NPASS Compound

Structure

CID124365 OpenBabel06191715482D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.7321 -0.0000 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 4.3301 -0.5000 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 4.3301 -1.5000 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 -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 3.4641 -2.0000 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 -1.5000 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 -0.5000 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 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 0.0000 -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 7 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 6 7 2 0 0 0 0 6 10 1 0 0 0 0 7 16 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 12 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 16 2 0 0 0 0 14 19 2 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.07
Volume:	282.482
LogP:	4.116
LogD:	2.832
LogS:	-6.134
# Rotatable Bonds:	1
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.715
Synthetic Accessibility Score:	2.345
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.075
MDCK Permeability:	1.517745931778336e-05
Pgp-inhibitor:	0.053
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	99.704345703125%
Volume Distribution (VD):	0.361
Pgp-substrate:	0.9842543005943298%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.839
CYP2C19-inhibitor:	0.156
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.63
CYP2C9-substrate:	0.555
CYP2D6-inhibitor:	0.254
CYP2D6-substrate:	0.256
CYP3A4-inhibitor:	0.597
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	10.03
Half-life (T1/2):	0.089

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.042
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.879
Rat Oral Acute Toxicity:	0.394
Maximum Recommended Daily Dose:	0.789
Skin Sensitization:	0.389
Carcinogencity:	0.904
Eye Corrosion:	0.005
Eye Irritation:	0.972
Respiratory Toxicity:	0.086

Download Data

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

Natural Product: NPC124365

Natural Product ID:	NPC124365
*Common Name:**	Islandicin 4-Methyl Ether
IUPAC Name:	4,5-dihydroxy-1-methoxy-2-methylanthracene-9,10-dione
Synonyms:	Islandicin 4-Methyl Ether
Standard InCHIKey:	NNCFIAAUBKRACV-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O5/c1-7-6-10(18)12-13(16(7)21-2)14(19)8-4-3-5-9(17)11(8)15(12)20/h3-6,17-18H,1-2H3
SMILES:	COc1c(C)cc(c2c1C(=O)c1cccc(c1C2=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478711
PubChem CID:	11119613
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
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374975]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23982	Ventilago leiocarpa	Species	Rhamnaceae	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
IC50	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1306	Cell Line	WISH	Homo sapiens	IC50	>	100000.0	nM	PMID[449623]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	>	100000.0	nM	PMID[449623]
NPT80	Cell Line	Raji	Homo sapiens	IC50	>	100000.0	nM	PMID[449623]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000.0	nM	PMID[449623]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[449623]
NPT1307	Cell Line	Calu-1	Homo sapiens	IC50	>	100000.0	nM	PMID[449623]

