NPASS Compound

Structure

CID51292 OpenBabel06191715382D 28 32 0 0 1 0 0 0 0 0999 V2000 -1.8569 -1.5721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8399 4.2573 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9528 -1.7640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8740 3.9436 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3346 -1.0771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5557 1.6795 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9372 2.3663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6627 2.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2701 0.8005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0332 2.1741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5695 -1.2690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6171 1.8207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6171 1.0334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8557 1.9350 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9762 2.4428 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.3661 0.6083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0965 1.9348 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7477 1.2951 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8559 0.9194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1878 -0.5820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9040 -0.1921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6108 0.2399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9764 0.4113 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0967 0.9192 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2800 -1.0364 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5147 0.4323 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1979 -0.6880 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 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 8 1 0 0 0 0 5 11 1 0 0 0 0 6 7 2 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 8 17 1 0 0 0 0 9 16 2 0 0 0 0 10 18 2 0 0 0 0 11 20 2 0 0 0 0 12 13 1 0 0 0 0 12 15 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 19 2 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 16 21 1 0 0 0 0 17 24 1 6 0 0 0 18 24 1 0 0 0 0 19 22 1 0 0 0 0 19 23 1 0 0 0 0 20 23 1 0 0 0 0 20 27 1 0 0 0 0 21 25 2 0 0 0 0 21 28 1 0 0 0 0 22 26 2 0 0 0 0 22 27 1 0 0 0 0 24 23 1 1 0 0 0 24 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.14
Volume:	327.905
LogP:	0.734
LogD:	0.714
LogS:	-2.247
# Rotatable Bonds:	3
TPSA:	94.59
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.205
Synthetic Accessibility Score:	5.285
Fsp3:	0.647
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.128
MDCK Permeability:	7.797328726155683e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.346
20% Bioavailability (F20%):	0.075
30% Bioavailability (F30%):	0.747

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107
Plasma Protein Binding (PPB):	55.888023376464844%
Volume Distribution (VD):	1.266
Pgp-substrate:	44.91813659667969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.153
CYP2C9-inhibitor:	0.05
CYP2C9-substrate:	0.071
CYP2D6-inhibitor:	0.282
CYP2D6-substrate:	0.176
CYP3A4-inhibitor:	0.135
CYP3A4-substrate:	0.225

ADMET: Excretion

Clearance (CL):	2.865
Half-life (T1/2):	0.773

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.893
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.87
Rat Oral Acute Toxicity:	0.362
Maximum Recommended Daily Dose:	0.281
Skin Sensitization:	0.61
Carcinogencity:	0.55
Eye Corrosion:	0.292
Eye Irritation:	0.214
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC51292

Natural Product ID:	NPC51292
*Common Name:**	Ansaspirolide
IUPAC Name:	n.a.
Synonyms:	Ansaspirolide
Standard InCHIKey:	KKXDPTDDMLHVAK-POLTTXONSA-N
Standard InCHI:	InChI=1S/C24H26O4/c1-3-5-11-20-23-13-12-15(14-19(23)22(26)27-20)17(8-4-2)24(23)18-10-7-6-9-16(18)21(25)28-24/h6-7,9-11,14-15,17H,3-5,8,12-13H2,1-2H3/b20-11-/t15?,17-,23?,24+/m1/s1
SMILES:	CCC/C=C/1OC(=O)C2=CC3CCC12[C@]1(OC(=O)c2c1cccc2)[C@@H]3CCC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482223
PubChem CID:	44575265
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0001578] Benzofuranones

*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
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374978]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679317]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	roots	purchased from Kiu Shun Trading Ltd., Vancouver, Canada	2000	PMID[16643021]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[17997069]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25538068]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27400088]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15462	Angelica sinensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11438	Angelica gigas	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2921	Angelica acutiloba	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15462	Angelica sinensis	Species	Apiaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1785	Individual Protein	Serotonin 7 (5-HT7) receptor	Homo sapiens	Inhibition	=	19.0	%	PMID[531592]

