NPASS Compound

Structure

CID277426 OpenBabel06191716082D 26 27 0 0 1 0 0 0 0 0999 V2000 -0.9749 1.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6798 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -4.0489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9499 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7818 -3.4254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1656 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 -4.2714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -3.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9478 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9749 0.2225 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2157 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9478 -2.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1656 -2.5245 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9499 -4.0489 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0817 -1.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2157 -1.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7317 -3.4254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1405 -2.7470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3837 -4.9499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0817 -0.0245 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5135 -4.0489 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5637 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8138 -3.0245 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 25 1 0 0 0 0 3 5 1 0 0 0 0 3 7 2 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 1 1 6 0 0 0 11 26 1 0 0 0 0 12 17 1 0 0 0 0 13 25 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 1 0 0 0 15 18 1 0 0 0 0 15 21 1 6 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 19 1 0 0 0 0 18 23 1 6 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.15
Volume:	365.78
LogP:	2.147
LogD:	2.257
LogS:	-3.459
# Rotatable Bonds:	1
TPSA:	116.45
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.439
Synthetic Accessibility Score:	4.533
Fsp3:	0.421
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:	-5.098
MDCK Permeability:	1.921649709402118e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.509
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.329
Plasma Protein Binding (PPB):	97.8525161743164%
Volume Distribution (VD):	0.833
Pgp-substrate:	4.878355026245117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.244
CYP1A2-substrate:	0.222
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.253
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.938
CYP2D6-inhibitor:	0.41
CYP2D6-substrate:	0.791
CYP3A4-inhibitor:	0.106
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	8.759
Half-life (T1/2):	0.84

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.533
Drug-inuced Liver Injury (DILI):	0.116
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.018
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.706
Carcinogencity:	0.697
Eye Corrosion:	0.004
Eye Irritation:	0.122
Respiratory Toxicity:	0.811

Download Data

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

Natural Product: NPC277426

Natural Product ID:	NPC277426
*Common Name:**	Zeaenol
IUPAC Name:	(2E,5S,6S,7S,8E,11S)-5,6,7,15-tetrahydroxy-17-methoxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,8,15,17-pentaen-13-one
Synonyms:	Zeaenol
Standard InCHIKey:	BPOLRDGTYHVUAY-YMFWJEOZSA-N
Standard InCHI:	InChI=1S/C19H24O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,14-15,18,20-23H,5,8H2,1-2H3/b6-4+,7-3+/t11-,14-,15-,18+/m0/s1
SMILES:	C[C@H]1C/C=C/[C@@H]([C@H]([C@H](C/C=C/c2cc(cc(c2C(=O)O1)O)OC)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1099228
PubChem CID:	46888372
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO33425	paecilomyces fungus	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[20429578]
NPO30448	Cochliobolus lunatus	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21348465]

☑ 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	9
MIC	4

Activity Type	# Activity
Cell Line	5
Individual Protein	2
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[545290]
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	100000.0	nM	PMID[545290]
NPT395	Cell Line	SF-268	Homo sapiens	IC50	>	100000.0	nM	PMID[545290]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	25000.0	nM	PMID[545290]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	>	25000.0	nM	PMID[545290]
NPT3442	Individual Protein	Mitogen-activated protein kinase kinase kinase 7	Homo sapiens	IC50	=	10000.0	nM	PMID[545292]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	50000.0	nM	PMID[545289]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	50000.0	nM	PMID[545290]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	500.0	ug.mL-1	PMID[545290]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	500.0	ug.mL-1	PMID[545290]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	500.0	ug.mL-1	PMID[545290]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	500.0	ug.mL-1	PMID[545290]

☑ 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 NPC277426 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	326
0.1-0.2	1351
0.2-0.3	3705
0.3-0.4	7891
0.4-0.5	10501
0.5-0.6	3510
0.6-0.7	5468
0.7-0.8	7429
0.8-0.85	2093
0.85-0.9	330
0.9-0.95	71
0.95-1	22

