NPASS Compound

Structure

CID91809 OpenBabel06191715432D 29 31 0 0 1 0 0 0 0 0999 V2000 -2.1907 -1.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 0.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 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 4.3301 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8637 -1.0353 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 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3120 0.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8978 -0.7765 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 -4.5708 -0.3282 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3461 0.8966 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 -2.6390 0.1895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6730 0.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5367 -0.5870 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0872 1.8625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4142 1.4142 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9659 -0.2588 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 14 1 0 0 0 0 5 22 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 12 1 0 0 0 0 7 14 2 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 10 28 1 0 0 0 0 11 18 1 0 0 0 0 12 15 1 0 0 0 0 13 23 1 0 0 0 0 14 28 1 0 0 0 0 15 19 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 21 1 0 0 0 0 17 25 2 0 0 0 0 18 20 1 0 0 0 0 19 21 1 0 0 0 0 19 26 2 0 0 0 0 20 27 2 0 0 0 0 20 29 1 0 0 0 0 21 2 1 1 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.1
Volume:	390.06
LogP:	1.833
LogD:	2.17
LogS:	-3.06
# Rotatable Bonds:	5
TPSA:	130.36
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.517
Synthetic Accessibility Score:	4.112
Fsp3:	0.19
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.256
MDCK Permeability:	2.0173929442535155e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.025
Human Intestinal Absorption (HIA):	0.904
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.061
Plasma Protein Binding (PPB):	78.35521697998047%
Volume Distribution (VD):	1.03
Pgp-substrate:	13.314382553100586%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.283
CYP2C19-inhibitor:	0.343
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.616
CYP2C9-substrate:	0.533
CYP2D6-inhibitor:	0.746
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.828
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	2.676
Half-life (T1/2):	0.93

ADMET: Toxicity

hERG Blockers:	0.03
Human Hepatotoxicity (H-HT):	0.952
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.787
Rat Oral Acute Toxicity:	0.673
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.945
Carcinogencity:	0.732
Eye Corrosion:	0.003
Eye Irritation:	0.235
Respiratory Toxicity:	0.254

Download Data

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

Natural Product: NPC91809

Natural Product ID:	NPC91809
*Common Name:**	(-)-Mitorubrinol
IUPAC Name:	[(7R)-3-[(E)-3-hydroxyprop-1-enyl]-7-methyl-6,8-dioxoisochromen-7-yl] 2,4-dihydroxy-6-methylbenzoate
Synonyms:
Standard InCHIKey:	NXJNWGPNUAVXHT-YEFOHOTDSA-N
Standard InCHI:	InChI=1S/C21H18O8/c1-11-6-13(23)9-16(24)18(11)20(27)29-21(2)17(25)8-12-7-14(4-3-5-22)28-10-15(12)19(21)26/h3-4,6-10,22-24H,5H2,1-2H3/b4-3+/t21-/m1/s1
SMILES:	Cc1cc(cc(c1C(=O)O[C@]1(C)C(=O)C=C2C=C(/C=C/CO)OC=C2C1=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3609760
PubChem CID:	11990358
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0003477] Azaphilones

*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
NPO10881	Gyrophyllum sibogae	Species	Pennatulidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15270580]
NPO3909	Leucas aspera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872130]
NPO33444	penicillium pinophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22264170]
NPO33444	penicillium pinophilum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26291474]
NPO33693	Talaromyces aculeatus DS-62013	Species	Trichocomaceae	Eukaryota	n.a.	saline-alkali soil, Shandong Province, China	2013-APR	PMID[28749670]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3909	Leucas aspera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5411	Talaromyces austrocalifornicus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15056	Helianthus pumilus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10881	Gyrophyllum sibogae	Species	Pennatulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3221	Schkuhria anthemoidea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3909	Leucas aspera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO263	Clibadium microcephalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17828	Talaromyces ruber	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9306	Globularia nudicaulis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15438	Stemona parviflora	Species	Stemonaceae	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
IC50	1

Activity Type	# Activity
PROTEIN FAMILY	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20648	PROTEIN FAMILY	Alpha glucosidase	Homo sapiens	IC50	>	200000.0	nM	PMID[538063]

