NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	760.29
Volume:	778.853
LogP:	8.393
LogD:	3.514
LogS:	-2.045
# Rotatable Bonds:	8
TPSA:	194.21
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	7
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.067
Synthetic Accessibility Score:	5.304
Fsp3:	0.289
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.841
MDCK Permeability:	7.025215836620191e-06
Pgp-inhibitor:	0.699
Pgp-substrate:	0.185
Human Intestinal Absorption (HIA):	0.149
20% Bioavailability (F20%):	0.891
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	98.09073638916016%
Volume Distribution (VD):	0.489
Pgp-substrate:	5.634170055389404%

ADMET: Metabolism

CYP1A2-inhibitor:	0.088
CYP1A2-substrate:	0.319
CYP2C19-inhibitor:	0.943
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.904
CYP2C9-substrate:	0.969
CYP2D6-inhibitor:	0.729
CYP2D6-substrate:	0.254
CYP3A4-inhibitor:	0.289
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	11.774
Half-life (T1/2):	0.036

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.968
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.056
Rat Oral Acute Toxicity:	0.831
Maximum Recommended Daily Dose:	0.959
Skin Sensitization:	0.942
Carcinogencity:	0.046
Eye Corrosion:	0.003
Eye Irritation:	0.863
Respiratory Toxicity:	0.065

Download Data

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

Natural Product: NPC477529

Natural Product ID:	NPC477529
*Common Name:**	(5aS,10aR)-2-[(1R,5S,6R)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,3,8-trihydroxy-5a-(3-methylbut-2-enyl)-10aH-[1]benzofuro[3,2-b]chromen-11-one
IUPAC Name:	(5aS,10aR)-2-[(1R,5S,6R)-6-[2,4-dihydroxy-3-(3-methylbut-2-enyl)benzoyl]-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,3,8-trihydroxy-5a-(3-methylbut-2-enyl)-10aH-[1]benzofuro[3,2-b]chromen-11-one
Synonyms:
Standard InCHIKey:	GCSSGYKMPPFQLH-KDJZGPCZSA-N
Standard InCHI:	InChI=1S/C45H44O11/c1-21(2)6-9-27-32(48)13-11-28(40(27)51)41(52)37-29(26-10-7-24(46)18-33(26)49)16-23(5)17-30(37)38-34(50)20-36-39(42(38)53)43(54)44-45(56-36,15-14-22(3)4)31-12-8-25(47)19-35(31)55-44/h6-8,10-14,17-20,29-30,37,44,46-51,53H,9,15-16H2,1-5H3/t29-,30-,37-,44+,45+/m1/s1
SMILES:	CC1=C[C@H]([C@@H]([C@H](C1)C2=C(C=C(C=C2)O)O)C(=O)C3=C(C(=C(C=C3)O)CC=C(C)C)O)C4=C(C5=C(C=C4O)O[C@@]6([C@H](C5=O)OC7=C6C=CC(=C7)O)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90681447
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO19738	Morus nigra	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[18330242]
NPO19738	Morus nigra	Species	Moraceae	Eukaryota	n.a.	twig	n.a.	PMID[21401118]
NPO19738	Morus nigra	Species	Moraceae	Eukaryota	twigs	Xinjiang Uygur Autonomous Region, China	2006-MAY	PMID[21401118]
NPO19738	Morus nigra	Species	Moraceae	Eukaryota	root bark	Konya, Turkey	2007-APR	PMID[24901948]
NPO19738	Morus nigra	Species	Moraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19738	Morus nigra	Species	Moraceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	4000	nM	PMID[24901948]

