NPASS Compound

Structure

NPC230848 OpenBabel07101718312D 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 -3.4641 -4.0000 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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 -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 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 0.0000 -1.0000 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 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 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 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 9 1 0 0 0 0 5 11 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 10 2 0 0 0 0 7 13 1 0 0 0 0 8 12 1 0 0 0 0 8 14 2 0 0 0 0 9 15 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 16 2 0 0 0 0 12 18 2 0 0 0 0 13 15 2 0 0 0 0 13 19 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 20 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	299.778
LogP:	3.332
LogD:	2.842
LogS:	-4.891
# Rotatable Bonds:	3
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.943
Synthetic Accessibility Score:	2.554
Fsp3:	0.176
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.95
MDCK Permeability:	3.846416439046152e-05
Pgp-inhibitor:	0.04
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.676
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.059
Plasma Protein Binding (PPB):	97.2959976196289%
Volume Distribution (VD):	0.46
Pgp-substrate:	1.5266531705856323%

ADMET: Metabolism

CYP1A2-inhibitor:	0.98
CYP1A2-substrate:	0.771
CYP2C19-inhibitor:	0.845
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.783
CYP2C9-substrate:	0.861
CYP2D6-inhibitor:	0.789
CYP2D6-substrate:	0.445
CYP3A4-inhibitor:	0.769
CYP3A4-substrate:	0.14

ADMET: Excretion

Clearance (CL):	6.823
Half-life (T1/2):	0.209

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.294
Drug-inuced Liver Injury (DILI):	0.778
AMES Toxicity:	0.849
Rat Oral Acute Toxicity:	0.788
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.851
Carcinogencity:	0.919
Eye Corrosion:	0.007
Eye Irritation:	0.958
Respiratory Toxicity:	0.329

Download Data

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

Natural Product: NPC230848

Natural Product ID:	NPC230848
*Common Name:**	3-Ethoxy-5-Hydroxy-7-Methoxyphenanthrene-1,4-Dione
IUPAC Name:	3-ethoxy-5-hydroxy-7-methoxyphenanthrene-1,4-dione
Synonyms:
Standard InCHIKey:	RNXYLFAKSJROKT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O5/c1-3-22-14-8-12(18)11-5-4-9-6-10(21-2)7-13(19)15(9)16(11)17(14)20/h4-8,19H,3H2,1-2H3
SMILES:	CCOC1=CC(=O)c2ccc3cc(cc(c3c2C1=O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500828
PubChem CID:	21668767
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0003007] Phenanthrols

*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
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[10514302]
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9461658]
NPO2022	Ephemerantha lonchophylla	n.a.	n.a.	n.a.	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	0.2	%	PMID[497460]

