NPASS Compound

Structure

NPC354984 OpenBabel07101719402D 22 24 0 0 1 0 0 0 0 0999 V2000 2.0731 -4.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -4.0981 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8660 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5000 -4.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4641 -3.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7588 -5.5640 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0731 -0.6589 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -4.5981 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 3 1 0 0 0 0 2 4 1 0 0 0 0 3 8 1 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 9 1 0 0 0 0 6 13 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 1 1 6 0 0 0 8 21 1 0 0 0 0 9 14 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 18 1 0 0 0 0 12 4 1 6 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 19 2 0 0 0 0 13 21 1 0 0 0 0 14 15 1 0 0 0 0 15 20 2 0 0 0 0 16 15 1 1 0 0 0 16 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	306.11
Volume:	299.182
LogP:	2.885
LogD:	2.254
LogS:	-3.51
# Rotatable Bonds:	0
TPSA:	96.36
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.559
Synthetic Accessibility Score:	4.359
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.866
MDCK Permeability:	2.3393917217617854e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.447

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199
Plasma Protein Binding (PPB):	78.31952667236328%
Volume Distribution (VD):	0.599
Pgp-substrate:	14.417230606079102%

ADMET: Metabolism

CYP1A2-inhibitor:	0.409
CYP1A2-substrate:	0.095
CYP2C19-inhibitor:	0.173
CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.282
CYP2C9-substrate:	0.822
CYP2D6-inhibitor:	0.607
CYP2D6-substrate:	0.233
CYP3A4-inhibitor:	0.645
CYP3A4-substrate:	0.195

ADMET: Excretion

Clearance (CL):	12.654
Half-life (T1/2):	0.762

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.867
AMES Toxicity:	0.435
Rat Oral Acute Toxicity:	0.705
Maximum Recommended Daily Dose:	0.756
Skin Sensitization:	0.633
Carcinogencity:	0.683
Eye Corrosion:	0.005
Eye Irritation:	0.065
Respiratory Toxicity:	0.448

Download Data

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

Natural Product: NPC354984

Natural Product ID:	NPC354984
*Common Name:**	BVDHPBILFRQGEC-XLIXJNEVSA-N
IUPAC Name:	n.a.
Synonyms:	10,11-Epoxycurvularin
Standard InCHIKey:	BVDHPBILFRQGEC-XLIXJNEVSA-N
Standard InCHI:	InChI=1S/C16H18O6/c1-8-3-2-4-12-16(22-12)15(20)14-9(6-13(19)21-8)5-10(17)7-11(14)18/h5,7-8,12,16-18H,2-4,6H2,1H3/t8-,12+,16-/m0/s1
SMILES:	C[C@H]1CCC[C@@H]2[C@@H](C(=O)c3c(cc(cc3O)O)CC(=O)O1)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1643632
PubChem CID:	14314906
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0003671] Aryl alkyl ketones

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	MIC	>	100000.0	nM	PMID[542322]

