NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	615.21
Volume:	609.906
LogP:	4.23
LogD:	2.822
LogS:	-6.356
# Rotatable Bonds:	10
TPSA:	112.91
# H-Bond Aceptor:	11
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.177
Synthetic Accessibility Score:	3.217
Fsp3:	0.294
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.5
MDCK Permeability:	4.112349051865749e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.503
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.091

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	74.2171401977539%
Volume Distribution (VD):	0.838
Pgp-substrate:	8.841778755187988%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.681
CYP2C19-substrate:	0.6
CYP2C9-inhibitor:	0.782
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.932
CYP3A4-inhibitor:	0.332
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	5.326
Half-life (T1/2):	0.345

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.02
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.313
Rat Oral Acute Toxicity:	0.436
Maximum Recommended Daily Dose:	0.374
Skin Sensitization:	0.026
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.556

Download Data

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

Natural Product: NPC476999

Natural Product ID:	NPC476999
*Common Name:**	Lamellarin C-diacetate
IUPAC Name:	[4-(7-acetyloxy-8,16,17,18-tetramethoxy-4-oxa-1-azapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-2(11),5,7,9,12,14,16,18-octaen-12-yl)-2-methoxyphenyl] acetate
Synonyms:	Lamellarin C-Diacetate
Standard InCHIKey:	MQCSKLLUQRBKBR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C34H33NO10/c1-17(36)44-24-9-8-19(12-26(24)38-3)30-31-22-14-27(39-4)28(45-18(2)37)15-25(22)43-16-23(31)35-11-10-20-21(32(30)35)13-29(40-5)34(42-7)33(20)41-6/h8-9,12-15H,10-11,16H2,1-7H3
SMILES:	CC(=O)OC1=C(C=C(C=C1)C2=C3C4=CC(=C(C(=C4CCN3C5=C2C6=CC(=C(C=C6OC5)OC(=O)C)OC)OC)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44559517
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000090] Pyrroles [CHEMONTID:0002257] Substituted pyrroles [CHEMONTID:0002334] Phenylpyrroles

*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
NPO16570	Didemnum obscurum	Species	Didemnidae	Eukaryota	n.a.	Tiruchandur coast in the Gulf of Mannar, Tamilnadu, India	2002-FEB	PMID[15270574]
NPO16570	Didemnum obscurum	Species	Didemnidae	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
Others	6

Activity Type	# Activity
Others	7

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity	Activity	=	0	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	30.95	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	61.9	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	Activity	=	92.84	%	PMID[15270574]
NPT1	Others	Radical scavenging activity	IC50	=	5870000	nM	PMID[15270574]
NPT2	Others	Unspecified	Ratio IC50	=	0.01	n.a.	PMID[15270574]

