NPASS Compound

Structure

CID10027 OpenBabel06191715332D 27 29 0 0 0 0 0 0 0 0999 V2000 6.9282 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 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 4.3301 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 6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 1.7321 2.0000 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 6.0622 4.5000 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 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 17 1 0 0 0 0 7 19 2 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 9 16 1 0 0 0 0 10 11 2 0 0 0 0 10 15 1 0 0 0 0 11 23 1 0 0 0 0 12 15 2 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 13 21 2 0 0 0 0 15 21 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 22 1 0 0 0 0 18 20 2 0 0 0 0 18 22 1 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 27 1 0 0 0 0 22 26 2 0 0 0 0 23 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	364.17
Volume:	392.128
LogP:	6.287
LogD:	4.543
LogS:	-3.328
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.59
Synthetic Accessibility Score:	2.969
Fsp3:	0.261
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.879
MDCK Permeability:	2.156198570446577e-05
Pgp-inhibitor:	0.955
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.065
30% Bioavailability (F30%):	0.058

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	101.33142852783203%
Volume Distribution (VD):	0.744
Pgp-substrate:	0.9536561369895935%

ADMET: Metabolism

CYP1A2-inhibitor:	0.899
CYP1A2-substrate:	0.353
CYP2C19-inhibitor:	0.918
CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.875
CYP2C9-substrate:	0.903
CYP2D6-inhibitor:	0.948
CYP2D6-substrate:	0.367
CYP3A4-inhibitor:	0.753
CYP3A4-substrate:	0.221

ADMET: Excretion

Clearance (CL):	8.481
Half-life (T1/2):	0.163

ADMET: Toxicity

hERG Blockers:	0.262
Human Hepatotoxicity (H-HT):	0.864
Drug-inuced Liver Injury (DILI):	0.237
AMES Toxicity:	0.087
Rat Oral Acute Toxicity:	0.242
Maximum Recommended Daily Dose:	0.9
Skin Sensitization:	0.181
Carcinogencity:	0.809
Eye Corrosion:	0.003
Eye Irritation:	0.166
Respiratory Toxicity:	0.864

Download Data

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

Natural Product: NPC10027

Natural Product ID:	NPC10027
*Common Name:**	Cudraphenone A
IUPAC Name:	(7-hydroxy-2,2-dimethylchromen-6-yl)-[3-hydroxy-2-(3-methylbut-2-enyl)phenyl]methanone
Synonyms:
Standard InCHIKey:	KOJDUQIWHNYJEM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H24O4/c1-14(2)8-9-16-17(6-5-7-19(16)24)22(26)18-12-15-10-11-23(3,4)27-21(15)13-20(18)25/h5-8,10-13,24-25H,9H2,1-4H3
SMILES:	CC(=CCc1c(cccc1O)C(=O)c1cc2C=CC(C)(C)Oc2cc1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517213
PubChem CID:	11793144
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000120] Benzophenones

*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
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[11170668]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[12932139]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23156	Maclura cochinchinensis	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	3

Activity Type	# Activity
Cell Line	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	CC50	=	170000.0	nM	PMID[480155]
NPT924	Cell Line	HSC-2	Homo sapiens	Ratio	=	2.5	n.a.	PMID[480155]
NPT27	Others	Unspecified		CC50	=	430000.0	nM	PMID[480155]

