NPASS Compound

Structure

NPC472087 OpenBabel07101719512D 41 44 0 0 0 0 0 0 0 0999 V2000 2.5403 5.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0807 1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0081 5.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7742 4.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9275 5.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 2.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6210 6.3556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4678 6.8444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2339 5.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4678 4.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0807 3.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 4.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 5.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 3.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6210 5.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0807 4.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 5.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 4.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3871 3.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3146 6.3556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3871 4.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 5.3778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2339 3.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3146 5.3778 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 -10.1614 6.8444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -1.4667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 5.3778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6936 5.8667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 5.8667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2339 2.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1614 4.8889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 -0.4889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 38 1 0 0 0 0 2 39 1 0 0 0 0 3 40 1 0 0 0 0 4 41 1 0 0 0 0 5 6 1 0 0 0 0 5 20 1 0 0 0 0 6 22 1 0 0 0 0 7 10 1 0 0 0 0 7 21 1 0 0 0 0 8 11 2 0 0 0 0 8 20 1 0 0 0 0 9 12 2 0 0 0 0 9 21 1 0 0 0 0 10 23 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 22 2 0 0 0 0 13 29 1 0 0 0 0 14 20 2 0 0 0 0 14 32 1 0 0 0 0 15 21 2 0 0 0 0 15 33 1 0 0 0 0 16 22 1 0 0 0 0 16 31 2 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 24 2 0 0 0 0 18 30 1 0 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 23 25 1 0 0 0 0 24 38 1 0 0 0 0 25 30 2 0 0 0 0 26 29 2 0 0 0 0 26 31 1 0 0 0 0 27 32 2 0 0 0 0 27 34 1 0 0 0 0 28 33 2 0 0 0 0 28 35 1 0 0 0 0 29 36 1 0 0 0 0 30 37 1 0 0 0 0 31 39 1 0 0 0 0 32 40 1 0 0 0 0 33 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.24
Volume:	583.782
LogP:	5.758
LogD:	4.129
LogS:	-4.044
# Rotatable Bonds:	12
TPSA:	117.84
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.174
Synthetic Accessibility Score:	2.791
Fsp3:	0.273
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.889
MDCK Permeability:	1.3412333828455303e-05
Pgp-inhibitor:	0.972
Pgp-substrate:	0.06
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.925

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	96.48172760009766%
Volume Distribution (VD):	0.579
Pgp-substrate:	1.770464301109314%

ADMET: Metabolism

CYP1A2-inhibitor:	0.452
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.803
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.579
CYP2C9-substrate:	0.971
CYP2D6-inhibitor:	0.294
CYP2D6-substrate:	0.964
CYP3A4-inhibitor:	0.331
CYP3A4-substrate:	0.886

ADMET: Excretion

Clearance (CL):	10.829
Half-life (T1/2):	0.877

ADMET: Toxicity

hERG Blockers:	0.22
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.284
AMES Toxicity:	0.067
Rat Oral Acute Toxicity:	0.228
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.949
Carcinogencity:	0.018
Eye Corrosion:	0.003
Eye Irritation:	0.797
Respiratory Toxicity:	0.211

Download Data

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

Natural Product: NPC472087

Natural Product ID:	NPC472087
*Common Name:**	MYXFYTSPQNYZQQ-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MYXFYTSPQNYZQQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C33H36O8/c1-38-24-17-23(10-7-21-9-12-28(35)33(15-21)41-4)25(30(37)18-24)19-26-29(36)13-22(16-31(26)39-2)6-5-20-8-11-27(34)32(14-20)40-3/h8-9,11-18,34-37H,5-7,10,19H2,1-4H3
SMILES:	COC1=CC(=C(C(=C1)O)CC2=C(C=C(C=C2OC)CCC3=CC(=C(C=C3)O)OC)O)CCC4=CC(=C(C=C4)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3337985
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002651] Linear diarylheptanoids

*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
NPO23332	Dendrobium fimbriatum	Species	Orchidaceae	Eukaryota	stems	n.a.	n.a.	PMID[25316316]
NPO23332	Dendrobium fimbriatum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23332	Dendrobium fimbriatum	Species	Orchidaceae	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
IC50	5

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	16340.0	nM	PMID[506395]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	=	18270.0	nM	PMID[506395]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	12670.0	nM	PMID[506395]
NPT660	Cell Line	SW480	Homo sapiens	IC50	=	17150.0	nM	PMID[506395]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16130.0	nM	PMID[506395]

