NPASS Compound

Structure

CID275575 OpenBabel06191716082D 36 40 0 0 0 0 0 0 0 0999 V2000 7.7942 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -4.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 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 -4.5000 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 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 1.7321 -1.0000 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 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 -1.7321 -4.0000 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 6.0622 -2.5000 0.0000 O 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 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 7 8 1 0 0 0 0 7 16 2 0 0 0 0 8 17 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 17 21 2 0 0 0 0 18 25 1 0 0 0 0 19 26 2 0 0 0 0 19 27 1 0 0 0 0 20 26 1 0 0 0 0 20 28 2 0 0 0 0 21 31 1 0 0 0 0 22 23 1 0 0 0 0 22 27 2 0 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 23 32 2 0 0 0 0 24 25 2 0 0 0 0 24 33 1 0 0 0 0 25 34 1 0 0 0 0 26 35 1 0 0 0 0 27 34 1 0 0 0 0 28 36 1 0 0 0 0 29 35 1 0 0 0 0 30 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	490.24
Volume:	513.667
LogP:	7.742
LogD:	4.48
LogS:	-1.914
# Rotatable Bonds:	3
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.403
Synthetic Accessibility Score:	3.47
Fsp3:	0.433
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:	-4.768
MDCK Permeability:	1.560629425512161e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.059
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	98.89020538330078%
Volume Distribution (VD):	0.819
Pgp-substrate:	4.1021552085876465%

ADMET: Metabolism

CYP1A2-inhibitor:	0.184
CYP1A2-substrate:	0.316
CYP2C19-inhibitor:	0.587
CYP2C19-substrate:	0.065
CYP2C9-inhibitor:	0.52
CYP2C9-substrate:	0.951
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.166
CYP3A4-inhibitor:	0.147
CYP3A4-substrate:	0.085

ADMET: Excretion

Clearance (CL):	2.722
Half-life (T1/2):	0.054

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.906
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.091
Rat Oral Acute Toxicity:	0.756
Maximum Recommended Daily Dose:	0.42
Skin Sensitization:	0.496
Carcinogencity:	0.117
Eye Corrosion:	0.003
Eye Irritation:	0.1
Respiratory Toxicity:	0.084

Download Data

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

Natural Product: NPC275575

Natural Product ID:	NPC275575
*Common Name:**	Dorsilurin K
IUPAC Name:	n.a.
Synonyms:	dorsilurin K
Standard InCHIKey:	JHDGWJWVSUFMAQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H34O6/c1-16(2)7-8-17-9-10-18(15-21(17)31)25-24(33)23(32)22-27(34-25)19-11-13-29(3,4)35-26(19)20-12-14-30(5,6)36-28(20)22/h7,9-10,15,31,33H,8,11-14H2,1-6H3
SMILES:	CC(=CCc1ccc(cc1O)c1c(c(=O)c2c(c3CCC(C)(C)Oc3c3CCC(C)(C)Oc23)o1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455686
PubChem CID:	25178185
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003504] 8-prenylated flavones

*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
NPO4673	Dorstenia psilurus	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061390]
NPO4673	Dorstenia psilurus	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[19061390]
NPO4673	Dorstenia psilurus	Species	Moraceae	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
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	43950.0	nM	PMID[534548]

