NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	3.021
LogD:	2.743
LogS:	-2.733
# Rotatable Bonds:	0
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	4.601
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.188
MDCK Permeability:	1.569259984535165e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.175
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.071

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.485
Plasma Protein Binding (PPB):	91.03031158447266%
Volume Distribution (VD):	1.519
Pgp-substrate:	15.233501434326172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.027
CYP1A2-substrate:	0.115
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.28
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.545
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.3
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	16.813
Half-life (T1/2):	0.731

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.607
Carcinogencity:	0.586
Eye Corrosion:	0.013
Eye Irritation:	0.214
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC183012

Natural Product ID:	NPC183012
*Common Name:**	Dendocarbin E
IUPAC Name:	(5aR,7S,9aS,9bR)-7-hydroxy-6,6,9a-trimethyl-5,5a,7,8,9,9b-hexahydrobenzo[e][2]benzofuran-1,3-dione
Synonyms:	Dendocarbin E
Standard InCHIKey:	IHYRQBZEYBEIMC-ZVXAKGHKSA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-14(2)9-5-4-8-11(13(18)19-12(8)17)15(9,3)7-6-10(14)16/h4,9-11,16H,5-7H2,1-3H3/t9-,10-,11+,15-/m0/s1
SMILES:	O=C1OC(=O)C2=CC[C@@H]3[C@]([C@@H]12)(C)CC[C@@H](C3(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL470894
PubChem CID:	11065317
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]
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]
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]

☑ 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[485635]
NPT168	Cell Line	P388	Mus musculus	IC50	=	22.5	ug.mL-1	PMID[485635]
NPT168	Cell Line	P388	Mus musculus	IC50	=	19.0	ug.mL-1	PMID[485635]

☑ 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 NPC183012 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	168
0.1-0.2	989
0.2-0.3	3708
0.3-0.4	7972
0.4-0.5	13629
0.5-0.6	6862
0.6-0.7	6136
0.7-0.8	2895
0.8-0.85	282
0.85-0.9	49
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9438	High Similarity	NPC186363
0.9438	High Similarity	NPC233345
0.9432	High Similarity	NPC168131
0.9101	High Similarity	NPC277771
0.9043	High Similarity	NPC23364
0.9043	High Similarity	NPC216478
0.9011	High Similarity	NPC72845
0.9	High Similarity	NPC73995
0.8947	High Similarity	NPC474012
0.8947	High Similarity	NPC476299
0.8936	High Similarity	NPC474343
0.8913	High Similarity	NPC139692
0.8901	High Similarity	NPC158488
0.8901	High Similarity	NPC152467
0.8889	High Similarity	NPC215831
0.8876	High Similarity	NPC6979
0.8876	High Similarity	NPC250981
0.8817	High Similarity	NPC470697
0.8817	High Similarity	NPC57117
0.8817	High Similarity	NPC250075
0.8817	High Similarity	NPC477129
0.8817	High Similarity	NPC477130
0.8791	High Similarity	NPC50488
0.8791	High Similarity	NPC474396
0.8791	High Similarity	NPC5509
0.8778	High Similarity	NPC305029
0.8778	High Similarity	NPC181103
0.8764	High Similarity	NPC52628
0.8763	High Similarity	NPC469606
0.8763	High Similarity	NPC31058
0.8763	High Similarity	NPC273005
0.875	High Similarity	NPC470948
0.875	High Similarity	NPC47024
0.875	High Similarity	NPC22611
0.871	High Similarity	NPC166346
0.87	High Similarity	NPC275539
0.87	High Similarity	NPC189075
0.8687	High Similarity	NPC469607
0.8681	High Similarity	NPC477302
0.8681	High Similarity	NPC226863
0.8681	High Similarity	NPC473229
0.8681	High Similarity	NPC136879
0.8681	High Similarity	NPC477128
