NPASS Compound

Structure

NPC471640 OpenBabel07101719132D 29 30 0 0 1 0 0 0 0 0999 V2000 -5.1962 3.0000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 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 2.5981 -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 -0.8660 -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 -4.3301 2.5000 0.0000 C 0 0 2 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 1.7321 -2.0000 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 2.5981 -0.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 -6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 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 2 15 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 14 1 0 0 0 0 9 17 1 0 0 0 0 10 16 2 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 1 1 6 0 0 0 14 28 1 0 0 0 0 15 23 2 0 0 0 0 15 28 1 0 0 0 0 16 22 1 0 0 0 0 17 29 1 0 0 0 0 18 26 1 0 0 0 0 19 22 1 0 0 0 0 19 24 2 0 0 0 0 20 22 2 0 0 0 0 20 29 1 0 0 0 0 21 25 2 0 0 0 0 21 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	404.18
Volume:	415.032
LogP:	4.079
LogD:	3.241
LogS:	-4.715
# Rotatable Bonds:	12
TPSA:	92.04
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.441
Synthetic Accessibility Score:	3.127
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.681
MDCK Permeability:	7.051265856716782e-05
Pgp-inhibitor:	0.952
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.909
Plasma Protein Binding (PPB):	91.5323257446289%
Volume Distribution (VD):	0.461
Pgp-substrate:	10.00171184539795%

ADMET: Metabolism

CYP1A2-inhibitor:	0.915
CYP1A2-substrate:	0.837
CYP2C19-inhibitor:	0.936
CYP2C19-substrate:	0.402
CYP2C9-inhibitor:	0.931
CYP2C9-substrate:	0.917
CYP2D6-inhibitor:	0.16
CYP2D6-substrate:	0.733
CYP3A4-inhibitor:	0.831
CYP3A4-substrate:	0.334

ADMET: Excretion

Clearance (CL):	3.423
Half-life (T1/2):	0.716

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.65
Drug-inuced Liver Injury (DILI):	0.867
AMES Toxicity:	0.199
Rat Oral Acute Toxicity:	0.543
Maximum Recommended Daily Dose:	0.795
Skin Sensitization:	0.824
Carcinogencity:	0.061
Eye Corrosion:	0.005
Eye Irritation:	0.076
Respiratory Toxicity:	0.071

Download Data

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

Natural Product: NPC471640

Natural Product ID:	NPC471640
*Common Name:**	Methyl 2-[2-[(6R)-6-Acetyloxyheptyl]-7-Methoxy-4-Oxochromen-5-Yl]Acetate
IUPAC Name:	methyl 2-[2-[(6R)-6-acetyloxyheptyl]-7-methoxy-4-oxochromen-5-yl]acetate
Synonyms:
Standard InCHIKey:	LIDOJFNNQVPBFX-CQSZACIVSA-N
Standard InCHI:	InChI=1S/C22H28O7/c1-14(28-15(2)23)8-6-5-7-9-17-12-19(24)22-16(11-21(25)27-4)10-18(26-3)13-20(22)29-17/h10,12-14H,5-9,11H2,1-4H3/t14-/m1/s1
SMILES:	COC(=O)Cc1cc(OC)cc2c1c(=O)cc(o2)CCCCC[C@H](OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3086813
PubChem CID:	72946055
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19117486]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	chinese mangrove plant Rhizophora mucronata	n.a.	n.a.	PMID[19271764]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	Chinese mangrove plant Rhizophoramucronata	n.a.	n.a.	PMID[19762244]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	Isolated from the branches of Podocarpus macrophyllus	Kunming World Horticultural Exposition Garden, Kunming, China	2002-NOV	PMID[21302965]
NPO33175	Pestalotiopsis sp.	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24168147]

☑ 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	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	500.0	ug.mL-1	PMID[509449]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	500.0	ug.mL-1	PMID[509449]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	500.0	ug.mL-1	PMID[509449]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	>	500.0	ug.mL-1	PMID[509449]

