NPASS Compound

Structure

NPC9370 OpenBabel07101718282D 25 26 0 0 1 0 0 0 0 0999 V2000 6.9282 -1.0000 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 -0.0000 2.0000 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 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 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 5.1962 0.0000 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 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 6.0622 1.5000 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 6.0622 0.5000 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 2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 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 23 1 0 0 0 0 2 24 1 0 0 0 0 3 6 2 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 16 1 0 0 0 0 8 12 2 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 12 18 1 0 0 0 0 13 15 2 0 0 0 0 13 21 1 0 0 0 0 14 16 2 0 0 0 0 14 25 1 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 17 10 1 6 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.12
Volume:	345.848
LogP:	0.929
LogD:	1.172
LogS:	-3.048
# Rotatable Bonds:	8
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.624
Synthetic Accessibility Score:	3.087
Fsp3:	0.278
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.425
MDCK Permeability:	6.458909410866909e-06
Pgp-inhibitor:	0.023
Pgp-substrate:	0.032
Human Intestinal Absorption (HIA):	0.159
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.093

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.93
Plasma Protein Binding (PPB):	90.99272155761719%
Volume Distribution (VD):	0.846
Pgp-substrate:	8.504913330078125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.441
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.605
CYP2C9-inhibitor:	0.063
CYP2C9-substrate:	0.708
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.513
CYP3A4-inhibitor:	0.203
CYP3A4-substrate:	0.406

ADMET: Excretion

Clearance (CL):	8.251
Half-life (T1/2):	0.856

ADMET: Toxicity

hERG Blockers:	0.072
Human Hepatotoxicity (H-HT):	0.049
Drug-inuced Liver Injury (DILI):	0.062
AMES Toxicity:	0.078
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.068
Carcinogencity:	0.035
Eye Corrosion:	0.004
Eye Irritation:	0.193
Respiratory Toxicity:	0.043

Download Data

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

Natural Product: NPC9370

Natural Product ID:	NPC9370
*Common Name:**	Threo-Guaiacylglycerol 8'-Vanillin Ether
IUPAC Name:	4-[(1R,2R)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxybenzaldehyde
Synonyms:
Standard InCHIKey:	BRWKQWFEHBAUSN-QZTJIDSGSA-N
Standard InCHI:	InChI=1S/C18H20O7/c1-23-15-8-12(4-5-13(15)21)18(22)17(10-20)25-14-6-3-11(9-19)7-16(14)24-2/h3-9,17-18,20-22H,10H2,1-2H3/t17-,18-/m1/s1
SMILES:	COc1cc(ccc1O)[C@H]([C@@H](CO)Oc1ccc(cc1OC)C=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2430313
PubChem CID:	73350869
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15739361]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	seed	n.a.	PMID[23845552]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	seeds	n.a.	n.a.	PMID[23999046]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12011	Crataegus pinnatifida	Species	Rosaceae	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	12
Others	1

Activity Type	# Activity
Cell Line	10
NON-MOLECULAR	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	IC50	>	50000.0	nM	PMID[565055]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[565055]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	32250.0	nM	PMID[565055]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	50000.0	nM	PMID[565055]
NPT453	Cell Line	HT-1080	Homo sapiens	IC50	>	50000.0	nM	PMID[565055]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[565055]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	>	50000.0	nM	PMID[565055]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[565055]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[565055]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[565055]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[565055]
NPT27	Others	Unspecified		Activity	=	116.4	%	PMID[565056]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	47590.0	nM	PMID[565056]