☑ 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 NPC354984 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	336
0.1-0.2	1432
0.2-0.3	3605
0.3-0.4	8600
0.4-0.5	10625
0.5-0.6	4981
0.6-0.7	7117
0.7-0.8	5539
0.8-0.85	366
0.85-0.9	76
0.9-0.95	18
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9559	High Similarity	NPC474849
0.9559	High Similarity	NPC178467
0.9559	High Similarity	NPC65837
0.9559	High Similarity	NPC474771
0.9559	High Similarity	NPC149372
0.9489	High Similarity	NPC475974
0.9362	High Similarity	NPC210966
0.9362	High Similarity	NPC126882
0.9362	High Similarity	NPC478203
0.9348	High Similarity	NPC9121
0.9348	High Similarity	NPC177307
0.9348	High Similarity	NPC472403
0.9296	High Similarity	NPC257558
0.9286	High Similarity	NPC478217
0.9286	High Similarity	NPC313123
0.9286	High Similarity	NPC244923
0.9281	High Similarity	NPC474655
0.9209	High Similarity	NPC191835
0.9155	High Similarity	NPC478202
0.9149	High Similarity	NPC478201
0.9149	High Similarity	NPC472035
0.9137	High Similarity	NPC70380
0.911	High Similarity	NPC56204
0.9097	High Similarity	NPC107625
0.9071	High Similarity	NPC33144
0.9071	High Similarity	NPC94248
0.9071	High Similarity	NPC478200
0.9071	High Similarity	NPC212693
0.9028	High Similarity	NPC83272
0.9007	High Similarity	NPC52358
0.9	High Similarity	NPC71256
0.8936	High Similarity	NPC472602
0.8926	High Similarity	NPC275837
0.8904	High Similarity	NPC472036
0.8897	High Similarity	NPC41263
0.8897	High Similarity	NPC472034
0.8889	High Similarity	NPC472006
0.8889	High Similarity	NPC51106
0.8881	High Similarity	NPC67650
0.8881	High Similarity	NPC1704
0.8881	High Similarity	NPC53649
0.8881	High Similarity	NPC472603
0.8873	High Similarity	NPC105456
0.8873	High Similarity	NPC139634
0.8867	High Similarity	NPC99381
0.8859	High Similarity	NPC213224
0.8849	High Similarity	NPC153783
0.8836	High Similarity	NPC472033
0.8811	High Similarity	NPC472600
0.8811	High Similarity	NPC158472
0.8811	High Similarity	NPC472601
0.88	High Similarity	NPC55092
0.8794	High Similarity	NPC235115
0.8776	High Similarity	NPC210320
0.8776	High Similarity	NPC14098
0.8768	High Similarity	NPC247477
0.8768	High Similarity	NPC17840
0.8759	High Similarity	NPC159721
0.875	High Similarity	NPC472605
0.875	High Similarity	NPC158634
0.875	High Similarity	NPC472604
0.8741	High Similarity	NPC268052
0.8741	High Similarity	NPC92655
0.8741	High Similarity	NPC32360
0.8732	High Similarity	NPC194579
0.8725	High Similarity	NPC469619
0.8725	High Similarity	NPC469670
0.8716	High Similarity	NPC471641
0.8716	High Similarity	NPC215711
0.8716	High Similarity	NPC73411
0.8716	High Similarity	NPC240622
0.8716	High Similarity	NPC240253
0.8716	High Similarity	NPC471642
0.8714	High Similarity	NPC48036
0.8705	High Similarity	NPC219892
0.8705	High Similarity	NPC189823
0.8705	High Similarity	NPC198249
0.8699	High Similarity	NPC42540
0.8699	High Similarity	NPC151607
0.869	High Similarity	NPC474385
0.8676	High Similarity	NPC477454
0.8676	High Similarity	NPC201728
0.8676	High Similarity	NPC262671
0.8667	High Similarity	NPC205918
0.8658	High Similarity	NPC198927
0.8658	High Similarity	NPC84142
0.8658	High Similarity	NPC120171
0.8643	High Similarity	NPC478190
0.8639	High Similarity	NPC312789
0.863	High Similarity	NPC472610
0.863	High Similarity	NPC469542
0.863	High Similarity	NPC471731
0.8621	High Similarity	NPC37530
0.8621	High Similarity	NPC475730
0.8618	High Similarity	NPC478221
0.8618	High Similarity	NPC208173
0.8618	High Similarity	NPC170189
0.8613	High Similarity	NPC473691
0.8611	High Similarity	NPC88269
0.8611	High Similarity	NPC275356
0.8609	High Similarity	NPC184284
0.8609	High Similarity	NPC76041
0.8609	High Similarity	NPC115249
