NPASS Compound

Structure

CID89625 OpenBabel06191715422D 27 28 0 0 0 0 0 0 0 0999 V2000 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 26 1 0 0 0 0 5 8 2 0 0 0 0 5 12 1 0 0 0 0 6 9 2 0 0 0 0 6 13 1 0 0 0 0 7 11 1 0 0 0 0 7 20 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 12 2 0 0 0 0 10 16 1 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 27 1 0 0 0 0 13 26 1 0 0 0 0 14 16 2 0 0 0 0 14 18 1 0 0 0 0 15 17 2 0 0 0 0 15 19 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 25 2 0 0 0 0 19 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.1
Volume:	366.661
LogP:	4.543
LogD:	2.45
LogS:	-3.588
# Rotatable Bonds:	6
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.414
Synthetic Accessibility Score:	2.779
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.546
MDCK Permeability:	6.0869401750096586e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.037
Human Intestinal Absorption (HIA):	0.161
20% Bioavailability (F20%):	0.028
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	97.39823150634766%
Volume Distribution (VD):	0.491
Pgp-substrate:	1.7714753150939941%

ADMET: Metabolism

CYP1A2-inhibitor:	0.09
CYP1A2-substrate:	0.423
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.355
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.079
CYP2D6-substrate:	0.128
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.08

ADMET: Excretion

Clearance (CL):	1.833
Half-life (T1/2):	0.876

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.04
Drug-inuced Liver Injury (DILI):	0.776
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.147
Maximum Recommended Daily Dose:	0.253
Skin Sensitization:	0.665
Carcinogencity:	0.03
Eye Corrosion:	0.004
Eye Irritation:	0.877
Respiratory Toxicity:	0.829

Download Data

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

Natural Product: NPC89625

Natural Product ID:	NPC89625
*Common Name:**	Baeomycesic Acid
IUPAC Name:	4-(3-formyl-2-hydroxy-4-methoxy-6-methylbenzoyl)oxy-2-hydroxy-3,6-dimethylbenzoic acid
Synonyms:
Standard InCHIKey:	DUIBXZLCROUOFD-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O8/c1-8-5-12(10(3)16(21)14(8)18(23)24)27-19(25)15-9(2)6-13(26-4)11(7-20)17(15)22/h5-7,21-22H,1-4H3,(H,23,24)
SMILES:	COc1cc(C)c(c(c1C=O)O)C(=O)Oc1cc(C)c(c(c1C)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2227773
PubChem CID:	5321461
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO12127	Parmelia saxatilis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14190	Streptopelia orientalis	Species	Columbidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2336.1	Thamnolia vermicularis var. subuliformis	Varieties	Icmadophilaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12127	Parmelia saxatilis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14190	Streptopelia orientalis	Species	Columbidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12127	Parmelia saxatilis	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2602	Usnea longissima	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14190	Streptopelia orientalis	Species	Columbidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12127	Parmelia saxatilis	Species	Parmeliaceae	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
ED50	6
Others	20