☑ 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 NPC9370 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	357
0.1-0.2	1469
0.2-0.3	4157
0.3-0.4	9853
0.4-0.5	8190
0.5-0.6	3389
0.6-0.7	5799
0.7-0.8	7504
0.8-0.85	1622
0.85-0.9	336
0.9-0.95	15
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC287495
0.9577	High Similarity	NPC472969
0.951	High Similarity	NPC98809
0.951	High Similarity	NPC476394
0.9433	High Similarity	NPC473090
0.9388	High Similarity	NPC300757
0.9388	High Similarity	NPC180901
0.9315	High Similarity	NPC75695
0.9252	High Similarity	NPC131121
0.922	High Similarity	NPC326065
0.9203	High Similarity	NPC476387
0.9203	High Similarity	NPC144662
0.9203	High Similarity	NPC249791
0.9203	High Similarity	NPC237594
0.9203	High Similarity	NPC119060
0.9178	High Similarity	NPC473091
0.9067	High Similarity	NPC471405
0.906	High Similarity	NPC194095
0.906	High Similarity	NPC327032
0.906	High Similarity	NPC191046
0.9048	High Similarity	NPC205054
0.9028	High Similarity	NPC46161
0.9028	High Similarity	NPC239608
0.9	High Similarity	NPC214729
0.9	High Similarity	NPC10205
0.8966	High Similarity	NPC469683
0.8966	High Similarity	NPC275278
0.8933	High Similarity	NPC25127
0.8933	High Similarity	NPC469888
0.8926	High Similarity	NPC36130
0.8926	High Similarity	NPC289438
0.8926	High Similarity	NPC134905
0.8913	High Similarity	NPC298268
0.8912	High Similarity	NPC294972
0.8904	High Similarity	NPC30890
0.8897	High Similarity	NPC469615
0.8889	High Similarity	NPC203020
0.8889	High Similarity	NPC239966
0.8889	High Similarity	NPC472962
0.8889	High Similarity	NPC472961
0.8882	High Similarity	NPC133984
0.8882	High Similarity	NPC470402
0.8881	High Similarity	NPC267291
0.8881	High Similarity	NPC474784
0.8867	High Similarity	NPC39732
0.8867	High Similarity	NPC137813
0.8867	High Similarity	NPC60972
0.8867	High Similarity	NPC257648
0.8867	High Similarity	NPC477231
0.8867	High Similarity	NPC157898
0.8865	High Similarity	NPC139519
0.8859	High Similarity	NPC243891
0.8851	High Similarity	NPC474903
0.8846	High Similarity	NPC43065
0.8844	High Similarity	NPC165389
0.8836	High Similarity	NPC207732
0.8831	High Similarity	NPC469889
0.8828	High Similarity	NPC312256
0.8824	High Similarity	NPC160780
0.8824	High Similarity	NPC289811
0.8819	High Similarity	NPC83375
0.8819	High Similarity	NPC224876
0.8816	High Similarity	NPC472916
0.8811	High Similarity	NPC325625
0.8808	High Similarity	NPC18727
0.8808	High Similarity	NPC287504
0.88	High Similarity	NPC267091
0.88	High Similarity	NPC31363
0.88	High Similarity	NPC151425
0.8792	High Similarity	NPC227980
0.8777	High Similarity	NPC66905
0.8776	High Similarity	NPC98356
0.8767	High Similarity	NPC50954
0.8766	High Similarity	NPC53889
0.8766	High Similarity	NPC476373
0.8759	High Similarity	NPC110419
0.8759	High Similarity	NPC278469
0.8759	High Similarity	NPC193722
0.8758	High Similarity	NPC299520
0.8758	High Similarity	NPC129684
0.8758	High Similarity	NPC474208
0.8758	High Similarity	NPC52530
0.8758	High Similarity	NPC156057
0.8758	High Similarity	NPC472598
0.8758	High Similarity	NPC472860
0.8758	High Similarity	NPC474055
0.8758	High Similarity	NPC99597
0.8758	High Similarity	NPC210084
0.8758	High Similarity	NPC475267
0.8758	High Similarity	NPC48208
0.8758	High Similarity	NPC291508
0.8758	High Similarity	NPC1913
0.8758	High Similarity	NPC226759
0.8758	High Similarity	NPC162869
0.8758	High Similarity	NPC474836
0.875	High Similarity	NPC2928
