NPASS Compound

Structure

CID155211 OpenBabel06191715522D 24 27 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 1.7321 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 -2.5981 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 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 -0.8660 0.5000 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 -0.0000 -0.0000 0.0000 C 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 -1.7321 -1.0000 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 -0.0000 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 8 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 5 2 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 8 1 0 0 0 0 7 13 2 0 0 0 0 9 14 2 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 16 2 0 0 0 0 11 20 1 0 0 0 0 12 17 2 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 1 0 0 0 0 18 23 2 0 0 0 0 19 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.07
Volume:	320.541
LogP:	4.678
LogD:	2.792
LogS:	-4.959
# Rotatable Bonds:	0
TPSA:	94.83
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.436
Synthetic Accessibility Score:	2.796
Fsp3:	0.053
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:	-5.11
MDCK Permeability:	7.877856660343241e-06
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.458
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	98.62479400634766%
Volume Distribution (VD):	0.313
Pgp-substrate:	2.0133533477783203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.173
CYP2C19-inhibitor:	0.236
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.717
CYP2C9-substrate:	0.557
CYP2D6-inhibitor:	0.467
CYP2D6-substrate:	0.203
CYP3A4-inhibitor:	0.181
CYP3A4-substrate:	0.077

ADMET: Excretion

Clearance (CL):	4.102
Half-life (T1/2):	0.479

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.297
Drug-inuced Liver Injury (DILI):	0.943
AMES Toxicity:	0.765
Rat Oral Acute Toxicity:	0.602
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.936
Carcinogencity:	0.845
Eye Corrosion:	0.019
Eye Irritation:	0.959
Respiratory Toxicity:	0.428

Download Data

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

Natural Product: NPC155211

Natural Product ID:	NPC155211
*Common Name:**	Anhydrolandomycinone
IUPAC Name:	1,8,11-trihydroxy-3-methylbenzo[a]anthracene-7,12-dione
Synonyms:	Anhydrolandomycinone
Standard InCHIKey:	MIQMSWIIJSSWOT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H12O5/c1-8-6-9-2-3-10-15(14(9)13(22)7-8)19(24)17-12(21)5-4-11(20)16(17)18(10)23/h2-7,20-22H,1H3
SMILES:	Cc1cc2ccc3c(c2c(c1)O)C(=O)c1c(ccc(c1C3=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668341
PubChem CID:	51354811
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003415] Angucyclines

*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
NPO19685	Streptomyces cyanogenus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21188999]
NPO19685	Streptomyces cyanogenus	Species	Streptomycetaceae	Bacteria	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

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1800.0	nM	PMID[465980]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2000.0	nM	PMID[465980]

