NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	408.29
Volume:	442.589
LogP:	4.801
LogD:	3.51
LogS:	-4.285
# Rotatable Bonds:	8
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.405
Synthetic Accessibility Score:	4.764
Fsp3:	0.792
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.156
MDCK Permeability:	2.039606806647498e-05
Pgp-inhibitor:	0.097
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.26
Plasma Protein Binding (PPB):	95.77763366699219%
Volume Distribution (VD):	1.209
Pgp-substrate:	2.964555501937866%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.589
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.886
CYP2C9-inhibitor:	0.149
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.385
CYP3A4-inhibitor:	0.182
CYP3A4-substrate:	0.117

ADMET: Excretion

Clearance (CL):	3.245
Half-life (T1/2):	0.365

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.441
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.143
Maximum Recommended Daily Dose:	0.096
Skin Sensitization:	0.464
Carcinogencity:	0.079
Eye Corrosion:	0.024
Eye Irritation:	0.233
Respiratory Toxicity:	0.026

Download Data

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

Natural Product: NPC476982

Natural Product ID:	NPC476982
*Common Name:**	Tasnemoxide A
IUPAC Name:	(2S)-2-[(3R,6R)-6-[(E)-4-hydroxy-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-2-enyl]-6-methyldioxan-3-yl]propanoic acid
Synonyms:
Standard InCHIKey:	IOPIOUHRQRYDMU-GGYDGERUSA-N
Standard InCHI:	InChI=1S/C24H40O5/c1-17-9-7-12-22(3,4)19(17)10-15-23(5,27)13-8-14-24(6)16-11-20(28-29-24)18(2)21(25)26/h8,13,18,20,27H,7,9-12,14-16H2,1-6H3,(H,25,26)/b13-8+/t18-,20+,23?,24-/m0/s1
SMILES:	CC1=C(C(CCC1)(C)C)CCC(C)(/C=C/C[C@]2(CC[C@@H](OO2)[C@H](C)C(=O)O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	11189028
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32571	diacarnus erythraenus	Species	Podospongiidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[11678661]
NPO32571	diacarnus erythraenus	Species	Podospongiidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[14738401]

☑ 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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	>	1	ug/ml	PMID[17618015]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	1	ug/ml	PMID[17618015]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	1	ug/ml	PMID[17618015]
NPT168	Cell Line	P388	Mus musculus	IC50	>	1	ug/ml	PMID[14738401]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	1	ug/ml	PMID[14738401]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	1	ug/ml	PMID[14738401]

