NPASS Compound

Structure

NPC79627 OpenBabel07101718292D 25 28 0 0 1 0 0 0 0 0999 V2000 -0.2588 -0.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 2.5000 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 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 4.3301 2.5000 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 3.4641 3.0000 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 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 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -0.7934 0.6088 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 9 1 0 0 0 0 4 11 2 0 0 0 0 5 6 2 0 0 0 0 5 8 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 12 2 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 13 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 17 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 21 2 0 0 0 0 16 22 2 0 0 0 0 17 18 1 0 0 0 0 17 23 2 0 0 0 0 18 19 1 6 0 0 0 18 24 1 0 0 0 0 19 1 1 1 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.08
Volume:	331.968
LogP:	3.354
LogD:	2.415
LogS:	-3.538
# Rotatable Bonds:	0
TPSA:	115.06
# H-Bond Aceptor:	6
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.284
Synthetic Accessibility Score:	3.532
Fsp3:	0.158
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.137
MDCK Permeability:	8.41408473206684e-06
Pgp-inhibitor:	0.021
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.892
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	98.58126831054688%
Volume Distribution (VD):	0.366
Pgp-substrate:	3.897597312927246%

ADMET: Metabolism

CYP1A2-inhibitor:	0.946
CYP1A2-substrate:	0.227
CYP2C19-inhibitor:	0.133
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.748
CYP2C9-substrate:	0.596
CYP2D6-inhibitor:	0.469
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.227
CYP3A4-substrate:	0.102

ADMET: Excretion

Clearance (CL):	1.467
Half-life (T1/2):	0.349

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.069
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.825
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.05
Skin Sensitization:	0.93
Carcinogencity:	0.589
Eye Corrosion:	0.003
Eye Irritation:	0.9
Respiratory Toxicity:	0.057

Download Data

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

Natural Product: NPC79627

Natural Product ID:	NPC79627
*Common Name:**	(2R,3R)-2,3,8-Trihydroxy-3-Methyl-3,4-Dihydrotetraphene-1,7,12(2H)-Trione
IUPAC Name:	(2R,3R)-2,3,8-trihydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione
Synonyms:	PD-116779
Standard InCHIKey:	ZGIMJLWQWQRQNJ-RBUKOAKNSA-N
Standard InCHI:	InChI=1S/C19H14O6/c1-19(25)7-8-5-6-10-14(12(8)17(23)18(19)24)16(22)9-3-2-4-11(20)13(9)15(10)21/h2-6,18,20,24-25H,7H2,1H3/t18-,19+/m0/s1
SMILES:	C[C@]1(Cc2ccc3c(c2C(=O)[C@@H]1O)C(=O)c1cccc(c1C3=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2208052
PubChem CID:	71461512
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
NPO33103	amycolatopsis sp. hca1	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23131338]

☑ 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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	37640.0	nM	PMID[548548]