0.8601	High Similarity	NPC135837
0.86	High Similarity	NPC472891
0.86	High Similarity	NPC164762
0.8592	High Similarity	NPC278375
0.8592	High Similarity	NPC27407
0.8591	High Similarity	NPC153417
0.8582	High Similarity	NPC180261
0.8582	High Similarity	NPC43627
0.8582	High Similarity	NPC37299
0.8581	High Similarity	NPC202112
0.8581	High Similarity	NPC51513
0.8581	High Similarity	NPC473023
0.8571	High Similarity	NPC277426
0.8571	High Similarity	NPC210425
0.8571	High Similarity	NPC280404
0.8571	High Similarity	NPC86373
0.8562	High Similarity	NPC469579
0.8562	High Similarity	NPC471733
0.8553	High Similarity	NPC137301
0.8553	High Similarity	NPC478231
0.8552	High Similarity	NPC99441
0.8552	High Similarity	NPC155205
0.8543	High Similarity	NPC91809
0.8533	High Similarity	NPC4423
0.8533	High Similarity	NPC77325
0.8531	High Similarity	NPC158481
0.8521	High Similarity	NPC474097
0.8521	High Similarity	NPC175943
0.8521	High Similarity	NPC474519
0.8521	High Similarity	NPC474394
0.8514	High Similarity	NPC473692
0.8511	High Similarity	NPC476389
0.8506	High Similarity	NPC472889
0.8506	High Similarity	NPC246466
0.8503	High Similarity	NPC471643
0.8503	High Similarity	NPC471639
0.85	High Similarity	NPC147757
0.8497	Intermediate Similarity	NPC472890
0.8497	Intermediate Similarity	NPC69043
0.8497	Intermediate Similarity	NPC478230
0.8497	Intermediate Similarity	NPC317585
0.8493	Intermediate Similarity	NPC90411
0.8487	Intermediate Similarity	NPC478224
0.8483	Intermediate Similarity	NPC162939
0.8483	Intermediate Similarity	NPC114620
0.8483	Intermediate Similarity	NPC103337
0.8477	Intermediate Similarity	NPC60413
0.8467	Intermediate Similarity	NPC221352
0.8462	Intermediate Similarity	NPC290803
0.8462	Intermediate Similarity	NPC142027
0.8462	Intermediate Similarity	NPC180905
0.8462	Intermediate Similarity	NPC182496
0.8435	Intermediate Similarity	NPC471644
0.8435	Intermediate Similarity	NPC471640
0.8435	Intermediate Similarity	NPC250755
0.8431	Intermediate Similarity	NPC472211
0.8429	Intermediate Similarity	NPC92624
0.8421	Intermediate Similarity	NPC215921
0.8421	Intermediate Similarity	NPC240768
0.8421	Intermediate Similarity	NPC70016
0.8421	Intermediate Similarity	NPC200773
0.8417	Intermediate Similarity	NPC209959
0.8414	Intermediate Similarity	NPC221104
0.8411	Intermediate Similarity	NPC237440
0.8411	Intermediate Similarity	NPC270160
0.8411	Intermediate Similarity	NPC6923
0.8408	Intermediate Similarity	NPC474096
0.8403	Intermediate Similarity	NPC474726
0.8403	Intermediate Similarity	NPC291454
0.8403	Intermediate Similarity	NPC475955
0.8403	Intermediate Similarity	NPC50455
0.8403	Intermediate Similarity	NPC118919
0.84	Intermediate Similarity	NPC166583
0.84	Intermediate Similarity	NPC259632
0.84	Intermediate Similarity	NPC471734
0.84	Intermediate Similarity	NPC53362
0.8389	Intermediate Similarity	NPC134621
0.8387	Intermediate Similarity	NPC478225
0.8387	Intermediate Similarity	NPC478226
0.8377	Intermediate Similarity	NPC79998
0.8369	Intermediate Similarity	NPC259942
0.8367	Intermediate Similarity	NPC307990
0.8367	Intermediate Similarity	NPC110810
0.8367	Intermediate Similarity	NPC16455
0.8367	Intermediate Similarity	NPC470842
0.8356	Intermediate Similarity	NPC471819
0.8356	Intermediate Similarity	NPC247409
0.8345	Intermediate Similarity	NPC261292
0.8345	Intermediate Similarity	NPC471452
0.8345	Intermediate Similarity	NPC301915
0.8344	Intermediate Similarity	NPC172329
0.8344	Intermediate Similarity	NPC2569
0.8344	Intermediate Similarity	NPC94781
0.8344	Intermediate Similarity	NPC201560
0.8333	Intermediate Similarity	NPC471735
0.8333	Intermediate Similarity	NPC130899
0.8333	Intermediate Similarity	NPC237208