☑ 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 NPC51292 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	329
0.1-0.2	1351
0.2-0.3	2039
0.3-0.4	5299
0.4-0.5	11327
0.5-0.6	14128
0.6-0.7	6992
0.7-0.8	1163
0.8-0.85	67
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.881	High Similarity	NPC121272
0.8538	High Similarity	NPC147561
0.8361	Intermediate Similarity	NPC307651
0.8333	Intermediate Similarity	NPC470278
0.8333	Intermediate Similarity	NPC232958
0.8284	Intermediate Similarity	NPC474608
0.8268	Intermediate Similarity	NPC50872
0.8248	Intermediate Similarity	NPC477904
0.8248	Intermediate Similarity	NPC183270
0.8235	Intermediate Similarity	NPC37622
0.8235	Intermediate Similarity	NPC30594
0.8222	Intermediate Similarity	NPC291638
0.8222	Intermediate Similarity	NPC473216
0.8222	Intermediate Similarity	NPC472577
0.8222	Intermediate Similarity	NPC473399
0.8222	Intermediate Similarity	NPC195647
0.8222	Intermediate Similarity	NPC17877
0.8222	Intermediate Similarity	NPC66761
0.8189	Intermediate Similarity	NPC77000
0.8189	Intermediate Similarity	NPC238861
0.8168	Intermediate Similarity	NPC169913
0.813	Intermediate Similarity	NPC128368
0.812	Intermediate Similarity	NPC471832
0.8102	Intermediate Similarity	NPC183122
0.8102	Intermediate Similarity	NPC283375
0.8102	Intermediate Similarity	NPC475373
0.8092	Intermediate Similarity	NPC470765
0.8092	Intermediate Similarity	NPC476599
0.8092	Intermediate Similarity	NPC275576
0.808	Intermediate Similarity	NPC149691
0.8077	Intermediate Similarity	NPC51079
0.8065	Intermediate Similarity	NPC196075
0.8049	Intermediate Similarity	NPC270699
0.8049	Intermediate Similarity	NPC82899
0.8049	Intermediate Similarity	NPC212415
0.8043	Intermediate Similarity	NPC475652
0.8043	Intermediate Similarity	NPC214550
0.8043	Intermediate Similarity	NPC210591
0.8033	Intermediate Similarity	NPC196246
0.8033	Intermediate Similarity	NPC214067
0.803	Intermediate Similarity	NPC473220
0.803	Intermediate Similarity	NPC470753
0.8029	Intermediate Similarity	NPC472551
0.8029	Intermediate Similarity	NPC472545
0.8015	Intermediate Similarity	NPC203486
0.8015	Intermediate Similarity	NPC329913
0.8015	Intermediate Similarity	NPC295664
0.8	Intermediate Similarity	NPC472394
0.8	Intermediate Similarity	NPC210092
0.8	Intermediate Similarity	NPC238370
0.8	Intermediate Similarity	NPC209632
0.8	Intermediate Similarity	NPC474095
0.7986	Intermediate Similarity	NPC211137
0.7986	Intermediate Similarity	NPC473112
0.7986	Intermediate Similarity	NPC473081
0.7986	Intermediate Similarity	NPC90614
0.7986	Intermediate Similarity	NPC43241
0.7986	Intermediate Similarity	NPC473613
0.7986	Intermediate Similarity	NPC473109
0.7986	Intermediate Similarity	NPC100913
0.7986	Intermediate Similarity	NPC171207
0.7986	Intermediate Similarity	NPC184747
0.7986	Intermediate Similarity	NPC476094
