NPASS Compound

Structure

NPC474107 OpenBabel07101719252D 34 39 0 0 1 0 0 0 0 0999 V2000 -0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 -2.5981 -2.5000 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 4.3301 -2.5000 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 -1.7321 -3.0000 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 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 -0.8660 -1.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 C 0 0 3 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 1.7321 -4.0000 0.0000 C 0 0 0 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 2.5981 -4.5000 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 -0.0000 -1.0000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 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 -0.0000 -4.0000 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 16 1 0 0 0 0 2 16 1 0 0 0 0 3 30 1 0 0 0 0 4 30 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 17 2 0 0 0 0 10 18 2 0 0 0 0 11 19 2 0 0 0 0 12 20 2 0 0 0 0 13 14 2 0 0 0 0 13 21 1 0 0 0 0 14 30 1 0 0 0 0 15 16 2 0 0 0 0 15 22 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 29 1 0 0 0 0 21 23 1 0 0 0 0 21 28 2 0 0 0 0 22 24 1 0 0 0 0 22 33 1 0 0 0 0 23 25 1 0 0 0 0 23 29 2 0 0 0 0 24 25 2 0 0 0 0 24 26 1 0 0 0 0 25 27 1 0 0 0 0 26 31 2 0 0 0 0 27 32 2 0 0 0 0 28 34 1 0 0 0 0 29 33 1 0 0 0 0 30 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.17
Volume:	476.984
LogP:	7.338
LogD:	4.561
LogS:	-3.787
# Rotatable Bonds:	1
TPSA:	58.92
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.295
Synthetic Accessibility Score:	3.362
Fsp3:	0.133
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.655
MDCK Permeability:	1.4742931853106711e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.071
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	101.1305923461914%
Volume Distribution (VD):	0.275
Pgp-substrate:	0.8567364811897278%

ADMET: Metabolism

CYP1A2-inhibitor:	0.592
CYP1A2-substrate:	0.166
CYP2C19-inhibitor:	0.9
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.858
CYP2C9-substrate:	0.753
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.786
CYP3A4-inhibitor:	0.256
CYP3A4-substrate:	0.202

ADMET: Excretion

Clearance (CL):	1.362
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.119
Human Hepatotoxicity (H-HT):	0.648
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.733
Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	0.844
Skin Sensitization:	0.768
Carcinogencity:	0.848
Eye Corrosion:	0.003
Eye Irritation:	0.184
Respiratory Toxicity:	0.692

Download Data

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

Natural Product: NPC474107

Natural Product ID:	NPC474107
*Common Name:**	Tecomaquinone
IUPAC Name:	n.a.
Synonyms:	tecomaquinone
Standard InCHIKey:	VYNGZASNGVAOMT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H24O4/c1-16(2)15-22-24-25(27(32)18-10-6-5-9-17(18)26(24)31)23-21-13-14-30(3,4)34-28(21)19-11-7-8-12-20(19)29(23)33-22/h5-15,22H,1-4H3
SMILES:	CC(=CC1C2=C(C3=C(O1)C4=CC=CC=C4C5=C3C=CC(O5)(C)C)C(=O)C6=CC=CC=C6C2=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL461909
PubChem CID:	3574508
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001649] Isochromanequinones [CHEMONTID:0002355] Benzoisochromanequinones

*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
NPO4592	Lippia sidoides	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421746]
NPO4592	Lippia sidoides	Species	Verbenaceae	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	6

Activity Type	# Activity
Cell Line	3
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[493600]
NPT1577	Cell Line	SW1573	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[493600]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[493600]
NPT2	Others	Unspecified		IC50	=	65.0	nM	PMID[493601]
NPT2	Others	Unspecified		IC50	=	112.0	nM	PMID[493601]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	22000.0	nM	PMID[493601]