0.875	High Similarity	NPC213622
0.875	High Similarity	NPC145425
0.875	High Similarity	NPC256612
0.875	High Similarity	NPC20830
0.8742	High Similarity	NPC302950
0.8742	High Similarity	NPC219582
0.8742	High Similarity	NPC236637
0.8741	High Similarity	NPC126206
0.8732	High Similarity	NPC274613
0.8725	High Similarity	NPC107636
0.8725	High Similarity	NPC111785
0.8723	High Similarity	NPC283823
0.8723	High Similarity	NPC159418
0.8718	High Similarity	NPC124038
0.871	High Similarity	NPC308992
0.871	High Similarity	NPC25389
0.871	High Similarity	NPC472859
0.871	High Similarity	NPC311803
0.8701	High Similarity	NPC172202
0.8701	High Similarity	NPC284127
0.8701	High Similarity	NPC476410
0.8701	High Similarity	NPC87317
0.8699	High Similarity	NPC28326
0.8696	High Similarity	NPC111247
0.8696	High Similarity	NPC147821
0.8696	High Similarity	NPC41706
0.8696	High Similarity	NPC292056
0.8696	High Similarity	NPC118787
0.8696	High Similarity	NPC183181
0.8696	High Similarity	NPC203719
0.8696	High Similarity	NPC163332
0.8696	High Similarity	NPC117237
0.8696	High Similarity	NPC319625
0.8693	High Similarity	NPC13858
0.8693	High Similarity	NPC265511
0.8693	High Similarity	NPC195796
0.8693	High Similarity	NPC320825
0.8693	High Similarity	NPC235165
0.8693	High Similarity	NPC291878
0.8693	High Similarity	NPC35038
0.8693	High Similarity	NPC278778
0.8693	High Similarity	NPC326037
0.8693	High Similarity	NPC255106
0.8684	High Similarity	NPC160951
0.8684	High Similarity	NPC274327
0.8684	High Similarity	NPC176775
0.8684	High Similarity	NPC472915
0.8684	High Similarity	NPC47781
0.8684	High Similarity	NPC145379
0.8684	High Similarity	NPC474000
0.8684	High Similarity	NPC183878
0.8684	High Similarity	NPC69394
0.8684	High Similarity	NPC255350
0.8684	High Similarity	NPC22519
0.8684	High Similarity	NPC231018
0.8671	High Similarity	NPC471665
0.8671	High Similarity	NPC471664
0.8667	High Similarity	NPC137062
0.8667	High Similarity	NPC223579
0.8667	High Similarity	NPC102003
0.8667	High Similarity	NPC92722
0.8667	High Similarity	NPC177298
0.8667	High Similarity	NPC48479
0.8667	High Similarity	NPC183950
0.8667	High Similarity	NPC287101
0.8667	High Similarity	NPC52005
0.8662	High Similarity	NPC135127
0.8662	High Similarity	NPC237330
0.8654	High Similarity	NPC33298
0.8654	High Similarity	NPC476247
0.8654	High Similarity	NPC148273
0.8654	High Similarity	NPC474034
0.8654	High Similarity	NPC476372
0.8654	High Similarity	NPC285108
0.8654	High Similarity	NPC476371
0.8654	High Similarity	NPC472964
0.8654	High Similarity	NPC474033
0.8652	High Similarity	NPC50763
0.8652	High Similarity	NPC111888
0.8649	High Similarity	NPC157133
0.8645	High Similarity	NPC263449
0.8645	High Similarity	NPC166277
0.8645	High Similarity	NPC282009
0.8645	High Similarity	NPC287328
0.8645	High Similarity	NPC24164
0.8645	High Similarity	NPC119125
0.8645	High Similarity	NPC472902
0.8639	High Similarity	NPC134975
0.8639	High Similarity	NPC474444
0.8639	High Similarity	NPC264706
0.8639	High Similarity	NPC284881
0.8639	High Similarity	NPC93433
0.8636	High Similarity	NPC222814
0.8636	High Similarity	NPC472914
0.8636	High Similarity	NPC472911
0.8636	High Similarity	NPC472910
0.8636	High Similarity	NPC38779
0.8636	High Similarity	NPC471479
0.8636	High Similarity	NPC471515
0.8636	High Similarity	NPC27337
0.8636	High Similarity	NPC245758
0.8636	High Similarity	NPC68324
0.8636	High Similarity	NPC472913
0.8636	High Similarity	NPC114179

