NPASS Compound

Structure

NPC474311 OpenBabel07101719122D 26 28 0 0 1 0 0 0 0 0999 V2000 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 8 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 14 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 15 1 0 0 0 0 12 16 2 0 0 0 0 13 16 1 0 0 0 0 13 17 1 0 0 0 0 14 21 2 0 0 0 0 15 22 2 0 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 17 24 2 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 18 25 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	356.13
Volume:	360.456
LogP:	3.592
LogD:	2.356
LogS:	-3.629
# Rotatable Bonds:	1
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.461
Synthetic Accessibility Score:	3.929
Fsp3:	0.3
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:	-5.023
MDCK Permeability:	1.400696964992676e-05
Pgp-inhibitor:	0.127
Pgp-substrate:	0.578
Human Intestinal Absorption (HIA):	0.065
20% Bioavailability (F20%):	0.312
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.042
Plasma Protein Binding (PPB):	98.57886505126953%
Volume Distribution (VD):	0.697
Pgp-substrate:	3.75150990486145%

ADMET: Metabolism

CYP1A2-inhibitor:	0.525
CYP1A2-substrate:	0.783
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.649
CYP2C9-inhibitor:	0.136
CYP2C9-substrate:	0.53
CYP2D6-inhibitor:	0.04
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.35
CYP3A4-substrate:	0.853

ADMET: Excretion

Clearance (CL):	2.113
Half-life (T1/2):	0.309

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.616
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.621
Skin Sensitization:	0.762
Carcinogencity:	0.449
Eye Corrosion:	0.003
Eye Irritation:	0.865
Respiratory Toxicity:	0.211

Download Data

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

Natural Product: NPC474311

Natural Product ID:	NPC474311
*Common Name:**	2-Hydroxygarveatin E
IUPAC Name:	7-ethyl-2,9-dihydroxy-2,4,4,6-tetramethylanthracene-1,3,5,8-tetrone
Synonyms:	2-Hydroxygarveatin E
Standard InCHIKey:	MEDXQZJJCUKMBX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-6-9-8(2)14(21)10-7-11-13(16(23)12(10)15(9)22)17(24)20(5,26)18(25)19(11,3)4/h7,23,26H,6H2,1-5H3
SMILES:	CCC1=C(C(=O)C2=CC3=C(C(=C2C1=O)O)C(=O)C(C(=O)C3(C)C)(C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465021
PubChem CID:	16091656
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO2240	Garveia annulata	Species	Bougainvilliidae	Eukaryota	n.a.	Northeastern Pacific	n.a.	PMID[17067170]
NPO2240	Garveia annulata	Species	Bougainvilliidae	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
Ki	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	Ki	=	1400.0	nM	PMID[512654]