☑ 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 NPC474107 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	463
0.1-0.2	1674
0.2-0.3	3781
0.3-0.4	10227
0.4-0.5	8723
0.5-0.6	4775
0.6-0.7	7521
0.7-0.8	5344
0.8-0.85	170
0.85-0.9	17
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8671	High Similarity	NPC470406
0.8581	High Similarity	NPC149780
0.8581	High Similarity	NPC3898
0.8571	High Similarity	NPC470407
0.8562	High Similarity	NPC301341
0.8523	High Similarity	NPC69755
0.8521	High Similarity	NPC57552
0.8487	Intermediate Similarity	NPC478018
0.8471	Intermediate Similarity	NPC67197
0.8467	Intermediate Similarity	NPC53016
0.8435	Intermediate Similarity	NPC284184
0.8435	Intermediate Similarity	NPC186647
0.8428	Intermediate Similarity	NPC472261
0.8421	Intermediate Similarity	NPC60389
0.8411	Intermediate Similarity	NPC308006
0.8411	Intermediate Similarity	NPC93241
0.8411	Intermediate Similarity	NPC27798
0.8356	Intermediate Similarity	NPC1249
0.8345	Intermediate Similarity	NPC183103
0.8345	Intermediate Similarity	NPC474340
0.8344	Intermediate Similarity	NPC117674
0.8333	Intermediate Similarity	NPC124365
0.8312	Intermediate Similarity	NPC472839
0.8301	Intermediate Similarity	NPC211565
0.8301	Intermediate Similarity	NPC300540
0.8301	Intermediate Similarity	NPC281398
0.8291	Intermediate Similarity	NPC276231
0.8291	Intermediate Similarity	NPC469507
0.8276	Intermediate Similarity	NPC477412
0.8252	Intermediate Similarity	NPC45537
0.8252	Intermediate Similarity	NPC298884
0.825	Intermediate Similarity	NPC284495
0.8243	Intermediate Similarity	NPC232996
0.8235	Intermediate Similarity	NPC49282
0.8235	Intermediate Similarity	NPC478019
0.8217	Intermediate Similarity	NPC24232
0.8205	Intermediate Similarity	NPC144010
0.8204	Intermediate Similarity	NPC102053
0.82	Intermediate Similarity	NPC476191
0.8188	Intermediate Similarity	NPC471542
0.8176	Intermediate Similarity	NPC22222
0.8176	Intermediate Similarity	NPC281513
0.8171	Intermediate Similarity	NPC76647
0.817	Intermediate Similarity	NPC189650
0.817	Intermediate Similarity	NPC472836
0.8165	Intermediate Similarity	NPC329844
0.8165	Intermediate Similarity	NPC179170
0.8165	Intermediate Similarity	NPC477691
0.816	Intermediate Similarity	NPC469664
0.8158	Intermediate Similarity	NPC329493
0.8153	Intermediate Similarity	NPC145830
0.8137	Intermediate Similarity	NPC186325
0.8133	Intermediate Similarity	NPC478002
0.8133	Intermediate Similarity	NPC475104
0.8125	Intermediate Similarity	NPC299094
0.8125	Intermediate Similarity	NPC428300
0.8125	Intermediate Similarity	NPC10051
0.8125	Intermediate Similarity	NPC44199
0.8121	Intermediate Similarity	NPC155211
0.8117	Intermediate Similarity	NPC179970
0.8113	Intermediate Similarity	NPC55662
0.8113	Intermediate Similarity	NPC166054
0.8113	Intermediate Similarity	NPC478161