☑ 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 NPC10027 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	418
0.1-0.2	1651
0.2-0.3	3919
0.3-0.4	10076
0.4-0.5	8158
0.5-0.6	3385
0.6-0.7	5342
0.7-0.8	5171
0.8-0.85	2454
0.85-0.9	1644
0.9-0.95	469
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC65775
0.9592	High Similarity	NPC178964
0.9592	High Similarity	NPC95842
0.9592	High Similarity	NPC280530
0.958	High Similarity	NPC311741
0.958	High Similarity	NPC234629
0.953	High Similarity	NPC268360
0.9521	High Similarity	NPC227122
0.9507	High Similarity	NPC156590
0.9507	High Similarity	NPC64908
0.9507	High Similarity	NPC118840
0.9507	High Similarity	NPC147688
0.9507	High Similarity	NPC205006
0.9459	High Similarity	NPC210942
0.9459	High Similarity	NPC329844
0.9459	High Similarity	NPC169990
0.9456	High Similarity	NPC258249
0.9452	High Similarity	NPC65589
0.9452	High Similarity	NPC97028
0.9452	High Similarity	NPC100985
0.9452	High Similarity	NPC158338
0.9452	High Similarity	NPC288036
0.9452	High Similarity	NPC97029
0.9441	High Similarity	NPC226636
0.9441	High Similarity	NPC11561
0.9441	High Similarity	NPC144499
0.9437	High Similarity	NPC475680
0.9437	High Similarity	NPC172986
0.9437	High Similarity	NPC235239
0.9437	High Similarity	NPC261227
0.9437	High Similarity	NPC305355
0.9437	High Similarity	NPC270883
0.9396	High Similarity	NPC55662
0.9396	High Similarity	NPC166054
0.9396	High Similarity	NPC99199
0.9392	High Similarity	NPC154683
0.9392	High Similarity	NPC40356
0.9388	High Similarity	NPC101957
0.9388	High Similarity	NPC120105
0.9384	High Similarity	NPC27221
0.9384	High Similarity	NPC37135
0.9384	High Similarity	NPC7025
0.9384	High Similarity	NPC186397
0.9384	High Similarity	NPC256672
0.9384	High Similarity	NPC266572
0.9379	High Similarity	NPC477955
0.9375	High Similarity	NPC106985
0.9375	High Similarity	NPC11700
0.9375	High Similarity	NPC166138
0.9375	High Similarity	NPC219915
0.9375	High Similarity	NPC18585
0.9375	High Similarity	NPC38219
0.9371	High Similarity	NPC49108
0.9371	High Similarity	NPC110969
0.9371	High Similarity	NPC103362
0.9366	High Similarity	NPC303633
0.9366	High Similarity	NPC96565
0.9366	High Similarity	NPC301217
0.9366	High Similarity	NPC220062
0.9366	High Similarity	NPC216978
0.9366	High Similarity	NPC55018
0.9329	High Similarity	NPC235333
0.9329	High Similarity	NPC214632
0.9329	High Similarity	NPC472462
0.9324	High Similarity	NPC474417
0.9324	High Similarity	NPC478148
0.9324	High Similarity	NPC149526
0.9324	High Similarity	NPC154345
0.9324	High Similarity	NPC305965
0.932	High Similarity	NPC266499
0.932	High Similarity	NPC473978
0.932	High Similarity	NPC223988
0.9315	High Similarity	NPC104406
0.9315	High Similarity	NPC24673
0.9315	High Similarity	NPC79469
0.9315	High Similarity	NPC123202
0.9315	High Similarity	NPC97716
0.9315	High Similarity	NPC7943
0.9315	High Similarity	NPC201731
0.9315	High Similarity	NPC22005
0.9315	High Similarity	NPC237635
0.9306	High Similarity	NPC78803
0.9306	High Similarity	NPC310340
0.9306	High Similarity	NPC293852
0.9306	High Similarity	NPC217083
0.9306	High Similarity	NPC214236
0.9306	High Similarity	NPC299080
0.9306	High Similarity	NPC62840
0.9306	High Similarity	NPC59739
0.9301	High Similarity	NPC159275
0.9301	High Similarity	NPC69769
0.9301	High Similarity	NPC241100
0.9301	High Similarity	NPC275734
0.9301	High Similarity	NPC150522
0.9296	High Similarity	NPC201395
0.9281	High Similarity	NPC329760