☑ 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 NPC477529 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	431
0.1-0.2	1519
0.2-0.3	3214
0.3-0.4	8317
0.4-0.5	10268
0.5-0.6	4331
0.6-0.7	5763
0.7-0.8	5538
0.8-0.85	2473
0.85-0.9	762
0.9-0.95	76
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9573	High Similarity	NPC147363
0.9573	High Similarity	NPC17105
0.9573	High Similarity	NPC474276
0.9573	High Similarity	NPC73899
0.9437	High Similarity	NPC195136
0.9387	High Similarity	NPC82330
0.9383	High Similarity	NPC473009
0.9375	High Similarity	NPC105584
0.9325	High Similarity	NPC473010
0.9321	High Similarity	NPC473012
0.9268	High Similarity	NPC251336
0.9259	High Similarity	NPC301256
0.9259	High Similarity	NPC312273
0.9255	High Similarity	NPC15815
0.9212	High Similarity	NPC292233
0.9198	High Similarity	NPC226462
0.9198	High Similarity	NPC98023
0.9198	High Similarity	NPC121647
0.9193	High Similarity	NPC1796
0.9193	High Similarity	NPC257166
0.9187	High Similarity	NPC79375
0.9187	High Similarity	NPC37253
0.9146	High Similarity	NPC63438
0.9136	High Similarity	NPC51247
0.9136	High Similarity	NPC295090
0.9136	High Similarity	NPC123544
0.913	High Similarity	NPC54830
0.913	High Similarity	NPC56049
0.9125	High Similarity	NPC121568
0.9102	High Similarity	NPC287884
0.9102	High Similarity	NPC8704
0.908	High Similarity	NPC42965
0.9074	High Similarity	NPC475184
0.9074	High Similarity	NPC208258
0.9024	High Similarity	NPC92589
0.9018	High Similarity	NPC51760
0.9018	High Similarity	NPC125969
0.9012	High Similarity	NPC20530
0.9012	High Similarity	NPC32867
0.9012	High Similarity	NPC69531
0.9012	High Similarity	NPC215917
0.9012	High Similarity	NPC10754
0.9006	High Similarity	NPC236756
0.9006	High Similarity	NPC311579
0.9	High Similarity	NPC178484
0.8982	High Similarity	NPC286230
0.8982	High Similarity	NPC253730
0.897	High Similarity	NPC475106
0.897	High Similarity	NPC473011
0.8957	High Similarity	NPC322459
0.8957	High Similarity	NPC323627
0.8957	High Similarity	NPC287789
0.8957	High Similarity	NPC271741
0.8957	High Similarity	NPC324358
0.8957	High Similarity	NPC318527
0.8951	High Similarity	NPC134171
0.8951	High Similarity	NPC300668
0.8951	High Similarity	NPC182555
0.8951	High Similarity	NPC66441
0.8944	High Similarity	NPC477957
0.8944	High Similarity	NPC115601
0.8944	High Similarity	NPC43345
0.8944	High Similarity	NPC473996
0.8944	High Similarity	NPC78324
0.8944	High Similarity	NPC208011
0.8944	High Similarity	NPC39154
0.8935	High Similarity	NPC118128
0.8929	High Similarity	NPC53252
0.8922	High Similarity	NPC476255
0.8916	High Similarity	NPC38591
0.8909	High Similarity	NPC476929
0.8902	High Similarity	NPC90497
0.8896	High Similarity	NPC61112
0.8896	High Similarity	NPC198489
0.8896	High Similarity	NPC309648
0.8889	High Similarity	NPC20907
0.8889	High Similarity	NPC244250
0.8889	High Similarity	NPC100134
0.8889	High Similarity	NPC293286
0.8889	High Similarity	NPC324447
0.8889	High Similarity	NPC209760
0.8882	High Similarity	NPC472636
0.8882	High Similarity	NPC476551
0.8882	High Similarity	NPC472580
0.8882	High Similarity	NPC476553
0.8882	High Similarity	NPC476552
0.8876	High Similarity	NPC279209
0.8876	High Similarity	NPC102277
0.8875	High Similarity	NPC3642
0.8869	High Similarity	NPC476459
0.8862	High Similarity	NPC169471
0.8848	High Similarity	NPC306978
0.8848	High Similarity	NPC172687
0.8841	High Similarity	NPC161650
0.8837	High Similarity	NPC476210
0.8837	High Similarity	NPC476199