☑ 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 NPC230848 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	396
0.1-0.2	1688
0.2-0.3	3897
0.3-0.4	9887
0.4-0.5	8424
0.5-0.6	3475
0.6-0.7	5691
0.7-0.8	6260
0.8-0.85	2518
0.85-0.9	412
0.9-0.95	47
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC80370
0.9342	High Similarity	NPC104876
0.9342	High Similarity	NPC245891
0.9262	High Similarity	NPC290954
0.9262	High Similarity	NPC255641
0.9257	High Similarity	NPC472841
0.9189	High Similarity	NPC312929
0.9189	High Similarity	NPC56433
0.9189	High Similarity	NPC245584
0.9189	High Similarity	NPC289042
0.9189	High Similarity	NPC190648
0.9189	High Similarity	NPC126767
0.9189	High Similarity	NPC118027
0.9184	High Similarity	NPC28632
0.9139	High Similarity	NPC40356
0.9139	High Similarity	NPC154683
0.9133	High Similarity	NPC470568
0.9133	High Similarity	NPC147735
0.9079	High Similarity	NPC208806
0.9073	High Similarity	NPC474414
0.9073	High Similarity	NPC470569
0.9026	High Similarity	NPC474637
0.9026	High Similarity	NPC201127
0.902	High Similarity	NPC226656
0.902	High Similarity	NPC66508
0.9007	High Similarity	NPC294646
0.9	High Similarity	NPC7025
0.9	High Similarity	NPC27221
0.9	High Similarity	NPC256672
0.8986	High Similarity	NPC475201
0.8986	High Similarity	NPC21599
0.8986	High Similarity	NPC193703
0.8986	High Similarity	NPC19896
0.898	High Similarity	NPC182255
0.898	High Similarity	NPC201297
0.898	High Similarity	NPC94076
0.8968	High Similarity	NPC324736
0.8954	High Similarity	NPC210942
0.8954	High Similarity	NPC169990
0.8947	High Similarity	NPC232645
0.8947	High Similarity	NPC258249
0.8947	High Similarity	NPC149526
0.8947	High Similarity	NPC474417
0.8947	High Similarity	NPC72958
0.894	High Similarity	NPC288036
0.894	High Similarity	NPC65589
0.894	High Similarity	NPC97029
0.894	High Similarity	NPC158338
0.894	High Similarity	NPC329933
0.894	High Similarity	NPC97028
0.894	High Similarity	NPC100985
0.8933	High Similarity	NPC34802
0.8933	High Similarity	NPC22005
0.8933	High Similarity	NPC7943
0.8933	High Similarity	NPC123202
0.8926	High Similarity	NPC49282
0.8924	High Similarity	NPC316262
0.8924	High Similarity	NPC314653
0.8919	High Similarity	NPC84266
0.891	High Similarity	NPC313368
0.8889	High Similarity	NPC87708
0.8882	High Similarity	NPC202595
0.8867	High Similarity	NPC470570
0.8859	High Similarity	NPC48762
0.8851	High Similarity	NPC103752
0.8851	High Similarity	NPC49108
0.8831	High Similarity	NPC107109
0.8831	High Similarity	NPC214632
0.8831	High Similarity	NPC329844
0.8824	High Similarity	NPC478148
0.8824	High Similarity	NPC189773
0.8824	High Similarity	NPC78505
0.8816	High Similarity	NPC10027
0.8816	High Similarity	NPC65775
0.88	High Similarity	NPC34482
0.8792	High Similarity	NPC167663
0.8784	High Similarity	NPC110810
0.8784	High Similarity	NPC101366
0.8782	High Similarity	NPC178976
0.8782	High Similarity	NPC96342
0.8782	High Similarity	NPC246647
0.8782	High Similarity	NPC164110
0.8782	High Similarity	NPC263483
0.8782	High Similarity	NPC212967
0.8767	High Similarity	NPC24394
0.8766	High Similarity	NPC28103
0.8766	High Similarity	NPC175978
0.8758	High Similarity	NPC13282
0.8758	High Similarity	NPC325983
0.8758	High Similarity	NPC119929
0.875	High Similarity	NPC172329
0.875	High Similarity	NPC2569
0.8742	High Similarity	NPC163846
0.8742	High Similarity	NPC202112
0.8742	High Similarity	NPC51513
0.8742	High Similarity	NPC225173
