NPASS Compound

Structure

NPC474414 OpenBabel07101718282D 24 26 0 0 0 0 0 0 0 0999 V2000 -4.3301 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 -0.0000 -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 0.8660 2.5000 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 1.7321 1.0000 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 -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 -0.0000 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 -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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 9 2 0 0 0 0 7 13 1 0 0 0 0 8 11 1 0 0 0 0 8 12 2 0 0 0 0 9 14 1 0 0 0 0 10 11 1 0 0 0 0 10 15 2 0 0 0 0 11 19 2 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 17 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 18 2 0 0 0 0 15 16 1 0 0 0 0 16 20 2 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.09
Volume:	325.865
LogP:	2.46
LogD:	2.27
LogS:	-4.644
# Rotatable Bonds:	4
TPSA:	71.06
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.859
Synthetic Accessibility Score:	2.543
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.713
MDCK Permeability:	3.464133624220267e-05
Pgp-inhibitor:	0.992
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	84.00081634521484%
Volume Distribution (VD):	0.589
Pgp-substrate:	13.859833717346191%

ADMET: Metabolism

CYP1A2-inhibitor:	0.901
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.833
CYP2C19-substrate:	0.815
CYP2C9-inhibitor:	0.725
CYP2C9-substrate:	0.892
CYP2D6-inhibitor:	0.291
CYP2D6-substrate:	0.624
CYP3A4-inhibitor:	0.766
CYP3A4-substrate:	0.484

ADMET: Excretion

Clearance (CL):	5.811
Half-life (T1/2):	0.418

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.588
Drug-inuced Liver Injury (DILI):	0.589
AMES Toxicity:	0.657
Rat Oral Acute Toxicity:	0.916
Maximum Recommended Daily Dose:	0.866
Skin Sensitization:	0.83
Carcinogencity:	0.821
Eye Corrosion:	0.009
Eye Irritation:	0.324
Respiratory Toxicity:	0.86

Download Data

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

Natural Product: NPC474414

Natural Product ID:	NPC474414
*Common Name:**	3,5,6,7-Tetramethoxyphenanthrene-1,4-Dione
IUPAC Name:	3,5,6,7-tetramethoxyphenanthrene-1,4-dione
Synonyms:
Standard InCHIKey:	VGIOMSHQGNUITE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-21-12-8-11(19)10-6-5-9-7-13(22-2)17(23-3)18(24-4)14(9)15(10)16(12)20/h5-8H,1-4H3
SMILES:	COC1=CC(=O)C2=C(C1=O)C3=C(C(=C(C=C3C=C2)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467548
PubChem CID:	21593745
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO13975	Calanthe arisanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18640035]
NPO13975	Calanthe arisanensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19193043]
NPO13975	Calanthe arisanensis	Species	Orchidaceae	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
EC50	7

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	EC50	=	7.06	ug.mL-1	PMID[512118]
NPT306	Cell Line	PC-3	Homo sapiens	EC50	=	7.81	ug.mL-1	PMID[512118]
NPT90	Cell Line	DU-145	Homo sapiens	EC50	=	4.4	ug.mL-1	PMID[512118]
NPT180	Cell Line	HCT-8	Homo sapiens	EC50	=	15.25	ug.mL-1	PMID[512118]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	5.33	ug.mL-1	PMID[512118]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	8.08	ug.mL-1	PMID[512118]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	9.14	ug.mL-1	PMID[512118]

