NPASS Compound

Structure

CID147616 OpenBabel06191715522D 25 28 0 0 1 0 0 0 0 0999 V2000 -4.5380 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8060 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5380 5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4041 5.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4041 3.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8089 4.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 2.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8060 2.4781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5380 4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0739 2.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2701 5.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2701 4.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 2.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9400 3.9781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2211 5.7872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2211 4.1691 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 3 5 2 0 0 0 0 3 14 1 0 0 0 0 4 6 2 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 7 12 1 0 0 0 0 7 14 1 0 0 0 0 8 14 2 0 0 0 0 8 18 1 0 0 0 0 9 15 2 0 0 0 0 9 19 1 0 0 0 0 10 22 1 0 0 0 0 10 24 1 0 0 0 0 11 23 1 0 0 0 0 11 25 1 0 0 0 0 12 1 1 6 0 0 0 12 13 1 0 0 0 0 13 2 1 6 0 0 0 13 20 1 0 0 0 0 15 20 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 19 2 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 20 21 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.15
Volume:	348.383
LogP:	4.405
LogD:	4.286
LogS:	-5.612
# Rotatable Bonds:	5
TPSA:	57.15
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.898
Synthetic Accessibility Score:	3.353
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.945
MDCK Permeability:	2.9847067708033137e-05
Pgp-inhibitor:	0.506
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.144
Plasma Protein Binding (PPB):	98.78067779541016%
Volume Distribution (VD):	0.912
Pgp-substrate:	2.290644407272339%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.165
CYP2C19-inhibitor:	0.981
CYP2C19-substrate:	0.338
CYP2C9-inhibitor:	0.909
CYP2C9-substrate:	0.891
CYP2D6-inhibitor:	0.989
CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.978
CYP3A4-substrate:	0.758

ADMET: Excretion

Clearance (CL):	18.218
Half-life (T1/2):	0.169

ADMET: Toxicity

hERG Blockers:	0.126
Human Hepatotoxicity (H-HT):	0.112
Drug-inuced Liver Injury (DILI):	0.611
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.024
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.307
Carcinogencity:	0.874
Eye Corrosion:	0.003
Eye Irritation:	0.049
Respiratory Toxicity:	0.062

Download Data

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

Natural Product: NPC147616

Natural Product ID:	NPC147616
*Common Name:**	Magnovatin A
IUPAC Name:	(1S,2R,3R)-1,4-bis(1,3-benzodioxol-5-yl)-2,3-dimethylbutan-1-ol
Synonyms:
Standard InCHIKey:	SDXLCXZRXWWAGW-IZDJOXEWSA-N
Standard InCHI:	InChI=1S/C20H22O5/c1-12(7-14-3-5-16-18(8-14)24-10-22-16)13(2)20(21)15-4-6-17-19(9-15)25-11-23-17/h3-6,8-9,12-13,20-21H,7,10-11H2,1-2H3/t12-,13-,20+/m1/s1
SMILES:	C[C@@H]([C@@H](c1ccc2c(c1)OCO2)O)[C@@H](Cc1ccc2c(c1)OCO2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077913
PubChem CID:	44254704
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001969] Dibenzylbutane lignans

*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
NPO27465	Sinularia erecta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27142697]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27742	Mollugo pentaphylla	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27742	Mollugo pentaphylla	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27465	Sinularia erecta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27593	Silene dioica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27742	Mollugo pentaphylla	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27570	Paederia foetida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27635	Laurencia dendroidea	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27339	Lactarius blennius	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16221	Dolichos kilimandscharicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27130	Tsuga sieboldii	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27520	Casuarina equisetifolia	Species	Casuarinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27777	Artemisia phaeolepis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5146	Tuta absoluta	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26934	Naucleopsis mello-barretoi	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	7

Activity Type	# Activity
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[545957]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	100.0	ug.mL-1	PMID[545957]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[545957]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[545957]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	>	100.0	ug.mL-1	PMID[545957]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	>	100.0	ug.mL-1	PMID[545957]
NPT2580	Organism	Candida dubliniensis	Candida dubliniensis	MIC	>	100.0	ug.mL-1	PMID[545957]

