NPASS Compound

Structure

NPC469670 OpenBabel07101719242D 27 29 0 0 1 0 0 0 0 0999 V2000 0.9749 1.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8138 -4.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7317 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9499 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1656 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0817 -3.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9478 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 -4.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9749 0.2225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9478 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2157 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1656 -2.5245 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0817 -1.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9499 -4.0489 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -4.0489 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2157 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7317 -3.4254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7818 -3.4254 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1405 -2.7470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0817 -0.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3837 -4.9499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5135 -4.0489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5637 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8138 -3.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9309 -4.4143 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 4 1 0 0 0 0 3 5 2 0 0 0 0 4 9 1 0 0 0 0 5 12 1 0 0 0 0 6 10 2 0 0 0 0 6 11 1 0 0 0 0 7 10 1 0 0 0 0 7 13 2 0 0 0 0 8 14 1 0 0 0 0 9 1 1 1 0 0 0 9 26 1 0 0 0 0 10 25 1 0 0 0 0 11 16 2 0 0 0 0 12 17 1 0 0 0 0 12 20 1 6 0 0 0 13 16 1 0 0 0 0 13 21 1 0 0 0 0 14 17 1 0 0 0 0 14 22 1 1 0 0 0 15 8 1 1 0 0 0 15 18 1 0 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 17 23 1 1 0 0 0 18 11 1 1 0 0 0 18 27 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.15
Volume:	368.65
LogP:	1.385
LogD:	1.682
LogS:	-3.265
# Rotatable Bonds:	1
TPSA:	128.98
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	4.823
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.603
MDCK Permeability:	4.472996079130098e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.04
Human Intestinal Absorption (HIA):	0.409
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.173
Plasma Protein Binding (PPB):	93.39360809326172%
Volume Distribution (VD):	0.729
Pgp-substrate:	6.00845193862915%

ADMET: Metabolism

CYP1A2-inhibitor:	0.076
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.414
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.15
CYP2D6-substrate:	0.409
CYP3A4-inhibitor:	0.168
CYP3A4-substrate:	0.149

ADMET: Excretion

Clearance (CL):	6.261
Half-life (T1/2):	0.677

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.673
Drug-inuced Liver Injury (DILI):	0.287
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.04
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.236
Carcinogencity:	0.822
Eye Corrosion:	0.003
Eye Irritation:	0.042
Respiratory Toxicity:	0.575

Download Data

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

Natural Product: NPC469670

Natural Product ID:	NPC469670
*Common Name:**	Aigialomycin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NWBBODCXRAHUEM-OSMRJIJKSA-N
Standard InCHI:	InChI=1S/C19H24O8/c1-9-4-3-5-12(20)17(23)14(22)8-15-18(27-15)11-6-10(25-2)7-13(21)16(11)19(24)26-9/h3,5-7,9,12,14-15,17-18,20-23H,4,8H2,1-2H3/b5-3+/t9-,12-,14-,15+,17+,18-/m0/s1
SMILES:	COc1cc2[C@@H]3O[C@@H]3C[C@H](O)[C@H](O)[C@@H](O)/C=C/C[C@@H](OC(=O)c2c(c1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1097787
PubChem CID:	44229571
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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
NPO33425	paecilomyces fungus	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[20429578]

☑ 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	2
Others	4

Activity Type	# Activity
Cell Line	4
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	Inhibition	=	0.0	%	PMID[521226]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Inhibition	=	2.3	%	PMID[521226]
NPT189	Cell Line	Vero	Chlorocebus aethiops	Inhibition	=	30.2	%	PMID[521226]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	650.0	nM	PMID[521226]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	13500.0	nM	PMID[521226]