0.7986	Intermediate Similarity	NPC200592
0.7986	Intermediate Similarity	NPC275592
0.7986	Intermediate Similarity	NPC473085
0.7986	Intermediate Similarity	NPC48017
0.7986	Intermediate Similarity	NPC473758
0.7986	Intermediate Similarity	NPC472547
0.7986	Intermediate Similarity	NPC97667
0.7986	Intermediate Similarity	NPC4341
0.7986	Intermediate Similarity	NPC473060
0.7986	Intermediate Similarity	NPC147880
0.7984	Intermediate Similarity	NPC144547
0.7971	Intermediate Similarity	NPC39549
0.7967	Intermediate Similarity	NPC474157
0.7967	Intermediate Similarity	NPC305912
0.7967	Intermediate Similarity	NPC1082
0.7951	Intermediate Similarity	NPC265407
0.7951	Intermediate Similarity	NPC10251
0.7951	Intermediate Similarity	NPC17417
0.7951	Intermediate Similarity	NPC83628
0.7941	Intermediate Similarity	NPC472656
0.7937	Intermediate Similarity	NPC226093
0.7937	Intermediate Similarity	NPC135730
0.7929	Intermediate Similarity	NPC291599
0.7929	Intermediate Similarity	NPC87448
0.7929	Intermediate Similarity	NPC97947
0.7929	Intermediate Similarity	NPC118080
0.7929	Intermediate Similarity	NPC41481
0.7929	Intermediate Similarity	NPC472576
0.7929	Intermediate Similarity	NPC27377
0.7929	Intermediate Similarity	NPC16912
0.7917	Intermediate Similarity	NPC114594
0.7907	Intermediate Similarity	NPC289432
0.7907	Intermediate Similarity	NPC988
0.7907	Intermediate Similarity	NPC473243
0.7886	Intermediate Similarity	NPC251854
0.7886	Intermediate Similarity	NPC93084
0.7883	Intermediate Similarity	NPC126516
0.7883	Intermediate Similarity	NPC48929
0.7879	Intermediate Similarity	NPC246166
0.7869	Intermediate Similarity	NPC56493
0.7857	Intermediate Similarity	NPC228936
0.7857	Intermediate Similarity	NPC475400
0.7842	Intermediate Similarity	NPC307401
0.7836	Intermediate Similarity	NPC115797
0.7836	Intermediate Similarity	NPC51448
0.7832	Intermediate Similarity	NPC471107
0.7832	Intermediate Similarity	NPC471100
0.7829	Intermediate Similarity	NPC204784
0.782	Intermediate Similarity	NPC470818
0.7817	Intermediate Similarity	NPC177340
0.7817	Intermediate Similarity	NPC191387
0.7817	Intermediate Similarity	NPC246480
0.7817	Intermediate Similarity	NPC191082
0.7817	Intermediate Similarity	NPC270498
0.7817	Intermediate Similarity	NPC147217
0.7817	Intermediate Similarity	NPC475429
0.7817	Intermediate Similarity	NPC163087
0.7817	Intermediate Similarity	NPC131966
0.7817	Intermediate Similarity	NPC473673
0.7817	Intermediate Similarity	NPC139067
0.7812	Intermediate Similarity	NPC152812
0.7805	Intermediate Similarity	NPC99846
0.7805	Intermediate Similarity	NPC469636
0.7805	Intermediate Similarity	NPC269023
0.7801	Intermediate Similarity	NPC224491
0.7801	Intermediate Similarity	NPC476191
0.7787	Intermediate Similarity	NPC119271
0.7786	Intermediate Similarity	NPC471542