0.8113	Intermediate Similarity	NPC478159
0.8107	Intermediate Similarity	NPC58538
0.8105	Intermediate Similarity	NPC215451
0.8105	Intermediate Similarity	NPC167663
0.8105	Intermediate Similarity	NPC277369
0.8101	Intermediate Similarity	NPC27615
0.8101	Intermediate Similarity	NPC477690
0.8101	Intermediate Similarity	NPC154683
0.8101	Intermediate Similarity	NPC40356
0.8089	Intermediate Similarity	NPC474660
0.8089	Intermediate Similarity	NPC477914
0.8086	Intermediate Similarity	NPC165549
0.8086	Intermediate Similarity	NPC18380
0.8086	Intermediate Similarity	NPC189552
0.8086	Intermediate Similarity	NPC273467
0.8086	Intermediate Similarity	NPC137232
0.8084	Intermediate Similarity	NPC85368
0.8084	Intermediate Similarity	NPC203751
0.8079	Intermediate Similarity	NPC1268
0.8079	Intermediate Similarity	NPC477408
0.8079	Intermediate Similarity	NPC223336
0.8077	Intermediate Similarity	NPC95526
0.8075	Intermediate Similarity	NPC324736
0.8075	Intermediate Similarity	NPC177650
0.8072	Intermediate Similarity	NPC313304
0.8063	Intermediate Similarity	NPC478223
0.8063	Intermediate Similarity	NPC180340
0.8063	Intermediate Similarity	NPC221992
0.8061	Intermediate Similarity	NPC234497
0.8061	Intermediate Similarity	NPC105414
0.8061	Intermediate Similarity	NPC470341
0.8061	Intermediate Similarity	NPC472058
0.8061	Intermediate Similarity	NPC473945
0.8061	Intermediate Similarity	NPC324522
0.8056	Intermediate Similarity	NPC177925
0.8054	Intermediate Similarity	NPC217914
0.8052	Intermediate Similarity	NPC274085
0.8052	Intermediate Similarity	NPC59522
0.8052	Intermediate Similarity	NPC89664
0.8052	Intermediate Similarity	NPC477913
0.805	Intermediate Similarity	NPC472408
0.805	Intermediate Similarity	NPC210942
0.805	Intermediate Similarity	NPC95842
0.805	Intermediate Similarity	NPC290927
0.805	Intermediate Similarity	NPC128961
0.805	Intermediate Similarity	NPC169990
0.805	Intermediate Similarity	NPC178964
0.805	Intermediate Similarity	NPC280530
0.8049	Intermediate Similarity	NPC26386
0.8047	Intermediate Similarity	NPC478000
0.8039	Intermediate Similarity	NPC52576
0.8038	Intermediate Similarity	NPC474417
0.8038	Intermediate Similarity	NPC149526
0.8036	Intermediate Similarity	NPC186800
0.8027	Intermediate Similarity	NPC279596
0.8027	Intermediate Similarity	NPC239134
0.8027	Intermediate Similarity	NPC164295
0.8026	Intermediate Similarity	NPC473499
0.8025	Intermediate Similarity	NPC312993
0.8025	Intermediate Similarity	NPC292863
0.8025	Intermediate Similarity	NPC184326
0.8024	Intermediate Similarity	NPC477836
0.8013	Intermediate Similarity	NPC233707
0.8013	Intermediate Similarity	NPC478163
0.8012	Intermediate Similarity	NPC478001
0.8012	Intermediate Similarity	NPC19097
0.8	Intermediate Similarity	NPC251336
0.8	Intermediate Similarity	NPC30027
