NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	316.13
Volume:	328.267
LogP:	3.277
LogD:	2.152
LogS:	-3.526
# Rotatable Bonds:	0
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.568
Synthetic Accessibility Score:	4.039
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.716
MDCK Permeability:	1.655853156989906e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.773
30% Bioavailability (F30%):	0.194

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.087
Plasma Protein Binding (PPB):	97.85002899169922%
Volume Distribution (VD):	0.383
Pgp-substrate:	2.041994333267212%

ADMET: Metabolism

CYP1A2-inhibitor:	0.893
CYP1A2-substrate:	0.117
CYP2C19-inhibitor:	0.654
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.651
CYP2C9-substrate:	0.976
CYP2D6-inhibitor:	0.886
CYP2D6-substrate:	0.431
CYP3A4-inhibitor:	0.692
CYP3A4-substrate:	0.095

ADMET: Excretion

Clearance (CL):	8.893
Half-life (T1/2):	0.931

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.132
Drug-inuced Liver Injury (DILI):	0.696
AMES Toxicity:	0.088
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.899
Skin Sensitization:	0.856
Carcinogencity:	0.831
Eye Corrosion:	0.02
Eye Irritation:	0.558
Respiratory Toxicity:	0.693

Download Data

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

Natural Product: NPC478201

Natural Product ID:	NPC478201
*Common Name:**	(4R,5S,6E)-5,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),6,15,17-tetraene-2,12-dione
IUPAC Name:	(4R,5S,6E)-5,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),6,15,17-tetraene-2,12-dione
Synonyms:
Standard InCHIKey:	PUBJBUSNXLSOQM-YWDVGMFKSA-N
Standard InCHI:	InChI=1S/C18H22O6/c1-11-15(21)7-5-3-2-4-6-13(19)8-12-9-14(20)10-16(22)17(12)18(23)24-11/h5,7,9-11,15,20-22H,2-4,6,8H2,1H3/b7-5+/t11-,15+/m1/s1
SMILES:	C[C@@H]1[C@H](/C=C/CCCCC(=O)CC2=C(C(=CC(=C2)O)O)C(=O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	146682745
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO33700	Paecilomyces sp. SC0924	Species	Clavicipitaceae	Eukaryota	n.a.	Dinghu Mountain Biosphere Reserve, Guangdong, China	2003-MAR	PMID[28749671]

☑ 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 NPC478201 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	321
0.1-0.2	1436
0.2-0.3	3556
0.3-0.4	7999
0.4-0.5	10615
0.5-0.6	3892
0.6-0.7	6730
0.7-0.8	6511
0.8-0.85	1322
0.85-0.9	224
0.9-0.95	73
0.95-1	18

