NPASS Compound

Structure

NPC273843 OpenBabel07101718192D 37 39 0 0 0 0 0 0 0 0999 V2000 2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 7.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 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 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 3.4641 -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 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 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 -2.5981 -0.5000 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 -0.8660 -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 -0.0000 -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 0.8660 -0.5000 0.0000 C 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 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 16 2 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 17 2 0 0 0 0 10 12 1 0 0 0 0 10 18 2 0 0 0 0 11 21 1 0 0 0 0 12 19 1 0 0 0 0 13 14 2 0 0 0 0 13 20 1 0 0 0 0 14 22 1 0 0 0 0 15 23 2 0 0 0 0 15 24 1 0 0 0 0 19 20 2 0 0 0 0 19 26 1 0 0 0 0 20 30 1 0 0 0 0 21 23 1 0 0 0 0 21 29 2 0 0 0 0 22 26 2 0 0 0 0 22 31 1 0 0 0 0 23 32 1 0 0 0 0 24 25 2 0 0 0 0 24 33 1 0 0 0 0 25 27 1 0 0 0 0 25 29 1 0 0 0 0 26 34 1 0 0 0 0 27 28 1 0 0 0 0 27 35 2 0 0 0 0 28 30 2 0 0 0 0 28 36 1 0 0 0 0 29 37 1 0 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	506.23
Volume:	534.297
LogP:	7.469
LogD:	3.5
LogS:	-2.293
# Rotatable Bonds:	8
TPSA:	131.36
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.169
Synthetic Accessibility Score:	3.449
Fsp3:	0.3
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.041
MDCK Permeability:	1.2038387467327993e-05
Pgp-inhibitor:	0.733
Pgp-substrate:	0.409
Human Intestinal Absorption (HIA):	0.104
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	89.68482208251953%
Volume Distribution (VD):	1.004
Pgp-substrate:	13.297553062438965%

ADMET: Metabolism

CYP1A2-inhibitor:	0.607
CYP1A2-substrate:	0.162
CYP2C19-inhibitor:	0.768
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.801
CYP2C9-substrate:	0.721
CYP2D6-inhibitor:	0.54
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.131
CYP3A4-substrate:	0.044

ADMET: Excretion

Clearance (CL):	8.053
Half-life (T1/2):	0.437

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.969
Drug-inuced Liver Injury (DILI):	0.976
AMES Toxicity:	0.509
Rat Oral Acute Toxicity:	0.223
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.897
Carcinogencity:	0.107
Eye Corrosion:	0.003
Eye Irritation:	0.756
Respiratory Toxicity:	0.095

Download Data

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

Natural Product: NPC273843

Natural Product ID:	NPC273843
*Common Name:**	Notabilisin C
IUPAC Name:	2-[2-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,4-dihydroxyphenyl]-3,5,7-trihydroxy-8-(3-methylbut-2-enyl)chromen-4-one
Synonyms:	Notabilisin C
Standard InCHIKey:	MQNQGTVUMGNSEG-VCHYOVAHSA-N
Standard InCHI:	InChI=1S/C30H34O7/c1-16(2)7-6-8-18(5)10-12-19-20(13-14-22(31)26(19)34)30-28(36)27(35)25-24(33)15-23(32)21(29(25)37-30)11-9-17(3)4/h7,9-10,13-15,31-34,36H,6,8,11-12H2,1-5H3/b18-10+
SMILES:	C/C(=CCc1c(O)c(O)ccc1c1oc2c(CC=C(C)C)c(O)cc(c2c(=O)c1O)O)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1808154
PubChem CID:	53363479
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0003587] 2'-prenylated flavones

*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
NPO27320	Morus notabilis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21737271]
NPO27320	Morus notabilis	Species	Moraceae	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
Others	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	312.24	%	PMID[551342]
NPT520	Cell Line	3T3-L1	Mus musculus	Activity	=	948.51	%	PMID[551342]

☑ 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 NPC273843 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	458
0.1-0.2	1894
0.2-0.3	4468
0.3-0.4	10922
0.4-0.5	6862
0.5-0.6	3601
0.6-0.7	4981
0.7-0.8	4992
0.8-0.85	2466
0.85-0.9	1324
0.9-0.95	652
0.95-1	77