☑ 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 NPC474311 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	375
0.1-0.2	1649
0.2-0.3	3780
0.3-0.4	10132
0.4-0.5	10024
0.5-0.6	6767
0.6-0.7	7650
0.7-0.8	2028
0.8-0.85	241
0.85-0.9	49
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC17083
0.8951	High Similarity	NPC474310
0.8897	High Similarity	NPC80035
0.8872	High Similarity	NPC171460
0.8806	High Similarity	NPC108129
0.8788	High Similarity	NPC254492
0.8768	High Similarity	NPC475957
0.875	High Similarity	NPC53896
0.8722	High Similarity	NPC72667
0.8722	High Similarity	NPC471530
0.8705	High Similarity	NPC13715
0.8696	High Similarity	NPC472308
0.8686	High Similarity	NPC202225
0.8686	High Similarity	NPC50924
0.8667	High Similarity	NPC198305
0.8667	High Similarity	NPC55949
0.8636	High Similarity	NPC310540
0.8613	High Similarity	NPC114183
0.8613	High Similarity	NPC254603
0.8613	High Similarity	NPC171968
0.8613	High Similarity	NPC115458
0.8611	High Similarity	NPC136878
0.8601	High Similarity	NPC29932
0.8601	High Similarity	NPC79627
0.8593	High Similarity	NPC303910
0.8593	High Similarity	NPC25736
0.8593	High Similarity	NPC146647
0.8593	High Similarity	NPC34414
0.8593	High Similarity	NPC278928
0.8582	High Similarity	NPC176130
0.8582	High Similarity	NPC78364
0.8582	High Similarity	NPC69424
0.8582	High Similarity	NPC84672
0.8571	High Similarity	NPC4214
0.8571	High Similarity	NPC230811
0.8571	High Similarity	NPC123506
0.8561	High Similarity	NPC86524
0.8561	High Similarity	NPC272268
0.8551	High Similarity	NPC12070
0.8551	High Similarity	NPC270899
0.854	High Similarity	NPC58685
0.8519	High Similarity	NPC48248
0.8507	High Similarity	NPC15837
0.8507	High Similarity	NPC231774
0.8507	High Similarity	NPC306765
0.85	High Similarity	NPC471452
0.85	High Similarity	NPC53001
0.8496	Intermediate Similarity	NPC142956
0.8496	Intermediate Similarity	NPC199273
0.8489	Intermediate Similarity	NPC283088
0.8489	Intermediate Similarity	NPC249272
0.8485	Intermediate Similarity	NPC307174
0.8478	Intermediate Similarity	NPC138472
0.8478	Intermediate Similarity	NPC52407
0.8478	Intermediate Similarity	NPC78307
0.8478	Intermediate Similarity	NPC477139
0.8478	Intermediate Similarity	NPC225051
0.8478	Intermediate Similarity	NPC193169
0.8473	Intermediate Similarity	NPC472046
0.8467	Intermediate Similarity	NPC244699
0.8467	Intermediate Similarity	NPC471851
0.8462	Intermediate Similarity	NPC193555
0.8451	Intermediate Similarity	NPC315578
0.844	Intermediate Similarity	NPC87723
0.8429	Intermediate Similarity	NPC155211
0.8429	Intermediate Similarity	NPC193358
0.8421	Intermediate Similarity	NPC273683
0.8417	Intermediate Similarity	NPC288089
0.8406	Intermediate Similarity	NPC88864
0.8406	Intermediate Similarity	NPC309430
0.8403	Intermediate Similarity	NPC143898
0.8394	Intermediate Similarity	NPC199253
0.8394	Intermediate Similarity	NPC136588
0.8382	Intermediate Similarity	NPC237225
0.8382	Intermediate Similarity	NPC96024
0.8382	Intermediate Similarity	NPC282923
0.838	Intermediate Similarity	NPC26924
0.838	Intermediate Similarity	NPC294330
0.838	Intermediate Similarity	NPC138099
0.838	Intermediate Similarity	NPC242994
0.837	Intermediate Similarity	NPC1991
0.837	Intermediate Similarity	NPC3224
0.8369	Intermediate Similarity	NPC36868
0.8369	Intermediate Similarity	NPC471905
0.8357	Intermediate Similarity	NPC258502
0.8356	Intermediate Similarity	NPC143685
0.8346	Intermediate Similarity	NPC282577
0.8345	Intermediate Similarity	NPC471906
0.8345	Intermediate Similarity	NPC4170
0.8345	Intermediate Similarity	NPC111845
0.8333	Intermediate Similarity	NPC205992
0.8333	Intermediate Similarity	NPC308572
0.8333	Intermediate Similarity	NPC291078
0.8322	Intermediate Similarity	NPC181560
0.8322	Intermediate Similarity	NPC169452
0.8321	Intermediate Similarity	NPC276238
0.8321	Intermediate Similarity	NPC99731
0.831	Intermediate Similarity	NPC51531
0.831	Intermediate Similarity	NPC477849
0.831	Intermediate Similarity	NPC23667
0.831	Intermediate Similarity	NPC46242