0.8834	High Similarity	NPC205026
0.8834	High Similarity	NPC207809
0.8834	High Similarity	NPC304207
0.8834	High Similarity	NPC100049
0.8834	High Similarity	NPC265624
0.8834	High Similarity	NPC121649
0.8834	High Similarity	NPC248739
0.8834	High Similarity	NPC217706
0.8834	High Similarity	NPC259710
0.8834	High Similarity	NPC215203
0.8834	High Similarity	NPC258474
0.8834	High Similarity	NPC52611
0.8834	High Similarity	NPC158027
0.8834	High Similarity	NPC111341
0.8834	High Similarity	NPC201227
0.8834	High Similarity	NPC48579
0.8834	High Similarity	NPC476169
0.8834	High Similarity	NPC304745
0.8834	High Similarity	NPC477958
0.8834	High Similarity	NPC186227
0.8834	High Similarity	NPC159707
0.8834	High Similarity	NPC14606
0.8834	High Similarity	NPC150908
0.8827	High Similarity	NPC171651
0.8827	High Similarity	NPC476238
0.8827	High Similarity	NPC216035
0.8827	High Similarity	NPC174086
0.8827	High Similarity	NPC327269
0.8827	High Similarity	NPC138288
0.8827	High Similarity	NPC31627
0.8827	High Similarity	NPC35567
0.8827	High Similarity	NPC243171
0.8827	High Similarity	NPC210597
0.8827	High Similarity	NPC217149
0.8824	High Similarity	NPC257667
0.8824	High Similarity	NPC186847
0.8824	High Similarity	NPC472454
0.8824	High Similarity	NPC476159
0.882	High Similarity	NPC476509
0.882	High Similarity	NPC472421
0.8817	High Similarity	NPC63514
0.8817	High Similarity	NPC107627
0.8817	High Similarity	NPC54903
0.8817	High Similarity	NPC286074
0.8812	High Similarity	NPC152233
0.8812	High Similarity	NPC122894
0.881	High Similarity	NPC62444
0.8802	High Similarity	NPC472581
0.8802	High Similarity	NPC290160
0.8802	High Similarity	NPC159508
0.8802	High Similarity	NPC469395
0.8795	High Similarity	NPC18380
0.8795	High Similarity	NPC137232
0.8795	High Similarity	NPC97812
0.8793	High Similarity	NPC150977
0.8788	High Similarity	NPC311574
0.8788	High Similarity	NPC264932
0.8786	High Similarity	NPC244903
0.8786	High Similarity	NPC121888
0.878	High Similarity	NPC192587
0.878	High Similarity	NPC78492
0.878	High Similarity	NPC146636
0.878	High Similarity	NPC208152
0.8779	High Similarity	NPC101991
0.8779	High Similarity	NPC156955
0.8773	High Similarity	NPC223701
0.8773	High Similarity	NPC303485
0.8773	High Similarity	NPC290830
0.8773	High Similarity	NPC7989
0.8773	High Similarity	NPC268193
0.8773	High Similarity	NPC203080
0.8773	High Similarity	NPC72425
0.8773	High Similarity	NPC472583
0.8773	High Similarity	NPC248793
0.8773	High Similarity	NPC180301
0.8773	High Similarity	NPC71061
0.8773	High Similarity	NPC194593
0.8772	High Similarity	NPC168789
0.8772	High Similarity	NPC475080
0.8772	High Similarity	NPC476311
0.8772	High Similarity	NPC476152
0.8772	High Similarity	NPC469393
0.8765	High Similarity	NPC254412
0.8765	High Similarity	NPC474744
0.8765	High Similarity	NPC471677
0.8765	High Similarity	NPC244577
0.8765	High Similarity	NPC474772
0.8765	High Similarity	NPC472423
0.8765	High Similarity	NPC262038
0.8765	High Similarity	NPC472422
0.8765	High Similarity	NPC262039
0.8765	High Similarity	NPC472420
0.8765	High Similarity	NPC476196
0.8765	High Similarity	NPC278476
0.8765	High Similarity	NPC471675
0.8765	High Similarity	NPC469344
0.8765	High Similarity	NPC263384
0.8765	High Similarity	NPC92815
0.8765	High Similarity	NPC471229
0.8765	High Similarity	NPC476162
0.8765	High Similarity	NPC319910
0.8765	High Similarity	NPC471676
0.8758	High Similarity	NPC473016
0.8758	High Similarity	NPC132345