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 NPC354984 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	285
0.1-0.2	961
0.2-0.3	1929
0.3-0.4	2730
0.4-0.5	1868
0.5-0.6	990
0.6-0.7	305
0.7-0.8	78
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8356	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD2534	Approved
0.8267	Intermediate Similarity	NPD2533	Approved
0.8267	Intermediate Similarity	NPD2532	Approved
0.8027	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7819	Suspended
0.7925	Intermediate Similarity	NPD7075	Discontinued
0.7908	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6799	Approved
0.7843	Intermediate Similarity	NPD7390	Discontinued
0.7823	Intermediate Similarity	NPD230	Phase 1
0.7799	Intermediate Similarity	NPD3817	Phase 2
0.7771	Intermediate Similarity	NPD6599	Discontinued
0.7736	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7411	Suspended
0.7688	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD1934	Approved
0.7673	Intermediate Similarity	NPD6801	Discontinued
0.7669	Intermediate Similarity	NPD6959	Discontinued
0.7667	Intermediate Similarity	NPD1510	Phase 2
0.764	Intermediate Similarity	NPD3882	Suspended
0.7635	Intermediate Similarity	NPD1240	Approved
0.7635	Intermediate Similarity	NPD943	Approved
0.7632	Intermediate Similarity	NPD1549	Phase 2
0.7622	Intermediate Similarity	NPD6232	Discontinued
0.759	Intermediate Similarity	NPD7473	Discontinued
0.7547	Intermediate Similarity	NPD4380	Phase 2
0.7533	Intermediate Similarity	NPD1607	Approved
0.7532	Intermediate Similarity	NPD3750	Approved
0.753	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6166	Phase 2
0.753	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD1512	Approved
0.7515	Intermediate Similarity	NPD5710	Approved
0.7515	Intermediate Similarity	NPD5711	Approved
0.75	Intermediate Similarity	NPD5404	Approved
0.75	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD5408	Approved
0.75	Intermediate Similarity	NPD5406	Approved
0.75	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD5405	Approved
0.7469	Intermediate Similarity	NPD5402	Approved
0.7447	Intermediate Similarity	NPD9545	Approved
0.7431	Intermediate Similarity	NPD9269	Phase 2
0.7427	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD6797	Phase 2
0.7407	Intermediate Similarity	NPD2801	Approved
0.7396	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD9268	Approved
0.7389	Intermediate Similarity	NPD1511	Approved
0.7378	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3749	Approved
0.7375	Intermediate Similarity	NPD3226	Approved
0.7368	Intermediate Similarity	NPD7251	Discontinued
0.7361	Intermediate Similarity	NPD1201	Approved
0.7358	Intermediate Similarity	NPD5403	Approved
0.7355	Intermediate Similarity	NPD2800	Approved
0.7355	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7808	Phase 3
0.7317	Intermediate Similarity	NPD7768	Phase 2
0.7305	Intermediate Similarity	NPD9493	Approved
0.7294	Intermediate Similarity	NPD5844	Phase 1
0.7288	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1470	Approved
0.7273	Intermediate Similarity	NPD1551	Phase 2
0.7267	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6190	Approved
0.7251	Intermediate Similarity	NPD7074	Phase 3
0.7235	Intermediate Similarity	NPD3818	Discontinued
0.7233	Intermediate Similarity	NPD5401	Approved
0.7233	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD919	Approved
0.7209	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD3748	Approved
0.7193	Intermediate Similarity	NPD7054	Approved
0.719	Intermediate Similarity	NPD6651	Approved
0.7183	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD1164	Approved
0.7159	Intermediate Similarity	NPD8150	Discontinued
0.7152	Intermediate Similarity	NPD3764	Approved
0.7151	Intermediate Similarity	NPD7472	Approved
0.7143	Intermediate Similarity	NPD920	Approved
0.7143	Intermediate Similarity	NPD1247	Approved
0.7135	Intermediate Similarity	NPD3751	Discontinued
0.7134	Intermediate Similarity	NPD1243	Approved
0.7101	Intermediate Similarity	NPD74	Approved
0.7101	Intermediate Similarity	NPD3787	Discontinued
0.7101	Intermediate Similarity	NPD9266	Approved
