NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	348.16
Volume:	356.99
LogP:	2.842
LogD:	2.422
LogS:	-3.578
# Rotatable Bonds:	1
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.599
Synthetic Accessibility Score:	4.157
Fsp3:	0.474
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:	-4.767
MDCK Permeability:	2.176403722842224e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.104
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.828
30% Bioavailability (F30%):	0.24

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	92.6355972290039%
Volume Distribution (VD):	0.537
Pgp-substrate:	4.496466636657715%

ADMET: Metabolism

CYP1A2-inhibitor:	0.675
CYP1A2-substrate:	0.131
CYP2C19-inhibitor:	0.194
CYP2C19-substrate:	0.095
CYP2C9-inhibitor:	0.478
CYP2C9-substrate:	0.958
CYP2D6-inhibitor:	0.741
CYP2D6-substrate:	0.237
CYP3A4-inhibitor:	0.542
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	8.829
Half-life (T1/2):	0.913

ADMET: Toxicity

hERG Blockers:	0.061
Human Hepatotoxicity (H-HT):	0.571
Drug-inuced Liver Injury (DILI):	0.891
AMES Toxicity:	0.077
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.964
Skin Sensitization:	0.718
Carcinogencity:	0.657
Eye Corrosion:	0.005
Eye Irritation:	0.1
Respiratory Toxicity:	0.417

Download Data

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

Natural Product: NPC478217

Natural Product ID:	NPC478217
*Common Name:**	4'-hydroxymonocillin IV
IUPAC Name:	(4R,6E,10R)-10,16,18-trihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),6,15,17-tetraene-2,12-dione
Synonyms:
Standard InCHIKey:	BOOGYPBXHOLWJD-FTYDKLPRSA-N
Standard InCHI:	InChI=1S/C18H22O6/c1-11-5-3-2-4-6-13(19)9-14(20)7-12-8-15(21)10-16(22)17(12)18(23)24-11/h2-3,8,10-11,13,19,21-22H,4-7,9H2,1H3/b3-2+/t11-,13-/m1/s1
SMILES:	C[C@@H]1C/C=C/CC[C@H](CC(=O)CC2=C(C(=CC(=C2)O)O)C(=O)O1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	139589761
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 NPC478217 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	318
0.1-0.2	1400
0.2-0.3	3396
0.3-0.4	7627
0.4-0.5	11017
0.5-0.6	3910
0.6-0.7	6723
0.7-0.8	6473
0.8-0.85	1489
0.85-0.9	240
0.9-0.95	84
0.95-1	20