☑ 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 NPC474414 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	516
0.1-0.2	1832
0.2-0.3	4505
0.3-0.4	11599
0.4-0.5	6313
0.5-0.6	3682
0.6-0.7	6090
0.7-0.8	6846
0.8-0.85	1194
0.85-0.9	113
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.947	High Similarity	NPC104876
0.947	High Similarity	NPC245891
0.9195	High Similarity	NPC80370
0.9116	High Similarity	NPC472836
0.9097	High Similarity	NPC470962
0.9073	High Similarity	NPC230848
0.9	High Similarity	NPC472841
0.8947	High Similarity	NPC78505
0.8926	High Similarity	NPC49282
0.8919	High Similarity	NPC167663
0.8903	High Similarity	NPC199463
0.8903	High Similarity	NPC37543
0.8903	High Similarity	NPC178976
0.8846	High Similarity	NPC125713
0.8839	High Similarity	NPC5379
0.8839	High Similarity	NPC14561
0.8839	High Similarity	NPC77807
0.8831	High Similarity	NPC473664
0.8824	High Similarity	NPC189773
0.8808	High Similarity	NPC58373
0.8808	High Similarity	NPC474999
0.8792	High Similarity	NPC476054
0.8767	High Similarity	NPC290601
0.875	High Similarity	NPC472839
0.875	High Similarity	NPC476058
0.8734	High Similarity	NPC311740
0.8726	High Similarity	NPC477410
0.8725	High Similarity	NPC28326
0.8725	High Similarity	NPC185607
0.871	High Similarity	NPC107109
0.8707	High Similarity	NPC44573
0.8701	High Similarity	NPC306011
0.8701	High Similarity	NPC472838
0.8699	High Similarity	NPC471182
0.8688	High Similarity	NPC26386
0.8684	High Similarity	NPC299923
0.8684	High Similarity	NPC77598
0.8679	High Similarity	NPC475144
0.8679	High Similarity	NPC108767
0.8675	High Similarity	NPC157133
0.8675	High Similarity	NPC474446
0.8671	High Similarity	NPC84571
0.8654	High Similarity	NPC234485
0.8649	High Similarity	NPC223336
0.8645	High Similarity	NPC312338
0.8645	High Similarity	NPC149889
0.8639	High Similarity	NPC186647
0.8636	High Similarity	NPC216917
0.8636	High Similarity	NPC58310
0.8636	High Similarity	NPC295977
0.863	High Similarity	NPC88065
0.863	High Similarity	NPC89504
0.863	High Similarity	NPC95485
0.8618	High Similarity	NPC216314
0.8618	High Similarity	NPC120924
0.8618	High Similarity	NPC310259
0.8618	High Similarity	NPC195919
0.8616	High Similarity	NPC66288
0.8609	High Similarity	NPC105213
0.8609	High Similarity	NPC189650
0.8609	High Similarity	NPC207732
0.8608	High Similarity	NPC250076
0.859	High Similarity	NPC93552
0.859	High Similarity	NPC127172
0.8581	High Similarity	NPC302783
0.8581	High Similarity	NPC220577
0.8581	High Similarity	NPC272566
0.8581	High Similarity	NPC473201
0.8571	High Similarity	NPC69752
0.8571	High Similarity	NPC300983
0.8562	High Similarity	NPC117463
0.8562	High Similarity	NPC245584
0.8562	High Similarity	NPC126767
0.8562	High Similarity	NPC190648
0.8562	High Similarity	NPC312929
0.8562	High Similarity	NPC289042
0.8562	High Similarity	NPC149389
0.8562	High Similarity	NPC118027
0.8562	High Similarity	NPC470511
0.8562	High Similarity	NPC56433
0.8553	High Similarity	NPC136278
0.8553	High Similarity	NPC471590
0.8553	High Similarity	NPC28632
0.8552	High Similarity	NPC183103
0.8545	High Similarity	NPC245975
0.8544	High Similarity	NPC474637
0.8543	High Similarity	NPC215451
0.8543	High Similarity	NPC277369
0.8535	High Similarity	NPC66508
0.8535	High Similarity	NPC226656
0.8533	High Similarity	NPC58229
0.8526	High Similarity	NPC164912
0.8526	High Similarity	NPC474993
0.8516	High Similarity	NPC259058
0.8516	High Similarity	NPC189270
0.8516	High Similarity	NPC290954
0.8516	High Similarity	NPC474660
0.8516	High Similarity	NPC255641
0.8516	High Similarity	NPC5840
0.8516	High Similarity	NPC201547
0.8516	High Similarity	NPC472279
0.8516	High Similarity	NPC470568
0.8509	High Similarity	NPC270837
0.8509	High Similarity	NPC197168
0.8506	High Similarity	NPC472056
0.8506	High Similarity	NPC476342
0.8506	High Similarity	NPC63256
