NPASS Compound

Structure

NPC190020 OpenBabel07101719402D 23 25 0 0 1 0 0 0 0 0999 V2000 4.9049 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 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 3.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9049 -1.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4049 -1.0000 0.0000 C 0 0 1 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 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 -2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 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 20 1 0 0 0 0 3 21 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 1 1 1 0 0 0 7 17 1 0 0 0 0 8 4 1 6 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 5 1 6 0 0 0 11 14 1 0 0 0 0 11 23 1 0 0 0 0 12 13 2 0 0 0 0 12 16 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 9 1 6 0 0 0 14 22 1 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.12
Volume:	310.609
LogP:	1.803
LogD:	0.967
LogS:	-2.778
# Rotatable Bonds:	4
TPSA:	94.45
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.811
Synthetic Accessibility Score:	4.037
Fsp3:	0.562
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:	-5.205
MDCK Permeability:	3.647846097010188e-05
Pgp-inhibitor:	0.03
Pgp-substrate:	0.077
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.813
Plasma Protein Binding (PPB):	59.4534797668457%
Volume Distribution (VD):	0.92
Pgp-substrate:	18.03649139404297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.109
CYP1A2-substrate:	0.726
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.11
CYP2C9-substrate:	0.788
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.343
CYP3A4-inhibitor:	0.249
CYP3A4-substrate:	0.423

ADMET: Excretion

Clearance (CL):	6.183
Half-life (T1/2):	0.531

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.634
Drug-inuced Liver Injury (DILI):	0.756
AMES Toxicity:	0.226
Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.931
Skin Sensitization:	0.444
Carcinogencity:	0.685
Eye Corrosion:	0.003
Eye Irritation:	0.085
Respiratory Toxicity:	0.774

Download Data

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

Natural Product: NPC190020

Natural Product ID:	NPC190020
*Common Name:**	(12R)-12-Hydroxymonocerin
IUPAC Name:	(2S,3aR,9bR)-6-hydroxy-2-[(2R)-2-hydroxypropyl]-7,8-dimethoxy-2,3,3a,9b-tetrahydrofuro[3,2-c]isochromen-5-one
Synonyms:	(12R)-12-Hydroxymonocerin
Standard InCHIKey:	OAWLQCWPKLOBPA-PCAXDNMNSA-N
Standard InCHI:	InChI=1S/C16H20O7/c1-7(17)4-8-5-11-14(22-8)9-6-10(20-2)15(21-3)13(18)12(9)16(19)23-11/h6-8,11,14,17-18H,4-5H2,1-3H3/t7-,8+,11-,14-/m1/s1
SMILES:	COc1cc2[C@H]3O[C@H](C[C@H]3OC(=O)c2c(c1OC)O)C[C@H](O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL488514
PubChem CID:	24896700
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003411] 2-benzopyrans

*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
NPO16252	Microdochium bolleyi	Species	Microdochiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18510362]
NPO40509	Setosphaeria sp. SCSIO41009	Strain	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30091601]
NPO16252	Microdochium bolleyi	Species	Microdochiaceae	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	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	IZ	=	0.0	mm	PMID[460140]
NPT1231	Organism	Microbotryum violaceum	Microbotryum violaceum	IZ	=	7.0	mm	PMID[460140]
NPT1234	Organism	Chlorella fusca	Chlorella fusca	IZ	=	6.0	mm	PMID[460140]
NPT1230	Organism	Bacillus megaterium	Bacillus megaterium	IZ	=	0.0	mm	PMID[460140]