☑ 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 NPC147616 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	344
0.1-0.2	1375
0.2-0.3	3592
0.3-0.4	10314
0.4-0.5	8662
0.5-0.6	5415
0.6-0.7	9050
0.7-0.8	2977
0.8-0.85	631
0.85-0.9	287
0.9-0.95	42
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC104077
1.0	High Similarity	NPC259742
1.0	High Similarity	NPC219671
0.9612	High Similarity	NPC135777
0.9612	High Similarity	NPC18576
0.9612	High Similarity	NPC142547
0.9535	High Similarity	NPC47181
0.9531	High Similarity	NPC471505
0.9531	High Similarity	NPC106739
0.9524	High Similarity	NPC158471
0.9524	High Similarity	NPC57119
0.9524	High Similarity	NPC226862
0.9524	High Similarity	NPC165128
0.952	High Similarity	NPC213711
0.952	High Similarity	NPC40352
0.9462	High Similarity	NPC174191
0.9394	High Similarity	NPC193666
0.9394	High Similarity	NPC123526
0.9394	High Similarity	NPC88640
0.9375	High Similarity	NPC271208
0.9375	High Similarity	NPC233224
0.9328	High Similarity	NPC302506
0.9318	High Similarity	NPC185908
0.9318	High Similarity	NPC469981
0.9313	High Similarity	NPC101624
0.9313	High Similarity	NPC150534
0.9313	High Similarity	NPC184938
0.9308	High Similarity	NPC169973
0.9308	High Similarity	NPC196937
0.9302	High Similarity	NPC82111
0.9302	High Similarity	NPC227160
0.9259	High Similarity	NPC474808
0.9259	High Similarity	NPC477898
0.9248	High Similarity	NPC156376
0.9231	High Similarity	NPC97316
0.9231	High Similarity	NPC7744
0.9225	High Similarity	NPC134764
0.9225	High Similarity	NPC171550
0.9219	High Similarity	NPC470084
0.9213	High Similarity	NPC206882
0.9191	High Similarity	NPC84181
0.9191	High Similarity	NPC179521
0.9185	High Similarity	NPC246947
0.9179	High Similarity	NPC46591
0.9179	High Similarity	NPC177868
0.9173	High Similarity	NPC474039
0.9173	High Similarity	NPC101807
0.9173	High Similarity	NPC283949
0.916	High Similarity	NPC136750
0.916	High Similarity	NPC266848
0.9154	High Similarity	NPC40432
0.9154	High Similarity	NPC158079
0.9154	High Similarity	NPC7171
0.9154	High Similarity	NPC27843
0.9154	High Similarity	NPC161557
0.9154	High Similarity	NPC228346
0.9154	High Similarity	NPC115207
0.9127	High Similarity	NPC249788
0.9124	High Similarity	NPC279298
0.9124	High Similarity	NPC22150
0.9124	High Similarity	NPC38041
0.912	High Similarity	NPC301641
0.912	High Similarity	NPC80241
0.9118	High Similarity	NPC298317
0.9118	High Similarity	NPC255566
0.9118	High Similarity	NPC265154
0.9111	High Similarity	NPC471908
0.9111	High Similarity	NPC472711
0.9091	High Similarity	NPC170779
0.9091	High Similarity	NPC90083
0.9084	High Similarity	NPC261812
0.9084	High Similarity	NPC207400
0.9084	High Similarity	NPC100223
0.9084	High Similarity	NPC171928
0.9084	High Similarity	NPC158526
0.9084	High Similarity	NPC16830
0.9084	High Similarity	NPC181049
0.9084	High Similarity	NPC65183
0.9084	High Similarity	NPC72046
0.9084	High Similarity	NPC129687
0.9084	High Similarity	NPC33611
0.9077	High Similarity	NPC241522
0.9077	High Similarity	NPC275950
0.9077	High Similarity	NPC257582
0.9077	High Similarity	NPC64201
0.9077	High Similarity	NPC187998
0.9077	High Similarity	NPC77040
0.9077	High Similarity	NPC173308
0.9077	High Similarity	NPC242807
0.9077	High Similarity	NPC174495
0.9077	High Similarity	NPC181079
0.9077	High Similarity	NPC153739
0.9077	High Similarity	NPC92164
0.9077	High Similarity	NPC145305
0.9077	High Similarity	NPC42300
0.907	High Similarity	NPC282703
