NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	398.21
Volume:	429.407
LogP:	3.424
LogD:	2.842
LogS:	-4.426
# Rotatable Bonds:	8
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.509
Synthetic Accessibility Score:	4.399
Fsp3:	0.417
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:	-4.569
MDCK Permeability:	1.780145066732075e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.62
Plasma Protein Binding (PPB):	95.20840454101562%
Volume Distribution (VD):	0.705
Pgp-substrate:	2.6154346466064453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.257
CYP1A2-substrate:	0.248
CYP2C19-inhibitor:	0.326
CYP2C19-substrate:	0.776
CYP2C9-inhibitor:	0.3
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.484
CYP2D6-substrate:	0.535
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.423

ADMET: Excretion

Clearance (CL):	6.202
Half-life (T1/2):	0.298

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.023
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.027
Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.03
Skin Sensitization:	0.173
Carcinogencity:	0.231
Eye Corrosion:	0.003
Eye Irritation:	0.051
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC477534

Natural Product ID:	NPC477534
*Common Name:**	mutisicoumaranone C
IUPAC Name:	2-hydroxy-2-[(2E,6E,9E)-11-hydroxy-3,7,11-trimethyl-8-oxododeca-2,6,9-trienyl]-4-methyl-1-benzofuran-3-one
Synonyms:	Mutisicoumaranone C
Standard InCHIKey:	GVTHSGZHUOJHBB-GCCVESNXSA-N
Standard InCHI:	InChI=1S/C24H30O5/c1-16(8-6-9-17(2)19(25)13-14-23(4,5)27)12-15-24(28)22(26)21-18(3)10-7-11-20(21)29-24/h7,9-14,27-28H,6,8,15H2,1-5H3/b14-13+,16-12+,17-9+
SMILES:	CC1=C2C(=CC=C1)OC(C2=O)(C/C=C(\C)/CC/C=C(\C)/C(=O)/C=C/C(C)(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10363493
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO15444	Mutisia friesiana	Species	Asteraceae	Eukaryota	aerial parts	Jujuy, Departamento de Humahuaca, Argentina	n.a.	PMID[15165137]

☑ 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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	IZ	=	14	mm	PMID[15165137]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10	mm	PMID[15165137]

☑ 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 NPC477534 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	331
0.1-0.2	1508
0.2-0.3	3615
0.3-0.4	9669
0.4-0.5	9277
0.5-0.6	4138
0.6-0.7	8742
0.7-0.8	5310
0.8-0.85	90
0.85-0.9	12
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9692	High Similarity	NPC477536
0.9627	High Similarity	NPC477537
0.9481	High Similarity	NPC477535
0.9242	High Similarity	NPC324488
0.8582	High Similarity	NPC477408
0.8542	High Similarity	NPC469385
0.8514	High Similarity	NPC175617
0.8493	Intermediate Similarity	NPC469425
0.8493	Intermediate Similarity	NPC252208
0.8478	Intermediate Similarity	NPC118253
0.8456	Intermediate Similarity	NPC471349
0.8456	Intermediate Similarity	NPC471347
0.844	Intermediate Similarity	NPC301341
0.8429	Intermediate Similarity	NPC22222
0.8429	Intermediate Similarity	NPC298900
0.8429	Intermediate Similarity	NPC281513
0.8406	Intermediate Similarity	NPC205360
0.8369	Intermediate Similarity	NPC232996
0.8345	Intermediate Similarity	NPC470160
0.8333	Intermediate Similarity	NPC470092
0.8311	Intermediate Similarity	NPC219560
0.831	Intermediate Similarity	NPC284184
0.8298	Intermediate Similarity	NPC217914
0.8273	Intermediate Similarity	NPC141549
0.8273	Intermediate Similarity	NPC7012
0.8261	Intermediate Similarity	NPC473019
0.8255	Intermediate Similarity	NPC471348
0.8255	Intermediate Similarity	NPC226578
0.8255	Intermediate Similarity	NPC228906
0.8255	Intermediate Similarity	NPC469416
0.8248	Intermediate Similarity	NPC470841
0.8235	Intermediate Similarity	NPC224657
0.8231	Intermediate Similarity	NPC473951
0.8231	Intermediate Similarity	NPC71210
0.8231	Intermediate Similarity	NPC47152
