NPASS Compound

Structure

NPC474703 OpenBabel07101719512D 28 28 0 0 1 0 0 0 0 0999 V2000 -0.4781 -1.7468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1691 -2.2820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 2.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9271 2.6831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7653 -1.0036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8271 0.8135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8090 2.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 2.4899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6180 1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9271 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4271 1.8171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0962 -1.7468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7226 -0.1810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9271 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8090 -0.5878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8090 -0.5878 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9271 0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4052 -2.6978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5316 -0.7688 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4271 1.8171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1180 -1.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 2 0 0 0 0 4 14 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 13 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 10 18 1 0 0 0 0 11 17 1 0 0 0 0 11 26 1 0 0 0 0 13 20 1 0 0 0 0 14 22 2 0 0 0 0 14 26 1 0 0 0 0 15 23 2 0 0 0 0 15 27 1 0 0 0 0 16 24 2 0 0 0 0 16 28 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 12 1 6 0 0 0 19 21 1 0 0 0 0 20 21 1 0 0 0 0 20 25 2 0 0 0 0 21 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.2
Volume:	408.929
LogP:	2.297
LogD:	1.799
LogS:	-3.083
# Rotatable Bonds:	8
TPSA:	95.97
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	4.619
Fsp3:	0.619
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.66
MDCK Permeability:	4.4083266402594745e-05
Pgp-inhibitor:	0.881
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.034
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.418

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.89
Plasma Protein Binding (PPB):	67.00479888916016%
Volume Distribution (VD):	0.387
Pgp-substrate:	52.57199478149414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.025
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.272
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.058
CYP3A4-inhibitor:	0.282
CYP3A4-substrate:	0.276

ADMET: Excretion

Clearance (CL):	2.887
Half-life (T1/2):	0.743

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.937
Drug-inuced Liver Injury (DILI):	0.866
AMES Toxicity:	0.447
Rat Oral Acute Toxicity:	0.052
Maximum Recommended Daily Dose:	0.403
Skin Sensitization:	0.523
Carcinogencity:	0.716
Eye Corrosion:	0.008
Eye Irritation:	0.045
Respiratory Toxicity:	0.038

Download Data

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

Natural Product: NPC474703

Natural Product ID:	NPC474703
*Common Name:**	Triacetoxy Pulicanone
IUPAC Name:	[(1E,7S,8S,9R)-7,9-diacetyloxy-5-methylidene-6-oxo-8-propan-2-ylcyclodecen-1-yl]methyl acetate
Synonyms:	Triacetoxy Pulicanone
Standard InCHIKey:	XFOYHMKDRKVKPJ-NRYJDXOVSA-N
Standard InCHI:	InChI=1S/C21H30O7/c1-12(2)19-18(27-15(5)23)10-17(11-26-14(4)22)9-7-8-13(3)20(25)21(19)28-16(6)24/h9,12,18-19,21H,3,7-8,10-11H2,1-2,4-6H3/b17-9+/t18-,19+,21+/m1/s1
SMILES:	CC(=O)OC/C/1=C/CCC(=C)C(=O)[C@H]([C@H]([C@@H](C1)OC(=O)C)C(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479700
PubChem CID:	11223151
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0002456] Germacrane sesquiterpenoids

*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
NPO1119	Pulicaria canariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844941]
NPO1119	Pulicaria canariensis	Species	Asteraceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	20000.0	nM	PMID[517620]

