NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.06
Volume:	256.396
LogP:	3.397
LogD:	2.058
LogS:	-3.949
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	2.465
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.068
MDCK Permeability:	7.776245183777064e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.989
20% Bioavailability (F20%):	0.969
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	97.63691711425781%
Volume Distribution (VD):	0.454
Pgp-substrate:	3.6758997440338135%

ADMET: Metabolism

CYP1A2-inhibitor:	0.954
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.358
CYP2C9-substrate:	0.362
CYP2D6-inhibitor:	0.606
CYP2D6-substrate:	0.205
CYP3A4-inhibitor:	0.194
CYP3A4-substrate:	0.068

ADMET: Excretion

Clearance (CL):	7.021
Half-life (T1/2):	0.712

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.025
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.755
Rat Oral Acute Toxicity:	0.051
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.956
Carcinogencity:	0.661
Eye Corrosion:	0.006
Eye Irritation:	0.939
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC93015

Natural Product ID:	NPC93015
*Common Name:**	2-Hydroxy-3-(Hydroxymethyl)Anthraquinone
IUPAC Name:	2-hydroxy-3-(hydroxymethyl)anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	LMXDYBJTJGPZPD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O4/c16-7-8-5-11-12(6-13(8)17)15(19)10-4-2-1-3-9(10)14(11)18/h1-6,16-17H,7H2
SMILES:	c1ccc2c(c1)C(=O)c1cc(CO)c(cc1C2=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251490
PubChem CID:	44445519
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11348221]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350148]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762798]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[15844957]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378361]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	fruits	Tahiti	n.a.	PMID[17378609]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[17480098]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[18076142]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21044847]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	roots	n.a.	n.a.	PMID[21973054]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	root	n.a.	PMID[21973054]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24224843]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27196335]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[32083868]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30972	Morinda officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16607	Rubia yunnanensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30972	Morinda officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4323	Morinda citrifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16607	Rubia yunnanensis	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
IC50	2
Others	2

Activity Type	# Activity
Cell Line	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3000.0	nM	PMID[448425]
NPT2	Others	Unspecified		Activity	=	0.94	uM	PMID[448424]
NPT27	Others	Unspecified		IC50	>	78000.0	nM	PMID[448424]
NPT2	Others	Unspecified		Ratio	>	83.0	n.a.	PMID[448424]