☑ 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 NPC472087 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	492
0.1-0.2	1798
0.2-0.3	5077
0.3-0.4	12556
0.4-0.5	5246
0.5-0.6	4052
0.6-0.7	7406
0.7-0.8	4861
0.8-0.85	693
0.85-0.9	399
0.9-0.95	106
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC472088
0.9925	High Similarity	NPC472089
0.9851	High Similarity	NPC472091
0.9851	High Similarity	NPC472090
0.9851	High Similarity	NPC472092
0.9562	High Similarity	NPC183709
0.95	High Similarity	NPC262297
0.9429	High Similarity	NPC126291
0.9343	High Similarity	NPC132804
0.9343	High Similarity	NPC275061
0.9343	High Similarity	NPC220344
0.9343	High Similarity	NPC243996
0.9281	High Similarity	NPC277784
0.9275	High Similarity	NPC308768
0.9275	High Similarity	NPC12668
0.927	High Similarity	NPC56329
0.927	High Similarity	NPC242715
0.927	High Similarity	NPC22902
0.927	High Similarity	NPC200935
0.927	High Similarity	NPC266453
0.927	High Similarity	NPC230919
0.9265	High Similarity	NPC10314
0.9265	High Similarity	NPC294884
0.9265	High Similarity	NPC200557
0.9265	High Similarity	NPC158142
0.9265	High Similarity	NPC108198
0.9265	High Similarity	NPC69029
0.9265	High Similarity	NPC313081
0.9231	High Similarity	NPC476969
0.9203	High Similarity	NPC243759
0.9203	High Similarity	NPC218131
0.9203	High Similarity	NPC55947
0.9203	High Similarity	NPC105847
0.9197	High Similarity	NPC30632
0.9197	High Similarity	NPC143139
0.9197	High Similarity	NPC202846
0.9191	High Similarity	NPC125649
0.9179	High Similarity	NPC126836
0.9143	High Similarity	NPC175838
0.913	High Similarity	NPC90615
0.913	High Similarity	NPC266006
0.913	High Similarity	NPC201145
0.913	High Similarity	NPC6262
0.913	High Similarity	NPC151656
0.913	High Similarity	NPC272157
0.913	High Similarity	NPC73535
0.913	High Similarity	NPC25111
0.9124	High Similarity	NPC241241
0.9111	High Similarity	NPC473309
0.9111	High Similarity	NPC471517
0.9097	High Similarity	NPC318373
0.9097	High Similarity	NPC321657
0.9065	High Similarity	NPC29868
0.9065	High Similarity	NPC6300
0.9065	High Similarity	NPC184613
0.9065	High Similarity	NPC114171
0.9065	High Similarity	NPC212942
0.9065	High Similarity	NPC79622
0.9065	High Similarity	NPC230124
0.9058	High Similarity	NPC476639
0.9058	High Similarity	NPC300846
0.9058	High Similarity	NPC114155
0.9051	High Similarity	NPC209199
0.9051	High Similarity	NPC160697
0.9051	High Similarity	NPC66840
0.9051	High Similarity	NPC256307
0.9044	High Similarity	NPC14224
0.9044	High Similarity	NPC161958
0.9	High Similarity	NPC22317
0.9	High Similarity	NPC295719
0.9	High Similarity	NPC273623
0.9	High Similarity	NPC73505
0.9	High Similarity	NPC165026
0.9	High Similarity	NPC34431
0.8986	High Similarity	NPC283009
0.8986	High Similarity	NPC261873
0.8986	High Similarity	NPC111655
0.8978	High Similarity	NPC32778
0.8971	High Similarity	NPC15543
0.8963	High Similarity	NPC471518
0.8963	High Similarity	NPC471519
0.8955	High Similarity	NPC293054
0.8955	High Similarity	NPC169474
0.8955	High Similarity	NPC82679
0.8955	High Similarity	NPC246620
0.8955	High Similarity	NPC74817
0.8955	High Similarity	NPC124452
0.8955	High Similarity	NPC324112
0.8955	High Similarity	NPC159968
0.8955	High Similarity	NPC236791
0.8955	High Similarity	NPC282000
0.8955	High Similarity	NPC236760
0.8944	High Similarity	NPC469630
0.8921	High Similarity	NPC205442
0.8913	High Similarity	NPC141023
0.8913	High Similarity	NPC103967
