NPASS Compound

Structure

NPC474546 OpenBabel07101718312D 30 30 0 0 1 0 0 0 0 0999 V2000 5.1962 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4641 0.0000 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 6.0622 4.5000 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 6.0622 5.5000 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 1.7321 0.0000 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 -0.5000 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 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 5.1962 6.0000 0.0000 C 0 0 3 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 0.8660 1.5000 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 2.5981 4.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 3 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 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 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 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 4 5 1 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 15 1 0 0 0 0 8 20 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 19 1 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 24 2 0 0 0 0 15 25 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 18 19 2 0 0 0 0 19 26 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 21 28 1 0 0 0 0 22 23 1 0 0 0 0 22 29 1 0 0 0 0 23 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.23
Volume:	443.52
LogP:	2.401
LogD:	1.379
LogS:	-3.859
# Rotatable Bonds:	14
TPSA:	132.13
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.205
Synthetic Accessibility Score:	3.826
Fsp3:	0.609
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.114
MDCK Permeability:	1.3892100469092838e-05
Pgp-inhibitor:	0.209
Pgp-substrate:	0.102
Human Intestinal Absorption (HIA):	0.975
20% Bioavailability (F20%):	0.93
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.831
Plasma Protein Binding (PPB):	74.59989929199219%
Volume Distribution (VD):	0.258
Pgp-substrate:	13.090888977050781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.059
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.282
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.171
CYP3A4-inhibitor:	0.05
CYP3A4-substrate:	0.138

ADMET: Excretion

Clearance (CL):	9.51
Half-life (T1/2):	0.698

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.658
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.792
Skin Sensitization:	0.536
Carcinogencity:	0.029
Eye Corrosion:	0.004
Eye Irritation:	0.059
Respiratory Toxicity:	0.601

Download Data

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

Natural Product: NPC474546

Natural Product ID:	NPC474546
*Common Name:**	3-(2,3-Dihydroxy-3-Methylbutyl)-6-Hydroxy-2-[(1E,5E)-3,4,10-Trihydroxyundeca-1,5-Dienyl]Benzaldehyde
IUPAC Name:	3-(2,3-dihydroxy-3-methylbutyl)-6-hydroxy-2-[(1E,5E)-3,4,10-trihydroxyundeca-1,5-dienyl]benzaldehyde
Synonyms:
Standard InCHIKey:	BAXXMNBFCLQTAK-VTKKNFPDSA-N
Standard InCHI:	InChI=1S/C23H34O7/c1-15(25)7-5-4-6-8-20(27)21(28)12-10-17-16(13-22(29)23(2,3)30)9-11-19(26)18(17)14-24/h6,8-12,14-15,20-22,25-30H,4-5,7,13H2,1-3H3/b8-6+,12-10+
SMILES:	CC(CCCC=CC(C(C=CC1=C(C=CC(=C1C=O)O)CC(C(C)(C)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471678
PubChem CID:	16091532
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002754] Cinnamyl alcohols

*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
NPO33429	menisporopsis theobromae bcc 3975	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[17067151]

☑ 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	4
MIC	1

Activity Type	# Activity
Cell Line	2
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	>	47300.0	nM	PMID[484301]
NPT639	Cell Line	NCI-H187	Homo sapiens	IC50	>	47300.0	nM	PMID[484301]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	47300.0	nM	PMID[484301]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	47300.0	nM	PMID[484301]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	473900.0	nM	PMID[484301]