0.8	Intermediate Similarity	NPC97662
0.8	Intermediate Similarity	NPC226656
0.8	Intermediate Similarity	NPC272502
0.8	Intermediate Similarity	NPC66508
0.7988	Intermediate Similarity	NPC289876
0.7987	Intermediate Similarity	NPC472840
0.7987	Intermediate Similarity	NPC476473
0.7986	Intermediate Similarity	NPC224657
0.7975	Intermediate Similarity	NPC269117
0.7975	Intermediate Similarity	NPC470568
0.7975	Intermediate Similarity	NPC473466
0.7975	Intermediate Similarity	NPC294646
0.7975	Intermediate Similarity	NPC24761
0.7972	Intermediate Similarity	NPC182646
0.7965	Intermediate Similarity	NPC224557
0.7965	Intermediate Similarity	NPC292706
0.7963	Intermediate Similarity	NPC55443
0.7963	Intermediate Similarity	NPC195167
0.7963	Intermediate Similarity	NPC471541
0.7963	Intermediate Similarity	NPC186113
0.7963	Intermediate Similarity	NPC477692
0.7963	Intermediate Similarity	NPC18699
0.7962	Intermediate Similarity	NPC472841
0.7962	Intermediate Similarity	NPC192069
0.7952	Intermediate Similarity	NPC225419
0.795	Intermediate Similarity	NPC288353
0.795	Intermediate Similarity	NPC279605
0.7949	Intermediate Similarity	NPC147250
0.7947	Intermediate Similarity	NPC245923
0.7939	Intermediate Similarity	NPC156432
0.7937	Intermediate Similarity	NPC214632
0.7937	Intermediate Similarity	NPC135522
0.7937	Intermediate Similarity	NPC84721
0.7935	Intermediate Similarity	NPC471451
0.7935	Intermediate Similarity	NPC245522
0.7935	Intermediate Similarity	NPC477409
0.7935	Intermediate Similarity	NPC114513
0.7935	Intermediate Similarity	NPC471600
0.7931	Intermediate Similarity	NPC474264
0.7931	Intermediate Similarity	NPC474737
0.7929	Intermediate Similarity	NPC470667
0.7927	Intermediate Similarity	NPC108767
0.7927	Intermediate Similarity	NPC101116
0.7927	Intermediate Similarity	NPC472402
0.7927	Intermediate Similarity	NPC146837
0.7927	Intermediate Similarity	NPC15374
0.7927	Intermediate Similarity	NPC212099
0.7927	Intermediate Similarity	NPC278329
0.7927	Intermediate Similarity	NPC473961
0.7925	Intermediate Similarity	NPC144283
0.7925	Intermediate Similarity	NPC72958
0.7925	Intermediate Similarity	NPC189773
0.7925	Intermediate Similarity	NPC478148
0.7925	Intermediate Similarity	NPC470569
0.7925	Intermediate Similarity	NPC232645
0.7922	Intermediate Similarity	NPC474300
0.7919	Intermediate Similarity	NPC225051
0.7917	Intermediate Similarity	NPC56332
0.7914	Intermediate Similarity	NPC472052
0.7914	Intermediate Similarity	NPC476506
0.7914	Intermediate Similarity	NPC472060
0.7914	Intermediate Similarity	NPC472618
0.7914	Intermediate Similarity	NPC470810
0.7914	Intermediate Similarity	NPC470342
0.7911	Intermediate Similarity	NPC65775
0.7911	Intermediate Similarity	NPC100985
0.7911	Intermediate Similarity	NPC300983
0.7911	Intermediate Similarity	NPC97028
0.7911	Intermediate Similarity	NPC97029