☑ 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 NPC474703 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	230
0.1-0.2	1448
0.2-0.3	5656
0.3-0.4	13369
0.4-0.5	11832
0.5-0.6	6568
0.6-0.7	2885
0.7-0.8	637
0.8-0.85	58
0.85-0.9	12
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8765	High Similarity	NPC281949
0.8765	High Similarity	NPC301477
0.8765	High Similarity	NPC25684
0.875	High Similarity	NPC270126
0.8734	High Similarity	NPC141789
0.8734	High Similarity	NPC171204
0.8734	High Similarity	NPC476028
0.8636	High Similarity	NPC476596
0.8608	High Similarity	NPC235906
0.8571	High Similarity	NPC255307
0.8537	High Similarity	NPC141810
0.8537	High Similarity	NPC471325
0.8523	High Similarity	NPC476597
0.8523	High Similarity	NPC475302
0.8523	High Similarity	NPC476598
0.8519	High Similarity	NPC178277
0.8481	Intermediate Similarity	NPC155587
0.8471	Intermediate Similarity	NPC305475
0.8471	Intermediate Similarity	NPC107787
0.8471	Intermediate Similarity	NPC475461
0.8471	Intermediate Similarity	NPC50637
0.8452	Intermediate Similarity	NPC476804
0.8452	Intermediate Similarity	NPC114979
0.8452	Intermediate Similarity	NPC141193
0.8452	Intermediate Similarity	NPC191476
0.8452	Intermediate Similarity	NPC96259
0.8415	Intermediate Similarity	NPC281132
0.8395	Intermediate Similarity	NPC128276
0.8391	Intermediate Similarity	NPC475971
0.8372	Intermediate Similarity	NPC266957
0.8353	Intermediate Similarity	NPC78089
0.8333	Intermediate Similarity	NPC473390
0.8333	Intermediate Similarity	NPC128429
0.8333	Intermediate Similarity	NPC222358
0.8333	Intermediate Similarity	NPC131669
0.8295	Intermediate Similarity	NPC469368
0.8293	Intermediate Similarity	NPC617
0.8276	Intermediate Similarity	NPC475902
0.8272	Intermediate Similarity	NPC474760
0.8272	Intermediate Similarity	NPC65603
0.8272	Intermediate Similarity	NPC476794
0.8272	Intermediate Similarity	NPC57744
0.8272	Intermediate Similarity	NPC97516
0.8272	Intermediate Similarity	NPC470240
0.8256	Intermediate Similarity	NPC279859
0.8256	Intermediate Similarity	NPC38576
0.8256	Intermediate Similarity	NPC150755
0.825	Intermediate Similarity	NPC244166
0.8235	Intermediate Similarity	NPC115786
0.8228	Intermediate Similarity	NPC295633
0.8228	Intermediate Similarity	NPC58956
0.8228	Intermediate Similarity	NPC269206
0.8214	Intermediate Similarity	NPC229825
0.8202	Intermediate Similarity	NPC20713
0.8182	Intermediate Similarity	NPC166919
0.8152	Intermediate Similarity	NPC471140
0.814	Intermediate Similarity	NPC165162
0.8125	Intermediate Similarity	NPC476355
0.8125	Intermediate Similarity	NPC140287
0.8118	Intermediate Similarity	NPC475989
0.8118	Intermediate Similarity	NPC40746
0.8118	Intermediate Similarity	NPC169575
0.8111	Intermediate Similarity	NPC165383
0.8101	Intermediate Similarity	NPC163003