☑ 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 NPC190020 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	340
0.1-0.2	1403
0.2-0.3	3245
0.3-0.4	7589
0.4-0.5	10558
0.5-0.6	4280
0.6-0.7	5195
0.7-0.8	7401
0.8-0.85	2173
0.85-0.9	465
0.9-0.95	39
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC77679
1.0	High Similarity	NPC84935
0.9933	High Similarity	NPC150227
0.9866	High Similarity	NPC16082
0.9866	High Similarity	NPC199926
0.9866	High Similarity	NPC82592
0.9799	High Similarity	NPC281477
0.9733	High Similarity	NPC79998
0.9597	High Similarity	NPC96501
0.9412	High Similarity	NPC227062
0.9404	High Similarity	NPC200773
0.9404	High Similarity	NPC70016
0.9404	High Similarity	NPC240768
0.9404	High Similarity	NPC215921
0.9281	High Similarity	NPC238672
0.9281	High Similarity	NPC144801
0.9281	High Similarity	NPC197188
0.9281	High Similarity	NPC116850
0.9281	High Similarity	NPC43872
0.9281	High Similarity	NPC291510
0.9276	High Similarity	NPC473732
0.9231	High Similarity	NPC200594
0.9231	High Similarity	NPC24627
0.9216	High Similarity	NPC295646
0.9216	High Similarity	NPC475116
0.9211	High Similarity	NPC179178
0.92	High Similarity	NPC32058
0.92	High Similarity	NPC85734
0.9195	High Similarity	NPC27106
0.9182	High Similarity	NPC472452
0.9177	High Similarity	NPC475985
0.9161	High Similarity	NPC54928
0.915	High Similarity	NPC228662
0.9145	High Similarity	NPC270160
0.9145	High Similarity	NPC237440
0.9128	High Similarity	NPC51106
0.9128	High Similarity	NPC469542
0.9119	High Similarity	NPC326520
0.9091	High Similarity	NPC167903
0.9085	High Similarity	NPC469670
0.9085	High Similarity	NPC469619
0.9074	High Similarity	NPC471181
0.9067	High Similarity	NPC280404
0.9067	High Similarity	NPC210425
0.9067	High Similarity	NPC277426
0.9067	High Similarity	NPC86373
0.9062	High Similarity	NPC170245
0.9062	High Similarity	NPC20237
0.906	High Similarity	NPC469579
0.9057	High Similarity	NPC249181
0.9051	High Similarity	NPC117985
0.9045	High Similarity	NPC329091
0.9045	High Similarity	NPC470339
0.9032	High Similarity	NPC287504
0.9032	High Similarity	NPC25127
0.9026	High Similarity	NPC204350
0.9006	High Similarity	NPC283041
0.9	High Similarity	NPC258307
0.9	High Similarity	NPC191930
0.9	High Similarity	NPC472006
0.8994	High Similarity	NPC472964
0.8994	High Similarity	NPC215612
0.8993	High Similarity	NPC90411
0.8993	High Similarity	NPC67650
0.8993	High Similarity	NPC1704
0.8987	High Similarity	NPC472902
0.8987	High Similarity	NPC472055
0.8987	High Similarity	NPC36217
0.8981	High Similarity	NPC300727
0.8981	High Similarity	NPC241904
0.8974	High Similarity	NPC20541
0.8974	High Similarity	NPC16286
0.8974	High Similarity	NPC67396
0.8974	High Similarity	NPC38898
0.8947	High Similarity	NPC260946
0.8947	High Similarity	NPC138978
0.8947	High Similarity	NPC107625
0.8938	High Similarity	NPC18100
0.8938	High Similarity	NPC7483
0.8938	High Similarity	NPC124038
0.8933	High Similarity	NPC474385
0.8931	High Similarity	NPC349525
0.8931	High Similarity	NPC103201
0.8931	High Similarity	NPC473106
0.8924	High Similarity	NPC477410
0.8924	High Similarity	NPC238381
0.8924	High Similarity	NPC279732
0.8924	High Similarity	NPC476242
0.8917	High Similarity	NPC301897
0.8917	High Similarity	NPC197751
0.8917	High Similarity	NPC274730
0.8917	High Similarity	NPC24640
0.891	High Similarity	NPC18727
0.8903	High Similarity	NPC151425
0.8896	High Similarity	NPC17219
0.8889	High Similarity	NPC166583