0.9276	High Similarity	NPC471973
0.9272	High Similarity	NPC136674
0.9267	High Similarity	NPC148938
0.9267	High Similarity	NPC472280
0.9267	High Similarity	NPC213936
0.9267	High Similarity	NPC297531
0.9257	High Similarity	NPC295036
0.9257	High Similarity	NPC29777
0.9257	High Similarity	NPC471115
0.9257	High Similarity	NPC472633
0.9257	High Similarity	NPC158866
0.9252	High Similarity	NPC6511
0.9252	High Similarity	NPC39195
0.9252	High Similarity	NPC37139
0.9247	High Similarity	NPC124729
0.9247	High Similarity	NPC196114
0.9241	High Similarity	NPC24821
0.9241	High Similarity	NPC293053
0.9241	High Similarity	NPC9117
0.9241	High Similarity	NPC212932
0.9241	High Similarity	NPC190637
0.9236	High Similarity	NPC268204
0.9236	High Similarity	NPC55832
0.9236	High Similarity	NPC26051
0.9236	High Similarity	NPC52789
0.9236	High Similarity	NPC282300
0.9231	High Similarity	NPC217186
0.9231	High Similarity	NPC78913
0.9231	High Similarity	NPC18260
0.9231	High Similarity	NPC472366
0.9231	High Similarity	NPC53181
0.9225	High Similarity	NPC228661
0.9205	High Similarity	NPC472455
0.9195	High Similarity	NPC23668
0.9195	High Similarity	NPC232645
0.9195	High Similarity	NPC72958
0.9195	High Similarity	NPC193976
0.9189	High Similarity	NPC317492
0.9189	High Similarity	NPC474052
0.9189	High Similarity	NPC221868
0.9189	High Similarity	NPC329933
0.9189	High Similarity	NPC269420
0.9189	High Similarity	NPC37208
0.9184	High Similarity	NPC126767
0.9184	High Similarity	NPC166757
0.9184	High Similarity	NPC56433
0.9184	High Similarity	NPC110303
0.9184	High Similarity	NPC245584
0.9184	High Similarity	NPC473077
0.9184	High Similarity	NPC312929
0.9184	High Similarity	NPC308200
0.9184	High Similarity	NPC289042
0.9184	High Similarity	NPC14001
0.9184	High Similarity	NPC259632
0.9184	High Similarity	NPC118027
0.9184	High Similarity	NPC190648
0.9184	High Similarity	NPC34802
0.9184	High Similarity	NPC296998
0.9184	High Similarity	NPC23728
0.9178	High Similarity	NPC476055
0.9178	High Similarity	NPC469953
0.9178	High Similarity	NPC271288
0.9178	High Similarity	NPC216538
0.9178	High Similarity	NPC117716
0.9178	High Similarity	NPC470673
0.9178	High Similarity	NPC470674
0.9178	High Similarity	NPC257236
0.9178	High Similarity	NPC326500
0.9178	High Similarity	NPC278175
0.9178	High Similarity	NPC273538
0.9178	High Similarity	NPC209040
0.9172	High Similarity	NPC200694
0.9172	High Similarity	NPC473042
0.9172	High Similarity	NPC1534
0.9167	High Similarity	NPC172250
0.9167	High Similarity	NPC215311
0.9167	High Similarity	NPC144118
0.9167	High Similarity	NPC80962
0.9167	High Similarity	NPC48624
0.9167	High Similarity	NPC326109
0.9167	High Similarity	NPC253822
0.9167	High Similarity	NPC219917
0.9167	High Similarity	NPC101366
0.9167	High Similarity	NPC204985
0.9167	High Similarity	NPC259166
0.9167	High Similarity	NPC213659
0.9161	High Similarity	NPC470669
0.9161	High Similarity	NPC21350
0.9161	High Similarity	NPC470668
0.9161	High Similarity	NPC131130
0.9156	High Similarity	NPC229632
0.9155	High Similarity	NPC13408
0.9145	High Similarity	NPC474681
0.9145	High Similarity	NPC212967
0.9145	High Similarity	NPC218313
0.9145	High Similarity	NPC96342
0.9145	High Similarity	NPC273843
0.9145	High Similarity	NPC44199
0.9145	High Similarity	NPC201127
0.9145	High Similarity	NPC476981
0.9145	High Similarity	NPC246647
0.9145	High Similarity	NPC164110
0.9139	High Similarity	NPC234255
0.9139	High Similarity	NPC254351