0.8222	Intermediate Similarity	NPC93730
0.8219	Intermediate Similarity	NPC471520
0.8201	Intermediate Similarity	NPC278787
0.8201	Intermediate Similarity	NPC7569
0.82	Intermediate Similarity	NPC475717
0.8188	Intermediate Similarity	NPC201419
0.8176	Intermediate Similarity	NPC308799
0.8175	Intermediate Similarity	NPC51037
0.8168	Intermediate Similarity	NPC477453
0.8163	Intermediate Similarity	NPC477409
0.8163	Intermediate Similarity	NPC274085
0.8163	Intermediate Similarity	NPC89664
0.8163	Intermediate Similarity	NPC306816
0.8162	Intermediate Similarity	NPC470163
0.8162	Intermediate Similarity	NPC470162
0.8156	Intermediate Similarity	NPC171968
0.8151	Intermediate Similarity	NPC329493
0.8151	Intermediate Similarity	NPC310128
0.8148	Intermediate Similarity	NPC311219
0.8146	Intermediate Similarity	NPC23668
0.8146	Intermediate Similarity	NPC193976
0.8143	Intermediate Similarity	NPC477412
0.8125	Intermediate Similarity	NPC98395
0.8121	Intermediate Similarity	NPC61284
0.8121	Intermediate Similarity	NPC113428
0.8121	Intermediate Similarity	NPC259632
0.8117	Intermediate Similarity	NPC161650
0.8112	Intermediate Similarity	NPC64157
0.8112	Intermediate Similarity	NPC278832
0.8105	Intermediate Similarity	NPC99199
0.8102	Intermediate Similarity	NPC287473
0.8099	Intermediate Similarity	NPC477210
0.8099	Intermediate Similarity	NPC265793
0.8095	Intermediate Similarity	NPC316691
0.8092	Intermediate Similarity	NPC207624
0.8092	Intermediate Similarity	NPC142308
0.8085	Intermediate Similarity	NPC477406
0.8069	Intermediate Similarity	NPC473988
0.8067	Intermediate Similarity	NPC280025
0.8065	Intermediate Similarity	NPC311574
0.8065	Intermediate Similarity	NPC264932
0.8058	Intermediate Similarity	NPC237225
0.8056	Intermediate Similarity	NPC471542
0.8056	Intermediate Similarity	NPC130976
0.8054	Intermediate Similarity	NPC211565
0.8054	Intermediate Similarity	NPC60389
0.8054	Intermediate Similarity	NPC301949
0.8045	Intermediate Similarity	NPC171023
0.8042	Intermediate Similarity	NPC22644
0.8041	Intermediate Similarity	NPC10302
0.8041	Intermediate Similarity	NPC471600
0.8041	Intermediate Similarity	NPC105381
0.8039	Intermediate Similarity	NPC84721
0.8039	Intermediate Similarity	NPC235333
0.8029	Intermediate Similarity	NPC56332
0.8029	Intermediate Similarity	NPC265910
0.8029	Intermediate Similarity	NPC91475
0.8028	Intermediate Similarity	NPC43627
0.8027	Intermediate Similarity	NPC96692
0.8026	Intermediate Similarity	NPC115324
0.8026	Intermediate Similarity	NPC58668
0.8026	Intermediate Similarity	NPC106372
0.8015	Intermediate Similarity	NPC46634
0.8013	Intermediate Similarity	NPC65775
0.8013	Intermediate Similarity	NPC313368
0.8013	Intermediate Similarity	NPC10027
0.8013	Intermediate Similarity	NPC172687
0.8013	Intermediate Similarity	NPC198927
0.8	Intermediate Similarity	NPC294300
0.8	Intermediate Similarity	NPC476404
0.8	Intermediate Similarity	NPC268360
0.8	Intermediate Similarity	NPC317900
0.8	Intermediate Similarity	NPC210048
0.8	Intermediate Similarity	NPC265181
0.8	Intermediate Similarity	NPC476930
0.7987	Intermediate Similarity	NPC297531
0.7987	Intermediate Similarity	NPC475923
0.7987	Intermediate Similarity	NPC474309
0.7987	Intermediate Similarity	NPC213936
0.7987	Intermediate Similarity	NPC148938
0.7986	Intermediate Similarity	NPC141934
0.7986	Intermediate Similarity	NPC298884
0.7986	Intermediate Similarity	NPC45537
0.7986	Intermediate Similarity	NPC472881
0.7986	Intermediate Similarity	NPC71525
0.7972	Intermediate Similarity	NPC474097
0.7962	Intermediate Similarity	NPC476929
0.7961	Intermediate Similarity	NPC158866
0.7959	Intermediate Similarity	NPC124365
0.7958	Intermediate Similarity	NPC312560
0.7956	Intermediate Similarity	NPC118853
0.7956	Intermediate Similarity	NPC182646
0.7947	Intermediate Similarity	NPC215711
0.7947	Intermediate Similarity	NPC73411
0.7947	Intermediate Similarity	NPC37139
