NPASS Compound

Structure

CID166067 OpenBabel06191715532D 27 31 0 0 1 0 0 0 0 0999 V2000 -1.4885 0.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2098 -3.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2108 -0.4318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2105 -1.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4666 -0.0017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7446 -2.1487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4891 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4888 -0.8592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4890 -1.7189 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4659 -1.7208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7221 -0.4312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2333 -0.4306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 -1.7190 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7445 -0.4300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7217 -1.2907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7442 -1.2895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2329 -1.2901 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9772 -1.7202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4884 -1.7196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7443 -0.4295 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2334 -2.1486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9768 -2.5797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4880 -2.5791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4656 -2.5803 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9778 -0.0011 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.8596 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 24 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 9 1 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 1 0 0 0 10 15 2 0 0 0 0 10 24 1 0 0 0 0 11 15 1 0 0 0 0 11 25 1 0 0 0 0 12 17 1 0 0 0 0 12 25 1 0 0 0 0 13 6 1 6 0 0 0 13 16 1 0 0 0 0 13 26 1 0 0 0 0 14 16 2 0 0 0 0 14 27 1 0 0 0 0 15 18 1 0 0 0 0 16 19 1 0 0 0 0 17 18 1 0 0 0 0 17 19 2 0 0 0 0 18 22 2 0 0 0 0 19 23 1 0 0 0 0 20 1 1 1 0 0 0 20 26 1 0 0 0 0 20 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.11
Volume:	354.77
LogP:	3.201
LogD:	2.243
LogS:	-4.591
# Rotatable Bonds:	1
TPSA:	98.36
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.636
Synthetic Accessibility Score:	4.803
Fsp3:	0.35
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:	-5.002
MDCK Permeability:	4.525656913756393e-05
Pgp-inhibitor:	0.183
Pgp-substrate:	0.83
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.227

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	83.96149444580078%
Volume Distribution (VD):	1.114
Pgp-substrate:	13.528132438659668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.331
CYP1A2-substrate:	0.98
CYP2C19-inhibitor:	0.063
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.676
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.286
CYP2D6-substrate:	0.355
CYP3A4-inhibitor:	0.451
CYP3A4-substrate:	0.47

ADMET: Excretion

Clearance (CL):	7.924
Half-life (T1/2):	0.227

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.925
Drug-inuced Liver Injury (DILI):	0.964
AMES Toxicity:	0.564
Rat Oral Acute Toxicity:	0.408
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.577
Carcinogencity:	0.966
Eye Corrosion:	0.003
Eye Irritation:	0.114
Respiratory Toxicity:	0.894

Download Data

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

Natural Product: NPC166067

Natural Product ID:	NPC166067
*Common Name:**	Chaetoxanthone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	PYEDKAHYOPGAKC-PDXJJUDESA-N
Standard InCHI:	InChI=1S/C20H18O7/c1-20-8-9(21)6-13(26-20)16-14(27-20)7-12-17(19(16)23)18(22)15-10(24-2)4-3-5-11(15)25-12/h3-5,7,9,13,21,23H,6,8H2,1-2H3/t9-,13+,20+/m1/s1
SMILES:	COc1cccc2c1c(=O)c1c(o2)cc2c(c1O)[C@@H]1C[C@H](C[C@](O2)(O1)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501998
PubChem CID:	44586905
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO31271	Chaetomium	Genus	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15784979]
NPO31271	Chaetomium	Genus	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17134253]
NPO31271	Chaetomium	Genus	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18683985]

☑ 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	5

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	IC50	=	59.1	ug.mL-1	PMID[483152]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	4.7	ug.mL-1	PMID[483152]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	>	10.0	ug.mL-1	PMID[483152]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	5.3	ug.mL-1	PMID[483152]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3.5	ug.mL-1	PMID[483152]