0.8506	High Similarity	NPC10304
0.8487	Intermediate Similarity	NPC293201
0.8487	Intermediate Similarity	NPC113089
0.8487	Intermediate Similarity	NPC308006
0.8487	Intermediate Similarity	NPC182842
0.8485	Intermediate Similarity	NPC65885
0.8481	Intermediate Similarity	NPC279605
0.8477	Intermediate Similarity	NPC312256
0.8477	Intermediate Similarity	NPC201297
0.8471	Intermediate Similarity	NPC472408
0.8467	Intermediate Similarity	NPC109007
0.8466	Intermediate Similarity	NPC234331
0.8462	Intermediate Similarity	NPC144283
0.8462	Intermediate Similarity	NPC256406
0.8462	Intermediate Similarity	NPC470569
0.8462	Intermediate Similarity	NPC118427
0.8462	Intermediate Similarity	NPC118332
0.8457	Intermediate Similarity	NPC25361
0.8457	Intermediate Similarity	NPC303174
0.8452	Intermediate Similarity	NPC329933
0.8452	Intermediate Similarity	NPC181250
0.8452	Intermediate Similarity	NPC134293
0.8447	Intermediate Similarity	NPC294965
0.8442	Intermediate Similarity	NPC205522
0.8442	Intermediate Similarity	NPC34802
0.8442	Intermediate Similarity	NPC294972
0.8431	Intermediate Similarity	NPC476362
0.8428	Intermediate Similarity	NPC201127
0.8428	Intermediate Similarity	NPC217677
0.8428	Intermediate Similarity	NPC165977
0.8428	Intermediate Similarity	NPC136674
0.8425	Intermediate Similarity	NPC153453
0.8421	Intermediate Similarity	NPC16353
0.8421	Intermediate Similarity	NPC9966
0.8421	Intermediate Similarity	NPC119663
0.8421	Intermediate Similarity	NPC70853
0.8421	Intermediate Similarity	NPC84266
0.8421	Intermediate Similarity	NPC50954
0.8418	Intermediate Similarity	NPC57674
0.8418	Intermediate Similarity	NPC230149
0.8418	Intermediate Similarity	NPC117992
0.8418	Intermediate Similarity	NPC168247
0.8418	Intermediate Similarity	NPC152951
0.8415	Intermediate Similarity	NPC99613
0.8415	Intermediate Similarity	NPC49487
0.8411	Intermediate Similarity	NPC110419
0.8408	Intermediate Similarity	NPC154683
0.8408	Intermediate Similarity	NPC166201
0.8408	Intermediate Similarity	NPC28103
0.8408	Intermediate Similarity	NPC40356
0.8408	Intermediate Similarity	NPC40033
0.8405	Intermediate Similarity	NPC298071
0.8405	Intermediate Similarity	NPC29160
0.8405	Intermediate Similarity	NPC477517
0.84	Intermediate Similarity	NPC470407
0.8397	Intermediate Similarity	NPC473466
0.8397	Intermediate Similarity	NPC85131
0.8397	Intermediate Similarity	NPC294646
0.8397	Intermediate Similarity	NPC147735
0.8395	Intermediate Similarity	NPC132054
0.8395	Intermediate Similarity	NPC476822
0.8395	Intermediate Similarity	NPC236132
0.8387	Intermediate Similarity	NPC261548
0.8385	Intermediate Similarity	NPC474239
0.8385	Intermediate Similarity	NPC474187
0.8383	Intermediate Similarity	NPC8127
0.8383	Intermediate Similarity	NPC49667
0.8378	Intermediate Similarity	NPC22644
0.8377	Intermediate Similarity	NPC473927
0.8377	Intermediate Similarity	NPC106461
0.8377	Intermediate Similarity	NPC215932
0.8377	Intermediate Similarity	NPC231013
0.8377	Intermediate Similarity	NPC40818
0.8377	Intermediate Similarity	NPC110639
0.8377	Intermediate Similarity	NPC12377
0.8377	Intermediate Similarity	NPC14958
0.8377	Intermediate Similarity	NPC165389
0.8375	Intermediate Similarity	NPC474043
0.8375	Intermediate Similarity	NPC45846
0.8375	Intermediate Similarity	NPC324736
0.8375	Intermediate Similarity	NPC235448
0.8366	Intermediate Similarity	NPC19896
0.8365	Intermediate Similarity	NPC474167
0.8365	Intermediate Similarity	NPC474983
0.8365	Intermediate Similarity	NPC265511
0.8365	Intermediate Similarity	NPC470762
0.8365	Intermediate Similarity	NPC472455
0.8365	Intermediate Similarity	NPC288353
0.8364	Intermediate Similarity	NPC476641
0.8356	Intermediate Similarity	NPC471983
0.8356	Intermediate Similarity	NPC149337
0.8355	Intermediate Similarity	NPC49108
0.8355	Intermediate Similarity	NPC29536