☑ 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 NPC155211 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	418
0.1-0.2	1809
0.2-0.3	4091
0.3-0.4	11338
0.4-0.5	7849
0.5-0.6	6324
0.6-0.7	7203
0.7-0.8	3310
0.8-0.85	248
0.85-0.9	79
0.9-0.95	24
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9767	High Similarity	NPC225051
0.9695	High Similarity	NPC474813
0.9621	High Similarity	NPC245923
0.9323	High Similarity	NPC80035
0.9313	High Similarity	NPC205992
0.9248	High Similarity	NPC50924
0.9237	High Similarity	NPC55949
0.9231	High Similarity	NPC48248
0.9225	High Similarity	NPC96915
0.9209	High Similarity	NPC471683
0.916	High Similarity	NPC34414
0.916	High Similarity	NPC146647
0.913	High Similarity	NPC69755
0.913	High Similarity	NPC239136
0.913	High Similarity	NPC19631
0.9124	High Similarity	NPC96421
0.9118	High Similarity	NPC13715
0.9111	High Similarity	NPC272268
0.9091	High Similarity	NPC136588
0.9091	High Similarity	NPC199253
0.9084	High Similarity	NPC282923
0.907	High Similarity	NPC142956
0.9065	High Similarity	NPC471682
0.9058	High Similarity	NPC246638
0.9037	High Similarity	NPC283088
0.903	High Similarity	NPC52407
0.9023	High Similarity	NPC244699
0.9023	High Similarity	NPC72669
0.9023	High Similarity	NPC474517
0.8993	High Similarity	NPC257644
0.8992	High Similarity	NPC375356
0.8955	High Similarity	NPC70622
0.8931	High Similarity	NPC306765
0.8915	High Similarity	NPC300274
0.8913	High Similarity	NPC143438
0.8905	High Similarity	NPC305060
0.8889	High Similarity	NPC53896
0.8889	High Similarity	NPC115458
0.8872	High Similarity	NPC99731
0.8865	High Similarity	NPC10764
0.8855	High Similarity	NPC103540
0.8841	High Similarity	NPC4214
0.8824	High Similarity	NPC287604
0.8824	High Similarity	NPC288089
0.8824	High Similarity	NPC472262
0.8824	High Similarity	NPC161964
0.8815	High Similarity	NPC58685
0.8811	High Similarity	NPC37709
0.8806	High Similarity	NPC31799
0.8806	High Similarity	NPC31539
0.8788	High Similarity	NPC160499
0.8786	High Similarity	NPC124365
0.8779	High Similarity	NPC173978
0.8777	High Similarity	NPC138099
0.8777	High Similarity	NPC26924
0.8777	High Similarity	NPC242994
0.8776	High Similarity	NPC66029
0.8769	High Similarity	NPC307174
0.8768	High Similarity	NPC53414
0.8768	High Similarity	NPC471905
0.8768	High Similarity	NPC53206
0.876	High Similarity	NPC472046
0.8759	High Similarity	NPC315520
0.8759	High Similarity	NPC258502
0.8732	High Similarity	NPC79627
0.8731	High Similarity	NPC278928
0.8722	High Similarity	NPC471530
0.8714	High Similarity	NPC181560
0.8714	High Similarity	NPC225243
0.8714	High Similarity	NPC169452
0.8714	High Similarity	NPC315578
0.8705	High Similarity	NPC416
0.8705	High Similarity	NPC61398
0.8696	High Similarity	NPC254847
0.8696	High Similarity	NPC472308
0.8681	High Similarity	NPC119767
0.8662	High Similarity	NPC296752
0.8657	High Similarity	NPC96024
0.8647	High Similarity	NPC3224
0.8636	High Similarity	NPC310540
0.8633	High Similarity	NPC147418
0.863	High Similarity	NPC205766
0.8626	High Similarity	NPC91478
0.8613	High Similarity	NPC294226
0.8613	High Similarity	NPC314048
0.8611	High Similarity	NPC314437
0.8611	High Similarity	NPC300540
0.8611	High Similarity	NPC147250
0.8603	High Similarity	NPC85342
0.8603	High Similarity	NPC93015
0.8601	High Similarity	NPC227841
0.8593	High Similarity	NPC276238
0.8592	High Similarity	NPC469520
0.8592	High Similarity	NPC193555
0.8581	High Similarity	NPC474824
0.8581	High Similarity	NPC470408
0.8581	High Similarity	NPC182921
0.8581	High Similarity	NPC218870
0.8561	High Similarity	NPC193358
0.8551	High Similarity	NPC12070
0.8551	High Similarity	NPC44437
0.855	High Similarity	NPC120545
0.854	High Similarity	NPC246693
0.854	High Similarity	NPC110609
