NPASS Compound

Structure

CID130459 OpenBabel06191715492D 22 26 0 0 1 0 0 0 0 0999 V2000 -0.0609 2.1054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7806 1.6054 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3251 2.1746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8538 3.2108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8538 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9269 2.6757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7806 2.6757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9269 -0.5351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8368 1.7376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9640 -0.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0449 0.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8802 1.4994 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5149 0.5685 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8538 1.0703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 1.0703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2806 0.7394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9269 1.6054 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7806 1.6054 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8914 1.3504 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2806 0.7394 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7806 -0.1267 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 6 1 0 0 0 0 4 7 1 0 0 0 0 5 8 1 0 0 0 0 5 14 1 0 0 0 0 6 17 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 19 1 6 0 0 0 13 19 1 6 0 0 0 14 17 1 6 0 0 0 14 18 1 0 0 0 0 15 17 1 6 0 0 0 15 20 1 0 0 0 0 16 18 1 0 0 0 0 16 21 2 0 0 0 0 16 22 1 0 0 0 0 17 1 1 6 0 0 0 18 2 1 6 0 0 0 19 3 1 1 0 0 0 20 11 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	326.638
LogP:	4.9
LogD:	4.049
LogS:	-3.991
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.76
Synthetic Accessibility Score:	6.052
Fsp3:	0.95
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:	-5.449
MDCK Permeability:	8.770977729000151e-06
Pgp-inhibitor:	0.382
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	90.79279327392578%
Volume Distribution (VD):	0.472
Pgp-substrate:	7.361903190612793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.675
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.178
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.732
CYP3A4-substrate:	0.165

ADMET: Excretion

Clearance (CL):	3.066
Half-life (T1/2):	0.319

ADMET: Toxicity

hERG Blockers:	0.042
Human Hepatotoxicity (H-HT):	0.521
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.6
Maximum Recommended Daily Dose:	0.402
Skin Sensitization:	0.877
Carcinogencity:	0.528
Eye Corrosion:	0.864
Eye Irritation:	0.372
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC130459

Natural Product ID:	NPC130459
*Common Name:**	FLGAFUAMEXILLB-KDGRZGFDSA-N
IUPAC Name:	n.a.
Synonyms:	Trachyloban-19-Oic Acid; Trachyloban-19-Oicacid
Standard InCHIKey:	FLGAFUAMEXILLB-KDGRZGFDSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-17-6-4-7-18(2,16(21)22)14(17)5-8-20-10-13-12(9-15(17)20)19(13,3)11-20/h12-15H,4-11H2,1-3H3,(H,21,22)/t12-,13+,14-,15-,17+,18-,19+,20-/m0/s1
SMILES:	OC(=O)[C@@]1(C)CCC[C@@]2([C@@H]1CC[C@]13[C@H]2C[C@H]2[C@@H](C1)[C@@]2(C3)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511801
PubChem CID:	44560009