Activity Type	# Activity
Individual Protein	2
Organism	24

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2701	Organism	Pythium debaryanum	Pythium debaryanum	ED50	=	143.5	ug ml-1	PMID[458523]
NPT961	Organism	Pythium aphanidermatum	Pythium aphanidermatum	ED50	=	148.9	ug ml-1	PMID[458523]
NPT2702	Organism	Fusarium udum	Fusarium udum	ED50	=	109.85	ug ml-1	PMID[458523]
NPT2703	Organism	Rhizoctonia bataticola	Rhizoctonia bataticola	ED50	=	149.87	ug ml-1	PMID[458523]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	ED50	=	71.28	ug ml-1	PMID[458523]
NPT722	Organism	Athelia rolfsii	Athelia rolfsii	ED50	=	86.65	ug ml-1	PMID[458523]
NPT2701	Organism	Pythium debaryanum	Pythium debaryanum	Inhibition	=	18.3	%	PMID[458523]
NPT2701	Organism	Pythium debaryanum	Pythium debaryanum	Inhibition	=	38.23	%	PMID[458523]
NPT2701	Organism	Pythium debaryanum	Pythium debaryanum	Inhibition	=	77.14	%	PMID[458523]
NPT961	Organism	Pythium aphanidermatum	Pythium aphanidermatum	Inhibition	=	11.36	%	PMID[458523]
NPT961	Organism	Pythium aphanidermatum	Pythium aphanidermatum	Inhibition	=	29.3	%	PMID[458523]
NPT961	Organism	Pythium aphanidermatum	Pythium aphanidermatum	Inhibition	=	44.4	%	PMID[458523]
NPT2702	Organism	Fusarium udum	Fusarium udum	Inhibition	=	33.46	%	PMID[458523]
NPT2702	Organism	Fusarium udum	Fusarium udum	Inhibition	=	47.13	%	PMID[458523]
NPT2702	Organism	Fusarium udum	Fusarium udum	Inhibition	=	57.86	%	PMID[458523]
NPT2703	Organism	Rhizoctonia bataticola	Rhizoctonia bataticola	Inhibition	=	17.1	%	PMID[458523]
NPT2703	Organism	Rhizoctonia bataticola	Rhizoctonia bataticola	Inhibition	=	28.4	%	PMID[458523]
NPT2703	Organism	Rhizoctonia bataticola	Rhizoctonia bataticola	Inhibition	=	49.13	%	PMID[458523]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	Inhibition	=	33.4	%	PMID[458523]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	Inhibition	=	61.4	%	PMID[458523]
NPT529	Organism	Rhizoctonia solani	Rhizoctonia solani	Inhibition	=	81.63	%	PMID[458523]
NPT722	Organism	Athelia rolfsii	Athelia rolfsii	Inhibition	=	32.2	%	PMID[458523]
NPT722	Organism	Athelia rolfsii	Athelia rolfsii	Inhibition	=	44.43	%	PMID[458523]
NPT722	Organism	Athelia rolfsii	Athelia rolfsii	Inhibition	=	72.4	%	PMID[458523]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	23.01	%	PMID[458524]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	46.77	%	PMID[458524]