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472035
0.9852	High Similarity	NPC313123
0.9852	High Similarity	NPC478217
0.9781	High Similarity	NPC478203
0.9781	High Similarity	NPC126882
0.9781	High Similarity	NPC210966
0.9776	High Similarity	NPC33144
0.9776	High Similarity	NPC177307
0.9776	High Similarity	NPC9121
0.9776	High Similarity	NPC478200
0.971	High Similarity	NPC472034
0.971	High Similarity	NPC257558
0.9708	High Similarity	NPC478202
0.964	High Similarity	NPC472033
0.963	High Similarity	NPC191835
0.963	High Similarity	NPC472403
0.9571	High Similarity	NPC472036
0.9556	High Similarity	NPC178467
0.9556	High Similarity	NPC70380
0.9556	High Similarity	NPC474849
0.9556	High Similarity	NPC474771
0.9556	High Similarity	NPC149372
0.9556	High Similarity	NPC65837
0.9489	High Similarity	NPC158472
0.9485	High Similarity	NPC94248
0.9485	High Similarity	NPC475974
0.9485	High Similarity	NPC212693
0.942	High Similarity	NPC158634
0.9416	High Similarity	NPC52358
0.9416	High Similarity	NPC92655
0.9412	High Similarity	NPC71256
0.9403	High Similarity	NPC43627
0.9403	High Similarity	NPC153783
0.9353	High Similarity	NPC474385
0.9343	High Similarity	NPC472602
0.9338	High Similarity	NPC235115
0.9333	High Similarity	NPC474097
0.9286	High Similarity	NPC472006
0.9281	High Similarity	NPC475730
0.9281	High Similarity	NPC1704
0.9281	High Similarity	NPC472603
0.9281	High Similarity	NPC67650
0.9281	High Similarity	NPC53649
0.9281	High Similarity	NPC244923
0.9275	High Similarity	NPC268052
0.9275	High Similarity	NPC32360
0.9275	High Similarity	NPC474655
0.9275	High Similarity	NPC139634
0.9275	High Similarity	NPC105456
0.9254	High Similarity	NPC219892
0.9254	High Similarity	NPC189823
0.9231	High Similarity	NPC240622
0.9231	High Similarity	NPC471641
0.9231	High Similarity	NPC215711
0.9231	High Similarity	NPC240253
0.9231	High Similarity	NPC73411
0.9231	High Similarity	NPC471642
0.922	High Similarity	NPC210425
0.922	High Similarity	NPC86373
0.922	High Similarity	NPC151607
0.922	High Similarity	NPC277426
0.922	High Similarity	NPC42540
0.922	High Similarity	NPC280404
0.9209	High Similarity	NPC472601
0.9209	High Similarity	NPC472600
0.9161	High Similarity	NPC210320
0.9155	High Similarity	NPC83272
0.9155	High Similarity	NPC312789
0.9149	High Similarity	NPC51106
0.9149	High Similarity	NPC159721
0.9149	High Similarity	NPC354984
0.9143	High Similarity	NPC472605
0.9143	High Similarity	NPC472604
0.913	High Similarity	NPC194579
0.913	High Similarity	NPC135837
0.9124	High Similarity	NPC27407
0.9103	High Similarity	NPC56204
0.9091	High Similarity	NPC107625
0.9071	High Similarity	NPC155205
0.9065	High Similarity	NPC221104
0.9051	High Similarity	NPC175943
0.9034	High Similarity	NPC84142
0.903	High Similarity	NPC41263
0.9014	High Similarity	NPC472610
0.9014	High Similarity	NPC469542
0.9014	High Similarity	NPC471731
0.9007	High Similarity	NPC37530
0.9007	High Similarity	NPC470842
0.9	High Similarity	NPC88269
0.8986	High Similarity	NPC182496
0.8986	High Similarity	NPC142027
0.8986	High Similarity	NPC180905
0.8973	High Similarity	NPC164762
0.8973	High Similarity	NPC472891
0.8971	High Similarity	NPC470831
0.8971	High Similarity	NPC214702
0.8966	High Similarity	NPC153417
0.8958	High Similarity	NPC473023
0.8944	High Similarity	NPC469579
0.8944	High Similarity	NPC471640