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 NPC477529 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	917
0.2-0.3	1645
0.3-0.4	2609
0.4-0.5	1999
0.5-0.6	1024
0.6-0.7	400
0.7-0.8	148
0.8-0.85	27
0.85-0.9	10
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8951	High Similarity	NPD8443	Clinical (unspecified phase)
0.8841	High Similarity	NPD7075	Discontinued
0.8706	High Similarity	NPD7804	Clinical (unspecified phase)
0.8683	High Similarity	NPD6959	Discontinued
0.8659	High Similarity	NPD7096	Clinical (unspecified phase)
0.8639	High Similarity	NPD7852	Clinical (unspecified phase)
0.8589	High Similarity	NPD4380	Phase 2
0.8529	High Similarity	NPD6168	Clinical (unspecified phase)
0.8529	High Similarity	NPD6166	Phase 2
0.8529	High Similarity	NPD6167	Clinical (unspecified phase)
0.8509	High Similarity	NPD4378	Clinical (unspecified phase)
0.8509	High Similarity	NPD7410	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD7768	Phase 2
0.8424	Intermediate Similarity	NPD7411	Suspended
0.8373	Intermediate Similarity	NPD6801	Discontinued
0.8323	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD7819	Suspended
0.8294	Intermediate Similarity	NPD5494	Approved
0.8284	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD1549	Phase 2
0.8232	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD3882	Suspended
0.8192	Intermediate Similarity	NPD7808	Phase 3
0.8187	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD3749	Approved
0.8155	Intermediate Similarity	NPD1934	Approved
0.8144	Intermediate Similarity	NPD6599	Discontinued
0.8136	Intermediate Similarity	NPD7251	Discontinued
0.8136	Intermediate Similarity	NPD6559	Discontinued
0.811	Intermediate Similarity	NPD6799	Approved
0.8079	Intermediate Similarity	NPD6797	Phase 2
0.8057	Intermediate Similarity	NPD7473	Discontinued
0.8045	Intermediate Similarity	NPD8312	Approved
0.8045	Intermediate Similarity	NPD8313	Approved
0.8023	Intermediate Similarity	NPD7074	Phase 3
0.8012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2796	Approved
0.7966	Intermediate Similarity	NPD7054	Approved
0.7966	Intermediate Similarity	NPD5844	Phase 1
0.7964	Intermediate Similarity	NPD5403	Approved
0.7953	Intermediate Similarity	NPD3817	Phase 2
0.795	Intermediate Similarity	NPD1510	Phase 2
0.7921	Intermediate Similarity	NPD7472	Approved
0.791	Intermediate Similarity	NPD3818	Discontinued
0.7886	Intermediate Similarity	NPD6232	Discontinued
0.7866	Intermediate Similarity	NPD2800	Approved
0.7861	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD5402	Approved
0.7844	Intermediate Similarity	NPD5401	Approved
0.7826	Intermediate Similarity	NPD1607	Approved
0.7826	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD8434	Phase 2
0.7814	Intermediate Similarity	NPD8150	Discontinued
0.7812	Intermediate Similarity	NPD1240	Approved
0.7798	Intermediate Similarity	NPD1512	Approved
0.7791	Intermediate Similarity	NPD2801	Approved
0.779	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7390	Discontinued
0.776	Intermediate Similarity	NPD7871	Phase 2
0.776	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD7870	Phase 2
0.7758	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD3750	Approved
0.7709	Intermediate Similarity	NPD3751	Discontinued
0.7708	Intermediate Similarity	NPD7435	Discontinued
0.7708	Intermediate Similarity	NPD7697	Approved
0.7708	Intermediate Similarity	NPD7696	Phase 3
0.7708	Intermediate Similarity	NPD7698	Approved
0.7688	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD8455	Phase 2
0.7679	Intermediate Similarity	NPD1511	Approved
0.7661	Intermediate Similarity	NPD7458	Discontinued
0.7644	Intermediate Similarity	NPD6777	Approved
0.7644	Intermediate Similarity	NPD6781	Approved
0.7644	Intermediate Similarity	NPD6779	Approved
0.7644	Intermediate Similarity	NPD6776	Approved
0.7644	Intermediate Similarity	NPD6782	Approved
0.7644	Intermediate Similarity	NPD6778	Approved
0.7644	Intermediate Similarity	NPD6780	Approved
0.764	Intermediate Similarity	NPD3926	Phase 2
0.7633	Intermediate Similarity	NPD2533	Approved
0.7633	Intermediate Similarity	NPD2534	Approved
0.7633	Intermediate Similarity	NPD2532	Approved
0.7627	Intermediate Similarity	NPD1247	Approved
0.7614	Intermediate Similarity	NPD919	Approved
0.7607	Intermediate Similarity	NPD6651	Approved
0.7596	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3787	Discontinued