0.8733	High Similarity	NPC471451
0.8726	High Similarity	NPC228654
0.8725	High Similarity	NPC55832
0.8725	High Similarity	NPC232021
0.8725	High Similarity	NPC26051
0.8725	High Similarity	NPC40118
0.8725	High Similarity	NPC18714
0.8725	High Similarity	NPC52789
0.8725	High Similarity	NPC126534
0.8725	High Similarity	NPC268204
0.8718	High Similarity	NPC77807
0.8718	High Similarity	NPC5379
0.8718	High Similarity	NPC180924
0.8718	High Similarity	NPC14561
0.8716	High Similarity	NPC295384
0.8716	High Similarity	NPC109007
0.8716	High Similarity	NPC472366
0.8716	High Similarity	NPC156872
0.8716	High Similarity	NPC49242
0.8712	High Similarity	NPC154986
0.871	High Similarity	NPC193200
0.871	High Similarity	NPC93552
0.871	High Similarity	NPC135522
0.8707	High Similarity	NPC23870
0.8704	High Similarity	NPC313717
0.8704	High Similarity	NPC315306
0.8701	High Similarity	NPC132990
0.8701	High Similarity	NPC46882
0.8693	High Similarity	NPC269420
0.869	High Similarity	NPC27643
0.8684	High Similarity	NPC77903
0.8684	High Similarity	NPC259632
0.8684	High Similarity	NPC17101
0.8684	High Similarity	NPC58373
0.8684	High Similarity	NPC71055
0.8684	High Similarity	NPC125801
0.8675	High Similarity	NPC478019
0.8675	High Similarity	NPC476055
0.8675	High Similarity	NPC469764
0.8675	High Similarity	NPC474630
0.8671	High Similarity	NPC472060
0.8671	High Similarity	NPC472052
0.8671	High Similarity	NPC470342
0.8671	High Similarity	NPC284495
0.8667	High Similarity	NPC310340
0.8667	High Similarity	NPC3732
0.8667	High Similarity	NPC277369
0.8667	High Similarity	NPC215451
0.8667	High Similarity	NPC297600
0.8662	High Similarity	NPC44199
0.8662	High Similarity	NPC37543
0.8662	High Similarity	NPC199463
0.8658	High Similarity	NPC144118
0.8658	High Similarity	NPC80962
0.8658	High Similarity	NPC213659
0.8658	High Similarity	NPC326109
0.8658	High Similarity	NPC265178
0.8658	High Similarity	NPC215311
0.8658	High Similarity	NPC219917
0.8658	High Similarity	NPC172250
0.8658	High Similarity	NPC253822
0.8658	High Similarity	NPC204985
0.8658	High Similarity	NPC48624
0.8658	High Similarity	NPC259166
0.8654	High Similarity	NPC148938
0.8649	High Similarity	NPC278323
0.8649	High Similarity	NPC90665
0.8649	High Similarity	NPC309154
0.8649	High Similarity	NPC470407
0.8649	High Similarity	NPC279668
0.8649	High Similarity	NPC25427
0.8649	High Similarity	NPC1268
0.8649	High Similarity	NPC55162
0.8649	High Similarity	NPC12175
0.8645	High Similarity	NPC470340
0.8639	High Similarity	NPC290601
0.8636	High Similarity	NPC227122
0.8636	High Similarity	NPC470107
0.8636	High Similarity	NPC295036
0.8636	High Similarity	NPC225854
0.8634	High Similarity	NPC477835
0.863	High Similarity	NPC22644
0.8627	High Similarity	NPC39195
0.8627	High Similarity	NPC472056
0.8618	High Similarity	NPC196114
0.8618	High Similarity	NPC469758
0.8618	High Similarity	NPC300540
0.8618	High Similarity	NPC130176
0.8618	High Similarity	NPC99454
0.8618	High Similarity	NPC178343
0.8618	High Similarity	NPC5820
0.8618	High Similarity	NPC306488
0.8616	High Similarity	NPC311740
0.8616	High Similarity	NPC219686
0.8616	High Similarity	NPC478134
0.8609	High Similarity	NPC105213
0.8609	High Similarity	NPC301751
0.8609	High Similarity	NPC245482
0.8609	High Similarity	NPC471906
0.8609	High Similarity	NPC189650
0.8608	High Similarity	NPC477410
0.86	High Similarity	NPC469404
0.86	High Similarity	NPC3188
0.8599	High Similarity	NPC472050