☑ 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 NPC124365 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	376
0.1-0.2	1641
0.2-0.3	3707
0.3-0.4	10181
0.4-0.5	8395
0.5-0.6	3707
0.6-0.7	7462
0.7-0.8	6241
0.8-0.85	803
0.85-0.9	168
0.9-0.95	13
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9704	High Similarity	NPC1268
0.964	High Similarity	NPC300540
0.9481	High Similarity	NPC141934
0.9333	High Similarity	NPC1249
0.9265	High Similarity	NPC281513
0.9265	High Similarity	NPC22222
0.9254	High Similarity	NPC205992
0.9236	High Similarity	NPC294646
0.9214	High Similarity	NPC69755
0.9104	High Similarity	NPC57552
0.9058	High Similarity	NPC474813
0.9058	High Similarity	NPC272268
0.903	High Similarity	NPC282923
0.9028	High Similarity	NPC56433
0.9028	High Similarity	NPC118027
0.9028	High Similarity	NPC289042
0.9028	High Similarity	NPC126767
0.9028	High Similarity	NPC245584
0.9028	High Similarity	NPC190648
0.9028	High Similarity	NPC312929
0.8993	High Similarity	NPC245923
0.8973	High Similarity	NPC147735
0.8973	High Similarity	NPC290954
0.8973	High Similarity	NPC255641
0.8951	High Similarity	NPC274085
0.8951	High Similarity	NPC89664
0.8912	High Similarity	NPC473201
0.8912	High Similarity	NPC302783
0.8905	High Similarity	NPC70622
0.8889	High Similarity	NPC478019
0.8881	High Similarity	NPC96915
0.8881	High Similarity	NPC476473
0.8881	High Similarity	NPC53016
0.8874	High Similarity	NPC284495
0.8857	High Similarity	NPC305060
0.8844	High Similarity	NPC470568
0.8841	High Similarity	NPC115458
0.8836	High Similarity	NPC5537
0.8824	High Similarity	NPC99731
0.8819	High Similarity	NPC193703
0.8819	High Similarity	NPC19896
0.8819	High Similarity	NPC21599
0.8819	High Similarity	NPC477409
0.8816	High Similarity	NPC311740
0.8815	High Similarity	NPC45537
0.8811	High Similarity	NPC474300
0.8806	High Similarity	NPC103540
0.8792	High Similarity	NPC208806
0.8792	High Similarity	NPC477691
0.8792	High Similarity	NPC135522
0.8786	High Similarity	NPC155211
0.8784	High Similarity	NPC470569
0.8776	High Similarity	NPC70764
0.8767	High Similarity	NPC478018
0.8767	High Similarity	NPC71055
0.8759	High Similarity	NPC136588
0.8759	High Similarity	NPC199253
0.875	High Similarity	NPC48248
0.875	High Similarity	NPC476506
0.875	High Similarity	NPC84571
0.8742	High Similarity	NPC44199
0.8742	High Similarity	NPC67197
0.8741	High Similarity	NPC149780
0.8733	High Similarity	NPC226656
0.8733	High Similarity	NPC66508
0.8732	High Similarity	NPC26924
0.8731	High Similarity	NPC173978
0.8731	High Similarity	NPC142956
0.8725	High Similarity	NPC477690
0.8725	High Similarity	NPC154683
0.8725	High Similarity	NPC40356
0.8725	High Similarity	NPC281272
0.8714	High Similarity	NPC283088
0.8699	High Similarity	NPC211565
0.8699	High Similarity	NPC147250
0.8699	High Similarity	NPC60389
0.8696	High Similarity	NPC205360
0.8696	High Similarity	NPC141549
0.869	High Similarity	NPC48762
0.8686	High Similarity	NPC146647
0.8686	High Similarity	NPC34414
0.8684	High Similarity	NPC324736
0.8681	High Similarity	NPC329493
0.8671	High Similarity	NPC315578
0.8667	High Similarity	NPC107109
0.8658	High Similarity	NPC118427
0.8658	High Similarity	NPC39819
0.8657	High Similarity	NPC375356
0.8649	High Similarity	NPC329933
0.8645	High Similarity	NPC26386
0.8643	High Similarity	NPC288089
0.8639	High Similarity	NPC119767
0.8639	High Similarity	NPC34802
0.8633	High Similarity	NPC474340
0.8633	High Similarity	NPC246693
0.8633	High Similarity	NPC110609
0.8633	High Similarity	NPC58685
0.8633	High Similarity	NPC242358
0.863	High Similarity	NPC49282