0.8673	High Similarity	NPC476237
0.8667	High Similarity	NPC477920
0.8667	High Similarity	NPC85698
0.8646	High Similarity	NPC478056
0.8636	High Similarity	NPC178676
0.8636	High Similarity	NPC186276
0.8632	High Similarity	NPC234993
0.8632	High Similarity	NPC242848
0.8632	High Similarity	NPC134072
0.8602	High Similarity	NPC252433
0.86	High Similarity	NPC110496
0.8587	High Similarity	NPC116620
0.8587	High Similarity	NPC206001
0.8587	High Similarity	NPC218927
0.8571	High Similarity	NPC476081
0.8571	High Similarity	NPC312561
0.8571	High Similarity	NPC470012
0.8571	High Similarity	NPC58329
0.8557	High Similarity	NPC476303
0.8556	High Similarity	NPC177932
0.8542	High Similarity	NPC132753
0.8542	High Similarity	NPC73911
0.8542	High Similarity	NPC91695
0.8542	High Similarity	NPC121402
0.8542	High Similarity	NPC175351
0.8542	High Similarity	NPC151681
0.8542	High Similarity	NPC70145
0.8542	High Similarity	NPC253826
0.8542	High Similarity	NPC224356
0.8526	High Similarity	NPC316215
0.8515	High Similarity	NPC476802
0.8515	High Similarity	NPC89171
0.8511	High Similarity	NPC475657
0.8511	High Similarity	NPC115021
0.85	High Similarity	NPC477125
0.8495	Intermediate Similarity	NPC212679
0.8495	Intermediate Similarity	NPC469595
0.8495	Intermediate Similarity	NPC281942
0.8495	Intermediate Similarity	NPC232426
0.8495	Intermediate Similarity	NPC220454
0.8485	Intermediate Similarity	NPC120321
0.8485	Intermediate Similarity	NPC176883
0.8469	Intermediate Similarity	NPC81530
0.8469	Intermediate Similarity	NPC303559
0.8469	Intermediate Similarity	NPC471412
0.8462	Intermediate Similarity	NPC329692
0.8462	Intermediate Similarity	NPC473226
0.8462	Intermediate Similarity	NPC9231
0.8462	Intermediate Similarity	NPC185638
0.8454	Intermediate Similarity	NPC159763
0.8454	Intermediate Similarity	NPC57079
0.8454	Intermediate Similarity	NPC473154
0.8454	Intermediate Similarity	NPC278386
0.8454	Intermediate Similarity	NPC124512
0.8454	Intermediate Similarity	NPC108368
0.8454	Intermediate Similarity	NPC316598
0.8444	Intermediate Similarity	NPC30486
0.8438	Intermediate Similarity	NPC472363
0.8438	Intermediate Similarity	NPC472362
0.8438	Intermediate Similarity	NPC202833
0.8438	Intermediate Similarity	NPC154526
0.8427	Intermediate Similarity	NPC226988
0.8421	Intermediate Similarity	NPC148000
0.8421	Intermediate Similarity	NPC469596
0.8421	Intermediate Similarity	NPC24861
0.8421	Intermediate Similarity	NPC225474
0.8409	Intermediate Similarity	NPC195424
0.8404	Intermediate Similarity	NPC141831
0.8404	Intermediate Similarity	NPC49420
0.84	Intermediate Similarity	NPC296950
0.84	Intermediate Similarity	NPC118911
0.8387	Intermediate Similarity	NPC174342
0.8387	Intermediate Similarity	NPC288699
0.8384	Intermediate Similarity	NPC32577
0.8384	Intermediate Similarity	NPC155332
0.8384	Intermediate Similarity	NPC136289
0.8384	Intermediate Similarity	NPC114540
0.8367	Intermediate Similarity	NPC476274
0.8367	Intermediate Similarity	NPC201406
0.8367	Intermediate Similarity	NPC117685
0.8367	Intermediate Similarity	NPC471413
0.8367	Intermediate Similarity	NPC472644
0.8365	Intermediate Similarity	NPC12046
0.8365	Intermediate Similarity	NPC194951
0.8352	Intermediate Similarity	NPC189311
0.8352	Intermediate Similarity	NPC110405
0.8352	Intermediate Similarity	NPC86316
0.8352	Intermediate Similarity	NPC65661
0.8352	Intermediate Similarity	NPC106416
0.8333	Intermediate Similarity	NPC259042
0.8333	Intermediate Similarity	NPC157686
0.8317	Intermediate Similarity	NPC1679
0.8316	Intermediate Similarity	NPC152778
0.8316	Intermediate Similarity	NPC162615
0.8316	Intermediate Similarity	NPC205034
0.8315	Intermediate Similarity	NPC38642
0.8315	Intermediate Similarity	NPC473420