☑ 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 NPC471640 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	403
0.1-0.2	1679
0.2-0.3	4131
0.3-0.4	9708
0.4-0.5	8832
0.5-0.6	3987
0.6-0.7	6013
0.7-0.8	5581
0.8-0.85	1843
0.85-0.9	475
0.9-0.95	36
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC471644
0.9781	High Similarity	NPC471643
0.9781	High Similarity	NPC471639
0.9574	High Similarity	NPC471641
0.9574	High Similarity	NPC471642
0.9574	High Similarity	NPC240253
0.9574	High Similarity	NPC240622
0.95	High Similarity	NPC312789
0.9225	High Similarity	NPC472034
0.9161	High Similarity	NPC472033
0.9155	High Similarity	NPC184702
0.9149	High Similarity	NPC297985
0.9149	High Similarity	NPC469579
0.9097	High Similarity	NPC472036
0.9085	High Similarity	NPC472006
0.9085	High Similarity	NPC478202
0.9078	High Similarity	NPC1704
0.9078	High Similarity	NPC67650
0.9071	High Similarity	NPC57380
0.9041	High Similarity	NPC60413
0.9028	High Similarity	NPC473927
0.9021	High Similarity	NPC95123
0.9021	High Similarity	NPC470932
0.9021	High Similarity	NPC66404
0.9014	High Similarity	NPC474385
0.8973	High Similarity	NPC6923
0.8963	High Similarity	NPC473907
0.8958	High Similarity	NPC134621
0.8951	High Similarity	NPC215451
0.8951	High Similarity	NPC469542
0.8951	High Similarity	NPC51106
0.8951	High Similarity	NPC277369
0.8944	High Similarity	NPC478201
0.8944	High Similarity	NPC158634
0.8944	High Similarity	NPC478217
0.8944	High Similarity	NPC475730
0.8944	High Similarity	NPC472035
0.8944	High Similarity	NPC313123
0.8936	High Similarity	NPC32360
0.8936	High Similarity	NPC92655
0.8936	High Similarity	NPC268052
0.8929	High Similarity	NPC135837
0.8929	High Similarity	NPC268081
0.8904	High Similarity	NPC153417
0.8897	High Similarity	NPC107625
0.8897	High Similarity	NPC237208
0.8897	High Similarity	NPC473894
0.8889	High Similarity	NPC280404
0.8889	High Similarity	NPC475496
0.8889	High Similarity	NPC189650
0.8889	High Similarity	NPC86373
0.8889	High Similarity	NPC277426
0.8889	High Similarity	NPC210425
0.8889	High Similarity	NPC49852
0.8881	High Similarity	NPC105648
0.8873	High Similarity	NPC136095
0.8873	High Similarity	NPC109007
0.8865	High Similarity	NPC191835
0.8865	High Similarity	NPC253616
0.8865	High Similarity	NPC478200
0.8865	High Similarity	NPC33144
0.8857	High Similarity	NPC242712
0.8851	High Similarity	NPC473732
0.8836	High Similarity	NPC210320
0.8836	High Similarity	NPC52106
0.8832	High Similarity	NPC473271
0.8828	High Similarity	NPC473692
0.8828	High Similarity	NPC171656
0.8828	High Similarity	NPC29577
0.8828	High Similarity	NPC294365
0.8811	High Similarity	NPC307990
0.8811	High Similarity	NPC220106
0.8811	High Similarity	NPC16455
0.8803	High Similarity	NPC36414
0.8794	High Similarity	NPC65837
0.8794	High Similarity	NPC474771
0.8794	High Similarity	NPC70380
0.8794	High Similarity	NPC178467
0.8794	High Similarity	NPC149372
0.8794	High Similarity	NPC254741
0.8794	High Similarity	NPC474849
0.8792	High Similarity	NPC475116
0.8786	High Similarity	NPC470844
0.8786	High Similarity	NPC180905
0.8786	High Similarity	NPC182496
0.8784	High Similarity	NPC295036
0.8784	High Similarity	NPC158866
0.8784	High Similarity	NPC474660
0.8777	High Similarity	NPC473655
0.8777	High Similarity	NPC101294
0.8776	High Similarity	NPC37139
0.8776	High Similarity	NPC73411
0.8776	High Similarity	NPC215711
0.8759	High Similarity	NPC210966
0.8759	High Similarity	NPC478203