☑ 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 NPC476982 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	172
0.1-0.2	985
0.2-0.3	4323
0.3-0.4	10737
0.4-0.5	12840
0.5-0.6	7181
0.6-0.7	5385
0.7-0.8	1022
0.8-0.85	33
0.85-0.9	13
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9383	High Similarity	NPC476983
0.9375	High Similarity	NPC172309
0.9375	High Similarity	NPC117960
0.9375	High Similarity	NPC14044
0.9157	High Similarity	NPC471344
0.9048	High Similarity	NPC476104
0.9	High Similarity	NPC121200
0.8889	High Similarity	NPC82488
0.8889	High Similarity	NPC308545
0.8875	High Similarity	NPC281296
0.8824	High Similarity	NPC262085
0.875	High Similarity	NPC469514
0.8675	High Similarity	NPC476988
0.8625	High Similarity	NPC60718
0.8571	High Similarity	NPC476984
0.8571	High Similarity	NPC475395
0.8537	High Similarity	NPC470905
0.8537	High Similarity	NPC476986
0.8519	High Similarity	NPC152754
0.8519	High Similarity	NPC59602
0.8519	High Similarity	NPC474447
0.8519	High Similarity	NPC476987
0.8471	Intermediate Similarity	NPC476100
0.8415	Intermediate Similarity	NPC476325
0.8415	Intermediate Similarity	NPC476264
0.8395	Intermediate Similarity	NPC199445
0.8372	Intermediate Similarity	NPC471343
0.8315	Intermediate Similarity	NPC471342
0.8315	Intermediate Similarity	NPC469866
0.8272	Intermediate Similarity	NPC330016
0.8256	Intermediate Similarity	NPC69469
0.8214	Intermediate Similarity	NPC254996
0.8214	Intermediate Similarity	NPC113363
0.8214	Intermediate Similarity	NPC268502
0.8182	Intermediate Similarity	NPC473226
0.8182	Intermediate Similarity	NPC475181
0.8148	Intermediate Similarity	NPC167145
0.814	Intermediate Similarity	NPC476292
0.814	Intermediate Similarity	NPC474605
0.8132	Intermediate Similarity	NPC36491
0.8095	Intermediate Similarity	NPC179028
0.8072	Intermediate Similarity	NPC476985
0.8072	Intermediate Similarity	NPC474316
0.8072	Intermediate Similarity	NPC475744
0.8025	Intermediate Similarity	NPC126061
0.8023	Intermediate Similarity	NPC79277
0.8023	Intermediate Similarity	NPC475481
0.8022	Intermediate Similarity	NPC214844
0.8	Intermediate Similarity	NPC246458
0.8	Intermediate Similarity	NPC174663
0.7978	Intermediate Similarity	NPC82979
0.7978	Intermediate Similarity	NPC470955
0.7976	Intermediate Similarity	NPC469867
0.7955	Intermediate Similarity	NPC295799
0.7927	Intermediate Similarity	NPC238425
0.7927	Intermediate Similarity	NPC472018
0.7927	Intermediate Similarity	NPC474543
0.7912	Intermediate Similarity	NPC97577
0.7889	Intermediate Similarity	NPC86005
0.7889	Intermediate Similarity	NPC128644
0.7882	Intermediate Similarity	NPC239098
0.7882	Intermediate Similarity	NPC321514
0.7872	Intermediate Similarity	NPC53565
0.7872	Intermediate Similarity	NPC266899
0.7872	Intermediate Similarity	NPC134067
0.7865	Intermediate Similarity	NPC269638
0.7857	Intermediate Similarity	NPC239127
0.7831	Intermediate Similarity	NPC474551
0.7826	Intermediate Similarity	NPC15059
0.7816	Intermediate Similarity	NPC327002
0.7812	Intermediate Similarity	NPC316598
0.7802	Intermediate Similarity	NPC104560
0.7789	Intermediate Similarity	NPC116457
0.7789	Intermediate Similarity	NPC132824
0.7778	Intermediate Similarity	NPC322159
0.7778	Intermediate Similarity	NPC198761
0.7766	Intermediate Similarity	NPC470958
0.7766	Intermediate Similarity	NPC470957
0.7765	Intermediate Similarity	NPC122847
0.7753	Intermediate Similarity	NPC120158
0.7753	Intermediate Similarity	NPC475193
0.7753	Intermediate Similarity	NPC165064
0.7738	Intermediate Similarity	NPC255060
0.7717	Intermediate Similarity	NPC118011
0.7717	Intermediate Similarity	NPC36668
0.7717	Intermediate Similarity	NPC256902
0.7717	Intermediate Similarity	NPC155479
0.7717	Intermediate Similarity	NPC118193
0.7717	Intermediate Similarity	NPC281524
0.7708	Intermediate Similarity	NPC57416
0.7708	Intermediate Similarity	NPC53844
0.7708	Intermediate Similarity	NPC254496
0.7708	Intermediate Similarity	NPC472851
0.7708	Intermediate Similarity	NPC107243
0.7701	Intermediate Similarity	NPC476265
0.7701	Intermediate Similarity	NPC157895
0.7701	Intermediate Similarity	NPC104120
0.7701	Intermediate Similarity	NPC148685
