NPASS Compound

Structure

NPC29577 OpenBabel07101718202D 32 33 0 0 0 0 0 0 0 0999 V2000 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 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 5.1962 -1.0000 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 5.1962 0.0000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 2.5981 1.5000 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 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 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 2.5981 0.5000 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 -0.0000 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 3.4641 3.0000 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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 16 20 1 0 0 0 0 16 24 2 0 0 0 0 17 21 2 0 0 0 0 17 23 1 0 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 21 26 1 0 0 0 0 22 28 1 0 0 0 0 23 29 1 0 0 0 0 24 32 1 0 0 0 0 25 26 2 0 0 0 0 25 30 1 0 0 0 0 26 27 1 0 0 0 0 27 31 2 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.27
Volume:	483.931
LogP:	8.259
LogD:	5.149
LogS:	-3.223
# Rotatable Bonds:	15
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	2.538
Fsp3:	0.519
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.337
MDCK Permeability:	1.3967041013529524e-05
Pgp-inhibitor:	0.485
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	100.36016845703125%
Volume Distribution (VD):	1.556
Pgp-substrate:	0.41102272272109985%

ADMET: Metabolism

CYP1A2-inhibitor:	0.745
CYP1A2-substrate:	0.177
CYP2C19-inhibitor:	0.907
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.297
CYP2C9-substrate:	0.981
CYP2D6-inhibitor:	0.872
CYP2D6-substrate:	0.336
CYP3A4-inhibitor:	0.34
CYP3A4-substrate:	0.039

ADMET: Excretion

Clearance (CL):	7.443
Half-life (T1/2):	0.576

ADMET: Toxicity

hERG Blockers:	0.411
Human Hepatotoxicity (H-HT):	0.035
Drug-inuced Liver Injury (DILI):	0.049
AMES Toxicity:	0.162
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.969
Carcinogencity:	0.03
Eye Corrosion:	0.039
Eye Irritation:	0.962
Respiratory Toxicity:	0.505

Download Data

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

Natural Product: NPC29577

Natural Product ID:	NPC29577
*Common Name:**	3-Heptyl-5-Hydroxyphenyl 2-Heptyl-4,6-Dihydroxybenzoate
IUPAC Name:	(3-heptyl-5-hydroxyphenyl) 2-heptyl-4,6-dihydroxybenzoate
Synonyms:
Standard InCHIKey:	FJYOXVSNSKDASL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C27H38O5/c1-3-5-7-9-11-13-20-15-22(28)18-24(16-20)32-27(31)26-21(14-12-10-8-6-4-2)17-23(29)19-25(26)30/h15-19,28-30H,3-14H2,1-2H3
SMILES:	CCCCCCCc1cc(O)cc(c1)OC(=O)c1c(O)cc(cc1CCCCCCC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467775
PubChem CID:	14581926
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001645] Depsides and depsidones

*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
NPO33495	Acremonium sp. BCC 14080	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[18363379]

☑ 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
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	13000.0	nM	PMID[564022]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	=	13600.0	nM	PMID[564022]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	34300.0	nM	PMID[564022]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	9900.0	nM	PMID[564022]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	>	100000.0	nM	PMID[564022]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	8800.0	nM	PMID[564022]