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC313123
0.9853	High Similarity	NPC478202
0.9852	High Similarity	NPC478201
0.9852	High Similarity	NPC472035
0.9776	High Similarity	NPC33144
0.9776	High Similarity	NPC191835
0.9776	High Similarity	NPC478200
0.9701	High Similarity	NPC474771
0.9701	High Similarity	NPC70380
0.9701	High Similarity	NPC149372
0.9701	High Similarity	NPC65837
0.9701	High Similarity	NPC474849
0.9701	High Similarity	NPC178467
0.9638	High Similarity	NPC210966
0.9638	High Similarity	NPC126882
0.9638	High Similarity	NPC478203
0.963	High Similarity	NPC177307
0.963	High Similarity	NPC212693
0.963	High Similarity	NPC475974
0.963	High Similarity	NPC9121
0.963	High Similarity	NPC94248
0.9568	High Similarity	NPC257558
0.9568	High Similarity	NPC472034
0.9556	High Similarity	NPC71256
0.95	High Similarity	NPC472033
0.9489	High Similarity	NPC158472
0.9485	High Similarity	NPC472403
0.9485	High Similarity	NPC472602
0.9433	High Similarity	NPC472036
0.9424	High Similarity	NPC472006
0.942	High Similarity	NPC472603
0.942	High Similarity	NPC158634
0.942	High Similarity	NPC53649
0.942	High Similarity	NPC67650
0.942	High Similarity	NPC1704
0.9416	High Similarity	NPC474655
0.9416	High Similarity	NPC139634
0.9416	High Similarity	NPC105456
0.9403	High Similarity	NPC153783
0.9357	High Similarity	NPC42540
0.9357	High Similarity	NPC151607
0.9353	High Similarity	NPC474385
0.9348	High Similarity	NPC472601
0.9348	High Similarity	NPC472600
0.9338	High Similarity	NPC235115
0.9291	High Similarity	NPC83272
0.9286	High Similarity	NPC354984
0.9286	High Similarity	NPC159721
0.9286	High Similarity	NPC51106
0.9281	High Similarity	NPC475730
0.9281	High Similarity	NPC472605
0.9281	High Similarity	NPC472604
0.9281	High Similarity	NPC244923
0.9275	High Similarity	NPC52358
0.9275	High Similarity	NPC268052
0.9275	High Similarity	NPC32360
0.9275	High Similarity	NPC92655
0.927	High Similarity	NPC194579
0.9265	High Similarity	NPC27407
0.9259	High Similarity	NPC43627
0.9254	High Similarity	NPC219892
0.9254	High Similarity	NPC189823
0.9231	High Similarity	NPC240622
0.9231	High Similarity	NPC471641
0.9231	High Similarity	NPC240253
0.9231	High Similarity	NPC471642
0.9225	High Similarity	NPC107625
0.922	High Similarity	NPC210425
0.922	High Similarity	NPC86373
0.922	High Similarity	NPC280404
0.922	High Similarity	NPC277426
0.9209	High Similarity	NPC155205
0.9191	High Similarity	NPC474097
0.9161	High Similarity	NPC210320
0.9155	High Similarity	NPC312789
0.9149	High Similarity	NPC471731
0.9149	High Similarity	NPC472610
0.9149	High Similarity	NPC469542
0.9143	High Similarity	NPC37530
0.9137	High Similarity	NPC88269
0.913	High Similarity	NPC135837
0.9124	High Similarity	NPC142027
0.9103	High Similarity	NPC56204
0.9097	High Similarity	NPC73411
0.9097	High Similarity	NPC215711
0.9091	High Similarity	NPC473023
0.9078	High Similarity	NPC250755
0.9078	High Similarity	NPC469579
0.9078	High Similarity	NPC471733
0.9071	High Similarity	NPC99441
0.9065	High Similarity	NPC221104
0.9058	High Similarity	NPC291454
0.9058	High Similarity	NPC158481
0.9051	High Similarity	NPC175943
0.9044	High Similarity	NPC476389
0.9037	High Similarity	NPC247477
0.9037	High Similarity	NPC17840
0.903	High Similarity	NPC41263
0.9028	High Similarity	NPC14098
0.9021	High Similarity	NPC473692