☑ 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 NPC469670 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	353
0.1-0.2	1417
0.2-0.3	3679
0.3-0.4	7882
0.4-0.5	10175
0.5-0.6	4197
0.6-0.7	5768
0.7-0.8	7277
0.8-0.85	1683
0.85-0.9	225
0.9-0.95	33
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC469619
0.9728	High Similarity	NPC99381
0.9658	High Similarity	NPC240768
0.9658	High Similarity	NPC200773
0.9658	High Similarity	NPC215921
0.9658	High Similarity	NPC70016
0.965	High Similarity	NPC83272
0.9583	High Similarity	NPC107625
0.958	High Similarity	NPC277426
0.958	High Similarity	NPC280404
0.958	High Similarity	NPC86373
0.958	High Similarity	NPC210425
0.951	High Similarity	NPC51106
0.9456	High Similarity	NPC56204
0.9441	High Similarity	NPC474385
0.9384	High Similarity	NPC210320
0.9375	High Similarity	NPC472006
0.9371	High Similarity	NPC1704
0.9371	High Similarity	NPC67650
0.932	High Similarity	NPC215711
0.932	High Similarity	NPC73411
0.9301	High Similarity	NPC158472
0.9257	High Similarity	NPC270160
0.9257	High Similarity	NPC237440
0.9252	High Similarity	NPC472036
0.9241	High Similarity	NPC469542
0.9236	High Similarity	NPC475730
0.9205	High Similarity	NPC82592
0.9205	High Similarity	NPC16082
0.9195	High Similarity	NPC179178
0.9184	High Similarity	NPC472033
0.9172	High Similarity	NPC469579
0.9161	High Similarity	NPC212693
0.9161	High Similarity	NPC94248
0.9139	High Similarity	NPC281477
0.9128	High Similarity	NPC476684
0.9116	High Similarity	NPC472034
0.9116	High Similarity	NPC257558
0.9103	High Similarity	NPC90411
0.9103	High Similarity	NPC158634
0.9091	High Similarity	NPC135837
0.9091	High Similarity	NPC70380
0.9091	High Similarity	NPC472055
0.9085	High Similarity	NPC77679
0.9085	High Similarity	NPC190020
0.9085	High Similarity	NPC84935
0.9079	High Similarity	NPC79998
0.9073	High Similarity	NPC167903
0.9048	High Similarity	NPC478203
0.9048	High Similarity	NPC126882
0.9048	High Similarity	NPC210966
0.9041	High Similarity	NPC250755
0.9028	High Similarity	NPC478200
0.9028	High Similarity	NPC33144
0.9028	High Similarity	NPC191835
0.9026	High Similarity	NPC470339
0.902	High Similarity	NPC150227
0.8993	High Similarity	NPC8817
0.8973	High Similarity	NPC313123
0.8973	High Similarity	NPC478217
0.8966	High Similarity	NPC105456
0.8966	High Similarity	NPC32360
0.8966	High Similarity	NPC139634
0.8958	High Similarity	NPC71256
0.8954	High Similarity	NPC199926
0.8951	High Similarity	NPC182496
0.8951	High Similarity	NPC180905
0.894	High Similarity	NPC96501
0.8933	High Similarity	NPC470359
0.8933	High Similarity	NPC240622
0.8933	High Similarity	NPC471641
0.8933	High Similarity	NPC471642
0.8933	High Similarity	NPC153417
0.8933	High Similarity	NPC240253
0.8926	High Similarity	NPC260946
0.8926	High Similarity	NPC470357
0.8926	High Similarity	NPC473023
0.8919	High Similarity	NPC470932
0.8897	High Similarity	NPC472602
0.8896	High Similarity	NPC472050
0.8896	High Similarity	NPC227062
0.8889	High Similarity	NPC155686
0.8874	High Similarity	NPC77325
0.8874	High Similarity	NPC4423
0.8867	High Similarity	NPC53362
0.8867	High Similarity	NPC137296
0.8867	High Similarity	NPC166583
0.8859	High Similarity	NPC75694
0.8859	High Similarity	NPC134621
0.8851	High Similarity	NPC478202
0.8844	High Similarity	NPC472604
0.8844	High Similarity	NPC53649
0.8844	High Similarity	NPC472035
0.8844	High Similarity	NPC244923
0.8844	High Similarity	NPC478201
0.8844	High Similarity	NPC472605