☑ 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 NPC29577 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	354
0.1-0.2	1630
0.2-0.3	3990
0.3-0.4	9615
0.4-0.5	8676
0.5-0.6	3375
0.6-0.7	5435
0.7-0.8	6098
0.8-0.85	2447
0.85-0.9	978
0.9-0.95	82
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
0.9928	High Similarity	NPC237208
0.9856	High Similarity	NPC134621
0.9784	High Similarity	NPC66404
0.9784	High Similarity	NPC95123
0.9783	High Similarity	NPC105648
0.9718	High Similarity	NPC6923
0.971	High Similarity	NPC220106
0.965	High Similarity	NPC307780
0.965	High Similarity	NPC309979
0.965	High Similarity	NPC60413
0.9648	High Similarity	NPC105415
0.958	High Similarity	NPC233267
0.958	High Similarity	NPC291049
0.9577	High Similarity	NPC12305
0.9574	High Similarity	NPC32470
0.9507	High Similarity	NPC267509
0.95	High Similarity	NPC250755
0.9448	High Similarity	NPC133856
0.9384	High Similarity	NPC273483
0.9306	High Similarity	NPC125801
0.9301	High Similarity	NPC312789
0.9296	High Similarity	NPC310340
0.9291	High Similarity	NPC67650
0.9291	High Similarity	NPC275734
0.9291	High Similarity	NPC1704
0.9257	High Similarity	NPC149618
0.9257	High Similarity	NPC89625
0.9252	High Similarity	NPC217447
0.9247	High Similarity	NPC194379
0.9241	High Similarity	NPC37139
0.9236	High Similarity	NPC225173
0.9236	High Similarity	NPC163846
0.9195	High Similarity	NPC146211
0.9184	High Similarity	NPC227166
0.9178	High Similarity	NPC476684
0.9161	High Similarity	NPC472006
0.9161	High Similarity	NPC51106
0.9161	High Similarity	NPC469542
0.9143	High Similarity	NPC135837
0.9137	High Similarity	NPC180905
0.9137	High Similarity	NPC182496
0.9128	High Similarity	NPC471800
0.9116	High Similarity	NPC295036
0.9116	High Similarity	NPC150928
0.9116	High Similarity	NPC158866
0.9116	High Similarity	NPC470107
0.911	High Similarity	NPC240253
0.911	High Similarity	NPC471642
0.911	High Similarity	NPC471641
0.911	High Similarity	NPC240622
0.911	High Similarity	NPC172329
0.911	High Similarity	NPC2569
0.9103	High Similarity	NPC473927
0.9103	High Similarity	NPC181388
0.9103	High Similarity	NPC154217
0.9091	High Similarity	NPC469579
0.9091	High Similarity	NPC474385
0.9091	High Similarity	NPC49108
0.9073	High Similarity	NPC474373
0.9071	High Similarity	NPC242712
0.9067	High Similarity	NPC54928
0.9065	High Similarity	NPC175943
0.906	High Similarity	NPC472799
0.9054	High Similarity	NPC478148
0.9048	High Similarity	NPC97028
0.9048	High Similarity	NPC288036
0.9048	High Similarity	NPC65775
0.9048	High Similarity	NPC100985
0.9048	High Similarity	NPC158338
0.9048	High Similarity	NPC473978
0.9048	High Similarity	NPC97029
0.9048	High Similarity	NPC65589
0.9048	High Similarity	NPC10027
0.9041	High Similarity	NPC259632
0.9034	High Similarity	NPC196137
0.9034	High Similarity	NPC469935
0.9034	High Similarity	NPC1886
0.9034	High Similarity	NPC131766
0.9034	High Similarity	NPC178627
0.9028	High Similarity	NPC36181
0.9021	High Similarity	NPC475730
0.9014	High Similarity	NPC57380
0.9013	High Similarity	NPC143050
0.9007	High Similarity	NPC194579
0.9007	High Similarity	NPC70380
0.9	High Similarity	NPC20541
0.8993	High Similarity	NPC142308
0.8986	High Similarity	NPC227122
0.8986	High Similarity	NPC475460
0.898	High Similarity	NPC256672
0.898	High Similarity	NPC27221
0.898	High Similarity	NPC7025
0.8973	High Similarity	NPC138978
0.8973	High Similarity	NPC470322
0.8973	High Similarity	NPC107625
0.8966	High Similarity	NPC280404