☑ 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 NPC89625 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	366
0.1-0.2	1761
0.2-0.3	4111
0.3-0.4	9615
0.4-0.5	8698
0.5-0.6	3599
0.6-0.7	5490
0.7-0.8	6204
0.8-0.85	2201
0.85-0.9	574
0.9-0.95	70
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC149618
0.9796	High Similarity	NPC133856
0.9735	High Similarity	NPC143050
0.966	High Similarity	NPC291049
0.966	High Similarity	NPC233267
0.9597	High Similarity	NPC273483
0.9592	High Similarity	NPC105415
0.9408	High Similarity	NPC146211
0.9388	High Similarity	NPC134621
0.9333	High Similarity	NPC60413
0.9324	High Similarity	NPC163846
0.9324	High Similarity	NPC225173
0.9324	High Similarity	NPC237208
0.932	High Similarity	NPC66404
0.932	High Similarity	NPC95123
0.9267	High Similarity	NPC6923
0.9262	High Similarity	NPC125801
0.9257	High Similarity	NPC29577
0.9245	High Similarity	NPC246716
0.9241	High Similarity	NPC272485
0.9241	High Similarity	NPC292788
0.9211	High Similarity	NPC217447
0.92	High Similarity	NPC37139
0.9195	High Similarity	NPC473927
0.9184	High Similarity	NPC105648
0.9182	High Similarity	NPC26568
0.915	High Similarity	NPC472799
0.9145	High Similarity	NPC478148
0.9145	High Similarity	NPC474417
0.9145	High Similarity	NPC232645
0.9145	High Similarity	NPC72958
0.9145	High Similarity	NPC149526
0.9139	High Similarity	NPC97029
0.9139	High Similarity	NPC65589
0.9139	High Similarity	NPC288036
0.9139	High Similarity	NPC158338
0.9139	High Similarity	NPC100985
0.9139	High Similarity	NPC97028
0.9133	High Similarity	NPC12305
0.913	High Similarity	NPC181523
0.9125	High Similarity	NPC20543
0.9125	High Similarity	NPC1827
0.9125	High Similarity	NPC239440
0.9125	High Similarity	NPC10576
0.9116	High Similarity	NPC37530
0.9116	High Similarity	NPC220106
0.9097	High Similarity	NPC263483
0.9085	High Similarity	NPC154683
0.9085	High Similarity	NPC87708
0.9085	High Similarity	NPC40356
0.9079	High Similarity	NPC307780
0.9079	High Similarity	NPC158866
0.9079	High Similarity	NPC119929
0.9079	High Similarity	NPC150928
0.9079	High Similarity	NPC309979
0.9074	High Similarity	NPC139350
0.9073	High Similarity	NPC7025
0.9073	High Similarity	NPC27221
0.9073	High Similarity	NPC256672
0.9067	High Similarity	NPC267509
0.9057	High Similarity	NPC20216
0.9054	High Similarity	NPC250755
0.9051	High Similarity	NPC156082
0.9048	High Similarity	NPC165172
0.9048	High Similarity	NPC99441
0.9026	High Similarity	NPC210942
0.9026	High Similarity	NPC169990
0.9007	High Similarity	NPC7943
0.9007	High Similarity	NPC123202
0.9007	High Similarity	NPC22005
0.9	High Similarity	NPC312789
0.9	High Similarity	NPC32470
0.8994	High Similarity	NPC112981
0.8993	High Similarity	NPC84266
0.8993	High Similarity	NPC159721
0.8986	High Similarity	NPC1704
0.8986	High Similarity	NPC67650
0.8974	High Similarity	NPC272196
0.8961	High Similarity	NPC175978
0.8961	High Similarity	NPC271681
0.8957	High Similarity	NPC289147
0.8954	High Similarity	NPC202595
0.8954	High Similarity	NPC473466
0.8954	High Similarity	NPC474660
0.8954	High Similarity	NPC325983
0.8947	High Similarity	NPC471641
0.8947	High Similarity	NPC240253
0.8947	High Similarity	NPC172329
0.8947	High Similarity	NPC240622
0.8947	High Similarity	NPC2569
0.8947	High Similarity	NPC471642
0.8938	High Similarity	NPC125465
0.8938	High Similarity	NPC30027
0.8933	High Similarity	NPC42540
0.8933	High Similarity	NPC151607
0.8926	High Similarity	NPC182255