0.7945	Intermediate Similarity	NPC268691
0.7945	Intermediate Similarity	NPC475045
0.7945	Intermediate Similarity	NPC1268
0.7945	Intermediate Similarity	NPC475012
0.7943	Intermediate Similarity	NPC198305
0.7943	Intermediate Similarity	NPC196621
0.7933	Intermediate Similarity	NPC471346
0.7929	Intermediate Similarity	NPC165257
0.7922	Intermediate Similarity	NPC470331
0.7922	Intermediate Similarity	NPC290927
0.7922	Intermediate Similarity	NPC189130
0.7922	Intermediate Similarity	NPC477691
0.7919	Intermediate Similarity	NPC471305
0.7919	Intermediate Similarity	NPC131043
0.7919	Intermediate Similarity	NPC198459
0.7919	Intermediate Similarity	NPC109812
0.7919	Intermediate Similarity	NPC313039
0.7919	Intermediate Similarity	NPC473976
0.7914	Intermediate Similarity	NPC306765
0.7911	Intermediate Similarity	NPC475106
0.7908	Intermediate Similarity	NPC39819
0.7908	Intermediate Similarity	NPC318424
0.7905	Intermediate Similarity	NPC133585
0.7905	Intermediate Similarity	NPC49108
0.7902	Intermediate Similarity	NPC470871
0.7899	Intermediate Similarity	NPC193805
0.7899	Intermediate Similarity	NPC310540
0.7899	Intermediate Similarity	NPC4012
0.7898	Intermediate Similarity	NPC269906
0.7895	Intermediate Similarity	NPC70764
0.7891	Intermediate Similarity	NPC475063
0.7891	Intermediate Similarity	NPC475044
0.7885	Intermediate Similarity	NPC212967
0.7885	Intermediate Similarity	NPC177742
0.7885	Intermediate Similarity	NPC164110
0.7885	Intermediate Similarity	NPC246647
0.7885	Intermediate Similarity	NPC473282
0.7885	Intermediate Similarity	NPC104380
0.7885	Intermediate Similarity	NPC217602
0.7885	Intermediate Similarity	NPC96342
0.7881	Intermediate Similarity	NPC472036
0.7881	Intermediate Similarity	NPC210320
0.7881	Intermediate Similarity	NPC478018
0.7877	Intermediate Similarity	NPC254841
0.7877	Intermediate Similarity	NPC475005
0.7877	Intermediate Similarity	NPC173980
0.7877	Intermediate Similarity	NPC475104
0.7877	Intermediate Similarity	NPC474943
0.7872	Intermediate Similarity	NPC187907
0.7872	Intermediate Similarity	NPC939
0.7871	Intermediate Similarity	NPC99381
0.7871	Intermediate Similarity	NPC56786
0.7871	Intermediate Similarity	NPC80534
0.7868	Intermediate Similarity	NPC272454
0.7868	Intermediate Similarity	NPC244994
0.7868	Intermediate Similarity	NPC179092
0.7868	Intermediate Similarity	NPC159760
0.7868	Intermediate Similarity	NPC301987
0.7868	Intermediate Similarity	NPC35856
0.7868	Intermediate Similarity	NPC178395
0.7868	Intermediate Similarity	NPC222876
0.7868	Intermediate Similarity	NPC26433
0.7868	Intermediate Similarity	NPC115188
0.7868	Intermediate Similarity	NPC292665
0.7867	Intermediate Similarity	NPC134621
0.7867	Intermediate Similarity	NPC312789
0.7867	Intermediate Similarity	NPC98926
0.7867	Intermediate Similarity	NPC472034
0.7867	Intermediate Similarity	NPC478019
0.7867	Intermediate Similarity	NPC29577

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 NPC477534 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	971
0.2-0.3	1511
0.3-0.4	2498
0.4-0.5	2053
0.5-0.6	1199
0.6-0.7	492
0.7-0.8	120
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.838	Intermediate Similarity	NPD2346	Discontinued
0.8309	Intermediate Similarity	NPD2798	Approved
0.8148	Intermediate Similarity	NPD9717	Approved
0.8112	Intermediate Similarity	NPD2799	Discontinued
0.8071	Intermediate Similarity	NPD2313	Discontinued
0.8028	Intermediate Similarity	NPD447	Suspended
0.8013	Intermediate Similarity	NPD3226	Approved
0.8	Intermediate Similarity	NPD1471	Phase 3
0.8	Intermediate Similarity	NPD2344	Approved
0.7943	Intermediate Similarity	NPD411	Approved
0.7931	Intermediate Similarity	NPD2935	Discontinued
0.7842	Intermediate Similarity	NPD1203	Approved
0.7785	Intermediate Similarity	NPD2309	Approved
0.7748	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD3882	Suspended