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC86373
1.0	High Similarity	NPC210425
1.0	High Similarity	NPC280404
0.9854	High Similarity	NPC474385
0.9786	High Similarity	NPC210320
0.9716	High Similarity	NPC215711
0.9716	High Similarity	NPC73411
0.9708	High Similarity	NPC158472
0.964	High Similarity	NPC51106
0.9638	High Similarity	NPC67650
0.9638	High Similarity	NPC475730
0.9638	High Similarity	NPC1704
0.958	High Similarity	NPC469619
0.958	High Similarity	NPC469670
0.9514	High Similarity	NPC240768
0.9514	High Similarity	NPC70016
0.9514	High Similarity	NPC215921
0.9514	High Similarity	NPC200773
0.9507	High Similarity	NPC472036
0.9504	High Similarity	NPC472034
0.95	High Similarity	NPC469542
0.95	High Similarity	NPC472006
0.9496	High Similarity	NPC158634
0.9489	High Similarity	NPC135837
0.9437	High Similarity	NPC472033
0.9429	High Similarity	NPC469579
0.942	High Similarity	NPC94248
0.942	High Similarity	NPC212693
0.942	High Similarity	NPC33144
0.942	High Similarity	NPC478200
0.9375	High Similarity	NPC476684
0.9375	High Similarity	NPC270160
0.9375	High Similarity	NPC237440
0.9366	High Similarity	NPC83272
0.9353	High Similarity	NPC32360
0.9348	High Similarity	NPC70380
0.9343	High Similarity	NPC180905
0.9343	High Similarity	NPC182496
0.932	High Similarity	NPC99381
0.9306	High Similarity	NPC240622
0.9306	High Similarity	NPC240253
0.9306	High Similarity	NPC471642
0.9306	High Similarity	NPC471641
0.9301	High Similarity	NPC107625
0.9291	High Similarity	NPC250755
0.9281	High Similarity	NPC191835
0.922	High Similarity	NPC478217
0.922	High Similarity	NPC478201
0.922	High Similarity	NPC90411
0.922	High Similarity	NPC313123
0.922	High Similarity	NPC472035
0.9214	High Similarity	NPC139634
0.9214	High Similarity	NPC268052
0.9214	High Similarity	NPC247409
0.9214	High Similarity	NPC105456
0.9209	High Similarity	NPC71256
0.9197	High Similarity	NPC153783
0.9189	High Similarity	NPC16082
0.9189	High Similarity	NPC82592
0.9184	High Similarity	NPC167903
0.9178	High Similarity	NPC179178
0.9167	High Similarity	NPC473023
0.9161	High Similarity	NPC95123
0.9161	High Similarity	NPC66404
0.9143	High Similarity	NPC472602
0.9137	High Similarity	NPC235115
0.9122	High Similarity	NPC281477
0.9097	High Similarity	NPC134621
0.9097	High Similarity	NPC257558
0.9097	High Similarity	NPC312789
0.9091	High Similarity	NPC478202
0.9085	High Similarity	NPC472605
0.9085	High Similarity	NPC244923
0.9085	High Similarity	NPC472604
0.9085	High Similarity	NPC53649
0.9067	High Similarity	NPC246466
0.9067	High Similarity	NPC190020
0.9067	High Similarity	NPC84935
0.9067	High Similarity	NPC77679
0.906	High Similarity	NPC79998
0.9054	High Similarity	NPC478224
0.9051	High Similarity	NPC219892
0.9051	High Similarity	NPC189823
0.9048	High Similarity	NPC56204
0.9048	High Similarity	NPC96501
0.9048	High Similarity	NPC472891
0.9034	High Similarity	NPC237208
0.9034	High Similarity	NPC225173
0.9034	High Similarity	NPC163846
0.9028	High Similarity	NPC210966
0.9028	High Similarity	NPC151607
0.9028	High Similarity	NPC42540
0.9028	High Similarity	NPC478203
0.9028	High Similarity	NPC126882
0.9021	High Similarity	NPC96692
0.9021	High Similarity	NPC82913
0.9021	High Similarity	NPC105648
0.9014	High Similarity	NPC472601
0.9014	High Similarity	NPC165172
0.9014	High Similarity	NPC472600