☑ 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 NPC166067 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	384
0.1-0.2	1720
0.2-0.3	3857
0.3-0.4	10035
0.4-0.5	8854
0.5-0.6	4282
0.6-0.7	6007
0.7-0.8	4489
0.8-0.85	2125
0.85-0.9	887
0.9-0.95	55
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC325429
0.9477	High Similarity	NPC190450
0.9379	High Similarity	NPC166934
0.9379	High Similarity	NPC220998
0.9379	High Similarity	NPC37496
0.9379	High Similarity	NPC167624
0.9379	High Similarity	NPC107572
0.9379	High Similarity	NPC227579
0.9379	High Similarity	NPC10937
0.9379	High Similarity	NPC40833
0.9379	High Similarity	NPC223500
0.9379	High Similarity	NPC76338
0.9379	High Similarity	NPC266725
0.9379	High Similarity	NPC1089
0.9379	High Similarity	NPC265040
0.9379	High Similarity	NPC78
0.9379	High Similarity	NPC166482
0.9379	High Similarity	NPC76372
0.9379	High Similarity	NPC324436
0.9379	High Similarity	NPC161506
0.9379	High Similarity	NPC177354
0.9379	High Similarity	NPC32739
0.9379	High Similarity	NPC66515
0.9379	High Similarity	NPC328164
0.9379	High Similarity	NPC306829
0.9379	High Similarity	NPC194432
0.9379	High Similarity	NPC148757
0.9379	High Similarity	NPC125855
0.9379	High Similarity	NPC64915
0.9379	High Similarity	NPC296917
0.9379	High Similarity	NPC228504
0.9379	High Similarity	NPC324134
0.9379	High Similarity	NPC182852
0.9351	High Similarity	NPC44947
0.9346	High Similarity	NPC97285
0.9346	High Similarity	NPC246469
0.9346	High Similarity	NPC271270
0.9346	High Similarity	NPC142860
0.9324	High Similarity	NPC161191
0.932	High Similarity	NPC470133
0.932	High Similarity	NPC88964
0.932	High Similarity	NPC246948
0.932	High Similarity	NPC176229
0.932	High Similarity	NPC267375
0.932	High Similarity	NPC472629
0.932	High Similarity	NPC475052
0.932	High Similarity	NPC109183
0.932	High Similarity	NPC470131
0.932	High Similarity	NPC111786
0.932	High Similarity	NPC83357
0.932	High Similarity	NPC142405
0.932	High Similarity	NPC301276
0.932	High Similarity	NPC54577
0.932	High Similarity	NPC470132
0.932	High Similarity	NPC312973
0.932	High Similarity	NPC473078
0.932	High Similarity	NPC214774
0.932	High Similarity	NPC470647
0.932	High Similarity	NPC20488
0.932	High Similarity	NPC67805
0.932	High Similarity	NPC470134
0.932	High Similarity	NPC195621
0.9315	High Similarity	NPC107177
0.9315	High Similarity	NPC223812
0.9315	High Similarity	NPC164980
0.9315	High Similarity	NPC175504
0.9315	High Similarity	NPC149026
0.9315	High Similarity	NPC77794
0.9315	High Similarity	NPC169591
0.9315	High Similarity	NPC39329
0.9315	High Similarity	NPC68104
0.9315	High Similarity	NPC257097
0.9315	High Similarity	NPC310130
0.9315	High Similarity	NPC478086
0.9315	High Similarity	NPC278249
0.9315	High Similarity	NPC85162
0.9315	High Similarity	NPC150408
0.9315	High Similarity	NPC91560
0.9315	High Similarity	NPC214166
0.9315	High Similarity	NPC185276
0.9315	High Similarity	NPC81697
0.9315	High Similarity	NPC143896
0.9315	High Similarity	NPC221432
0.9315	High Similarity	NPC316816
0.9315	High Similarity	NPC125894
0.9315	High Similarity	NPC75049
0.931	High Similarity	NPC279650
0.931	High Similarity	NPC312391
0.931	High Similarity	NPC258630
0.931	High Similarity	NPC17170
0.931	High Similarity	NPC110038
0.931	High Similarity	NPC248372
0.931	High Similarity	NPC166689
0.931	High Similarity	NPC324386
0.931	High Similarity	NPC213322
0.931	High Similarity	NPC4743