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 NPC9370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	326
0.1-0.2	869
0.2-0.3	1762
0.3-0.4	2576
0.4-0.5	1820
0.5-0.6	1037
0.6-0.7	594
0.7-0.8	146
0.8-0.85	15
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8742	High Similarity	NPD1934	Approved
0.8696	High Similarity	NPD9494	Approved
0.8693	High Similarity	NPD3882	Suspended
0.8684	High Similarity	NPD2801	Approved
0.8571	High Similarity	NPD4868	Clinical (unspecified phase)
0.8562	High Similarity	NPD2393	Clinical (unspecified phase)
0.8503	High Similarity	NPD4628	Phase 3
0.8438	Intermediate Similarity	NPD3818	Discontinued
0.8428	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD6166	Phase 2
0.8333	Intermediate Similarity	NPD1511	Approved
0.8272	Intermediate Similarity	NPD7054	Approved
0.8224	Intermediate Similarity	NPD1512	Approved
0.8221	Intermediate Similarity	NPD7074	Phase 3
0.8221	Intermediate Similarity	NPD7472	Approved
0.8207	Intermediate Similarity	NPD230	Phase 1
0.82	Intermediate Similarity	NPD6190	Approved
0.8182	Intermediate Similarity	NPD3027	Phase 3
0.8153	Intermediate Similarity	NPD3817	Phase 2
0.8143	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8061	Intermediate Similarity	NPD6797	Phase 2
0.8049	Intermediate Similarity	NPD5844	Phase 1
0.8013	Intermediate Similarity	NPD4380	Phase 2
0.8012	Intermediate Similarity	NPD7251	Discontinued
0.8012	Intermediate Similarity	NPD7685	Pre-registration
0.7975	Intermediate Similarity	NPD1465	Phase 2
0.7974	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD7808	Phase 3
0.795	Intermediate Similarity	NPD5494	Approved
0.7937	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD1613	Approved
0.7881	Intermediate Similarity	NPD1549	Phase 2
0.7857	Intermediate Similarity	NPD6799	Approved
0.7848	Intermediate Similarity	NPD6385	Approved
0.7848	Intermediate Similarity	NPD6386	Approved
0.7838	Intermediate Similarity	NPD447	Suspended
0.7829	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD7075	Discontinued
0.7815	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD2796	Approved
0.7744	Intermediate Similarity	NPD6232	Discontinued
0.7707	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD5402	Approved
0.7697	Intermediate Similarity	NPD7266	Discontinued
0.7692	Intermediate Similarity	NPD6559	Discontinued
0.7688	Intermediate Similarity	NPD6801	Discontinued
0.7683	Intermediate Similarity	NPD1247	Approved
0.7682	Intermediate Similarity	NPD1510	Phase 2
0.7651	Intermediate Similarity	NPD1240	Approved
0.7651	Intermediate Similarity	NPD943	Approved
0.7643	Intermediate Similarity	NPD5536	Phase 2
0.7635	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD1551	Phase 2
0.7632	Intermediate Similarity	NPD2935	Discontinued
0.7619	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7473	Discontinued
0.7589	Intermediate Similarity	NPD9545	Approved
0.7588	Intermediate Similarity	NPD7039	Approved
0.7588	Intermediate Similarity	NPD7038	Approved
0.7584	Intermediate Similarity	NPD6233	Phase 2
0.7569	Intermediate Similarity	NPD1608	Approved
0.7562	Intermediate Similarity	NPD6599	Discontinued
0.7561	Intermediate Similarity	NPD6234	Discontinued
0.7561	Intermediate Similarity	NPD919	Approved
0.7551	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD1607	Approved
0.7547	Intermediate Similarity	NPD1653	Approved
0.7531	Intermediate Similarity	NPD7819	Suspended
0.7515	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3455	Phase 2
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5242	Approved
0.7485	Intermediate Similarity	NPD5353	Approved
0.7485	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3926	Phase 2
0.7484	Intermediate Similarity	NPD5403	Approved
0.7471	Intermediate Similarity	NPD8434	Phase 2
0.747	Intermediate Similarity	NPD7199	Phase 2
0.7469	Intermediate Similarity	NPD37	Approved
0.7468	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD2344	Approved
0.7464	Intermediate Similarity	NPD228	Approved
0.7448	Intermediate Similarity	NPD9269	Phase 2
0.7439	Intermediate Similarity	NPD4967	Phase 2
0.7439	Intermediate Similarity	NPD4965	Approved
0.7439	Intermediate Similarity	NPD4966	Approved
0.7436	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD4110	Phase 3
0.7436	Intermediate Similarity	NPD3750	Approved
0.7419	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7411	Suspended
0.74	Intermediate Similarity	NPD6798	Discontinued