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	small food enterprises (Zvijezda d.d., Zagreb, Croatia)	n.a.	DOI[10.1002/EJLT.200900231]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16660462]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	flower petals	n.a.	n.a.	PMID[17480100]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[6361218]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Oil	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Pollen Or Spore	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	Flower Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27199	Croton macrostachys	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO454	Helianthus annuus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27199	Croton macrostachys	Species	Euphorbiaceae	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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	128.0	ug.mL-1	PMID[558336]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.25	ug.mL-1	PMID[558337]
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	=	6.25	ug.mL-1	PMID[558337]

☑ 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 NPC130459 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	329
0.1-0.2	4669
0.2-0.3	17988
0.3-0.4	7215
0.4-0.5	5955
0.5-0.6	4711
0.6-0.7	1479
0.7-0.8	288
0.8-0.85	38
0.85-0.9	18
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474221
1.0	High Similarity	NPC478180
0.9538	High Similarity	NPC477850
0.9524	High Similarity	NPC42060
0.9524	High Similarity	NPC477931
0.9524	High Similarity	NPC268736
0.9385	High Similarity	NPC474962
0.9091	High Similarity	NPC196197
0.9091	High Similarity	NPC476734
0.9091	High Similarity	NPC64466
0.9091	High Similarity	NPC252032
0.9091	High Similarity	NPC319671
0.9091	High Similarity	NPC469941
0.8955	High Similarity	NPC477929
0.8955	High Similarity	NPC108131
0.8824	High Similarity	NPC469940
0.8571	High Similarity	NPC167702
0.8571	High Similarity	NPC477930
0.8571	High Similarity	NPC280026
0.8551	High Similarity	NPC473267
0.8551	High Similarity	NPC472309
0.8472	Intermediate Similarity	NPC474404
0.8451	Intermediate Similarity	NPC212733
0.8451	Intermediate Similarity	NPC477934
0.8451	Intermediate Similarity	NPC472311
0.8429	Intermediate Similarity	NPC330659
0.8429	Intermediate Similarity	NPC161187
0.8429	Intermediate Similarity	NPC244708
0.8382	Intermediate Similarity	NPC473225
0.8378	Intermediate Similarity	NPC477851
0.8333	Intermediate Similarity	NPC246445
0.8333	Intermediate Similarity	NPC4209
0.8333	Intermediate Similarity	NPC477932
0.8333	Intermediate Similarity	NPC477933
0.8267	Intermediate Similarity	NPC12933
0.8219	Intermediate Similarity	NPC66105
0.8219	Intermediate Similarity	NPC180199
0.8219	Intermediate Similarity	NPC207010
0.8219	Intermediate Similarity	NPC317913
0.8219	Intermediate Similarity	NPC143133
0.8219	Intermediate Similarity	NPC477919
0.8219	Intermediate Similarity	NPC68828
0.8219	Intermediate Similarity	NPC477918
0.8219	Intermediate Similarity	NPC298168
0.8194	Intermediate Similarity	NPC273366
0.8116	Intermediate Similarity	NPC31187
0.8116	Intermediate Similarity	NPC100917
0.8116	Intermediate Similarity	NPC470956
0.8116	Intermediate Similarity	NPC281203
0.8116	Intermediate Similarity	NPC469724
0.8108	Intermediate Similarity	NPC329117
0.8108	Intermediate Similarity	NPC476732
0.8108	Intermediate Similarity	NPC185465
0.8108	Intermediate Similarity	NPC34046
0.8108	Intermediate Similarity	NPC171426
0.8108	Intermediate Similarity	NPC321690
0.8108	Intermediate Similarity	NPC199965
0.8108	Intermediate Similarity	NPC324700
0.8108	Intermediate Similarity	NPC224802
0.8108	Intermediate Similarity	NPC80089
0.8082	Intermediate Similarity	NPC20466