0.8889	High Similarity	NPC8817
0.8889	High Similarity	NPC53362
0.8889	High Similarity	NPC471180
0.8889	High Similarity	NPC6588
0.8889	High Similarity	NPC476463
0.8889	High Similarity	NPC210320
0.8889	High Similarity	NPC477154
0.8889	High Similarity	NPC117854
0.8882	High Similarity	NPC473286
0.8882	High Similarity	NPC471788
0.8882	High Similarity	NPC475888
0.8882	High Similarity	NPC83272
0.8882	High Similarity	NPC472277
0.8875	High Similarity	NPC201800
0.8875	High Similarity	NPC48860
0.8875	High Similarity	NPC472635
0.8875	High Similarity	NPC211107
0.8875	High Similarity	NPC144843
0.8868	High Similarity	NPC161947
0.8868	High Similarity	NPC321399
0.8868	High Similarity	NPC14353
0.8868	High Similarity	NPC155302
0.8868	High Similarity	NPC56085
0.8868	High Similarity	NPC292415
0.8868	High Similarity	NPC472624
0.8868	High Similarity	NPC470358
0.8868	High Similarity	NPC228785
0.8861	High Similarity	NPC129684
0.8861	High Similarity	NPC474836
0.8861	High Similarity	NPC474055
0.8861	High Similarity	NPC162869
0.8861	High Similarity	NPC299520
0.8861	High Similarity	NPC179732
0.8861	High Similarity	NPC473395
0.8861	High Similarity	NPC475267
0.8861	High Similarity	NPC156057
0.8861	High Similarity	NPC108456
0.8861	High Similarity	NPC472598
0.8861	High Similarity	NPC469584
0.8861	High Similarity	NPC48208
0.8861	High Similarity	NPC474208
0.8859	High Similarity	NPC471819
0.8854	High Similarity	NPC477503
0.8854	High Similarity	NPC45849
0.8854	High Similarity	NPC470327
0.8854	High Similarity	NPC200761
0.8854	High Similarity	NPC99381
0.8846	High Similarity	NPC219582
0.8846	High Similarity	NPC199773
0.8846	High Similarity	NPC302950
0.8846	High Similarity	NPC289968
0.8846	High Similarity	NPC236637
0.8839	High Similarity	NPC338131
0.8839	High Similarity	NPC151473
0.8831	High Similarity	NPC215711
0.8831	High Similarity	NPC73411
0.8827	High Similarity	NPC477517
0.8827	High Similarity	NPC207575
0.8827	High Similarity	NPC13481
0.8824	High Similarity	NPC268366
0.8824	High Similarity	NPC473023
0.8824	High Similarity	NPC470357
0.882	High Similarity	NPC205265
0.882	High Similarity	NPC476822
0.882	High Similarity	NPC472281
0.882	High Similarity	NPC186686
0.882	High Similarity	NPC474350
0.882	High Similarity	NPC474240
0.882	High Similarity	NPC133065
0.8816	High Similarity	NPC470932
0.8812	High Similarity	NPC112418
0.8812	High Similarity	NPC87431
0.8812	High Similarity	NPC474186
0.8812	High Similarity	NPC278052
0.8812	High Similarity	NPC201560
0.8812	High Similarity	NPC40491
0.8812	High Similarity	NPC61010
0.8812	High Similarity	NPC474779
0.8805	High Similarity	NPC315157
0.8805	High Similarity	NPC85121
0.8805	High Similarity	NPC210459
0.8805	High Similarity	NPC45846
0.8805	High Similarity	NPC100123
0.8805	High Similarity	NPC87317
0.88	High Similarity	NPC158472
0.8797	High Similarity	NPC326037
0.8797	High Similarity	NPC320825
0.8797	High Similarity	NPC255106
0.8797	High Similarity	NPC195796
0.8797	High Similarity	NPC278778
0.8797	High Similarity	NPC209614
0.8797	High Similarity	NPC250922
0.8797	High Similarity	NPC472050
0.8797	High Similarity	NPC235165
0.8797	High Similarity	NPC291878
0.8797	High Similarity	NPC317383
0.8797	High Similarity	NPC472626
0.8797	High Similarity	NPC470328
0.8797	High Similarity	NPC35038
0.8797	High Similarity	NPC13858
0.8792	High Similarity	NPC94248
0.8792	High Similarity	NPC472602
0.8792	High Similarity	NPC212693
0.879	High Similarity	NPC301233