0.8315	Intermediate Similarity	NPC475665
0.83	Intermediate Similarity	NPC112009
0.83	Intermediate Similarity	NPC254202
0.83	Intermediate Similarity	NPC36688
0.8298	Intermediate Similarity	NPC51486
0.8298	Intermediate Similarity	NPC280149
0.8298	Intermediate Similarity	NPC310479
0.8298	Intermediate Similarity	NPC221111
0.8298	Intermediate Similarity	NPC78973
0.8286	Intermediate Similarity	NPC157441
0.8283	Intermediate Similarity	NPC63249
0.8283	Intermediate Similarity	NPC224720
0.8283	Intermediate Similarity	NPC476240
0.8283	Intermediate Similarity	NPC235142
0.8283	Intermediate Similarity	NPC115862
0.8283	Intermediate Similarity	NPC476223
0.8283	Intermediate Similarity	NPC472637
0.828	Intermediate Similarity	NPC104560
0.8265	Intermediate Similarity	NPC252295
0.8265	Intermediate Similarity	NPC234617
0.8265	Intermediate Similarity	NPC124703
0.8261	Intermediate Similarity	NPC131813
0.8247	Intermediate Similarity	NPC165528
0.8247	Intermediate Similarity	NPC93245
0.8247	Intermediate Similarity	NPC284518
0.8247	Intermediate Similarity	NPC307164
0.8247	Intermediate Similarity	NPC228766
0.8242	Intermediate Similarity	NPC159635
0.8242	Intermediate Similarity	NPC470011
0.8235	Intermediate Similarity	NPC67321
0.8235	Intermediate Similarity	NPC301666
0.8235	Intermediate Similarity	NPC187435
0.8229	Intermediate Similarity	NPC476415
0.8229	Intermediate Similarity	NPC38830
0.8229	Intermediate Similarity	NPC53685
0.8229	Intermediate Similarity	NPC471720
0.8229	Intermediate Similarity	NPC91010
0.8218	Intermediate Similarity	NPC146731
0.8218	Intermediate Similarity	NPC189616
0.8211	Intermediate Similarity	NPC177037
0.8211	Intermediate Similarity	NPC297265
0.8211	Intermediate Similarity	NPC472814
0.8211	Intermediate Similarity	NPC303697
0.8211	Intermediate Similarity	NPC65513
0.82	Intermediate Similarity	NPC134077
0.82	Intermediate Similarity	NPC162973
0.82	Intermediate Similarity	NPC137430
0.82	Intermediate Similarity	NPC165250
0.819	Intermediate Similarity	NPC476801
0.8182	Intermediate Similarity	NPC35574
0.8182	Intermediate Similarity	NPC266955
0.8182	Intermediate Similarity	NPC470761
0.8182	Intermediate Similarity	NPC473219
0.8182	Intermediate Similarity	NPC470906
0.8173	Intermediate Similarity	NPC286880
0.8173	Intermediate Similarity	NPC5103
0.8172	Intermediate Similarity	NPC175293
0.8163	Intermediate Similarity	NPC254496
0.8163	Intermediate Similarity	NPC38530
0.8163	Intermediate Similarity	NPC84335

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 NPC183012 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1278
0.2-0.3	3457
0.3-0.4	2696
0.4-0.5	1009
0.5-0.6	273
0.6-0.7	211
0.7-0.8	84
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
0.8556	High Similarity	NPD1694	Approved
0.8454	Intermediate Similarity	NPD4225	Approved
0.8081	Intermediate Similarity	NPD7638	Approved
0.8022	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7640	Approved
0.8	Intermediate Similarity	NPD7639	Approved
0.798	Intermediate Similarity	NPD7902	Approved
0.7938	Intermediate Similarity	NPD6399	Phase 3
0.789	Intermediate Similarity	NPD7115	Discovery
0.7872	Intermediate Similarity	NPD3618	Phase 1
0.7857	Intermediate Similarity	NPD7748	Approved
0.7835	Intermediate Similarity	NPD7515	Phase 2
0.7677	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7900	Approved
0.76	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6649	Approved
0.7593	Intermediate Similarity	NPD6650	Approved
0.757	Intermediate Similarity	NPD6372	Approved
0.757	Intermediate Similarity	NPD6373	Approved
0.7547	Intermediate Similarity	NPD5697	Approved
0.7525	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6011	Approved
0.7477	Intermediate Similarity	NPD6881	Approved