0.8944	High Similarity	NPC471733
0.8944	High Similarity	NPC250755
0.8944	High Similarity	NPC471644
0.8936	High Similarity	NPC99441
0.8921	High Similarity	NPC291454
0.8921	High Similarity	NPC158481
0.8912	High Similarity	NPC91809
0.8905	High Similarity	NPC476389
0.8904	High Similarity	NPC476684
0.8897	High Similarity	NPC14098
0.8897	High Similarity	NPC247477
0.8897	High Similarity	NPC17840
0.8889	High Similarity	NPC473692
0.8881	High Similarity	NPC471639
0.8881	High Similarity	NPC471643
0.8881	High Similarity	NPC95309
0.8873	High Similarity	NPC90411
0.8865	High Similarity	NPC275356
0.8865	High Similarity	NPC247409
0.8859	High Similarity	NPC472890
0.8859	High Similarity	NPC99381
0.8857	High Similarity	NPC301915
0.8857	High Similarity	NPC261292
0.8851	High Similarity	NPC478224
0.8851	High Similarity	NPC115249
0.8851	High Similarity	NPC184284
0.8851	High Similarity	NPC76041
0.8844	High Similarity	NPC469670
0.8844	High Similarity	NPC60413
0.8844	High Similarity	NPC469619
0.8836	High Similarity	NPC221352
0.8819	High Similarity	NPC66404
0.8819	High Similarity	NPC95123
0.8816	High Similarity	NPC298401
0.8811	High Similarity	NPC96692
0.8811	High Similarity	NPC49108
0.8806	High Similarity	NPC262671
0.8806	High Similarity	NPC201728
0.8792	High Similarity	NPC137301
0.8786	High Similarity	NPC50455
0.8784	High Similarity	NPC70016
0.8784	High Similarity	NPC215921
0.8784	High Similarity	NPC240768
0.8784	High Similarity	NPC200773
0.8776	High Similarity	NPC6923
0.8767	High Similarity	NPC471734
0.8759	High Similarity	NPC134621
0.8758	High Similarity	NPC473696
0.8742	High Similarity	NPC472889
0.8742	High Similarity	NPC478225
0.8741	High Similarity	NPC307990
0.8741	High Similarity	NPC16455
0.8733	High Similarity	NPC478221
0.8733	High Similarity	NPC478230
0.8733	High Similarity	NPC170189
0.8733	High Similarity	NPC208173
0.8733	High Similarity	NPC69043
0.8732	High Similarity	NPC471819
0.8732	High Similarity	NPC57380
0.8732	High Similarity	NPC162939
0.8723	High Similarity	NPC472367
0.8723	High Similarity	NPC473391
0.8723	High Similarity	NPC472364
0.8723	High Similarity	NPC476333
0.8716	High Similarity	NPC295036
0.8707	High Similarity	NPC2569
0.8707	High Similarity	NPC172329
0.8705	High Similarity	NPC48036
0.8699	High Similarity	NPC471735
0.8699	High Similarity	NPC237208
0.8699	High Similarity	NPC51513
0.8699	High Similarity	NPC202112
0.8699	High Similarity	NPC163846
0.8699	High Similarity	NPC225173
0.8699	High Similarity	NPC470570
0.869	High Similarity	NPC184702
0.8681	High Similarity	NPC105648
0.8681	High Similarity	NPC82913
0.8675	High Similarity	NPC472050
0.8671	High Similarity	NPC165172
0.8671	High Similarity	NPC156872
0.8667	High Similarity	NPC478231
0.8667	High Similarity	NPC477454
0.8662	High Similarity	NPC126739
0.8662	High Similarity	NPC197666
0.8652	High Similarity	NPC474726
0.8652	High Similarity	NPC472599
0.8652	High Similarity	NPC475955
0.8649	High Similarity	NPC237440
0.8649	High Similarity	NPC77325
0.8649	High Similarity	NPC4423
0.8649	High Similarity	NPC270160
0.8645	High Similarity	NPC173352
0.8645	High Similarity	NPC58653
0.8639	High Similarity	NPC81835
0.8639	High Similarity	NPC137296
0.8639	High Similarity	NPC125801
0.8639	High Similarity	NPC166583
0.8639	High Similarity	NPC53362
0.8639	High Similarity	NPC476463

