NPASS Compound

Structure

NPC149780 OpenBabel07101718232D 22 24 0 0 0 0 0 0 0 0999 V2000 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 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 2.5981 1.5000 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 1.7321 2.0000 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 0.0000 2.0000 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 -3.4641 2.0000 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 -2.5981 1.5000 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 -0.8660 1.5000 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 11 2 0 0 0 0 7 13 2 0 0 0 0 8 11 1 0 0 0 0 8 14 2 0 0 0 0 9 12 1 0 0 0 0 9 15 2 0 0 0 0 10 12 1 0 0 0 0 10 19 2 0 0 0 0 11 13 1 0 0 0 0 12 17 2 0 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	296.1
Volume:	308.284
LogP:	4.225
LogD:	3.435
LogS:	-5.847
# Rotatable Bonds:	4
TPSA:	44.76
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.542
Synthetic Accessibility Score:	2.32
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.773
MDCK Permeability:	3.0588322260882705e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.498
Plasma Protein Binding (PPB):	88.76597595214844%
Volume Distribution (VD):	0.618
Pgp-substrate:	6.371786594390869%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.858
CYP2C19-substrate:	0.853
CYP2C9-inhibitor:	0.507
CYP2C9-substrate:	0.898
CYP2D6-inhibitor:	0.295
CYP2D6-substrate:	0.872
CYP3A4-inhibitor:	0.63
CYP3A4-substrate:	0.32

ADMET: Excretion

Clearance (CL):	4.827
Half-life (T1/2):	0.25

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.038
Drug-inuced Liver Injury (DILI):	0.543
AMES Toxicity:	0.797
Rat Oral Acute Toxicity:	0.113
Maximum Recommended Daily Dose:	0.424
Skin Sensitization:	0.761
Carcinogencity:	0.474
Eye Corrosion:	0.018
Eye Irritation:	0.918
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC149780

Natural Product ID:	NPC149780
*Common Name:**	1,4,10-Trimethoxyanthracene-2-Carbaldehyde
IUPAC Name:	1,4,10-trimethoxyanthracene-2-carbaldehyde
Synonyms:
Standard InCHIKey:	HJNRNEPJAUPFHZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O4/c1-20-15-9-12(10-19)17(21-2)14-8-11-6-4-5-7-13(11)18(22-3)16(14)15/h4-10H,1-3H3
SMILES:	COc1cc(C=O)c(c2cc3ccccc3c(c12)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456869
PubChem CID:	10017444
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO1719	Coussarea macrophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880304]
NPO1719	Coussarea macrophylla	Species	Rubiaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	12.0	mm	PMID[507780]
NPT176	Organism	Artemia salina	Artemia salina	LC50	>	280.0	ppm	PMID[507780]