0.831	Intermediate Similarity	NPC473779
0.831	Intermediate Similarity	NPC473479
0.831	Intermediate Similarity	NPC50615
0.831	Intermediate Similarity	NPC149773
0.831	Intermediate Similarity	NPC289358
0.831	Intermediate Similarity	NPC245760
0.831	Intermediate Similarity	NPC91887
0.831	Intermediate Similarity	NPC114333
0.831	Intermediate Similarity	NPC469857
0.831	Intermediate Similarity	NPC173980
0.831	Intermediate Similarity	NPC165191
0.831	Intermediate Similarity	NPC28592
0.831	Intermediate Similarity	NPC5014
0.831	Intermediate Similarity	NPC297797
0.831	Intermediate Similarity	NPC42384
0.831	Intermediate Similarity	NPC157284
0.8298	Intermediate Similarity	NPC254847
0.8298	Intermediate Similarity	NPC315275
0.8288	Intermediate Similarity	NPC474630
0.8284	Intermediate Similarity	NPC375356
0.8276	Intermediate Similarity	NPC53016
0.8276	Intermediate Similarity	NPC471682
0.8276	Intermediate Similarity	NPC66593
0.8276	Intermediate Similarity	NPC163948
0.8273	Intermediate Similarity	NPC70622
0.8271	Intermediate Similarity	NPC154696
0.8264	Intermediate Similarity	NPC290550
0.8261	Intermediate Similarity	NPC31799
0.8258	Intermediate Similarity	NPC285829
0.8258	Intermediate Similarity	NPC206778
0.8255	Intermediate Similarity	NPC315520
0.8252	Intermediate Similarity	NPC114620
0.8252	Intermediate Similarity	NPC103337
0.8252	Intermediate Similarity	NPC143438
0.8248	Intermediate Similarity	NPC3009
0.8243	Intermediate Similarity	NPC112816
0.8239	Intermediate Similarity	NPC53414
0.8239	Intermediate Similarity	NPC53206
0.8239	Intermediate Similarity	NPC245923
0.8239	Intermediate Similarity	NPC118366
0.8235	Intermediate Similarity	NPC96915
0.8235	Intermediate Similarity	NPC51037
0.8235	Intermediate Similarity	NPC71610
0.8224	Intermediate Similarity	NPC474360
0.8222	Intermediate Similarity	NPC152525
0.8222	Intermediate Similarity	NPC68756
0.8209	Intermediate Similarity	NPC300274
0.8207	Intermediate Similarity	NPC135524
0.8207	Intermediate Similarity	NPC19631
0.8207	Intermediate Similarity	NPC239136
0.8207	Intermediate Similarity	NPC248068
0.8207	Intermediate Similarity	NPC257644
0.8194	Intermediate Similarity	NPC471853
0.8194	Intermediate Similarity	NPC473527
0.8194	Intermediate Similarity	NPC96421
0.8182	Intermediate Similarity	NPC61398
0.8182	Intermediate Similarity	NPC416
0.8176	Intermediate Similarity	NPC10842
0.8176	Intermediate Similarity	NPC5568
0.8176	Intermediate Similarity	NPC478018
0.8169	Intermediate Similarity	NPC7464
0.8169	Intermediate Similarity	NPC191976
0.8169	Intermediate Similarity	NPC474813
0.8169	Intermediate Similarity	NPC475549
0.8169	Intermediate Similarity	NPC471670
0.8163	Intermediate Similarity	NPC471683
0.8163	Intermediate Similarity	NPC12402
0.8162	Intermediate Similarity	NPC103540
0.8156	Intermediate Similarity	NPC282780
0.8156	Intermediate Similarity	NPC166480
0.8148	Intermediate Similarity	NPC275145
0.8143	Intermediate Similarity	NPC246693
0.8143	Intermediate Similarity	NPC110609
0.8143	Intermediate Similarity	NPC242358
0.8138	Intermediate Similarity	NPC246638
0.8138	Intermediate Similarity	NPC305845
0.8138	Intermediate Similarity	NPC204045
0.8138	Intermediate Similarity	NPC110810
0.8133	Intermediate Similarity	NPC48949
0.8129	Intermediate Similarity	NPC253488
0.8129	Intermediate Similarity	NPC117609
0.8129	Intermediate Similarity	NPC27659
0.8125	Intermediate Similarity	NPC190457
0.8121	Intermediate Similarity	NPC94781
0.8121	Intermediate Similarity	NPC470479
0.8112	Intermediate Similarity	NPC277559
0.8112	Intermediate Similarity	NPC305060
0.8108	Intermediate Similarity	NPC314437
0.8102	Intermediate Similarity	NPC472047
0.8102	Intermediate Similarity	NPC160499
0.8099	Intermediate Similarity	NPC153088
0.8095	Intermediate Similarity	NPC244691
0.8095	Intermediate Similarity	NPC144247
0.8095	Intermediate Similarity	NPC145301
0.8095	Intermediate Similarity	NPC294679
0.8095	Intermediate Similarity	NPC469856
0.8095	Intermediate Similarity	NPC469854
0.8095	Intermediate Similarity	NPC8493
0.8095	Intermediate Similarity	NPC469375

