NPASS Compound

Structure

NPC39029 OpenBabel07101718322D 31 32 0 0 0 0 0 0 0 0999 V2000 -2.5981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -6.5000 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 6.9282 -3.0000 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 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -0.8660 -3.5000 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 4.3301 -3.5000 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 2.5981 -1.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 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 -1.7321 -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 1.7321 -2.0000 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 0.8660 -1.5000 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 2.5981 -3.5000 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 0.0000 -0.0000 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 2.5981 -4.5000 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 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 17 2 0 0 0 0 8 19 1 0 0 0 0 9 12 1 0 0 0 0 9 18 2 0 0 0 0 10 11 1 0 0 0 0 10 19 2 0 0 0 0 11 20 1 0 0 0 0 12 22 1 0 0 0 0 13 20 2 0 0 0 0 13 26 1 0 0 0 0 14 21 2 0 0 0 0 14 24 1 0 0 0 0 15 21 1 0 0 0 0 15 25 2 0 0 0 0 16 23 2 0 0 0 0 16 27 1 0 0 0 0 20 23 1 0 0 0 0 21 23 1 0 0 0 0 22 24 2 0 0 0 0 22 25 1 0 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 26 27 2 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.25
Volume:	469.868
LogP:	7.363
LogD:	4.598
LogS:	-2.108
# Rotatable Bonds:	8
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.275
Synthetic Accessibility Score:	3.147
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.991
MDCK Permeability:	1.6122619854286313e-05
Pgp-inhibitor:	0.286
Pgp-substrate:	0.184
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	98.1911849975586%
Volume Distribution (VD):	2.593
Pgp-substrate:	1.0665372610092163%

ADMET: Metabolism

CYP1A2-inhibitor:	0.917
CYP1A2-substrate:	0.186
CYP2C19-inhibitor:	0.923
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.705
CYP2C9-substrate:	0.943
CYP2D6-inhibitor:	0.954
CYP2D6-substrate:	0.799
CYP3A4-inhibitor:	0.195
CYP3A4-substrate:	0.133

ADMET: Excretion

Clearance (CL):	13.429
Half-life (T1/2):	0.585

ADMET: Toxicity

hERG Blockers:	0.182
Human Hepatotoxicity (H-HT):	0.853
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.038
Maximum Recommended Daily Dose:	0.845
Skin Sensitization:	0.962
Carcinogencity:	0.026
Eye Corrosion:	0.003
Eye Irritation:	0.905
Respiratory Toxicity:	0.553

Download Data

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

Natural Product: NPC39029

Natural Product ID:	NPC39029
*Common Name:**	Clusiparalicoline A
IUPAC Name:	5-[2-[(2E)-3,7-dimethylocta-2,6-dienyl]-4,5-dihydroxyphenyl]-2-(3-methylbut-2-enyl)benzene-1,3-diol
Synonyms:
Standard InCHIKey:	UXVUTAYGHIXRNS-VXLYETTFSA-N
Standard InCHI:	InChI=1S/C27H34O4/c1-17(2)7-6-8-19(5)10-11-20-13-26(30)27(31)16-23(20)21-14-24(28)22(25(29)15-21)12-9-18(3)4/h7,9-10,13-16,28-31H,6,8,11-12H2,1-5H3/b19-10+
SMILES:	C/C(=CCc1cc(O)c(cc1c1cc(O)c(c(c1)O)CC=C(C)C)O)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479283
PubChem CID:	10070892
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000041] Biphenyls and derivatives

*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
NPO17121	Clusia paralicola	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579857]
NPO17121	Clusia paralicola	Species	Clusiaceae	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
EC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	EC50	=	3.8	ug.mL-1	PMID[491770]
NPT2	Others	Unspecified		Activity	=	77.0	%	PMID[491770]