Similarity Score	Similarity Level	Natural Product ID
0.9933	High Similarity	NPC13779
0.9933	High Similarity	NPC475799
0.9732	High Similarity	NPC37684
0.9732	High Similarity	NPC63187
0.9732	High Similarity	NPC157784
0.9669	High Similarity	NPC3980
0.9664	High Similarity	NPC304295
0.9664	High Similarity	NPC59162
0.9664	High Similarity	NPC205046
0.9605	High Similarity	NPC237418
0.9603	High Similarity	NPC80534
0.9603	High Similarity	NPC133392
0.9603	High Similarity	NPC56786
0.9597	High Similarity	NPC88804
0.9597	High Similarity	NPC3825
0.9542	High Similarity	NPC210459
0.9484	High Similarity	NPC211107
0.9481	High Similarity	NPC321399
0.9477	High Similarity	NPC236796
0.947	High Similarity	NPC249570
0.9419	High Similarity	NPC278427
0.9416	High Similarity	NPC46736
0.9416	High Similarity	NPC197856
0.9416	High Similarity	NPC280680
0.9412	High Similarity	NPC142339
0.9408	High Similarity	NPC476631
0.9408	High Similarity	NPC170492
0.9404	High Similarity	NPC154345
0.94	High Similarity	NPC270465
0.94	High Similarity	NPC87125
0.9363	High Similarity	NPC475888
0.9359	High Similarity	NPC329760
0.9359	High Similarity	NPC201800
0.9359	High Similarity	NPC78332
0.9355	High Similarity	NPC320359
0.9355	High Similarity	NPC45146
0.9355	High Similarity	NPC476280
0.9355	High Similarity	NPC471973
0.9355	High Similarity	NPC36217
0.9355	High Similarity	NPC119224
0.9355	High Similarity	NPC235018
0.9355	High Similarity	NPC297212
0.9351	High Similarity	NPC136674
0.9351	High Similarity	NPC476630
0.9351	High Similarity	NPC218871
0.9346	High Similarity	NPC67396
0.9342	High Similarity	NPC471982
0.9338	High Similarity	NPC286342
0.9338	High Similarity	NPC188871
0.9338	High Similarity	NPC149127
0.9329	High Similarity	NPC179271
0.9329	High Similarity	NPC20791
0.9304	High Similarity	NPC39091
0.9299	High Similarity	NPC189473
0.9299	High Similarity	NPC474240
0.9299	High Similarity	NPC23298
0.9299	High Similarity	NPC207690
0.9299	High Similarity	NPC186686
0.9295	High Similarity	NPC32694
0.9295	High Similarity	NPC187354
0.9295	High Similarity	NPC40491
0.9295	High Similarity	NPC278052
0.929	High Similarity	NPC235448
0.929	High Similarity	NPC22192
0.929	High Similarity	NPC100123
0.929	High Similarity	NPC85121
0.9286	High Similarity	NPC472907
0.9286	High Similarity	NPC24640
0.9286	High Similarity	NPC471985
0.9286	High Similarity	NPC276444
0.9286	High Similarity	NPC153512
0.9281	High Similarity	NPC179126
0.9281	High Similarity	NPC89474
0.9281	High Similarity	NPC189130
0.9281	High Similarity	NPC78326
0.9281	High Similarity	NPC270620
0.9281	High Similarity	NPC213896
0.9281	High Similarity	NPC192083
0.9281	High Similarity	NPC236223
0.9281	High Similarity	NPC298692
0.9276	High Similarity	NPC200740
0.9276	High Similarity	NPC260895
0.9276	High Similarity	NPC125062
0.9276	High Similarity	NPC252933
0.9276	High Similarity	NPC54394
0.9272	High Similarity	NPC269420
0.9267	High Similarity	NPC108406
0.9267	High Similarity	NPC51443
0.9267	High Similarity	NPC74881
0.9245	High Similarity	NPC476306
0.9245	High Similarity	NPC218226
0.9241	High Similarity	NPC239752
0.9241	High Similarity	NPC293319
0.9241	High Similarity	NPC156432
0.9241	High Similarity	NPC275780
0.9241	High Similarity	NPC472450
0.9236	High Similarity	NPC206605
0.9231	High Similarity	NPC56085
0.9231	High Similarity	NPC282009