0.8101	Intermediate Similarity	NPC129665
0.8095	Intermediate Similarity	NPC42470
0.8095	Intermediate Similarity	NPC52861
0.8095	Intermediate Similarity	NPC24417
0.809	Intermediate Similarity	NPC144133
0.809	Intermediate Similarity	NPC179394
0.809	Intermediate Similarity	NPC329857
0.809	Intermediate Similarity	NPC469718
0.8085	Intermediate Similarity	NPC164598
0.8085	Intermediate Similarity	NPC474339
0.8072	Intermediate Similarity	NPC98557
0.8072	Intermediate Similarity	NPC167881
0.8068	Intermediate Similarity	NPC476803
0.8068	Intermediate Similarity	NPC471047
0.8068	Intermediate Similarity	NPC469628
0.8068	Intermediate Similarity	NPC475906
0.8068	Intermediate Similarity	NPC476805
0.8068	Intermediate Similarity	NPC469653
0.8068	Intermediate Similarity	NPC469631
0.8065	Intermediate Similarity	NPC54843
0.8046	Intermediate Similarity	NPC261721
0.8043	Intermediate Similarity	NPC172998
0.8043	Intermediate Similarity	NPC301596
0.8043	Intermediate Similarity	NPC299396
0.8025	Intermediate Similarity	NPC193351
0.8025	Intermediate Similarity	NPC138408
0.8025	Intermediate Similarity	NPC226669
0.8023	Intermediate Similarity	NPC159635
0.8023	Intermediate Similarity	NPC474359
0.8023	Intermediate Similarity	NPC158756
0.8022	Intermediate Similarity	NPC148463
0.8022	Intermediate Similarity	NPC121825
0.8	Intermediate Similarity	NPC85772
0.8	Intermediate Similarity	NPC219874
0.8	Intermediate Similarity	NPC35556
0.8	Intermediate Similarity	NPC89555
0.8	Intermediate Similarity	NPC173609
0.7978	Intermediate Similarity	NPC151770
0.7976	Intermediate Similarity	NPC304795
0.7935	Intermediate Similarity	NPC470974
0.7935	Intermediate Similarity	NPC470978
0.7935	Intermediate Similarity	NPC273197
0.7935	Intermediate Similarity	NPC234339
0.7935	Intermediate Similarity	NPC474947
0.7931	Intermediate Similarity	NPC470755
0.7931	Intermediate Similarity	NPC261380
0.7927	Intermediate Similarity	NPC123360
0.7927	Intermediate Similarity	NPC474527
0.7927	Intermediate Similarity	NPC471726
0.7912	Intermediate Similarity	NPC469645
0.7912	Intermediate Similarity	NPC475838
0.7912	Intermediate Similarity	NPC469692
0.7912	Intermediate Similarity	NPC125674
0.7912	Intermediate Similarity	NPC228451
0.7907	Intermediate Similarity	NPC59097
0.7907	Intermediate Similarity	NPC318468
0.7907	Intermediate Similarity	NPC53867
0.7901	Intermediate Similarity	NPC259599
0.7901	Intermediate Similarity	NPC117746
0.7901	Intermediate Similarity	NPC294434
0.7901	Intermediate Similarity	NPC15499
0.7895	Intermediate Similarity	NPC477511
0.7895	Intermediate Similarity	NPC264477
0.7889	Intermediate Similarity	NPC471818
0.7889	Intermediate Similarity	NPC475855
0.7889	Intermediate Similarity	NPC312042
0.7882	Intermediate Similarity	NPC39411
0.7882	Intermediate Similarity	NPC255580