0.7701	Intermediate Similarity	NPC274522
0.7692	Intermediate Similarity	NPC171722
0.7692	Intermediate Similarity	NPC477926
0.7684	Intermediate Similarity	NPC290481
0.7683	Intermediate Similarity	NPC69462
0.7683	Intermediate Similarity	NPC472017
0.7677	Intermediate Similarity	NPC475050
0.7677	Intermediate Similarity	NPC90177
0.7674	Intermediate Similarity	NPC247783
0.7674	Intermediate Similarity	NPC269543
0.7667	Intermediate Similarity	NPC76333
0.7667	Intermediate Similarity	NPC474369
0.766	Intermediate Similarity	NPC476416
0.766	Intermediate Similarity	NPC115021
0.7653	Intermediate Similarity	NPC244456
0.7653	Intermediate Similarity	NPC282524
0.7653	Intermediate Similarity	NPC115862
0.7653	Intermediate Similarity	NPC469657
0.764	Intermediate Similarity	NPC474809
0.764	Intermediate Similarity	NPC477373
0.7624	Intermediate Similarity	NPC64844
0.7624	Intermediate Similarity	NPC42847
0.7619	Intermediate Similarity	NPC18819
0.7619	Intermediate Similarity	NPC46610
0.7614	Intermediate Similarity	NPC473420
0.7614	Intermediate Similarity	NPC229584
0.7614	Intermediate Similarity	NPC14151
0.7614	Intermediate Similarity	NPC88735
0.7614	Intermediate Similarity	NPC14203
0.7609	Intermediate Similarity	NPC1753
0.7609	Intermediate Similarity	NPC474511
0.7609	Intermediate Similarity	NPC72397
0.7604	Intermediate Similarity	NPC235053
0.7604	Intermediate Similarity	NPC469369
0.7604	Intermediate Similarity	NPC469528
0.76	Intermediate Similarity	NPC239162
0.76	Intermediate Similarity	NPC220964
0.76	Intermediate Similarity	NPC475676
0.7586	Intermediate Similarity	NPC327674
0.7582	Intermediate Similarity	NPC73038
0.7582	Intermediate Similarity	NPC475753
0.7582	Intermediate Similarity	NPC470415
0.7582	Intermediate Similarity	NPC202394
0.7582	Intermediate Similarity	NPC116575
0.7582	Intermediate Similarity	NPC194417
0.7579	Intermediate Similarity	NPC475572
0.7579	Intermediate Similarity	NPC148964
0.7579	Intermediate Similarity	NPC53685
0.7579	Intermediate Similarity	NPC6818
0.7579	Intermediate Similarity	NPC114159
0.7579	Intermediate Similarity	NPC191412
0.7576	Intermediate Similarity	NPC475091
0.7576	Intermediate Similarity	NPC183571
0.7561	Intermediate Similarity	NPC107130
0.7558	Intermediate Similarity	NPC74995
0.7558	Intermediate Similarity	NPC107668
0.7558	Intermediate Similarity	NPC61952
0.7556	Intermediate Similarity	NPC31086
0.7556	Intermediate Similarity	NPC472326
0.7553	Intermediate Similarity	NPC282616
0.7553	Intermediate Similarity	NPC155120
0.7553	Intermediate Similarity	NPC288833
0.7553	Intermediate Similarity	NPC471588
0.7553	Intermediate Similarity	NPC324341
0.7553	Intermediate Similarity	NPC45269
0.7553	Intermediate Similarity	NPC228784
0.7553	Intermediate Similarity	NPC472814
0.7553	Intermediate Similarity	NPC966
0.7553	Intermediate Similarity	NPC177037
0.7553	Intermediate Similarity	NPC6255
0.7551	Intermediate Similarity	NPC35239
0.7551	Intermediate Similarity	NPC474718
0.7551	Intermediate Similarity	NPC54705
0.7551	Intermediate Similarity	NPC241221
0.7549	Intermediate Similarity	NPC322903
0.7528	Intermediate Similarity	NPC474252
0.7528	Intermediate Similarity	NPC73882
0.7528	Intermediate Similarity	NPC7414
0.7528	Intermediate Similarity	NPC279186
0.7527	Intermediate Similarity	NPC214387
0.7527	Intermediate Similarity	NPC474700
0.7526	Intermediate Similarity	NPC170131
0.7526	Intermediate Similarity	NPC124246
0.7526	Intermediate Similarity	NPC187933
0.7526	Intermediate Similarity	NPC285513
0.7525	Intermediate Similarity	NPC475802
0.75	Intermediate Similarity	NPC476409
0.75	Intermediate Similarity	NPC158141
0.75	Intermediate Similarity	NPC72151
0.75	Intermediate Similarity	NPC4620
0.75	Intermediate Similarity	NPC69171
0.75	Intermediate Similarity	NPC231599
0.75	Intermediate Similarity	NPC477959
0.75	Intermediate Similarity	NPC271104
0.75	Intermediate Similarity	NPC474165
0.75	Intermediate Similarity	NPC96496
0.75	Intermediate Similarity	NPC181327
0.75	Intermediate Similarity	NPC173089
0.75	Intermediate Similarity	NPC195715
0.75	Intermediate Similarity	NPC312215
0.75	Intermediate Similarity	NPC37038
0.75	Intermediate Similarity	NPC312561