☑ 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 NPC474546 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	272
0.1-0.2	1262
0.2-0.3	2976
0.3-0.4	8414
0.4-0.5	11207
0.5-0.6	5258
0.6-0.7	9761
0.7-0.8	3308
0.8-0.85	212
0.85-0.9	26
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8923	High Similarity	NPC85342
0.8898	High Similarity	NPC167055
0.8898	High Similarity	NPC240744
0.8828	High Similarity	NPC49647
0.8828	High Similarity	NPC136342
0.8828	High Similarity	NPC295202
0.8828	High Similarity	NPC227741
0.875	High Similarity	NPC131799
0.8741	High Similarity	NPC206207
0.8699	High Similarity	NPC477453
0.8527	High Similarity	NPC68756
0.8527	High Similarity	NPC152525
0.8527	High Similarity	NPC74507
0.8527	High Similarity	NPC234890
0.8504	High Similarity	NPC292665
0.8504	High Similarity	NPC115188
0.8504	High Similarity	NPC244994
0.8504	High Similarity	NPC26433
0.8504	High Similarity	NPC178395
0.8504	High Similarity	NPC159760
0.8504	High Similarity	NPC35856
0.8504	High Similarity	NPC222876
0.8504	High Similarity	NPC272454
0.8504	High Similarity	NPC179092
0.8504	High Similarity	NPC301987
0.8496	Intermediate Similarity	NPC41847
0.8473	Intermediate Similarity	NPC473787
0.8468	Intermediate Similarity	NPC474486
0.8467	Intermediate Similarity	NPC141368
0.8444	Intermediate Similarity	NPC474394
0.8433	Intermediate Similarity	NPC110609
0.8433	Intermediate Similarity	NPC242358
0.8433	Intermediate Similarity	NPC246693
0.8429	Intermediate Similarity	NPC199936
0.8425	Intermediate Similarity	NPC7151
0.8425	Intermediate Similarity	NPC473662
0.8425	Intermediate Similarity	NPC216297
0.8421	Intermediate Similarity	NPC62219
0.8413	Intermediate Similarity	NPC184527
0.8409	Intermediate Similarity	NPC767
0.8409	Intermediate Similarity	NPC247250
0.8409	Intermediate Similarity	NPC3009
0.8406	Intermediate Similarity	NPC162939
0.838	Intermediate Similarity	NPC473023
0.837	Intermediate Similarity	NPC314048
0.8346	Intermediate Similarity	NPC233165
0.8346	Intermediate Similarity	NPC184579
0.8346	Intermediate Similarity	NPC473767
0.8321	Intermediate Similarity	NPC315275
0.8309	Intermediate Similarity	NPC204582
0.8309	Intermediate Similarity	NPC474519
0.8296	Intermediate Similarity	NPC470160
0.8286	Intermediate Similarity	NPC187843
0.8284	Intermediate Similarity	NPC17840
0.8284	Intermediate Similarity	NPC247477
0.8271	Intermediate Similarity	NPC48248
0.8268	Intermediate Similarity	NPC41567
0.8261	Intermediate Similarity	NPC71256
0.8258	Intermediate Similarity	NPC473691
0.8258	Intermediate Similarity	NPC306765
0.8258	Intermediate Similarity	NPC71610
0.8248	Intermediate Similarity	NPC278375
0.8239	Intermediate Similarity	NPC79627
0.8235	Intermediate Similarity	NPC180261
0.8235	Intermediate Similarity	NPC37299
0.8235	Intermediate Similarity	NPC52407
0.8231	Intermediate Similarity	NPC244351
0.8231	Intermediate Similarity	NPC283514
0.8231	Intermediate Similarity	NPC474000
0.8231	Intermediate Similarity	NPC307174
0.8227	Intermediate Similarity	NPC329493
0.8227	Intermediate Similarity	NPC474961
0.8222	Intermediate Similarity	NPC244699
0.8217	Intermediate Similarity	NPC216216
0.8217	Intermediate Similarity	NPC190971
0.8214	Intermediate Similarity	NPC158472
0.8209	Intermediate Similarity	NPC99731
0.8203	Intermediate Similarity	NPC182240
0.8189	Intermediate Similarity	NPC125252
0.8189	Intermediate Similarity	NPC174087
0.8188	Intermediate Similarity	NPC86524
0.8182	Intermediate Similarity	NPC477454
0.8175	Intermediate Similarity	NPC282780
0.8175	Intermediate Similarity	NPC202225
0.8175	Intermediate Similarity	NPC166480
0.8168	Intermediate Similarity	NPC198014
0.8162	Intermediate Similarity	NPC17843
0.8156	Intermediate Similarity	NPC106519
0.8156	Intermediate Similarity	NPC472904
0.8156	Intermediate Similarity	NPC470842
0.8156	Intermediate Similarity	NPC91019
0.8154	Intermediate Similarity	NPC198336
0.8154	Intermediate Similarity	NPC253627
0.8154	Intermediate Similarity	NPC295034
0.8148	Intermediate Similarity	NPC117609
0.8148	Intermediate Similarity	NPC259942
0.8148	Intermediate Similarity	NPC199253
0.8148	Intermediate Similarity	NPC136588