0.8839	High Similarity	NPC246466
0.8839	High Similarity	NPC473395
0.8836	High Similarity	NPC247409
0.8836	High Similarity	NPC268052
0.8831	High Similarity	NPC69043
0.8831	High Similarity	NPC68727
0.8831	High Similarity	NPC478230
0.8824	High Similarity	NPC470340
0.8824	High Similarity	NPC474843
0.8824	High Similarity	NPC470338
0.8824	High Similarity	NPC470337
0.8824	High Similarity	NPC268992
0.8824	High Similarity	NPC51824
0.8824	High Similarity	NPC273483
0.8824	High Similarity	NPC478224
0.8824	High Similarity	NPC113608
0.8816	High Similarity	NPC475460
0.8811	High Similarity	NPC153783
0.8808	High Similarity	NPC2569
0.8808	High Similarity	NPC172329
0.88	High Similarity	NPC163846
0.88	High Similarity	NPC237208
0.88	High Similarity	NPC225173
0.8792	High Similarity	NPC66404
0.8792	High Similarity	NPC95123
0.8792	High Similarity	NPC184702
0.8792	High Similarity	NPC151607
0.8792	High Similarity	NPC42540
0.879	High Similarity	NPC117985
0.8784	High Similarity	NPC49108
0.8784	High Similarity	NPC82913
0.8784	High Similarity	NPC96692
0.8782	High Similarity	NPC279732
0.8776	High Similarity	NPC165172
0.8776	High Similarity	NPC472601
0.8776	High Similarity	NPC472600
0.8774	High Similarity	NPC54928
0.8767	High Similarity	NPC475974
0.8767	High Similarity	NPC197666
0.8767	High Similarity	NPC126739
0.8766	High Similarity	NPC197188
0.8766	High Similarity	NPC478231
0.8766	High Similarity	NPC238672
0.8766	High Similarity	NPC43872
0.8766	High Similarity	NPC291510
0.8766	High Similarity	NPC137301
0.8766	High Similarity	NPC116850
0.8766	High Similarity	NPC144801
0.8759	High Similarity	NPC235115
0.8758	High Similarity	NPC204350
0.8758	High Similarity	NPC228662
0.8758	High Similarity	NPC46882
0.8758	High Similarity	NPC132990
0.875	High Similarity	NPC283041
0.8742	High Similarity	NPC81835
0.8742	High Similarity	NPC125801
0.8742	High Similarity	NPC14098
0.8742	High Similarity	NPC7752
0.8742	High Similarity	NPC191930
0.8742	High Similarity	NPC472049
0.8734	High Similarity	NPC48860
0.8733	High Similarity	NPC29577
0.8733	High Similarity	NPC312789
0.8726	High Similarity	NPC24627
0.8726	High Similarity	NPC470358
0.8725	High Similarity	NPC159721
0.8725	High Similarity	NPC471731
0.8725	High Similarity	NPC354984
0.8718	High Similarity	NPC472889
0.8716	High Similarity	NPC472603
0.871	High Similarity	NPC16286
0.871	High Similarity	NPC208173
0.871	High Similarity	NPC472890
0.871	High Similarity	NPC170189
0.871	High Similarity	NPC67396
0.871	High Similarity	NPC317585
0.8707	High Similarity	NPC275356
0.8707	High Similarity	NPC471819
0.8701	High Similarity	NPC115249
0.8701	High Similarity	NPC184284
0.8701	High Similarity	NPC76041
0.8701	High Similarity	NPC180944
0.8701	High Similarity	NPC271681
0.8701	High Similarity	NPC295646
0.8699	High Similarity	NPC474849
0.8699	High Similarity	NPC474771
0.8699	High Similarity	NPC178467
0.8699	High Similarity	NPC149372
0.8699	High Similarity	NPC194579
0.8699	High Similarity	NPC65837
0.8693	High Similarity	NPC470107
0.8693	High Similarity	NPC60413
0.8693	High Similarity	NPC119929
0.8693	High Similarity	NPC472891
0.8693	High Similarity	NPC295036
0.869	High Similarity	NPC142027
0.8688	High Similarity	NPC20237
0.8684	High Similarity	NPC221352
0.8684	High Similarity	NPC37139
0.8679	High Similarity	NPC249181
0.8675	High Similarity	NPC32058
0.8675	High Similarity	NPC85734
0.8675	High Similarity	NPC138978
0.8671	High Similarity	NPC96031