☑ 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 NPC476999 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	446
0.1-0.2	2253
0.2-0.3	10834
0.3-0.4	6724
0.4-0.5	9356
0.5-0.6	10837
0.6-0.7	2012
0.7-0.8	220
0.8-0.85	9
0.85-0.9	0
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9573	High Similarity	NPC476995
0.9289	High Similarity	NPC476996
0.9289	High Similarity	NPC476998
0.9242	High Similarity	NPC476994
0.9242	High Similarity	NPC476997
0.8609	High Similarity	NPC318068
0.8534	High Similarity	NPC129897
0.8142	Intermediate Similarity	NPC255800
0.8142	Intermediate Similarity	NPC96584
0.8133	Intermediate Similarity	NPC201508
0.8056	Intermediate Similarity	NPC290689
0.7934	Intermediate Similarity	NPC31930
0.7917	Intermediate Similarity	NPC284685
0.7907	Intermediate Similarity	NPC476581
0.7907	Intermediate Similarity	NPC16452
0.7907	Intermediate Similarity	NPC36229
0.79	Intermediate Similarity	NPC296482
0.79	Intermediate Similarity	NPC53069
0.79	Intermediate Similarity	NPC202768
0.7884	Intermediate Similarity	NPC191489
0.784	Intermediate Similarity	NPC476582
0.784	Intermediate Similarity	NPC4071
0.784	Intermediate Similarity	NPC476578
0.7834	Intermediate Similarity	NPC313189
0.7812	Intermediate Similarity	NPC174049
0.7803	Intermediate Similarity	NPC473822
0.7755	Intermediate Similarity	NPC88923
0.7755	Intermediate Similarity	NPC315634
0.7755	Intermediate Similarity	NPC100734
0.7738	Intermediate Similarity	NPC171409
0.7738	Intermediate Similarity	NPC96405
0.7723	Intermediate Similarity	NPC23614
0.7723	Intermediate Similarity	NPC100079
0.7703	Intermediate Similarity	NPC149471
0.7703	Intermediate Similarity	NPC271215
0.7689	Intermediate Similarity	NPC148409
0.7671	Intermediate Similarity	NPC135549
0.7665	Intermediate Similarity	NPC122463
0.7661	Intermediate Similarity	NPC164374
0.7661	Intermediate Similarity	NPC137929
0.7658	Intermediate Similarity	NPC202605
0.7658	Intermediate Similarity	NPC112206
0.7647	Intermediate Similarity	NPC219664
0.7642	Intermediate Similarity	NPC133140
0.7642	Intermediate Similarity	NPC195268
0.7639	Intermediate Similarity	NPC477019
0.7619	Intermediate Similarity	NPC249996
0.7611	Intermediate Similarity	NPC46451
0.7608	Intermediate Similarity	NPC476202
0.7589	Intermediate Similarity	NPC235076
0.7578	Intermediate Similarity	NPC203168
0.7568	Intermediate Similarity	NPC188420
0.7565	Intermediate Similarity	NPC200888
0.756	Intermediate Similarity	NPC195538
0.7553	Intermediate Similarity	NPC119134
0.7545	Intermediate Similarity	NPC474594
0.7534	Intermediate Similarity	NPC469440
0.7531	Intermediate Similarity	NPC284141
0.75	Intermediate Similarity	NPC251160
0.7479	Intermediate Similarity	NPC217554
0.7479	Intermediate Similarity	NPC49672
0.7477	Intermediate Similarity	NPC234197
0.7468	Intermediate Similarity	NPC469792
0.7458	Intermediate Similarity	NPC124313
0.7432	Intermediate Similarity	NPC474595
0.743	Intermediate Similarity	NPC469390
0.7424	Intermediate Similarity	NPC54066
0.7416	Intermediate Similarity	NPC293093
0.7415	Intermediate Similarity	NPC90875
0.7409	Intermediate Similarity	NPC66815
0.7404	Intermediate Similarity	NPC233334
0.7395	Intermediate Similarity	NPC11408
0.7375	Intermediate Similarity	NPC207283
0.7375	Intermediate Similarity	NPC84164
0.7373	Intermediate Similarity	NPC329631
0.7362	Intermediate Similarity	NPC475253
0.7359	Intermediate Similarity	NPC280272
0.7359	Intermediate Similarity	NPC118121
0.7336	Intermediate Similarity	NPC204446
0.7327	Intermediate Similarity	NPC85381
0.7318	Intermediate Similarity	NPC11017
0.7315	Intermediate Similarity	NPC41122
0.7315	Intermediate Similarity	NPC318805
0.7309	Intermediate Similarity	NPC472111
0.7308	Intermediate Similarity	NPC312872
0.7306	Intermediate Similarity	NPC183537
0.7277	Intermediate Similarity	NPC299990
0.7277	Intermediate Similarity	NPC73492
0.7273	Intermediate Similarity	NPC10908
0.7273	Intermediate Similarity	NPC227060
0.7273	Intermediate Similarity	NPC477533
0.7273	Intermediate Similarity	NPC276890
0.7273	Intermediate Similarity	NPC76682
0.7273	Intermediate Similarity	NPC317439
0.7273	Intermediate Similarity	NPC63646
0.7273	Intermediate Similarity	NPC198498
0.7273	Intermediate Similarity	NPC115284