☑ 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 NPC149780 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	451
0.1-0.2	1780
0.2-0.3	4348
0.3-0.4	12265
0.4-0.5	6023
0.5-0.6	4675
0.6-0.7	7750
0.7-0.8	5192
0.8-0.85	188
0.85-0.9	24
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8828	High Similarity	NPC300540
0.8824	High Similarity	NPC57552
0.8777	High Similarity	NPC274876
0.8777	High Similarity	NPC1249
0.8768	High Similarity	NPC474340
0.8759	High Similarity	NPC49282
0.8741	High Similarity	NPC124365
0.8733	High Similarity	NPC3898
0.8621	High Similarity	NPC167663
0.8618	High Similarity	NPC67197
0.8581	High Similarity	NPC474107
0.8571	High Similarity	NPC60389
0.8571	High Similarity	NPC211565
0.8571	High Similarity	NPC470406
0.8552	High Similarity	NPC329493
0.8552	High Similarity	NPC69755
0.854	High Similarity	NPC45537
0.8503	High Similarity	NPC478019
0.8497	Intermediate Similarity	NPC44199
0.8477	Intermediate Similarity	NPC3744
0.8477	Intermediate Similarity	NPC24232
0.8472	Intermediate Similarity	NPC1268
0.8467	Intermediate Similarity	NPC294646
0.8456	Intermediate Similarity	NPC56332
0.8451	Intermediate Similarity	NPC281513
0.8451	Intermediate Similarity	NPC22222
0.8442	Intermediate Similarity	NPC324736
0.8442	Intermediate Similarity	NPC477692
0.8431	Intermediate Similarity	NPC279605
0.8421	Intermediate Similarity	NPC208806
0.8421	Intermediate Similarity	NPC477691
0.8421	Intermediate Similarity	NPC135522
0.8389	Intermediate Similarity	NPC478018
0.8369	Intermediate Similarity	NPC183103
0.8367	Intermediate Similarity	NPC53016
0.8367	Intermediate Similarity	NPC163948
0.8366	Intermediate Similarity	NPC226656
0.8366	Intermediate Similarity	NPC66508
0.8355	Intermediate Similarity	NPC477690
0.8355	Intermediate Similarity	NPC137125
0.8344	Intermediate Similarity	NPC290954
0.8344	Intermediate Similarity	NPC147735
0.8344	Intermediate Similarity	NPC470568
0.8344	Intermediate Similarity	NPC255641
0.8333	Intermediate Similarity	NPC186647
0.8333	Intermediate Similarity	NPC474264
0.8333	Intermediate Similarity	NPC5537
0.8322	Intermediate Similarity	NPC39361
0.8311	Intermediate Similarity	NPC93241
0.8311	Intermediate Similarity	NPC27798
0.8311	Intermediate Similarity	NPC189650
0.8298	Intermediate Similarity	NPC85342
0.8291	Intermediate Similarity	NPC26386
0.8289	Intermediate Similarity	NPC470569
0.8289	Intermediate Similarity	NPC70320
0.8278	Intermediate Similarity	NPC472298
0.8278	Intermediate Similarity	NPC329933
0.8273	Intermediate Similarity	NPC428300
0.8273	Intermediate Similarity	NPC298884
0.8269	Intermediate Similarity	NPC476506
0.8269	Intermediate Similarity	NPC284495
0.8267	Intermediate Similarity	NPC245584
0.8267	Intermediate Similarity	NPC190648
0.8267	Intermediate Similarity	NPC56433
0.8267	Intermediate Similarity	NPC34802
0.8267	Intermediate Similarity	NPC312929
0.8267	Intermediate Similarity	NPC71055
0.8267	Intermediate Similarity	NPC118027
0.8267	Intermediate Similarity	NPC289042
0.8267	Intermediate Similarity	NPC126767
0.8264	Intermediate Similarity	NPC141934
0.8248	Intermediate Similarity	NPC182646
0.8247	Intermediate Similarity	NPC233776
0.8247	Intermediate Similarity	NPC66029
0.8235	Intermediate Similarity	NPC40356
0.8235	Intermediate Similarity	NPC154683
0.8235	Intermediate Similarity	NPC164912
0.8235	Intermediate Similarity	NPC175978
0.8231	Intermediate Similarity	NPC187843
0.8228	Intermediate Similarity	NPC101769
0.8224	Intermediate Similarity	NPC474660
0.8219	Intermediate Similarity	NPC223336
0.8219	Intermediate Similarity	NPC470407
0.8219	Intermediate Similarity	NPC476191
0.8217	Intermediate Similarity	NPC472261
0.8217	Intermediate Similarity	NPC24761
0.8214	Intermediate Similarity	NPC48248
0.8212	Intermediate Similarity	NPC472841
0.8212	Intermediate Similarity	NPC95526
0.8212	Intermediate Similarity	NPC476058
0.8212	Intermediate Similarity	NPC472056
0.8207	Intermediate Similarity	NPC301341
0.8207	Intermediate Similarity	NPC471542
0.8207	Intermediate Similarity	NPC245923
0.8205	Intermediate Similarity	NPC186113
0.8201	Intermediate Similarity	NPC227741
0.8201	Intermediate Similarity	NPC295202
0.8201	Intermediate Similarity	NPC49647