0.907	High Similarity	NPC11258
0.907	High Similarity	NPC45774
0.907	High Similarity	NPC184733
0.907	High Similarity	NPC128208
0.907	High Similarity	NPC129570
0.907	High Similarity	NPC21867
0.9062	High Similarity	NPC274356
0.9058	High Similarity	NPC112861
0.9058	High Similarity	NPC93610
0.9058	High Similarity	NPC241846
0.9055	High Similarity	NPC18449
0.9055	High Similarity	NPC121783
0.9055	High Similarity	NPC34902
0.9051	High Similarity	NPC239254
0.9051	High Similarity	NPC172171
0.9044	High Similarity	NPC287124
0.9037	High Similarity	NPC56091
0.9037	High Similarity	NPC226547
0.9023	High Similarity	NPC474139
0.9023	High Similarity	NPC189474
0.9015	High Similarity	NPC58585
0.9008	High Similarity	NPC277804
0.9008	High Similarity	NPC476345
0.9008	High Similarity	NPC192255
0.9	High Similarity	NPC475875
0.8992	High Similarity	NPC118533
0.8992	High Similarity	NPC158737
0.8992	High Similarity	NPC165045
0.8986	High Similarity	NPC18979
0.8986	High Similarity	NPC180953
0.8986	High Similarity	NPC475868
0.8984	High Similarity	NPC148627
0.8978	High Similarity	NPC185071
0.8978	High Similarity	NPC470950
0.8978	High Similarity	NPC12728
0.8978	High Similarity	NPC185307
0.8968	High Similarity	NPC126935
0.8968	High Similarity	NPC216929
0.8968	High Similarity	NPC312713
0.8968	High Similarity	NPC172676
0.8968	High Similarity	NPC57268
0.8968	High Similarity	NPC65933
0.8963	High Similarity	NPC9068
0.896	High Similarity	NPC344161
0.8955	High Similarity	NPC25695
0.8955	High Similarity	NPC172818
0.8947	High Similarity	NPC31530
0.8939	High Similarity	NPC4940
0.8931	High Similarity	NPC63574
0.8929	High Similarity	NPC304048
0.8929	High Similarity	NPC226153
0.8921	High Similarity	NPC205796
0.8921	High Similarity	NPC276753
0.8921	High Similarity	NPC3982
0.8921	High Similarity	NPC212890
0.8913	High Similarity	NPC477701
0.8913	High Similarity	NPC166884
0.8913	High Similarity	NPC470235
0.8913	High Similarity	NPC129417
0.8913	High Similarity	NPC141569
0.8913	High Similarity	NPC283995
0.8905	High Similarity	NPC36531
0.8905	High Similarity	NPC230538
0.8905	High Similarity	NPC253878
0.8905	High Similarity	NPC229172
0.8905	High Similarity	NPC103637
0.8905	High Similarity	NPC476356
0.8881	High Similarity	NPC126409
0.8881	High Similarity	NPC25333
0.8881	High Similarity	NPC99572
0.8881	High Similarity	NPC236522
0.8881	High Similarity	NPC49235
0.8881	High Similarity	NPC148893
0.8872	High Similarity	NPC26394
0.8872	High Similarity	NPC112237
0.8865	High Similarity	NPC55158
0.8865	High Similarity	NPC286235
0.8865	High Similarity	NPC51328
0.8855	High Similarity	NPC476748
0.8849	High Similarity	NPC477702
0.8849	High Similarity	NPC43508
0.8849	High Similarity	NPC476301
0.8849	High Similarity	NPC469586
0.8846	High Similarity	NPC5428
0.8841	High Similarity	NPC46092
0.8841	High Similarity	NPC324962
0.8832	High Similarity	NPC471414
0.8828	High Similarity	NPC471693
0.8815	High Similarity	NPC199459
0.8815	High Similarity	NPC121651
0.8815	High Similarity	NPC197166
0.8815	High Similarity	NPC177035
0.8815	High Similarity	NPC52277
0.8806	High Similarity	NPC470881
0.8806	High Similarity	NPC287745
0.8806	High Similarity	NPC67247
0.8803	High Similarity	NPC98624
0.8803	High Similarity	NPC475224
0.88	High Similarity	NPC474040
0.8797	High Similarity	NPC230219
0.8794	High Similarity	NPC248132
0.8794	High Similarity	NPC130449
0.8786	High Similarity	NPC154971
0.8786	High Similarity	NPC252286

