NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	2.538
LogD:	2.465
LogS:	-2.741
# Rotatable Bonds:	1
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.729
Synthetic Accessibility Score:	4.695
Fsp3:	0.6
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:	-5.259
MDCK Permeability:	1.4538813957187813e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.016
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.357
Plasma Protein Binding (PPB):	93.81204986572266%
Volume Distribution (VD):	1.342
Pgp-substrate:	11.156084060668945%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.44
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.477
CYP2C9-inhibitor:	0.056
CYP2C9-substrate:	0.223
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.27
CYP3A4-inhibitor:	0.13
CYP3A4-substrate:	0.194

ADMET: Excretion

Clearance (CL):	14.216
Half-life (T1/2):	0.789

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.225
Drug-inuced Liver Injury (DILI):	0.308
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.439
Skin Sensitization:	0.791
Carcinogencity:	0.818
Eye Corrosion:	0.01
Eye Irritation:	0.194
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC168131

Natural Product ID:	NPC168131
*Common Name:**	Dendocarbin F
IUPAC Name:	(5aR,6R,9aS,9bR)-6-(hydroxymethyl)-6,9a-dimethyl-5,5a,7,8,9,9b-hexahydrobenzo[e][2]benzofuran-1,3-dione
Synonyms:	Dendocarbin F
Standard InCHIKey:	NBIGOHIZOSNUHI-JLUCKKNBSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-14(8-16)6-3-7-15(2)10(14)5-4-9-11(15)13(18)19-12(9)17/h4,10-11,16H,3,5-8H2,1-2H3/t10-,11+,14-,15-/m0/s1
SMILES:	OC[C@]1(C)CCC[C@]2([C@H]1CC=C1[C@@H]2C(=O)OC1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470895
PubChem CID:	11129173
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO8660	Dendrodoris carbunculosa	Species	Dendrodorididae	Eukaryota	n.a.	Amatsu-kominato, Boso Peninsula, central Japan (35 07N, 140 11E)	1999-NOV	PMID[11421732]
NPO7781	Piper scutifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18031016]
NPO6857	Actinidia eriantha	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6857	Actinidia eriantha	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1548	Nardia succulenta	Species	Solenostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24628	Lamium galeobdolon	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5268	Chenopodium hircinum	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8660	Dendrodoris carbunculosa	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO578	Eriope blanchetii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2429	Gracilariopsis lemaneiformis	Species	Gracilariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7781	Piper scutifolium	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7474	Sicya macularia	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7919	Hedysarum sericeum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5987	Hypericum yojiroanum	Species	Hypericaceae	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
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	25.0	ug.mL-1	PMID[466499]
NPT168	Cell Line	P388	Mus musculus	IC50	=	22.0	ug.mL-1	PMID[466499]

☑ 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 NPC168131 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	157
0.1-0.2	937
0.2-0.3	4138
0.3-0.4	10849
0.4-0.5	11718
0.5-0.6	6933
0.6-0.7	5594
0.7-0.8	2199
0.8-0.85	147
0.85-0.9	19
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9432	High Similarity	NPC183012
0.9277	High Similarity	NPC22611
0.9205	High Similarity	NPC166346
0.9157	High Similarity	NPC186276
0.9121	High Similarity	NPC23364
0.908	High Similarity	NPC5509
0.8916	High Similarity	NPC195424
0.8876	High Similarity	NPC233345
0.8876	High Similarity	NPC186363
0.8864	High Similarity	NPC174342
0.8837	High Similarity	NPC65661
0.8837	High Similarity	NPC86316
0.8837	High Similarity	NPC106416
0.875	High Similarity	NPC226863
