NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	556.14
Volume:	544.385
LogP:	6.353
LogD:	2.373
LogS:	-3.841
# Rotatable Bonds:	3
TPSA:	170.05
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	6
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.116
Synthetic Accessibility Score:	3.467
Fsp3:	0.129
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.533
MDCK Permeability:	7.289137556654168e-06
Pgp-inhibitor:	0.241
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.959
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	81.75078582763672%
Volume Distribution (VD):	0.341
Pgp-substrate:	41.85311508178711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.542
CYP1A2-substrate:	0.841
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.06
CYP2C9-inhibitor:	0.639
CYP2C9-substrate:	0.59
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.237
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.038

ADMET: Excretion

Clearance (CL):	2.339
Half-life (T1/2):	0.177

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.052
Drug-inuced Liver Injury (DILI):	0.984
AMES Toxicity:	0.192
Rat Oral Acute Toxicity:	0.059
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.891
Carcinogencity:	0.026
Eye Corrosion:	0.003
Eye Irritation:	0.897
Respiratory Toxicity:	0.07

Download Data

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

Natural Product: NPC477835

Natural Product ID:	NPC477835
*Common Name:**	9,10-Dihydroxy-7-methoxy-5-(1,8-dihydroxy-3-methoxy-6-methyl-9,10-dioxo-9,10-dihydroanthracene-2-yl)-3-methyl-3,4-dihydro-1H-naphtho[2,3-c]pyran-1-one
IUPAC Name:	2-(9,10-dihydroxy-7-methoxy-3-methyl-1-oxo-3,4-dihydrobenzo[g]isochromen-5-yl)-1,8-dihydroxy-3-methoxy-6-methylanthracene-9,10-dione
Synonyms:
Standard InCHIKey:	BUWQXVFFIWOOMQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C31H24O10/c1-11-5-16-23(18(32)6-11)28(35)24-17(27(16)34)10-20(40-4)26(30(24)37)21-14-7-12(2)41-31(38)25(14)29(36)22-15(21)8-13(39-3)9-19(22)33/h5-6,8-10,12,32-33,36-37H,7H2,1-4H3
SMILES:	CC1CC2=C(C3=C(C(=CC(=C3)OC)O)C(=C2C(=O)O1)O)C4=C(C=C5C(=C4O)C(=O)C6=C(C5=O)C=C(C=C6O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122178801
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001610] Arylnaphthalene lignans

*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
NPO33555	Pyrenacantha kaurabassana	Species	Icacinaceae	Eukaryota	tubers	n.a.	n.a.	PMID[25756503]

☑ 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
MIC	3
Others	1

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	Activity	=	179.8	nM	PMID[25756503]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	89900	nM	PMID[25756503]

