NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	470.19
Volume:	461.416
LogP:	2.573
LogD:	1.699
LogS:	-4.394
# Rotatable Bonds:	2
TPSA:	115.57
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	5.894
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.38
MDCK Permeability:	1.628651807550341e-05
Pgp-inhibitor:	0.991
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	0.804

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.87
Plasma Protein Binding (PPB):	77.37726593017578%
Volume Distribution (VD):	1.53
Pgp-substrate:	19.692472457885742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.79
CYP2C9-inhibitor:	0.316
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.69
CYP3A4-substrate:	0.656

ADMET: Excretion

Clearance (CL):	8.233
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.379
Drug-inuced Liver Injury (DILI):	0.216
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.98
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.175
Carcinogencity:	0.375
Eye Corrosion:	0.038
Eye Irritation:	0.12
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC476860

Natural Product ID:	NPC476860
*Common Name:**	(1R,2R,4S,7S,8S,10S,15R,16R,19R)-7-(furan-3-yl)-16-(2-hydroxypropan-2-yl)-1,8,15-trimethyl-3,6,11-trioxapentacyclo[8.8.1.02,4.02,8.015,19]nonadec-13-ene-5,12,18-trione
IUPAC Name:	(1R,2R,4S,7S,8S,10S,15R,16R,19R)-7-(furan-3-yl)-16-(2-hydroxypropan-2-yl)-1,8,15-trimethyl-3,6,11-trioxapentacyclo[8.8.1.02,4.02,8.015,19]nonadec-13-ene-5,12,18-trione
Synonyms:
Standard InCHIKey:	JDBBJFOPZDNBDA-CHALWBKJSA-N
Standard InCHI:	InChI=1S/C26H30O8/c1-22(2,30)15-10-16(27)25(5)18-14(32-17(28)6-8-23(15,18)3)11-24(4)19(13-7-9-31-12-13)33-21(29)20-26(24,25)34-20/h6-9,12,14-15,18-20,30H,10-11H2,1-5H3/t14-,15-,18+,19-,20+,23-,24-,25+,26+/m0/s1
SMILES:	C[C@@]12C[C@H]3[C@@H]4[C@@](C=CC(=O)O3)([C@@H](CC(=O)[C@]4([C@@]15[C@H](O5)C(=O)O[C@H]2C6=COC=C6)C)C(C)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90670774
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO33678	Clausena emarginata	Species	Rutaceae	Eukaryota	stems	Xishuangbanna, Yunnan Province, China	2010-AUG	PMID[24593150]

☑ 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	5

Activity Type	# Activity
Cell Line	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT1820	Cell Line	NCI-H1650	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT146	Cell Line	SK-OV-3	Homo sapiens	IC50	>	10000	nM	PMID[24593150]
NPT2	Others	Unspecified		IC50	>	10000	nM	PMID[24593150]

