NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	950.19
Volume:	890.985
LogP:	4.497
LogD:	1.357
LogS:	-5.696
# Rotatable Bonds:	5
TPSA:	372.87
# H-Bond Aceptor:	21
# H-Bond Donor:	12
# Rings:	9
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.086
Synthetic Accessibility Score:	5.827
Fsp3:	0.25
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.517
MDCK Permeability:	5.541508926398819e-06
Pgp-inhibitor:	0.885
Pgp-substrate:	0.543
Human Intestinal Absorption (HIA):	0.993
20% Bioavailability (F20%):	0.134
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	82.21514892578125%
Volume Distribution (VD):	0.288
Pgp-substrate:	6.726081848144531%

ADMET: Metabolism

CYP1A2-inhibitor:	0.133
CYP1A2-substrate:	0.777
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.046
CYP2C9-inhibitor:	0.158
CYP2C9-substrate:	0.03
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.024
CYP3A4-substrate:	0.031

ADMET: Excretion

Clearance (CL):	1.675
Half-life (T1/2):	0.006

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.04
Drug-inuced Liver Injury (DILI):	0.987
AMES Toxicity:	0.175
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.107
Skin Sensitization:	0.036
Carcinogencity:	0.001
Eye Corrosion:	0.003
Eye Irritation:	0.107
Respiratory Toxicity:	0.005

Download Data

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

Natural Product: NPC477991

Natural Product ID:	NPC477991
*Common Name:**	(2R,3R)-5-[2,8-dihydroxy-6-methoxy-3-methyl-9,10-dioxo-5-[(5S,6R,7S,8R)-4,5,6,7,8-pentahydroxy-2-methoxy-7-methyl-9,10-dioxo-6,8-dihydro-5H-anthracen-1-yl]anthracen-1-yl]-1,2,3,4,8-pentahydroxy-6-methoxy-3-methyl-2H-anthracene-9,10-dione
IUPAC Name:	(2R,3R)-5-[2,8-dihydroxy-6-methoxy-3-methyl-9,10-dioxo-5-[(5S,6R,7S,8R)-4,5,6,7,8-pentahydroxy-2-methoxy-7-methyl-9,10-dioxo-6,8-dihydro-5H-anthracen-1-yl]anthracen-1-yl]-1,2,3,4,8-pentahydroxy-6-methoxy-3-methyl-2H-anthracene-9,10-dione
Synonyms:
Standard InCHIKey:	XYZZDUHWDNYLFK-ZSSKLDDPSA-N
Standard InCHI:	InChI=1S/C48H38O21/c1-11-7-12-19(26(34(11)52)25-18(69-6)10-15(51)22-29(25)40(58)33-31(38(22)56)42(60)46(64)48(3,66)44(33)62)36(54)20-13(49)8-16(67-4)23(27(20)35(12)53)24-17(68-5)9-14(50)21-28(24)39(57)32-30(37(21)55)41(59)45(63)47(2,65)43(32)61/h7-10,41,43,45-46,49-52,59-66H,1-6H3/t41-,43+,45+,46+,47-,48-/m0/s1
SMILES:	CC1=CC2=C(C(=C1O)C3=C(C=C(C4=C3C(=O)C5=C([C@]([C@@H](C(=C5C4=O)O)O)(C)O)O)O)OC)C(=O)C6=C(C2=O)C(=C(C=C6O)OC)C7=C(C=C(C8=C7C(=O)C9=C(C8=O)[C@@H]([C@H]([C@@]([C@@H]9O)(C)O)O)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	136986996
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	Mentha pulegium	n.a.	n.a.	PMID[19271717]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19271717]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	Stems	n.a.	n.a.	PMID[23664494]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	Eukaryota	isolated from fresh Juncus acutus	Lake Wadi el Natrun, Egypt	2012-NOV	PMID[25010124]
NPO16860	Stemphylium globuliferum	Species	Pleosporaceae	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
MIC	3
Others	1

Activity Type	# Activity
Cell Line	2
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1864	Cell Line	L5178Y	Mus musculus	IC50	>	10000	nM	PMID[25010124]
NPT1864	Cell Line	L5178Y	Mus musculus	GI	=	0	%	PMID[25010124]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	64	ug/ml	PMID[25010124]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	64	ug/ml	PMID[25010124]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	64	ug/ml	PMID[25010124]