0.7778	Intermediate Similarity	NPC477411
0.7778	Intermediate Similarity	NPC153053
0.7778	Intermediate Similarity	NPC474935
0.777	Intermediate Similarity	NPC472372
0.777	Intermediate Similarity	NPC472374
0.7769	Intermediate Similarity	NPC31786
0.7762	Intermediate Similarity	NPC475122
0.7762	Intermediate Similarity	NPC470152
0.7762	Intermediate Similarity	NPC241951
0.7762	Intermediate Similarity	NPC51314
0.7762	Intermediate Similarity	NPC67777
0.7762	Intermediate Similarity	NPC95265
0.7762	Intermediate Similarity	NPC472569
0.7762	Intermediate Similarity	NPC163719
0.7762	Intermediate Similarity	NPC472573
0.7762	Intermediate Similarity	NPC11685
0.7762	Intermediate Similarity	NPC70716
0.7762	Intermediate Similarity	NPC188865
0.7762	Intermediate Similarity	NPC125106
0.7762	Intermediate Similarity	NPC25768
0.7762	Intermediate Similarity	NPC95810
0.7762	Intermediate Similarity	NPC475759
0.7762	Intermediate Similarity	NPC57628
0.7762	Intermediate Similarity	NPC476974
0.7762	Intermediate Similarity	NPC470231
0.7762	Intermediate Similarity	NPC472570
0.7754	Intermediate Similarity	NPC310662
0.7754	Intermediate Similarity	NPC298547
0.7754	Intermediate Similarity	NPC324898
0.7754	Intermediate Similarity	NPC134937
0.775	Intermediate Similarity	NPC45613
0.7746	Intermediate Similarity	NPC183540
0.7746	Intermediate Similarity	NPC472546
0.7746	Intermediate Similarity	NPC34012
0.7742	Intermediate Similarity	NPC174099
0.774	Intermediate Similarity	NPC303429
0.774	Intermediate Similarity	NPC222102
0.7731	Intermediate Similarity	NPC325497
0.7727	Intermediate Similarity	NPC472703
0.7721	Intermediate Similarity	NPC475508
0.7717	Intermediate Similarity	NPC186933
0.7717	Intermediate Similarity	NPC221275
0.7714	Intermediate Similarity	NPC327511
0.7714	Intermediate Similarity	NPC470742
0.7714	Intermediate Similarity	NPC205305
0.7708	Intermediate Similarity	NPC29704
0.7708	Intermediate Similarity	NPC469349
0.7708	Intermediate Similarity	NPC471104
0.7708	Intermediate Similarity	NPC472568
0.7708	Intermediate Similarity	NPC177940
0.7708	Intermediate Similarity	NPC476973
0.7708	Intermediate Similarity	NPC472572
0.7708	Intermediate Similarity	NPC470159
0.7708	Intermediate Similarity	NPC70403
0.7708	Intermediate Similarity	NPC96903
0.7708	Intermediate Similarity	NPC174982
0.7708	Intermediate Similarity	NPC184817
0.7708	Intermediate Similarity	NPC200471
0.7708	Intermediate Similarity	NPC472575
0.7708	Intermediate Similarity	NPC473088
0.7708	Intermediate Similarity	NPC158663
0.7708	Intermediate Similarity	NPC472571
0.7708	Intermediate Similarity	NPC171525
0.7708	Intermediate Similarity	NPC470157
0.7698	Intermediate Similarity	NPC92941
0.7698	Intermediate Similarity	NPC477893
0.7698	Intermediate Similarity	NPC477896
0.7698	Intermediate Similarity	NPC13784
0.7698	Intermediate Similarity	NPC149401