0.8966	High Similarity	NPC210425
0.8966	High Similarity	NPC470296
0.8966	High Similarity	NPC188632
0.8966	High Similarity	NPC94794
0.8966	High Similarity	NPC87609
0.8966	High Similarity	NPC277426
0.8966	High Similarity	NPC112791
0.8966	High Similarity	NPC196459
0.8966	High Similarity	NPC86373
0.8961	High Similarity	NPC284007
0.8958	High Similarity	NPC96692
0.8954	High Similarity	NPC303565
0.8951	High Similarity	NPC165172
0.8951	High Similarity	NPC254994
0.8951	High Similarity	NPC241975
0.8951	High Similarity	NPC19476
0.8947	High Similarity	NPC238381
0.8944	High Similarity	NPC472602
0.8944	High Similarity	NPC94248
0.8944	High Similarity	NPC191835
0.8944	High Similarity	NPC212693
0.894	High Similarity	NPC4547
0.8936	High Similarity	NPC50455
0.8933	High Similarity	NPC475895
0.8933	High Similarity	NPC210942
0.8933	High Similarity	NPC169990
0.8926	High Similarity	NPC58668
0.8926	High Similarity	NPC23668
0.8926	High Similarity	NPC106372
0.8926	High Similarity	NPC232645
0.8926	High Similarity	NPC149526
0.8926	High Similarity	NPC193976
0.8926	High Similarity	NPC72958
0.8926	High Similarity	NPC474417
0.8919	High Similarity	NPC469932
0.8912	High Similarity	NPC140120
0.8912	High Similarity	NPC22005
0.8912	High Similarity	NPC142863
0.8912	High Similarity	NPC7943
0.8912	High Similarity	NPC123202
0.8904	High Similarity	NPC472034
0.8903	High Similarity	NPC267153
0.8903	High Similarity	NPC7752
0.8897	High Similarity	NPC73028
0.8897	High Similarity	NPC471643
0.8897	High Similarity	NPC84266
0.8897	High Similarity	NPC471639
0.8896	High Similarity	NPC93739
0.8889	High Similarity	NPC90411
0.8889	High Similarity	NPC53649
0.8889	High Similarity	NPC477272
0.8889	High Similarity	NPC158634
0.8881	High Similarity	NPC470083
0.8881	High Similarity	NPC199458
0.8881	High Similarity	NPC219584
0.8881	High Similarity	NPC183639
0.8881	High Similarity	NPC124269
0.8881	High Similarity	NPC32360
0.8881	High Similarity	NPC472368
0.8874	High Similarity	NPC297531
0.8874	High Similarity	NPC213936
0.8873	High Similarity	NPC476333
0.8873	High Similarity	NPC473391
0.8873	High Similarity	NPC13408
0.8873	High Similarity	NPC472364
0.8873	High Similarity	NPC472367
0.8873	High Similarity	NPC71256
0.8867	High Similarity	NPC87708
0.8867	High Similarity	NPC474843
0.8867	High Similarity	NPC175978
0.8867	High Similarity	NPC207624
0.8867	High Similarity	NPC154683
0.8867	High Similarity	NPC40356
0.8859	High Similarity	NPC325983
0.8859	High Similarity	NPC473466
0.8859	High Similarity	NPC474660
0.8859	High Similarity	NPC119929
0.8857	High Similarity	NPC10971
0.8857	High Similarity	NPC153783
0.8851	High Similarity	NPC106328
0.8851	High Similarity	NPC161864
0.8851	High Similarity	NPC469933
0.8851	High Similarity	NPC208303
0.8851	High Similarity	NPC35150
0.8851	High Similarity	NPC221352
0.8849	High Similarity	NPC219892
0.8849	High Similarity	NPC189823
0.8844	High Similarity	NPC196114
0.8844	High Similarity	NPC57470
0.8844	High Similarity	NPC472033
0.8844	High Similarity	NPC24136
0.8844	High Similarity	NPC187282
0.8844	High Similarity	NPC290133
0.8844	High Similarity	NPC153758
0.8844	High Similarity	NPC130176
0.8844	High Similarity	NPC99454
0.8839	High Similarity	NPC474350
0.8839	High Similarity	NPC156082
0.8839	High Similarity	NPC300984
0.8836	High Similarity	NPC11700
0.8836	High Similarity	NPC470932
0.8828	High Similarity	NPC471644
0.8828	High Similarity	NPC471640
0.8828	High Similarity	NPC182255