0.806	Intermediate Similarity	NPC128608
0.8028	Intermediate Similarity	NPC197701
0.8028	Intermediate Similarity	NPC320549
0.8028	Intermediate Similarity	NPC151018
0.8028	Intermediate Similarity	NPC156277
0.8028	Intermediate Similarity	NPC58057
0.8	Intermediate Similarity	NPC201276
0.8	Intermediate Similarity	NPC213178
0.8	Intermediate Similarity	NPC131892
0.8	Intermediate Similarity	NPC80891
0.8	Intermediate Similarity	NPC321732
0.8	Intermediate Similarity	NPC158846
0.8	Intermediate Similarity	NPC6120
0.8	Intermediate Similarity	NPC324607
0.8	Intermediate Similarity	NPC327728
0.8	Intermediate Similarity	NPC320144
0.8	Intermediate Similarity	NPC192744
0.7973	Intermediate Similarity	NPC212661
0.7973	Intermediate Similarity	NPC264602
0.7973	Intermediate Similarity	NPC471035
0.7973	Intermediate Similarity	NPC475031
0.7949	Intermediate Similarity	NPC319909
0.7945	Intermediate Similarity	NPC179858
0.7941	Intermediate Similarity	NPC19311
0.7941	Intermediate Similarity	NPC230047
0.7941	Intermediate Similarity	NPC469791
0.7917	Intermediate Similarity	NPC310766
0.7917	Intermediate Similarity	NPC232112
0.7895	Intermediate Similarity	NPC472853
0.7895	Intermediate Similarity	NPC261616
0.7887	Intermediate Similarity	NPC476731
0.7857	Intermediate Similarity	NPC474954
0.7821	Intermediate Similarity	NPC259173
0.7812	Intermediate Similarity	NPC474105
0.7808	Intermediate Similarity	NPC472854
0.7808	Intermediate Similarity	NPC254340
0.7792	Intermediate Similarity	NPC58631
0.7778	Intermediate Similarity	NPC89310
0.7763	Intermediate Similarity	NPC472310
0.7763	Intermediate Similarity	NPC52951
0.775	Intermediate Similarity	NPC70661
0.775	Intermediate Similarity	NPC302111
0.7714	Intermediate Similarity	NPC41542
0.7703	Intermediate Similarity	NPC21220
0.7703	Intermediate Similarity	NPC24014
0.7703	Intermediate Similarity	NPC195155
0.7703	Intermediate Similarity	NPC97534
0.7703	Intermediate Similarity	NPC27349
0.7703	Intermediate Similarity	NPC174964
0.7703	Intermediate Similarity	NPC125767
0.7703	Intermediate Similarity	NPC201027
0.7692	Intermediate Similarity	NPC61107
0.7692	Intermediate Similarity	NPC289486
0.7692	Intermediate Similarity	NPC477936
0.7692	Intermediate Similarity	NPC477935
0.7692	Intermediate Similarity	NPC121121
0.7692	Intermediate Similarity	NPC30583
0.7671	Intermediate Similarity	NPC36310
0.7671	Intermediate Similarity	NPC474123
0.7671	Intermediate Similarity	NPC279241
0.76	Intermediate Similarity	NPC475742
0.76	Intermediate Similarity	NPC472487
0.76	Intermediate Similarity	NPC5767
0.76	Intermediate Similarity	NPC472486
0.7595	Intermediate Similarity	NPC245866
0.7595	Intermediate Similarity	NPC15821
0.7595	Intermediate Similarity	NPC167103
0.7595	Intermediate Similarity	NPC472740
0.7576	Intermediate Similarity	NPC476735
0.7568	Intermediate Similarity	NPC255168
0.7568	Intermediate Similarity	NPC133922
0.7564	Intermediate Similarity	NPC147066
0.7564	Intermediate Similarity	NPC77311
0.7564	Intermediate Similarity	NPC469745
0.7561	Intermediate Similarity	NPC146937
0.7538	Intermediate Similarity	NPC151464
0.7538	Intermediate Similarity	NPC143597
0.7534	Intermediate Similarity	NPC478227
0.75	Intermediate Similarity	NPC238227
0.75	Intermediate Similarity	NPC476038
0.75	Intermediate Similarity	NPC473336
0.75	Intermediate Similarity	NPC288296
0.75	Intermediate Similarity	NPC23884
0.75	Intermediate Similarity	NPC471044
0.75	Intermediate Similarity	NPC221420
0.75	Intermediate Similarity	NPC53245
0.75	Intermediate Similarity	NPC194937
0.75	Intermediate Similarity	NPC295788