0.8723	High Similarity	NPC63249
0.8667	High Similarity	NPC65513
0.8636	High Similarity	NPC312561
0.8632	High Similarity	NPC134077
0.8621	High Similarity	NPC189311
0.8602	High Similarity	NPC474343
0.8571	High Similarity	NPC475657
0.8571	High Similarity	NPC115021
0.8556	High Similarity	NPC51486
0.8556	High Similarity	NPC158488
0.8556	High Similarity	NPC281942
0.8556	High Similarity	NPC212679
0.8556	High Similarity	NPC220454
0.8556	High Similarity	NPC469595
0.8556	High Similarity	NPC232426
0.8539	High Similarity	NPC215831
0.8539	High Similarity	NPC277771
0.8511	High Similarity	NPC216478
0.8488	Intermediate Similarity	NPC200513
0.8488	Intermediate Similarity	NPC178676
0.8478	Intermediate Similarity	NPC476415
0.8478	Intermediate Similarity	NPC477129
0.8478	Intermediate Similarity	NPC477130
0.8478	Intermediate Similarity	NPC250075
0.8462	Intermediate Similarity	NPC72845
0.8462	Intermediate Similarity	NPC477783
0.8462	Intermediate Similarity	NPC141831
0.8444	Intermediate Similarity	NPC474396
0.8444	Intermediate Similarity	NPC50488
0.8444	Intermediate Similarity	NPC73995
0.8438	Intermediate Similarity	NPC31058
0.8438	Intermediate Similarity	NPC273005
0.8438	Intermediate Similarity	NPC469606
0.8421	Intermediate Similarity	NPC474012
0.8421	Intermediate Similarity	NPC476299
0.8409	Intermediate Similarity	NPC30984
0.8409	Intermediate Similarity	NPC52628
0.8404	Intermediate Similarity	NPC208094
0.8391	Intermediate Similarity	NPC470948
0.8387	Intermediate Similarity	NPC295347
0.8387	Intermediate Similarity	NPC209355
0.8372	Intermediate Similarity	NPC229584
0.8372	Intermediate Similarity	NPC40228
0.8372	Intermediate Similarity	NPC14203
0.837	Intermediate Similarity	NPC151722
0.837	Intermediate Similarity	NPC139692
0.8352	Intermediate Similarity	NPC159748
0.8352	Intermediate Similarity	NPC101651
0.8352	Intermediate Similarity	NPC152467
0.8352	Intermediate Similarity	NPC477782
0.8333	Intermediate Similarity	NPC477128
0.8333	Intermediate Similarity	NPC316500
0.8315	Intermediate Similarity	NPC250981
0.8315	Intermediate Similarity	NPC474062
0.8315	Intermediate Similarity	NPC6979
0.8315	Intermediate Similarity	NPC85698
0.828	Intermediate Similarity	NPC470697
0.828	Intermediate Similarity	NPC53685
0.828	Intermediate Similarity	NPC57117
0.8265	Intermediate Similarity	NPC296950
0.8261	Intermediate Similarity	NPC303697
0.8261	Intermediate Similarity	NPC252433
0.8261	Intermediate Similarity	NPC179517
0.8261	Intermediate Similarity	NPC177037
0.8261	Intermediate Similarity	NPC472814
0.8261	Intermediate Similarity	NPC165904
0.8242	Intermediate Similarity	NPC251528
0.8242	Intermediate Similarity	NPC477973
0.8229	Intermediate Similarity	NPC47024
0.8222	Intermediate Similarity	NPC181103
0.8222	Intermediate Similarity	NPC305029
0.8214	Intermediate Similarity	NPC41017
0.8211	Intermediate Similarity	NPC91695
0.8211	Intermediate Similarity	NPC257726
0.8211	Intermediate Similarity	NPC204054
0.8211	Intermediate Similarity	NPC70145
0.8202	Intermediate Similarity	NPC177932
0.8202	Intermediate Similarity	NPC110405
0.82	Intermediate Similarity	NPC275539
0.82	Intermediate Similarity	NPC189075
0.8191	Intermediate Similarity	NPC293052
0.8182	Intermediate Similarity	NPC469607
0.8182	Intermediate Similarity	NPC193198
0.8182	Intermediate Similarity	NPC477125
0.8182	Intermediate Similarity	NPC97913
0.8172	Intermediate Similarity	NPC476416
0.8163	Intermediate Similarity	NPC476237
0.8152	Intermediate Similarity	NPC469372
0.8144	Intermediate Similarity	NPC244456
0.8144	Intermediate Similarity	NPC469657
0.814	Intermediate Similarity	NPC327674
0.8132	Intermediate Similarity	NPC473229
0.8132	Intermediate Similarity	NPC477302
0.8132	Intermediate Similarity	NPC136879
0.8125	Intermediate Similarity	NPC316598
0.8125	Intermediate Similarity	NPC478056
0.8125	Intermediate Similarity	NPC98868
0.8118	Intermediate Similarity	NPC41780
0.8118	Intermediate Similarity	NPC187568