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 NPC474414 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	449
0.1-0.2	1010
0.2-0.3	1616
0.3-0.4	2735
0.4-0.5	1804
0.5-0.6	990
0.6-0.7	390
0.7-0.8	139
0.8-0.85	15
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8679	High Similarity	NPD6232	Discontinued
0.8634	High Similarity	NPD7473	Discontinued
0.8323	Intermediate Similarity	NPD5494	Approved
0.8303	Intermediate Similarity	NPD5844	Phase 1
0.8282	Intermediate Similarity	NPD3926	Phase 2
0.825	Intermediate Similarity	NPD3882	Suspended
0.8205	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD3817	Phase 2
0.816	Intermediate Similarity	NPD1247	Approved
0.8148	Intermediate Similarity	NPD919	Approved
0.805	Intermediate Similarity	NPD6599	Discontinued
0.8012	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2801	Approved
0.8012	Intermediate Similarity	NPD7819	Suspended
0.7962	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD3748	Approved
0.795	Intermediate Similarity	NPD1934	Approved
0.7908	Intermediate Similarity	NPD2796	Approved
0.7898	Intermediate Similarity	NPD6799	Approved
0.7866	Intermediate Similarity	NPD7075	Discontinued
0.7843	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6801	Discontinued
0.7829	Intermediate Similarity	NPD1607	Approved
0.7799	Intermediate Similarity	NPD1512	Approved
0.7798	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6166	Phase 2
0.7798	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD1465	Phase 2
0.7727	Intermediate Similarity	NPD1510	Phase 2
0.7725	Intermediate Similarity	NPD6959	Discontinued
0.7716	Intermediate Similarity	NPD4380	Phase 2
0.7708	Intermediate Similarity	NPD1651	Approved
0.7707	Intermediate Similarity	NPD3750	Approved
0.7697	Intermediate Similarity	NPD1240	Approved
0.7697	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1511	Approved
0.7633	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD2533	Approved
0.7625	Intermediate Similarity	NPD2532	Approved
0.7625	Intermediate Similarity	NPD2534	Approved
0.7622	Intermediate Similarity	NPD37	Approved
0.7619	Intermediate Similarity	NPD3972	Approved
0.7602	Intermediate Similarity	NPD3818	Discontinued
0.7546	Intermediate Similarity	NPD3226	Approved
0.7542	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5242	Approved
0.7528	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD3751	Discontinued
0.7486	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7808	Phase 3
0.7485	Intermediate Similarity	NPD4966	Approved
0.7485	Intermediate Similarity	NPD4967	Phase 2
0.7485	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6797	Phase 2
0.7468	Intermediate Similarity	NPD943	Approved
0.7468	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1549	Phase 2
0.7455	Intermediate Similarity	NPD7411	Suspended
0.7453	Intermediate Similarity	NPD7390	Discontinued
0.7448	Intermediate Similarity	NPD5536	Phase 2
0.7432	Intermediate Similarity	NPD1281	Approved
0.7429	Intermediate Similarity	NPD7251	Discontinued
0.7425	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5402	Approved
0.7423	Intermediate Similarity	NPD920	Approved
0.7421	Intermediate Similarity	NPD1243	Approved
0.7421	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7074	Phase 3
0.7412	Intermediate Similarity	NPD7199	Phase 2
0.7405	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2346	Discontinued
0.7405	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1876	Approved
0.7396	Intermediate Similarity	NPD6234	Discontinued
0.7389	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7003	Approved
0.7375	Intermediate Similarity	NPD4628	Phase 3
0.736	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD7054	Approved
0.7346	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6099	Approved
0.7342	Intermediate Similarity	NPD2935	Discontinued
0.7342	Intermediate Similarity	NPD6100	Approved
0.7342	Intermediate Similarity	NPD2438	Suspended
0.7337	Intermediate Similarity	NPD3749	Approved
0.7333	Intermediate Similarity	NPD7458	Discontinued
0.733	Intermediate Similarity	NPD6559	Discontinued
0.7321	Intermediate Similarity	NPD5978	Approved
0.7321	Intermediate Similarity	NPD5977	Approved
0.7317	Intermediate Similarity	NPD5403	Approved
0.7314	Intermediate Similarity	NPD7472	Approved
0.7301	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD5401	Approved