0.931	High Similarity	NPC96408
0.931	High Similarity	NPC156190
0.929	High Similarity	NPC257566
0.929	High Similarity	NPC124155
0.9286	High Similarity	NPC47923
0.9276	High Similarity	NPC206378
0.9262	High Similarity	NPC3642
0.9262	High Similarity	NPC473016
0.9257	High Similarity	NPC473077
0.9257	High Similarity	NPC296998
0.9257	High Similarity	NPC472627
0.9257	High Similarity	NPC23728
0.9257	High Similarity	NPC283234
0.9257	High Similarity	NPC110303
0.9252	High Similarity	NPC209040
0.9252	High Similarity	NPC470135
0.9252	High Similarity	NPC235217
0.9252	High Similarity	NPC124780
0.9252	High Similarity	NPC131568
0.9252	High Similarity	NPC39045
0.9252	High Similarity	NPC87486
0.9252	High Similarity	NPC470136
0.9252	High Similarity	NPC131579
0.9252	High Similarity	NPC473014
0.9252	High Similarity	NPC470890
0.9252	High Similarity	NPC473015
0.9252	High Similarity	NPC473013
0.9252	High Similarity	NPC236766
0.9252	High Similarity	NPC319752
0.9252	High Similarity	NPC197252
0.9241	High Similarity	NPC188243
0.9241	High Similarity	NPC110228
0.9241	High Similarity	NPC6407
0.9226	High Similarity	NPC259834
0.9221	High Similarity	NPC472320
0.9216	High Similarity	NPC473512
0.9216	High Similarity	NPC129827
0.9216	High Similarity	NPC23817
0.9216	High Similarity	NPC44931
0.9216	High Similarity	NPC65003
0.9211	High Similarity	NPC97052
0.9211	High Similarity	NPC169248
0.9211	High Similarity	NPC39351
0.9211	High Similarity	NPC72649
0.9211	High Similarity	NPC26195
0.9205	High Similarity	NPC475790
0.9195	High Similarity	NPC132592
0.9195	High Similarity	NPC160821
0.9195	High Similarity	NPC189087
0.9195	High Similarity	NPC321623
0.9195	High Similarity	NPC122894
0.9189	High Similarity	NPC127059
0.9189	High Similarity	NPC474161
0.9189	High Similarity	NPC285630
0.9189	High Similarity	NPC228779
0.9189	High Similarity	NPC476088
0.9184	High Similarity	NPC471621
0.9178	High Similarity	NPC3188
0.9172	High Similarity	NPC265871
0.9172	High Similarity	NPC329203
0.9172	High Similarity	NPC150648
0.9172	High Similarity	NPC225153
0.9172	High Similarity	NPC274784
0.9172	High Similarity	NPC310135
0.9172	High Similarity	NPC222342
0.9172	High Similarity	NPC20709
0.9172	High Similarity	NPC140890
0.9161	High Similarity	NPC303913
0.9161	High Similarity	NPC175513
0.9156	High Similarity	NPC22062
0.9156	High Similarity	NPC473634
0.9156	High Similarity	NPC138811
0.915	High Similarity	NPC170475
0.9145	High Similarity	NPC112701
0.9145	High Similarity	NPC106625
0.9145	High Similarity	NPC109594
0.9145	High Similarity	NPC326592
0.9139	High Similarity	NPC474023
0.9139	High Similarity	NPC209142
0.9139	High Similarity	NPC312549
0.9139	High Similarity	NPC474021
0.9133	High Similarity	NPC104236
0.9133	High Similarity	NPC19238
0.9133	High Similarity	NPC5173
0.9133	High Similarity	NPC164205
0.9133	High Similarity	NPC472628
0.9128	High Similarity	NPC10990
0.9128	High Similarity	NPC300988
0.9122	High Similarity	NPC224714
0.9122	High Similarity	NPC271288
0.9116	High Similarity	NPC147145
0.911	High Similarity	NPC159275
0.911	High Similarity	NPC129853
0.911	High Similarity	NPC241100
0.911	High Similarity	NPC69769
0.911	High Similarity	NPC76445
0.911	High Similarity	NPC284550
0.9103	High Similarity	NPC475382
0.9103	High Similarity	NPC131745
0.9097	High Similarity	NPC153342
0.9097	High Similarity	NPC187379
0.9097	High Similarity	NPC473623
0.9091	High Similarity	NPC475184
0.9085	High Similarity	NPC95090