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 NPC469670 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	922
0.2-0.3	1908
0.3-0.4	2536
0.4-0.5	1825
0.5-0.6	1066
0.6-0.7	426
0.7-0.8	148
0.8-0.85	20
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8859	High Similarity	NPD2534	Approved
0.8859	High Similarity	NPD2533	Approved
0.8859	High Similarity	NPD2532	Approved
0.8836	High Similarity	NPD970	Clinical (unspecified phase)
0.8526	High Similarity	NPD7819	Suspended
0.85	High Similarity	NPD6232	Discontinued
0.8452	Intermediate Similarity	NPD4380	Phase 2
0.8408	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD7075	Discontinued
0.8344	Intermediate Similarity	NPD1934	Approved
0.8344	Intermediate Similarity	NPD7473	Discontinued
0.8302	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD3817	Phase 2
0.8228	Intermediate Similarity	NPD6801	Discontinued
0.8182	Intermediate Similarity	NPD6799	Approved
0.8182	Intermediate Similarity	NPD3818	Discontinued
0.8176	Intermediate Similarity	NPD2801	Approved
0.8176	Intermediate Similarity	NPD230	Phase 1
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD6166	Phase 2
0.8146	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD1510	Phase 2
0.8129	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD5402	Approved
0.8108	Intermediate Similarity	NPD1240	Approved
0.8105	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD6599	Discontinued
0.8098	Intermediate Similarity	NPD6959	Discontinued
0.8092	Intermediate Similarity	NPD1549	Phase 2
0.8084	Intermediate Similarity	NPD7074	Phase 3
0.8079	Intermediate Similarity	NPD2935	Discontinued
0.8075	Intermediate Similarity	NPD3882	Suspended
0.8065	Intermediate Similarity	NPD1511	Approved
0.805	Intermediate Similarity	NPD7411	Suspended
0.8049	Intermediate Similarity	NPD5711	Approved
0.8049	Intermediate Similarity	NPD5710	Approved
0.8047	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7054	Approved
0.8024	Intermediate Similarity	NPD5844	Phase 1
0.8012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1607	Approved
0.7987	Intermediate Similarity	NPD4628	Phase 3
0.7987	Intermediate Similarity	NPD3750	Approved
0.7976	Intermediate Similarity	NPD7472	Approved
0.7962	Intermediate Similarity	NPD1512	Approved
0.7961	Intermediate Similarity	NPD2796	Approved
0.795	Intermediate Similarity	NPD1465	Phase 2
0.7929	Intermediate Similarity	NPD6797	Phase 2
0.7917	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD3749	Approved
0.7911	Intermediate Similarity	NPD5403	Approved
0.7886	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6559	Discontinued
0.7882	Intermediate Similarity	NPD7251	Discontinued
0.7853	Intermediate Similarity	NPD7768	Phase 2
0.7852	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1551	Phase 2
0.7836	Intermediate Similarity	NPD7808	Phase 3
0.7824	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD3226	Approved
0.7806	Intermediate Similarity	NPD2800	Approved
0.7785	Intermediate Similarity	NPD5401	Approved
0.7785	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD37	Approved
0.7758	Intermediate Similarity	NPD6234	Discontinued
0.7744	Intermediate Similarity	NPD4966	Approved
0.7744	Intermediate Similarity	NPD4967	Phase 2
0.7744	Intermediate Similarity	NPD4965	Approved
0.7711	Intermediate Similarity	NPD5494	Approved
0.7697	Intermediate Similarity	NPD447	Suspended
0.7688	Intermediate Similarity	NPD920	Approved
0.7665	Intermediate Similarity	NPD7199	Phase 2
0.7662	Intermediate Similarity	NPD3748	Approved
0.7647	Intermediate Similarity	NPD6651	Approved
0.7647	Intermediate Similarity	NPD3751	Discontinued
0.7632	Intermediate Similarity	NPD943	Approved
0.7619	Intermediate Similarity	NPD3787	Discontinued
0.7616	Intermediate Similarity	NPD5953	Discontinued
0.7586	Intermediate Similarity	NPD8312	Approved
0.7586	Intermediate Similarity	NPD8313	Approved
0.758	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD9545	Approved
0.7564	Intermediate Similarity	NPD2346	Discontinued
0.7562	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD9717	Approved
0.7548	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2799	Discontinued
0.7544	Intermediate Similarity	NPD7228	Approved
0.7532	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD7286	Phase 2