0.7285	Intermediate Similarity	NPD1283	Approved
0.7284	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD7768	Phase 2
0.7273	Intermediate Similarity	NPD4625	Phase 3
0.7267	Intermediate Similarity	NPD3787	Discontinued
0.7267	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD3018	Phase 2
0.7246	Intermediate Similarity	NPD5089	Approved
0.7246	Intermediate Similarity	NPD6385	Approved
0.7246	Intermediate Similarity	NPD5090	Approved
0.7246	Intermediate Similarity	NPD6386	Approved
0.7244	Intermediate Similarity	NPD2979	Phase 3
0.7235	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5353	Approved
0.7205	Intermediate Similarity	NPD2800	Approved
0.7197	Intermediate Similarity	NPD1933	Approved
0.7197	Intermediate Similarity	NPD230	Phase 1
0.7184	Intermediate Similarity	NPD2403	Approved
0.7172	Intermediate Similarity	NPD5283	Phase 1
0.717	Intermediate Similarity	NPD2799	Discontinued
0.7168	Intermediate Similarity	NPD7229	Phase 3
0.7166	Intermediate Similarity	NPD6777	Approved
0.7166	Intermediate Similarity	NPD6781	Approved
0.7166	Intermediate Similarity	NPD6780	Approved
0.7166	Intermediate Similarity	NPD6782	Approved
0.7166	Intermediate Similarity	NPD6776	Approved
0.7166	Intermediate Similarity	NPD6779	Approved
0.7166	Intermediate Similarity	NPD6778	Approved
0.7161	Intermediate Similarity	NPD3027	Phase 3
0.716	Intermediate Similarity	NPD4585	Approved
0.7152	Intermediate Similarity	NPD2981	Phase 2
0.7152	Intermediate Similarity	NPD6651	Approved
0.7143	Intermediate Similarity	NPD7435	Discontinued
0.7143	Intermediate Similarity	NPD9494	Approved
0.7127	Intermediate Similarity	NPD8150	Discontinued
0.7127	Intermediate Similarity	NPD8434	Phase 2
0.7125	Intermediate Similarity	NPD5405	Approved
0.7125	Intermediate Similarity	NPD5406	Approved
0.7125	Intermediate Similarity	NPD5404	Approved
0.7125	Intermediate Similarity	NPD5408	Approved
0.7124	Intermediate Similarity	NPD1470	Approved
0.7117	Intermediate Similarity	NPD6190	Approved
0.7114	Intermediate Similarity	NPD5691	Approved
0.7105	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD2982	Phase 2
0.7105	Intermediate Similarity	NPD2983	Phase 2
0.7102	Intermediate Similarity	NPD7228	Approved
0.7091	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2344	Approved
0.7078	Intermediate Similarity	NPD2798	Approved
0.7069	Intermediate Similarity	NPD5710	Approved
0.7069	Intermediate Similarity	NPD5711	Approved
0.7067	Intermediate Similarity	NPD4626	Approved
0.7056	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7697	Approved
0.7053	Intermediate Similarity	NPD7696	Phase 3
0.7053	Intermediate Similarity	NPD7698	Approved
0.7047	Intermediate Similarity	NPD8151	Discontinued
0.7041	Intermediate Similarity	NPD6873	Phase 2
0.703	Intermediate Similarity	NPD4357	Discontinued
0.7025	Intermediate Similarity	NPD4307	Phase 2
0.7025	Intermediate Similarity	NPD4060	Phase 1
0.7019	Intermediate Similarity	NPD1551	Phase 2
0.7019	Intermediate Similarity	NPD2531	Phase 2
0.7018	Intermediate Similarity	NPD4288	Approved
0.7016	Intermediate Similarity	NPD7870	Phase 2
0.7016	Intermediate Similarity	NPD7871	Phase 2
0.7012	Intermediate Similarity	NPD3887	Approved
0.7006	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7177	Discontinued
0.6994	Remote Similarity	NPD2654	Approved
0.6988	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4107	Approved
0.6983	Remote Similarity	NPD5953	Discontinued
0.6982	Remote Similarity	NPD7028	Phase 2
0.6981	Remote Similarity	NPD447	Suspended
0.6975	Remote Similarity	NPD2353	Approved
0.6975	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD17	Approved
0.6946	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7240	Approved
0.6923	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7874	Approved
0.6918	Remote Similarity	NPD1613	Approved
0.6918	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.691	Remote Similarity	NPD2163	Approved
0.6909	Remote Similarity	NPD2309	Approved
0.6907	Remote Similarity	NPD7701	Phase 2
0.6903	Remote Similarity	NPD3266	Approved
0.6903	Remote Similarity	NPD3267	Approved
0.6899	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2313	Discontinued
0.6899	Remote Similarity	NPD6798	Discontinued
0.6899	Remote Similarity	NPD3764	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