0.9007	High Similarity	NPC9121
0.9007	High Similarity	NPC177307
0.9007	High Similarity	NPC475974
0.9007	High Similarity	NPC470339
0.9	High Similarity	NPC472050
0.9	High Similarity	NPC150227
0.9	High Similarity	NPC227062
0.8993	High Similarity	NPC175943
0.898	High Similarity	NPC77325
0.898	High Similarity	NPC4423
0.8973	High Similarity	NPC14098
0.8973	High Similarity	NPC8817
0.8973	High Similarity	NPC125801
0.8966	High Similarity	NPC29577
0.8958	High Similarity	NPC471731
0.8958	High Similarity	NPC159721
0.8951	High Similarity	NPC220106
0.8951	High Similarity	NPC472603
0.8947	High Similarity	NPC472055
0.8944	High Similarity	NPC52358
0.8936	High Similarity	NPC178467
0.8936	High Similarity	NPC474771
0.8936	High Similarity	NPC474849
0.8936	High Similarity	NPC65837
0.8936	High Similarity	NPC194579
0.8936	High Similarity	NPC149372
0.8933	High Similarity	NPC199926
0.8933	High Similarity	NPC208173
0.8933	High Similarity	NPC69043
0.8933	High Similarity	NPC170189
0.8933	High Similarity	NPC478230
0.8929	High Similarity	NPC142027
0.8926	High Similarity	NPC76041
0.8926	High Similarity	NPC273483
0.8926	High Similarity	NPC115249
0.8926	High Similarity	NPC184284
0.8919	High Similarity	NPC475460
0.8912	High Similarity	NPC37139
0.8912	High Similarity	NPC153417
0.8904	High Similarity	NPC260946
0.8904	High Similarity	NPC470357
0.8904	High Similarity	NPC138978
0.8897	High Similarity	NPC470932
0.8889	High Similarity	NPC471733
0.8889	High Similarity	NPC471640
0.8889	High Similarity	NPC49108
0.8889	High Similarity	NPC471644
0.8881	High Similarity	NPC155205
0.8873	High Similarity	NPC126739
0.8873	High Similarity	NPC472403
0.8873	High Similarity	NPC197666
0.8867	High Similarity	NPC137301
0.8859	High Similarity	NPC46882
0.8859	High Similarity	NPC132990
0.8859	High Similarity	NPC204350
0.8851	High Similarity	NPC291049
0.8851	High Similarity	NPC233267
0.8849	High Similarity	NPC470160
0.8844	High Similarity	NPC166583
0.8844	High Similarity	NPC53362
0.8844	High Similarity	NPC137296
0.8844	High Similarity	NPC12305
0.8841	High Similarity	NPC42292
0.8841	High Similarity	NPC307732
0.8836	High Similarity	NPC473692
0.8836	High Similarity	NPC75694
0.8832	High Similarity	NPC293453
0.8828	High Similarity	NPC472610
0.8828	High Similarity	NPC471643
0.8828	High Similarity	NPC471639
0.8819	High Similarity	NPC130485
0.8816	High Similarity	NPC472889
0.8816	High Similarity	NPC473395
0.8811	High Similarity	NPC92655
0.8811	High Similarity	NPC88269
0.8811	High Similarity	NPC471819
0.8811	High Similarity	NPC474655
0.8808	High Similarity	NPC67396
0.8808	High Similarity	NPC472890
0.8803	High Similarity	NPC472364
0.8803	High Similarity	NPC476333
0.8803	High Similarity	NPC470397
0.8803	High Similarity	NPC472367
0.8803	High Similarity	NPC473391
0.88	High Similarity	NPC470340
0.88	High Similarity	NPC268992
0.88	High Similarity	NPC295646
0.88	High Similarity	NPC470337
0.88	High Similarity	NPC51824
0.88	High Similarity	NPC474843
0.88	High Similarity	NPC470338
0.88	High Similarity	NPC113608
0.8794	High Similarity	NPC27407
0.8792	High Similarity	NPC60413
0.8792	High Similarity	NPC158866
0.8792	High Similarity	NPC85131
0.8792	High Similarity	NPC295036
0.8786	High Similarity	NPC203817
0.8784	High Similarity	NPC105415
0.8784	High Similarity	NPC470359