0.8201	Intermediate Similarity	NPC136342
0.82	Intermediate Similarity	NPC281398
0.8194	Intermediate Similarity	NPC221992
0.8188	Intermediate Similarity	NPC300603
0.8188	Intermediate Similarity	NPC470162
0.8188	Intermediate Similarity	NPC21599
0.8188	Intermediate Similarity	NPC470163
0.8188	Intermediate Similarity	NPC91694
0.8188	Intermediate Similarity	NPC193703
0.817	Intermediate Similarity	NPC118427
0.817	Intermediate Similarity	NPC149526
0.817	Intermediate Similarity	NPC474417
0.8169	Intermediate Similarity	NPC164295
0.8169	Intermediate Similarity	NPC477412
0.8163	Intermediate Similarity	NPC473499
0.8153	Intermediate Similarity	NPC143050
0.8153	Intermediate Similarity	NPC470342
0.8153	Intermediate Similarity	NPC472052
0.8153	Intermediate Similarity	NPC78944
0.8153	Intermediate Similarity	NPC472060
0.8151	Intermediate Similarity	NPC233707
0.8141	Intermediate Similarity	NPC212967
0.8141	Intermediate Similarity	NPC96342
0.8141	Intermediate Similarity	NPC164110
0.8141	Intermediate Similarity	NPC246647
0.8138	Intermediate Similarity	NPC155211
0.8138	Intermediate Similarity	NPC232996
0.8138	Intermediate Similarity	NPC474813
0.8133	Intermediate Similarity	NPC34482
0.8129	Intermediate Similarity	NPC131799
0.8121	Intermediate Similarity	NPC215451
0.8121	Intermediate Similarity	NPC84266
0.8121	Intermediate Similarity	NPC277369
0.8121	Intermediate Similarity	NPC117674
0.8117	Intermediate Similarity	NPC130015
0.8117	Intermediate Similarity	NPC38361
0.8117	Intermediate Similarity	NPC281272
0.8113	Intermediate Similarity	NPC476505
0.8105	Intermediate Similarity	NPC144010
0.8105	Intermediate Similarity	NPC227122
0.8105	Intermediate Similarity	NPC473466
0.8105	Intermediate Similarity	NPC205766
0.8101	Intermediate Similarity	NPC311740
0.8099	Intermediate Similarity	NPC31539
0.8095	Intermediate Similarity	NPC477408
0.8082	Intermediate Similarity	NPC284184
0.8079	Intermediate Similarity	NPC301949
0.8079	Intermediate Similarity	NPC470570
0.8079	Intermediate Similarity	NPC473927
0.8079	Intermediate Similarity	NPC308799
0.8079	Intermediate Similarity	NPC120924
0.8079	Intermediate Similarity	NPC225173
0.8079	Intermediate Similarity	NPC195919
0.8079	Intermediate Similarity	NPC216314
0.8079	Intermediate Similarity	NPC163846
0.8077	Intermediate Similarity	NPC469507
0.8077	Intermediate Similarity	NPC146211
0.8077	Intermediate Similarity	NPC180924
0.8074	Intermediate Similarity	NPC171023
0.8071	Intermediate Similarity	NPC474737
0.8071	Intermediate Similarity	NPC177925
0.8069	Intermediate Similarity	NPC217914
0.8067	Intermediate Similarity	NPC470932
0.8067	Intermediate Similarity	NPC10764
0.8067	Intermediate Similarity	NPC290038
0.8067	Intermediate Similarity	NPC274085
0.8067	Intermediate Similarity	NPC48762
0.8067	Intermediate Similarity	NPC89664
0.8067	Intermediate Similarity	NPC19896
0.8067	Intermediate Similarity	NPC472836
0.8065	Intermediate Similarity	NPC210942
0.8065	Intermediate Similarity	NPC169990
0.8065	Intermediate Similarity	NPC329844
0.8065	Intermediate Similarity	NPC290927
0.8058	Intermediate Similarity	NPC4012
0.8054	Intermediate Similarity	NPC49108
0.8054	Intermediate Similarity	NPC182255
0.8054	Intermediate Similarity	NPC94076
0.8052	Intermediate Similarity	NPC232645
0.8052	Intermediate Similarity	NPC75377
0.8052	Intermediate Similarity	NPC145830
0.8052	Intermediate Similarity	NPC478148
0.8052	Intermediate Similarity	NPC39819
0.8052	Intermediate Similarity	NPC72958
0.805	Intermediate Similarity	NPC473961
0.805	Intermediate Similarity	NPC108767
0.8042	Intermediate Similarity	NPC205360
0.8042	Intermediate Similarity	NPC239134
0.8042	Intermediate Similarity	NPC205992
0.8041	Intermediate Similarity	NPC109007
0.8039	Intermediate Similarity	NPC70764
0.8039	Intermediate Similarity	NPC158338
0.8039	Intermediate Similarity	NPC288036
0.8039	Intermediate Similarity	NPC100985
0.8039	Intermediate Similarity	NPC266499
0.8039	Intermediate Similarity	NPC97029
0.8039	Intermediate Similarity	NPC97028
0.8039	Intermediate Similarity	NPC65589
0.8038	Intermediate Similarity	NPC84571
0.8037	Intermediate Similarity	NPC477836
0.8027	Intermediate Similarity	NPC475104
0.8027	Intermediate Similarity	NPC206207