0.854	High Similarity	NPC242358
0.8538	High Similarity	NPC285829
0.8538	High Similarity	NPC206778
0.8531	High Similarity	NPC313047
0.8531	High Similarity	NPC66593
0.8531	High Similarity	NPC474203
0.8531	High Similarity	NPC451542
0.8531	High Similarity	NPC295712
0.8531	High Similarity	NPC53016
0.8529	High Similarity	NPC108129
0.8529	High Similarity	NPC198305
0.8521	High Similarity	NPC204045
0.8521	High Similarity	NPC477275
0.8521	High Similarity	NPC305845
0.8511	High Similarity	NPC1268
0.8511	High Similarity	NPC190457
0.8507	High Similarity	NPC136342
0.8507	High Similarity	NPC295202
0.8507	High Similarity	NPC231774
0.8507	High Similarity	NPC227741
0.8507	High Similarity	NPC49647
0.8507	High Similarity	NPC1991
0.85	High Similarity	NPC62272
0.8496	Intermediate Similarity	NPC152525
0.8496	Intermediate Similarity	NPC68756
0.8489	Intermediate Similarity	NPC161632
0.8489	Intermediate Similarity	NPC249272
0.8478	Intermediate Similarity	NPC267205
0.8478	Intermediate Similarity	NPC171968
0.8478	Intermediate Similarity	NPC114183
0.8472	Intermediate Similarity	NPC244691
0.8472	Intermediate Similarity	NPC193703
0.8472	Intermediate Similarity	NPC471906
0.8472	Intermediate Similarity	NPC21599
0.8467	Intermediate Similarity	NPC474861
0.8462	Intermediate Similarity	NPC232178
0.8462	Intermediate Similarity	NPC135524
0.8462	Intermediate Similarity	NPC85310
0.8444	Intermediate Similarity	NPC176130
0.8444	Intermediate Similarity	NPC78364
0.8444	Intermediate Similarity	NPC69424
0.8444	Intermediate Similarity	NPC84672
0.8433	Intermediate Similarity	NPC131799
0.8429	Intermediate Similarity	NPC191976
0.8429	Intermediate Similarity	NPC474311
0.8425	Intermediate Similarity	NPC290194
0.8425	Intermediate Similarity	NPC478018
0.8417	Intermediate Similarity	NPC202225
0.8417	Intermediate Similarity	NPC282780
0.8417	Intermediate Similarity	NPC270899
0.8417	Intermediate Similarity	NPC166480
0.8414	Intermediate Similarity	NPC12402
0.8411	Intermediate Similarity	NPC67197
0.8403	Intermediate Similarity	NPC238629
0.8403	Intermediate Similarity	NPC293545
0.8403	Intermediate Similarity	NPC174905
0.84	Intermediate Similarity	NPC226656
0.84	Intermediate Similarity	NPC318270
0.84	Intermediate Similarity	NPC66508
0.8392	Intermediate Similarity	NPC187843
0.8392	Intermediate Similarity	NPC290550
0.8382	Intermediate Similarity	NPC237225
0.8378	Intermediate Similarity	NPC294646
0.837	Intermediate Similarity	NPC254492
0.8369	Intermediate Similarity	NPC44960
0.8369	Intermediate Similarity	NPC53001
0.8369	Intermediate Similarity	NPC474110
0.8358	Intermediate Similarity	NPC236189
0.8358	Intermediate Similarity	NPC164014
0.8358	Intermediate Similarity	NPC234890
0.8358	Intermediate Similarity	NPC199273
0.8358	Intermediate Similarity	NPC74507
0.8357	Intermediate Similarity	NPC22222
0.8357	Intermediate Similarity	NPC281513
0.8356	Intermediate Similarity	NPC110882
0.8356	Intermediate Similarity	NPC85393
0.8356	Intermediate Similarity	NPC285122
0.8356	Intermediate Similarity	NPC271944
0.8356	Intermediate Similarity	NPC143685
0.8355	Intermediate Similarity	NPC324736
0.8345	Intermediate Similarity	NPC48762
0.8345	Intermediate Similarity	NPC470406
0.8333	Intermediate Similarity	NPC471851
0.8333	Intermediate Similarity	NPC474300
0.8333	Intermediate Similarity	NPC474961
0.8333	Intermediate Similarity	NPC17083
0.8333	Intermediate Similarity	NPC73061
0.8322	Intermediate Similarity	NPC35
0.831	Intermediate Similarity	NPC87723
0.831	Intermediate Similarity	NPC206207
0.8309	Intermediate Similarity	NPC72667
0.8308	Intermediate Similarity	NPC269414
0.8301	Intermediate Similarity	NPC284495
0.8301	Intermediate Similarity	NPC476506
0.8299	Intermediate Similarity	NPC472135
0.8298	Intermediate Similarity	NPC315275