☑ 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 NPC79627 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	360
0.1-0.2	1535
0.2-0.3	3477
0.3-0.4	9107
0.4-0.5	10010
0.5-0.6	5583
0.6-0.7	8034
0.7-0.8	4202
0.8-0.85	311
0.85-0.9	73
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9343	High Similarity	NPC80035
0.9143	High Similarity	NPC13715
0.8921	High Similarity	NPC225051
0.8921	High Similarity	NPC52407
0.8904	High Similarity	NPC314437
0.8844	High Similarity	NPC478018
0.8841	High Similarity	NPC199253
0.8841	High Similarity	NPC136588
0.8803	High Similarity	NPC475957
0.8794	High Similarity	NPC258502
0.8786	High Similarity	NPC53896
0.8776	High Similarity	NPC136878
0.8767	High Similarity	NPC471906
0.8767	High Similarity	NPC244691
0.8767	High Similarity	NPC29932
0.8741	High Similarity	NPC416
0.8741	High Similarity	NPC61398
0.8741	High Similarity	NPC4214
0.8732	High Similarity	NPC315275
0.8732	High Similarity	NPC155211
0.8723	High Similarity	NPC50924
0.8714	High Similarity	NPC70622
0.8705	High Similarity	NPC31799
0.8699	High Similarity	NPC53016
0.869	High Similarity	NPC204045
0.869	High Similarity	NPC305845
0.8681	High Similarity	NPC26924
0.8652	High Similarity	NPC294226
0.8652	High Similarity	NPC115458
0.8649	High Similarity	NPC285122
0.8649	High Similarity	NPC143685
0.8643	High Similarity	NPC93015
0.8633	High Similarity	NPC34414
0.8633	High Similarity	NPC146647
0.863	High Similarity	NPC469520
0.863	High Similarity	NPC135524
0.8627	High Similarity	NPC474861
0.8621	High Similarity	NPC315578
0.8621	High Similarity	NPC96421
0.8601	High Similarity	NPC474311
0.8571	High Similarity	NPC66593
0.8562	High Similarity	NPC294501
0.8561	High Similarity	NPC48248
0.8561	High Similarity	NPC282923
0.8543	High Similarity	NPC315520
0.8542	High Similarity	NPC305060
0.854	High Similarity	NPC142956
0.8531	High Similarity	NPC283088
0.8521	High Similarity	NPC78307
0.8521	High Similarity	NPC314048
0.8511	High Similarity	NPC244699
0.8503	High Similarity	NPC248068
0.8503	High Similarity	NPC73061
0.8503	High Similarity	NPC19631
0.8503	High Similarity	NPC239136
0.8503	High Similarity	NPC193555
0.8503	High Similarity	NPC85310
0.8503	High Similarity	NPC69755
0.85	High Similarity	NPC99731
0.85	High Similarity	NPC478021
0.8497	Intermediate Similarity	NPC472211
0.8497	Intermediate Similarity	NPC218870
0.8497	Intermediate Similarity	NPC474824
0.8497	Intermediate Similarity	NPC470408
0.8497	Intermediate Similarity	NPC182921
0.8483	Intermediate Similarity	NPC173980
0.8477	Intermediate Similarity	NPC474310
0.8477	Intermediate Similarity	NPC44378
0.8477	Intermediate Similarity	NPC280753
0.8477	Intermediate Similarity	NPC478219
0.8472	Intermediate Similarity	NPC86524
0.8472	Intermediate Similarity	NPC474813
0.8472	Intermediate Similarity	NPC272268
0.8467	Intermediate Similarity	NPC375356
0.8462	Intermediate Similarity	NPC284495
0.8462	Intermediate Similarity	NPC288089
0.8462	Intermediate Similarity	NPC202225
0.8456	Intermediate Similarity	NPC170055
0.8456	Intermediate Similarity	NPC478019
0.8451	Intermediate Similarity	NPC17843
0.8446	Intermediate Similarity	NPC471682
0.8446	Intermediate Similarity	NPC143898
0.844	Intermediate Similarity	NPC55949
0.8435	Intermediate Similarity	NPC246638
0.8429	Intermediate Similarity	NPC767
0.8429	Intermediate Similarity	NPC247250
0.8425	Intermediate Similarity	NPC103337
0.8425	Intermediate Similarity	NPC242994
0.8425	Intermediate Similarity	NPC114620
0.8425	Intermediate Similarity	NPC138099
0.8425	Intermediate Similarity	NPC190457
0.8414	Intermediate Similarity	NPC245923
0.8414	Intermediate Similarity	NPC53414
0.8414	Intermediate Similarity	NPC471905
0.8414	Intermediate Similarity	NPC53206
0.8411	Intermediate Similarity	NPC94781
0.8406	Intermediate Similarity	NPC152525
0.8406	Intermediate Similarity	NPC68756
0.8394	Intermediate Similarity	NPC300274
0.8389	Intermediate Similarity	NPC218866
0.8389	Intermediate Similarity	NPC84568
0.8389	Intermediate Similarity	NPC48762
0.8389	Intermediate Similarity	NPC300684