☑ 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 NPC476860 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	364
0.1-0.2	1501
0.2-0.3	3315
0.3-0.4	5929
0.4-0.5	10552
0.5-0.6	10098
0.6-0.7	9055
0.7-0.8	1475
0.8-0.85	255
0.85-0.9	94
0.9-0.95	43
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
0.9935	High Similarity	NPC23387
0.9744	High Similarity	NPC476853
0.9742	High Similarity	NPC476858
0.9742	High Similarity	NPC476857
0.9742	High Similarity	NPC476856
0.9675	High Similarity	NPC25255
0.9618	High Similarity	NPC476861
0.9618	High Similarity	NPC476850
0.9613	High Similarity	NPC193798
0.9608	High Similarity	NPC263265
0.949	High Similarity	NPC123088
0.9484	High Similarity	NPC237155
0.9481	High Similarity	NPC126723
0.9427	High Similarity	NPC234660
0.9427	High Similarity	NPC51568
0.9423	High Similarity	NPC472653
0.9371	High Similarity	NPC472775
0.9371	High Similarity	NPC173516
0.9371	High Similarity	NPC472774
0.9371	High Similarity	NPC472282
0.9363	High Similarity	NPC5079
0.9363	High Similarity	NPC470939
0.9359	High Similarity	NPC475295
0.9359	High Similarity	NPC477403
0.9359	High Similarity	NPC473473
0.9355	High Similarity	NPC60973
0.9313	High Similarity	NPC160651
0.9313	High Similarity	NPC471397
0.9304	High Similarity	NPC134254
0.9304	High Similarity	NPC302369
0.9304	High Similarity	NPC39986
0.9304	High Similarity	NPC292389
0.9304	High Similarity	NPC477405
0.9304	High Similarity	NPC469338
0.9299	High Similarity	NPC335761
0.9299	High Similarity	NPC305016
0.9295	High Similarity	NPC286722
0.925	High Similarity	NPC472651
0.9245	High Similarity	NPC470940
0.9245	High Similarity	NPC469849
0.9245	High Similarity	NPC276551
0.9241	High Similarity	NPC472771
0.9241	High Similarity	NPC329938
0.9241	High Similarity	NPC117986
0.9241	High Similarity	NPC96443
0.9241	High Similarity	NPC69028
0.9241	High Similarity	NPC290400
0.9231	High Similarity	NPC107646
0.9231	High Similarity	NPC209364
0.9193	High Similarity	NPC472652
0.9187	High Similarity	NPC470875
0.9182	High Similarity	NPC472773
0.9177	High Similarity	NPC477402
0.9177	High Similarity	NPC475381
0.9172	High Similarity	NPC472283
0.9172	High Similarity	NPC472772
0.913	High Similarity	NPC473753
0.913	High Similarity	NPC473766
0.9125	High Similarity	NPC271657
0.9119	High Similarity	NPC263432
0.9119	High Similarity	NPC82851
0.9119	High Similarity	NPC149896
0.9119	High Similarity	NPC18347
0.9074	High Similarity	NPC271235
0.9051	High Similarity	NPC299038
0.9051	High Similarity	NPC45101
0.9051	High Similarity	NPC249021
0.9051	High Similarity	NPC187149
0.9051	High Similarity	NPC167142
0.9045	High Similarity	NPC264943
0.9045	High Similarity	NPC214541
0.9045	High Similarity	NPC469336
0.9045	High Similarity	NPC44675
0.9045	High Similarity	NPC469850
0.9038	High Similarity	NPC75906
0.902	High Similarity	NPC262198
0.8994	High Similarity	NPC475967
0.8987	High Similarity	NPC469485
0.8981	High Similarity	NPC178932
0.8981	High Similarity	NPC57998
0.8944	High Similarity	NPC419
0.8944	High Similarity	NPC476197
0.8944	High Similarity	NPC469846
0.8938	High Similarity	NPC191828
0.8931	High Similarity	NPC36655
0.8931	High Similarity	NPC261597
0.8931	High Similarity	NPC173544
0.891	High Similarity	NPC196864
0.891	High Similarity	NPC469335
0.891	High Similarity	NPC477404
0.891	High Similarity	NPC159927
0.8882	High Similarity	NPC200782
0.8875	High Similarity	NPC473368
0.8861	High Similarity	NPC282445
0.8854	High Similarity	NPC18135
0.8839	High Similarity	NPC221809
0.8834	High Similarity	NPC475779
0.8834	High Similarity	NPC478178