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 NPC149780 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	998
0.2-0.3	1381
0.3-0.4	2755
0.4-0.5	1963
0.5-0.6	1126
0.6-0.7	401
0.7-0.8	118
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
0.8333	Intermediate Similarity	NPD2935	Discontinued
0.8276	Intermediate Similarity	NPD2346	Discontinued
0.805	Intermediate Similarity	NPD6232	Discontinued
0.8039	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD3226	Approved
0.7901	Intermediate Similarity	NPD7473	Discontinued
0.7883	Intermediate Similarity	NPD1651	Approved
0.7875	Intermediate Similarity	NPD6959	Discontinued
0.7867	Intermediate Similarity	NPD7003	Approved
0.7834	Intermediate Similarity	NPD7819	Suspended
0.7832	Intermediate Similarity	NPD6832	Phase 2
0.7817	Intermediate Similarity	NPD2798	Approved
0.7812	Intermediate Similarity	NPD5494	Approved
0.7808	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD5844	Phase 1
0.774	Intermediate Similarity	NPD2979	Phase 3
0.7724	Intermediate Similarity	NPD2313	Discontinued
0.7718	Intermediate Similarity	NPD5406	Approved
0.7718	Intermediate Similarity	NPD2796	Approved
0.7718	Intermediate Similarity	NPD5404	Approved
0.7718	Intermediate Similarity	NPD5408	Approved
0.7718	Intermediate Similarity	NPD5405	Approved
0.7714	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1281	Approved
0.7673	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2533	Approved
0.7662	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2534	Approved
0.7662	Intermediate Similarity	NPD2532	Approved
0.7651	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2799	Discontinued
0.7625	Intermediate Similarity	NPD7768	Phase 2
0.7622	Intermediate Similarity	NPD1470	Approved
0.76	Intermediate Similarity	NPD1551	Phase 2
0.7597	Intermediate Similarity	NPD7390	Discontinued
0.7589	Intermediate Similarity	NPD1611	Approved
0.7564	Intermediate Similarity	NPD920	Approved
0.756	Intermediate Similarity	NPD6559	Discontinued
0.7552	Intermediate Similarity	NPD1283	Approved
0.7548	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD1247	Approved
0.7535	Intermediate Similarity	NPD3972	Approved
0.7533	Intermediate Similarity	NPD1510	Phase 2
0.7517	Intermediate Similarity	NPD1607	Approved
0.75	Intermediate Similarity	NPD5691	Approved
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4307	Phase 2
0.7484	Intermediate Similarity	NPD7411	Suspended
0.7483	Intermediate Similarity	NPD2438	Suspended
0.7465	Intermediate Similarity	NPD1201	Approved
0.7457	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5402	Approved
0.7436	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1471	Phase 3
0.7431	Intermediate Similarity	NPD1876	Approved
0.7421	Intermediate Similarity	NPD4380	Phase 2
0.7417	Intermediate Similarity	NPD3748	Approved
0.7391	Intermediate Similarity	NPD2801	Approved
0.7383	Intermediate Similarity	NPD1240	Approved
0.7371	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD8312	Approved
0.7368	Intermediate Similarity	NPD8313	Approved
0.7368	Intermediate Similarity	NPD2531	Phase 2
0.7338	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1933	Approved
0.7329	Intermediate Similarity	NPD6844	Discontinued
0.7329	Intermediate Similarity	NPD1019	Discontinued
0.7324	Intermediate Similarity	NPD4626	Approved
0.732	Intermediate Similarity	NPD2344	Approved
0.7312	Intermediate Similarity	NPD6599	Discontinued
0.7308	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4308	Phase 3
0.7284	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6273	Approved
0.7273	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1549	Phase 2
0.726	Intermediate Similarity	NPD1203	Approved
0.7256	Intermediate Similarity	NPD3749	Approved
0.725	Intermediate Similarity	NPD7458	Discontinued
0.7248	Intermediate Similarity	NPD411	Approved
0.7244	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1934	Approved
0.7219	Intermediate Similarity	NPD447	Suspended
0.7219	Intermediate Similarity	NPD7177	Discontinued
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD919	Approved
0.7208	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD4625	Phase 3
0.7179	Intermediate Similarity	NPD3750	Approved
0.7179	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD9717	Approved
0.7152	Intermediate Similarity	NPD6799	Approved