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 NPC10027 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	386
0.1-0.2	980
0.2-0.3	1503
0.3-0.4	2597
0.4-0.5	1903
0.5-0.6	1080
0.6-0.7	476
0.7-0.8	163
0.8-0.85	39
0.85-0.9	21
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9178	High Similarity	NPD7410	Clinical (unspecified phase)
0.9178	High Similarity	NPD4378	Clinical (unspecified phase)
0.9073	High Similarity	NPD7819	Suspended
0.8824	High Similarity	NPD2393	Clinical (unspecified phase)
0.8819	High Similarity	NPD1510	Phase 2
0.8776	High Similarity	NPD3750	Approved
0.8767	High Similarity	NPD1549	Phase 2
0.8759	High Similarity	NPD2796	Approved
0.8725	High Similarity	NPD1511	Approved
0.8701	High Similarity	NPD2801	Approved
0.8699	High Similarity	NPD1552	Clinical (unspecified phase)
0.8699	High Similarity	NPD1550	Clinical (unspecified phase)
0.8671	High Similarity	NPD1240	Approved
0.8654	High Similarity	NPD3749	Approved
0.8645	High Similarity	NPD8443	Clinical (unspecified phase)
0.8639	High Similarity	NPD970	Clinical (unspecified phase)
0.8627	High Similarity	NPD4380	Phase 2
0.8609	High Similarity	NPD1512	Approved
0.8608	High Similarity	NPD6959	Discontinued
0.8571	High Similarity	NPD7411	Suspended
0.8562	High Similarity	NPD1509	Clinical (unspecified phase)
0.8552	High Similarity	NPD1607	Approved
0.8535	High Similarity	NPD7075	Discontinued
0.8516	High Similarity	NPD1934	Approved
0.8471	Intermediate Similarity	NPD3882	Suspended
0.8462	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD2800	Approved
0.8442	Intermediate Similarity	NPD3226	Approved
0.8438	Intermediate Similarity	NPD6232	Discontinued
0.8435	Intermediate Similarity	NPD3748	Approved
0.8421	Intermediate Similarity	NPD2533	Approved
0.8421	Intermediate Similarity	NPD2532	Approved
0.8421	Intermediate Similarity	NPD2534	Approved
0.8397	Intermediate Similarity	NPD6801	Discontinued
0.8395	Intermediate Similarity	NPD7473	Discontinued
0.8354	Intermediate Similarity	NPD7768	Phase 2
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD2346	Discontinued
0.8313	Intermediate Similarity	NPD5494	Approved
0.8311	Intermediate Similarity	NPD2799	Discontinued
0.8302	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD6099	Approved
0.8255	Intermediate Similarity	NPD2935	Discontinued
0.8255	Intermediate Similarity	NPD6100	Approved
0.8235	Intermediate Similarity	NPD6799	Approved
0.8232	Intermediate Similarity	NPD3818	Discontinued
0.8212	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD1243	Approved
0.82	Intermediate Similarity	NPD2344	Approved
0.8176	Intermediate Similarity	NPD3817	Phase 2
0.8153	Intermediate Similarity	NPD6599	Discontinued
0.8151	Intermediate Similarity	NPD2313	Discontinued
0.8117	Intermediate Similarity	NPD7390	Discontinued
0.811	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD6166	Phase 2
0.8082	Intermediate Similarity	NPD4625	Phase 3
0.8077	Intermediate Similarity	NPD920	Approved
0.8072	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD5844	Phase 1
0.8041	Intermediate Similarity	NPD943	Approved
0.8039	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1551	Phase 2
0.8012	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1465	Phase 2
0.7988	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD2309	Approved
0.7976	Intermediate Similarity	NPD5953	Discontinued
0.7964	Intermediate Similarity	NPD7054	Approved
0.795	Intermediate Similarity	NPD5402	Approved
0.7949	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6651	Approved
0.7931	Intermediate Similarity	NPD1470	Approved
0.7929	Intermediate Similarity	NPD6559	Discontinued
0.7922	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7472	Approved
0.7917	Intermediate Similarity	NPD7074	Phase 3
0.7905	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD2798	Approved
0.787	Intermediate Similarity	NPD6797	Phase 2
0.7857	Intermediate Similarity	NPD7286	Phase 2
0.7848	Intermediate Similarity	NPD5403	Approved
0.7831	Intermediate Similarity	NPD3926	Phase 2
0.7824	Intermediate Similarity	NPD7251	Discontinued
0.7818	Intermediate Similarity	NPD1247	Approved
0.7808	Intermediate Similarity	NPD1203	Approved
0.7805	Intermediate Similarity	NPD919	Approved
0.7785	Intermediate Similarity	NPD3764	Approved
0.7785	Intermediate Similarity	NPD3268	Approved
0.7785	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5408	Approved
0.7778	Intermediate Similarity	NPD5406	Approved
0.7778	Intermediate Similarity	NPD1201	Approved
0.7778	Intermediate Similarity	NPD5404	Approved