0.8143	Intermediate Similarity	NPC472903
0.814	Intermediate Similarity	NPC206778
0.814	Intermediate Similarity	NPC285829
0.8129	Intermediate Similarity	NPC194579
0.8129	Intermediate Similarity	NPC305060
0.8125	Intermediate Similarity	NPC120536
0.8125	Intermediate Similarity	NPC63918
0.8125	Intermediate Similarity	NPC285122
0.812	Intermediate Similarity	NPC473751
0.8116	Intermediate Similarity	NPC283088
0.8112	Intermediate Similarity	NPC29932
0.8112	Intermediate Similarity	NPC244691
0.8108	Intermediate Similarity	NPC475770
0.8106	Intermediate Similarity	NPC173978
0.8106	Intermediate Similarity	NPC231767
0.8106	Intermediate Similarity	NPC199273
0.8102	Intermediate Similarity	NPC40524
0.8102	Intermediate Similarity	NPC53896
0.8102	Intermediate Similarity	NPC78307
0.8102	Intermediate Similarity	NPC477139
0.8102	Intermediate Similarity	NPC139074
0.8102	Intermediate Similarity	NPC213485
0.8099	Intermediate Similarity	NPC135524
0.8099	Intermediate Similarity	NPC477209
0.8099	Intermediate Similarity	NPC85310
0.8095	Intermediate Similarity	NPC473931
0.8095	Intermediate Similarity	NPC474114
0.8095	Intermediate Similarity	NPC474050
0.8092	Intermediate Similarity	NPC282577
0.8092	Intermediate Similarity	NPC475192
0.8092	Intermediate Similarity	NPC86900
0.8092	Intermediate Similarity	NPC11250
0.8088	Intermediate Similarity	NPC474517
0.8088	Intermediate Similarity	NPC473777
0.8088	Intermediate Similarity	NPC7012
0.8088	Intermediate Similarity	NPC72669
0.8088	Intermediate Similarity	NPC471851
0.8088	Intermediate Similarity	NPC475042
0.8074	Intermediate Similarity	NPC34414
0.8074	Intermediate Similarity	NPC146647
0.8074	Intermediate Similarity	NPC92624
0.8071	Intermediate Similarity	NPC475974
0.8071	Intermediate Similarity	NPC94248
0.8071	Intermediate Similarity	NPC212693
0.806	Intermediate Similarity	NPC471530
0.8058	Intermediate Similarity	NPC118919
0.8058	Intermediate Similarity	NPC291454
0.8058	Intermediate Similarity	NPC191976
0.8056	Intermediate Similarity	NPC68441
0.8056	Intermediate Similarity	NPC83272
0.8056	Intermediate Similarity	NPC478019
0.8056	Intermediate Similarity	NPC170055
0.8049	Intermediate Similarity	NPC317305
0.8047	Intermediate Similarity	NPC28169
0.8047	Intermediate Similarity	NPC269414
0.8045	Intermediate Similarity	NPC137750
0.8045	Intermediate Similarity	NPC475733
0.8045	Intermediate Similarity	NPC472592
0.8045	Intermediate Similarity	NPC127975
0.8045	Intermediate Similarity	NPC123506
0.8043	Intermediate Similarity	NPC474097
0.8043	Intermediate Similarity	NPC50924
0.8042	Intermediate Similarity	NPC471731
0.8031	Intermediate Similarity	NPC161304
0.803	Intermediate Similarity	NPC375356
0.8029	Intermediate Similarity	NPC302844
0.8029	Intermediate Similarity	NPC70622
0.8028	Intermediate Similarity	NPC472605
0.8028	Intermediate Similarity	NPC472604
0.8028	Intermediate Similarity	NPC305845
0.8028	Intermediate Similarity	NPC204045
0.8016	Intermediate Similarity	NPC28784
0.8016	Intermediate Similarity	NPC296144
0.8016	Intermediate Similarity	NPC242136
0.8015	Intermediate Similarity	NPC147757
0.8015	Intermediate Similarity	NPC31799
0.8	Intermediate Similarity	NPC265454
0.8	Intermediate Similarity	NPC476535
0.8	Intermediate Similarity	NPC474771
0.8	Intermediate Similarity	NPC143685
0.8	Intermediate Similarity	NPC96024
0.8	Intermediate Similarity	NPC178467
0.8	Intermediate Similarity	NPC149372
0.8	Intermediate Similarity	NPC34634
0.8	Intermediate Similarity	NPC65837
0.8	Intermediate Similarity	NPC70380
0.8	Intermediate Similarity	NPC474849
0.8	Intermediate Similarity	NPC53001
0.8	Intermediate Similarity	NPC290030
0.8	Intermediate Similarity	NPC282923
0.8	Intermediate Similarity	NPC136878
0.8	Intermediate Similarity	NPC475957
0.7987	Intermediate Similarity	NPC472211
0.7986	Intermediate Similarity	NPC48130
0.7986	Intermediate Similarity	NPC469854
0.7986	Intermediate Similarity	NPC70859
0.7986	Intermediate Similarity	NPC142027
0.7986	Intermediate Similarity	NPC300684
0.7986	Intermediate Similarity	NPC290803
0.7986	Intermediate Similarity	NPC151607
0.7986	Intermediate Similarity	NPC103910
0.7986	Intermediate Similarity	NPC42540