☑ 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 NPC477991 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	454
0.1-0.2	1662
0.2-0.3	3482
0.3-0.4	8777
0.4-0.5	9994
0.5-0.6	4130
0.6-0.7	5857
0.7-0.8	6401
0.8-0.85	1680
0.85-0.9	239
0.9-0.95	12
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477992
0.9691	High Similarity	NPC105414
0.9691	High Similarity	NPC472058
0.9691	High Similarity	NPC324522
0.9691	High Similarity	NPC470341
0.9691	High Similarity	NPC234497
0.9448	High Similarity	NPC472051
0.9448	High Similarity	NPC472057
0.9387	High Similarity	NPC472053
0.9325	High Similarity	NPC472059
0.9321	High Similarity	NPC472060
0.9321	High Similarity	NPC470342
0.9321	High Similarity	NPC472052
0.9141	High Similarity	NPC324736
0.9053	High Similarity	NPC477836
0.9042	High Similarity	NPC477835
0.903	High Similarity	NPC472261
0.9012	High Similarity	NPC155686
0.8982	High Similarity	NPC469664
0.8957	High Similarity	NPC66508
0.8957	High Similarity	NPC226656
0.8914	High Similarity	NPC87583
0.8889	High Similarity	NPC470569
0.8889	High Similarity	NPC46882
0.8889	High Similarity	NPC132990
0.8834	High Similarity	NPC470340
0.8827	High Similarity	NPC147735
0.8827	High Similarity	NPC470568
0.8817	High Similarity	NPC178173
0.8802	High Similarity	NPC189552
0.8802	High Similarity	NPC273467
0.8793	High Similarity	NPC114257
0.8793	High Similarity	NPC299149
0.8793	High Similarity	NPC277710
0.8793	High Similarity	NPC153578
0.8779	High Similarity	NPC154986
0.875	High Similarity	NPC15374
0.8743	High Similarity	NPC284495
0.8743	High Similarity	NPC186325
0.8743	High Similarity	NPC476506
0.8743	High Similarity	NPC312993
0.8736	High Similarity	NPC470334
0.8735	High Similarity	NPC208258
0.8727	High Similarity	NPC68727
0.872	High Similarity	NPC470338
0.872	High Similarity	NPC113608
0.872	High Similarity	NPC268992
0.872	High Similarity	NPC51824
0.872	High Similarity	NPC43345
0.872	High Similarity	NPC180944
0.872	High Similarity	NPC470337
0.8712	High Similarity	NPC255641
0.8712	High Similarity	NPC290954
0.8706	High Similarity	NPC251336
0.8701	High Similarity	NPC473686
0.8701	High Similarity	NPC229817
0.8701	High Similarity	NPC475220
0.8701	High Similarity	NPC221140
0.8701	High Similarity	NPC475352
0.8693	High Similarity	NPC473717
0.8693	High Similarity	NPC475662
0.8693	High Similarity	NPC473631
0.8693	High Similarity	NPC293227
0.8693	High Similarity	NPC313452
0.869	High Similarity	NPC137232
0.869	High Similarity	NPC219686
0.869	High Similarity	NPC18380
0.8683	High Similarity	NPC228654
0.8683	High Similarity	NPC177650
0.8678	High Similarity	NPC46958
0.8671	High Similarity	NPC469393
0.8659	High Similarity	NPC476551
0.8659	High Similarity	NPC476552
0.8659	High Similarity	NPC476553
0.8655	High Similarity	NPC253730
0.8655	High Similarity	NPC286230
0.8655	High Similarity	NPC76647
0.865	High Similarity	NPC477221
0.8642	High Similarity	NPC34802
0.8642	High Similarity	NPC190648
0.8642	High Similarity	NPC312929
0.8642	High Similarity	NPC37709
0.8642	High Similarity	NPC126767
0.8642	High Similarity	NPC245584
0.8642	High Similarity	NPC118027
0.8642	High Similarity	NPC56433
0.8642	High Similarity	NPC289042
0.8642	High Similarity	NPC290194
0.8636	High Similarity	NPC208069
0.8636	High Similarity	NPC315221
0.8631	High Similarity	NPC470810
0.8631	High Similarity	NPC195136
0.8631	High Similarity	NPC292863
0.8631	High Similarity	NPC184326
0.8629	High Similarity	NPC477683
0.8629	High Similarity	NPC477682
0.8614	High Similarity	NPC37253
0.8614	High Similarity	NPC79375
0.8613	High Similarity	NPC271385
0.8613	High Similarity	NPC76128