0.8827	High Similarity	NPC224394
0.8827	High Similarity	NPC663
0.8805	High Similarity	NPC281258
0.8805	High Similarity	NPC476262
0.8802	High Similarity	NPC262386
0.8797	High Similarity	NPC476201
0.8797	High Similarity	NPC268905
0.8797	High Similarity	NPC469503
0.879	High Similarity	NPC46551
0.879	High Similarity	NPC476122
0.8788	High Similarity	NPC470995
0.8766	High Similarity	NPC86935
0.8765	High Similarity	NPC472668
0.8765	High Similarity	NPC197596
0.875	High Similarity	NPC478177
0.8735	High Similarity	NPC159232
0.872	High Similarity	NPC121995
0.872	High Similarity	NPC149945
0.8718	High Similarity	NPC255414
0.8718	High Similarity	NPC470941
0.8713	High Similarity	NPC247563
0.8713	High Similarity	NPC105395
0.8713	High Similarity	NPC242068
0.8704	High Similarity	NPC470789
0.8704	High Similarity	NPC287559
0.8688	High Similarity	NPC75310
0.8683	High Similarity	NPC469848
0.8679	High Similarity	NPC44577
0.8675	High Similarity	NPC82602
0.8675	High Similarity	NPC302392
0.8667	High Similarity	NPC270312
0.8667	High Similarity	NPC476224
0.8667	High Similarity	NPC478179
0.8667	High Similarity	NPC472764
0.8659	High Similarity	NPC56358
0.8659	High Similarity	NPC470182
0.865	High Similarity	NPC18986
0.865	High Similarity	NPC472767
0.865	High Similarity	NPC471166
0.865	High Similarity	NPC471167
0.865	High Similarity	NPC6326
0.865	High Similarity	NPC188649
0.865	High Similarity	NPC207978
0.8645	High Similarity	NPC476944
0.8645	High Similarity	NPC251865
0.8642	High Similarity	NPC307383
0.8636	High Similarity	NPC121158
0.8631	High Similarity	NPC236004
0.8631	High Similarity	NPC471437
0.8625	High Similarity	NPC30222
0.8623	High Similarity	NPC169299
0.8623	High Similarity	NPC285227
0.8623	High Similarity	NPC160818
0.8614	High Similarity	NPC472766
0.8614	High Similarity	NPC472765
0.8608	High Similarity	NPC69647
0.8608	High Similarity	NPC125182
0.8608	High Similarity	NPC195325
0.8606	High Similarity	NPC472141
0.8606	High Similarity	NPC93172
0.8606	High Similarity	NPC97574
0.8598	High Similarity	NPC88841
0.8598	High Similarity	NPC471168
0.8598	High Similarity	NPC472669
0.8598	High Similarity	NPC288602
0.8598	High Similarity	NPC472139
0.8581	High Similarity	NPC243577
0.858	High Similarity	NPC195954
0.8571	High Similarity	NPC35000
0.8562	High Similarity	NPC475777
0.8553	High Similarity	NPC156189
0.8537	High Similarity	NPC211777
0.8537	High Similarity	NPC68848
0.8535	High Similarity	NPC346
0.8521	High Similarity	NPC471632
0.8521	High Similarity	NPC94763
0.8519	High Similarity	NPC204663
0.8519	High Similarity	NPC41880
0.8509	High Similarity	NPC114880
0.85	High Similarity	NPC272590
0.8497	Intermediate Similarity	NPC476943
0.8491	Intermediate Similarity	NPC211625
0.8491	Intermediate Similarity	NPC472654
0.8485	Intermediate Similarity	NPC198047
0.8485	Intermediate Similarity	NPC285567
0.8485	Intermediate Similarity	NPC165218
0.8481	Intermediate Similarity	NPC250228
0.8466	Intermediate Similarity	NPC88007
0.8466	Intermediate Similarity	NPC472776
0.8466	Intermediate Similarity	NPC195131
0.8466	Intermediate Similarity	NPC81405
0.8466	Intermediate Similarity	NPC472778
0.8466	Intermediate Similarity	NPC472777
0.8462	Intermediate Similarity	NPC267632
0.8457	Intermediate Similarity	NPC92979
0.8452	Intermediate Similarity	NPC472659
0.8447	Intermediate Similarity	NPC147168
0.8434	Intermediate Similarity	NPC146991
0.8434	Intermediate Similarity	NPC261184
0.843	Intermediate Similarity	NPC470938
0.8428	Intermediate Similarity	NPC19747
0.8421	Intermediate Similarity	NPC472665