0.7563	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7563	Intermediate Similarity	NPD7874	Approved
0.7562	Intermediate Similarity	NPD4908	Phase 1
0.7551	Intermediate Similarity	NPD7701	Phase 2
0.7544	Intermediate Similarity	NPD920	Approved
0.753	Intermediate Similarity	NPD2344	Approved
0.7525	Intermediate Similarity	NPD7801	Approved
0.7513	Intermediate Similarity	NPD8151	Discontinued
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD8320	Phase 1
0.7487	Intermediate Similarity	NPD8319	Approved
0.747	Intermediate Similarity	NPD6100	Approved
0.747	Intermediate Similarity	NPD1551	Phase 2
0.747	Intermediate Similarity	NPD6099	Approved
0.7457	Intermediate Similarity	NPD3226	Approved
0.7448	Intermediate Similarity	NPD7699	Phase 2
0.7448	Intermediate Similarity	NPD7700	Phase 2
0.7444	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1243	Approved
0.7427	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3748	Approved
0.741	Intermediate Similarity	NPD2799	Discontinued
0.7403	Intermediate Similarity	NPD2403	Approved
0.7391	Intermediate Similarity	NPD5953	Discontinued
0.7382	Intermediate Similarity	NPD4363	Phase 3
0.7382	Intermediate Similarity	NPD4360	Phase 2
0.7382	Intermediate Similarity	NPD6534	Approved
0.7382	Intermediate Similarity	NPD6535	Approved
0.7381	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD7286	Phase 2
0.7365	Intermediate Similarity	NPD2935	Discontinued
0.7362	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD2309	Approved
0.735	Intermediate Similarity	NPD7783	Phase 2
0.735	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6355	Discontinued
0.7323	Intermediate Similarity	NPD7584	Approved
0.7322	Intermediate Similarity	NPD7228	Approved
0.7308	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6823	Phase 2
0.7294	Intermediate Similarity	NPD7003	Approved
0.7293	Intermediate Similarity	NPD7229	Phase 3
0.7288	Intermediate Similarity	NPD5761	Phase 2
0.7288	Intermediate Similarity	NPD5760	Phase 2
0.7288	Intermediate Similarity	NPD1465	Phase 2
0.7282	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD4287	Approved
0.7256	Intermediate Similarity	NPD6798	Discontinued
0.7238	Intermediate Similarity	NPD7199	Phase 2
0.7232	Intermediate Similarity	NPD37	Approved
0.7228	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6234	Discontinued
0.7222	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2346	Discontinued
0.7207	Intermediate Similarity	NPD4967	Phase 2
0.7207	Intermediate Similarity	NPD4965	Approved
0.7207	Intermediate Similarity	NPD4966	Approved
0.7198	Intermediate Similarity	NPD5710	Approved
0.7198	Intermediate Similarity	NPD5711	Approved
0.7194	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4361	Phase 2
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD5408	Approved
0.716	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD8127	Discontinued
0.7143	Intermediate Similarity	NPD7097	Phase 1
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7126	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5124	Phase 1
0.7125	Intermediate Similarity	NPD1610	Phase 2
0.7125	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD1471	Phase 3
0.7118	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6233	Phase 2
0.7101	Intermediate Similarity	NPD7033	Discontinued
0.7093	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6273	Approved
0.7074	Intermediate Similarity	NPD7685	Pre-registration
0.7056	Intermediate Similarity	NPD8285	Discontinued
0.7052	Intermediate Similarity	NPD6190	Approved
0.7048	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD3764	Approved
0.7043	Intermediate Similarity	NPD7799	Discontinued
0.7043	Intermediate Similarity	NPD7177	Discontinued
0.7039	Intermediate Similarity	NPD7577	Discontinued
0.7033	Intermediate Similarity	NPD7907	Approved
0.7015	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2798	Approved
0.6988	Remote Similarity	NPD4625	Phase 3
0.6984	Remote Similarity	NPD6765	Approved
0.6984	Remote Similarity	NPD7240	Approved
0.6984	Remote Similarity	NPD6764	Approved
0.6977	Remote Similarity	NPD2424	Discontinued
0.6971	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD1729	Discontinued
0.6964	Remote Similarity	NPD943	Approved
0.6964	Remote Similarity	NPD1613	Approved
0.6964	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4060	Phase 1

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