0.7368	Intermediate Similarity	NPD1933	Approved
0.7368	Intermediate Similarity	NPD6355	Discontinued
0.7365	Intermediate Similarity	NPD6959	Discontinued
0.7365	Intermediate Similarity	NPD8127	Discontinued
0.7361	Intermediate Similarity	NPD17	Approved
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5401	Approved
0.7357	Intermediate Similarity	NPD1241	Discontinued
0.7353	Intermediate Similarity	NPD2163	Approved
0.7353	Intermediate Similarity	NPD7228	Approved
0.7353	Intermediate Similarity	NPD3751	Discontinued
0.7351	Intermediate Similarity	NPD4062	Phase 3
0.7338	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD2799	Discontinued
0.7329	Intermediate Similarity	NPD3972	Approved
0.7312	Intermediate Similarity	NPD6273	Approved
0.7303	Intermediate Similarity	NPD1558	Phase 1
0.7297	Intermediate Similarity	NPD1203	Approved
0.7296	Intermediate Similarity	NPD4357	Discontinued
0.7288	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3764	Approved
0.7284	Intermediate Similarity	NPD824	Approved
0.7284	Intermediate Similarity	NPD3226	Approved
0.7278	Intermediate Similarity	NPD3887	Approved
0.7278	Intermediate Similarity	NPD2354	Approved
0.7278	Intermediate Similarity	NPD2309	Approved
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD920	Approved
0.7267	Intermediate Similarity	NPD6832	Phase 2
0.7255	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2532	Approved
0.725	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD3146	Approved
0.725	Intermediate Similarity	NPD2533	Approved
0.725	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD2534	Approved
0.7244	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5283	Phase 1
0.7229	Intermediate Similarity	NPD7768	Phase 2
0.7226	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3787	Discontinued
0.7215	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5761	Phase 2
0.7212	Intermediate Similarity	NPD5760	Phase 2
0.7211	Intermediate Similarity	NPD1481	Phase 2
0.7208	Intermediate Similarity	NPD6653	Approved
0.72	Intermediate Similarity	NPD8313	Approved
0.72	Intermediate Similarity	NPD8312	Approved
0.72	Intermediate Similarity	NPD2861	Phase 2
0.7197	Intermediate Similarity	NPD2424	Discontinued
0.719	Intermediate Similarity	NPD4060	Phase 1
0.7178	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD2651	Approved
0.7178	Intermediate Similarity	NPD2649	Approved
0.7172	Intermediate Similarity	NPD9268	Approved
0.7171	Intermediate Similarity	NPD2313	Discontinued
0.7152	Intermediate Similarity	NPD6844	Discontinued
0.7152	Intermediate Similarity	NPD2800	Approved
0.7143	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1535	Discovery
0.7135	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2346	Discontinued
0.7125	Intermediate Similarity	NPD7440	Discontinued
0.7122	Intermediate Similarity	NPD2684	Approved
0.7117	Intermediate Similarity	NPD3687	Approved
0.7117	Intermediate Similarity	NPD3686	Approved
0.7115	Intermediate Similarity	NPD4308	Phase 3
0.7115	Intermediate Similarity	NPD3748	Approved
0.7111	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD8455	Phase 2
0.7108	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD8166	Discontinued
0.7105	Intermediate Similarity	NPD7095	Approved
0.7103	Intermediate Similarity	NPD1894	Discontinued
0.7095	Intermediate Similarity	NPD9717	Approved
0.7083	Intermediate Similarity	NPD3749	Approved
0.7078	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD3620	Phase 2
0.7078	Intermediate Similarity	NPD3142	Approved
0.7078	Intermediate Similarity	NPD3140	Approved
0.7073	Intermediate Similarity	NPD7458	Discontinued
0.707	Intermediate Similarity	NPD6100	Approved
0.707	Intermediate Similarity	NPD6099	Approved
0.7067	Intermediate Similarity	NPD2797	Approved
0.7059	Intermediate Similarity	NPD3268	Approved
0.7051	Intermediate Similarity	NPD4538	Approved
0.7051	Intermediate Similarity	NPD4536	Approved
0.7051	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2983	Phase 2
0.7047	Intermediate Similarity	NPD2982	Phase 2
0.7044	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD3060	Approved
0.7042	Intermediate Similarity	NPD7843	Approved
0.7039	Intermediate Similarity	NPD4908	Phase 1
0.7037	Intermediate Similarity	NPD4661	Approved
0.7037	Intermediate Similarity	NPD4662	Approved
0.7035	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD4340	Discontinued
0.7029	Intermediate Similarity	NPD3823	Discontinued

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