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 NPC147616 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	274
0.1-0.2	865
0.2-0.3	1648
0.3-0.4	2752
0.4-0.5	1819
0.5-0.6	1074
0.6-0.7	609
0.7-0.8	101
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8672	High Similarity	NPD3705	Approved
0.8583	High Similarity	NPD1357	Approved
0.8571	High Similarity	NPD3027	Phase 3
0.84	Intermediate Similarity	NPD5283	Phase 1
0.8322	Intermediate Similarity	NPD4967	Phase 2
0.8322	Intermediate Similarity	NPD4965	Approved
0.8322	Intermediate Similarity	NPD4966	Approved
0.8243	Intermediate Similarity	NPD37	Approved
0.8194	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD6234	Discontinued
0.7917	Intermediate Similarity	NPD6674	Discontinued
0.7883	Intermediate Similarity	NPD2861	Phase 2
0.7857	Intermediate Similarity	NPD3620	Phase 2
0.7857	Intermediate Similarity	NPD1613	Approved
0.7857	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7228	Approved
0.7829	Intermediate Similarity	NPD2978	Approved
0.7829	Intermediate Similarity	NPD2977	Approved
0.7812	Intermediate Similarity	NPD228	Approved
0.7778	Intermediate Similarity	NPD7266	Discontinued
0.7756	Intermediate Similarity	NPD7199	Phase 2
0.7704	Intermediate Similarity	NPD1091	Approved
0.7671	Intermediate Similarity	NPD4237	Approved
0.7671	Intermediate Similarity	NPD4236	Phase 3
0.7656	Intermediate Similarity	NPD3022	Approved
0.7656	Intermediate Similarity	NPD3021	Approved
0.7655	Intermediate Similarity	NPD1375	Discontinued
0.7635	Intermediate Similarity	NPD5058	Phase 3
0.7591	Intermediate Similarity	NPD2982	Phase 2
0.7591	Intermediate Similarity	NPD2983	Phase 2
0.7591	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3060	Approved
0.7547	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7240	Approved
0.7518	Intermediate Similarity	NPD2981	Phase 2
0.7516	Intermediate Similarity	NPD7028	Phase 2
0.75	Intermediate Similarity	NPD4110	Phase 3
0.75	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3018	Phase 2
0.7483	Intermediate Similarity	NPD4060	Phase 1
0.7464	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD5536	Phase 2
0.7452	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD4908	Phase 1
0.7444	Intermediate Similarity	NPD7157	Approved
0.7442	Intermediate Similarity	NPD2684	Approved
0.7434	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD5735	Approved
0.7426	Intermediate Similarity	NPD5126	Approved
0.7426	Intermediate Similarity	NPD5125	Phase 3
0.7407	Intermediate Similarity	NPD3818	Discontinued
0.7386	Intermediate Similarity	NPD1653	Approved
0.7383	Intermediate Similarity	NPD6331	Phase 2
0.7372	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2238	Phase 2
0.7348	Intermediate Similarity	NPD7843	Approved
0.7347	Intermediate Similarity	NPD2161	Phase 2
0.7343	Intermediate Similarity	NPD5110	Phase 2
0.7343	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD5111	Phase 2
0.7343	Intermediate Similarity	NPD5109	Approved
0.7319	Intermediate Similarity	NPD1610	Phase 2
0.7315	Intermediate Similarity	NPD5177	Phase 3
0.7315	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD6355	Discontinued
0.731	Intermediate Similarity	NPD3657	Discovery
0.7297	Intermediate Similarity	NPD5762	Approved
0.7297	Intermediate Similarity	NPD5763	Approved
0.7285	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD5588	Approved
0.7279	Intermediate Similarity	NPD4108	Discontinued
0.7278	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7262	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4140	Approved
0.7241	Intermediate Similarity	NPD1558	Phase 1
0.7233	Intermediate Similarity	NPD5604	Discontinued
0.7229	Intermediate Similarity	NPD7685	Pre-registration
0.7222	Intermediate Similarity	NPD3020	Approved
0.7219	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5241	Discontinued
0.7214	Intermediate Similarity	NPD3685	Discontinued
0.7212	Intermediate Similarity	NPD7074	Phase 3
0.7211	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4536	Approved
0.7211	Intermediate Similarity	NPD4538	Approved
0.7202	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4123	Phase 3
0.7183	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD8651	Approved
0.7161	Intermediate Similarity	NPD4210	Discontinued
0.7161	Intermediate Similarity	NPD3686	Approved
0.7161	Intermediate Similarity	NPD3687	Approved