0.8926	High Similarity	NPC94076
0.8917	High Similarity	NPC474373
0.891	High Similarity	NPC4547
0.8909	High Similarity	NPC113446
0.8903	High Similarity	NPC329844
0.8903	High Similarity	NPC208806
0.8896	High Similarity	NPC227166
0.8889	High Similarity	NPC476684
0.8889	High Similarity	NPC109827
0.8889	High Similarity	NPC124470
0.8889	High Similarity	NPC17219
0.8882	High Similarity	NPC34802
0.8874	High Similarity	NPC473692
0.8874	High Similarity	NPC75694
0.8867	High Similarity	NPC51106
0.8867	High Similarity	NPC471731
0.8867	High Similarity	NPC472006
0.8867	High Similarity	NPC469542
0.8867	High Similarity	NPC310340
0.8859	High Similarity	NPC16455
0.8859	High Similarity	NPC307990
0.8854	High Similarity	NPC44199
0.8844	High Similarity	NPC135837
0.8831	High Similarity	NPC194379
0.8831	High Similarity	NPC470568
0.8827	High Similarity	NPC49487
0.8827	High Similarity	NPC99613
0.8816	High Similarity	NPC99454
0.8816	High Similarity	NPC290133
0.8816	High Similarity	NPC24136
0.8816	High Similarity	NPC187282
0.8816	High Similarity	NPC130176
0.8816	High Similarity	NPC470322
0.8816	High Similarity	NPC154217
0.8812	High Similarity	NPC474350
0.8808	High Similarity	NPC189650
0.88	High Similarity	NPC474385
0.88	High Similarity	NPC471733
0.88	High Similarity	NPC469579
0.8797	High Similarity	NPC85121
0.8795	High Similarity	NPC329161
0.8795	High Similarity	NPC470091
0.8795	High Similarity	NPC240887
0.8792	High Similarity	NPC472601
0.8792	High Similarity	NPC168471
0.8792	High Similarity	NPC472600
0.879	High Similarity	NPC54928
0.879	High Similarity	NPC180924
0.8782	High Similarity	NPC214632
0.8782	High Similarity	NPC135522
0.8782	High Similarity	NPC475895
0.8776	High Similarity	NPC158481
0.8774	High Similarity	NPC209142
0.8774	High Similarity	NPC312549
0.8774	High Similarity	NPC470569
0.8774	High Similarity	NPC258249
0.8773	High Similarity	NPC298778
0.8773	High Similarity	NPC477573
0.8773	High Similarity	NPC477571
0.8773	High Similarity	NPC477572
0.8766	High Similarity	NPC329933
0.8766	High Similarity	NPC10027
0.8766	High Similarity	NPC473978
0.8766	High Similarity	NPC65775
0.8765	High Similarity	NPC76647
0.8758	High Similarity	NPC142863
0.8758	High Similarity	NPC245584
0.8758	High Similarity	NPC137296
0.8758	High Similarity	NPC289042
0.8758	High Similarity	NPC118027
0.8758	High Similarity	NPC56433
0.8758	High Similarity	NPC190648
0.8758	High Similarity	NPC8817
0.8758	High Similarity	NPC126767
0.8758	High Similarity	NPC312929
0.875	High Similarity	NPC472034
0.875	High Similarity	NPC1886
0.875	High Similarity	NPC271288
0.875	High Similarity	NPC196137
0.8742	High Similarity	NPC36181
0.8742	High Similarity	NPC186325
0.8742	High Similarity	NPC471639
0.8742	High Similarity	NPC47623
0.8742	High Similarity	NPC471643
0.8742	High Similarity	NPC470810
0.8742	High Similarity	NPC243701
0.8734	High Similarity	NPC96342
0.8734	High Similarity	NPC212967
0.8734	High Similarity	NPC246647
0.8734	High Similarity	NPC164110
0.8734	High Similarity	NPC201127
0.8733	High Similarity	NPC275734
0.8733	High Similarity	NPC472604
0.8733	High Similarity	NPC475730
0.8733	High Similarity	NPC472603
0.8733	High Similarity	NPC472605
0.8727	High Similarity	NPC474345
0.872	High Similarity	NPC158226
0.8716	High Similarity	NPC194579
0.8716	High Similarity	NPC70380
0.871	High Similarity	NPC474735
0.871	High Similarity	NPC255641
0.871	High Similarity	NPC475460
0.871	High Similarity	NPC227122

