NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	260.1
Volume:	264.305
LogP:	1.735
LogD:	1.813
LogS:	-3.602
# Rotatable Bonds:	0
TPSA:	64.35
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.67
Synthetic Accessibility Score:	4.408
Fsp3:	0.533
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.834
MDCK Permeability:	2.540893001423683e-05
Pgp-inhibitor:	0.106
Pgp-substrate:	0.143
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.029

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.357
Plasma Protein Binding (PPB):	85.10736083984375%
Volume Distribution (VD):	0.81
Pgp-substrate:	17.213354110717773%

ADMET: Metabolism

CYP1A2-inhibitor:	0.38
CYP1A2-substrate:	0.523
CYP2C19-inhibitor:	0.36
CYP2C19-substrate:	0.631
CYP2C9-inhibitor:	0.245
CYP2C9-substrate:	0.126
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.396
CYP3A4-inhibitor:	0.547
CYP3A4-substrate:	0.333

ADMET: Excretion

Clearance (CL):	10.181
Half-life (T1/2):	0.708

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.916
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.889
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.402
Carcinogencity:	0.654
Eye Corrosion:	0.011
Eye Irritation:	0.03
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC18904

Natural Product ID:	NPC18904
*Common Name:**	Chlorantene D
IUPAC Name:	(8R,8aR)-8-hydroxy-3,5,8a-trimethyl-8,9-dihydro-7H-benzo[f][1]benzofuran-4,6-dione
Synonyms:	Chlorantene D
Standard InCHIKey:	FMBVVKHYOPPYEC-ABAIWWIYSA-N
Standard InCHI:	InChI=1S/C15H16O4/c1-7-6-19-10-5-15(3)11(17)4-9(16)8(2)13(15)14(18)12(7)10/h6,11,17H,4-5H2,1-3H3/t11-,15+/m1/s1
SMILES:	O=C1C[C@@H](O)[C@]2(C(=C1C)C(=O)c1c(C2)occ1C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456139
PubChem CID:	25147590
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0003655] Eremophilane, 8,9-secoeremophilane and furoeremophilane 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
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19053511]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22372956]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27588583]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30724564]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21178	Chloranthus serratus	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT452	Organism	Helicobacter pylori SS1	Helicobacter pylori SS1	MIC	=	25.0	ug.mL-1	PMID[487558]

