5401	Approved
0.805	Intermediate Similarity	NPD2532	Approved
0.8049	Intermediate Similarity	NPD5402	Approved
0.8049	Intermediate Similarity	NPD3817	Phase 2
0.8025	Intermediate Similarity	NPD4380	Phase 2
0.7988	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD5494	Approved
0.7963	Intermediate Similarity	NPD3226	Approved
0.7962	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7473	Discontinued
0.7935	Intermediate Similarity	NPD1510	Phase 2
0.7927	Intermediate Similarity	NPD1934	Approved
0.7911	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD1240	Approved
0.7904	Intermediate Similarity	NPD919	Approved
0.7898	Intermediate Similarity	NPD8434	Phase 2
0.7892	Intermediate Similarity	NPD7768	Phase 2
0.7885	Intermediate Similarity	NPD1551	Phase 2
0.7885	Intermediate Similarity	NPD2796	Approved
0.7882	Intermediate Similarity	NPD2403	Approved
0.7879	Intermediate Similarity	NPD2801	Approved
0.787	Intermediate Similarity	NPD6232	Discontinued
0.7848	Intermediate Similarity	NPD1243	Approved
0.784	Intermediate Similarity	NPD920	Approved
0.7821	Intermediate Similarity	NPD2799	Discontinued
0.7821	Intermediate Similarity	NPD3748	Approved
0.7811	Intermediate Similarity	NPD1247	Approved
0.7806	Intermediate Similarity	NPD1607	Approved
0.7798	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3818	Discontinued
0.7784	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1512	Approved
0.7778	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3268	Approved
0.7778	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6166	Phase 2
0.7771	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6099	Approved
0.7771	Intermediate Similarity	NPD6100	Approved
0.7722	Intermediate Similarity	NPD2346	Discontinued
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD6559	Discontinued
0.7702	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2313	Discontinued
0.7657	Intermediate Similarity	NPD6797	Phase 2
0.7654	Intermediate Similarity	NPD1511	Approved
0.7644	Intermediate Similarity	NPD5844	Phase 1
0.7616	Intermediate Similarity	NPD3926	Phase 2
0.7614	Intermediate Similarity	NPD7251	Discontinued
0.761	Intermediate Similarity	NPD1471	Phase 3
0.761	Intermediate Similarity	NPD2344	Approved
0.7602	Intermediate Similarity	NPD6959	Discontinued
0.76	Intermediate Similarity	NPD9717	Approved
0.7586	Intermediate Similarity	NPD3751	Discontinued
0.758	Intermediate Similarity	NPD6651	Approved
0.7578	Intermediate Similarity	NPD4628	Phase 3
0.7571	Intermediate Similarity	NPD7808	Phase 3
0.7566	Intermediate Similarity	NPD1203	Approved
0.756	Intermediate Similarity	NPD1465	Phase 2
0.7558	Intermediate Similarity	NPD5711	Approved
0.7558	Intermediate Similarity	NPD5710	Approved
0.7557	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD5953	Discontinued
0.7548	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD2935	Discontinued
0.7516	Intermediate Similarity	NPD447	Suspended
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD7074	Phase 3
0.7484	Intermediate Similarity	NPD7033	Discontinued
0.7472	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD3267	Approved
0.7451	Intermediate Similarity	NPD3266	Approved
0.7451	Intermediate Similarity	NPD2797	Approved
0.7444	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7286	Phase 2
0.7443	Intermediate Similarity	NPD7054	Approved
0.7436	Intermediate Similarity	NPD3764	Approved
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7423	Intermediate Similarity	NPD2309	Approved
0.7419	Intermediate Similarity	NPD6832	Phase 2
0.7418	Intermediate Similarity	NPD4287	Approved
0.741	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD1933	Approved
0.7405	Intermediate Similarity	NPD6355	Discontinued
0.7403	Intermediate Similarity	NPD2798	Approved
0.7401	Intermediate Similarity	NPD7472	Approved
0.7394	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4308	Phase 3
0.7366	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.7321	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD4749	Approved
0.7318	Intermediate Similarity	NPD6765	Approved
0.7318	Intermediate Similarity	NPD6764	Approved
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7299	Intermediate Similarity	NPD7199	Phase 2
0.7296	Intermediate Similarity	NPD5124	Phase 1
0.7296	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7229	Phase 3
0.7255	Intermediate Similarity	NPD1608	Approved
0.7249	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD9493	Approved
0.7233	Intermediate Similarity	NPD4060	Phase 1
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7215	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6798	Discontinued
0.7215	Intermediate Similarity	NPD411	Approved
0.7215	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2354	Approved
0.7209	Intermediate Similarity	NPD4288	Approved
0.7197	Intermediate Similarity	NPD4908	Phase 1
0.7193	Intermediate Similarity	NPD37	Approved
0.7191	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD422	Phase 1
0.719	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD230	Phase 1
0.7184	Intermediate Similarity	NPD6234	Discontinued
0.7178	Intermediate Similarity	NPD6005	Phase 3
0.7178	Intermediate Similarity	NPD6004	Phase 3
0.7178	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6002	Phase 3
0.7176	Intermediate Similarity	NPD6585	Discontinued
0.7168	Intermediate Similarity	NPD4967	Phase 2
0.7168	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD4966	Approved
0.7161	Intermediate Similarity	NPD3225	Approved
0.716	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6780	Approved
0.7158	Intermediate Similarity	NPD6778	Approved
0.7158	Intermediate Similarity	NPD6784	Approved
0.7158	Intermediate Similarity	NPD6781	Approved
0.7158	Intermediate Similarity	NPD6776	Approved
0.7158	Intermediate Similarity	NPD6782	Approved
0.7158	Intermediate Similarity	NPD6777	Approved
0.7158	Intermediate Similarity	NPD6785	Approved
0.7158	Intermediate Similarity	NPD6779	Approved
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7151	Intermediate Similarity	NPD5760	Phase 2
0.7151	Intermediate Similarity	NPD5761	Phase 2
0.7143	Intermediate Similarity	NPD5049	Phase 3
0.7135	Intermediate Similarity	NPD5889	Approved
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5890	Approved
0.7126	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD943	Approved
0.7125	Intermediate Similarity	NPD4307	Phase 2
0.7108	Intermediate Similarity	NPD3887	Approved
0.7092	Intermediate Similarity	NPD7874	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2654	Approved
0.7081	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1610	Phase 2
0.7073	Intermediate Similarity	NPD5763	Approved
0.7073	Intermediate Similarity	NPD5762	Approved
0.7073	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2353	Approved
0.707	Intermediate Similarity	NPD1019	Discontinued
0.707	Intermediate Similarity	NPD5647	Approved
0.7062	Intermediate Similarity	NPD6808	Phase 2
0.7059	Intermediate Similarity	NPD17	Approved
0.7048	Intermediate Similarity	NPD7003	Approved
0.7047	Intermediate Similarity	NPD7696	Phase 3
0.7047	Intermediate Similarity	NPD7698	Approved
0.7047	Intermediate Similarity	NPD7697	Approved
0.7043	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD9545	Approved
0.7037	Intermediate Similarity	NPD4361	Phase 2
0.7037	Intermediate Similarity	NPD4362	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