☑ 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 NPC477835 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	389
0.1-0.2	1693
0.2-0.3	3476
0.3-0.4	8497
0.4-0.5	10235
0.5-0.6	3793
0.6-0.7	5749
0.7-0.8	5923
0.8-0.85	2383
0.85-0.9	506
0.9-0.95	51
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC477836
0.943	High Similarity	NPC472052
0.943	High Similarity	NPC470342
0.943	High Similarity	NPC472060
0.9299	High Similarity	NPC66508
0.9299	High Similarity	NPC226656
0.9245	High Similarity	NPC324736
0.9193	High Similarity	NPC15374
0.9167	High Similarity	NPC470568
0.913	High Similarity	NPC18380
0.9125	High Similarity	NPC195167
0.9108	High Similarity	NPC470569
0.9085	High Similarity	NPC472058
0.9085	High Similarity	NPC105414
0.9085	High Similarity	NPC324522
0.9085	High Similarity	NPC470341
0.9085	High Similarity	NPC234497
0.908	High Similarity	NPC469664
0.9068	High Similarity	NPC184326
0.9068	High Similarity	NPC292863
0.9068	High Similarity	NPC186325
0.9062	High Similarity	NPC263483
0.9051	High Similarity	NPC154683
0.9051	High Similarity	NPC40356
0.9045	High Similarity	NPC205766
0.9042	High Similarity	NPC477992
0.9042	High Similarity	NPC477991
0.9024	High Similarity	NPC30027
0.9012	High Similarity	NPC273467
0.9012	High Similarity	NPC189552
0.9012	High Similarity	NPC137232
0.9006	High Similarity	NPC51760
0.9006	High Similarity	NPC177650
0.9	High Similarity	NPC146211
0.8994	High Similarity	NPC153578
0.8994	High Similarity	NPC299149
0.8994	High Similarity	NPC114257
0.8994	High Similarity	NPC277710
0.8987	High Similarity	NPC232645
0.8987	High Similarity	NPC72958
0.8982	High Similarity	NPC472054
0.8974	High Similarity	NPC190648
0.8974	High Similarity	NPC118027
0.8974	High Similarity	NPC126767
0.8974	High Similarity	NPC289042
0.8974	High Similarity	NPC312929
0.8974	High Similarity	NPC245584
0.8974	High Similarity	NPC56433
0.897	High Similarity	NPC76647
0.8951	High Similarity	NPC312993
0.8944	High Similarity	NPC208258
0.8938	High Similarity	NPC79375
0.8938	High Similarity	NPC37253
0.8938	High Similarity	NPC66029
0.8931	High Similarity	NPC87708
0.8929	High Similarity	NPC68381
0.8924	High Similarity	NPC290954
0.8924	High Similarity	NPC255641
0.8924	High Similarity	NPC147735
0.8917	High Similarity	NPC2569
0.8917	High Similarity	NPC172329
0.891	High Similarity	NPC470570
0.8909	High Similarity	NPC125465
0.8902	High Similarity	NPC290160
0.8896	High Similarity	NPC472261
0.8889	High Similarity	NPC55443
0.8889	High Similarity	NPC473631
0.8889	High Similarity	NPC293227
0.8889	High Similarity	NPC473717
0.8889	High Similarity	NPC475662
0.8889	High Similarity	NPC18699
0.8889	High Similarity	NPC105584
0.8868	High Similarity	NPC149526
0.8868	High Similarity	NPC474417
0.8854	High Similarity	NPC37709
0.8854	High Similarity	NPC34802
0.8846	High Similarity	NPC34482
0.8844	High Similarity	NPC105591
0.8834	High Similarity	NPC226462
0.8834	High Similarity	NPC195136
0.8834	High Similarity	NPC98023
0.883	High Similarity	NPC475161
0.883	High Similarity	NPC477860
0.8827	High Similarity	NPC322459
0.8827	High Similarity	NPC323627
0.8827	High Similarity	NPC318527
0.8827	High Similarity	NPC324358
0.8824	High Similarity	NPC207467
0.8824	High Similarity	NPC470334
0.882	High Similarity	NPC66441
0.882	High Similarity	NPC300668
0.882	High Similarity	NPC182555
0.882	High Similarity	NPC254351
0.882	High Similarity	NPC134171
0.8812	High Similarity	NPC175978