☑ 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 NPC18904 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	309
0.1-0.2	1482
0.2-0.3	3441
0.3-0.4	8871
0.4-0.5	11880
0.5-0.6	6702
0.6-0.7	8455
0.7-0.8	1503
0.8-0.85	42
0.85-0.9	9
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8849	High Similarity	NPC177262
0.8836	High Similarity	NPC472787
0.8803	High Similarity	NPC64568
0.8784	High Similarity	NPC179170
0.8784	High Similarity	NPC472786
0.8658	High Similarity	NPC472785
0.8658	High Similarity	NPC88958
0.8649	High Similarity	NPC475777
0.8649	High Similarity	NPC145830
0.8621	High Similarity	NPC97904
0.8592	High Similarity	NPC61157
0.8592	High Similarity	NPC473681
0.8592	High Similarity	NPC218204
0.8543	High Similarity	NPC221992
0.8533	High Similarity	NPC75310
0.8493	Intermediate Similarity	NPC233763
0.8487	Intermediate Similarity	NPC140952
0.8446	Intermediate Similarity	NPC211625
0.8435	Intermediate Similarity	NPC224418
0.8421	Intermediate Similarity	NPC81405
0.8414	Intermediate Similarity	NPC103134
0.8394	Intermediate Similarity	NPC329707
0.837	Intermediate Similarity	NPC178382
0.8367	Intermediate Similarity	NPC62799
0.8366	Intermediate Similarity	NPC299094
0.8366	Intermediate Similarity	NPC10051
0.8345	Intermediate Similarity	NPC52412
0.8344	Intermediate Similarity	NPC114880
0.8312	Intermediate Similarity	NPC287559
0.8311	Intermediate Similarity	NPC281398
0.8299	Intermediate Similarity	NPC185456
0.8288	Intermediate Similarity	NPC205071
0.8278	Intermediate Similarity	NPC471613
0.8269	Intermediate Similarity	NPC56358
0.8269	Intermediate Similarity	NPC472664
0.8231	Intermediate Similarity	NPC117674
0.8217	Intermediate Similarity	NPC121995
0.8214	Intermediate Similarity	NPC61788
0.8212	Intermediate Similarity	NPC144010
0.8201	Intermediate Similarity	NPC59502
0.82	Intermediate Similarity	NPC192069
0.8194	Intermediate Similarity	NPC471996
0.8194	Intermediate Similarity	NPC472376
0.8182	Intermediate Similarity	NPC304692
0.8176	Intermediate Similarity	NPC44602
0.817	Intermediate Similarity	NPC42458
0.817	Intermediate Similarity	NPC158261
0.8165	Intermediate Similarity	NPC270312
0.8156	Intermediate Similarity	NPC471995
0.8143	Intermediate Similarity	NPC45947
0.8141	Intermediate Similarity	NPC18986
0.8138	Intermediate Similarity	NPC265181
0.8133	Intermediate Similarity	NPC252208
0.8133	Intermediate Similarity	NPC19747
0.8129	Intermediate Similarity	NPC476404
0.8129	Intermediate Similarity	NPC474611
0.8129	Intermediate Similarity	NPC294300
0.8129	Intermediate Similarity	NPC317900
0.8125	Intermediate Similarity	NPC4764
0.8117	Intermediate Similarity	NPC104736
0.8117	Intermediate Similarity	NPC41880
0.8108	Intermediate Similarity	NPC84479
0.8105	Intermediate Similarity	NPC178932
0.8101	Intermediate Similarity	NPC475779
0.8095	Intermediate Similarity	NPC20578
0.8095	Intermediate Similarity	NPC263337
0.8095	Intermediate Similarity	NPC62103
0.8082	Intermediate Similarity	NPC148374
0.8077	Intermediate Similarity	NPC333139
0.8067	Intermediate Similarity	NPC302987
0.8058	Intermediate Similarity	NPC184391
0.8054	Intermediate Similarity	NPC114513
0.8054	Intermediate Similarity	NPC27798
0.8054	Intermediate Similarity	NPC41182
0.8054	Intermediate Similarity	NPC245522
0.8054	Intermediate Similarity	NPC93241
0.8052	Intermediate Similarity	NPC469336
0.805	Intermediate Similarity	NPC472784
0.8045	Intermediate Similarity	NPC59035
0.8045	Intermediate Similarity	NPC79202
0.8041	Intermediate Similarity	NPC267632
0.8015	Intermediate Similarity	NPC97566
0.8014	Intermediate Similarity	NPC202260
0.8013	Intermediate Similarity	NPC217602
0.8013	Intermediate Similarity	NPC473282
0.8013	Intermediate Similarity	NPC104380
0.7987	Intermediate Similarity	NPC476944
0.7987	Intermediate Similarity	NPC158871
0.7986	Intermediate Similarity	NPC158525
0.7975	Intermediate Similarity	NPC283209
0.7975	Intermediate Similarity	NPC472780
0.7975	Intermediate Similarity	NPC472783
0.7973	Intermediate Similarity	NPC473152
0.7972	Intermediate Similarity	NPC293253
0.7972	Intermediate Similarity	NPC218838
0.7961	Intermediate Similarity	NPC280025
0.7959	Intermediate Similarity	NPC90296
0.7959	Intermediate Similarity	NPC67003