☑ 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 NPC275575 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	463
0.1-0.2	1976
0.2-0.3	4880
0.3-0.4	11206
0.4-0.5	6459
0.5-0.6	3977
0.6-0.7	5427
0.7-0.8	4537
0.8-0.85	2549
0.85-0.9	1068
0.9-0.95	151
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9864	High Similarity	NPC142527
0.973	High Similarity	NPC45934
0.966	High Similarity	NPC269420
0.9603	High Similarity	NPC282390
0.9603	High Similarity	NPC281137
0.9459	High Similarity	NPC296869
0.9404	High Similarity	NPC193200
0.9392	High Similarity	NPC166757
0.9392	High Similarity	NPC14001
0.9333	High Similarity	NPC472633
0.9329	High Similarity	NPC244407
0.9324	High Similarity	NPC124729
0.9324	High Similarity	NPC220418
0.932	High Similarity	NPC190637
0.932	High Similarity	NPC212932
0.932	High Similarity	NPC293053
0.932	High Similarity	NPC9117
0.932	High Similarity	NPC219915
0.932	High Similarity	NPC24821
0.9257	High Similarity	NPC216538
0.9257	High Similarity	NPC326500
0.9257	High Similarity	NPC273538
0.9252	High Similarity	NPC200694
0.9252	High Similarity	NPC473042
0.9221	High Similarity	NPC237418
0.9205	High Similarity	NPC101957
0.9205	High Similarity	NPC120105
0.9195	High Similarity	NPC196114
0.9195	High Similarity	NPC5820
0.9195	High Similarity	NPC178343
0.9195	High Similarity	NPC306488
0.9189	High Similarity	NPC38219
0.915	High Similarity	NPC329844
0.915	High Similarity	NPC169990
0.915	High Similarity	NPC280530
0.915	High Similarity	NPC210942
0.915	High Similarity	NPC178964
0.915	High Similarity	NPC311579
0.915	High Similarity	NPC236756
0.915	High Similarity	NPC95842
0.9139	High Similarity	NPC474052
0.9139	High Similarity	NPC223988
0.9133	High Similarity	NPC296998
0.9133	High Similarity	NPC283234
0.9133	High Similarity	NPC473077
0.9122	High Similarity	NPC217083
0.9122	High Similarity	NPC299080
0.9122	High Similarity	NPC78803
0.9122	High Similarity	NPC59739
0.9122	High Similarity	NPC214236
0.9122	High Similarity	NPC62840
0.9122	High Similarity	NPC293852
0.9122	High Similarity	NPC144499
0.9091	High Similarity	NPC55662
0.9091	High Similarity	NPC166054
0.9091	High Similarity	NPC48579
0.9091	High Similarity	NPC207809
0.9091	High Similarity	NPC476169
0.9091	High Similarity	NPC259710
0.9091	High Similarity	NPC304207
0.9091	High Similarity	NPC217706
0.9085	High Similarity	NPC37684
0.9085	High Similarity	NPC63187
0.9085	High Similarity	NPC157784
0.9079	High Similarity	NPC29777
0.9079	High Similarity	NPC61258
0.9079	High Similarity	NPC471115
0.9073	High Similarity	NPC186397
0.9073	High Similarity	NPC37135
0.9073	High Similarity	NPC161191
0.9073	High Similarity	NPC160821
0.9073	High Similarity	NPC132592
0.9067	High Similarity	NPC473132
0.9067	High Similarity	NPC473135
0.9067	High Similarity	NPC20488
0.9067	High Similarity	NPC111786
0.9067	High Similarity	NPC83357
0.9067	High Similarity	NPC267375
0.9067	High Similarity	NPC88964
0.9067	High Similarity	NPC301276
0.9067	High Similarity	NPC214774
0.9067	High Similarity	NPC195621
0.9067	High Similarity	NPC54577
0.9067	High Similarity	NPC475052
0.9067	High Similarity	NPC246948
0.9067	High Similarity	NPC67805
0.9067	High Similarity	NPC312973
0.9067	High Similarity	NPC470647
0.9067	High Similarity	NPC290133
0.9067	High Similarity	NPC142405
0.9067	High Similarity	NPC176229
0.9067	High Similarity	NPC24136
0.9067	High Similarity	NPC470676
0.9067	High Similarity	NPC187282
0.906	High Similarity	NPC166138