0.7477	Intermediate Similarity	NPD6899	Approved
0.7475	Intermediate Similarity	NPD6079	Approved
0.7453	Intermediate Similarity	NPD6675	Approved
0.7453	Intermediate Similarity	NPD5739	Approved
0.7453	Intermediate Similarity	NPD7128	Approved
0.7453	Intermediate Similarity	NPD6402	Approved
0.7449	Intermediate Similarity	NPD5328	Approved
0.7447	Intermediate Similarity	NPD3667	Approved
0.7407	Intermediate Similarity	NPD6012	Approved
0.7407	Intermediate Similarity	NPD6013	Approved
0.7407	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6014	Approved
0.7383	Intermediate Similarity	NPD5701	Approved
0.7374	Intermediate Similarity	NPD5785	Approved
0.7353	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5222	Approved
0.7353	Intermediate Similarity	NPD5221	Approved
0.7339	Intermediate Similarity	NPD7290	Approved
0.7339	Intermediate Similarity	NPD7102	Approved
0.7339	Intermediate Similarity	NPD6883	Approved
0.7333	Intermediate Similarity	NPD7632	Discontinued
0.732	Intermediate Similarity	NPD6409	Approved
0.732	Intermediate Similarity	NPD6684	Approved
0.732	Intermediate Similarity	NPD7521	Approved
0.732	Intermediate Similarity	NPD5330	Approved
0.732	Intermediate Similarity	NPD7334	Approved
0.732	Intermediate Similarity	NPD7146	Approved
0.7315	Intermediate Similarity	NPD6686	Approved
0.7315	Intermediate Similarity	NPD7320	Approved
0.73	Intermediate Similarity	NPD8035	Phase 2
0.73	Intermediate Similarity	NPD8034	Phase 2
0.7292	Intermediate Similarity	NPD3133	Approved
0.7292	Intermediate Similarity	NPD3666	Approved
0.7292	Intermediate Similarity	NPD4786	Approved
0.7292	Intermediate Similarity	NPD3665	Phase 1
0.729	Intermediate Similarity	NPD6008	Approved
0.7282	Intermediate Similarity	NPD5173	Approved
0.7282	Intermediate Similarity	NPD6083	Phase 2
0.7282	Intermediate Similarity	NPD6084	Phase 2
0.7273	Intermediate Similarity	NPD6617	Approved
0.7273	Intermediate Similarity	NPD6869	Approved
0.7273	Intermediate Similarity	NPD6847	Approved
0.7273	Intermediate Similarity	NPD8130	Phase 1
0.7255	Intermediate Similarity	NPD5695	Phase 3
0.7255	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD3573	Approved
0.7228	Intermediate Similarity	NPD4202	Approved
0.7222	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5696	Approved
0.7207	Intermediate Similarity	NPD6882	Approved
0.7207	Intermediate Similarity	NPD8297	Approved
0.7172	Intermediate Similarity	NPD6672	Approved
0.7172	Intermediate Similarity	NPD6903	Approved
0.7172	Intermediate Similarity	NPD5737	Approved
0.7172	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5211	Phase 2
0.7143	Intermediate Similarity	NPD5285	Approved
0.7143	Intermediate Similarity	NPD5286	Approved
0.7143	Intermediate Similarity	NPD4696	Approved
0.7143	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6411	Approved
0.7129	Intermediate Similarity	NPD5693	Phase 1
0.7117	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4755	Approved
0.7075	Intermediate Similarity	NPD5223	Approved
0.7059	Intermediate Similarity	NPD5779	Approved
0.7059	Intermediate Similarity	NPD5778	Approved
0.7053	Intermediate Similarity	NPD4695	Discontinued
0.7041	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5141	Approved
0.7018	Intermediate Similarity	NPD6274	Approved
0.7018	Intermediate Similarity	NPD6868	Approved
0.7009	Intermediate Similarity	NPD4633	Approved
0.7009	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD5226	Approved
0.7009	Intermediate Similarity	NPD5225	Approved
0.7009	Intermediate Similarity	NPD5224	Approved
0.6991	Remote Similarity	NPD4632	Approved
0.699	Remote Similarity	NPD6001	Approved
0.6981	Remote Similarity	NPD4700	Approved
0.697	Remote Similarity	NPD5279	Phase 3