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 NPC166067 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	352
0.1-0.2	934
0.2-0.3	1591
0.3-0.4	2684
0.4-0.5	2058
0.5-0.6	1079
0.6-0.7	283
0.7-0.8	125
0.8-0.85	33
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9057	High Similarity	NPD7804	Clinical (unspecified phase)
0.9034	High Similarity	NPD1550	Clinical (unspecified phase)
0.9034	High Similarity	NPD1552	Clinical (unspecified phase)
0.8973	High Similarity	NPD1549	Phase 2
0.8968	High Similarity	NPD4381	Clinical (unspecified phase)
0.8889	High Similarity	NPD7411	Suspended
0.8882	High Similarity	NPD7074	Phase 3
0.8867	High Similarity	NPD4378	Clinical (unspecified phase)
0.8839	High Similarity	NPD8443	Clinical (unspecified phase)
0.8824	High Similarity	NPD4380	Phase 2
0.8774	High Similarity	NPD2393	Clinical (unspecified phase)
0.8742	High Similarity	NPD7410	Clinical (unspecified phase)
0.8726	High Similarity	NPD7075	Discontinued
0.8704	High Similarity	NPD7054	Approved
0.8654	High Similarity	NPD7096	Clinical (unspecified phase)
0.865	High Similarity	NPD7472	Approved
0.8598	High Similarity	NPD6797	Phase 2
0.859	High Similarity	NPD6801	Discontinued
0.8581	High Similarity	NPD2796	Approved
0.8562	High Similarity	NPD6959	Discontinued
0.8545	High Similarity	NPD7251	Discontinued
0.8535	High Similarity	NPD7819	Suspended
0.8519	High Similarity	NPD6167	Clinical (unspecified phase)
0.8519	High Similarity	NPD7852	Clinical (unspecified phase)
0.8519	High Similarity	NPD6168	Clinical (unspecified phase)
0.8519	High Similarity	NPD6166	Phase 2
0.8514	High Similarity	NPD1510	Phase 2
0.8494	Intermediate Similarity	NPD7808	Phase 3
0.8493	Intermediate Similarity	NPD1240	Approved
0.8471	Intermediate Similarity	NPD1934	Approved
0.8378	Intermediate Similarity	NPD1607	Approved
0.8323	Intermediate Similarity	NPD6559	Discontinued
0.8313	Intermediate Similarity	NPD7768	Phase 2
0.8312	Intermediate Similarity	NPD6799	Approved
0.8303	Intermediate Similarity	NPD3818	Discontinued
0.8289	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD5494	Approved
0.8153	Intermediate Similarity	NPD5403	Approved
0.8117	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD3750	Approved
0.8113	Intermediate Similarity	NPD6599	Discontinued
0.8108	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD1511	Approved
0.8075	Intermediate Similarity	NPD2801	Approved
0.8037	Intermediate Similarity	NPD3749	Approved
0.8025	Intermediate Similarity	NPD5401	Approved
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD1512	Approved
0.7975	Intermediate Similarity	NPD3882	Suspended
0.7974	Intermediate Similarity	NPD1551	Phase 2
0.7935	Intermediate Similarity	NPD2800	Approved
0.7929	Intermediate Similarity	NPD5844	Phase 1
0.7914	Intermediate Similarity	NPD3817	Phase 2
0.7895	Intermediate Similarity	NPD6651	Approved
0.7871	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2935	Discontinued
0.7849	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD5953	Discontinued
0.7829	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD5124	Phase 1
0.7824	Intermediate Similarity	NPD7286	Phase 2
0.7821	Intermediate Similarity	NPD1243	Approved
0.7812	Intermediate Similarity	NPD920	Approved
0.7805	Intermediate Similarity	NPD5402	Approved
0.7803	Intermediate Similarity	NPD8313	Approved
0.7803	Intermediate Similarity	NPD8312	Approved
0.7799	Intermediate Similarity	NPD2533	Approved
0.7799	Intermediate Similarity	NPD2534	Approved
0.7799	Intermediate Similarity	NPD2532	Approved
0.7797	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD2799	Discontinued
0.7792	Intermediate Similarity	NPD3748	Approved
0.7792	Intermediate Similarity	NPD7033	Discontinued
0.7785	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4628	Phase 3
0.7744	Intermediate Similarity	NPD8455	Phase 2
0.774	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6232	Discontinued
0.7733	Intermediate Similarity	NPD4908	Phase 1
0.7716	Intermediate Similarity	NPD7458	Discontinued
0.7709	Intermediate Similarity	NPD4363	Phase 3
0.7709	Intermediate Similarity	NPD4360	Phase 2
0.7706	Intermediate Similarity	NPD7473	Discontinued
0.7688	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3751	Discontinued
0.7651	Intermediate Similarity	NPD1203	Approved
0.7634	Intermediate Similarity	NPD7584	Approved
0.7633	Intermediate Similarity	NPD3787	Discontinued
0.7632	Intermediate Similarity	NPD2313	Discontinued
0.7624	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD6832	Phase 2
0.76	Intermediate Similarity	NPD2798	Approved