0.7857	Intermediate Similarity	NPC182550
0.7857	Intermediate Similarity	NPC89128
0.7849	Intermediate Similarity	NPC17585
0.7841	Intermediate Similarity	NPC469910
0.7831	Intermediate Similarity	NPC187568
0.7831	Intermediate Similarity	NPC180290
0.7831	Intermediate Similarity	NPC41780
0.7826	Intermediate Similarity	NPC473330
0.7826	Intermediate Similarity	NPC476267
0.7826	Intermediate Similarity	NPC474247
0.7826	Intermediate Similarity	NPC473316
0.7826	Intermediate Similarity	NPC140543
0.7812	Intermediate Similarity	NPC471148
0.7812	Intermediate Similarity	NPC149371
0.7802	Intermediate Similarity	NPC284185
0.7802	Intermediate Similarity	NPC70595
0.7802	Intermediate Similarity	NPC74103
0.7802	Intermediate Similarity	NPC150978
0.7802	Intermediate Similarity	NPC123177
0.7791	Intermediate Similarity	NPC221231
0.7791	Intermediate Similarity	NPC471326
0.7765	Intermediate Similarity	NPC69271
0.7765	Intermediate Similarity	NPC74673
0.7765	Intermediate Similarity	NPC276356
0.7765	Intermediate Similarity	NPC302426
0.7753	Intermediate Similarity	NPC231889
0.7742	Intermediate Similarity	NPC471141
0.7738	Intermediate Similarity	NPC471465
0.7738	Intermediate Similarity	NPC196653
0.7738	Intermediate Similarity	NPC93763
0.7738	Intermediate Similarity	NPC108816
0.7727	Intermediate Similarity	NPC96621
0.7727	Intermediate Similarity	NPC474547
0.7717	Intermediate Similarity	NPC162205
0.7717	Intermediate Similarity	NPC273579
0.7717	Intermediate Similarity	NPC295204
0.7717	Intermediate Similarity	NPC288240
0.7708	Intermediate Similarity	NPC128733
0.7708	Intermediate Similarity	NPC185141
0.7708	Intermediate Similarity	NPC473384
0.7708	Intermediate Similarity	NPC133907
0.7708	Intermediate Similarity	NPC110443
0.7708	Intermediate Similarity	NPC47880
0.7708	Intermediate Similarity	NPC46998
0.7701	Intermediate Similarity	NPC193198
0.7701	Intermediate Similarity	NPC475947
0.7701	Intermediate Similarity	NPC272814
0.7701	Intermediate Similarity	NPC39588
0.7692	Intermediate Similarity	NPC129419
0.7692	Intermediate Similarity	NPC62815
0.7692	Intermediate Similarity	NPC475748
0.7692	Intermediate Similarity	NPC253144
0.7683	Intermediate Similarity	NPC474758
0.7674	Intermediate Similarity	NPC112868
0.7674	Intermediate Similarity	NPC475481
0.7674	Intermediate Similarity	NPC470241
0.7674	Intermediate Similarity	NPC79277
0.7674	Intermediate Similarity	NPC325031
0.7674	Intermediate Similarity	NPC286229
0.7667	Intermediate Similarity	NPC477302
0.7667	Intermediate Similarity	NPC475819
0.766	Intermediate Similarity	NPC230800
0.766	Intermediate Similarity	NPC476275
0.766	Intermediate Similarity	NPC279621
0.7653	Intermediate Similarity	NPC471143
0.7653	Intermediate Similarity	NPC477510
0.7647	Intermediate Similarity	NPC470244
0.7647	Intermediate Similarity	NPC264227