0.8613	High Similarity	NPC30432
0.8613	High Similarity	NPC473113
0.8613	High Similarity	NPC111536
0.8613	High Similarity	NPC5029
0.8606	High Similarity	NPC40356
0.8606	High Similarity	NPC154683
0.8605	High Similarity	NPC300307
0.8605	High Similarity	NPC54903
0.8605	High Similarity	NPC469486
0.8605	High Similarity	NPC264063
0.8605	High Similarity	NPC286074
0.8598	High Similarity	NPC294646
0.8598	High Similarity	NPC225854
0.8596	High Similarity	NPC469394
0.8588	High Similarity	NPC290160
0.8588	High Similarity	NPC473009
0.858	High Similarity	NPC185275
0.8571	High Similarity	NPC105584
0.8571	High Similarity	NPC15815
0.8571	High Similarity	NPC55443
0.8571	High Similarity	NPC216307
0.8571	High Similarity	NPC475233
0.8571	High Similarity	NPC51760
0.8571	High Similarity	NPC18699
0.8571	High Similarity	NPC475246
0.8571	High Similarity	NPC195167
0.8571	High Similarity	NPC90497
0.8563	High Similarity	NPC472054
0.8563	High Similarity	NPC470333
0.8563	High Similarity	NPC98776
0.8563	High Similarity	NPC472050
0.8563	High Similarity	NPC85368
0.8563	High Similarity	NPC470336
0.8563	High Similarity	NPC470335
0.8554	High Similarity	NPC107109
0.8554	High Similarity	NPC324447
0.8545	High Similarity	NPC149526
0.8545	High Similarity	NPC474417
0.8545	High Similarity	NPC478148
0.8538	High Similarity	NPC472049
0.8538	High Similarity	NPC473010
0.8538	High Similarity	NPC169471
0.8538	High Similarity	NPC26386
0.8537	High Similarity	NPC329933
0.8531	High Similarity	NPC477860
0.8531	High Similarity	NPC475161
0.8529	High Similarity	NPC149389
0.8529	High Similarity	NPC473012
0.8523	High Similarity	NPC265380
0.8523	High Similarity	NPC471789
0.8521	High Similarity	NPC472055
0.8521	High Similarity	NPC226462
0.8521	High Similarity	NPC98023
0.8519	High Similarity	NPC34482
0.8514	High Similarity	NPC300657
0.8514	High Similarity	NPC68381
0.8514	High Similarity	NPC3718
0.8512	High Similarity	NPC37543
0.8512	High Similarity	NPC257166
0.8512	High Similarity	NPC474637
0.8512	High Similarity	NPC199463
0.8508	High Similarity	NPC264302
0.8506	High Similarity	NPC477529
0.8506	High Similarity	NPC4200
0.8497	Intermediate Similarity	NPC53252
0.8492	Intermediate Similarity	NPC112380
0.8488	Intermediate Similarity	NPC85047
0.8488	Intermediate Similarity	NPC120857
0.8488	Intermediate Similarity	NPC17274
0.8485	Intermediate Similarity	NPC477914
0.8483	Intermediate Similarity	NPC478001
0.8483	Intermediate Similarity	NPC150977
0.848	Intermediate Similarity	NPC476505
0.8476	Intermediate Similarity	NPC152233
0.8475	Intermediate Similarity	NPC324742
0.8471	Intermediate Similarity	NPC301256
0.8471	Intermediate Similarity	NPC312273
0.8466	Intermediate Similarity	NPC289876
0.8466	Intermediate Similarity	NPC470570
0.8462	Intermediate Similarity	NPC470339
0.8462	Intermediate Similarity	NPC472617
0.8462	Intermediate Similarity	NPC51247
0.8457	Intermediate Similarity	NPC19896
0.8457	Intermediate Similarity	NPC227841
0.8457	Intermediate Similarity	NPC203751
0.8457	Intermediate Similarity	NPC48762
0.8457	Intermediate Similarity	NPC131862
0.8457	Intermediate Similarity	NPC244691
0.8457	Intermediate Similarity	NPC229051
0.8457	Intermediate Similarity	NPC213052
0.8453	Intermediate Similarity	NPC314672
0.8452	Intermediate Similarity	NPC78492
0.8452	Intermediate Similarity	NPC54830
0.8452	Intermediate Similarity	NPC478223
0.8452	Intermediate Similarity	NPC56049
0.8452	Intermediate Similarity	NPC14561
0.8452	Intermediate Similarity	NPC77807
0.8452	Intermediate Similarity	NPC208152
0.8452	Intermediate Similarity	NPC5379
0.8448	Intermediate Similarity	NPC241387