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 NPC155211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	960
0.2-0.3	1358
0.3-0.4	2844
0.4-0.5	2186
0.5-0.6	990
0.6-0.7	336
0.7-0.8	71
0.8-0.85	3
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8855	High Similarity	NPD1470	Approved
0.8696	High Similarity	NPD1509	Clinical (unspecified phase)
0.8601	High Similarity	NPD7390	Discontinued
0.855	High Similarity	NPD1201	Approved
0.85	High Similarity	NPD5404	Approved
0.85	High Similarity	NPD5408	Approved
0.85	High Similarity	NPD5406	Approved
0.85	High Similarity	NPD5405	Approved
0.8231	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD3226	Approved
0.8056	Intermediate Similarity	NPD2346	Discontinued
0.7785	Intermediate Similarity	NPD3300	Phase 2
0.774	Intermediate Similarity	NPD2935	Discontinued
0.7736	Intermediate Similarity	NPD6232	Discontinued
0.7702	Intermediate Similarity	NPD7473	Discontinued
0.7687	Intermediate Similarity	NPD2344	Approved
0.7674	Intermediate Similarity	NPD2342	Discontinued
0.7673	Intermediate Similarity	NPD6959	Discontinued
0.7652	Intermediate Similarity	NPD7635	Approved
0.7651	Intermediate Similarity	NPD7003	Approved
0.7643	Intermediate Similarity	NPD1164	Approved
0.7639	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD2313	Discontinued
0.7483	Intermediate Similarity	NPD2309	Approved
0.7471	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD3019	Approved
0.7432	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5951	Approved
0.7391	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD3764	Approved
0.7372	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD2798	Approved
0.7338	Intermediate Similarity	NPD2932	Approved
0.7338	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD2799	Discontinued
0.7297	Intermediate Similarity	NPD1607	Approved
0.7289	Intermediate Similarity	NPD5844	Phase 1
0.7267	Intermediate Similarity	NPD3749	Approved
0.7261	Intermediate Similarity	NPD7458	Discontinued
0.7251	Intermediate Similarity	NPD8150	Discontinued
0.7241	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6213	Phase 3
0.7241	Intermediate Similarity	NPD6212	Phase 3
0.7226	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1471	Phase 3
0.72	Intermediate Similarity	NPD6534	Approved
0.72	Intermediate Similarity	NPD1510	Phase 2
0.72	Intermediate Similarity	NPD6535	Approved
0.7192	Intermediate Similarity	NPD7008	Discontinued
0.7188	Intermediate Similarity	NPD7819	Suspended
0.7176	Intermediate Similarity	NPD8312	Approved
0.7176	Intermediate Similarity	NPD8313	Approved
0.7162	Intermediate Similarity	NPD1240	Approved
0.7153	Intermediate Similarity	NPD497	Approved
0.7143	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7177	Discontinued
0.7124	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2532	Approved
0.7115	Intermediate Similarity	NPD2534	Approved
0.7115	Intermediate Similarity	NPD2533	Approved
0.7108	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4380	Phase 2
0.7105	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7768	Phase 2
0.7095	Intermediate Similarity	NPD6776	Approved
0.7095	Intermediate Similarity	NPD6777	Approved
0.7095	Intermediate Similarity	NPD6779	Approved
0.7095	Intermediate Similarity	NPD6782	Approved
0.7095	Intermediate Similarity	NPD6781	Approved
0.7095	Intermediate Similarity	NPD6780	Approved
0.7095	Intermediate Similarity	NPD6778	Approved
0.709	Intermediate Similarity	NPD9266	Approved
0.709	Intermediate Similarity	NPD74	Approved
0.7083	Intermediate Similarity	NPD1283	Approved
0.7081	Intermediate Similarity	NPD2801	Approved
0.7081	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD495	Approved
0.708	Intermediate Similarity	NPD498	Approved
0.708	Intermediate Similarity	NPD496	Approved
0.7079	Intermediate Similarity	NPD7699	Phase 2
0.7079	Intermediate Similarity	NPD7700	Phase 2
0.7063	Intermediate Similarity	NPD4878	Approved
0.7063	Intermediate Similarity	NPD7411	Suspended
0.705	Intermediate Similarity	NPD9493	Approved
0.7042	Intermediate Similarity	NPD3023	Approved
0.7042	Intermediate Similarity	NPD3026	Approved
0.7033	Intermediate Similarity	NPD7870	Phase 2
0.7033	Intermediate Similarity	NPD7871	Phase 2