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 NPC474311 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	994
0.2-0.3	1689
0.3-0.4	2901
0.4-0.5	2069
0.5-0.6	819
0.6-0.7	310
0.7-0.8	25
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8298	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD1470	Approved
0.7955	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD1201	Approved
0.7852	Intermediate Similarity	NPD7390	Discontinued
0.7793	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD3300	Phase 2
0.7778	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5404	Approved
0.774	Intermediate Similarity	NPD5406	Approved
0.774	Intermediate Similarity	NPD5405	Approved
0.774	Intermediate Similarity	NPD5408	Approved
0.7712	Intermediate Similarity	NPD3226	Approved
0.7687	Intermediate Similarity	NPD2346	Discontinued
0.7591	Intermediate Similarity	NPD2932	Approved
0.7566	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD3019	Approved
0.745	Intermediate Similarity	NPD1471	Phase 3
0.7432	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2800	Approved
0.7279	Intermediate Similarity	NPD943	Approved
0.7279	Intermediate Similarity	NPD5951	Approved
0.7267	Intermediate Similarity	NPD2935	Discontinued
0.7226	Intermediate Similarity	NPD2533	Approved
0.7226	Intermediate Similarity	NPD2534	Approved
0.7226	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD2532	Approved
0.7219	Intermediate Similarity	NPD2344	Approved
0.7195	Intermediate Similarity	NPD6232	Discontinued
0.7169	Intermediate Similarity	NPD7473	Discontinued
0.7153	Intermediate Similarity	NPD1164	Approved
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7134	Intermediate Similarity	NPD6959	Discontinued
0.7092	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2799	Discontinued
0.7078	Intermediate Similarity	NPD7003	Approved
0.7067	Intermediate Similarity	NPD6651	Approved
0.7063	Intermediate Similarity	NPD3972	Approved
0.7052	Intermediate Similarity	NPD8150	Discontinued
0.7042	Intermediate Similarity	NPD3026	Approved
0.7042	Intermediate Similarity	NPD3023	Approved
0.7032	Intermediate Similarity	NPD2309	Approved
0.7021	Intermediate Similarity	NPD3024	Approved
0.7021	Intermediate Similarity	NPD3025	Approved
0.7007	Intermediate Similarity	NPD7635	Approved
0.7006	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2798	Approved
0.6975	Remote Similarity	NPD7819	Suspended
0.6963	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1607	Approved
0.6937	Remote Similarity	NPD7458	Discontinued
0.6928	Remote Similarity	NPD6100	Approved
0.6928	Remote Similarity	NPD6099	Approved
0.6913	Remote Similarity	NPD3764	Approved
0.691	Remote Similarity	NPD6534	Approved
0.691	Remote Similarity	NPD6535	Approved
0.6903	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2342	Discontinued
0.6879	Remote Similarity	NPD7236	Approved
0.6871	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD1510	Phase 2
0.686	Remote Similarity	NPD5031	Approved
0.686	Remote Similarity	NPD5029	Approved
0.686	Remote Similarity	NPD5027	Approved
0.6859	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD8166	Discontinued
0.6839	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5028	Approved
0.6821	Remote Similarity	NPD4954	Approved
0.6821	Remote Similarity	NPD5026	Approved
0.6821	Remote Similarity	NPD5034	Approved
0.6821	Remote Similarity	NPD4955	Approved
0.6821	Remote Similarity	NPD36	Approved
0.6821	Remote Similarity	NPD1240	Approved
0.6812	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7700	Phase 2
0.6796	Remote Similarity	NPD7699	Phase 2
0.679	Remote Similarity	NPD4380	Phase 2
0.679	Remote Similarity	NPD6599	Discontinued
0.677	Remote Similarity	NPD7239	Suspended
0.6765	Remote Similarity	NPD5033	Approved
0.6763	Remote Similarity	NPD5030	Phase 2
0.6761	Remote Similarity	NPD8434	Phase 2
0.6755	Remote Similarity	NPD6663	Approved
0.675	Remote Similarity	NPD1512	Approved
0.6748	Remote Similarity	NPD7411	Suspended
0.6747	Remote Similarity	NPD7075	Discontinued
0.6739	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5032	Approved
0.6721	Remote Similarity	NPD6780	Approved
0.6721	Remote Similarity	NPD6778	Approved