0.8111	Intermediate Similarity	NPC185638
0.8111	Intermediate Similarity	NPC220478
0.8111	Intermediate Similarity	NPC329692
0.8111	Intermediate Similarity	NPC9231
0.8111	Intermediate Similarity	NPC477920
0.8105	Intermediate Similarity	NPC242848
0.8105	Intermediate Similarity	NPC234993
0.8105	Intermediate Similarity	NPC134072
0.8105	Intermediate Similarity	NPC112654
0.81	Intermediate Similarity	NPC91034
0.81	Intermediate Similarity	NPC110496
0.8095	Intermediate Similarity	NPC476795
0.809	Intermediate Similarity	NPC472865
0.809	Intermediate Similarity	NPC30486
0.809	Intermediate Similarity	NPC164577
0.8081	Intermediate Similarity	NPC146731
0.8065	Intermediate Similarity	NPC470113
0.8061	Intermediate Similarity	NPC58329
0.8061	Intermediate Similarity	NPC476081
0.8046	Intermediate Similarity	NPC271104
0.8043	Intermediate Similarity	NPC284561
0.8043	Intermediate Similarity	NPC116620
0.8043	Intermediate Similarity	NPC218927
0.8043	Intermediate Similarity	NPC206001
0.8041	Intermediate Similarity	NPC477720
0.8041	Intermediate Similarity	NPC472644
0.8041	Intermediate Similarity	NPC476303
0.8041	Intermediate Similarity	NPC476274
0.8039	Intermediate Similarity	NPC5103
0.8023	Intermediate Similarity	NPC35574
0.8023	Intermediate Similarity	NPC198240
0.8022	Intermediate Similarity	NPC470012
0.8022	Intermediate Similarity	NPC171722
0.8022	Intermediate Similarity	NPC167877
0.8021	Intermediate Similarity	NPC475709
0.8021	Intermediate Similarity	NPC253826
0.8021	Intermediate Similarity	NPC224356
0.8021	Intermediate Similarity	NPC202705
0.8021	Intermediate Similarity	NPC132753
0.8021	Intermediate Similarity	NPC73911
0.8021	Intermediate Similarity	NPC175351
0.8021	Intermediate Similarity	NPC170131
0.8021	Intermediate Similarity	NPC151681
0.8021	Intermediate Similarity	NPC121402
0.802	Intermediate Similarity	NPC476802
0.802	Intermediate Similarity	NPC89171
0.8	Intermediate Similarity	NPC217394
0.8	Intermediate Similarity	NPC316215
0.8	Intermediate Similarity	NPC473251
0.8	Intermediate Similarity	NPC42586
0.8	Intermediate Similarity	NPC329738
0.798	Intermediate Similarity	NPC120321
0.798	Intermediate Similarity	NPC176883
0.7979	Intermediate Similarity	NPC472871
0.7979	Intermediate Similarity	NPC472303
0.7959	Intermediate Similarity	NPC476223
0.7959	Intermediate Similarity	NPC81530
0.7959	Intermediate Similarity	NPC471412
0.7959	Intermediate Similarity	NPC224720
0.7959	Intermediate Similarity	NPC476240
0.7959	Intermediate Similarity	NPC303559
0.7957	Intermediate Similarity	NPC15059
0.7957	Intermediate Similarity	NPC476437
0.7957	Intermediate Similarity	NPC469368
0.7957	Intermediate Similarity	NPC472307
0.7957	Intermediate Similarity	NPC476369
0.7955	Intermediate Similarity	NPC475665
0.7955	Intermediate Similarity	NPC327002
0.7955	Intermediate Similarity	NPC282293
0.7955	Intermediate Similarity	NPC38642
0.7941	Intermediate Similarity	NPC137911
0.7941	Intermediate Similarity	NPC228477
0.7938	Intermediate Similarity	NPC278386
0.7938	Intermediate Similarity	NPC108368
0.7938	Intermediate Similarity	NPC473154
0.7938	Intermediate Similarity	NPC222011
0.7938	Intermediate Similarity	NPC57079
0.7938	Intermediate Similarity	NPC124512
0.7938	Intermediate Similarity	NPC159763
0.7935	Intermediate Similarity	NPC24816
0.7935	Intermediate Similarity	NPC472870
0.7935	Intermediate Similarity	NPC472302
0.7931	Intermediate Similarity	NPC470244
0.7931	Intermediate Similarity	NPC470239
0.7921	Intermediate Similarity	NPC475294
0.7917	Intermediate Similarity	NPC29952
0.7917	Intermediate Similarity	NPC154526

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 NPC168131 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	133
0.1-0.2	1227
0.2-0.3	3597
0.3-0.4	2769
0.4-0.5	882
0.5-0.6	281
0.6-0.7	209
0.7-0.8	50
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
0.8488	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD1694	Approved
0.7938	Intermediate Similarity	NPD4225	Approved