0.8389	Intermediate Similarity	NPC21599
0.8389	Intermediate Similarity	NPC48130
0.8389	Intermediate Similarity	NPC193703
0.838	Intermediate Similarity	NPC72669
0.838	Intermediate Similarity	NPC474517
0.838	Intermediate Similarity	NPC205992
0.8378	Intermediate Similarity	NPC474961
0.8378	Intermediate Similarity	NPC257644
0.8367	Intermediate Similarity	NPC181560
0.8367	Intermediate Similarity	NPC169452
0.8366	Intermediate Similarity	NPC118427
0.8345	Intermediate Similarity	NPC193358
0.8345	Intermediate Similarity	NPC254847
0.8345	Intermediate Similarity	NPC103540
0.8344	Intermediate Similarity	NPC119767
0.8344	Intermediate Similarity	NPC472135
0.8333	Intermediate Similarity	NPC471683
0.8333	Intermediate Similarity	NPC34482
0.8333	Intermediate Similarity	NPC478160
0.8323	Intermediate Similarity	NPC266469
0.8323	Intermediate Similarity	NPC318270
0.8322	Intermediate Similarity	NPC58685
0.8312	Intermediate Similarity	NPC164912
0.831	Intermediate Similarity	NPC117609
0.831	Intermediate Similarity	NPC198305
0.8301	Intermediate Similarity	NPC280295
0.8298	Intermediate Similarity	NPC234175
0.8289	Intermediate Similarity	NPC112816
0.8289	Intermediate Similarity	NPC142846
0.8288	Intermediate Similarity	NPC147418
0.8288	Intermediate Similarity	NPC264022
0.8286	Intermediate Similarity	NPC96915
0.8286	Intermediate Similarity	NPC231774
0.8278	Intermediate Similarity	NPC470570
0.8278	Intermediate Similarity	NPC472134
0.8278	Intermediate Similarity	NPC147250
0.8273	Intermediate Similarity	NPC74507
0.8273	Intermediate Similarity	NPC173978
0.8273	Intermediate Similarity	NPC310540
0.8273	Intermediate Similarity	NPC234890
0.8269	Intermediate Similarity	NPC478223
0.8267	Intermediate Similarity	NPC469856
0.8267	Intermediate Similarity	NPC469854
0.8264	Intermediate Similarity	NPC171968
0.8264	Intermediate Similarity	NPC477139
0.8264	Intermediate Similarity	NPC254603
0.8261	Intermediate Similarity	NPC91478
0.8261	Intermediate Similarity	NPC307174
0.8258	Intermediate Similarity	NPC474621
0.8258	Intermediate Similarity	NPC474622
0.8255	Intermediate Similarity	NPC30846
0.8255	Intermediate Similarity	NPC469855
0.8255	Intermediate Similarity	NPC471972
0.8255	Intermediate Similarity	NPC471971
0.8255	Intermediate Similarity	NPC308572
0.8252	Intermediate Similarity	NPC471851
0.825	Intermediate Similarity	NPC478022
0.825	Intermediate Similarity	NPC478020
0.8247	Intermediate Similarity	NPC473201
0.8247	Intermediate Similarity	NPC302783
0.8247	Intermediate Similarity	NPC205918
0.8247	Intermediate Similarity	NPC144283
0.8243	Intermediate Similarity	NPC471853
0.8243	Intermediate Similarity	NPC203063
0.8239	Intermediate Similarity	NPC474546
0.8235	Intermediate Similarity	NPC120171
0.8231	Intermediate Similarity	NPC206207
0.8224	Intermediate Similarity	NPC215593
0.8221	Intermediate Similarity	NPC473113
0.8217	Intermediate Similarity	NPC317580
0.8217	Intermediate Similarity	NPC10051
0.8217	Intermediate Similarity	NPC299094
0.8212	Intermediate Similarity	NPC73416
0.8212	Intermediate Similarity	NPC160777
0.821	Intermediate Similarity	NPC175477
0.8207	Intermediate Similarity	NPC161964
0.8207	Intermediate Similarity	NPC287604
0.8207	Intermediate Similarity	NPC44437
0.8207	Intermediate Similarity	NPC472262
0.8205	Intermediate Similarity	NPC478133
0.8205	Intermediate Similarity	NPC3449
0.8205	Intermediate Similarity	NPC314257
0.82	Intermediate Similarity	NPC478164
0.82	Intermediate Similarity	NPC296752
0.8194	Intermediate Similarity	NPC309430
0.8194	Intermediate Similarity	NPC246693
0.8194	Intermediate Similarity	NPC242358
0.8194	Intermediate Similarity	NPC110609
0.8188	Intermediate Similarity	NPC106519
0.8188	Intermediate Similarity	NPC290550
0.8188	Intermediate Similarity	NPC91019
0.8188	Intermediate Similarity	NPC120545
0.8188	Intermediate Similarity	NPC477275
0.8182	Intermediate Similarity	NPC255641
0.8182	Intermediate Similarity	NPC290954
0.8182	Intermediate Similarity	NPC205766
0.8182	Intermediate Similarity	NPC108129