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 NPC474107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	978
0.2-0.3	1412
0.3-0.4	2618
0.4-0.5	2081
0.5-0.6	1085
0.6-0.7	431
0.7-0.8	139
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8255	Intermediate Similarity	NPD2346	Discontinued
0.8025	Intermediate Similarity	NPD3226	Approved
0.7975	Intermediate Similarity	NPD6959	Discontinued
0.7911	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD2313	Discontinued
0.7805	Intermediate Similarity	NPD5494	Approved
0.7798	Intermediate Similarity	NPD5844	Phase 1
0.7712	Intermediate Similarity	NPD2796	Approved
0.7708	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD1471	Phase 3
0.7662	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD7003	Approved
0.7607	Intermediate Similarity	NPD7819	Suspended
0.7571	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD2344	Approved
0.7546	Intermediate Similarity	NPD6844	Discontinued
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD6232	Discontinued
0.75	Intermediate Similarity	NPD1651	Approved
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7471	Intermediate Similarity	NPD8312	Approved
0.7471	Intermediate Similarity	NPD8313	Approved
0.7471	Intermediate Similarity	NPD7473	Discontinued
0.7466	Intermediate Similarity	NPD1611	Approved
0.7455	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD5402	Approved
0.745	Intermediate Similarity	NPD2798	Approved
0.7438	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD3751	Discontinued
0.7427	Intermediate Similarity	NPD7177	Discontinued
0.7419	Intermediate Similarity	NPD3748	Approved
0.7418	Intermediate Similarity	NPD8285	Discontinued
0.7415	Intermediate Similarity	NPD3972	Approved
0.7394	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD6273	Approved
0.7386	Intermediate Similarity	NPD4307	Phase 2
0.7386	Intermediate Similarity	NPD2979	Phase 3
0.7378	Intermediate Similarity	NPD7411	Suspended
0.7362	Intermediate Similarity	NPD7458	Discontinued
0.7358	Intermediate Similarity	NPD2309	Approved
0.7351	Intermediate Similarity	NPD6832	Phase 2
0.7338	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4380	Phase 2
0.731	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD2801	Approved
0.7283	Intermediate Similarity	NPD6779	Approved
0.7283	Intermediate Similarity	NPD6782	Approved
0.7283	Intermediate Similarity	NPD6780	Approved
0.7283	Intermediate Similarity	NPD6778	Approved
0.7283	Intermediate Similarity	NPD6777	Approved
0.7283	Intermediate Similarity	NPD6776	Approved
0.7283	Intermediate Similarity	NPD6781	Approved
0.7267	Intermediate Similarity	NPD7390	Discontinued
0.7267	Intermediate Similarity	NPD1470	Approved
0.7262	Intermediate Similarity	NPD3749	Approved
0.725	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD8150	Discontinued
0.7239	Intermediate Similarity	NPD920	Approved
0.7235	Intermediate Similarity	NPD1247	Approved
0.723	Intermediate Similarity	NPD1281	Approved
0.7229	Intermediate Similarity	NPD6280	Approved
0.7229	Intermediate Similarity	NPD6279	Approved
0.7222	Intermediate Similarity	NPD2533	Approved
0.7222	Intermediate Similarity	NPD2534	Approved
0.7222	Intermediate Similarity	NPD2532	Approved
0.7219	Intermediate Similarity	NPD7870	Phase 2
0.7219	Intermediate Similarity	NPD7871	Phase 2
0.7209	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD6166	Phase 2
0.7209	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7768	Phase 2
0.72	Intermediate Similarity	NPD1876	Approved
0.7197	Intermediate Similarity	NPD4308	Phase 3
0.7197	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD3787	Discontinued
0.7188	Intermediate Similarity	NPD4628	Phase 3
0.7188	Intermediate Similarity	NPD3750	Approved
0.7186	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1549	Phase 2
0.7169	Intermediate Similarity	NPD5890	Approved
0.7169	Intermediate Similarity	NPD5889	Approved
0.7166	Intermediate Similarity	NPD7698	Approved
0.7166	Intermediate Similarity	NPD7696	Phase 3
0.7166	Intermediate Similarity	NPD7697	Approved
0.7166	Intermediate Similarity	NPD7435	Discontinued
0.7152	Intermediate Similarity	NPD2438	Suspended
0.7152	Intermediate Similarity	NPD5404	Approved
0.7152	Intermediate Similarity	NPD5406	Approved
0.7152	Intermediate Similarity	NPD5408	Approved