0.8905	High Similarity	NPC131128
0.8905	High Similarity	NPC474134
0.8905	High Similarity	NPC228843
0.8904	High Similarity	NPC477612
0.8897	High Similarity	NPC281549
0.8897	High Similarity	NPC254000
0.8889	High Similarity	NPC154866
0.8881	High Similarity	NPC15659
0.8881	High Similarity	NPC28730
0.8881	High Similarity	NPC214406
0.8881	High Similarity	NPC304894
0.8881	High Similarity	NPC44748
0.8881	High Similarity	NPC78974
0.8881	High Similarity	NPC223136
0.8881	High Similarity	NPC103823
0.8881	High Similarity	NPC18924
0.8857	High Similarity	NPC71465
0.8857	High Similarity	NPC472646
0.8857	High Similarity	NPC35550
0.8849	High Similarity	NPC37410
0.8844	High Similarity	NPC329343
0.8844	High Similarity	NPC324517
0.8844	High Similarity	NPC321972
0.8832	High Similarity	NPC471983
0.8832	High Similarity	NPC149337
0.8832	High Similarity	NPC282508
0.8832	High Similarity	NPC474238
0.8828	High Similarity	NPC153182
0.8828	High Similarity	NPC174251
0.8815	High Similarity	NPC127587
0.8815	High Similarity	NPC266555
0.8811	High Similarity	NPC173203
0.8811	High Similarity	NPC163508
0.8806	High Similarity	NPC57490
0.8806	High Similarity	NPC475169
0.8806	High Similarity	NPC116907
0.8806	High Similarity	NPC221077
0.8806	High Similarity	NPC298757
0.8806	High Similarity	NPC208950
0.8806	High Similarity	NPC472093
0.8806	High Similarity	NPC117214
0.8806	High Similarity	NPC113495
0.8806	High Similarity	NPC193544
0.8806	High Similarity	NPC299584
0.8806	High Similarity	NPC105925
0.8806	High Similarity	NPC82483
0.8806	High Similarity	NPC203133
0.8806	High Similarity	NPC251855
0.8806	High Similarity	NPC234400
0.8806	High Similarity	NPC60885
0.8806	High Similarity	NPC17943
0.8806	High Similarity	NPC265483
0.8806	High Similarity	NPC233410
0.8792	High Similarity	NPC157333
0.8786	High Similarity	NPC191462
0.8786	High Similarity	NPC133463
0.8786	High Similarity	NPC472648
0.8786	High Similarity	NPC206525
0.8786	High Similarity	NPC170328
0.8786	High Similarity	NPC472647
0.8786	High Similarity	NPC472649
0.8777	High Similarity	NPC469659
0.8777	High Similarity	NPC56764
0.8777	High Similarity	NPC276026
0.8777	High Similarity	NPC555
0.8777	High Similarity	NPC188378
0.8777	High Similarity	NPC289258
0.8777	High Similarity	NPC7515
0.8777	High Similarity	NPC206737
0.8768	High Similarity	NPC73656
0.8768	High Similarity	NPC303144
0.8768	High Similarity	NPC189482
0.8768	High Similarity	NPC6451
0.8768	High Similarity	NPC218884
0.8767	High Similarity	NPC329836
0.8759	High Similarity	NPC311680
0.8759	High Similarity	NPC215678
0.8759	High Similarity	NPC299221
0.8759	High Similarity	NPC234488
0.8759	High Similarity	NPC51840
0.8759	High Similarity	NPC233980
0.8759	High Similarity	NPC274454
0.875	High Similarity	NPC469795
0.875	High Similarity	NPC171932
0.875	High Similarity	NPC28440
0.875	High Similarity	NPC28765
0.8741	High Similarity	NPC76451
0.8741	High Similarity	NPC191231
0.8741	High Similarity	NPC223953
0.8733	High Similarity	NPC202104
0.8732	High Similarity	NPC262189
0.8732	High Similarity	NPC291101
0.8732	High Similarity	NPC266197
0.8723	High Similarity	NPC474390
0.8723	High Similarity	NPC48956
0.8714	High Similarity	NPC214853
0.8714	High Similarity	NPC258780
0.8714	High Similarity	NPC240279
0.8714	High Similarity	NPC180602
0.8714	High Similarity	NPC55239
0.8707	High Similarity	NPC211561
0.8707	High Similarity	NPC470098
0.8707	High Similarity	NPC473266
0.8707	High Similarity	NPC470826