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 NPC89625 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	336
0.1-0.2	1034
0.2-0.3	1728
0.3-0.4	2609
0.4-0.5	1771
0.5-0.6	1092
0.6-0.7	383
0.7-0.8	152
0.8-0.85	36
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9026	High Similarity	NPD7819	Suspended
0.8874	High Similarity	NPD2532	Approved
0.8874	High Similarity	NPD2534	Approved
0.8874	High Similarity	NPD2533	Approved
0.8725	High Similarity	NPD970	Clinical (unspecified phase)
0.8688	High Similarity	NPD6959	Discontinued
0.8654	High Similarity	NPD7411	Suspended
0.8634	High Similarity	NPD6232	Discontinued
0.8591	High Similarity	NPD1551	Phase 2
0.8526	High Similarity	NPD3226	Approved
0.8506	High Similarity	NPD4378	Clinical (unspecified phase)
0.85	High Similarity	NPD7075	Discontinued
0.8491	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8476	Intermediate Similarity	NPD7473	Discontinued
0.8428	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD5844	Phase 1
0.8354	Intermediate Similarity	NPD6599	Discontinued
0.8323	Intermediate Similarity	NPD7768	Phase 2
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8289	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD1607	Approved
0.825	Intermediate Similarity	NPD6801	Discontinued
0.8247	Intermediate Similarity	NPD3750	Approved
0.8235	Intermediate Similarity	NPD1549	Phase 2
0.8225	Intermediate Similarity	NPD6559	Discontinued
0.8224	Intermediate Similarity	NPD2935	Discontinued
0.8205	Intermediate Similarity	NPD6799	Approved
0.8182	Intermediate Similarity	NPD5710	Approved
0.8182	Intermediate Similarity	NPD5711	Approved
0.8182	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD920	Approved
0.816	Intermediate Similarity	NPD3749	Approved
0.8158	Intermediate Similarity	NPD1510	Phase 2
0.8148	Intermediate Similarity	NPD3817	Phase 2
0.8141	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD1934	Approved
0.8133	Intermediate Similarity	NPD1240	Approved
0.8125	Intermediate Similarity	NPD4380	Phase 2
0.8121	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD2796	Approved
0.8098	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1243	Approved
0.8052	Intermediate Similarity	NPD2346	Discontinued
0.8039	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD919	Approved
0.7988	Intermediate Similarity	NPD3882	Suspended
0.7975	Intermediate Similarity	NPD2801	Approved
0.7975	Intermediate Similarity	NPD1465	Phase 2
0.7975	Intermediate Similarity	NPD7390	Discontinued
0.7975	Intermediate Similarity	NPD1511	Approved
0.7953	Intermediate Similarity	NPD5953	Discontinued
0.7949	Intermediate Similarity	NPD2800	Approved
0.7939	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD2799	Discontinued
0.7922	Intermediate Similarity	NPD3748	Approved
0.7875	Intermediate Similarity	NPD1512	Approved
0.7871	Intermediate Similarity	NPD6100	Approved
0.7871	Intermediate Similarity	NPD6099	Approved
0.787	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6166	Phase 2
0.787	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD6832	Phase 2
0.784	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6651	Approved
0.7791	Intermediate Similarity	NPD7074	Phase 3
0.7785	Intermediate Similarity	NPD1203	Approved
0.7778	Intermediate Similarity	NPD3818	Discontinued
0.7756	Intermediate Similarity	NPD5408	Approved
0.7756	Intermediate Similarity	NPD5406	Approved
0.7756	Intermediate Similarity	NPD5404	Approved
0.7756	Intermediate Similarity	NPD5405	Approved
0.7738	Intermediate Similarity	NPD5494	Approved
0.7733	Intermediate Similarity	NPD7054	Approved
0.7733	Intermediate Similarity	NPD7286	Phase 2
0.7716	Intermediate Similarity	NPD5403	Approved
0.7711	Intermediate Similarity	NPD5402	Approved
0.7709	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4625	Phase 3
0.7688	Intermediate Similarity	NPD7472	Approved
0.7673	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD411	Approved
0.7647	Intermediate Similarity	NPD3268	Approved
0.7647	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7229	Phase 3
0.7644	Intermediate Similarity	NPD6797	Phase 2
0.7614	Intermediate Similarity	NPD8313	Approved
0.7614	Intermediate Similarity	NPD8312	Approved
0.7613	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7251	Discontinued
0.76	Intermediate Similarity	NPD1283	Approved
0.7598	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD5401	Approved