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 NPC474546 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	260
0.1-0.2	897
0.2-0.3	1548
0.3-0.4	2666
0.4-0.5	2072
0.5-0.6	1158
0.6-0.7	496
0.7-0.8	50
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8056	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD1201	Approved
0.7969	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD1470	Approved
0.7746	Intermediate Similarity	NPD5404	Approved
0.7746	Intermediate Similarity	NPD2935	Discontinued
0.7746	Intermediate Similarity	NPD5408	Approved
0.7746	Intermediate Similarity	NPD5405	Approved
0.7746	Intermediate Similarity	NPD5406	Approved
0.7676	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1164	Approved
0.7552	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3300	Phase 2
0.7518	Intermediate Similarity	NPD943	Approved
0.75	Intermediate Similarity	NPD7390	Discontinued
0.7463	Intermediate Similarity	NPD2932	Approved
0.7463	Intermediate Similarity	NPD3019	Approved
0.7424	Intermediate Similarity	NPD9493	Approved
0.7403	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD9266	Approved
0.7344	Intermediate Similarity	NPD74	Approved
0.7333	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD2534	Approved
0.7333	Intermediate Similarity	NPD2533	Approved
0.7333	Intermediate Similarity	NPD4626	Approved
0.7324	Intermediate Similarity	NPD6663	Approved
0.732	Intermediate Similarity	NPD4380	Phase 2
0.731	Intermediate Similarity	NPD2799	Discontinued
0.729	Intermediate Similarity	NPD7819	Suspended
0.7286	Intermediate Similarity	NPD5736	Approved
0.7286	Intermediate Similarity	NPD9494	Approved
0.7279	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD9267	Approved
0.7266	Intermediate Similarity	NPD9263	Approved
0.7266	Intermediate Similarity	NPD9264	Approved
0.7226	Intermediate Similarity	NPD3092	Approved
0.7211	Intermediate Similarity	NPD2346	Discontinued
0.7185	Intermediate Similarity	NPD3091	Approved
0.7181	Intermediate Similarity	NPD8166	Discontinued
0.7154	Intermediate Similarity	NPD3022	Approved
0.7154	Intermediate Similarity	NPD3021	Approved
0.7153	Intermediate Similarity	NPD4060	Phase 1
0.7152	Intermediate Similarity	NPD7075	Discontinued
0.7143	Intermediate Similarity	NPD3094	Phase 2
0.7134	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD3764	Approved
0.7132	Intermediate Similarity	NPD5691	Approved
0.7121	Intermediate Similarity	NPD7635	Approved
0.7115	Intermediate Similarity	NPD1934	Approved
0.7105	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD2798	Approved
0.7081	Intermediate Similarity	NPD6232	Discontinued
0.7077	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD1510	Phase 2
0.7075	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD1283	Approved
0.707	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD7003	Approved
0.7067	Intermediate Similarity	NPD4628	Phase 3
0.7059	Intermediate Similarity	NPD9545	Approved
0.7055	Intermediate Similarity	NPD7473	Discontinued
0.7048	Intermediate Similarity	NPD6559	Discontinued
0.7045	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1240	Approved
0.7032	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3023	Approved
0.7029	Intermediate Similarity	NPD3026	Approved
0.7019	Intermediate Similarity	NPD6959	Discontinued
0.7016	Intermediate Similarity	NPD844	Approved
0.7016	Intermediate Similarity	NPD1809	Phase 2
0.7015	Intermediate Similarity	NPD9281	Approved
0.7007	Intermediate Similarity	NPD3025	Approved
0.7007	Intermediate Similarity	NPD1651	Approved
0.7007	Intermediate Similarity	NPD3024	Approved
0.7	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD845	Approved
0.6986	Remote Similarity	NPD6355	Discontinued
0.6984	Remote Similarity	NPD3020	Approved
0.6981	Remote Similarity	NPD7768	Phase 2
0.698	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2344	Approved
0.696	Remote Similarity	NPD288	Approved
0.6957	Remote Similarity	NPD3095	Discontinued
0.6954	Remote Similarity	NPD3400	Discontinued
0.6953	Remote Similarity	NPD9261	Approved
0.6948	Remote Similarity	NPD6273	Approved
0.6941	Remote Similarity	NPD8150	Discontinued
0.6939	Remote Similarity	NPD1607	Approved
0.6935	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1549	Phase 2