0.75	Intermediate Similarity	NPC306750
0.747	Intermediate Similarity	NPC24705
0.747	Intermediate Similarity	NPC56962
0.7468	Intermediate Similarity	NPC477858
0.7468	Intermediate Similarity	NPC170985
0.7467	Intermediate Similarity	NPC159789
0.7407	Intermediate Similarity	NPC201655
0.7407	Intermediate Similarity	NPC264317
0.7407	Intermediate Similarity	NPC283733
0.7407	Intermediate Similarity	NPC294438
0.7403	Intermediate Similarity	NPC63020
0.7385	Intermediate Similarity	NPC184819
0.7381	Intermediate Similarity	NPC77756
0.7375	Intermediate Similarity	NPC477852
0.7375	Intermediate Similarity	NPC472744
0.7375	Intermediate Similarity	NPC471037
0.7368	Intermediate Similarity	NPC89294
0.7368	Intermediate Similarity	NPC471046
0.7368	Intermediate Similarity	NPC104806
0.7361	Intermediate Similarity	NPC36616
0.7361	Intermediate Similarity	NPC260319
0.7361	Intermediate Similarity	NPC290445
0.7361	Intermediate Similarity	NPC180777
0.7361	Intermediate Similarity	NPC103647
0.7361	Intermediate Similarity	NPC2568
0.7342	Intermediate Similarity	NPC38350
0.7342	Intermediate Similarity	NPC201912
0.7342	Intermediate Similarity	NPC232625
0.7324	Intermediate Similarity	NPC84562
0.7317	Intermediate Similarity	NPC92139
0.7317	Intermediate Similarity	NPC80590
0.7317	Intermediate Similarity	NPC475007
0.7317	Intermediate Similarity	NPC2783
0.7317	Intermediate Similarity	NPC472272
0.7317	Intermediate Similarity	NPC186975
0.7317	Intermediate Similarity	NPC12774
0.7313	Intermediate Similarity	NPC162685
0.7308	Intermediate Similarity	NPC201459
0.7308	Intermediate Similarity	NPC477371
0.7308	Intermediate Similarity	NPC245029
0.7308	Intermediate Similarity	NPC215843
0.7308	Intermediate Similarity	NPC31302
0.7297	Intermediate Similarity	NPC126642
0.7294	Intermediate Similarity	NPC52756
0.7286	Intermediate Similarity	NPC69149
0.7284	Intermediate Similarity	NPC474996
0.7284	Intermediate Similarity	NPC263974
0.7273	Intermediate Similarity	NPC471899
0.7273	Intermediate Similarity	NPC471897
0.7273	Intermediate Similarity	NPC107039
0.7273	Intermediate Similarity	NPC169389

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 NPC130459 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	406
0.1-0.2	4018
0.2-0.3	3416
0.3-0.4	755
0.4-0.5	250
0.5-0.6	240
0.6-0.7	38
0.7-0.8	24
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9219	High Similarity	NPD4224	Phase 2
0.8824	High Similarity	NPD6081	Approved
0.8571	High Similarity	NPD6113	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD5360	Phase 3
0.8382	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6117	Approved
0.8219	Intermediate Similarity	NPD6116	Phase 1
0.8209	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD3702	Approved
0.8143	Intermediate Similarity	NPD4789	Approved
0.8108	Intermediate Similarity	NPD6118	Approved
0.8108	Intermediate Similarity	NPD6114	Approved
0.8108	Intermediate Similarity	NPD6115	Approved
0.8108	Intermediate Similarity	NPD6697	Approved
0.8028	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD4758	Discontinued
0.8	Intermediate Similarity	NPD3698	Phase 2
0.8	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD4244	Approved
0.7887	Intermediate Similarity	NPD4245	Approved
0.7778	Intermediate Similarity	NPD5777	Approved
0.7467	Intermediate Similarity	NPD3703	Phase 2
0.7407	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5364	Discontinued
0.7179	Intermediate Similarity	NPD3671	Phase 1
0.697	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD3617	Approved
0.6951	Remote Similarity	NPD4788	Approved