☑ 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 NPC39029 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	365
0.1-0.2	1719
0.2-0.3	5012
0.3-0.4	13712
0.4-0.5	5245
0.5-0.6	5509
0.6-0.7	8094
0.7-0.8	2541
0.8-0.85	385
0.85-0.9	98
0.9-0.95	10
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9576	High Similarity	NPC224342
0.9565	High Similarity	NPC217174
0.9487	High Similarity	NPC237667
0.9478	High Similarity	NPC144343
0.9402	High Similarity	NPC24125
0.9397	High Similarity	NPC191866
0.9386	High Similarity	NPC472893
0.9328	High Similarity	NPC53567
0.9304	High Similarity	NPC115808
0.9224	High Similarity	NPC277588
0.9224	High Similarity	NPC470760
0.8992	High Similarity	NPC472071
0.8957	High Similarity	NPC166995
0.8879	High Similarity	NPC263753
0.8879	High Similarity	NPC23804
0.887	High Similarity	NPC268032
0.8803	High Similarity	NPC107240
0.8769	High Similarity	NPC35550
0.875	High Similarity	NPC176893
0.874	High Similarity	NPC15543
0.8718	High Similarity	NPC117846
0.8707	High Similarity	NPC224527
0.8696	High Similarity	NPC202647
0.8696	High Similarity	NPC19808
0.8696	High Similarity	NPC33728
0.8682	High Similarity	NPC125649
0.8678	High Similarity	NPC475245
0.8661	High Similarity	NPC126836
0.864	High Similarity	NPC82299
0.8632	High Similarity	NPC43525
0.8632	High Similarity	NPC471179
0.8626	High Similarity	NPC242715
0.8626	High Similarity	NPC56329
0.8626	High Similarity	NPC22902
0.8621	High Similarity	NPC224870
0.8615	High Similarity	NPC69029
0.8615	High Similarity	NPC294884
0.8615	High Similarity	NPC158142
0.8615	High Similarity	NPC200557
0.8615	High Similarity	NPC108198
0.8615	High Similarity	NPC10314
0.8609	High Similarity	NPC233835
0.8609	High Similarity	NPC34864
0.8609	High Similarity	NPC174981
0.8609	High Similarity	NPC58427
0.8609	High Similarity	NPC114392
0.8609	High Similarity	NPC105727
0.8605	High Similarity	NPC474453
0.8605	High Similarity	NPC32778
0.8596	High Similarity	NPC99836
0.8596	High Similarity	NPC12640
0.8596	High Similarity	NPC201662
0.8571	High Similarity	NPC246760
0.8571	High Similarity	NPC84999
0.8571	High Similarity	NPC473221
0.8561	High Similarity	NPC220344
0.8561	High Similarity	NPC243996
0.8561	High Similarity	NPC132804
0.8561	High Similarity	NPC275061
0.855	High Similarity	NPC202846
0.855	High Similarity	NPC143139
0.855	High Similarity	NPC30632
0.8547	High Similarity	NPC225679
0.8547	High Similarity	NPC151537
0.8547	High Similarity	NPC476632
0.8547	High Similarity	NPC165770
0.8547	High Similarity	NPC4493
0.8538	High Similarity	NPC7515
0.8538	High Similarity	NPC188378
0.8538	High Similarity	NPC289258
0.8538	High Similarity	NPC555
0.8538	High Similarity	NPC56764
0.8538	High Similarity	NPC206737
0.8538	High Similarity	NPC209199
0.8538	High Similarity	NPC469659
0.8538	High Similarity	NPC276026
0.8534	High Similarity	NPC186385
0.8534	High Similarity	NPC228343
0.8534	High Similarity	NPC254833
0.8534	High Similarity	NPC299568
0.8522	High Similarity	NPC232523
0.8522	High Similarity	NPC204901
0.8522	High Similarity	NPC158253
0.8522	High Similarity	NPC176527
0.8512	High Similarity	NPC9592
0.8512	High Similarity	NPC206
0.8512	High Similarity	NPC48781
0.8509	High Similarity	NPC37802
0.8509	High Similarity	NPC246056
0.8504	High Similarity	NPC154866
0.8496	Intermediate Similarity	NPC12668
0.8496	Intermediate Similarity	NPC308768
0.8485	Intermediate Similarity	NPC266453
0.8485	Intermediate Similarity	NPC200935
0.8485	Intermediate Similarity	NPC230919
0.8473	Intermediate Similarity	NPC240279
0.8473	Intermediate Similarity	NPC241241
0.8473	Intermediate Similarity	NPC214853
0.8473	Intermediate Similarity	NPC55239
0.8473	Intermediate Similarity	NPC180602
0.8473	Intermediate Similarity	NPC313081
0.8435	Intermediate Similarity	NPC302681
0.8435	Intermediate Similarity	NPC39097
0.8435	Intermediate Similarity	NPC39664
0.8435	Intermediate Similarity	NPC109691