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 NPC29577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	322
0.1-0.2	999
0.2-0.3	1596
0.3-0.4	2579
0.4-0.5	1808
0.5-0.6	1138
0.6-0.7	495
0.7-0.8	145
0.8-0.85	55
0.85-0.9	11
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9149	High Similarity	NPD970	Clinical (unspecified phase)
0.906	High Similarity	NPD7819	Suspended
0.8759	High Similarity	NPD3750	Approved
0.8649	High Similarity	NPD2534	Approved
0.8649	High Similarity	NPD4378	Clinical (unspecified phase)
0.8649	High Similarity	NPD2533	Approved
0.8649	High Similarity	NPD2532	Approved
0.8636	High Similarity	NPD3749	Approved
0.8552	High Similarity	NPD1552	Clinical (unspecified phase)
0.8552	High Similarity	NPD1550	Clinical (unspecified phase)
0.8521	High Similarity	NPD1240	Approved
0.8516	High Similarity	NPD7075	Discontinued
0.8511	High Similarity	NPD6859	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD1549	Phase 2
0.8456	Intermediate Similarity	NPD6799	Approved
0.8456	Intermediate Similarity	NPD1511	Approved
0.8452	Intermediate Similarity	NPD7768	Phase 2
0.8442	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8431	Intermediate Similarity	NPD7411	Suspended
0.8418	Intermediate Similarity	NPD6232	Discontinued
0.8414	Intermediate Similarity	NPD1510	Phase 2
0.8414	Intermediate Similarity	NPD3748	Approved
0.8403	Intermediate Similarity	NPD1607	Approved
0.84	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8387	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD1934	Approved
0.8375	Intermediate Similarity	NPD7473	Discontinued
0.8366	Intermediate Similarity	NPD6599	Discontinued
0.8356	Intermediate Similarity	NPD2796	Approved
0.8356	Intermediate Similarity	NPD2935	Discontinued
0.8356	Intermediate Similarity	NPD1551	Phase 2
0.8354	Intermediate Similarity	NPD6959	Discontinued
0.8344	Intermediate Similarity	NPD1512	Approved
0.8323	Intermediate Similarity	NPD2801	Approved
0.8323	Intermediate Similarity	NPD1465	Phase 2
0.8311	Intermediate Similarity	NPD1243	Approved
0.8301	Intermediate Similarity	NPD3226	Approved
0.8286	Intermediate Similarity	NPD1203	Approved
0.8269	Intermediate Similarity	NPD3817	Phase 2
0.8255	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD6099	Approved
0.8231	Intermediate Similarity	NPD6100	Approved
0.8217	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD3882	Suspended
0.8199	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD2800	Approved
0.8163	Intermediate Similarity	NPD2799	Discontinued
0.816	Intermediate Similarity	NPD5844	Phase 1
0.8141	Intermediate Similarity	NPD6801	Discontinued
0.8112	Intermediate Similarity	NPD6832	Phase 2
0.8071	Intermediate Similarity	NPD1608	Approved
0.8071	Intermediate Similarity	NPD9717	Approved
0.8067	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8054	Intermediate Similarity	NPD2346	Discontinued
0.805	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD2797	Approved
0.8013	Intermediate Similarity	NPD4380	Phase 2
0.8013	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD422	Phase 1
0.8	Intermediate Similarity	NPD3268	Approved
0.7975	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD6166	Phase 2
0.7975	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5710	Approved
0.7963	Intermediate Similarity	NPD5711	Approved
0.7939	Intermediate Similarity	NPD7054	Approved
0.7935	Intermediate Similarity	NPD920	Approved
0.7933	Intermediate Similarity	NPD2344	Approved
0.7908	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD6651	Approved
0.7895	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD7472	Approved
0.7879	Intermediate Similarity	NPD3818	Discontinued
0.7877	Intermediate Similarity	NPD411	Approved
0.7857	Intermediate Similarity	NPD17	Approved
0.7857	Intermediate Similarity	NPD7390	Discontinued
0.7844	Intermediate Similarity	NPD5953	Discontinued
0.7838	Intermediate Similarity	NPD447	Suspended
0.7838	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7286	Phase 2
0.7821	Intermediate Similarity	NPD5403	Approved
0.7812	Intermediate Similarity	NPD4288	Approved
0.7812	Intermediate Similarity	NPD5402	Approved
0.7806	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD4308	Phase 3
0.7798	Intermediate Similarity	NPD7251	Discontinued
0.7778	Intermediate Similarity	NPD919	Approved
0.777	Intermediate Similarity	NPD943	Approved
0.7755	Intermediate Similarity	NPD3764	Approved
0.7755	Intermediate Similarity	NPD2313	Discontinued
0.7751	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7808	Phase 3