0.6961	Remote Similarity	NPD5281	Approved
0.6961	Remote Similarity	NPD5284	Approved
0.6957	Remote Similarity	NPD6317	Approved
0.6944	Remote Similarity	NPD5174	Approved
0.6944	Remote Similarity	NPD5175	Approved
0.6939	Remote Similarity	NPD3668	Phase 3
0.6939	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD6101	Approved
0.6931	Remote Similarity	NPD4753	Phase 2
0.6923	Remote Similarity	NPD4629	Approved
0.6923	Remote Similarity	NPD5210	Approved
0.6903	Remote Similarity	NPD6053	Discontinued
0.6897	Remote Similarity	NPD6335	Approved
0.6897	Remote Similarity	NPD6314	Approved
0.6897	Remote Similarity	NPD6313	Approved
0.6869	Remote Similarity	NPD5363	Approved
0.6869	Remote Similarity	NPD1696	Phase 3
0.6863	Remote Similarity	NPD46	Approved
0.6863	Remote Similarity	NPD6698	Approved
0.6863	Remote Similarity	NPD5207	Approved
0.6838	Remote Similarity	NPD7101	Approved
0.6838	Remote Similarity	NPD7100	Approved
0.681	Remote Similarity	NPD6009	Approved
0.68	Remote Similarity	NPD4519	Discontinued
0.68	Remote Similarity	NPD4623	Approved
0.6789	Remote Similarity	NPD4754	Approved
0.678	Remote Similarity	NPD6319	Approved
0.6777	Remote Similarity	NPD7507	Approved
0.6765	Remote Similarity	NPD6673	Approved
0.6765	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD6080	Approved
0.6765	Remote Similarity	NPD6904	Approved
0.6765	Remote Similarity	NPD6051	Approved
0.6759	Remote Similarity	NPD5344	Discontinued
0.6735	Remote Similarity	NPD4221	Approved
0.6735	Remote Similarity	NPD4223	Phase 3
0.6726	Remote Similarity	NPD6371	Approved
0.6723	Remote Similarity	NPD5983	Phase 2
0.6702	Remote Similarity	NPD8039	Approved
0.6699	Remote Similarity	NPD5692	Phase 3
0.6696	Remote Similarity	NPD5168	Approved
0.6696	Remote Similarity	NPD4730	Approved
0.6696	Remote Similarity	NPD4729	Approved
0.6696	Remote Similarity	NPD5128	Approved
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD4767	Approved
0.6667	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6616	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6637	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7637	Suspended
0.6635	Remote Similarity	NPD5694	Approved
0.6635	Remote Similarity	NPD6050	Approved
0.6634	Remote Similarity	NPD5690	Phase 2
0.6634	Remote Similarity	NPD5786	Approved
0.6632	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD7319	Approved
0.6612	Remote Similarity	NPD7604	Phase 2
0.6607	Remote Similarity	NPD6412	Phase 2
0.6607	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD1695	Approved
0.66	Remote Similarity	NPD4197	Approved
0.6598	Remote Similarity	NPD7645	Phase 2
0.6585	Remote Similarity	NPD7078	Approved
0.6583	Remote Similarity	NPD6015	Approved
0.6583	Remote Similarity	NPD6908	Approved
0.6583	Remote Similarity	NPD6016	Approved
0.6583	Remote Similarity	NPD6909	Approved
0.6579	Remote Similarity	NPD5250	Approved
0.6579	Remote Similarity	NPD4634	Approved
0.6579	Remote Similarity	NPD5248	Approved
0.6579	Remote Similarity	NPD5169	Approved
0.6579	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5251	Approved
0.6579	Remote Similarity	NPD5247	Approved
0.6579	Remote Similarity	NPD5249	Phase 3
0.6579	Remote Similarity	NPD5135	Approved
0.6574	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4269	Approved
0.6566	Remote Similarity	NPD5209	Approved
0.6566	Remote Similarity	NPD4270	Approved
0.6549	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5329	Approved
0.6535	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7736	Approved
0.6531	Remote Similarity	NPD7525	Registered
0.6531	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5988	Approved
0.6529	Remote Similarity	NPD6370	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