0.6929	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD9717	Approved
0.6923	Remote Similarity	NPD7458	Discontinued
0.6923	Remote Similarity	NPD3226	Approved
0.6908	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4954	Approved
0.6905	Remote Similarity	NPD36	Approved
0.6905	Remote Similarity	NPD4955	Approved
0.6905	Remote Similarity	NPD5034	Approved
0.6905	Remote Similarity	NPD5026	Approved
0.6905	Remote Similarity	NPD5028	Approved
0.6899	Remote Similarity	NPD1237	Approved
0.6899	Remote Similarity	NPD6801	Discontinued
0.6897	Remote Similarity	NPD2313	Discontinued
0.689	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.689	Remote Similarity	NPD6166	Phase 2
0.6889	Remote Similarity	NPD5951	Approved
0.6889	Remote Similarity	NPD2629	Approved
0.6887	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.688	Remote Similarity	NPD2860	Approved
0.688	Remote Similarity	NPD2859	Approved
0.6879	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6832	Phase 2
0.6875	Remote Similarity	NPD3882	Suspended
0.6871	Remote Similarity	NPD447	Suspended
0.6871	Remote Similarity	NPD230	Phase 1
0.687	Remote Similarity	NPD2342	Discontinued
0.6867	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8312	Approved
0.6864	Remote Similarity	NPD8313	Approved
0.686	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1281	Approved
0.6855	Remote Similarity	NPD2801	Approved
0.6845	Remote Similarity	NPD5030	Phase 2
0.6842	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1876	Approved
0.6826	Remote Similarity	NPD7074	Phase 3
0.6824	Remote Similarity	NPD6651	Approved
0.6821	Remote Similarity	NPD2424	Discontinued
0.6818	Remote Similarity	NPD1511	Approved
0.6809	Remote Similarity	NPD9269	Phase 2
0.6803	Remote Similarity	NPD826	Approved
0.6803	Remote Similarity	NPD825	Approved
0.6803	Remote Similarity	NPD2979	Phase 3
0.68	Remote Similarity	NPD4476	Approved
0.68	Remote Similarity	NPD4477	Approved
0.68	Remote Similarity	NPD2933	Approved
0.68	Remote Similarity	NPD2438	Suspended
0.68	Remote Similarity	NPD2934	Approved
0.68	Remote Similarity	NPD2796	Approved
0.68	Remote Similarity	NPD1551	Phase 2
0.6797	Remote Similarity	NPD2309	Approved
0.6783	Remote Similarity	NPD1203	Approved
0.6781	Remote Similarity	NPD6798	Discontinued
0.6781	Remote Similarity	NPD411	Approved
0.6772	Remote Similarity	NPD9495	Approved
0.6766	Remote Similarity	NPD7054	Approved
0.6766	Remote Similarity	NPD5844	Phase 1
0.6761	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD846	Approved
0.6744	Remote Similarity	NPD5037	Approved
0.6744	Remote Similarity	NPD940	Approved
0.6744	Remote Similarity	NPD5038	Approved
0.6736	Remote Similarity	NPD258	Approved
0.6736	Remote Similarity	NPD257	Approved
0.6735	Remote Similarity	NPD520	Approved
0.6732	Remote Similarity	NPD3750	Approved
0.6731	Remote Similarity	NPD1512	Approved
0.673	Remote Similarity	NPD7411	Suspended
0.6726	Remote Similarity	NPD7472	Approved
0.6716	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7157	Approved
0.6714	Remote Similarity	NPD4059	Approved
0.6712	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.671	Remote Similarity	NPD6799	Approved
0.6709	Remote Similarity	NPD2651	Approved
0.6709	Remote Similarity	NPD2649	Approved
0.6709	Remote Similarity	NPD3455	Phase 2
0.6707	Remote Similarity	NPD3818	Discontinued
0.6691	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.669	Remote Similarity	NPD4208	Discontinued
0.669	Remote Similarity	NPD3972	Approved
0.6689	Remote Similarity	NPD9570	Approved
0.6688	Remote Similarity	NPD6190	Approved
0.6687	Remote Similarity	NPD6844	Discontinued
0.6686	Remote Similarity	NPD5036	Approved
0.6667	Remote Similarity	NPD4661	Approved
0.6667	Remote Similarity	NPD4662	Approved
0.6667	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD5711	Approved
0.6667	Remote Similarity	NPD5710	Approved
0.6667	Remote Similarity	NPD2800	Approved
0.6647	Remote Similarity	NPD7251	Discontinued
0.6646	Remote Similarity	NPD5494	Approved
0.6645	Remote Similarity	NPD5763	Approved
0.6645	Remote Similarity	NPD5762	Approved
0.6644	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD1755	Approved
0.6643	Remote Similarity	NPD9268	Approved
0.6642	Remote Similarity	NPD4750	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