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 NPC476982 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1388
0.2-0.3	3631
0.3-0.4	2544
0.4-0.5	895
0.5-0.6	330
0.6-0.7	194
0.7-0.8	15
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8132	Intermediate Similarity	NPD6411	Approved
0.8043	Intermediate Similarity	NPD5778	Approved
0.8043	Intermediate Similarity	NPD5779	Approved
0.7912	Intermediate Similarity	NPD6101	Approved
0.7912	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4270	Approved
0.7528	Intermediate Similarity	NPD4269	Approved
0.75	Intermediate Similarity	NPD4822	Approved
0.75	Intermediate Similarity	NPD4820	Approved
0.75	Intermediate Similarity	NPD4819	Approved
0.75	Intermediate Similarity	NPD4821	Approved
0.7471	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7154	Phase 3
0.7368	Intermediate Similarity	NPD7637	Suspended
0.7368	Intermediate Similarity	NPD7983	Approved
0.7303	Intermediate Similarity	NPD4252	Approved
0.7292	Intermediate Similarity	NPD6399	Phase 3
0.7283	Intermediate Similarity	NPD5363	Approved
0.7273	Intermediate Similarity	NPD4271	Approved
0.7273	Intermediate Similarity	NPD4268	Approved
0.7263	Intermediate Similarity	NPD5785	Approved
0.7253	Intermediate Similarity	NPD5362	Discontinued
0.7245	Intermediate Similarity	NPD7839	Suspended
0.7222	Intermediate Similarity	NPD5369	Approved
0.7204	Intermediate Similarity	NPD5786	Approved
0.7126	Intermediate Similarity	NPD8039	Approved
0.7111	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD46	Approved
0.7083	Intermediate Similarity	NPD6698	Approved
0.7041	Intermediate Similarity	NPD5282	Discontinued
0.701	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD7115	Discovery
0.6989	Remote Similarity	NPD4786	Approved
0.697	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3667	Approved
0.6931	Remote Similarity	NPD4225	Approved
0.6923	Remote Similarity	NPD5368	Approved
0.6882	Remote Similarity	NPD5332	Approved
0.6882	Remote Similarity	NPD5331	Approved
0.6869	Remote Similarity	NPD7748	Approved
0.6848	Remote Similarity	NPD4790	Discontinued
0.6842	Remote Similarity	NPD4623	Approved
0.6842	Remote Similarity	NPD4519	Discontinued
0.6837	Remote Similarity	NPD5281	Approved
0.6837	Remote Similarity	NPD5284	Approved
0.6832	Remote Similarity	NPD6084	Phase 2
0.6832	Remote Similarity	NPD6083	Phase 2
0.6832	Remote Similarity	NPD7902	Approved
0.6809	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5695	Phase 3
0.6774	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6435	Approved
0.6759	Remote Similarity	NPD6371	Approved
0.6742	Remote Similarity	NPD8264	Approved
0.6739	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4695	Discontinued
0.6731	Remote Similarity	NPD5211	Phase 2
0.6729	Remote Similarity	NPD6881	Approved
0.6729	Remote Similarity	NPD6686	Approved
0.6729	Remote Similarity	NPD6899	Approved
0.6698	Remote Similarity	NPD6675	Approved
0.6698	Remote Similarity	NPD7128	Approved
0.6698	Remote Similarity	NPD6402	Approved
0.6698	Remote Similarity	NPD5739	Approved
0.6697	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5697	Approved
0.6633	Remote Similarity	NPD4753	Phase 2
0.6633	Remote Similarity	NPD5370	Suspended
0.6633	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3133	Approved
0.6632	Remote Similarity	NPD3665	Phase 1
0.6632	Remote Similarity	NPD3666	Approved
0.6632	Remote Similarity	NPD3668	Phase 3
0.6632	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD7102	Approved
0.6606	Remote Similarity	NPD6883	Approved
0.6606	Remote Similarity	NPD7290	Approved
0.6604	Remote Similarity	NPD5141	Approved
0.6602	Remote Similarity	NPD5696	Approved
0.6602	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4250	Approved
0.6598	Remote Similarity	NPD4251	Approved
0.6588	Remote Similarity	NPD7331	Phase 2
0.6574	Remote Similarity	NPD7320	Approved
0.6562	Remote Similarity	NPD1694	Approved
0.6559	Remote Similarity	NPD7332	Phase 2
0.6559	Remote Similarity	NPD6931	Approved
0.6559	Remote Similarity	NPD7514	Phase 3
0.6559	Remote Similarity	NPD6930	Phase 2
0.6545	Remote Similarity	NPD6847	Approved
0.6545	Remote Similarity	NPD6649	Approved
0.6545	Remote Similarity	NPD6650	Approved