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 NPC277426 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	870
0.2-0.3	1843
0.3-0.4	2514
0.4-0.5	1841
0.5-0.6	1111
0.6-0.7	489
0.7-0.8	167
0.8-0.85	31
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9214	High Similarity	NPD970	Clinical (unspecified phase)
0.8836	High Similarity	NPD2532	Approved
0.8836	High Similarity	NPD2533	Approved
0.8836	High Similarity	NPD2534	Approved
0.8618	High Similarity	NPD7819	Suspended
0.8514	High Similarity	NPD6799	Approved
0.8497	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8452	Intermediate Similarity	NPD7075	Discontinued
0.8431	Intermediate Similarity	NPD1934	Approved
0.8421	Intermediate Similarity	NPD4380	Phase 2
0.8377	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6232	Discontinued
0.8345	Intermediate Similarity	NPD1510	Phase 2
0.8323	Intermediate Similarity	NPD3817	Phase 2
0.8322	Intermediate Similarity	NPD1240	Approved
0.8312	Intermediate Similarity	NPD6801	Discontinued
0.8311	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD6599	Discontinued
0.8299	Intermediate Similarity	NPD1549	Phase 2
0.8269	Intermediate Similarity	NPD3882	Suspended
0.8267	Intermediate Similarity	NPD1511	Approved
0.8264	Intermediate Similarity	NPD230	Phase 1
0.8258	Intermediate Similarity	NPD2801	Approved
0.8217	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8207	Intermediate Similarity	NPD1607	Approved
0.8199	Intermediate Similarity	NPD7473	Discontinued
0.8188	Intermediate Similarity	NPD4628	Phase 3
0.8188	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD2796	Approved
0.8163	Intermediate Similarity	NPD2935	Discontinued
0.8163	Intermediate Similarity	NPD1551	Phase 2
0.8158	Intermediate Similarity	NPD1512	Approved
0.8153	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD6166	Phase 2
0.8129	Intermediate Similarity	NPD7411	Suspended
0.8105	Intermediate Similarity	NPD5403	Approved
0.8098	Intermediate Similarity	NPD7054	Approved
0.8098	Intermediate Similarity	NPD5844	Phase 1
0.8089	Intermediate Similarity	NPD5402	Approved
0.8089	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD6959	Discontinued
0.8049	Intermediate Similarity	NPD7074	Phase 3
0.8049	Intermediate Similarity	NPD7472	Approved
0.8038	Intermediate Similarity	NPD7768	Phase 2
0.8037	Intermediate Similarity	NPD3818	Discontinued
0.8012	Intermediate Similarity	NPD5710	Approved
0.8012	Intermediate Similarity	NPD5711	Approved
0.8012	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6797	Phase 2
0.7987	Intermediate Similarity	NPD3749	Approved
0.7974	Intermediate Similarity	NPD5401	Approved
0.7952	Intermediate Similarity	NPD7251	Discontinued
0.7914	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD7808	Phase 3
0.7899	Intermediate Similarity	NPD9545	Approved
0.7879	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD9717	Approved
0.7857	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD3748	Approved
0.7852	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD6559	Discontinued
0.7799	Intermediate Similarity	NPD1465	Phase 2
0.777	Intermediate Similarity	NPD447	Suspended
0.7763	Intermediate Similarity	NPD2800	Approved
0.7763	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7754	Intermediate Similarity	NPD9493	Approved
0.7746	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD7199	Phase 2
0.7718	Intermediate Similarity	NPD6651	Approved
0.7712	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD1203	Approved
0.7703	Intermediate Similarity	NPD943	Approved
0.7687	Intermediate Similarity	NPD411	Approved
0.7679	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD422	Phase 1
0.7671	Intermediate Similarity	NPD6832	Phase 2
0.7669	Intermediate Similarity	NPD5494	Approved
0.7658	Intermediate Similarity	NPD3226	Approved
0.7647	Intermediate Similarity	NPD1243	Approved
0.7643	Intermediate Similarity	NPD920	Approved
0.7628	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD37	Approved
0.7616	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2799	Discontinued
0.7616	Intermediate Similarity	NPD7033	Discontinued
0.7613	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD919	Approved
0.7607	Intermediate Similarity	NPD6234	Discontinued
0.7593	Intermediate Similarity	NPD4967	Phase 2
0.7593	Intermediate Similarity	NPD4965	Approved