0.906	High Similarity	NPC18585
0.906	High Similarity	NPC106985
0.906	High Similarity	NPC158874
0.9054	High Similarity	NPC156590
0.9054	High Similarity	NPC118840
0.9054	High Similarity	NPC205006
0.9054	High Similarity	NPC147688
0.9054	High Similarity	NPC64908
0.9048	High Similarity	NPC55018
0.9048	High Similarity	NPC96565
0.9048	High Similarity	NPC216978
0.9048	High Similarity	NPC220062
0.9048	High Similarity	NPC301217
0.9048	High Similarity	NPC303633
0.9032	High Similarity	NPC146636
0.9032	High Similarity	NPC192587
0.9026	High Similarity	NPC100134
0.9026	High Similarity	NPC170492
0.9026	High Similarity	NPC209760
0.9026	High Similarity	NPC248793
0.9026	High Similarity	NPC180301
0.902	High Similarity	NPC205046
0.902	High Similarity	NPC59162
0.902	High Similarity	NPC478148
0.902	High Similarity	NPC304295
0.9013	High Similarity	NPC473016
0.9013	High Similarity	NPC158338
0.9013	High Similarity	NPC470461
0.9013	High Similarity	NPC266499
0.9013	High Similarity	NPC65775
0.9013	High Similarity	NPC65589
0.9013	High Similarity	NPC5173
0.9013	High Similarity	NPC288036
0.9013	High Similarity	NPC97029
0.9013	High Similarity	NPC10027
0.9013	High Similarity	NPC97028
0.9013	High Similarity	NPC100985
0.9007	High Similarity	NPC79469
0.9007	High Similarity	NPC110303
0.9007	High Similarity	NPC23728
0.9007	High Similarity	NPC140120
0.9007	High Similarity	NPC97716
0.9007	High Similarity	NPC104406
0.9007	High Similarity	NPC237635
0.9007	High Similarity	NPC24673
0.9007	High Similarity	NPC201731
0.9	High Similarity	NPC311741
0.9	High Similarity	NPC234629
0.8993	High Similarity	NPC226636
0.8993	High Similarity	NPC1534
0.8993	High Similarity	NPC11561
0.8986	High Similarity	NPC159275
0.8986	High Similarity	NPC305355
0.8986	High Similarity	NPC150522
0.8986	High Similarity	NPC172986
0.8986	High Similarity	NPC69769
0.8986	High Similarity	NPC475680
0.8986	High Similarity	NPC270883
0.8986	High Similarity	NPC241100
0.8986	High Similarity	NPC235239
0.8986	High Similarity	NPC261227
0.8981	High Similarity	NPC172687
0.898	High Similarity	NPC201395
0.8974	High Similarity	NPC471209
0.8974	High Similarity	NPC284820
0.8974	High Similarity	NPC273843
0.8974	High Similarity	NPC476630
0.8974	High Similarity	NPC473272
0.8974	High Similarity	NPC218871
0.8974	High Similarity	NPC201127
0.8974	High Similarity	NPC210048
0.8968	High Similarity	NPC477958
0.8968	High Similarity	NPC111341
0.8968	High Similarity	NPC304745
0.8968	High Similarity	NPC133392
0.8961	High Similarity	NPC138288
0.8961	High Similarity	NPC475790
0.8961	High Similarity	NPC217447
0.8961	High Similarity	NPC210597
0.8954	High Similarity	NPC227122
0.8954	High Similarity	NPC188403
0.8954	High Similarity	NPC88804
0.8954	High Similarity	NPC37348
0.8954	High Similarity	NPC3825
0.8947	High Similarity	NPC256672
0.8947	High Similarity	NPC6511
0.8947	High Similarity	NPC266572
0.8947	High Similarity	NPC7025
0.8947	High Similarity	NPC145467
0.8947	High Similarity	NPC321623
0.8947	High Similarity	NPC470460
0.8947	High Similarity	NPC189087
0.8947	High Similarity	NPC27221
0.894	High Similarity	NPC285630
0.894	High Similarity	NPC477955
0.894	High Similarity	NPC127059
0.894	High Similarity	NPC472629
0.894	High Similarity	NPC470458
0.894	High Similarity	NPC329678
0.8938	High Similarity	NPC272502
0.8938	High Similarity	NPC471213
0.8933	High Similarity	NPC11700
0.8933	High Similarity	NPC478086
0.8933	High Similarity	NPC185276
0.8933	High Similarity	NPC316816