0.7789	Intermediate Similarity	NPD6399	Phase 3
0.7629	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7475	Intermediate Similarity	NPD7902	Approved
0.7475	Intermediate Similarity	NPD6083	Phase 2
0.7475	Intermediate Similarity	NPD6084	Phase 2
0.7449	Intermediate Similarity	NPD5695	Phase 3
0.7431	Intermediate Similarity	NPD7115	Discovery
0.74	Intermediate Similarity	NPD5696	Approved
0.7396	Intermediate Similarity	NPD5785	Approved
0.7368	Intermediate Similarity	NPD6672	Approved
0.7368	Intermediate Similarity	NPD5737	Approved
0.7347	Intermediate Similarity	NPD7748	Approved
0.734	Intermediate Similarity	NPD6409	Approved
0.734	Intermediate Similarity	NPD3618	Phase 1
0.734	Intermediate Similarity	NPD6684	Approved
0.734	Intermediate Similarity	NPD7521	Approved
0.734	Intermediate Similarity	NPD5330	Approved
0.734	Intermediate Similarity	NPD7334	Approved
0.734	Intermediate Similarity	NPD7146	Approved
0.7333	Intermediate Similarity	NPD6686	Approved
0.732	Intermediate Similarity	NPD5693	Phase 1
0.732	Intermediate Similarity	NPD7515	Phase 2
0.7312	Intermediate Similarity	NPD3133	Approved
0.7312	Intermediate Similarity	NPD3665	Phase 1
0.7312	Intermediate Similarity	NPD3666	Approved
0.7283	Intermediate Similarity	NPD3667	Approved
0.7253	Intermediate Similarity	NPD4695	Discontinued
0.7188	Intermediate Similarity	NPD6903	Approved
0.7188	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD7900	Approved
0.7143	Intermediate Similarity	NPD5281	Approved
0.7143	Intermediate Similarity	NPD5284	Approved
0.713	Intermediate Similarity	NPD6650	Approved
0.713	Intermediate Similarity	NPD6649	Approved
0.7128	Intermediate Similarity	NPD4786	Approved
0.7113	Intermediate Similarity	NPD4753	Phase 2
0.7103	Intermediate Similarity	NPD6372	Approved
0.7103	Intermediate Similarity	NPD6373	Approved
0.71	Intermediate Similarity	NPD4629	Approved
0.71	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD5210	Approved
0.7079	Intermediate Similarity	NPD8039	Approved
0.7075	Intermediate Similarity	NPD5697	Approved
0.7041	Intermediate Similarity	NPD5207	Approved
0.7037	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4697	Phase 3
0.7009	Intermediate Similarity	NPD6011	Approved
0.7009	Intermediate Similarity	NPD6881	Approved
0.7009	Intermediate Similarity	NPD6899	Approved
0.6981	Remote Similarity	NPD6675	Approved
0.6981	Remote Similarity	NPD5739	Approved
0.6981	Remote Similarity	NPD7128	Approved
0.6981	Remote Similarity	NPD6402	Approved
0.6979	Remote Similarity	NPD4623	Approved
0.6979	Remote Similarity	NPD5279	Phase 3
0.6979	Remote Similarity	NPD4519	Discontinued
0.6979	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6411	Approved
0.697	Remote Similarity	NPD6079	Approved
0.6947	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6012	Approved
0.6944	Remote Similarity	NPD6013	Approved
0.6944	Remote Similarity	NPD6014	Approved
0.6939	Remote Similarity	NPD6673	Approved
0.6939	Remote Similarity	NPD6904	Approved
0.6939	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5328	Approved
0.6939	Remote Similarity	NPD6080	Approved
0.6916	Remote Similarity	NPD5701	Approved
0.6915	Remote Similarity	NPD4223	Phase 3
0.6915	Remote Similarity	NPD4221	Approved
0.6909	Remote Similarity	NPD6053	Discontinued
0.6907	Remote Similarity	NPD3573	Approved
0.69	Remote Similarity	NPD5779	Approved
0.69	Remote Similarity	NPD5778	Approved
0.6881	Remote Similarity	NPD7102	Approved
0.6881	Remote Similarity	NPD7290	Approved
0.6881	Remote Similarity	NPD6883	Approved
0.6875	Remote Similarity	NPD5363	Approved
0.6869	Remote Similarity	NPD5692	Phase 3
0.6869	Remote Similarity	NPD46	Approved
0.6869	Remote Similarity	NPD6698	Approved
0.6863	Remote Similarity	NPD5221	Approved
0.6863	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5222	Approved
0.6857	Remote Similarity	NPD7632	Discontinued
0.6852	Remote Similarity	NPD7320	Approved
0.6837	Remote Similarity	NPD5208	Approved
0.6832	Remote Similarity	NPD6001	Approved