0.7597	Intermediate Similarity	NPD1933	Approved
0.758	Intermediate Similarity	NPD2344	Approved
0.7578	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD3268	Approved
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.7516	Intermediate Similarity	NPD6099	Approved
0.7516	Intermediate Similarity	NPD6100	Approved
0.75	Intermediate Similarity	NPD6777	Approved
0.75	Intermediate Similarity	NPD6776	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD6780	Approved
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6778	Approved
0.75	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD6782	Approved
0.75	Intermediate Similarity	NPD6779	Approved
0.7485	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD7783	Phase 2
0.7473	Intermediate Similarity	NPD7697	Approved
0.7473	Intermediate Similarity	NPD7696	Phase 3
0.7473	Intermediate Similarity	NPD7698	Approved
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7466	Intermediate Similarity	NPD1548	Phase 1
0.746	Intermediate Similarity	NPD8151	Discontinued
0.7456	Intermediate Similarity	NPD919	Approved
0.7452	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD9717	Approved
0.7438	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD1465	Phase 2
0.7417	Intermediate Similarity	NPD2797	Approved
0.7391	Intermediate Similarity	NPD2309	Approved
0.7389	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD422	Phase 1
0.738	Intermediate Similarity	NPD7435	Discontinued
0.7377	Intermediate Similarity	NPD4361	Phase 2
0.7377	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7199	Phase 2
0.7356	Intermediate Similarity	NPD7228	Approved
0.7351	Intermediate Similarity	NPD3225	Approved
0.734	Intermediate Similarity	NPD7871	Phase 2
0.734	Intermediate Similarity	NPD7870	Phase 2
0.7326	Intermediate Similarity	NPD5711	Approved
0.7326	Intermediate Similarity	NPD5710	Approved
0.7316	Intermediate Similarity	NPD7701	Phase 2
0.7308	Intermediate Similarity	NPD943	Approved
0.7308	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1613	Approved
0.7305	Intermediate Similarity	NPD5889	Approved
0.7305	Intermediate Similarity	NPD5890	Approved
0.7301	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6798	Discontinued
0.7273	Intermediate Similarity	NPD1729	Discontinued
0.7267	Intermediate Similarity	NPD1247	Approved
0.7267	Intermediate Similarity	NPD2654	Approved
0.7262	Intermediate Similarity	NPD37	Approved
0.7235	Intermediate Similarity	NPD4967	Phase 2
0.7235	Intermediate Similarity	NPD4966	Approved
0.7235	Intermediate Similarity	NPD4965	Approved
0.7234	Intermediate Similarity	NPD6823	Phase 2
0.7233	Intermediate Similarity	NPD4308	Phase 3
0.723	Intermediate Similarity	NPD9545	Approved
0.7228	Intermediate Similarity	NPD6535	Approved
0.7228	Intermediate Similarity	NPD6534	Approved
0.7226	Intermediate Similarity	NPD4625	Phase 3
0.7225	Intermediate Similarity	NPD7585	Approved
0.7222	Intermediate Similarity	NPD7003	Approved
0.7204	Intermediate Similarity	NPD7699	Phase 2
0.7204	Intermediate Similarity	NPD7700	Phase 2
0.7195	Intermediate Similarity	NPD7213	Phase 3
0.7195	Intermediate Similarity	NPD7212	Phase 2
0.719	Intermediate Similarity	NPD3266	Approved
0.719	Intermediate Similarity	NPD3267	Approved
0.7184	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD3926	Phase 2
0.7176	Intermediate Similarity	NPD4288	Approved
0.7173	Intermediate Similarity	NPD7583	Approved
0.717	Intermediate Similarity	NPD7097	Phase 1
0.716	Intermediate Similarity	NPD6844	Discontinued
0.716	Intermediate Similarity	NPD1652	Phase 2
0.7158	Intermediate Similarity	NPD8320	Phase 1
0.7158	Intermediate Similarity	NPD8319	Approved
0.7152	Intermediate Similarity	NPD1091	Approved
0.7152	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD6234	Discontinued
0.715	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD7874	Approved
0.7143	Intermediate Similarity	NPD6585	Discontinued
0.7143	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1653	Approved
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7113	Intermediate Similarity	NPD7801	Approved
0.7108	Intermediate Similarity	NPD6273	Approved
0.7105	Intermediate Similarity	NPD1608	Approved
0.7105	Intermediate Similarity	NPD3972	Approved
0.7104	Intermediate Similarity	NPD4287	Approved
0.7099	Intermediate Similarity	NPD2424	Discontinued
0.7095	Intermediate Similarity	NPD6104	Discontinued
0.7095	Intermediate Similarity	NPD9493	Approved
0.7088	Intermediate Similarity	NPD8150	Discontinued
0.7081	Intermediate Similarity	NPD5405	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