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 NPC472087 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	414
0.1-0.2	974
0.2-0.3	1726
0.3-0.4	2815
0.4-0.5	1633
0.5-0.6	924
0.6-0.7	551
0.7-0.8	106
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8551	High Similarity	NPD3027	Phase 3
0.8345	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1613	Approved
0.8214	Intermediate Similarity	NPD4908	Phase 1
0.8099	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD4625	Phase 3
0.8014	Intermediate Similarity	NPD3018	Phase 2
0.7937	Intermediate Similarity	NPD6232	Discontinued
0.7901	Intermediate Similarity	NPD7473	Discontinued
0.7862	Intermediate Similarity	NPD6234	Discontinued
0.7857	Intermediate Similarity	NPD2982	Phase 2
0.7857	Intermediate Similarity	NPD2983	Phase 2
0.7844	Intermediate Similarity	NPD8054	Approved
0.7844	Intermediate Similarity	NPD8053	Approved
0.7786	Intermediate Similarity	NPD2981	Phase 2
0.7771	Intermediate Similarity	NPD37	Approved
0.7744	Intermediate Similarity	NPD7228	Approved
0.774	Intermediate Similarity	NPD3620	Phase 2
0.774	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4749	Approved
0.7714	Intermediate Similarity	NPD1610	Phase 2
0.7704	Intermediate Similarity	NPD5283	Phase 1
0.7692	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD228	Approved
0.7682	Intermediate Similarity	NPD6674	Discontinued
0.7654	Intermediate Similarity	NPD7199	Phase 2
0.7625	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4966	Approved
0.7625	Intermediate Similarity	NPD4965	Approved
0.7625	Intermediate Similarity	NPD4967	Phase 2
0.7622	Intermediate Similarity	NPD6166	Phase 2
0.7622	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5844	Phase 1
0.7561	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD1548	Phase 1
0.7547	Intermediate Similarity	NPD1934	Approved
0.75	Intermediate Similarity	NPD2801	Approved
0.7483	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6959	Discontinued
0.7434	Intermediate Similarity	NPD3540	Phase 1
0.7425	Intermediate Similarity	NPD8252	Approved
0.7425	Intermediate Similarity	NPD8099	Discontinued
0.7425	Intermediate Similarity	NPD8251	Approved
0.7407	Intermediate Similarity	NPD3021	Approved
0.7407	Intermediate Similarity	NPD3022	Approved
0.7396	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1465	Phase 2
0.7391	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4060	Phase 1
0.7381	Intermediate Similarity	NPD8156	Discontinued
0.7368	Intermediate Similarity	NPD3539	Phase 1
0.7368	Intermediate Similarity	NPD6099	Approved
0.7368	Intermediate Similarity	NPD6100	Approved
0.7358	Intermediate Similarity	NPD4005	Discontinued
0.7337	Intermediate Similarity	NPD7074	Phase 3
0.7325	Intermediate Similarity	NPD7447	Phase 1
0.7301	Intermediate Similarity	NPD7768	Phase 2
0.7301	Intermediate Similarity	NPD3882	Suspended
0.7296	Intermediate Similarity	NPD1653	Approved
0.7285	Intermediate Similarity	NPD4097	Suspended
0.7279	Intermediate Similarity	NPD4750	Phase 3
0.7279	Intermediate Similarity	NPD2861	Phase 2
0.7278	Intermediate Similarity	NPD7054	Approved
0.7261	Intermediate Similarity	NPD1511	Approved
0.7256	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4055	Discovery
0.7251	Intermediate Similarity	NPD7240	Approved
0.7239	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7472	Approved
0.7233	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3705	Approved
0.7215	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7266	Discontinued
0.7203	Intermediate Similarity	NPD4626	Approved
0.72	Intermediate Similarity	NPD7906	Approved
0.7197	Intermediate Similarity	NPD7124	Phase 2
0.7192	Intermediate Similarity	NPD8651	Approved
0.7184	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3750	Approved
0.7178	Intermediate Similarity	NPD7819	Suspended
0.717	Intermediate Similarity	NPD1512	Approved
0.7152	Intermediate Similarity	NPD7041	Phase 2
0.7152	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1558	Phase 1
0.7152	Intermediate Similarity	NPD7213	Phase 3
0.7152	Intermediate Similarity	NPD7390	Discontinued
0.7152	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7212	Phase 2