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 NPC190020 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	301
0.1-0.2	851
0.2-0.3	1914
0.3-0.4	2554
0.4-0.5	1918
0.5-0.6	982
0.6-0.7	452
0.7-0.8	147
0.8-0.85	26
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8846	High Similarity	NPD1934	Approved
0.8758	High Similarity	NPD2534	Approved
0.8758	High Similarity	NPD2533	Approved
0.8758	High Similarity	NPD2532	Approved
0.8679	High Similarity	NPD4868	Clinical (unspecified phase)
0.8679	High Similarity	NPD3882	Suspended
0.8671	High Similarity	NPD2393	Clinical (unspecified phase)
0.8659	High Similarity	NPD3818	Discontinued
0.8642	High Similarity	NPD6232	Discontinued
0.8609	High Similarity	NPD970	Clinical (unspecified phase)
0.8553	High Similarity	NPD2801	Approved
0.8537	High Similarity	NPD6167	Clinical (unspecified phase)
0.8537	High Similarity	NPD6168	Clinical (unspecified phase)
0.8537	High Similarity	NPD6166	Phase 2
0.8485	Intermediate Similarity	NPD7473	Discontinued
0.8443	Intermediate Similarity	NPD7074	Phase 3
0.8438	Intermediate Similarity	NPD1465	Phase 2
0.8402	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD3817	Phase 2
0.8383	Intermediate Similarity	NPD5844	Phase 1
0.8383	Intermediate Similarity	NPD7054	Approved
0.8344	Intermediate Similarity	NPD6234	Discontinued
0.8333	Intermediate Similarity	NPD230	Phase 1
0.8333	Intermediate Similarity	NPD7472	Approved
0.8293	Intermediate Similarity	NPD5494	Approved
0.8261	Intermediate Similarity	NPD37	Approved
0.825	Intermediate Similarity	NPD4380	Phase 2
0.8221	Intermediate Similarity	NPD4966	Approved
0.8221	Intermediate Similarity	NPD4965	Approved
0.8221	Intermediate Similarity	NPD4967	Phase 2
0.8217	Intermediate Similarity	NPD1511	Approved
0.8214	Intermediate Similarity	NPD7228	Approved
0.821	Intermediate Similarity	NPD7819	Suspended
0.8193	Intermediate Similarity	NPD5711	Approved
0.8193	Intermediate Similarity	NPD5710	Approved
0.8176	Intermediate Similarity	NPD6797	Phase 2
0.8176	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7075	Discontinued
0.8129	Intermediate Similarity	NPD7251	Discontinued
0.8113	Intermediate Similarity	NPD1512	Approved
0.8098	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7808	Phase 3
0.8061	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD7199	Phase 2
0.7987	Intermediate Similarity	NPD6799	Approved
0.7952	Intermediate Similarity	NPD3749	Approved
0.7949	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD6801	Discontinued
0.7919	Intermediate Similarity	NPD6559	Discontinued
0.7917	Intermediate Similarity	NPD6959	Discontinued
0.7914	Intermediate Similarity	NPD6599	Discontinued
0.7904	Intermediate Similarity	NPD919	Approved
0.7898	Intermediate Similarity	NPD1549	Phase 2
0.7857	Intermediate Similarity	NPD447	Suspended
0.7848	Intermediate Similarity	NPD2800	Approved
0.7841	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD5402	Approved
0.7829	Intermediate Similarity	NPD3027	Phase 3
0.7826	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1510	Phase 2
0.7809	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD4628	Phase 3
0.7799	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1240	Approved
0.7792	Intermediate Similarity	NPD943	Approved
0.7771	Intermediate Similarity	NPD2935	Discontinued
0.7764	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD7411	Suspended
0.7746	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5353	Approved
0.7725	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3926	Phase 2
0.7714	Intermediate Similarity	NPD7240	Approved
0.7714	Intermediate Similarity	NPD7685	Pre-registration
0.7706	Intermediate Similarity	NPD1247	Approved
0.7692	Intermediate Similarity	NPD1607	Approved
0.7688	Intermediate Similarity	NPD3750	Approved
0.7683	Intermediate Similarity	NPD1653	Approved
0.7677	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1613	Approved
0.7658	Intermediate Similarity	NPD2796	Approved
0.764	Intermediate Similarity	NPD6190	Approved
0.7622	Intermediate Similarity	NPD5403	Approved
0.7622	Intermediate Similarity	NPD920	Approved
0.76	Intermediate Similarity	NPD9269	Phase 2
0.7582	Intermediate Similarity	NPD9494	Approved
0.7574	Intermediate Similarity	NPD7768	Phase 2