0.7153	Intermediate Similarity	NPD7095	Approved
0.7152	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5772	Approved
0.7152	Intermediate Similarity	NPD5773	Approved
0.7152	Intermediate Similarity	NPD7054	Approved
0.7143	Intermediate Similarity	NPD2232	Approved
0.7143	Intermediate Similarity	NPD2231	Phase 2
0.7143	Intermediate Similarity	NPD2235	Phase 2
0.7143	Intermediate Similarity	NPD2230	Approved
0.7143	Intermediate Similarity	NPD6653	Approved
0.7143	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2233	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7115	Intermediate Similarity	NPD4005	Discontinued
0.7113	Intermediate Similarity	NPD3094	Phase 2
0.7108	Intermediate Similarity	NPD7472	Approved
0.7107	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2560	Approved
0.7107	Intermediate Similarity	NPD2563	Approved
0.7105	Intermediate Similarity	NPD2677	Approved
0.7099	Intermediate Similarity	NPD8127	Discontinued
0.7095	Intermediate Similarity	NPD7097	Phase 1
0.7095	Intermediate Similarity	NPD6896	Approved
0.7095	Intermediate Similarity	NPD6895	Approved
0.7092	Intermediate Similarity	NPD5327	Phase 3
0.7089	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1934	Approved
0.7086	Intermediate Similarity	NPD4162	Approved
0.7083	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD3092	Approved
0.7067	Intermediate Similarity	NPD6005	Phase 3
0.7067	Intermediate Similarity	NPD6004	Phase 3
0.7067	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6002	Phase 3
0.7063	Intermediate Similarity	NPD4624	Approved
0.7063	Intermediate Similarity	NPD6584	Phase 3
0.7059	Intermediate Similarity	NPD6671	Approved
0.7059	Intermediate Similarity	NPD7124	Phase 2
0.7059	Intermediate Similarity	NPD709	Approved
0.7055	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2667	Approved
0.705	Intermediate Similarity	NPD4626	Approved
0.705	Intermediate Similarity	NPD5846	Approved
0.705	Intermediate Similarity	NPD6516	Phase 2
0.705	Intermediate Similarity	NPD2668	Approved
0.7047	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD5960	Phase 3
0.7044	Intermediate Similarity	NPD8455	Phase 2
0.7042	Intermediate Similarity	NPD1283	Approved
0.7032	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD52	Approved
0.7032	Intermediate Similarity	NPD7526	Approved
0.7029	Intermediate Similarity	NPD3091	Approved
0.7029	Intermediate Similarity	NPD5582	Discontinued
0.7029	Intermediate Similarity	NPD1548	Phase 1
0.7027	Intermediate Similarity	NPD6353	Approved
0.7023	Intermediate Similarity	NPD968	Approved
0.7013	Intermediate Similarity	NPD4357	Discontinued
0.7012	Intermediate Similarity	NPD2970	Approved
0.7012	Intermediate Similarity	NPD2969	Approved
0.7006	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3847	Discontinued
0.6992	Remote Similarity	NPD5451	Approved
0.6986	Remote Similarity	NPD6798	Discontinued
0.6986	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD2859	Approved
0.6984	Remote Similarity	NPD2860	Approved
0.6982	Remote Similarity	NPD7808	Phase 3
0.6978	Remote Similarity	NPD5585	Approved
0.6972	Remote Similarity	NPD4749	Approved
0.697	Remote Similarity	NPD290	Approved
0.6968	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6797	Phase 2
0.6963	Remote Similarity	NPD1138	Approved
0.6963	Remote Similarity	NPD5535	Approved
0.6962	Remote Similarity	NPD4678	Approved
0.6962	Remote Similarity	NPD4675	Approved
0.6957	Remote Similarity	NPD3882	Suspended
0.6954	Remote Similarity	NPD3540	Phase 1
0.6951	Remote Similarity	NPD3051	Approved
0.6946	Remote Similarity	NPD5844	Phase 1
0.6944	Remote Similarity	NPD7680	Approved
0.6939	Remote Similarity	NPD6233	Phase 2
0.6939	Remote Similarity	NPD2674	Phase 3
0.6937	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD6387	Discontinued
0.6933	Remote Similarity	NPD5494	Approved
0.6933	Remote Similarity	NPD7033	Discontinued
0.6929	Remote Similarity	NPD17	Approved
0.6929	Remote Similarity	NPD3095	Discontinued
0.6928	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2922	Phase 1
0.6923	Remote Similarity	NPD6696	Suspended
0.6923	Remote Similarity	NPD7251	Discontinued
0.6923	Remote Similarity	NPD6559	Discontinued
0.6918	Remote Similarity	NPD4625	Phase 3
0.6914	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD2492	Phase 1

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data