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 NPC477991 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	394
0.1-0.2	980
0.2-0.3	1792
0.3-0.4	2678
0.4-0.5	1908
0.5-0.6	920
0.6-0.7	320
0.7-0.8	133
0.8-0.85	24
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8802	High Similarity	NPD6959	Discontinued
0.8488	Intermediate Similarity	NPD7473	Discontinued
0.8457	Intermediate Similarity	NPD7390	Discontinued
0.8436	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD6232	Discontinued
0.8343	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8263	Intermediate Similarity	NPD8151	Discontinued
0.8263	Intermediate Similarity	NPD4380	Phase 2
0.8258	Intermediate Similarity	NPD8313	Approved
0.8258	Intermediate Similarity	NPD8312	Approved
0.8176	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7819	Suspended
0.8114	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7768	Phase 2
0.8012	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD6166	Phase 2
0.8011	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD5844	Phase 1
0.7964	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD7871	Phase 2
0.7958	Intermediate Similarity	NPD7870	Phase 2
0.7923	Intermediate Similarity	NPD8150	Discontinued
0.7877	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD7075	Discontinued
0.7857	Intermediate Similarity	NPD2533	Approved
0.7857	Intermediate Similarity	NPD2534	Approved
0.7857	Intermediate Similarity	NPD2532	Approved
0.7845	Intermediate Similarity	NPD6559	Discontinued
0.7842	Intermediate Similarity	NPD6778	Approved
0.7842	Intermediate Similarity	NPD6781	Approved
0.7842	Intermediate Similarity	NPD6780	Approved
0.7842	Intermediate Similarity	NPD6782	Approved
0.7842	Intermediate Similarity	NPD6777	Approved
0.7842	Intermediate Similarity	NPD6779	Approved
0.7842	Intermediate Similarity	NPD6776	Approved
0.7816	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD7696	Phase 3
0.7812	Intermediate Similarity	NPD7435	Discontinued
0.7812	Intermediate Similarity	NPD7698	Approved
0.7812	Intermediate Similarity	NPD7697	Approved
0.7791	Intermediate Similarity	NPD7411	Suspended
0.7771	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD3749	Approved
0.7751	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD1934	Approved
0.7744	Intermediate Similarity	NPD1510	Phase 2
0.7744	Intermediate Similarity	NPD7701	Phase 2
0.7735	Intermediate Similarity	NPD7472	Approved
0.7735	Intermediate Similarity	NPD7074	Phase 3
0.773	Intermediate Similarity	NPD1607	Approved
0.7705	Intermediate Similarity	NPD7808	Phase 3
0.7701	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD7054	Approved
0.7674	Intermediate Similarity	NPD3226	Approved
0.7665	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD7874	Approved
0.765	Intermediate Similarity	NPD7251	Discontinued
0.7644	Intermediate Similarity	NPD6801	Discontinued
0.7644	Intermediate Similarity	NPD7700	Phase 2
0.7644	Intermediate Similarity	NPD7699	Phase 2
0.7626	Intermediate Similarity	NPD7801	Approved
0.7624	Intermediate Similarity	NPD3818	Discontinued
0.7624	Intermediate Similarity	NPD3751	Discontinued
0.7607	Intermediate Similarity	NPD1240	Approved
0.7605	Intermediate Similarity	NPD1549	Phase 2
0.76	Intermediate Similarity	NPD2801	Approved
0.7596	Intermediate Similarity	NPD6797	Phase 2
0.759	Intermediate Similarity	NPD5406	Approved
0.759	Intermediate Similarity	NPD5408	Approved
0.759	Intermediate Similarity	NPD5405	Approved
0.759	Intermediate Similarity	NPD5404	Approved
0.7584	Intermediate Similarity	NPD5494	Approved
0.7579	Intermediate Similarity	NPD6535	Approved
0.7579	Intermediate Similarity	NPD6534	Approved
0.7577	Intermediate Similarity	NPD6823	Phase 2
0.7545	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD7783	Phase 2
0.7515	Intermediate Similarity	NPD7003	Approved
0.7514	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8319	Approved
0.75	Intermediate Similarity	NPD8320	Phase 1
0.7485	Intermediate Similarity	NPD2796	Approved
0.7485	Intermediate Similarity	NPD1511	Approved
0.7471	Intermediate Similarity	NPD7458	Discontinued
0.7463	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5402	Approved
0.7447	Intermediate Similarity	NPD8434	Phase 2
0.7429	Intermediate Similarity	NPD6599	Discontinued
0.7412	Intermediate Similarity	NPD3750	Approved