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 NPC478201 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	939
0.2-0.3	1733
0.3-0.4	2593
0.4-0.5	1938
0.5-0.6	1142
0.6-0.7	383
0.7-0.8	131
0.8-0.85	17
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8865	High Similarity	NPD970	Clinical (unspecified phase)
0.8543	High Similarity	NPD7819	Suspended
0.8503	High Similarity	NPD2533	Approved
0.8503	High Similarity	NPD2532	Approved
0.8503	High Similarity	NPD2534	Approved
0.831	Intermediate Similarity	NPD230	Phase 1
0.8289	Intermediate Similarity	NPD7411	Suspended
0.8264	Intermediate Similarity	NPD1510	Phase 2
0.8239	Intermediate Similarity	NPD1240	Approved
0.8219	Intermediate Similarity	NPD1549	Phase 2
0.8209	Intermediate Similarity	NPD9545	Approved
0.8188	Intermediate Similarity	NPD6799	Approved
0.8151	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8151	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD7075	Discontinued
0.8129	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1607	Approved
0.8108	Intermediate Similarity	NPD3750	Approved
0.8108	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8082	Intermediate Similarity	NPD2796	Approved
0.8065	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.806	Intermediate Similarity	NPD9493	Approved
0.8014	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1934	Approved
0.7987	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD4380	Phase 2
0.7962	Intermediate Similarity	NPD3882	Suspended
0.7959	Intermediate Similarity	NPD1551	Phase 2
0.7959	Intermediate Similarity	NPD2935	Discontinued
0.7937	Intermediate Similarity	NPD6232	Discontinued
0.7919	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD3749	Approved
0.7901	Intermediate Similarity	NPD7473	Discontinued
0.7898	Intermediate Similarity	NPD3817	Phase 2
0.7885	Intermediate Similarity	NPD6801	Discontinued
0.7875	Intermediate Similarity	NPD6959	Discontinued
0.7862	Intermediate Similarity	NPD943	Approved
0.7848	Intermediate Similarity	NPD7768	Phase 2
0.7847	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD2801	Approved
0.7829	Intermediate Similarity	NPD1511	Approved
0.7806	Intermediate Similarity	NPD3226	Approved
0.7799	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD3748	Approved
0.7736	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1512	Approved
0.7724	Intermediate Similarity	NPD3764	Approved
0.7718	Intermediate Similarity	NPD5406	Approved
0.7718	Intermediate Similarity	NPD5404	Approved
0.7718	Intermediate Similarity	NPD5408	Approved
0.7718	Intermediate Similarity	NPD5405	Approved
0.7716	Intermediate Similarity	NPD5711	Approved
0.7716	Intermediate Similarity	NPD5710	Approved
0.7712	Intermediate Similarity	NPD7390	Discontinued
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7677	Intermediate Similarity	NPD5403	Approved
0.7673	Intermediate Similarity	NPD5402	Approved
0.766	Intermediate Similarity	NPD9717	Approved
0.7636	Intermediate Similarity	NPD3818	Discontinued
0.7632	Intermediate Similarity	NPD4628	Phase 3
0.7622	Intermediate Similarity	NPD6166	Phase 2
0.7622	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7054	Approved
0.7566	Intermediate Similarity	NPD1243	Approved
0.7566	Intermediate Similarity	NPD2800	Approved
0.7564	Intermediate Similarity	NPD920	Approved
0.7548	Intermediate Similarity	NPD5401	Approved
0.7545	Intermediate Similarity	NPD7074	Phase 3
0.7545	Intermediate Similarity	NPD7472	Approved
0.7536	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD9269	Phase 2
0.7533	Intermediate Similarity	NPD2799	Discontinued
0.7532	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD6651	Approved
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD9268	Approved
0.75	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7485	Intermediate Similarity	NPD5494	Approved
0.7483	Intermediate Similarity	NPD411	Approved
0.7466	Intermediate Similarity	NPD6832	Phase 2
0.7465	Intermediate Similarity	NPD1201	Approved
0.7463	Intermediate Similarity	NPD74	Approved
0.7463	Intermediate Similarity	NPD9266	Approved
0.7456	Intermediate Similarity	NPD7251	Discontinued
0.7456	Intermediate Similarity	NPD6559	Discontinued
0.745	Intermediate Similarity	NPD447	Suspended
0.7436	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2346	Discontinued