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 NPC51292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	828
0.2-0.3	1145
0.3-0.4	2722
0.4-0.5	2443
0.5-0.6	1378
0.6-0.7	320
0.7-0.8	31
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8189	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7951	Intermediate Similarity	NPD2182	Approved
0.7852	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD164	Approved
0.771	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD7236	Approved
0.7578	Intermediate Similarity	NPD5951	Approved
0.752	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2346	Discontinued
0.745	Intermediate Similarity	NPD7239	Suspended
0.741	Intermediate Similarity	NPD3764	Approved
0.7388	Intermediate Similarity	NPD6287	Discontinued
0.7372	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD7008	Discontinued
0.7308	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8032	Phase 2
0.7211	Intermediate Similarity	NPD7003	Approved
0.7211	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6273	Approved
0.72	Intermediate Similarity	NPD5909	Discontinued
0.7188	Intermediate Similarity	NPD2067	Discontinued
0.7183	Intermediate Similarity	NPD4307	Phase 2
0.7163	Intermediate Similarity	NPD2313	Discontinued
0.7154	Intermediate Similarity	NPD1238	Approved
0.7123	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD7057	Phase 3
0.7115	Intermediate Similarity	NPD7058	Phase 2
0.7103	Intermediate Similarity	NPD2799	Discontinued
0.7103	Intermediate Similarity	NPD3748	Approved
0.7063	Intermediate Similarity	NPD2979	Phase 3
0.7023	Intermediate Similarity	NPD6858	Approved
0.7023	Intermediate Similarity	NPD7094	Approved
0.7007	Intermediate Similarity	NPD1281	Approved
0.7007	Intermediate Similarity	NPD1471	Phase 3
0.7	Intermediate Similarity	NPD2798	Approved
0.6993	Remote Similarity	NPD7961	Discontinued
0.6992	Remote Similarity	NPD3495	Discontinued
0.6986	Remote Similarity	NPD4308	Phase 3
0.6984	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD1929	Approved
0.6984	Remote Similarity	NPD1930	Approved
0.6978	Remote Similarity	NPD1876	Approved
0.6957	Remote Similarity	NPD3972	Approved
0.6948	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD3226	Approved
0.6939	Remote Similarity	NPD2935	Discontinued
0.6933	Remote Similarity	NPD7799	Discontinued
0.6929	Remote Similarity	NPD3266	Approved
0.6929	Remote Similarity	NPD2797	Approved
0.6929	Remote Similarity	NPD3267	Approved
0.6918	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6917	Remote Similarity	NPD2629	Approved
0.6912	Remote Similarity	NPD5691	Approved
0.6912	Remote Similarity	NPD3025	Approved
0.6912	Remote Similarity	NPD3024	Approved
0.6908	Remote Similarity	NPD2532	Approved
0.6908	Remote Similarity	NPD2533	Approved
0.6908	Remote Similarity	NPD2534	Approved
0.6901	Remote Similarity	NPD6832	Phase 2
0.6885	Remote Similarity	NPD1202	Approved
0.688	Remote Similarity	NPD2066	Phase 3
0.6875	Remote Similarity	NPD6663	Approved
0.687	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD8166	Discontinued
0.6867	Remote Similarity	NPD3750	Approved
0.6866	Remote Similarity	NPD4198	Discontinued
0.6861	Remote Similarity	NPD2932	Approved
0.6857	Remote Similarity	NPD1283	Approved
0.6838	Remote Similarity	NPD7009	Phase 2
0.6824	Remote Similarity	NPD2438	Suspended
0.6812	Remote Similarity	NPD3026	Approved
0.6812	Remote Similarity	NPD3023	Approved
0.6806	Remote Similarity	NPD3268	Approved
0.6803	Remote Similarity	NPD7631	Approved
0.6795	Remote Similarity	NPD7028	Phase 2
0.6788	Remote Similarity	NPD5585	Approved
0.6781	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7610	Discontinued
0.6765	Remote Similarity	NPD8434	Phase 2
0.6755	Remote Similarity	NPD4628	Phase 3
0.6748	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD17	Approved
0.6739	Remote Similarity	NPD3019	Approved
0.6739	Remote Similarity	NPD4626	Approved
0.6731	Remote Similarity	NPD7458	Discontinued
0.6723	Remote Similarity	NPD9257	Approved
0.6723	Remote Similarity	NPD9259	Approved
0.6721	Remote Similarity	NPD7609	Phase 3
0.6714	Remote Similarity	NPD9717	Approved
0.6714	Remote Similarity	NPD4878	Approved
0.6713	Remote Similarity	NPD5736	Approved
0.6711	Remote Similarity	NPD5406	Approved
0.6711	Remote Similarity	NPD5408	Approved