0.6923	Remote Similarity	NPD3186	Phase 1
0.6897	Remote Similarity	NPD8034	Phase 2
0.6897	Remote Similarity	NPD8035	Phase 2
0.6829	Remote Similarity	NPD4221	Approved
0.6829	Remote Similarity	NPD4223	Phase 3
0.6774	Remote Similarity	NPD634	Phase 3
0.6714	Remote Similarity	NPD3198	Approved
0.6707	Remote Similarity	NPD4139	Approved
0.6707	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6629	Remote Similarity	NPD6399	Phase 3
0.6627	Remote Similarity	NPD3667	Approved
0.6622	Remote Similarity	NPD375	Phase 2
0.6588	Remote Similarity	NPD5329	Approved
0.6579	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5281	Approved
0.6517	Remote Similarity	NPD5284	Approved
0.6512	Remote Similarity	NPD6098	Approved
0.6512	Remote Similarity	NPD5205	Approved
0.6512	Remote Similarity	NPD4688	Approved
0.6512	Remote Similarity	NPD4138	Approved
0.6512	Remote Similarity	NPD4690	Approved
0.6512	Remote Similarity	NPD4693	Phase 3
0.6512	Remote Similarity	NPD4689	Approved
0.6494	Remote Similarity	NPD4787	Phase 1
0.6471	Remote Similarity	NPD3133	Approved
0.6471	Remote Similarity	NPD3665	Phase 1
0.6471	Remote Similarity	NPD3666	Approved
0.6383	Remote Similarity	NPD8418	Phase 2
0.6374	Remote Similarity	NPD6001	Approved
0.6364	Remote Similarity	NPD5737	Approved
0.6364	Remote Similarity	NPD6672	Approved
0.6364	Remote Similarity	NPD5208	Approved
0.6364	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6083	Phase 2
0.6344	Remote Similarity	NPD6084	Phase 2
0.6322	Remote Similarity	NPD7521	Approved
0.6322	Remote Similarity	NPD5690	Phase 2
0.6322	Remote Similarity	NPD5330	Approved
0.6322	Remote Similarity	NPD4694	Approved
0.6322	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD7334	Approved
0.6322	Remote Similarity	NPD7146	Approved
0.6322	Remote Similarity	NPD5280	Approved
0.6322	Remote Similarity	NPD6409	Approved
0.6322	Remote Similarity	NPD3618	Phase 1
0.6322	Remote Similarity	NPD6684	Approved
0.6304	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5695	Phase 3
0.6292	Remote Similarity	NPD6673	Approved
0.6292	Remote Similarity	NPD4753	Phase 2
0.6292	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5328	Approved
0.6292	Remote Similarity	NPD6080	Approved
0.6292	Remote Similarity	NPD6904	Approved
0.629	Remote Similarity	NPD387	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5696	Approved
0.6264	Remote Similarity	NPD5133	Approved
0.6234	Remote Similarity	NPD6705	Phase 1
0.6232	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6903	Approved
0.6154	Remote Similarity	NPD5693	Phase 1
0.6154	Remote Similarity	NPD6079	Approved
0.6154	Remote Similarity	NPD7515	Phase 2
0.6136	Remote Similarity	NPD5279	Phase 3
0.6092	Remote Similarity	NPD3668	Phase 3
0.6087	Remote Similarity	NPD4202	Approved
0.6076	Remote Similarity	NPD4747	Approved
0.6071	Remote Similarity	NPD4195	Approved
0.6044	Remote Similarity	NPD5692	Phase 3
0.6044	Remote Similarity	NPD5207	Approved
0.6042	Remote Similarity	NPD6404	Discontinued
0.6022	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD6928	Phase 2
0.6	Remote Similarity	NPD5959	Approved
0.6	Remote Similarity	NPD4695	Discontinued
0.6	Remote Similarity	NPD4243	Approved
0.5978	Remote Similarity	NPD5694	Approved
0.5978	Remote Similarity	NPD6050	Approved
0.5957	Remote Similarity	NPD5210	Approved
0.5957	Remote Similarity	NPD4629	Approved
0.5955	Remote Similarity	NPD4623	Approved
0.5955	Remote Similarity	NPD4519	Discontinued
0.5949	Remote Similarity	NPD3726	Approved
0.5949	Remote Similarity	NPD3725	Approved
0.5949	Remote Similarity	NPD4137	Phase 3