0.863	High Similarity	NPC34482
0.863	High Similarity	NPC73416
0.863	High Similarity	NPC160777
0.8623	High Similarity	NPC278787
0.8623	High Similarity	NPC7569
0.8623	High Similarity	NPC55949
0.8621	High Similarity	NPC167663
0.8621	High Similarity	NPC66593
0.8618	High Similarity	NPC178976
0.8611	High Similarity	NPC145673
0.8609	High Similarity	NPC66029
0.8609	High Similarity	NPC3898
0.8603	High Similarity	NPC306765
0.8603	High Similarity	NPC3224
0.8601	High Similarity	NPC471602
0.8601	High Similarity	NPC256463
0.8601	High Similarity	NPC29771
0.8601	High Similarity	NPC477408
0.8601	High Similarity	NPC470407
0.8601	High Similarity	NPC306835
0.8601	High Similarity	NPC111422
0.8601	High Similarity	NPC143438
0.8601	High Similarity	NPC476477
0.8601	High Similarity	NPC216312
0.8601	High Similarity	NPC299405
0.86	High Similarity	NPC164912
0.86	High Similarity	NPC3744
0.86	High Similarity	NPC175978
0.8591	High Similarity	NPC227122
0.8582	High Similarity	NPC300274
0.8581	High Similarity	NPC2569
0.8581	High Similarity	NPC172329
0.8581	High Similarity	NPC101769
0.8571	High Similarity	NPC314048
0.8571	High Similarity	NPC470570
0.8571	High Similarity	NPC225051
0.8571	High Similarity	NPC52407
0.8562	High Similarity	NPC186113
0.8553	High Similarity	NPC279605
0.8553	High Similarity	NPC5379
0.8553	High Similarity	NPC14561
0.8553	High Similarity	NPC77807
0.8552	High Similarity	NPC49108
0.8552	High Similarity	NPC182255
0.8552	High Similarity	NPC94076
0.8551	High Similarity	NPC206028
0.8551	High Similarity	NPC278928
0.8543	High Similarity	NPC214632
0.8543	High Similarity	NPC290927
0.8542	High Similarity	NPC37992
0.8542	High Similarity	NPC147542
0.8542	High Similarity	NPC42262
0.8542	High Similarity	NPC327916
0.8542	High Similarity	NPC220496
0.8542	High Similarity	NPC32749
0.8542	High Similarity	NPC241349
0.854	High Similarity	NPC470841
0.8535	High Similarity	NPC234331
0.8533	High Similarity	NPC144283
0.8531	High Similarity	NPC13715
0.8531	High Similarity	NPC475104
0.8523	High Similarity	NPC80370
0.8523	High Similarity	NPC266499
0.8519	High Similarity	NPC182646
0.8516	High Similarity	NPC146837
0.8516	High Similarity	NPC278329
0.8511	High Similarity	NPC274876
0.8506	High Similarity	NPC470342
0.8506	High Similarity	NPC472060
0.8506	High Similarity	NPC472052
0.8503	High Similarity	NPC471683
0.85	High Similarity	NPC118253
0.85	High Similarity	NPC309430
0.8497	Intermediate Similarity	NPC37543
0.8497	Intermediate Similarity	NPC263483
0.8497	Intermediate Similarity	NPC199463
0.8493	Intermediate Similarity	NPC84266
0.8493	Intermediate Similarity	NPC163948
0.8489	Intermediate Similarity	NPC198305
0.8489	Intermediate Similarity	NPC475741
0.8489	Intermediate Similarity	NPC31799
0.8483	Intermediate Similarity	NPC257003
0.8483	Intermediate Similarity	NPC187843
0.8483	Intermediate Similarity	NPC283292
0.8483	Intermediate Similarity	NPC471444
0.8477	Intermediate Similarity	NPC137125
0.8477	Intermediate Similarity	NPC149889
0.8477	Intermediate Similarity	NPC312338
0.8472	Intermediate Similarity	NPC18457
0.8472	Intermediate Similarity	NPC223336
0.8472	Intermediate Similarity	NPC242994
0.8472	Intermediate Similarity	NPC138099
0.8471	Intermediate Similarity	NPC29160
0.8467	Intermediate Similarity	NPC205766
0.8467	Intermediate Similarity	NPC315520
0.8467	Intermediate Similarity	NPC202595
0.8462	Intermediate Similarity	NPC471905
0.8462	Intermediate Similarity	NPC53206
0.8462	Intermediate Similarity	NPC476505
0.8462	Intermediate Similarity	NPC53414
0.8456	Intermediate Similarity	NPC186397