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 NPC79627 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	960
0.2-0.3	1441
0.3-0.4	2812
0.4-0.5	2103
0.5-0.6	1048
0.6-0.7	373
0.7-0.8	83
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8345	Intermediate Similarity	NPD1470	Approved
0.8345	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD1201	Approved
0.7919	Intermediate Similarity	NPD5408	Approved
0.7919	Intermediate Similarity	NPD5404	Approved
0.7919	Intermediate Similarity	NPD5405	Approved
0.7919	Intermediate Similarity	NPD5406	Approved
0.7908	Intermediate Similarity	NPD7390	Discontinued
0.7843	Intermediate Similarity	NPD3300	Phase 2
0.7771	Intermediate Similarity	NPD3226	Approved
0.7754	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD8150	Discontinued
0.7703	Intermediate Similarity	NPD943	Approved
0.7616	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD6535	Approved
0.7557	Intermediate Similarity	NPD6534	Approved
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.747	Intermediate Similarity	NPD6232	Discontinued
0.7444	Intermediate Similarity	NPD6780	Approved
0.7444	Intermediate Similarity	NPD6778	Approved
0.7444	Intermediate Similarity	NPD6782	Approved
0.7444	Intermediate Similarity	NPD6781	Approved
0.7444	Intermediate Similarity	NPD6779	Approved
0.7444	Intermediate Similarity	NPD6776	Approved
0.7444	Intermediate Similarity	NPD6777	Approved
0.744	Intermediate Similarity	NPD7473	Discontinued
0.743	Intermediate Similarity	NPD7700	Phase 2
0.743	Intermediate Similarity	NPD7699	Phase 2
0.741	Intermediate Similarity	NPD6959	Discontinued
0.7403	Intermediate Similarity	NPD1471	Phase 3
0.7391	Intermediate Similarity	NPD4380	Phase 2
0.7362	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7458	Discontinued
0.7322	Intermediate Similarity	NPD7435	Discontinued
0.7317	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD4954	Approved
0.7283	Intermediate Similarity	NPD5026	Approved
0.7283	Intermediate Similarity	NPD4955	Approved
0.7283	Intermediate Similarity	NPD36	Approved
0.7283	Intermediate Similarity	NPD5034	Approved
0.7283	Intermediate Similarity	NPD5028	Approved
0.7283	Intermediate Similarity	NPD8319	Approved
0.7283	Intermediate Similarity	NPD8320	Phase 1
0.7278	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6166	Phase 2
0.7278	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7003	Approved
0.7261	Intermediate Similarity	NPD8166	Discontinued
0.7241	Intermediate Similarity	NPD8312	Approved
0.7241	Intermediate Similarity	NPD8313	Approved
0.723	Intermediate Similarity	NPD1164	Approved
0.7229	Intermediate Similarity	NPD7075	Discontinued
0.7228	Intermediate Similarity	NPD7697	Approved
0.7228	Intermediate Similarity	NPD7698	Approved
0.7228	Intermediate Similarity	NPD7696	Phase 3
0.7226	Intermediate Similarity	NPD2935	Discontinued
0.7225	Intermediate Similarity	NPD5030	Phase 2
0.7222	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD6213	Phase 3
0.7207	Intermediate Similarity	NPD6212	Phase 3
0.7197	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD1934	Approved
0.7193	Intermediate Similarity	NPD3751	Discontinued
0.7189	Intermediate Similarity	NPD7871	Phase 2
0.7189	Intermediate Similarity	NPD7870	Phase 2
0.7188	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2344	Approved
0.7172	Intermediate Similarity	NPD3019	Approved
0.7169	Intermediate Similarity	NPD3882	Suspended
0.7166	Intermediate Similarity	NPD7701	Phase 2
0.7161	Intermediate Similarity	NPD1510	Phase 2
0.7152	Intermediate Similarity	NPD7819	Suspended
0.7152	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD5035	Approved
0.7143	Intermediate Similarity	NPD1607	Approved
0.7134	Intermediate Similarity	NPD7411	Suspended
0.7119	Intermediate Similarity	NPD5037	Approved
0.7119	Intermediate Similarity	NPD5038	Approved
0.7107	Intermediate Similarity	NPD6190	Approved
0.7105	Intermediate Similarity	NPD3764	Approved
0.7103	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6801	Discontinued
0.709	Intermediate Similarity	NPD7874	Approved
0.709	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5036	Approved
0.7055	Intermediate Similarity	NPD2932	Approved
0.7053	Intermediate Similarity	NPD7801	Approved