0.6827	Remote Similarity	NPD6404	Discontinued
0.6822	Remote Similarity	NPD6008	Approved
0.6818	Remote Similarity	NPD6617	Approved
0.6818	Remote Similarity	NPD6869	Approved
0.6818	Remote Similarity	NPD8130	Phase 1
0.6818	Remote Similarity	NPD6847	Approved
0.6804	Remote Similarity	NPD5690	Phase 2
0.68	Remote Similarity	NPD5694	Approved
0.68	Remote Similarity	NPD8034	Phase 2
0.68	Remote Similarity	NPD8035	Phase 2
0.68	Remote Similarity	NPD6050	Approved
0.6796	Remote Similarity	NPD5173	Approved
0.6771	Remote Similarity	NPD3668	Phase 3
0.6771	Remote Similarity	NPD4197	Approved
0.6768	Remote Similarity	NPD6101	Approved
0.6768	Remote Similarity	NPD6051	Approved
0.6768	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6882	Approved
0.6757	Remote Similarity	NPD8297	Approved
0.6733	Remote Similarity	NPD4202	Approved
0.6727	Remote Similarity	NPD6371	Approved
0.6701	Remote Similarity	NPD5329	Approved
0.6701	Remote Similarity	NPD1696	Phase 3
0.6698	Remote Similarity	NPD5211	Phase 2
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6635	Remote Similarity	NPD4755	Approved
0.6634	Remote Similarity	NPD7637	Suspended
0.6633	Remote Similarity	NPD4689	Approved
0.6633	Remote Similarity	NPD4138	Approved
0.6633	Remote Similarity	NPD4693	Phase 3
0.6633	Remote Similarity	NPD6098	Approved
0.6633	Remote Similarity	NPD4688	Approved
0.6633	Remote Similarity	NPD4690	Approved
0.6633	Remote Similarity	NPD5280	Approved
0.6633	Remote Similarity	NPD4694	Approved
0.6633	Remote Similarity	NPD5205	Approved
0.6633	Remote Similarity	NPD5786	Approved
0.6606	Remote Similarity	NPD6412	Phase 2
0.6606	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD5223	Approved
0.66	Remote Similarity	NPD1695	Approved
0.6581	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6868	Approved
0.6579	Remote Similarity	NPD6274	Approved
0.6574	Remote Similarity	NPD5141	Approved
0.6571	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4269	Approved
0.6562	Remote Similarity	NPD5209	Approved
0.6562	Remote Similarity	NPD4270	Approved
0.6549	Remote Similarity	NPD4632	Approved
0.6542	Remote Similarity	NPD5226	Approved
0.6542	Remote Similarity	NPD5225	Approved
0.6542	Remote Similarity	NPD5224	Approved
0.6542	Remote Similarity	NPD4633	Approved
0.6538	Remote Similarity	NPD7614	Phase 1
0.6531	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6317	Approved
0.6509	Remote Similarity	NPD4700	Approved
0.6505	Remote Similarity	NPD5282	Discontinued
0.6495	Remote Similarity	NPD4788	Approved
0.6481	Remote Similarity	NPD6052	Approved
0.6481	Remote Similarity	NPD5175	Approved
0.6481	Remote Similarity	NPD5174	Approved
0.6466	Remote Similarity	NPD6335	Approved
0.6466	Remote Similarity	NPD6313	Approved
0.6466	Remote Similarity	NPD6314	Approved
0.6458	Remote Similarity	NPD5369	Approved
0.6452	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4691	Approved
0.6442	Remote Similarity	NPD5654	Approved
0.6421	Remote Similarity	NPD4195	Approved
0.641	Remote Similarity	NPD7100	Approved
0.641	Remote Similarity	NPD7101	Approved
0.6383	Remote Similarity	NPD4756	Discovery
0.6381	Remote Similarity	NPD7732	Phase 3
0.6379	Remote Similarity	NPD6009	Approved
0.6373	Remote Similarity	NPD7838	Discovery
0.6371	Remote Similarity	NPD7260	Phase 2
0.6364	Remote Similarity	NPD7507	Approved
0.6356	Remote Similarity	NPD6319	Approved
0.6354	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4252	Approved
0.6344	Remote Similarity	NPD7339	Approved
0.6344	Remote Similarity	NPD6942	Approved
0.6333	Remote Similarity	NPD4137	Phase 3
0.633	Remote Similarity	NPD4754	Approved
0.6321	Remote Similarity	NPD5959	Approved
0.6306	Remote Similarity	NPD6614	Approved
0.6303	Remote Similarity	NPD5983	Phase 2
0.6296	Remote Similarity	NPD5344	Discontinued
0.6281	Remote Similarity	NPD7492	Approved
0.6264	Remote Similarity	NPD4747	Approved
0.625	Remote Similarity	NPD5128	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data