0.7152	Intermediate Similarity	NPD5405	Approved
0.7152	Intermediate Similarity	NPD3267	Approved
0.7152	Intermediate Similarity	NPD3266	Approved
0.7143	Intermediate Similarity	NPD5691	Approved
0.7143	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6801	Discontinued
0.7126	Intermediate Similarity	NPD1934	Approved
0.7117	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6585	Discontinued
0.7108	Intermediate Similarity	NPD6599	Discontinued
0.7107	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD6534	Approved
0.7104	Intermediate Similarity	NPD6535	Approved
0.7101	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6808	Phase 2
0.7089	Intermediate Similarity	NPD1510	Phase 2
0.7086	Intermediate Similarity	NPD1283	Approved
0.7083	Intermediate Similarity	NPD1241	Discontinued
0.7062	Intermediate Similarity	NPD6559	Discontinued
0.7059	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7075	Discontinued
0.7056	Intermediate Similarity	NPD8434	Phase 2
0.7052	Intermediate Similarity	NPD3926	Phase 2
0.7049	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6212	Phase 3
0.7049	Intermediate Similarity	NPD6213	Phase 3
0.7044	Intermediate Similarity	NPD2531	Phase 2
0.7041	Intermediate Similarity	NPD3817	Phase 2
0.7032	Intermediate Similarity	NPD7985	Registered
0.7032	Intermediate Similarity	NPD3268	Approved
0.703	Intermediate Similarity	NPD5403	Approved
0.7019	Intermediate Similarity	NPD1243	Approved
0.7016	Intermediate Similarity	NPD7701	Phase 2
0.7012	Intermediate Similarity	NPD5401	Approved
0.7	Intermediate Similarity	NPD1201	Approved
0.6995	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD7783	Phase 2
0.6994	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7699	Phase 2
0.6989	Remote Similarity	NPD7700	Phase 2
0.6987	Remote Similarity	NPD8032	Phase 2
0.6981	Remote Similarity	NPD7033	Discontinued
0.698	Remote Similarity	NPD17	Approved
0.6968	Remote Similarity	NPD7008	Discontinued
0.6962	Remote Similarity	NPD1607	Approved
0.6951	Remote Similarity	NPD6799	Approved
0.6951	Remote Similarity	NPD1511	Approved
0.6946	Remote Similarity	NPD2649	Approved
0.6946	Remote Similarity	NPD2651	Approved
0.6943	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD7874	Approved
0.6937	Remote Similarity	NPD6099	Approved
0.6937	Remote Similarity	NPD6100	Approved
0.6933	Remote Similarity	NPD3887	Approved
0.6932	Remote Similarity	NPD3818	Discontinued
0.6931	Remote Similarity	NPD6823	Phase 2
0.6928	Remote Similarity	NPD2797	Approved
0.6923	Remote Similarity	NPD6798	Discontinued
0.6919	Remote Similarity	NPD919	Approved
0.6914	Remote Similarity	NPD2800	Approved
0.6907	Remote Similarity	NPD7801	Approved
0.6901	Remote Similarity	NPD3882	Suspended
0.6899	Remote Similarity	NPD1933	Approved
0.6897	Remote Similarity	NPD7229	Phase 3
0.6893	Remote Similarity	NPD7054	Approved
0.6892	Remote Similarity	NPD7644	Approved
0.6883	Remote Similarity	NPD1019	Discontinued
0.6882	Remote Similarity	NPD5761	Phase 2
0.6882	Remote Similarity	NPD5760	Phase 2
0.6879	Remote Similarity	NPD6233	Phase 2
0.6871	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4626	Approved
0.6867	Remote Similarity	NPD1512	Approved
0.6859	Remote Similarity	NPD4625	Phase 3
0.6854	Remote Similarity	NPD7472	Approved
0.6854	Remote Similarity	NPD7074	Phase 3
0.6852	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD2897	Discontinued
0.6842	Remote Similarity	NPD1608	Approved
0.6842	Remote Similarity	NPD2296	Approved
0.6835	Remote Similarity	NPD1240	Approved
0.6833	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4477	Approved
0.6832	Remote Similarity	NPD4476	Approved
0.6832	Remote Similarity	NPD1551	Phase 2
0.6824	Remote Similarity	NPD7577	Discontinued
0.6824	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3496	Discontinued
0.6818	Remote Similarity	NPD1203	Approved
0.6816	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD6797	Phase 2
0.6815	Remote Similarity	NPD3764	Approved
0.6815	Remote Similarity	NPD411	Approved
0.6815	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7097	Phase 1
0.6807	Remote Similarity	NPD4662	Approved
0.6807	Remote Similarity	NPD4661	Approved
0.6804	Remote Similarity	NPD8151	Discontinued
0.68	Remote Similarity	NPD5585	Approved
0.6797	Remote Similarity	NPD5327	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data