0.7021	Intermediate Similarity	NPD3024	Approved
0.7021	Intermediate Similarity	NPD3025	Approved
0.7021	Intermediate Similarity	NPD1651	Approved
0.7015	Intermediate Similarity	NPD9267	Approved
0.7015	Intermediate Similarity	NPD9263	Approved
0.7015	Intermediate Similarity	NPD9264	Approved
0.6978	Remote Similarity	NPD7697	Approved
0.6978	Remote Similarity	NPD7698	Approved
0.6978	Remote Similarity	NPD7696	Phase 3
0.6978	Remote Similarity	NPD7435	Discontinued
0.6972	Remote Similarity	NPD2286	Discontinued
0.697	Remote Similarity	NPD5494	Approved
0.6968	Remote Similarity	NPD3750	Approved
0.6968	Remote Similarity	NPD8166	Discontinued
0.6948	Remote Similarity	NPD1549	Phase 2
0.6948	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3972	Approved
0.6943	Remote Similarity	NPD1511	Approved
0.6933	Remote Similarity	NPD2296	Approved
0.6918	Remote Similarity	NPD1203	Approved
0.6914	Remote Similarity	NPD1934	Approved
0.6914	Remote Similarity	NPD6844	Discontinued
0.6894	Remote Similarity	NPD1932	Approved
0.6883	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1281	Approved
0.6875	Remote Similarity	NPD1611	Approved
0.6863	Remote Similarity	NPD4308	Phase 3
0.686	Remote Similarity	NPD5027	Approved
0.686	Remote Similarity	NPD5031	Approved
0.686	Remote Similarity	NPD5029	Approved
0.6855	Remote Similarity	NPD1512	Approved
0.6855	Remote Similarity	NPD6273	Approved
0.6849	Remote Similarity	NPD1876	Approved
0.6846	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD288	Approved
0.6842	Remote Similarity	NPD1930	Approved
0.6842	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1929	Approved
0.6829	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD7701	Phase 2
0.6821	Remote Similarity	NPD4954	Approved
0.6821	Remote Similarity	NPD5026	Approved
0.6821	Remote Similarity	NPD5034	Approved
0.6821	Remote Similarity	NPD5028	Approved
0.6821	Remote Similarity	NPD4955	Approved
0.6821	Remote Similarity	NPD36	Approved
0.6812	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6166	Phase 2
0.6805	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.68	Remote Similarity	NPD411	Approved
0.6795	Remote Similarity	NPD2800	Approved
0.6792	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD9281	Approved
0.6776	Remote Similarity	NPD447	Suspended
0.6769	Remote Similarity	NPD844	Approved
0.6765	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6559	Discontinued
0.6763	Remote Similarity	NPD5030	Phase 2
0.6757	Remote Similarity	NPD8320	Phase 1
0.6757	Remote Similarity	NPD8319	Approved
0.6755	Remote Similarity	NPD7874	Approved
0.6755	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6663	Approved
0.6752	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7075	Discontinued
0.6739	Remote Similarity	NPD6823	Phase 2
0.6736	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4626	Approved
0.6727	Remote Similarity	NPD5402	Approved
0.6725	Remote Similarity	NPD3751	Discontinued
0.672	Remote Similarity	NPD7801	Approved
0.6716	Remote Similarity	NPD9261	Approved
0.6715	Remote Similarity	NPD2329	Discontinued
0.6715	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD9717	Approved
0.6711	Remote Similarity	NPD5736	Approved
0.6711	Remote Similarity	NPD2979	Phase 3
0.671	Remote Similarity	NPD1551	Phase 2
0.671	Remote Similarity	NPD6099	Approved
0.671	Remote Similarity	NPD2796	Approved
0.671	Remote Similarity	NPD6100	Approved
0.6702	Remote Similarity	NPD8151	Discontinued
0.669	Remote Similarity	NPD4879	Approved
0.6689	Remote Similarity	NPD3268	Approved
0.6687	Remote Similarity	NPD3882	Suspended
0.6687	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6020	Phase 2
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1465	Phase 2
0.6667	Remote Similarity	NPD1237	Approved
0.6667	Remote Similarity	NPD1755	Approved
0.6667	Remote Similarity	NPD5038	Approved
0.6667	Remote Similarity	NPD5037	Approved
0.6647	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4628	Phase 3
0.6645	Remote Similarity	NPD3748	Approved
0.6643	Remote Similarity	NPD7610	Discontinued
0.6627	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD4625	Phase 3
0.662	Remote Similarity	NPD3317	Approved
0.6619	Remote Similarity	NPD4141	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