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 NPC474703 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	232
0.1-0.2	2048
0.2-0.3	3750
0.3-0.4	2069
0.4-0.5	727
0.5-0.6	247
0.6-0.7	73
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7528	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1695	Approved
0.7386	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1694	Approved
0.7157	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD46	Approved
0.7128	Intermediate Similarity	NPD5785	Approved
0.7128	Intermediate Similarity	NPD6698	Approved
0.7	Intermediate Similarity	NPD5209	Approved
0.6957	Remote Similarity	NPD5363	Approved
0.6923	Remote Similarity	NPD7154	Phase 3
0.6915	Remote Similarity	NPD5737	Approved
0.6915	Remote Similarity	NPD6672	Approved
0.6914	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5693	Phase 1
0.6818	Remote Similarity	NPD4756	Discovery
0.6813	Remote Similarity	NPD4269	Approved
0.6813	Remote Similarity	NPD4270	Approved
0.6813	Remote Similarity	NPD6435	Approved
0.6792	Remote Similarity	NPD6371	Approved
0.6782	Remote Similarity	NPD8039	Approved
0.6778	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD7838	Discovery
0.6739	Remote Similarity	NPD5362	Discontinued
0.6735	Remote Similarity	NPD5282	Discontinued
0.6703	Remote Similarity	NPD5369	Approved
0.6702	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6634	Remote Similarity	NPD4225	Approved
0.6634	Remote Similarity	NPD5696	Approved
0.6633	Remote Similarity	NPD6399	Phase 3
0.6633	Remote Similarity	NPD5778	Approved
0.6633	Remote Similarity	NPD5779	Approved
0.6593	Remote Similarity	NPD4822	Approved
0.6593	Remote Similarity	NPD4819	Approved
0.6593	Remote Similarity	NPD4252	Approved
0.6593	Remote Similarity	NPD4820	Approved
0.6593	Remote Similarity	NPD5368	Approved
0.6593	Remote Similarity	NPD4821	Approved
0.6566	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7900	Approved
0.6556	Remote Similarity	NPD4271	Approved
0.6556	Remote Similarity	NPD4268	Approved
0.6556	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6083	Phase 2
0.6535	Remote Similarity	NPD6084	Phase 2
0.6531	Remote Similarity	NPD7983	Approved
0.6526	Remote Similarity	NPD6684	Approved
0.6526	Remote Similarity	NPD7521	Approved
0.6526	Remote Similarity	NPD5330	Approved
0.6526	Remote Similarity	NPD7146	Approved
0.6526	Remote Similarity	NPD7334	Approved
0.6526	Remote Similarity	NPD6409	Approved
0.6509	Remote Similarity	NPD5697	Approved
0.6495	Remote Similarity	NPD6673	Approved
0.6495	Remote Similarity	NPD6080	Approved
0.6495	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD6904	Approved
0.6495	Remote Similarity	NPD6101	Approved
0.6449	Remote Similarity	NPD6881	Approved
0.6449	Remote Similarity	NPD6686	Approved
0.6449	Remote Similarity	NPD6899	Approved
0.6429	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5692	Phase 3
0.6422	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6650	Approved
0.6422	Remote Similarity	NPD6649	Approved
0.6415	Remote Similarity	NPD5739	Approved
0.6415	Remote Similarity	NPD6675	Approved
0.6415	Remote Similarity	NPD6402	Approved
0.6415	Remote Similarity	NPD7128	Approved
0.6413	Remote Similarity	NPD4695	Discontinued
0.6392	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6903	Approved
0.6389	Remote Similarity	NPD6013	Approved
0.6389	Remote Similarity	NPD6373	Approved
0.6389	Remote Similarity	NPD6372	Approved
0.6389	Remote Similarity	NPD6012	Approved
0.6389	Remote Similarity	NPD6014	Approved
0.6373	Remote Similarity	NPD7902	Approved
0.6364	Remote Similarity	NPD6411	Approved
0.6364	Remote Similarity	NPD6050	Approved
0.6364	Remote Similarity	NPD5694	Approved
0.6355	Remote Similarity	NPD5701	Approved
0.6354	Remote Similarity	NPD6098	Approved
0.6354	Remote Similarity	NPD4249	Approved
0.633	Remote Similarity	NPD2067	Discontinued
0.633	Remote Similarity	NPD7290	Approved
0.633	Remote Similarity	NPD6883	Approved
0.633	Remote Similarity	NPD7102	Approved
0.6311	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7320	Approved
0.6296	Remote Similarity	NPD6011	Approved
0.6289	Remote Similarity	NPD4251	Approved
0.6289	Remote Similarity	NPD4250	Approved