☑ 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 NPC91809 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	342
0.1-0.2	1522
0.2-0.3	3609
0.3-0.4	8021
0.4-0.5	10352
0.5-0.6	4274
0.6-0.7	6511
0.7-0.8	7131
0.8-0.85	789
0.85-0.9	116
0.9-0.95	24
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC164762
0.9861	High Similarity	NPC84142
0.9533	High Similarity	NPC472889
0.953	High Similarity	NPC317585
0.9527	High Similarity	NPC478224
0.94	High Similarity	NPC208173
0.94	High Similarity	NPC69043
0.94	High Similarity	NPC478221
0.94	High Similarity	NPC472890
0.94	High Similarity	NPC478230
0.94	High Similarity	NPC170189
0.9392	High Similarity	NPC472891
0.9346	High Similarity	NPC317544
0.9333	High Similarity	NPC137301
0.9276	High Similarity	NPC478225
0.9267	High Similarity	NPC76041
0.9267	High Similarity	NPC115249
0.9267	High Similarity	NPC184284
0.9205	High Similarity	NPC478231
0.9172	High Similarity	NPC158634
0.9167	High Similarity	NPC52358
0.915	High Similarity	NPC246466
0.9041	High Similarity	NPC244923
0.9034	High Similarity	NPC32360
0.9034	High Similarity	NPC268052
0.9026	High Similarity	NPC478226
0.9	High Similarity	NPC215711
0.9	High Similarity	NPC73411
0.8994	High Similarity	NPC328321
0.8966	High Similarity	NPC478200
0.8966	High Similarity	NPC33144
0.8954	High Similarity	NPC471695
0.894	High Similarity	NPC77325
0.894	High Similarity	NPC4423
0.8933	High Similarity	NPC210320
0.8931	High Similarity	NPC283041
0.8919	High Similarity	NPC478202
0.8912	High Similarity	NPC472035
0.8912	High Similarity	NPC478201
0.8904	High Similarity	NPC92655
0.8882	High Similarity	NPC56204
0.8868	High Similarity	NPC20237
0.8851	High Similarity	NPC474385
0.8844	High Similarity	NPC156872
0.8844	High Similarity	NPC158472
0.8836	High Similarity	NPC212693
0.8836	High Similarity	NPC191835
0.8836	High Similarity	NPC94248
0.8819	High Similarity	NPC175943
0.8808	High Similarity	NPC472036
0.8808	High Similarity	NPC52106
0.8805	High Similarity	NPC191930
0.88	High Similarity	NPC472034
0.88	High Similarity	NPC257558
0.8784	High Similarity	NPC53649
0.8784	High Similarity	NPC478217
0.8784	High Similarity	NPC313123
0.8776	High Similarity	NPC247409
0.8774	High Similarity	NPC99381
0.8767	High Similarity	NPC70380
0.875	High Similarity	NPC240622
0.875	High Similarity	NPC471641
0.875	High Similarity	NPC240253
0.875	High Similarity	NPC471642
0.875	High Similarity	NPC153783
0.8742	High Similarity	NPC249181
0.8742	High Similarity	NPC472033
0.8733	High Similarity	NPC210966
0.8733	High Similarity	NPC475201
0.8733	High Similarity	NPC210425
0.8733	High Similarity	NPC478203
0.8733	High Similarity	NPC277426
0.8733	High Similarity	NPC126882
0.8733	High Similarity	NPC42540
0.8733	High Similarity	NPC86373
0.8733	High Similarity	NPC151607
0.8733	High Similarity	NPC280404
0.8718	High Similarity	NPC472050
0.8707	High Similarity	NPC472602
0.8707	High Similarity	NPC9121
0.8707	High Similarity	NPC177307
0.8699	High Similarity	NPC235115
0.8693	High Similarity	NPC270160
0.8693	High Similarity	NPC237440
0.8693	High Similarity	NPC476684
0.8684	High Similarity	NPC259632
0.8675	High Similarity	NPC312789
0.8667	High Similarity	NPC51106
0.8667	High Similarity	NPC469542
0.8667	High Similarity	NPC472006
0.8667	High Similarity	NPC159721
0.8667	High Similarity	NPC471731
0.8658	High Similarity	NPC472604
0.8658	High Similarity	NPC475730
0.8658	High Similarity	NPC67650
0.8658	High Similarity	NPC1704
0.8658	High Similarity	NPC472605
0.8658	High Similarity	NPC472603
0.8649	High Similarity	NPC139634
0.8649	High Similarity	NPC105456
0.8639	High Similarity	NPC71256
0.8639	High Similarity	NPC135837