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 NPC275575 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	411
0.1-0.2	1017
0.2-0.3	1794
0.3-0.4	2725
0.4-0.5	1790
0.5-0.6	945
0.6-0.7	303
0.7-0.8	124
0.8-0.85	25
0.85-0.9	15
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9257	High Similarity	NPD4378	Clinical (unspecified phase)
0.8874	High Similarity	NPD7410	Clinical (unspecified phase)
0.8805	High Similarity	NPD6959	Discontinued
0.8782	High Similarity	NPD2393	Clinical (unspecified phase)
0.8712	High Similarity	NPD7804	Clinical (unspecified phase)
0.8693	High Similarity	NPD1512	Approved
0.8642	High Similarity	NPD6166	Phase 2
0.8642	High Similarity	NPD6168	Clinical (unspecified phase)
0.8642	High Similarity	NPD6167	Clinical (unspecified phase)
0.8616	High Similarity	NPD7075	Discontinued
0.8608	High Similarity	NPD8443	Clinical (unspecified phase)
0.859	High Similarity	NPD4380	Phase 2
0.8562	High Similarity	NPD1511	Approved
0.8544	High Similarity	NPD7096	Clinical (unspecified phase)
0.8544	High Similarity	NPD7819	Suspended
0.8533	High Similarity	NPD1550	Clinical (unspecified phase)
0.8533	High Similarity	NPD1552	Clinical (unspecified phase)
0.8481	Intermediate Similarity	NPD1934	Approved
0.8477	Intermediate Similarity	NPD1549	Phase 2
0.8443	Intermediate Similarity	NPD7251	Discontinued
0.8428	Intermediate Similarity	NPD2801	Approved
0.8418	Intermediate Similarity	NPD7411	Suspended
0.84	Intermediate Similarity	NPD1510	Phase 2
0.8393	Intermediate Similarity	NPD7808	Phase 3
0.8389	Intermediate Similarity	NPD1607	Approved
0.8383	Intermediate Similarity	NPD6797	Phase 2
0.8373	Intermediate Similarity	NPD7054	Approved
0.8344	Intermediate Similarity	NPD2796	Approved
0.8323	Intermediate Similarity	NPD7074	Phase 3
0.8323	Intermediate Similarity	NPD7472	Approved
0.8272	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD3817	Phase 2
0.8255	Intermediate Similarity	NPD1240	Approved
0.825	Intermediate Similarity	NPD6801	Discontinued
0.8224	Intermediate Similarity	NPD6100	Approved
0.8224	Intermediate Similarity	NPD6099	Approved
0.821	Intermediate Similarity	NPD3882	Suspended
0.8193	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD5494	Approved
0.8144	Intermediate Similarity	NPD7473	Discontinued
0.8129	Intermediate Similarity	NPD3750	Approved
0.8125	Intermediate Similarity	NPD6599	Discontinued
0.8098	Intermediate Similarity	NPD7768	Phase 2
0.8089	Intermediate Similarity	NPD7390	Discontinued
0.8089	Intermediate Similarity	NPD6799	Approved
0.8072	Intermediate Similarity	NPD6232	Discontinued
0.8065	Intermediate Similarity	NPD2800	Approved
0.8049	Intermediate Similarity	NPD3749	Approved
0.8038	Intermediate Similarity	NPD2533	Approved
0.8038	Intermediate Similarity	NPD2534	Approved
0.8038	Intermediate Similarity	NPD2532	Approved
0.8013	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6559	Discontinued
0.8	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2935	Discontinued
0.7965	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD3226	Approved
0.7941	Intermediate Similarity	NPD5844	Phase 1
0.7935	Intermediate Similarity	NPD2346	Discontinued
0.7927	Intermediate Similarity	NPD5402	Approved
0.7922	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD3818	Discontinued
0.7879	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD1551	Phase 2
0.7849	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1243	Approved
0.7834	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD5403	Approved
0.7815	Intermediate Similarity	NPD4625	Phase 3
0.7806	Intermediate Similarity	NPD3748	Approved
0.7792	Intermediate Similarity	NPD6651	Approved
0.7763	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2313	Discontinued
0.7716	Intermediate Similarity	NPD920	Approved
0.7702	Intermediate Similarity	NPD5401	Approved
0.7692	Intermediate Similarity	NPD1247	Approved
0.7692	Intermediate Similarity	NPD2799	Discontinued
0.7679	Intermediate Similarity	NPD919	Approved
0.7657	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1465	Phase 2
0.7647	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD7286	Phase 2
0.7614	Intermediate Similarity	NPD8312	Approved
0.7614	Intermediate Similarity	NPD8313	Approved
0.7595	Intermediate Similarity	NPD2344	Approved
0.7593	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD7698	Approved
0.7581	Intermediate Similarity	NPD7697	Approved
0.7581	Intermediate Similarity	NPD7696	Phase 3
0.758	Intermediate Similarity	NPD4308	Phase 3
0.7578	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD943	Approved