0.7273	Intermediate Similarity	NPC317145
0.7269	Intermediate Similarity	NPC277351
0.7265	Intermediate Similarity	NPC203373
0.726	Intermediate Similarity	NPC234318
0.7256	Intermediate Similarity	NPC14507
0.7256	Intermediate Similarity	NPC47077
0.7246	Intermediate Similarity	NPC24019
0.7244	Intermediate Similarity	NPC470931
0.7243	Intermediate Similarity	NPC61350
0.7243	Intermediate Similarity	NPC204385
0.7238	Intermediate Similarity	NPC129518
0.7238	Intermediate Similarity	NPC108342
0.7238	Intermediate Similarity	NPC251580
0.7238	Intermediate Similarity	NPC41376
0.7238	Intermediate Similarity	NPC12424
0.7235	Intermediate Similarity	NPC114335
0.7235	Intermediate Similarity	NPC141915
0.7235	Intermediate Similarity	NPC475597
0.7235	Intermediate Similarity	NPC473716
0.7235	Intermediate Similarity	NPC280964
0.7233	Intermediate Similarity	NPC470042
0.7232	Intermediate Similarity	NPC304183
0.7217	Intermediate Similarity	NPC206201
0.7208	Intermediate Similarity	NPC473183
0.7208	Intermediate Similarity	NPC182907
0.7208	Intermediate Similarity	NPC189903
0.7202	Intermediate Similarity	NPC15406
0.7202	Intermediate Similarity	NPC475190
0.7202	Intermediate Similarity	NPC279401
0.7202	Intermediate Similarity	NPC79293
0.7193	Intermediate Similarity	NPC472098
0.7178	Intermediate Similarity	NPC166722
0.7176	Intermediate Similarity	NPC116465
0.7176	Intermediate Similarity	NPC212237
0.7167	Intermediate Similarity	NPC295228
0.7166	Intermediate Similarity	NPC302807
0.7166	Intermediate Similarity	NPC77878
0.7163	Intermediate Similarity	NPC302275
0.7162	Intermediate Similarity	NPC236668
0.7149	Intermediate Similarity	NPC127085
0.7143	Intermediate Similarity	NPC107123
0.7137	Intermediate Similarity	NPC469589
0.713	Intermediate Similarity	NPC95426
0.713	Intermediate Similarity	NPC146976
0.713	Intermediate Similarity	NPC16357
0.713	Intermediate Similarity	NPC302245
0.7125	Intermediate Similarity	NPC473184
0.7124	Intermediate Similarity	NPC469439
0.712	Intermediate Similarity	NPC472589
0.7118	Intermediate Similarity	NPC94157
0.7116	Intermediate Similarity	NPC30779
0.711	Intermediate Similarity	NPC281581
0.7104	Intermediate Similarity	NPC224928
0.7103	Intermediate Similarity	NPC243454
0.7103	Intermediate Similarity	NPC475479
0.7098	Intermediate Similarity	NPC473660
0.7097	Intermediate Similarity	NPC139783
0.7097	Intermediate Similarity	NPC65312
0.7083	Intermediate Similarity	NPC22481
0.707	Intermediate Similarity	NPC286119
0.707	Intermediate Similarity	NPC239584
0.7066	Intermediate Similarity	NPC471303
0.7064	Intermediate Similarity	NPC275680
0.7064	Intermediate Similarity	NPC22115
0.7064	Intermediate Similarity	NPC210434
0.7056	Intermediate Similarity	NPC134637
0.7054	Intermediate Similarity	NPC34770
0.7052	Intermediate Similarity	NPC120513
0.7051	Intermediate Similarity	NPC132642
0.7051	Intermediate Similarity	NPC472099
0.7049	Intermediate Similarity	NPC99891
0.7049	Intermediate Similarity	NPC210296
0.7045	Intermediate Similarity	NPC24260
0.7045	Intermediate Similarity	NPC302001
0.704	Intermediate Similarity	NPC472588
0.7037	Intermediate Similarity	NPC90998
0.7037	Intermediate Similarity	NPC8836
0.7037	Intermediate Similarity	NPC217748
0.7037	Intermediate Similarity	NPC7715
0.7037	Intermediate Similarity	NPC182052
0.7037	Intermediate Similarity	NPC285931
0.7037	Intermediate Similarity	NPC222661
0.7037	Intermediate Similarity	NPC290005
0.7037	Intermediate Similarity	NPC54654
0.7037	Intermediate Similarity	NPC15414
0.7037	Intermediate Similarity	NPC328155
0.7037	Intermediate Similarity	NPC229373
0.7037	Intermediate Similarity	NPC311973
0.7037	Intermediate Similarity	NPC42663
0.7037	Intermediate Similarity	NPC185639
0.7037	Intermediate Similarity	NPC290582
0.7037	Intermediate Similarity	NPC49075
0.7037	Intermediate Similarity	NPC279228
0.7037	Intermediate Similarity	NPC181796
0.7037	Intermediate Similarity	NPC223690
0.7037	Intermediate Similarity	NPC239824
0.7037	Intermediate Similarity	NPC258657
0.7037	Intermediate Similarity	NPC271013
0.7037	Intermediate Similarity	NPC251735
0.7037	Intermediate Similarity	NPC104196
0.7035	Intermediate Similarity	NPC470930
0.7029	Intermediate Similarity	NPC278525
0.7028	Intermediate Similarity	NPC67401