0.7484	Intermediate Similarity	NPD6190	Approved
0.7483	Intermediate Similarity	NPD6832	Phase 2
0.7471	Intermediate Similarity	NPD7685	Pre-registration
0.7471	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1243	Approved
0.7459	Intermediate Similarity	NPD7435	Discontinued
0.7458	Intermediate Similarity	NPD8150	Discontinued
0.7453	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD8151	Discontinued
0.744	Intermediate Similarity	NPD919	Approved
0.7438	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7033	Discontinued
0.7434	Intermediate Similarity	NPD3027	Phase 3
0.7432	Intermediate Similarity	NPD9269	Phase 2
0.7431	Intermediate Similarity	NPD9493	Approved
0.7412	Intermediate Similarity	NPD7229	Phase 3
0.74	Intermediate Similarity	NPD1203	Approved
0.7391	Intermediate Similarity	NPD6776	Approved
0.7391	Intermediate Similarity	NPD6779	Approved
0.7391	Intermediate Similarity	NPD6780	Approved
0.7391	Intermediate Similarity	NPD6777	Approved
0.7391	Intermediate Similarity	NPD6781	Approved
0.7391	Intermediate Similarity	NPD6778	Approved
0.7391	Intermediate Similarity	NPD6782	Approved
0.7389	Intermediate Similarity	NPD6099	Approved
0.7389	Intermediate Similarity	NPD6100	Approved
0.7386	Intermediate Similarity	NPD3764	Approved
0.7386	Intermediate Similarity	NPD411	Approved
0.7378	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3926	Phase 2
0.7365	Intermediate Similarity	NPD422	Phase 1
0.736	Intermediate Similarity	NPD8434	Phase 2
0.7355	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4626	Approved
0.7342	Intermediate Similarity	NPD2344	Approved
0.7317	Intermediate Similarity	NPD1653	Approved
0.7315	Intermediate Similarity	NPD1608	Approved
0.7303	Intermediate Similarity	NPD9494	Approved
0.7303	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1613	Approved
0.729	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4060	Phase 1
0.7289	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD9268	Approved
0.7279	Intermediate Similarity	NPD5691	Approved
0.7278	Intermediate Similarity	NPD5406	Approved
0.7278	Intermediate Similarity	NPD5404	Approved
0.7278	Intermediate Similarity	NPD5405	Approved
0.7278	Intermediate Similarity	NPD5408	Approved
0.7277	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7783	Phase 2
0.7273	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2313	Discontinued
0.7267	Intermediate Similarity	NPD5242	Approved
0.7262	Intermediate Similarity	NPD5353	Approved
0.7251	Intermediate Similarity	NPD1247	Approved
0.725	Intermediate Similarity	NPD2654	Approved
0.725	Intermediate Similarity	NPD1652	Phase 2
0.7244	Intermediate Similarity	NPD6355	Discontinued
0.7244	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5124	Phase 1
0.7237	Intermediate Similarity	NPD1019	Discontinued
0.7233	Intermediate Similarity	NPD6002	Phase 3
0.7233	Intermediate Similarity	NPD6005	Phase 3
0.7233	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD6004	Phase 3
0.7232	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7874	Approved
0.7195	Intermediate Similarity	NPD6273	Approved
0.7181	Intermediate Similarity	NPD7697	Approved
0.7181	Intermediate Similarity	NPD7696	Phase 3
0.7181	Intermediate Similarity	NPD7698	Approved
0.7175	Intermediate Similarity	NPD7240	Approved
0.7171	Intermediate Similarity	NPD2797	Approved
0.717	Intermediate Similarity	NPD2438	Suspended
0.7165	Intermediate Similarity	NPD7930	Approved
0.7161	Intermediate Similarity	NPD3268	Approved
0.7161	Intermediate Similarity	NPD6798	Discontinued
0.716	Intermediate Similarity	NPD4288	Approved
0.716	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7134	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6823	Phase 2
0.7124	Intermediate Similarity	NPD5647	Approved
0.7124	Intermediate Similarity	NPD2798	Approved
0.712	Intermediate Similarity	NPD7701	Phase 2
0.712	Intermediate Similarity	NPD6535	Approved
0.712	Intermediate Similarity	NPD6534	Approved
0.7114	Intermediate Similarity	NPD1778	Approved
0.7114	Intermediate Similarity	NPD17	Approved
0.7112	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1283	Approved
0.7101	Intermediate Similarity	NPD8455	Phase 2
0.7099	Intermediate Similarity	NPD7003	Approved
0.7089	Intermediate Similarity	NPD6653	Approved

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