0.9231	High Similarity	NPC299436
0.9231	High Similarity	NPC287328
0.9231	High Similarity	NPC80375
0.9231	High Similarity	NPC476283
0.9231	High Similarity	NPC14353
0.9231	High Similarity	NPC228785
0.9231	High Similarity	NPC246478
0.9231	High Similarity	NPC470183
0.9226	High Similarity	NPC472963
0.9221	High Similarity	NPC472280
0.9221	High Similarity	NPC321779
0.9221	High Similarity	NPC234255
0.9216	High Similarity	NPC237994
0.9216	High Similarity	NPC82325
0.9216	High Similarity	NPC55205
0.9216	High Similarity	NPC106976
0.9216	High Similarity	NPC279989
0.9211	High Similarity	NPC50728
0.9211	High Similarity	NPC85131
0.9211	High Similarity	NPC166753
0.92	High Similarity	NPC169749
0.9195	High Similarity	NPC190637
0.9195	High Similarity	NPC9117
0.9195	High Similarity	NPC212932
0.9195	High Similarity	NPC24821
0.9195	High Similarity	NPC293053
0.9195	High Similarity	NPC279121
0.9182	High Similarity	NPC43319
0.9182	High Similarity	NPC37870
0.9182	High Similarity	NPC472449
0.9177	High Similarity	NPC7483
0.9177	High Similarity	NPC270837
0.9177	High Similarity	NPC476295
0.9177	High Similarity	NPC12461
0.9177	High Similarity	NPC236132
0.9177	High Similarity	NPC220313
0.9177	High Similarity	NPC472625
0.9172	High Similarity	NPC61010
0.9172	High Similarity	NPC471499
0.9172	High Similarity	NPC474239
0.9172	High Similarity	NPC289771
0.9172	High Similarity	NPC474187
0.9167	High Similarity	NPC469658
0.9167	High Similarity	NPC172770
0.9167	High Similarity	NPC185258
0.9161	High Similarity	NPC274730
0.9161	High Similarity	NPC209614
0.9161	High Similarity	NPC68093
0.9161	High Similarity	NPC291878
0.9161	High Similarity	NPC265511
0.9161	High Similarity	NPC472626
0.9161	High Similarity	NPC49824
0.9161	High Similarity	NPC282307
0.9161	High Similarity	NPC170026
0.9161	High Similarity	NPC470328
0.9161	High Similarity	NPC195796
0.9161	High Similarity	NPC472455
0.9161	High Similarity	NPC471500
0.9161	High Similarity	NPC191146
0.9161	High Similarity	NPC278778
0.9161	High Similarity	NPC35038
0.9156	High Similarity	NPC473664
0.9156	High Similarity	NPC33051
0.9156	High Similarity	NPC472905
0.9156	High Similarity	NPC58382
0.9156	High Similarity	NPC227337
0.9156	High Similarity	NPC74924
0.9156	High Similarity	NPC162351
0.9156	High Similarity	NPC273462
0.9156	High Similarity	NPC49402
0.9156	High Similarity	NPC93552
0.9156	High Similarity	NPC70433
0.915	High Similarity	NPC236769
0.915	High Similarity	NPC133953
0.915	High Similarity	NPC202157
0.915	High Similarity	NPC50403
0.915	High Similarity	NPC28274
0.9145	High Similarity	NPC183950
0.9145	High Similarity	NPC52005
0.9145	High Similarity	NPC137062
0.9145	High Similarity	NPC65775
0.9145	High Similarity	NPC177298
0.9145	High Similarity	NPC48479
0.9145	High Similarity	NPC287101
0.9145	High Similarity	NPC195351
0.9145	High Similarity	NPC38545
0.9145	High Similarity	NPC171916
0.9145	High Similarity	NPC10027
0.9145	High Similarity	NPC223579
0.9145	High Similarity	NPC159103
0.9139	High Similarity	NPC259632
0.9133	High Similarity	NPC216538
0.9133	High Similarity	NPC326500
0.9133	High Similarity	NPC70136
0.9133	High Similarity	NPC273538
0.9128	High Similarity	NPC473042
0.9128	High Similarity	NPC175013
0.9128	High Similarity	NPC200694
0.9125	High Similarity	NPC126204
0.9119	High Similarity	NPC303174
0.9119	High Similarity	NPC62261