0.6283	Remote Similarity	NPD7115	Discovery
0.6273	Remote Similarity	NPD6617	Approved
0.6273	Remote Similarity	NPD6847	Approved
0.6273	Remote Similarity	NPD8130	Phase 1
0.6273	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD6648	Approved
0.6238	Remote Similarity	NPD7748	Approved
0.6216	Remote Similarity	NPD8297	Approved
0.6216	Remote Similarity	NPD6882	Approved
0.6216	Remote Similarity	NPD6053	Discontinued
0.6211	Remote Similarity	NPD5332	Approved
0.6211	Remote Similarity	NPD5331	Approved
0.619	Remote Similarity	NPD5344	Discontinued
0.617	Remote Similarity	NPD4790	Discontinued
0.6154	Remote Similarity	NPD7638	Approved
0.6122	Remote Similarity	NPD3573	Approved
0.6117	Remote Similarity	NPD7839	Suspended
0.6111	Remote Similarity	NPD6008	Approved
0.6095	Remote Similarity	NPD7640	Approved
0.6095	Remote Similarity	NPD7639	Approved
0.6071	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6274	Approved
0.6047	Remote Similarity	NPD3704	Approved
0.6042	Remote Similarity	NPD6110	Phase 1
0.604	Remote Similarity	NPD7515	Phase 2
0.602	Remote Similarity	NPD6422	Discontinued
0.602	Remote Similarity	NPD5279	Phase 3
0.6019	Remote Similarity	NPD5654	Approved
0.6019	Remote Similarity	NPD5210	Approved
0.6019	Remote Similarity	NPD4629	Approved
0.6019	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD5370	Suspended
0.6	Remote Similarity	NPD4753	Phase 2
0.6	Remote Similarity	NPD3197	Phase 1
0.5982	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5211	Phase 2
0.5979	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD3668	Phase 3
0.5943	Remote Similarity	NPD5286	Approved
0.5943	Remote Similarity	NPD4696	Approved
0.5943	Remote Similarity	NPD5285	Approved
0.5941	Remote Similarity	NPD5207	Approved
0.5938	Remote Similarity	NPD3667	Approved
0.5938	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6614	Approved
0.5905	Remote Similarity	NPD5959	Approved
0.5905	Remote Similarity	NPD4755	Approved
0.59	Remote Similarity	NPD5208	Approved
0.5897	Remote Similarity	NPD7101	Approved
0.5897	Remote Similarity	NPD6927	Phase 3
0.5897	Remote Similarity	NPD7100	Approved
0.5893	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD7260	Phase 2
0.5882	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD5281	Approved
0.5882	Remote Similarity	NPD7637	Suspended
0.5882	Remote Similarity	NPD5284	Approved
0.5872	Remote Similarity	NPD5141	Approved
0.5862	Remote Similarity	NPD7331	Phase 2
0.5862	Remote Similarity	NPD6317	Approved
0.5859	Remote Similarity	NPD3618	Phase 1
0.5856	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5847	Remote Similarity	NPD6319	Approved
0.5841	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5226	Approved
0.5833	Remote Similarity	NPD5225	Approved
0.5833	Remote Similarity	NPD5224	Approved
0.5833	Remote Similarity	NPD4633	Approved
0.5816	Remote Similarity	NPD3666	Approved
0.5816	Remote Similarity	NPD3133	Approved
0.5816	Remote Similarity	NPD4786	Approved
0.5816	Remote Similarity	NPD3665	Phase 1
0.5814	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD6313	Approved
0.5812	Remote Similarity	NPD6335	Approved
0.5812	Remote Similarity	NPD6314	Approved
0.581	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.581	Remote Similarity	NPD4697	Phase 3
0.581	Remote Similarity	NPD5221	Approved
0.581	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.581	Remote Similarity	NPD5222	Approved
0.5804	Remote Similarity	NPD2182	Approved
0.5804	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD4700	Approved
0.578	Remote Similarity	NPD5175	Approved
0.578	Remote Similarity	NPD5174	Approved
0.5776	Remote Similarity	NPD6868	Approved
0.5769	Remote Similarity	NPD6001	Approved
0.5755	Remote Similarity	NPD5173	Approved
0.5747	Remote Similarity	NPD7341	Phase 2
0.5741	Remote Similarity	NPD5223	Approved
0.5739	Remote Similarity	NPD4632	Approved
0.5729	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD8035	Phase 2
0.5728	Remote Similarity	NPD8034	Phase 2
0.5726	Remote Similarity	NPD6009	Approved
0.5702	Remote Similarity	NPD8328	Phase 3
0.57	Remote Similarity	NPD5690	Phase 2
0.5696	Remote Similarity	NPD29	Approved
0.5696	Remote Similarity	NPD28	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