0.7692	Intermediate Similarity	NPD7819	Suspended
0.7681	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD6832	Phase 2
0.7655	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2533	Approved
0.7632	Intermediate Similarity	NPD2534	Approved
0.7632	Intermediate Similarity	NPD2532	Approved
0.763	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4308	Phase 3
0.76	Intermediate Similarity	NPD3750	Approved
0.7589	Intermediate Similarity	NPD2797	Approved
0.7584	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD3268	Approved
0.7566	Intermediate Similarity	NPD6799	Approved
0.7547	Intermediate Similarity	NPD3749	Approved
0.7535	Intermediate Similarity	NPD1019	Discontinued
0.7534	Intermediate Similarity	NPD6355	Discontinued
0.7532	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD9493	Approved
0.7483	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD3496	Discontinued
0.7468	Intermediate Similarity	NPD1512	Approved
0.7468	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4060	Phase 1
0.7465	Intermediate Similarity	NPD1470	Approved
0.7448	Intermediate Similarity	NPD3764	Approved
0.7438	Intermediate Similarity	NPD7075	Discontinued
0.7436	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1201	Approved
0.7426	Intermediate Similarity	NPD6671	Approved
0.7421	Intermediate Similarity	NPD3817	Phase 2
0.7419	Intermediate Similarity	NPD5403	Approved
0.7417	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD2800	Approved
0.7415	Intermediate Similarity	NPD1933	Approved
0.741	Intermediate Similarity	NPD4626	Approved
0.7403	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1876	Approved
0.7394	Intermediate Similarity	NPD3818	Discontinued
0.7383	Intermediate Similarity	NPD3748	Approved
0.7379	Intermediate Similarity	NPD7095	Approved
0.7376	Intermediate Similarity	NPD1608	Approved
0.7368	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD6273	Approved
0.7355	Intermediate Similarity	NPD5049	Phase 3
0.7353	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1549	Phase 2
0.7347	Intermediate Similarity	NPD4307	Phase 2
0.7347	Intermediate Similarity	NPD1240	Approved
0.7338	Intermediate Similarity	NPD1511	Approved
0.7333	Intermediate Similarity	NPD2796	Approved
0.7333	Intermediate Similarity	NPD1551	Phase 2
0.7329	Intermediate Similarity	NPD6798	Discontinued
0.7329	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD6559	Discontinued
0.732	Intermediate Similarity	NPD2354	Approved
0.7296	Intermediate Similarity	NPD6844	Discontinued
0.7296	Intermediate Similarity	NPD6801	Discontinued
0.7296	Intermediate Similarity	NPD1934	Approved
0.729	Intermediate Similarity	NPD5401	Approved
0.7289	Intermediate Similarity	NPD3751	Discontinued
0.7285	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1241	Discontinued
0.7273	Intermediate Similarity	NPD6696	Suspended
0.7267	Intermediate Similarity	NPD1510	Phase 2
0.7262	Intermediate Similarity	NPD6797	Phase 2
0.7255	Intermediate Similarity	NPD7003	Approved
0.7255	Intermediate Similarity	NPD4628	Phase 3
0.725	Intermediate Similarity	NPD2801	Approved
0.7248	Intermediate Similarity	NPD1607	Approved
0.7246	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD8313	Approved
0.7235	Intermediate Similarity	NPD8312	Approved
0.7233	Intermediate Similarity	NPD7411	Suspended
0.7222	Intermediate Similarity	NPD3267	Approved
0.7222	Intermediate Similarity	NPD3266	Approved
0.7219	Intermediate Similarity	NPD7251	Discontinued
0.7219	Intermediate Similarity	NPD6099	Approved
0.7219	Intermediate Similarity	NPD6100	Approved
0.7214	Intermediate Similarity	NPD5691	Approved
0.7205	Intermediate Similarity	NPD2296	Approved
0.7195	Intermediate Similarity	NPD6959	Discontinued
0.719	Intermediate Similarity	NPD1243	Approved
0.7178	Intermediate Similarity	NPD919	Approved
0.7176	Intermediate Similarity	NPD7808	Phase 3
0.7172	Intermediate Similarity	NPD5647	Approved