0.7152	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD2797	Approved
0.7143	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD3926	Phase 2
0.7134	Intermediate Similarity	NPD2309	Approved
0.7134	Intermediate Similarity	NPD3817	Phase 2
0.7133	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6801	Discontinued
0.7115	Intermediate Similarity	NPD1243	Approved
0.7101	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD6166	Phase 2
0.7091	Intermediate Similarity	NPD3882	Suspended
0.7091	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD6780	Approved
0.7088	Intermediate Similarity	NPD6776	Approved
0.7088	Intermediate Similarity	NPD6781	Approved
0.7088	Intermediate Similarity	NPD6778	Approved
0.7088	Intermediate Similarity	NPD6779	Approved
0.7088	Intermediate Similarity	NPD6777	Approved
0.7088	Intermediate Similarity	NPD6782	Approved
0.7083	Intermediate Similarity	NPD5710	Approved
0.7083	Intermediate Similarity	NPD5711	Approved
0.7083	Intermediate Similarity	NPD7229	Phase 3
0.707	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7008	Discontinued
0.7055	Intermediate Similarity	NPD5890	Approved
0.7055	Intermediate Similarity	NPD5889	Approved
0.7045	Intermediate Similarity	NPD8150	Discontinued
0.7044	Intermediate Similarity	NPD1511	Approved
0.7042	Intermediate Similarity	NPD9493	Approved
0.7042	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1164	Approved
0.7027	Intermediate Similarity	NPD7871	Phase 2
0.7027	Intermediate Similarity	NPD7870	Phase 2
0.702	Intermediate Similarity	NPD3268	Approved
0.702	Intermediate Similarity	NPD3764	Approved
0.7019	Intermediate Similarity	NPD5403	Approved
0.7018	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD37	Approved
0.7012	Intermediate Similarity	NPD6279	Approved
0.7012	Intermediate Similarity	NPD6280	Approved
0.7011	Intermediate Similarity	NPD6823	Phase 2
0.7	Intermediate Similarity	NPD5401	Approved
0.6974	Remote Similarity	NPD6233	Phase 2
0.6974	Remote Similarity	NPD8032	Phase 2
0.6973	Remote Similarity	NPD7697	Approved
0.6973	Remote Similarity	NPD7696	Phase 3
0.6973	Remote Similarity	NPD7435	Discontinued
0.6973	Remote Similarity	NPD7698	Approved
0.697	Remote Similarity	NPD5760	Phase 2
0.697	Remote Similarity	NPD5761	Phase 2
0.6962	Remote Similarity	NPD4628	Phase 3
0.6957	Remote Similarity	NPD1512	Approved
0.6954	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.695	Remote Similarity	NPD1241	Discontinued
0.6946	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6100	Approved
0.6923	Remote Similarity	NPD4476	Approved
0.6923	Remote Similarity	NPD4477	Approved
0.6923	Remote Similarity	NPD6099	Approved
0.6919	Remote Similarity	NPD3751	Discontinued
0.6919	Remote Similarity	NPD3818	Discontinued
0.6918	Remote Similarity	NPD3496	Discontinued
0.6908	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6798	Discontinued
0.6899	Remote Similarity	NPD2800	Approved
0.6897	Remote Similarity	NPD5585	Approved
0.6895	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD7783	Phase 2
0.6892	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6585	Discontinued
0.6886	Remote Similarity	NPD4967	Phase 2
0.6886	Remote Similarity	NPD4966	Approved
0.6886	Remote Similarity	NPD4965	Approved
0.6883	Remote Similarity	NPD4622	Approved
0.6883	Remote Similarity	NPD4618	Approved
0.6882	Remote Similarity	NPD6808	Phase 2
0.6882	Remote Similarity	NPD3787	Discontinued
0.6879	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7635	Approved
0.6875	Remote Similarity	NPD5536	Phase 2
0.6864	Remote Similarity	NPD6746	Phase 2
0.6851	Remote Similarity	NPD6212	Phase 3
0.6851	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD6213	Phase 3
0.6849	Remote Similarity	NPD17	Approved
0.6848	Remote Similarity	NPD8285	Discontinued
0.6839	Remote Similarity	NPD4097	Suspended
0.6835	Remote Similarity	NPD2897	Discontinued
0.6835	Remote Similarity	NPD2182	Approved
0.6831	Remote Similarity	NPD498	Approved
0.6831	Remote Similarity	NPD496	Approved
0.6831	Remote Similarity	NPD495	Approved
0.6829	Remote Similarity	NPD2651	Approved
0.6829	Remote Similarity	NPD2649	Approved
0.6825	Remote Similarity	NPD7701	Phase 2
0.6821	Remote Similarity	NPD9494	Approved
0.6818	Remote Similarity	NPD943	Approved
0.6818	Remote Similarity	NPD4060	Phase 1

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