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 NPC124365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	348
0.1-0.2	980
0.2-0.3	1363
0.3-0.4	2552
0.4-0.5	2046
0.5-0.6	1201
0.6-0.7	486
0.7-0.8	161
0.8-0.85	9
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8904	High Similarity	NPD3226	Approved
0.8806	High Similarity	NPD1470	Approved
0.8794	High Similarity	NPD2346	Discontinued
0.8592	High Similarity	NPD2935	Discontinued
0.8507	High Similarity	NPD1201	Approved
0.8392	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6232	Discontinued
0.8239	Intermediate Similarity	NPD7473	Discontinued
0.8227	Intermediate Similarity	NPD2313	Discontinued
0.8125	Intermediate Similarity	NPD1607	Approved
0.8071	Intermediate Similarity	NPD2798	Approved
0.8014	Intermediate Similarity	NPD1510	Phase 2
0.8014	Intermediate Similarity	NPD2799	Discontinued
0.8013	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7003	Approved
0.7987	Intermediate Similarity	NPD6959	Discontinued
0.7986	Intermediate Similarity	NPD1240	Approved
0.7959	Intermediate Similarity	NPD5408	Approved
0.7959	Intermediate Similarity	NPD5404	Approved
0.7959	Intermediate Similarity	NPD5405	Approved
0.7959	Intermediate Similarity	NPD5406	Approved
0.7949	Intermediate Similarity	NPD7819	Suspended
0.7926	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD2344	Approved
0.7895	Intermediate Similarity	NPD2532	Approved
0.7895	Intermediate Similarity	NPD2533	Approved
0.7895	Intermediate Similarity	NPD2534	Approved
0.7882	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD2801	Approved
0.7834	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD7390	Discontinued
0.7806	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1283	Approved
0.78	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8313	Approved
0.7784	Intermediate Similarity	NPD8312	Approved
0.7778	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD4380	Phase 2
0.7754	Intermediate Similarity	NPD1651	Approved
0.7748	Intermediate Similarity	NPD3750	Approved
0.7748	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1549	Phase 2
0.7724	Intermediate Similarity	NPD3764	Approved
0.7718	Intermediate Similarity	NPD1551	Phase 2
0.7714	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7697	Intermediate Similarity	NPD2309	Approved
0.7676	Intermediate Similarity	NPD1876	Approved
0.7673	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1471	Phase 3
0.7667	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1934	Approved
0.7625	Intermediate Similarity	NPD7768	Phase 2
0.7622	Intermediate Similarity	NPD1203	Approved
0.7597	Intermediate Similarity	NPD1511	Approved
0.7595	Intermediate Similarity	NPD7411	Suspended
0.7593	Intermediate Similarity	NPD5494	Approved
0.7589	Intermediate Similarity	NPD1281	Approved
0.758	Intermediate Similarity	NPD7458	Discontinued
0.7578	Intermediate Similarity	NPD3749	Approved
0.7571	Intermediate Similarity	NPD6782	Approved
0.7571	Intermediate Similarity	NPD6779	Approved
0.7571	Intermediate Similarity	NPD6778	Approved
0.7571	Intermediate Similarity	NPD4626	Approved
0.7571	Intermediate Similarity	NPD6776	Approved
0.7571	Intermediate Similarity	NPD6781	Approved
0.7571	Intermediate Similarity	NPD6777	Approved
0.7571	Intermediate Similarity	NPD6780	Approved
0.7562	Intermediate Similarity	NPD5402	Approved
0.7547	Intermediate Similarity	NPD6844	Discontinued
0.7535	Intermediate Similarity	NPD3972	Approved
0.7533	Intermediate Similarity	NPD4308	Phase 3
0.75	Intermediate Similarity	NPD1512	Approved
0.7483	Intermediate Similarity	NPD2796	Approved
0.7483	Intermediate Similarity	NPD411	Approved
0.7469	Intermediate Similarity	NPD7075	Discontinued
0.7465	Intermediate Similarity	NPD1611	Approved
0.7456	Intermediate Similarity	NPD6559	Discontinued
0.7451	Intermediate Similarity	NPD2800	Approved
0.745	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD447	Suspended
0.7444	Intermediate Similarity	NPD7696	Phase 3
0.7444	Intermediate Similarity	NPD7435	Discontinued
0.7444	Intermediate Similarity	NPD7697	Approved
0.7444	Intermediate Similarity	NPD7698	Approved
0.7442	Intermediate Similarity	NPD8150	Discontinued
0.7425	Intermediate Similarity	NPD7177	Discontinued
0.7419	Intermediate Similarity	NPD3300	Phase 2
0.7417	Intermediate Similarity	NPD3748	Approved