0.8759	High Similarity	NPC27106
0.8759	High Similarity	NPC126882
0.875	High Similarity	NPC250755
0.875	High Similarity	NPC96692
0.8742	High Similarity	NPC474983
0.8741	High Similarity	NPC472515
0.8732	High Similarity	NPC472602
0.8732	High Similarity	NPC103001
0.8732	High Similarity	NPC94248
0.8732	High Similarity	NPC475974
0.8732	High Similarity	NPC472403
0.8732	High Similarity	NPC9121
0.8732	High Similarity	NPC212693
0.8732	High Similarity	NPC177307
0.8725	High Similarity	NPC133856
0.8723	High Similarity	NPC99854
0.8723	High Similarity	NPC235115
0.8716	High Similarity	NPC473978
0.8716	High Similarity	NPC233267
0.8716	High Similarity	NPC291049
0.8716	High Similarity	NPC476684
0.8714	High Similarity	NPC175943
0.8707	High Similarity	NPC14098
0.8707	High Similarity	NPC259632
0.8707	High Similarity	NPC12305
0.8705	High Similarity	NPC278556
0.8699	High Similarity	NPC257558
0.869	High Similarity	NPC310340
0.8681	High Similarity	NPC53649
0.8681	High Similarity	NPC470856
0.8681	High Similarity	NPC472603
0.8681	High Similarity	NPC90411
0.8676	High Similarity	NPC101894
0.8675	High Similarity	NPC89625
0.8675	High Similarity	NPC149618
0.8667	High Similarity	NPC273483
0.8658	High Similarity	NPC475460
0.8658	High Similarity	NPC473466
0.8652	High Similarity	NPC125269
0.8652	High Similarity	NPC298900
0.8649	High Similarity	NPC105415
0.8643	High Similarity	NPC153783
0.8643	High Similarity	NPC10971
0.8643	High Similarity	NPC203817
0.8639	High Similarity	NPC267509
0.8621	High Similarity	NPC24075
0.8621	High Similarity	NPC29536
0.8621	High Similarity	NPC22467
0.8611	High Similarity	NPC472601
0.8611	High Similarity	NPC473209
0.8611	High Similarity	NPC139554
0.8611	High Similarity	NPC158472
0.8611	High Similarity	NPC472600
0.8609	High Similarity	NPC472799
0.8601	High Similarity	NPC259685
0.86	High Similarity	NPC215921
0.86	High Similarity	NPC72958
0.86	High Similarity	NPC70016
0.86	High Similarity	NPC232645
0.8592	High Similarity	NPC46869
0.8591	High Similarity	NPC97028
0.8591	High Similarity	NPC237440
0.8591	High Similarity	NPC288036
0.8591	High Similarity	NPC164299
0.8591	High Similarity	NPC4423
0.8591	High Similarity	NPC65589
0.8591	High Similarity	NPC158338
0.8591	High Similarity	NPC97029
0.8591	High Similarity	NPC77325
0.8591	High Similarity	NPC100985
0.8591	High Similarity	NPC270160
0.8582	High Similarity	NPC223354
0.8582	High Similarity	NPC292998
0.8582	High Similarity	NPC247743
0.8582	High Similarity	NPC223457
0.8571	High Similarity	NPC475589
0.8571	High Similarity	NPC32470
0.8571	High Similarity	NPC471590
0.8571	High Similarity	NPC31872
0.8571	High Similarity	NPC473584
0.8571	High Similarity	NPC284424
0.8562	High Similarity	NPC70853
0.8562	High Similarity	NPC112829
0.8562	High Similarity	NPC159721
0.8562	High Similarity	NPC246466
0.8562	High Similarity	NPC294432
0.8562	High Similarity	NPC73028
0.8562	High Similarity	NPC263483
0.8562	High Similarity	NPC9966
0.8562	High Similarity	NPC470556
0.8552	High Similarity	NPC171094
0.8552	High Similarity	NPC472605
0.8552	High Similarity	NPC244923
0.8552	High Similarity	NPC472604
0.8552	High Similarity	NPC275734
0.8552	High Similarity	NPC474037
0.8543	High Similarity	NPC271681
0.8543	High Similarity	NPC474843
0.8543	High Similarity	NPC87708
0.8542	High Similarity	NPC247409
0.8542	High Similarity	NPC105456
0.8542	High Similarity	NPC131130
0.8542	High Similarity	NPC474655
0.8542	High Similarity	NPC139634
0.8535	High Similarity	NPC472895