0.8435	Intermediate Similarity	NPC118286
0.8435	Intermediate Similarity	NPC470700
0.8433	Intermediate Similarity	NPC472089
0.8425	Intermediate Similarity	NPC282000
0.8425	Intermediate Similarity	NPC82679
0.8425	Intermediate Similarity	NPC169474
0.8425	Intermediate Similarity	NPC236791
0.8425	Intermediate Similarity	NPC74817
0.8425	Intermediate Similarity	NPC246620
0.8425	Intermediate Similarity	NPC159968
0.8425	Intermediate Similarity	NPC324112
0.8425	Intermediate Similarity	NPC293054
0.8425	Intermediate Similarity	NPC266555
0.8425	Intermediate Similarity	NPC236760
0.8425	Intermediate Similarity	NPC124452
0.8425	Intermediate Similarity	NPC252131
0.8421	Intermediate Similarity	NPC212942
0.8421	Intermediate Similarity	NPC244513
0.8421	Intermediate Similarity	NPC227458
0.8421	Intermediate Similarity	NPC243759
0.8421	Intermediate Similarity	NPC471183
0.8421	Intermediate Similarity	NPC79622
0.8421	Intermediate Similarity	NPC29868
0.8421	Intermediate Similarity	NPC105847
0.8421	Intermediate Similarity	NPC218879
0.8421	Intermediate Similarity	NPC218131
0.8413	Intermediate Similarity	NPC33654
0.8409	Intermediate Similarity	NPC300846
0.8409	Intermediate Similarity	NPC476639
0.8409	Intermediate Similarity	NPC114155
0.8409	Intermediate Similarity	NPC133025
0.8403	Intermediate Similarity	NPC471485
0.8403	Intermediate Similarity	NPC261343
0.8403	Intermediate Similarity	NPC317869
0.84	Intermediate Similarity	NPC84086
0.84	Intermediate Similarity	NPC136319
0.8397	Intermediate Similarity	NPC160697
0.8385	Intermediate Similarity	NPC14224
0.8385	Intermediate Similarity	NPC161958
0.8374	Intermediate Similarity	NPC69006
0.8374	Intermediate Similarity	NPC223451
0.837	Intermediate Similarity	NPC472088
0.837	Intermediate Similarity	NPC183709
0.837	Intermediate Similarity	NPC175838
0.837	Intermediate Similarity	NPC472087
0.837	Intermediate Similarity	NPC470917
0.8362	Intermediate Similarity	NPC54844
0.8359	Intermediate Similarity	NPC28765
0.8348	Intermediate Similarity	NPC474839
0.8348	Intermediate Similarity	NPC134829
0.8348	Intermediate Similarity	NPC292452
0.8346	Intermediate Similarity	NPC6262
0.8346	Intermediate Similarity	NPC46277
0.8346	Intermediate Similarity	NPC272157
0.8346	Intermediate Similarity	NPC151656
0.8346	Intermediate Similarity	NPC266006
0.8346	Intermediate Similarity	NPC18924
0.8346	Intermediate Similarity	NPC78974
0.8346	Intermediate Similarity	NPC301765
0.8346	Intermediate Similarity	NPC223136
0.8346	Intermediate Similarity	NPC3072
0.8346	Intermediate Similarity	NPC156948
0.8346	Intermediate Similarity	NPC201145
0.8346	Intermediate Similarity	NPC73535
0.8346	Intermediate Similarity	NPC103823
0.8346	Intermediate Similarity	NPC25111
0.8346	Intermediate Similarity	NPC28730
0.8346	Intermediate Similarity	NPC86605
0.8346	Intermediate Similarity	NPC90615
0.8346	Intermediate Similarity	NPC214406
0.8346	Intermediate Similarity	NPC44748
0.8346	Intermediate Similarity	NPC223953
0.8346	Intermediate Similarity	NPC76451
0.8333	Intermediate Similarity	NPC249270
0.8333	Intermediate Similarity	NPC120280
0.8319	Intermediate Similarity	NPC473521
0.8319	Intermediate Similarity	NPC46940
0.8308	Intermediate Similarity	NPC469907
0.8308	Intermediate Similarity	NPC232275
0.8296	Intermediate Similarity	NPC71046
0.8296	Intermediate Similarity	NPC265075
0.8295	Intermediate Similarity	NPC212015
0.8293	Intermediate Similarity	NPC151197
0.8291	Intermediate Similarity	NPC63698
0.8291	Intermediate Similarity	NPC61885
0.8284	Intermediate Similarity	NPC184613
0.8284	Intermediate Similarity	NPC230124
0.8284	Intermediate Similarity	NPC114171
0.8284	Intermediate Similarity	NPC6300
0.8281	Intermediate Similarity	NPC127587
0.8279	Intermediate Similarity	NPC16030
0.8276	Intermediate Similarity	NPC248904
0.8271	Intermediate Similarity	NPC205442
0.8271	Intermediate Similarity	NPC234952
0.8268	Intermediate Similarity	NPC472093