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 NPC476999 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	246
0.1-0.2	669
0.2-0.3	956
0.3-0.4	1584
0.4-0.5	2808
0.5-0.6	2157
0.6-0.7	672
0.7-0.8	58
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7917	Intermediate Similarity	NPD7222	Phase 2
0.7917	Intermediate Similarity	NPD7956	Approved
0.7917	Intermediate Similarity	NPD7955	Approved
0.7905	Intermediate Similarity	NPD4418	Discontinued
0.79	Intermediate Similarity	NPD3816	Phase 1
0.79	Intermediate Similarity	NPD3815	Phase 1
0.7884	Intermediate Similarity	NPD7708	Approved
0.7755	Intermediate Similarity	NPD7803	Approved
0.7702	Intermediate Similarity	NPD7417	Discontinued
0.7671	Intermediate Similarity	NPD7452	Approved
0.7671	Intermediate Similarity	NPD7453	Approved
0.7667	Intermediate Similarity	NPD6503	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD3924	Approved
0.7642	Intermediate Similarity	NPD3921	Approved
0.7642	Intermediate Similarity	NPD3923	Approved
0.7642	Intermediate Similarity	NPD3922	Approved
0.7621	Intermediate Similarity	NPD3920	Phase 2
0.7617	Intermediate Similarity	NPD6550	Discontinued
0.7611	Intermediate Similarity	NPD3763	Approved
0.7597	Intermediate Similarity	NPD6494	Phase 2
0.749	Intermediate Similarity	NPD7862	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7169	Suspended
0.7434	Intermediate Similarity	NPD5902	Approved
0.7434	Intermediate Similarity	NPD5903	Approved
0.7432	Intermediate Similarity	NPD5429	Discontinued
0.7422	Intermediate Similarity	NPD7069	Discontinued
0.7419	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD7859	Phase 2
0.7407	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD6741	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7719	Discontinued
0.7336	Intermediate Similarity	NPD6525	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD7395	Discontinued
0.7321	Intermediate Similarity	NPD5658	Approved
0.7321	Intermediate Similarity	NPD8156	Discontinued
0.7319	Intermediate Similarity	NPD8052	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6773	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7886	Phase 2
0.7292	Intermediate Similarity	NPD7885	Phase 2
0.7284	Intermediate Similarity	NPD8100	Phase 3
0.7277	Intermediate Similarity	NPD4889	Approved
0.7277	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD8251	Approved
0.7273	Intermediate Similarity	NPD8252	Approved
0.7273	Intermediate Similarity	NPD8099	Discontinued
0.7265	Intermediate Similarity	NPD3946	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD6988	Phase 1
0.7243	Intermediate Similarity	NPD5256	Discontinued
0.7237	Intermediate Similarity	NPD7571	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6553	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD6716	Phase 1
0.7227	Intermediate Similarity	NPD7558	Phase 2
0.7215	Intermediate Similarity	NPD5512	Phase 3
0.7209	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6964	Approved
0.7197	Intermediate Similarity	NPD6963	Approved
0.7195	Intermediate Similarity	NPD8101	Phase 3
0.7175	Intermediate Similarity	NPD6477	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6569	Phase 2
0.715	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.7149	Intermediate Similarity	NPD7025	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7678	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD7180	Phase 3
0.7124	Intermediate Similarity	NPD5930	Phase 3
0.7114	Intermediate Similarity	NPD7868	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD4885	Approved
0.7089	Intermediate Similarity	NPD7994	Phase 2
0.7056	Intermediate Similarity	NPD5482	Discontinued
0.7046	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7046	Intermediate Similarity	NPD7675	Phase 3
0.7046	Intermediate Similarity	NPD7674	Phase 3
0.7043	Intermediate Similarity	NPD5866	Approved
0.7039	Intermediate Similarity	NPD6568	Discontinued
0.7037	Intermediate Similarity	NPD8054	Approved
0.7037	Intermediate Similarity	NPD8053	Approved
0.7037	Intermediate Similarity	NPD7729	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1483	Discontinued
0.7018	Intermediate Similarity	NPD5863	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD7194	Discontinued
0.7004	Intermediate Similarity	NPD3003	Approved
0.7004	Intermediate Similarity	NPD5530	Phase 1
0.7004	Intermediate Similarity	NPD8359	Phase 2
0.7	Intermediate Similarity	NPD4502	Phase 2
0.6992	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5677	Discontinued
0.6983	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD3477	Phase 2