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 NPC471640 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	1004
0.2-0.3	1767
0.3-0.4	2612
0.4-0.5	1830
0.5-0.6	1057
0.6-0.7	372
0.7-0.8	129
0.8-0.85	30
0.85-0.9	11
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8936	High Similarity	NPD970	Clinical (unspecified phase)
0.8794	High Similarity	NPD2796	Approved
0.8733	High Similarity	NPD7819	Suspended
0.8503	High Similarity	NPD6799	Approved
0.8462	Intermediate Similarity	NPD3748	Approved
0.8431	Intermediate Similarity	NPD3817	Phase 2
0.8356	Intermediate Similarity	NPD1243	Approved
0.8355	Intermediate Similarity	NPD7411	Suspended
0.8322	Intermediate Similarity	NPD2533	Approved
0.8322	Intermediate Similarity	NPD2534	Approved
0.8322	Intermediate Similarity	NPD2532	Approved
0.8289	Intermediate Similarity	NPD6599	Discontinued
0.8247	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8219	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD920	Approved
0.82	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6801	Discontinued
0.8176	Intermediate Similarity	NPD3750	Approved
0.8169	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1549	Phase 2
0.8129	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD7075	Discontinued
0.8082	Intermediate Similarity	NPD1510	Phase 2
0.8079	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8065	Intermediate Similarity	NPD1934	Approved
0.805	Intermediate Similarity	NPD6959	Discontinued
0.8038	Intermediate Similarity	NPD919	Approved
0.8028	Intermediate Similarity	NPD6832	Phase 2
0.8013	Intermediate Similarity	NPD1511	Approved
0.8013	Intermediate Similarity	NPD2801	Approved
0.8012	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD5494	Approved
0.7974	Intermediate Similarity	NPD5403	Approved
0.7962	Intermediate Similarity	NPD5402	Approved
0.7961	Intermediate Similarity	NPD5401	Approved
0.7933	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD1240	Approved
0.7911	Intermediate Similarity	NPD3882	Suspended
0.7908	Intermediate Similarity	NPD1512	Approved
0.7905	Intermediate Similarity	NPD1551	Phase 2
0.7877	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7871	Intermediate Similarity	NPD3226	Approved
0.7862	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD3749	Approved
0.7843	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1247	Approved
0.7823	Intermediate Similarity	NPD1607	Approved
0.7821	Intermediate Similarity	NPD4380	Phase 2
0.7817	Intermediate Similarity	NPD3267	Approved
0.7817	Intermediate Similarity	NPD3266	Approved
0.7799	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7768	Phase 2
0.7778	Intermediate Similarity	NPD6232	Discontinued
0.7758	Intermediate Similarity	NPD5844	Phase 1
0.7758	Intermediate Similarity	NPD7054	Approved
0.7748	Intermediate Similarity	NPD2654	Approved
0.7748	Intermediate Similarity	NPD2800	Approved
0.7744	Intermediate Similarity	NPD7473	Discontinued
0.7718	Intermediate Similarity	NPD2799	Discontinued
0.7711	Intermediate Similarity	NPD7472	Approved
0.7697	Intermediate Similarity	NPD3818	Discontinued
0.7697	Intermediate Similarity	NPD4628	Phase 3
0.7683	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD6166	Phase 2
0.7683	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD3268	Approved
0.7671	Intermediate Similarity	NPD1296	Phase 2
0.7669	Intermediate Similarity	NPD5710	Approved
0.7669	Intermediate Similarity	NPD5711	Approved
0.7667	Intermediate Similarity	NPD2935	Discontinued
0.7665	Intermediate Similarity	NPD6797	Phase 2
0.7643	Intermediate Similarity	NPD17	Approved
0.7639	Intermediate Similarity	NPD1019	Discontinued
0.7628	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD3926	Phase 2
0.7619	Intermediate Similarity	NPD7251	Discontinued
0.7616	Intermediate Similarity	NPD2346	Discontinued
0.7606	Intermediate Similarity	NPD9717	Approved
0.7605	Intermediate Similarity	NPD7074	Phase 3
0.7582	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7808	Phase 3
0.755	Intermediate Similarity	NPD6099	Approved
0.755	Intermediate Similarity	NPD6100	Approved
0.7545	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD422	Phase 1
0.7517	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD1471	Phase 3
0.7485	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD7033	Discontinued
0.7483	Intermediate Similarity	NPD1608	Approved