0.7748	Intermediate Similarity	NPD5404	Approved
0.7748	Intermediate Similarity	NPD5408	Approved
0.7748	Intermediate Similarity	NPD5405	Approved
0.7748	Intermediate Similarity	NPD5406	Approved
0.7744	Intermediate Similarity	NPD7229	Phase 3
0.7738	Intermediate Similarity	NPD6797	Phase 2
0.773	Intermediate Similarity	NPD5494	Approved
0.7727	Intermediate Similarity	NPD2309	Approved
0.7718	Intermediate Similarity	NPD230	Phase 1
0.7708	Intermediate Similarity	NPD3225	Approved
0.7692	Intermediate Similarity	NPD6559	Discontinued
0.7692	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5401	Approved
0.7687	Intermediate Similarity	NPD4625	Phase 3
0.7683	Intermediate Similarity	NPD7199	Phase 2
0.7682	Intermediate Similarity	NPD7033	Discontinued
0.7655	Intermediate Similarity	NPD3266	Approved
0.7655	Intermediate Similarity	NPD3267	Approved
0.7635	Intermediate Similarity	NPD1296	Phase 2
0.7633	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4908	Phase 1
0.761	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD2798	Approved
0.7595	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3926	Phase 2
0.7586	Intermediate Similarity	NPD4287	Approved
0.7544	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4307	Phase 2
0.7533	Intermediate Similarity	NPD4060	Phase 1
0.7532	Intermediate Similarity	NPD6273	Approved
0.7517	Intermediate Similarity	NPD4749	Approved
0.7517	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1201	Approved
0.75	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1610	Phase 2
0.7483	Intermediate Similarity	NPD6355	Discontinued
0.7469	Intermediate Similarity	NPD37	Approved
0.7466	Intermediate Similarity	NPD1283	Approved
0.7465	Intermediate Similarity	NPD9545	Approved
0.7455	Intermediate Similarity	NPD6234	Discontinued
0.7451	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD9493	Approved
0.7439	Intermediate Similarity	NPD4965	Approved
0.7439	Intermediate Similarity	NPD4966	Approved
0.7439	Intermediate Similarity	NPD4967	Phase 2
0.7436	Intermediate Similarity	NPD7003	Approved
0.7432	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1470	Approved
0.7415	Intermediate Similarity	NPD1164	Approved
0.7407	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD4477	Approved
0.7403	Intermediate Similarity	NPD4476	Approved
0.74	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD8313	Approved
0.7399	Intermediate Similarity	NPD8312	Approved
0.7386	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2654	Approved
0.7368	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5124	Phase 1
0.7368	Intermediate Similarity	NPD1933	Approved
0.7365	Intermediate Similarity	NPD1019	Discontinued
0.7361	Intermediate Similarity	NPD4626	Approved
0.7355	Intermediate Similarity	NPD1471	Phase 3
0.7353	Intermediate Similarity	NPD7177	Discontinued
0.7351	Intermediate Similarity	NPD8032	Phase 2
0.7343	Intermediate Similarity	NPD1548	Phase 1
0.7333	Intermediate Similarity	NPD7095	Approved
0.7329	Intermediate Similarity	NPD1481	Phase 2
0.7308	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD6971	Discontinued
0.7285	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6798	Discontinued
0.7284	Intermediate Similarity	NPD7458	Discontinued
0.7267	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1247	Approved
0.726	Intermediate Similarity	NPD1281	Approved
0.726	Intermediate Similarity	NPD1535	Discovery
0.726	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD3751	Discontinued
0.7251	Intermediate Similarity	NPD7228	Approved
0.7241	Intermediate Similarity	NPD1778	Approved
0.7238	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3787	Discontinued
0.7211	Intermediate Similarity	NPD9269	Phase 2
0.7211	Intermediate Similarity	NPD3972	Approved
0.7196	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7783	Phase 2
0.719	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1613	Approved
0.719	Intermediate Similarity	NPD2979	Phase 3
0.7184	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8151	Discontinued
0.7176	Intermediate Similarity	NPD5242	Approved
0.7175	Intermediate Similarity	NPD8434	Phase 2
0.7172	Intermediate Similarity	NPD9268	Approved
0.7172	Intermediate Similarity	NPD5691	Approved
0.717	Intermediate Similarity	NPD2354	Approved
0.7169	Intermediate Similarity	NPD2296	Approved
0.7163	Intermediate Similarity	NPD5535	Approved
0.7151	Intermediate Similarity	NPD7893	Clinical (unspecified phase)

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