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 NPC39029 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	989
0.2-0.3	1617
0.3-0.4	3113
0.4-0.5	1629
0.5-0.6	985
0.6-0.7	405
0.7-0.8	62
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8534	High Similarity	NPD4750	Phase 3
0.8534	High Similarity	NPD3022	Approved
0.8534	High Similarity	NPD3021	Approved
0.8087	Intermediate Similarity	NPD846	Approved
0.8087	Intermediate Similarity	NPD940	Approved
0.8017	Intermediate Similarity	NPD7635	Approved
0.8015	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD1242	Phase 1
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD4625	Phase 3
0.7759	Intermediate Similarity	NPD3020	Approved
0.775	Intermediate Similarity	NPD2342	Discontinued
0.7704	Intermediate Similarity	NPD943	Approved
0.7704	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7704	Intermediate Similarity	NPD1613	Approved
0.7652	Intermediate Similarity	NPD844	Approved
0.7652	Intermediate Similarity	NPD2859	Approved
0.7652	Intermediate Similarity	NPD2860	Approved
0.7586	Intermediate Similarity	NPD288	Approved
0.7565	Intermediate Similarity	NPD2934	Approved
0.7565	Intermediate Similarity	NPD2933	Approved
0.7557	Intermediate Similarity	NPD4749	Approved
0.7519	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD3094	Phase 2
0.7431	Intermediate Similarity	NPD7390	Discontinued
0.7407	Intermediate Similarity	NPD4908	Phase 1
0.7405	Intermediate Similarity	NPD3092	Approved
0.7379	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD3018	Phase 2
0.7299	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1610	Phase 2
0.7265	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD2286	Discontinued
0.725	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5283	Phase 1
0.7231	Intermediate Similarity	NPD3091	Approved
0.7222	Intermediate Similarity	NPD228	Approved
0.7209	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1809	Phase 2
0.7194	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD3620	Phase 2
0.7188	Intermediate Similarity	NPD497	Approved
0.7185	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD5408	Approved
0.7183	Intermediate Similarity	NPD6099	Approved
0.7183	Intermediate Similarity	NPD5404	Approved
0.7183	Intermediate Similarity	NPD5406	Approved
0.7183	Intermediate Similarity	NPD5405	Approved
0.7183	Intermediate Similarity	NPD6100	Approved
0.7174	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD2982	Phase 2
0.7164	Intermediate Similarity	NPD2983	Phase 2
0.7143	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7121	Intermediate Similarity	NPD3019	Approved
0.7121	Intermediate Similarity	NPD2932	Approved
0.7121	Intermediate Similarity	NPD4059	Approved
0.7115	Intermediate Similarity	NPD6232	Discontinued
0.7111	Intermediate Similarity	NPD5311	Approved
0.7111	Intermediate Similarity	NPD5310	Approved
0.7109	Intermediate Similarity	NPD495	Approved
0.7109	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD496	Approved
0.7109	Intermediate Similarity	NPD498	Approved
0.7099	Intermediate Similarity	NPD1548	Phase 1
0.709	Intermediate Similarity	NPD2981	Phase 2
0.709	Intermediate Similarity	NPD9269	Phase 2
0.7089	Intermediate Similarity	NPD7473	Discontinued
0.7075	Intermediate Similarity	NPD2421	Approved
0.7075	Intermediate Similarity	NPD2420	Approved
0.7071	Intermediate Similarity	NPD4060	Phase 1
0.7059	Intermediate Similarity	NPD3053	Approved
0.7059	Intermediate Similarity	NPD3055	Approved
0.7045	Intermediate Similarity	NPD4093	Discontinued
0.7043	Intermediate Similarity	NPD9094	Approved
0.7039	Intermediate Similarity	NPD37	Approved
0.7037	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD845	Approved
0.7031	Intermediate Similarity	NPD9379	Approved
0.7031	Intermediate Similarity	NPD9377	Approved
0.7015	Intermediate Similarity	NPD1201	Approved
0.7014	Intermediate Similarity	NPD7266	Discontinued
0.6993	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD3095	Discontinued
0.6992	Remote Similarity	NPD4626	Approved
0.6985	Remote Similarity	NPD6696	Suspended
0.6972	Remote Similarity	NPD5314	Approved
0.6959	Remote Similarity	NPD1511	Approved
0.6953	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.695	Remote Similarity	NPD3062	Approved