0.9014	High Similarity	NPC471643
0.9014	High Similarity	NPC471639
0.9007	High Similarity	NPC470842
0.9	High Similarity	NPC275356
0.8993	High Similarity	NPC301915
0.8993	High Similarity	NPC261292
0.8986	High Similarity	NPC182496
0.8986	High Similarity	NPC180905
0.8973	High Similarity	NPC469670
0.8973	High Similarity	NPC60413
0.8973	High Similarity	NPC469619
0.8973	High Similarity	NPC472891
0.8971	High Similarity	NPC214702
0.8971	High Similarity	NPC470831
0.8966	High Similarity	NPC153417
0.8966	High Similarity	NPC221352
0.8944	High Similarity	NPC471640
0.8944	High Similarity	NPC96692
0.8944	High Similarity	NPC471644
0.8921	High Similarity	NPC50455
0.8912	High Similarity	NPC200773
0.8912	High Similarity	NPC70016
0.8912	High Similarity	NPC240768
0.8912	High Similarity	NPC215921
0.8904	High Similarity	NPC84142
0.8904	High Similarity	NPC6923
0.8904	High Similarity	NPC476684
0.8897	High Similarity	NPC471734
0.8889	High Similarity	NPC134621
0.8873	High Similarity	NPC307990
0.8873	High Similarity	NPC16455
0.8873	High Similarity	NPC90411
0.8865	High Similarity	NPC247409
0.8859	High Similarity	NPC99381
0.8851	High Similarity	NPC478224
0.8851	High Similarity	NPC115249
0.8851	High Similarity	NPC184284
0.8851	High Similarity	NPC76041
0.8844	High Similarity	NPC164762
0.8841	High Similarity	NPC48036
0.8828	High Similarity	NPC237208
0.8828	High Similarity	NPC163846
0.8828	High Similarity	NPC225173
0.8828	High Similarity	NPC471735
0.8819	High Similarity	NPC66404
0.8819	High Similarity	NPC95123
0.8811	High Similarity	NPC82913
0.8811	High Similarity	NPC49108
0.8806	High Similarity	NPC477454
0.8806	High Similarity	NPC262671
0.8806	High Similarity	NPC201728
0.8803	High Similarity	NPC165172
0.8792	High Similarity	NPC137301
0.8786	High Similarity	NPC472599
0.8784	High Similarity	NPC91809
0.8776	High Similarity	NPC4423
0.8776	High Similarity	NPC270160
0.8776	High Similarity	NPC77325
0.8776	High Similarity	NPC237440
0.8767	High Similarity	NPC125801
0.8767	High Similarity	NPC166583
0.8767	High Similarity	NPC53362
0.8767	High Similarity	NPC476463
0.8759	High Similarity	NPC29577
0.8741	High Similarity	NPC473691
0.8741	High Similarity	NPC95309
0.8733	High Similarity	NPC208173
0.8733	High Similarity	NPC478230
0.8733	High Similarity	NPC79998
0.8733	High Similarity	NPC170189
0.8733	High Similarity	NPC472890
0.8733	High Similarity	NPC69043
0.8732	High Similarity	NPC57380
0.8732	High Similarity	NPC162939
0.8732	High Similarity	NPC471819
0.8725	High Similarity	NPC213224
0.8723	High Similarity	NPC245058
0.8716	High Similarity	NPC158866
0.8714	High Similarity	NPC278375
0.8707	High Similarity	NPC2569
0.8707	High Similarity	NPC37139
0.8707	High Similarity	NPC172329
0.8705	High Similarity	NPC37299
0.8705	High Similarity	NPC180261
0.8701	High Similarity	NPC470081
0.8699	High Similarity	NPC202112
0.8699	High Similarity	NPC51513
0.8699	High Similarity	NPC470570
0.8696	High Similarity	NPC7012
0.8693	High Similarity	NPC298401
0.869	High Similarity	NPC184702
0.869	High Similarity	NPC470932
0.8686	High Similarity	NPC92624
0.8681	High Similarity	NPC105648
0.8675	High Similarity	NPC472050
0.8671	High Similarity	NPC168471
0.8667	High Similarity	NPC478231
0.8667	High Similarity	NPC470102
0.8667	High Similarity	NPC275837
0.8667	High Similarity	NPC55092