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 NPC273843 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	410
0.1-0.2	1005
0.2-0.3	1730
0.3-0.4	2699
0.4-0.5	1769
0.5-0.6	952
0.6-0.7	403
0.7-0.8	127
0.8-0.85	34
0.85-0.9	15
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9329	High Similarity	NPD1512	Approved
0.9281	High Similarity	NPD2393	Clinical (unspecified phase)
0.9195	High Similarity	NPD1511	Approved
0.9133	High Similarity	NPD4378	Clinical (unspecified phase)
0.9032	High Similarity	NPD2801	Approved
0.8968	High Similarity	NPD1934	Approved
0.8797	High Similarity	NPD3882	Suspended
0.8765	High Similarity	NPD6166	Phase 2
0.8765	High Similarity	NPD6168	Clinical (unspecified phase)
0.8765	High Similarity	NPD6167	Clinical (unspecified phase)
0.8734	High Similarity	NPD3817	Phase 2
0.8671	High Similarity	NPD7819	Suspended
0.8625	High Similarity	NPD7075	Discontinued
0.8598	High Similarity	NPD7473	Discontinued
0.8563	High Similarity	NPD7251	Discontinued
0.8553	High Similarity	NPD7096	Clinical (unspecified phase)
0.8528	High Similarity	NPD6232	Discontinued
0.8516	High Similarity	NPD7410	Clinical (unspecified phase)
0.8503	High Similarity	NPD6797	Phase 2
0.8494	Intermediate Similarity	NPD7054	Approved
0.8481	Intermediate Similarity	NPD4380	Phase 2
0.8443	Intermediate Similarity	NPD7472	Approved
0.8443	Intermediate Similarity	NPD7074	Phase 3
0.8434	Intermediate Similarity	NPD3818	Discontinued
0.8402	Intermediate Similarity	NPD7808	Phase 3
0.8385	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD6801	Discontinued
0.8354	Intermediate Similarity	NPD6959	Discontinued
0.8301	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD5494	Approved
0.8289	Intermediate Similarity	NPD1510	Phase 2
0.8258	Intermediate Similarity	NPD3750	Approved
0.8247	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD1549	Phase 2
0.8235	Intermediate Similarity	NPD2796	Approved
0.8221	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6799	Approved
0.821	Intermediate Similarity	NPD1465	Phase 2
0.8171	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD5844	Phase 1
0.8146	Intermediate Similarity	NPD1240	Approved
0.8146	Intermediate Similarity	NPD943	Approved
0.8137	Intermediate Similarity	NPD6599	Discontinued
0.8086	Intermediate Similarity	NPD7411	Suspended
0.8077	Intermediate Similarity	NPD2800	Approved
0.805	Intermediate Similarity	NPD2534	Approved
0.805	Intermediate Similarity	NPD2533	Approved
0.805	Intermediate Similarity	NPD2532	Approved
0.8039	Intermediate Similarity	NPD1607	Approved
0.8024	Intermediate Similarity	NPD1247	Approved
0.8012	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD7768	Phase 2
0.7965	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD3226	Approved
0.7952	Intermediate Similarity	NPD3749	Approved
0.7939	Intermediate Similarity	NPD5402	Approved
0.7935	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD3748	Approved
0.7929	Intermediate Similarity	NPD3926	Phase 2
0.7885	Intermediate Similarity	NPD2935	Discontinued
0.7885	Intermediate Similarity	NPD6100	Approved
0.7885	Intermediate Similarity	NPD6099	Approved
0.7882	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7390	Discontinued
0.784	Intermediate Similarity	NPD5403	Approved
0.7834	Intermediate Similarity	NPD2346	Discontinued
0.7816	Intermediate Similarity	NPD6559	Discontinued
0.7815	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1243	Approved
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5401	Approved
0.7709	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2799	Discontinued
0.7692	Intermediate Similarity	NPD6651	Approved
0.7677	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1613	Approved
0.767	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD2313	Discontinued
0.7628	Intermediate Similarity	NPD230	Phase 1
0.7622	Intermediate Similarity	NPD920	Approved
0.761	Intermediate Similarity	NPD2344	Approved
0.7602	Intermediate Similarity	NPD7199	Phase 2
0.7597	Intermediate Similarity	NPD4625	Phase 3
0.7588	Intermediate Similarity	NPD6234	Discontinued
0.7586	Intermediate Similarity	NPD3751	Discontinued
0.7578	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD3787	Discontinued
0.7547	Intermediate Similarity	NPD1551	Phase 2
0.7543	Intermediate Similarity	NPD7286	Phase 2