0.8636	High Similarity	NPC158866
0.8636	High Similarity	NPC295036
0.8627	High Similarity	NPC37139
0.8627	High Similarity	NPC221352
0.8618	High Similarity	NPC51513
0.8618	High Similarity	NPC202112
0.8618	High Similarity	NPC473023
0.8611	High Similarity	NPC189823
0.8611	High Similarity	NPC219892
0.86	High Similarity	NPC82913
0.86	High Similarity	NPC471733
0.86	High Similarity	NPC469579
0.86	High Similarity	NPC250755
0.8591	High Similarity	NPC155205
0.8591	High Similarity	NPC230902
0.8591	High Similarity	NPC472601
0.8591	High Similarity	NPC49242
0.8591	High Similarity	NPC472600
0.859	High Similarity	NPC155686
0.859	High Similarity	NPC472799
0.8581	High Similarity	NPC46882
0.8581	High Similarity	NPC472403
0.8581	High Similarity	NPC475974
0.8581	High Similarity	NPC70016
0.8581	High Similarity	NPC215921
0.8581	High Similarity	NPC132990
0.8571	High Similarity	NPC50455
0.8553	High Similarity	NPC472055
0.8553	High Similarity	NPC83272
0.8544	High Similarity	NPC263483
0.8543	High Similarity	NPC354984
0.8526	High Similarity	NPC470340
0.8523	High Similarity	NPC25427
0.8523	High Similarity	NPC295339
0.8516	High Similarity	NPC150928
0.8516	High Similarity	NPC469670
0.8516	High Similarity	NPC469619
0.8514	High Similarity	NPC474771
0.8514	High Similarity	NPC149372
0.8514	High Similarity	NPC474849
0.8514	High Similarity	NPC194579
0.8514	High Similarity	NPC178467
0.8514	High Similarity	NPC65837
0.8506	High Similarity	NPC172329
0.8506	High Similarity	NPC153417
0.8506	High Similarity	NPC2569
0.8503	High Similarity	NPC142027
0.8503	High Similarity	NPC27407
0.8503	High Similarity	NPC182496
0.8503	High Similarity	NPC180905
0.85	High Similarity	NPC117985
0.8497	Intermediate Similarity	NPC225173
0.8497	Intermediate Similarity	NPC153758
0.8497	Intermediate Similarity	NPC107625
0.8497	Intermediate Similarity	NPC163846
0.8491	Intermediate Similarity	NPC470339
0.8487	Intermediate Similarity	NPC95123
0.8487	Intermediate Similarity	NPC470216
0.8487	Intermediate Similarity	NPC66404
0.8477	Intermediate Similarity	NPC49108
0.8476	Intermediate Similarity	NPC193698
0.8471	Intermediate Similarity	NPC169990
0.8471	Intermediate Similarity	NPC210942
0.8467	Intermediate Similarity	NPC109007
0.8462	Intermediate Similarity	NPC240768
0.8462	Intermediate Similarity	NPC200773
0.8462	Intermediate Similarity	NPC230848
0.8457	Intermediate Similarity	NPC472049
0.8456	Intermediate Similarity	NPC61590
0.8452	Intermediate Similarity	NPC65775
0.8452	Intermediate Similarity	NPC474052
0.8452	Intermediate Similarity	NPC10027
0.8447	Intermediate Similarity	NPC473022
0.8446	Intermediate Similarity	NPC158481
0.8442	Intermediate Similarity	NPC125801
0.8442	Intermediate Similarity	NPC471734
0.8442	Intermediate Similarity	NPC12305
0.8442	Intermediate Similarity	NPC14098
0.8438	Intermediate Similarity	NPC243701
0.8435	Intermediate Similarity	NPC474097
0.8431	Intermediate Similarity	NPC474630
0.8431	Intermediate Similarity	NPC28632
0.8431	Intermediate Similarity	NPC134621
0.8421	Intermediate Similarity	NPC215451
0.8421	Intermediate Similarity	NPC277369
0.8421	Intermediate Similarity	NPC472610
0.8418	Intermediate Similarity	NPC80534
0.8418	Intermediate Similarity	NPC237560
0.8418	Intermediate Similarity	NPC56786
0.8415	Intermediate Similarity	NPC473095
0.8415	Intermediate Similarity	NPC473096
0.8411	Intermediate Similarity	NPC37530
0.8411	Intermediate Similarity	NPC90411
0.8408	Intermediate Similarity	NPC271681
0.8408	Intermediate Similarity	NPC167903
0.8408	Intermediate Similarity	NPC273483
0.84	Intermediate Similarity	NPC88269
0.84	Intermediate Similarity	NPC474655