0.6545	Remote Similarity	NPD8130	Phase 1
0.6545	Remote Similarity	NPD6869	Approved
0.6545	Remote Similarity	NPD6617	Approved
0.6538	Remote Similarity	NPD5286	Approved
0.6538	Remote Similarity	NPD5285	Approved
0.6538	Remote Similarity	NPD7640	Approved
0.6538	Remote Similarity	NPD4696	Approved
0.6538	Remote Similarity	NPD7639	Approved
0.6535	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD7900	Approved
0.6531	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6672	Approved
0.6531	Remote Similarity	NPD6903	Approved
0.6531	Remote Similarity	NPD5737	Approved
0.6526	Remote Similarity	NPD6695	Phase 3
0.6522	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6013	Approved
0.6514	Remote Similarity	NPD6012	Approved
0.6514	Remote Similarity	NPD6373	Approved
0.6514	Remote Similarity	NPD6014	Approved
0.6514	Remote Similarity	NPD6372	Approved
0.6505	Remote Similarity	NPD4755	Approved
0.65	Remote Similarity	NPD6079	Approved
0.6495	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD4249	Approved
0.6495	Remote Similarity	NPD5279	Phase 3
0.6495	Remote Similarity	NPD3618	Phase 1
0.6495	Remote Similarity	NPD6422	Discontinued
0.6486	Remote Similarity	NPD8297	Approved
0.6486	Remote Similarity	NPD6053	Discontinued
0.6486	Remote Similarity	NPD6882	Approved
0.6481	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5701	Approved
0.6471	Remote Similarity	NPD5210	Approved
0.6471	Remote Similarity	NPD4629	Approved
0.6471	Remote Similarity	NPD7341	Phase 2
0.6466	Remote Similarity	NPD8517	Approved
0.6466	Remote Similarity	NPD8516	Approved
0.6466	Remote Similarity	NPD8515	Approved
0.6466	Remote Similarity	NPD8513	Phase 3
0.6465	Remote Similarity	NPD5328	Approved
0.6452	Remote Similarity	NPD6929	Approved
0.6444	Remote Similarity	NPD6926	Approved
0.6444	Remote Similarity	NPD6924	Approved
0.6442	Remote Similarity	NPD7638	Approved
0.6436	Remote Similarity	NPD4202	Approved
0.6429	Remote Similarity	NPD3573	Approved
0.6422	Remote Similarity	NPD6011	Approved
0.6422	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD4221	Approved
0.6421	Remote Similarity	NPD4223	Phase 3
0.6415	Remote Similarity	NPD4633	Approved
0.6415	Remote Similarity	NPD5224	Approved
0.6415	Remote Similarity	NPD5226	Approved
0.6415	Remote Similarity	NPD5225	Approved
0.6413	Remote Similarity	NPD4756	Discovery
0.64	Remote Similarity	NPD7838	Discovery
0.6392	Remote Similarity	NPD5329	Approved
0.6392	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4700	Approved
0.6364	Remote Similarity	NPD4518	Approved
0.6355	Remote Similarity	NPD5174	Approved
0.6355	Remote Similarity	NPD5175	Approved
0.6353	Remote Similarity	NPD3197	Phase 1
0.6344	Remote Similarity	NPD3732	Approved
0.6344	Remote Similarity	NPD7145	Approved
0.6337	Remote Similarity	NPD8035	Phase 2
0.6337	Remote Similarity	NPD8034	Phase 2
0.633	Remote Similarity	NPD6412	Phase 2
0.6327	Remote Similarity	NPD6098	Approved
0.6327	Remote Similarity	NPD5690	Phase 2
0.6322	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5344	Discontinued
0.6321	Remote Similarity	NPD5223	Approved
0.6316	Remote Similarity	NPD6902	Approved
0.631	Remote Similarity	NPD368	Approved
0.631	Remote Similarity	NPD4191	Approved
0.631	Remote Similarity	NPD4192	Approved
0.631	Remote Similarity	NPD4194	Approved
0.631	Remote Similarity	NPD4193	Approved
0.6306	Remote Similarity	NPD4634	Approved
0.6304	Remote Similarity	NPD6933	Approved
0.63	Remote Similarity	NPD6051	Approved
0.63	Remote Similarity	NPD6080	Approved
0.63	Remote Similarity	NPD6673	Approved
0.63	Remote Similarity	NPD6904	Approved
0.6289	Remote Similarity	NPD4197	Approved
0.6263	Remote Similarity	NPD7524	Approved
0.6263	Remote Similarity	NPD7750	Discontinued
0.625	Remote Similarity	NPD3194	Approved
0.625	Remote Similarity	NPD3195	Phase 2
0.625	Remote Similarity	NPD4266	Approved
0.625	Remote Similarity	NPD5222	Approved
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3196	Approved
0.625	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5221	Approved
0.625	Remote Similarity	NPD5209	Approved
0.6239	Remote Similarity	NPD6319	Approved
0.6237	Remote Similarity	NPD6932	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