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 NPC230848 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	368
0.1-0.2	1005
0.2-0.3	1485
0.3-0.4	2615
0.4-0.5	1913
0.5-0.6	1114
0.6-0.7	439
0.7-0.8	178
0.8-0.85	30
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8553	High Similarity	NPD4378	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7819	Suspended
0.8447	Intermediate Similarity	NPD6232	Discontinued
0.8446	Intermediate Similarity	NPD1510	Phase 2
0.8446	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD1607	Approved
0.8411	Intermediate Similarity	NPD3750	Approved
0.8405	Intermediate Similarity	NPD7473	Discontinued
0.8385	Intermediate Similarity	NPD6959	Discontinued
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.8312	Intermediate Similarity	NPD2534	Approved
0.8312	Intermediate Similarity	NPD2532	Approved
0.8312	Intermediate Similarity	NPD2533	Approved
0.8299	Intermediate Similarity	NPD1240	Approved
0.8278	Intermediate Similarity	NPD1549	Phase 2
0.825	Intermediate Similarity	NPD3882	Suspended
0.8239	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD5844	Phase 1
0.8165	Intermediate Similarity	NPD6599	Discontinued
0.8165	Intermediate Similarity	NPD4380	Phase 2
0.8158	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD3226	Approved
0.8079	Intermediate Similarity	NPD3748	Approved
0.8077	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6801	Discontinued
0.8063	Intermediate Similarity	NPD1934	Approved
0.8026	Intermediate Similarity	NPD2796	Approved
0.8025	Intermediate Similarity	NPD1512	Approved
0.8013	Intermediate Similarity	NPD6799	Approved
0.8	Intermediate Similarity	NPD7411	Suspended
0.7987	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD3749	Approved
0.7943	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7768	Phase 2
0.7908	Intermediate Similarity	NPD6100	Approved
0.7908	Intermediate Similarity	NPD6099	Approved
0.7904	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD2801	Approved
0.7898	Intermediate Similarity	NPD7390	Discontinued
0.7898	Intermediate Similarity	NPD1511	Approved
0.7871	Intermediate Similarity	NPD2800	Approved
0.7857	Intermediate Similarity	NPD2346	Discontinued
0.7853	Intermediate Similarity	NPD3817	Phase 2
0.7852	Intermediate Similarity	NPD4625	Phase 3
0.7821	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3751	Discontinued
0.7805	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6166	Phase 2
0.7798	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2935	Discontinued
0.7792	Intermediate Similarity	NPD1551	Phase 2
0.7791	Intermediate Similarity	NPD1465	Phase 2
0.7771	Intermediate Similarity	NPD5494	Approved
0.7765	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD2344	Approved
0.7733	Intermediate Similarity	NPD6559	Discontinued
0.7725	Intermediate Similarity	NPD1247	Approved
0.7711	Intermediate Similarity	NPD919	Approved
0.7707	Intermediate Similarity	NPD4628	Phase 3
0.7707	Intermediate Similarity	NPD7003	Approved
0.7707	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1470	Approved
0.7682	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5711	Approved
0.7679	Intermediate Similarity	NPD5710	Approved
0.7651	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD920	Approved
0.7636	Intermediate Similarity	NPD5402	Approved
0.7635	Intermediate Similarity	NPD1283	Approved
0.7633	Intermediate Similarity	NPD3926	Phase 2
0.7628	Intermediate Similarity	NPD1471	Phase 3
0.7602	Intermediate Similarity	NPD3818	Discontinued
0.7597	Intermediate Similarity	NPD6651	Approved
0.7586	Intermediate Similarity	NPD1651	Approved
0.7582	Intermediate Similarity	NPD943	Approved
0.7574	Intermediate Similarity	NPD7229	Phase 3
0.7572	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD6797	Phase 2
0.7572	Intermediate Similarity	NPD5953	Discontinued
0.7566	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3764	Approved
0.7564	Intermediate Similarity	NPD5404	Approved
0.7564	Intermediate Similarity	NPD5408	Approved
0.7564	Intermediate Similarity	NPD5406	Approved
0.7564	Intermediate Similarity	NPD5405	Approved
0.7547	Intermediate Similarity	NPD2309	Approved
0.7546	Intermediate Similarity	NPD7458	Discontinued
0.7541	Intermediate Similarity	NPD6781	Approved