0.747	Intermediate Similarity	NPD2403	Approved
0.7467	Intermediate Similarity	NPD6651	Approved
0.7456	Intermediate Similarity	NPD5953	Discontinued
0.7455	Intermediate Similarity	NPD6808	Phase 2
0.7453	Intermediate Similarity	NPD1465	Phase 2
0.7448	Intermediate Similarity	NPD1203	Approved
0.7447	Intermediate Similarity	NPD5691	Approved
0.7432	Intermediate Similarity	NPD411	Approved
0.7432	Intermediate Similarity	NPD2313	Discontinued
0.7415	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6559	Discontinued
0.7407	Intermediate Similarity	NPD5353	Approved
0.7407	Intermediate Similarity	NPD4288	Approved
0.74	Intermediate Similarity	NPD1933	Approved
0.74	Intermediate Similarity	NPD447	Suspended
0.7397	Intermediate Similarity	NPD2798	Approved
0.7394	Intermediate Similarity	NPD7199	Phase 2
0.7391	Intermediate Similarity	NPD1241	Discontinued
0.7389	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7229	Phase 3
0.7337	Intermediate Similarity	NPD7286	Phase 2
0.7333	Intermediate Similarity	NPD4307	Phase 2
0.7329	Intermediate Similarity	NPD5889	Approved
0.7329	Intermediate Similarity	NPD5890	Approved
0.7329	Intermediate Similarity	NPD2797	Approved
0.7315	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5124	Phase 1
0.7285	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2344	Approved
0.7273	Intermediate Similarity	NPD1778	Approved
0.7273	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD3225	Approved
0.7254	Intermediate Similarity	NPD9545	Approved
0.7246	Intermediate Similarity	NPD3787	Discontinued
0.7241	Intermediate Similarity	NPD3972	Approved
0.7233	Intermediate Similarity	NPD6273	Approved
0.7219	Intermediate Similarity	NPD2979	Phase 3
0.7215	Intermediate Similarity	NPD7390	Discontinued
0.7208	Intermediate Similarity	NPD2438	Suspended
0.7202	Intermediate Similarity	NPD5242	Approved
0.7197	Intermediate Similarity	NPD3887	Approved
0.7179	Intermediate Similarity	NPD1652	Phase 2
0.7178	Intermediate Similarity	NPD37	Approved
0.7176	Intermediate Similarity	NPD3751	Discontinued
0.7172	Intermediate Similarity	NPD1281	Approved
0.7171	Intermediate Similarity	NPD6355	Discontinued
0.716	Intermediate Similarity	NPD6585	Discontinued
0.7153	Intermediate Similarity	NPD4626	Approved
0.7152	Intermediate Similarity	NPD4965	Approved
0.7152	Intermediate Similarity	NPD8032	Phase 2
0.7152	Intermediate Similarity	NPD4966	Approved
0.7152	Intermediate Similarity	NPD4967	Phase 2
0.7143	Intermediate Similarity	NPD1876	Approved
0.7143	Intermediate Similarity	NPD4308	Phase 3
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD9493	Approved
0.7105	Intermediate Similarity	NPD3140	Approved
0.7105	Intermediate Similarity	NPD943	Approved
0.7105	Intermediate Similarity	NPD3142	Approved
0.7103	Intermediate Similarity	NPD3496	Discontinued
0.7097	Intermediate Similarity	NPD4476	Approved
0.7097	Intermediate Similarity	NPD4477	Approved
0.7089	Intermediate Similarity	NPD2309	Approved
0.7088	Intermediate Similarity	NPD8285	Discontinued
0.7086	Intermediate Similarity	NPD6798	Discontinued
0.7083	Intermediate Similarity	NPD1651	Approved
0.7083	Intermediate Similarity	NPD5585	Approved
0.7067	Intermediate Similarity	NPD4908	Phase 1
0.7066	Intermediate Similarity	NPD6234	Discontinued
0.7049	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8313	Approved
0.7029	Intermediate Similarity	NPD8312	Approved
0.7027	Intermediate Similarity	NPD1283	Approved
0.7014	Intermediate Similarity	NPD1548	Phase 1
0.7012	Intermediate Similarity	NPD6385	Approved
0.7012	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD6386	Approved
0.7006	Intermediate Similarity	NPD8434	Phase 2
0.7006	Intermediate Similarity	NPD6971	Discontinued
0.7	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4060	Phase 1
0.6987	Remote Similarity	NPD5404	Approved
0.6987	Remote Similarity	NPD5405	Approved
0.6987	Remote Similarity	NPD2531	Phase 2
0.6987	Remote Similarity	NPD5406	Approved
0.6987	Remote Similarity	NPD5408	Approved
0.6978	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7177	Discontinued
0.6974	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3764	Approved
0.697	Remote Similarity	NPD6279	Approved
0.697	Remote Similarity	NPD6844	Discontinued
0.697	Remote Similarity	NPD6280	Approved
0.6961	Remote Similarity	NPD4360	Phase 2
0.6961	Remote Similarity	NPD4363	Phase 3

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