0.741	Intermediate Similarity	NPD6651	Approved
0.7403	Intermediate Similarity	NPD3787	Discontinued
0.7401	Intermediate Similarity	NPD1465	Phase 2
0.7401	Intermediate Similarity	NPD8455	Phase 2
0.7399	Intermediate Similarity	NPD1512	Approved
0.7381	Intermediate Similarity	NPD2935	Discontinued
0.7371	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD3817	Phase 2
0.7353	Intermediate Similarity	NPD2800	Approved
0.7345	Intermediate Similarity	NPD37	Approved
0.7337	Intermediate Similarity	NPD7228	Approved
0.7326	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD5710	Approved
0.7308	Intermediate Similarity	NPD5711	Approved
0.7302	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6799	Approved
0.7278	Intermediate Similarity	NPD6100	Approved
0.7278	Intermediate Similarity	NPD6099	Approved
0.7257	Intermediate Similarity	NPD5403	Approved
0.7254	Intermediate Similarity	NPD6213	Phase 3
0.7254	Intermediate Similarity	NPD6212	Phase 3
0.7254	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6234	Discontinued
0.7235	Intermediate Similarity	NPD2346	Discontinued
0.7231	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4966	Approved
0.7222	Intermediate Similarity	NPD4965	Approved
0.7222	Intermediate Similarity	NPD4967	Phase 2
0.7209	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4628	Phase 3
0.7209	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD943	Approved
0.7178	Intermediate Similarity	NPD1470	Approved
0.7174	Intermediate Similarity	NPD3926	Phase 2
0.7151	Intermediate Similarity	NPD7177	Discontinued
0.7143	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5401	Approved
0.7135	Intermediate Similarity	NPD2344	Approved
0.7128	Intermediate Similarity	NPD5953	Discontinued
0.7123	Intermediate Similarity	NPD8059	Phase 3
0.7123	Intermediate Similarity	NPD8058	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD7229	Phase 3
0.7118	Intermediate Similarity	NPD3748	Approved
0.709	Intermediate Similarity	NPD7240	Approved
0.7089	Intermediate Similarity	NPD7654	Discontinued
0.7076	Intermediate Similarity	NPD1551	Phase 2
0.7071	Intermediate Similarity	NPD8285	Discontinued
0.7062	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD920	Approved
0.7035	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD7286	Phase 2
0.7018	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD8166	Discontinued
0.7006	Intermediate Similarity	NPD4625	Phase 3
0.6973	Remote Similarity	NPD1247	Approved
0.6973	Remote Similarity	NPD7199	Phase 2
0.6971	Remote Similarity	NPD2309	Approved
0.6968	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1243	Approved
0.6949	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD230	Phase 1
0.6933	Remote Similarity	NPD1201	Approved
0.6923	Remote Similarity	NPD4287	Approved
0.6923	Remote Similarity	NPD5761	Phase 2
0.6923	Remote Similarity	NPD5760	Phase 2
0.6919	Remote Similarity	NPD2799	Discontinued
0.6912	Remote Similarity	NPD7584	Approved
0.6911	Remote Similarity	NPD7685	Pre-registration
0.691	Remote Similarity	NPD6273	Approved
0.6875	Remote Similarity	NPD6190	Approved
0.6869	Remote Similarity	NPD4360	Phase 2
0.6869	Remote Similarity	NPD4363	Phase 3
0.6865	Remote Similarity	NPD919	Approved
0.6864	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3764	Approved
0.6845	Remote Similarity	NPD4908	Phase 1
0.6836	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD3300	Phase 2
0.6826	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD3027	Phase 3
0.6791	Remote Similarity	NPD8127	Discontinued
0.6765	Remote Similarity	NPD2313	Discontinued
0.6762	Remote Similarity	NPD7930	Approved
0.6761	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1651	Approved
0.6729	Remote Similarity	NPD7907	Approved
0.6726	Remote Similarity	NPD2798	Approved
0.6707	Remote Similarity	NPD1283	Approved
0.6701	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3972	Approved
0.6686	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD1613	Approved
0.6686	Remote Similarity	NPD2438	Suspended
0.6685	Remote Similarity	NPD6844	Discontinued
0.6683	Remote Similarity	NPD7680	Approved
0.6667	Remote Similarity	NPD6973	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD8366	Approved
0.665	Remote Similarity	NPD7237	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