0.6721	Remote Similarity	NPD6782	Approved
0.6721	Remote Similarity	NPD6776	Approved
0.6721	Remote Similarity	NPD6777	Approved
0.6721	Remote Similarity	NPD6781	Approved
0.6721	Remote Similarity	NPD6779	Approved
0.6715	Remote Similarity	NPD74	Approved
0.6715	Remote Similarity	NPD9266	Approved
0.6712	Remote Similarity	NPD4878	Approved
0.6711	Remote Similarity	NPD5736	Approved
0.6707	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.669	Remote Similarity	NPD9493	Approved
0.6687	Remote Similarity	NPD3882	Suspended
0.6686	Remote Similarity	NPD5711	Approved
0.6686	Remote Similarity	NPD5710	Approved
0.6686	Remote Similarity	NPD5035	Approved
0.6685	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1755	Approved
0.6667	Remote Similarity	NPD5038	Approved
0.6667	Remote Similarity	NPD5037	Approved
0.6647	Remote Similarity	NPD3749	Approved
0.6646	Remote Similarity	NPD3750	Approved
0.6646	Remote Similarity	NPD4628	Phase 3
0.6645	Remote Similarity	NPD7961	Discontinued
0.6643	Remote Similarity	NPD7610	Discontinued
0.6642	Remote Similarity	NPD9264	Approved
0.6642	Remote Similarity	NPD9267	Approved
0.6642	Remote Similarity	NPD9263	Approved
0.6641	Remote Similarity	NPD1809	Phase 2
0.6626	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1511	Approved
0.6624	Remote Similarity	NPD1549	Phase 2
0.6623	Remote Similarity	NPD7008	Discontinued
0.6622	Remote Similarity	NPD1283	Approved
0.6622	Remote Similarity	NPD1876	Approved
0.6621	Remote Similarity	NPD4626	Approved
0.6621	Remote Similarity	NPD4059	Approved
0.662	Remote Similarity	NPD3317	Approved
0.6613	Remote Similarity	NPD7435	Discontinued
0.6613	Remote Similarity	NPD7696	Phase 3
0.6613	Remote Similarity	NPD7697	Approved
0.6613	Remote Similarity	NPD7698	Approved
0.6611	Remote Similarity	NPD5968	Phase 3
0.661	Remote Similarity	NPD5036	Approved
0.6608	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6801	Discontinued
0.6606	Remote Similarity	NPD1934	Approved
0.6597	Remote Similarity	NPD3091	Approved
0.6592	Remote Similarity	NPD6836	Approved
0.6591	Remote Similarity	NPD3495	Discontinued
0.6579	Remote Similarity	NPD3268	Approved
0.6578	Remote Similarity	NPD7871	Phase 2
0.6578	Remote Similarity	NPD7870	Phase 2
0.6578	Remote Similarity	NPD8320	Phase 1
0.6578	Remote Similarity	NPD8319	Approved
0.6575	Remote Similarity	NPD4879	Approved
0.6575	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6212	Phase 3
0.6575	Remote Similarity	NPD6213	Phase 3
0.6571	Remote Similarity	NPD5039	Approved
0.6567	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4956	Approved
0.6547	Remote Similarity	NPD4750	Phase 3
0.6544	Remote Similarity	NPD1237	Approved
0.6543	Remote Similarity	NPD6273	Approved
0.6543	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4308	Phase 3
0.6527	Remote Similarity	NPD2296	Approved
0.6522	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD844	Approved
0.6512	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6166	Phase 2
0.6512	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.651	Remote Similarity	NPD7301	Phase 3
0.651	Remote Similarity	NPD6696	Suspended
0.6497	Remote Similarity	NPD8312	Approved
0.6497	Remote Similarity	NPD8313	Approved
0.6497	Remote Similarity	NPD2796	Approved
0.6494	Remote Similarity	NPD5844	Phase 1
0.6494	Remote Similarity	NPD6020	Phase 2
0.649	Remote Similarity	NPD4208	Discontinued
0.6486	Remote Similarity	NPD9269	Phase 2
0.6483	Remote Similarity	NPD7009	Phase 2
0.6474	Remote Similarity	NPD7701	Phase 2
0.6471	Remote Similarity	NPD1930	Approved
0.6471	Remote Similarity	NPD1929	Approved
0.6471	Remote Similarity	NPD5494	Approved
0.6471	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD411	Approved
0.6467	Remote Similarity	NPD1203	Approved
0.6467	Remote Similarity	NPD3094	Phase 2
0.6466	Remote Similarity	NPD288	Approved
0.6457	Remote Similarity	NPD5190	Phase 2
0.6452	Remote Similarity	NPD447	Suspended
0.6438	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD9268	Approved
0.6437	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD3751	Discontinued
0.6434	Remote Similarity	NPD9281	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