0.8812	High Similarity	NPC217447
0.8812	High Similarity	NPC174086
0.881	High Similarity	NPC271385
0.881	High Similarity	NPC111536
0.881	High Similarity	NPC30432
0.881	High Similarity	NPC5029
0.881	High Similarity	NPC76128
0.8805	High Similarity	NPC119929
0.8805	High Similarity	NPC473466
0.8805	High Similarity	NPC474660
0.8805	High Similarity	NPC294646
0.8802	High Similarity	NPC300307
0.8795	High Similarity	NPC251336
0.879	High Similarity	NPC163846
0.879	High Similarity	NPC225173
0.8788	High Similarity	NPC38591
0.8786	High Similarity	NPC221140
0.8786	High Similarity	NPC473686
0.8786	High Similarity	NPC475352
0.8786	High Similarity	NPC87583
0.8786	High Similarity	NPC475220
0.8786	High Similarity	NPC229817
0.8782	High Similarity	NPC48762
0.8782	High Similarity	NPC19896
0.878	High Similarity	NPC312273
0.878	High Similarity	NPC301256
0.8773	High Similarity	NPC15815
0.8772	High Similarity	NPC473785
0.8765	High Similarity	NPC61112
0.8765	High Similarity	NPC198489
0.8765	High Similarity	NPC46958
0.8765	High Similarity	NPC471787
0.8765	High Similarity	NPC32867
0.8765	High Similarity	NPC309648
0.8765	High Similarity	NPC475246
0.8765	High Similarity	NPC69531
0.8765	High Similarity	NPC472050
0.8758	High Similarity	NPC214632
0.8758	High Similarity	NPC208806
0.8758	High Similarity	NPC329844
0.8757	High Similarity	NPC85368
0.8757	High Similarity	NPC470336
0.8757	High Similarity	NPC131862
0.8757	High Similarity	NPC470335
0.8757	High Similarity	NPC229051
0.875	High Similarity	NPC316960
0.875	High Similarity	NPC133856
0.875	High Similarity	NPC204561
0.875	High Similarity	NPC477571
0.875	High Similarity	NPC309512
0.875	High Similarity	NPC478148
0.875	High Similarity	NPC477572
0.875	High Similarity	NPC477573
0.875	High Similarity	NPC317715
0.875	High Similarity	NPC78835
0.875	High Similarity	NPC298778
0.875	High Similarity	NPC148945
0.8742	High Similarity	NPC3642
0.8742	High Similarity	NPC158338
0.8742	High Similarity	NPC233267
0.8742	High Similarity	NPC97028
0.8742	High Similarity	NPC288036
0.8742	High Similarity	NPC65589
0.8742	High Similarity	NPC100985
0.8742	High Similarity	NPC291049
0.8742	High Similarity	NPC97029
0.8742	High Similarity	NPC329933
0.8735	High Similarity	NPC472051
0.8735	High Similarity	NPC471788
0.8735	High Similarity	NPC472057
0.8734	High Similarity	NPC119767
0.8734	High Similarity	NPC290194
0.8734	High Similarity	NPC125801
0.8727	High Similarity	NPC473012
0.8727	High Similarity	NPC315772
0.8727	High Similarity	NPC473022
0.8726	High Similarity	NPC49282
0.8721	High Similarity	NPC315221
0.8721	High Similarity	NPC208069
0.872	High Similarity	NPC42965
0.872	High Similarity	NPC284495
0.872	High Similarity	NPC476506
0.872	High Similarity	NPC472055
0.8718	High Similarity	NPC159721
0.8718	High Similarity	NPC472006
0.8718	High Similarity	NPC167663
0.8718	High Similarity	NPC84266
0.8712	High Similarity	NPC257166
0.8712	High Similarity	NPC271741
0.8712	High Similarity	NPC287789
0.8712	High Similarity	NPC1796
0.8712	High Similarity	NPC317580
0.8712	High Similarity	NPC475184
0.8712	High Similarity	NPC201127
0.8706	High Similarity	NPC300657
0.8706	High Similarity	NPC3718
0.8704	High Similarity	NPC258474
0.8704	High Similarity	NPC89625
0.8704	High Similarity	NPC201227
0.8704	High Similarity	NPC318270
0.8704	High Similarity	NPC149618
0.8698	High Similarity	NPC4200
0.8698	High Similarity	NPC473113
0.8696	High Similarity	NPC208011
0.8696	High Similarity	NPC43345