0.7091	Intermediate Similarity	NPD1465	Phase 2
0.7089	Intermediate Similarity	NPD4628	Phase 3
0.7089	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5494	Approved
0.7069	Intermediate Similarity	NPD6559	Discontinued
0.7051	Intermediate Similarity	NPD6100	Approved
0.7051	Intermediate Similarity	NPD6099	Approved
0.7034	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD9263	Approved
0.7029	Intermediate Similarity	NPD9267	Approved
0.7029	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD9264	Approved
0.7019	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD5953	Discontinued
0.7006	Intermediate Similarity	NPD2346	Discontinued
0.7	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3300	Phase 2
0.6994	Remote Similarity	NPD7286	Phase 2
0.6987	Remote Similarity	NPD2799	Discontinued
0.6959	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD9717	Approved
0.6928	Remote Similarity	NPD3268	Approved
0.6928	Remote Similarity	NPD37	Approved
0.6923	Remote Similarity	NPD6234	Discontinued
0.6919	Remote Similarity	NPD2403	Approved
0.6918	Remote Similarity	NPD2654	Approved
0.6905	Remote Similarity	NPD4967	Phase 2
0.6905	Remote Similarity	NPD4966	Approved
0.6905	Remote Similarity	NPD4965	Approved
0.6903	Remote Similarity	NPD447	Suspended
0.6898	Remote Similarity	NPD7435	Discontinued
0.6883	Remote Similarity	NPD6663	Approved
0.6879	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD8320	Phase 1
0.6862	Remote Similarity	NPD8319	Approved
0.686	Remote Similarity	NPD3926	Phase 2
0.6842	Remote Similarity	NPD5736	Approved
0.6839	Remote Similarity	NPD4060	Phase 1
0.6831	Remote Similarity	NPD6535	Approved
0.6831	Remote Similarity	NPD6534	Approved
0.6829	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1203	Approved
0.6818	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD411	Approved
0.681	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD4750	Phase 3
0.6806	Remote Similarity	NPD9281	Approved
0.6802	Remote Similarity	NPD7229	Phase 3
0.6797	Remote Similarity	NPD6832	Phase 2
0.6796	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD6355	Discontinued
0.6792	Remote Similarity	NPD2344	Approved
0.6792	Remote Similarity	NPD1471	Phase 3
0.6788	Remote Similarity	NPD846	Approved
0.6788	Remote Similarity	NPD940	Approved
0.6779	Remote Similarity	NPD422	Phase 1
0.6778	Remote Similarity	NPD8434	Phase 2
0.6774	Remote Similarity	NPD520	Approved
0.6772	Remote Similarity	NPD7033	Discontinued
0.6757	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD4626	Approved
0.6747	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7199	Phase 2
0.6742	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD9261	Approved
0.6738	Remote Similarity	NPD6777	Approved
0.6738	Remote Similarity	NPD6779	Approved
0.6738	Remote Similarity	NPD6778	Approved
0.6738	Remote Similarity	NPD6776	Approved
0.6738	Remote Similarity	NPD6780	Approved
0.6738	Remote Similarity	NPD6781	Approved
0.6738	Remote Similarity	NPD6782	Approved
0.6733	Remote Similarity	NPD1608	Approved
0.6725	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.672	Remote Similarity	NPD7700	Phase 2
0.672	Remote Similarity	NPD7699	Phase 2
0.6719	Remote Similarity	NPD8151	Discontinued
0.671	Remote Similarity	NPD2313	Discontinued
0.671	Remote Similarity	NPD6798	Discontinued
0.6704	Remote Similarity	NPD8312	Approved
0.6704	Remote Similarity	NPD8313	Approved
0.6689	Remote Similarity	NPD5691	Approved
0.6687	Remote Similarity	NPD7236	Approved
0.6684	Remote Similarity	NPD7874	Approved
0.6684	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3400	Discontinued
0.6667	Remote Similarity	NPD8166	Discontinued
0.6667	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD1019	Discontinued
0.6649	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7228	Approved
0.6647	Remote Similarity	NPD5353	Approved
0.6647	Remote Similarity	NPD4288	Approved
0.6646	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3019	Approved
0.6644	Remote Similarity	NPD2932	Approved
0.6632	Remote Similarity	NPD7698	Approved
0.6632	Remote Similarity	NPD7697	Approved
0.6632	Remote Similarity	NPD7696	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