0.7051	Intermediate Similarity	NPD2799	Discontinued
0.7044	Intermediate Similarity	NPD4628	Phase 3
0.7042	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1512	Approved
0.7037	Intermediate Similarity	NPD6273	Approved
0.7025	Intermediate Similarity	NPD1549	Phase 2
0.7022	Intermediate Similarity	NPD8434	Phase 2
0.7013	Intermediate Similarity	NPD1240	Approved
0.7007	Intermediate Similarity	NPD1237	Approved
0.7	Intermediate Similarity	NPD2309	Approved
0.6993	Remote Similarity	NPD2313	Discontinued
0.6993	Remote Similarity	NPD5951	Approved
0.6978	Remote Similarity	NPD2342	Discontinued
0.6975	Remote Similarity	NPD2532	Approved
0.6975	Remote Similarity	NPD2534	Approved
0.6975	Remote Similarity	NPD2533	Approved
0.697	Remote Similarity	NPD6599	Discontinued
0.6968	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3787	Discontinued
0.6954	Remote Similarity	NPD2798	Approved
0.6954	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2801	Approved
0.6941	Remote Similarity	NPD5494	Approved
0.6932	Remote Similarity	NPD5031	Approved
0.6932	Remote Similarity	NPD5029	Approved
0.6932	Remote Similarity	NPD5027	Approved
0.6928	Remote Similarity	NPD7008	Discontinued
0.6923	Remote Similarity	NPD3749	Approved
0.6923	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1511	Approved
0.6905	Remote Similarity	NPD5402	Approved
0.6898	Remote Similarity	NPD6823	Phase 2
0.6897	Remote Similarity	NPD3818	Discontinued
0.6875	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6797	Phase 2
0.6872	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7768	Phase 2
0.6864	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD8151	Discontinued
0.6852	Remote Similarity	NPD7236	Approved
0.6846	Remote Similarity	NPD3092	Approved
0.6846	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6663	Approved
0.6836	Remote Similarity	NPD6559	Discontinued
0.6836	Remote Similarity	NPD7251	Discontinued
0.6824	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1283	Approved
0.6818	Remote Similarity	NPD4956	Approved
0.6818	Remote Similarity	NPD7074	Phase 3
0.6818	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD970	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6799	Approved
0.6805	Remote Similarity	NPD3817	Phase 2
0.6803	Remote Similarity	NPD3091	Approved
0.68	Remote Similarity	NPD3972	Approved
0.68	Remote Similarity	NPD7177	Discontinued
0.6798	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7808	Phase 3
0.6798	Remote Similarity	NPD5032	Approved
0.6797	Remote Similarity	NPD9494	Approved
0.6797	Remote Similarity	NPD5736	Approved
0.6795	Remote Similarity	NPD4060	Phase 1
0.6792	Remote Similarity	NPD2796	Approved
0.6788	Remote Similarity	NPD5403	Approved
0.6781	Remote Similarity	NPD9493	Approved
0.6779	Remote Similarity	NPD3026	Approved
0.6779	Remote Similarity	NPD3023	Approved
0.6776	Remote Similarity	NPD3094	Phase 2
0.6776	Remote Similarity	NPD5968	Phase 3
0.6768	Remote Similarity	NPD5401	Approved
0.6761	Remote Similarity	NPD7054	Approved
0.6757	Remote Similarity	NPD1651	Approved
0.6757	Remote Similarity	NPD3024	Approved
0.6757	Remote Similarity	NPD3025	Approved
0.6747	Remote Similarity	NPD7239	Suspended
0.6742	Remote Similarity	NPD5039	Approved
0.6736	Remote Similarity	NPD7635	Approved
0.6734	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD3750	Approved
0.6723	Remote Similarity	NPD7472	Approved
0.6711	Remote Similarity	NPD1876	Approved
0.6705	Remote Similarity	NPD1247	Approved
0.6702	Remote Similarity	NPD4914	Approved
0.669	Remote Similarity	NPD9266	Approved
0.669	Remote Similarity	NPD74	Approved
0.6689	Remote Similarity	NPD4878	Approved
0.6686	Remote Similarity	NPD6844	Discontinued
0.6667	Remote Similarity	NPD6836	Approved
0.6667	Remote Similarity	NPD6798	Discontinued
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD230	Phase 1
0.6643	Remote Similarity	NPD3022	Approved
0.6643	Remote Similarity	NPD3021	Approved
0.6625	Remote Similarity	NPD4308	Phase 3
0.6624	Remote Similarity	NPD7961	Discontinued
0.6623	Remote Similarity	NPD1281	Approved
0.662	Remote Similarity	NPD9264	Approved
0.662	Remote Similarity	NPD9263	Approved
0.662	Remote Similarity	NPD9267	Approved
0.6614	Remote Similarity	NPD7501	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