0.7778	Intermediate Similarity	NPD7808	Phase 3
0.7778	Intermediate Similarity	NPD5405	Approved
0.7771	Intermediate Similarity	NPD5710	Approved
0.7771	Intermediate Similarity	NPD5711	Approved
0.773	Intermediate Similarity	NPD4288	Approved
0.7727	Intermediate Similarity	NPD1471	Phase 3
0.7727	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5401	Approved
0.7722	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD4308	Phase 3
0.7712	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD4628	Phase 3
0.7687	Intermediate Similarity	NPD2797	Approved
0.7665	Intermediate Similarity	NPD7229	Phase 3
0.7651	Intermediate Similarity	NPD4908	Phase 1
0.764	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4287	Approved
0.7603	Intermediate Similarity	NPD1608	Approved
0.7603	Intermediate Similarity	NPD9717	Approved
0.7597	Intermediate Similarity	NPD7033	Discontinued
0.7588	Intermediate Similarity	NPD3751	Discontinued
0.7558	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4749	Approved
0.7542	Intermediate Similarity	NPD4360	Phase 2
0.7542	Intermediate Similarity	NPD4363	Phase 3
0.7534	Intermediate Similarity	NPD422	Phase 1
0.7534	Intermediate Similarity	NPD1610	Phase 2
0.7534	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6832	Phase 2
0.7529	Intermediate Similarity	NPD8313	Approved
0.7529	Intermediate Similarity	NPD8312	Approved
0.7516	Intermediate Similarity	NPD447	Suspended
0.7516	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4361	Phase 2
0.75	Intermediate Similarity	NPD1548	Phase 1
0.75	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7003	Approved
0.7456	Intermediate Similarity	NPD3787	Discontinued
0.7451	Intermediate Similarity	NPD4307	Phase 2
0.745	Intermediate Similarity	NPD3267	Approved
0.745	Intermediate Similarity	NPD3266	Approved
0.7434	Intermediate Similarity	NPD411	Approved
0.7432	Intermediate Similarity	NPD6779	Approved
0.7432	Intermediate Similarity	NPD6780	Approved
0.7432	Intermediate Similarity	NPD6781	Approved
0.7432	Intermediate Similarity	NPD6777	Approved
0.7432	Intermediate Similarity	NPD6782	Approved
0.7432	Intermediate Similarity	NPD6776	Approved
0.7432	Intermediate Similarity	NPD6778	Approved
0.7417	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2296	Approved
0.7403	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD230	Phase 1
0.7403	Intermediate Similarity	NPD5124	Phase 1
0.7403	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD17	Approved
0.7396	Intermediate Similarity	NPD7199	Phase 2
0.7391	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7177	Discontinued
0.7383	Intermediate Similarity	NPD3225	Approved
0.7365	Intermediate Similarity	NPD3972	Approved
0.7363	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5760	Phase 2
0.7349	Intermediate Similarity	NPD5761	Phase 2
0.7346	Intermediate Similarity	NPD6273	Approved
0.7338	Intermediate Similarity	NPD4060	Phase 1
0.7333	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1164	Approved
0.7329	Intermediate Similarity	NPD1651	Approved
0.732	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7458	Discontinued
0.7314	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7435	Discontinued
0.7312	Intermediate Similarity	NPD7697	Approved
0.7312	Intermediate Similarity	NPD7698	Approved
0.7312	Intermediate Similarity	NPD7696	Phase 3
0.731	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8434	Phase 2
0.7303	Intermediate Similarity	NPD8150	Discontinued
0.7299	Intermediate Similarity	NPD1729	Discontinued
0.7296	Intermediate Similarity	NPD2654	Approved
0.7289	Intermediate Similarity	NPD6844	Discontinued
0.7289	Intermediate Similarity	NPD37	Approved
0.7278	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6234	Discontinued
0.7273	Intermediate Similarity	NPD6585	Discontinued
0.7273	Intermediate Similarity	NPD7871	Phase 2
0.7273	Intermediate Similarity	NPD7870	Phase 2
0.7267	Intermediate Similarity	NPD1283	Approved
0.7267	Intermediate Similarity	NPD1876	Approved
0.7262	Intermediate Similarity	NPD4965	Approved
0.7262	Intermediate Similarity	NPD4967	Phase 2
0.7262	Intermediate Similarity	NPD4966	Approved
0.7226	Intermediate Similarity	NPD1613	Approved
0.7226	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4476	Approved
0.7215	Intermediate Similarity	NPD4477	Approved
0.7211	Intermediate Similarity	NPD8151	Discontinued
0.7208	Intermediate Similarity	NPD1296	Phase 2
0.72	Intermediate Similarity	NPD3600	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