☑ 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 NPC93015 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	369
0.1-0.2	1666
0.2-0.3	3730
0.3-0.4	10175
0.4-0.5	8643
0.5-0.6	5158
0.6-0.7	8353
0.7-0.8	4082
0.8-0.85	387
0.85-0.9	117
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9531	High Similarity	NPC52407
0.9449	High Similarity	NPC31799
0.9297	High Similarity	NPC136588
0.9297	High Similarity	NPC199253
0.9274	High Similarity	NPC91478
0.9248	High Similarity	NPC190457
0.9194	High Similarity	NPC120545
0.9154	High Similarity	NPC70622
0.9111	High Similarity	NPC305845
0.9111	High Similarity	NPC204045
0.9098	High Similarity	NPC53414
0.9098	High Similarity	NPC53206
0.9044	High Similarity	NPC73061
0.9044	High Similarity	NPC135524
0.903	High Similarity	NPC4214
0.9023	High Similarity	NPC254847
0.9015	High Similarity	NPC44437
0.9015	High Similarity	NPC202225
0.8963	High Similarity	NPC242994
0.8963	High Similarity	NPC138099
0.8955	High Similarity	NPC471905
0.8931	High Similarity	NPC471851
0.8923	High Similarity	NPC99731
0.8921	High Similarity	NPC314437
0.8913	High Similarity	NPC244691
0.8913	High Similarity	NPC193703
0.8913	High Similarity	NPC471906
0.8913	High Similarity	NPC21599
0.8898	High Similarity	NPC375356
0.8897	High Similarity	NPC181560
0.8897	High Similarity	NPC169452
0.8872	High Similarity	NPC50924
0.8849	High Similarity	NPC478019
0.8846	High Similarity	NPC96024
0.8846	High Similarity	NPC282923
0.8846	High Similarity	NPC234175
0.8841	High Similarity	NPC66593
0.8828	High Similarity	NPC142956
0.8824	High Similarity	NPC143438
0.8819	High Similarity	NPC300274
0.8815	High Similarity	NPC475957
0.8806	High Similarity	NPC80035
0.8806	High Similarity	NPC258502
0.8797	High Similarity	NPC225051
0.8797	High Similarity	NPC294226
0.8797	High Similarity	NPC314048
0.8797	High Similarity	NPC267205
0.8797	High Similarity	NPC78307
0.8779	High Similarity	NPC276238
0.8779	High Similarity	NPC303910
0.8777	High Similarity	NPC48762
0.8769	High Similarity	NPC84672
0.8769	High Similarity	NPC69424
0.8769	High Similarity	NPC176130
0.8769	High Similarity	NPC78364
0.8768	High Similarity	NPC474961
0.8768	High Similarity	NPC193555
0.876	High Similarity	NPC103540
0.875	High Similarity	NPC416
0.875	High Similarity	NPC13715
0.875	High Similarity	NPC61398
0.8741	High Similarity	NPC315275
0.8714	High Similarity	NPC34482
0.8712	High Similarity	NPC108129
0.8712	High Similarity	NPC27659
0.8702	High Similarity	NPC48248
0.8696	High Similarity	NPC290550
0.8696	High Similarity	NPC246638
0.8692	High Similarity	NPC254492
0.8692	High Similarity	NPC96915
0.8692	High Similarity	NPC160499
0.8682	High Similarity	NPC199273
0.8672	High Similarity	NPC282577
0.8671	High Similarity	NPC290954
0.8671	High Similarity	NPC255641
0.8667	High Similarity	NPC283088
0.8657	High Similarity	NPC53896
0.8657	High Similarity	NPC477139
0.8652	High Similarity	NPC470570
0.8647	High Similarity	NPC244699
0.8647	High Similarity	NPC205992
0.8643	High Similarity	NPC79627
0.8636	High Similarity	NPC34414
0.8636	High Similarity	NPC146647
0.8633	High Similarity	NPC469520
0.8626	High Similarity	NPC72667
0.8623	High Similarity	NPC203063
0.8603	High Similarity	NPC191976
0.8603	High Similarity	NPC155211
0.8593	High Similarity	NPC288089
0.8593	High Similarity	NPC166480
0.8593	High Similarity	NPC282780
0.8561	High Similarity	NPC95537
0.8561	High Similarity	NPC3009
0.8551	High Similarity	NPC26924
0.8542	High Similarity	NPC147735
0.8538	High Similarity	NPC68756
0.8538	High Similarity	NPC152525
0.8538	High Similarity	NPC173978
0.8527	High Similarity	NPC307174
0.8521	High Similarity	NPC143685
0.8521	High Similarity	NPC300540
0.8519	High Similarity	NPC115458
0.8519	High Similarity	NPC59459
0.8516	High Similarity	NPC190971
0.8516	High Similarity	NPC216216