0.7544	Intermediate Similarity	NPD5710	Approved
0.7544	Intermediate Similarity	NPD5711	Approved
0.7543	Intermediate Similarity	NPD5953	Discontinued
0.7533	Intermediate Similarity	NPD4749	Approved
0.7527	Intermediate Similarity	NPD4360	Phase 2
0.7527	Intermediate Similarity	NPD4363	Phase 3
0.7516	Intermediate Similarity	NPD4908	Phase 1
0.7514	Intermediate Similarity	NPD6777	Approved
0.7514	Intermediate Similarity	NPD6782	Approved
0.7514	Intermediate Similarity	NPD6779	Approved
0.7514	Intermediate Similarity	NPD6778	Approved
0.7514	Intermediate Similarity	NPD6776	Approved
0.7514	Intermediate Similarity	NPD6780	Approved
0.7514	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD3926	Phase 2
0.7487	Intermediate Similarity	NPD7435	Discontinued
0.7486	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7453	Intermediate Similarity	NPD4628	Phase 3
0.7453	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD7870	Phase 2
0.7447	Intermediate Similarity	NPD7871	Phase 2
0.7446	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3787	Discontinued
0.7434	Intermediate Similarity	NPD1203	Approved
0.7421	Intermediate Similarity	NPD7701	Phase 2
0.7421	Intermediate Similarity	NPD5406	Approved
0.7421	Intermediate Similarity	NPD5408	Approved
0.7421	Intermediate Similarity	NPD5404	Approved
0.7421	Intermediate Similarity	NPD5405	Approved
0.7419	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3268	Approved
0.741	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7458	Discontinued
0.7407	Intermediate Similarity	NPD2309	Approved
0.7403	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5124	Phase 1
0.7386	Intermediate Similarity	NPD2798	Approved
0.7358	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD4307	Phase 2
0.7321	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2797	Approved
0.7312	Intermediate Similarity	NPD7699	Phase 2
0.7312	Intermediate Similarity	NPD7700	Phase 2
0.7308	Intermediate Similarity	NPD411	Approved
0.7308	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7783	Phase 2
0.7292	Intermediate Similarity	NPD8151	Discontinued
0.729	Intermediate Similarity	NPD6832	Phase 2
0.7285	Intermediate Similarity	NPD1201	Approved
0.7285	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1610	Phase 2
0.7285	Intermediate Similarity	NPD422	Phase 1
0.7278	Intermediate Similarity	NPD6844	Discontinued
0.7277	Intermediate Similarity	NPD7584	Approved
0.7267	Intermediate Similarity	NPD1471	Phase 3
0.7255	Intermediate Similarity	NPD3225	Approved
0.7254	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD7874	Approved
0.725	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1548	Phase 1
0.7243	Intermediate Similarity	NPD6535	Approved
0.7243	Intermediate Similarity	NPD6534	Approved
0.7241	Intermediate Similarity	NPD7229	Phase 3
0.7239	Intermediate Similarity	NPD7003	Approved
0.7238	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD9717	Approved
0.7237	Intermediate Similarity	NPD1608	Approved
0.7234	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7801	Approved
0.7215	Intermediate Similarity	NPD1613	Approved
0.7215	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1470	Approved
0.7204	Intermediate Similarity	NPD4361	Phase 2
0.7204	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD8434	Phase 2
0.7193	Intermediate Similarity	NPD4288	Approved
0.7186	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD8320	Phase 1
0.7173	Intermediate Similarity	NPD8319	Approved
0.717	Intermediate Similarity	NPD447	Suspended
0.717	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6585	Discontinued
0.7158	Intermediate Similarity	NPD6823	Phase 2
0.7135	Intermediate Similarity	NPD8455	Phase 2
0.7124	Intermediate Similarity	NPD3972	Approved
0.712	Intermediate Similarity	NPD4287	Approved
0.7097	Intermediate Similarity	NPD3266	Approved
0.7097	Intermediate Similarity	NPD3267	Approved
0.7079	Intermediate Similarity	NPD7177	Discontinued
0.7079	Intermediate Similarity	NPD7228	Approved
0.7073	Intermediate Similarity	NPD2654	Approved
0.7066	Intermediate Similarity	NPD7447	Phase 1
0.7063	Intermediate Similarity	NPD230	Phase 1
0.7062	Intermediate Similarity	NPD2403	Approved
0.7062	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3300	Phase 2
0.7047	Intermediate Similarity	NPD6671	Approved
0.7039	Intermediate Similarity	NPD17	Approved
0.7035	Intermediate Similarity	NPD5760	Phase 2
0.7035	Intermediate Similarity	NPD5761	Phase 2
0.7025	Intermediate Similarity	NPD7095	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