0.7945	Intermediate Similarity	NPC236532
0.7937	Intermediate Similarity	NPC136641
0.7935	Intermediate Similarity	NPC290927
0.7935	Intermediate Similarity	NPC25351
0.7931	Intermediate Similarity	NPC46896
0.7931	Intermediate Similarity	NPC146872
0.7922	Intermediate Similarity	NPC121615
0.7922	Intermediate Similarity	NPC75906
0.7922	Intermediate Similarity	NPC294511
0.7919	Intermediate Similarity	NPC243577
0.7919	Intermediate Similarity	NPC476946
0.7917	Intermediate Similarity	NPC471998
0.7917	Intermediate Similarity	NPC200718
0.7911	Intermediate Similarity	NPC472781
0.7911	Intermediate Similarity	NPC472782
0.7911	Intermediate Similarity	NPC68848
0.7908	Intermediate Similarity	NPC226578
0.7908	Intermediate Similarity	NPC212257
0.7902	Intermediate Similarity	NPC473982
0.7902	Intermediate Similarity	NPC477412
0.7895	Intermediate Similarity	NPC93666
0.7883	Intermediate Similarity	NPC79557
0.7881	Intermediate Similarity	NPC471292
0.7881	Intermediate Similarity	NPC346
0.7877	Intermediate Similarity	NPC42400
0.7871	Intermediate Similarity	NPC282793
0.7867	Intermediate Similarity	NPC199044
0.7867	Intermediate Similarity	NPC238843
0.7867	Intermediate Similarity	NPC142113
0.7862	Intermediate Similarity	NPC285567
0.7857	Intermediate Similarity	NPC272590
0.7848	Intermediate Similarity	NPC476349
0.7848	Intermediate Similarity	NPC476350
0.7847	Intermediate Similarity	NPC477406
0.7847	Intermediate Similarity	NPC470740
0.7843	Intermediate Similarity	NPC472654
0.7843	Intermediate Similarity	NPC470998
0.7843	Intermediate Similarity	NPC195325
0.7838	Intermediate Similarity	NPC477408
0.7834	Intermediate Similarity	NPC472772
0.7834	Intermediate Similarity	NPC194499
0.7826	Intermediate Similarity	NPC323118
0.7821	Intermediate Similarity	NPC469966
0.7821	Intermediate Similarity	NPC281258
0.7821	Intermediate Similarity	NPC35000
0.7821	Intermediate Similarity	NPC264943
0.7821	Intermediate Similarity	NPC92979
0.7818	Intermediate Similarity	NPC472665
0.7806	Intermediate Similarity	NPC470996
0.7806	Intermediate Similarity	NPC469503
0.7806	Intermediate Similarity	NPC246164
0.7801	Intermediate Similarity	NPC290955
0.78	Intermediate Similarity	NPC329493
0.7799	Intermediate Similarity	NPC313368
0.7799	Intermediate Similarity	NPC69028
0.7799	Intermediate Similarity	NPC188649
0.7792	Intermediate Similarity	NPC469335
0.7792	Intermediate Similarity	NPC159927
0.7792	Intermediate Similarity	NPC228842
0.7792	Intermediate Similarity	NPC470997
0.7785	Intermediate Similarity	NPC84349
0.7785	Intermediate Similarity	NPC205765
0.7778	Intermediate Similarity	NPC191012
0.7771	Intermediate Similarity	NPC295914
0.777	Intermediate Similarity	NPC272899
0.777	Intermediate Similarity	NPC474722
0.7764	Intermediate Similarity	NPC100849
0.7763	Intermediate Similarity	NPC262198
0.7756	Intermediate Similarity	NPC44606
0.7756	Intermediate Similarity	NPC67654
0.7756	Intermediate Similarity	NPC30222
0.7756	Intermediate Similarity	NPC57998
0.7755	Intermediate Similarity	NPC473268
0.7755	Intermediate Similarity	NPC310043
0.7755	Intermediate Similarity	NPC307401
0.7755	Intermediate Similarity	NPC310830
0.775	Intermediate Similarity	NPC88841
0.775	Intermediate Similarity	NPC224394
0.775	Intermediate Similarity	NPC269117
0.775	Intermediate Similarity	NPC663
0.775	Intermediate Similarity	NPC288602
0.7748	Intermediate Similarity	NPC251865
0.7746	Intermediate Similarity	NPC26532
0.7746	Intermediate Similarity	NPC279877
0.774	Intermediate Similarity	NPC159786
0.774	Intermediate Similarity	NPC476947
0.7736	Intermediate Similarity	NPC472299
0.7736	Intermediate Similarity	NPC477402
0.7733	Intermediate Similarity	NPC289660
0.7733	Intermediate Similarity	NPC82920
0.7733	Intermediate Similarity	NPC164697
0.7733	Intermediate Similarity	NPC121158
0.773	Intermediate Similarity	NPC23086
0.7727	Intermediate Similarity	NPC234494
0.7722	Intermediate Similarity	NPC474386
0.7722	Intermediate Similarity	NPC197137
0.7722	Intermediate Similarity	NPC88007
0.7722	Intermediate Similarity	NPC195954
0.7722	Intermediate Similarity	NPC247677
0.7722	Intermediate Similarity	NPC160015
0.7716	Intermediate Similarity	NPC473753
0.7716	Intermediate Similarity	NPC473766