0.7572	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD1551	Phase 2
0.7516	Intermediate Similarity	NPD1243	Approved
0.7514	Intermediate Similarity	NPD5242	Approved
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD8151	Discontinued
0.7486	Intermediate Similarity	NPD3751	Discontinued
0.7469	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD3787	Discontinued
0.743	Intermediate Similarity	NPD8313	Approved
0.743	Intermediate Similarity	NPD8312	Approved
0.7425	Intermediate Similarity	NPD3226	Approved
0.7419	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7403	Intermediate Similarity	NPD8150	Discontinued
0.7394	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2346	Discontinued
0.7389	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD3748	Approved
0.7358	Intermediate Similarity	NPD6651	Approved
0.7356	Intermediate Similarity	NPD7229	Phase 3
0.7354	Intermediate Similarity	NPD5005	Approved
0.7354	Intermediate Similarity	NPD5006	Approved
0.734	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD9268	Approved
0.7329	Intermediate Similarity	NPD6099	Approved
0.7329	Intermediate Similarity	NPD6100	Approved
0.7325	Intermediate Similarity	NPD3764	Approved
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7301	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1933	Approved
0.7289	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD2344	Approved
0.7267	Intermediate Similarity	NPD2799	Discontinued
0.7267	Intermediate Similarity	NPD7033	Discontinued
0.7263	Intermediate Similarity	NPD5953	Discontinued
0.7249	Intermediate Similarity	NPD6776	Approved
0.7249	Intermediate Similarity	NPD6782	Approved
0.7249	Intermediate Similarity	NPD6780	Approved
0.7249	Intermediate Similarity	NPD6778	Approved
0.7249	Intermediate Similarity	NPD6777	Approved
0.7249	Intermediate Similarity	NPD6781	Approved
0.7249	Intermediate Similarity	NPD6779	Approved
0.7247	Intermediate Similarity	NPD7286	Phase 2
0.7235	Intermediate Similarity	NPD6386	Approved
0.7235	Intermediate Similarity	NPD6385	Approved
0.7234	Intermediate Similarity	NPD4420	Approved
0.7229	Intermediate Similarity	NPD7390	Discontinued
0.7225	Intermediate Similarity	NPD7680	Approved
0.7219	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD8127	Discontinued
0.7195	Intermediate Similarity	NPD1652	Phase 2
0.7195	Intermediate Similarity	NPD2654	Approved
0.719	Intermediate Similarity	NPD3705	Approved
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7182	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7266	Discontinued
0.7175	Intermediate Similarity	NPD2403	Approved
0.7152	Intermediate Similarity	NPD9545	Approved
0.7152	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4060	Phase 1
0.7115	Intermediate Similarity	NPD1203	Approved
0.7108	Intermediate Similarity	NPD2309	Approved
0.7097	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7874	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6832	Phase 2
0.7081	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5124	Phase 1
0.7078	Intermediate Similarity	NPD422	Phase 1
0.7073	Intermediate Similarity	NPD6005	Phase 3
0.7073	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD6002	Phase 3
0.7073	Intermediate Similarity	NPD6004	Phase 3
0.7073	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7696	Phase 3
0.7047	Intermediate Similarity	NPD7698	Approved
0.7047	Intermediate Similarity	NPD7697	Approved
0.7043	Intermediate Similarity	NPD4287	Approved
0.7041	Intermediate Similarity	NPD6273	Approved
0.7035	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7930	Approved
0.7032	Intermediate Similarity	NPD1608	Approved
0.703	Intermediate Similarity	NPD2424	Discontinued
0.702	Intermediate Similarity	NPD9493	Approved
0.7019	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3620	Phase 2
0.7012	Intermediate Similarity	NPD5405	Approved
0.7012	Intermediate Similarity	NPD5404	Approved
0.7012	Intermediate Similarity	NPD5406	Approved
0.7012	Intermediate Similarity	NPD5408	Approved
0.701	Intermediate Similarity	NPD7870	Phase 2
0.701	Intermediate Similarity	NPD7871	Phase 2
0.7	Intermediate Similarity	NPD2313	Discontinued
0.7	Intermediate Similarity	NPD411	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