0.695	Remote Similarity	NPD3061	Approved
0.695	Remote Similarity	NPD3059	Approved
0.6944	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7228	Approved
0.6934	Remote Similarity	NPD1470	Approved
0.6929	Remote Similarity	NPD1792	Phase 2
0.6928	Remote Similarity	NPD1934	Approved
0.6918	Remote Similarity	NPD6674	Discontinued
0.6903	Remote Similarity	NPD4965	Approved
0.6903	Remote Similarity	NPD4967	Phase 2
0.6903	Remote Similarity	NPD4966	Approved
0.6901	Remote Similarity	NPD230	Phase 1
0.6883	Remote Similarity	NPD2801	Approved
0.6883	Remote Similarity	NPD1465	Phase 2
0.6871	Remote Similarity	NPD8166	Discontinued
0.6871	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6671	Approved
0.6867	Remote Similarity	NPD1512	Approved
0.6866	Remote Similarity	NPD9381	Approved
0.6866	Remote Similarity	NPD9384	Approved
0.6866	Remote Similarity	NPD1751	Approved
0.6853	Remote Similarity	NPD2568	Approved
0.6853	Remote Similarity	NPD4097	Suspended
0.6846	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD2228	Approved
0.6846	Remote Similarity	NPD2234	Approved
0.6846	Remote Similarity	NPD2229	Approved
0.6842	Remote Similarity	NPD4005	Discontinued
0.6842	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2861	Phase 2
0.6835	Remote Similarity	NPD5736	Approved
0.6829	Remote Similarity	NPD3028	Approved
0.6809	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.68	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3882	Suspended
0.6791	Remote Similarity	NPD9268	Approved
0.6791	Remote Similarity	NPD1651	Approved
0.679	Remote Similarity	NPD5844	Phase 1
0.6788	Remote Similarity	NPD9622	Approved
0.6783	Remote Similarity	NPD111	Approved
0.6781	Remote Similarity	NPD3540	Phase 1
0.6765	Remote Similarity	NPD3705	Approved
0.6765	Remote Similarity	NPD422	Phase 1
0.6761	Remote Similarity	NPD6405	Approved
0.6761	Remote Similarity	NPD6407	Approved
0.6757	Remote Similarity	NPD3750	Approved
0.6752	Remote Similarity	NPD4055	Discovery
0.6742	Remote Similarity	NPD709	Approved
0.6741	Remote Similarity	NPD4589	Approved
0.6739	Remote Similarity	NPD1283	Approved
0.6736	Remote Similarity	NPD1607	Approved
0.6735	Remote Similarity	NPD970	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7199	Phase 2
0.672	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD5303	Approved
0.6716	Remote Similarity	NPD5304	Approved
0.6715	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD1558	Phase 1
0.6712	Remote Similarity	NPD3539	Phase 1
0.6693	Remote Similarity	NPD1444	Approved
0.6693	Remote Similarity	NPD1445	Approved
0.6692	Remote Similarity	NPD7340	Approved
0.6691	Remote Similarity	NPD3026	Approved
0.6691	Remote Similarity	NPD3023	Approved
0.6667	Remote Similarity	NPD3025	Approved
0.6667	Remote Similarity	NPD5762	Approved
0.6667	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5691	Approved
0.6667	Remote Similarity	NPD5735	Approved
0.6667	Remote Similarity	NPD3024	Approved
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD3845	Phase 1
0.6667	Remote Similarity	NPD7124	Phase 2
0.6647	Remote Similarity	NPD8053	Approved
0.6647	Remote Similarity	NPD8054	Approved
0.6646	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3892	Phase 2
0.6644	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2195	Approved
0.6643	Remote Similarity	NPD258	Approved
0.6643	Remote Similarity	NPD2194	Approved
0.6643	Remote Similarity	NPD9619	Approved
0.6643	Remote Similarity	NPD257	Approved
0.6643	Remote Similarity	NPD9621	Approved
0.6643	Remote Similarity	NPD6663	Approved
0.6643	Remote Similarity	NPD9620	Approved
0.6642	Remote Similarity	NPD1611	Approved
0.6625	Remote Similarity	NPD6959	Discontinued
0.662	Remote Similarity	NPD5156	Approved
0.662	Remote Similarity	NPD7095	Approved
0.662	Remote Similarity	NPD5155	Approved
0.6619	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7157	Approved
0.6605	Remote Similarity	NPD6166	Phase 2
0.6605	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.66	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6190	Approved
0.66	Remote Similarity	NPD302	Approved
0.6597	Remote Similarity	NPD2238	Phase 2

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