0.6982	Remote Similarity	NPD3478	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3386	Phase 2
0.6975	Remote Similarity	NPD7426	Phase 1
0.6966	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6985	Discontinued
0.6966	Remote Similarity	NPD5632	Approved
0.6964	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6958	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD5612	Discontinued
0.6937	Remote Similarity	NPD6590	Discontinued
0.6936	Remote Similarity	NPD6974	Phase 3
0.6933	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD8049	Phase 2
0.6905	Remote Similarity	NPD8463	Approved
0.6901	Remote Similarity	NPD7796	Approved
0.6901	Remote Similarity	NPD7797	Approved
0.6898	Remote Similarity	NPD4204	Approved
0.6898	Remote Similarity	NPD4203	Approved
0.6897	Remote Similarity	NPD4927	Discontinued
0.6897	Remote Similarity	NPD7684	Approved
0.6897	Remote Similarity	NPD7682	Approved
0.6892	Remote Similarity	NPD6361	Phase 2
0.6888	Remote Similarity	NPD4952	Phase 3
0.6886	Remote Similarity	NPD4033	Approved
0.6886	Remote Similarity	NPD4036	Approved
0.6886	Remote Similarity	NPD4037	Approved
0.6886	Remote Similarity	NPD4038	Approved
0.6886	Remote Similarity	NPD4035	Approved
0.6886	Remote Similarity	NPD31	Approved
0.6886	Remote Similarity	NPD4122	Approved
0.6886	Remote Similarity	NPD32	Approved
0.6886	Remote Similarity	NPD4039	Approved
0.6886	Remote Similarity	NPD4034	Approved
0.688	Remote Similarity	NPD8102	Discontinued
0.6877	Remote Similarity	NPD8442	Discontinued
0.687	Remote Similarity	NPD8016	Phase 3
0.687	Remote Similarity	NPD8017	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD3514	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD6219	Discontinued
0.6856	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6243	Phase 3
0.6853	Remote Similarity	NPD6244	Phase 3
0.6846	Remote Similarity	NPD8364	Approved
0.6846	Remote Similarity	NPD8363	Approved
0.684	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD7673	Phase 3
0.6833	Remote Similarity	NPD3263	Phase 3
0.683	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6230	Discontinued
0.6824	Remote Similarity	NPD8091	Phase 3
0.682	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8467	Approved
0.6818	Remote Similarity	NPD8465	Approved
0.6818	Remote Similarity	NPD8466	Approved
0.6814	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD3397	Phase 2
0.6804	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4373	Phase 2
0.68	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5944	Phase 1
0.6795	Remote Similarity	NPD5945	Phase 1
0.6794	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD3875	Discontinued
0.679	Remote Similarity	NPD6962	Phase 2
0.6786	Remote Similarity	NPD3324	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8244	Phase 2
0.6783	Remote Similarity	NPD8403	Phase 1
0.6781	Remote Similarity	NPD6220	Phase 3
0.6781	Remote Similarity	NPD4131	Phase 3
0.678	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5559	Phase 2
0.6776	Remote Similarity	NPD7807	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD8358	Approved
0.6766	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD3590	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7224	Discontinued
0.6763	Remote Similarity	NPD7223	Discontinued
0.6763	Remote Similarity	NPD7051	Phase 3
0.6763	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD4876	Phase 3
0.6747	Remote Similarity	NPD4875	Phase 3
0.6747	Remote Similarity	NPD6517	Phase 3
0.6742	Remote Similarity	NPD1034	Phase 3
0.6742	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.674	Remote Similarity	NPD1768	Approved
0.6736	Remote Similarity	NPD5507	Approved
0.6736	Remote Similarity	NPD5506	Approved
0.6736	Remote Similarity	NPD5147	Discontinued
0.6734	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD5450	Discontinued
0.6725	Remote Similarity	NPD5005	Approved
0.6725	Remote Similarity	NPD5006	Approved
0.6724	Remote Similarity	NPD7671	Approved
0.6724	Remote Similarity	NPD7672	Approved
0.6721	Remote Similarity	NPD5805	Approved
0.672	Remote Similarity	NPD7592	Phase 2
0.6716	Remote Similarity	NPD8459	Approved
0.6716	Remote Similarity	NPD8426	Approved
0.6716	Remote Similarity	NPD8425	Approved
0.6716	Remote Similarity	NPD8460	Approved
0.6712	Remote Similarity	NPD7549	Discontinued
0.6712	Remote Similarity	NPD7906	Approved
0.671	Remote Similarity	NPD5601	Phase 2
0.6709	Remote Similarity	NPD5416	Discontinued
0.6709	Remote Similarity	NPD7468	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