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 NPC477835 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	1011
0.2-0.3	1655
0.3-0.4	2573
0.4-0.5	1959
0.5-0.6	1052
0.6-0.7	352
0.7-0.8	162
0.8-0.85	31
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.925	High Similarity	NPD6959	Discontinued
0.8848	High Similarity	NPD7852	Clinical (unspecified phase)
0.8841	High Similarity	NPD6232	Discontinued
0.8795	High Similarity	NPD7473	Discontinued
0.8758	High Similarity	NPD7819	Suspended
0.8662	High Similarity	NPD7390	Discontinued
0.8634	High Similarity	NPD7411	Suspended
0.8537	High Similarity	NPD7768	Phase 2
0.8491	Intermediate Similarity	NPD2532	Approved
0.8491	Intermediate Similarity	NPD2533	Approved
0.8491	Intermediate Similarity	NPD2534	Approved
0.8485	Intermediate Similarity	NPD3749	Approved
0.8476	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD5844	Phase 1
0.8418	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8409	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7075	Discontinued
0.8344	Intermediate Similarity	NPD4380	Phase 2
0.8333	Intermediate Similarity	NPD8313	Approved
0.8333	Intermediate Similarity	NPD8151	Discontinued
0.8333	Intermediate Similarity	NPD8312	Approved
0.8313	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD3226	Approved
0.8269	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD5404	Approved
0.8217	Intermediate Similarity	NPD5408	Approved
0.8217	Intermediate Similarity	NPD5406	Approved
0.8217	Intermediate Similarity	NPD5405	Approved
0.8193	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD7003	Approved
0.8114	Intermediate Similarity	NPD6559	Discontinued
0.8113	Intermediate Similarity	NPD1549	Phase 2
0.8081	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD6166	Phase 2
0.8081	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD1510	Phase 2
0.8037	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1607	Approved
0.8024	Intermediate Similarity	NPD6801	Discontinued
0.8012	Intermediate Similarity	NPD3750	Approved
0.7968	Intermediate Similarity	NPD7435	Discontinued
0.7965	Intermediate Similarity	NPD5710	Approved
0.7965	Intermediate Similarity	NPD5711	Approved
0.795	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD2346	Discontinued
0.7926	Intermediate Similarity	NPD7870	Phase 2
0.7926	Intermediate Similarity	NPD7871	Phase 2
0.7917	Intermediate Similarity	NPD1934	Approved
0.7904	Intermediate Similarity	NPD6599	Discontinued
0.7903	Intermediate Similarity	NPD6778	Approved
0.7903	Intermediate Similarity	NPD6779	Approved
0.7903	Intermediate Similarity	NPD6780	Approved
0.7903	Intermediate Similarity	NPD6782	Approved
0.7903	Intermediate Similarity	NPD6776	Approved
0.7903	Intermediate Similarity	NPD6781	Approved
0.7903	Intermediate Similarity	NPD6777	Approved
0.7898	Intermediate Similarity	NPD1240	Approved
0.7875	Intermediate Similarity	NPD2935	Discontinued
0.7875	Intermediate Similarity	NPD2796	Approved
0.787	Intermediate Similarity	NPD1465	Phase 2
0.7849	Intermediate Similarity	NPD5494	Approved
0.7844	Intermediate Similarity	NPD7458	Discontinued
0.7841	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7074	Phase 3
0.779	Intermediate Similarity	NPD8150	Discontinued
0.7784	Intermediate Similarity	NPD7177	Discontinued
0.7778	Intermediate Similarity	NPD7698	Approved
0.7778	Intermediate Similarity	NPD7696	Phase 3
0.7778	Intermediate Similarity	NPD7697	Approved
0.7764	Intermediate Similarity	NPD1551	Phase 2
0.7758	Intermediate Similarity	NPD6799	Approved
0.7753	Intermediate Similarity	NPD5953	Discontinued
0.774	Intermediate Similarity	NPD7054	Approved
0.772	Intermediate Similarity	NPD7874	Approved
0.772	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD5402	Approved
0.7719	Intermediate Similarity	NPD3817	Phase 2
0.7711	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD3748	Approved
0.7697	Intermediate Similarity	NPD7472	Approved
0.7684	Intermediate Similarity	NPD3818	Discontinued
0.7683	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD3882	Suspended
0.7667	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD2801	Approved
0.7654	Intermediate Similarity	NPD6797	Phase 2
0.7634	Intermediate Similarity	NPD6534	Approved
0.7634	Intermediate Similarity	NPD6535	Approved
0.7622	Intermediate Similarity	NPD1243	Approved