0.7415	Intermediate Similarity	NPD4625	Phase 3
0.7413	Intermediate Similarity	NPD9717	Approved
0.741	Intermediate Similarity	NPD9493	Approved
0.741	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3882	Suspended
0.7403	Intermediate Similarity	NPD7871	Phase 2
0.7403	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4628	Phase 3
0.7403	Intermediate Similarity	NPD7870	Phase 2
0.7391	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6273	Approved
0.7389	Intermediate Similarity	NPD6823	Phase 2
0.7383	Intermediate Similarity	NPD943	Approved
0.7383	Intermediate Similarity	NPD2979	Phase 3
0.7368	Intermediate Similarity	NPD6099	Approved
0.7368	Intermediate Similarity	NPD6100	Approved
0.7365	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6832	Phase 2
0.7312	Intermediate Similarity	NPD6599	Discontinued
0.731	Intermediate Similarity	NPD6696	Suspended
0.7305	Intermediate Similarity	NPD6166	Phase 2
0.7305	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1608	Approved
0.7289	Intermediate Similarity	NPD5710	Approved
0.7289	Intermediate Similarity	NPD5711	Approved
0.7288	Intermediate Similarity	NPD6535	Approved
0.7288	Intermediate Similarity	NPD6534	Approved
0.7283	Intermediate Similarity	NPD7701	Phase 2
0.7267	Intermediate Similarity	NPD4307	Phase 2
0.726	Intermediate Similarity	NPD2797	Approved
0.726	Intermediate Similarity	NPD1164	Approved
0.7256	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD5691	Approved
0.7248	Intermediate Similarity	NPD3268	Approved
0.7246	Intermediate Similarity	NPD7635	Approved
0.7232	Intermediate Similarity	NPD6212	Phase 3
0.7232	Intermediate Similarity	NPD6213	Phase 3
0.7232	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6801	Discontinued
0.7219	Intermediate Similarity	NPD3751	Discontinued
0.7219	Intermediate Similarity	NPD3818	Discontinued
0.7215	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD7874	Approved
0.7203	Intermediate Similarity	NPD3019	Approved
0.7195	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD6651	Approved
0.7167	Intermediate Similarity	NPD7699	Phase 2
0.7167	Intermediate Similarity	NPD7700	Phase 2
0.7166	Intermediate Similarity	NPD7801	Approved
0.7162	Intermediate Similarity	NPD2861	Phase 2
0.7152	Intermediate Similarity	NPD6799	Approved
0.7152	Intermediate Similarity	NPD4060	Phase 1
0.7143	Intermediate Similarity	NPD5951	Approved
0.7134	Intermediate Similarity	NPD2296	Approved
0.7134	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD3817	Phase 2
0.7132	Intermediate Similarity	NPD2342	Discontinued
0.7126	Intermediate Similarity	NPD1247	Approved
0.7125	Intermediate Similarity	NPD920	Approved
0.7125	Intermediate Similarity	NPD5403	Approved
0.7123	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD37	Approved
0.7107	Intermediate Similarity	NPD5401	Approved
0.7105	Intermediate Similarity	NPD1933	Approved
0.7093	Intermediate Similarity	NPD5953	Discontinued
0.7092	Intermediate Similarity	NPD6671	Approved
0.7083	Intermediate Similarity	NPD17	Approved
0.7083	Intermediate Similarity	NPD2932	Approved
0.7083	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD1465	Phase 2
0.7071	Intermediate Similarity	NPD1398	Phase 1
0.7067	Intermediate Similarity	NPD7008	Discontinued
0.7055	Intermediate Similarity	NPD1481	Phase 2
0.7047	Intermediate Similarity	NPD9494	Approved
0.7045	Intermediate Similarity	NPD8434	Phase 2
0.7044	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7340	Approved
0.7035	Intermediate Similarity	NPD7074	Phase 3
0.7034	Intermediate Similarity	NPD3496	Discontinued
0.7032	Intermediate Similarity	NPD2531	Phase 2
0.7032	Intermediate Similarity	NPD4477	Approved
0.7032	Intermediate Similarity	NPD4476	Approved
0.7032	Intermediate Similarity	NPD2438	Suspended
0.7027	Intermediate Similarity	NPD3267	Approved
0.7027	Intermediate Similarity	NPD3266	Approved
0.7025	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1243	Approved
0.7006	Intermediate Similarity	NPD6234	Discontinued
0.7006	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4967	Phase 2
0.6988	Remote Similarity	NPD4966	Approved
0.6988	Remote Similarity	NPD4965	Approved
0.6986	Remote Similarity	NPD1535	Discovery
0.698	Remote Similarity	NPD1019	Discontinued
0.6977	Remote Similarity	NPD7054	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