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 NPC476860 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	1061
0.2-0.3	2200
0.3-0.4	2655
0.4-0.5	1838
0.5-0.6	812
0.6-0.7	250
0.7-0.8	20
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD8434	Phase 2
0.8253	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD5761	Phase 2
0.8232	Intermediate Similarity	NPD5760	Phase 2
0.7841	Intermediate Similarity	NPD6764	Approved
0.7841	Intermediate Similarity	NPD6765	Approved
0.7667	Intermediate Similarity	NPD6785	Approved
0.7667	Intermediate Similarity	NPD6784	Approved
0.7588	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7075	Discontinued
0.7515	Intermediate Similarity	NPD6599	Discontinued
0.7384	Intermediate Similarity	NPD7819	Suspended
0.7348	Intermediate Similarity	NPD6559	Discontinued
0.733	Intermediate Similarity	NPD1247	Approved
0.7326	Intermediate Similarity	NPD6801	Discontinued
0.7317	Intermediate Similarity	NPD1471	Phase 3
0.7289	Intermediate Similarity	NPD4628	Phase 3
0.7283	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5494	Approved
0.7273	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7411	Suspended
0.7262	Intermediate Similarity	NPD6799	Approved
0.7251	Intermediate Similarity	NPD3226	Approved
0.7241	Intermediate Similarity	NPD5402	Approved
0.7241	Intermediate Similarity	NPD3817	Phase 2
0.7216	Intermediate Similarity	NPD919	Approved
0.7164	Intermediate Similarity	NPD8404	Phase 2
0.7159	Intermediate Similarity	NPD3749	Approved
0.7143	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD920	Approved
0.7127	Intermediate Similarity	NPD3751	Discontinued
0.7126	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3882	Suspended
0.7095	Intermediate Similarity	NPD3787	Discontinued
0.7088	Intermediate Similarity	NPD5844	Phase 1
0.7035	Intermediate Similarity	NPD5403	Approved
0.7027	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5401	Approved
0.7017	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4380	Phase 2
0.7006	Intermediate Similarity	NPD2346	Discontinued
0.7006	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2799	Discontinued
0.6978	Remote Similarity	NPD7473	Discontinued
0.6968	Remote Similarity	NPD8150	Discontinued
0.6966	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.694	Remote Similarity	NPD3818	Discontinued
0.694	Remote Similarity	NPD7799	Discontinued
0.6932	Remote Similarity	NPD1934	Approved
0.6923	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6166	Phase 2
0.6923	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2533	Approved
0.6919	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2532	Approved
0.6919	Remote Similarity	NPD2534	Approved
0.6906	Remote Similarity	NPD6232	Discontinued
0.6904	Remote Similarity	NPD7435	Discontinued
0.6901	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD7236	Approved
0.6898	Remote Similarity	NPD8313	Approved
0.6898	Remote Similarity	NPD8312	Approved
0.6882	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6273	Approved
0.6868	Remote Similarity	NPD3926	Phase 2
0.6864	Remote Similarity	NPD1549	Phase 2
0.6862	Remote Similarity	NPD8407	Phase 2
0.6851	Remote Similarity	NPD8127	Discontinued
0.6851	Remote Similarity	NPD6959	Discontinued
0.6848	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2796	Approved
0.6828	Remote Similarity	NPD6797	Phase 2
0.6807	Remote Similarity	NPD6355	Discontinued
0.6805	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7239	Suspended
0.6798	Remote Similarity	NPD2801	Approved
0.6791	Remote Similarity	NPD8368	Discontinued
0.6791	Remote Similarity	NPD7251	Discontinued
0.6786	Remote Similarity	NPD8285	Discontinued
0.6776	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7458	Discontinued
0.6755	Remote Similarity	NPD7808	Phase 3
0.6751	Remote Similarity	NPD6778	Approved
0.6751	Remote Similarity	NPD6776	Approved
0.6751	Remote Similarity	NPD6781	Approved
0.6751	Remote Similarity	NPD6780	Approved
0.6751	Remote Similarity	NPD6779	Approved
0.6751	Remote Similarity	NPD6782	Approved
0.6751	Remote Similarity	NPD6777	Approved
0.6746	Remote Similarity	NPD6100	Approved
0.6746	Remote Similarity	NPD6099	Approved