0.5946	Remote Similarity	NPD9656	Approved
0.5938	Remote Similarity	NPD7638	Approved
0.5909	Remote Similarity	NPD345	Approved
0.5909	Remote Similarity	NPD344	Approved
0.5909	Remote Similarity	NPD343	Approved
0.59	Remote Similarity	NPD7128	Approved
0.59	Remote Similarity	NPD5739	Approved
0.59	Remote Similarity	NPD6402	Approved
0.59	Remote Similarity	NPD6675	Approved
0.5895	Remote Similarity	NPD4697	Phase 3
0.5895	Remote Similarity	NPD7614	Phase 1
0.5895	Remote Similarity	NPD5222	Approved
0.5895	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5221	Approved
0.5876	Remote Similarity	NPD7639	Approved
0.5876	Remote Similarity	NPD7640	Approved
0.5875	Remote Similarity	NPD4691	Approved
0.5873	Remote Similarity	NPD2270	Approved
0.587	Remote Similarity	NPD4096	Approved
0.5862	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD4784	Approved
0.5854	Remote Similarity	NPD4785	Approved
0.5842	Remote Similarity	NPD5701	Approved
0.5842	Remote Similarity	NPD5697	Approved
0.5833	Remote Similarity	NPD7902	Approved
0.5833	Remote Similarity	NPD4755	Approved
0.5833	Remote Similarity	NPD5173	Approved
0.5823	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.5821	Remote Similarity	NPD2266	Phase 2
0.5814	Remote Similarity	NPD7525	Registered
0.5806	Remote Similarity	NPD9448	Phase 2
0.5806	Remote Similarity	NPD77	Approved
0.5806	Remote Similarity	NPD9450	Approved
0.5806	Remote Similarity	NPD633	Phase 3
0.58	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5797	Remote Similarity	NPD9638	Phase 2
0.5789	Remote Similarity	NPD5654	Approved
0.5784	Remote Similarity	NPD7320	Approved
0.5784	Remote Similarity	NPD6881	Approved
0.5784	Remote Similarity	NPD6899	Approved
0.5784	Remote Similarity	NPD6011	Approved
0.5783	Remote Similarity	NPD7339	Approved
0.5783	Remote Similarity	NPD4190	Phase 3
0.5783	Remote Similarity	NPD6942	Approved
0.5783	Remote Similarity	NPD5275	Approved
0.5765	Remote Similarity	NPD4802	Phase 2
0.5765	Remote Similarity	NPD4238	Approved
0.5765	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD7632	Discontinued
0.5753	Remote Similarity	NPD9438	Approved
0.5753	Remote Similarity	NPD9439	Approved
0.5728	Remote Similarity	NPD6013	Approved
0.5728	Remote Similarity	NPD6014	Approved
0.5728	Remote Similarity	NPD6372	Approved
0.5728	Remote Similarity	NPD6012	Approved
0.5728	Remote Similarity	NPD6373	Approved
0.5714	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7909	Approved
0.5714	Remote Similarity	NPD4700	Approved
0.5714	Remote Similarity	NPD4696	Approved
0.5714	Remote Similarity	NPD5285	Approved
0.5714	Remote Similarity	NPD3573	Approved
0.5714	Remote Similarity	NPD5286	Approved
0.5673	Remote Similarity	NPD6883	Approved
0.5673	Remote Similarity	NPD7102	Approved
0.5673	Remote Similarity	NPD7290	Approved
0.5663	Remote Similarity	NPD5733	Approved
0.5663	Remote Similarity	NPD4058	Approved
0.5663	Remote Similarity	NPD4687	Approved
0.566	Remote Similarity	NPD8298	Phase 2
0.5657	Remote Similarity	NPD5223	Approved
0.5657	Remote Similarity	NPD1700	Approved
0.5652	Remote Similarity	NPD4518	Approved
0.5632	Remote Similarity	NPD9385	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD8130	Phase 1
0.5619	Remote Similarity	NPD6650	Approved
0.5619	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6869	Approved
0.5619	Remote Similarity	NPD6847	Approved
0.5619	Remote Similarity	NPD6617	Approved
0.5619	Remote Similarity	NPD6649	Approved
0.561	Remote Similarity	NPD5276	Approved
0.5606	Remote Similarity	NPD3199	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