0.7134	Intermediate Similarity	NPD3817	Phase 2
0.7134	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD7843	Approved
0.7118	Intermediate Similarity	NPD3818	Discontinued
0.711	Intermediate Similarity	NPD7808	Phase 3
0.7107	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD5735	Approved
0.7099	Intermediate Similarity	NPD4380	Phase 2
0.7092	Intermediate Similarity	NPD7157	Approved
0.7075	Intermediate Similarity	NPD6696	Suspended
0.7073	Intermediate Similarity	NPD8455	Phase 2
0.707	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD8166	Discontinued
0.7067	Intermediate Similarity	NPD7095	Approved
0.7065	Intermediate Similarity	NPD7680	Approved
0.7063	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1607	Approved
0.7052	Intermediate Similarity	NPD7251	Discontinued
0.7048	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7831	Phase 2
0.7048	Intermediate Similarity	NPD7833	Phase 2
0.7044	Intermediate Similarity	NPD4357	Discontinued
0.7037	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD8127	Discontinued
0.702	Intermediate Similarity	NPD5110	Phase 2
0.702	Intermediate Similarity	NPD5111	Phase 2
0.702	Intermediate Similarity	NPD5109	Approved
0.7015	Intermediate Similarity	NPD940	Approved
0.7015	Intermediate Similarity	NPD846	Approved
0.7013	Intermediate Similarity	NPD6111	Discontinued
0.7011	Intermediate Similarity	NPD7549	Discontinued
0.7007	Intermediate Similarity	NPD2342	Discontinued
0.7	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6797	Phase 2
0.6993	Remote Similarity	NPD5536	Phase 2
0.6993	Remote Similarity	NPD3657	Discovery
0.6988	Remote Similarity	NPD6788	Approved
0.6987	Remote Similarity	NPD5762	Approved
0.6987	Remote Similarity	NPD5763	Approved
0.6986	Remote Similarity	NPD422	Phase 1
0.698	Remote Similarity	NPD4624	Approved
0.698	Remote Similarity	NPD6584	Phase 3
0.6972	Remote Similarity	NPD6671	Approved
0.6971	Remote Similarity	NPD8312	Approved
0.6971	Remote Similarity	NPD8313	Approved
0.6968	Remote Similarity	NPD1510	Phase 2
0.6962	Remote Similarity	NPD7466	Approved
0.6962	Remote Similarity	NPD7003	Approved
0.6962	Remote Similarity	NPD3892	Phase 2
0.6951	Remote Similarity	NPD5090	Approved
0.6951	Remote Similarity	NPD5089	Approved
0.6946	Remote Similarity	NPD7075	Discontinued
0.6943	Remote Similarity	NPD7037	Approved
0.6943	Remote Similarity	NPD970	Clinical (unspecified phase)
0.694	Remote Similarity	NPD1242	Phase 1
0.694	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1240	Approved
0.6923	Remote Similarity	NPD5408	Approved
0.6923	Remote Similarity	NPD5404	Approved
0.6923	Remote Similarity	NPD5406	Approved
0.6923	Remote Similarity	NPD5405	Approved
0.6918	Remote Similarity	NPD5241	Discontinued
0.6914	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3094	Phase 2
0.6908	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD6798	Discontinued
0.6906	Remote Similarity	NPD5451	Approved
0.6901	Remote Similarity	NPD2489	Approved
0.6901	Remote Similarity	NPD27	Approved
0.6899	Remote Similarity	NPD5177	Phase 3
0.6899	Remote Similarity	NPD3060	Approved
0.6897	Remote Similarity	NPD1651	Approved
0.6897	Remote Similarity	NPD5691	Approved
0.6894	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD5327	Phase 3
0.689	Remote Similarity	NPD4678	Approved
0.689	Remote Similarity	NPD4675	Approved
0.6889	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7229	Phase 3
0.6882	Remote Similarity	NPD3051	Approved
0.6882	Remote Similarity	NPD3787	Discontinued
0.6879	Remote Similarity	NPD7635	Approved
0.6875	Remote Similarity	NPD4577	Approved
0.6875	Remote Similarity	NPD7313	Approved
0.6875	Remote Similarity	NPD7310	Approved
0.6875	Remote Similarity	NPD7312	Approved
0.6875	Remote Similarity	NPD4578	Approved
0.6875	Remote Similarity	NPD7311	Approved
0.6871	Remote Similarity	NPD3092	Approved
0.6867	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5494	Approved
0.6863	Remote Similarity	NPD2674	Phase 3
0.6859	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3748	Approved
0.6857	Remote Similarity	NPD6559	Discontinued
0.6854	Remote Similarity	NPD4663	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