0.7423	Intermediate Similarity	NPD919	Approved
0.7412	Intermediate Similarity	NPD7808	Phase 3
0.7391	Intermediate Similarity	NPD1465	Phase 2
0.7388	Intermediate Similarity	NPD9264	Approved
0.7388	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD9263	Approved
0.7388	Intermediate Similarity	NPD9267	Approved
0.7381	Intermediate Similarity	NPD7286	Phase 2
0.7381	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD1164	Approved
0.7371	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6099	Approved
0.7368	Intermediate Similarity	NPD6100	Approved
0.7365	Intermediate Similarity	NPD3268	Approved
0.7355	Intermediate Similarity	NPD6190	Approved
0.7343	Intermediate Similarity	NPD422	Phase 1
0.7342	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD8150	Discontinued
0.7338	Intermediate Similarity	NPD2654	Approved
0.7333	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2344	Approved
0.7294	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD1247	Approved
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD1019	Discontinued
0.7211	Intermediate Similarity	NPD2798	Approved
0.7203	Intermediate Similarity	NPD4626	Approved
0.719	Intermediate Similarity	NPD7033	Discontinued
0.7172	Intermediate Similarity	NPD1608	Approved
0.7159	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9281	Approved
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7134	Intermediate Similarity	NPD4288	Approved
0.7134	Intermediate Similarity	NPD2309	Approved
0.7133	Intermediate Similarity	NPD2313	Discontinued
0.7133	Intermediate Similarity	NPD5691	Approved
0.7133	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7199	Phase 2
0.7118	Intermediate Similarity	NPD3751	Discontinued
0.7117	Intermediate Similarity	NPD37	Approved
0.711	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6234	Discontinued
0.7101	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD4966	Approved
0.7091	Intermediate Similarity	NPD4967	Phase 2
0.7091	Intermediate Similarity	NPD4965	Approved
0.709	Intermediate Similarity	NPD9261	Approved
0.7088	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD520	Approved
0.7083	Intermediate Similarity	NPD1778	Approved
0.7083	Intermediate Similarity	NPD7229	Phase 3
0.708	Intermediate Similarity	NPD2182	Approved
0.707	Intermediate Similarity	NPD8166	Discontinued
0.707	Intermediate Similarity	NPD7003	Approved
0.7069	Intermediate Similarity	NPD8313	Approved
0.7069	Intermediate Similarity	NPD8312	Approved
0.7063	Intermediate Similarity	NPD6273	Approved
0.7047	Intermediate Similarity	NPD9494	Approved
0.7044	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7458	Discontinued
0.703	Intermediate Similarity	NPD5353	Approved
0.7027	Intermediate Similarity	NPD3266	Approved
0.7027	Intermediate Similarity	NPD3267	Approved
0.7027	Intermediate Similarity	NPD2797	Approved
0.702	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4908	Phase 1
0.7	Intermediate Similarity	NPD6534	Approved
0.7	Intermediate Similarity	NPD6535	Approved
0.6993	Remote Similarity	NPD5124	Phase 1
0.6993	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1471	Phase 3
0.6986	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD3787	Discontinued
0.6982	Remote Similarity	NPD6808	Phase 2
0.6974	Remote Similarity	NPD6663	Approved
0.6973	Remote Similarity	NPD7435	Discontinued
0.6968	Remote Similarity	NPD4308	Phase 3
0.6968	Remote Similarity	NPD8151	Discontinued
0.6966	Remote Similarity	NPD4287	Approved
0.6966	Remote Similarity	NPD17	Approved
0.6959	Remote Similarity	NPD3225	Approved
0.6959	Remote Similarity	NPD1283	Approved
0.6954	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8434	Phase 2
0.6941	Remote Similarity	NPD5242	Approved
0.6939	Remote Similarity	NPD3972	Approved
0.6935	Remote Similarity	NPD8320	Phase 1
0.6935	Remote Similarity	NPD8319	Approved
0.6933	Remote Similarity	NPD5736	Approved
0.6933	Remote Similarity	NPD3455	Phase 2
0.6928	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7177	Discontinued
0.6918	Remote Similarity	NPD3496	Discontinued
0.6908	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1296	Phase 2
0.6902	Remote Similarity	NPD6781	Approved
0.6902	Remote Similarity	NPD6782	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