0.7619	Intermediate Similarity	NPD5403	Approved
0.7619	Intermediate Similarity	NPD920	Approved
0.7617	Intermediate Similarity	NPD7701	Phase 2
0.7611	Intermediate Similarity	NPD7251	Discontinued
0.7602	Intermediate Similarity	NPD37	Approved
0.7593	Intermediate Similarity	NPD2799	Discontinued
0.759	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7783	Phase 2
0.7586	Intermediate Similarity	NPD6234	Discontinued
0.7584	Intermediate Similarity	NPD3751	Discontinued
0.7584	Intermediate Similarity	NPD7228	Approved
0.7576	Intermediate Similarity	NPD4628	Phase 3
0.7572	Intermediate Similarity	NPD4966	Approved
0.7572	Intermediate Similarity	NPD4967	Phase 2
0.7572	Intermediate Similarity	NPD4965	Approved
0.7569	Intermediate Similarity	NPD7808	Phase 3
0.7557	Intermediate Similarity	NPD7229	Phase 3
0.7552	Intermediate Similarity	NPD8320	Phase 1
0.7552	Intermediate Similarity	NPD8319	Approved
0.7546	Intermediate Similarity	NPD6100	Approved
0.7546	Intermediate Similarity	NPD6099	Approved
0.7545	Intermediate Similarity	NPD1511	Approved
0.7539	Intermediate Similarity	NPD6823	Phase 2
0.7515	Intermediate Similarity	NPD2800	Approved
0.7515	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD4287	Approved
0.7513	Intermediate Similarity	NPD7699	Phase 2
0.7513	Intermediate Similarity	NPD7700	Phase 2
0.7512	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7801	Approved
0.7485	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6651	Approved
0.7458	Intermediate Similarity	NPD3787	Discontinued
0.7457	Intermediate Similarity	NPD8455	Phase 2
0.7456	Intermediate Similarity	NPD6273	Approved
0.7456	Intermediate Similarity	NPD1512	Approved
0.7452	Intermediate Similarity	NPD1470	Approved
0.7446	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7286	Phase 2
0.7438	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3764	Approved
0.7438	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD3926	Phase 2
0.7394	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6212	Phase 3
0.7394	Intermediate Similarity	NPD6213	Phase 3
0.7389	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD919	Approved
0.7375	Intermediate Similarity	NPD4625	Phase 3
0.7368	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2313	Discontinued
0.7321	Intermediate Similarity	NPD2309	Approved
0.7312	Intermediate Similarity	NPD4908	Phase 1
0.7303	Intermediate Similarity	NPD7199	Phase 2
0.7301	Intermediate Similarity	NPD230	Phase 1
0.7292	Intermediate Similarity	NPD8285	Discontinued
0.7278	Intermediate Similarity	NPD1283	Approved
0.7254	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD943	Approved
0.7229	Intermediate Similarity	NPD2438	Suspended
0.7228	Intermediate Similarity	NPD7240	Approved
0.7222	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8434	Phase 2
0.7205	Intermediate Similarity	NPD6832	Phase 2
0.7197	Intermediate Similarity	NPD1201	Approved
0.7189	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD8166	Discontinued
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2979	Phase 3
0.7129	Intermediate Similarity	NPD7654	Discontinued
0.7125	Intermediate Similarity	NPD1203	Approved
0.7121	Intermediate Similarity	NPD6973	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4288	Approved
0.7111	Intermediate Similarity	NPD1247	Approved
0.7091	Intermediate Similarity	NPD5124	Phase 1
0.7091	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1281	Approved
0.7083	Intermediate Similarity	NPD4363	Phase 3
0.7083	Intermediate Similarity	NPD4360	Phase 2
0.7081	Intermediate Similarity	NPD2798	Approved
0.707	Intermediate Similarity	NPD4626	Approved
0.7066	Intermediate Similarity	NPD7033	Discontinued
0.7066	Intermediate Similarity	NPD4308	Phase 3
0.7056	Intermediate Similarity	NPD6746	Phase 2
0.7055	Intermediate Similarity	NPD7008	Discontinued
0.7019	Intermediate Similarity	NPD1164	Approved
0.7018	Intermediate Similarity	NPD6190	Approved
0.7012	Intermediate Similarity	NPD3268	Approved
0.7012	Intermediate Similarity	NPD411	Approved
0.7012	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1651	Approved
0.7006	Intermediate Similarity	NPD5691	Approved
0.7	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8059	Phase 3
0.6988	Remote Similarity	NPD1899	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