0.85	High Similarity	NPC19631
0.85	High Similarity	NPC257644
0.85	High Similarity	NPC239136
0.85	High Similarity	NPC85310
0.85	High Similarity	NPC137649
0.8496	Intermediate Similarity	NPC171460
0.8489	Intermediate Similarity	NPC315578
0.8489	Intermediate Similarity	NPC471853
0.8489	Intermediate Similarity	NPC183345
0.8483	Intermediate Similarity	NPC118427
0.8483	Intermediate Similarity	NPC470569
0.8473	Intermediate Similarity	NPC123506
0.8468	Intermediate Similarity	NPC196673
0.8462	Intermediate Similarity	NPC289042
0.8462	Intermediate Similarity	NPC312929
0.8462	Intermediate Similarity	NPC245584
0.8462	Intermediate Similarity	NPC119767
0.8462	Intermediate Similarity	NPC190648
0.8462	Intermediate Similarity	NPC126767
0.8462	Intermediate Similarity	NPC118027
0.8462	Intermediate Similarity	NPC56433
0.8451	Intermediate Similarity	NPC478160
0.845	Intermediate Similarity	NPC295034
0.844	Intermediate Similarity	NPC471682
0.844	Intermediate Similarity	NPC238629
0.8433	Intermediate Similarity	NPC147757
0.8433	Intermediate Similarity	NPC31539
0.8433	Intermediate Similarity	NPC55949
0.8429	Intermediate Similarity	NPC187843
0.8429	Intermediate Similarity	NPC91019
0.8429	Intermediate Similarity	NPC106519
0.8425	Intermediate Similarity	NPC164912
0.8414	Intermediate Similarity	NPC470568
0.8414	Intermediate Similarity	NPC205766
0.8409	Intermediate Similarity	NPC8745
0.8409	Intermediate Similarity	NPC15837
0.8409	Intermediate Similarity	NPC3224
0.8406	Intermediate Similarity	NPC305060
0.8406	Intermediate Similarity	NPC36868
0.8406	Intermediate Similarity	NPC264022
0.8406	Intermediate Similarity	NPC53001
0.8406	Intermediate Similarity	NPC147418
0.8397	Intermediate Similarity	NPC234890
0.8397	Intermediate Similarity	NPC181334
0.8397	Intermediate Similarity	NPC74507
0.8397	Intermediate Similarity	NPC164014
0.8397	Intermediate Similarity	NPC236189
0.8394	Intermediate Similarity	NPC161632
0.8394	Intermediate Similarity	NPC153088
0.8392	Intermediate Similarity	NPC147250
0.8385	Intermediate Similarity	NPC217756
0.8385	Intermediate Similarity	NPC176208
0.8385	Intermediate Similarity	NPC283514
0.8382	Intermediate Similarity	NPC111845
0.8382	Intermediate Similarity	NPC263817
0.838	Intermediate Similarity	NPC19896
0.8372	Intermediate Similarity	NPC248363
0.837	Intermediate Similarity	NPC474517
0.837	Intermediate Similarity	NPC72669
0.837	Intermediate Similarity	NPC85342
0.837	Intermediate Similarity	NPC41847
0.8369	Intermediate Similarity	NPC248068
0.8369	Intermediate Similarity	NPC69755
0.8367	Intermediate Similarity	NPC218870
0.8367	Intermediate Similarity	NPC470408
0.8367	Intermediate Similarity	NPC474824
0.8367	Intermediate Similarity	NPC182921
0.8367	Intermediate Similarity	NPC208806
0.8359	Intermediate Similarity	NPC473767
0.8357	Intermediate Similarity	NPC96421
0.8356	Intermediate Similarity	NPC230848
0.8345	Intermediate Similarity	NPC80370
0.8345	Intermediate Similarity	NPC87723
0.8345	Intermediate Similarity	NPC173980
0.8333	Intermediate Similarity	NPC272268
0.8333	Intermediate Similarity	NPC290194
0.8333	Intermediate Similarity	NPC10926
0.8333	Intermediate Similarity	NPC86524
0.8333	Intermediate Similarity	NPC137750
0.8333	Intermediate Similarity	NPC37709
0.8333	Intermediate Similarity	NPC118919
0.8333	Intermediate Similarity	NPC474813
0.8322	Intermediate Similarity	NPC471683
0.8321	Intermediate Similarity	NPC474519
0.8321	Intermediate Similarity	NPC274876
0.8321	Intermediate Similarity	NPC471187
0.8321	Intermediate Similarity	NPC12070
0.831	Intermediate Similarity	NPC296752
0.831	Intermediate Similarity	NPC478164
0.831	Intermediate Similarity	NPC313047
0.831	Intermediate Similarity	NPC451542
0.831	Intermediate Similarity	NPC295712
0.831	Intermediate Similarity	NPC474203
0.8309	Intermediate Similarity	NPC58685