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 NPC91809 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	298
0.1-0.2	947
0.2-0.3	1751
0.3-0.4	2612
0.4-0.5	1957
0.5-0.6	1088
0.6-0.7	343
0.7-0.8	142
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8649	High Similarity	NPD970	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD7819	Suspended
0.8313	Intermediate Similarity	NPD7075	Discontinued
0.8302	Intermediate Similarity	NPD3817	Phase 2
0.8291	Intermediate Similarity	NPD6801	Discontinued
0.8247	Intermediate Similarity	NPD6799	Approved
0.82	Intermediate Similarity	NPD1510	Phase 2
0.8194	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD2533	Approved
0.8194	Intermediate Similarity	NPD2532	Approved
0.8194	Intermediate Similarity	NPD2534	Approved
0.817	Intermediate Similarity	NPD3750	Approved
0.8165	Intermediate Similarity	NPD6599	Discontinued
0.8125	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8089	Intermediate Similarity	NPD5403	Approved
0.8075	Intermediate Similarity	NPD5402	Approved
0.8052	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD4380	Phase 2
0.8025	Intermediate Similarity	NPD3882	Suspended
0.8	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD7411	Suspended
0.7964	Intermediate Similarity	NPD7473	Discontinued
0.7962	Intermediate Similarity	NPD5401	Approved
0.7962	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD1607	Approved
0.7933	Intermediate Similarity	NPD1240	Approved
0.7922	Intermediate Similarity	NPD1549	Phase 2
0.7911	Intermediate Similarity	NPD1512	Approved
0.7908	Intermediate Similarity	NPD2796	Approved
0.7895	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6797	Phase 2
0.7866	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD3749	Approved
0.7857	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD3748	Approved
0.7843	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7251	Discontinued
0.7831	Intermediate Similarity	NPD6959	Discontinued
0.7798	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6166	Phase 2
0.7798	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1551	Phase 2
0.7791	Intermediate Similarity	NPD7808	Phase 3
0.7791	Intermediate Similarity	NPD2801	Approved
0.7791	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1511	Approved
0.7765	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD230	Phase 1
0.7744	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD1934	Approved
0.7727	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD8150	Discontinued
0.7707	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3818	Discontinued
0.7697	Intermediate Similarity	NPD7768	Phase 2
0.7677	Intermediate Similarity	NPD2935	Discontinued
0.7673	Intermediate Similarity	NPD7390	Discontinued
0.7661	Intermediate Similarity	NPD7054	Approved
0.7661	Intermediate Similarity	NPD5844	Phase 1
0.7658	Intermediate Similarity	NPD6190	Approved
0.7654	Intermediate Similarity	NPD3226	Approved
0.7639	Intermediate Similarity	NPD9545	Approved
0.7616	Intermediate Similarity	NPD7472	Approved
0.7605	Intermediate Similarity	NPD919	Approved
0.7597	Intermediate Similarity	NPD6651	Approved
0.759	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5710	Approved
0.7574	Intermediate Similarity	NPD5711	Approved
0.7566	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3764	Approved
0.7564	Intermediate Similarity	NPD5404	Approved
0.7564	Intermediate Similarity	NPD5408	Approved
0.7564	Intermediate Similarity	NPD5406	Approved
0.7564	Intermediate Similarity	NPD5405	Approved
0.7532	Intermediate Similarity	NPD2800	Approved
0.7532	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6559	Discontinued
0.7514	Intermediate Similarity	NPD7074	Phase 3
0.75	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD9493	Approved
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD943	Approved
0.7452	Intermediate Similarity	NPD6099	Approved
0.7452	Intermediate Similarity	NPD6100	Approved
0.7423	Intermediate Similarity	NPD920	Approved
0.7421	Intermediate Similarity	NPD1243	Approved
0.7419	Intermediate Similarity	NPD7435	Discontinued
0.7405	Intermediate Similarity	NPD2346	Discontinued
0.7391	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5953	Discontinued
0.7365	Intermediate Similarity	NPD1465	Phase 2
0.7351	Intermediate Similarity	NPD1470	Approved
0.7326	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD3926	Phase 2