0.7541	Intermediate Similarity	NPD6780	Approved
0.7541	Intermediate Similarity	NPD6776	Approved
0.7541	Intermediate Similarity	NPD6777	Approved
0.7541	Intermediate Similarity	NPD6778	Approved
0.7541	Intermediate Similarity	NPD6779	Approved
0.7541	Intermediate Similarity	NPD6782	Approved
0.7532	Intermediate Similarity	NPD230	Phase 1
0.7532	Intermediate Similarity	NPD1243	Approved
0.7531	Intermediate Similarity	NPD5403	Approved
0.7529	Intermediate Similarity	NPD7251	Discontinued
0.7528	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD5401	Approved
0.7514	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3972	Approved
0.75	Intermediate Similarity	NPD7177	Discontinued
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7808	Phase 3
0.7486	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD4060	Phase 1
0.7434	Intermediate Similarity	NPD4908	Phase 1
0.7432	Intermediate Similarity	NPD1610	Phase 2
0.7432	Intermediate Similarity	NPD1201	Approved
0.7432	Intermediate Similarity	NPD1281	Approved
0.7427	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4288	Approved
0.7423	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD7696	Phase 3
0.7419	Intermediate Similarity	NPD7698	Approved
0.7419	Intermediate Similarity	NPD7697	Approved
0.7416	Intermediate Similarity	NPD8150	Discontinued
0.7414	Intermediate Similarity	NPD7074	Phase 3
0.741	Intermediate Similarity	NPD37	Approved
0.7405	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1876	Approved
0.7396	Intermediate Similarity	NPD6234	Discontinued
0.7389	Intermediate Similarity	NPD4308	Phase 3
0.7386	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7381	Intermediate Similarity	NPD4965	Approved
0.738	Intermediate Similarity	NPD7871	Phase 2
0.738	Intermediate Similarity	NPD7870	Phase 2
0.7368	Intermediate Similarity	NPD3787	Discontinued
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7286	Phase 2
0.7356	Intermediate Similarity	NPD7054	Approved
0.7355	Intermediate Similarity	NPD2979	Phase 3
0.7338	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2313	Discontinued
0.7333	Intermediate Similarity	NPD4749	Approved
0.7318	Intermediate Similarity	NPD8434	Phase 2
0.7316	Intermediate Similarity	NPD8151	Discontinued
0.7314	Intermediate Similarity	NPD7472	Approved
0.7303	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD4626	Approved
0.7279	Intermediate Similarity	NPD1548	Phase 1
0.7279	Intermediate Similarity	NPD9545	Approved
0.7277	Intermediate Similarity	NPD7874	Approved
0.7277	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6535	Approved
0.7268	Intermediate Similarity	NPD6534	Approved
0.7267	Intermediate Similarity	NPD1608	Approved
0.7263	Intermediate Similarity	NPD7701	Phase 2
0.7258	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6273	Approved
0.7247	Intermediate Similarity	NPD8312	Approved
0.7247	Intermediate Similarity	NPD8313	Approved
0.7233	Intermediate Similarity	NPD2438	Suspended
0.723	Intermediate Similarity	NPD5691	Approved
0.7226	Intermediate Similarity	NPD3268	Approved
0.7222	Intermediate Similarity	NPD6190	Approved
0.7209	Intermediate Similarity	NPD7199	Phase 2
0.7195	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2798	Approved
0.7151	Intermediate Similarity	NPD7699	Phase 2
0.7151	Intermediate Similarity	NPD7700	Phase 2
0.715	Intermediate Similarity	NPD7801	Approved
0.7143	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9494	Approved
0.7135	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD1613	Approved
0.7134	Intermediate Similarity	NPD4307	Phase 2
0.7134	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2531	Phase 2
0.7124	Intermediate Similarity	NPD1203	Approved
0.7124	Intermediate Similarity	NPD2797	Approved
0.7115	Intermediate Similarity	NPD6798	Discontinued
0.7105	Intermediate Similarity	NPD8320	Phase 1
0.7105	Intermediate Similarity	NPD8319	Approved
0.7105	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7228	Approved
0.7099	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7086	Intermediate Similarity	NPD422	Phase 1
0.7086	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD17	Approved
0.7067	Intermediate Similarity	NPD3412	Clinical (unspecified phase)

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