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 NPC93015 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	358
0.1-0.2	966
0.2-0.3	1374
0.3-0.4	2714
0.4-0.5	2074
0.5-0.6	1120
0.6-0.7	455
0.7-0.8	83
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9023	High Similarity	NPD1509	Clinical (unspecified phase)
0.876	High Similarity	NPD1470	Approved
0.845	Intermediate Similarity	NPD1201	Approved
0.8273	Intermediate Similarity	NPD5406	Approved
0.8273	Intermediate Similarity	NPD5405	Approved
0.8273	Intermediate Similarity	NPD5408	Approved
0.8273	Intermediate Similarity	NPD5404	Approved
0.8125	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7390	Discontinued
0.8043	Intermediate Similarity	NPD943	Approved
0.7926	Intermediate Similarity	NPD1164	Approved
0.7817	Intermediate Similarity	NPD1510	Phase 2
0.7744	Intermediate Similarity	NPD3019	Approved
0.7733	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1607	Approved
0.7669	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3764	Approved
0.7643	Intermediate Similarity	NPD6232	Discontinued
0.7639	Intermediate Similarity	NPD2935	Discontinued
0.7616	Intermediate Similarity	NPD3226	Approved
0.7612	Intermediate Similarity	NPD2932	Approved
0.761	Intermediate Similarity	NPD7473	Discontinued
0.7586	Intermediate Similarity	NPD2346	Discontinued
0.7559	Intermediate Similarity	NPD2342	Discontinued
0.7551	Intermediate Similarity	NPD7003	Approved
0.7535	Intermediate Similarity	NPD1240	Approved
0.7534	Intermediate Similarity	NPD1549	Phase 2
0.7532	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD7458	Discontinued
0.7483	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6959	Discontinued
0.7466	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD1283	Approved
0.7451	Intermediate Similarity	NPD4380	Phase 2
0.7432	Intermediate Similarity	NPD3750	Approved
0.7424	Intermediate Similarity	NPD5951	Approved
0.7407	Intermediate Similarity	NPD5844	Phase 1
0.7407	Intermediate Similarity	NPD1651	Approved
0.7351	Intermediate Similarity	NPD2533	Approved
0.7351	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2534	Approved
0.7351	Intermediate Similarity	NPD2532	Approved
0.7347	Intermediate Similarity	NPD2344	Approved
0.7323	Intermediate Similarity	NPD1237	Approved
0.7319	Intermediate Similarity	NPD3972	Approved
0.7308	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3023	Approved
0.7299	Intermediate Similarity	NPD3026	Approved
0.7297	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD3024	Approved
0.7279	Intermediate Similarity	NPD3025	Approved
0.7261	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD1281	Approved
0.7237	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD74	Approved
0.7231	Intermediate Similarity	NPD9266	Approved
0.7222	Intermediate Similarity	NPD6663	Approved
0.7219	Intermediate Similarity	NPD3300	Phase 2
0.7214	Intermediate Similarity	NPD1876	Approved
0.7211	Intermediate Similarity	NPD2799	Discontinued
0.7206	Intermediate Similarity	NPD9545	Approved
0.7206	Intermediate Similarity	NPD3091	Approved
0.72	Intermediate Similarity	NPD8166	Discontinued
0.72	Intermediate Similarity	NPD4628	Phase 3
0.7194	Intermediate Similarity	NPD9269	Phase 2
0.7193	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6273	Approved
0.7185	Intermediate Similarity	NPD9493	Approved
0.7183	Intermediate Similarity	NPD5736	Approved
0.7179	Intermediate Similarity	NPD7411	Suspended
0.7171	Intermediate Similarity	NPD1511	Approved
0.717	Intermediate Similarity	NPD3749	Approved
0.716	Intermediate Similarity	NPD8150	Discontinued
0.7154	Intermediate Similarity	NPD9267	Approved
0.7154	Intermediate Similarity	NPD9264	Approved
0.7154	Intermediate Similarity	NPD9263	Approved
0.7153	Intermediate Similarity	NPD9268	Approved
0.7153	Intermediate Similarity	NPD2313	Discontinued
0.7152	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD7635	Approved
0.7134	Intermediate Similarity	NPD1934	Approved
0.7124	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD230	Phase 1
0.7114	Intermediate Similarity	NPD1471	Phase 3
0.7107	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4626	Approved
0.7101	Intermediate Similarity	NPD2286	Discontinued
0.7101	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3748	Approved
0.7095	Intermediate Similarity	NPD4308	Phase 3