0.6711	Remote Similarity	NPD5404	Approved
0.6711	Remote Similarity	NPD5405	Approved
0.6711	Remote Similarity	NPD2531	Phase 2
0.6691	Remote Similarity	NPD9493	Approved
0.669	Remote Similarity	NPD1470	Approved
0.6689	Remote Similarity	NPD2569	Approved
0.6689	Remote Similarity	NPD2567	Approved
0.6687	Remote Similarity	NPD4965	Approved
0.6687	Remote Similarity	NPD4966	Approved
0.6687	Remote Similarity	NPD4967	Phase 2
0.6667	Remote Similarity	NPD1087	Approved
0.6667	Remote Similarity	NPD7055	Discontinued
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5760	Phase 2
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD447	Suspended
0.6667	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1651	Approved
0.6667	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD5761	Phase 2
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7819	Suspended
0.6667	Remote Similarity	NPD6765	Approved
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD6004	Phase 3
0.6667	Remote Similarity	NPD1088	Approved
0.6647	Remote Similarity	NPD8407	Phase 2
0.6643	Remote Similarity	NPD1611	Approved
0.6643	Remote Similarity	NPD1019	Discontinued
0.6641	Remote Similarity	NPD1932	Approved
0.664	Remote Similarity	NPD1989	Approved
0.6623	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD6234	Discontinued
0.6599	Remote Similarity	NPD4140	Approved
0.6596	Remote Similarity	NPD1608	Approved
0.6596	Remote Similarity	NPD6637	Approved
0.6593	Remote Similarity	NPD1241	Discontinued
0.6593	Remote Similarity	NPD6010	Discontinued
0.6591	Remote Similarity	NPD2329	Discontinued
0.6587	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD2800	Approved
0.6579	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD411	Approved
0.6573	Remote Similarity	NPD1203	Approved
0.6569	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD8368	Discontinued
0.656	Remote Similarity	NPD1693	Approved
0.6554	Remote Similarity	NPD4622	Approved
0.6554	Remote Similarity	NPD4618	Approved
0.6554	Remote Similarity	NPD1933	Approved
0.6549	Remote Similarity	NPD4359	Approved
0.6544	Remote Similarity	NPD4766	Approved
0.6543	Remote Similarity	NPD3749	Approved
0.6541	Remote Similarity	NPD5239	Approved
0.6541	Remote Similarity	NPD5235	Approved
0.6541	Remote Similarity	NPD5236	Approved
0.6541	Remote Similarity	NPD5240	Approved
0.6541	Remote Similarity	NPD5237	Approved
0.6531	Remote Similarity	NPD7713	Phase 3
0.6529	Remote Similarity	NPD650	Approved
0.6525	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD1201	Approved
0.6525	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD8127	Discontinued
0.6522	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7644	Approved
0.6512	Remote Similarity	NPD6784	Approved
0.6512	Remote Similarity	NPD6785	Approved
0.6507	Remote Similarity	NPD7095	Approved
0.6504	Remote Similarity	NPD1089	Approved
0.6504	Remote Similarity	NPD1086	Approved
0.6504	Remote Similarity	NPD1090	Approved
0.6504	Remote Similarity	NPD9256	Approved
0.6504	Remote Similarity	NPD9258	Approved
0.65	Remote Similarity	NPD37	Approved
0.65	Remote Similarity	NPD5125	Phase 3
0.65	Remote Similarity	NPD5126	Approved
0.6497	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD920	Approved
0.6496	Remote Similarity	NPD3317	Approved
0.6493	Remote Similarity	NPD2201	Approved
0.649	Remote Similarity	NPD6099	Approved
0.649	Remote Similarity	NPD6100	Approved
0.6486	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD6232	Discontinued
0.6478	Remote Similarity	NPD6599	Discontinued
0.6475	Remote Similarity	NPD9545	Approved
0.6475	Remote Similarity	NPD7741	Discontinued
0.6474	Remote Similarity	NPD8150	Discontinued
0.6471	Remote Similarity	NPD1243	Approved
0.6467	Remote Similarity	NPD7473	Discontinued
0.6467	Remote Similarity	NPD5688	Approved
0.6467	Remote Similarity	NPD5689	Approved
0.6463	Remote Similarity	NPD5494	Approved
0.6463	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD6647	Phase 2
0.6462	Remote Similarity	NPD9261	Approved
0.6454	Remote Similarity	NPD3496	Discontinued
0.6452	Remote Similarity	NPD3300	Phase 2
0.6449	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2344	Approved
0.6443	Remote Similarity	NPD6355	Discontinued

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