0.759	Intermediate Similarity	NPD37	Approved
0.7588	Intermediate Similarity	NPD7199	Phase 2
0.7588	Intermediate Similarity	NPD1247	Approved
0.7584	Intermediate Similarity	NPD1608	Approved
0.7584	Intermediate Similarity	NPD9717	Approved
0.758	Intermediate Similarity	NPD4308	Phase 3
0.7574	Intermediate Similarity	NPD6234	Discontinued
0.7572	Intermediate Similarity	NPD7177	Discontinued
0.7562	Intermediate Similarity	NPD7003	Approved
0.756	Intermediate Similarity	NPD4966	Approved
0.756	Intermediate Similarity	NPD4965	Approved
0.756	Intermediate Similarity	NPD4967	Phase 2
0.7557	Intermediate Similarity	NPD7808	Phase 3
0.7557	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD2797	Approved
0.7548	Intermediate Similarity	NPD4060	Phase 1
0.7546	Intermediate Similarity	NPD6273	Approved
0.7543	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2313	Discontinued
0.7532	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD422	Phase 1
0.75	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4626	Approved
0.75	Intermediate Similarity	NPD230	Phase 1
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.7485	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2344	Approved
0.7468	Intermediate Similarity	NPD7033	Discontinued
0.7436	Intermediate Similarity	NPD2979	Phase 3
0.7432	Intermediate Similarity	NPD5691	Approved
0.7421	Intermediate Similarity	NPD2438	Suspended
0.7421	Intermediate Similarity	NPD4477	Approved
0.7421	Intermediate Similarity	NPD4476	Approved
0.7419	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7458	Discontinued
0.7403	Intermediate Similarity	NPD4908	Phase 1
0.74	Intermediate Similarity	NPD1281	Approved
0.7399	Intermediate Similarity	NPD3926	Phase 2
0.7396	Intermediate Similarity	NPD4288	Approved
0.7396	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7783	Phase 2
0.7394	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5124	Phase 1
0.7389	Intermediate Similarity	NPD447	Suspended
0.7383	Intermediate Similarity	NPD17	Approved
0.7382	Intermediate Similarity	NPD8151	Discontinued
0.7375	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3225	Approved
0.7325	Intermediate Similarity	NPD943	Approved
0.7325	Intermediate Similarity	NPD4307	Phase 2
0.7321	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD3267	Approved
0.732	Intermediate Similarity	NPD3266	Approved
0.7308	Intermediate Similarity	NPD3764	Approved
0.7308	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD4749	Approved
0.7302	Intermediate Similarity	NPD7435	Discontinued
0.7301	Intermediate Similarity	NPD2309	Approved
0.7293	Intermediate Similarity	NPD8150	Discontinued
0.7285	Intermediate Similarity	NPD1610	Phase 2
0.7285	Intermediate Similarity	NPD1201	Approved
0.7273	Intermediate Similarity	NPD7228	Approved
0.7267	Intermediate Similarity	NPD1471	Phase 3
0.7267	Intermediate Similarity	NPD1778	Approved
0.7258	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD9545	Approved
0.7234	Intermediate Similarity	NPD6777	Approved
0.7234	Intermediate Similarity	NPD6782	Approved
0.7234	Intermediate Similarity	NPD6780	Approved
0.7234	Intermediate Similarity	NPD6781	Approved
0.7234	Intermediate Similarity	NPD6776	Approved
0.7234	Intermediate Similarity	NPD6778	Approved
0.7234	Intermediate Similarity	NPD6779	Approved
0.7213	Intermediate Similarity	NPD4287	Approved
0.7212	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1470	Approved
0.7208	Intermediate Similarity	NPD1164	Approved
0.7205	Intermediate Similarity	NPD2531	Phase 2
0.72	Intermediate Similarity	NPD1651	Approved
0.7197	Intermediate Similarity	NPD1296	Phase 2
0.7171	Intermediate Similarity	NPD1611	Approved
0.717	Intermediate Similarity	NPD6355	Discontinued
0.7161	Intermediate Similarity	NPD1019	Discontinued
0.7161	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD2798	Approved
0.7151	Intermediate Similarity	NPD4360	Phase 2
0.7151	Intermediate Similarity	NPD4363	Phase 3
0.7135	Intermediate Similarity	NPD5760	Phase 2
0.7135	Intermediate Similarity	NPD5761	Phase 2
0.7133	Intermediate Similarity	NPD1548	Phase 1
0.7124	Intermediate Similarity	NPD3972	Approved
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.712	Intermediate Similarity	NPD7698	Approved
0.7114	Intermediate Similarity	NPD9493	Approved
0.7112	Intermediate Similarity	NPD4361	Phase 2
0.7112	Intermediate Similarity	NPD4362	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