0.7083	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1512	Approved
0.7071	Intermediate Similarity	NPD4878	Approved
0.7063	Intermediate Similarity	NPD9494	Approved
0.7063	Intermediate Similarity	NPD7075	Discontinued
0.7047	Intermediate Similarity	NPD1551	Phase 2
0.7047	Intermediate Similarity	NPD2796	Approved
0.7042	Intermediate Similarity	NPD1203	Approved
0.7042	Intermediate Similarity	NPD3094	Phase 2
0.7039	Intermediate Similarity	NPD6190	Approved
0.7012	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6535	Approved
0.7011	Intermediate Similarity	NPD6534	Approved
0.7	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7768	Phase 2
0.7	Intermediate Similarity	NPD3882	Suspended
0.7	Intermediate Similarity	NPD3092	Approved
0.7	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2798	Approved
0.6992	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD288	Approved
0.6982	Remote Similarity	NPD8312	Approved
0.6982	Remote Similarity	NPD8313	Approved
0.6981	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2801	Approved
0.6981	Remote Similarity	NPD1465	Phase 2
0.6978	Remote Similarity	NPD3095	Discontinued
0.6978	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7008	Discontinued
0.6957	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6213	Phase 3
0.6954	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6212	Phase 3
0.694	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD2979	Phase 3
0.6933	Remote Similarity	NPD6099	Approved
0.6933	Remote Similarity	NPD6100	Approved
0.6928	Remote Similarity	NPD3818	Discontinued
0.6928	Remote Similarity	NPD7177	Discontinued
0.6918	Remote Similarity	NPD6801	Discontinued
0.6918	Remote Similarity	NPD3268	Approved
0.6912	Remote Similarity	NPD9281	Approved
0.691	Remote Similarity	NPD6780	Approved
0.691	Remote Similarity	NPD6779	Approved
0.691	Remote Similarity	NPD6777	Approved
0.691	Remote Similarity	NPD6781	Approved
0.691	Remote Similarity	NPD6776	Approved
0.691	Remote Similarity	NPD6782	Approved
0.691	Remote Similarity	NPD6778	Approved
0.6909	Remote Similarity	NPD6166	Phase 2
0.6909	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5691	Approved
0.6905	Remote Similarity	NPD844	Approved
0.6901	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6599	Discontinued
0.6899	Remote Similarity	NPD1932	Approved
0.6893	Remote Similarity	NPD7699	Phase 2
0.6893	Remote Similarity	NPD7700	Phase 2
0.6879	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD3020	Approved
0.6871	Remote Similarity	NPD5494	Approved
0.6864	Remote Similarity	NPD6559	Discontinued
0.6846	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD9261	Approved
0.6846	Remote Similarity	NPD1929	Approved
0.6846	Remote Similarity	NPD1930	Approved
0.6838	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD3751	Discontinued
0.6824	Remote Similarity	NPD4307	Phase 2
0.6824	Remote Similarity	NPD4060	Phase 1
0.6822	Remote Similarity	NPD1242	Phase 1
0.6821	Remote Similarity	NPD2438	Suspended
0.6818	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD37	Approved
0.6806	Remote Similarity	NPD2797	Approved
0.6805	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD411	Approved
0.6797	Remote Similarity	NPD2800	Approved
0.6796	Remote Similarity	NPD7435	Discontinued
0.6796	Remote Similarity	NPD7698	Approved
0.6796	Remote Similarity	NPD7696	Phase 3
0.6796	Remote Similarity	NPD7697	Approved
0.6791	Remote Similarity	NPD3021	Approved
0.6791	Remote Similarity	NPD3022	Approved
0.6791	Remote Similarity	NPD4750	Phase 3
0.6788	Remote Similarity	NPD497	Approved
0.6788	Remote Similarity	NPD5711	Approved
0.6788	Remote Similarity	NPD5710	Approved
0.6786	Remote Similarity	NPD6020	Phase 2
0.6783	Remote Similarity	NPD1755	Approved
0.6774	Remote Similarity	NPD7236	Approved
0.6772	Remote Similarity	NPD2860	Approved
0.6772	Remote Similarity	NPD2859	Approved
0.6758	Remote Similarity	NPD7871	Phase 2
0.6758	Remote Similarity	NPD8320	Phase 1
0.6758	Remote Similarity	NPD8319	Approved
0.6758	Remote Similarity	NPD7870	Phase 2
0.6757	Remote Similarity	NPD520	Approved
0.6753	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD3400	Discontinued
0.6738	Remote Similarity	NPD4059	Approved
0.6735	Remote Similarity	NPD4625	Phase 3
0.6733	Remote Similarity	NPD4097	Suspended

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