0.732	Intermediate Similarity	NPD6832	Phase 2
0.7318	Intermediate Similarity	NPD8434	Phase 2
0.7317	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1201	Approved
0.7301	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD8320	Phase 1
0.7287	Intermediate Similarity	NPD8319	Approved
0.7283	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2799	Discontinued
0.7278	Intermediate Similarity	NPD7033	Discontinued
0.7268	Intermediate Similarity	NPD6535	Approved
0.7268	Intermediate Similarity	NPD6534	Approved
0.7267	Intermediate Similarity	NPD3787	Discontinued
0.7267	Intermediate Similarity	NPD9717	Approved
0.726	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6780	Approved
0.7258	Intermediate Similarity	NPD6781	Approved
0.7258	Intermediate Similarity	NPD6777	Approved
0.7258	Intermediate Similarity	NPD6776	Approved
0.7258	Intermediate Similarity	NPD6778	Approved
0.7258	Intermediate Similarity	NPD6779	Approved
0.7258	Intermediate Similarity	NPD6782	Approved
0.7251	Intermediate Similarity	NPD5494	Approved
0.7238	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1203	Approved
0.7229	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD411	Approved
0.7219	Intermediate Similarity	NPD4288	Approved
0.7209	Intermediate Similarity	NPD7199	Phase 2
0.7209	Intermediate Similarity	NPD1247	Approved
0.7202	Intermediate Similarity	NPD37	Approved
0.72	Intermediate Similarity	NPD422	Phase 1
0.7195	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2798	Approved
0.7188	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7874	Approved
0.7188	Intermediate Similarity	NPD2344	Approved
0.7178	Intermediate Similarity	NPD7236	Approved
0.7176	Intermediate Similarity	NPD4967	Phase 2
0.7176	Intermediate Similarity	NPD4966	Approved
0.7176	Intermediate Similarity	NPD4965	Approved
0.717	Intermediate Similarity	NPD4308	Phase 3
0.7167	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7286	Phase 2
0.7151	Intermediate Similarity	NPD7699	Phase 2
0.7151	Intermediate Similarity	NPD8313	Approved
0.7151	Intermediate Similarity	NPD7700	Phase 2
0.7151	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD7697	Approved
0.7143	Intermediate Similarity	NPD7698	Approved
0.7143	Intermediate Similarity	NPD7696	Phase 3
0.7115	Intermediate Similarity	NPD3268	Approved
0.7115	Intermediate Similarity	NPD2313	Discontinued
0.7105	Intermediate Similarity	NPD7870	Phase 2
0.7105	Intermediate Similarity	NPD7871	Phase 2
0.7093	Intermediate Similarity	NPD6234	Discontinued
0.7089	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD447	Suspended
0.7089	Intermediate Similarity	NPD5124	Phase 1
0.7086	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1471	Phase 3
0.7073	Intermediate Similarity	NPD3300	Phase 2
0.7066	Intermediate Similarity	NPD7239	Suspended
0.7055	Intermediate Similarity	NPD8166	Discontinued
0.7055	Intermediate Similarity	NPD7003	Approved
0.7048	Intermediate Similarity	NPD6273	Approved
0.7047	Intermediate Similarity	NPD8151	Discontinued
0.7039	Intermediate Similarity	NPD9269	Phase 2
0.7025	Intermediate Similarity	NPD4060	Phase 1
0.7024	Intermediate Similarity	NPD7458	Discontinued
0.7013	Intermediate Similarity	NPD2797	Approved
0.7013	Intermediate Similarity	NPD1164	Approved
0.7012	Intermediate Similarity	NPD2309	Approved
0.7006	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9268	Approved
0.6995	Remote Similarity	NPD7701	Phase 2
0.6994	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2654	Approved
0.6993	Remote Similarity	NPD4749	Approved
0.6971	Remote Similarity	NPD7229	Phase 3
0.6964	Remote Similarity	NPD1653	Approved
0.6957	Remote Similarity	NPD4287	Approved
0.6957	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4626	Approved
0.6944	Remote Similarity	NPD9266	Approved
0.6944	Remote Similarity	NPD74	Approved
0.6944	Remote Similarity	NPD7685	Pre-registration
0.6943	Remote Similarity	NPD4625	Phase 3
0.6928	Remote Similarity	NPD3972	Approved
0.6928	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD4307	Phase 2
0.6918	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7177	Discontinued
0.691	Remote Similarity	NPD7228	Approved
0.691	Remote Similarity	NPD7799	Discontinued
0.6899	Remote Similarity	NPD6798	Discontinued
0.6895	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD2403	Approved
0.6888	Remote Similarity	NPD7801	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data