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 NPC18904 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	1016
0.2-0.3	1867
0.3-0.4	2759
0.4-0.5	2059
0.5-0.6	894
0.6-0.7	243
0.7-0.8	26
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8138	Intermediate Similarity	NPD1471	Phase 3
0.8077	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2344	Approved
0.7667	Intermediate Similarity	NPD2800	Approved
0.7633	Intermediate Similarity	NPD8434	Phase 2
0.7595	Intermediate Similarity	NPD5760	Phase 2
0.7595	Intermediate Similarity	NPD5761	Phase 2
0.7566	Intermediate Similarity	NPD2309	Approved
0.7533	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD6765	Approved
0.7337	Intermediate Similarity	NPD6764	Approved
0.7308	Intermediate Similarity	NPD2532	Approved
0.7308	Intermediate Similarity	NPD2534	Approved
0.7308	Intermediate Similarity	NPD2533	Approved
0.7303	Intermediate Similarity	NPD2346	Discontinued
0.7273	Intermediate Similarity	NPD4628	Phase 3
0.7233	Intermediate Similarity	NPD3226	Approved
0.7215	Intermediate Similarity	NPD920	Approved
0.7171	Intermediate Similarity	NPD2799	Discontinued
0.7169	Intermediate Similarity	NPD6808	Phase 2
0.7168	Intermediate Similarity	NPD6785	Approved
0.7168	Intermediate Similarity	NPD6784	Approved
0.7153	Intermediate Similarity	NPD3972	Approved
0.7114	Intermediate Similarity	NPD2313	Discontinued
0.7108	Intermediate Similarity	NPD1247	Approved
0.7101	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD6279	Approved
0.7099	Intermediate Similarity	NPD6280	Approved
0.7089	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6273	Approved
0.7039	Intermediate Similarity	NPD6651	Approved
0.7032	Intermediate Similarity	NPD1549	Phase 2
0.7013	Intermediate Similarity	NPD2796	Approved
0.7012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2296	Approved
0.7	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6599	Discontinued
0.6962	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7819	Suspended
0.6936	Remote Similarity	NPD6559	Discontinued
0.6929	Remote Similarity	NPD1241	Discontinued
0.6923	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6959	Discontinued
0.689	Remote Similarity	NPD1934	Approved
0.6879	Remote Similarity	NPD1243	Approved
0.6867	Remote Similarity	NPD3882	Suspended
0.6846	Remote Similarity	NPD2798	Approved
0.6845	Remote Similarity	NPD5494	Approved
0.6839	Remote Similarity	NPD1510	Phase 2
0.6829	Remote Similarity	NPD7411	Suspended
0.6828	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3749	Approved
0.6824	Remote Similarity	NPD3926	Phase 2
0.6824	Remote Similarity	NPD1876	Approved
0.6818	Remote Similarity	NPD1607	Approved
0.6803	Remote Similarity	NPD9717	Approved
0.6802	Remote Similarity	NPD3818	Discontinued
0.6797	Remote Similarity	NPD1240	Approved
0.6795	Remote Similarity	NPD1551	Phase 2
0.6795	Remote Similarity	NPD2935	Discontinued
0.6788	Remote Similarity	NPD6844	Discontinued
0.6786	Remote Similarity	NPD919	Approved
0.6776	Remote Similarity	NPD3268	Approved
0.677	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4380	Phase 2
0.6765	Remote Similarity	NPD5711	Approved
0.6765	Remote Similarity	NPD5710	Approved
0.6755	Remote Similarity	NPD6832	Phase 2
0.6753	Remote Similarity	NPD447	Suspended
0.675	Remote Similarity	NPD7236	Approved
0.6747	Remote Similarity	NPD2801	Approved
0.6747	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD1778	Approved
0.6708	Remote Similarity	NPD6799	Approved
0.6708	Remote Similarity	NPD1511	Approved
0.6689	Remote Similarity	NPD1608	Approved
0.6689	Remote Similarity	NPD9494	Approved
0.6688	Remote Similarity	NPD6099	Approved
0.6688	Remote Similarity	NPD6100	Approved
0.6686	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6166	Phase 2
0.6686	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1203	Approved
0.6667	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD411	Approved
0.6645	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD6355	Discontinued
0.6627	Remote Similarity	NPD7075	Discontinued
0.6626	Remote Similarity	NPD1512	Approved
0.6625	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD4110	Phase 3