0.7593	Intermediate Similarity	NPD4966	Approved
0.7574	Intermediate Similarity	NPD5953	Discontinued
0.7566	Intermediate Similarity	NPD6099	Approved
0.7566	Intermediate Similarity	NPD6100	Approved
0.7547	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD4626	Approved
0.7533	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD2654	Approved
0.753	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD9269	Phase 2
0.75	Intermediate Similarity	NPD3027	Phase 3
0.7483	Intermediate Similarity	NPD9494	Approved
0.747	Intermediate Similarity	NPD3787	Discontinued
0.7467	Intermediate Similarity	NPD4060	Phase 1
0.7465	Intermediate Similarity	NPD5691	Approved
0.7456	Intermediate Similarity	NPD7286	Phase 2
0.7452	Intermediate Similarity	NPD7390	Discontinued
0.7452	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5408	Approved
0.7451	Intermediate Similarity	NPD5406	Approved
0.7451	Intermediate Similarity	NPD5404	Approved
0.7451	Intermediate Similarity	NPD5405	Approved
0.745	Intermediate Similarity	NPD3764	Approved
0.7442	Intermediate Similarity	NPD8313	Approved
0.7442	Intermediate Similarity	NPD8312	Approved
0.7436	Intermediate Similarity	NPD6190	Approved
0.7429	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD1652	Phase 2
0.7417	Intermediate Similarity	NPD6355	Discontinued
0.7417	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD5124	Phase 1
0.7415	Intermediate Similarity	NPD1019	Discontinued
0.7413	Intermediate Similarity	NPD1778	Approved
0.7403	Intermediate Similarity	NPD2344	Approved
0.7396	Intermediate Similarity	NPD7228	Approved
0.7384	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1653	Approved
0.7365	Intermediate Similarity	NPD7229	Phase 3
0.7358	Intermediate Similarity	NPD6273	Approved
0.7351	Intermediate Similarity	NPD1613	Approved
0.7351	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2797	Approved
0.7343	Intermediate Similarity	NPD9268	Approved
0.7333	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6798	Discontinued
0.7322	Intermediate Similarity	NPD7435	Discontinued
0.7321	Intermediate Similarity	NPD3926	Phase 2
0.7317	Intermediate Similarity	NPD5353	Approved
0.7317	Intermediate Similarity	NPD4288	Approved
0.7315	Intermediate Similarity	NPD4908	Phase 1
0.7314	Intermediate Similarity	NPD8150	Discontinued
0.7312	Intermediate Similarity	NPD8151	Discontinued
0.7297	Intermediate Similarity	NPD2798	Approved
0.7297	Intermediate Similarity	NPD5647	Approved
0.7292	Intermediate Similarity	NPD17	Approved
0.729	Intermediate Similarity	NPD6002	Phase 3
0.729	Intermediate Similarity	NPD6004	Phase 3
0.729	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6005	Phase 3
0.729	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD1283	Approved
0.7278	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD7003	Approved
0.7255	Intermediate Similarity	NPD6653	Approved
0.7253	Intermediate Similarity	NPD6779	Approved
0.7253	Intermediate Similarity	NPD6780	Approved
0.7253	Intermediate Similarity	NPD6781	Approved
0.7253	Intermediate Similarity	NPD6776	Approved
0.7253	Intermediate Similarity	NPD6777	Approved
0.7253	Intermediate Similarity	NPD6778	Approved
0.7253	Intermediate Similarity	NPD6782	Approved
0.7241	Intermediate Similarity	NPD3496	Discontinued
0.7226	Intermediate Similarity	NPD2438	Suspended
0.7225	Intermediate Similarity	NPD7685	Pre-registration
0.7222	Intermediate Similarity	NPD7458	Discontinued
0.7219	Intermediate Similarity	NPD5242	Approved
0.7219	Intermediate Similarity	NPD1296	Phase 2
0.7219	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8434	Phase 2
0.7215	Intermediate Similarity	NPD2309	Approved
0.7202	Intermediate Similarity	NPD1247	Approved
0.7192	Intermediate Similarity	NPD1201	Approved
0.7192	Intermediate Similarity	NPD1610	Phase 2
0.719	Intermediate Similarity	NPD1933	Approved
0.7181	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5762	Approved
0.7179	Intermediate Similarity	NPD5763	Approved
0.7174	Intermediate Similarity	NPD74	Approved
0.7174	Intermediate Similarity	NPD9266	Approved
0.7171	Intermediate Similarity	NPD6233	Phase 2
0.7162	Intermediate Similarity	NPD3225	Approved
0.7161	Intermediate Similarity	NPD4308	Phase 3
0.7159	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD7782	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