0.7542	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD447	Suspended
0.7515	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD3027	Phase 3
0.7469	Intermediate Similarity	NPD4628	Phase 3
0.7459	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD5953	Discontinued
0.7457	Intermediate Similarity	NPD7229	Phase 3
0.7457	Intermediate Similarity	NPD5710	Approved
0.7457	Intermediate Similarity	NPD5711	Approved
0.7452	Intermediate Similarity	NPD4060	Phase 1
0.7436	Intermediate Similarity	NPD3268	Approved
0.7436	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8312	Approved
0.743	Intermediate Similarity	NPD8313	Approved
0.7423	Intermediate Similarity	NPD2309	Approved
0.7417	Intermediate Similarity	NPD1201	Approved
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7403	Intermediate Similarity	NPD2798	Approved
0.7403	Intermediate Similarity	NPD8150	Discontinued
0.7396	Intermediate Similarity	NPD37	Approved
0.7391	Intermediate Similarity	NPD1471	Phase 3
0.7386	Intermediate Similarity	NPD7228	Approved
0.7368	Intermediate Similarity	NPD4966	Approved
0.7368	Intermediate Similarity	NPD4965	Approved
0.7368	Intermediate Similarity	NPD4967	Phase 2
0.7362	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD4360	Phase 2
0.7351	Intermediate Similarity	NPD4363	Phase 3
0.734	Intermediate Similarity	NPD6776	Approved
0.734	Intermediate Similarity	NPD6779	Approved
0.734	Intermediate Similarity	NPD6781	Approved
0.734	Intermediate Similarity	NPD6780	Approved
0.734	Intermediate Similarity	NPD6777	Approved
0.734	Intermediate Similarity	NPD6778	Approved
0.734	Intermediate Similarity	NPD6782	Approved
0.7338	Intermediate Similarity	NPD1470	Approved
0.7338	Intermediate Similarity	NPD2797	Approved
0.7338	Intermediate Similarity	NPD1203	Approved
0.7333	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD5408	Approved
0.7329	Intermediate Similarity	NPD5405	Approved
0.7329	Intermediate Similarity	NPD5404	Approved
0.7329	Intermediate Similarity	NPD5406	Approved
0.7317	Intermediate Similarity	NPD6190	Approved
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.731	Intermediate Similarity	NPD4288	Approved
0.7308	Intermediate Similarity	NPD4908	Phase 1
0.7273	Intermediate Similarity	NPD3300	Phase 2
0.7255	Intermediate Similarity	NPD1608	Approved
0.7225	Intermediate Similarity	NPD7698	Approved
0.7225	Intermediate Similarity	NPD7697	Approved
0.7225	Intermediate Similarity	NPD7696	Phase 3
0.7219	Intermediate Similarity	NPD4361	Phase 2
0.7219	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8151	Discontinued
0.7208	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6832	Phase 2
0.719	Intermediate Similarity	NPD422	Phase 1
0.719	Intermediate Similarity	NPD1610	Phase 2
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD6355	Discontinued
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7188	Intermediate Similarity	NPD1933	Approved
0.7175	Intermediate Similarity	NPD2403	Approved
0.7165	Intermediate Similarity	NPD7701	Phase 2
0.716	Intermediate Similarity	NPD4308	Phase 3
0.716	Intermediate Similarity	NPD7033	Discontinued
0.716	Intermediate Similarity	NPD1653	Approved
0.7152	Intermediate Similarity	NPD1548	Phase 1
0.7152	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7135	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD9494	Approved
0.7127	Intermediate Similarity	NPD7685	Pre-registration
0.7118	Intermediate Similarity	NPD7458	Discontinued
0.7115	Intermediate Similarity	NPD3267	Approved
0.7115	Intermediate Similarity	NPD3266	Approved
0.7113	Intermediate Similarity	NPD7584	Approved
0.7107	Intermediate Similarity	NPD6798	Discontinued
0.7107	Intermediate Similarity	NPD3764	Approved
0.7097	Intermediate Similarity	NPD4749	Approved
0.7092	Intermediate Similarity	NPD7874	Approved
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6535	Approved
0.7074	Intermediate Similarity	NPD6534	Approved
0.7059	Intermediate Similarity	NPD17	Approved
0.7056	Intermediate Similarity	NPD7801	Approved
0.7056	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7783	Phase 2
0.7053	Intermediate Similarity	NPD7700	Phase 2
0.7053	Intermediate Similarity	NPD7699	Phase 2
0.7051	Intermediate Similarity	NPD3225	Approved

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