0.6624	Remote Similarity	NPD7033	Discontinued
0.6623	Remote Similarity	NPD5647	Approved
0.6623	Remote Similarity	NPD1019	Discontinued
0.6607	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3817	Phase 2
0.6606	Remote Similarity	NPD7458	Discontinued
0.6606	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD2424	Discontinued
0.659	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.659	Remote Similarity	NPD2403	Approved
0.6587	Remote Similarity	NPD6801	Discontinued
0.6581	Remote Similarity	NPD4140	Approved
0.657	Remote Similarity	NPD6232	Discontinued
0.6564	Remote Similarity	NPD4661	Approved
0.6564	Remote Similarity	NPD4662	Approved
0.6556	Remote Similarity	NPD3267	Approved
0.6556	Remote Similarity	NPD3266	Approved
0.6556	Remote Similarity	NPD1470	Approved
0.6552	Remote Similarity	NPD7473	Discontinued
0.6545	Remote Similarity	NPD7239	Suspended
0.6541	Remote Similarity	NPD6004	Phase 3
0.6541	Remote Similarity	NPD6002	Phase 3
0.6541	Remote Similarity	NPD6005	Phase 3
0.6541	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6541	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6534	Remote Similarity	NPD7074	Phase 3
0.6531	Remote Similarity	NPD1651	Approved
0.6531	Remote Similarity	NPD8404	Phase 2
0.6522	Remote Similarity	NPD7003	Approved
0.6522	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3750	Approved
0.6519	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD8032	Phase 2
0.6512	Remote Similarity	NPD8127	Discontinued
0.6509	Remote Similarity	NPD5402	Approved
0.6507	Remote Similarity	NPD9092	Discovery
0.6506	Remote Similarity	NPD2651	Approved
0.6506	Remote Similarity	NPD2649	Approved
0.6494	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.649	Remote Similarity	NPD1283	Approved
0.6486	Remote Similarity	NPD17	Approved
0.6483	Remote Similarity	NPD7157	Approved
0.6479	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5844	Phase 1
0.6477	Remote Similarity	NPD7054	Approved
0.6477	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD3140	Approved
0.6474	Remote Similarity	NPD3142	Approved
0.6471	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6798	Discontinued
0.6452	Remote Similarity	NPD7985	Registered
0.6452	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2797	Approved
0.6443	Remote Similarity	NPD3496	Discontinued
0.6441	Remote Similarity	NPD7472	Approved
0.6425	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3751	Discontinued
0.642	Remote Similarity	NPD2163	Approved
0.6419	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD5585	Approved
0.6415	Remote Similarity	NPD4308	Phase 3
0.6415	Remote Similarity	NPD3748	Approved
0.6413	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD6797	Phase 2
0.64	Remote Similarity	NPD1201	Approved
0.6389	Remote Similarity	NPD8313	Approved
0.6389	Remote Similarity	NPD8312	Approved
0.6387	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5403	Approved
0.638	Remote Similarity	NPD3887	Approved
0.6379	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD4477	Approved
0.6375	Remote Similarity	NPD4476	Approved
0.6374	Remote Similarity	NPD7768	Phase 2
0.6369	Remote Similarity	NPD2979	Phase 3
0.6369	Remote Similarity	NPD7028	Phase 2
0.6369	Remote Similarity	NPD7251	Discontinued
0.6364	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5401	Approved
0.6358	Remote Similarity	NPD2654	Approved
0.6351	Remote Similarity	NPD1894	Discontinued
0.6351	Remote Similarity	NPD9545	Approved
0.6346	Remote Similarity	NPD3764	Approved
0.6338	Remote Similarity	NPD2182	Approved
0.6333	Remote Similarity	NPD7808	Phase 3
0.6333	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD5890	Approved
0.6331	Remote Similarity	NPD5889	Approved
0.6329	Remote Similarity	NPD5735	Approved
0.6327	Remote Similarity	NPD9493	Approved
0.6324	Remote Similarity	NPD3269	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5327	Phase 3
0.6313	Remote Similarity	NPD5953	Discontinued
0.6309	Remote Similarity	NPD5691	Approved
0.6306	Remote Similarity	NPD6233	Phase 2
0.6304	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4534	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