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 NPC478217 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	932
0.2-0.3	1676
0.3-0.4	2586
0.4-0.5	1973
0.5-0.6	1148
0.6-0.7	409
0.7-0.8	135
0.8-0.85	16
0.85-0.9	5
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)
0.863	High Similarity	NPD2532	Approved
0.863	High Similarity	NPD2534	Approved
0.863	High Similarity	NPD2533	Approved
0.8543	High Similarity	NPD7819	Suspended
0.8289	Intermediate Similarity	NPD7411	Suspended
0.8276	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8264	Intermediate Similarity	NPD1510	Phase 2
0.8247	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1240	Approved
0.8219	Intermediate Similarity	NPD1549	Phase 2
0.8182	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD230	Phase 1
0.8141	Intermediate Similarity	NPD7075	Discontinued
0.8133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1607	Approved
0.8117	Intermediate Similarity	NPD1934	Approved
0.8108	Intermediate Similarity	NPD3750	Approved
0.8082	Intermediate Similarity	NPD2796	Approved
0.8074	Intermediate Similarity	NPD9545	Approved
0.8067	Intermediate Similarity	NPD6799	Approved
0.8065	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD6232	Discontinued
0.8014	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7473	Discontinued
0.7987	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD4380	Phase 2
0.7987	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6959	Discontinued
0.7959	Intermediate Similarity	NPD2935	Discontinued
0.7926	Intermediate Similarity	NPD9493	Approved
0.7919	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD3749	Approved
0.7898	Intermediate Similarity	NPD3817	Phase 2
0.7891	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD6801	Discontinued
0.7862	Intermediate Similarity	NPD943	Approved
0.7848	Intermediate Similarity	NPD7768	Phase 2
0.7848	Intermediate Similarity	NPD3882	Suspended
0.7847	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD1551	Phase 2
0.7834	Intermediate Similarity	NPD2801	Approved
0.7829	Intermediate Similarity	NPD7390	Discontinued
0.7829	Intermediate Similarity	NPD1511	Approved
0.7826	Intermediate Similarity	NPD5711	Approved
0.7826	Intermediate Similarity	NPD5710	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)
0.773	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD6166	Phase 2
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
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7682	Intermediate Similarity	NPD2800	Approved
0.7651	Intermediate Similarity	NPD7074	Phase 3
0.7636	Intermediate Similarity	NPD3818	Discontinued
0.7635	Intermediate Similarity	NPD6651	Approved
0.7632	Intermediate Similarity	NPD4628	Phase 3
0.759	Intermediate Similarity	NPD7054	Approved
0.7589	Intermediate Similarity	NPD1201	Approved
0.7566	Intermediate Similarity	NPD1243	Approved
0.7564	Intermediate Similarity	NPD5403	Approved
0.7564	Intermediate Similarity	NPD920	Approved
0.7562	Intermediate Similarity	NPD5402	Approved
0.7545	Intermediate Similarity	NPD7472	Approved
0.7535	Intermediate Similarity	NPD9717	Approved
0.7533	Intermediate Similarity	NPD2799	Discontinued
0.7532	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1470	Approved
0.75	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD6797	Phase 2
0.7485	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5494	Approved
0.7483	Intermediate Similarity	NPD6100	Approved
0.7483	Intermediate Similarity	NPD3268	Approved
0.7483	Intermediate Similarity	NPD6099	Approved
0.7456	Intermediate Similarity	NPD7251	Discontinued
0.7456	Intermediate Similarity	NPD6559	Discontinued
0.7436	Intermediate Similarity	NPD5401	Approved
0.7436	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD2346	Discontinued
0.7423	Intermediate Similarity	NPD919	Approved
0.7413	Intermediate Similarity	NPD9269	Phase 2
0.7412	Intermediate Similarity	NPD7808	Phase 3
0.741	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1465	Phase 2
0.7381	Intermediate Similarity	NPD7286	Phase 2
0.7379	Intermediate Similarity	NPD1203	Approved
0.7379	Intermediate Similarity	NPD1164	Approved
0.7376	Intermediate Similarity	NPD9268	Approved
0.7371	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD411	Approved
0.7347	Intermediate Similarity	NPD6832	Phase 2
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	NPD74	Approved
0.7333	Intermediate Similarity	NPD9266	Approved
0.7333	Intermediate Similarity	NPD447	Suspended
0.7325	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD4626	Approved
0.732	Intermediate Similarity	NPD2344	Approved
0.7303	Intermediate Similarity	NPD7033	Discontinued
0.7294	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1608	Approved
0.7259	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD9267	Approved
0.7259	Intermediate Similarity	NPD9263	Approved
0.7259	Intermediate Similarity	NPD9264	Approved
0.7254	Intermediate Similarity	NPD5691	Approved
0.725	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD6190	Approved
0.7229	Intermediate Similarity	NPD7199	Phase 2
0.7229	Intermediate Similarity	NPD1247	Approved
0.7222	Intermediate Similarity	NPD37	Approved
0.7219	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6234	Discontinued
0.7211	Intermediate Similarity	NPD2798	Approved
0.7209	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4966	Approved
0.7195	Intermediate Similarity	NPD4965	Approved
0.7195	Intermediate Similarity	NPD4967	Phase 2
0.7186	Intermediate Similarity	NPD7229	Phase 3
0.7159	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD2797	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	NPD4196	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD4908	Phase 1
0.7105	Intermediate Similarity	NPD5124	Phase 1
0.7105	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD1019	Discontinued
0.7088	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6663	Approved
0.7083	Intermediate Similarity	NPD17	Approved
0.7083	Intermediate Similarity	NPD1778	Approved
0.7075	Intermediate Similarity	NPD1283	Approved
0.707	Intermediate Similarity	NPD7003	Approved
0.707	Intermediate Similarity	NPD8166	Discontinued
0.7069	Intermediate Similarity	NPD8312	Approved
0.7069	Intermediate Similarity	NPD8313	Approved
0.7063	Intermediate Similarity	NPD6273	Approved
0.7047	Intermediate Similarity	NPD5736	Approved
0.7039	Intermediate Similarity	NPD4060	Phase 1
0.7037	Intermediate Similarity	NPD7458	Discontinued
0.7021	Intermediate Similarity	NPD9281	Approved
0.702	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1296	Phase 2
0.7018	Intermediate Similarity	NPD3751	Discontinued
0.7018	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD940	Approved
0.7015	Intermediate Similarity	NPD846	Approved
0.7	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6535	Approved
0.7	Intermediate Similarity	NPD6534	Approved
0.6993	Remote Similarity	NPD6355	Discontinued
0.6987	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1471	Phase 3
0.6987	Remote Similarity	NPD6002	Phase 3
0.6987	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6004	Phase 3
0.6987	Remote Similarity	NPD6005	Phase 3
0.6986	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD1610	Phase 2
0.6982	Remote Similarity	NPD3787	Discontinued
0.6982	Remote Similarity	NPD6808	Phase 2
0.6974	Remote Similarity	NPD520	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
0.6963	Remote Similarity	NPD9261	Approved
0.6959	Remote Similarity	NPD3225	Approved
0.6957	Remote Similarity	NPD2182	Approved
0.6954	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4625	Phase 3
0.6954	Remote Similarity	NPD3027	Phase 3
0.6952	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7615	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