0.7171	Intermediate Similarity	NPD6005	Phase 3
0.7171	Intermediate Similarity	NPD6004	Phase 3
0.7171	Intermediate Similarity	NPD5762	Approved
0.7171	Intermediate Similarity	NPD5763	Approved
0.7171	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2353	Approved
0.7171	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6002	Phase 3
0.7169	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6166	Phase 2
0.7163	Intermediate Similarity	NPD1778	Approved
0.7163	Intermediate Similarity	NPD17	Approved
0.7162	Intermediate Similarity	NPD8032	Phase 2
0.7161	Intermediate Similarity	NPD3300	Phase 2
0.716	Intermediate Similarity	NPD7768	Phase 2
0.7153	Intermediate Similarity	NPD1283	Approved
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7152	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3787	Discontinued
0.7134	Intermediate Similarity	NPD5494	Approved
0.7133	Intermediate Similarity	NPD3972	Approved
0.7115	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3926	Phase 2
0.7107	Intermediate Similarity	NPD2651	Approved
0.7107	Intermediate Similarity	NPD7458	Discontinued
0.7107	Intermediate Similarity	NPD2649	Approved
0.7105	Intermediate Similarity	NPD4477	Approved
0.7105	Intermediate Similarity	NPD4476	Approved
0.7101	Intermediate Similarity	NPD7074	Phase 3
0.7099	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3887	Approved
0.7092	Intermediate Similarity	NPD1651	Approved
0.7091	Intermediate Similarity	NPD1247	Approved
0.709	Intermediate Similarity	NPD9264	Approved
0.709	Intermediate Similarity	NPD9267	Approved
0.709	Intermediate Similarity	NPD9263	Approved
0.7089	Intermediate Similarity	NPD920	Approved
0.7076	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD4662	Approved
0.707	Intermediate Similarity	NPD4661	Approved
0.7063	Intermediate Similarity	NPD4380	Phase 2
0.7063	Intermediate Similarity	NPD1611	Approved
0.7059	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6232	Discontinued
0.7047	Intermediate Similarity	NPD6233	Phase 2
0.7041	Intermediate Similarity	NPD7054	Approved
0.7037	Intermediate Similarity	NPD9266	Approved
0.7037	Intermediate Similarity	NPD74	Approved
0.7027	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD7473	Discontinued
0.702	Intermediate Similarity	NPD6653	Approved
0.7014	Intermediate Similarity	NPD1481	Phase 2
0.7013	Intermediate Similarity	NPD2897	Discontinued
0.7011	Intermediate Similarity	NPD8434	Phase 2
0.7006	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7472	Approved
0.7	Intermediate Similarity	NPD2979	Phase 3
0.6994	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD5404	Approved
0.6993	Remote Similarity	NPD5406	Approved
0.6993	Remote Similarity	NPD5408	Approved
0.6993	Remote Similarity	NPD5405	Approved
0.6975	Remote Similarity	NPD6279	Approved
0.6975	Remote Similarity	NPD6280	Approved
0.6972	Remote Similarity	NPD5585	Approved
0.6964	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7028	Phase 2
0.6946	Remote Similarity	NPD5711	Approved
0.6946	Remote Similarity	NPD5710	Approved
0.6944	Remote Similarity	NPD1281	Approved
0.6944	Remote Similarity	NPD1535	Discovery
0.6943	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5844	Phase 1
0.6937	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4062	Phase 3
0.6932	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD709	Approved
0.6928	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3225	Approved
0.6913	Remote Similarity	NPD4625	Phase 3
0.6912	Remote Similarity	NPD2182	Approved
0.6906	Remote Similarity	NPD1398	Phase 1
0.6903	Remote Similarity	NPD2424	Discontinued
0.6901	Remote Similarity	NPD9545	Approved
0.6892	Remote Similarity	NPD1712	Approved
0.6892	Remote Similarity	NPD9494	Approved
0.689	Remote Similarity	NPD7318	Phase 3
0.6884	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7177	Discontinued

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