0.6746	Remote Similarity	NPD2935	Discontinued
0.6746	Remote Similarity	NPD1551	Phase 2
0.6742	Remote Similarity	NPD37	Approved
0.6727	Remote Similarity	NPD3268	Approved
0.6727	Remote Similarity	NPD2313	Discontinued
0.6725	Remote Similarity	NPD2800	Approved
0.6725	Remote Similarity	NPD1243	Approved
0.6724	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD4966	Approved
0.6722	Remote Similarity	NPD4965	Approved
0.6722	Remote Similarity	NPD4967	Phase 2
0.6706	Remote Similarity	NPD2344	Approved
0.6702	Remote Similarity	NPD7685	Pre-registration
0.67	Remote Similarity	NPD7874	Approved
0.67	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7907	Approved
0.6687	Remote Similarity	NPD6233	Phase 2
0.6686	Remote Similarity	NPD3750	Approved
0.6686	Remote Similarity	NPD7033	Discontinued
0.6684	Remote Similarity	NPD7074	Phase 3
0.6683	Remote Similarity	NPD4111	Phase 1
0.6667	Remote Similarity	NPD4107	Approved
0.6667	Remote Similarity	NPD970	Clinical (unspecified phase)
0.665	Remote Similarity	NPD7696	Phase 3
0.665	Remote Similarity	NPD7698	Approved
0.665	Remote Similarity	NPD7697	Approved
0.6649	Remote Similarity	NPD2403	Approved
0.6648	Remote Similarity	NPD6234	Discontinued
0.6648	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD6190	Approved
0.6647	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3887	Approved
0.6635	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD7054	Approved
0.663	Remote Similarity	NPD6808	Phase 2
0.663	Remote Similarity	NPD7768	Phase 2
0.6627	Remote Similarity	NPD6798	Discontinued
0.6617	Remote Similarity	NPD7871	Phase 2
0.6617	Remote Similarity	NPD7870	Phase 2
0.6611	Remote Similarity	NPD1465	Phase 2
0.6608	Remote Similarity	NPD5763	Approved
0.6608	Remote Similarity	NPD5762	Approved
0.6606	Remote Similarity	NPD6832	Phase 2
0.6603	Remote Similarity	NPD4665	Approved
0.6596	Remote Similarity	NPD7472	Approved
0.6591	Remote Similarity	NPD1512	Approved
0.659	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3748	Approved
0.6588	Remote Similarity	NPD1510	Phase 2
0.6576	Remote Similarity	NPD7199	Phase 2
0.6566	Remote Similarity	NPD7095	Approved
0.6552	Remote Similarity	NPD2354	Approved
0.6552	Remote Similarity	NPD2309	Approved
0.655	Remote Similarity	NPD4482	Phase 3
0.6546	Remote Similarity	NPD8435	Approved
0.6543	Remote Similarity	NPD1608	Approved
0.6541	Remote Similarity	NPD5711	Approved
0.6541	Remote Similarity	NPD5710	Approved
0.6541	Remote Similarity	NPD7229	Phase 3
0.6538	Remote Similarity	NPD7057	Phase 3
0.6538	Remote Similarity	NPD7058	Phase 2
0.6535	Remote Similarity	NPD8319	Approved
0.6535	Remote Similarity	NPD8320	Phase 1
0.6529	Remote Similarity	NPD7097	Phase 1
0.6527	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD3764	Approved
0.6524	Remote Similarity	NPD3266	Approved
0.6524	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD3267	Approved
0.652	Remote Similarity	NPD7701	Phase 2
0.6517	Remote Similarity	NPD3057	Approved
0.6509	Remote Similarity	NPD447	Suspended
0.6505	Remote Similarity	NPD7801	Approved
0.65	Remote Similarity	NPD4580	Approved
0.6497	Remote Similarity	NPD6535	Approved
0.6497	Remote Similarity	NPD6534	Approved
0.6497	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD4110	Phase 3
0.6494	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7003	Approved
0.6491	Remote Similarity	NPD4308	Phase 3
0.6489	Remote Similarity	NPD7228	Approved
0.6485	Remote Similarity	NPD7497	Discontinued
0.6477	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD1511	Approved
0.6474	Remote Similarity	NPD5953	Discontinued
0.6471	Remote Similarity	NPD1607	Approved
0.6462	Remote Similarity	NPD8360	Approved
0.6462	Remote Similarity	NPD8361	Approved
0.645	Remote Similarity	NPD1240	Approved
0.645	Remote Similarity	NPD4060	Phase 1
0.6443	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD3533	Approved
0.6436	Remote Similarity	NPD2972	Approved
0.6432	Remote Similarity	NPD2975	Approved
0.6432	Remote Similarity	NPD2974	Approved
0.6432	Remote Similarity	NPD2973	Approved
0.6432	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8455	Phase 2

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